JP2005501834A - ヘテロアリールヘテロアルキルアミン誘導体、および一酸化窒素合成酵素阻害剤としてのその使用 - Google Patents
ヘテロアリールヘテロアルキルアミン誘導体、および一酸化窒素合成酵素阻害剤としてのその使用 Download PDFInfo
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- JP2005501834A JP2005501834A JP2003517022A JP2003517022A JP2005501834A JP 2005501834 A JP2005501834 A JP 2005501834A JP 2003517022 A JP2003517022 A JP 2003517022A JP 2003517022 A JP2003517022 A JP 2003517022A JP 2005501834 A JP2005501834 A JP 2005501834A
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- Prior art keywords
- pyridinecarbonitrile
- amino
- formula
- compound
- trifluoromethyl
- Prior art date
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- 239000000236 nitric oxide synthase inhibitor Substances 0.000 title 1
- CSYSULGPHGCBQD-UHFFFAOYSA-N s-ethylisothiouronium diethylphosphate Chemical compound CCSC(N)=N.CCOP(O)(=O)OCC CSYSULGPHGCBQD-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 255
- 238000000034 method Methods 0.000 claims abstract description 101
- 150000003839 salts Chemical class 0.000 claims abstract description 56
- 102000008299 Nitric Oxide Synthase Human genes 0.000 claims abstract description 22
- 108010021487 Nitric Oxide Synthase Proteins 0.000 claims abstract description 22
- 229910052727 yttrium Inorganic materials 0.000 claims abstract description 13
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 12
- 239000003814 drug Substances 0.000 claims abstract description 11
- 230000002265 prevention Effects 0.000 claims abstract description 11
- 229910052720 vanadium Inorganic materials 0.000 claims abstract description 10
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- -1 —Z—NR 7 R 8 Chemical group 0.000 claims description 76
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 201000010099 disease Diseases 0.000 claims description 19
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 229910052721 tungsten Inorganic materials 0.000 claims description 14
- 229910052770 Uranium Inorganic materials 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 230000005764 inhibitory process Effects 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000001153 fluoro group Chemical group F* 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 230000000694 effects Effects 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 8
- 208000015114 central nervous system disease Diseases 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 208000002193 Pain Diseases 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 229940111134 coxibs Drugs 0.000 claims description 6
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- HPDMWCWPDMHUHY-MRXNPFEDSA-N 2-[(1r)-3-[2-hydroxyethyl(methyl)amino]-1-phenylpropyl]sulfanyl-6-(trifluoromethyl)pyridine-3-carbonitrile Chemical compound S([C@H](CCN(CCO)C)C=1C=CC=CC=1)C1=NC(C(F)(F)F)=CC=C1C#N HPDMWCWPDMHUHY-MRXNPFEDSA-N 0.000 claims description 4
- LEVUEKTWPOROQL-SNVBAGLBSA-N 2-[(1r)-3-amino-1-(1,2-oxazol-3-yl)propoxy]-6-(trifluoromethyl)pyridine-3-carbonitrile Chemical compound O([C@H](CCN)C1=NOC=C1)C1=NC(C(F)(F)F)=CC=C1C#N LEVUEKTWPOROQL-SNVBAGLBSA-N 0.000 claims description 4
- MNUUOMWLAUYYOF-MRVPVSSYSA-N 2-[(1r)-3-amino-1-(3-chloro-1,2-oxazol-5-yl)propoxy]-6-(trifluoromethyl)pyridine-3-carbonitrile Chemical compound O([C@H](CCN)C=1ON=C(Cl)C=1)C1=NC(C(F)(F)F)=CC=C1C#N MNUUOMWLAUYYOF-MRVPVSSYSA-N 0.000 claims description 4
- GCSSUWJSVJIHFL-LLVKDONJSA-N 2-[(1r)-3-amino-1-(3-chloro-1,2-oxazol-5-yl)propyl]sulfanyl-6-methylpyridine-3-carbonitrile Chemical compound CC1=CC=C(C#N)C(S[C@H](CCN)C=2ON=C(Cl)C=2)=N1 GCSSUWJSVJIHFL-LLVKDONJSA-N 0.000 claims description 4
- LDAUFMYFIINTDH-OAHLLOKOSA-N 2-[(1r)-3-amino-1-phenylpropyl]sulfanyl-6-methylpyridine-3-carbonitrile Chemical compound CC1=CC=C(C#N)C(S[C@H](CCN)C=2C=CC=CC=2)=N1 LDAUFMYFIINTDH-OAHLLOKOSA-N 0.000 claims description 4
- KNKHDXZXJHXLLL-UHFFFAOYSA-N 2-[3-amino-1-(3-methyl-1,2-oxazol-4-yl)propoxy]-6-(trifluoromethyl)pyridine-3-carbonitrile Chemical compound CC1=NOC=C1C(CCN)OC1=NC(C(F)(F)F)=CC=C1C#N KNKHDXZXJHXLLL-UHFFFAOYSA-N 0.000 claims description 4
- ZUPHQWMJXVCEQK-UHFFFAOYSA-N 2-[4-amino-1-(1,2-oxazol-5-yl)butoxy]-6-(trifluoromethyl)pyridine-3-carbonitrile Chemical compound C=1C=NOC=1C(CCCN)OC1=NC(C(F)(F)F)=CC=C1C#N ZUPHQWMJXVCEQK-UHFFFAOYSA-N 0.000 claims description 4
- KYPXPCZETJUTRK-UHFFFAOYSA-N 2-[4-amino-1-(1,2-oxazol-5-yl)butyl]sulfanyl-6-methylpyridine-3-carbonitrile Chemical compound CC1=CC=C(C#N)C(SC(CCCN)C=2ON=CC=2)=N1 KYPXPCZETJUTRK-UHFFFAOYSA-N 0.000 claims description 4
- XOEODTPRSHKJPP-LLVKDONJSA-N 4-[(1r)-3-amino-1-(1,2-oxazol-5-yl)propyl]sulfanyl-6-methoxypyridine-3-carbonitrile Chemical compound C1=NC(OC)=CC(S[C@H](CCN)C=2ON=CC=2)=C1C#N XOEODTPRSHKJPP-LLVKDONJSA-N 0.000 claims description 4
- BUIYENROECNMGC-UHFFFAOYSA-N 4-[3-amino-1-(4-chloro-1,3-thiazol-5-yl)propyl]sulfanyl-6-methylpyridine-3-carbonitrile Chemical compound C1=NC(C)=CC(SC(CCN)C2=C(N=CS2)Cl)=C1C#N BUIYENROECNMGC-UHFFFAOYSA-N 0.000 claims description 4
- 208000019695 Migraine disease Diseases 0.000 claims description 4
- 239000002671 adjuvant Substances 0.000 claims description 4
- 230000009286 beneficial effect Effects 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 206010027599 migraine Diseases 0.000 claims description 4
- RMICWZZXYUFGMG-MRXNPFEDSA-N 2-[(1r)-3-(3-hydroxypropylamino)-1-phenylpropoxy]-6-(trifluoromethyl)pyridine-3-carbonitrile Chemical compound O([C@H](CCNCCCO)C=1C=CC=CC=1)C1=NC(C(F)(F)F)=CC=C1C#N RMICWZZXYUFGMG-MRXNPFEDSA-N 0.000 claims description 3
- QECWHWXKXTUVDA-HXUWFJFHSA-N 2-[(1r)-3-(benzylamino)-1-phenylpropoxy]-6-(trifluoromethyl)pyridine-3-carbonitrile Chemical compound FC(F)(F)C1=CC=C(C#N)C(O[C@H](CCNCC=2C=CC=CC=2)C=2C=CC=CC=2)=N1 QECWHWXKXTUVDA-HXUWFJFHSA-N 0.000 claims description 3
- ZXISHAGLOKGKTE-MRXNPFEDSA-N 2-[(1r)-3-(tert-butylamino)-1-phenylpropoxy]-6-(trifluoromethyl)pyridine-3-carbonitrile Chemical compound O([C@H](CCNC(C)(C)C)C=1C=CC=CC=1)C1=NC(C(F)(F)F)=CC=C1C#N ZXISHAGLOKGKTE-MRXNPFEDSA-N 0.000 claims description 3
- OYUGWWNWBBEXRG-OAQYLSRUSA-N 2-[(1r)-3-[2-(4-hydroxyphenyl)ethylamino]-1-phenylpropoxy]-6-(trifluoromethyl)pyridine-3-carbonitrile Chemical compound C1=CC(O)=CC=C1CCNCC[C@H](C=1C=CC=CC=1)OC1=NC(C(F)(F)F)=CC=C1C#N OYUGWWNWBBEXRG-OAQYLSRUSA-N 0.000 claims description 3
- HSCNTCYDIHFTES-GOSISDBHSA-N 2-[(1r)-3-[2-hydroxyethyl(propyl)amino]-1-phenylpropoxy]-6-(trifluoromethyl)pyridine-3-carbonitrile Chemical compound O([C@H](CCN(CCO)CCC)C=1C=CC=CC=1)C1=NC(C(F)(F)F)=CC=C1C#N HSCNTCYDIHFTES-GOSISDBHSA-N 0.000 claims description 3
- RRVHCQZHFRSZNI-QGZVFWFLSA-N 2-[(1r)-3-[methyl(propyl)amino]-1-phenylpropoxy]-6-(trifluoromethyl)pyridine-3-carbonitrile Chemical compound O([C@H](CCN(C)CCC)C=1C=CC=CC=1)C1=NC(C(F)(F)F)=CC=C1C#N RRVHCQZHFRSZNI-QGZVFWFLSA-N 0.000 claims description 3
- WXXXERJBGXUURW-GFCCVEGCSA-N 2-[(1r)-3-amino-1-(1,2-oxazol-5-yl)propyl]sulfanyl-6-methylpyridine-3-carbonitrile Chemical compound CC1=CC=C(C#N)C(S[C@H](CCN)C=2ON=CC=2)=N1 WXXXERJBGXUURW-GFCCVEGCSA-N 0.000 claims description 3
- QFKAMKPRDAKZNA-CYBMUJFWSA-N 4-[(1r)-3-(2-hydroxyethylamino)-1-(1,2-oxazol-5-yl)propyl]sulfanyl-6-methoxypyridine-3-carbonitrile Chemical compound C1=NC(OC)=CC(S[C@H](CCNCCO)C=2ON=CC=2)=C1C#N QFKAMKPRDAKZNA-CYBMUJFWSA-N 0.000 claims description 3
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- 201000008482 osteoarthritis Diseases 0.000 claims description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- HZQWBARNMWLARE-CQSZACIVSA-N 2-[(1r)-3-(3-hydroxypropylamino)-1-thiophen-3-ylpropoxy]-6-(trifluoromethyl)pyridine-3-carbonitrile Chemical compound O([C@H](CCNCCCO)C1=CSC=C1)C1=NC(C(F)(F)F)=CC=C1C#N HZQWBARNMWLARE-CQSZACIVSA-N 0.000 claims description 2
- DCZGHJSYXIVUNM-LLVKDONJSA-N 2-[(1r)-3-(dimethylamino)-1-(1,2-oxazol-5-yl)propoxy]-6-(trifluoromethyl)pyridine-3-carbonitrile Chemical compound O([C@H](CCN(C)C)C=1ON=CC=1)C1=NC(C(F)(F)F)=CC=C1C#N DCZGHJSYXIVUNM-LLVKDONJSA-N 0.000 claims description 2
- RBORJKIDHBJUQQ-CQSZACIVSA-N 2-[(1r)-3-(methylamino)-1-phenylpropoxy]-6-(trifluoromethyl)pyridine-3-carbonitrile Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=NC(C(F)(F)F)=CC=C1C#N RBORJKIDHBJUQQ-CQSZACIVSA-N 0.000 claims description 2
- SDRHZGGFUFCFFW-SECBINFHSA-N 2-[(1r)-3-amino-1-(1,2-oxazol-5-yl)propoxy]-6-(trifluoromethyl)pyridine-3-carbonitrile Chemical compound O([C@H](CCN)C=1ON=CC=1)C1=NC(C(F)(F)F)=CC=C1C#N SDRHZGGFUFCFFW-SECBINFHSA-N 0.000 claims description 2
- DUEKNAAQSVRWQG-SECBINFHSA-N 2-[(1r)-3-amino-1-(1,3-thiazol-2-yl)propoxy]-6-(trifluoromethyl)pyridine-3-carbonitrile Chemical compound O([C@H](CCN)C=1SC=CN=1)C1=NC(C(F)(F)F)=CC=C1C#N DUEKNAAQSVRWQG-SECBINFHSA-N 0.000 claims description 2
- UGNOOBLDWIVKMG-LLVKDONJSA-N 2-[(1r)-3-amino-1-(5-methyl-1,2-oxazol-3-yl)propoxy]-6-(trifluoromethyl)pyridine-3-carbonitrile Chemical compound O1C(C)=CC([C@@H](CCN)OC=2C(=CC=C(N=2)C(F)(F)F)C#N)=N1 UGNOOBLDWIVKMG-LLVKDONJSA-N 0.000 claims description 2
- XKAPSSDIEFDKIV-CQSZACIVSA-N 2-[(1r)-3-amino-1-phenylpropyl]sulfanyl-6-(difluoromethyl)pyridine-3-carbonitrile Chemical compound S([C@H](CCN)C=1C=CC=CC=1)C1=NC(C(F)F)=CC=C1C#N XKAPSSDIEFDKIV-CQSZACIVSA-N 0.000 claims description 2
- FUBZBQIQVFYNPQ-OAHLLOKOSA-N 2-[(1r)-3-amino-1-phenylpropyl]sulfanyl-6-(fluoromethyl)pyridine-3-carbonitrile Chemical compound S([C@H](CCN)C=1C=CC=CC=1)C1=NC(CF)=CC=C1C#N FUBZBQIQVFYNPQ-OAHLLOKOSA-N 0.000 claims description 2
- UKYGHQXHBGSVDH-LLVKDONJSA-N 2-[(1r)-3-amino-1-thiophen-3-ylpropoxy]-6-(trifluoromethyl)pyridine-3-carbonitrile Chemical compound O([C@H](CCN)C1=CSC=C1)C1=NC(C(F)(F)F)=CC=C1C#N UKYGHQXHBGSVDH-LLVKDONJSA-N 0.000 claims description 2
- ZXIGADVZANEJTH-UHFFFAOYSA-N 2-[1-(3-fluorophenyl)-3-(methylamino)propoxy]pyridine-3-carbonitrile Chemical compound C=1C=CC(F)=CC=1C(CCNC)OC1=NC=CC=C1C#N ZXIGADVZANEJTH-UHFFFAOYSA-N 0.000 claims description 2
- DMUABTNYQVTBRJ-UHFFFAOYSA-N 2-[1-(4-chloro-1,3-thiazol-5-yl)-3-(methylamino)propoxy]-6-methylpyridine-3-carbonitrile Chemical compound S1C=NC(Cl)=C1C(CCNC)OC1=NC(C)=CC=C1C#N DMUABTNYQVTBRJ-UHFFFAOYSA-N 0.000 claims description 2
- NAFKZLAHLFKWBM-UHFFFAOYSA-N 2-[3-amino-1-(1,2-thiazol-3-yl)propoxy]-6-methylpyridine-3-carbonitrile Chemical compound CC1=CC=C(C#N)C(OC(CCN)C2=NSC=C2)=N1 NAFKZLAHLFKWBM-UHFFFAOYSA-N 0.000 claims description 2
- SRIXQYHBIVCPIP-UHFFFAOYSA-N 2-[3-amino-1-(1,2-thiazol-5-yl)propoxy]-6-methylpyridine-3-carbonitrile Chemical compound CC1=CC=C(C#N)C(OC(CCN)C=2SN=CC=2)=N1 SRIXQYHBIVCPIP-UHFFFAOYSA-N 0.000 claims description 2
- RUQXIEACHVGVRW-UHFFFAOYSA-N 2-[3-amino-1-(1,2-thiazol-5-yl)propyl]sulfanyl-6-(trifluoromethyl)pyridine-3-carbonitrile Chemical compound C=1C=NSC=1C(CCN)SC1=NC(C(F)(F)F)=CC=C1C#N RUQXIEACHVGVRW-UHFFFAOYSA-N 0.000 claims description 2
- AZMAQLJSGUKPOB-UHFFFAOYSA-N 2-[3-amino-1-(1,2-thiazol-5-yl)propyl]sulfanyl-6-methylpyridine-3-carbonitrile Chemical compound CC1=CC=C(C#N)C(SC(CCN)C=2SN=CC=2)=N1 AZMAQLJSGUKPOB-UHFFFAOYSA-N 0.000 claims description 2
- KJCALSCYOYQNAP-UHFFFAOYSA-N 2-[3-amino-1-(1,3-oxazol-2-yl)propoxy]-6-(trifluoromethyl)pyridine-3-carbonitrile Chemical compound N=1C=COC=1C(CCN)OC1=NC(C(F)(F)F)=CC=C1C#N KJCALSCYOYQNAP-UHFFFAOYSA-N 0.000 claims description 2
- HWVHVQMPKIYIMI-UHFFFAOYSA-N 2-[3-amino-1-(4-methyl-1,2-oxazol-3-yl)propyl]sulfanyl-6-methylpyridine-3-carbonitrile Chemical compound CC1=CON=C1C(CCN)SC1=NC(C)=CC=C1C#N HWVHVQMPKIYIMI-UHFFFAOYSA-N 0.000 claims description 2
- WGOKYTMAFAZIMT-CQSZACIVSA-N 3-[[(3r)-3-[3-cyano-6-(trifluoromethyl)pyridin-2-yl]oxy-3-thiophen-3-ylpropyl]amino]-n-methylpropanamide Chemical compound O([C@H](CCNCCC(=O)NC)C1=CSC=C1)C1=NC(C(F)(F)F)=CC=C1C#N WGOKYTMAFAZIMT-CQSZACIVSA-N 0.000 claims description 2
- FFRROXVROXPSHG-LLVKDONJSA-N 4-[(1r)-3-amino-1-(1,2-oxazol-3-yl)propoxy]-6-methoxypyridine-3-carbonitrile Chemical compound C1=NC(OC)=CC(O[C@H](CCN)C2=NOC=C2)=C1C#N FFRROXVROXPSHG-LLVKDONJSA-N 0.000 claims description 2
- KLQOQANQYCEAGM-UHFFFAOYSA-N 4-[4-amino-1-(1,2-oxazol-5-yl)butyl]sulfanyl-6-methoxypyridine-3-carbonitrile Chemical compound C1=NC(OC)=CC(SC(CCCN)C=2ON=CC=2)=C1C#N KLQOQANQYCEAGM-UHFFFAOYSA-N 0.000 claims description 2
- PEUQULCDMRGSMZ-MRXNPFEDSA-N 5-fluoro-6-methyl-2-[(1r)-3-(methylamino)-1-phenylpropyl]sulfanylpyridine-3-carbonitrile Chemical compound S([C@H](CCNC)C=1C=CC=CC=1)C1=NC(C)=C(F)C=C1C#N PEUQULCDMRGSMZ-MRXNPFEDSA-N 0.000 claims description 2
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- UUDSAHWWESHIDZ-SNVBAGLBSA-N 6-amino-4-[(1r)-3-amino-1-(1,2-oxazol-5-yl)propyl]sulfanylpyridine-3-carbonitrile Chemical compound S([C@H](CCN)C=1ON=CC=1)C1=CC(N)=NC=C1C#N UUDSAHWWESHIDZ-SNVBAGLBSA-N 0.000 claims description 2
- XNPLFGIYZCJXEL-QGZVFWFLSA-N 6-ethyl-5-fluoro-2-[(1r)-3-(methylamino)-1-phenylpropyl]sulfanylpyridine-3-carbonitrile Chemical compound C1=C(F)C(CC)=NC(S[C@H](CCNC)C=2C=CC=CC=2)=C1C#N XNPLFGIYZCJXEL-QGZVFWFLSA-N 0.000 claims description 2
- 150000001540 azides Chemical class 0.000 claims description 2
- 150000003949 imides Chemical class 0.000 claims description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
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- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 abstract description 8
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- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 36
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 35
- 239000002904 solvent Substances 0.000 description 34
- 239000000284 extract Substances 0.000 description 30
- 239000003921 oil Substances 0.000 description 29
- 235000019198 oils Nutrition 0.000 description 29
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 25
- 238000000746 purification Methods 0.000 description 22
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 19
- 239000011541 reaction mixture Substances 0.000 description 19
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- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
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- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3
-
- 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
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07D417/02—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
- C07D417/12—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 linked by a chain containing hetero atoms as chain links
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Neurosurgery (AREA)
- Pulmonology (AREA)
- Diabetes (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Dermatology (AREA)
- Rheumatology (AREA)
- Endocrinology (AREA)
- Immunology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Obesity (AREA)
- Ophthalmology & Optometry (AREA)
- Cardiology (AREA)
- Hematology (AREA)
- Emergency Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0102641A SE0102641D0 (sv) | 2001-07-31 | 2001-07-31 | Novel compounds |
| PCT/SE2002/001413 WO2003011830A1 (en) | 2001-07-31 | 2002-07-26 | Heteroarylheteroalkylamine derivatives and their use as inhibitors of nitric oxide synthase |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005501834A true JP2005501834A (ja) | 2005-01-20 |
| JP2005501834A5 JP2005501834A5 (enExample) | 2006-01-12 |
Family
ID=20284966
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003517022A Withdrawn JP2005501834A (ja) | 2001-07-31 | 2002-07-26 | ヘテロアリールヘテロアルキルアミン誘導体、および一酸化窒素合成酵素阻害剤としてのその使用 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20040176422A1 (enExample) |
| EP (1) | EP1414802B1 (enExample) |
| JP (1) | JP2005501834A (enExample) |
| AT (1) | ATE324368T1 (enExample) |
| DE (1) | DE60210981T2 (enExample) |
| ES (1) | ES2261696T3 (enExample) |
| SE (1) | SE0102641D0 (enExample) |
| WO (1) | WO2003011830A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010529124A (ja) * | 2007-06-04 | 2010-08-26 | イントラ−セルラー・セラピーズ・インコーポレイテッド | 新規方法 |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0004152D0 (en) | 2000-02-23 | 2000-04-12 | Astrazeneca Uk Ltd | Novel compounds |
| SE0102639D0 (sv) * | 2001-07-31 | 2001-07-31 | Astrazeneca Ab | Novel compounds |
| SE0102640D0 (sv) | 2001-07-31 | 2001-07-31 | Astrazeneca Ab | Novel compounds |
| SE0203304D0 (sv) * | 2002-11-07 | 2002-11-07 | Astrazeneca Ab | Novel Coumpounds |
| RU2392273C2 (ru) * | 2004-09-10 | 2010-06-20 | Синджента Лимитед | Замещенные изоксазолы в качестве фунгицидов |
| DE102006031813B4 (de) * | 2006-07-07 | 2011-04-28 | Christian-Albrechts-Universität Zu Kiel | Verwendung basischer Acetophenone als Hemmstoffe von NO-Synthasen |
| CN102775365A (zh) * | 2011-05-10 | 2012-11-14 | 无锡立诺康医药科技有限公司 | 5-氨基取代基-异噁唑类化合物或其酸式盐的合成工艺 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US139350A (en) * | 1873-05-27 | Improvement in cutters for sewing-machines | ||
| JPS5144934B1 (enExample) * | 1969-12-09 | 1976-12-01 | ||
| US4314081A (en) * | 1974-01-10 | 1982-02-02 | Eli Lilly And Company | Arloxyphenylpropylamines |
| US4330546A (en) * | 1979-09-14 | 1982-05-18 | John Wyeth & Brother Limited | 3-Aryl-3-aryloxypropylamines |
| GB2060622B (en) * | 1979-09-14 | 1983-05-25 | Wyeth John & Brother Ltd | 3-aryl-3-aryloxyalkylamines |
| US4295126A (en) * | 1980-10-02 | 1981-10-13 | Itt Industries, Inc. | MOS-Binary-to-decimal code converter |
| DE3138550A1 (de) * | 1981-09-28 | 1983-04-07 | Boehringer Ingelheim KG, 6507 Ingelheim | Substituierte 2-phenyl-2-(pyridyloxy)-ethylamine und isostere verbindungen, verfahren zu ihrer herstellung und verwendung |
| US4902710A (en) * | 1988-12-14 | 1990-02-20 | Eli Lilly And Company | Serotonin and norepinephrine uptake inhibitors |
| DK258389D0 (da) * | 1989-05-26 | 1989-05-26 | Ferrosan As | Aryloxyphenylpropylaminer, deres fremstilling og anvendelse |
| EP0571685A1 (en) * | 1992-05-27 | 1993-12-01 | Novo Nordisk A/S | Aryloxyheteroarylpropylamines, their preparation and use |
| DK0707007T3 (da) * | 1994-10-14 | 2002-03-18 | Merck Patent Gmbh | Amino(thio)etherderivater som CNS-aktive midler |
| GB0004149D0 (en) * | 2000-02-23 | 2000-04-12 | Astrazeneca Uk Ltd | Novel compounds |
-
2001
- 2001-07-31 SE SE0102641A patent/SE0102641D0/xx unknown
-
2002
- 2002-07-26 AT AT02749497T patent/ATE324368T1/de not_active IP Right Cessation
- 2002-07-26 ES ES02749497T patent/ES2261696T3/es not_active Expired - Lifetime
- 2002-07-26 DE DE60210981T patent/DE60210981T2/de not_active Expired - Fee Related
- 2002-07-26 JP JP2003517022A patent/JP2005501834A/ja not_active Withdrawn
- 2002-07-26 WO PCT/SE2002/001413 patent/WO2003011830A1/en not_active Ceased
- 2002-07-26 US US10/483,140 patent/US20040176422A1/en not_active Abandoned
- 2002-07-26 EP EP02749497A patent/EP1414802B1/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010529124A (ja) * | 2007-06-04 | 2010-08-26 | イントラ−セルラー・セラピーズ・インコーポレイテッド | 新規方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1414802A1 (en) | 2004-05-06 |
| DE60210981D1 (de) | 2006-06-01 |
| EP1414802B1 (en) | 2006-04-26 |
| DE60210981T2 (de) | 2007-05-10 |
| SE0102641D0 (sv) | 2001-07-31 |
| US20040176422A1 (en) | 2004-09-09 |
| WO2003011830A1 (en) | 2003-02-13 |
| ES2261696T3 (es) | 2006-11-16 |
| ATE324368T1 (de) | 2006-05-15 |
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