NO320299B1 - Heterocykliske forbindelser og anvendelse av slike forbindelser for fremstilling av medikamenter. - Google Patents
Heterocykliske forbindelser og anvendelse av slike forbindelser for fremstilling av medikamenter. Download PDFInfo
- Publication number
- NO320299B1 NO320299B1 NO20005881A NO20005881A NO320299B1 NO 320299 B1 NO320299 B1 NO 320299B1 NO 20005881 A NO20005881 A NO 20005881A NO 20005881 A NO20005881 A NO 20005881A NO 320299 B1 NO320299 B1 NO 320299B1
- Authority
- NO
- Norway
- Prior art keywords
- carboxamide
- indole
- benzylpiperidinyl
- piperazinyl
- alkyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 125
- 239000003814 drug Substances 0.000 title claims description 18
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- 229940079593 drug Drugs 0.000 title description 12
- 150000002391 heterocyclic compounds Chemical class 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 26
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 19
- 125000005843 halogen group Chemical group 0.000 claims abstract description 12
- 125000001424 substituent group Chemical group 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 7
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 5
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 3
- -1 C 1 -C 6 alkoxy Chemical group 0.000 claims description 48
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 22
- 125000003386 piperidinyl group Chemical group 0.000 claims description 13
- XQIKXPXSWYNRSF-UHFFFAOYSA-N 2-(4-benzylpiperidin-1-yl)-1h-indole-5-carboxamide Chemical compound C=1C2=CC(C(=O)N)=CC=C2NC=1N(CC1)CCC1CC1=CC=CC=C1 XQIKXPXSWYNRSF-UHFFFAOYSA-N 0.000 claims description 10
- 206010019280 Heart failures Diseases 0.000 claims description 9
- 125000004193 piperazinyl group Chemical group 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 7
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- UHYKYBSPFDZEGC-UHFFFAOYSA-N 2-(4-benzylpiperidin-1-yl)-6-methoxy-1h-indole-5-carboxamide Chemical compound C=1C=2C=C(C(N)=O)C(OC)=CC=2NC=1N(CC1)CCC1CC1=CC=CC=C1 UHYKYBSPFDZEGC-UHFFFAOYSA-N 0.000 claims description 5
- 206010061218 Inflammation Diseases 0.000 claims description 5
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 5
- 230000004054 inflammatory process Effects 0.000 claims description 5
- 206010007559 Cardiac failure congestive Diseases 0.000 claims description 4
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 4
- 208000009525 Myocarditis Diseases 0.000 claims description 4
- 125000002757 morpholinyl group Chemical group 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 3
- GQMYQEAXTITUAE-UHFFFAOYSA-N 1H-indole-5-carboxamide Chemical compound NC(=O)C1=CC=C2NC=CC2=C1 GQMYQEAXTITUAE-UHFFFAOYSA-N 0.000 claims description 3
- VVDLGDFMJJGBIW-UHFFFAOYSA-N 2-[4-benzyl-3-(2,2,2-trifluoroacetyl)piperidin-1-yl]-1h-indole-5-carboxamide Chemical compound C=1C2=CC(C(=O)N)=CC=C2NC=1N(CC1C(=O)C(F)(F)F)CCC1CC1=CC=CC=C1 VVDLGDFMJJGBIW-UHFFFAOYSA-N 0.000 claims description 3
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 3
- 125000000520 N-substituted aminocarbonyl group Chemical group [*]NC(=O)* 0.000 claims description 3
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- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- KJLFFCRGGGXQKE-UHFFFAOYSA-N 1h-indole-6-carboxamide Chemical compound NC(=O)C1=CC=C2C=CNC2=C1 KJLFFCRGGGXQKE-UHFFFAOYSA-N 0.000 claims description 2
- SCBGJAMOFAPVJB-UHFFFAOYSA-N 2-(4-benzylpiperidin-1-yl)-4-methoxy-1h-indole-5-carboxamide Chemical compound C=1C=2C(OC)=C(C(N)=O)C=CC=2NC=1N(CC1)CCC1CC1=CC=CC=C1 SCBGJAMOFAPVJB-UHFFFAOYSA-N 0.000 claims description 2
- DBCREKNQLGREHQ-UHFFFAOYSA-N 2-(4-benzylpiperidin-1-yl)-n-[2-hydroxy-3-(propylamino)propyl]-1h-indole-5-carboxamide Chemical compound C=1C2=CC(C(=O)NCC(O)CNCCC)=CC=C2NC=1N(CC1)CCC1CC1=CC=CC=C1 DBCREKNQLGREHQ-UHFFFAOYSA-N 0.000 claims description 2
- UHGDXXRCTDEHQD-UHFFFAOYSA-N 2-(4-benzylpiperidin-1-yl)-n-[3-(cyclohexylmethylamino)-2-hydroxypropyl]-1h-indole-5-carboxamide Chemical compound C=1C=C2NC(N3CCC(CC=4C=CC=CC=4)CC3)=CC2=CC=1C(=O)NCC(O)CNCC1CCCCC1 UHGDXXRCTDEHQD-UHFFFAOYSA-N 0.000 claims description 2
- SMXYQSMGYLNSBS-UHFFFAOYSA-N 2-(4-benzylpiperidin-1-yl)-n-propanoyl-1h-indole-5-carboxamide Chemical compound C=1C2=CC(C(=O)NC(=O)CC)=CC=C2NC=1N(CC1)CCC1CC1=CC=CC=C1 SMXYQSMGYLNSBS-UHFFFAOYSA-N 0.000 claims description 2
- OTRLVAHNGOIIIM-UHFFFAOYSA-N 2-[4-[(4-fluorophenyl)methyl]piperidin-1-yl]-4-methoxy-1h-indole-5-carboxamide Chemical compound C=1C=2C(OC)=C(C(N)=O)C=CC=2NC=1N(CC1)CCC1CC1=CC=C(F)C=C1 OTRLVAHNGOIIIM-UHFFFAOYSA-N 0.000 claims description 2
- INJUDDVHJZUWTQ-UHFFFAOYSA-N 2-[4-[(4-fluorophenyl)methyl]piperidin-1-yl]-6-methoxy-1h-indole-5-carboxamide Chemical compound C=1C=2C=C(C(N)=O)C(OC)=CC=2NC=1N(CC1)CCC1CC1=CC=C(F)C=C1 INJUDDVHJZUWTQ-UHFFFAOYSA-N 0.000 claims description 2
- LOJJLAGBTAGITQ-UHFFFAOYSA-N 2-[4-[(4-methylsulfanylphenyl)methyl]piperazin-1-yl]-3h-benzimidazole-5-carboxamide Chemical compound C1=CC(SC)=CC=C1CN1CCN(C=2NC3=CC(=CC=C3N=2)C(N)=O)CC1 LOJJLAGBTAGITQ-UHFFFAOYSA-N 0.000 claims description 2
- PBONXFAGZYYDTE-UHFFFAOYSA-N 4-chloro-2-[4-[(4-fluorophenyl)methyl]piperidin-1-yl]-1h-indole-5-carboxamide Chemical compound C=1C2=C(Cl)C(C(=O)N)=CC=C2NC=1N(CC1)CCC1CC1=CC=C(F)C=C1 PBONXFAGZYYDTE-UHFFFAOYSA-N 0.000 claims description 2
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 208000009304 Acute Kidney Injury Diseases 0.000 claims description 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 2
- 206010056370 Congestive cardiomyopathy Diseases 0.000 claims description 2
- 206010019196 Head injury Diseases 0.000 claims description 2
- 208000033626 Renal failure acute Diseases 0.000 claims description 2
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 2
- 206010046851 Uveitis Diseases 0.000 claims description 2
- 201000011040 acute kidney failure Diseases 0.000 claims description 2
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 201000011304 dilated cardiomyopathy 1A Diseases 0.000 claims description 2
- HDCXQTPVTAIPNZ-UHFFFAOYSA-N n-({[4-(aminosulfonyl)phenyl]amino}carbonyl)-4-methylbenzenesulfonamide Chemical group C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NC1=CC=C(S(N)(=O)=O)C=C1 HDCXQTPVTAIPNZ-UHFFFAOYSA-N 0.000 claims description 2
- 230000007112 pro inflammatory response Effects 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- MZUBLCVAGGWWCH-UHFFFAOYSA-N 2-(4-benzylpiperazin-1-yl)-3h-benzimidazole-5-carboxamide Chemical compound N1C2=CC(C(=O)N)=CC=C2N=C1N(CC1)CCN1CC1=CC=CC=C1 MZUBLCVAGGWWCH-UHFFFAOYSA-N 0.000 claims 1
- XASBBUBUFRHSCO-UHFFFAOYSA-N 2-(4-benzylpiperidin-1-yl)-n-(pyridin-4-ylmethyl)-1h-indole-5-carboxamide Chemical compound C=1C=C2NC(N3CCC(CC=4C=CC=CC=4)CC3)=CC2=CC=1C(=O)NCC1=CC=NC=C1 XASBBUBUFRHSCO-UHFFFAOYSA-N 0.000 claims 1
- NEOZRCLVNSDKMU-UHFFFAOYSA-N 2-(4-benzylpiperidin-1-yl)-n-(pyridine-4-carbonyl)-1h-indole-5-carboxamide Chemical compound C=1C=NC=CC=1C(=O)NC(=O)C(C=C1C=2)=CC=C1NC=2N(CC1)CCC1CC1=CC=CC=C1 NEOZRCLVNSDKMU-UHFFFAOYSA-N 0.000 claims 1
- JPURORVGEFTMTK-UHFFFAOYSA-N 2-[4-(2,4-dichlorobenzoyl)piperazin-1-yl]-3h-benzimidazole-5-carboxamide Chemical compound N1C2=CC(C(=O)N)=CC=C2N=C1N(CC1)CCN1C(=O)C1=CC=C(Cl)C=C1Cl JPURORVGEFTMTK-UHFFFAOYSA-N 0.000 claims 1
- ORTIJHMNUXUBGD-UHFFFAOYSA-N 2-[4-[(2,6-difluorophenyl)methyl]piperazin-1-yl]-3h-benzimidazole-5-carboxamide Chemical compound N1C2=CC(C(=O)N)=CC=C2N=C1N(CC1)CCN1CC1=C(F)C=CC=C1F ORTIJHMNUXUBGD-UHFFFAOYSA-N 0.000 claims 1
- ZCSUNFCPZFPDKE-UHFFFAOYSA-N 2-[4-[(3,5-difluorophenyl)methyl]piperazin-1-yl]-3h-benzimidazole-5-carboxamide Chemical compound N1C2=CC(C(=O)N)=CC=C2N=C1N(CC1)CCN1CC1=CC(F)=CC(F)=C1 ZCSUNFCPZFPDKE-UHFFFAOYSA-N 0.000 claims 1
- VEBVLTONVCROFJ-UHFFFAOYSA-N 2-[4-[(4-chlorophenyl)methyl]piperazin-1-yl]-3h-benzimidazole-5-carboxamide Chemical compound N1C2=CC(C(=O)N)=CC=C2N=C1N(CC1)CCN1CC1=CC=C(Cl)C=C1 VEBVLTONVCROFJ-UHFFFAOYSA-N 0.000 claims 1
- TVYNASBBVFFQNH-UHFFFAOYSA-N 2-[4-[(4-methoxyphenyl)methyl]piperazin-1-yl]-3h-benzimidazole-5-carboxamide Chemical compound C1=CC(OC)=CC=C1CN1CCN(C=2NC3=CC(=CC=C3N=2)C(N)=O)CC1 TVYNASBBVFFQNH-UHFFFAOYSA-N 0.000 claims 1
- GZHGTLVTMXEPRL-UHFFFAOYSA-N 2-[4-[(4-methylphenyl)methyl]piperazin-1-yl]-3h-benzimidazole-5-carboxamide Chemical compound C1=CC(C)=CC=C1CN1CCN(C=2NC3=CC(=CC=C3N=2)C(N)=O)CC1 GZHGTLVTMXEPRL-UHFFFAOYSA-N 0.000 claims 1
- CBXLQGOZYCGGAV-QPJJXVBHSA-N 2-[4-[(e)-3-[3-(trifluoromethyl)phenyl]prop-2-enoyl]piperazin-1-yl]-3h-benzimidazole-5-carboxamide Chemical compound N1C2=CC(C(=O)N)=CC=C2N=C1N(CC1)CCN1C(=O)\C=C\C1=CC=CC(C(F)(F)F)=C1 CBXLQGOZYCGGAV-QPJJXVBHSA-N 0.000 claims 1
- GJUCDCMLPQLTFD-UHFFFAOYSA-N 2-[4-[[4-(6-carbamoyl-1h-benzimidazol-2-yl)piperazin-1-yl]methyl]phenyl]acetic acid Chemical compound N1C2=CC(C(=O)N)=CC=C2N=C1N(CC1)CCN1CC1=CC=C(CC(O)=O)C=C1 GJUCDCMLPQLTFD-UHFFFAOYSA-N 0.000 claims 1
- IIIFMPAEYWELPE-UHFFFAOYSA-N 2-[4-[[4-(trifluoromethoxy)phenyl]methyl]piperazin-1-yl]-3h-benzimidazole-5-carboxamide Chemical compound N1C2=CC(C(=O)N)=CC=C2N=C1N(CC1)CCN1CC1=CC=C(OC(F)(F)F)C=C1 IIIFMPAEYWELPE-UHFFFAOYSA-N 0.000 claims 1
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- UZJFRGXTJWDZDM-UHFFFAOYSA-N 6-chloro-3-[4-[(4-fluorophenyl)methyl]piperidin-1-yl]-1h-indole-2-carboxamide Chemical compound NC(=O)C=1NC2=CC(Cl)=CC=C2C=1N(CC1)CCC1CC1=CC=C(F)C=C1 UZJFRGXTJWDZDM-UHFFFAOYSA-N 0.000 claims 1
- 208000012998 acute renal failure Diseases 0.000 claims 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 208000002551 irritable bowel syndrome Diseases 0.000 claims 1
- 208000037906 ischaemic injury Diseases 0.000 claims 1
- 230000000302 ischemic effect Effects 0.000 claims 1
- ONAGBIKLKHGIBV-UHFFFAOYSA-N n-(1-acetyl-4-benzylpiperidin-2-yl)-1h-indole-5-carboxamide Chemical compound C1C(NC(=O)C=2C=C3C=CNC3=CC=2)N(C(=O)C)CCC1CC1=CC=CC=C1 ONAGBIKLKHGIBV-UHFFFAOYSA-N 0.000 claims 1
- CHZJGXQHTNZZIX-UHFFFAOYSA-N n-(4-benzyl-2-chloropiperidin-1-yl)-1h-indole-5-carboxamide Chemical compound C1CN(NC(=O)C=2C=C3C=CNC3=CC=2)C(Cl)CC1CC1=CC=CC=C1 CHZJGXQHTNZZIX-UHFFFAOYSA-N 0.000 claims 1
- OLSQLKPRUPCEFP-UHFFFAOYSA-N n-(4-benzyl-4-chloropiperidin-1-yl)-1h-indole-5-carboxamide Chemical compound C1CN(NC(=O)C=2C=C3C=CNC3=CC=2)CCC1(Cl)CC1=CC=CC=C1 OLSQLKPRUPCEFP-UHFFFAOYSA-N 0.000 claims 1
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- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
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Classifications
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- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- 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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms
-
- 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
- C07D401/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Urology & Nephrology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Neurology (AREA)
- Transplantation (AREA)
- Ophthalmology & Optometry (AREA)
- Biomedical Technology (AREA)
- Vascular Medicine (AREA)
- Neurosurgery (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Dermatology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8653198P | 1998-05-22 | 1998-05-22 | |
| US09/128,137 US6130235A (en) | 1998-05-22 | 1998-08-03 | Compounds and methods to treat cardiac failure and other disorders |
| US09/275,176 US6340685B1 (en) | 1998-05-22 | 1999-03-24 | Compounds and methods to treat cardiac failure and other disorders |
| PCT/US1999/011222 WO1999061426A1 (en) | 1998-05-22 | 1999-05-21 | Heterocyclic compounds and methods to treat cardiac failure and other disorders |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20005881D0 NO20005881D0 (no) | 2000-11-21 |
| NO20005881L NO20005881L (no) | 2001-01-09 |
| NO320299B1 true NO320299B1 (no) | 2005-11-21 |
Family
ID=46203611
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20005881A NO320299B1 (no) | 1998-05-22 | 2000-11-21 | Heterocykliske forbindelser og anvendelse av slike forbindelser for fremstilling av medikamenter. |
Country Status (15)
| Country | Link |
|---|---|
| EP (1) | EP1080078B1 (https=) |
| JP (1) | JP2002516314A (https=) |
| KR (1) | KR100605140B1 (https=) |
| CN (1) | CN1229351C (https=) |
| AT (1) | ATE316961T1 (https=) |
| AU (2) | AU769465B2 (https=) |
| BR (1) | BR9911069A (https=) |
| CA (1) | CA2332459A1 (https=) |
| DE (1) | DE69929689T2 (https=) |
| ES (1) | ES2258331T3 (https=) |
| HU (1) | HUP0203657A3 (https=) |
| NO (1) | NO320299B1 (https=) |
| NZ (1) | NZ508790A (https=) |
| PL (1) | PL346345A1 (https=) |
| WO (1) | WO1999061426A1 (https=) |
Families Citing this family (56)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US6514977B1 (en) | 1997-05-22 | 2003-02-04 | G.D. Searle & Company | Substituted pyrazoles as p38 kinase inhibitors |
| EP1019394A1 (en) | 1997-05-22 | 2000-07-19 | G.D. Searle & Co. | PYRAZOLE DERIVATIVES AS p38 KINASE INHIBITORS |
| US6979686B1 (en) | 2001-12-07 | 2005-12-27 | Pharmacia Corporation | Substituted pyrazoles as p38 kinase inhibitors |
| US6867209B1 (en) | 1998-05-22 | 2005-03-15 | Scios, Inc. | Indole-type derivatives as inhibitors of p38 kinase |
| US6448257B1 (en) | 1998-05-22 | 2002-09-10 | Scios, Inc. | Compounds and methods to treat cardiac failure and other disorders |
| US6589954B1 (en) | 1998-05-22 | 2003-07-08 | Scios, Inc. | Compounds and methods to treat cardiac failure and other disorders |
| US6858617B2 (en) | 1998-05-26 | 2005-02-22 | Smithkline Beecham Corporation | Substituted imidazole compounds |
| MXPA01002173A (es) * | 1998-08-28 | 2003-07-14 | Scios Inc | Inhibidores de p38-alfa cinasa. |
| DE69914357T2 (de) | 1998-11-04 | 2004-11-11 | Smithkline Beecham Corp. | Pyridin-4-yl oder pyrimidin-4-yl substituierte pyrazine |
| RU2278115C2 (ru) * | 1999-05-21 | 2006-06-20 | Сайос Инк. | ПРОИЗВОДНЫЕ ИНДОЛЬНОГО РЯДА В КАЧЕСТВЕ ИНГИБИТОРОВ p38 КИНАЗЫ |
| IL146309A (en) | 1999-05-21 | 2008-03-20 | Scios Inc | Derivatives of the indole type and pharmaceutical preparations containing them as inhibitors of kinase p38 |
| JP2003500403A (ja) * | 1999-05-21 | 2003-01-07 | サイオス，インコーポレーテッド | ｐ３８キナーゼのインヒビターとしてのインドール型誘導体 |
| US6541477B2 (en) | 1999-08-27 | 2003-04-01 | Scios, Inc. | Inhibitors of p38-a kinase |
| EP1233950B1 (en) | 1999-11-23 | 2005-10-05 | Smithkline Beecham Corporation | 3,4-DIHYDRO-(1H)QUINAZOLIN-2-ONE COMPOUNDS AS CSBP/P39 kINASE INHIBITORS |
| JP2003514900A (ja) | 1999-11-23 | 2003-04-22 | スミスクライン・ビーチャム・コーポレイション | ＣＳＢＰ／ｐ３８キナーゼ阻害剤としての３，４−ジヒドロ−（１Ｈ）−キナゾリン−２−オン化合物 |
| ATE281439T1 (de) | 1999-11-23 | 2004-11-15 | Smithkline Beecham Corp | 3,4-dihydro-(1h)chinazolin-2-on-verbindungen als csbp/p38-kinase-inhibitoren |
| US6372752B1 (en) * | 2000-02-07 | 2002-04-16 | Genzyme Corporation | Inha inhibitors and methods of use thereof |
| AU2001241927A1 (en) * | 2000-02-28 | 2001-09-12 | Scios Inc. | Inhibitors of p38-alpha kinase |
| US7235551B2 (en) | 2000-03-02 | 2007-06-26 | Smithkline Beecham Corporation | 1,5-disubstituted-3,4-dihydro-1h-pyrimido[4,5-d]pyrimidin-2-one compounds and their use in treating csbp/p38 kinase mediated diseases |
| JP5260818B2 (ja) * | 2000-09-29 | 2013-08-14 | ノバルティス・インターナショナル・ファーマシューティカル・リミテッド | 高親和性低分子Ｃ５ａ受容体調節物質 |
| EP1339708A2 (en) | 2000-11-20 | 2003-09-03 | Scios Inc. | Indole-type inhibitors of p38 kinase |
| EP1341782A2 (en) | 2000-11-20 | 2003-09-10 | Scios Inc. | Inhibitors of p38 kinase |
| DE60125980T2 (de) * | 2000-11-20 | 2007-10-25 | Scios Inc., Sunnyvale | P38kinase-inhibitoren vom piperidin/piperazin-typ |
| WO2003041644A2 (en) * | 2001-11-09 | 2003-05-22 | Scios Inc. | Method to treat cystic fibrosis |
| US20030225089A1 (en) * | 2002-04-10 | 2003-12-04 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Pharmaceutical compositions based on anticholinergics and p38 kinase inhibitors |
| ES2278170T3 (es) | 2002-07-09 | 2007-08-01 | BOEHRINGER INGELHEIM PHARMA GMBH & CO.KG | Composiciones farmaceuticas de anticolinergicos e inhibidores de la quinasa p38 en el tratamiento de enfermedades respiratorias. |
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| US4179505A (en) * | 1977-03-30 | 1979-12-18 | Janssen Pharmaceutica N.V. | 5-[4-(Diarylmethyl)-1-piperazinylalkyl]benzimidazole derivatives |
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| EP0318235A3 (en) * | 1987-11-25 | 1991-05-02 | Takeda Chemical Industries, Ltd. | Paf antagonist, 1,4-disubstituted piperazine compounds and production thereof |
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| FR2753706B1 (fr) * | 1996-09-20 | 1998-10-30 | Nouvelles amines cycliques n-substituees, leur procede de preparation et les compositions pharmaceutiques les renfermant | |
| JP2002515891A (ja) * | 1997-12-19 | 2002-05-28 | スミスクライン・ビーチャム・コーポレイション | 新規なピペリジン含有化合物 |
| GB9804734D0 (en) * | 1998-03-05 | 1998-04-29 | Pfizer Ltd | Compounds |
-
1999
- 1999-05-21 KR KR1020007013126A patent/KR100605140B1/ko not_active Expired - Fee Related
- 1999-05-21 BR BR9911069-5A patent/BR9911069A/pt not_active Application Discontinuation
- 1999-05-21 CN CNB998071528A patent/CN1229351C/zh not_active Expired - Fee Related
- 1999-05-21 JP JP2000550832A patent/JP2002516314A/ja active Pending
- 1999-05-21 NZ NZ508790A patent/NZ508790A/en unknown
- 1999-05-21 CA CA002332459A patent/CA2332459A1/en not_active Abandoned
- 1999-05-21 HU HU0203657A patent/HUP0203657A3/hu unknown
- 1999-05-21 PL PL99346345A patent/PL346345A1/xx not_active IP Right Cessation
- 1999-05-21 DE DE69929689T patent/DE69929689T2/de not_active Expired - Fee Related
- 1999-05-21 AU AU40920/99A patent/AU769465B2/en not_active Ceased
- 1999-05-21 AT AT99924412T patent/ATE316961T1/de not_active IP Right Cessation
- 1999-05-21 EP EP99924412A patent/EP1080078B1/en not_active Expired - Lifetime
- 1999-05-21 WO PCT/US1999/011222 patent/WO1999061426A1/en not_active Ceased
- 1999-05-21 ES ES99924412T patent/ES2258331T3/es not_active Expired - Lifetime
-
2000
- 2000-11-21 NO NO20005881A patent/NO320299B1/no unknown
-
2004
- 2004-04-29 AU AU2004201809A patent/AU2004201809A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| CN1305464A (zh) | 2001-07-25 |
| AU2004201809A1 (en) | 2004-05-27 |
| CA2332459A1 (en) | 1999-12-02 |
| AU769465B2 (en) | 2004-01-29 |
| WO1999061426A1 (en) | 1999-12-02 |
| NO20005881D0 (no) | 2000-11-21 |
| ES2258331T3 (es) | 2006-08-16 |
| DE69929689D1 (de) | 2006-04-13 |
| HK1034707A1 (en) | 2001-11-02 |
| EP1080078A1 (en) | 2001-03-07 |
| KR100605140B1 (ko) | 2006-07-28 |
| KR20010070946A (ko) | 2001-07-28 |
| NO20005881L (no) | 2001-01-09 |
| HUP0203657A2 (hu) | 2003-03-28 |
| EP1080078B1 (en) | 2006-02-01 |
| AU4092099A (en) | 1999-12-13 |
| JP2002516314A (ja) | 2002-06-04 |
| NZ508790A (en) | 2003-10-31 |
| HUP0203657A3 (en) | 2005-03-29 |
| DE69929689T2 (de) | 2006-11-02 |
| ATE316961T1 (de) | 2006-02-15 |
| BR9911069A (pt) | 2001-02-06 |
| CN1229351C (zh) | 2005-11-30 |
| PL346345A1 (en) | 2002-02-11 |
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