US4639446A
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US
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Aminoacyllabdanes, pharmaceutical compositions and use
Assignee: Aventis Pharmaceuticals Inc
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Filing: 1985-12-04
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Granted: 1987-01-27
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Expires: 2005-12-04
Abstract
Abstract Novel aminoacyllabdanes, 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 11:35
CPC Classifications
C; C07; C07D; C07D405/00; C07D405/02; C07D405/12; C07D311/00; C07D311/02; C07D311/78; C07D311/92; C07D493/00; C07D493/02; C07D493/04; C07D497/00; C07D497/02; C07D497/04
Claims Analysis
Total Claims: 31
Claim 1
Independent Claim
177 words
A compound of the formula wherein R 1 is R 2 R 3 NCHR 4 CO wherein R 2 is hydrogen, loweralkyl or benzyl, R 3 is hydrogen or loweralkyl and R 4 is hydrogen, loweralkyl or benzyl; R 2 and R 3 taken together with the nitrogen atom to which they are attached form a group of the formula ##STR7## wherein X is CO, O, S, SO, SO 2 ; a group of the formula CHR 9 wherein R 9 is hydrogen, loweralkyl or a group of the formula OR 10 wherein R 10 is hydrogen or COR 11 wherein R 11 is loweralkyl; or a group of the formula NR 12 wherein R 12 is loweralkyl; n is 1 or 0; R 6 is hydrogen or a group of the formula R 5 CO wherein R 5 is hydrogen or loweralkyl; R 7 is hydrogen or a group of the formula R 8 CO wherein R 8 is hydrogen or loweralkyl; the optical and geometric isomers thereof, or a pharmaceutically acceptable acid addition salt thereof.
Claim 2
Dependent Claim
177 words
A compound of the formula wherein R 1 is R 2 R 3 NCHR 4 CO wherein R 2 is hydrogen, loweralkyl or benzyl, R 3 is hydrogen or loweralkyl and R 4 is hydrogen, loweralkyl or benzyl; R 2 and R 3 taken together with the nitrogen atom to which they are attached form a group of the formula ##STR7## wherein X is CO, O, S, SO, SO 2 ; a group of the formula CHR 9 wherein R 9 is hydrogen, loweralkyl or a group of the formula OR 10 wherein R 10 is hydrogen or COR 11 wherein R 11 is loweralkyl; or a group of the formula NR 12 wherein R 12 is loweralkyl; n is 1 or 0; R 6 is hydrogen or a group of the formula R 5 CO wherein R 5 is hydrogen or loweralkyl; R 7 is hydrogen or a group of the formula R 8 CO wherein R 8 is hydrogen or loweralkyl; the optical and geometric isomers thereof, or a pharmaceutically acceptable acid addition salt thereof.
Claim 3
Dependent Claim
16 words
A compound according to claim 1 wherein R 2 and R 3 are hydrogen or loweralkyl.
Claim 4
Dependent Claim
16 words
A compound according to claim 1 wherein R 2 is hydrogen and R 3 is loweralkyl.
Claim 5
Dependent Claim
98 words
A compound according to claim 1 wherein R 2 and R 3 taken together with the nitrogen atom to which they are attached form a group of the formula ##STR8## wherein X is CO, O, S, SO, SO 2 , a group of the formula CHR 9 wherein R 9 is hydrogen, loweralkyl or a group of the formula OR 10 wherein R 10 is hydrogen or a group of the formula COR 11 wherein R 11 is loweralkyl, or a group of the formula NR 12 wherein R 12 is loweralkyl, and n is 0 or 1.
Claim 6
Dependent Claim
13 words
A compound according to claim 1 wherein R 4 is hydrogen or loweralkyl.
Claim 7
Dependent Claim
11 words
A compound according to claim 1 wherein R 4 is benzyl.
Claim 8
Dependent Claim
26 words
A compound according to claim 1 wherein R 6 is hydrogen or a group of the formula R 5 CO wherein R 5 is as hereinbeforedefined.
Claim 9
Dependent Claim
25 words
A compound according to claim 1 wherein R 7 is hydrogen or a group of the formula R 8 CO wherein R 8 is hereinbeforedefined.
Claim 10
Dependent Claim
8 words
The compound of claim 2 which is 7β-acetoxy-8,13-epoxy-1α-(diethylaminoacetoxy)-6β,9α-dihydroxylabd-14-en-11-one.
Claim 11
Dependent Claim
8 words
The compound of claim 2 which is 7β-acetoxy-8,13-epoxy-1α-(dimethylaminoacetoxy)-6β,9.alpha.-dihydroxylabd-14-en-11-one.
Claim 12
Dependent Claim
8 words
The compound of claim 2 which is 7β-acetoxy-8,13-epoxy-1α-(di-n-propylaminoacetoxy)-6β,9.alpha.-dihydroxylabd-14-en-11-one.
Claim 13
Dependent Claim
8 words
The compound of claim 2 which is 8,13-epoxy-1α-(diethylaminoacetoxy)-6β,7β,9α-trihydroxylabd-14-en-11-one.
Claim 14
Dependent Claim
8 words
The compound of claim 3 which is 7β-acetoxy-8,13-epoxy-1α-(isopropylaminoacetoxy)-6β,9.alpha.-dihydroxylabd-14-en-11-one.
Claim 15
Dependent Claim
8 words
The compound of claim 3 which is 7β-acetoxy-8,13-epoxy-1α-(t-butylaminoacetoxy)-6β,9α-dihydroxylabd-14-en-11-one.
Claim 16
Dependent Claim
8 words
The compound of claim 4 wich is 7β-acetoxy-8,13-epoxy-1α-[(pyrrolidin-1-yl)acetoxy]-6β,9.alpha.-dihydroxylabd-14-en-11-one.
Claim 17
Dependent Claim
8 words
The compound of claim 4 which is 7β-acetoxy-8,13-epoxy-1α-[(morpholin-4-yl)acetoxy]-6β,9.alpha.-dihydroxylabd-14-en-11-one.
Claim 18
Dependent Claim
8 words
The compound of claim 4 which is 7β-acetoxy-8,13-epoxy-1α-[(1-hydroxypiperidin-4-yl)acetoxy]-6.beta.,9α-dihydroxylabd-14-en-11-one.
Claim 19
Dependent Claim
8 words
The compound of claim 4 which is 7β-acetoxy-8,13-epoxy-1α-[(thiomorpholin-4-yl)acetoxy]-6β,9α-dihydroxylabd-14-en-11-one.
Claim 20
Dependent Claim
8 words
The compound of claim 4 which is 7β-acetoxy-8,13-epoxy-1α-[(piperidin-1-yl)acetoxy]-6β,9.alpha.-dihydroxylabd-14-en-11-one.
Claim 21
Independent Claim
203 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 of the formula ##STR9## wherein R 1 is R 2 R 3 NCHR 4 CO wherein R 2 is hydrogen, loweralkyl or benzyl, R 3 is hydrogen or loweralkyl and R 4 is hydrogen, loweralkyl or benzyl; R 2 and R 3 taken together with the nitrogen atom to which they are attached form a group of the formula ##STR10## wherein X is CO, O, S, SO, SO 2 , a group of the formula CHR 9 wherein R 9 is hydrogen, loweralkyl or a group of the formula OR 10 wherein R 10 is hydrogen or COR 11 wherein R 11 is loweralkyl, or a group of the formula NR 12 wherein R 12 is loweralkyl; n is 0 or 1; R 6 is hydrogen or a group of the formula R 5 CO wherein R 5 is hydrogen or or loweralkyl; R 7 as hydrogen or a group of the formula R 8 CO wherein R 8 is hydrogen or loweralkyl; the optical and geometric isomers thereof, or a pharmaceutically acceptable acid addition salt thereof.
Claim 22
Independent Claim
203 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 of the formula ##STR9## wherein R 1 is R 2 R 3 NCHR 4 CO wherein R 2 is hydrogen, loweralkyl or benzyl, R 3 is hydrogen or loweralkyl and R 4 is hydrogen, loweralkyl or benzyl; R 2 and R 3 taken together with the nitrogen atom to which they are attached form a group of the formula ##STR10## wherein X is CO, O, S, SO, SO 2 , a group of the formula CHR 9 wherein R 9 is hydrogen, loweralkyl or a group of the formula OR 10 wherein R 10 is hydrogen or COR 11 wherein R 11 is loweralkyl, or a group of the formula NR 12 wherein R 12 is loweralkyl; n is 0 or 1; R 6 is hydrogen or a group of the formula R 5 CO wherein R 5 is hydrogen or or loweralkyl; R 7 as hydrogen or a group of the formula R 8 CO wherein R 8 is hydrogen or loweralkyl; the optical and geometric isomers thereof, or a pharmaceutically acceptable acid addition salt thereof.
Claim 23
Dependent Claim
11 words
A method according to claim 20 wherein the compound is 7β-acetoxy-8,13-epoxy-1α-(diethylaminoacetoxy)-6β,9α-dihydroxylabd-14-en-11-one.
Claim 24
Dependent Claim
11 words
A method according to claim 20 wherein the compound is 7β-acetoxy-8-13-epoxy-1α-[(morpholin-4-yl)acetoxy]-6β,9.alpha.-dihydroxylabd-14-en-11-one.
Claim 25
Dependent Claim
199 words
An intraocular pressure reducing composition comprising an inert adjuvant and as the active ingredient, an amount effective in reducing intraocular pressure of a compound of the formula ##STR11## wherein R 1 is R 2 R 3 NCHR 4 CO wherein R 2 is hydrogen, loweralkyl or benzyl, R 3 is hydrogen or loweralkyl and R 4 is hydrogen, loweralkyl or benzyl; R 2 and R 3 taken together with the nitrogen atom to which they are attached form a group of the formula ##STR12## wherein X is CO, O, S, SO, SO 2 , a group of the formula CHR 9 wherein R 9 is hydrogen, loweralkyl or a group of the formula OR 10 wherein R 10 is hydrogen or COR 11 wherein R 11 is loweralkyl, or a group of the formula NR 12 wherein R 12 is loweralkyl; n is 0 or 1; R 6 is hydrogen or a group of the formula R 5 CO wherein R 5 hydrogen or loweralkyl; R 7 as hydrogen or a group of the formula R 8 CO wherein R 8 is hydrogen or loweralkyl; the optical and geometric isomers thereof, or a pharmaceutically acceptable acid addition salt thereof.
Claim 26
Dependent Claim
199 words
An intraocular pressure reducing composition comprising an inert adjuvant and as the active ingredient, an amount effective in reducing intraocular pressure of a compound of the formula ##STR11## wherein R 1 is R 2 R 3 NCHR 4 CO wherein R 2 is hydrogen, loweralkyl or benzyl, R 3 is hydrogen or loweralkyl and R 4 is hydrogen, loweralkyl or benzyl; R 2 and R 3 taken together with the nitrogen atom to which they are attached form a group of the formula ##STR12## wherein X is CO, O, S, SO, SO 2 , a group of the formula CHR 9 wherein R 9 is hydrogen, loweralkyl or a group of the formula OR 10 wherein R 10 is hydrogen or COR 11 wherein R 11 is loweralkyl, or a group of the formula NR 12 wherein R 12 is loweralkyl; n is 0 or 1; R 6 is hydrogen or a group of the formula R 5 CO wherein R 5 hydrogen or loweralkyl; R 7 as hydrogen or a group of the formula R 8 CO wherein R 8 is hydrogen or loweralkyl; the optical and geometric isomers thereof, or a pharmaceutically acceptable acid addition salt thereof.
Claim 27
Dependent Claim
11 words
A composition according to claim 23 wherein the compound is 7β-acetoxy-8,13-epoxy-1α-(diethylaminoacetoxy)-6β,9α-dihydroxylabd-14-en-11-one.
Claim 28
Dependent Claim
11 words
A composition according to claim 23 wherein the compound is 7β-acetoxy-8,13-epoxy-1α-[(morpholin-4-yl)acetoxy]-6β,9.alpha.-dihydroxylabd-14-en-11-one.
Claim 29
Dependent Claim
8 words
The compound of claim 3 which is 7β-acetoxy-8,13-epoxy-1α-[2-(ethylamino)propionyloxy]-6β,9α-dihydroxylabd-14-en-11-one.
Claim 30
Dependent Claim
8 words
The compound of claim 4 which is 7β-acetoxy-8,13-epoxy-1α-[2-(morpholin-4-yl)propionyloxy]-6.beta.,9α-dihydroxylabd-14-en-11-one.
Claim 31
Dependent Claim
8 words
The compound of claim 4 which is 7β-acetoxy-8,13-epoxy-1α-(4-methylpiperazin-1-yl)acetoxy-6.beta.,9α-dihydroxylabd-14-en-11-one.
References Cited (Backward Citations)
US4134986A
Cited
US4517200A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 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 |