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Pub. No.:    WO/1998/014432    International Application No.:    PCT/EP1997/005322
Publication Date: 09.04.1998 International Filing Date: 24.09.1997
Chapter 2 Demand Filed:    13.03.1998    
C07D 233/48 (2006.01), C07D 233/88 (2006.01), C07D 405/12 (2006.01)
Applicants: JANSSEN PHARMACEUTICA N.V. [BE/BE]; Turnhoutseweg 30, B-2340 Beerse (BE) (For All Designated States Except US).
FREYNE, Eddy, Jean, Edgard [BE/BE]; (BE) (For US Only).
FERNANDEZ-GADEA, Francisco Javier [ES/ES]; (ES) (For US Only).
ANDRES-GIL, José Ignacio [ES/ES]; (ES) (For US Only)
Inventors: FREYNE, Eddy, Jean, Edgard; (BE).
FERNANDEZ-GADEA, Francisco Javier; (ES).
ANDRES-GIL, José Ignacio; (ES)
Agent: QUAGHEBEUR, Luc; Janssen Pharmaceutica N.V., Patent Dept., Turnhoutseweg 30, B-2340 Beerse (BE)
Priority Data:
96202749.6 02.10.1996 EP
Abstract: front page image
(EN)The present invention concerns 2-cyanoiminoimidazole derivatives having formula (I) the $i(N)-oxide forms, the pharmaceutically acceptable addition salts and the stereochemically isomeric forms thereof, wherein R?1¿ and R?2¿ each independently are hydrogen; C¿1-6?alkyl; difluoromethyl; trifluoromethyl; C¿3-6?cycloalkyl; a saturated 5-, 6- or 7-membered heterocycle containing one or two heteroatoms selected from oxygen, sulfur or nitrogen; indanyl; 6,7-dihydro-5$i(H)-cyclopentapyridinyl; bicyclo[2.2.1]-2-heptenyl; bicyclo[2.2.1]heptanyl; C¿1-6?alkylsulfonyl; arylsulfonyl; or substituted C¿1-10?alkyl; R?3¿ is hydrogen, halo or C¿1-6?alkyloxy; R?4¿ is hydrogen; halo; C¿1-6?alkyl; trifluoromethyl; C¿3-6?cycloalkyl; carboxyl; C¿1-4?alkyloxycarbonyl; C¿3-6?cycloalkylaminocarbonyl; aryl; Het?1¿; or substituted C¿1-6?alkyl; or R?4¿ is -O-R?7¿ or -NH-R?8¿; R?5¿ is hydrogen, halo, hydroxy, C¿1-6?alkyl or C¿1-6?alkyloxy; R?6¿ is a hydrogen or C¿1-4?alkyl; or R?4¿ and R?6¿, or R?4¿ and R?5¿ taken together may form a bivalent radical; -A-B- is -CR?10¿=CR?11¿- or -CHR?10¿-CHR?11¿-; L is hydrogen; C¿1-6?alkyl; C¿1-6?alkylcarbonyl; C¿1-6?alkyloxycarbonyl; substituted C¿1-6?alkyl; C¿3-6?alkenyl; substituted C¿3-6?alkenyl; piperidinyl; substituted piperidinyl; C¿1-6?alkylsulfonyl or arylsulfonyl; having PDE IV and cytokine inhibiting activity. The invention also relates to processes for preparing the compounds of formula (I) and pharmaceutical compositions thereof.
(FR)L'invention concerne des dérivés de 2-cyanoiminoimidazole présentant la formule (I), les formes de $i(N)-oxyde, les sels d'addition pharmaceutiquement acceptables et les formes stéréochimiquement isomériques de ces derniers. Dans la formule, R?1¿ et R?2¿ sont chacun indépendamment de l'hydrogène, de l'alkyle C¿1-6?, difluorométhyle, trifluorométhyle, cycloalkyle C¿3-6?; un hétérocycle saturé à 5 ou 6 éléments contenant un ou deux hétéroatomes sélectionnés parmi de l'oxygène, du soufre ou de l'azote; indanyle; 6,7-dihydro-5$i(H)-cyclopentapyridinyle; bicyclo(2.2.1)-2-heptényle; bicyclo(2.2.1.)heptanyle; alkylsulfonyle C¿1-6?; arylsulfonyle, ou de l'alkyle C¿1-10? substitué. R?3¿ représente hydrogène, halo ou alkyloxy C¿1-6?; R?4¿ représente hydrogène, halo; alkyle C¿1-6?, trifluorométhyle, cycloalkyle C¿3-6?, carboxyle, alkyloxycarbonyle C¿1-4?, cycloalkyle C¿3-6? aminocarbonyle; aryle; Het?1¿, ou alkyle C¿1-6? substitué; ou R?4¿ est -O-R?7¿ ou -NH-R?8¿. R?5¿ est hydrogène, halo, hydroxy, alkyle C¿1-6? ou alkyloxy C¿1-6?. R?6¿ est un hydrogène ou un alkyle C¿1-4? ou R?4¿ et R?6¿, ou R?4¿ et R?5¿ pris ensemble forment un radical bivalent. -A-B- est -CR?10¿=CR?11¿- ou -CHR?10¿-CHR?11¿-; L est hydrogène, alkyle C¿1-6?, alkylcarbonyle C¿1-6?; alkyloxycarbonyle C¿1-6?; alkyle C¿1-6? substitué, alkényle C¿3-6?, alkényle C¿3-6? substitué, pipéridinyle, pipéridinyle substitué, alkylsulfonyle C¿1-6? ou arylsulfonyle, présentant une activité inhibant la cytokine et la phosphodiesterase IV. L'invention concerne aussi des procédés de préparation des composés de la formule (I) et des compositions pharmaceutiques de ces derniers.
Designated States: AL, AM, AT, AU, AZ, BA, BB, BG, BR, BY, CA, CH, CN, CU, CZ, DE, DK, EE, ES, FI, GB, GE, GH, HU, IL, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MD, MG, MK, MN, MW, MX, NO, NZ, PL, PT, RO, RU, SD, SE, SG, SI, SK, SL, TJ, TM, TR, TT, UA, UG, US, UZ, VN, YU, ZW.
African Regional Intellectual Property Organization (GH, KE, LS, MW, SD, SZ, UG, ZW)
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)