DE68905215T2 - Tetralinester von phenolen oder benzoesaeuren mit retinoidaehnlicher aktivitaet. - Google Patents

Tetralinester von phenolen oder benzoesaeuren mit retinoidaehnlicher aktivitaet.

Info

Publication number
DE68905215T2
DE68905215T2 DE8989303490T DE68905215T DE68905215T2 DE 68905215 T2 DE68905215 T2 DE 68905215T2 DE 8989303490 T DE8989303490 T DE 8989303490T DE 68905215 T DE68905215 T DE 68905215T DE 68905215 T2 DE68905215 T2 DE 68905215T2
Authority
DE
Germany
Prior art keywords
lower alkyl
retinoid
activity
hydrogen
tetralinester
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
DE8989303490T
Other languages
English (en)
Other versions
DE68905215D1 (de
Inventor
Roshantha A S Chandraratna
Robert J Weinkam
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Allergan Inc
Original Assignee
Allergan Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Allergan Inc filed Critical Allergan Inc
Application granted granted Critical
Publication of DE68905215D1 publication Critical patent/DE68905215D1/de
Publication of DE68905215T2 publication Critical patent/DE68905215T2/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
    • C07C69/86—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with esterified hydroxyl groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/46—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/12—Acetic acid esters
    • C07C69/14—Acetic acid esters of monohydroxylic compounds
    • C07C69/145—Acetic acid esters of monohydroxylic compounds of unsaturated alcohols
    • C07C69/157—Acetic acid esters of monohydroxylic compounds of unsaturated alcohols containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/80—Phthalic acid esters
    • C07C69/82—Terephthalic acid esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
DE8989303490T 1988-04-11 1989-04-10 Tetralinester von phenolen oder benzoesaeuren mit retinoidaehnlicher aktivitaet. Expired - Lifetime DE68905215T2 (de)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US17970088A 1988-04-11 1988-04-11

Publications (2)

Publication Number Publication Date
DE68905215D1 DE68905215D1 (de) 1993-04-15
DE68905215T2 true DE68905215T2 (de) 1993-08-19

Family

ID=22657612

Family Applications (1)

Application Number Title Priority Date Filing Date
DE8989303490T Expired - Lifetime DE68905215T2 (de) 1988-04-11 1989-04-10 Tetralinester von phenolen oder benzoesaeuren mit retinoidaehnlicher aktivitaet.

Country Status (18)

Country Link
US (1) US5130335A (de)
EP (1) EP0337689B1 (de)
JP (1) JPH0794407B2 (de)
KR (1) KR0139216B1 (de)
CN (1) CN1027065C (de)
AT (1) ATE86601T1 (de)
AU (1) AU618590B2 (de)
CA (1) CA1330567C (de)
DE (1) DE68905215T2 (de)
DK (1) DK171689A (de)
ES (1) ES2053982T3 (de)
HU (1) HU201727B (de)
IE (1) IE63712B1 (de)
NO (1) NO170008C (de)
NZ (1) NZ228682A (de)
PT (1) PT90251B (de)
SG (1) SG32564G (de)
ZA (1) ZA892583B (de)

Families Citing this family (80)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5602130A (en) * 1987-03-20 1997-02-11 Allergan Disubstituted acetylenes bearing heteroaromatic and heterobicyclic groups having retinoid like activity
US5234926A (en) * 1987-03-20 1993-08-10 Allergan, Inc. Disubstituted acetylenes bearing heteroaromatic and heterobicyclic groups having retinoid like activity
US5264578A (en) * 1987-03-20 1993-11-23 Allergan, Inc. Disubstituted acetylenes bearing heterobicyclic groups and heteroaromatic or phenyl groups having retinoid like activity
US5183827A (en) * 1989-09-19 1993-02-02 Allergan, Inc. Acetylenes disubstituted with a heteroaromatic group and a 2-substituted chromanyl, thiochromanyl or 1,2,3,4-tetrahydroquinolinyl group having retinoid-like activity
US5399561A (en) * 1989-09-19 1995-03-21 Allergan, Inc. Acetylenes disubstituted with a phenyl or heteroaryl group and a 2-oxochromanyl, 2-oxothiochromanyl or 2-oxo-1,2,3,4-tetrahydro-quinolinyl group having retinoid-like biological activity
US5272156A (en) * 1989-09-19 1993-12-21 Allergan, Inc. Acetylenes disubstituted with a heteroaromatic group and a 2-substituted 1,2,3,4-tetrahydroquinolinyl group having retinoid-like activity
US5264456A (en) * 1989-12-29 1993-11-23 Allergan, Inc. Acetylenes disubstituted with a furyl group and a substituted phenyl group having retinoid like activity
US5006550A (en) * 1989-12-29 1991-04-09 Allergan, Inc. Chroman esters of phenols and benzoic acids having retinoid-like activity
US5202471A (en) * 1990-02-06 1993-04-13 Allergan, Inc. Alkyl, alkoxy and thioalkoxy substituted diphenyl acetylenes having retinoid like activity
JP3062248B2 (ja) * 1991-02-13 2000-07-10 アラーガン、インコーポレイテッド レチノイド様生物学的活性を有する７位にフェニルエチニル置換基を有するクロマンおよびチオクロマン
GB9104286D0 (en) * 1991-02-28 1991-04-17 Phytopharm Ltd Pharmaceutical compositions for the treatment of skin disorders
IE920949A1 (en) * 1991-03-26 1992-10-07 Allergan Inc Chromans and thiochromans with heteroarylethynyl¹substituents at the 7-position having retinoid-like¹biological activity
US5134159A (en) * 1991-03-26 1992-07-28 Allergan, Inc. 7-chromanyl esters of phenols and benzoic acids having retinoid-like activity
CA2129831A1 (en) * 1992-02-11 1993-08-19 Roshantha A. S. Chandraratna Heteroaryl substituted phenylethenyl compounds having retinoid-like biological activity
US5324840A (en) * 1992-06-11 1994-06-28 Allergan, Inc. Method of treatment with compounds having retinoid-like activity and reduced skin toxicity and lacking teratogenic effects
US5455265A (en) 1993-02-11 1995-10-03 Allergan, Inc. Method of treatment with compounds having selective agonist-like activity on RXR retinoid receptors
US6172115B1 (en) 1993-02-11 2001-01-09 Allergan Sales, Inc. Method for preventing onset of restenosis after angioplasty employing an RXR-specific retinoid
US5399586A (en) * 1993-03-11 1995-03-21 Allergan, Inc. Treatment of mammals afflicted with tumors with compounds having RXR retinoid receptor agonist activity
US5344959A (en) * 1993-05-18 1994-09-06 Allergan, Inc. Tetrahydronaphthyl and cyclopropyl substituted 1,3-butadienes having retinoid-like activity
US5475022A (en) * 1993-10-18 1995-12-12 Allergan, Inc. Phenyl or heteroaryl and tetrahydronaphthyl substituted diene compounds having retinoid like biological activity
US5470999A (en) * 1993-12-30 1995-11-28 Allergan, Inc. Cyclohexene and bicyclic aromatic substituted ethyne compounds having retinoid-like biological activity
US5426118A (en) * 1993-12-30 1995-06-20 Allergan, Inc. [4-(1,2-epoxycyclohexanyl)but-3-en-1-ynyl]aromatic and heteroaromatic acids and derivatives having retinoid-like biological activity
US5451605A (en) * 1993-12-30 1995-09-19 Allergan, Inc. 1,2-epoxycyclohexanyl and bicyclic aromatic substituted ethyne compounds having retinoid-like biological activity
CA2137997A1 (en) * 1994-01-03 1995-07-04 John E. Starrett, Jr. Retinoid-like compounds
US5648385A (en) * 1994-01-03 1997-07-15 Bristol-Myers Squibb Co. Retinoid-like compounds
US5498755A (en) * 1994-08-23 1996-03-12 Chandraratna; Roshantha A. Disubstituted aryl and heteroaryl imines having retinoid-like biological activity
US5489584A (en) * 1994-12-29 1996-02-06 Allergan, Inc. Acetylenes disubstituted with a 5-amino or substituted 5-amino substituted tetrahydronaphthyl group and with an aryl or heteroaryl group having retinoid-like biological activity
US5618943A (en) * 1994-12-29 1997-04-08 Allergan Acetylenes disubstituted with a 5 OXO substituted tetrahydronaphthyl group and with an aryl or heteroaryl group having retinoid-like biological activity
US5618931A (en) * 1994-12-29 1997-04-08 Allergan Acetylenes disubstituted with a 5 substituted dihydronaphthyl group and with an aryl or heteroaryl group having retinoid-like biological activity
US5648514A (en) 1994-12-29 1997-07-15 Allergan Substituted acetylenes having retinoid-like biological activity
US5514825A (en) * 1994-12-29 1996-05-07 Allergan, Inc. Acetylenes disubstituted with a 5 substituted tetrahydronaphthyl group and with an aryl or heteroaryl group having retinoid-like biological activity
US5543534A (en) * 1994-12-29 1996-08-06 Allergan Acetylenes disubstituted with a 5 substituted tetrahydronaphthyl group and with an aryl or heteroaryl groups having retinoid-like biological activity
US5599967A (en) * 1994-12-29 1997-02-04 Allergan Acetylenes disubstituted with a 5 substituted tetrahydronaphthyl group and with an aryl of heteroaryl group having retinoid-like biological activity
US5556996A (en) * 1994-12-29 1996-09-17 Allergan Oxiranyls disubstituted with a phenyl group and a substituted chromanyl or tetrahydroquinolinyl group having retinoid like activity
US5534641A (en) * 1994-12-29 1996-07-09 Allergan Acetylenes disubstituted with 2-tetrahydropyranoxyaryl and aryl or heteroaryl groups having retinoid-like biological activity
US5559248A (en) * 1995-04-05 1996-09-24 Bristol-Myers Squibb Co. Retinoid-like heterocycles
US6025388A (en) 1995-04-26 2000-02-15 Allergan Sales, Inc. Method for inhibiting gene expression promoted by AP1 protein with RARβ selective retinoids and method for treatment of diseases and conditions with such retinoids
US5616712A (en) * 1995-05-16 1997-04-01 Allergan Acetylenes disubstituted with a phenyl or heteroaryl group and a 2-thio-1,2,3,4-tetrahdroquinolinyl, 2-alkylthio-3,4-dihydroquinolinyl or 2-alkoxy-3,4-dihydroquinolinyl group having retinoid-like biological activity
US5917082A (en) * 1995-06-06 1999-06-29 Allergan Sales, Inc. 2,4-pentadienoic acid derivatives having retinoid-like biological activity
US5675033A (en) * 1995-06-06 1997-10-07 Allergan 2,4-pentadienoic acid derivatives having retinoid-like biological activity
US5958954A (en) * 1995-09-01 1999-09-28 Allergan Sales, Inc. Synthesis and use of retinoid compounds having negative hormone and/or antagonist activities
US5952345A (en) * 1995-09-01 1999-09-14 Allergan Sales, Inc. Synthesis and use of retinoid compounds having negative hormone and/or antagonist activities
US6942980B1 (en) 1995-09-01 2005-09-13 Allergan, Inc. Methods of identifying compounds having nuclear receptor negative hormone and/or antagonist activities
US6218128B1 (en) 1997-09-12 2001-04-17 Allergan Sales, Inc. Methods of identifying compounds having nuclear receptor negative hormone and/or antagonist activities
US6008204A (en) 1995-09-01 1999-12-28 Allergan Sales, Inc. Synthesis and use of retinoid compounds having negative hormone and/or antagonist activities
AU7598596A (en) * 1995-11-01 1997-05-22 Allergan, Inc. Sulfides, sulfoxides and sulfones disubstituted with a tetrahydronaphthalenyl, chromanyl, thiochromanyl or tetrahydroquinolinyl and substituted phenyl or heteroaryl group, having retinoid-like biological activity
US5663357A (en) 1995-11-22 1997-09-02 Allergan Substituted heteroarylamides having retinoid-like biological activity
US5675024A (en) * 1995-11-22 1997-10-07 Allergan Aryl or heteroaryl amides of tetrahydronaphthalene, chroman, thiochroman and 1,2,3,4,-tetrahydroquinoline carboxylic acids, having an electron withdrawing substituent in the aromatic or heteroaromatic moiety, having retinoid-like biological activity
US5965606A (en) 1995-12-29 1999-10-12 Allergan Sales, Inc. Methods of treatment with compounds having RAR.sub.α receptor specific or selective activity
US5688957A (en) * 1995-12-29 1997-11-18 Allergan (3"-thioxacyclohex-1"-enyl)!-but-3'-ene-1'-ynyl!aryl and (3"-thioxacyclohex-1"-enyl)!-but-3'-ene-1'-ynyl!heteroaryl carboxylic acids and esters having retinoid-like biological activity
US20030219832A1 (en) * 1996-03-11 2003-11-27 Klein Elliott S. Synthesis and use of retinoid compounds having negative hormone and/or antagonist activities
US5723666A (en) * 1996-06-21 1998-03-03 Allergan Oxime substituted tetrahydronaphthalene derivatives having retinoid and/or retinoid antagonist-like biological activity
US6555690B2 (en) 1996-06-21 2003-04-29 Allergan, Inc. Alkyl or aryl substituted dihydronaphthalene derivatives having retinoid and/or retinoid antagonist-like biological activity
US5808124A (en) * 1996-06-21 1998-09-15 Allergan O- or S-substituted dihydronaphthalene derivatives having retinoid and/or retinoid antagonist-like biological activity
US5747542A (en) * 1996-06-21 1998-05-05 Allergan Oxo-substituted tetrahydronaphthalene derivatives having retinold and/or retinoid antagonist-like biological activity
US5741896A (en) 1996-06-21 1998-04-21 Allergan O- or S- substituted tetrahydronaphthalene derivatives having retinoid and/or retinoid antagonist-like biological activity
US5763635A (en) * 1996-06-21 1998-06-09 Allergan Tetrahydronaphthalene derivatives substituted in the 8 position with alkyhidene groups having retinoid and/or retinoid antagonist-like biological activity
US5773594A (en) 1996-06-21 1998-06-30 Allergan Alkyl or aryl substituted dihydronaphthalene derivatives having retinoid and/or retinoid antagonist-like biological activity
US5739338A (en) * 1996-11-05 1998-04-14 Allergan N-aryl substituted tetrahydroquinolines having retinoid agonist, retinoid antagonist or retinoid inverse agonist type biological activity
US5728846A (en) 1996-12-12 1998-03-17 Allergan Benzo 1,2-g!-chrom-3-ene and benzo 1,2-g!-thiochrom-3-ene derivatives
US5760276A (en) * 1997-03-06 1998-06-02 Allergan Aryl-and heteroarylcyclohexenyl substituted alkenes having retinoid agonist, antagonist or inverse agonist type biological activity
US6037488A (en) 1997-04-19 2000-03-14 Allergan Sales, Inc. Trisubstituted phenyl derivatives having retinoid agonist, antagonist or inverse agonist type biological activity
US5919970A (en) 1997-04-24 1999-07-06 Allergan Sales, Inc. Substituted diaryl or diheteroaryl methanes, ethers and amines having retinoid agonist, antagonist or inverse agonist type biological activity
US6274608B1 (en) 1999-04-20 2001-08-14 Novo Nordisk A/S Compounds, their preparation and use
AU3958200A (en) * 1999-04-20 2000-11-02 Novo Nordisk A/S New compounds, their preparation and use
JO2178B1 (en) * 1999-10-19 2003-04-23 اف . هوفمان لاروش ايه جي Treatment of invasive diseases, using selected anti-PAR materials
US6252090B1 (en) 2000-08-29 2001-06-26 Allergan Sales, Inc. Compounds having activity as inhibitors of cytochrome P450RAI
US6380256B1 (en) 2000-08-29 2002-04-30 Allergan Sales, Inc. Compounds having activity as inhibitors of cytochrome P450RAI
US6313107B1 (en) 2000-08-29 2001-11-06 Allergan Sales, Inc. Methods of providing and using compounds having activity as inhibitors of cytochrome P450RAI
US6369225B1 (en) 2000-08-29 2002-04-09 Allergan Sales, Inc. Compounds having activity as inhibitors of cytochrome P450RAI
US7211267B2 (en) * 2001-04-05 2007-05-01 Collagenex Pharmaceuticals, Inc. Methods of treating acne
JP2005020400A (ja) 2003-06-26 2005-01-20 Hitachi Communication Technologies Ltd 無線基地局、無線通信システム、無線基地局の通信制御方法、および、無線通信網の構築方法
WO2004064743A2 (en) * 2003-01-17 2004-08-05 Wisconsin Alumni Research Foundation Modified retinoid compounds and their uses
EP2204168B1 (de) 2003-04-07 2015-01-14 Supernus Pharmaceuticals, Inc. Einmal täglich einzunehmende Tetrazyklinzubereitung
US9192615B2 (en) 2008-08-06 2015-11-24 Medicis Pharmaceutical Corporation Method for the treatment of acne and certain dosage forms thereof
US7544373B2 (en) 2007-04-02 2009-06-09 Medicis Pharmaceutical Corporation Minocycline oral dosage forms for the treatment of acne
US7541347B2 (en) 2007-04-02 2009-06-02 Medicis Pharmaceutical Coropration Minocycline oral dosage forms for the treatment of acne
CN101450912B (zh) * 2007-11-24 2012-05-30 山东轩竹医药科技有限公司 四氢化萘取代的苯甲酸衍生物
CA2809374C (en) 2010-09-01 2021-02-23 Thomas Jefferson University A composition comprising a retinoic acid receptor gamma agonist and its use for muscle repair and regeneration
CN106278883A (zh) * 2016-08-04 2017-01-04 暨南大学 一种尼泊金十四酯的催化合成方法

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4085091A (en) * 1976-12-16 1978-04-18 E. I. Dupont De Nemours And Company Thermally stable, rigid polyesters from thermally stable, rigid dibasic acids and aromatic dihydroxy compounds
DK159967C (da) * 1977-12-22 1991-06-03 Hoffmann La Roche Analogifremgangsmaade til fremstilling af terapeutisk aktive stilbenderivater
EP0047817A3 (de) * 1980-08-14 1982-05-26 F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft Hydrierte Naphthaline, deren Herstellung und Verwendung sowie derartige Naphthaline enthaltende Gemische
DE3202100A1 (de) * 1982-01-23 1983-08-04 Basf Ag, 6700 Ludwigshafen Substituierte benzoesaeure-4-hydroxyanilide, ihre herstellung und diese enthaltende pharmazeutische zubereitungen
FR2555571B1 (fr) * 1983-11-28 1986-11-28 Interna Rech Dermatolo Centre Derives du naphtalene, leur procede de preparation et leur application dans le domaine therapeutique
JPS60222445A (ja) * 1984-04-19 1985-11-07 Yoshitomi Pharmaceut Ind Ltd フタル酸化合物
EP0170105B1 (de) * 1984-07-07 1990-10-17 Koichi Prof. Dr. Shudo Benzoesäurederivate
LU85544A1 (fr) * 1984-09-19 1986-04-03 Cird Derives heterocycliques aromatiques,leur procede de preparation et leur application dans les domaines therapeutique et cosmetique
IL80270A0 (en) * 1985-10-11 1987-01-30 Cird Naphthalene derivatives,their preparation and pharmaceutical compositions containing them
DE3615157A1 (de) * 1986-05-05 1987-11-12 Schwabe Willmar Gmbh & Co 5-arylalkyl-4-alkoxy-2(5h)-furanone, zwischenprodukte und verfahren zu ihrer herstellung sowie ihre anwendung als therapeutische wirkstoffe
US4810804A (en) * 1987-03-26 1989-03-07 Allergan, Inc. Acetylenes disubstituted with a phenyl group and a heterobicyclic group having retinoid-like activity

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Publication number Publication date
AU3258589A (en) 1989-10-12
ZA892583B (en) 1989-12-27
SG32564G (en) 1995-09-01
DK171689A (da) 1989-10-12
IE63712B1 (en) 1995-05-31
NO170008B (no) 1992-05-25
IE891135L (en) 1989-10-11
PT90251B (pt) 1994-06-30
CN1027065C (zh) 1994-12-21
AU618590B2 (en) 1992-01-02
PT90251A (pt) 1989-11-10
HU201727B (en) 1990-12-28
CA1330567C (en) 1994-07-05
EP0337689B1 (de) 1993-03-10
KR0139216B1 (ko) 1998-05-01
JPH026437A (ja) 1990-01-10
CN1038092A (zh) 1989-12-20
NO891466L (no) 1989-10-12
ATE86601T1 (de) 1993-03-15
NZ228682A (en) 1991-07-26
DE68905215D1 (de) 1993-04-15
US5130335A (en) 1992-07-14
KR890015988A (ko) 1989-11-27
NO891466D0 (no) 1989-04-10
ES2053982T3 (es) 1994-08-01
JPH0794407B2 (ja) 1995-10-11
NO170008C (no) 1992-09-02
DK171689D0 (da) 1989-04-10
EP0337689A1 (de) 1989-10-18
HUT50100A (en) 1989-12-28

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