JP2003517013A5 - - Google Patents
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- Publication number
- JP2003517013A5 JP2003517013A5 JP2001544882A JP2001544882A JP2003517013A5 JP 2003517013 A5 JP2003517013 A5 JP 2003517013A5 JP 2001544882 A JP2001544882 A JP 2001544882A JP 2001544882 A JP2001544882 A JP 2001544882A JP 2003517013 A5 JP2003517013 A5 JP 2003517013A5
- Authority
- JP
- Japan
- Prior art keywords
- phenoxy
- propanol
- alkyl
- hydroxy
- group
- 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.)
- Granted
Links
- -1 t-butoxycarbonyl group Chemical group 0.000 description 16
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 229960004592 isopropanol Drugs 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000012453 solvate Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 2
- XLHUBROMZOAQMV-UHFFFAOYSA-N 1,4-benzosemiquinone Chemical group [O]C1=CC=C(O)C=C1 XLHUBROMZOAQMV-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000003818 flash chromatography Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 208000002551 irritable bowel syndrome Diseases 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- 0 *c(ccc(OCI)c1)c1N Chemical compound *c(ccc(OCI)c1)c1N 0.000 description 1
- MXKMYDLASXNPAP-YMQLSTQVSA-N 4-bromo-n-[4-[2-[[(2s)-2-hydroxy-3-[4-hydroxy-3-(methanesulfonamido)phenoxy]propyl]amino]piperidin-1-yl]phenyl]benzenesulfonamide Chemical compound C1=C(O)C(NS(=O)(=O)C)=CC(OC[C@@H](O)CNC2N(CCCC2)C=2C=CC(NS(=O)(=O)C=3C=CC(Br)=CC=3)=CC=2)=C1 MXKMYDLASXNPAP-YMQLSTQVSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 241000009298 Trigla lyra Species 0.000 description 1
- 208000036029 Uterine contractions during pregnancy Diseases 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000001430 anti-depressive effect Effects 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
- 125000003865 brosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)S(*)(=O)=O 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- WOTZFWTUWUQBLQ-FQEVSTJZSA-N ethyl 4-[4-[[(2s)-2-hydroxy-3-[4-hydroxy-3-(methylsulfamoyl)phenoxy]propyl]amino]piperidin-1-yl]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1N1CCC(NC[C@H](O)COC=2C=C(C(O)=CC=2)S(=O)(=O)NC)CC1 WOTZFWTUWUQBLQ-FQEVSTJZSA-N 0.000 description 1
- MRTINNCFOIVQPO-NRFANRHFSA-N ethyl 4-[4-[[[(2s)-2-hydroxy-3-[4-hydroxy-3-(methanesulfonamido)phenoxy]propyl]amino]methyl]piperidin-1-yl]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1N1CCC(CNC[C@H](O)COC=2C=C(NS(C)(=O)=O)C(O)=CC=2)CC1 MRTINNCFOIVQPO-NRFANRHFSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 230000004130 lipolysis Effects 0.000 description 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
- VWMBXJFXWFYPFO-IBGZPJMESA-N n-[5-[(2s)-3-[[1-(4-cyanophenyl)piperidin-4-yl]amino]-2-hydroxypropoxy]-2-hydroxyphenyl]methanesulfonamide Chemical compound C1=C(O)C(NS(=O)(=O)C)=CC(OC[C@@H](O)CNC2CCN(CC2)C=2C=CC(=CC=2)C#N)=C1 VWMBXJFXWFYPFO-IBGZPJMESA-N 0.000 description 1
- KUVWNDAUQMBWDS-UHFFFAOYSA-N n-[6-[4-[[2-hydroxy-3-(4-hydroxyphenoxy)propyl]amino]piperidin-1-yl]pyridin-3-yl]-4-propan-2-ylbenzenesulfonamide Chemical compound C1=CC(C(C)C)=CC=C1S(=O)(=O)NC1=CC=C(N2CCC(CC2)NCC(O)COC=2C=CC(O)=CC=2)N=C1 KUVWNDAUQMBWDS-UHFFFAOYSA-N 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 230000000506 psychotropic effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000037390 scarring Effects 0.000 description 1
- QMPLQMSXKMRVAL-NRFANRHFSA-N tert-butyl 4-[4-[[(2s)-2-hydroxy-3-[4-hydroxy-3-(methanesulfonamido)phenoxy]propyl]amino]piperidin-1-yl]benzoate Chemical compound C1=CC(C(=O)OC(C)(C)C)=CC=C1N1CCC(NC[C@H](O)COC=2C=C(NS(C)(=O)=O)C(O)=CC=2)CC1 QMPLQMSXKMRVAL-NRFANRHFSA-N 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9915931A FR2802531B1 (fr) | 1999-12-17 | 1999-12-17 | Phenoxypropanolamines, procede pour leur preparation et compositions pharmaceutiques les contenant |
| FR99/15932 | 1999-12-17 | ||
| FR9915932A FR2802529B1 (fr) | 1999-12-17 | 1999-12-17 | Phenoxypropanolamines, procede pour les preparer et compositions pharmaceutiques les contenant |
| FR99/15931 | 1999-12-17 | ||
| PCT/FR2000/003535 WO2001043744A1 (fr) | 1999-12-17 | 2000-12-14 | Phenoxypropanolamines, procede pour leur preparation et compositions pharmaceutiques les contenant |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003517013A JP2003517013A (ja) | 2003-05-20 |
| JP2003517013A5 true JP2003517013A5 (enExample) | 2008-02-14 |
| JP4782342B2 JP4782342B2 (ja) | 2011-09-28 |
Family
ID=26235183
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001544882A Expired - Fee Related JP4782342B2 (ja) | 1999-12-17 | 2000-12-14 | フェノキシプロパノールアミン類、それらの製造方法およびそれらを含む医薬組成物 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6867220B2 (enExample) |
| EP (1) | EP1242083B1 (enExample) |
| JP (1) | JP4782342B2 (enExample) |
| AT (1) | ATE356624T1 (enExample) |
| AU (1) | AU2525801A (enExample) |
| DE (1) | DE60033964T2 (enExample) |
| WO (1) | WO2001043744A1 (enExample) |
Families Citing this family (27)
| 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 |
| US7074934B2 (en) * | 2000-06-13 | 2006-07-11 | Tularik Limited | Serine protease inhibitors |
| US7005439B2 (en) | 2000-06-20 | 2006-02-28 | Astrazeneca Ab | Compounds |
| AR028948A1 (es) | 2000-06-20 | 2003-05-28 | Astrazeneca Ab | Compuestos novedosos |
| US6537994B2 (en) | 2000-07-17 | 2003-03-25 | Wyeth | Heterocyclic β3 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 |
| US6410734B1 (en) | 2000-07-17 | 2002-06-25 | Wyeth | 2-substituted thiazolidinones as beta-3 adrenergic receptor agonists |
| US6465501B2 (en) | 2000-07-17 | 2002-10-15 | Wyeth | Azolidines as β3 adrenergic receptor agonists |
| US6525202B2 (en) | 2000-07-17 | 2003-02-25 | Wyeth | Cyclic amine phenyl beta-3 adrenergic receptor agonists |
| US6498170B2 (en) | 2000-07-17 | 2002-12-24 | Wyeth | Cyclamine sulfonamides as β-3 adrenergic receptor agonists |
| US6444685B1 (en) * | 2000-07-17 | 2002-09-03 | Wyeth | N-(4-sulfonylaryl)Cyclylamine 2-hydroxyethylamines as beta-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 |
| SE0301369D0 (sv) | 2003-05-09 | 2003-05-09 | Astrazeneca Ab | Chemical compounds |
| 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 |
| MA44037B1 (fr) | 2016-06-06 | 2020-03-31 | Arena Pharm Inc | Modulateurs du récepteur adrénergique bêta 3 utile dans le traitement ou la prévention de troubles associés à ceux-ci |
| TN2019000290A1 (en) | 2017-03-20 | 2021-05-07 | Forma Therapeutics Inc | Pyrrolopyrrole compositions as pyruvate kinase (pkr) activators |
| TWI822713B (zh) * | 2017-12-06 | 2023-11-21 | 美商艾尼納製藥公司 | 適用於治療或預防與其相關之病症之β－３腎上腺素受體的調節劑 |
| BR112021005188A2 (pt) | 2018-09-19 | 2021-06-08 | Forma Therapeutics, Inc. | tratamento de anemia falciforme com um composto de ativação de piruvato cinase r |
| JP7450610B2 (ja) | 2018-09-19 | 2024-03-15 | ノヴォ・ノルディスク・ヘルス・ケア・アーゲー | ピルビン酸キナーゼｒの活性化 |
| BR112022004715A2 (pt) | 2019-09-19 | 2022-06-14 | Forma Therapeutics Inc | Composições de ativação de piruvato quinase r (pkr) |
| US12128035B2 (en) | 2021-03-19 | 2024-10-29 | Novo Nordisk Health Care Ag | Activating pyruvate kinase R |
Family Cites Families (9)
| 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 |
| PE92198A1 (es) * | 1996-08-01 | 1999-01-09 | Banyu Pharma Co Ltd | Derivados de 1,4-piperidina disustituida que contienen fluor |
| KR20010042587A (ko) * | 1998-04-09 | 2001-05-25 | 기따자또 이찌로 | 인테그린 알파브이베타3 길항제로서 아미노피페리딘 유도체 |
| FR2780057B1 (fr) * | 1998-06-18 | 2002-09-13 | Sanofi Sa | Phenoxypropanolamines, procede pour leur preparation et compositions pharmaceutiques les contenant |
| US6525202B2 (en) * | 2000-07-17 | 2003-02-25 | Wyeth | Cyclic amine phenyl beta-3 adrenergic receptor agonists |
| US6444685B1 (en) * | 2000-07-17 | 2002-09-03 | Wyeth | N-(4-sulfonylaryl)Cyclylamine 2-hydroxyethylamines as beta-3 adrenergic receptor agonists |
-
2000
- 2000-12-14 WO PCT/FR2000/003535 patent/WO2001043744A1/fr not_active Ceased
- 2000-12-14 EP EP00988915A patent/EP1242083B1/fr not_active Expired - Lifetime
- 2000-12-14 US US10/149,497 patent/US6867220B2/en not_active Expired - Fee Related
- 2000-12-14 DE DE60033964T patent/DE60033964T2/de not_active Expired - Lifetime
- 2000-12-14 AU AU25258/01A patent/AU2525801A/en not_active Abandoned
- 2000-12-14 AT AT00988915T patent/ATE356624T1/de not_active IP Right Cessation
- 2000-12-14 JP JP2001544882A patent/JP4782342B2/ja not_active Expired - Fee Related
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