US2008114165A1PendingUtilityA1
Methods for the Preparation of {2-[(8,9)-Dioxo-2,6-diaza-bicyclo[5.2.0]-non-1(7)-en-2-yl]ethyl} Phosphonic Acid and Esters Thereof
Est. expiryOct 22, 2023(expired)· nominal 20-yr term from priority
A61P 9/12A61P 25/00C07F 9/645
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Claims
Abstract
The present invention provides methods for the preparation of {2-[(8,9)-dioxo-2,6-diaza-bicyclo[5.2.0]-non-1(7)-en-2-yl]ethyl} phosphonic acid, and esters thereof.
Claims
exact text as granted — not AI-modified1 . A method for preparing a compound of Formula IV:
wherein R 1 and R 2 are independently C 1-6 alkyl or C 1-6 haloalkyl;
comprising the step of reacting, in a solvent, a compound of Formula II:
with a compound of Formula III:
wherein:
Q 1 and Q 2 are each independently OH, halogen, or OX 1 , where X 1 is C 1-6 alkyl, C 1-6 haloalkyl or aryl; and
said solvent has the formula HOX 1 ;
to produce said compound of Formula IV.
2 . The method of claim 1 further comprising the step of hydrolyzing said compound of Formula IV to provide a compound of Formula I:
3 . The method of claim 1 wherein said compound of Formula II is prepared by reacting a compound of Formula V or Formula VI:
wherein X is a leaving group, with 1,3-diaminopropane.
4 . The method of claim 1 wherein R 1 and R 2 are each independently methyl, ethyl, propyl, or butyl.
5 . The method of claim 1 wherein R 1 and R 2 are each ethyl.
6 . The method of claim 1 wherein R 1 and R 2 are the same.
7 . The method of claim 1 wherein said solvent is methanol or ethanol.
8 . The method of claim 1 wherein Q 1 and Q 2 are each OH.
9 . The method of claim 1 wherein Q 1 and Q 2 are each halogen.
10 . The method of claim 1 wherein Q 1 and Q 2 are each OX 1 wherein X 1 is C 1-6 alkyl.
11 . The method of claim 1 wherein Q 1 and Q 2 are each OX 1 wherein X 1 is methyl, ethyl, isopropyl or n-butyl.
12 . The method of claim 10 wherein Q 1 and Q 2 are the same.
13 . The method of claim 1 wherein Q 1 and Q 2 are each OCH 2 CH 3 .
14 . The method of claim 1 wherein Q 1 and Q 2 are each OCH 2 CH 3 , and said solvent is methanol.
15 . The method of claim 1 wherein Q 1 and Q 2 are each OH, and said solvent is methanol.
16 . The method of claim 1 wherein each Q 1 and Q 2 are each OX 1 wherein X 1 is haloalkyl.
17 . The method of claim 1 wherein each Q 1 and Q 2 are each OX 1 wherein X 1 is aryl.
18 . The method of claim 1 wherein R 1 and R 2 are each independently methyl or ethyl; each of said Q 1 and Q 2 is OX 1 wherein X 1 is independently methyl, ethyl, isopropyl or n-butyl; and said solvent is methanol or ethanol.
19 . The method of claim 3 wherein the molar ratio of said 1,3-diaminopropane to said compound of Formula V or Formula VI is at least about 2:1.
20 . The method of claim 3 wherein X is halo.
21 . The method of claim 3 wherein said compound of Formula II is prepared by reacting 1,3-diaminopropane with said compound of Formula V.
22 . The method of claim 3 wherein compound of Formula II is prepared by reacting 1,3-diaminopropane with a compound of Formula VI.
23 . The method of claim 1 wherein said compound of Formula II and said compound of Formula III are reacted in substantially equimolar amounts.
24 . A product made by the process comprising:
a) reacting, in a solvent, a compound of Formula II: wherein R 1 and R 2 are independently C 1-6 alkyl or C 1-6 haloalkyl; with a compound of Formula III: wherein Q 1 and Q 2 are each independently OH, halogen, or OX 1 , wherein X 1 is C 1-6 alkyl, C 1-6 haloalkyl or aryl; and said solvent has the formula HOX 1 ; to produce a compound of Formula IV: b) hydrolyzing said compound of Formula IV to provide a compound of Formula I:
25 . The product of claim 24 comprising at least one compound selected from Formulas VII, VIII, IX, and X:
26 . A composition comprising a compound of Formula IV:
wherein R 1 and R 2 are independently C 1-6 alkyl or C 1-6 haloalkyl;
and at least one compound selected from Formulas VII, VIII, IX, and X:
wherein X 1 is C 1-6 alkyl, C 1-6 haloalkyl or aryl.
27 . The composition of claim 26 wherein X 1 is ethyl.
28 . The composition of claim 26 wherein R 1 and R 2 are ethyl.
29 . A composition comprising a compound of Formula I:
and at least one compound selected from Formulas VII, VIII, IX, and X:
wherein X 1 is C 1-6 alkyl, C 1-6 haloalkyl or aryl.Join the waitlist — get patent alerts
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