US2003229067A1PendingUtilityA1
Pyrrolopyrimidine A2b selective antagonist compounds, their synthesis and use
Priority: Dec 20, 2001Filed: Dec 20, 2002Published: Dec 11, 2003
Est. expiryDec 20, 2021(expired)· nominal 20-yr term from priority
A61P 9/00A61P 35/00A61P 43/00A61P 35/04A61P 9/12A61P 37/08A61P 3/10A61P 9/10A61P 29/00A61P 27/02A61P 19/02A61P 1/04A61P 17/00A61P 17/04A61P 1/12C07D 487/04A61P 11/06A61P 13/00
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Claims
Abstract
The subject invention provides compounds having the structure: wherein, R 1 is a substituted or unsubstituted alkyl, wherein the substituent is hydroxyl, dihydroxy, carboxyl, —C(═O)NR a R b , —NR a R b , —NR a C(═O)NR a R b , —NR a C(═O)OR a , —OC(═O)NR a R b , or —NHC(═O)R a ; R 2 is hydrogen or a substituted or unsubstituted alkyl, wherein the substituent is hydroxyl, dihydroxy, carboxyl, —C(═O)NR a R b , —NR a R b , —NR a C(═O)NR a R b , —NR a C(═O)OR a , —OC(═O)NR a R b , or —NHC(═O)R a , or R 1 , R 2 and N together form a substituted piperazine, substituted azetidine ring, or a pyrrolidine ring substituted with —(CH 2 ) 2 OH or —CH 2 C(═O)OH; R 3 is a substituted or unsubstituted phenyl or a 5-6 membered heteroaryl ring, wherein the substituent is halogen, hydroxyl, cyano, (C 1 -C 15 )alkyl, (C 1 -C 15 )alkoxy, or —NR a R b ; R 4 is hydrogen or substituted or unsubstituted (C 1 -C 15 )alkyl; R 5 is —(CH 2 ) m OR 6 , —CHNOR 7 , —C(═O)NR 8 R 9 , —(CH 2 ) m C(═O)OR 10 , —(CH 2 ) k C(═O)NR 11 R 12 ; wherein R 6 is a substituted or unsubstituted (C 1 -C 30 )alkyl, (C 3 -C 10 )cycloalkyl, or an aryl, heteroaryl or 4-8 membered heterocyclic ring; R 7 is hydrogen, or a substituted or unsubstituted (C 1 -C 30 )alkyl, (C 1 -C 30 )alkylaryl; R 8 and R 9 are each independently hydrogen, or a substituted or unsubstituted (C 1 -C 30 )alkyl, (C 1 -C 30 )alkylaryl, (C 1 -C 30 )alkylamino, (C 1 -C 30 )alkoxy, or a saturated or unsaturated, monocyclic or bicyclic, carbocyclic or heterocyclic ring, or R 8 , N, and R 9 together form a substituted or unsubstituted 4-8 membered heterocyclic ring; R 10 is hydrogen or a substituted or unsubstituted (C 1 -C 30 )alkyl, (C 3 -C 10 )cycloalkyl, or an aryl, heteroaryl or heterocyclic ring; R 11 , N and R 12 together form a 4-8 membered heterocyclic ring; R a and R b are each independently hydrogen or alkyl; m is 0, 1, 2 or 3; and k is 1, 2 or 3, or a specific enantiomer thereof, or a specific tautomer thereof, or a pharmaceutically acceptable salt thereof, and a method for treating a disease associated with the A 2b adenosine receptor in a subject in need of such treatment comprising administering to the subject a therapeutically effective amount of the compounds of the invention.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1 . A compound having the structure:
wherein,
R 1 is a substituted or unsubstituted alkyl, wherein the substituent is hydroxyl, dihydroxy, carboxyl, —C(═O)NR a R b , —NR a R b , —NR a C(═O)NR a R b , —NR a C(═O)OR a , —OC(═O)NR a R b , or —NHC(═O)R a ;
R 2 is hydrogen or a substituted or unsubstituted alkyl, wherein the substituent is hydroxyl, dihydroxy, carboxyl, —C(═O)NR a R b , —NR a R b , —NR a C(═O)NR a R b , —NR a C(═O)OR a , —OC(═O)NR a R b , or —NHC(═O)R a , or
R 1 , R 2 and N together form a substituted piperazine, substituted azetidine ring, or a pyrrolidine ring substituted with —(CH 2 ) 2 OH or —CH 2 C(═O)OH;
R 3 is a substituted or unsubstituted phenyl or a 5-6 membered heteroaryl ring, wherein the substituent is halogen, hydroxyl, cyano, (C 1 -C 15 )alkyl, (C 1 -C 15 )alkoxy, or —NR a R b ;
R 4 is hydrogen or substituted or unsubstituted (C 1 -C 15 )alkyl;
R 5 is —(CH 2 ) m OR 6 , —CHNOR 7 , —C(═O)NR 8 R 9 , —(CH 2 ) m C(═O)OR 10 , —(CH 2 ) k C(═O)NR 11 R 12 ;
wherein R 6 is a substituted or unsubstituted (C 1 -C 30 )alkyl,
(C 3 -C 10 )cycloalkyl, or an aryl, heteroaryl or 4-8 membered heterocyclic ring;
R 7 is hydrogen, or a substituted or unsubstituted (C 1 -C 30 )alkyl, (C 1 -C 30 )alkylaryl;
R 8 and R 9 are each independently hydrogen, or a substituted or unsubstituted (C 1 -C 30 )alkyl, (C 1 -C 30 )alkylaryl, (C 1 -C 30 )alkylamino, (C 1 -C 30 )alkoxy, or a saturated or unsaturated, monocyclic or bicyclic, carbocyclic or heterocyclic ring, or
R 8 , N, and R 9 together form a substituted or unsubstituted 4-8 membered heterocyclic ring;
R 10 is hydrogen or a substituted or unsubstituted (C 1 -C 30 )alkyl, (C 3 -C 10 )cycloalkyl, or an aryl, heteroaryl or heterocyclic ring;
R 11 , N and R 12 together form a 4-8 membered heterocyclic ring;
R a and R b are each independently hydrogen or alkyl;
m is 0, 1, 2 or 3; and
k is 1, 2 or 3,
or a specific enantiomer thereof, or a specific tautomer thereof, or a pharmaceutically acceptable salt thereof.
2 . The compound of claim 1 , wherein any heterocyclic or heteroaryl ring, if present, is a piperazine, piperidine, pyrazine, pyridine, pyrrolidine, pyrazole, pyrimidine, thiophene, imidazole, azetidine, pyrrole, benzothiazole, benzodioxolane, dithiolane, oxathiine, imidazolidine, quinoline, isoquinoline, dihydro-1H-isoquinoline, dihydro-2H-pyridine, 1,3,4,9-tetrahydro-β-carboline, 2,8-diazaspiro[4.5]decane, 2,5-diazabicyclo[2.2.1]heptane, or [1,4]diazepane ring, dihydroisoquinoline, indole, isoindole, triazaspiro[4.5]decane, morpholine, furan or an isothiazole ring.
3 . The compound of claim 1 , having the structure:
wherein,
R 1 is hydrogen or methyl;
R 2 is —(CH 2 ) 2 NHC(═O)CH 3 , —(CH 2 ) 2 OH, —(CH 2 ) 2 NHC(═O)NHCH 3 , —CH 2 CH(CH 3 )OH, —CH(CH 2 OH)CH 2 CH(CH 3 ) 2 , —CH(CH 2 OH) 2 , —CH(CH 3 )CH 2 OH, —CH(CH 2 OH)CH(CH 3 ) 2 , —(CH 2 ) 3 OH, —(CH 2 ) 2 NH 2 , —(CH 2 ) 2 NHC(═O)N(CH 3 ) 2 , —(CH 2 ) 2 C(═O)NH 2 , —CH 2 C(═O)NH 2 , —CH 3 , —CH 2 CH(OH)CH 2 OH, —CH 2 C(═O)(NC 5 H 8 [OCH 3 ])(C 6 H 4 Cl) or
R 1 , R 2 and N together form a pyrrolidine ring substituted with —(CH 2 ) 2 OH or —CH 2 C(═O)OH, a piperazine ring substituted with —C(═O)CH 3 , or an azetidine ring substituted with —OH or CH 2 OH;
R 4 is hydrogen, or methyl; and
R 5 is —CH 2 O(C 6 H 5 ), —CH 2 O(C 6 H 4 Cl), —CH 2 O(C 6 H 4 Br), —CH 2 O(C 6 H 4 F), —CHNOCH 2 (C 6 H 5 ), —CH 2 O(C 6 H[OCH 3 ]), —CH 2 O(C 6 H 4 [CH 3 ]), —CHNOC(CH 3 ) 3 , —CH 2 O(C 5 H 4 N), —CH 2 (NC 5 H 4 [O]), —CH 2 O(C 6 H 4 [NH 2 ]), —CH 2 O(C 5 H 9 N)SO 2 (C 6 H 5 ), —CH 2 O(C 5 H 9 N)SO 2 CH 2 (C 6 H 5 ), —CH 2 O(C 6 H 4 [NHC(═O)CH 3 ]), —CH 2 O(C 5 H 9 N)(CH 2 ) P (C 6 H 5 ), —CH 2 O(C 5 H 9 N)(CH 2 ) P (C 6 H 4 Br), —CH 2 O(C 5 H 9 N)(CH 2 ) P (C 6 H 4 Cl), —CH 2 O(C 5 H 9 N)(CH 2 ) P (C 6 H 4 [OCH 3 ]), —CH 2 O(C 5 H 9 N)(CH 2 ) P (C 6 H 3 FCl), —CH 2 O(C 5 H 9 N)(CH 2 ) P (C 6 H4[CF 3 ]), —CH 2 O(CH 2 ) 2 CH(OH)(C 6 H 5 ), —CH 2 NOCH 2 (C 6 H 5 ), —CH 2 NOC(CH 3 ) 3 , —C(═O)(NC 4 H 8 O), —C(═O)(NC 4 HgN)CH 2 CHCH(C 6 H 5 ), —C(═O)(NC 4 H 8 N)(CH 2 ) P (C 6 H 5 ), —C(═O)(NC 4 H 8 N)(CH 2 ) 2 O(C 6 H 4 Cl), —C(═O)(NC 5 H 8 [CN])(C 6 H 5 ), —C(═O)(NC 4 H 8 N)CH 2 C 2 (C 6 H 5 ), —C(═O)(NC 4 (CH 3 ) 2 N)(CH 2 ) P (C 6 H 5 ), —C(═O)(NC 5 H 9 )CH(OH)(C 6 H 4 F), —C(═O)(NC 4 (CH 3 ) 2 NH), —C(═O)(NC 5 H 8 [CH 3 ])(C 6 H 5 ), —C(═O)(NC 4 H 8 N)(C 5 H 3 N[CF 3 ]), —C(═O)(NC 5 H 8 [OCH 3 ])(C 6 H 4 [C 6 H 4 Cl]), —C(═O)(NC 5 H 8 [OCH 3 ])(C 6 H 4 Cl), —C(═O)(NC 5 H 8 [OH])(C 6 H 4 Cl), —C(═O)(NC 5 H 8 [OH])(C 6 H 4 [C 6 H 4 Cl]), —C(═O)(NC 5 H 8 [OCH 3 ])(C 6 H 4 F), —C(═O)NH(C 5 H 9 N)(CH 2 ) P (C 6 H 5 ), —C(═O)(NC 5 H 9 )(CH 2 ) P (C 6 H 5 ), —C(O)(NC 5 H 9 )(NC 4 H 8 ), —C(═O)(NC 4 H 8 N)(CH 2 ) P (C 6 H 11 ), —C (═O)(NC 4 H 8 N)(CH 2 ) P CH(CH 3 ) 2 , —C(═O)(NC 5 H 9 [NC 5 H 10 ]), —C(═O)(NC 4 H 8 N)(C 5 H 9 ), —C(O)(NC 5 H 9 )NH 2 , —C(═O)(NC 5 H 8 [C(═O)CH 3 ])(C 6 H 5 ), —C(═O)(NC 5 H 7 )C 2 (C 6 H 5 ), —C(═O)(NC 5 H 9 )(C(CH 3 ) 3 , —C(═O)(NC 4 H 8 N)CH 2 C 2 (C 6 H[CN]), —C(═O)(NC 5 H 8 [C(═O)OCH 3 )(C 6 H 5 ), —C(═O)(NC 5 H 8 [C(═O)O(CH 2 ) P CH 3 ])(C 6 H 5 ), —C(═O)(NC 5 H 8 [C(═O)NH 2 ])(C 6 H 5 ), —C(═O)(NC 5 H 8 [C(═O)NHCH 3 ])(C 6 H 5 ), —C(═O)(NC 5 H 8 [NHC(═O)CH 3 ])(C 6 H 5 ), —C(═O)(NC 5 H 8 [C(═O)N(CH 3 ) 2 ])(C 6 H 5 ), —C(═O)(NC 5 H 8 [C(═O)NHCH 2 (C 6 H 5 )])(C 6 H 5 ), —C(═O)(NC 5 H 8 [C(═O)NH(CH 2 ) P CH 3 ])(C 6 H 5 ), —C(═O)(NC 5 H 8 [C(═O)N {(CH 2 ) P CH 3 } 2 ])(C 6 H 5 ), —C(═O)(NC 5 H 8 [C(═O)(NC 3 H 6 )])(C 6 H 5 ), —C(═O)(NC 5 H 8 [C(═O)OC(CH 3 ) 2 ])(C 6 H 5 ), —C(═O)(NC 5 H 8 [C(═O)NH 2 ])(NECH 2 CH 3 ), —C(═O)(NC 5 H 8 [OCH 3 ])(C 6 H 4 [OCH 3 ]), —C(═O)(NC 5 H 5 [C(—O)NH 2 ])(NC 4 H 8 ), —C(═O)(NC 5 H 7 )(C 6 H 4 [OCH 3 ]), —C(═O)(NC 5 H 8 [NH 2 ])(C 6 H 5 ), —C(═O)(NC 5 H 8 [C(═O)H])(C 6 H 5 ), —C(═O)(NC 5 H 8 [OCH 3 ])(CH 2 ) P (C 6 H 5 ), —C(═O)(NC 5 H 8 [OCH 3 ])(C 6 H 4 [CH 3 ]), —C(═O)(NC 5 H 8 [(CH 2 ) P OCH 3 ])(C 6 H 5 ), —C(═O)NH(C 4 H 7 N)(CH 2 ) P (C 6 H 5 ), —C(═O)(NC 4 H 8 N)(CH 2 ) P (C 6 H 4 Cl), —C(═O)(NC 4 H 8 N)(CH 2 ) P (C 6 H 4 [OCH 3 ]), —C(═O)NH(CH 2 ) P (C 6 H 4 [C 2 HSN 2 ], —C(═O)(NC 4 H 8 N)C(═O)(CH 2 ) P (C 6 H 4 Cl), —C(═O)(NC 5 H 9 )(C 3 N 2 H 2 )(C 6 H 4 Cl), —C(═O)(NC 4 H 8 N)CH 2 C(═O)N(CH 3 )(C 6 H 5 ), —C(═O)(NC 4 H 8 N)C(═O)O(CH 2 ) P (C 6 H 5 ), —C(═O)(NC 5 H 8 [C 2 H 3 N 2 O])(C 6 H 5 ), —C(═O)(NC 5 H 9 )N(CH 3 )(CH 2 ) P (C 6 H 5 ), —C(═O)(NC 5 H 9 )NH(CH 2 ) P (C 6 H 5 ), —C(═O)(NC 5 H 9 )NH(CH 2 ) P (C 6 H 4 Cl), —C(═O)(NC 5 H 9 )NH(CH 2 ) P (C 3 N 2 H 3 ), —C(═O)(NC 5 H 9 )NH(CH 2 ) P (C 5 H 4 N), —C(═O)(NC 5 H 9 )NH(CH 2 ) P (C 6 H 5 ), —C(═O)(NC 5 H 9 )N(CH 3 )(CH 2 ) P (C 6 H 5 ), —C(═O)(NC 5 H 9 )NHCH(CH 3 )(C 6 H 5 ), —(CH 2 )PC(═O)(NC 4 H 8 N)(CH 2 ) P (C 6 H 5 ), —C(═O)NH(CH 2 ) P (C 6 H 5 ), —C(═O)NHCH[(CH 2 ) P OH] 2 —C(═O)NH(CH 2 ) P (OH)(C 6 H 10 ), —C(═O)NH(CH 2 ) P (C 6 H 4 {O[C 6 H 5 ]}), —C(═O)(NC 4 H 7 )(CH 2 ) P NH(C 6 H 5 ), —C(═O)(NC 4 H 8 N)(CH 2 ) P (C 6 H 4 )CF 3 , —C(═O)(NC 4 H 8 N)(CH 2 ) P (C 6 H 4 F), —C(═O)(NC 4 H 8 N)(CH 2 ) P (C 7 O 2 H 5 ), —C(═O)(NC 4 H 8 N)(CH 2 ) P (C 6 H 4 )CH 3 , —C(═O)(NC 4 H 8 N)(CH 2 ) P (C 6 H 5 ), —C(═O)(NC 4 H 8 N)(CH 2 ) P (C 6 H 3 Cl 2 ), —C(═O)(NC 5 H 8 N)(CH 2 ) P (C 6 H 5 ), —C(═O)(NC 4 H 8 )(C 6 H 4 )NHC(═O)CH 3 , —C(═O)(NC 4 H 8 N)(C 6 H 4 [CN]), —C(═O)(NC 4 H 8 N)(C 6 H 4 [N(CH 3 )C(═O)CH 3 ]), —C(═O)(NC 4 H 8 N)(C 6 H 3 [(CH 3 ) 2 ]), —C(═O)(NC 4 H 8 N)(C 6 H 4 Cl), —C(═O)(NC 4 H 8 N)(C 6 H 3 [OCH 3 ) 2 ]), —C(═O)(NC 4 H 8 N)(C 6 H 3 Cl[(OCH 3 )]), —C(═O)(NC 5 H 9 N)(CH 2 ) P O(C 6 H 4 Cl), —C(—O)(NC 5 H 8 N)(CH 2 ) P (C 6 H 5 ), —C(═O)(NC 5 H 9 )(CH 2 ) P O(C 6 H 5 ), —C(═O)(NC 5 H 9 )(CH 2 ) P O(C 6 H 4 [CN]), —C(═O)(NC 4 H 8 N)(C 6 H 4 [NO 2 ]), —C(═O)(NC 4 H 8 N)(C 6 H 4 [C(═O)OCH 3 ]), —C(═O)(NC 4 H 8 N)(C 6 H 4 [CH 3 ]), —C(═O)(NC 5 H 9 )(CH 2 ) P O(C 6 H 3 Cl 2 ), —C(═O)(NC 5 H 9 )(CH 2 ) P O(C 6 H 3 [CN]), —C(═O)(NC 5 H 9 [CN])(C 6 H 4 Cl), —C(═O)(NC 5 H 8 N)(C 6 H 4 [C(═O)NH 2 ]), —C(═O)(NC 5 H 8 [CN])(C 6 H 4 [OCH 3 ]), —C(═O)(NC 5 H 8 [CN])(C 6 H 4 Cl), —C(═O)(NC 5 H 8 N[C(═O)(NC 4 H 8 )])(C 6 H 5 ), —C(═O)(NC 5 H 5 [C(═O)(NC 5 H 10 )])(C 6 H 5 ), —C(═O)(NC 5 H 8 [C(═O)(NC 4 H 8 O)])(C 6 H 5 ), —C(═O)(NC 5 H 8 [C(═O)NHC(CH 3 ) 3 ])(C 6 H 5 ), —C(═O)(NC 5 H 8 [C(═O)(NC 3 H 6 )])(C 6 H 5 ), —C(═O)(NC 5 H 8 [CH(CH 3 ) 2 ])(C 6 H 5 ), —C(═O)(NC 4 H 8 N)CH 2 C 2 (C 4 H 3 S), —C(═O)(NC 5 H 8 [C(═O)OCH 2 (C 4 H 7 )])(C 6 H 5 ), —C(═O)(NC 5 H 8 [OCH 3 ])(C 6 H 4 Cl), —C(═O)(NC 5 H 8 [OCH 3 ])(C 6 H 4 [CF 3 ]), —C(═O)(NC 5 H 8 [OCH 3 ])(C(CH 3 ) 2 ), —C(═O)(NC 4 H 8 N)(CH 2 ) P (C 6 H[CN]), —C(═O)(NC 5 H 8 )(C 6 H 5 ) 2 —CH 2 O(CH 2 ) P N(CH 3 )CH 2 CHCH(C 6 H 5 ), or —CH 2 O(CH 2 ) P NH(CH 2 ) 3 (C 6 H 5 );
wherein p is 0, 1, 2, 3 or 4,
or a specific enantiomer thereof, or a specific tautomer thereof, or a pharmaceutically acceptable salt thereof.
4 . The compound of claim 1 , having the structure:
wherein,
R 1 , R 2 and N together form a substituted azetidine or piperazine ring;
R 4 is H; and
R 6 is a substituted or unsubstituted aryl or heteroaryl ring.
5 . The compound of claim 4 , wherein R 1 , R 2 and N together form a substituted azetidine ring.
6 . The compound of claim 4 , wherein R 1 , R 2 and N together form a substituted piperazine ring.
7 . The compound of claim 1 , having the structure:
wherein,
R 6 is a substituted or unsubstituted aryl or heteroaryl ring; and
m is 0, 1, 2 or 3.
8 . The compound of claim 9 , wherein R 4 is H.
9 . The compound of claim 8 , wherein R 3 is substituted or unsubstituted phenyl.
10 . The compound of claim 9 , wherein,
R 1 is —(CH 2 ) 2 NHC(═O)CH 3 ; R 2 is hydrogen or methyl; R 4 is hydrogen or methyl; and R 6 is substituted or unsubstituted phenyl or pytidine.
11 . The compound of claim 10 , wherein R 2 is H.
12 . The compound of claim 11 , wherein R 6 is substituted phenyl.
13 . The compound of claim 1 , having the structure:
wherein,
R 6 is a substituted or unsubstituted (C 1 -C 30 )alkyl or (C 3 -C 10 )cycloalkyl;
m is 0, 1, 2 or 3.
14 . The compound of claim 13 , wherein R 4 is H;
15 . The compound of claim 14 , wherein R 3 is substituted or unsubstituted phenyl.
16 . The compound of claim 15 , wherein,
R 1 is —(CH 2 ) 2 NHC(═O)CH 3 ; R 2 is hydrogen or methyl; R 4 is hydrogen or methyl; and R 6 is substituted or unsubstituted cyclopentyl.
17 . The compound of claim 16 , wherein R 2 is H.
18 . The compound of claim 1 , having the structure:
wherein,
R 6 is a substituted or unsubstituted 4-8 membered heterocyclic ring; and
m is 0, 1, 2 or 3.
19 . The compound of claim 18 , wherein R 4 is H.
20 . The compound of claim 19 , wherein R 3 is substituted or unsubstituted phenyl;
21 . The compound of claim 20 , wherein,
R 1 is —(CH 2 ) 2 NHC(═O)CH 3 ; R 2 is hydrogen or methyl; R 4 is hydrogen or methyl; and R 6 is substituted or unsubstituted piperidine.
22 . The compound of claim 21 , wherein R 2 is H.
23 . The compound of claim 1 , having the structure:
wherein,
R 7 is hydrogen, or a substituted or unsubstituted (C 1 -C 30 )alkyl, (C 1 -C 30 )alkylaryl.
24 . The compound of claim 23 , wherein R 3 is substituted or unsubstituted phenyl.
25 . The compound of claim 24 , wherein R 4 is hydrogen.
26 . The compound of claim 1 , having the structure:
wherein,
R 8 , N, and R 9 together form a substituted or unsubstituted 4-8 membered heterocyclic ring.
27 . The compound of claim 26 , wherein R 8 NR 9 together form a substituted or unsubstituted azetidine, pyrrolidine, piperazine, piperidine, morpholine, azocane, dihydro-1H-isoquinoline, 1,2,3,6-tetrahydropyridine, dihydro-2H-pyridine, 1,3,4,9-tetrahydro-β-carboline, 1,3,8-triazaspiro[4.5]decane, 2,8-diazaspiro[4.5]decane, 2,5-diazabicyclo[2.2.1]heptane, 1,4-dioxa-8-azaspiro[4.5]decane, or [1.4]diazepane ring.
28 . The compound of claim 27 , wherein R 8 NR 9 together form a substituted or unsubstituted azetidine, pyrrolidine, piperazine, piperidine or [1.4]diazepane ring.
29 . The compound of claim 27 , wherein the ring formed by R 8 NR 9 is substituted with one or more aryl, heteroaryl, (C 1 -C 30 )alkylaryl, (C 1 -C 30 )alkylheteroaryl, (C 1 -C 30 )alkenylaryl, (C 1 -C 30 )alkenylheteroaryl, (C 1 -C 30 )alkynylaryl, or (C 1 -C 30 )allynylheteroaryl moiety, which itself can be substituted.
30 . The compound of claim 26 , wherein R 3 is a substituted or unsubstituted phenyl.
31 . The compound of claim 30 , wherein
R 1 is —(CH 2 ) 2 NHC(═O)CH 3 ; R 2 is hydrogen or methyl; and R 4 is hydrogen or methyl.
32 . The compound of claim 1 , having the structure:
wherein,
R 8 and R 9 are each independently hydrogen, or a substituted or unsubstituted (C 1 -C 30 )alkyl, (C 1 -C 30 )alkylaryl, (C 1 -C 30 )alkylamino, (C 1 -C 30 )alkoxy, or a saturated or unsaturated, monocyclic or bicyclic, carbocyclic or heterocyclic ring.
33 . The compound of claim 32 , wherein R 8 or R 9 is a (C 1 -C 30 )alkyl substituted with one or more hydroxy, dihydroxy or amino moiety.
34 . The compound of claim 32 , wherein R 8 or R 9 is a substituted or unsubstituted pyrrolidine, piperidine, bicycle[2.2.1]heptane, 2-oxoazepan, indane, or cyclopropylbenzene ring.
35 . The compound of claim 1 , having the structure:
wherein,
R 10 is hydrogen or a substituted or unsubstituted (C 1 -C 30 )alkyl, (C 3 -C 10 )cycloalkyl, or an aryl, heteroaryl or heterocyclic ring.
36 . The compound of claim 35 , wherein R 10 is a substituted or unsubstituted piperidine ring.
37 . The compound of claim 35 , wherein R 3 is a substituted or unsubstitited phenyl.
38 . The compound of claim 37 , wherein R 4 is hydrogen.
39 . The compound of claim 38 , wherein R 1 is —(CH 2 ) 2 NHC(═O)CH 3 ;
40 . The compound of claim 39 , wherein R 2 is hydrogen.
41 . The compound of claim 35 , having the structure:
42 . The compound of claim 1 , having the structure:
wherein,
R 11 NR 12 together form a substituted or unsubstituted 4-8 membered heterocyclic ring; and
k is 1, 2 or 3.
43 . The compound of claim 42 , wherein R 11 NR 12 together form a substituted or unsubstituted azetidine, pyrrolidine, piperazine, piperidine, morpholine, azocane, dihydro-1H-isoquinoline, 1,2,3,6-tetrahydropyridine, dihydro-2H-pyridine, 1,3,4,9-tetrahydro-β-carboline, 1,3,8-triazaspiro[4.5]decane, 2,8-diazaspiro[4.5]decane, 2,5-diazabicyclo[2.2.1]heptane, 1,4-dioxa-8-azaspiro[4.5]decane, or [1.4]diazepane ring.
44 . The compound of claim 43 , wherein R 11 NR 12 together form a substituted or unsubstituted azetidine, pyrrolidine, piperazine, piperidine or [1.4]diazepane ring.
45 . The compound of claim 43 , wherein the ring formed by R 11 NR 12 is substituted with one or more aryl, heteroaryl, (C 1 -C 30 )alkylaryl, (C 1 -C 30 )alkylheteroaryl, (C 1 -C 30 )alkenylaryl, (C 1 -C 30 )alkenylheteroaryl, (C 1 -C 30 )alkynylaryl, or (C 1 -C 30 )alkynylheteroaryl moieties, which itself can be substituted.
46 . The compound of claim 42 , wherein R 3 is a substituted or unsubstituted phenyl.
47 . The compound of claim 46 , wherein R 4 is hydrogen.
48 . The compound of claim 47 , wherein R 1 is —(CH 2 ) 2 NHC(═O)CH 3 .
49 . The compound of claim 1 , having the structure:
wherein,
R 11 NR 12 together form a substituted or unsubstituted 4-8 membered heterocyclic ring; and
k is 1, 2 or 3.
50 . The compound of claim 49 , wherein R 11 NR 12 together form a substituted or unsubstituted azetidine, pyrroliaine, piperazine, piperidine, morpholine, azocane, dihydro-1H-isoquinoline, 1,2,3,6-tetrahydropyridine, dihydro-2H-pyridine, 1,3,4,9-tetrahydro-β-carboline, 1,3,8-triazaspiro[4.5]decane, 2,8-diazaspiro[4.5]decane, 2,5-diazabicyclo[2.2.1]heptane, 1,4-dioxa-8-azaspiro[4.5]decane, or [1.4]diazepane ring.
51 . The compound of claim 50 , wherein R 11 NR 12 together form a substituted or unsubstituted azetidine, pyrrolidine, piperazine, piperidine or [1.4]diazepane ring.
52 . The compound of claim 50 , wherein the ring formed by R 11 NR 12 is substituted with one or more aryl, heteroaryl, (C 1 -C 30 )alkylaryl, (C 1 -C 30 )alkylheteroaryl, (C 1 -C 30 )alkenylaryl, (C 1 -C 30 )alkenylheteroaryl, (C 1 -C 30 )alkynylaryl, or (C 1 -C 30 )alkynylheteroaryl moiety.
53 . The compound of claim 49 , wherein R 3 is a substituted or unsubstituted phenyl.
54 . The compound of claim 53 , wherein R 4 is hydrogen.
55 . The compound of claim 54 , wherein R 1 is —(CH 2 ) 2 NHC(═O)CH 3 .
56 . A compound having the structure:
wherein,
R 13 and R 14 are each independently a hydrogen atom or a substituted or unsubstituted alkyl or alkylaryl moiety;
or R 13 NR 14 together form a substituted or unsubstituted 4 membered heterocyclic ring, a substituted or unsubstituted 5 membered ring, or a substituted or unsubstituted piperazine, wherein the five-membered ring is substituted with —CH 2 C(═O)OH;
R 15 is hydrogen or a substituted or unsubstituted alkyl; and
R 16 is —CH 2 NR 17 , —CH 2 OR 17 , —CH 2 CH 2 C(═O)OR 17 , CH 2 CH 2 C(═O)NR 18 R 19 , —C(═O)NR 18 R 19 , or —C(═O)OR 17 , wherein R 17 , R 18 and R 19 are each independently a hydrogen atom, a substituted or unsubstituted alkyl, aryl or alkylaryl moiety, or R 14 NR 15 together form a substituted or unsubstituted 4 to 8 membered heterocyclic ring.
57 . The compound of claim 56 , wherein any alkyl is a straight chain (C 1 -C 30 )alkyl or a branched chain (C 3 -C 30 )alkyl.
58 . The compound of claim 57 , wherein any heterocyclic ring, if present, is a substituted or unsubstituted morpholine, pyrrolidine, piperazine, piperidine, azocane, dihydro-1H-isoquinoline, dihydro-2H-pyridine, 1,3,4,9-tetrahydro-β-carboline, 1,3,8-triazaspiro[4.5]decane, 2,8-diazaspiro[4.5]decane, 2,5-diazabicyclo[2.2.1]heptane, or [1,4]diazepane ring.
59 . The compound of claim 7 , wherein the compound is selected from the group consisting of:
N-{2-[6-(4-Fluorophenoxymethyl)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-ethyl}-acetamide; N-{2-[6-(4-Methoxyphenoxymethyl)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-ethyl}-acetamide; N-[2-(2-Phenyl-6-m-tolyloxymethyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-ethyl]-acetamide; N-{2-[6-(3-Bromophenoxymethyl)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-ethyl}-acetamide; 3-[4-(2-Acetylaminoethylamino)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-6-ylmethoxy]-benzoic acid methyl ester; N-{2-[6-(4-Chlorophenoxymethyl)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-ethyl}-acetamide; and N-{2-[6-(3-Methoxyphenoxymelhyl)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-ethyl}-acetamide.
60 . The compound of claim 18 , wherein the compound is selected from the group consisting of:
N-(2-{6-[1-(Benzenesulfonyl)piperidin-4-yloxymethyl]-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}ethyl)acetamide; N-{2-[6-(1-Phenethylpiperidin-4-yloxymethyl)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]ethyl}acetamide; N-[2-{6-[1-(3-Phenylpropyl)piperidin-4-yloxymethyl]-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}ethyl]acetamide; N-(2-{6-[1-(4-Bromobenzyl)piperidin-4-yloxymethyl]-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}ethyl)acetamide; N-[2-(6-{1-[2-(2-Chlorophenyl)ethyl]piperidin-4-yloxymethyl}-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)ethyl]acetamide; N-[2-(6-{1-[2-(3-Chlorophenyl)ethyl]piperidin-4-yloxymethyl}-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)ethyl]acetamide; N-(2-{6-[1-(3-Chlorobenzyl)piperidin-4-yloxymethyl]-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}ethyl)acetamide; N-[2-(6-{1-[2-(4-Chlorophenyl)ethyl]piperidin-4-yloxymethyl}-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)ethyl]acetamide; N-[2-(6-{1-[2-(2-Methoxyphenyl)ethyl]piperidin-4-yloxymethyl}-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)ethyl]acetamide; N-[2-(6-{1-[2-(3-Methoxyphenyl)ethyl]piperidin-4-yloxymethyl}-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-4ylamino)ethyl]acetamide; N-[2-(6-{1-[2-(4-Methoxyphenyl)ethyl]piperidin-4-yloxymethyl}-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)ethyl]acetamide; N-[2-(6-{1-[2-(4-Fluorophenyl)ethyl]piperidin-4-yloxymethyl}-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)ethyl]acetamide; N-[2-(6-{1-[2-(2-Chloro-4-fluorophenyl)ethyl]piperidin-4-yloxymethyl}-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)ethyl]acetamide; N-[2-(6-{1-[2-(2-Chloro-6-fluorophenyl)ethyl]piperidin-4-yloxymethyl}-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)ethyl]acetamide; N-[2-(6-{1-[2-(2-Trifluoromethylphenyl)ethyl]piperidin-4-yloxymethyl}-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)ethyl]acetamide; and N-[2-(6-{1-[2-(2-Bromophenyl)ethyl]piperidin-4-yloxymethyl}-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)ethyl]acetamide.
61 . The compound of claim 13 , wherein the compound is N-(2-(6-{2-[Methyl-(3-phenylallyl)amino]ethoxymethyl}-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}ethyl]acetamide
62 . The compound of claim 26 , wherein the compound is selected from the group consisting of:
N-(2-{2-Phenyl-6-[4-(3-phenylallyl)-piperazine-1-carbonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; N-{2-[6-(4-Hydroxy4-isopropylpiperidine-1-carbonyl)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-ethyl}-acetamide; N-(2-{2-Phenyl-6-[4-(3-phenylpropyl)-piperazine-1-carhonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; N-{2-[6-(4-Phenethylpiperazine-1-carbonyl)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-ethyl}-acetamide; 2-{2-Phenyl-6-[4-(3-phenylpropyl)-piperazine-1-carbonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-acetamide; N-[2-(6-{4-[2-(4-Chlorophenoxy)-ethyl]-piperazine-1-carbonyl}-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-ethyl]-acetamide; N-{2-[6-(4-Cyano-4-phenylpiperidine-1-carbonyl)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-ethyl}-acetamide; N-(2-{2-Phenyl-6-[4-(3-phenylprop-2-ynyl)-piperazine-1-carbonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; N-(2-{6-[cis-3,5-Dimethyl4-(3-phenylpropyl)-piperazine-1-carbonyl]-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; N-{2-[6-(4,4-Diphenylpiperidine-1-carbonyl)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-ethyl}-acetamide; N-{2-[6-(3,3-Diphenylpiperidine-1-carbonyl)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-ethyl}-acetamide; N-{2-[6-(4-Methoxy4-phenylpiperidine-1-carbonyl)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-ethyl}-acetamide; N-(2-{6-[trans-2,5-Dimethyl-4-(3-phenylpropyl)-piperazine-1-carbonyl]-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; N-{2-[6-(trans-2,5-Dimethylpiperazine-1-carbonyl)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-ethyl}-acetamide; N-{2-[6-(4-Benzyl-cis-3,5-dimethylpiperazine-1-carbonyl)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-ethyl}-acetamide; N-{2-[6-(cis-3,5-Dimethyl4-phenethylpiperazine-1-carbonyl)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-ethyl}-acetamide; N-{2-[6-(3-Methyl-3-phenylpiperidine-1-carbonyl)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-ethyl}-acetamide; N-(2-{2-Phenyl-6-[4-(5-trifluoromethylpyridin-2-yl)-piperazine-1-carbonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; N-(2-{6-[4-(2′-Chlorobiphenyl-2-yl)-4-methoxypiperidine-1-carbonyl]-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; N-(2-{6-[4-(2-Chlorophenyl) 4 -methoxypiperidine-1-carbonyl]-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; N-(2-{6-[4-(2-Chlorophenyl) 4 -hydroxypiperidine-1-carbonyl]-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; N-(2-{6-[4-(2′-Chlorobiphenyl-2-yl)-4-hydroxypiperidine-1-carbonyl]-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; N-(2-{6-[4-(4-Fluorophenyl)-4-methoxypiperidine-1-carbonyl]-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; N-(2-{2-Phenyl-6-[4-(4-phenylbutyl)-piperazine-1-carbonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; N-(2-{2-Phenyl-6-[4-(3-phenylpropyl)-piperidine-1-carbonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; N-{2-[2-Phenyl-6-(4-pyrrolidin-1-yl-piperidine-1-carbonyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-ethyl}-acetamide; N-(2-{6-[4-(3-Cyclohexylpropyl)-piperazine-1-carbonyl]-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; N-(2-{6-[4-(4-Methylpentyl)-piperazine-1-carbonyl]-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; N-{2-[6-([1,4′]Bipiperidinyl-1′-carbonyl)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-ethyl}-acetamide; N-{2-[6-(4-Cyclopentylpiperazine-1-carbonyl)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-ethyl}-acetamide; N-{2-[6-(4-Aminopiperidine-1-carbonyl)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-ethyl}-acetamide; N-{2-[6-(4-Acetyl-4-phenylpiperidine-1-carbonyl)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-ethyl}-acetamide; N-(2-{6-[4-(2-Cyclohexylethyl)-piperazine-1-carbonyl]-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; N-{2-[2-Phenyl-6-(4-phenylethynyl-3,6-dihydro-2H-pyridine-1-carbonyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-ethyl}-acetamide; N-{2-[6-(4-tert-Butylpiperidine-1-carbonyl)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-ethyl}-acetamide; N-{2-[6-(4-Phenethylpiperidine-1-carbonyl)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-ethyl}-acetamide; N-[2-(6-{4-[3-(2-Cyanophenyl)-prop-2-ynyl]-piperazine-1-carbonyl}-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-ethyl]-acetamide; N-[2-(6-{4-[3-(3-Cyanophenyl)-prop-2-ynyl]-piperazine-1-carbonyl}-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-ethyl]-acetamide; N-[2-(6-{4-[3-(4-Cyanophenyl)-prop-2-ynyl]-piperazine-1-carbonyl}-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-ethyl]-acetamide; 1-[4-(2-Acetylaminoethylamino)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidine-6-carbonyl]-4-phenylpiperidine-4-carboxylic acid methyl ester; N-(2-{6-[4-(1-Hydroxyethyl)-4-phenylpiperidine-1-carbonyl]-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; N-[2-(6-{4-[3-(4-Cyanophenyl)-propyl]-piperazine-1-carbonyl}-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-ethyl]-acetamide; 1-[4-(2-Acetylaminoethylamino)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidine-6-carbonyl]-4-phenylpiperidine-4-carboxylic acid ethyl ester; 1-[4-(2-Acetylaminoethylamino)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidine-6-carbonyl]-4-phenylpiperidine-4-carboxylic acid amide; 1-[4-(2-Acetylaminoethylamino)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidine-6-carbonyl]-4-phenylpiperidine-4-carboxylic acid methylamide; 1-[4-(2-Acetylaminoethylamino)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidine-6-carbonyl]-4-phenylpiperidine-4-carboxylic acid dimethylamide; 1-[4-(2-Acetylaminoethylamino)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidine-6-carbonyl]-4-phenylpiperidine-4-carboxylic acid benzylamide; 1-[4-(2-Acetylaminoethylamino)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidine-6-carbonyl]-4-phenylpiperidine-4-carboxylic acid ethylamide; 1-[4-(2-Acetylaminoethylamino)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidine-6-carbonyl]-4-phenylpiperidine-4-carboxylic acid diethylamide; N-(2-{6-[4-(Azetidine-1-carbonyl)-4-phenylpiperidine-1-carbonyl]-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; N-(2-{2-Phenyl-6-[4-phenyl-4-(pyrrolidine-1-carbonyl)-piperidine-1-carbonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; N-(2-{2-Phenyl-6-[4-phenyl-4-(piperidine-1-carbonyl)-piperidine-1-carbonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; N-(2-{6-[4-(Morpholine-4-carbonyl)-4-phenylpiperidine-1-carbonyl]-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; 1-[4-(2-Acetylaminoethylamino)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidine-6-carbonyl]-4-phenylpiperidine-4-carboxylic acid tert-butylamide; N-{2-[6-(4-Isopropyl-4-phenylpiperidine-1-carbonyl)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-ethyl}-acetamide; N-(2-{2-Phenyl-6-[4-(3-thiophen-2-yl-prop-2-ynyl)-piperazine-1-carbonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; 1-[4-(2-Acetylaminoethylamino)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidine-6-carbonyl]-4-phenylpiperidine-4-carboxylic acid cyclobutylmethyl ester; N-(2-{6-[4-(4-Chlorophenyl)-4-methoxypiperidine-1-carbonyl]-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; N-(2-{6-[4-Methoxy-4-(3-trifluoromethylphenyl)-piperidine-1-carbonyl]-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; N-{2-[6-(4-Isopropyl-4-methoxypiperidine-1-carbonyl)-2-pbenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-ethyl}-acetamide; N-{2-[6-(4-Acetylamino-4-phenylpiperidine-1-carbonyl)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-ethyl}-acetamide; 1-[4-(2-Acetylaminoethylamino)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidine-6-carbonyl]-4-phenylpiperidine-4-carboxylic acid isopropyl ester; 1-[4-(2-Acetylaminoethylamino)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidine-6-carbonyl]-4-ethylaminopiperidine-4-carboxylic acid amide; N-(2-{6-[4-Methoxy-4-(3-methoxyphenyl)-piperidine-1-carbonyl]-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; 1-[4-(2-Acetylaminoethylamino)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidine-6-carbonyl]-4-pyrrolidin-1-ylpiperidine-4-carboxylic acid amide; N-(2-{6-[4-(2-Methoxyphenyl)-3,6-dihydro-2H-pyridine-1-carbonyl]-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; N-{2-[6-(4-Amino-4-phenylpiperidine-1-carbonyl)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-ethyl}-acetamide; N-{2-[6-(4-Formyl-4-phenylpiperidine-1-carbonyl)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-ethyl}-acetamide; N-{2-[6-(4-Benzyl4-methoxypiperidine-1-carbonyl)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-ethyl}-acetamide; N-{2-[6-(4-Methoxy-4-o-tolylpiperidine-1-carbonyl)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-ethyl}-acetamide; N-{2-[6-(4-Methoxymethyl-4-phenylpiperidine-1-carbonyl)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-ethyl}-acetamide; N-[2-(6-{4-[3-(2-Chlorophenyl)-propyl]-piperazine-1-carbonyl}-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-ethyl]-acetamide; N-[2-(6-{4-[3-(3-Chlorophenyl)-propyl]-piperazine-1-carbonyl}-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-ethyl]-acetamide; N-[2-(6-{4-[3-(4-Chlorophenyl)-propyl]-piperazine-1-carbonyl}-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-ethyl]-acetamide; N-[2-(6-{4-[3-(2-Methoxyphenyl)-propyl]-piperazine-1-carbonyl}-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-ethyl]-acetamide; N-[2-(6-{4-[3-(3-Methoxyphenyl)-propyl]-piperazine-1-carbonyl}-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-ethyl]-acetamide; N-[2-(6-{4-[3-(4-Methoxyphenyl)-propyl]-piperazine-1-carbonyl}-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-ethyl]-acetamide; N-[2-(6-{4-[3-(4-Chlorophenyl)-propionyl]-piperazine-1-carbonyl}-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-ethyl]-acetamide; N-[2-(6-{4-[3-(3-Chlorophenyl)-propionyl]-piperazine-1-carbonyl}-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-ethyl]-acetamide; N-[2-(6-{4-[3-(2-Chlorophenyl)propionyl]-piperazine-1-carbonyl}-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-ethyl]-acetamide; N-[2-(6-{4-[5-(4-Chlorophenyl)-2H-pyrazol-3-yl]-piperidine-1-carbonyl}-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-ethyl]-acetamide; 2-{4-[4-(2-Acetylaminoethylamino)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidine-6-carbonyl]-piperazin-1-yl}-N-methyl-N-phenylacetamide; 4-[4-(2-Acetylaminoethylamino)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidine-6-carbonyl]-piperazine-1-carboxylic acid benzyl ester; N-{2-[6-(4-Oxo-1-phenyl-1,3,8-triazaspiro[4 .5]decane-8-carbonyl)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-ethyl}-acetamide; N-(2-{6-[4-(Methylphenethylamino)-piperidine-1-carbonyl]-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; N-{2-[6-(4-Phenethylaminopiperidine-1-carbonyl)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-ethyl}-acetamide; N-[2-(6-{4-[2-(4-Chlorophenyl)-ethylamino]-piperidine-1-carbonyl}-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-ethyl]-acetamide; N-[2-(6-{4-[2-(3H-Imidazol-4-yl)-ethylamino]-piperidine-1-carbonyl}-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-ethyl]-acetamide; N-(2-{2-Phenyl-6-[4-(2-pyridin-4-ylethylamino)-piperidine-1-carbonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; N-(2-{2-Phenyl-6-[4-(2-pyridin-2-ylethylamino)-piperidine-1-carbonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; N-{2-[6-(4-Benzylaminopiperidine-1-carbonyl)-2-phenyl-7H-pyrrolo[2,3-d]-pyrimidin-4-ylamino]-ethyl}-acetamide; N-(2-{6-[4-(Benzylmethylamino)-piperidine-1-carbonyl]-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; N-[2-(2-Phenyl-6-{4-[(pyridin-4-ylmethyl)-amino]-piperidine-1-carbonyl}-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-ethyl]-acetamide; N-(2-{2-Phenyl-6-[4-(2-pyridin-3-ylethylamino)-piperidine-1-carbonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; N-{2-[2-Phenyl-6-((S)-2-phenylaminomethylpyrrolidine-1-carbonyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-ethyl}-acetamide; N-[2-(2-Phenyl-6-{4-[3-(4-trifluoromethylphenyl)-propyl]-piperazine-1-carbonyl}-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-ethyl]-acetamide; N-[2-(6-{4-[3-(4-Fluorophenyl)-propyl]-piperazine-1-carbonyl}-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-ethyl]-acetamide; N-(2-{6-[4-(3-Benzo[1,3]dioxol-5-yl-propyl)-piperazine-1-carbonyl]-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; N-(2-{2-Phenyl-6-[4-(3-p-tolylpropyl)-piperazine-1-carbonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; N-[2-(6-{4-[3-(4-Bromophenyl)-propyl]-piperazine- -carbonyl}-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-ethyl]-acetamide; N-[2-(6-{4-[3-(3,4-Dichlorophenyl)-propyl]-piperazine-1-carbonyl}-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-ethyl]-acetamide; N-[2-(6-{4-[3-(2,4-Dichlorophenyl)-propyl]-piperazine-1-carbonyl}-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-ethyl]-acetamide; N-{2-[6-(4-Benzyl-[1,4]diazepane-1-carbonyl)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-ethyl}-acetamide; N-{2-[6-(4-Phenethyl-[1,4]diazepane-1-carbonyl)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-ethyl}-acetamide; N-(2-{2-Phenyl-6-[4-(3-phenylpropyl)-[1,4]diazepane-1-carbonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; N-(2-{6-[4-(4-Acetylaminophenyl)-piperazine-1-carbonyl]-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; N-(2-{6-[4-(2-Cyanophenyl)-piperazine-1-carbonyl]-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; N-[2-(6-{4-[4-(Acetylmethylamino)-phenyl]-piperazine-1-carbonyl}-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-ethyl]-acetamide; N-(2-{6-[4-(2,6-Dimethylphenyl)-piperazine-1-carbonyl]-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; N-(2-{6-[4-(2-Chlorophenyl)-piperazine-1-carbonyl]-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; N-(2-{6-[4-(2,4-Dimethoxyphenyl)-piperazine-1-carbonyl]-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; N-(2-{6-[4-(5-Chloro-2-methoxyphenyl)-piperazine-1-carbonyl]-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; N-(2-{6-[4-(4-Chlorophenoxymethyl)-piperidine-1-carbonyl]-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; N-{2-[6-(5-Benzyl-2,5-diazabicyclo[2.2.1]heptane-2-carbonyl)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-ethyl}-acetamide; N-{2-[6-(4-Phenoxymethylpiperidine-1-carbonyl)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-ethyl}-acetamide; N-(2-{6-[4-(4-Cyanophenoxymethyl)-piperidine-1-carbonyl]-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; N-(2-{6-[4-(3-Cyanophenoxymethyl)-piperidine-1-carbonyl]-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; N-(2-{6-[4-(2-Nitrophenyl)-piperazine-1-carbonyl]-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; 2-{4-[4-(2-Acetylaminoethylamino)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidine-6-carbonyl]-piperazin-1-yl}-benzoic acid methyl ester; N-{2-[2-Phenyl-6-(4-o-tolylpiperazine-1-carbonyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino]-ethyl}-acetamide; N-(2-{6-[4-(3,4-Dichlorophenoxymethyl)-piperidine-1-carbonyl]-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; N-(2-{6-[4-(2-Cyanophenoxymethyl)-piperidine-1-carbonyl]-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; N-(2-{6-[4-(2-Chlorophenyl)-4-cyanopiperidine-1-carbonyl]-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; 2-{4-[4-(2-Acetylaminoethylamino)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidine-6-carbonyl]-piperazin-1-yl}-benzamide;
N-(2-{6-[4-Cyano-4-(2-methoxyphenyl)-piperidine-1-carbonyl]-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide;
N-(2-{6-[4-(3-Chlorophenyl)-4-cyanopiperidine-1-carbonyl]-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide;
N-(2-{6-[4-Cyano4-(3-methoxyphenyl)-piperidine-1-carbonyl]-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide; and
N-(2-{6-[4-Cyano-4-(4-methoxyphenyl)-piperidine-1-carbonyl]-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide.
63 . The compound of claim 32 , wherein the compound is selected from the group consisting of:
4-(2-Acetylaminoethylamino)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid (3-phenoxyphenyl)-amide; 4-(2-Acetylaminoethylamino)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid (1-benzylpiperidin4-yl)-amide; 4-(2-Acetylaminoethylamino)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid (1-benzylpyrrolidin-3-yl)-amide; 4-(2-Acetylaminoethylamino)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid 4-[1,2,3]thiadiazol-4-yl-benzylamide; 4-(2-Acetylaminoethylamino)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid benzylamide; 4-(2-Acetylaminoethylamino)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid (2-hydroxy-1-hydroxymethylethyl)-amide; 4-(2-Acetylaminoethylamino)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid (1-hydroxycyclohexylmethyl)-amide; and 4-(2-Acetylaminoethylamino)-2-phenyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid [2-(4-phenoxyphenyl)-ethyl]-amide.
64 . The compound of claim 42 , wherein the compound is N-(2-{6-[3-(4-Benzylpiperazin-1-yl)-3-oxopropyl]-2-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-ethyl)-acetamide.
65 . A compound having the structure:
wherein
R 3 is a substituted or unsubstituted 4-10 membered aryl, heteroaryl or heterocyclic ring;
R 20 is halogen or —NH(CHR 20 ′) n NHC(═O)CH 3 , where R 20 ′ is H, OH, alkyl, hydroxyalkyl, cycloalkyl, heteroalkyl, or amino;
R 21 is H or —C(═O)OH;
R 22 is H or SO 2 Ph; and
n is 2, 3, 4 or 5;
wherein when R 20 is —NH(CHR 20 ′) n NHC(═O)CH 3 , R 21 is —C(═O)OH.
66 . The compound of claim 65 , wherein R 3 is substituted or unsubstituted phenyl.
67 . The compound of claim 66 , wherein R 20 is Cl.
68 . The compound of claim 67 , wherein R 22 is SO 2 Ph.
69 . The compound of claim 68 , wherein R 21 is H.
70 . The compound of claim 69 , wherein R 21 is —C(═O)OH.
71 . The compound of claim 67 , wherein R 20 is —NH(CH 2 ) n NHC(═O)CH 3 and R 21 is —C(═O)OH.
72 . The compound of claim 71 , wherein R 22 is H.
73 . The compound of claim 71 , wherein R 22 is SO 2 Ph.
74 . A method for treating a disease associated with the A 2b adenosine receptor in a subject in need of such treatment comprising administering to the subject a therapeutically effective amount of the compound of claim 1 so as to thereby treat the disease associated with the A 2b adenosine receptor in the subject, wherein the disease associated with the A 2b adenosine receptor is asthma, urticaria, scleroderm arthritis, myocardial infarction, myocardial reperfusion after ischemia, diabetic retinopathy, retinopathy of prematurity, diabetes, diarrhea, inflammatory bowel disease, proliferating tumor or is associated with mast cell degranulation, vasodilation, hypertension, hypersensitivity or the release of allergic mediators.
75 . The method of claim 74 , wherein the disease associated with the A 2b adenosine receptor is diabetes.
76 . The method of claim 74 , wherein the disease associated with the A 2b adenosine receptor is asthma.
77 . The method of claim 74 , wherein the disease associated with the A 2b adenosine receptor is associated with mast cell degranulation.
78 . The method of claim 74 , wherein the disease associated with the A 2b adenosine receptor is a proliferating tumor.
79 . A method for treating a disease associated with the A 2b adenosine receptor in a subject in need of such treatment comprising administering to the subject a therapeutically effective amount of the compound of claim 1 so as to thereby treat the disease associated with the A 2b adenosine receptor in the subject, wherein the disease associated with the A 2b adenosine receptor is asthma, urticaria, scleroderm arthritis, myocardial infarction, myocardial reperfusion after ischemia, diabetic retinopathy, retinopathy of prematurity, diabetes, diarrhea, inflammatory bowel disease, proliferating tumor or is associated with mast cell degranulation, vasodilation, hypertension, hypersensitivity or the release of allergic mediators.
80 . A pharmaceutical composition comprising the compound of claim 1 , 3 , 4 , 7 , 13 , 18 , 23 , 26 , 32 , 35 , 42 or 49 and a pharmaceutically acceptable carrier.
81 . The pharmaceutical composition of claim 80 , formulated for oral, topical, parenteral or nasal administration.
82 . A process for the manufacture of a pharmaceutical composition comprising admixing the compound of claim 1 , 3 , 4 , 7 , 13 , 18 , 23 , 26 , 32 , 35 , 42 or 49 with a pharmaceutically acceptable carrier.
83 . An article of manufacture comprising
packaging material; the pharmaceutical composition of claim 80; and instructions for use of the pharmaceutical composition in the treatment of a disease associated with the A 2b adenosine receptor.
84 . A process of manufacturing a compound having the structure:
wherein,
R 8 and R 9 are each independently hydrogen, or a substituted or unsubstituted (C 1 -C 30 )alkyl, (C 1 -C 30 )alkylaryl, (C 1 -C 30 )alkylamino, (C 1 -C 30 )alkoxy, or a saturated or unsaturated, monocyclic or bicyclic, carbocyclic or heterocyclic ring, or
R 8 , N, and R 9 together form a substituted or unsubstituted 4-8 membered heterocyclic ring,
comprising:
(a) reacting
with PhSO 2 Cl and a reducing agent in the presence of solvent to produce:
(b) reacting the product of step (a) with CO 2 in the presence of lithium diisopropylamide (LDA) and a solvent to produce:
(c) reacting the product of step (b) with
in the presence solvent to produce:
(d) reacting the product of step (c) with a hydroxide base in solution to produce:
(e) reacting the product of step (d) with HNR 7 R 8 in the presence of a base and a coupling agent to produce the compound.
85 . The process of claim 84 , wherein the reducing agent in step (a) is NaH and the solvent is dimethylformamide (DMF).
86 . The process of claim 84 , wherein the solvent in step (b) is tetrahydrofuran (THF).
87 . The process of claim 84 , wherein the solvent in step (c) is dimethyl sulfoxide (DMSO).
88 . The process of claim 84 , wherein the hydroxide base in step (d) is sodium hydroxide.
89 . The process of claim 84 , wherein the base in step (e) is triethylamine, the coupling agent is O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU), benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate, or 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide (EDC) and N-Hydroxybenzotriazole, and the solvent is DMF.
90 . The process of claim 84 , wherein the order of the steps is (a), (b), (c), (e), then (d).
91 . A compound produced by the process of claim 84 .
92 . Use of the compound of any one of claims 1 - 64 for manufacturing a medicament useful for treating a disease associated with the A 2b adenosine receptor in a subject, wherein the disease associated with the A 2b adenosine receptor is asthma, urticaria, scleroderm arthritis, myocardial infarction, myocardial reperfusion after ischemia, diabetic retinopathy, retinopathy of prematurity, diabetes, diarrhea, inflammatory bowel disease, proliferating tumor, or is associated with mast cell degranulation, vasodilation, hypertension, hypersensitivity or the release of allergic mediators.
93 . The use of claim 92 , wherein the disease associated with the A 2b adenosine receptor is diabetes.
94 . The use of claim 92 , wherein the disease associated with the A 2b adenosine receptor is asthma.
95 . The use of claim 92 , whereinr the disease associated with the A 2b adenosine receptor is associated with mast cell degranulation.
96 . The use of claim 92 , wherein the disease associated with the A 2b adenosine receptor is a proliferating tumor.
97 . The compound of any one of claims 1 , 2 , 4 - 30 , 32 - 46 , 49 - 53 , or 56 - 58 , wherein any substituent, if present, is selected from halogen, hydroxyl, carbonyl, straight chain (C 1 -C 30 )alkyl, branched chain (C 3 -C 30 )alkyl, (C 3 -C 10 )cycloalkyl, straight chain(C 1 -C 30 )alkylcarbonyloxy, branched chain (C 3 -C 30 )alkylcarbonyloxy, arylcarbonyloxy, straight chain(C 1 -C 30 )alkoxycarbonyloxy, branched chain(C 3 -C 30 )alkoxycarbonyloxy, aryloxycarbonyloxy, carboxylate, straight chain(C 1 -C 30 )alkylcarbonyl, branched chain (C 3 -C 30 )alkylcarbonyl, arylcarbonyl, straight chain (C 1 -C 30 )alkoxycarbonyl, branched chain (C 3 -C 30 )alkoxycarbonyl, aminocarbonyl, straight chain (C 1 -C 30 )alkylthiocarbonyl, branched chain (C 3 -C 30 )alkylthiocarbonyl, straight chain (C 1 -C 30 )alkylsulfonyl, branched chain (C 3 -C 30 )alkylsulfonyl, straight chain (C 1 -C 30 )alkoxyl, branched chain (C 1 -C 30 )alkoxyl, phosphate, phosphonato, cyano, amino, straight chain (C 1 -C 30 )alkylamino, branched chain (C 3 -C 30 )alkylamino, straight chain (C 1 -C 30 )dialkylamino, branched chain (C 3 -C 30 )dialkylamino, arylamino, diarylamino, straight chain (C 1 -C 30 )alkylarylamino, branched chain (C 3 -C 30 )alkylarylamino, acylamino, straight chain (C 1 -C 30 )alkylcarbonylamino, branched chain (C 3 -C 30 )alkylcarbonylamino, arylcarbonylamino, carbamoyl, ureido, amidino, imino, sulfhydryl, straight chain (C 1 -C 30 )alkylthio, branched chain (C 3 -C 30 )alkylthio, arylthio, thiocarboxylate, sulfates, sulfonato, sulfamoyl, sulfonamido, sulfonyl, benzenesulfonyl, nitro, trifluoromethyl, azido, 6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole, 3,4-dihydroxy-5-methoxytetrahydrofuran, 4-10 membered heterocyclyl, straight chain (C 1 -C 30 )alkylaryl, branched chain (C 3 -C 30 )alkylaryl, straight chain (C 1 -C 30 )alkylheteroaryl, branched chain (C 3 -C 30 )alkylheteroaryl, (C 1 -C 30 )alkenylaryl, (C 1 -C 30 )alkenylheteroaryl, (C 1 -C 30 )alkynylaryl, (C 1 -C 30 )alkynylheteroaryl or an aromatic or 5-6 membered heteroaromatic moiety,
which substituent may be further substituted by any of the above.Cited by (0)
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