WO2000068190A3 - 1-alkoxy and 1-acyloxy substituted cyclohex-1-ene compounds and sulfur and 1-alkoxycarbonyl analogs having retinoid-like biological activity - Google Patents

1-alkoxy and 1-acyloxy substituted cyclohex-1-ene compounds and sulfur and 1-alkoxycarbonyl analogs having retinoid-like biological activity Download PDF

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Publication number
WO2000068190A3
WO2000068190A3 PCT/US2000/011975 US0011975W WO0068190A3 WO 2000068190 A3 WO2000068190 A3 WO 2000068190A3 US 0011975 W US0011975 W US 0011975W WO 0068190 A3 WO0068190 A3 WO 0068190A3
Authority
WO
WIPO (PCT)
Prior art keywords
retinoid
biological activity
alkoxycarbonyl
analogs
alkoxy
Prior art date
Application number
PCT/US2000/011975
Other languages
French (fr)
Other versions
WO2000068190A2 (en
Inventor
Richard L Beard
Diana F Colon
Roshantha A Chandraratna
Original Assignee
Allergan Sales 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 Sales Inc filed Critical Allergan Sales Inc
Priority to AU48156/00A priority Critical patent/AU4815600A/en
Publication of WO2000068190A2 publication Critical patent/WO2000068190A2/en
Publication of WO2000068190A3 publication Critical patent/WO2000068190A3/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
    • C07C403/02—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains containing only carbon and hydrogen atoms
    • 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
    • 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
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Dermatology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Compounds of Formula (1) and Formula (2) where the symbols have the meaning defined in the specification, have retinoid, retinoid antagonist or retinoid negative hormone like biological activity.
PCT/US2000/011975 1999-05-07 2000-05-03 1-alkoxy and 1-acyloxy substituted cyclohex-1-ene compounds and sulfur and 1-alkoxycarbonyl analogs having retinoid-like biological activity WO2000068190A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU48156/00A AU4815600A (en) 1999-05-07 2000-05-03 1-alkoxy and 1-acyloxy substituted cyclohex-1-ene compounds and sulfur and 1-alkoxycarbonyl analogs having retinoid-like biological activity

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US09/307,073 1999-05-07
US09/307,073 US6177588B1 (en) 1999-05-07 1999-05-07 1-alkoxy and 1-acyloxy substituted cyclohex-1-ene compounds and sulfur and 1-alkoxycarbonyl analogs having retinoid-like biological activity

Publications (2)

Publication Number Publication Date
WO2000068190A2 WO2000068190A2 (en) 2000-11-16
WO2000068190A3 true WO2000068190A3 (en) 2001-01-18

Family

ID=23188130

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2000/011975 WO2000068190A2 (en) 1999-05-07 2000-05-03 1-alkoxy and 1-acyloxy substituted cyclohex-1-ene compounds and sulfur and 1-alkoxycarbonyl analogs having retinoid-like biological activity

Country Status (3)

Country Link
US (2) US6177588B1 (en)
AU (1) AU4815600A (en)
WO (1) WO2000068190A2 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2001290816A1 (en) 2000-09-13 2002-03-26 Bristol-Myers Squibb Company Retinoic acid receptor antagonists as promoters of angiogenesis
US10265585B2 (en) 2010-12-03 2019-04-23 Sumitomo Rubber Industries, Ltd. Golf ball

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0265069A1 (en) * 1986-09-22 1988-04-27 Allergan, Inc Ethynylphenyl-containing retinoic acid derivatives
EP0272921A1 (en) * 1986-12-24 1988-06-29 Allergan, Inc Ethynylheteroaromatic acids having retinoic acid-like activity
US5760276A (en) * 1997-03-06 1998-06-02 Allergan Aryl-and heteroarylcyclohexenyl substituted alkenes having retinoid agonist, antagonist or inverse agonist type biological activity

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0047817A3 (en) 1980-08-14 1982-05-26 F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft Hydrogenated naphthalines, their preparation and application, and mixtures containing such naphthalines
US4539154A (en) 1983-06-15 1985-09-03 Hoffmann-La Roche Inc. Polyene compounds
US4927947A (en) 1986-12-24 1990-05-22 Allergan, Inc. Ethynylheteroaromatic-acids having retinoic acid-like activity
US4923884A (en) 1986-12-24 1990-05-08 Allergan, Inc. Ethynylheteroaromatic-acids having retinoic acid-like activity
DE617614T1 (en) 1991-12-18 1995-06-08 Salk Inst For Biological Studi MEANS FOR MODULATING PROCESSES BY RETINOID RECEPTORS AND USEFUL CONNECTIONS THEREFOR.
US5455265A (en) 1993-02-11 1995-10-03 Allergan, Inc. Method of treatment with compounds having selective agonist-like activity on RXR retinoid receptors
US5451605A (en) 1993-12-30 1995-09-19 Allergan, Inc. 1,2-epoxycyclohexanyl and bicyclic aromatic substituted ethyne 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
US5877207A (en) 1996-03-11 1999-03-02 Allergan Sales, Inc. Synthesis and use of retinoid compounds having negative hormone and/or antagonist activities

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0265069A1 (en) * 1986-09-22 1988-04-27 Allergan, Inc Ethynylphenyl-containing retinoic acid derivatives
EP0272921A1 (en) * 1986-12-24 1988-06-29 Allergan, Inc Ethynylheteroaromatic acids having retinoic acid-like activity
US5760276A (en) * 1997-03-06 1998-06-02 Allergan Aryl-and heteroarylcyclohexenyl substituted alkenes having retinoid agonist, antagonist or inverse agonist type biological activity

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
KOELLING, ELISABETH ET AL: "Regulation of the 6-S-equilibrium conformation of retinal in bacteriorhodopsins by substitution at C-5; 5-methoxy- and 5-ethylretinalbacteriorhodopsin", ANGEWANDTE CHEMIE. INTERNATIONAL EDITION., vol. 26, no. 6, 1987, VERLAG CHEMIE. WEINHEIM., DE, pages 580 - 583, XP002149573, ISSN: 0570-0833 *
VOGEL, CLAUS ET AL: "Cycloalkano-2H-pyrrole as a stable intermediate in the conversion of beta-cycloalkenyl-alpha-azidoacrylates to cycloalkano-1H-pyrroles", ANGEW. CHEM., INT. ED. ENGL., 1993, 32(7), 1051-2), XP002149574 *

Also Published As

Publication number Publication date
US6465646B1 (en) 2002-10-15
US6177588B1 (en) 2001-01-23
AU4815600A (en) 2000-11-21
WO2000068190A2 (en) 2000-11-16

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