US4515722A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Phosphatidyl inositol analogs useful as anti-inflammatory/analgesic agents
Assignee: Merck and Co Inc
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Filing: 1982-03-30
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Granted: 1985-05-07
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Expires: 2002-03-30
Abstract
Abstract Phosphatidyl inositol analogs are found to be effective phospholipase C inhibitors and thereby potent anti-inflammatory and analgesic agents. These phosphatidyl inositol analogs are prepared by condensation of a protected inositol with a substituted phosphonic or phosphorous acid followed by removal of protecting groups.
Inventors
- 👤 Shu S. Yang
- 👤 Thomas R. Beattie
- 👤 Philippe L. Durette
- 👤 Timothy F. Gallagher
- 👤 Tsung-Ying Shen
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 20:28
CPC Classifications
C; C07; C07D; C07D493/00; C07D493/02; C07D493/10; C07C; C07C43/00; C07C43/02; C07C43/18; C07C43/192; C07C43/196; C07F; C07F9/00; C07F9/02; C07F9/06; C07F9/08; C07F9/09; C07F9/117; C07F9/28; C07F9/38; C07F9/40; C07F9/4071; C07F9/4081; C07H; C07H15/00; C07H15/18; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 4
Claim 1
Independent Claim
256 words
A compound of formula: ##STR23## or a pharmaceutically acceptable acid, ester, ether or carbonate thereof, wherein: L is (a) hydrogen; (b) R 1 ; where R 1 is (1) straight or branched-chain alkyl having from 1 to 20 carbon atoms especially C 1-6 alkyl; (2) aryl having from 6 to 10 carbon atoms; (3) cycloalkyl having from 3 to 8 carbon atoms; (4) alkenyl having from 2 to 20 carbon atoms especially C 8-20 alkenyl; (5) cycloalkenyl having from 5 to 8 carbon atoms; (6) aralkyl, alkaryl, aralkenyl, alkenylaryl wherein alkyl, aryl, and alkenyl are as previously defined; The above groups (1) to (6) are unsubstituted or substituted by hydroxy; alkoxy; halo; cyano; carboxy; amino; substituted amino; carbamoyl; sulfonyl; sulfinyl; thio; alkylthio; or nitro; (c) ##STR24## where R 2 and R 3 independently are: ##STR25## n is an integer from 1 to 4; or (d) ##STR26## wherein R 2 , R 3 , and n are as defined previously; R is (a) hydrogen; (b) loweralkyl; (c) cycloalkyl having from 3 to 8 carbon atoms; or (d) aralkyl; Y is oxygen or methylene; and A is a radical of (a) myo-inositol or a configuration isomer thereof; (b) branched chain myo-inositol; (c) 2-,4 or 5-positional isomer of myo-inositol; (d) inositol substituted with amino; azido; deoxy; halo; or (e) branched-chain inositol of the structural formula (e); ##STR27## where R 4 is C 1-6 alkyl or substituted C 1-6 alkyl; (f) phosphoryl inositols having one or more of its hydroxy groups coupled with another ##STR28## group; or (g) epimeric myo-inositol.
Claim 2
Dependent Claim
256 words
A compound of formula: ##STR23## or a pharmaceutically acceptable acid, ester, ether or carbonate thereof, wherein: L is (a) hydrogen; (b) R 1 ; where R 1 is (1) straight or branched-chain alkyl having from 1 to 20 carbon atoms especially C 1-6 alkyl; (2) aryl having from 6 to 10 carbon atoms; (3) cycloalkyl having from 3 to 8 carbon atoms; (4) alkenyl having from 2 to 20 carbon atoms especially C 8-20 alkenyl; (5) cycloalkenyl having from 5 to 8 carbon atoms; (6) aralkyl, alkaryl, aralkenyl, alkenylaryl wherein alkyl, aryl, and alkenyl are as previously defined; The above groups (1) to (6) are unsubstituted or substituted by hydroxy; alkoxy; halo; cyano; carboxy; amino; substituted amino; carbamoyl; sulfonyl; sulfinyl; thio; alkylthio; or nitro; (c) ##STR24## where R 2 and R 3 independently are: ##STR25## n is an integer from 1 to 4; or (d) ##STR26## wherein R 2 , R 3 , and n are as defined previously; R is (a) hydrogen; (b) loweralkyl; (c) cycloalkyl having from 3 to 8 carbon atoms; or (d) aralkyl; Y is oxygen or methylene; and A is a radical of (a) myo-inositol or a configuration isomer thereof; (b) branched chain myo-inositol; (c) 2-,4 or 5-positional isomer of myo-inositol; (d) inositol substituted with amino; azido; deoxy; halo; or (e) branched-chain inositol of the structural formula (e); ##STR27## where R 4 is C 1-6 alkyl or substituted C 1-6 alkyl; (f) phosphoryl inositols having one or more of its hydroxy groups coupled with another ##STR28## group; or (g) epimeric myo-inositol.
Claim 3
Dependent Claim
77 words
The compound of claim 1 wherein: L is (a) R 1 ; or (b) ##STR29## where R 2 and R 3 are as previously defined; R is (a) hydrogen; (b) C 1-6 alkyl; or (c) benzyl; Y is oxygen or methylene; and A is a radical of (a) myo-inositol; (b) branched-chain myo-inositol; (c) branced-chain inositol of formula (e); (d) epimeric myo-inositol; (e) phosphoryl inositol having one or more of its hydroxy groups coupled with another ##STR30## group.
Claim 4
Dependent Claim
76 words
The compound of claim 1 wherein: L is (a) ##STR31## where R 2 and R 3 independently are (1) R 1 where R 1 is C 7-20 alkyl; ##STR32## (2) ##STR33## where R 1 is C 7-20 alkyl, ##STR34## (3) ##STR35## where R 1 is C 7-20 alkyl; or (b) straight or branched C 7-20 alkyl; n is 1-2; R is hydrogen or C 1-6 alkyl; Y is oxygen; and A is a radical of myo-inositol.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-05-06 | 1988-11-05 | 1989-05-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-05-06 | 1992-11-05 | 1993-05-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-05-06 | 1996-11-05 | 1997-05-07 | $7700.00 | Window Closed / Lapsed |