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3-Aminomethylene-6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydro-1-quinoline carboxylic acid esters and intermediates leading thereto

Assignee: Pfizer Inc
•
Filing: 1975-11-04
•
Granted: 1976-08-31
•
Expires: 1995-11-04
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Abstract

Abstract Racemic 3-aminomethylene-6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydro-1-qui noline carboxylic acid, alkyl, phenyl and benzyl esters as analgesic agents, synthesized from 3-hydroxymethylene-6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydro-1-q uinoline carboxylic acid, alkyl, phenyl and benzyl esters and the dextrorotatory enantiomer 3-aminomethylene-6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydro-1-qui noline carboxylic acid, ethyl ester, an outstanding analgesic agent.

Inventors

  • 👤 Michael R. Johnson
  • 👤 Jacob J. Plattner

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-09 20:17
CPC Classifications
C; C07; C07D; C07D215/00; C07D215/02; C07D215/16; C07D215/20; C07D215/22; C07D215/233; A; A61; A61P; A61P25/00; A61P25/04

Claims Analysis

Total Claims: 17
Claim 1
Independent Claim 151 words
A racemic compound selected from the group consisting of ##SPC13## wherein R 1 taken separately is selected from the group consisting of hydrogen and methyl; R 2 taken separately is selected from the group consisting of hydrogen, alkyl having from one to five carbon atoms, propargyl, phenyl, naphthyl, phenylalkylene wherein said alkylene has from one to four carbon atoms, naphthylalkylene wherein said alkylene has from one to four carbon atoms, dimethylaminoalkylene wherein said alkylene has from two to four carbon atoms and mono-substituted 2-ethyl wherein said substituent is selected from the group consisting of methoxy and phenoxy; R 3 is selected from the group consisting of alkyl having from one to five carbon atoms, phenyl, benzyl and mono-substituted benzyl and phenyl wherein said substituent is selected from the group consisting of fluoro, chloro, methyl, methoxy and trifluoromethyl; and the pharmaceutically acceptable acid addition salts thereof wherein R 2 is said dimethylaminoalkylene.
Claim 2
Dependent Claim 151 words
A racemic compound selected from the group consisting of ##SPC13## wherein R 1 taken separately is selected from the group consisting of hydrogen and methyl; R 2 taken separately is selected from the group consisting of hydrogen, alkyl having from one to five carbon atoms, propargyl, phenyl, naphthyl, phenylalkylene wherein said alkylene has from one to four carbon atoms, naphthylalkylene wherein said alkylene has from one to four carbon atoms, dimethylaminoalkylene wherein said alkylene has from two to four carbon atoms and mono-substituted 2-ethyl wherein said substituent is selected from the group consisting of methoxy and phenoxy; R 3 is selected from the group consisting of alkyl having from one to five carbon atoms, phenyl, benzyl and mono-substituted benzyl and phenyl wherein said substituent is selected from the group consisting of fluoro, chloro, methyl, methoxy and trifluoromethyl; and the pharmaceutically acceptable acid addition salts thereof wherein R 2 is said dimethylaminoalkylene.
Claim 3
Dependent Claim 22 words
A compound of claim 1 wherein R 1 is hydrogen and R 3 is alkyl having from one to five carbon atoms.
Claim 4
Dependent Claim 15 words
The compound of claim 2 wherein R 2 is hydrogen and R 3 is ethyl.
Claim 5
Dependent Claim 15 words
The compound of claim 2 wherein R 2 is benzyl and R 3 is ethyl.
Claim 6
Dependent Claim 15 words
The compound of claim 2 wherein R 2 is methoxyethyl and R 3 is ethyl.
Claim 7
Dependent Claim 15 words
The compound of claim 2 wherein R 2 is methyl and R 3 is ethyl.
Claim 8
Dependent Claim 15 words
A compound of claim 1 wherein R 1 is hydrogen and R 3 is benzyl.
Claim 9
Dependent Claim 10 words
The compound of claim 7 wherein R 2 is hydrogen.
Claim 10
Dependent Claim 21 words
A compound of claim 1 wherein R 1 is methyl and R 3 is alkyl having one to five carbon atoms.
Claim 11
Dependent Claim 15 words
The compound of claim 9 wherein R 2 is methyl and R 3 is ethyl.
Claim 12
Dependent Claim 48 words
A racemic compound of the formula ##SPC14## wherein R 3 is selected from the group consisting of alkyl having from one to five carbon atoms, phenyl, benzyl and mono-substituted benzyl and phenyl wherein said substituent is selected from the group consisting of fluoro, chloro, methyl, methoxy and trifluoromethyl.
Claim 13
Dependent Claim 48 words
A racemic compound of the formula ##SPC14## wherein R 3 is selected from the group consisting of alkyl having from one to five carbon atoms, phenyl, benzyl and mono-substituted benzyl and phenyl wherein said substituent is selected from the group consisting of fluoro, chloro, methyl, methoxy and trifluoromethyl.
Claim 14
Dependent Claim 10 words
The compound of claim 11 wherein R 3 is ethyl.
Claim 15
Dependent Claim 10 words
The compound of claim 11 wherein R 3 is benzyl.
Claim 16
Dependent Claim 10 words
The dextrorotatory enantiomer of the compound of the formula ##SPC15##
Claim 17
Dependent Claim 10 words
The dextrorotatory enantiomer of the compound of the formula ##SPC15##

References Cited (Backward Citations)

US2421693A Cited
US3347856A Cited
US3455929A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1979-08-31 1980-03-01 1980-08-31 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1983-08-31 1984-03-01 1984-08-31 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1987-08-31 1988-03-01 1988-08-31 $7700.00 Window Closed / Lapsed

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