US4181719A
Expired / Lapsed
US
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Analgesic N-acetyl-para-aminophenyl N'-acetylaminothioalkanoates
Assignee: Sanofi SA
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Filing: 1978-05-26
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Granted: 1980-01-01
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Expires: 1998-05-26
Abstract
Abstract N-acetyl-para-aminophenyl N'-acetylaminothioalkanoates I are new analgesic compounds with greatly reduced hepatotoxic effects, when taken in overdose, relative to N-acetyl-para-aminophenol. They are prepared by reacting an N-acetylaminothioalkanoic acid IV with a reactive organic chloride V to form a mixed anhydride II and then reacting the latter with N-acetyl-para-aminophenol. The mixed anhydrides II are new and useful intermediates. Alternatively the derivatives I may be prepared by reacting the acid IV with bis-(4-nitrophenyl) sulfite to form a para-nitrophenyl N-acetylaminothioalkanoic acid ester VIII, reducing the latter to a para-aminophenyl N-acetylaminothioalkanoate VII, and acetylating this product. The esters VII and VIII are new and useful intermediates. Both reactions may pass through S-blocked intermediates, which are also new. Pharmaceutical compositions containing the derivatives I are disclosed, and also analgesic methods using them.
Inventors
- 👤 George Margetts
- 👤 Roderic S. Andrews
- 👤 Jean Legros
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 17:30
CPC Classifications
A; A61; A61K; A61K31/00; A61K31/33; A61K31/395; A61K31/435; A61K31/47; A61K31/485; A61K31/21; A61K31/215; A61K31/22; A61K31/495; A61K31/505; A61K31/519; A61K31/52; A61K31/54
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
52 words
N-acetyl-para-aminophenyl N'-acetylaminothioalkanoate having the general formula ##STR23## wherein n is 1 or 2, X is a hydrogen atom, a methyl group or a grouping of general formula ##STR24## wherein n' is 1 or 2 and p is zero or 1, in the form of its D or L isomer or mixtures thereof.
Claim 2
Dependent Claim
52 words
N-acetyl-para-aminophenyl N'-acetylaminothioalkanoate having the general formula ##STR23## wherein n is 1 or 2, X is a hydrogen atom, a methyl group or a grouping of general formula ##STR24## wherein n' is 1 or 2 and p is zero or 1, in the form of its D or L isomer or mixtures thereof.
Claim 3
Dependent Claim
16 words
N-Acetyl-para-aminophenyl N'-acetylmethionate, in the form of its D or L isomer or the racemic mixture thereof.
Claim 4
Dependent Claim
16 words
N-Acetyl-para-aminophenyl N'-acetylmethionate, in the form of its D or L isomer or the racemic mixture thereof.
Claim 5
Dependent Claim
16 words
N-Acetyl-para-aminophenyl N'-acetyl-cysteinate, in the form of its D or L isomer or the racemic mixture thereof.
Claim 6
Dependent Claim
16 words
N-Acetyl-para-aminophenyl N'-acetyl-cysteinate, in the form of its D or L isomer or the racemic mixture thereof.
Claim 7
Dependent Claim
20 words
Di-(N-acetyl-para-aminophenyl) N',N"-diacetylcystinate, in the form of its D or L isomer or the racemic mixture thereof, according to claim 1.
Claim 8
Dependent Claim
20 words
Di-(N-acetyl-para-aminophenyl) N',N"-diacetylcystathionate, in the form of its D or L isomer or the racemic mixture thereof, according to claim 1.
Claim 9
Dependent Claim
20 words
N-Acetyl-para-aminophenyl N'-acetyl-S-methylcysteinate, in the form of its D or L isomer or the racemic mixture thereof, according to claim 1.
Claim 10
Dependent Claim
20 words
N-Acetyl-para-aminophenyl N'-acetyl-homocysteinate, in the form of its D or L isomer or the racemic mixture thereof, according to claim 1.
Claim 11
Dependent Claim
17 words
The N-acetyl-para-aminophenyl N'-acetyl-aminothioalkanoic acid ester derivative according to claim 1, in the form of its L isomer.
Claim 12
Dependent Claim
73 words
Pharmaceutical composition for use as an analgesic containing a pain relieving effective amount of one or more of the N-acetyl-para-aminophenyl N'-acetylaminothioalkanoates having the general formula ##STR25## in which n is 1 or 2, and X is a hydrogen atom, a methyl group or a grouping of general formula ##STR26## wherein n' is 1 or 2, and p is zero or 1 as claimed in claim 1, in association with a suitable pharmaceutical vehicle.
Claim 13
Dependent Claim
81 words
A composition as claimed in claim 9, in which the pharmaceutical vehicle is: (a) the ingestible excipient of a tablet, coated tablet, or pill; the ingestible container of a capsule or cachet; the ingestible pulverulent solid carrier of a powder; or the ingestible liquid medium or a syrup, solution, suspension or elixir; or (b) a base material of low melting point capable of releasing the active ingredient to perform its pharmacological function, which base material is shaped to form a suppository.
Claim 14
Dependent Claim
26 words
A composition as claimed in claim 9, presented in the form of solid unit-doses wherein each solid unit-dose contains substantially 500 mg of the N-acetyl-para-aminophenyl N'-acetylaminothioalkanoate(s).
Claim 15
Dependent Claim
45 words
A composition as claimed in claim 9, which additionally contains one or more of the following other pharmacologically-active ingredients namely N-acetyl-para-aminophenol, codeine, codeine phosphate, caffeine, caffeine hydrate, caffeine citrate, butobarbitone, famprofazone, propyphenazone, chlormezanone, phenolphthalein, aspirin, acetomenaphthone, orphenadrine citrate, phenobarbitone, dihydrocodeine tartrate, dextropropoxyphene and pseudoephedrine hydrochloride.
Claim 16
Dependent Claim
26 words
A method of relieving pain by administering to a patient a pain relieving effective amount of one or more N-acetyl-para-aminophenyl N'-acetylaminothioalkanoate(s) as claimed in claim 1.
Claim 17
Dependent Claim
41 words
A method of relieving pain as claimed in claim 13, in which the analgesic is administered to the patient at a dosage rate of from 1 gram to 4 grams of the N-acetyl-para-aminophenyl N'-acetylaminothioalkanoate(s) per day in the adult human being.
References Cited (Backward Citations)
US3983138A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-12-31 | 1983-07-02 | 1984-01-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-12-31 | 1987-07-02 | 1988-01-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-12-31 | 1991-07-02 | 1992-01-01 | $7700.00 | Window Closed / Lapsed |