Patent US5015658A successfully refreshed from Google Patents.
US5015658A
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Thiochroman esters of phenols and terephthallates having retinoid-like activity
Assignee: Allergan Inc
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Filing: 1989-06-15
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Granted: 1991-05-14
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Expires: 2009-06-15
Abstract
Abstract Compounds of formula I ##STR1## in which: the R groups are independently hydrogen or lower alkyl; one of A and B is O or S and the other is --C(O)--, A being attached to the thiochroman ring at the 6 or 7-position; n is 0-5; and Z is H, an acid or acid derivative, an alcohol or alcohol derivative, acetal or acetal derivative or ketone or ketone derivative, or a pharmaceutically acceptable salt, have retinoid-like activity.
Inventors
- 👤 Roshantha A. S. Chandraratna
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 11:37
CPC Classifications
C; C07; C07D; C07D335/00; C07D335/04; C07D335/06
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
251 words
A Compound of the formula ##STR9## in which: the R groups are independently hydrogen or lower alkyl; R 5 is lower alkyl, R 5 being attached to the thiochroman ring at the 6 or at the 7-position; one of A and B is O or S and the other is --C(O)--, being attached to the thiochroman ring at the unoccupied 6 or 7-position; n is 0-5; and Z is H, or Z is --COD where D is --OH, or OM wherein M is a pharmaceutically acceptable cation, or D is OR 1 where R 1 is a lower alkyl group, or D is --N(R 4 ) 2 where R 4 is hydrogen or a lower alkyl group, or Z is --OE where E is hydrogen or a C 1-20 aliphatic, cycloaliphatic, or aliphatic-phenyl ether-forming group, or a C 1-10 aliphatic or cycloaliphatic carboxylic acid ester forming group, or a phenyl or lower alkyl phenyl carboxylic acid ester forming group, or Z is --CHO or an acetal derivative thereof formed with a lower alkyl or cycloalkyl alcohol, or an acetal derivative thereof formed with an alkyl diol having 2 to 6 carbon atoms, or Z is --COR 3 where R 3 is --(CH 2 ) m CH 3 where m is 0-4 and the sum of n and m does not exceed 4, or a ketal derivative thereof formed with a lower alkyl or cycloalkyl alcohol, or a ketal derivative thereof formed with an alkyl diol having 2 to 6 carbon atoms.
Claim 2
Dependent Claim
251 words
A Compound of the formula ##STR9## in which: the R groups are independently hydrogen or lower alkyl; R 5 is lower alkyl, R 5 being attached to the thiochroman ring at the 6 or at the 7-position; one of A and B is O or S and the other is --C(O)--, being attached to the thiochroman ring at the unoccupied 6 or 7-position; n is 0-5; and Z is H, or Z is --COD where D is --OH, or OM wherein M is a pharmaceutically acceptable cation, or D is OR 1 where R 1 is a lower alkyl group, or D is --N(R 4 ) 2 where R 4 is hydrogen or a lower alkyl group, or Z is --OE where E is hydrogen or a C 1-20 aliphatic, cycloaliphatic, or aliphatic-phenyl ether-forming group, or a C 1-10 aliphatic or cycloaliphatic carboxylic acid ester forming group, or a phenyl or lower alkyl phenyl carboxylic acid ester forming group, or Z is --CHO or an acetal derivative thereof formed with a lower alkyl or cycloalkyl alcohol, or an acetal derivative thereof formed with an alkyl diol having 2 to 6 carbon atoms, or Z is --COR 3 where R 3 is --(CH 2 ) m CH 3 where m is 0-4 and the sum of n and m does not exceed 4, or a ketal derivative thereof formed with a lower alkyl or cycloalkyl alcohol, or a ketal derivative thereof formed with an alkyl diol having 2 to 6 carbon atoms.
Claim 3
Dependent Claim
19 words
A compound of claim 1 where A is O and is attached to the thiochroman ring at the 6-position.
Claim 4
Dependent Claim
22 words
A compound of claim 2 where Z is COOH or said ester or said amide thereof, or said pharmaceutically acceptable salt thereof.
Claim 5
Dependent Claim
19 words
A compound of claim 1 where A is O and is attached to the thiochroman ring at the 7-position.
Claim 6
Dependent Claim
22 words
A compound of claim 4 where Z is COOH or said ester or said amide thereof, or said pharmaceutically acceptable salt thereof.
Claim 7
Dependent Claim
19 words
A compound of claim 1 where A is C═O and is attached to the thiochroman ring at the 6-position.
Claim 8
Dependent Claim
22 words
A compound of claim 6 where Z is COOH or said ester or said amide thereof, or said pharmaceutically acceptable salt thereof.
Claim 9
Dependent Claim
19 words
A compound of claim 7 which is ethyl 4-(4,4,7-trimethyl-6-thiochromanoyloxy)benzoate, 4-(4,4,7-trimethyl-6-thiochromanoyloxy)benzoic acid, or a pharmaceutically acceptable salt of the acid.
Claim 10
Dependent Claim
19 words
A compound of claim 7 which is ethyl 4-(2,2,4,4,7-pentamethyl-6-thiochromanoyloxy)benzoate, 4-(2,2,4,4,7-pentamethyl-6-thiochromanoyloxy)benzoic acid, or a pharamaceutically acceptable salt of the acid.
Claim 11
Dependent Claim
19 words
A compound of claim 1 where A is C═O and is attached to the thiochroman ring at the 7-position.
Claim 12
Dependent Claim
22 words
A compound of claim 10 where Z is COOH or said ester or said amide thereof, or said pharmaceutically acceptable salt thereof.
Claim 13
Dependent Claim
16 words
A compound of the formula ##STR10## where R 1 is H or a lower alkyl group.
Claim 14
Dependent Claim
16 words
A compound of the formula ##STR10## where R 1 is H or a lower alkyl group.
Claim 15
Dependent Claim
10 words
A compound of claim 12 where R 1 is hydrogen.
Claim 16
Dependent Claim
10 words
A compound of claim 12 where R 1 is ethyl.
Claim 17
Dependent Claim
14 words
A pharmaceutical composition comprising a pharmaceutically acceptable excipient and a compound of claim 1.
Claim 18
Dependent Claim
29 words
A method for treating psoriasis in a mammal which method comprises administering, alone or with a pharmaceutically acceptable excipient, a therapeutically effective amount of a compound of claim 1.
References Cited (Backward Citations)
US4788213A
Cited
US4895868A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1994-05-13 | 1994-11-12 | 1995-05-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1998-05-13 | 1998-11-12 | 1999-05-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2002-05-13 | 2002-11-12 | 2003-05-14 | $7700.00 | Window Closed / Lapsed |