NO312833B1 - Indazolkarboksamider, fremgangsmåte for fremstilling derav, anvendelse av forbindelsene samt farmasöytiske preparaterinneholdende disse - Google Patents

Indazolkarboksamider, fremgangsmåte for fremstilling derav, anvendelse av forbindelsene samt farmasöytiske preparaterinneholdende disse Download PDF

Info

Publication number: NO312833B1
Authority: NO; Norway
Prior art keywords: alkyl; compound; mmol; indazole; piperidinyl
Prior art date: 1995-03-16

Application number

NO19974221A

Other languages

English (en)

Norwegian (no)

Other versions

NO974221D0 (no

NO974221L (no

Inventor

John T Catlow

Marlene Lois Cohen

Michael John Martinelli

John Mehnert Schaus

Steven P Swanson

Dennis C Thompson

Thomas Michael Wilson

Original Assignee

Lilly Co Eli

Priority date (The priority date 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 date listed.)

1995-03-16

Filing date

1997-09-12

Publication date

2002-07-08

1995-06-07 Priority claimed from US08/485,956 external-priority patent/US5654320A/en

1997-09-12 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

1997-09-12 Publication of NO974221D0 publication Critical patent/NO974221D0/no

1997-10-27 Publication of NO974221L publication Critical patent/NO974221L/no

2002-07-08 Publication of NO312833B1 publication Critical patent/NO312833B1/no

Links

238000002360 preparation method Methods 0.000 title claims description 82
150000001875 compounds Chemical class 0.000 title claims description 75
238000000034 method Methods 0.000 title claims description 33
DITBWPUMEUDVLU-UHFFFAOYSA-N 1h-indazole-3-carboxamide Chemical class C1=CC=C2C(C(=O)N)=NNC2=C1 DITBWPUMEUDVLU-UHFFFAOYSA-N 0.000 title abstract description 4
230000008569 process Effects 0.000 title description 8
239000008194 pharmaceutical composition Substances 0.000 title 1
238000011282 treatment Methods 0.000 claims abstract description 17
-1 1-piperazinyl Chemical group 0.000 claims description 39
125000001624 naphthyl group Chemical group 0.000 claims description 25
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
229910052739 hydrogen Inorganic materials 0.000 claims description 24
239000001257 hydrogen Substances 0.000 claims description 23
150000003839 salts Chemical class 0.000 claims description 19
125000000217 alkyl group Chemical group 0.000 claims description 16
108091005482 5-HT4 receptors Proteins 0.000 claims description 15
238000006243 chemical reaction Methods 0.000 claims description 15
229910052757 nitrogen Inorganic materials 0.000 claims description 15
125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
150000002431 hydrogen Chemical group 0.000 claims description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
239000000825 pharmaceutical preparation Substances 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 7
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 7
208000002193 Pain Diseases 0.000 claims description 6
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
238000011321 prophylaxis Methods 0.000 claims description 6
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 5
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
125000005073 adamantyl group Chemical class C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 4
239000007822 coupling agent Substances 0.000 claims description 4
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206010012289 Dementia Diseases 0.000 claims description 3
206010028813 Nausea Diseases 0.000 claims description 3
206010046543 Urinary incontinence Diseases 0.000 claims description 3
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230000036506 anxiety Effects 0.000 claims description 3
230000006793 arrhythmia Effects 0.000 claims description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
201000006549 dyspepsia Diseases 0.000 claims description 3
208000021302 gastroesophageal reflux disease Diseases 0.000 claims description 3
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229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
208000002551 irritable bowel syndrome Diseases 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
230000027939 micturition Effects 0.000 claims description 3
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201000000980 schizophrenia Diseases 0.000 claims description 3
230000006794 tachycardia Effects 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 2
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125000002757 morpholinyl group Chemical group 0.000 claims description 2
125000004193 piperazinyl group Chemical group 0.000 claims description 2
GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 2
QEZYDSSGVBTNBH-UHFFFAOYSA-N n-[2-[4-(adamantane-1-carbonylamino)piperidin-1-yl]ethyl]-1-propan-2-ylindazole-3-carboxamide Chemical compound C12=CC=CC=C2N(C(C)C)N=C1C(=O)NCCN1CCC(NC(=O)C23CC4CC(CC(C4)C2)C3)CC1 QEZYDSSGVBTNBH-UHFFFAOYSA-N 0.000 claims 2
208000001871 Tachycardia Diseases 0.000 claims 1
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FEDKTGOMGVYEHB-UHFFFAOYSA-N benzyl n-[1-[2-[(1-propan-2-ylindazole-3-carbonyl)amino]ethyl]piperidin-4-yl]carbamate Chemical compound C12=CC=CC=C2N(C(C)C)N=C1C(=O)NCCN(CC1)CCC1NC(=O)OCC1=CC=CC=C1 FEDKTGOMGVYEHB-UHFFFAOYSA-N 0.000 claims 1
KHGJIEFWRMMWSG-UHFFFAOYSA-N n-[2-(4-acetamidopiperidin-1-yl)ethyl]-1-propan-2-ylindazole-3-carboxamide Chemical compound C12=CC=CC=C2N(C(C)C)N=C1C(=O)NCCN1CCC(NC(C)=O)CC1 KHGJIEFWRMMWSG-UHFFFAOYSA-N 0.000 claims 1
HMNUTMYCGLRBNS-UHFFFAOYSA-N n-[2-[4-[(3-hydroxyadamantane-1-carbonyl)amino]piperidin-1-yl]ethyl]-1-propan-2-ylindazole-3-carboxamide Chemical compound C12=CC=CC=C2N(C(C)C)N=C1C(=O)NCCN1CCC(NC(=O)C23CC4(O)CC(CC(C4)C2)C3)CC1 HMNUTMYCGLRBNS-UHFFFAOYSA-N 0.000 claims 1
MIDLORDGBDNOLV-UHFFFAOYSA-N n-[2-[4-[(4-hydroxyadamantane-1-carbonyl)amino]piperidin-1-yl]ethyl]-1-propan-2-ylindazole-3-carboxamide Chemical compound C12=CC=CC=C2N(C(C)C)N=C1C(=O)NCCN1CCC(NC(=O)C23CC4CC(CC(C4O)C3)C2)CC1 MIDLORDGBDNOLV-UHFFFAOYSA-N 0.000 claims 1
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 abstract description 11
239000005557 antagonist Substances 0.000 abstract description 5
239000004031 partial agonist Substances 0.000 abstract description 4
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239000000203 mixture Substances 0.000 description 55
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 54
239000003921 oil Substances 0.000 description 49
235000019198 oils Nutrition 0.000 description 49
238000001819 mass spectrum Methods 0.000 description 47
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
238000002844 melting Methods 0.000 description 37
230000008018 melting Effects 0.000 description 37
239000000047 product Substances 0.000 description 34
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
239000013078 crystal Substances 0.000 description 32
238000002425 crystallisation Methods 0.000 description 32
230000008025 crystallization Effects 0.000 description 32
238000004458 analytical method Methods 0.000 description 28
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
239000012458 free base Substances 0.000 description 19
150000003891 oxalate salts Chemical class 0.000 description 19
238000001704 evaporation Methods 0.000 description 18
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239000007787 solid Substances 0.000 description 18
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
239000000706 filtrate Substances 0.000 description 16
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
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PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 15
239000002024 ethyl acetate extract Substances 0.000 description 15
238000005406 washing Methods 0.000 description 14
238000000605 extraction Methods 0.000 description 13
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BHXVYTQDWMQVBI-UHFFFAOYSA-N 1h-indazole-3-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=NNC2=C1 BHXVYTQDWMQVBI-UHFFFAOYSA-N 0.000 description 12
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
238000003818 flash chromatography Methods 0.000 description 12
239000013067 intermediate product Substances 0.000 description 12
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239000012312 sodium hydride Substances 0.000 description 11
229910000104 sodium hydride Inorganic materials 0.000 description 11
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239000006185 dispersion Substances 0.000 description 10
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125000001424 substituent group Chemical group 0.000 description 10
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125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
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HWIFQIWWFGXKKP-UHFFFAOYSA-N n-[2-(4-benzylpiperazin-1-yl)ethyl]-1-propan-2-ylindazole-3-carboxamide;dihydrochloride Chemical compound Cl.Cl.C12=CC=CC=C2N(C(C)C)N=C1C(=O)NCCN(CC1)CCN1CC1=CC=CC=C1 HWIFQIWWFGXKKP-UHFFFAOYSA-N 0.000 description 1
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PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
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239000002858 neurotransmitter agent Substances 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
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239000003182 parenteral nutrition solution Substances 0.000 description 1
XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 1
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DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
DYUMLJSJISTVPV-UHFFFAOYSA-N phenyl propanoate Chemical compound CCC(=O)OC1=CC=CC=C1 DYUMLJSJISTVPV-UHFFFAOYSA-N 0.000 description 1
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XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
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239000002244 precipitate Substances 0.000 description 1
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KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
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UORVCLMRJXCDCP-UHFFFAOYSA-M propynoate Chemical compound [O-]C(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-M 0.000 description 1
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YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000007789 sealing Methods 0.000 description 1
229940116351 sebacate Drugs 0.000 description 1
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230000001688 serotonin response Effects 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
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239000007858 starting material Substances 0.000 description 1
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210000002784 stomach Anatomy 0.000 description 1
238000003860 storage Methods 0.000 description 1
TYFQFVWCELRYAO-UHFFFAOYSA-L suberate(2-) Chemical compound [O-]C(=O)CCCCCCC([O-])=O TYFQFVWCELRYAO-UHFFFAOYSA-L 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
150000003461 sulfonyl halides Chemical class 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
230000009747 swallowing Effects 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000007885 tablet disintegrant Substances 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
238000001665 trituration Methods 0.000 description 1
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
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238000005550 wet granulation Methods 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
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive 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
- 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
- A61P25/28—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
- 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
- A61P9/06—Antiarrhythmics
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Psychiatry (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Anesthesiology (AREA)
Hospice & Palliative Care (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Paper (AREA)
Luminescent Compositions (AREA)

NO19974221A 1995-03-16 1997-09-12 Indazolkarboksamider, fremgangsmåte for fremstilling derav, anvendelse av forbindelsene samt farmasöytiske preparaterinneholdende disse NO312833B1 (no)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US40511995A	1995-03-16	1995-03-16
US08/485,956 US5654320A (en)	1995-03-16	1995-06-07	Indazolecarboxamides
PCT/US1996/003551 WO1996033713A1 (en)	1995-03-16	1996-03-14	Indazolecarboxamides

Publications (3)

Publication Number	Publication Date
NO974221D0 NO974221D0 (no)	1997-09-12
NO974221L NO974221L (no)	1997-10-27
NO312833B1 true NO312833B1 (no)	2002-07-08

Family

ID=27018928

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19974221A NO312833B1 (no)	1995-03-16	1997-09-12	Indazolkarboksamider, fremgangsmåte for fremstilling derav, anvendelse av forbindelsene samt farmasöytiske preparaterinneholdende disse

Country Status (23)

Country	Link
US (2)	US5817676A (de)
EP (1)	EP0732333B1 (de)
JP (1)	JPH11502230A (de)
CN (1)	CN1112923C (de)
AT (1)	ATE203748T1 (de)
AU (1)	AU700842B2 (de)
BR (1)	BR9608223A (de)
CA (1)	CA2215359A1 (de)
DE (1)	DE69614164T2 (de)
DK (1)	DK0732333T3 (de)
EA (1)	EA000699B1 (de)
ES (1)	ES2159345T3 (de)
GR (1)	GR3037029T3 (de)
HU (1)	HU223973B1 (de)
IL (1)	IL117438A (de)
NO (1)	NO312833B1 (de)
NZ (1)	NZ315971A (de)
PL (1)	PL183867B1 (de)
PT (1)	PT732333E (de)
RO (1)	RO119617B1 (de)
SK (1)	SK283924B6 (de)
TR (1)	TR199700956T1 (de)
WO (1)	WO1996033713A1 (de)

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* Cited by examiner, † Cited by third party
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IT1291569B1 (it) *	1997-04-15	1999-01-11	Angelini Ricerche Spa	Indazolammidi come agenti serotoninergici
US5914405A (en) *	1997-10-07	1999-06-22	Eli Lilly And Company	Process for preparing 3-substituted indazoles
US6069152A (en) *	1997-10-07	2000-05-30	Eli Lilly And Company	5-HT4 agonists and antagonists
ES2257869T3 (es) *	1998-08-21	2006-08-01	Novartis Ag	Nueva formulacion oral para agonistas o antagonistas de 5-ht4.
KR100413150B1 (ko)	1998-09-10	2003-12-31	에프. 호프만-라 로슈 아게	5-에이치티4 수용체 길항제로서의 디하이드로벤조디옥신 카복스아미드 및 케톤 유도체
US6743820B2 (en)	2000-07-07	2004-06-01	University Of Toledo	Methods for protection of stratified squamous epithelium against injury by noxious substances and novel agents for use therefor
CA2418904A1 (en) *	2000-08-07	2002-02-14	Laboratoire Glaxosmithkline S.A.S.	Use of 5ht4 receptor antagonists in the manufacture of a medicament for the prophylaxis or treatment of atrial fibrillation
EP1321142A1 (de) *	2001-12-21	2003-06-25	Novartis AG	Feste orale Zubereitung mit Tegaserod
ATE401072T1 (de)	2002-02-12	2008-08-15	Organon Nv	1-arylsulfonyl-3-substituierte indol und indolinederivate verwendbar zur behandlung von erkrankungen des zentralnervensystem
ITMI20030287A1 (it)	2003-02-18	2004-08-19	Acraf	Indazolammidi dotate di attivita' analgesica metodo, per
ITMI20031468A1 (it) *	2003-07-18	2005-01-19	Acraf	Farmaco ativo nel dolore neuropatico
ITMI20031467A1 (it) *	2003-07-18	2005-01-19	Acraf	Farmaco attivo nel dolore neuropatico
SE0401969D0 (sv) *	2004-08-02	2004-08-02	Astrazeneca Ab	Piperidine derivatives
CA2615611C (en) *	2005-07-22	2011-09-27	Pfizer Inc.	Indazole derivatives
WO2009106980A2 (en) *	2008-02-29	2009-09-03	Pfizer Inc.	Indazole derivatives
GB201511382D0 (en)	2015-06-29	2015-08-12	Imp Innovations Ltd	Novel compounds and their use in therapy
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1996
- 1996-03-11 IL IL11743896A patent/IL117438A/en active IP Right Grant
- 1996-03-12 ES ES96301682T patent/ES2159345T3/es not_active Expired - Lifetime
- 1996-03-12 PT PT96301682T patent/PT732333E/pt unknown
- 1996-03-12 EP EP96301682A patent/EP0732333B1/de not_active Expired - Lifetime
- 1996-03-12 AT AT96301682T patent/ATE203748T1/de not_active IP Right Cessation
- 1996-03-12 DK DK96301682T patent/DK0732333T3/da active
- 1996-03-12 DE DE69614164T patent/DE69614164T2/de not_active Expired - Fee Related
- 1996-03-14 PL PL96322362A patent/PL183867B1/pl not_active IP Right Cessation
- 1996-03-14 JP JP8528690A patent/JPH11502230A/ja not_active Ceased
- 1996-03-14 EA EA199700242A patent/EA000699B1/ru not_active IP Right Cessation
- 1996-03-14 SK SK1242-97A patent/SK283924B6/sk unknown
- 1996-03-14 RO RO97-01719A patent/RO119617B1/ro unknown
- 1996-03-14 TR TR97/00956T patent/TR199700956T1/xx unknown
- 1996-03-14 CA CA002215359A patent/CA2215359A1/en not_active Abandoned
- 1996-03-14 BR BR9608223A patent/BR9608223A/pt not_active IP Right Cessation
- 1996-03-14 NZ NZ315971A patent/NZ315971A/xx unknown
- 1996-03-14 HU HU9801386A patent/HU223973B1/hu not_active IP Right Cessation
- 1996-03-14 CN CN96193677A patent/CN1112923C/zh not_active Expired - Fee Related
- 1996-03-14 AU AU68948/96A patent/AU700842B2/en not_active Ceased
- 1996-03-14 WO PCT/US1996/003551 patent/WO1996033713A1/en not_active Ceased
1997
- 1997-01-10 US US08/782,478 patent/US5817676A/en not_active Expired - Fee Related
- 1997-01-10 US US08/781,421 patent/US5798367A/en not_active Expired - Fee Related
- 1997-09-12 NO NO19974221A patent/NO312833B1/no unknown
2001
- 2001-10-26 GR GR20010401899T patent/GR3037029T3/el not_active IP Right Cessation

Also Published As

Publication number	Publication date
RO119617B1 (ro)	2005-01-28
IL117438A0 (en)	1996-07-23
EP0732333A1 (de)	1996-09-18
PT732333E (pt)	2001-11-30
DE69614164T2 (de)	2002-04-25
AU6894896A (en)	1996-11-18
US5798367A (en)	1998-08-25
TR199700956T1 (xx)	1998-02-21
ES2159345T3 (es)	2001-10-01
AU700842B2 (en)	1999-01-14
CN1183041A (zh)	1998-05-27
US5817676A (en)	1998-10-06
JPH11502230A (ja)	1999-02-23
EP0732333B1 (de)	2001-08-01
MX9706967A (es)	1997-11-29
EA000699B1 (ru)	2000-02-28
PL322362A1 (en)	1998-01-19
PL183867B1 (pl)	2002-07-31
DK0732333T3 (da)	2001-10-08
NZ315971A (en)	1999-01-28
GR3037029T3 (en)	2002-01-31
WO1996033713A1 (en)	1996-10-31
CN1112923C (zh)	2003-07-02
HUP9801386A3 (en)	2000-03-28
NO974221D0 (no)	1997-09-12
CA2215359A1 (en)	1996-10-31
ATE203748T1 (de)	2001-08-15
SK283924B6 (sk)	2004-05-04
DE69614164D1 (de)	2001-09-06
NO974221L (no)	1997-10-27
SK124297A3 (en)	1998-02-04
HU223973B1 (hu)	2005-03-29
HUP9801386A2 (hu)	1999-06-28
BR9608223A (pt)	1998-12-29
EA199700242A1 (ru)	1998-04-30
IL117438A (en)	2001-12-23

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