EA004035B1 - Производные изоиндолоиндолона, способ их получения и содержащие их фармацевтические композиции - Google Patents
Производные изоиндолоиндолона, способ их получения и содержащие их фармацевтические композиции Download PDFInfo
- Publication number
- EA004035B1 EA004035B1 EA200200241A EA200200241A EA004035B1 EA 004035 B1 EA004035 B1 EA 004035B1 EA 200200241 A EA200200241 A EA 200200241A EA 200200241 A EA200200241 A EA 200200241A EA 004035 B1 EA004035 B1 EA 004035B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- formula
- compound
- branched
- linear
- group
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 23
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 10
- 238000002360 preparation method Methods 0.000 title claims abstract description 4
- UNRFFBAJODEDDJ-UHFFFAOYSA-N C1=CC2=C3NC=CC3=CC=C2C2=C1C(=O)N=C2 Chemical class C1=CC2=C3NC=CC3=CC=C2C2=C1C(=O)N=C2 UNRFFBAJODEDDJ-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 60
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 9
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims abstract description 9
- 239000002253 acid Substances 0.000 claims abstract description 8
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000003118 aryl group Chemical group 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 230000003287 optical effect Effects 0.000 claims abstract description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- IRPIYZBBHNVOHO-UHFFFAOYSA-N 2-hydroxy-8,9-dimethoxyisoindolo[2,3-a]indol-6-one Chemical compound OC1=CC=C2N3C(=O)C(C=C(C(=C4)OC)OC)=C4C3=CC2=C1 IRPIYZBBHNVOHO-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000005530 alkylenedioxy group Chemical group 0.000 claims abstract description 4
- 239000003814 drug Substances 0.000 claims abstract description 4
- 229940079593 drug Drugs 0.000 claims abstract description 4
- 238000000926 separation method Methods 0.000 claims abstract description 4
- 239000004480 active ingredient Substances 0.000 claims abstract description 3
- 239000000654 additive Substances 0.000 claims abstract 3
- 230000000996 additive effect Effects 0.000 claims abstract 3
- APRMMGIMYPZNPC-UHFFFAOYSA-N 1,3-dimethoxyisoindolo[2,3-a]indol-6-one Chemical compound C12=CC=CC=C2C(=O)N2C1=CC1=C(OC)C=C(OC)C=C12 APRMMGIMYPZNPC-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000000969 carrier Substances 0.000 claims abstract 2
- 231100000252 nontoxic Toxicity 0.000 claims abstract 2
- 230000003000 nontoxic effect Effects 0.000 claims abstract 2
- 238000011282 treatment Methods 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 208000035475 disorder Diseases 0.000 claims description 6
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 238000004140 cleaning Methods 0.000 claims 1
- 125000006823 (C1-C6) acyl group Chemical group 0.000 abstract description 2
- 238000000746 purification Methods 0.000 abstract description 2
- 238000007363 ring formation reaction Methods 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 230000001193 melatoninergic effect Effects 0.000 abstract 1
- 230000008929 regeneration Effects 0.000 abstract 1
- 238000011069 regeneration method Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 22
- 238000002844 melting Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- XLYPHUGUKGMURE-UHFFFAOYSA-N 5-hydroxy-2-nitrobenzaldehyde Chemical compound OC1=CC=C([N+]([O-])=O)C(C=O)=C1 XLYPHUGUKGMURE-UHFFFAOYSA-N 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- DRLFMBDRBRZALE-UHFFFAOYSA-N melatonin Chemical compound COC1=CC=C2NC=C(CCNC(C)=O)C2=C1 DRLFMBDRBRZALE-UHFFFAOYSA-N 0.000 description 5
- 238000004452 microanalysis Methods 0.000 description 5
- 230000000144 pharmacologic effect Effects 0.000 description 5
- 102000005962 receptors Human genes 0.000 description 5
- 108020003175 receptors Proteins 0.000 description 5
- 208000019116 sleep disease Diseases 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- YJPIGAIKUZMOQA-UHFFFAOYSA-N Melatonin Natural products COC1=CC=C2N(C(C)=O)C=C(CCN)C2=C1 YJPIGAIKUZMOQA-UHFFFAOYSA-N 0.000 description 4
- 229960003987 melatonin Drugs 0.000 description 4
- 230000007170 pathology Effects 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- HWIZGBVJDMPJRO-UHFFFAOYSA-N 6-hydroxy-3h-2-benzofuran-1-one Chemical compound OC1=CC=C2COC(=O)C2=C1 HWIZGBVJDMPJRO-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 102000001419 Melatonin receptor Human genes 0.000 description 3
- 108050009605 Melatonin receptor Proteins 0.000 description 3
- 208000008589 Obesity Diseases 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 3
- -1 alkoxy radical Chemical class 0.000 description 3
- 230000027288 circadian rhythm Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 230000001771 impaired effect Effects 0.000 description 3
- JBXRLVPILRXPNH-UHFFFAOYSA-N indol-6-one Chemical compound O=C1C=CC2=CC=NC2=C1 JBXRLVPILRXPNH-UHFFFAOYSA-N 0.000 description 3
- 206010022437 insomnia Diseases 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 235000020824 obesity Nutrition 0.000 description 3
- 208000012672 seasonal affective disease Diseases 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- FJPMLTZXTKBVKX-UHFFFAOYSA-N 4,6-Dimethoxy-phthalide Chemical compound COC1=CC(OC)=CC2=C1COC2=O FJPMLTZXTKBVKX-UHFFFAOYSA-N 0.000 description 2
- UKFAWRZYFYOXEG-UHFFFAOYSA-N 5,6-dimethoxy-3H-isobenzofuran-1-one Chemical compound C1=C(OC)C(OC)=CC2=C1C(=O)OC2 UKFAWRZYFYOXEG-UHFFFAOYSA-N 0.000 description 2
- PTWPWUVEQZXOFJ-UHFFFAOYSA-N 7-hydroxy-3h-2-benzofuran-1-one Chemical compound OC1=CC=CC2=C1C(=O)OC2 PTWPWUVEQZXOFJ-UHFFFAOYSA-N 0.000 description 2
- 208000024827 Alzheimer disease Diseases 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 208000018737 Parkinson disease Diseases 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000002249 anxiolytic agent Substances 0.000 description 2
- 230000000949 anxiolytic effect Effects 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 206010012601 diabetes mellitus Diseases 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000002526 effect on cardiovascular system Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229940088597 hormone Drugs 0.000 description 2
- 239000005556 hormone Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000016087 ovulation Effects 0.000 description 2
- 208000022925 sleep disturbance Diseases 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- AIFAWXWFXVGQRW-UHFFFAOYSA-M (5,6-dimethoxy-3-oxo-1h-2-benzofuran-1-yl)-triphenylphosphanium;bromide Chemical compound [Br-].O1C(=O)C=2C=C(OC)C(OC)=CC=2C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 AIFAWXWFXVGQRW-UHFFFAOYSA-M 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- WPRBUGIFHCMJKG-UHFFFAOYSA-N 16-hydroxy-5,7-dioxa-1-azapentacyclo[10.7.0.02,10.04,8.013,18]nonadeca-2,4(8),9,11,13(18),14,16-heptaen-19-one Chemical compound C1=C2N3C(=O)C4=CC(O)=CC=C4C3=CC2=CC2=C1OCO2 WPRBUGIFHCMJKG-UHFFFAOYSA-N 0.000 description 1
- OWXQQVBJEAJOBD-UHFFFAOYSA-N 2,7,10-trihydroxyisoindolo[2,3-a]indol-6-one Chemical compound OC1=CC=C(O)C2=C1C1=CC3=CC(O)=CC=C3N1C2=O OWXQQVBJEAJOBD-UHFFFAOYSA-N 0.000 description 1
- UFMFGBMKHDMOTF-UHFFFAOYSA-N 2,7-dihydroxy-10-methoxyisoindolo[2,3-a]indol-6-one Chemical compound OC1=CC=C2N3C(=O)C(C(O)=CC=C4OC)=C4C3=CC2=C1 UFMFGBMKHDMOTF-UHFFFAOYSA-N 0.000 description 1
- RXDSFAJOOCXCSI-UHFFFAOYSA-N 2,7-dihydroxyisoindolo[2,3-a]indol-6-one Chemical compound C12=CC3=CC(O)=CC=C3N2C(=O)C2=C1C=CC=C2O RXDSFAJOOCXCSI-UHFFFAOYSA-N 0.000 description 1
- NNMPLRXTMYAJJC-UHFFFAOYSA-N 2,8-dihydroxyisoindolo[2,3-a]indol-6-one Chemical compound OC1=CC=C2N3C(=O)C4=CC(O)=CC=C4C3=CC2=C1 NNMPLRXTMYAJJC-UHFFFAOYSA-N 0.000 description 1
- QQSPFGXBBDZYBI-UHFFFAOYSA-N 2-(5-hydroxy-1h-indol-2-yl)-4,5-dimethoxybenzoic acid Chemical compound C1=C(OC)C(OC)=CC(C(O)=O)=C1C1=CC2=CC(O)=CC=C2N1 QQSPFGXBBDZYBI-UHFFFAOYSA-N 0.000 description 1
- MLDPDFBFSLRRTK-UHFFFAOYSA-N 2-(8,9-dimethoxy-6-oxoisoindolo[2,1-a]indol-1-yl)propanoic acid Chemical compound C1=CC=C2N3C(=O)C(C=C(C(=C4)OC)OC)=C4C3=CC2=C1C(C)C(O)=O MLDPDFBFSLRRTK-UHFFFAOYSA-N 0.000 description 1
- SKHSZPJWOKSLCB-UHFFFAOYSA-N 2-hydroxy-7,10-dimethoxyisoindolo[2,3-a]indol-6-one Chemical compound OC1=CC=C2N(C(=O)C=3C(OC)=CC=C(OC)C=33)C3=CC2=C1 SKHSZPJWOKSLCB-UHFFFAOYSA-N 0.000 description 1
- YKLHOQNHOKVXOY-UHFFFAOYSA-N 2-hydroxy-8,10-dimethoxyisoindolo[2,3-a]indol-6-one Chemical compound OC1=CC=C2N3C(=O)C(C=C(C=C4OC)OC)=C4C3=CC2=C1 YKLHOQNHOKVXOY-UHFFFAOYSA-N 0.000 description 1
- BRFFHYIWDJAXGJ-UHFFFAOYSA-N 2-hydroxy-8-methoxyisoindolo[2,3-a]indol-6-one Chemical compound OC1=CC=C2N3C(=O)C4=CC(OC)=CC=C4C3=CC2=C1 BRFFHYIWDJAXGJ-UHFFFAOYSA-N 0.000 description 1
- JGZQPIGFZOWNRX-UHFFFAOYSA-N 3-(2-formyl-3-nitrophenyl)propanoic acid Chemical compound OC(=O)CCC1=CC=CC([N+]([O-])=O)=C1C=O JGZQPIGFZOWNRX-UHFFFAOYSA-N 0.000 description 1
- VVMDRNIEBWCPRX-UHFFFAOYSA-N 3-[(2-amino-5-hydroxyphenyl)methylidene]-5,6-dimethoxy-2-benzofuran-1-one Chemical compound C1=2C=C(OC)C(OC)=CC=2C(=O)OC1=CC1=CC(O)=CC=C1N VVMDRNIEBWCPRX-UHFFFAOYSA-N 0.000 description 1
- AXNRNAXJBJIXIV-UHFFFAOYSA-N 3-[(5-hydroxy-2-nitrophenyl)methylidene]-5,6-dimethoxy-2-benzofuran-1-one Chemical compound C1=2C=C(OC)C(OC)=CC=2C(=O)OC1=CC1=CC(O)=CC=C1[N+]([O-])=O AXNRNAXJBJIXIV-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- CRNIEXJWYHGTGR-UHFFFAOYSA-N 3-bromo-5,6-dimethoxy-3h-2-benzofuran-1-one Chemical compound C1=C(OC)C(OC)=CC2=C1C(=O)OC2Br CRNIEXJWYHGTGR-UHFFFAOYSA-N 0.000 description 1
- KGXOQXGHUJDCCU-UHFFFAOYSA-N 4,6-dimethyl-3-oxo-1h-2-benzofuran-5-carboxylic acid Chemical compound CC1=C(C(O)=O)C(C)=CC2=C1C(=O)OC2 KGXOQXGHUJDCCU-UHFFFAOYSA-N 0.000 description 1
- HFWBBGYPGAWRIT-UHFFFAOYSA-N 4,7-dihydroxy-3h-2-benzofuran-1-one Chemical compound OC1=CC=C(O)C2=C1COC2=O HFWBBGYPGAWRIT-UHFFFAOYSA-N 0.000 description 1
- ABFJCCZUMNBAAI-UHFFFAOYSA-N 4,7-dimethoxy-3h-2-benzofuran-1-one Chemical compound COC1=CC=C(OC)C2=C1COC2=O ABFJCCZUMNBAAI-UHFFFAOYSA-N 0.000 description 1
- KWHZIUXAQFIEPP-UHFFFAOYSA-N 4-benzyl-5-hydroxy-2-nitrobenzaldehyde Chemical compound OC1=CC(C=O)=C([N+]([O-])=O)C=C1CC1=CC=CC=C1 KWHZIUXAQFIEPP-UHFFFAOYSA-N 0.000 description 1
- HTONKCSNONAUAZ-UHFFFAOYSA-N 4-methoxy-3h-2-benzofuran-1-one Chemical compound COC1=CC=CC2=C1COC2=O HTONKCSNONAUAZ-UHFFFAOYSA-N 0.000 description 1
- SBRSQZDGPDFDNI-UHFFFAOYSA-N 5-hydroxy-6-methoxy-3h-2-benzofuran-1-one Chemical compound C1=C(O)C(OC)=CC2=C1COC2=O SBRSQZDGPDFDNI-UHFFFAOYSA-N 0.000 description 1
- BNTDDWPHSMILHQ-UHFFFAOYSA-N 5-methoxy-2-nitrobenzaldehyde Chemical compound COC1=CC=C([N+]([O-])=O)C(C=O)=C1 BNTDDWPHSMILHQ-UHFFFAOYSA-N 0.000 description 1
- 229940097276 5-methoxytryptamine Drugs 0.000 description 1
- YEGQYRDJSUITQT-UHFFFAOYSA-N 6-methoxy-3h-2-benzofuran-1-one Chemical compound COC1=CC=C2COC(=O)C2=C1 YEGQYRDJSUITQT-UHFFFAOYSA-N 0.000 description 1
- NRZWECORTTWSEF-UHFFFAOYSA-N 6-nitro-1,3-benzodioxole-5-carbaldehyde Chemical compound C1=C(C=O)C([N+](=O)[O-])=CC2=C1OCO2 NRZWECORTTWSEF-UHFFFAOYSA-N 0.000 description 1
- VBVSGUYGUBBWFG-UHFFFAOYSA-N 7-hydroxy-4-methoxy-3h-2-benzofuran-1-one Chemical compound COC1=CC=C(O)C2=C1COC2=O VBVSGUYGUBBWFG-UHFFFAOYSA-N 0.000 description 1
- KNYHQEDKIVXXOI-UHFFFAOYSA-N 8-hydroxy-2-methoxyisoindolo[2,3-a]indol-6-one Chemical compound OC1=CC=C2C3=CC4=CC(OC)=CC=C4N3C(=O)C2=C1 KNYHQEDKIVXXOI-UHFFFAOYSA-N 0.000 description 1
- 208000000044 Amnesia Diseases 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 208000027559 Appetite disease Diseases 0.000 description 1
- LSPHULWDVZXLIL-UHFFFAOYSA-N Camphoric acid Natural products CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 description 1
- 206010008190 Cerebrovascular accident Diseases 0.000 description 1
- 241000699800 Cricetinae Species 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 208000019454 Feeding and Eating disease Diseases 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 208000026139 Memory disease Diseases 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 206010033664 Panic attack Diseases 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 206010039966 Senile dementia Diseases 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 230000001270 agonistic effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 230000036528 appetite Effects 0.000 description 1
- 235000019789 appetite Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical compound CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 229960004106 citric acid Drugs 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 210000002249 digestive system Anatomy 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 230000002519 immonomodulatory effect Effects 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000004807 localization Effects 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229940098895 maleic acid Drugs 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 230000006984 memory degeneration Effects 0.000 description 1
- 208000023060 memory loss Diseases 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 208000019906 panic disease Diseases 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000021907 regulation of circadian rhythm Effects 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 230000009834 selective interaction Effects 0.000 description 1
- 230000036299 sexual function Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/06—Peri-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Psychiatry (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Obesity (AREA)
- Cardiology (AREA)
- Hospice & Palliative Care (AREA)
- Child & Adolescent Psychology (AREA)
- Emergency Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Psychology (AREA)
- Anesthesiology (AREA)
- Reproductive Health (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0103293A FR2821843B1 (fr) | 2001-03-12 | 2001-03-12 | Nouveaux derives d'isoindoloindolones, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA200200241A1 EA200200241A1 (ru) | 2002-10-31 |
| EA004035B1 true EA004035B1 (ru) | 2003-12-25 |
Family
ID=8860976
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA200200241A EA004035B1 (ru) | 2001-03-12 | 2002-03-11 | Производные изоиндолоиндолона, способ их получения и содержащие их фармацевтические композиции |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US6465660B1 (enExample) |
| EP (1) | EP1241169B1 (enExample) |
| JP (1) | JP3842151B2 (enExample) |
| KR (1) | KR100450313B1 (enExample) |
| CN (1) | CN1159316C (enExample) |
| AR (1) | AR034583A1 (enExample) |
| AT (1) | ATE248171T1 (enExample) |
| AU (1) | AU779702B2 (enExample) |
| BR (1) | BR0200721A (enExample) |
| CA (1) | CA2376876C (enExample) |
| DE (1) | DE60200023T2 (enExample) |
| DK (1) | DK1241169T3 (enExample) |
| EA (1) | EA004035B1 (enExample) |
| ES (1) | ES2206438T3 (enExample) |
| FR (1) | FR2821843B1 (enExample) |
| HK (1) | HK1049000B (enExample) |
| HU (1) | HUP0200913A3 (enExample) |
| MX (1) | MXPA02002601A (enExample) |
| NO (1) | NO20021198L (enExample) |
| NZ (1) | NZ517742A (enExample) |
| PL (1) | PL352750A1 (enExample) |
| PT (1) | PT1241169E (enExample) |
| SI (1) | SI1241169T1 (enExample) |
| ZA (1) | ZA200202030B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2387655C2 (ru) * | 2004-08-09 | 2010-04-27 | Бристол-Маерс Сквибб Компани | Ингибиторы репликации вируса гепатита с |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2826009B1 (fr) * | 2001-06-13 | 2003-08-15 | Servier Lab | Nouveaux derives d'indenoindolones, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| EP1537113B9 (en) * | 2002-06-21 | 2010-05-26 | Suven Life Sciences Limited | Arylalkyl indoles having serotonin receptor affinity useful as therapeutic agents, process for their preparation and pharmaceutical compositions containing them |
| CA2490002C (en) * | 2002-06-21 | 2009-07-07 | Suven Life Sciences Limited | Novel tetracyclic arylcarbonyl indoles having serotonin receptor affinity useful as therapeutic agents, process for their preparation and pharmaceutical compositions containing them |
| ES2425143T3 (es) * | 2002-11-28 | 2013-10-11 | Suven Life Sciences Limited | N-Arilsulfonil-3-aminoalcoxiindoles |
| KR100739987B1 (ko) * | 2002-12-18 | 2007-07-16 | 수벤 라이프 사이언시스 리미티드 | 세로토닌 수용체 친화력을 가지는 테트라사이클릭 3-치환인돌 |
| ES2580702B1 (es) | 2015-02-25 | 2017-06-08 | Palobiofarma, S.L. | Derivados de 2-aminopiridina como antagonistas del receptor A2b de adenosina y ligandos del receptor MT3 de melatonina |
| JP2025530666A (ja) | 2022-09-02 | 2025-09-17 | デックスコム・インコーポレーテッド | 連続分析物センサデバイス及び方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5377098A (en) * | 1976-12-16 | 1978-07-08 | Sumitomo Chem Co Ltd | Preparation of indoloisoquinoline derivative |
| US4452808A (en) * | 1982-12-07 | 1984-06-05 | Smithkline Beckman Corporation | 4-Aminoalkyl-2(3H)-indolones |
| US5441955A (en) * | 1993-11-19 | 1995-08-15 | Pathogenesis Corporation | Indolo[2,1-biquinazoline-6,12-dione antibacterial compounds and methods of use thereof |
| FR2743365A1 (fr) * | 1996-01-10 | 1997-07-11 | Rhone Poulenc Rorer Sa | Derives de 5h,10h-imidazo(1,2-a)indolo(3,2-e)pyrazine-4-one, leur preparation et les medicaments les contenant |
| US20020040018A1 (en) * | 2000-06-23 | 2002-04-04 | Jones Robert M. | Subtype selective melatonergics |
-
2001
- 2001-03-12 FR FR0103293A patent/FR2821843B1/fr not_active Expired - Fee Related
-
2002
- 2002-02-26 US US10/083,074 patent/US6465660B1/en not_active Expired - Fee Related
- 2002-03-09 KR KR10-2002-0012699A patent/KR100450313B1/ko not_active Expired - Fee Related
- 2002-03-11 CA CA002376876A patent/CA2376876C/fr not_active Expired - Fee Related
- 2002-03-11 PT PT02290598T patent/PT1241169E/pt unknown
- 2002-03-11 NZ NZ517742A patent/NZ517742A/xx unknown
- 2002-03-11 ES ES02290598T patent/ES2206438T3/es not_active Expired - Lifetime
- 2002-03-11 NO NO20021198A patent/NO20021198L/no not_active Application Discontinuation
- 2002-03-11 EA EA200200241A patent/EA004035B1/ru unknown
- 2002-03-11 JP JP2002065233A patent/JP3842151B2/ja not_active Expired - Fee Related
- 2002-03-11 AR ARP020100863A patent/AR034583A1/es active IP Right Grant
- 2002-03-11 SI SI200230002T patent/SI1241169T1/xx unknown
- 2002-03-11 AT AT02290598T patent/ATE248171T1/de not_active IP Right Cessation
- 2002-03-11 MX MXPA02002601A patent/MXPA02002601A/es active IP Right Grant
- 2002-03-11 HU HU0200913A patent/HUP0200913A3/hu unknown
- 2002-03-11 DE DE60200023T patent/DE60200023T2/de not_active Expired - Fee Related
- 2002-03-11 BR BR0200721-5A patent/BR0200721A/pt not_active IP Right Cessation
- 2002-03-11 DK DK02290598T patent/DK1241169T3/da active
- 2002-03-11 EP EP02290598A patent/EP1241169B1/fr not_active Expired - Lifetime
- 2002-03-12 CN CNB021070547A patent/CN1159316C/zh not_active Expired - Fee Related
- 2002-03-12 AU AU23242/02A patent/AU779702B2/en not_active Ceased
- 2002-03-12 PL PL02352750A patent/PL352750A1/xx not_active Application Discontinuation
- 2002-03-12 ZA ZA200202030A patent/ZA200202030B/xx unknown
-
2003
- 2003-02-18 HK HK03101182.3A patent/HK1049000B/zh not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2387655C2 (ru) * | 2004-08-09 | 2010-04-27 | Бристол-Маерс Сквибб Компани | Ингибиторы репликации вируса гепатита с |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR910001042B1 (ko) | 4-아미노알킬-2(3h)-인돌론 및 이의 제조방법 | |
| JPWO1998030548A1 (ja) | ５−ＨＴ▲下２ｃ▼受容体作用薬及びアミノアルキルインダゾール誘導体 | |
| JPH05505599A (ja) | 治療上有用な複素環インドール化合物類 | |
| JPWO2002074746A1 (ja) | ベンゾアゼピン誘導体 | |
| CA2152630C (en) | Enantiomers of carbazole derivatives as 5-ht1-like agonists | |
| JPH03291275A (ja) | 新規の（１−ナフチル）ピペラジン誘導体、その製造方法およびそれを含有する薬剤組成物 | |
| US5840764A (en) | Substituted hydroxy-anilino derivatives of cyclobutene-3,4-diones | |
| JPH06510056A (ja) | 新規なイサチンオキシム誘導体類、その製造および使用 | |
| EA004035B1 (ru) | Производные изоиндолоиндолона, способ их получения и содержащие их фармацевтические композиции | |
| JPH06506442A (ja) | １−（４−アシルアミノフェニル）−７，８−メチレンジオキシ−５ｈ−２，３−ベンゾ−ジアゼピン誘導体及びその酸付加塩、それを含む製薬学的組成物及びその製造方法 | |
| WO1998033763A1 (en) | Substituted hydroxy-anilino derivatives of cyclobutene-3,4-diones | |
| JP3886829B2 (ja) | 新規インデノインドロン化合物、それらの調製方法およびそれらを含む医薬組成物 | |
| JPH02167279A (ja) | アポビンカミン酸誘導体 | |
| US4778812A (en) | 2,3-dihydro-9-methyl-1H-pyrrolo[1,2-a]indol-1-amines and derivatives thereof | |
| BG107864A (bg) | Производни на заместени пиразинохиноксалини като агонисти и антагонисти на серотонинов рецептор | |
| CA2317515A1 (en) | Oxazole derivatives as serotonin-1a receptor agonists | |
| JP2008013558A (ja) | 新規ナフタレン化合物、その製造法、およびそれを含有する薬学的組成物 | |
| JPS6130588A (ja) | ベンゾ〔ｃ〕〔１，８〕ナフチリジン、その製造方法及びその使用、並びにこれらの化合物を含有する調製剤 | |
| JPH02504629A (ja) | 縮合ベンズアゼピン | |
| CA2756876A1 (en) | A process for the preparation of frovatriptan and frovatriptan succinate and their synthetic intermediates | |
| NZ299232A (en) | (+)-6-carboxamido-3-n-ethylamino-1,2,3,4- tetrahydrocarbazoles; medicaments thereof | |
| JPWO1995026187A1 (ja) | 抗不安薬 |