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US5015658A Expired / Lapsed US ⏱️ 0.0 years remaining

Thiochroman esters of phenols and terephthallates having retinoid-like activity

Assignee: Allergan Inc
•
Filing: 1989-06-15
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Granted: 1991-05-14
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Expires: 2009-06-15
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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 06:47
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

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