JP2003523992A5 - - Google Patents
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- JP2003523992A5 JP2003523992A5 JP2001561723A JP2001561723A JP2003523992A5 JP 2003523992 A5 JP2003523992 A5 JP 2003523992A5 JP 2001561723 A JP2001561723 A JP 2001561723A JP 2001561723 A JP2001561723 A JP 2001561723A JP 2003523992 A5 JP2003523992 A5 JP 2003523992A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- chloro
- alkyl
- benzonitrile
- compound
- 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.)
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- 150000001875 compounds Chemical class 0.000 description 34
- 125000000217 alkyl group Chemical group 0.000 description 32
- 150000003839 salts Chemical class 0.000 description 23
- 125000003545 alkoxy group Chemical group 0.000 description 22
- 238000000034 method Methods 0.000 description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 16
- 229910052736 halogen Inorganic materials 0.000 description 14
- 150000002367 halogens Chemical class 0.000 description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 13
- 201000010099 disease Diseases 0.000 description 11
- 125000005842 heteroatom Chemical group 0.000 description 11
- 208000027866 inflammatory disease Diseases 0.000 description 11
- 229910052760 oxygen Inorganic materials 0.000 description 11
- 229910052717 sulfur Inorganic materials 0.000 description 11
- 102000008299 Nitric Oxide Synthase Human genes 0.000 description 10
- 108010021487 Nitric Oxide Synthase Proteins 0.000 description 10
- 229910052799 carbon Inorganic materials 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 6
- 108010076864 Nitric Oxide Synthase Type II Proteins 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- 102000004190 Enzymes Human genes 0.000 description 5
- 108090000790 Enzymes Proteins 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 206010061218 Inflammation Diseases 0.000 description 4
- 102100022397 Nitric oxide synthase, brain Human genes 0.000 description 4
- 101710111444 Nitric oxide synthase, brain Proteins 0.000 description 4
- 101710090055 Nitric oxide synthase, endothelial Proteins 0.000 description 4
- 102000001708 Protein Isoforms Human genes 0.000 description 4
- 108010029485 Protein Isoforms Proteins 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 229940111134 coxibs Drugs 0.000 description 4
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 230000004054 inflammatory process Effects 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 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 description 3
- 102000011779 Nitric Oxide Synthase Type II Human genes 0.000 description 3
- 102100029438 Nitric oxide synthase, inducible Human genes 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000001939 inductive effect Effects 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 2
- -1 NR 6 R 7 Chemical group 0.000 description 2
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 2
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 2
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000001537 neural effect Effects 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 201000008482 osteoarthritis Diseases 0.000 description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- KMECBOCJLJFKTJ-INIZCTEOSA-N (3r)-3-(2,5-dichlorophenoxy)-n-methyl-4-(4-methylphenyl)butan-1-amine Chemical compound C([C@H](CCNC)OC=1C(=CC=C(Cl)C=1)Cl)C1=CC=C(C)C=C1 KMECBOCJLJFKTJ-INIZCTEOSA-N 0.000 description 1
- DXQJUBYNQJSPKH-HNNXBMFYSA-N (3r)-3-(2,5-dichlorophenoxy)-n-methyl-4-phenylbutan-1-amine Chemical compound C([C@H](CCNC)OC=1C(=CC=C(Cl)C=1)Cl)C1=CC=CC=C1 DXQJUBYNQJSPKH-HNNXBMFYSA-N 0.000 description 1
- RFNWSUKUCZJGFZ-MRXNPFEDSA-N (4r)-4-(2,5-dichlorophenoxy)-4-(4-fluorophenyl)-n-methylbutan-1-amine Chemical compound O([C@H](CCCNC)C=1C=CC(F)=CC=1)C1=CC(Cl)=CC=C1Cl RFNWSUKUCZJGFZ-MRXNPFEDSA-N 0.000 description 1
- JXTJXWVYFOIRGC-UHFFFAOYSA-N 1-[4-(2,5-dichlorophenoxy)-4-phenylbutyl]piperazine Chemical compound ClC1=CC=C(Cl)C(OC(CCCN2CCNCC2)C=2C=CC=CC=2)=C1 JXTJXWVYFOIRGC-UHFFFAOYSA-N 0.000 description 1
- RRBQJTSKEIWUJL-UHFFFAOYSA-N 1-[4-(2,5-dichlorophenoxy)-4-phenylbutyl]piperidin-4-ol Chemical compound C1CC(O)CCN1CCCC(C=1C=CC=CC=1)OC1=CC(Cl)=CC=C1Cl RRBQJTSKEIWUJL-UHFFFAOYSA-N 0.000 description 1
- ZZKHGFVETXSRDK-UHFFFAOYSA-N 1-[4-(2,5-dichlorophenoxy)-4-thiophen-2-ylbutyl]-4-methylpiperazine Chemical compound C1CN(C)CCN1CCCC(C=1SC=CC=1)OC1=CC(Cl)=CC=C1Cl ZZKHGFVETXSRDK-UHFFFAOYSA-N 0.000 description 1
- MCXINTWIYVVYOK-UHFFFAOYSA-N 2-(4-amino-1-pyridin-3-ylbutoxy)-4-chlorobenzonitrile Chemical compound C=1C=CN=CC=1C(CCCN)OC1=CC(Cl)=CC=C1C#N MCXINTWIYVVYOK-UHFFFAOYSA-N 0.000 description 1
- UBTIFTSQKLAYOE-UHFFFAOYSA-N 2-[(1-amino-6-methylheptan-4-yl)amino]-4-(trifluoromethyl)benzonitrile Chemical compound NCCCC(CC(C)C)NC1=CC(C(F)(F)F)=CC=C1C#N UBTIFTSQKLAYOE-UHFFFAOYSA-N 0.000 description 1
- AYJOGVXCOKOMPQ-CYBMUJFWSA-N 2-[(1r)-4-amino-1-(1-methylimidazol-2-yl)butoxy]-4-chloro-5-fluorobenzonitrile Chemical compound CN1C=CN=C1[C@@H](CCCN)OC1=CC(Cl)=C(F)C=C1C#N AYJOGVXCOKOMPQ-CYBMUJFWSA-N 0.000 description 1
- JNNQAKOEHNBNET-CQSZACIVSA-N 2-[(1r)-4-amino-1-(furan-3-yl)butoxy]-4-chloro-5-fluorobenzonitrile Chemical compound O([C@H](CCCN)C1=COC=C1)C1=CC(Cl)=C(F)C=C1C#N JNNQAKOEHNBNET-CQSZACIVSA-N 0.000 description 1
- PLDOAPUZJMTNCD-UHFFFAOYSA-N 2-[(4-amino-1-phenylbutyl)amino]-4-chlorobenzonitrile Chemical compound C=1C=CC=CC=1C(CCCN)NC1=CC(Cl)=CC=C1C#N PLDOAPUZJMTNCD-UHFFFAOYSA-N 0.000 description 1
- GDTQOEMSLHKILE-UHFFFAOYSA-N 2-[4-amino-1-(1,3-thiazol-2-yl)butoxy]-4-chlorobenzonitrile Chemical compound N=1C=CSC=1C(CCCN)OC1=CC(Cl)=CC=C1C#N GDTQOEMSLHKILE-UHFFFAOYSA-N 0.000 description 1
- QCHUYECHYFCHLQ-UHFFFAOYSA-N 2-[4-amino-1-(2-methoxypyridin-3-yl)butoxy]-4-chlorobenzonitrile Chemical compound COC1=NC=CC=C1C(CCCN)OC1=CC(Cl)=CC=C1C#N QCHUYECHYFCHLQ-UHFFFAOYSA-N 0.000 description 1
- BIHUPSJDIQBJMG-UHFFFAOYSA-N 2-[4-amino-1-(2-oxo-1h-pyridin-3-yl)butoxy]-4-chlorobenzonitrile Chemical compound C=1C=CNC(=O)C=1C(CCCN)OC1=CC(Cl)=CC=C1C#N BIHUPSJDIQBJMG-UHFFFAOYSA-N 0.000 description 1
- IVHMMFHIQCJCEB-UHFFFAOYSA-N 2-[4-amino-1-(furan-3-yl)butoxy]-4-chlorobenzonitrile Chemical compound C1=COC=C1C(CCCN)OC1=CC(Cl)=CC=C1C#N IVHMMFHIQCJCEB-UHFFFAOYSA-N 0.000 description 1
- QBQXIVSTBUZLOG-UHFFFAOYSA-N 2-[[4-(2,5-dichlorophenoxy)-4-phenylbutyl]-methylamino]ethanol Chemical compound C=1C=CC=CC=1C(CCCN(CCO)C)OC1=CC(Cl)=CC=C1Cl QBQXIVSTBUZLOG-UHFFFAOYSA-N 0.000 description 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
- WMGALHHWGZJOKF-UHFFFAOYSA-N 4-(2,5-dichlorophenoxy)-n-methyl-4-thiophen-2-ylbutan-1-amine Chemical compound C=1C=CSC=1C(CCCNC)OC1=CC(Cl)=CC=C1Cl WMGALHHWGZJOKF-UHFFFAOYSA-N 0.000 description 1
- ICJONTSMLLXXCO-UHFFFAOYSA-N 4-[2-chloro-5-(trifluoromethyl)phenoxy]-4-(1,3-thiazol-2-yl)butan-1-amine Chemical compound N=1C=CSC=1C(CCCN)OC1=CC(C(F)(F)F)=CC=C1Cl ICJONTSMLLXXCO-UHFFFAOYSA-N 0.000 description 1
- PFFMNXUIZGUQAZ-UHFFFAOYSA-N 4-[2-chloro-5-(trifluoromethyl)phenoxy]-4-(2-methyl-1,2,4-triazol-3-yl)butan-1-amine Chemical compound CN1N=CN=C1C(CCCN)OC1=CC(C(F)(F)F)=CC=C1Cl PFFMNXUIZGUQAZ-UHFFFAOYSA-N 0.000 description 1
- VGFNLQZVFKBTPY-JOCHJYFZSA-N 4-chloro-2-[(1r)-1-phenyl-4-(pyridin-3-ylmethylamino)butoxy]benzonitrile Chemical compound ClC1=CC=C(C#N)C(O[C@H](CCCNCC=2C=NC=CC=2)C=2C=CC=CC=2)=C1 VGFNLQZVFKBTPY-JOCHJYFZSA-N 0.000 description 1
- UOZARJXEZPWSBH-HXUWFJFHSA-N 4-chloro-2-[(1r)-1-phenyl-4-pyrrolidin-1-ylbutoxy]benzonitrile Chemical compound ClC1=CC=C(C#N)C(O[C@H](CCCN2CCCC2)C=2C=CC=CC=2)=C1 UOZARJXEZPWSBH-HXUWFJFHSA-N 0.000 description 1
- FAQOVRHAGUJGJJ-GOSISDBHSA-N 4-chloro-2-[(1r)-4-(2-hydroxyethylamino)-1-phenylbutoxy]benzonitrile Chemical compound O([C@H](CCCNCCO)C=1C=CC=CC=1)C1=CC(Cl)=CC=C1C#N FAQOVRHAGUJGJJ-GOSISDBHSA-N 0.000 description 1
- FQHJXPDAFFSZLM-LJQANCHMSA-N 4-chloro-2-[(1r)-4-(3-hydroxypropylamino)-1-phenylbutoxy]benzonitrile Chemical compound O([C@H](CCCNCCCO)C=1C=CC=CC=1)C1=CC(Cl)=CC=C1C#N FQHJXPDAFFSZLM-LJQANCHMSA-N 0.000 description 1
- UKNKORSKHIJECC-LJQANCHMSA-N 4-chloro-2-[(1r)-4-(cyclopropylamino)-1-phenylbutoxy]benzonitrile Chemical compound ClC1=CC=C(C#N)C(O[C@H](CCCNC2CC2)C=2C=CC=CC=2)=C1 UKNKORSKHIJECC-LJQANCHMSA-N 0.000 description 1
- CMTRTMNNCATGTQ-QGZVFWFLSA-N 4-chloro-2-[(1r)-4-(methylamino)-1-phenylbutoxy]benzonitrile Chemical compound O([C@H](CCCNC)C=1C=CC=CC=1)C1=CC(Cl)=CC=C1C#N CMTRTMNNCATGTQ-QGZVFWFLSA-N 0.000 description 1
- FXXVGHDSDZQSIZ-OAQYLSRUSA-N 4-chloro-2-[(1r)-4-[2-(1h-imidazol-5-yl)ethylamino]-1-phenylbutoxy]benzonitrile Chemical compound ClC1=CC=C(C#N)C(O[C@H](CCCNCCC=2NC=NC=2)C=2C=CC=CC=2)=C1 FXXVGHDSDZQSIZ-OAQYLSRUSA-N 0.000 description 1
- SIHYEEYEMBGQOD-DNVCBOLYSA-N 4-chloro-2-[(1r)-4-[[(2r)-1-hydroxypropan-2-yl]amino]-1-phenylbutoxy]benzonitrile Chemical compound O([C@H](CCCN[C@@H](CO)C)C=1C=CC=CC=1)C1=CC(Cl)=CC=C1C#N SIHYEEYEMBGQOD-DNVCBOLYSA-N 0.000 description 1
- SIHYEEYEMBGQOD-HNAYVOBHSA-N 4-chloro-2-[(1r)-4-[[(2s)-1-hydroxypropan-2-yl]amino]-1-phenylbutoxy]benzonitrile Chemical compound O([C@H](CCCN[C@H](CO)C)C=1C=CC=CC=1)C1=CC(Cl)=CC=C1C#N SIHYEEYEMBGQOD-HNAYVOBHSA-N 0.000 description 1
- BEHQHZICCZXWAO-HXUWFJFHSA-N 4-chloro-2-[(1r)-4-[ethyl(2-hydroxyethyl)amino]-1-phenylbutoxy]benzonitrile Chemical compound O([C@H](CCCN(CCO)CC)C=1C=CC=CC=1)C1=CC(Cl)=CC=C1C#N BEHQHZICCZXWAO-HXUWFJFHSA-N 0.000 description 1
- PTFCRSMCXDMEMX-LJQANCHMSA-N 4-chloro-2-[(1r)-4-imidazol-1-yl-1-phenylbutoxy]benzonitrile Chemical compound ClC1=CC=C(C#N)C(O[C@H](CCCN2C=NC=C2)C=2C=CC=CC=2)=C1 PTFCRSMCXDMEMX-LJQANCHMSA-N 0.000 description 1
- YCBPABBMUOXUTK-HXUWFJFHSA-N 4-chloro-2-[(1r)-4-morpholin-4-yl-1-phenylbutoxy]benzonitrile Chemical compound ClC1=CC=C(C#N)C(O[C@H](CCCN2CCOCC2)C=2C=CC=CC=2)=C1 YCBPABBMUOXUTK-HXUWFJFHSA-N 0.000 description 1
- JQRGYJPOOIXAHS-UHFFFAOYSA-N 4-chloro-2-[1-(furan-2-yl)-4-(methylamino)butoxy]benzonitrile Chemical compound C=1C=COC=1C(CCCNC)OC1=CC(Cl)=CC=C1C#N JQRGYJPOOIXAHS-UHFFFAOYSA-N 0.000 description 1
- HTRWYKSUHJPUCZ-UHFFFAOYSA-N 4-chloro-2-[1-(furan-3-yl)-4-(methylamino)butoxy]benzonitrile Chemical compound C1=COC=C1C(CCCNC)OC1=CC(Cl)=CC=C1C#N HTRWYKSUHJPUCZ-UHFFFAOYSA-N 0.000 description 1
- HUBAABOYKIMKKP-UHFFFAOYSA-N 4-chloro-2-[4-(2-hydroxyethylamino)-1-pyridin-4-ylbutoxy]benzonitrile Chemical compound C=1C=NC=CC=1C(CCCNCCO)OC1=CC(Cl)=CC=C1C#N HUBAABOYKIMKKP-UHFFFAOYSA-N 0.000 description 1
- ZOXZOHSSFMBIBR-UHFFFAOYSA-N 4-chloro-2-[4-(ethylamino)-1-pyridin-2-ylbutoxy]benzonitrile Chemical compound C=1C=CC=NC=1C(CCCNCC)OC1=CC(Cl)=CC=C1C#N ZOXZOHSSFMBIBR-UHFFFAOYSA-N 0.000 description 1
- LBPFQRXZCJJPRJ-UHFFFAOYSA-N 4-chloro-2-[4-(ethylamino)-1-pyridin-4-ylbutoxy]benzonitrile Chemical compound C=1C=NC=CC=1C(CCCNCC)OC1=CC(Cl)=CC=C1C#N LBPFQRXZCJJPRJ-UHFFFAOYSA-N 0.000 description 1
- UHQJWLBEUOILOD-UHFFFAOYSA-N 4-chloro-2-[4-(methylamino)-1-pyridin-2-ylbutoxy]benzonitrile Chemical compound C=1C=CC=NC=1C(CCCNC)OC1=CC(Cl)=CC=C1C#N UHQJWLBEUOILOD-UHFFFAOYSA-N 0.000 description 1
- MIRPOWUUORUFBQ-UHFFFAOYSA-N 4-chloro-2-[4-(methylamino)-1-pyridin-3-ylbutoxy]benzonitrile Chemical compound C=1C=CN=CC=1C(CCCNC)OC1=CC(Cl)=CC=C1C#N MIRPOWUUORUFBQ-UHFFFAOYSA-N 0.000 description 1
- LDXIPWPOZJKKFF-UHFFFAOYSA-N 4-chloro-2-[4-(methylamino)-1-pyridin-4-ylbutoxy]benzonitrile Chemical compound C=1C=NC=CC=1C(CCCNC)OC1=CC(Cl)=CC=C1C#N LDXIPWPOZJKKFF-UHFFFAOYSA-N 0.000 description 1
- ZNWRXFGRRLWBKK-UHFFFAOYSA-N 4-chloro-2-[4-(methylamino)-1-thiophen-3-ylbutoxy]benzonitrile Chemical compound C1=CSC=C1C(CCCNC)OC1=CC(Cl)=CC=C1C#N ZNWRXFGRRLWBKK-UHFFFAOYSA-N 0.000 description 1
- UTTARCOGRMPBHU-OAHLLOKOSA-N 4-chloro-5-fluoro-2-[(1r)-1-(furan-3-yl)-4-(methylamino)butoxy]benzonitrile Chemical compound O([C@H](CCCNC)C1=COC=C1)C1=CC(Cl)=C(F)C=C1C#N UTTARCOGRMPBHU-OAHLLOKOSA-N 0.000 description 1
- UQQMUHUYOAGIED-UHFFFAOYSA-N 4-chloro-5-fluoro-2-[4-(methylamino)-1-pyridin-2-ylbutoxy]benzonitrile Chemical compound C=1C=CC=NC=1C(CCCNC)OC1=CC(Cl)=C(F)C=C1C#N UQQMUHUYOAGIED-UHFFFAOYSA-N 0.000 description 1
- 201000006474 Brain Ischemia Diseases 0.000 description 1
- 206010008120 Cerebral ischaemia Diseases 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 1
- 229930064664 L-arginine Natural products 0.000 description 1
- 235000014852 L-arginine Nutrition 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229940124639 Selective inhibitor Drugs 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 1
- 230000008827 biological function Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 206010008118 cerebral infarction Diseases 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000003511 endothelial effect Effects 0.000 description 1
- 210000004962 mammalian cell Anatomy 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0004149.1A GB0004149D0 (en) | 2000-02-23 | 2000-02-23 | Novel compounds |
| GB0004149.1 | 2000-02-23 | ||
| PCT/SE2001/000370 WO2001062713A1 (en) | 2000-02-23 | 2001-02-20 | Novel phenylheteroalkylamine derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003523992A JP2003523992A (ja) | 2003-08-12 |
| JP2003523992A5 true JP2003523992A5 (enExample) | 2008-04-10 |
Family
ID=9886161
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001561723A Withdrawn JP2003523992A (ja) | 2000-02-23 | 2001-02-20 | 新規フェニルヘテロアリールアルキルアミン誘導体 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6743939B2 (enExample) |
| EP (1) | EP1263714B1 (enExample) |
| JP (1) | JP2003523992A (enExample) |
| AR (1) | AR028220A1 (enExample) |
| AT (1) | ATE265422T1 (enExample) |
| AU (1) | AU2001234313A1 (enExample) |
| CO (1) | CO5290257A1 (enExample) |
| DE (1) | DE60103033T2 (enExample) |
| GB (1) | GB0004149D0 (enExample) |
| WO (1) | WO2001062713A1 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0004151D0 (en) * | 2000-02-23 | 2000-04-12 | Astrazeneca Uk Ltd | Novel use |
| GB0004152D0 (en) * | 2000-02-23 | 2000-04-12 | Astrazeneca Uk Ltd | Novel compounds |
| AR035700A1 (es) * | 2001-05-08 | 2004-06-23 | Astrazeneca Ab | Derivados de arilheteroalquilamina, composicion farmaceutica, usos de estos derivados para la fabricacion de medicamentos, metodos de tratamiento, y proceso para la preparacion de estos derivados |
| SE0102640D0 (sv) * | 2001-07-31 | 2001-07-31 | Astrazeneca Ab | Novel compounds |
| SE0102641D0 (sv) * | 2001-07-31 | 2001-07-31 | Astrazeneca Ab | Novel compounds |
| SE0202280D0 (sv) | 2002-07-19 | 2002-07-19 | Astrazeneca Ab | Novel compounds |
| SE0202279D0 (sv) * | 2002-07-19 | 2002-07-19 | Astrazeneca Ab | Novel comppounds |
| SE0203304D0 (sv) * | 2002-11-07 | 2002-11-07 | Astrazeneca Ab | Novel Coumpounds |
| US8604031B2 (en) | 2006-05-18 | 2013-12-10 | Mannkind Corporation | Intracellular kinase inhibitors |
| DE102006031813B4 (de) * | 2006-07-07 | 2011-04-28 | Christian-Albrechts-Universität Zu Kiel | Verwendung basischer Acetophenone als Hemmstoffe von NO-Synthasen |
| US9771316B2 (en) | 2013-01-21 | 2017-09-26 | Osaka University | Phenoxyalkylamine compound |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5144934B1 (enExample) * | 1969-12-09 | 1976-12-01 | ||
| JPS52941B1 (enExample) * | 1969-12-09 | 1977-01-11 | ||
| US4314081A (en) * | 1974-01-10 | 1982-02-02 | Eli Lilly And Company | Arloxyphenylpropylamines |
| FR2432500A1 (fr) * | 1978-02-24 | 1980-02-29 | Roussel Uclaf | Nouveaux derives de la benzene propanamine et leurs sels, procede de preparation et application a titre de medicaments |
| KR880007433A (ko) | 1986-12-22 | 1988-08-27 | 메리 앤 터커 | 3-아릴옥시-3-치환된 프로판아민 |
| US4902710A (en) * | 1988-12-14 | 1990-02-20 | Eli Lilly And Company | Serotonin and norepinephrine uptake inhibitors |
| US5320825A (en) | 1991-05-01 | 1994-06-14 | Trustees Of The University Of Pennsylvania | Serotonin reuptake inhibitors for S.P.E.C.T. imaging |
| EP0576766A1 (en) | 1992-06-29 | 1994-01-05 | Novo Nordisk A/S | Propanolamine derivatives, their preparation and use |
| HN1998000118A (es) | 1997-08-27 | 1999-02-09 | Pfizer Prod Inc | 2 - aminopiridinas que contienen sustituyentes de anillos condensados. |
| HN1998000125A (es) * | 1997-08-28 | 1999-02-09 | Pfizer Prod Inc | 2-aminopiridinas con sustituyentes alcoxi ramificados |
| CN1303379A (zh) * | 1998-06-03 | 2001-07-11 | 辉瑞产品公司 | 作为氧化氮合酶抑制剂的含稠环取代基的2－氨基吡啶 |
-
2000
- 2000-02-23 GB GBGB0004149.1A patent/GB0004149D0/en not_active Ceased
-
2001
- 2001-02-20 JP JP2001561723A patent/JP2003523992A/ja not_active Withdrawn
- 2001-02-20 CO CO01013432A patent/CO5290257A1/es not_active Application Discontinuation
- 2001-02-20 WO PCT/SE2001/000370 patent/WO2001062713A1/en not_active Ceased
- 2001-02-20 AU AU2001234313A patent/AU2001234313A1/en not_active Abandoned
- 2001-02-20 DE DE60103033T patent/DE60103033T2/de not_active Expired - Fee Related
- 2001-02-20 US US10/204,815 patent/US6743939B2/en not_active Expired - Fee Related
- 2001-02-20 AT AT01906490T patent/ATE265422T1/de not_active IP Right Cessation
- 2001-02-20 EP EP01906490A patent/EP1263714B1/en not_active Expired - Lifetime
- 2001-02-21 AR ARP010100772A patent/AR028220A1/es unknown
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