US3984465A
Expired / Lapsed
US
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1-Oxo-2,2-disubstituted-5-indanyloxy(or thio)alkanoic acids
Assignee: Merck and Co Inc
•
Filing: 1973-09-21
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Granted: 1976-10-05
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Expires: 1993-09-21
Abstract
Abstract 1-Oxo-2,2-disubstituted-5-indanyloxy(or thio)alkanoic acids and their salt, ester, anhydride, amide and 5-tetrazolyl derivatives are disclosed. The products display a dual pharmaceutical utility in that they exhibit diuretic, saluretic and uricosuric activity. The acid products are prepared by treating a 2,2-disubstituted-5-hydroxy(or mercapto)-1-indanone with an haloalkanoic acid or ester thereof and, if the ester is employed, hydrolyzing the ester.
Inventors
- 👤 Edward J. Cragoe, Jr.
- 👤 Otto W. WOLTERSDORF, Jr.
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 09:31
CPC Classifications
C; C07; C07D; C07D257/00; C07D257/02; C07D257/04; A; A61; A61P; A61P19/00; A61P19/06; A61P9/00; A61P9/12; C07C; C07C323/00; C07C45/00; C07C45/45; C07C45/46; C07C45/61; C07C45/63; C07C45/65; C07C45/67; C07C45/673; C07C45/68; C07C45/70; C07C45/71; C07C45/72; C07C45/74; C07C45/75; C07C51/00; C07C51/42; C07C51/487; C07C51/54; C07C51/56; C07C59/00; C07C59/40; C07C59/76; C07C59/90; C07C2603/00; C07C2603/02; C07C2603/04; C07C2603/06; C07C2603/10; C07C2603/12; C07C2603/18
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
126 words
A compound of the formula ##SPC22## wherein A is oxygen; R is lower alkyl or cycloalkyl having from 3-6 carbon atoms; R 1 is lower alkyl, lower alkenyl, halo lower alkenyl, lower alkynyl, phenyl lower alkyl, phenyl lower alkenyl, hydroxy lower alkyl, lower alkoxy lower alkyl, oxo lower alkyl or hydroxy cycloalkyl having 4-6 carbon atoms, cycloalkyl alkyl containing 4-7 carbon atoms; R 2 is hydrogen, halo, lower alkyl, phenyl or substituted phenyl wherein the substituent is lower alkyl or halo; R n is hydrogen or methyl; X 1 is hydrogen, methyl or halo; and X 2 is methyl or halo; and Y is alkylene or haloalkylene containing a maximum of 4 carbon atoms, and the non-toxic pharmacologically acceptable salt and lower alkyl ester derivatives thereof.
Claim 2
Dependent Claim
126 words
A compound of the formula ##SPC22## wherein A is oxygen; R is lower alkyl or cycloalkyl having from 3-6 carbon atoms; R 1 is lower alkyl, lower alkenyl, halo lower alkenyl, lower alkynyl, phenyl lower alkyl, phenyl lower alkenyl, hydroxy lower alkyl, lower alkoxy lower alkyl, oxo lower alkyl or hydroxy cycloalkyl having 4-6 carbon atoms, cycloalkyl alkyl containing 4-7 carbon atoms; R 2 is hydrogen, halo, lower alkyl, phenyl or substituted phenyl wherein the substituent is lower alkyl or halo; R n is hydrogen or methyl; X 1 is hydrogen, methyl or halo; and X 2 is methyl or halo; and Y is alkylene or haloalkylene containing a maximum of 4 carbon atoms, and the non-toxic pharmacologically acceptable salt and lower alkyl ester derivatives thereof.
Claim 3
Dependent Claim
17 words
The acid and non-toxic pharmacologically acceptable salts compounds of claim 1 wherein Y is --CH 2 --.
Claim 4
Dependent Claim
59 words
A compound of the formula: ##SPC23## wherein R 3 is lower alkyl, cycloalkyl containing from 5-6 nuclear carbon atoms, hydroxy cycloalkyl containing 4-6 carbon atoms, or phenyl lower alkyl; R 4 is lower alkyl and X 3 and X 4 are the same or different radicals selected from methyl or chloro, and the non-toxic, pharmacologically acceptable salt derivatives thereof.
Claim 5
Dependent Claim
59 words
A compound of the formula: ##SPC23## wherein R 3 is lower alkyl, cycloalkyl containing from 5-6 nuclear carbon atoms, hydroxy cycloalkyl containing 4-6 carbon atoms, or phenyl lower alkyl; R 4 is lower alkyl and X 3 and X 4 are the same or different radicals selected from methyl or chloro, and the non-toxic, pharmacologically acceptable salt derivatives thereof.
Claim 6
Dependent Claim
27 words
A compound according to claim 3 wherein R 3 is cyclopentyl; R 4 is methyl and X 3 and X 4 are chloro which is (1-oxo-2-cyclopentyl-2-methyl-6,7-dichloro-5-indanyloxy)acetic acid.
Claim 7
Dependent Claim
9 words
The sodium salt of the compound of claim 4.
Claim 8
Dependent Claim
13 words
The dextro enantiomer of the compound of claim 4 which is (+)-(1-oxo-2-cyclopentyl-2-methyl-6,7-dichloro-5-indanyloxy)acetic acid.
Claim 9
Dependent Claim
13 words
The levo enantiomer of the compound of claim 4 which is (-)-(1-oxo-2-cyclopentyl-2-methyl-6,7-dichloro-5-indanyloxy)acetic acid.
Claim 10
Dependent Claim
27 words
A compound according to claim 3 wherein R 3 is isopropyl; R 4 is methyl and X 3 and X 4 are chloro which is (1-oxo-2-methyl-2-isopropyl-6,7-dichloro-5-indanyloxy)acetic acid.
Claim 11
Dependent Claim
14 words
The levo enantiomer of the compound of claim 8 which is (-) -(1-oxo-2-methyl-2-isopropyl-6,7-dichloro-5-indanyloxy)acetic acid.
Claim 12
Dependent Claim
13 words
The dextro enantiomer of the compound of claim 8 which is (+)-(1-oxo-2-methyl-2-isopropyl-6,7-dichloro-5-indanyloxy)acetic acid.
Claim 13
Dependent Claim
27 words
A compound according to claim 3 wherein R 3 is benzyl; R 4 is methyl and X 3 and X 4 are chloro; which is (1-oxo-2-benzyl-2-methyl-6,7-dichloro-5-indanyloxy)acetic acid.
Claim 14
Dependent Claim
27 words
A compound according to claim 3 wherein R 3 is ethyl; R 4 is methyl and X 3 and X 4 are chloro; which is (1-oxo-2-ethyl-2-methyl-6,7-dichloro-5-indanyloxy)acetic acid.
Claim 15
Dependent Claim
29 words
A compound according to claim 3 wherein R 3 is hydroxy cyclopentyl; R 4 is methyl and X 3 and X 4 are chloro; which is (1-oxo-2-hydroxy cyclopentyl-2-methyl-6,7-dichloro-5-indanyloxy)acetic acid.
Claim 16
Dependent Claim
35 words
A compound according to claim 1 wherein R is isopropyl; R' is hydroxymethyl and X 1 and X 2 are chloro; A is oxygen, Y is methylene; R n is hydrogen; which is (1-oxo-2-hydroxymethyl-2-isopropyl-6,7-dichloro-5-indanyloxy)acetic acid.
Claim 17
Dependent Claim
41 words
A compound according to claim 1 wherein R is isopropyl; R 1 is t-butoxymethyl R 2 is hydrogen and X 1 and X 2 are chloro; A is oxygen and Y is methylene; R n is hydrogen; which is (1-oxo-2-isopropyl-2-tert.-butoxymethyl)-6,7-dichloro-5-indanyloxy)acetic acid.
Claim 18
Dependent Claim
26 words
A compound according to claim 3 wherein R 3 and R 4 are methyl and X 3 and X 4 are chloro; which is (1-oxo-2,2-dimethyl-6,7-dichloro-5-indanyloxy)acetic acid.
Claim 19
Dependent Claim
28 words
A compound according to claim 3 wherein R 3 is cyclopentyl; R 4 is methyl; X 3 is methyl and X 4 is chloro; which is (1-oxo-2-cyclopentyl-2,6-dimethyl-7-chloro-5-indanyloxy)acetic acid.
Claim 20
Dependent Claim
37 words
A compound according to claim 1 wherein R, R 1 and R n are methyl; R 2 is phenyl; A is oxygen; Y is methylene and X 1 and X 2 are chloro; which is (1-oxo-2,2,3-trimethyl-3-phenyl-6,7-dichloro-5-indanyloxy)acetic acid.
Claim 21
Dependent Claim
40 words
A compound according to claim 1 wherein R is methyl; R 1 is ethyl; R 2 is phenyl; R n is hydrogen; A is oxygen; Y is methylene and X 1 and X 2 are chloro; which is (1-oxo-2-ethyl-2-methyl-3-phenyl-6,7-dichloro-5-indanyloxy)acetic acid.
References Cited (Backward Citations)
US3668241A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-10-05 | 1980-04-05 | 1980-10-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-10-05 | 1984-04-05 | 1984-10-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-10-05 | 1988-04-05 | 1988-10-05 | $7700.00 | Window Closed / Lapsed |