US4639443A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Labdane compounds, pharmaceutical compositions and use
Assignee: Aventis Pharmaceuticals Inc
•
Filing: 1986-04-04
•
Granted: 1987-01-27
•
Expires: 2006-04-04
Abstract
Abstract Novel labdanes, intermediates and processes for the preparation thereof, and methods for reducing intraocular pressure utilizing compounds or compositions thereof are disclosed.
Inventors
- 👤 Raymond W. Kosley, Jr.
- 👤 Robert J. Cherill
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 22:12
CPC Classifications
C; C07; C07D; C07D407/00; C07D407/02; C07D407/12; C07D311/00; C07D311/02; C07D311/78; C07D311/92; C07D493/00; C07D493/02; C07D493/04; C07D493/10; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/18; C07F7/1804; C07F9/00; C07F9/02; C07F9/547; C07F9/655; C07F9/65502
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
299 words
A compound of the formula wherein: (a) R 6 and R 7 are each independently hydrogen, a group of the formula R 8 CO wherein R 8 is hydrogen, loweralkyl, ##STR13## a group of the formula R 10 OCR 31 R 32 (CH 2 ) n wherein R 10 is hydrogen or loweralkyl, R 31 is hydrogen or loweralkyl, R 32 is hydrogen or loweralkyl, and n is 0, 1, 2, or 3, a group of the formula R 11 R 12 NCHR 13 wherein R 11 is hydrogen, loweralkyl, a group of the formula ##STR14## a group of the formula ##STR15## or a group of the formula R 14 CO wherein R 14 is hydrogen or loweralkyl; R 12 is hydrogen or loweralkyl; R 13 is hydrogen, loweralkyl, benzyl or a group of the formula CH 2 OH; R 11 and R 12 taken together with the nitrogen atom to which they are attached form a group of the formula ##STR16## wherein X is O, S or a group of the formula CHR 15 wherein R 15 is hydrogen, loweralkyl or a group of the formula OR 16 wherein R 16 is hydrogen, loweralkyl or a group of the formula COR 17 wherein R 17 is loweralkyl, and m is 0 or 1; a group of the formula NR 18 wherein R 18 is loweralkyl; (b) R 1 and R 9 taken together form a group of the formula CHNR 19 R 20 wherein R 19 and R 20 are each independently loweralkyl; and R 19 and R 20 taken together with the nitrogen atom to which they are attached form a group of the formula ##STR17## wherein X and m are as hereinbeforedescribed; the optical and geometric isomers thereof, or a pharmaceutically acceptable acid addition salt thereof.
Claim 2
Dependent Claim
299 words
A compound of the formula wherein: (a) R 6 and R 7 are each independently hydrogen, a group of the formula R 8 CO wherein R 8 is hydrogen, loweralkyl, ##STR13## a group of the formula R 10 OCR 31 R 32 (CH 2 ) n wherein R 10 is hydrogen or loweralkyl, R 31 is hydrogen or loweralkyl, R 32 is hydrogen or loweralkyl, and n is 0, 1, 2, or 3, a group of the formula R 11 R 12 NCHR 13 wherein R 11 is hydrogen, loweralkyl, a group of the formula ##STR14## a group of the formula ##STR15## or a group of the formula R 14 CO wherein R 14 is hydrogen or loweralkyl; R 12 is hydrogen or loweralkyl; R 13 is hydrogen, loweralkyl, benzyl or a group of the formula CH 2 OH; R 11 and R 12 taken together with the nitrogen atom to which they are attached form a group of the formula ##STR16## wherein X is O, S or a group of the formula CHR 15 wherein R 15 is hydrogen, loweralkyl or a group of the formula OR 16 wherein R 16 is hydrogen, loweralkyl or a group of the formula COR 17 wherein R 17 is loweralkyl, and m is 0 or 1; a group of the formula NR 18 wherein R 18 is loweralkyl; (b) R 1 and R 9 taken together form a group of the formula CHNR 19 R 20 wherein R 19 and R 20 are each independently loweralkyl; and R 19 and R 20 taken together with the nitrogen atom to which they are attached form a group of the formula ##STR17## wherein X and m are as hereinbeforedescribed; the optical and geometric isomers thereof, or a pharmaceutically acceptable acid addition salt thereof.
Claim 3
Dependent Claim
9 words
The compound of claim 1 which is 7β-acetoxy-8,13-epoxy-1α,6β,9α-trihydroxylabd-14-en-11-one-1,9-dimethylformamide acetal.
Claim 4
Dependent Claim
9 words
The compound of claim 1 which is 6β-acetoxy-8,13-epoxy-1α,7β,9α-trihydroxylabd-14-en-11-one-1,9-dimethylformamide acetal.
Claim 5
Dependent Claim
9 words
The compound of claim 1 which is 8,13-epoxy-1α,6β,7β,9α-tetrahydroxylabd-14-en-11-one-1,9-dimethylformamide acetal.
Claim 6
Dependent Claim
9 words
The compound of claim 1 which is 7β-(N,N-diethylaminoacetoxy)-8,13-epoxy-1α,6β,9α-trihydroxylabd-14-en-11-one-1,9-dimethylformamide acetal.
Claim 7
Dependent Claim
9 words
A compound of claim 1 which is 7β-(1-piperidinoacetoxy)-8,13-epoxy-1α,6β,9α-trihydroxylabd-14-en-11-one-1,9-dimethylformamide acetal.
Claim 8
Dependent Claim
9 words
A compound of claim 1 which is 7β-(N,N-dimethylaminoacetoxy)-8,13-epoxy-1α,6β,9α-trihydroxylabd-14-en-11-one-1,9-dimethylformamide acetal.
Claim 9
Dependent Claim
38 words
A method of reducing intraocular pressure in mammals comprising administering to a mammal requiring intraocular pressure reduction, an intraocular pressure reducing effective amount of a compound or a pharmaceutically acceptable acid addition salt thereof according to claim 1.
Claim 10
Dependent Claim
38 words
An intraocular pressure reducing composition comprising an inert intraocular pressure reducing adjuvant and as the active ingredient, an intraocular pressure reducing effective amount of a compound or a pharmaceutically acceptable acid addition salt thereof according to claim 1.
References Cited (Backward Citations)
US45172A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1990-01-26 | 1990-07-28 | 1991-01-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-01-26 | 1994-07-28 | 1995-01-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-01-26 | 1998-07-28 | 1999-01-27 | $7700.00 | Window Closed / Lapsed |