SI9200378B - Fluorofenilbenzopirani in njihova uporaba pri zdravljenju nekaterih motenj centralnega živčnega sistema - Google Patents
Fluorofenilbenzopirani in njihova uporaba pri zdravljenju nekaterih motenj centralnega živčnega sistema Download PDFInfo
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- SI9200378B SI9200378B SI9200378A SI9200378A SI9200378B SI 9200378 B SI9200378 B SI 9200378B SI 9200378 A SI9200378 A SI 9200378A SI 9200378 A SI9200378 A SI 9200378A SI 9200378 B SI9200378 B SI 9200378B
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- benzopyran
- dihydro
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- dimethyl
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- KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical compound C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 title 1
- 239000013543 active substance Substances 0.000 title 1
- 125000000623 heterocyclic group Chemical group 0.000 title 1
- -1 heteroarylsulphinyl Chemical group 0.000 claims abstract 37
- 239000001257 hydrogen Substances 0.000 claims abstract 31
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 31
- 125000000217 alkyl group Chemical group 0.000 claims abstract 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 14
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 11
- 150000001875 compounds Chemical class 0.000 claims abstract 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 9
- 125000003118 aryl group Chemical group 0.000 claims abstract 8
- 150000002431 hydrogen Chemical class 0.000 claims abstract 8
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims abstract 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 7
- 239000001301 oxygen Substances 0.000 claims abstract 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 6
- 150000003839 salts Chemical class 0.000 claims abstract 6
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims abstract 5
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 4
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims abstract 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 4
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims abstract 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract 3
- 125000005129 aryl carbonyl group Chemical group 0.000 claims abstract 3
- 125000001589 carboacyl group Chemical group 0.000 claims abstract 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract 3
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims abstract 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract 3
- 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims abstract 2
- 125000004685 alkoxythiocarbonyl group Chemical group 0.000 claims abstract 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract 2
- 239000001961 anticonvulsive agent Substances 0.000 claims abstract 2
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims abstract 2
- 239000003814 drug Substances 0.000 claims abstract 2
- 125000001207 fluorophenyl group Chemical group 0.000 claims abstract 2
- 238000011321 prophylaxis Methods 0.000 claims abstract 2
- 238000011282 treatment Methods 0.000 claims abstract 2
- LKXADRQJLNYNQL-UHFFFAOYSA-N 2h-chromen-3-ol Chemical compound C1=CC=C2OCC(O)=CC2=C1 LKXADRQJLNYNQL-UHFFFAOYSA-N 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims 3
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 2
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 2
- 239000005977 Ethylene Substances 0.000 claims 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 2
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000005150 heteroarylsulfinyl group Chemical group 0.000 claims 2
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- RXUGYQLKENNLFS-MOPGFXCFSA-N (3s,4r)-4-[[2-(4-fluorophenyl)-2-oxoethyl]amino]-3-hydroxy-2,2-dimethyl-3,4-dihydrochromene-6-carbonitrile Chemical compound N([C@@H]1C2=CC(=CC=C2OC([C@H]1O)(C)C)C#N)CC(=O)C1=CC=C(F)C=C1 RXUGYQLKENNLFS-MOPGFXCFSA-N 0.000 claims 1
- SVDBMPXQEJMAAV-UXHICEINSA-N (3s,4r)-4-[[3-(4-fluorophenyl)-3-oxopropyl]amino]-3-hydroxy-2,2-dimethyl-3,4-dihydrochromene-6-carbonitrile Chemical compound N([C@@H]1C2=CC(=CC=C2OC([C@H]1O)(C)C)C#N)CCC(=O)C1=CC=C(F)C=C1 SVDBMPXQEJMAAV-UXHICEINSA-N 0.000 claims 1
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- HMMYJCOLDIAMDJ-MSOLQXFVSA-N 1-(4-fluorophenyl)-2-[[(3s,4r)-3-hydroxy-2,2-dimethyl-6-(trifluoromethyl)-3,4-dihydrochromen-4-yl]amino]ethanone Chemical compound N([C@@H]1C2=CC(=CC=C2OC([C@H]1O)(C)C)C(F)(F)F)CC(=O)C1=CC=C(F)C=C1 HMMYJCOLDIAMDJ-MSOLQXFVSA-N 0.000 claims 1
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 1
- JMXDINQBLUIWRZ-UXHICEINSA-N 2-[[(3s,4r)-6-ethyl-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl]amino]-1-(4-fluorophenyl)ethanone Chemical compound N([C@H]1[C@H](O)C(C)(C)OC2=CC=C(C=C21)CC)CC(=O)C1=CC=C(F)C=C1 JMXDINQBLUIWRZ-UXHICEINSA-N 0.000 claims 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
- DBDAAGUPCXKKIW-RTWAWAEBSA-N 3-[[(3s,4r)-6-ethyl-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl]amino]-1-(4-fluorophenyl)propan-1-one Chemical compound N([C@H]1[C@H](O)C(C)(C)OC2=CC=C(C=C21)CC)CCC(=O)C1=CC=C(F)C=C1 DBDAAGUPCXKKIW-RTWAWAEBSA-N 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- ANLNMIMEUGLOSV-SJORKVTESA-N 4-fluoro-n-[(3s,4r)-3-hydroxy-2,2,6-trimethyl-3,4-dihydrochromen-4-yl]benzamide Chemical compound N([C@H]1[C@H](O)C(C)(C)OC2=CC=C(C=C21)C)C(=O)C1=CC=C(F)C=C1 ANLNMIMEUGLOSV-SJORKVTESA-N 0.000 claims 1
- FIJXVTLETUCGPX-SJORKVTESA-N 4-fluoro-n-[(3s,4r)-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl]-n-methylbenzamide Chemical compound CN([C@@H]1C2=CC=CC=C2OC(C)(C)[C@H]1O)C(=O)C1=CC=C(F)C=C1 FIJXVTLETUCGPX-SJORKVTESA-N 0.000 claims 1
- RHCWEVZGWRKVCA-CVEARBPZSA-N 4-fluoro-n-[(3s,4r)-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl]benzamide Chemical compound N([C@@H]1C2=CC=CC=C2OC([C@H]1O)(C)C)C(=O)C1=CC=C(F)C=C1 RHCWEVZGWRKVCA-CVEARBPZSA-N 0.000 claims 1
- CLMSNNJYGHOESW-CVEARBPZSA-N 4-fluoro-n-[(3s,4r)-3-hydroxy-2,2-dimethyl-6-(1,1,2,2,2-pentafluoroethyl)-3,4-dihydrochromen-4-yl]benzamide Chemical compound N([C@@H]1C2=CC(=CC=C2OC([C@H]1O)(C)C)C(F)(F)C(F)(F)F)C(=O)C1=CC=C(F)C=C1 CLMSNNJYGHOESW-CVEARBPZSA-N 0.000 claims 1
- HXUNYSGWGDZMFF-CVEARBPZSA-N 4-fluoro-n-[(3s,4r)-3-hydroxy-2,2-dimethyl-6-(trifluoromethyl)-3,4-dihydrochromen-4-yl]benzamide Chemical compound N([C@@H]1C2=CC(=CC=C2OC([C@H]1O)(C)C)C(F)(F)F)C(=O)C1=CC=C(F)C=C1 HXUNYSGWGDZMFF-CVEARBPZSA-N 0.000 claims 1
- MBWWQPBRAYWCEQ-CVEARBPZSA-N 4-fluoro-n-[(3s,4r)-3-hydroxy-2,2-dimethyl-6-nitro-3,4-dihydrochromen-4-yl]benzamide Chemical compound N([C@@H]1C2=CC(=CC=C2OC([C@H]1O)(C)C)[N+]([O-])=O)C(=O)C1=CC=C(F)C=C1 MBWWQPBRAYWCEQ-CVEARBPZSA-N 0.000 claims 1
- ZGSSQCRTIJGLTO-YADHBBJMSA-N 4-fluoro-n-[(3s,4r)-3-hydroxy-2,2-dimethyl-6-phenyl-3,4-dihydrochromen-4-yl]benzamide Chemical compound N([C@@H]1C2=CC(=CC=C2OC([C@H]1O)(C)C)C=1C=CC=CC=1)C(=O)C1=CC=C(F)C=C1 ZGSSQCRTIJGLTO-YADHBBJMSA-N 0.000 claims 1
- CNDMZYVKIJHLPT-CVEARBPZSA-N 4-fluoro-n-[(3s,4r)-3-hydroxy-2,2-dimethyl-7-nitro-3,4-dihydrochromen-4-yl]benzamide Chemical compound N([C@@H]1C2=CC=C(C=C2OC([C@H]1O)(C)C)[N+]([O-])=O)C(=O)C1=CC=C(F)C=C1 CNDMZYVKIJHLPT-CVEARBPZSA-N 0.000 claims 1
- LXNJVUUFSNLJMJ-CVEARBPZSA-N 4-fluoro-n-[(3s,4r)-3-hydroxy-6-iodo-2,2-dimethyl-3,4-dihydrochromen-4-yl]benzamide Chemical compound N([C@@H]1C2=CC(I)=CC=C2OC([C@H]1O)(C)C)C(=O)C1=CC=C(F)C=C1 LXNJVUUFSNLJMJ-CVEARBPZSA-N 0.000 claims 1
- BQSLVHLLTYHDDK-SJORKVTESA-N 4-fluoro-n-[(3s,4r)-3-hydroxy-6-methoxy-2,2-dimethyl-3,4-dihydrochromen-4-yl]benzamide Chemical compound N([C@H]1[C@H](O)C(C)(C)OC2=CC=C(C=C21)OC)C(=O)C1=CC=C(F)C=C1 BQSLVHLLTYHDDK-SJORKVTESA-N 0.000 claims 1
- XWZIQODWNJQJSN-CVEARBPZSA-N 4-fluoro-n-[(3s,4r)-6-fluoro-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl]benzamide Chemical compound N([C@@H]1C2=CC(F)=CC=C2OC([C@H]1O)(C)C)C(=O)C1=CC=C(F)C=C1 XWZIQODWNJQJSN-CVEARBPZSA-N 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 125000001091 aminosulfinyl group Chemical group [H]N([H])S(*)=O 0.000 claims 1
- 229940125681 anticonvulsant agent Drugs 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- CHNUOJQWGUIOLD-NFZZJPOKSA-N epalrestat Chemical compound C=1C=CC=CC=1\C=C(/C)\C=C1/SC(=S)N(CC(O)=O)C1=O CHNUOJQWGUIOLD-NFZZJPOKSA-N 0.000 claims 1
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
- SWOCNAZMBQHTAS-SJORKVTESA-N methyl (3s,4r)-4-[(4-fluorobenzoyl)amino]-3-hydroxy-2,2-dimethyl-3,4-dihydrochromene-6-carboxylate Chemical compound N([C@H]1[C@H](O)C(C)(C)OC2=CC=C(C=C21)C(=O)OC)C(=O)C1=CC=C(F)C=C1 SWOCNAZMBQHTAS-SJORKVTESA-N 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- YRLYDZPUXKKDLC-MSOLQXFVSA-N n-[(3s,4r)-6-(2-amino-2-oxoethyl)-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl]-4-fluorobenzamide Chemical compound N([C@@H]1C2=CC(CC(N)=O)=CC=C2OC([C@H]1O)(C)C)C(=O)C1=CC=C(F)C=C1 YRLYDZPUXKKDLC-MSOLQXFVSA-N 0.000 claims 1
- MNHSKPTYDJCZFV-YADHBBJMSA-N n-[(3s,4r)-6-(benzenesulfonyl)-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl]-4-fluorobenzamide Chemical compound N([C@@H]1C2=CC(=CC=C2OC([C@H]1O)(C)C)S(=O)(=O)C=1C=CC=CC=1)C(=O)C1=CC=C(F)C=C1 MNHSKPTYDJCZFV-YADHBBJMSA-N 0.000 claims 1
- PGBHMPBORVWCPX-MSOLQXFVSA-N n-[(3s,4r)-6-acetyl-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl]-3-fluorobenzamide Chemical compound N([C@H]1[C@H](O)C(C)(C)OC2=CC=C(C=C21)C(=O)C)C(=O)C1=CC=CC(F)=C1 PGBHMPBORVWCPX-MSOLQXFVSA-N 0.000 claims 1
- YHDZJQFARWNKLZ-MSOLQXFVSA-N n-[(3s,4r)-6-cyano-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl]-3,4-difluoro-n-methylbenzamide Chemical compound CN([C@@H]1C2=CC(=CC=C2OC(C)(C)[C@H]1O)C#N)C(=O)C1=CC=C(F)C(F)=C1 YHDZJQFARWNKLZ-MSOLQXFVSA-N 0.000 claims 1
- FZNJQMSFIUKHIA-RTWAWAEBSA-N n-[(3s,4r)-6-cyclopentyl-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl]-4-fluorobenzamide Chemical compound N([C@@H]1C2=CC(=CC=C2OC([C@H]1O)(C)C)C1CCCC1)C(=O)C1=CC=C(F)C=C1 FZNJQMSFIUKHIA-RTWAWAEBSA-N 0.000 claims 1
- LCVQFLJYTBRTOX-MSOLQXFVSA-N n-[(3s,4r)-6-ethyl-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl]-4-fluorobenzamide Chemical compound N([C@H]1[C@H](O)C(C)(C)OC2=CC=C(C=C21)CC)C(=O)C1=CC=C(F)C=C1 LCVQFLJYTBRTOX-MSOLQXFVSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 1
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 2
- 125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 abstract 1
- 208000019901 Anxiety disease Diseases 0.000 abstract 1
- 206010026749 Mania Diseases 0.000 abstract 1
- 229910004679 ONO2 Inorganic materials 0.000 abstract 1
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 abstract 1
- 125000004691 alkyl thio carbonyl group Chemical group 0.000 abstract 1
- 230000036506 anxiety Effects 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 125000005469 ethylenyl group Chemical group 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 125000001893 nitrooxy group Chemical group [O-][N+](=O)O* 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 208000011580 syndromic disease Diseases 0.000 abstract 1
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Abstract
Opisana je spojina s formulo (I) ali njena farmacevtsko sprejemljiva sol kjer je bodisi Y N in je R2 vodik ali je Y C-R1, kjer je katerikoli od R1 IN R2 vodik in drugega izberemo iz razreda, v katerem so vodik, C3-8cikloalkil, C1-6alkil, v danem primeru prekinjen s kisikom ali substituiran s hidroksi, C1-6alkoksi ali substituiranim aminokarbonilom, C1-6alkilkarbonil, C1-6alkoksikarbonil, C1-6alkilkarboniloksi, C1-6alkoksi, nitro, ciano, halo, trifluorometil, CF3S ali skupina CF3-A-, kjer je A -CF2-,-CO-,-CH2- ali CH(OH), trifluorometoksi, C1-6alkilsulfinil, C1-6alkilsulfonil, C1-6alkoksisulfonil, C1-6alkoksisulfonil, aril, heteroaril, arilkarbonil, heteroarilkarbonil, arilsulfinil, heteroarilsulfinil, arilsulfonil, heteroarilsulfonil, kjer je katerikoli aromatski del v danem primeru substituiran, C1-6alkilkarbonilamino, C1-6alkoksikarbonilamino, C1-6alkiltiokarbonil, C1-6alkoksitiokarbonil, C1-6alkiltiokarboniloksi, 1-merkapto-C2-7alkil, formil ali aminosulfinil, aminosulfonil ali aminokarbonil, pri čemerje katerikoli amino del v danem primeru substituiran z eno ali dvema C1-6alkilnima skupinama, ali C1-6alkilsulfinilamino, C1-6alkilsulfonilamino, C1-6alkoksisulfinilamino ali C1-6alkoksisulfonilamino ali etilenil, terminalno substituiran s C1-6alkilkarbonilom, nitro ali ciano, ali -C(C1-6alkil)NOH ali -C(C1-6alkil)NNH2, ali je eden od R1 in R2nitro, ciano ali C1-3alkilkarbonil in je drugi metoksi ali amino, v danem primeru substituiran z enim ali dvema C1-6alkiloma ali s C2-7alkanoilom; eden od R3 in R4 jevodik ali C1-4alkil in drugi C1-4alkil ali sta R3 in R4 skupaj C2-5polimetilen; R5 je C1-6alkilkarboniloksi, benzoiloksi, ONO2, benziloksi, feniloksi ali C1-6alkoksi ter sta R6 in R9 vodik ali je R5hidroksi in R6 vodik ali C1-6alkil in je R9vodik; R7 je fluorofenil; R8 je vodik ali C1-6alkil; pri čemer je skupina R8-N-CO-R7trans glede na skupino R5; in je X kisik ali NR10, kjer je R10 vodik ali C1-6alkil, ki jo uporabimo pri pripravi zdravila za zdravljenje in/ali profilakse zaskrbljenosti in/ali manijein/ali depresije in/ali učinkov, združenih z odtegnitvijo snovi, ki povzročajo zasvojenost, in/ali motenj, ki se jih da zdraviti in/ali preprečevati z antikonvulzivnimi sredstvi.
Claims (15)
1 EP O 587 645 Patentni zahtevki 1. Uporaba spojine s formulo (I) ali njene farmacevtsko sprejemljive soli
kjer je bodisi Y N in je R2 vodik ali je Y C-R1? kjer je katerikoli od R\ in R2 vodik in drugega izberemo iz razreda, v katerem so vodik, C3.8cikloalkil, Ci.6alkil, v danem primeru prekinjen s kisikom ali substituiran s hidroksi, C^alkoksi ali substituiranim aminokarbonilom, Ci.6alkilkarbonil, Ci^alkoksikarbonil, C|.6alkilkarboniloksi, Ci_6alkoksi, nitro, ciano, halo, trifulorometil, CF3S ali skupina CF3-A-, kjer je A CF2-, -CO-, -CH2- ali CH(OH), trifluorometoksi, Ci^alkilsulfinil, Ci^alkilsulfonil, Ci_6alkoksisulfinil, C].6alkoksisulfonil, aril, heteroaril, arilkarbonil, heteroarilkarbonil, arilsulfmil, heteroarilsulfinil, arilsulfonil, heteroarilsulfonil, kjer je katerikoli aromatski del v danem primeru substituiran, C^alkilkarbonilamino, Ci.6alkoksikarbonilamino, Ci.6alkil-tiokarbonil, Ci_6alkoksi-tiokarbonil, Ci_6alkil-tiokarboniloksi, 1-merkapto-C2.7alkil, formil ali aminosulfinil, aminosulfonil ali aminokarbonil, pri Čemer je katerikoli amino del v danem primeru substituiran z eno ali dvema C^alkilnima skupinama, ali Ci_6alkilsulfinilamino, Ci_6alkilsulfonilamino, Ci.6alkoksisulfinilamino ali Ci.6alkoksisulfonilamino ali etilenil, terminalno substituiran s Ci_6alkilkarbonilom, nitro ali ciano, ali -C(Ci_6alkil)NOH ali -C(Ci.6alkil)NNH2, ali je eden od R| in R2 nitro, ciano ali Ci.3alkilkarbonil in je drugi metoksi ali amino, v danem primeru substituiran z enim ali dvema Ci_6alkiloma ali s C2.7alkanoilom; 2 eden od R3 in R4 je vodik ali Ci_4alkil in je drugi Ci_4alkil ali sta R3 in R4 skupaj C2-5polimetilen; R5 je Ci.6alkilkarboniloksi, benzoiloksi, 0N02, benziloksi, feniloksi ali C^alkoksi ter sta R^ in R9 vodik, ali je R5 hidroksi in je R^ vodik ali C^alkil in je R9 vodik; R7 je fluorofenil; R8 je vodik ali Ci_6alkil; pri Čemer je skupina R8-N-CO-R7 trans glede na R5 skupino; in je X kisik ali NR10, kjer je Ri0 vodik ali Ci^alkil; kjer aril pomeni fenil ali naftil in heteroaril pomeni 5- ali 6-člensko monociklično ali 9- ali 10-člensko biciklično skupino, ki vsebuje do tri heteroatome, ki so enaki ali različni in so izbrani izmed kisika, dušika in žvepla; in vsaka arilna ali heteroarilna skupina je v danem primeru substituirana z do tremi substituenti, neodvisno izbranimi izmed C^alkila, C]4alkoksi, halo hidroksi, nitro, ciano in SOnH, kjer je n=0 do 2; za pripravo zdravila za zdravljenje in/ali profilakso motenj, ki se jih da zdraviti ali preprečevati z antikonvulzivnimi sredstvi.
2. Uporaba po zahtevku 1, kjer ima spojina (I) naslednje spremenljivke, kjer je: Y C-Rh kjer je katerikoli od Rj in R2 vodik in je drugi izbran izmed naslednjih, kot so vodik, C^alkilkarbonil, C1_6alkoksikarbonil, C^alkilkarboniloksi, Ci.6alkilhidroksimetil, 3 nitro, ciano, kloro, trifluorometil, trifluorometoksi, Ci.6alkilsulfmil, Ci.6alkilsulfonil, C1.6alkoksisulfinil, Ci_6alkoksisulfonil, Ci_6alkilkarbonilamino, C i _6alkoksikarbonilamino Ci.6alkil-tiokarbonil, Ci^alkoksi-tiokarbonil, Ci_6alkil-tiokarboniloksi, 1-merkapto-C2-7alkil, formil ali aminosulfmil, aminosulfonil ali aminokarbonil, pri čemer je amino del v danem primeru substituiran z eno ali dvema C^alkilnima skupinama, ali Ci.6alkilsulfmilamino, Ci^alkilsulfonilamino, Ci_ 6alkoksisulfinilamino ali C i _6alkoksisul fonilamino ali etilenil, terminalno substituiran s C|_6alkiIkarbonilom, nitro ali ciano, ali -C(Ci_6alkil)NOH ali -C(Ci.6alkil)NNH2, ali je eden od R| in R2 nitro, ciano ali C^alkilkarbonil in je drugi metoksi ali amino, v danem primeru substituiran z enim ali dvema Ci_6alkiloma ali s C2.7alkanoilom; je eden od R3 in R4 vodik ali C^alkil in je drugi Ci_4alkil ali sta R3 in R4 skupaj C2.5polimetilen; R5 je hidroksi in R^ je vodik; R7je fluorofepil; R8 je vodik ali C].6aljcil; in R9 je vodik; pri čemer je skupina R8-N-CO-R7 trans glede na R5 skupino.
3. Uporaba po zahtevku 1, kjer je spojina izbrana izmed: trans-6-ciano-3,4-dihidro-2,2-dimetil-4-(3-fluoro-benzoilamino)2H-1 -benzopiran-3 -ola, trans-6-ciano-3,4-dihidro-2,2-dimetil-4-(2-fluoro-benzoilamino)2H-1-benzopiran-3-ola, 4 trans-6-tri fluorometoksi-3,4-dihidro-2,2-dimeti 1-4-(3-fluoro-benzoilamino)2H-1 -benzopiran-3 -ola, trans-6-ciano-4S-(3-fluorobenzoilamino)-3,4-dihidro-2,2-dimetil-2H-1 -benzopiran-3R-ola, trans-6-ciano-4R-(3-fluorobenzoilamino)-3,4-dihidro-2,2-dimetil-2H-1 -benzopiran-3 S-ola, trans-6-ciano-4S-(2-fluorobenzoilamino)-3,4-dihidro-2,2-dimetil-2H-1 -benzopiran-3R-ola, tnms-6-ciano-4S-(2,4-difluorobenzoilamino)-3,4-dihidro-2,2-dimetil-2H-1 -benzopiran-3R-ola, trans-6-acetil-4-(3-fluorobenzoilamino)-3,4-dihidro-2,2-dimetil-2H-1-benzopiran-3-ola, trans-6-ciano-4-(3,4-difluorobenzoil-metilamino)-3,4-dihidro-2,2-dimetil-2H-1-benzopiran-3-ola in trans-6-ciano-4S-(3,4-difluorobenzoilamino)-3,4-dihidro-2,2-dimetil-2H-1 -benzopiran-3R-ola, ali njegove farmacevtsko sprejemljive soli. 5
4. Uporaba po zahtevku 1, kjer je spojina s formulo (I) spojina s formulo (Ib) ali njene farmacevtsko sprejemljive soli:
kjer so spremenljivke R3, R4, R5, R6, R7, R8, R9 in X kot je definirano v zvezi s formulo (I) v zahtevku 1 in je Y' CRi, kjer sta Ri in R2 oba vodik ali je eden od R] in R2 trifluorometoksi, Ci.6alkil, prekinjen s kisikom ali substituiran s hidroksi, C].6alkoksi ali substituiranim amino-karbonilom, CF3A- (kjer je A -CF2-, -CO-,-CH2 ali CH(OH)), aril sulfonil, aril, C3.8cikloalkil, Ci_6alkoksi, heteroaril, arilkarbonil, heteroarilkarbonil, arilsulfinil, heteroarilsulfinil, heteroarilsulfonil, kjer je katerikoli aromatski del v danem primeru substituiran, in je drugi vodik.
5. Uporaba po zahtevku 4, kjer je spojina izbrana izmed: trans-3,4-dihidro-2,2-dimetil-4-(4-fluorobenzoilamino)-2H-1 -benzopiran-3-ola, trans-4-(4-fluorobenzoilamino)-3,4-dihidro-2,2,6-trimetil-2H-l-benzopiran-3-ola, trans-6-etil-4-(4-fluorobenzoilamino)-3,4-dihidro-2,2-dimetil-2H-1 -benzopiran-3 -ola, trans-6-etil-4-(4-fluorobenzoiletilamino)-3,4-dihidro-2,2-dimetil-2H-1 -benzopiran-3-ola, trans-6-etil-4-(4-fluorobenzoilmetilamino)-3,4-dihidro-2,2-dimetil-2H-1 -benzopiran-3 -ola, 6 trans-4-(4-fluorobenzoilamino)-6-pentafluoroetil-3,4-dihidro-2,2-dimetil-2H-1 -benzopiran-3-ola, trans-4-(4-fluorobenzoilamino)-3,4-dihidro-2,2-dimetil-6-fenilsulfonil-2H- l-benzopiran-3-ola, trans-4-(4-fluorobenzoilamino)-3,4-dihidro-2,2-dimetil-6-fenil-2H- l-benzopiran-3-ola, trans-6-etil-4S-(4-fluorobenzoilamino)-3,4-dihidro-2,2-dimetil-2H-1 -benzopiran-3R-ola, trans-4R-(4-fluorobenzoilamino)-3.4-dihidro-6-(l-hidroksietil)-2.2-dimetil-2H-1 -benzopiran-3 S-ola, trans-4S-(4-fluorobenzoilamino)-3,4-dihidro-6-(l-hidroksietil)-2,2-dimetil-2H-1 -benzopiran-3R-ola, trans-4-(4-fluorobenzoil-metilamino)-3,4-dihidro-2,2-dimetil-2H-1 -benzopiran-3-ola, trans-6-t-butil-4-(4-fluorobenzoilamino)-3,4-dihidro-2,2-dimetil-2H-1 -benzopiran-3 -ola, trans-4-(4-fluorobenzoilamino)-3,4-dihidro-2,2-dimetil-6-ciklopentil-2H-1-benzopiran-3-ola in trans-4-(4-fluorobenzoilamino)-3,4-dihidro-6-metoksi-2,2-dimetil-2H-1-benzopiran-3-ola 7 ali njihove farmacevtsko sprejemljive soli.
6. Uporaba po zahtevku 1, kjer je spojina izbrana izmed trans-6-ciano-3,4-dihidro-2,2-dimetil-4-(4-fluoro-benzoilamino)2H-1 -benzopiran-3 -ola, trans-6-kloro-3.4-dihidro-2.2-dimetil-4-(4-fluoro-benzoilamino)2H-1-benzopiran-3-ola, trans-6-trifluorometil-4-(4-fluorobenzoilamino)-3,4-dihidro-2,2-dimetil-2H-1 -benzopiran-3-ola, trans-6-ciano-4-(4-fluorobenzoilmetilamino)-3,4-dihidro-2,2-dimetil-2H-l- benzopiran-3-ola, trans-6-etilkarbonil-3,4-dihidro-2,2-dimetil-4-(4-fluorobenzoilamino)2H-l- benzopiran-3-ola, trans-6-etilkarbonil-3.4-dihidro-2,2-dimetil-4-(4-fluorobenzoilmetilamino)2H-l- benzopiran-3-ola, tmns-6-acetil-4-(4-fluorobenzoilmetilamino)-3,4-dihidro-2,2-dimetil-2H-1 -benzopiran-3-ola, ttans-6-ciano-3,4-dihidro-4-(4-fluorobenzoiletilamino)-2,2-dimetil-2H-1 -benzopiran-3-ola, trans-4-(4-fluorobenzoilamino)-3,4-dihidro-2,2-dimetil-7-nitro-2H-1 -benzopiran-3-ola, 8 trans-6-acetil-4R-(4-fluorobenzoilamino)-3,4-dihidro-2,2-dimetil-2H-1 -benzopiran-3 S-ola, trans-6-acetil-4S-(4-fluorobenzoilamino)-3,4-dihidro-2,2-dimetil-2H-1 -benzopiran-3R-ola, trans-6-ciano-4S-(4-fluorobenzoilamino)-3.4-dihidro-2,2-dimetil-2H-1 -benzopiran-3R-ola, trans-6-ciano-4-(4-fluorobenzoilamino)-3,4-dihidro-2,2,3-trimetil-2H-1 -benzopiran-3 -ola, trans-4-(4-fluorobenzoilamino)-3,4-dihidro-2,2-dimetil-6-nitro-2H- l-benzopiran-3-ola, trans-4-(4-fluorobenzoilamino)-3,4-dihidro-6-metoksikarbonil-2,2-dimetil-2H-1 -benzopiran-3 -ola, trans-6-fluoro-4-(4-fluorobenzoilamino)-3,4-dihidro-2,2-dimetil-2H-1-benzopiran-3-ola, trans-4-(4-fluorobenzoilmetilamino)-6-trifluorometil-3,4-dihidro-2,2-dimetil-2H-1 -benzopiran-3-ola, trans-4-(4-fluorobenzoilamino)-3,4-dihidro-6-iodo-2,2-dimetil-2H-l-benzopiran-3-ola in, trans-6-aminokarbonilmetil-4-(4-fluorobenzoilamino)-3,4-dihidro-2,2-dimetil-2H-1 -benzopiran-3 -ola, ali njihove farmacevtsko sprejemljive soli. 9
7. Uporaba po zahtevku 4, kjer sta R3 in R4 oba metil.
8. Uporaba po zahtevku 4, kjer je R5 hidroksi in sta R6 in R9 vodik.
9. Uporaba po zahtevku 4, kjer je X kisik.
10. Uporaba po zahtevku 4, kjer je Y CR[ in je Ri ciano, metoksi, trifluorometoksi, kloro, trifluorometil, etilkarbonil, acetil, vodik, metil, etil, izo-propil, terc.-butil, nitro, C2F5, metoksikarbonil, fenilsulfonil, fenil, fluoro, jodo, ciklopentil, aminokarbonilmetil in 1-hidroksietil in je R2 vodik.
11. Uporaba po zahtevku 4, kjer je Rj ciano, etil ali acetil in je R2 vodik.
12. Uporaba po zahtevku 4, kjer je R7 2-fluorofenil, 3-fluorofenil, 4-fluorofenil, 2.4- difluorofenil ali 3,4-difluorofenil.
13. Uporaba po zahtevku 4, kjer je Rg vodik, metil ali etil.
14. Uporaba po zahtevku 1 ali 4, kjer ima spojina 4S,3R konfiguracijo.
15. Uporaba po zahtevku 14, kjer je spojina trans-6-acetil-4S(4-fluorobenzoilamino)- 3.4- dihidro-2,2-dimetil-2H-l-benzopiran-3R-ol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SI9200378A SI9200378B (sl) | 1992-12-11 | 1992-12-11 | Fluorofenilbenzopirani in njihova uporaba pri zdravljenju nekaterih motenj centralnega živčnega sistema |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SI9200378A SI9200378B (sl) | 1992-12-11 | 1992-12-11 | Fluorofenilbenzopirani in njihova uporaba pri zdravljenju nekaterih motenj centralnega živčnega sistema |
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| Publication Number | Publication Date |
|---|---|
| SI9200378A SI9200378A (en) | 1994-06-30 |
| SI9200378B true SI9200378B (sl) | 2009-04-30 |
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| Application Number | Title | Priority Date | Filing Date |
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| SI9200378A SI9200378B (sl) | 1992-12-11 | 1992-12-11 | Fluorofenilbenzopirani in njihova uporaba pri zdravljenju nekaterih motenj centralnega živčnega sistema |
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| Country | Link |
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| SI (1) | SI9200378B (sl) |
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| Publication number | Publication date |
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| SI9200378A (en) | 1994-06-30 |
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