US2010249239A1PendingUtilityA1
Bis(thio-hydrazide amide) formulation
Est. expiryAug 16, 2025(expired)· nominal 20-yr term from priority
A61K 31/4025A61K 31/444A61P 35/00A61K 31/165A61K 31/16A61P 35/04A61K 31/277
53
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Claims
Abstract
Disclosed herein are compositions comprising a compound represented by structural formula (I): 2 g of which is reconstitutable in 10 mL of a water in less than 10 minutes, and methods for preparing these compositions. Also disclosed are compositions comprising a compound represented by structural formula (I) and a pharmaceutically acceptable excipient, wherein the molar ratio of said compound to said excipient is from 1:20 to 1:1, and methods for preparing these compositions.
Claims
exact text as granted — not AI-modified1 . A composition comprising a compound represented by the following structural formula:
wherein:
Y is a covalent bond or a substituted or unsubstituted straight chained hydrocarbyl group;
R 1 -R 4 are independently —H, an aliphatic group, a substituted aliphatic group, an aryl group or a substituted aryl group, or R 1 and R 3 taken together with the carbon and nitrogen atoms to which they are bonded, and/or R 2 and R 4 taken together with the carbon and nitrogen atoms to which they are bonded, form a non-aromatic heterocyclic ring optionally fused to an aromatic ring;
Z is —O or —S; and
M + is a pharmaceutically acceptable monovalent cation and M 2+ is a pharmaceutically acceptable divalent cation; and
wherein 2 g of said composition is reconstitutable in 10 mL of a water in less than 10 minutes.
2 . The composition of claim 1 , wherein the composition further comprises a pharmaceutically acceptable excipient, and wherein the molar ratio of said compound to said excipient is from 1:20 to 1:1.
3 . The composition of claim 2 , wherein the pharmaceutically acceptable excipient is a crystalline bulking excipient.
4 . The composition of claim 3 , wherein the pharmaceutically acceptable cation is Na + or K + .
5 . The composition of claim 4 , wherein Z is O; R 1 and R 2 are the same; and R 3 and R 4 are the same.
6 . The composition of claim 5 , wherein:
Y is a covalent bond, —C(R 5 R 6 )—, —(CH 2 CH 2 )—, trans-(CH═CH)—, cis-(CH═CH)— or —(CC)— group; and R 5 and R 6 are each independently —H, an aliphatic or substituted aliphatic group, or R 5 is —H and R 6 is a substituted or unsubstituted aryl group, or R 5 and R 6 , taken together, are a C2-C6 substituted or unsubstituted alkylene group.
7 . The composition of claim 6 , wherein:
Y is —C(R 5 R 6 )—; R 1 and R 2 are each a substituted or unsubstituted aryl group; and R 3 and R 4 are each a substituted or unsubstituted aliphatic group.
8 . The composition of claim 7 , wherein: R 3 and R 4 are each an alkyl group; R 5 is —H; and R 6 is —H or methyl.
9 . The composition of claim 8 , wherein R 1 and R 2 are each a substituted or unsubstituted phenyl group and R 3 and R 4 are each methyl or ethyl.
10 . The composition of claim 6 , wherein
Y is —CR 5 R 6 —; R 1 and R 2 are both a substituted or unsubstituted aliphatic group; R 5 is —H; and R 6 is —H or an optionally substituted aliphatic group.
11 . The composition of claim 10 , wherein R 1 and R 2 are both a C3-C8 cycloalkyl group optionally substituted with at least one alkyl group; R 3 and R 4 are both an alkyl group; and R 6 is —H or methyl.
12 . The composition of claim 11 , wherein R 1 and R 2 are both cyclopropyl or 1-methylcyclopropyl.
13 . The composition of claim 3 , wherein the compound is represented by the following structural formula:
wherein:
R 1 and R 2 are both phenyl; R 3 and R 4 are both methyl; R 5 and R 6 are both —H;
R 1 and R 2 are both phenyl; R 3 and R 4 are both ethyl; R 5 and R 6 are both —H;
R 1 and R 2 are both 4-cyanophenyl; R 3 and R 4 are both methyl; R 5 is methyl; R 6 is —H;
R 1 and R 2 are both 4-methoxyphenyl; R 3 and R 4 are both methyl; R 5 and R 6 are both —H;
R 1 and R 2 are both phenyl; R 3 and R 4 are both methyl; R 5 is methyl; R 6 is —H;
R 1 and R 2 are both phenyl; R 3 and R 4 are both ethyl; R 5 is methyl; R 6 is —H;
R 1 and R 2 are both 4-cyanophenyl; R 3 and R 4 are both methyl; R 5 and R 6 are both —H;
R 1 and R 2 are both 2,5-dimethoxyphenyl; R 3 and R 4 are both methyl; R 5 and R 6 are both —H;
R 1 and R 2 are both 2,5-dimethoxyphenyl; R 3 and R 4 are both methyl; R 5 is methyl; R 6 is —H;
R 1 and R 2 are both 3-cyanophenyl; R 3 and R 4 are both methyl; R 5 and R 6 are both —H;
R 1 and R 2 are both 3-fluorophenyl; R 3 and R 4 are both methyl; R 5 and R 6 are both —H;
R 1 and R 2 are both 4-chlorophenyl; R 3 and R 4 are both methyl; R 5 is methyl; R 6 is —H;
R 1 and R 2 are both 2-dimethoxyphenyl; R 3 and R 4 are both methyl; R 5 and R 6 are both —H;
R 1 and R 2 are both 3-methoxyphenyl; R 3 and R 4 are both methyl; R 5 and R 6 are both —H;
R 1 and R 2 are both 2,3-dimethoxyphenyl; R 3 and R 4 are both methyl; R 5 and R 6 are both —H;
R 1 and R 2 are both 2,3-dimethoxyphenyl; R 3 and R 4 are both methyl; R 5 is methyl; R 6 is —H;
R 1 and R 2 are both 2,5-difluorophenyl; R 3 and R 4 are both methyl; R 5 and R 6 are both —H;
R 1 and R 2 are both 2,5-difluorophenyl; R 3 and R 4 are both methyl; R 5 is methyl; R 6 is —H;
R 1 and R 2 are both 2,5-dichlorophenyl; R 3 and R 4 are both methyl; R 5 and R 6 are both —H;
R 1 and R 2 are both 2,5-dimethylphenyl; R 3 and R 4 are both methyl; R 5 and R 6 are both —H;
R 1 and R 2 are both 2,5-dimethoxyphenyl; R 3 and R 4 are both methyl; R 5 and R 6 are both —H;
R 1 and R 2 are both phenyl; R 3 and R 4 are both methyl; R 5 and R 6 are both —H; R 1 and R 2 are both 2,5-dimethoxyphenyl; R 3 and R 4 are both methyl; R 5 is methyl; R 6 is —H;
R 1 and R 2 are both cyclopropyl; R 3 and R 4 are both methyl; R 5 and R 6 are both —H;
R 1 , and R 2 are both cyclopropyl; R 3 and R 4 are both ethyl; R 5 and R 6 are both —H;
R 1 and R 2 are both cyclopropyl; R 3 and R 4 are both methyl; R 5 is methyl; R 6 is —H;
R 1 and R 2 are both 1-methylcyclopropyl; R 3 and R 4 are both methyl; R 5 and R 6 are both —H;
R 1 and R 2 are both 1-methylcyclopropyl; R 3 and R 4 are both methyl; R 5 is methyl and R 6 is —H;
R 1 and R 2 are both 1-methylcyclopropyl; R 3 and R 4 are both methyl; R 5 is ethyl and R 6 is —H;
R 1 and R 2 are both 1-methylcyclopropyl; R 3 and R 4 are both methyl; R 5 is n-propyl and R 6 is —H;
R 1 and R 2 are both 1-methylcyclopropyl; R 3 and R 4 are both methyl; R 5 and R 6 are both methyl;
R 1 and R 2 are both 1-methylcyclopropyl; R 3 and R 4 are both ethyl; R 5 and R 6 are both —H;
R 1 and R 2 are both 1-methylcyclopropyl; R 3 is methyl, and R 4 is ethyl; R 5 and R 6 are both —H;
R 1 and R 2 are both 2-methylcyclopropyl; R 3 and R 4 are both methyl; R 5 and R 6 are both —H;
R 1 and R 2 are both 2-phenylcyclopropyl; R 3 and R 4 are both methyl; R 5 and R 6 are both —H;
R 1 and R 2 are both 1-phenylcyclopropyl; R 3 and R 4 are both methyl; R 5 and are both —H;
R 1 and R 2 are both cyclobutyl; R 3 and R 4 are both methyl; R 5 and R 6 are both —H;
R 1 and R 2 , are both cyclopentyl; R 3 and R 4 are both methyl; R 5 and R 6 are both —H;
R 1 and R 2 are both cyclohexyl; R 3 and R 4 are both methyl; R 5 and R 6 are both —H;
R 1 and R 2 are both cyclohexyl; R 3 and R 4 are both phenyl; R 5 and R 6 are both —H;
R 1 and R 2 are both methyl; R 3 and R 4 are both methyl; R 5 and R 6 are both —H;
R 1 and R 2 are both methyl; R 3 and R 4 are both t-butyl; R 5 and R 6 are both —H;
R 1 and R 2 are both methyl; R 3 and R 4 are both phenyl; R 5 and R 6 are both —H;
R 1 and R 2 are both t-butyl; R 3 and R 4 are both methyl; R 5 and R 6 are both —H;
R 1 and R 2 are ethyl; R 3 and R 4 are both methyl; R 5 and R 6 are both —H; or
R 1 and R 2 are both n-propyl; R 3 and R 4 are both methyl; R 5 and R 6 are both —H.
14 . The composition of claim 9 , wherein said composition is reconstitutable in a water in less than 2 minutes.
15 . The composition of claim 9 , wherein said composition is reconstitutable in a water in less than 1 minute.
16 . The composition of claim 14 , wherein the composition is a lyophilizate.
17 . The composition of claim 16 , wherein the crystalline bulking excipient, is selected from the group consisting of glycine, mannitol, dextran, dextrose, lactose, sucrose, polyvinylpyrrolidone, trehalose, glucose and combinations thereof.
18 . The composition of claim 17 , wherein the molar ratio of said compound to said excipient is from 1:10 to 1:1.
19 . The composition of claim 18 , wherein the molar ratio of said compound to said excipient is from 1:5.5 to 1:2.
20 . The composition of claim 19 , wherein the crystalline bulking excipient is glycine or mannitol.
21 . The composition of claim 20 , wherein the crystalline bulking excipient is mannitol.
22 . The composition of claim 21 , wherein the composition is an annealed composition.
23 . The composition of claim 22 , wherein said composition is reconstitutable in a water in less than 30 seconds.
24 . A composition comprising a compound represented by the following structural formula:
wherein:
Y is a covalent bond or a substituted or unsubstituted straight chained hydrocarbyl group;
R 1 -R 4 are independently —H, an aliphatic group, a substituted aliphatic group, an aryl group or a substituted aryl group, or R 1 and R 3 taken together with the carbon and nitrogen atoms to which they are bonded, and/or R 2 and R 4 taken together with the carbon and nitrogen atoms to which they are bonded, form a non-aromatic heterocyclic ring optionally fused to an aromatic ring;
Z is —O or —S; and
M + is a pharmaceutically acceptable monovalent cation and M 2+ is a pharmaceutically acceptable divalent cation; and
a pharmaceutically acceptable excipient, wherein the molar ratio of said compound to said excipient is from 1:20 to 1:1.
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