US4987223A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Derivatives of the uronic acid
Assignee: CIVILE DE GESTION DE DROITS DE PROPRIETE INDUSTRIELLE CHOAY "DROPIC" Ste
•
Filing: 1982-10-27
•
Granted: 1991-01-22
•
Expires: 2002-10-27
Abstract
Abstract The invention relates to derivatives with a uronic acid structure having substituents selected among a reactive group, a functionalisable group and -OH functions blocked by protective groups. These derivatives are useful for preparing glycosides, particularly enzyme substrates.
Inventors
- 👤 Jean Choay
- 👤 Jean-Claude Jacquinet
- 👤 Maurice Petitou
- 👤 Pierre Sinay
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 15:37
CPC Classifications
C; C07; C07H; C07H7/00; C07H7/02; C07H7/033; C07H11/00; C07H3/00; C07H3/06; C07H9/00; C07H9/02; C07H9/04; C08; C08B; C08B37/00; C08B37/006; C08B37/0063; C08B37/0075; C08B37/0078; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
261 words
A compound having the following formula: ##STR10## wherein a. R 1 is selected from group consisting of i. Br, ii. Cl, iii. --O-- imidoyl, iv. --O-allyl, v. --O-vinyl, vi. --OCH 3 , vii. --O--C 6 H 5 , viii. --O--CO--CH 3 , Xi. --OH, x. an orthoester which together with --OR 2 forms --OH(CH 3 )OtBu)O--, xi. an orthoester which together with --OR 2 forms --OC(CH 3 )(OCH 3 )O--, and xii. --O-nitrophenyl; b. R 2 is selected from the group consisting of i. methyl, ii. benzyl, iii. acetyl, iv. benzoyl, v. chloroacetyl, vi. allyl, vii. vinyl, viii. an orthoester which together with --OR 1 forms --OC(CH 3 )(OtBu)O--, and ix. an orthoester which together with --OR 1 forms--OC(CH 3 )(OCH 3 )O--; c. R 3 is selected from the group consisting of i. methyl, ii. benzyl, iii. acetyl, iv. benzoyl, v. chloroacetyl, vi. allyl, and vii. vinyl; d. R 4 is selected from the group consisting of i. methyl, ii. benzyl, iii. acetyl, iv. benzoyl, v. chloroacetyl, vi. allyl, vii. vinyl, and viii. paramethoxy benzyl; e. R 6 is selected from the group consisting of i. methyl, ii. benzoyl, and iii. a cation of a pharmaceutically acceptable salt; provided that where R 1 is a methoxy group, R 4 is not methyl, where COOR 6 is in the glucuronic position, R 2 , R 3 , and R 4 are not identical, where R 1 and R 2 form an orthoester, R 3 and R 4 are not acetyl, at least one of R 2 or R 3 is acetyl.
Claim 2
Dependent Claim
261 words
A compound having the following formula: ##STR10## wherein a. R 1 is selected from group consisting of i. Br, ii. Cl, iii. --O-- imidoyl, iv. --O-allyl, v. --O-vinyl, vi. --OCH 3 , vii. --O--C 6 H 5 , viii. --O--CO--CH 3 , Xi. --OH, x. an orthoester which together with --OR 2 forms --OH(CH 3 )OtBu)O--, xi. an orthoester which together with --OR 2 forms --OC(CH 3 )(OCH 3 )O--, and xii. --O-nitrophenyl; b. R 2 is selected from the group consisting of i. methyl, ii. benzyl, iii. acetyl, iv. benzoyl, v. chloroacetyl, vi. allyl, vii. vinyl, viii. an orthoester which together with --OR 1 forms --OC(CH 3 )(OtBu)O--, and ix. an orthoester which together with --OR 1 forms--OC(CH 3 )(OCH 3 )O--; c. R 3 is selected from the group consisting of i. methyl, ii. benzyl, iii. acetyl, iv. benzoyl, v. chloroacetyl, vi. allyl, and vii. vinyl; d. R 4 is selected from the group consisting of i. methyl, ii. benzyl, iii. acetyl, iv. benzoyl, v. chloroacetyl, vi. allyl, vii. vinyl, and viii. paramethoxy benzyl; e. R 6 is selected from the group consisting of i. methyl, ii. benzoyl, and iii. a cation of a pharmaceutically acceptable salt; provided that where R 1 is a methoxy group, R 4 is not methyl, where COOR 6 is in the glucuronic position, R 2 , R 3 , and R 4 are not identical, where R 1 and R 2 form an orthoester, R 3 and R 4 are not acetyl, at least one of R 2 or R 3 is acetyl.
Claim 3
Dependent Claim
185 words
A compound having the following formula: ##STR11## wherein a. R 1 is selected from group consisting of i. --O-allyl, ii. --O-vinyl, and iii. --OH; b. R 2 is selected from the group consisting of i. methyl, ii. benzyl, iii. acetyl, iv. benzoyl, v. chloroacetyle, vi. allyl, vii. vinyl, viii. or orthoester which together with --OR 1 forms --OC(CH 3 )(OtBu)O--, and ix. an orthoester which together with --OR 1 forms --OC(CH 3 (OCH 3 )O--; c. R 3 is selected from the group consisting of i. methyl, ii. benzyl, iii. acetyl, iv. benzoyl, v. chloroacetyl, vi. allyl, and vii. vinyl; d. R 4 is selected from the group consisting of i. monochloroacetyl, ii. acetyl, iii. benzyl, vi. p-methoxybenzyl, v. allyl, and vi. vinyl; e. R 6 is selected from the group consisting of i. methyl, ii. benzyl, and iii. a cation of a pharmaceutically acceptable salt; provided that where COOR 6 is in the glucuronic position, R 2 , R 3 , and R 4 are not identical where R 1 and R 2 form an orthoester, R 3 and R 4 are not acetyl.
Claim 4
Dependent Claim
185 words
A compound having the following formula: ##STR11## wherein a. R 1 is selected from group consisting of i. --O-allyl, ii. --O-vinyl, and iii. --OH; b. R 2 is selected from the group consisting of i. methyl, ii. benzyl, iii. acetyl, iv. benzoyl, v. chloroacetyle, vi. allyl, vii. vinyl, viii. or orthoester which together with --OR 1 forms --OC(CH 3 )(OtBu)O--, and ix. an orthoester which together with --OR 1 forms --OC(CH 3 (OCH 3 )O--; c. R 3 is selected from the group consisting of i. methyl, ii. benzyl, iii. acetyl, iv. benzoyl, v. chloroacetyl, vi. allyl, and vii. vinyl; d. R 4 is selected from the group consisting of i. monochloroacetyl, ii. acetyl, iii. benzyl, vi. p-methoxybenzyl, v. allyl, and vi. vinyl; e. R 6 is selected from the group consisting of i. methyl, ii. benzyl, and iii. a cation of a pharmaceutically acceptable salt; provided that where COOR 6 is in the glucuronic position, R 2 , R 3 , and R 4 are not identical where R 1 and R 2 form an orthoester, R 3 and R 4 are not acetyl.
Claim 5
Dependent Claim
162 words
A compound having the following formula: ##STR12## wherein a. R 1 is --OH; b. R 2 is selected from the group consisting of i. methyl, ii. benzyl, iii. acetyl, iv. benzoyl, v. chloroacetyl, vi. allyl, vii. vinyl, viii. an orthoester which together with --OR 1 forms --OC(CH 3 )(OtBu)O--, and ix. an orthoester which together with --OR 1 forms --OC(CH 3 )(OCH 3 )O--; c. R 3 is selected from the group consisting of i. methyl, ii. benzyl, iii. acetyl, iv. benzoyl, v. chloroacetyl, vi. allyl, and vii. vinyl; d. R 4 is selected from the group consisting of i. methyl, ii. benzyl, iii. acetyl, iv. benzoyl, v. chloroacetyl, vi. allyl, vii. vinyl, and viii. paramethoxy benzyl; e. R 6 is selected from the group consisting of i. methyl, ii. benzyl, and iii. a cation of a pharmaceutically acceptable salt; provided that where COOR 6 is in the glucuronic position, R 2 , R 3 , and R 4 are not identical.
Claim 6
Dependent Claim
162 words
A compound having the following formula: ##STR12## wherein a. R 1 is --OH; b. R 2 is selected from the group consisting of i. methyl, ii. benzyl, iii. acetyl, iv. benzoyl, v. chloroacetyl, vi. allyl, vii. vinyl, viii. an orthoester which together with --OR 1 forms --OC(CH 3 )(OtBu)O--, and ix. an orthoester which together with --OR 1 forms --OC(CH 3 )(OCH 3 )O--; c. R 3 is selected from the group consisting of i. methyl, ii. benzyl, iii. acetyl, iv. benzoyl, v. chloroacetyl, vi. allyl, and vii. vinyl; d. R 4 is selected from the group consisting of i. methyl, ii. benzyl, iii. acetyl, iv. benzoyl, v. chloroacetyl, vi. allyl, vii. vinyl, and viii. paramethoxy benzyl; e. R 6 is selected from the group consisting of i. methyl, ii. benzyl, and iii. a cation of a pharmaceutically acceptable salt; provided that where COOR 6 is in the glucuronic position, R 2 , R 3 , and R 4 are not identical.
Claim 7
Dependent Claim
11 words
A compound according to claim 1, wherein R 1 is --OH.
Claim 8
Dependent Claim
117 words
A compound having the following formula ##STR13## wherein a. R 1 is --O-allyl; b. R 2 is selected from the group consisting of i. methyl, ii. benzyl, iii. acetyl, iv. benzoyl, v. chloroacetyl, vi. allyl, vii. vinyl, viii. an orthoester which together with --OR 1 forms --OC(CH 3 )(OtBu)O--, and ix. an orthoester which together with --OR 1 forms --OC(CH 3 )(OCH 3 )O--; c. R 3 is selected from the group consisting of i. methyl, ii. benzyl, iii. acetyl, iv. benzoyl, v. chloroacetyl, vi. allyl, and vii. vinyl; d. R 4 is --OH; e. R 6 is selected from the group consisting of i. methyl, ii. benzyl, and iii. a cation of a pharmaceutically acceptable salt.
Claim 9
Dependent Claim
117 words
A compound having the following formula ##STR13## wherein a. R 1 is --O-allyl; b. R 2 is selected from the group consisting of i. methyl, ii. benzyl, iii. acetyl, iv. benzoyl, v. chloroacetyl, vi. allyl, vii. vinyl, viii. an orthoester which together with --OR 1 forms --OC(CH 3 )(OtBu)O--, and ix. an orthoester which together with --OR 1 forms --OC(CH 3 )(OCH 3 )O--; c. R 3 is selected from the group consisting of i. methyl, ii. benzyl, iii. acetyl, iv. benzoyl, v. chloroacetyl, vi. allyl, and vii. vinyl; d. R 4 is --OH; e. R 6 is selected from the group consisting of i. methyl, ii. benzyl, and iii. a cation of a pharmaceutically acceptable salt.
Claim 10
Dependent Claim
16 words
A compound according to claim 1, wherein R 4 is --OH, and R 1 is --O-allyl.
References Cited (Backward Citations)
US2845439A
Cited
US2650237A
Cited
US2798079A
Cited
US2985664A
Cited
US2938900A
Cited
US3356674A
Cited
US3632802A
Cited
US3959253A
Cited
US4238473A
Cited
US4107425A
Cited
US4335236A
Cited
US4424348A
Cited
US4316983A
Cited
US4442284A
Cited
US4464531A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1994-01-21 | 1994-07-23 | 1995-01-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1998-01-21 | 1998-07-23 | 1999-01-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2002-01-21 | 2002-07-23 | 2003-01-22 | $7700.00 | Window Closed / Lapsed |