NO316271B1 - Nye indol- og indazolforbindelser, en fremgangsmåte ved deres fremstillingog farmasöytiske sammensetninger som inneholder dem - Google Patents
Nye indol- og indazolforbindelser, en fremgangsmåte ved deres fremstillingog farmasöytiske sammensetninger som inneholder dem Download PDFInfo
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- NO316271B1 NO316271B1 NO19984033A NO984033A NO316271B1 NO 316271 B1 NO316271 B1 NO 316271B1 NO 19984033 A NO19984033 A NO 19984033A NO 984033 A NO984033 A NO 984033A NO 316271 B1 NO316271 B1 NO 316271B1
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- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 238000000034 method Methods 0.000 title claims description 39
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title claims description 12
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 title claims description 9
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 title claims description 9
- 125000003453 indazolyl group Chemical class N1N=C(C2=C1C=CC=C2)* 0.000 title claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 6
- 230000008569 process Effects 0.000 title claims description 4
- -1 1-Substituted indole Chemical class 0.000 claims abstract description 9
- 208000019695 Migraine disease Diseases 0.000 claims abstract description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 6
- 208000035475 disorder Diseases 0.000 claims abstract description 6
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims abstract description 4
- 230000009467 reduction Effects 0.000 claims abstract description 4
- 239000003814 drug Substances 0.000 claims abstract description 3
- 208000019553 vascular disease Diseases 0.000 claims abstract description 3
- 201000002282 venous insufficiency Diseases 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 122
- 229910052757 nitrogen Inorganic materials 0.000 claims description 34
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 11
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 125000005936 piperidyl group Chemical group 0.000 claims description 10
- 239000007858 starting material Substances 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000001425 triazolyl group Chemical group 0.000 claims description 6
- 125000001041 indolyl group Chemical group 0.000 claims description 5
- 125000004385 trihaloalkyl group Chemical group 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 230000031709 bromination Effects 0.000 claims description 4
- 238000005893 bromination reaction Methods 0.000 claims description 4
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 206010027599 migraine Diseases 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- ZUJDNIMRBMTNOL-UHFFFAOYSA-N 1-[3-[4-(5-methoxypyrimidin-4-yl)piperazin-1-yl]propyl]-6-(1,2,4-triazol-4-yl)indazole Chemical compound COC1=CN=CN=C1N1CCN(CCCN2C3=CC(=CC=C3C=N2)N2C=NN=C2)CC1 ZUJDNIMRBMTNOL-UHFFFAOYSA-N 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- NVCPCYQVOPADQZ-UHFFFAOYSA-N n,n-dimethyl-2-[6-(1,2,4-triazol-4-yl)indazol-1-yl]ethanamine Chemical compound C1=C2N(CCN(C)C)N=CC2=CC=C1N1C=NN=C1 NVCPCYQVOPADQZ-UHFFFAOYSA-N 0.000 claims 2
- 238000006268 reductive amination reaction Methods 0.000 claims 2
- HYKVXKSWHRUKHQ-UHFFFAOYSA-N 1-[3-[4-(5-methoxypyrimidin-4-yl)piperazin-1-yl]propyl]-6-(1,2,4-triazol-4-yl)indole Chemical compound COC1=CN=CN=C1N1CCN(CCCN2C3=CC(=CC=C3C=C2)N2C=NN=C2)CC1 HYKVXKSWHRUKHQ-UHFFFAOYSA-N 0.000 claims 1
- 238000006722 reduction reaction Methods 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 abstract description 2
- 208000002193 Pain Diseases 0.000 abstract description 2
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 abstract 1
- HLDVKIKLLBOOPW-UHFFFAOYSA-N 2-methyl-1h-indol-3-ol Chemical class C1=CC=C2C(O)=C(C)NC2=C1 HLDVKIKLLBOOPW-UHFFFAOYSA-N 0.000 abstract 1
- JXZZHCVPKCNLHP-UHFFFAOYSA-N N1C=NN=C1.N1N=CC2=CC=CC=C12 Chemical class N1C=NN=C1.N1N=CC2=CC=CC=C12 JXZZHCVPKCNLHP-UHFFFAOYSA-N 0.000 abstract 1
- 208000008589 Obesity Diseases 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 150000001540 azides Chemical class 0.000 abstract 1
- AYTAYKXVFZPRAF-KQQUZDAGSA-N n'-[(e)-dimethylaminomethylideneamino]-n,n-dimethylmethanimidamide Chemical compound CN(C)\C=N\N=C\N(C)C AYTAYKXVFZPRAF-KQQUZDAGSA-N 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 235000020824 obesity Nutrition 0.000 abstract 1
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- 239000000047 product Substances 0.000 description 40
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- 229910052739 hydrogen Inorganic materials 0.000 description 17
- 229910052799 carbon Inorganic materials 0.000 description 16
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 12
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
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- 238000004587 chromatography analysis Methods 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
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- 229910002027 silica gel Inorganic materials 0.000 description 6
- DWLADVOODHZCFV-UHFFFAOYSA-N tert-butyl 3-formylpyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(C=O)C1 DWLADVOODHZCFV-UHFFFAOYSA-N 0.000 description 6
- IPONLHAIQBCUCY-UHFFFAOYSA-N 1h-indole;dihydrochloride Chemical compound Cl.Cl.C1=CC=C2NC=CC2=C1 IPONLHAIQBCUCY-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 230000000144 pharmacologic effect Effects 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 108020003175 receptors Proteins 0.000 description 5
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- ABGXADJDTPFFSZ-UHFFFAOYSA-N 4-benzylpiperidine Chemical compound C=1C=CC=CC=1CC1CCNCC1 ABGXADJDTPFFSZ-UHFFFAOYSA-N 0.000 description 4
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- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- PSWCIARYGITEOY-UHFFFAOYSA-N 6-nitro-1h-indole Chemical compound [O-][N+](=O)C1=CC=C2C=CNC2=C1 PSWCIARYGITEOY-UHFFFAOYSA-N 0.000 description 3
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CDTKEHYOEXOBQV-UHFFFAOYSA-N 1-(1-benzylpiperidin-4-yl)-6-(1,2,4-triazol-4-ylmethyl)indole;dihydrochloride Chemical compound Cl.Cl.C=1C=CC=CC=1CN(CC1)CCC1N(C1=C2)C=CC1=CC=C2CN1C=NN=C1 CDTKEHYOEXOBQV-UHFFFAOYSA-N 0.000 description 2
- UZNBFEKZQFEGFX-UHFFFAOYSA-N 1-[3-[4-(2-phenylethyl)piperazin-1-yl]propyl]-6-(1,2,4-triazol-4-yl)indole;dihydrochloride Chemical compound Cl.Cl.C1=CC2=CC=C(N3C=NN=C3)C=C2N1CCCN(CC1)CCN1CCC1=CC=CC=C1 UZNBFEKZQFEGFX-UHFFFAOYSA-N 0.000 description 2
- IDMFVGRBITWGLW-UHFFFAOYSA-N 5-methoxy-4-piperazin-1-ylpyrimidine Chemical compound COC1=CN=CN=C1N1CCNCC1 IDMFVGRBITWGLW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
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- KQKPFRSPSRPDEB-UHFFFAOYSA-N sumatriptan Chemical compound CNS(=O)(=O)CC1=CC=C2NC=C(CCN(C)C)C2=C1 KQKPFRSPSRPDEB-UHFFFAOYSA-N 0.000 description 2
- 229960003708 sumatriptan Drugs 0.000 description 2
- YGIDJVVUMQKGMN-UHFFFAOYSA-N tert-butyl 3-[[6-(1,2,4-triazol-4-yl)indol-1-yl]methyl]pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC1CN1C2=CC(N3C=NN=C3)=CC=C2C=C1 YGIDJVVUMQKGMN-UHFFFAOYSA-N 0.000 description 2
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 2
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- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
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- HWKXLBWBBJYYHI-UHFFFAOYSA-N 1-(1-benzylpiperidin-4-yl)-6-(1,2,4-triazol-4-yl)indole;dihydrochloride Chemical compound Cl.Cl.C=1C=CC=CC=1CN(CC1)CCC1N(C1=C2)C=CC1=CC=C2N1C=NN=C1 HWKXLBWBBJYYHI-UHFFFAOYSA-N 0.000 description 1
- ABLHHCAFZRLTPU-UHFFFAOYSA-N 1-(1-benzylpiperidin-4-yl)indol-6-amine Chemical compound C12=CC(N)=CC=C2C=CN1C(CC1)CCN1CC1=CC=CC=C1 ABLHHCAFZRLTPU-UHFFFAOYSA-N 0.000 description 1
- KPKRLFXIDRBMPW-UHFFFAOYSA-N 1-(1-methylpiperidin-4-yl)-6-nitro-2,3-dihydroindole Chemical compound C1CN(C)CCC1N1C2=CC([N+]([O-])=O)=CC=C2CC1 KPKRLFXIDRBMPW-UHFFFAOYSA-N 0.000 description 1
- FHQAWIBKAPLIGF-UHFFFAOYSA-N 1-(1-methylpiperidin-4-yl)-6-nitroindole Chemical compound C1CN(C)CCC1N1C2=CC([N+]([O-])=O)=CC=C2C=C1 FHQAWIBKAPLIGF-UHFFFAOYSA-N 0.000 description 1
- CFJSTCSYECXWIB-UHFFFAOYSA-N 1-(1-methylpiperidin-4-yl)indol-6-amine Chemical compound C1CN(C)CCC1N1C2=CC(N)=CC=C2C=C1 CFJSTCSYECXWIB-UHFFFAOYSA-N 0.000 description 1
- LKUAPSRIYZLAAO-UHFFFAOYSA-N 1-(2-phenylethyl)piperazine Chemical compound C1CNCCN1CCC1=CC=CC=C1 LKUAPSRIYZLAAO-UHFFFAOYSA-N 0.000 description 1
- YAGQQFXVXRVORK-UHFFFAOYSA-N 1-(3-bromopropyl)-6-nitroindazole Chemical compound [O-][N+](=O)C1=CC=C2C=NN(CCCBr)C2=C1 YAGQQFXVXRVORK-UHFFFAOYSA-N 0.000 description 1
- MMYMZCNVQIRKOF-UHFFFAOYSA-N 1-(pyrrolidin-3-ylmethyl)-6-(1,2,4-triazol-4-yl)indole;dihydrochloride Chemical compound Cl.Cl.C1=CC2=CC=C(N3C=NN=C3)C=C2N1CC1CCNC1 MMYMZCNVQIRKOF-UHFFFAOYSA-N 0.000 description 1
- PNPZTVKNNUXCMZ-UHFFFAOYSA-N 1-[1-(3-phenylpropyl)piperidin-4-yl]-6-(1,2,4-triazol-4-yl)indole;dihydrochloride Chemical compound Cl.Cl.C=1C=CC=CC=1CCCN(CC1)CCC1N(C1=C2)C=CC1=CC=C2N1C=NN=C1 PNPZTVKNNUXCMZ-UHFFFAOYSA-N 0.000 description 1
- NMLMAJOVSWGCQS-UHFFFAOYSA-N 1-[2-(dimethylamino)ethyl]indol-6-amine Chemical compound C1=C(N)C=C2N(CCN(C)C)C=CC2=C1 NMLMAJOVSWGCQS-UHFFFAOYSA-N 0.000 description 1
- SUJSRBRZNFPWMO-UHFFFAOYSA-N 1-[3-(4-benzylpiperidin-1-yl)propyl]-6-(1,2,4-triazol-4-yl)indole;dihydrochloride Chemical compound Cl.Cl.C1=CC2=CC=C(N3C=NN=C3)C=C2N1CCCN(CC1)CCC1CC1=CC=CC=C1 SUJSRBRZNFPWMO-UHFFFAOYSA-N 0.000 description 1
- GIFIFTPNZIJBFL-UHFFFAOYSA-N 1-[3-(4-benzylpiperidin-1-yl)propyl]-6-nitroindole Chemical compound C12=CC([N+](=O)[O-])=CC=C2C=CN1CCCN(CC1)CCC1CC1=CC=CC=C1 GIFIFTPNZIJBFL-UHFFFAOYSA-N 0.000 description 1
- GOYHYRYWKKQFEK-UHFFFAOYSA-N 1-[3-(4-benzylpiperidin-1-yl)propyl]indol-6-amine Chemical compound C12=CC(N)=CC=C2C=CN1CCCN(CC1)CCC1CC1=CC=CC=C1 GOYHYRYWKKQFEK-UHFFFAOYSA-N 0.000 description 1
- CKJYYTCXWHPFHM-UHFFFAOYSA-N 1-[3-(4-pyridin-2-ylpiperazin-1-yl)propyl]-6-(1,2,4-triazol-4-yl)indole;dihydrochloride Chemical compound Cl.Cl.C1=CC2=CC=C(N3C=NN=C3)C=C2N1CCCN(CC1)CCN1C1=CC=CC=N1 CKJYYTCXWHPFHM-UHFFFAOYSA-N 0.000 description 1
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- BLQQXWILHAIWDC-UHFFFAOYSA-N tert-butyl 3-[(6-nitro-2,3-dihydroindol-1-yl)methyl]pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC1CN1C2=CC([N+]([O-])=O)=CC=C2CC1 BLQQXWILHAIWDC-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- A61P25/06—Antimigraine 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
- A61P9/00—Drugs for disorders of the cardiovascular 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
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9710939A FR2767827A1 (fr) | 1997-09-03 | 1997-09-03 | Nouveaux derives de l'indole et de l'indazole, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO984033D0 NO984033D0 (no) | 1998-09-02 |
| NO984033L NO984033L (no) | 1999-03-04 |
| NO316271B1 true NO316271B1 (no) | 2004-01-05 |
Family
ID=9510710
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19984033A NO316271B1 (no) | 1997-09-03 | 1998-09-02 | Nye indol- og indazolforbindelser, en fremgangsmåte ved deres fremstillingog farmasöytiske sammensetninger som inneholder dem |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US6020336A (pt) |
| EP (1) | EP0902027B1 (pt) |
| JP (1) | JPH11130773A (pt) |
| CN (2) | CN1510034A (pt) |
| AT (1) | ATE203531T1 (pt) |
| AU (1) | AU736602B2 (pt) |
| BR (1) | BR9803318A (pt) |
| CA (1) | CA2246485C (pt) |
| DE (1) | DE69801196T2 (pt) |
| DK (1) | DK0902027T5 (pt) |
| ES (1) | ES2162404T3 (pt) |
| FR (1) | FR2767827A1 (pt) |
| GR (1) | GR3036678T3 (pt) |
| HK (1) | HK1019738A1 (pt) |
| HU (1) | HUP9801977A1 (pt) |
| NO (1) | NO316271B1 (pt) |
| NZ (1) | NZ331683A (pt) |
| PL (1) | PL328323A1 (pt) |
| PT (1) | PT902027E (pt) |
| ZA (1) | ZA988072B (pt) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU779073B2 (en) * | 1998-12-23 | 2005-01-06 | Nps Allelix Corp. | Indole and indolizidine derivatives for the treatment of migraine |
| YU54202A (sh) * | 2000-01-18 | 2006-01-16 | Agouron Pharmaceuticals Inc. | Jedinjenja indazola, farmaceutske smeše i postupci za stimulisanje i inhibiranje ćelijske proliferacije |
| HN2001000008A (es) | 2000-01-21 | 2003-12-11 | Inc Agouron Pharmaceuticals | Compuesto de amida y composiciones farmaceuticas para inhibir proteinquinasas, y su modo de empleo |
| WO2001079198A1 (en) | 2000-04-18 | 2001-10-25 | Agouron Pharmaceuticals, Inc. | Pyrazoles for inhibiting protein kinase |
| US7589202B2 (en) | 2000-08-14 | 2009-09-15 | Ortho Mcneil Pharmaceutical, Inc. | Substituted pyrazoles |
| US7332494B2 (en) | 2000-08-14 | 2008-02-19 | Janssen Pharmaceutica, N.V. | Method for treating allergies using substituted pyrazoles |
| US20070105841A1 (en) * | 2000-08-14 | 2007-05-10 | Breitenbucher J G | Method for treating allergies using substituted pyrazoles |
| FR2829134B1 (fr) | 2001-08-28 | 2006-11-24 | Atofina | Procede de preparation de (meth) acrylates d'alkylimidazolidone |
| US20030073672A1 (en) * | 2001-09-05 | 2003-04-17 | Breitenbucher J. Guy | Method for treating allergies using substituted pyrazoles |
| WO2012086735A1 (ja) * | 2010-12-22 | 2012-06-28 | 大正製薬株式会社 | 縮合複素環化合物 |
| CN102617548A (zh) * | 2011-01-31 | 2012-08-01 | 北京赛林泰医药技术有限公司 | 作为gpr受体激动剂的双环杂芳基化合物及其组合物和应用 |
| WO2014102589A1 (en) | 2012-12-27 | 2014-07-03 | Purdue Pharma L.P. | Quinazolin-4(3h)-one-type piperidine compounds and uses thereof |
| US9963458B2 (en) | 2012-12-27 | 2018-05-08 | Purdue Pharma L.P. | Indole and indoline-type piperidine compounds and uses thereof |
| US20150252051A1 (en) * | 2014-03-10 | 2015-09-10 | Innov17 Llc | Retinoic acid receptor-related orphan receptor modulators and uses thereof |
| EP3116504A4 (en) * | 2014-03-10 | 2017-08-09 | Innov17 LLC | Retinoic acid receptor-related orphan receptor modulators and uses thereof |
| WO2018106667A1 (en) * | 2016-12-05 | 2018-06-14 | Microbiotix, Inc. | Broad-spectrum inhibitors of filoviruses |
Family Cites Families (10)
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|---|---|---|---|---|
| HU198036B (en) * | 1983-08-22 | 1989-07-28 | Hoechst Roussel Pharma | Process for production of derivatives of 3-piperidil-/1h/-indasole and medical preparatives containing them |
| TW203049B (pt) * | 1990-04-13 | 1993-04-01 | Yamanouchi Pharma Co Ltd | |
| AU658729B2 (en) * | 1992-03-27 | 1995-04-27 | Kyoto Pharmaceutical Industries, Ltd. | 3-(1H-imidazol-1-ylmethyl)-1H-indole derivatives |
| IL106445A (en) * | 1992-07-30 | 1998-01-04 | Merck Sharp & Dohme | History of 1,2,4-Trans-Triazole 4-Transform, Preparation and Pharmaceutical Preparations Containing Them |
| GB9402016D0 (en) * | 1994-02-02 | 1994-03-30 | Merck Sharp & Dohme | Therapeutic agents |
| GB2289465A (en) * | 1994-05-19 | 1995-11-22 | Merck Sharp & Dohme | Five-membered heteroaromatic 5-HT receptor agonists |
| US5807857A (en) * | 1994-05-19 | 1998-09-15 | Merck Sharp & Dohme Ltd. | Piperazine, piperidine and tetrahydropyridine derivative of indol-3-alkyl as 5-HT1D-α agonists |
| US5854268A (en) * | 1994-08-02 | 1998-12-29 | Merck Sharp & Dohme, Ltd. | Azetidine, pyrrolidine and piperidine derivatives |
| ZA965837B (en) * | 1995-07-11 | 1997-01-31 | Merck & Co Inc | A triazolylmethyl-indole ethylamine bisulfate salt |
| US5889008A (en) * | 1995-08-07 | 1999-03-30 | Merck Sharp & Dohme, Ltd. | Substituted 1-indolylpropyl-4-phenethylpiperazadine derivatives |
-
1997
- 1997-09-03 FR FR9710939A patent/FR2767827A1/fr not_active Withdrawn
-
1998
- 1998-09-01 AT AT98402154T patent/ATE203531T1/de not_active IP Right Cessation
- 1998-09-01 PT PT98402154T patent/PT902027E/pt unknown
- 1998-09-01 ES ES98402154T patent/ES2162404T3/es not_active Expired - Lifetime
- 1998-09-01 EP EP98402154A patent/EP0902027B1/fr not_active Expired - Lifetime
- 1998-09-01 BR BR9803318-2A patent/BR9803318A/pt not_active IP Right Cessation
- 1998-09-01 DE DE69801196T patent/DE69801196T2/de not_active Expired - Fee Related
- 1998-09-01 DK DK98402154T patent/DK0902027T5/da active
- 1998-09-02 US US09/146,009 patent/US6020336A/en not_active Expired - Fee Related
- 1998-09-02 CN CNA021184682A patent/CN1510034A/zh active Pending
- 1998-09-02 NO NO19984033A patent/NO316271B1/no not_active IP Right Cessation
- 1998-09-02 PL PL98328323A patent/PL328323A1/xx unknown
- 1998-09-02 CN CN98124581A patent/CN1087741C/zh not_active Expired - Fee Related
- 1998-09-02 HU HU9801977A patent/HUP9801977A1/hu unknown
- 1998-09-02 NZ NZ331683A patent/NZ331683A/xx unknown
- 1998-09-03 JP JP10249314A patent/JPH11130773A/ja active Pending
- 1998-09-03 ZA ZA988072A patent/ZA988072B/xx unknown
- 1998-09-03 CA CA002246485A patent/CA2246485C/fr not_active Expired - Fee Related
- 1998-09-03 AU AU83068/98A patent/AU736602B2/en not_active Ceased
-
1999
- 1999-04-26 US US09/299,314 patent/US6046205A/en not_active Expired - Fee Related
- 1999-10-28 HK HK99104871A patent/HK1019738A1/xx not_active IP Right Cessation
-
2001
- 2001-09-20 GR GR20010401535T patent/GR3036678T3/el not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ES2162404T3 (es) | 2001-12-16 |
| JPH11130773A (ja) | 1999-05-18 |
| DK0902027T5 (da) | 2001-12-03 |
| AU736602B2 (en) | 2001-08-02 |
| HK1019738A1 (en) | 2000-02-25 |
| EP0902027A1 (fr) | 1999-03-17 |
| NZ331683A (en) | 2000-01-28 |
| HU9801977D0 (en) | 1998-10-28 |
| GR3036678T3 (en) | 2001-12-31 |
| ZA988072B (en) | 1999-03-09 |
| EP0902027B1 (fr) | 2001-07-25 |
| DE69801196D1 (de) | 2001-08-30 |
| DK0902027T3 (da) | 2001-10-15 |
| US6046205A (en) | 2000-04-04 |
| CA2246485A1 (fr) | 1999-03-03 |
| US6020336A (en) | 2000-02-01 |
| PL328323A1 (en) | 1999-03-15 |
| AU8306898A (en) | 1999-03-18 |
| ATE203531T1 (de) | 2001-08-15 |
| CN1218052A (zh) | 1999-06-02 |
| DE69801196T2 (de) | 2002-03-14 |
| PT902027E (pt) | 2001-11-30 |
| FR2767827A1 (fr) | 1999-02-26 |
| NO984033D0 (no) | 1998-09-02 |
| NO984033L (no) | 1999-03-04 |
| HUP9801977A1 (hu) | 2000-11-28 |
| CN1087741C (zh) | 2002-07-17 |
| CN1510034A (zh) | 2004-07-07 |
| BR9803318A (pt) | 2000-02-08 |
| CA2246485C (fr) | 2004-04-20 |
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