JP2005501834A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2005501834A5 JP2005501834A5 JP2003517022A JP2003517022A JP2005501834A5 JP 2005501834 A5 JP2005501834 A5 JP 2005501834A5 JP 2003517022 A JP2003517022 A JP 2003517022A JP 2003517022 A JP2003517022 A JP 2003517022A JP 2005501834 A5 JP2005501834 A5 JP 2005501834A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridinecarbonitrile
- amino
- formula
- compound
- trifluoromethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 208000015114 central nervous system disease Diseases 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 12
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 201000010099 disease Diseases 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 6
- 238000004519 manufacturing process Methods 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 208000027866 inflammatory disease Diseases 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 230000002265 prevention Effects 0.000 claims 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 102000008299 Nitric Oxide Synthase Human genes 0.000 claims 2
- 108010021487 Nitric Oxide Synthase Proteins 0.000 claims 2
- 230000009286 beneficial effect Effects 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 230000005764 inhibitory process Effects 0.000 claims 2
- -1 —Z—NR 7 R 8 Chemical group 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- NCDDLOUERWJAQB-UHFFFAOYSA-N 6-acetyl-2-[3-(methylamino)-1-phenylpropyl]sulfanylpyridine-3-carbonitrile Chemical compound C=1C=CC=CC=1C(CCNC)SC1=NC(C(C)=O)=CC=C1C#N NCDDLOUERWJAQB-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 208000019695 Migraine disease Diseases 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 150000001540 azides Chemical class 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 229940111134 coxibs Drugs 0.000 claims 1
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 150000003949 imides Chemical class 0.000 claims 1
- 206010027599 migraine Diseases 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
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 JP2005501834A (ja) | 2005-01-20 |
| JP2005501834A5 true 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) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0004152D0 (en) | 2000-02-23 | 2000-04-12 | Astrazeneca Uk Ltd | Novel compounds |
| SE0102640D0 (sv) | 2001-07-31 | 2001-07-31 | Astrazeneca Ab | Novel compounds |
| SE0102639D0 (sv) * | 2001-07-31 | 2001-07-31 | Astrazeneca Ab | Novel compounds |
| SE0203304D0 (sv) * | 2002-11-07 | 2002-11-07 | Astrazeneca Ab | Novel Coumpounds |
| MX2007002929A (es) * | 2004-09-10 | 2007-08-16 | Syngenta Ltd | Isoxazoles sustituidos como funguicidas. |
| DE102006031813B4 (de) * | 2006-07-07 | 2011-04-28 | Christian-Albrechts-Universität Zu Kiel | Verwendung basischer Acetophenone als Hemmstoffe von NO-Synthasen |
| EP2161998B1 (en) * | 2007-06-04 | 2015-09-02 | Intra-Cellular Therapies, Inc. | Pyridine derivatives as NET/SERT modulators |
| 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 |
| PT707007E (pt) * | 1994-10-14 | 2002-06-28 | Merck Patent Gmbh | Derivados amino(tio)eter como agentes activos no snc |
| 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 JP JP2003517022A patent/JP2005501834A/ja not_active Withdrawn
- 2002-07-26 WO PCT/SE2002/001413 patent/WO2003011830A1/en not_active Ceased
- 2002-07-26 EP EP02749497A patent/EP1414802B1/en not_active Expired - Lifetime
- 2002-07-26 DE DE60210981T patent/DE60210981T2/de not_active Expired - Fee Related
- 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 US US10/483,140 patent/US20040176422A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2361860C2 (ru) | Новые замещенные 3-сера-индолы | |
| CA2628844A1 (en) | Pyrazole derivatives and their medical use | |
| JP2005506308A5 (enExample) | ||
| JP2011504497A5 (enExample) | ||
| JP5379690B2 (ja) | ５員複素環化合物 | |
| JP2007502806A5 (enExample) | ||
| JP2004524301A5 (enExample) | ||
| RU2009148673A (ru) | Производные пиразинона и их применение для лечения легочных заболеваний | |
| JP2014523400A (ja) | 芳香族アミド類およびそれらの使用 | |
| JP2005538955A5 (enExample) | ||
| JP2010518026A5 (enExample) | ||
| JP2012503018A5 (enExample) | ||
| CN1419552A (zh) | 2－氨基－3－烷基嘧啶酮衍生物作为GSK3β抑制剂 | |
| JP2013517283A5 (enExample) | ||
| JP2005536475A5 (enExample) | ||
| JPH11193281A (ja) | アデノシンａ３受容体拮抗剤およびチアゾール化合物 | |
| JP2004517049A5 (enExample) | ||
| JP2004520292A5 (enExample) | ||
| JP2004532229A5 (enExample) | ||
| JP2007511485A5 (enExample) | ||
| WO2004072018A1 (ja) | アミン誘導体 | |
| JP2003516987A5 (enExample) | ||
| JP2014523400A5 (enExample) | ||
| JP2005500370A5 (enExample) | ||
| JP2016514141A5 (enExample) |