JP2003528046A5 - - Google Patents
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- JP2003528046A5 JP2003528046A5 JP2001544717A JP2001544717A JP2003528046A5 JP 2003528046 A5 JP2003528046 A5 JP 2003528046A5 JP 2001544717 A JP2001544717 A JP 2001544717A JP 2001544717 A JP2001544717 A JP 2001544717A JP 2003528046 A5 JP2003528046 A5 JP 2003528046A5
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- JP
- Japan
- Prior art keywords
- alkyl
- formula
- compound
- group
- preparation
- 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.)
- Ceased
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- LRKHNHJSKZSLQL-UHFFFAOYSA-N 3-methylsulfinyl-4-phenylmethoxyphenol Chemical compound CS(=O)C1=CC(O)=CC=C1OCC1=CC=CC=C1 LRKHNHJSKZSLQL-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- MOHYOXXOKFQHDC-UHFFFAOYSA-N 1-(chloromethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CCl)C=C1 MOHYOXXOKFQHDC-UHFFFAOYSA-N 0.000 description 1
- UJUKHOATWVVDER-UHFFFAOYSA-N 1-amino-1-phenoxypropan-1-ol Chemical compound CCC(N)(O)OC1=CC=CC=C1 UJUKHOATWVVDER-UHFFFAOYSA-N 0.000 description 1
- WDTHTDJKIDUSQR-UHFFFAOYSA-N 3-ethylsulfinyl-4-phenylmethoxyphenol Chemical compound CCS(=O)C1=CC(O)=CC=C1OCC1=CC=CC=C1 WDTHTDJKIDUSQR-UHFFFAOYSA-N 0.000 description 1
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 1
- IBFVCMAHXVYHFQ-UHFFFAOYSA-N 6-(4-aminopiperidin-1-yl)pyridine-3-carboxamide Chemical compound C1CC(N)CCN1C1=CC=C(C(N)=O)C=N1 IBFVCMAHXVYHFQ-UHFFFAOYSA-N 0.000 description 1
- ZIJAZUBWHAZHPL-UHFFFAOYSA-N 6-chloropyridine-3-carboxamide Chemical compound NC(=O)C1=CC=C(Cl)N=C1 ZIJAZUBWHAZHPL-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 208000036029 Uterine contractions during pregnancy Diseases 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000003178 anti-diabetic effect Effects 0.000 description 1
- 230000001384 anti-glaucoma Effects 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- ZLZGWYCDEZAFBU-UHFFFAOYSA-N ethyl 6-(4-aminopiperidin-1-yl)pyridine-3-carboxylate Chemical compound N1=CC(C(=O)OCC)=CC=C1N1CCC(N)CC1 ZLZGWYCDEZAFBU-UHFFFAOYSA-N 0.000 description 1
- IUXHIOYHTYULMV-UHFFFAOYSA-N ethyl 6-[4-[(2-methylpropan-2-yl)oxycarbonylamino]piperidin-1-yl]pyridine-3-carboxylate Chemical compound N1=CC(C(=O)OCC)=CC=C1N1CCC(NC(=O)OC(C)(C)C)CC1 IUXHIOYHTYULMV-UHFFFAOYSA-N 0.000 description 1
- ILDJJTQWIZLGPO-UHFFFAOYSA-N ethyl 6-chloropyridine-3-carboxylate Chemical compound CCOC(=O)C1=CC=C(Cl)N=C1 ILDJJTQWIZLGPO-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- UUBJKHVFGWGJKX-UHFFFAOYSA-N hydrate tetrahydrochloride Chemical compound O.Cl.Cl.Cl.Cl UUBJKHVFGWGJKX-UHFFFAOYSA-N 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 208000002551 irritable bowel syndrome Diseases 0.000 description 1
- 230000004130 lipolysis Effects 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 230000000506 psychotropic effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000037390 scarring Effects 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR99/15933 | 1999-12-17 | ||
| FR9915933A FR2802533B1 (fr) | 1999-12-17 | 1999-12-17 | Phenoxypropanolamines, leur preparation et leur application en therapeutique |
| PCT/FR2000/003559 WO2001044227A1 (fr) | 1999-12-17 | 2000-12-15 | Phenoxypropanolamines, leur preparation et leur application en therapeutique |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003528046A JP2003528046A (ja) | 2003-09-24 |
| JP2003528046A5 true JP2003528046A5 (enExample) | 2008-02-14 |
Family
ID=9553378
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001544717A Ceased JP2003528046A (ja) | 1999-12-17 | 2000-12-15 | フェノキシプロパノールアミン類、それらの製造および治療的使用 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6852736B2 (enExample) |
| EP (1) | EP1242404B1 (enExample) |
| JP (1) | JP2003528046A (enExample) |
| AT (1) | ATE270668T1 (enExample) |
| AU (1) | AU2527301A (enExample) |
| DE (1) | DE60012048T2 (enExample) |
| FR (1) | FR2802533B1 (enExample) |
| WO (1) | WO2001044227A1 (enExample) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE9902987D0 (sv) | 1999-08-24 | 1999-08-24 | Astra Pharma Prod | Novel compounds |
| CO5300399A1 (es) | 2000-02-25 | 2003-07-31 | Astrazeneca Ab | Heterocicliocs que contienen nitrogeno, proceso para su preparacion y composiciones farmaceuticas que los contienen |
| US7005439B2 (en) | 2000-06-20 | 2006-02-28 | Astrazeneca Ab | Compounds |
| AR028948A1 (es) | 2000-06-20 | 2003-05-28 | Astrazeneca Ab | Compuestos novedosos |
| US6525202B2 (en) | 2000-07-17 | 2003-02-25 | Wyeth | Cyclic amine phenyl beta-3 adrenergic receptor agonists |
| US6537994B2 (en) | 2000-07-17 | 2003-03-25 | Wyeth | Heterocyclic β3 adrenergic receptor agonists |
| US6444685B1 (en) | 2000-07-17 | 2002-09-03 | Wyeth | N-(4-sulfonylaryl)Cyclylamine 2-hydroxyethylamines as beta-3 adrenergic receptor agonists |
| US6458817B1 (en) | 2000-07-17 | 2002-10-01 | Wyeth | Substituted arylsulfides, arylsulfoxides and arylsulfones as beta-3 adrenergic receptor agonists |
| US6506901B2 (en) | 2000-07-17 | 2003-01-14 | Wyeth | Substituted 2-(S)-hydroxy-3-(piperidin-4-yl-methylamino)-propyl ethers and substituted 2-aryl-2-(R)-hydroxy-1-(piperidin-4-yl-methyl)-ethylamine β-3 adrenergic receptor agonists |
| US6451814B1 (en) | 2000-07-17 | 2002-09-17 | Wyeth | Heterocyclic β-3 adrenergic receptor agonists |
| US6509358B2 (en) | 2000-07-17 | 2003-01-21 | Wyeth | Piperidino-phenyl amino squarate and thiadiazole dioxide beta-3 adrenergic receptor agonists |
| US6465501B2 (en) | 2000-07-17 | 2002-10-15 | Wyeth | Azolidines as β3 adrenergic receptor agonists |
| US6395762B1 (en) | 2000-07-17 | 2002-05-28 | American Home Products Corporation | Phenyl amino squarate and thiadiazole dioxide beta-3 adrenergic receptor agonists |
| US6514991B2 (en) | 2000-07-17 | 2003-02-04 | Wyeth | Phenyl-oxo-tetrahydroquinolin-3-yl beta-3 adrenergic receptor agonists |
| US6410734B1 (en) | 2000-07-17 | 2002-06-25 | Wyeth | 2-substituted thiazolidinones as beta-3 adrenergic receptor agonists |
| US6498170B2 (en) | 2000-07-17 | 2002-12-24 | Wyeth | Cyclamine sulfonamides as β-3 adrenergic receptor agonists |
| GB0104050D0 (en) | 2001-02-19 | 2001-04-04 | Astrazeneca Ab | Chemical compounds |
| AR035230A1 (es) | 2001-03-19 | 2004-05-05 | Astrazeneca Ab | Compuestos de bencimidazol, proceso para su preparacion, composicion farmaceutica, proceso para la preparacion de dicha composicion farmaceutica, y usos de estos compuestos para la elaboracion de medicamentos |
| GB0107228D0 (en) | 2001-03-22 | 2001-05-16 | Astrazeneca Ab | Chemical compounds |
| SE0101038D0 (sv) | 2001-03-23 | 2001-03-23 | Astrazeneca Ab | Novel compounds |
| SE0103818D0 (sv) | 2001-11-15 | 2001-11-15 | Astrazeneca Ab | Chemical compounds |
| SE0300458D0 (sv) * | 2003-02-19 | 2003-02-19 | Astrazeneca Ab | Novel compounds |
| SE0300456D0 (sv) * | 2003-02-19 | 2003-02-19 | Astrazeneca Ab | Novel compounds |
| SE0300457D0 (sv) * | 2003-02-19 | 2003-02-19 | Astrazeneca Ab | Novel compounds |
| SE0301369D0 (sv) | 2003-05-09 | 2003-05-09 | Astrazeneca Ab | Chemical compounds |
| CN1980929A (zh) * | 2004-02-24 | 2007-06-13 | 比奥阿克松医疗技术股份有限公司 | 4－取代哌啶衍生物 |
| TW200738634A (en) | 2005-08-02 | 2007-10-16 | Astrazeneca Ab | New salt |
| EP1947103A1 (en) * | 2007-01-22 | 2008-07-23 | 4Sc Ag | Aryloxypropanolamines, methods of preparation thereof and use of aryloxypropanolamines as medicaments |
| JP2010535172A (ja) * | 2007-08-02 | 2010-11-18 | エフ．ホフマン−ラ ロシュ アーゲー | Ｃｎｓ障害の処置のためのベンズアミド誘導体の使用 |
| US9452980B2 (en) * | 2009-12-22 | 2016-09-27 | Hoffmann-La Roche Inc. | Substituted benzamides |
| CN108713019B (zh) | 2016-03-17 | 2021-06-15 | 豪夫迈·罗氏有限公司 | 具有作为taar的激动剂的活性的5-乙基-4-甲基-吡唑-3-甲酰胺衍生物 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0095454A3 (de) * | 1982-05-13 | 1985-04-03 | Gerot-Pharmazeutika Gesellschaft m.b.H. | Neue kernsubstituierte Pyrogallol-Derivate |
| DE3524955A1 (de) * | 1984-07-19 | 1986-01-30 | Sandoz-Patent-GmbH, 7850 Lörrach | 3-aminopropoxyaryl-derivate, ihre herstellung und sie enthaltende arzneimittel |
| GB2163150B (en) * | 1984-07-19 | 1988-05-25 | Sandoz Ltd | 3-aminopropoxyaryl derivatives |
| US5627196A (en) * | 1995-01-17 | 1997-05-06 | Eli Lilly And Company | Compounds having effects on serotonin-related systems |
| FR2780057B1 (fr) * | 1998-06-18 | 2002-09-13 | Sanofi Sa | Phenoxypropanolamines, procede pour leur preparation et compositions pharmaceutiques les contenant |
-
1999
- 1999-12-17 FR FR9915933A patent/FR2802533B1/fr not_active Expired - Fee Related
-
2000
- 2000-12-15 EP EP00988936A patent/EP1242404B1/fr not_active Expired - Lifetime
- 2000-12-15 WO PCT/FR2000/003559 patent/WO2001044227A1/fr not_active Ceased
- 2000-12-15 AT AT00988936T patent/ATE270668T1/de not_active IP Right Cessation
- 2000-12-15 JP JP2001544717A patent/JP2003528046A/ja not_active Ceased
- 2000-12-15 AU AU25273/01A patent/AU2527301A/en not_active Abandoned
- 2000-12-15 US US10/149,626 patent/US6852736B2/en not_active Expired - Fee Related
- 2000-12-15 DE DE60012048T patent/DE60012048T2/de not_active Expired - Lifetime
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