US3978116A
Expired / Lapsed
US
⏱️ 0.0 years remaining
2-naphthyl acetic acid derivatives and compositions and methods thereof
Assignee: Roche Palo Alto LLC
•
Filing: 1975-03-17
•
Granted: 1976-08-31
•
Expires: 1995-03-17
Abstract
Abstract 2-Naphthyl acetic acid derivatives and the corresponding amides, esters, hydroxamic acids and addition salts thereof, optionally substituted at the α-position on the acetic acid moiety and/or at position 6 and/or at positions 1, 4, 7 or 8 on the naphthyl ring and optionally saturated at positions 3 and 4, are anti-inflammatory, analgesic, anti-pyretic and anti-pruritic agents. A pharmaceutical method of effecting treatment of inflammation, pain, pyrexia and pruritus by the administration of naphthyl acetic acid derivatives. A pharmaceutical composition for use in the treatment of the above maladies comprising a naphthyl acetic acid derivative.
Inventors
- 👤 John H. Fried
- 👤 Ian T. Harrison
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 05:04
CPC Classifications
C; C07; C07C; C07C255/00; C07C45/00; C07C45/27; C07C45/28; C07C45/45; C07C45/46; C07C57/00; C07C57/52; C07C57/58; C07C59/00; C07C59/40; C07C59/42; C07C59/52; C07C59/58; C07C59/72; C07C59/74; C07C59/76; C07C59/84; C07C59/90; C07C63/00; C07C63/33
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
259 words
The compounds of the formulas: ##SPC9## wherein one of R 1 and R 2 is hydrogen and the other is difluoromethyl, fluoro, or chloro; or R 1 and R 2 taken together are alkylidene, halomethylene, or ethylene; R 3 is trifluoromethyl, difluoromethoxy, alkoxymethyloxy, alkylthio, difluoromethylthio, alkoxymethylthio or alkylthiomethylthio; R 4 is cycloalkyl, hydroxymethyl, alkoxymethyl, trifluoromethyl, vinyl, ethynyl, alkoxymethyloxy, alkylthiomethylthio, difluoromethoxy, alkoxymethylthio, alkylthiomethyloxy, difluoromethylthio, formyl, carboxy, acetyl, or aryl; each of R 5 (at position 4, 7, or 8) and R 6 (at position 1, 4, 7, or 8) is alkyl, trifluoromethyl, fluoro, chloro, hydroxy, alkoxy, difluoromethoxy, alkoxymethyloxy, alkylthiomethyloxy, alkylthio, difluoromethylthio, alkoxymethylthio or alkylthiomethylthio; provided that R 5 (when at position 7) is other than alkyl; R 7 is alkyl, cycloalkyl, hydroxymethyl, alkoxymethyl, trifluoromethyl, vinyl, ethynyl, fluoro, chloro, hydroxy, alkoxy, difluoromethoxy, alkoxymethyloxy, alkylthiomethyloxy, alkylthio, difluoromethylthio, alkoxymethylthio or alkylthiomethylthio, formyl, carboxy, acetyl, or aryl; each of R 8 and R 9 (at position 1, 4, 7, or 8) is alkyl, fluoro, chloro, hydroxy, alkoxy, difluoromethoxy, alkoxymethyloxy, alkylthiomethyloxy, alkylthio, difluoromethylthio, alkoxymethylthio or alkylthiomethylthio; provided that when one of R 8 and R 9 is hydroxy, alkoxy, difluoromethoxy, alkoxymethyloxy, alkylthiomethyloxy, alkylthio, difluoromethylthio, alkoxymethylthio or alkylthiomethylthio, the other is the identical group or alkyl, fluoro, or chloro; one of R 10 and R 11 is hydrogen, the other being methyl, ethyl, difluoromethyl, fluoro, or chloro; or R 10 and R 11 taken together are alkylidene, halomethylene, or ethylene; provided that when one of R 10 or R 11 is methyl or ethyl, R 6 (when at position 1 or 7) is other than alkyl.
Claim 2
Dependent Claim
259 words
The compounds of the formulas: ##SPC9## wherein one of R 1 and R 2 is hydrogen and the other is difluoromethyl, fluoro, or chloro; or R 1 and R 2 taken together are alkylidene, halomethylene, or ethylene; R 3 is trifluoromethyl, difluoromethoxy, alkoxymethyloxy, alkylthio, difluoromethylthio, alkoxymethylthio or alkylthiomethylthio; R 4 is cycloalkyl, hydroxymethyl, alkoxymethyl, trifluoromethyl, vinyl, ethynyl, alkoxymethyloxy, alkylthiomethylthio, difluoromethoxy, alkoxymethylthio, alkylthiomethyloxy, difluoromethylthio, formyl, carboxy, acetyl, or aryl; each of R 5 (at position 4, 7, or 8) and R 6 (at position 1, 4, 7, or 8) is alkyl, trifluoromethyl, fluoro, chloro, hydroxy, alkoxy, difluoromethoxy, alkoxymethyloxy, alkylthiomethyloxy, alkylthio, difluoromethylthio, alkoxymethylthio or alkylthiomethylthio; provided that R 5 (when at position 7) is other than alkyl; R 7 is alkyl, cycloalkyl, hydroxymethyl, alkoxymethyl, trifluoromethyl, vinyl, ethynyl, fluoro, chloro, hydroxy, alkoxy, difluoromethoxy, alkoxymethyloxy, alkylthiomethyloxy, alkylthio, difluoromethylthio, alkoxymethylthio or alkylthiomethylthio, formyl, carboxy, acetyl, or aryl; each of R 8 and R 9 (at position 1, 4, 7, or 8) is alkyl, fluoro, chloro, hydroxy, alkoxy, difluoromethoxy, alkoxymethyloxy, alkylthiomethyloxy, alkylthio, difluoromethylthio, alkoxymethylthio or alkylthiomethylthio; provided that when one of R 8 and R 9 is hydroxy, alkoxy, difluoromethoxy, alkoxymethyloxy, alkylthiomethyloxy, alkylthio, difluoromethylthio, alkoxymethylthio or alkylthiomethylthio, the other is the identical group or alkyl, fluoro, or chloro; one of R 10 and R 11 is hydrogen, the other being methyl, ethyl, difluoromethyl, fluoro, or chloro; or R 10 and R 11 taken together are alkylidene, halomethylene, or ethylene; provided that when one of R 10 or R 11 is methyl or ethyl, R 6 (when at position 1 or 7) is other than alkyl.
Claim 3
Dependent Claim
224 words
The compounds according to claim 1 wherein one of R 1 and R 2 is hydrogen and the other is difluoromethyl, fluoro, or chloro; or R 1 and R 2 taken together are methylene or difluoromethylene; R 3 is difluoromethoxy, methoxymethyloxy, methylthio, difluoromethylthio, or methoxymethylthio; R 4 is cyclopropyl, vinyl, ethynyl, trifluoromethyl, difluoromethoxy, methoxymethyloxy, ethoxymethyloxy, n-propoxymethyloxy, difluoromethylthio, or methoxymethylthio; each of R 5 (at position 4, 7, or 8), R 6 (at position 1, 4, 7, or 8), R 8 and R 9 (at position 1, 4, 7, or 8) is fluoro, chloro, methyl, ethyl, isopropyl, methoxy, methoxymethyloxy, difluoromethoxy, methylthio, difluoromethylthio, or methoxymethylthio; provided that R 5 (when at position 7) is other than methyl, ethyl, or isopropyl; provided that when one of R 8 or R 9 is methoxy, methoxymethyloxy, difluoromethoxy, methylthio, difluoromethylthio, or methoxymethylthio, the other is the identical group or fluoro, chloro, methyl, ethyl, or isopropyl; R 7 is methyl, ethyl, isopropyl, cyclopropyl, trifluoromethyl, vinyl, ethynyl, fluoro, chloro, methoxy, methoxymethyloxy, difluoromethoxy, methylthio, methoxymethylthio, or difluoromethylthio; one of R 10 and R 11 is hydrogen, the other being methyl or difluoromethyl; or R 10 and R 11 taken together are methylene or difluoromethylene; provided that when one of R 10 and R 11 is methyl or ethyl, R 6 (when at position 1 or 7) is other than methyl, ethyl, or isopropyl.
Claim 4
Dependent Claim
28 words
The compound of formula XIV according to claim 1 wherein R 7 is methyl; one of R 10 and R 11 is hydrogen and the other is methyl.
Claim 5
Dependent Claim
28 words
The compound of formula XIV according to claim 1 wherein R 7 is ethyl; one of R 10 and R 11 is hydrogen and the other is methyl.
Claim 6
Dependent Claim
28 words
The compound of formula XIV according to claim 1 wherein R 7 is trifluoromethyl; one of R 10 and R 11 is hydrogen and the other is methyl.
Claim 7
Dependent Claim
28 words
The compound of formula XIV according to claim 1 wherein R 7 is fluoro; one of R 10 and R 11 is hydrogen and the other is methyl.
Claim 8
Dependent Claim
28 words
The compound of formula XIV according to claim 1 wherein R 7 is chloro; one of R 10 and R 11 is hydrogen and the other is methyl.
Claim 9
Dependent Claim
28 words
The compound of formula XIV according to claim 1 wherein R 7 is methoxy; one of R 10 and R 11 is hydrogen and the other is methyl.
Claim 10
Dependent Claim
28 words
The compound of formula XIV according to claim 1 wherein R 7 is difluoromethoxy; one of R 10 and R 11 is hydrogen and the other is methyl.
Claim 11
Dependent Claim
28 words
The compound of formula XIV according to claim 1 wherein R 7 is methoxymethyloxy; one of R 10 and R 11 is hydrogen and the other is methyl.
Claim 12
Dependent Claim
28 words
The compound of formula XIV according to claim 1 wherein R 7 is methylthio; one of R 10 and R 11 is hydrogen and the other is methyl.
Claim 13
Dependent Claim
28 words
The compound of formula XIV according to claim 1 wherein R 7 is difluoromethylthio; one of R 10 and R 11 is hydrogen and the other is methyl.
Claim 14
Dependent Claim
28 words
The compound of formula XIV according to claim 1 wherein R 7 is methoxy; one of R 10 and R 11 is hydrogen and the other is difluoromethyl.
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) | 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 |