US3960871A
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Esters of thienobenzopyrans and thiopyranobenzopyrans
Assignee: Sharps Associates
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Filing: 1974-03-05
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Granted: 1976-06-01
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Expires: 1994-03-05
Abstract
Abstract Novel thienobenzopyran and thiopyranobenzopyran esters represented by the formula ##SPC1## Wherein n is 0 to 3 and m is 0 to 3 and m + n = 2 or 3, R 1 is lower alkyl, R 2 is alkyl or cycloalkyl-lower alkyl, R 4 is hydrogen or lower alkyl, R 5 is hydrogen or lower alkyl, and R 3 is ##EQU1## wherein Y is a straight or branched chain C 1 to C 8 alkylene, R 6 is hydrogen or a lower alkyl, a is an integer from 1 to 4, b is an integer from 1 to 4, X is CH 2 , O, S or NR 7 wherein R 7 is hydrogen or lower alkyl, with the limitation that when X is O, S or NR 7 , a and b each must be 2; and the acid addition salts thereof.
Inventors
- 👤 Louis Selig Harris
- 👤 Harry George Pars
- 👤 Raj Kumar Razdan
- 👤 John Clark Sheehan
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 22:59
CPC Classifications
C; C07; C07D; C07D495/00; C07D495/02; C07D495/04; C07D333/00; C07D333/02; C07D333/04; C07D333/26; C07D333/38
Claims Analysis
Total Claims: 36
Claim 1
Independent Claim
155 words
A compound of the formula ##SPC26## wherein n is 0 to 3, and m is 0 to 3 and m + n = 2 or 3, R 1 is lower alkyl, R 2 is a C 1 to C 20 alkyl or a C 3 to C 8 cycloalkyl- C 1 to C 6 loweralkyl, R 4 is hydrogen or lower alkyl, R 5 is hydrogen or lower alkyl, and R 3 is ##EQU7## wherein Y is a straight or branched chain C 1 to C 8 alkylene, R 6 is hydrogen or lower alkyl, a is an integer from 1 to 4, b is an integer from 1 to 4, X is CH 2 , S or NR 7 wherein R 7 is hydrogen or lower alkyl, with the limitation that when X is S or NR 7 , a and b each must be 2; or a pharmaceutically acceptable acid addition salt thereof.
Claim 2
Dependent Claim
155 words
A compound of the formula ##SPC26## wherein n is 0 to 3, and m is 0 to 3 and m + n = 2 or 3, R 1 is lower alkyl, R 2 is a C 1 to C 20 alkyl or a C 3 to C 8 cycloalkyl- C 1 to C 6 loweralkyl, R 4 is hydrogen or lower alkyl, R 5 is hydrogen or lower alkyl, and R 3 is ##EQU7## wherein Y is a straight or branched chain C 1 to C 8 alkylene, R 6 is hydrogen or lower alkyl, a is an integer from 1 to 4, b is an integer from 1 to 4, X is CH 2 , S or NR 7 wherein R 7 is hydrogen or lower alkyl, with the limitation that when X is S or NR 7 , a and b each must be 2; or a pharmaceutically acceptable acid addition salt thereof.
Claim 3
Dependent Claim
117 words
A compound of the formula ##SPC27## wherein n is 0 to 3, and m is 0 to 3 and m + n equals 2 or 3, R 1 is lower alkyl, R 2 is a C 1 to C 20 alkyl or C 3 to C 8 cycloalkyl-C 1 to C 6 loweralkyl, R 4 is hydrogen or lower alkyl, R 5 is hydrogen or lower alkyl, and R 3 is ##EQU8## wherein Y is a straight or branched chain C 1 to C 8 alkylene, R 6 is hydrogen or lower alkyl, a is an integer from 1 to 4, b is an integer from 1 to 4, or a pharmaceutically acceptable acid addition salt thereof.
Claim 4
Dependent Claim
117 words
A compound of the formula ##SPC27## wherein n is 0 to 3, and m is 0 to 3 and m + n equals 2 or 3, R 1 is lower alkyl, R 2 is a C 1 to C 20 alkyl or C 3 to C 8 cycloalkyl-C 1 to C 6 loweralkyl, R 4 is hydrogen or lower alkyl, R 5 is hydrogen or lower alkyl, and R 3 is ##EQU8## wherein Y is a straight or branched chain C 1 to C 8 alkylene, R 6 is hydrogen or lower alkyl, a is an integer from 1 to 4, b is an integer from 1 to 4, or a pharmaceutically acceptable acid addition salt thereof.
Claim 5
Dependent Claim
45 words
A compound in accordance with claim 2 wherein m is 1, n is 1 and said compound is represented by the formula ##SPC28## wherein R 1 , R 2 , R 3 , R 4 and R 5 have the meaning assigned in claim 2.
Claim 6
Dependent Claim
18 words
A compound in accordance with claim 3 wherein for R 3 , Y contains three or four carbons.
Claim 7
Dependent Claim
45 words
A compound in accordance with claim 2, wherein m is 0, n is 2 and said compound is represented by the formula ##SPC29## wherein R 1 , R 2 , R 3 , R 4 and R 5 have the meaning assigned in claim 2.
Claim 8
Dependent Claim
18 words
A compound in accordance with claim 5 wherein for R 3 , Y contains three or four carbons.
Claim 9
Dependent Claim
46 words
A compound in accordance with claim 2 wherein m is 1 and n is 2 and said compound is represented by the formula ##SPC30## wherein R 1 , R 2 , R 3 , R 4 and R 5 have the meaning assigned in claim 2.
Claim 10
Dependent Claim
18 words
A compound in accordance with claim 7 wherein for R 3 , Y contains three or four carbons.
Claim 11
Dependent Claim
45 words
A compound in accordance with claim 2 wherein m is 0, n is 3 and the compound is represented by the formula ##SPC31## wherein R 1 , R 2 , R 3 , R 4 and R 5 have the meaning assigned in claim 2.
Claim 12
Dependent Claim
18 words
A compound in accordance with claim 9 wherein for R 3 , Y contains three or four carbons.
Claim 13
Dependent Claim
17 words
A compound in accordance with claim 10 named 2,3-dihydro-5,5-dimethyl-8-(3-methyl-2-octyl)-10-[4-(piperidino)-butyryloxy]-4H,5H-thiopyrano[3,2-c][1]benzopyran or a pharmaceutically acceptable acid addition salt thereof.
Claim 14
Dependent Claim
46 words
A compound in accordance with claim 2 wherein m is 2 and n is 0 and said compound is represented by the formula ##SPC32## wherein R 1 , R 2 , R 3 , R 4 and R 5 have the meaning assigned in claim 2.
Claim 15
Dependent Claim
18 words
A compound in accordance with claim 12 wherein for R 3 , Y contains three or four carbons.
Claim 16
Dependent Claim
12 words
A compound named 1,2-dihydro-4,4-dimethyl-9-[4-(piperidino)butyryloxy]-7-(3-methyl-2-octyl)-4H-thieno[2,3-c][1]benzopyran or a pharmaceutically acceptable acid addition salt thereof.
Claim 17
Dependent Claim
12 words
A compound named 1,2-dihydro-4,4-dimethyl-9-[4-(piperidino)butyryloxy]-7-(3-methyl-2-octyl)-4H-thieno[2,3-c][1]benzopyran or a pharmaceutically acceptable acid addition salt thereof.
Claim 18
Dependent Claim
12 words
A compound named 1,2-dihydro-7-(3-methyl-2-octyl)-9-[2-methyl-4-(piperidino)butyryloxy]-1,4,4-trimethyl-4H-thieno[2,3-c][1]benzopyran or a pharmaceutically acceptale acid addition salt thereof.
Claim 19
Dependent Claim
12 words
A compound named 1,2-dihydro-7-(3-methyl-2-octyl)-9-[2-methyl-4-(piperidino)butyryloxy]-1,4,4-trimethyl-4H-thieno[2,3-c][1]benzopyran or a pharmaceutically acceptale acid addition salt thereof.
Claim 20
Dependent Claim
18 words
A compound in accordance with claim 13 named, 1,2-dihydro-7-(3-methyl-2-octyl)-9-[4-(pyrrolidino) butyryloxy]-2,2,4,4-tetramethyl-4H-thieno-[2,3-c][1]benzopyran or a pharmaceutically acceptable acid addition salt thereof.
Claim 21
Dependent Claim
12 words
A compound named 1,2-dihydro-7-(3-methyl-2-octyl)-9-[4-(piperidino)butyryloxy]-1,4,4-trimethyl-4H-thieno[2,3-c][1]benzopyran or a pharmaceutically acceptable acid addition salt thereof.
Claim 22
Dependent Claim
12 words
A compound named 1,2-dihydro-7-(3-methyl-2-octyl)-9-[4-(piperidino)butyryloxy]-1,4,4-trimethyl-4H-thieno[2,3-c][1]benzopyran or a pharmaceutically acceptable acid addition salt thereof.
Claim 23
Dependent Claim
46 words
A compound in accordance with claim 2 wherein m is two and n is one and said compound is represented by the formula ##SPC33## wherein R 1 , R 2 , R 3 , R 4 and R 5 have the meaning assigned in claim 2.
Claim 24
Dependent Claim
18 words
A compound in accordance with claim 18 wherein for R 3 , Y contains three or four carbons.
Claim 25
Dependent Claim
46 words
A compound in accordance with claim 2 wherein n is 0 and m is 3 and said compound is represented by the formula ##SPC34## wherein R 1 , R 2 , R 3 , R 4 and R 5 have the meaning assigned in claim 2.
Claim 26
Dependent Claim
18 words
A compound in accordance with claim 20 wherein for R 3 , Y contains three or four carbons.
Claim 27
Dependent Claim
13 words
A compound named 1,2-dihydro-5,5-dimethyl-8-(3-methyl-2-octyl)-10-[4-(piperidino) butyryloxy]-3H,5H-thiopyrano[2,3-c][1]benzopyran or a pharmaceutically acceptable acid addition salt thereof.
Claim 28
Dependent Claim
13 words
A compound named 1,2-dihydro-5,5-dimethyl-8-(3-methyl-2-octyl)-10-[4-(piperidino) butyryloxy]-3H,5H-thiopyrano[2,3-c][1]benzopyran or a pharmaceutically acceptable acid addition salt thereof.
Claim 29
Dependent Claim
12 words
A compound named 1,2-dihydro-5,5-dimethyl-8-(3-methyl-2-octyl)-10-[2-methyl-4-(piperidino)butyryloxy]-3H,5H-thiopyrano[2,3-c][1]benzopyran. or a pharmaceutically acceptable acid addition salt thereof.
Claim 30
Dependent Claim
12 words
A compound named 1,2-dihydro-5,5-dimethyl-8-(3-methyl-2-octyl)-10-[2-methyl-4-(piperidino)butyryloxy]-3H,5H-thiopyrano[2,3-c][1]benzopyran. or a pharmaceutically acceptable acid addition salt thereof.
Claim 31
Dependent Claim
18 words
A compound in accordance with claim 21 named 1,2-dihydro-8-(3-methyl-2-octyl)-10-[2-methyl-4-piperidino) butyryloxy]-1,5,5-trimethyl-3H,5H-thiopyrano[2,3-c][1]benzopyran or a pharmaceutically acceptable acid addition salt thereof.
Claim 32
Dependent Claim
98 words
A compound of the formula ##SPC35## wherein R 1 is a lower alkyl group, R 2 is a C 1 to C 20 alkyl or a C 3 to C 8 cycloalkyl-C 1 to C 6 lower alkyl group and R 3 represents a group of the formula ##EQU9## wherein Y is an alkylene having two to five carbons with at least two carbons between the carbonyl group and the nitrogen atom, R 9 is piperidino, pyrrolidino or homopiperidino, and R 4 and R 5 are hydrogen or lower alkyl, or a pharmaceutically acceptable acid addition salt thereof.
Claim 33
Dependent Claim
98 words
A compound of the formula ##SPC35## wherein R 1 is a lower alkyl group, R 2 is a C 1 to C 20 alkyl or a C 3 to C 8 cycloalkyl-C 1 to C 6 lower alkyl group and R 3 represents a group of the formula ##EQU9## wherein Y is an alkylene having two to five carbons with at least two carbons between the carbonyl group and the nitrogen atom, R 9 is piperidino, pyrrolidino or homopiperidino, and R 4 and R 5 are hydrogen or lower alkyl, or a pharmaceutically acceptable acid addition salt thereof.
Claim 34
Dependent Claim
15 words
A compound in accordance with claim 25 named 1,2-dihydro-9-[3-(piperidino)propionyloxy]-4,4,7-trimethyl-4H-thieno[2,3-c][1]benzopyran or an acid addition salt thereof.
Claim 35
Dependent Claim
95 words
A compound of the formula ##SPC36## wherein R 1 is a lower alkyl group, R 2 is a C 1 to C 20 alkyl or a C 3 to C 8 cycloalkyl-C 1 to C 6 lower alkyl, R 3 represents a group of the formula ##EQU10## wherein Y is an alkylene having two to four carbons with at least two carbons between the carbonyl group and the nitrogen atom, R 10 is piperidino or pyrrolidino, and R 4 and R 5 are hydrogen or lower alkyl, or a pharmaceutically acceptable acid addition salt thereof.
Claim 36
Dependent Claim
95 words
A compound of the formula ##SPC36## wherein R 1 is a lower alkyl group, R 2 is a C 1 to C 20 alkyl or a C 3 to C 8 cycloalkyl-C 1 to C 6 lower alkyl, R 3 represents a group of the formula ##EQU10## wherein Y is an alkylene having two to four carbons with at least two carbons between the carbonyl group and the nitrogen atom, R 10 is piperidino or pyrrolidino, and R 4 and R 5 are hydrogen or lower alkyl, or a pharmaceutically acceptable acid addition salt thereof.
References Cited (Backward Citations)
US3656906A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-06-01 | 1979-12-01 | 1980-06-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-06-01 | 1983-12-01 | 1984-06-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-06-01 | 1987-12-01 | 1988-06-01 | $7700.00 | Window Closed / Lapsed |