DE60002043T2 - 4-oxo-3,5-dihydro-4h-pyridazino[4,5-b]indol-1-carboxamid-derivate, ihre herstellung und therapeutische verwendung - Google Patents
4-oxo-3,5-dihydro-4h-pyridazino[4,5-b]indol-1-carboxamid-derivate, ihre herstellung und therapeutische verwendung Download PDFInfo
- Publication number
- DE60002043T2 DE60002043T2 DE60002043T DE60002043T DE60002043T2 DE 60002043 T2 DE60002043 T2 DE 60002043T2 DE 60002043 T DE60002043 T DE 60002043T DE 60002043 T DE60002043 T DE 60002043T DE 60002043 T2 DE60002043 T2 DE 60002043T2
- Authority
- DE
- Germany
- Prior art keywords
- mmol
- oxo
- dihydro
- methyl
- pyridazino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 230000001225 therapeutic effect Effects 0.000 title description 3
- 238000002360 preparation method Methods 0.000 title description 2
- KUVBJWGMAORROJ-UHFFFAOYSA-N 4-oxo-3,5-dihydropyridazino[4,5-b]indole-1-carboxamide Chemical class N1C2=CC=CC=C2C2=C1C(=O)NN=C2C(=O)N KUVBJWGMAORROJ-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 42
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 3
- 125000002757 morpholinyl group Chemical group 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000012876 carrier material Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 230000008018 melting Effects 0.000 description 11
- 238000002844 melting Methods 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 238000004440 column chromatography Methods 0.000 description 10
- 239000003480 eluent Substances 0.000 description 10
- 239000000377 silicon dioxide Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000004696 coordination complex Chemical class 0.000 description 5
- YAIVDGZDNCFDNH-UHFFFAOYSA-N ethyl 6-chloro-3-(2-ethoxy-2-oxoacetyl)-1-methylindole-2-carboxylate Chemical compound ClC1=CC=C2C(C(=O)C(=O)OCC)=C(C(=O)OCC)N(C)C2=C1 YAIVDGZDNCFDNH-UHFFFAOYSA-N 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 3
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 210000000256 facial nerve Anatomy 0.000 description 3
- 238000011835 investigation Methods 0.000 description 3
- 230000000508 neurotrophic effect Effects 0.000 description 3
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- 239000002904 solvent Substances 0.000 description 3
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 2
- RAFKIFPDMATLBG-UHFFFAOYSA-N 7-chloro-3-(3-chlorophenyl)-5-methyl-1-(pyrrolidine-1-carbonyl)pyridazino[4,5-b]indol-4-one Chemical compound O=C1C=2N(C)C3=CC(Cl)=CC=C3C=2C(C(=O)N2CCCC2)=NN1C1=CC=CC(Cl)=C1 RAFKIFPDMATLBG-UHFFFAOYSA-N 0.000 description 2
- IEVSHILPTOJQFZ-UHFFFAOYSA-N 7-chloro-n,n,5-trimethyl-4-oxo-3-phenylpyridazino[4,5-b]indole-1-carboxamide Chemical compound O=C1C=2N(C)C3=CC(Cl)=CC=C3C=2C(C(=O)N(C)C)=NN1C1=CC=CC=C1 IEVSHILPTOJQFZ-UHFFFAOYSA-N 0.000 description 2
- HJRLVCHTLOOVRV-UHFFFAOYSA-N 7-chloro-n,n-diethyl-3-(3-methoxyphenyl)-5-methyl-4-oxopyridazino[4,5-b]indole-1-carboxamide Chemical compound O=C1C=2N(C)C3=CC(Cl)=CC=C3C=2C(C(=O)N(CC)CC)=NN1C1=CC=CC(OC)=C1 HJRLVCHTLOOVRV-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 208000034189 Sclerosis Diseases 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 229940049706 benzodiazepine Drugs 0.000 description 2
- 230000027455 binding Effects 0.000 description 2
- 230000002354 daily effect Effects 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- QMVJTCIUKISOGR-UHFFFAOYSA-N ethyl 6-chloro-1-methylindole-2-carboxylate Chemical compound C1=C(Cl)C=C2N(C)C(C(=O)OCC)=CC2=C1 QMVJTCIUKISOGR-UHFFFAOYSA-N 0.000 description 2
- BZTTWVSCPUWUPH-UHFFFAOYSA-N ethyl 7-chloro-3-(3-chlorophenyl)-5-methyl-4-oxopyridazino[4,5-b]indole-1-carboxylate Chemical compound O=C1C=2N(C)C3=CC(Cl)=CC=C3C=2C(C(=O)OCC)=NN1C1=CC=CC(Cl)=C1 BZTTWVSCPUWUPH-UHFFFAOYSA-N 0.000 description 2
- OZXKUHMJKZOWAA-UHFFFAOYSA-N ethyl 7-chloro-3-(3-methoxyphenyl)-5-methyl-4-oxopyridazino[4,5-b]indole-1-carboxylate Chemical compound O=C1C=2N(C)C3=CC(Cl)=CC=C3C=2C(C(=O)OCC)=NN1C1=CC=CC(OC)=C1 OZXKUHMJKZOWAA-UHFFFAOYSA-N 0.000 description 2
- JJCGYLAKDUJYLK-UHFFFAOYSA-N ethyl 7-chloro-5-methyl-4-oxo-3-phenylpyridazino[4,5-b]indole-1-carboxylate Chemical compound O=C1C=2N(C)C3=CC(Cl)=CC=C3C=2C(C(=O)OCC)=NN1C1=CC=CC=C1 JJCGYLAKDUJYLK-UHFFFAOYSA-N 0.000 description 2
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- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 2
- 229940067157 phenylhydrazine Drugs 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
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- 238000000926 separation method Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 2
- CRRIAWUJYMLJOE-UHFFFAOYSA-N (3-chlorophenyl)hydrazine;hydron;chloride Chemical compound Cl.NNC1=CC=CC(Cl)=C1 CRRIAWUJYMLJOE-UHFFFAOYSA-N 0.000 description 1
- SKVGLOFWEJFQKU-UHFFFAOYSA-N (3-fluorophenyl)hydrazine;hydron;chloride Chemical compound Cl.NNC1=CC=CC(F)=C1 SKVGLOFWEJFQKU-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- MANJIGKYCYWWBD-UHFFFAOYSA-N 2-chloro-2-oxoacetic acid Chemical compound OC(=O)C(Cl)=O MANJIGKYCYWWBD-UHFFFAOYSA-N 0.000 description 1
- BKPSJOSKWKTWAG-UHFFFAOYSA-N 6-chloro-1h-indole-2-carboxylic acid Chemical class C1=C(Cl)C=C2NC(C(=O)O)=CC2=C1 BKPSJOSKWKTWAG-UHFFFAOYSA-N 0.000 description 1
- QPPVZPAYYSTDAN-UHFFFAOYSA-N 7-chloro-3-(3-chlorophenyl)-n,n,5-trimethyl-4-oxopyridazino[4,5-b]indole-1-carboxamide Chemical compound O=C1C=2N(C)C3=CC(Cl)=CC=C3C=2C(C(=O)N(C)C)=NN1C1=CC=CC(Cl)=C1 QPPVZPAYYSTDAN-UHFFFAOYSA-N 0.000 description 1
- FFAPQAZWUVSBCM-UHFFFAOYSA-N 7-chloro-3-(3-fluorophenyl)-n,n,5-trimethyl-4-oxopyridazino[4,5-b]indole-1-carboxamide Chemical compound O=C1C=2N(C)C3=CC(Cl)=CC=C3C=2C(C(=O)N(C)C)=NN1C1=CC=CC(F)=C1 FFAPQAZWUVSBCM-UHFFFAOYSA-N 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 206010002027 Amyotrophy Diseases 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 208000021401 Facial Nerve injury Diseases 0.000 description 1
- 102000004300 GABA-A Receptors Human genes 0.000 description 1
- 108090000839 GABA-A Receptors Proteins 0.000 description 1
- 208000033463 Ischaemic neuropathy Diseases 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 108010025020 Nerve Growth Factor Proteins 0.000 description 1
- 102000007072 Nerve Growth Factors Human genes 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
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- 150000005690 diesters Chemical class 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- FSMZLIBWSAMADK-UHFFFAOYSA-N ethyl 6-chloro-1h-indole-2-carboxylate Chemical compound C1=C(Cl)C=C2NC(C(=O)OCC)=CC2=C1 FSMZLIBWSAMADK-UHFFFAOYSA-N 0.000 description 1
- PEYVMWBTZRUKBN-UHFFFAOYSA-N ethyl 7-chloro-3-(3-fluorophenyl)-5-methyl-4-oxopyridazino[4,5-b]indole-1-carboxylate Chemical compound O=C1C=2N(C)C3=CC(Cl)=CC=C3C=2C(C(=O)OCC)=NN1C1=CC=CC(F)=C1 PEYVMWBTZRUKBN-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- OEXNQFWEJRSZBW-UHFFFAOYSA-N ethyl indole-1-carboxylate Chemical compound C1=CC=C2N(C(=O)OCC)C=CC2=C1 OEXNQFWEJRSZBW-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
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- 230000008014 freezing Effects 0.000 description 1
- 239000007897 gelcap Substances 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- GMXFZBZOVZOYNQ-UHFFFAOYSA-N hydron;(3-methoxyphenyl)hydrazine;chloride Chemical compound Cl.COC1=CC=CC(NN)=C1 GMXFZBZOVZOYNQ-UHFFFAOYSA-N 0.000 description 1
- 230000002519 immonomodulatory effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- CQILOHWHIWNQOE-UHFFFAOYSA-N indole-1-carboxamide Chemical compound C1=CC=C2N(C(=O)N)C=CC2=C1 CQILOHWHIWNQOE-UHFFFAOYSA-N 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
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- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
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- 230000001537 neural effect Effects 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 201000001119 neuropathy Diseases 0.000 description 1
- 230000007823 neuropathy Effects 0.000 description 1
- 230000000324 neuroprotective effect Effects 0.000 description 1
- 239000003900 neurotrophic factor Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 208000027232 peripheral nervous system disease Diseases 0.000 description 1
- 208000033808 peripheral neuropathy Diseases 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003334 secondary amides Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
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- 239000003826 tablet Substances 0.000 description 1
- 150000003511 tertiary amides Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000000472 traumatic effect Effects 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 238000005303 weighing Methods 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
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9900805A FR2788776B1 (fr) | 1999-01-26 | 1999-01-26 | Derives de 4-oxo-3, 5-dihydro-4h-pyridazino [4,5-b] indole-1 -carboxamide, leur preparation et leur application en therapeutique |
| FR9900805 | 1999-01-26 | ||
| PCT/FR2000/000134 WO2000044751A1 (fr) | 1999-01-26 | 2000-01-21 | DERIVES DE 4-OXO-3,5-DIHYDRO-4H-PYRIDAZINO[4,5-b]INDOLE-1-CARBOXAMIDE, LEUR PREPARATION ET LEUR APPLICATION EN THERAPEUTIQUE |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60002043D1 DE60002043D1 (de) | 2003-05-15 |
| DE60002043T2 true DE60002043T2 (de) | 2004-02-19 |
Family
ID=9541211
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60002043T Expired - Lifetime DE60002043T2 (de) | 1999-01-26 | 2000-01-21 | 4-oxo-3,5-dihydro-4h-pyridazino[4,5-b]indol-1-carboxamid-derivate, ihre herstellung und therapeutische verwendung |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6451795B1 (enExample) |
| EP (1) | EP1149101B1 (enExample) |
| JP (1) | JP4574860B2 (enExample) |
| AR (1) | AR030016A1 (enExample) |
| AT (1) | ATE236905T1 (enExample) |
| AU (1) | AU3057800A (enExample) |
| CO (1) | CO5160255A1 (enExample) |
| DE (1) | DE60002043T2 (enExample) |
| ES (1) | ES2194696T3 (enExample) |
| FR (1) | FR2788776B1 (enExample) |
| WO (1) | WO2000044751A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2788696B1 (fr) * | 1999-01-26 | 2004-03-05 | Synthelabo | Utilisation de derives de pyridazino [4,5-b] indole-1-acetamide pour la preparation de medicaments destines aux maladies du systeme nerveux central |
| FR2811990A1 (fr) * | 2000-07-24 | 2002-01-25 | Sanofi Synthelabo | DERIVES DE 1-(4-OXO-3,5-DIHYDRO-4H-PYRIDAZINO[4,5-b]INDOLE-1 -CARBONYL)PIPERAZINE, LEUR PREPARATION ET LEUR APPLICATION EN THERAPEUTIQUE |
| FR2833953B1 (fr) * | 2001-12-21 | 2004-12-03 | Sanofi Synthelabo | DERIVES DE 3-HETEROARYL-3,5-DIHYDRO-4-OXO-4H-PYRIDAZINO [4,5-b]INDOLE-1-CARBOXAMIDE, LEUR PREPARATION ET LEUR APPLICATION EN THERAPEUTIQUE |
| FR2838124B1 (fr) * | 2002-04-03 | 2004-05-28 | Sanofi Synthelabo | Derives de 3-heteroaryl-3,5-dihydro-4-oxo-4h-pyridazino [4,5-b]indole-1-acetamide, leur preparation et leur application en therapeutique |
| GB0523506D0 (en) * | 2005-11-18 | 2005-12-28 | Hammersmith Imanet Ltd | Novel in vivo imaging compounds |
| GB0818738D0 (en) * | 2008-10-13 | 2008-11-19 | Ge Healthcare Ltd | Imaging neuroflammation |
| GB0905328D0 (en) | 2009-03-27 | 2009-05-13 | Ge Healthcare Ltd | Indole derivatives |
| CN102834379B (zh) * | 2010-03-26 | 2014-12-24 | 通用电气健康护理有限公司 | 作为pbr配体的三环吲哚衍生物 |
| US9220795B2 (en) | 2011-09-22 | 2015-12-29 | Ge Healthcare Limited | Indole derivatives |
| GB201312768D0 (en) * | 2013-07-17 | 2013-08-28 | Ge Healthcare Ltd | Work-up procedure |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9109972D0 (en) * | 1991-05-09 | 1991-07-03 | Ici Plc | Therapeutic compounds |
| GB9411955D0 (en) * | 1994-06-15 | 1994-08-03 | Merck Sharp & Dohme | Therapeutic agents |
| FR2754262B1 (fr) * | 1996-10-08 | 1998-10-30 | Synthelabo | Derives de 1h-pyrido[3,4-b]indole-4-carboxamide, leur preparation et leur application en therapeutique |
| FR2766823B1 (fr) * | 1997-07-30 | 1999-10-08 | Synthelabo | Derives de 4-oxo-3,5-dihydro-4h-pyridazino[4,5-b] indole-1-acetamide, leur preparation et leur application en therapeutique |
-
1999
- 1999-01-26 FR FR9900805A patent/FR2788776B1/fr not_active Expired - Fee Related
-
2000
- 2000-01-21 AT AT00900636T patent/ATE236905T1/de active
- 2000-01-21 WO PCT/FR2000/000134 patent/WO2000044751A1/fr not_active Ceased
- 2000-01-21 JP JP2000596007A patent/JP4574860B2/ja not_active Expired - Fee Related
- 2000-01-21 ES ES00900636T patent/ES2194696T3/es not_active Expired - Lifetime
- 2000-01-21 DE DE60002043T patent/DE60002043T2/de not_active Expired - Lifetime
- 2000-01-21 AU AU30578/00A patent/AU3057800A/en not_active Abandoned
- 2000-01-21 EP EP00900636A patent/EP1149101B1/fr not_active Expired - Lifetime
- 2000-01-21 US US09/889,984 patent/US6451795B1/en not_active Expired - Fee Related
- 2000-01-25 CO CO00003864A patent/CO5160255A1/es unknown
- 2000-01-25 AR ARP000100304A patent/AR030016A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ATE236905T1 (de) | 2003-04-15 |
| WO2000044751A1 (fr) | 2000-08-03 |
| CO5160255A1 (es) | 2002-05-30 |
| ES2194696T3 (es) | 2003-12-01 |
| DE60002043D1 (de) | 2003-05-15 |
| FR2788776A1 (fr) | 2000-07-28 |
| US6451795B1 (en) | 2002-09-17 |
| AU3057800A (en) | 2000-08-18 |
| AR030016A1 (es) | 2003-08-13 |
| EP1149101A1 (fr) | 2001-10-31 |
| FR2788776B1 (fr) | 2001-02-23 |
| EP1149101B1 (fr) | 2003-04-09 |
| JP4574860B2 (ja) | 2010-11-04 |
| JP2002535406A (ja) | 2002-10-22 |
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Owner name: SANOFI-AVENTIS, PARIS, FR |