KR880011138A - 레티노이드와 같은 작용성을 가지며 페닐그룹과 이종이환식 그룹으로 치환된 아세틸렌 - Google Patents

레티노이드와 같은 작용성을 가지며 페닐그룹과 이종이환식 그룹으로 치환된 아세틸렌 Download PDF

Info

Publication number
KR880011138A
KR880011138A KR1019880003216A KR880003216A KR880011138A KR 880011138 A KR880011138 A KR 880011138A KR 1019880003216 A KR1019880003216 A KR 1019880003216A KR 880003216 A KR880003216 A KR 880003216A KR 880011138 A KR880011138 A KR 880011138A
Authority
KR
South Korea
Prior art keywords
carbon atoms
lower alkyl
compound
saturated aliphatic
cyclic
Prior art date
Application number
KR1019880003216A
Other languages
English (en)
Other versions
KR960016543B1 (ko
Inventor
에이.에스.챤드 라라트라 로산타
Original Assignee
제임스 엠.케나지
알러겐, 인크.
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 제임스 엠.케나지, 알러겐, 인크. filed Critical 제임스 엠.케나지
Publication of KR880011138A publication Critical patent/KR880011138A/ko
Application granted granted Critical
Publication of KR960016543B1 publication Critical patent/KR960016543B1/ko

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
    • C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D215/14—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pain & Pain Management (AREA)
  • Immunology (AREA)
  • Rheumatology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Dermatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Pyrane Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Quinoline Compounds (AREA)
  • Peptides Or Proteins (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

내용 없음

Description

레티노이드와 같은 작용성을 가지며 페닐그룹과 이종이환식 그룹으로 치환된 아세틸렌
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (18)

  1. X가 S,O 또는 R1가 수소 또는 저급알킬인 NR1이며 ; R이 수소이거나 저급알킬이며 ; n이 0-5이고 ; A는 H이거나 A가 -COOH, 이것의 제약학적으로 허용되는 염, 탄소원자수가 10개 또는 그 이하의 포화된 지방족 알코올이거나 5 내지 10개 탄소원자수의 환식 또는 포화된 지방족 환식 알코올의 또는 페놀의 에스테르 또는 탄소수가 10개 또는 그 이하의 포화된 지방족 알코올의 아미드나 일-또는 이-치환된 아미드, 또는 이것의 5 내지 10개 탄소원자수의 환식 또는 포화된 지방족 환식기, 또는 A가 -CH2OH 이거나 탄소원자수가 10개 도는 그 이하의 포화된 지방족산의 저급알킬 에테르나 에스테르 또는 5 내지 10개 탄소원자수의 환식 또는 포화된 지방족 환식산이나 벤조산의 저급알킬 에테르나 에스테르, 또는 A가 -CHO 이거나 이것의 저급알킬 아세탈 유도체, 또는 m이 0-4 이고 R1이 -(CH2)mCH3인 -COR1이거나 이것으리 저급 알킬케탈 유도체인 다음 일반식의 화합물 또는 제학적으로 허용되는 이것의 염.
  2. X가 S이며, n이 0,1 또는 2인 제1항의 화합물.
  3. A가 -COOH, 또는 제약학적으로 허용되는 이것의 염, 에스테르 또는 아미드인 제2항의 화합물.
  4. 4-[4,5-디메틸티오크로만-6-일에티닐]벤조산 또는 제약학적으로 허용되는 이것의 염 또는 에틸 4-[4,4-디메틸티오크로만-6-일에티닐]벤조에이트인 제3항의 화합물.
  5. A가 수소인 제2항의 화합물.
  6. A가 -CH2OH 또는 이것의 에테르나 에스테르 유도체인 제2항의 화합물.
  7. A가 -CHO 또는 이것의 아세탈 유도체인 제2항의 화합물.
  8. A가 R가 -(CH2)mCH3이며 m이 0-4인 -COR2이거나 이것의 케탈유도체인 제2항의 화합물.
  9. X가 0,n이 0,1 또는 2인 제1항의 화합물.
  10. A가 -COOH, 또는 제약학적으로 허용되는 이것의 염, 에스테르 또는 아미드인 제9항의 화합물.
  11. 에틸 4-[4,4-디메틸크로만-6-일에티닐]벤조에이트 또는 4-[4,4-디메틸크로만-6-일에티닐]벤조산 또는 제약학적으로 허용되는 이것의 염, 에스테르 또는 아미드인 제10항의 화합물.
  12. A가 수소인 제9항의 화합물.
  13. A가 -CH2OH 또는 이것의 에테르 혹은 에스테르 유도체인 제9항의 화합물.
  14. A가 -CHO 또는 이것의 아세탈 유도체인 제9항의 화합물.
  15. A가 R2가 -(CH2)mCH3이며 m이 0-4인 -COR2이거나 이것의 케탈 유도체인 제9항의 화합물.
  16. X가 S,O 또는 R1가 수소 또는 저급알킬인 NR1이며 ; R이 수소이거나 저급알킬이며 ; n이 0-5이고 ; A는 H이거나 A가 -COOH, 이것의 제약학적으로 허용되는 염, 탄소원자수가 10개 또는 그 이하의 포화된 지방족 알코올이나 5 내지 10개 탄소원자수의 환식 또는 포화된 지방족 환식 알코올의 또는 페놀의 에스테르 또는 탄소수가 10개 또는 그 이하의 포화된 지방족 알코올의 아미드나 일-또는 이-치환된 아미드, 또는 이것의 5 내지 10개 탄소원자수의 환식 또는 포화된 지방족 환식기, 또는 A가 -CH2OH 이거나 탄소원자수가 10개 또는 그 이하의 포화된 지방족산의 저급알킬 에테르나 에스테르 또는 5 내지 10개 탄소원자수의 환식 또는 포화된 지방족 환식산이나 벤조산의 저급알킬 에테르나 에스테르, 또는 A가 -CHO 이거나 이것의 저급알킬 아세탈 유도체, 또는 m이 0-4 이고 R1이 -(CH2)mCH3인 -COR1이거나 이것의 저급 알킬케탈 유도체인 다음 일반식의 화합물 또는 제학적으로 허용되는 이것의 염과 제약학적으로 허용되는 이것의 염과 제약학적으로 허용되는 부형제로 이루오지는 제약학적 조성물.
  17. 포유동물에서 황건선 작용을 갖는 제16항에 따른 조성물.
  18. X가 S,O 이거나 R1가 수소 또는 저급알킬인 NR1이며 ; R이 수소이거나 저급알킬이며 ; n이 0-5이고 ; A는 H이거나 A가 -COOH, 이것의 제약학적으로 허용되는 염, 탄소원자수가 10개 또는 그 이하의 포화된 지방족 알코올이나 5 내지 10개 탄소원자수의 환식 또는 포화된 지방족 환식 알코올의 또는 페놀의 에스테르 또는 탄소수가 10개 또는 그 이하의 포화된 지방족 알코올의 아미드나 일-또는 이-치환된 아미드, 또는 이것의 5 내지 10개 탄소원자수의 환식 또는 포화된 지방족 환식기, 또는 A가 -CH2OH 이거나 탄소원자수가 10개 또는 그 이하의 포화된 지방족산의 저급알킬 에테르나 에스테르 또는 5 내지 10개 탄소원자수의 환식 또는 포화된 지방족 환식산이나 벤조산의 저급알킬 에테르나 에스테르, 또는 A가 -CHO 이거나 이것의 저급알킬 아세탈 유도체, 또는 m이 0-4 이고 R1이 -(CH2)mCH3인 -COR1이거나 이것의 저급 알킬케탈 유도체인 다음 일반식의 화합물 또는 제학적으로 허용되는 이것의 염과 제약학적으로 허용되는 이것의 염과 제약학적으로 허용되는 부형제를 함께 또는 단독으로 투여하는 것으로 이루어지는, 포유동물에서 건선을 치료하는 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019880003216A 1987-03-26 1988-03-25 레티노이드-유사활성을 가지며 페닐그룹과 헤테로이환식 그룹으로 이치환된 아세틸렌 KR960016543B1 (ko)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US031,476 1987-03-26
US07/031,476 US4810804A (en) 1987-03-26 1987-03-26 Acetylenes disubstituted with a phenyl group and a heterobicyclic group having retinoid-like activity

Publications (2)

Publication Number Publication Date
KR880011138A true KR880011138A (ko) 1988-10-26
KR960016543B1 KR960016543B1 (ko) 1996-12-14

Family

ID=21859663

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019880003216A KR960016543B1 (ko) 1987-03-26 1988-03-25 레티노이드-유사활성을 가지며 페닐그룹과 헤테로이환식 그룹으로 이치환된 아세틸렌

Country Status (22)

Country Link
US (1) US4810804A (ko)
EP (1) EP0290130B1 (ko)
JP (1) JP2820690B2 (ko)
KR (1) KR960016543B1 (ko)
CN (1) CN1032204C (ko)
AT (1) ATE69224T1 (ko)
AU (1) AU613608B2 (ko)
CA (1) CA1314891C (ko)
DE (1) DE3866010D1 (ko)
DK (1) DK156588A (ko)
ES (1) ES2038752T3 (ko)
FI (1) FI92485C (ko)
GR (1) GR3003556T3 (ko)
HU (1) HU201041B (ko)
IE (1) IE62775B1 (ko)
IL (1) IL85795A (ko)
MY (1) MY103250A (ko)
NO (1) NO171636C (ko)
NZ (1) NZ224009A (ko)
PH (1) PH27108A (ko)
PT (1) PT86976B (ko)
ZA (1) ZA881516B (ko)

Families Citing this family (94)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5149705A (en) * 1987-03-13 1992-09-22 Allergan, Inc. Acetylenes disubstituted with a heteroaromatic group and a tetralin group and having retinoid like activity
US5602130A (en) * 1987-03-20 1997-02-11 Allergan Disubstituted acetylenes bearing heteroaromatic and heterobicyclic groups having retinoid like activity
US5089509A (en) * 1988-09-15 1992-02-18 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
US5234926A (en) * 1987-03-20 1993-08-10 Allergan, Inc. Disubstituted acetylenes bearing heteroaromatic and heterobicyclic groups having retinoid like activity
US5231113A (en) * 1988-04-11 1993-07-27 Allergan, Inc. Tetralin esters of phenols or benzoic acids having retinoid like activity
KR0139216B1 (ko) * 1988-04-11 1998-05-01 제임스 엠. 캐내지 레티노이드 유사활성을 갖는 페놀 또는 벤조산의 테트랄린 에스테르
US4895868A (en) * 1988-06-29 1990-01-23 Allergan, Inc. Thiochroman esters of phenols and terephthallates having retinoid-like activity
US5068252A (en) * 1989-07-26 1991-11-26 Allergan, Inc. Methods of using phenylethenyl compounds having retinoid-like activity
US4992468A (en) * 1989-07-26 1991-02-12 Allergan, Inc. Phenylethenyl compounds having retinoid-like activity
DE3926148A1 (de) * 1989-08-08 1991-02-28 Basf Ag Diarylacetylene, ihre herstellung und verwendung
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
US5053523A (en) * 1989-09-19 1991-10-01 Allergan, Inc. Ethynyl-chroman compounds
US5023341A (en) * 1989-09-19 1991-06-11 Allergan, Inc. Compounds having a disubstituted acetylene moiety and retinoic acid-like biological activity
US4980369A (en) * 1989-09-19 1990-12-25 Allergan, Inc. Acetylenes disubstituted with a phenyl group and a 2-substituted chromanyl or thiochromanyl group having retinoid-like activity
US5162546A (en) * 1989-09-19 1992-11-10 Allergan, Inc. Acetylenes disubstituted with a phenyl group and a 2-substituted chromanyl, thiochromanyl or 1,2,3,4-tetrahydroquinolinyl group 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
US5248777A (en) * 1989-09-19 1993-09-28 Allergan, Inc. Process and intermediates for preparing compounds having a disubstituted acetylene moiety and retinoic acid-like biological activity
US4946860A (en) * 1989-11-03 1990-08-07 Rorer Pharmaceutical Corporation Benzothiopyranyl derivatives as HMG-CoA reductase inhibitors
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
US5175185A (en) * 1989-12-29 1992-12-29 Allergan, Inc. Acetylenes disubstituted with a heteroaromatic group and a substituted phenyl group 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
HUT63405A (en) * 1990-10-09 1993-08-30 Allergan Inc Process for producing acetylene derivatives substituted with chromanyl, thiochromanyl or tetrahydroquinolinyl group and having retinoid-like activity, as well as pharmaceutical compositions comprising same as active ingredient
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
US5134159A (en) * 1991-03-26 1992-07-28 Allergan, Inc. 7-chromanyl esters of phenols and benzoic acids having retinoid-like activity
WO1992017471A1 (en) * 1991-03-26 1992-10-15 Allergan, Inc. Chromans and thiochromans with heteroarylethynyl substituents at the 7-position having retinoid-like biological activity
US5326898A (en) * 1992-02-11 1994-07-05 Allergan, Inc. Substituted phenylethenyl compounds having retinoid-like biological activity
WO1993016067A1 (en) * 1992-02-11 1993-08-19 Allergan, Inc. Heteroaryl substituted phenylethenyl compounds having retinoid-like biological activity
CA2093577C (en) * 1992-05-07 2006-01-03 Michael Klaus Alkyl or alkoxy substituted s-heterocyclic retinoids
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
US6172115B1 (en) 1993-02-11 2001-01-09 Allergan Sales, Inc. Method for preventing onset of restenosis after angioplasty employing an RXR-specific retinoid
US5455265A (en) 1993-02-11 1995-10-03 Allergan, Inc. Method of treatment with compounds having selective agonist-like activity on RXR retinoid receptors
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
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
US5420295A (en) * 1994-01-19 1995-05-30 Allergan, Inc. Process for preparing 4,4-dialkyl-6-halo-chromans or thiochromans useful as pharmaceutical intermediates
ZA954599B (en) * 1994-06-07 1996-01-26 Allergan Inc Stable gel formulation for topical treatment of skin conditions
US5498755A (en) * 1994-08-23 1996-03-12 Chandraratna; Roshantha A. Disubstituted aryl and heteroaryl imines 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
US5534641A (en) * 1994-12-29 1996-07-09 Allergan Acetylenes disubstituted with 2-tetrahydropyranoxyaryl and aryl or heteroaryl groups 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
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
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
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
US5648514A (en) * 1994-12-29 1997-07-15 Allergan Substituted acetylenes having retinoid-like biological activity
AU698527B2 (en) * 1994-12-29 1998-10-29 Allergan, Inc. Acetylenes disubstituted with a 5 or 8 substituted tetrahydronaphthyl or dihydronaphthyl group and with an aryl or heteroaryl groups 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
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
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
US5675033A (en) * 1995-06-06 1997-10-07 Allergan 2,4-pentadienoic acid derivatives 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
US6942980B1 (en) 1995-09-01 2005-09-13 Allergan, 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
US5958954A (en) * 1995-09-01 1999-09-28 Allergan Sales, Inc. Synthesis and use of retinoid compounds having 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
US5952345A (en) * 1995-09-01 1999-09-14 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
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
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
US20030219832A1 (en) * 1996-03-11 2003-11-27 Klein Elliott S. Synthesis and use of retinoid compounds having negative hormone and/or antagonist activities
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
US5723666A (en) * 1996-06-21 1998-03-03 Allergan Oxime substituted tetrahydronaphthalene derivatives 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
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
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
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
CA2350599A1 (en) * 1998-11-20 2000-06-02 Genentech, Inc. Method of inhibiting angiogenesis
US6903121B1 (en) 2000-08-17 2005-06-07 Allergan, Inc. Treatment of tumors with acetylenes disubstituted with a phenyl or heteroaromatic group and a substituted chromanyl, thiochromanyl or tetrahydroquinolinyl group in combination with other anti-tumor agents
US6313107B1 (en) * 2000-08-29 2001-11-06 Allergan Sales, Inc. Methods of providing and using compounds having activity as inhibitors of cytochrome P450RAI
US6683092B1 (en) 2003-04-09 2004-01-27 Allergan, Inc. [3-(c5-14alkyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-3-oxo-propenyl]-phenyl and [3-(c5-14alkyl-2-oxo-1,2,3,4- tetrahydro-quinolin-6-yl)-3-oxo-propenyl]-heteroaryl derivatives having anti-tumor activity
JP2007525188A (ja) 2003-05-16 2007-09-06 インターミューン インコーポレイテッド 合成ケモカイン受容体リガンドおよびその使用方法
US6734193B1 (en) 2003-06-03 2004-05-11 Allergan, Inc. (1,2,3,4-tetrahydroquinolin-8-yl)-heptatrienoic acid derivatives having serum glucose reducing activity
US6963002B2 (en) 2003-07-04 2005-11-08 Glenmark Pharmaceuticals Limited Process for the preparation of 4,4-dimethyl-6-ethynylthiochroman
WO2005003125A1 (en) * 2003-07-04 2005-01-13 Glenmark Pharmaceuticals Limited Process for the preparation of 4,4-dimethyl-6-ethynylthiochroman
WO2005040758A2 (en) * 2003-10-24 2005-05-06 Intermune, Inc. Use of pirfenidone in therapeutic regimens
WO2005123713A1 (en) * 2004-06-17 2005-12-29 Glenmark Pharmaceuticals Limited Process for the preparation of disubstituted acetylenes bearing heteroaromatic and heterobicyclic groups
JP2008513356A (ja) * 2004-08-09 2008-05-01 アリオス バイオファーマ インク． 合成高度糖鎖付加プロテアーゼ耐性ポリペプチド変異体、それを使用する経口製剤および方法
US7597884B2 (en) * 2004-08-09 2009-10-06 Alios Biopharma, Inc. Hyperglycosylated polypeptide variants and methods of use
US20100081904A1 (en) * 2008-09-30 2010-04-01 Nellcor Puritan Bennett Llc Device And Method For Securing A Medical Sensor to An Infant's Head
PL3204357T3 (pl) * 2014-10-10 2022-04-25 High Force Research Limited Fluorescencyjne retinoidy syntetyczne
CN107176945B (zh) * 2016-03-11 2021-06-08 中国科学院上海有机化学研究所 一种视黄酸类化合物、其制备方法、中间体及应用

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH651034A5 (de) * 1982-05-12 1985-08-30 Hoffmann La Roche Chroman-, thiochroman- oder 1,2,3,4-tetrahydrochinolinderivate und ihre verwendung als arzneimittel-wirkstoffe.
DE3475305D1 (en) * 1983-07-05 1988-12-29 Pfizer Carboxylic acid derivatives useful for inhibiting the degradation of cartilage
DE3434946A1 (de) * 1984-09-22 1986-04-03 Basf Ag, 6700 Ludwigshafen Diarylacetylene, ihre herstellung und verwendung
DE3434942A1 (de) * 1984-09-22 1986-04-03 Basf Ag, 6700 Ludwigshafen Tetralin-derivate, ihre herstellung und verwendung

Also Published As

Publication number Publication date
MY103250A (en) 1993-05-29
GR3003556T3 (ko) 1993-03-16
HU201041B (en) 1990-09-28
DE3866010D1 (de) 1991-12-12
IE880907L (en) 1988-09-26
AU1373288A (en) 1988-09-29
JP2820690B2 (ja) 1998-11-05
JPS63264578A (ja) 1988-11-01
EP0290130A1 (en) 1988-11-09
IE62775B1 (en) 1995-02-22
NO171636B (no) 1993-01-04
FI881446A0 (fi) 1988-03-25
PT86976B (pt) 1992-06-30
IL85795A0 (en) 1988-09-30
DK156588D0 (da) 1988-03-22
FI92485C (fi) 1994-11-25
IL85795A (en) 1992-08-18
FI881446A (fi) 1988-09-27
KR960016543B1 (ko) 1996-12-14
AU613608B2 (en) 1991-08-08
PH27108A (en) 1993-03-16
EP0290130B1 (en) 1991-11-06
PT86976A (pt) 1988-04-01
FI92485B (fi) 1994-08-15
NZ224009A (en) 1990-04-26
HUT50153A (en) 1989-12-28
CN1031230A (zh) 1989-02-22
ES2038752T3 (es) 1993-08-01
CA1314891C (en) 1993-03-23
ATE69224T1 (de) 1991-11-15
NO881326D0 (no) 1988-03-25
DK156588A (da) 1988-09-27
US4810804A (en) 1989-03-07
ZA881516B (en) 1989-01-25
CN1032204C (zh) 1996-07-03
NO171636C (no) 1993-04-14
NO881326L (no) 1988-09-27

Similar Documents

Publication Publication Date Title
KR880011138A (ko) 레티노이드와 같은 작용성을 가지며 페닐그룹과 이종이환식 그룹으로 치환된 아세틸렌
KR880011068A (ko) 이종방향족 그룹과 테트랄린 그룹으로서 이중 치환되고 레티노이드와 같은 작용성을 갖는 아세틸렌
KR880011148A (ko) 레티노이드와 같은 작용성을 가지며 이종방향족 그룹과 이종이환식 그룹을 갖는 치환된 아세틸렌
KR880003893A (ko) 에티닐페닐을 함유하고 있는 레티오익산 유도체들
KR880007411A (ko) 레티논산과 같은 작용을 갖는 에티닐헤테로 방향족-산류
KR830006174A (ko) 기관지 항경련성 화합물 제조방법
DK564181A (da) Carbacykliner fremgangsmaade til fremstilling heraf og anvendelse heraf som laegemiddel
FR2405245A1 (fr) Insecticides et acaricides a base de carboxylates de benzyl-pyrrolyl-methyle
KR950000663A (ko) 트리테르펜 유도체 및 이를 함유하는 엔도텔린-수용체 길항물질
SE7710367L (sv) Azabicyklohexaner, dess anvendningssett och framstellning
IE32334L (en) Glyceryl esters
ES461598A1 (es) Procedimiento para la preparacion de n-cicloalcohilmetil-2- fenilamino-imidazolinas-(2).
JPS55145650A (en) Intermediate and its preparation
CA1093578A (en) Process for the preparation of p.isobutyl hydratropate of guaiacol
JPS6462377A (en) Fluorinated dibenzylidene polyhydric alcohol derivative, nonaqueous gelatinizing agent containing said derivative and cosmetic using said derivative
ES8105254A1 (es) Un procedimiento para la preparacion de acido 2-(4-dimetil- vinilfenil) propionico
GB1498394A (en) Behenic acid esters of 9-thiaxanthene propylidene heterocyclic alcohols and their use in pharmaceutical composition
ES399873A1 (es) Procedimiento para la preparacion de nuevos i-fenoxi-2- idroxi-3-alcahilamino propanos recemicos u opticamenacti- vos.
KR840005713A (ko) [3.2.0]비시클로헵탄온 옥심 에테르류의 제조방법
KR910016313A (ko) 멜라닌 생성억제 외용제
ES390720A1 (es) Procedimiento de preparacion de nuevos derivados de la ci- clopentanona.
SE7706481L (sv) Farmaceutiskt preparat innehallande subsituerad fenyl-amino-alkohol, och forfaringssett for framstellning av dylikt preparat
DK227289D0 (da) Makrolidforbindelser
KR910011740A (ko) 알파-알콕시 아세트산 및 그의염의 제조방법
KR910000641A (ko) 도파민 효능제 비스 (벤질피롤리딘) 유도체

Legal Events

Date Code Title Description
A201 Request for examination
E902 Notification of reason for refusal
G160 Decision to publish patent application
E701 Decision to grant or registration of patent right
GRNT Written decision to grant
FPAY Annual fee payment

Payment date: 20041206

Year of fee payment: 9

LAPS Lapse due to unpaid annual fee