JP2003523995A5 - - Google Patents
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- Publication number
- JP2003523995A5 JP2003523995A5 JP2001561730A JP2001561730A JP2003523995A5 JP 2003523995 A5 JP2003523995 A5 JP 2003523995A5 JP 2001561730 A JP2001561730 A JP 2001561730A JP 2001561730 A JP2001561730 A JP 2001561730A JP 2003523995 A5 JP2003523995 A5 JP 2003523995A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- alkyl
- pharmaceutically acceptable
- acceptable salt
- 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- Withdrawn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 description 44
- 125000000217 alkyl group Chemical group 0.000 description 30
- 150000003839 salts Chemical class 0.000 description 26
- 238000000034 method Methods 0.000 description 21
- 201000010099 disease Diseases 0.000 description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 20
- 125000003545 alkoxy group Chemical group 0.000 description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 13
- 102000008299 Nitric Oxide Synthase Human genes 0.000 description 12
- 108010021487 Nitric Oxide Synthase Proteins 0.000 description 12
- 229910052736 halogen Inorganic materials 0.000 description 11
- 229910052799 carbon Inorganic materials 0.000 description 10
- 150000002367 halogens Chemical class 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- 208000027866 inflammatory disease Diseases 0.000 description 10
- 230000005764 inhibitory process Effects 0.000 description 9
- 229910052717 sulfur Inorganic materials 0.000 description 9
- 102000004190 Enzymes Human genes 0.000 description 8
- 108090000790 Enzymes Proteins 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 108010076864 Nitric Oxide Synthase Type II Proteins 0.000 description 7
- 102000001708 Protein Isoforms Human genes 0.000 description 7
- 108010029485 Protein Isoforms Proteins 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- 230000002265 prevention Effects 0.000 description 7
- 239000003814 drug Substances 0.000 description 6
- 230000001939 inductive effect Effects 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- -1 NR 6 R 7 Chemical group 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
- 102100029438 Nitric oxide synthase, inducible Human genes 0.000 description 4
- 239000002671 adjuvant Substances 0.000 description 4
- 229940111134 coxibs Drugs 0.000 description 4
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 239000008194 pharmaceutical composition Substances 0.000 description 4
- 206010061218 Inflammation Diseases 0.000 description 3
- 102000011779 Nitric Oxide Synthase Type II Human genes 0.000 description 3
- 230000004054 inflammatory process Effects 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 2
- 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 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 208000022559 Inflammatory bowel disease Diseases 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
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 229910052731 fluorine Inorganic materials 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
- 230000003287 optical effect Effects 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
- 125000001544 thienyl group Chemical group 0.000 description 2
- FSKTULCOBFTYFO-OAHLLOKOSA-N (1r)-n-[2-chloro-5-(trifluoromethyl)phenyl]-n'-methyl-1-phenylpropane-1,3-diamine Chemical compound N([C@H](CCNC)C=1C=CC=CC=1)C1=CC(C(F)(F)F)=CC=C1Cl FSKTULCOBFTYFO-OAHLLOKOSA-N 0.000 description 1
- NUCXQAXKICUYCE-OAHLLOKOSA-N 2-[(1r)-3-amino-1-phenylpropyl]sulfanyl-4-(trifluoromethyl)benzonitrile Chemical compound S([C@H](CCN)C=1C=CC=CC=1)C1=CC(C(F)(F)F)=CC=C1C#N NUCXQAXKICUYCE-OAHLLOKOSA-N 0.000 description 1
- OLZXHHOEVBLJLQ-OAHLLOKOSA-N 2-[(1r)-3-amino-1-phenylpropyl]sulfanyl-4-chlorobenzonitrile Chemical compound S([C@H](CCN)C=1C=CC=CC=1)C1=CC(Cl)=CC=C1C#N OLZXHHOEVBLJLQ-OAHLLOKOSA-N 0.000 description 1
- OYZNFNQMOVSAAW-OAHLLOKOSA-N 2-[[(1r)-3-amino-1-phenylpropyl]amino]-4-chloro-5-fluorobenzonitrile Chemical compound N([C@H](CCN)C=1C=CC=CC=1)C1=CC(Cl)=C(F)C=C1C#N OYZNFNQMOVSAAW-OAHLLOKOSA-N 0.000 description 1
- LPFUTOIWAPQWNU-UHFFFAOYSA-N 2-[[3-(dimethylamino)-1-phenylpropyl]amino]-4-(trifluoromethyl)benzonitrile Chemical compound C=1C=CC=CC=1C(CCN(C)C)NC1=CC(C(F)(F)F)=CC=C1C#N LPFUTOIWAPQWNU-UHFFFAOYSA-N 0.000 description 1
- XIIWKAOOAOYUGP-UHFFFAOYSA-N 3-(2,5-dichlorophenyl)sulfanyl-3-(1,3-oxazol-2-yl)propan-1-amine Chemical compound N=1C=COC=1C(CCN)SC1=CC(Cl)=CC=C1Cl XIIWKAOOAOYUGP-UHFFFAOYSA-N 0.000 description 1
- XFCPDHXTMYHGOX-UHFFFAOYSA-N 4-bromo-2-[3-(methylamino)-1-phenylpropyl]sulfanylbenzonitrile Chemical compound C=1C=CC=CC=1C(CCNC)SC1=CC(Br)=CC=C1C#N XFCPDHXTMYHGOX-UHFFFAOYSA-N 0.000 description 1
- YOHGBLUSMJJZIO-UHFFFAOYSA-N 4-chloro-2-[3-(methylamino)-1-phenylpropyl]sulfanylbenzonitrile Chemical compound C=1C=CC=CC=1C(CCNC)SC1=CC(Cl)=CC=C1C#N YOHGBLUSMJJZIO-UHFFFAOYSA-N 0.000 description 1
- FQLGXOWCYLLKRS-UHFFFAOYSA-N 4-chloro-2-[methyl-[3-(methylamino)-1-phenylpropyl]amino]benzonitrile Chemical compound C=1C=CC=CC=1C(CCNC)N(C)C1=CC(Cl)=CC=C1C#N FQLGXOWCYLLKRS-UHFFFAOYSA-N 0.000 description 1
- RCRGHHSVZNIRSC-MRXNPFEDSA-N 4-chloro-5-fluoro-2-[[(1r)-3-(methylamino)-1-phenylpropyl]amino]benzonitrile Chemical compound N([C@H](CCNC)C=1C=CC=CC=1)C1=CC(Cl)=C(F)C=C1C#N RCRGHHSVZNIRSC-MRXNPFEDSA-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
- 239000013543 active substance 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
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000003511 endothelial effect Effects 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 210000004962 mammalian cell Anatomy 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000005322 morpholin-1-yl group Chemical group 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 239000000825 pharmaceutical preparation 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
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0004151.7 | 2000-02-23 | ||
| GBGB0004151.7A GB0004151D0 (en) | 2000-02-23 | 2000-02-23 | Novel use |
| PCT/SE2001/000371 WO2001062721A1 (en) | 2000-02-23 | 2001-02-20 | Novel use of phenylheteroalkylamine derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003523995A JP2003523995A (ja) | 2003-08-12 |
| JP2003523995A5 true JP2003523995A5 (enExample) | 2008-04-03 |
Family
ID=9886163
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001561730A Withdrawn JP2003523995A (ja) | 2000-02-23 | 2001-02-20 | フェニルヘテロアルキルアミン誘導体の新規なる使用 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US6953797B2 (enExample) |
| EP (1) | EP1263718B1 (enExample) |
| JP (1) | JP2003523995A (enExample) |
| KR (1) | KR100721087B1 (enExample) |
| CN (1) | CN1210270C (enExample) |
| AT (1) | ATE265428T1 (enExample) |
| AU (1) | AU780781B2 (enExample) |
| BR (1) | BR0108539A (enExample) |
| CA (1) | CA2396960A1 (enExample) |
| CO (1) | CO5660084A1 (enExample) |
| DE (1) | DE60103035T2 (enExample) |
| GB (1) | GB0004151D0 (enExample) |
| IL (1) | IL150640A0 (enExample) |
| MX (1) | MXPA02008204A (enExample) |
| NO (1) | NO20024013L (enExample) |
| WO (1) | WO2001062721A1 (enExample) |
| ZA (1) | ZA200205801B (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| JP2004537531A (ja) * | 2001-06-12 | 2004-12-16 | エスケー コーポレイション | 新規フェニルアルキルジアミンおよびアミド類似体 |
| SE0102640D0 (sv) | 2001-07-31 | 2001-07-31 | Astrazeneca Ab | Novel compounds |
| SE0203304D0 (sv) * | 2002-11-07 | 2002-11-07 | Astrazeneca Ab | Novel Coumpounds |
Family Cites Families (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US466910A (en) * | 1892-01-12 | Machine for covering wire | ||
| GB765849A (en) | 1953-09-21 | 1957-01-16 | Univ Leeds | Improvements in or relating to new aminoalkyl phenyl ethers |
| GB922600A (en) | 1960-05-06 | 1963-04-03 | Crookes Lab Ltd | Ortho-tertiary-butyl phenolethers |
| US3205136A (en) | 1962-12-24 | 1965-09-07 | Smith Kline French Lab | Antidepressant phenyloxyalkylamines |
| 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 |
| JPS52941A (en) | 1975-06-24 | 1977-01-06 | Hitachi Chem Co Ltd | Polyurethane insulating coating composition |
| 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 |
| GB2060620B (en) | 1979-09-14 | 1983-05-25 | Wyeth John & Brother Ltd | 3-aryl-3-aryloxypropylamines |
| GB2060621A (en) | 1979-09-14 | 1981-05-07 | Wyeth John & Brother Ltd | 3-Aryl-3-aryloxypropylamines |
| GB2060622B (en) | 1979-09-14 | 1983-05-25 | Wyeth John & Brother Ltd | 3-aryl-3-aryloxyalkylamines |
| 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 |
| KR880007433A (ko) | 1986-12-22 | 1988-08-27 | 메리 앤 터커 | 3-아릴옥시-3-치환된 프로판아민 |
| DK630987D0 (da) | 1987-12-01 | 1987-12-01 | Ferrosan As | Aryloxyphenylpropylaminer, deres fremstilling og anvendelse |
| 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 |
| US5320825A (en) | 1991-05-01 | 1994-06-14 | Trustees Of The University Of Pennsylvania | Serotonin reuptake inhibitors for S.P.E.C.T. imaging |
| FR2676054B1 (fr) | 1991-05-03 | 1993-09-03 | Sanofi Elf | Nouveaux composes n-alkylenepiperidino et leurs enantiomeres, procede pour leur preparation et compositions pharmaceutiques les contenant. |
| EP0571685A1 (en) | 1992-05-27 | 1993-12-01 | Novo Nordisk A/S | Aryloxyheteroarylpropylamines, their preparation and use |
| EP0576766A1 (en) * | 1992-06-29 | 1994-01-05 | Novo Nordisk A/S | Propanolamine derivatives, their preparation and use |
| EP0661266A1 (en) | 1993-12-27 | 1995-07-05 | Toa Eiyo Ltd. | Substituted cyclic amine compounds as 5HT2 antagonists |
| DK0707007T3 (da) | 1994-10-14 | 2002-03-18 | Merck Patent Gmbh | Amino(thio)etherderivater som CNS-aktive midler |
| 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 |
| CA2319781A1 (en) | 1998-02-02 | 1999-08-05 | Liping Wang | Cyclic amine modulators of chemokine receptor activity |
| HUP0102236A3 (en) | 1998-06-03 | 2003-01-28 | Pfizer Prod Inc | 2-aminopyridines containing fused ring substituents as nitric oxide synthase inhibitors and pharmaceutical compositions containing them and their use |
| SE9803773D0 (sv) | 1998-11-05 | 1998-11-05 | Astra Pharma Prod | Compounds |
| KR20010108394A (ko) | 1999-03-26 | 2001-12-07 | 다비드 에 질레스 | 신규 화합물 |
| GB0004149D0 (en) * | 2000-02-23 | 2000-04-12 | Astrazeneca Uk Ltd | Novel compounds |
| GB0021670D0 (en) | 2000-09-04 | 2000-10-18 | Astrazeneca Ab | Chemical compounds |
| AU2002215928A1 (en) | 2000-10-09 | 2002-04-22 | Novartis Pharma Gmbh | N-(4-aryloxypiperidin-1-ylalkyl) cinnamic amides as ccr3 receptor antagonists |
| JP4716655B2 (ja) * | 2001-11-21 | 2011-07-06 | ユニバーシティ・オブ・オーフース | 抗炎症剤としてのモノ−およびジアシルグリセロールのグリコシドの使用 |
-
2000
- 2000-02-23 GB GBGB0004151.7A patent/GB0004151D0/en not_active Ceased
-
2001
- 2001-02-20 CN CNB018054560A patent/CN1210270C/zh not_active Expired - Fee Related
- 2001-02-20 MX MXPA02008204A patent/MXPA02008204A/es active IP Right Grant
- 2001-02-20 CO CO01013435A patent/CO5660084A1/es not_active Application Discontinuation
- 2001-02-20 BR BR0108539-5A patent/BR0108539A/pt not_active IP Right Cessation
- 2001-02-20 KR KR1020027010954A patent/KR100721087B1/ko not_active Expired - Fee Related
- 2001-02-20 AU AU32601/01A patent/AU780781B2/en not_active Ceased
- 2001-02-20 DE DE60103035T patent/DE60103035T2/de not_active Expired - Fee Related
- 2001-02-20 EP EP01904777A patent/EP1263718B1/en not_active Expired - Lifetime
- 2001-02-20 AT AT01904777T patent/ATE265428T1/de not_active IP Right Cessation
- 2001-02-20 CA CA002396960A patent/CA2396960A1/en not_active Abandoned
- 2001-02-20 WO PCT/SE2001/000371 patent/WO2001062721A1/en not_active Ceased
- 2001-02-20 IL IL15064001A patent/IL150640A0/xx not_active IP Right Cessation
- 2001-02-20 US US10/204,808 patent/US6953797B2/en not_active Expired - Fee Related
- 2001-02-20 JP JP2001561730A patent/JP2003523995A/ja not_active Withdrawn
-
2002
- 2002-07-19 ZA ZA200205801A patent/ZA200205801B/en unknown
- 2002-08-22 NO NO20024013A patent/NO20024013L/no not_active Application Discontinuation
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