NO320387B1 - Piperidin-4-sulfonamidforbindelser, fremgangsmate ved deres fremstilling og farmasoytiske sammensetninger inneholdende dem, samt anvendelse av forbindelsene - Google Patents
Piperidin-4-sulfonamidforbindelser, fremgangsmate ved deres fremstilling og farmasoytiske sammensetninger inneholdende dem, samt anvendelse av forbindelsene Download PDFInfo
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- NO320387B1 NO320387B1 NO20010522A NO20010522A NO320387B1 NO 320387 B1 NO320387 B1 NO 320387B1 NO 20010522 A NO20010522 A NO 20010522A NO 20010522 A NO20010522 A NO 20010522A NO 320387 B1 NO320387 B1 NO 320387B1
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- 150000001875 compounds Chemical class 0.000 title claims description 253
- 238000002360 preparation method Methods 0.000 title claims description 165
- 238000000034 method Methods 0.000 title claims description 116
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 6
- SMXMELMJCICPJG-UHFFFAOYSA-N piperidine-4-sulfonamide Chemical class NS(=O)(=O)C1CCNCC1 SMXMELMJCICPJG-UHFFFAOYSA-N 0.000 title description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 31
- 230000002829 reductive effect Effects 0.000 claims description 29
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- 230000002792 vascular Effects 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 206010048554 Endothelial dysfunction Diseases 0.000 claims description 14
- 230000008694 endothelial dysfunction Effects 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
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- 238000011282 treatment Methods 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 238000003786 synthesis reaction Methods 0.000 claims description 13
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 11
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
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- 125000003118 aryl group Chemical group 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
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- 238000007796 conventional method Methods 0.000 claims description 5
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- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 4
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- 125000006833 (C1-C5) alkylene group Chemical group 0.000 claims description 2
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 2
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- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
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- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 238000006268 reductive amination reaction Methods 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 150000003456 sulfonamides Chemical class 0.000 claims description 2
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 2
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- BPLKQGGAXWRFOE-UHFFFAOYSA-M trimethylsulfoxonium iodide Chemical compound [I-].C[S+](C)(C)=O BPLKQGGAXWRFOE-UHFFFAOYSA-M 0.000 claims 1
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- 239000003153 chemical reaction reagent Substances 0.000 description 26
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 24
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- 229910002027 silica gel Inorganic materials 0.000 description 20
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- ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 description 5
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- BTVFGXFUSWHJCW-UHFFFAOYSA-N n-[[1-[2-(1-benzofuran-3-yl)ethyl]piperidin-4-yl]methyl]-n-methylisoquinoline-5-sulfonamide Chemical compound N1=CC=C2C(S(=O)(=O)N(CC3CCN(CCC=4C5=CC=CC=C5OC=4)CC3)C)=CC=CC2=C1 BTVFGXFUSWHJCW-UHFFFAOYSA-N 0.000 description 1
- BMKNMUONFJQLQE-UHFFFAOYSA-N n-[[1-[2-(5-fluoro-1-benzofuran-3-yl)ethyl]-4-hydroxypiperidin-4-yl]methyl]-n-methylisoquinoline-5-sulfonamide Chemical compound N1=CC=C2C(S(=O)(=O)N(CC3(O)CCN(CCC=4C5=CC(F)=CC=C5OC=4)CC3)C)=CC=CC2=C1 BMKNMUONFJQLQE-UHFFFAOYSA-N 0.000 description 1
- SRSNJOWRMCMLQR-UHFFFAOYSA-N n-[[1-[2-(5-fluoro-1-benzofuran-3-yl)ethyl]-4-hydroxypiperidin-4-yl]methyl]isoquinoline-5-sulfonamide Chemical compound C1=C(F)C=C2C(CCN3CCC(CC3)(CNS(=O)(=O)C=3C4=CC=NC=C4C=CC=3)O)=COC2=C1 SRSNJOWRMCMLQR-UHFFFAOYSA-N 0.000 description 1
- AGLCMALXYUIADL-UHFFFAOYSA-N n-[[4-hydroxy-1-[2-(3h-inden-1-yl)ethyl]piperidin-4-yl]methyl]-n-methylisoquinoline-5-sulfonamide Chemical compound N1=CC=C2C(S(=O)(=O)N(CC3(O)CCN(CCC=4C5=CC=CC=C5CC=4)CC3)C)=CC=CC2=C1 AGLCMALXYUIADL-UHFFFAOYSA-N 0.000 description 1
- GWADYZAYWCMXJH-UHFFFAOYSA-N n-[[4-hydroxy-1-[2-(3h-inden-1-yl)ethyl]piperidin-4-yl]methyl]isoquinoline-5-sulfonamide Chemical compound C1=CC=C2C(CCN3CCC(CC3)(CNS(=O)(=O)C=3C4=CC=NC=C4C=CC=3)O)=CCC2=C1 GWADYZAYWCMXJH-UHFFFAOYSA-N 0.000 description 1
- XOKRIMITEZHOEO-UHFFFAOYSA-N n-[[4-hydroxy-1-[2-(5-methoxy-1-benzofuran-3-yl)ethyl]piperidin-4-yl]methyl]-2,1,3-benzoxadiazole-4-sulfonamide Chemical compound C1=CC2=NON=C2C(S(=O)(=O)NCC2(CCN(CC2)CCC2=COC3=CC=C(C=C32)OC)O)=C1 XOKRIMITEZHOEO-UHFFFAOYSA-N 0.000 description 1
- ZLSJELLLXWPQCC-UHFFFAOYSA-N n-[[4-hydroxy-1-[2-(5-methoxy-1-benzofuran-3-yl)ethyl]piperidin-4-yl]methyl]isoquinoline-5-sulfonamide Chemical compound N1=CC=C2C(S(=O)(=O)NCC3(CCN(CC3)CCC3=COC4=CC=C(C=C43)OC)O)=CC=CC2=C1 ZLSJELLLXWPQCC-UHFFFAOYSA-N 0.000 description 1
- XUVPHDGZURKNAS-UHFFFAOYSA-N n-[[4-hydroxy-1-[2-(7-methoxy-1-benzofuran-3-yl)ethyl]piperidin-4-yl]methyl]-n-methyl-2,1,3-benzoxadiazole-4-sulfonamide Chemical compound C1=CC2=NON=C2C(S(=O)(=O)N(C)CC2(CCN(CC2)CCC=2C=3C=CC=C(C=3OC=2)OC)O)=C1 XUVPHDGZURKNAS-UHFFFAOYSA-N 0.000 description 1
- AGPIFGBSWFMSSU-UHFFFAOYSA-N n-[[4-hydroxy-1-[2-(7-methoxy-1-benzofuran-3-yl)ethyl]piperidin-4-yl]methyl]-n-methylisoquinoline-5-sulfonamide Chemical compound N1=CC=C2C(S(=O)(=O)N(C)CC3(CCN(CC3)CCC=3C=4C=CC=C(C=4OC=3)OC)O)=CC=CC2=C1 AGPIFGBSWFMSSU-UHFFFAOYSA-N 0.000 description 1
- VBHXCAKPNNIEMZ-UHFFFAOYSA-N n-[[4-hydroxy-1-[2-(7-methoxy-1-benzofuran-3-yl)ethyl]piperidin-4-yl]methyl]isoquinoline-5-sulfonamide Chemical compound N1=CC=C2C(S(=O)(=O)NCC3(CCN(CC3)CCC=3C=4C=CC=C(C=4OC=3)OC)O)=CC=CC2=C1 VBHXCAKPNNIEMZ-UHFFFAOYSA-N 0.000 description 1
- DASJFYAPNPUBGG-UHFFFAOYSA-N naphthalene-1-sulfonyl chloride Chemical compound C1=CC=C2C(S(=O)(=O)Cl)=CC=CC2=C1 DASJFYAPNPUBGG-UHFFFAOYSA-N 0.000 description 1
- 229940100662 nasal drops Drugs 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229940116315 oxalic acid Drugs 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- FERZDALKDCSVRX-UHFFFAOYSA-M potassium;carbamate Chemical compound [K+].NC([O-])=O FERZDALKDCSVRX-UHFFFAOYSA-M 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- CDRNYKLYADJTMN-UHFFFAOYSA-N pyridine-3-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CN=C1 CDRNYKLYADJTMN-UHFFFAOYSA-N 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 238000003127 radioimmunoassay Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 208000037803 restenosis Diseases 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 210000000329 smooth muscle myocyte Anatomy 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- KVCXSAPEPMSWPO-UHFFFAOYSA-N tert-butyl n-[1-(4-methoxy-1-benzofuran-3-carbonyl)piperidin-4-yl]carbamate Chemical compound C1=2C(OC)=CC=CC=2OC=C1C(=O)N1CCC(NC(=O)OC(C)(C)C)CC1 KVCXSAPEPMSWPO-UHFFFAOYSA-N 0.000 description 1
- AEMFVGBMVHIVBU-UHFFFAOYSA-N tert-butyl n-[1-[2-(1-benzofuran-3-yl)-2-oxoethyl]piperidin-4-yl]carbamate Chemical compound C1CC(NC(=O)OC(C)(C)C)CCN1CC(=O)C1=COC2=CC=CC=C12 AEMFVGBMVHIVBU-UHFFFAOYSA-N 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 230000002537 thrombolytic effect Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- YRYSAWZMIRQUBO-UHFFFAOYSA-N trimethylsulfoxonium Chemical compound C[S+](C)(C)=O YRYSAWZMIRQUBO-UHFFFAOYSA-N 0.000 description 1
- 230000025033 vasoconstriction Effects 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
- A61P9/10—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
-
- 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
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0001171A FR2804429B1 (fr) | 2000-01-31 | 2000-01-31 | Nouveaux derives de 4-sulfonamides piperidine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20010522D0 NO20010522D0 (no) | 2001-01-30 |
| NO20010522L NO20010522L (no) | 2001-08-01 |
| NO320387B1 true NO320387B1 (no) | 2005-11-28 |
Family
ID=8846469
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20010522A NO320387B1 (no) | 2000-01-31 | 2001-01-30 | Piperidin-4-sulfonamidforbindelser, fremgangsmate ved deres fremstilling og farmasoytiske sammensetninger inneholdende dem, samt anvendelse av forbindelsene |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US6323217B2 (ru) |
| EP (1) | EP1122254B1 (ru) |
| JP (1) | JP3513493B2 (ru) |
| KR (1) | KR100463369B1 (ru) |
| CN (1) | CN1298705C (ru) |
| AR (1) | AR027335A1 (ru) |
| AT (1) | ATE294175T1 (ru) |
| AU (1) | AU774808B2 (ru) |
| BR (1) | BR0100234A (ru) |
| CA (1) | CA2332513C (ru) |
| DE (1) | DE60110278T2 (ru) |
| DK (1) | DK1122254T3 (ru) |
| EA (1) | EA003096B1 (ru) |
| ES (1) | ES2241757T3 (ru) |
| FR (1) | FR2804429B1 (ru) |
| HK (1) | HK1039117B (ru) |
| HU (1) | HUP0100489A3 (ru) |
| MX (1) | MXPA01000945A (ru) |
| NO (1) | NO320387B1 (ru) |
| NZ (1) | NZ509636A (ru) |
| PL (1) | PL345528A1 (ru) |
| PT (1) | PT1122254E (ru) |
| SI (1) | SI1122254T1 (ru) |
| ZA (1) | ZA200100864B (ru) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1535912A1 (en) * | 2000-04-28 | 2005-06-01 | Arcadia Pharmaceuticals Inc. | Muscarinic agonists |
| US6627645B2 (en) * | 2000-04-28 | 2003-09-30 | Acadia Pharmaceuticals, Inc. | Muscarinic agonists |
| AR040336A1 (es) * | 2002-06-26 | 2005-03-30 | Glaxo Group Ltd | Compuesto de piperidina, uso del mismo para la fabricacion de un medicamento, composicion farmaceutica que lo comprende y procedimiento para preparar dicho compuesto |
| JPWO2004046110A1 (ja) * | 2002-11-15 | 2006-03-16 | アステラス製薬株式会社 | メラニン凝集ホルモン受容体拮抗剤 |
| JP2008507492A (ja) * | 2004-07-23 | 2008-03-13 | バイエル・クロツプサイエンス・エス・アー | 殺菌剤としてのｎ−［２−（４−ピリジニル）エチル］ベンズアミド誘導体 |
| EP1787991B2 (en) * | 2004-07-28 | 2020-06-24 | Takeda Pharmaceutical Company Limited | PYRROLO[2,3-c]PYRIDINE COMPOUND, PROCESS FOR PRODUCING THE SAME, AND USE |
| TW200630337A (en) * | 2004-10-14 | 2006-09-01 | Euro Celtique Sa | Piperidinyl compounds and the use thereof |
| US7872136B2 (en) | 2005-02-25 | 2011-01-18 | Kowa Co., Ltd. | Process for production of 4-fluoroisoquinoline-5-sulfonyl halide or salt thereof |
| WO2007110449A1 (en) | 2006-03-29 | 2007-10-04 | Euro-Celtique S.A. | Benzenesulfonamide compounds and their use |
| TW200815353A (en) | 2006-04-13 | 2008-04-01 | Euro Celtique Sa | Benzenesulfonamide compounds and their use |
| US8937181B2 (en) | 2006-04-13 | 2015-01-20 | Purdue Pharma L.P. | Benzenesulfonamide compounds and the use thereof |
| PE20080932A1 (es) * | 2006-11-10 | 2008-07-13 | Wyeth Corp | Piperidinil 4-arilsulfonamidas n-sustituidas como moduladores de la proteina 1 secretada relacionada con frizzled (sfrp-1) |
| US8399486B2 (en) * | 2007-04-09 | 2013-03-19 | Purdue Pharma L.P. | Benzenesulfonyl compounds and the use thereof |
| US8765736B2 (en) | 2007-09-28 | 2014-07-01 | Purdue Pharma L.P. | Benzenesulfonamide compounds and the use thereof |
| AR080374A1 (es) | 2010-03-05 | 2012-04-04 | Sanofi Aventis | Procedimiento para la preparcion de 2-(ciclohexilmetil)-n-(2-((2s)-1-metilpirrolidin-2-il) etil)- 1,2,3,4-tetrahidroisoquinolin-7- sulfonamida |
| PL395470A1 (pl) * | 2011-06-29 | 2013-01-07 | Adamed Spólka Z Ograniczona Odpowiedzialnoscia | Sulfonamidowe pochodne amin alicyklicznych do leczenia chorób osrodkowego ukladu nerwowego |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4956382A (en) * | 1987-02-07 | 1990-09-11 | Pfizer Inc. | Sulfonamide anti-arrhythmic agents |
| US4857301A (en) * | 1987-09-25 | 1989-08-15 | Schering Corporation | Sulfonamide compounds, compositions and method of use |
| FR2679906B1 (fr) * | 1991-07-31 | 1995-01-20 | Adir | Nouvelles (isoquinolein-5 yl) sulfonamides, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| DK148392D0 (da) * | 1992-12-09 | 1992-12-09 | Lundbeck & Co As H | Heterocykliske forbindelser |
| AU6971794A (en) * | 1993-05-26 | 1994-12-20 | Smithkline Beecham Laboratoires Pharmaceutiques | Novel compounds |
| FR2716679B1 (fr) * | 1994-02-25 | 1996-04-05 | Adir | Nouvelles sulfonamides substituées, leur procédé de préparation et les compositions pharmaceutiques les renfermant. |
| HN1997000027A (es) * | 1996-12-06 | 1997-06-05 | Pfizer Prod Inc | Derivados de 6-fenil piridil - 2 amina |
-
2000
- 2000-01-31 FR FR0001171A patent/FR2804429B1/fr not_active Expired - Fee Related
-
2001
- 2001-01-23 CN CNB011123346A patent/CN1298705C/zh not_active Expired - Fee Related
- 2001-01-26 MX MXPA01000945A patent/MXPA01000945A/es unknown
- 2001-01-30 DK DK01400225T patent/DK1122254T3/da active
- 2001-01-30 ES ES01400225T patent/ES2241757T3/es not_active Expired - Lifetime
- 2001-01-30 SI SI200130342T patent/SI1122254T1/xx unknown
- 2001-01-30 EP EP01400225A patent/EP1122254B1/fr not_active Expired - Lifetime
- 2001-01-30 HU HU0100489A patent/HUP0100489A3/hu unknown
- 2001-01-30 NO NO20010522A patent/NO320387B1/no unknown
- 2001-01-30 PT PT01400225T patent/PT1122254E/pt unknown
- 2001-01-30 AT AT01400225T patent/ATE294175T1/de not_active IP Right Cessation
- 2001-01-30 CA CA002332513A patent/CA2332513C/fr not_active Expired - Fee Related
- 2001-01-30 US US09/772,569 patent/US6323217B2/en not_active Expired - Fee Related
- 2001-01-30 NZ NZ509636A patent/NZ509636A/en unknown
- 2001-01-30 DE DE60110278T patent/DE60110278T2/de not_active Expired - Fee Related
- 2001-01-30 EA EA200100090A patent/EA003096B1/ru unknown
- 2001-01-31 BR BR0100234-1A patent/BR0100234A/pt not_active IP Right Cessation
- 2001-01-31 PL PL01345528A patent/PL345528A1/xx unknown
- 2001-01-31 KR KR10-2001-0004591A patent/KR100463369B1/ko not_active IP Right Cessation
- 2001-01-31 AR ARP010100429A patent/AR027335A1/es not_active Application Discontinuation
- 2001-01-31 JP JP2001022954A patent/JP3513493B2/ja not_active Expired - Fee Related
- 2001-01-31 AU AU16747/01A patent/AU774808B2/en not_active Ceased
- 2001-01-31 ZA ZA200100864A patent/ZA200100864B/xx unknown
-
2002
- 2002-01-16 HK HK02100331.6A patent/HK1039117B/zh not_active IP Right Cessation
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