NZ509119A - Substituted N-piperidinylethyl-1-indolinecarboxamide derivatives and their use in endothelial dysfunction conditions. - Google Patents
Substituted N-piperidinylethyl-1-indolinecarboxamide derivatives and their use in endothelial dysfunction conditions.Info
- Publication number
- NZ509119A NZ509119A NZ509119A NZ50911900A NZ509119A NZ 509119 A NZ509119 A NZ 509119A NZ 509119 A NZ509119 A NZ 509119A NZ 50911900 A NZ50911900 A NZ 50911900A NZ 509119 A NZ509119 A NZ 509119A
- Authority
- NZ
- New Zealand
- Prior art keywords
- formula
- group
- compounds
- linear
- product
- Prior art date
Links
- 206010048554 Endothelial dysfunction Diseases 0.000 title claims description 15
- 230000008694 endothelial dysfunction Effects 0.000 title claims description 15
- ITBUIFXIFMDNRK-UHFFFAOYSA-N N-(2-piperidin-1-ylethyl)-2,3-dihydroindole-1-carboxamide Chemical class N1(CCCCC1)CCNC(=O)N1CCC2=CC=CC=C12 ITBUIFXIFMDNRK-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 271
- -1 cyclic ureas Chemical class 0.000 claims abstract description 39
- 230000002792 vascular Effects 0.000 claims abstract description 26
- 208000031225 myocardial ischemia Diseases 0.000 claims abstract description 6
- 208000032928 Dyslipidaemia Diseases 0.000 claims abstract description 5
- 206010019280 Heart failures Diseases 0.000 claims abstract description 5
- 206010034576 Peripheral ischaemia Diseases 0.000 claims abstract description 5
- 206010064911 Pulmonary arterial hypertension Diseases 0.000 claims abstract description 5
- 208000037849 arterial hypertension Diseases 0.000 claims abstract description 5
- 238000011161 development Methods 0.000 claims abstract description 5
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 5
- 230000002107 myocardial effect Effects 0.000 claims abstract description 5
- 238000002054 transplantation Methods 0.000 claims abstract description 5
- 230000003143 atherosclerotic effect Effects 0.000 claims abstract description 4
- 230000003902 lesion Effects 0.000 claims abstract description 4
- 230000009885 systemic effect Effects 0.000 claims abstract description 4
- 239000003814 drug Substances 0.000 claims abstract 3
- 238000002360 preparation method Methods 0.000 claims description 240
- 238000000034 method Methods 0.000 claims description 149
- 230000009471 action Effects 0.000 claims description 75
- 125000002947 alkylene group Chemical group 0.000 claims description 30
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 21
- 239000012453 solvate Substances 0.000 claims description 21
- 150000004677 hydrates Chemical class 0.000 claims description 20
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
- 125000004532 benzofuran-3-yl group Chemical group O1C=C(C2=C1C=CC=C2)* 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 238000011282 treatment Methods 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 238000003786 synthesis reaction Methods 0.000 claims description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 8
- 230000001575 pathological effect Effects 0.000 claims description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 125000002619 bicyclic group Chemical group 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 238000007796 conventional method Methods 0.000 claims description 5
- HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 239000005864 Sulphur Substances 0.000 claims description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 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
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000004385 trihaloalkyl group Chemical group 0.000 claims description 4
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 claims description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
- WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical group CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000005046 dihydronaphthyl group Chemical group 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 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
- 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
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000004952 trihaloalkoxy group Chemical group 0.000 claims description 2
- 101100370100 Mus musculus Tor3a gene Proteins 0.000 claims 1
- 235000013877 carbamide Nutrition 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 314
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 305
- 239000000758 substrate Substances 0.000 description 116
- 239000000243 solution Substances 0.000 description 103
- 238000004452 microanalysis Methods 0.000 description 99
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 96
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 90
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 79
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 79
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 60
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
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- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 24
- 238000002844 melting Methods 0.000 description 23
- 230000008018 melting Effects 0.000 description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 19
- 239000000203 mixture Substances 0.000 description 19
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 14
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 13
- 239000000741 silica gel Substances 0.000 description 13
- 229910002027 silica gel Inorganic materials 0.000 description 13
- OFLWZAHKUJNRML-UHFFFAOYSA-N 2,3-dihydroindole-1-carboxamide Chemical compound C1=CC=C2N(C(=O)N)CCC2=C1 OFLWZAHKUJNRML-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 238000004587 chromatography analysis Methods 0.000 description 12
- 239000012074 organic phase Substances 0.000 description 11
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 8
- 229960004373 acetylcholine Drugs 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- ODFFPRGJZRXNHZ-UHFFFAOYSA-N 5-fluoroindole Chemical compound FC1=CC=C2NC=CC2=C1 ODFFPRGJZRXNHZ-UHFFFAOYSA-N 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
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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
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000003857 carboxamides Chemical class 0.000 description 6
- ZOOGRGPOEVQQDX-UHFFFAOYSA-N cyclic GMP Natural products O1C2COP(O)(=O)OC2C(O)C1N1C=NC2=C1NC(N)=NC2=O ZOOGRGPOEVQQDX-UHFFFAOYSA-N 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- CQILOHWHIWNQOE-UHFFFAOYSA-N indole-1-carboxamide Chemical compound C1=CC=C2N(C(=O)N)C=CC2=C1 CQILOHWHIWNQOE-UHFFFAOYSA-N 0.000 description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 5
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- 230000007246 mechanism Effects 0.000 description 5
- 230000001681 protective effect Effects 0.000 description 5
- VFHUJFBEFDVZPJ-UHFFFAOYSA-N 1h-indole-2-carboxamide Chemical compound C1=CC=C2NC(C(=O)N)=CC2=C1 VFHUJFBEFDVZPJ-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
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- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 4
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- 230000000144 pharmacologic effect Effects 0.000 description 4
- 125000005936 piperidyl group Chemical group 0.000 description 4
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Classifications
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
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- C—CHEMISTRY; METALLURGY
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- 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
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- C07—ORGANIC CHEMISTRY
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- 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
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- C—CHEMISTRY; METALLURGY
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- 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
- C07D417/02—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 two hetero rings
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- 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
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F21—LIGHTING
- F21V—FUNCTIONAL FEATURES OR DETAILS OF LIGHTING DEVICES OR SYSTEMS THEREOF; STRUCTURAL COMBINATIONS OF LIGHTING DEVICES WITH OTHER ARTICLES, NOT OTHERWISE PROVIDED FOR
- F21V21/00—Supporting, suspending, or attaching arrangements for lighting devices; Hand grips
- F21V21/02—Wall, ceiling, or floor bases; Fixing pendants or arms to the bases
- F21V21/04—Recessed bases
- F21V21/041—Mounting arrangements specially adapted for false ceiling panels or partition walls made of plates
- F21V21/042—Mounting arrangements specially adapted for false ceiling panels or partition walls made of plates using clamping means, e.g. for clamping with panel or wall
- F21V21/043—Mounting arrangements specially adapted for false ceiling panels or partition walls made of plates using clamping means, e.g. for clamping with panel or wall actuated by screwing
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (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)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Obesity (AREA)
- General Engineering & Computer Science (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Vascular Medicine (AREA)
- Emergency Medicine (AREA)
- Architecture (AREA)
- Urology & Nephrology (AREA)
- Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9916701A FR2803298A1 (fr) | 1999-12-30 | 1999-12-30 | Nouvelles urees lineaires ou cycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ509119A true NZ509119A (en) | 2001-09-28 |
Family
ID=9554011
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ509119A NZ509119A (en) | 1999-12-30 | 2000-12-22 | Substituted N-piperidinylethyl-1-indolinecarboxamide derivatives and their use in endothelial dysfunction conditions. |
Country Status (23)
| Country | Link |
|---|---|
| US (4) | US6566364B2 (enExample) |
| EP (2) | EP1113014B1 (enExample) |
| JP (2) | JP3396671B2 (enExample) |
| KR (2) | KR100511134B1 (enExample) |
| CN (1) | CN1189466C (enExample) |
| AT (1) | ATE294170T1 (enExample) |
| AU (1) | AU776125B2 (enExample) |
| BR (1) | BR0007348A (enExample) |
| CA (1) | CA2330351C (enExample) |
| CY (1) | CY1106396T1 (enExample) |
| DE (2) | DE60019716T2 (enExample) |
| DK (2) | DK1113014T3 (enExample) |
| EA (1) | EA004040B1 (enExample) |
| ES (2) | ES2240035T3 (enExample) |
| FR (1) | FR2803298A1 (enExample) |
| HU (1) | HUP0005014A2 (enExample) |
| MX (1) | MXPA00012672A (enExample) |
| NO (1) | NO20006708L (enExample) |
| NZ (1) | NZ509119A (enExample) |
| PL (1) | PL344854A1 (enExample) |
| PT (2) | PT1266896E (enExample) |
| SI (2) | SI1113014T1 (enExample) |
| ZA (1) | ZA200100022B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1535912A1 (en) * | 2000-04-28 | 2005-06-01 | Arcadia Pharmaceuticals Inc. | Muscarinic agonists |
| RU2269523C2 (ru) * | 2000-04-28 | 2006-02-10 | Акадиа Фармасьютикалз, Инк. | Мускариновые агонисты |
| JPWO2004011430A1 (ja) * | 2002-07-25 | 2005-11-24 | アステラス製薬株式会社 | ナトリウムチャネル阻害剤 |
| CN106661009B (zh) * | 2014-04-28 | 2019-11-26 | 江苏康缘药业股份有限公司 | 抗肠病毒71噻二唑烷衍生物 |
| WO2015184222A1 (en) * | 2014-05-30 | 2015-12-03 | Southern Research Institute | Inhibitors of hepatocyte growth factor [hgf] and macrophage stimulating protein [msp] maturation |
| CN109824600B (zh) * | 2017-11-23 | 2020-10-02 | 中国科学院大连化学物理研究所 | 一种钯催化2-羟基嘧啶化合物的不对称氢化合成手性环状脲的方法 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1695735A1 (de) * | 1966-06-14 | 1971-04-22 | Searle & Co | Verfahren zur Herstellung neuer 3-Phenyl-2-(1H)-chinazolinon-Derivate |
| CH598251A5 (enExample) * | 1972-08-24 | 1978-04-28 | Ciba Geigy Ag | |
| FR2300563A1 (fr) * | 1975-02-13 | 1976-09-10 | Sandoz Sa | Nouveaux derives du thiazole, leur preparation et leur application comme medicaments |
| ZA76475B (en) * | 1975-03-10 | 1977-08-31 | Ciba Geigy Ag | Indolyalkylpiperidines |
| DE2701794A1 (de) * | 1976-01-21 | 1977-07-28 | Ciba Geigy Ag | Oxigenierte n-aryl-diazacyclen |
| DE2924064A1 (de) * | 1979-06-15 | 1980-12-18 | Boehringer Sohn Ingelheim | Neue 1- eckige klammer auf n-phenylalkyl-piperidyl-(4) eckige klammer zu -imidazolidinone-(2) und verfahren zu ihrer herstellung |
| JPS62135464A (ja) * | 1985-12-10 | 1987-06-18 | Nippon Kayaku Co Ltd | フエニルピペラジン誘導体 |
| EP0536279A1 (en) * | 1990-06-29 | 1993-04-14 | The Upjohn Company | Substituted 1-(alkoxyphenyl)piperazines with cns and antihypertensive activity |
| EP0597112A4 (en) * | 1992-03-27 | 1994-06-22 | Kyoto Pharma Ind | Novel imidazole derivative, pharmaceutical use thereof, and intermediate therefor. |
| CA2107196A1 (en) * | 1992-09-29 | 1994-03-30 | Mitsubishi Chemical Corporation | Carboxamide derivatives |
| DK148392D0 (da) * | 1992-12-09 | 1992-12-09 | Lundbeck & Co As H | Heterocykliske forbindelser |
| US5362744A (en) * | 1993-11-22 | 1994-11-08 | Warner-Lambert Company | Tetrazole-substituted urea acat inhibitors |
| IL114027A (en) * | 1994-06-08 | 1999-11-30 | Lundbeck & Co As H | 4-Phenyl piperazine (piperidine or tetrahydropyridine) derivatives serotinin 5-HT1A and dopamin D2 receptor ligand pharmaceutical compositions containing them |
| FR2744451B1 (fr) * | 1996-02-01 | 1998-04-24 | Pf Medicament | Nouvelles imidazolidinones, pyrimidinones, et 1,3-diazepin-2 -ones, leur preparation et leurs applications en therapeutique |
| FR2749304B1 (fr) * | 1996-06-04 | 1998-06-26 | Adir | Nouveaux derives du 3-(piperid-4-yl)1,2-benzisoxazole et du 3-(piperazin-4-yl)1,2-benzisoxazole, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2750991A1 (fr) * | 1996-07-12 | 1998-01-16 | Pf Medicament | Nouveaux benzodioxannes et 1-(2h)-benzopyrannes, leur preparation et leur utilisation comme medicament |
| FR2755690B1 (fr) * | 1996-11-08 | 1998-12-18 | Adir | Nouveaux derives aminomethyl heterocycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2761069A1 (fr) * | 1997-03-20 | 1998-09-25 | Pf Medicament | Spiroamines derivees de dihydrobenzofuranes, leur preparation et leur application comme medicaments |
| US6110930A (en) * | 1997-04-10 | 2000-08-29 | Ono Pharmaceutical Co., Ltd. | Condensed piperidine compound |
-
1999
- 1999-12-30 FR FR9916701A patent/FR2803298A1/fr active Pending
-
2000
- 2000-12-18 MX MXPA00012672A patent/MXPA00012672A/es active IP Right Grant
- 2000-12-22 NZ NZ509119A patent/NZ509119A/en unknown
- 2000-12-26 PT PT02078578T patent/PT1266896E/pt unknown
- 2000-12-26 DE DE60019716T patent/DE60019716T2/de not_active Expired - Fee Related
- 2000-12-26 DK DK00403673T patent/DK1113014T3/da active
- 2000-12-26 EP EP00403673A patent/EP1113014B1/fr not_active Expired - Lifetime
- 2000-12-26 DK DK02078578T patent/DK1266896T3/da active
- 2000-12-26 ES ES00403673T patent/ES2240035T3/es not_active Expired - Lifetime
- 2000-12-26 DE DE60033060T patent/DE60033060T2/de not_active Expired - Fee Related
- 2000-12-26 AT AT00403673T patent/ATE294170T1/de not_active IP Right Cessation
- 2000-12-26 PT PT00403673T patent/PT1113014E/pt unknown
- 2000-12-26 SI SI200030677T patent/SI1113014T1/xx unknown
- 2000-12-26 EP EP02078578A patent/EP1266896B1/fr not_active Expired - Lifetime
- 2000-12-26 SI SI200030933T patent/SI1266896T1/sl unknown
- 2000-12-26 ES ES02078578T patent/ES2280482T3/es not_active Expired - Lifetime
- 2000-12-27 JP JP2000397321A patent/JP3396671B2/ja not_active Expired - Fee Related
- 2000-12-28 HU HU0005014A patent/HUP0005014A2/hu unknown
- 2000-12-28 KR KR10-2000-0083628A patent/KR100511134B1/ko not_active Expired - Fee Related
- 2000-12-28 PL PL00344854A patent/PL344854A1/xx unknown
- 2000-12-29 CN CNB001374338A patent/CN1189466C/zh not_active Expired - Fee Related
- 2000-12-29 CA CA002330351A patent/CA2330351C/fr not_active Expired - Fee Related
- 2000-12-29 NO NO20006708A patent/NO20006708L/no unknown
- 2000-12-29 EA EA200001248A patent/EA004040B1/ru unknown
- 2000-12-29 AU AU72594/00A patent/AU776125B2/en not_active Ceased
- 2000-12-29 US US09/751,716 patent/US6566364B2/en not_active Expired - Fee Related
- 2000-12-29 BR BR0007348-2A patent/BR0007348A/pt not_active Application Discontinuation
-
2001
- 2001-01-02 ZA ZA200100022A patent/ZA200100022B/xx unknown
-
2002
- 2002-04-09 JP JP2002106212A patent/JP3942935B2/ja not_active Expired - Fee Related
- 2002-11-12 US US10/292,358 patent/US6908922B2/en not_active Expired - Fee Related
-
2003
- 2003-02-20 US US10/369,860 patent/US6903103B2/en not_active Expired - Fee Related
- 2003-02-20 US US10/371,128 patent/US6780868B2/en not_active Expired - Fee Related
-
2004
- 2004-03-26 KR KR10-2004-0020630A patent/KR100477384B1/ko not_active Expired - Fee Related
-
2007
- 2007-03-16 CY CY20071100379T patent/CY1106396T1/el unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ASS | Change of ownership |
Owner name: LES LABORATOIRES SERVIER, FR Free format text: OLD OWNER(S): ADIR ET COMPAGNIE |
|
| PSEA | Patent sealed | ||
| RENW | Renewal (renewal fees accepted) | ||
| RENW | Renewal (renewal fees accepted) |