US4760057A
Expired / Lapsed
US
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(Acyloxyalkoxy)carbonyl derivatives as bioreversible prodrug moieties for primary and secondary amine functions in drugs
Assignee: Merck and Co Inc
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Filing: 1985-04-22
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Granted: 1988-07-26
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Expires: 2005-04-22
Abstract
Abstract This invention relates to novel (acyloxyalkoxy)carbonyl derivatives as bioreversible prodrug moieties for primary and secondary amine functions in drugs having a primary or secondary amine function thereon. Hydrolytic enzymes are used to trigger the regeneration of the parent amine drug of the carbamate prodrug moiety. The case also contains pharmaceutical composition, method of treatment and process claims.
Inventors
- 👤 Jose Alexander
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 02:40
CPC Classifications
C; C07; C07D; C07D285/00; C07D285/01; C07D285/02; C07D285/04; C07D285/10; C07D215/00; C07D215/02; C07D215/16; C07D215/48; C07D215/54; C07D215/56; C07D417/00; C07D417/02; C07D417/04
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
88 words
A compound of the formula: ##STR4## wherein RR'N represents an amino substituted primary or secondary amine pharmaceutical; R 1 and R 2 are selected from the group consisting of hydrogen, and substituted C 1-6 alkyl or alkyl wherein the substituents are carboxy or C 1-5 alkoxy carbonyl R 3 is selected from the group consisting of C 1-20 alkyl C 2-20 alkenyl C 2-5 alkynyl aryl C 6-8 aralkyl C 3-8 cycloalkyl C 3-10 cycloalkenyl carboxy C 2-20 alkyl carboxy C 5-20 cycloalkyl halo (C 2-20 ) alkyl.
Claim 2
Dependent Claim
88 words
A compound of the formula: ##STR4## wherein RR'N represents an amino substituted primary or secondary amine pharmaceutical; R 1 and R 2 are selected from the group consisting of hydrogen, and substituted C 1-6 alkyl or alkyl wherein the substituents are carboxy or C 1-5 alkoxy carbonyl R 3 is selected from the group consisting of C 1-20 alkyl C 2-20 alkenyl C 2-5 alkynyl aryl C 6-8 aralkyl C 3-8 cycloalkyl C 3-10 cycloalkenyl carboxy C 2-20 alkyl carboxy C 5-20 cycloalkyl halo (C 2-20 ) alkyl.
Claim 3
Dependent Claim
66 words
A compound of claim 1 wherein the RR'N group is an amino substituted primary or secondary amine pharmaceutical; R 1 and R 2 are the same or different and are selected from the group consisting of hydrogen and C 1-5 alkyl and R 3 is selected from the group consisting of C 1-10 alkyl carboxy C 2-10 alkyl and C 1-5 alkoxy carboxyl C 2-10 alkyl.
Claim 4
Dependent Claim
39 words
A compound of claim 1 wherein the RR'N primary or secondary amine pharmaceutical is selected from the group consisting of timolol, thiabendazole, norfloxacin, dimethoxyphenethylamine, propranolol, atenolol, pindolol, methyldopa, epinephrine, dopamine, metoprolol, cartelolol, pipemidic acid, 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylic acid and 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperezinyl)-3-quinolinecarboxylic acid.
Claim 5
Dependent Claim
8 words
A compound of claim 1 which is 1-(Acetoxymethoxy)carbonyl-2-(4-thiazolyl)benzimidazole.
Claim 6
Dependent Claim
8 words
A compound of claim 1 which is 3-[3-(N-acetoxymethoxycarbonyl)tert-butylamino-2-hydroxypropoxy]-4-morpholino-l,2,5-thiadiazole.
Claim 7
Dependent Claim
9 words
A compound of claim 1 which is 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-[4-(acetoxymethoxycarbonyl-1-piperazinyl]-3-quinolinecarboxylic acid.
Claim 8
Dependent Claim
9 words
A compound of claim 1 which is 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-[(4-octanoyloxymethoxycarbonyl)1-piperazinyl]-3-quinolinecarboxylic acid.
Claim 9
Dependent Claim
9 words
A compound of claim 1 which is 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-[4-(1-acetoxyethoxycarbonyl)-1-piperazinyl]-3-quinolinecarboxylic acid.
Claim 10
Dependent Claim
8 words
A compound of claim 1 which is 1-[N-(1-acetoxyethoxycarbonyl)isopropylamino]-3-(1-naphthloxy)-2-propanol.
Claim 11
Dependent Claim
14 words
A pharmaceutical composition comprising a compound of claim 1 and a suitable pharmaceutical carrier.
Claim 12
Dependent Claim
14 words
A pharmaceutical composition comprising a compound of claim 2 and a suitable pharmaceutical carrier.
Claim 13
Dependent Claim
14 words
A pharmaceutical composition comprising a compound of claim 3 and a suitable pharmaceutical carrier.
Claim 14
Dependent Claim
34 words
A method for alleviating pain or disease symptoms in a warm-blooded animal exhibiting pain or disease symptoms which comprises administering thereto an anti-pain or anti-disease symptom effective amount of a compound of claim 1.
Claim 15
Dependent Claim
36 words
A method for alleviating pain or disease symptoms in or on a warm-blooded animal exhibiting pain or disease symptoms which comprises administering thereto an anti-pain or anti-disease symptom effective amount of a compound of claim 2.
Claim 16
Dependent Claim
36 words
A method for alleviating pain or disease symptoms in or on a warm-blooded animal exhibiting pain or disease symptoms which comprises administering thereto an anti-pain or anti-disease symptom effective amount of a compound of claim 3.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1991-07-26 | 1992-01-25 | 1992-07-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-07-26 | 1996-01-25 | 1996-07-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-07-26 | 2000-01-25 | 2000-07-26 | $7700.00 | Window Closed / Lapsed |