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WO1997019052B1 - Arylamides ou hetero-arylamides de tetrahydronaphtalene, de chromane, de thiochromane et d'acides carboxyliques 1,2,3,4-tetrahydroquinoliniques ayant une activite biologique de type retinoide - Google Patents

Arylamides ou hetero-arylamides de tetrahydronaphtalene, de chromane, de thiochromane et d'acides carboxyliques 1,2,3,4-tetrahydroquinoliniques ayant une activite biologique de type retinoide

Info

Publication number
WO1997019052B1
WO1997019052B1 PCT/US1996/018580 US9618580W WO9719052B1 WO 1997019052 B1 WO1997019052 B1 WO 1997019052B1 US 9618580 W US9618580 W US 9618580W WO 9719052 B1 WO9719052 B1 WO 9719052B1
Authority
WO
WIPO (PCT)
Prior art keywords
carbons
alkyl
compound
fluoro
carbamoyl
Prior art date
Application number
PCT/US1996/018580
Other languages
English (en)
Other versions
WO1997019052A1 (fr
Filing date
Publication date
Priority claimed from US08/562,000 external-priority patent/US5675024A/en
Priority to NZ323581A priority Critical patent/NZ323581A/xx
Priority to IL12459796A priority patent/IL124597A/en
Priority to HU9902536A priority patent/HUP9902536A3/hu
Priority to EP96941408A priority patent/EP0876330B1/fr
Priority to JP51985297A priority patent/JP4112003B2/ja
Priority to AU10560/97A priority patent/AU702499B2/en
Priority to KR1019980703816A priority patent/KR100483442B1/ko
Application filed filed Critical
Priority to AT96941408T priority patent/ATE200074T1/de
Priority to PL96327457A priority patent/PL186404B1/pl
Priority to DE69612303T priority patent/DE69612303T2/de
Priority to DK96941408T priority patent/DK0876330T3/da
Priority to BR9611758A priority patent/BR9611758A/pt
Priority to CA002238274A priority patent/CA2238274C/fr
Publication of WO1997019052A1 publication Critical patent/WO1997019052A1/fr
Publication of WO1997019052B1 publication Critical patent/WO1997019052B1/fr
Priority to GR20010400830T priority patent/GR3035979T3/el

Links

Abstract

Composés de formule (I) où X est S, O, NR', où R' est H ou alkyle avec 1 à 6 carbones, ou X est [C(R1)2]n où n est un entier compris entre 0 et 2; 1; Y est un groupe phényle ou naphtyle, ou un groupe hétéroaryle; W est un substituant choisi dans le groupe constitué de F, Br, Cl, I, C1-6 alkyle, C1-6 alkyle fluoro-substitué, NO2, N3, OH, OCH2OCH3, OC1-10 alkyle, tétrazole, CN, SO2C1-6-alkyle, SO2C1-6 alkyle fluoro-substitué, SO-C1-6 alkyle, CO-C1-6 alkyle, COOR8, phényle, le phényle étant substitué avec un groupe W autre que phényle ou phényle substitué; L est -(C=Z)-NH- or -HN-(C=Z)-; Z est O ou S; A est (CH2)q où q est 0-5, alkyle inférieur à chaîne ramifiée possédant 3-6 carbones, cycloalkyle possédant 3-6 carbones, alcényle possédant 2-6 carbones et 1 ou 2 doubles liaisons, alcynyle possédant 2-6 carbones et 1 ou 2 triples liaisons; et B est COOH ou un de ses sels pharmaceutiquement acceptables COOR8, CONR9R10, -CH2OH, CH2OR11, CH2OCOR11, CHO, CH(OR12)2, CHOR13O, -COR7, CR7(OR12)2, CR7OR13O, où R1 -R13 et o, p, m, n, r sont tels que définis dans la revendication 1. Ces composés ont une activité biologique de type rétinoïde.
PCT/US1996/018580 1995-11-22 1996-11-18 Arylamides ou hetero-arylamides de tetrahydronaphtalene, de chromane, de thiochromane et d'acides carboxyliques 1,2,3,4-tetrahydroquinoliniques ayant une activite biologique de type retinoide WO1997019052A1 (fr)

Priority Applications (14)

Application Number Priority Date Filing Date Title
CA002238274A CA2238274C (fr) 1995-11-22 1996-11-18 Arylamides ou hetero-arylamides de tetrahydronaphtalene, de chromane, de thiochromane et d'acides carboxyliques 1,2,3,4-tetrahydroquinoliniques ayant une activite biologique de type retinoide
AT96941408T ATE200074T1 (de) 1995-11-22 1996-11-18 Aryl oder heteroarylamide von tetrahydronaphthalin, chroman, thiochroman oder 1,2,3,4-tetrahydrochinolin-carbonsäuren mit einer retinoid-ähnlichen biologischen aktivität
HU9902536A HUP9902536A3 (en) 1996-11-18 1996-11-18 Aryl or heteroaryl amides of tetrahydronaphtalene, chroman, thiochroman and 1,2,3,4-tetrahydroquinoline carboxylic acids having retinoid-like biological activity
EP96941408A EP0876330B1 (fr) 1995-11-22 1996-11-18 Arylamides ou hetero-arylamides de tetrahydronaphtalene, de chromane, de thiochromane et d'acides carboxyliques 1,2,3,4-tetrahydroquinoliniques ayant une activite biologique de type retinoide
JP51985297A JP4112003B2 (ja) 1995-11-22 1996-11-18 レチノイド様生物学的活性を有する、テトラヒドロナフタレン、クロマン、チオクロマンおよび１，２，３，４―テトラヒドロキノリンカルボン酸のアリールまたはヘテロアリールアミド
AU10560/97A AU702499B2 (en) 1995-11-22 1996-11-18 Aryl or heteroaryl amides of tetrahydronaphthalene, chroman, thiochroman and 1,2,3,4-tetrahydroquinoline carboxylic acids having retinoid-like biological activity
KR1019980703816A KR100483442B1 (ko) 1995-11-22 1996-11-18 레티노이드형생리활성을갖는테트라히드로나프타렌,크로만,티오크로만및1,2,3,4-테트라히드퀴놀린카르복실산의아릴또는헤테로아릴아미드
NZ323581A NZ323581A (en) 1995-11-22 1996-11-18 Aryl or heteroaryl amides of tetrahydronaphthalene, chroman, thiochroman and 1,2,3,4-tetrahydroquinoline carboxylic acids having retinoid-like biological activity
DE69612303T DE69612303T2 (de) 1995-11-22 1996-11-18 Aryl oder heteroarylamide von tetrahydronaphthalin, chroman, thiochroman oder 1,2,3,4-tetrahydrochinolin-carbonsäuren mit einer retinoid-ähnlichen biologischen aktivität
IL12459796A IL124597A (en) 1995-11-22 1996-11-18 Amides of acrylic acids, troaryl, tetrahydronaphthalene, chromium, theochroman and 1,2,3,4 tetrahydroquinoline carboxyls are converted in the aromatic or trohromatic green, electron-withdrawing transducer, having retinal-like biological activity
PL96327457A PL186404B1 (pl) 1995-11-22 1996-11-18 Arylowe i heteroarylowe amidy kwasów karboksylowych posiadające czynność retynopodobną
DK96941408T DK0876330T3 (da) 1995-11-22 1996-11-18 Aryl- eller heteroarylamider af tetrahydronapthylen-, chroman-, thiochroman- og 1,2,3,4-tetrahydroquinolincarboxylsyrer, som har retinoidlignende biologisk aktivitet
BR9611758A BR9611758A (pt) 1995-11-22 1996-11-18 Aril e heteroaril amidas de tetraidronaftaleno cromano tiocromano e ácidos 1,2,3,4-tetraidroquinolina carboxílicos tendo atividade biológica semelhante a retinóide
GR20010400830T GR3035979T3 (en) 1995-11-22 2001-05-31 Aryl or heteroaryl amides of tetrahydronaphthalene, chroman, thiochroman and 1,2,3,4-tetrahydroquinoline carboxylic acids having retinoid-like biological activity

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US08/562,000 US5675024A (en) 1995-11-22 1995-11-22 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
US08/562,000 1995-11-22

Publications (2)

Publication Number Publication Date
WO1997019052A1 WO1997019052A1 (fr) 1997-05-29
WO1997019052B1 true WO1997019052B1 (fr) 1997-06-26

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1996/018580 WO1997019052A1 (fr) 1995-11-22 1996-11-18 Arylamides ou hetero-arylamides de tetrahydronaphtalene, de chromane, de thiochromane et d'acides carboxyliques 1,2,3,4-tetrahydroquinoliniques ayant une activite biologique de type retinoide

Country Status (20)

Country Link
US (5) US5675024A (fr)
EP (1) EP0876330B1 (fr)
JP (1) JP4112003B2 (fr)
KR (1) KR100450498B1 (fr)
CN (1) CN1117070C (fr)
AT (1) ATE200074T1 (fr)
AU (1) AU702499B2 (fr)
BR (1) BR9611758A (fr)
CA (1) CA2238274C (fr)
DE (1) DE69612303T2 (fr)
DK (1) DK0876330T3 (fr)
ES (1) ES2157470T3 (fr)
GR (1) GR3035979T3 (fr)
IL (1) IL124597A (fr)
MX (1) MX9804087A (fr)
NZ (1) NZ323581A (fr)
PL (1) PL186404B1 (fr)
PT (1) PT876330E (fr)
RU (1) RU2163906C2 (fr)
WO (1) WO1997019052A1 (fr)

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