AU774808B2 - New piperdine-4-sulphonamide compounds, a process for their preparation and pharmaceutical compositions containing them - Google Patents
New piperdine-4-sulphonamide compounds, a process for their preparation and pharmaceutical compositions containing them Download PDFInfo
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- AU774808B2 AU774808B2 AU16747/01A AU1674701A AU774808B2 AU 774808 B2 AU774808 B2 AU 774808B2 AU 16747/01 A AU16747/01 A AU 16747/01A AU 1674701 A AU1674701 A AU 1674701A AU 774808 B2 AU774808 B2 AU 774808B2
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- Prior art keywords
- ethyl
- formula
- methyl
- compounds
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- 238000002360 preparation method Methods 0.000 title claims description 166
- 238000000034 method Methods 0.000 title claims description 133
- 230000008569 process Effects 0.000 title claims description 120
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 262
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 148
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 84
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 83
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 64
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 59
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 48
- 230000002829 reductive effect Effects 0.000 claims description 30
- 230000002792 vascular Effects 0.000 claims description 23
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 20
- -1 isoquinolin-5-yl group Chemical group 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 16
- 238000011282 treatment Methods 0.000 claims description 16
- 206010048554 Endothelial dysfunction Diseases 0.000 claims description 15
- 239000000460 chlorine Substances 0.000 claims description 15
- 230000008694 endothelial dysfunction Effects 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 150000004677 hydrates Chemical class 0.000 claims description 13
- 239000012453 solvate Substances 0.000 claims description 13
- 229940124530 sulfonamide Drugs 0.000 claims description 13
- 238000003786 synthesis reaction Methods 0.000 claims description 13
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 11
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000002619 bicyclic group Chemical group 0.000 claims description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 8
- 230000001575 pathological effect Effects 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
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- 206010034576 Peripheral ischaemia Diseases 0.000 claims description 5
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- 125000003277 amino group Chemical group 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 238000007796 conventional method Methods 0.000 claims description 5
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 238000002054 transplantation Methods 0.000 claims description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
- 230000009471 action Effects 0.000 claims description 4
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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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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 230000003902 lesion Effects 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 238000000746 purification Methods 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000004385 trihaloalkyl group Chemical group 0.000 claims description 4
- NOQLHWMOGZSFEV-UHFFFAOYSA-N 7-methoxy-1h-pyrrolo[2,3-c]pyridine-3-sulfonyl chloride Chemical compound COC1=NC=CC2=C1NC=C2S(Cl)(=O)=O NOQLHWMOGZSFEV-UHFFFAOYSA-N 0.000 claims description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 3
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- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 3
- 239000012312 sodium hydride Substances 0.000 claims description 3
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- 239000007858 starting material Substances 0.000 claims description 3
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- KVUXGIFBUWVWFL-UHFFFAOYSA-N 1-[1-[2-(1-benzofuran-2-yl)ethyl]piperidin-4-yl]-n-methylmethanamine Chemical compound C1CC(CNC)CCN1CCC1=CC2=CC=CC=C2O1 KVUXGIFBUWVWFL-UHFFFAOYSA-N 0.000 claims description 2
- FVFSAJPDOBUCEU-UHFFFAOYSA-N 1-[2-(6-methoxy-3h-inden-1-yl)ethyl]piperidin-4-amine Chemical compound C12=CC(OC)=CC=C2CC=C1CCN1CCC(N)CC1 FVFSAJPDOBUCEU-UHFFFAOYSA-N 0.000 claims description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000005864 Sulphur Substances 0.000 claims description 2
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims description 2
- 150000001408 amides Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 239000007822 coupling agent Substances 0.000 claims description 2
- 125000005046 dihydronaphthyl group Chemical group 0.000 claims description 2
- 229960001760 dimethyl sulfoxide Drugs 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- ZNCQTGJPCLMLRL-UHFFFAOYSA-N n-[1-[2-(1-benzofuran-3-yl)ethyl]piperidin-4-yl]isoquinoline-5-sulfonamide Chemical compound N1=CC=C2C(S(=O)(NC3CCN(CCC=4C5=CC=CC=C5OC=4)CC3)=O)=CC=CC2=C1 ZNCQTGJPCLMLRL-UHFFFAOYSA-N 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 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
- 238000006268 reductive amination reaction Methods 0.000 claims description 2
- 238000000926 separation method Methods 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
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 2
- BPLKQGGAXWRFOE-UHFFFAOYSA-M trimethylsulfoxonium iodide Chemical compound [I-].C[S+](C)(C)=O BPLKQGGAXWRFOE-UHFFFAOYSA-M 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 8
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 claims 4
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 3
- GZZCYMXZJQCAJU-UHFFFAOYSA-N isoquinoline-1-sulfonamide Chemical compound C1=CC=C2C(S(=O)(=O)N)=NC=CC2=C1 GZZCYMXZJQCAJU-UHFFFAOYSA-N 0.000 claims 3
- RQXCLMGKHJWMOA-UHFFFAOYSA-N pridinol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)CCN1CCCCC1 RQXCLMGKHJWMOA-UHFFFAOYSA-N 0.000 claims 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- GWPTXNUDBQIEBP-UHFFFAOYSA-N 1-[2-(1-benzofuran-3-yl)ethyl]-n-methylpiperidin-4-amine Chemical compound C1CC(NC)CCN1CCC1=COC2=CC=CC=C12 GWPTXNUDBQIEBP-UHFFFAOYSA-N 0.000 claims 2
- 241001092040 Crataegus Species 0.000 claims 2
- 235000009917 Crataegus X brevipes Nutrition 0.000 claims 2
- 235000013204 Crataegus X haemacarpa Nutrition 0.000 claims 2
- 235000009685 Crataegus X maligna Nutrition 0.000 claims 2
- 235000009444 Crataegus X rubrocarnea Nutrition 0.000 claims 2
- 235000009486 Crataegus bullatus Nutrition 0.000 claims 2
- 235000017181 Crataegus chrysocarpa Nutrition 0.000 claims 2
- 235000009682 Crataegus limnophila Nutrition 0.000 claims 2
- 235000004423 Crataegus monogyna Nutrition 0.000 claims 2
- 235000002313 Crataegus paludosa Nutrition 0.000 claims 2
- 235000009840 Crataegus x incaedua Nutrition 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000006833 (C1-C5) alkylene group Chemical group 0.000 claims 1
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
- CPDNXWUPDIHYPE-UHFFFAOYSA-N 1-(1-benzofuran-3-ylmethyl)piperidin-4-amine Chemical compound C1CC(N)CCN1CC1=COC2=CC=CC=C12 CPDNXWUPDIHYPE-UHFFFAOYSA-N 0.000 claims 1
- JOCHPWBPQAYQRP-UHFFFAOYSA-N 1-(4-aminopiperidin-1-yl)-3-(1-benzofuran-3-yl)propan-2-ol Chemical compound C1CC(N)CCN1CC(O)CC1=COC2=CC=CC=C12 JOCHPWBPQAYQRP-UHFFFAOYSA-N 0.000 claims 1
- GMFICMXNHDLJPM-UHFFFAOYSA-N 1-[(4-methoxy-1-benzofuran-3-yl)methyl]piperidin-4-amine Chemical compound C1=2C(OC)=CC=CC=2OC=C1CN1CCC(N)CC1 GMFICMXNHDLJPM-UHFFFAOYSA-N 0.000 claims 1
- AGTNSZZLLVDXSI-UHFFFAOYSA-N 3-(2-aminophenyl)-n-[1-[3-(1-benzofuran-3-yl)-2-hydroxypropyl]piperidin-4-yl]benzenesulfonamide Chemical compound NC1=CC=CC=C1C1=CC=CC(S(=O)(=O)NC2CCN(CC(O)CC=3C4=CC=CC=C4OC=3)CC2)=C1 AGTNSZZLLVDXSI-UHFFFAOYSA-N 0.000 claims 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims 1
- WGWCIGSJURBOSC-UHFFFAOYSA-N 4-(aminomethyl)-1-[2-(5-fluoro-1-benzofuran-3-yl)ethyl]piperidin-4-ol Chemical compound C1CC(CN)(O)CCN1CCC1=COC2=CC=C(F)C=C12 WGWCIGSJURBOSC-UHFFFAOYSA-N 0.000 claims 1
- IJPQYBRPCAKAOE-UHFFFAOYSA-N 5-methyl-2,1,3-benzoxadiazole-4-sulfonamide Chemical compound CC1=C(C=2C(=NON=2)C=C1)S(=O)(=O)N IJPQYBRPCAKAOE-UHFFFAOYSA-N 0.000 claims 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 1
- 101100269376 Mus musculus Agfg2 gene Proteins 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 claims 1
- GRHUCFHDSVGPLX-UHFFFAOYSA-N n-[1-[2-(1-benzofuran-3-yl)ethyl]piperidin-4-yl]-4-bromoisoquinoline-5-sulfonamide Chemical compound C1=CC=C2C(CCN3CCC(CC3)NS(=O)(=O)C=3C=CC=C4C=NC=C(C=34)Br)=COC2=C1 GRHUCFHDSVGPLX-UHFFFAOYSA-N 0.000 claims 1
- JFDDFJXHUHJCPK-UHFFFAOYSA-N n-[1-[2-(1-benzofuran-3-yl)ethyl]piperidin-4-yl]-4-fluoroisoquinoline-5-sulfonamide Chemical compound C1=CC=C2C(CCN3CCC(CC3)NS(=O)(=O)C=3C=CC=C4C=NC=C(C=34)F)=COC2=C1 JFDDFJXHUHJCPK-UHFFFAOYSA-N 0.000 claims 1
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- 238000002844 melting Methods 0.000 description 91
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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 6
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- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
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- 238000001816 cooling Methods 0.000 description 5
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 230000007246 mechanism Effects 0.000 description 5
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 230000003511 endothelial effect Effects 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
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Classifications
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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
- C07D401/12—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
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- 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
-
- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Hospice & Palliative Care (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0001171 | 2000-01-31 | ||
| 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 (2)
| Publication Number | Publication Date |
|---|---|
| AU1674701A AU1674701A (en) | 2001-08-02 |
| AU774808B2 true AU774808B2 (en) | 2004-07-08 |
Family
ID=8846469
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU16747/01A Ceased AU774808B2 (en) | 2000-01-31 | 2001-01-31 | New piperdine-4-sulphonamide compounds, a process for their preparation and pharmaceutical compositions containing them |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US6323217B2 (enExample) |
| EP (1) | EP1122254B1 (enExample) |
| JP (1) | JP3513493B2 (enExample) |
| KR (1) | KR100463369B1 (enExample) |
| CN (1) | CN1298705C (enExample) |
| AR (1) | AR027335A1 (enExample) |
| AT (1) | ATE294175T1 (enExample) |
| AU (1) | AU774808B2 (enExample) |
| BR (1) | BR0100234A (enExample) |
| CA (1) | CA2332513C (enExample) |
| DE (1) | DE60110278T2 (enExample) |
| DK (1) | DK1122254T3 (enExample) |
| EA (1) | EA003096B1 (enExample) |
| ES (1) | ES2241757T3 (enExample) |
| FR (1) | FR2804429B1 (enExample) |
| HK (1) | HK1039117B (enExample) |
| HU (1) | HUP0100489A3 (enExample) |
| MX (1) | MXPA01000945A (enExample) |
| NO (1) | NO320387B1 (enExample) |
| NZ (1) | NZ509636A (enExample) |
| PL (1) | PL345528A1 (enExample) |
| PT (1) | PT1122254E (enExample) |
| SI (1) | SI1122254T1 (enExample) |
| ZA (1) | ZA200100864B (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ521978A (en) * | 2000-04-28 | 2004-10-29 | Acadia Pharm Inc | Compounds that affect cholinergic receptors and are particularly muscarinic agonists |
| EP1535912A1 (en) * | 2000-04-28 | 2005-06-01 | Arcadia 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 |
| AU2003284402A1 (en) * | 2002-11-15 | 2004-06-15 | Yamanouchi Pharmaceutical Co., Ltd. | Antagonist to melanin-concentrating hormone receptor |
| 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 |
| ATE527258T1 (de) * | 2004-07-28 | 2011-10-15 | Takeda Pharmaceutical | Pyrroloä2,3-cüpyridinverbindung, verfahren zu deren herstellung und anwendung |
| TW200630337A (en) * | 2004-10-14 | 2006-09-01 | Euro Celtique Sa | Piperidinyl compounds and the use thereof |
| ES2362617T3 (es) * | 2005-02-25 | 2011-07-08 | Kowa Company, Ltd. | Proceso para la producción de haluro de 4-fluoroisoquinolin-5-sulfonilo o una de sus sales. |
| WO2007110449A1 (en) | 2006-03-29 | 2007-10-04 | Euro-Celtique S.A. | Benzenesulfonamide compounds and their use |
| TW200812963A (en) | 2006-04-13 | 2008-03-16 | Euro Celtique Sa | Benzenesulfonamide compounds and the use thereof |
| US8791264B2 (en) | 2006-04-13 | 2014-07-29 | Purdue Pharma L.P. | Benzenesulfonamide compounds and their use as blockers of calcium channels |
| CL2007003223A1 (es) * | 2006-11-10 | 2008-01-11 | Wyeth Corp | Compuestos derivados de piperidinil 4-arilsulfonamidas n-sustituidas, que actuan como moduladores de la proteina sfrp-1; proceso para preparar los compuestos; co mposicion farmaceutica que comprende a dichos copmpuestos y uso de los compuestos para preparar medicamentos para el tratamiento de enfermedades. |
| WO2008124118A1 (en) * | 2007-04-09 | 2008-10-16 | Purdue Pharma L.P. | Benzenesulfonyl compounds and the use therof |
| US8765736B2 (en) | 2007-09-28 | 2014-07-01 | Purdue Pharma L.P. | Benzenesulfonamide compounds and the use thereof |
| AR080375A1 (es) | 2010-03-05 | 2012-04-04 | Sanofi Aventis | Procedimiento para la preparacion de 2-(cicloheximetil)-n-{2-[(2s)-1-metilpirrolidin-2-il] etil}-1,2,3,4-tetrahidroisoquinolina- 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 US US09/772,569 patent/US6323217B2/en not_active Expired - Fee Related
- 2001-01-30 EP EP01400225A patent/EP1122254B1/fr not_active Expired - Lifetime
- 2001-01-30 NO NO20010522A patent/NO320387B1/no unknown
- 2001-01-30 CA CA002332513A patent/CA2332513C/fr not_active Expired - Fee Related
- 2001-01-30 HU HU0100489A patent/HUP0100489A3/hu unknown
- 2001-01-30 ES ES01400225T patent/ES2241757T3/es not_active Expired - Lifetime
- 2001-01-30 DK DK01400225T patent/DK1122254T3/da active
- 2001-01-30 NZ NZ509636A patent/NZ509636A/en unknown
- 2001-01-30 EA EA200100090A patent/EA003096B1/ru unknown
- 2001-01-30 AT AT01400225T patent/ATE294175T1/de not_active IP Right Cessation
- 2001-01-30 PT PT01400225T patent/PT1122254E/pt unknown
- 2001-01-30 SI SI200130342T patent/SI1122254T1/xx unknown
- 2001-01-30 DE DE60110278T patent/DE60110278T2/de not_active Expired - Fee Related
- 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 PL PL01345528A patent/PL345528A1/xx unknown
- 2001-01-31 ZA ZA200100864A patent/ZA200100864B/xx unknown
- 2001-01-31 KR KR10-2001-0004591A patent/KR100463369B1/ko not_active Expired - Fee Related
- 2001-01-31 BR BR0100234-1A patent/BR0100234A/pt not_active IP Right Cessation
- 2001-01-31 AU AU16747/01A patent/AU774808B2/en not_active Ceased
-
2002
- 2002-01-16 HK HK02100331.6A patent/HK1039117B/zh not_active IP Right Cessation
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Legal Events
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| PC1 | Assignment before grant (sect. 113) |
Owner name: LES LABORATOIRES SERVIER Free format text: THE FORMER OWNER WAS: ADIR ET COMPAGNIE |
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| FGA | Letters patent sealed or granted (standard patent) |