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1. (WO1997016422) SULFIDES, SULFOXIDES AND SULFONES DISUBSTITUTED WITH A TETRAHYDRONAPHTHALENYL, CHROMANYL, THIOCHROMANYL OR TETRAHYDROQUINOLINYL AND SUBSTITUTED PHENYL OR HETEROARYL GROUP, HAVING RETINOID-LIKE BIOLOGICAL ACTIVITY
Latest bibliographic data on file with the International Bureau

Pub. No.: WO/1997/016422 International Application No.: PCT/US1996/017295
Publication Date: 09.05.1997 International Filing Date: 29.10.1996
Chapter 2 Demand Filed: 15.05.1997
IPC:
C07C 317/44 (2006.01) ,C07C 323/62 (2006.01) ,C07D 213/80 (2006.01) ,C07D 277/56 (2006.01)
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
317
Sulfones; Sulfoxides
44
having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
323
Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
50
containing thio groups and carboxyl groups bound to the same carbon skeleton
62
having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
213
Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
02
having three double bonds between ring members or between ring members and non-ring members
04
having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
60
with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
78
Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
79
Acids; Esters
80
in position 3
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
277
Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
02
not condensed with other rings
20
having two or three double bonds between ring members or between ring members and non-ring members
32
with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
56
Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Applicants:
ALLERGAN [US/US]; 2525 Dupont Drive, T-2, 2-E Post Office Box 19534 Irvine, CA 92623-9534 USA, US
Inventors:
BEARD, Richard, L.; US
COLON, Diana, F.; US
CHANDRARATNA, Roshantha, A.; US
Agent:
BARAN, Robert, J. ; Allergan, Inc. 2525 Dupont Drive P.O. Box 19534 Irvine, CA 92623-9534, US
Priority Data:
08/552,96501.11.1995US
Title (EN) SULFIDES, SULFOXIDES AND SULFONES DISUBSTITUTED WITH A TETRAHYDRONAPHTHALENYL, CHROMANYL, THIOCHROMANYL OR TETRAHYDROQUINOLINYL AND SUBSTITUTED PHENYL OR HETEROARYL GROUP, HAVING RETINOID-LIKE BIOLOGICAL ACTIVITY
(FR) SULFURES, SULFOXYDES ET SULFONES DISUBSTITUES AVEC UN GROUPE TETRAHYDRONAPHTALENYLE, CHROMANYLE, THIOCHROMANYLE OU TETRAHYDROQUINOLEINYLE ET UN GROUPE HETEROARYLE OU PHENYLE SUBSTITUE, EXERÇANT UNE ACTIVITE BIOLOGIQUE ANALOGUE A CELLE DU RETINOÏDE
Abstract:
(EN) Compounds of formula (1) wherein X is S, O, NR' where R' is H or alkyl of 1 to 6 carbons, or X is [C(R1)2]n where n is an integer between 0 and 2; R1 is independently H or alkyl of 1 to 6 carbons; R2 is hydrogen, lower alkyl of 1 to 6 carbons, F, Cl, Br, I, fluoro substituted alkyl of 1 to 6 carbons, OH, SH, alkoxy of 1 to 6 carbons, or alkylthio of 1 to 6 carbons; R3 is hydrogen, lower alkyl of 1 to 6 carbons or F; m is an integer having the value of 0-3; o is an integer having the value of 0-4; p is an integer having the value of 0-2; Y is a phenyl or naphthyl group, or heteroaryl selected from a group consisting of pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, oxazolyl, imidazolyl and pyrrazolyl, said phenyl and heteroaryl groups being optionally substituted with one or two R2 groups; A is (CH2)q where q is 0-5, lower branched chain alkyl having 3-6 carbons, cycloalkyl having 3-6 carbons, alkenyl having 2-6 carbons and 1 or 2 double bonds, alkynyl having 2-6 carbons and 1 or 2 triple bonds, and B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR8, CONR9R10, -CH2OH, CH2OR11, CH2OCOR11, CHO, CH(OR12)2, CHOR13O, -COR7, CR7(OR12)2, CR7OR13O, or tri-lower alkylsilyl, where R7 is an alkyl, cycloalkyl or alkenyl group containing 1 to 5 carbons, R8 is an alkyl group of 1 to 10 carbons or (trimethylsilyl)alkyl where the alkyl group has 1 to 10 carbons, or a cycloalkyl group of 5 to 10 carbons, or R8 is phenyl or lower alkylphenyl, R9 and R10 independently are hydrogen, an alkyl group of 1 to 10 carbons or a cycloalkyl group of 5-10 carbons, or phenyl or lower alkylphenyl, R11 is lower alkyl, phenyl or lower alkylphenyl, R12 is lower alkyl, and R13 is divalent alkyl radical of 2-5 carbons, are selective agonists of RXR retinoid receptors.
(FR) Composés de la formule (1). Dans cette formule, X est S, O, NR' considérant que R' est H ou un alkyle de 1 à 6 atomes de carbone, ou X est [C(R1)2]n considérant que n est un entier entre 0 et 2; R1 est indépendamment H ou un alkyle de 1 à 6 atomes de carbone; R2 est hydrogène, un alkyle inférieur de 1 à 6 atomes de carbone, F, Cl, Br, I, un alkyle à substitution fluoro de 1 à 6 atomes de carbone, OH, SH, alcoxy de 1 à 6 atomes de carbone, ou alkylthio de 1 à 6 atomes de carbone; R3 est hydrogène, un alkyle inférieur de 1 à 6 atomes de carbone ou F; m est un entier d'une valeur de 0 à 3; o est un entier d'une valeur de 0 à 4; p est un entier d'une valeur de 0 à 2; Y est un groupe phényle ou naphtyle, ou un hétéroaryle choisi dans le groupe constitué par pyridyle, thiényle, furyle, pyridazinyle, primidinyle, pyrazinyle, thiazolyle, oxazolyle, imidazolyle et pyrrazolyle, lesdits groupes phényle et hétéroaryle étant éventuellement substitués par un ou deux groupes R2; A est (CH2)q, considérant que q est compris entre 0 et 5, une chaîne alkyle inférieure ramifiée comptant de 3 à 6 atomes de carbone, un cycloalkyle comptant de 3 à 6 atomes de carbone, un alcényle comptant de 2 à 6 atomes de carbone et une ou deux liaisons doubles, un alcynyle comptant de 2 à 6 atomes de carbone et une ou deux liaisons triples, et B est hydrogène, COOH ou un sel pharmaceutiquement acceptable de ceux-ci, COOR8, CONR9R10, -CH2OH, CH2OR11, CH2OCOR11, CHO, CH(OR12)2, CHOR13O, -COR7, CR7(OR12)2, CR7OR13O, ou un tri-alkylsilyle inférieur, considérant que R7 est un groupe alkyle, cycloalkyle ou alcényle comptant de 1 à 5 atomes de carbone, R8 est un groupe alkyle comptant de 1 à 10 atomes de carbone ou un (triméthylsilyle)alkyle dans lequel le groupe alkyle compte de 1 à 10 atomes de carbone, ou un groupe cycloalkyle comptant de 5 à 10 atomes de carbone, ou R8 est phényle ou alkylphényle inférieur, R9 et R10 sont indépendamment hydrogène, un groupe alkyle comptant de 1 à 10 atomes de carbone ou un groupe cycloalkyle comptant de 5 à 10 atomes de carbone, ou phényle ou alkylphényle inférieur, R11 est alkyle inférieur, phényle ou alkylphényle inférieur, R12 est alkyle inférieur et R13 est un radical alkyle bivalent comptant de 2 à 5 atomes de carbone. Ces composés se révèlent des agonistes sélectifs des récepteurs RXR de rétinoïde.
Designated States: AL, AM, AT, AU, AZ, BB, BG, BR, BY, CA, CH, CN, CZ, DE, DK, EE, ES, FI, GB, GE, HU, IL, IS, JP, KE, KG, KP, KR, KZ, LK, LR, LS, LT, LU, LV, MD, MG, MK, MN, MW, MX, NO, NZ, PL, PT, RO, RU, SD, SE, SG, SI, SK, TJ, TM, TR, TT, UA, UG, UZ, VN
African Regional Intellectual Property Organization (ARIPO) (KE, LS, MW, SD, SZ, UG)
Eurasian Patent Organization (AM, AZ, BY, KG, KZ, MD, RU, TJ, TM)
European Patent Office (AT, BE, CH, DE, DK, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE)
African Intellectual Property Organization (BF, BJ, CF, CG, CI, CM, GA, GN, ML, MR, NE, SN, TD, TG)
Publication Language: English (EN)
Filing Language: English (EN)
Also published as:
AU1996075985