JP2005520805A5 - - Google Patents
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- Publication number
- JP2005520805A5 JP2005520805A5 JP2003559510A JP2003559510A JP2005520805A5 JP 2005520805 A5 JP2005520805 A5 JP 2005520805A5 JP 2003559510 A JP2003559510 A JP 2003559510A JP 2003559510 A JP2003559510 A JP 2003559510A JP 2005520805 A5 JP2005520805 A5 JP 2005520805A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- phenyl
- absent
- optionally substituted
- alk
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 claims description 28
- -1 C 1 -C 6 alkyl Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 14
- 229910052799 carbon Inorganic materials 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
- 238000000034 method Methods 0.000 description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 239000013058 crude material Substances 0.000 description 10
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 229910004298 SiO 2 Inorganic materials 0.000 description 4
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 206010003668 atrial tachycardia Diseases 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000003818 flash chromatography Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- QGMGHALXLXKCBD-UHFFFAOYSA-N 4-amino-n-(2-aminophenyl)benzamide Chemical compound C1=CC(N)=CC=C1C(=O)NC1=CC=CC=C1N QGMGHALXLXKCBD-UHFFFAOYSA-N 0.000 description 1
- 0 CC(C)CN(c(c(N1)ccc2)c2OC[C@](CNC(C)(C)Cc(cc2)ccc2Oc(nc2)ccc2C(*)=O)O)C1=O Chemical compound CC(C)CN(c(c(N1)ccc2)c2OC[C@](CNC(C)(C)Cc(cc2)ccc2Oc(nc2)ccc2C(*)=O)O)C1=O 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34814402P | 2002-01-11 | 2002-01-11 | |
| PCT/US2002/038982 WO2003059348A1 (en) | 2002-01-11 | 2002-12-24 | 2-oxo-benzimidazolyl substituted ethanolamine derivatives and their use as beta3 agonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005520805A JP2005520805A (ja) | 2005-07-14 |
| JP2005520805A5 true JP2005520805A5 (https=) | 2006-02-16 |
Family
ID=23366814
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003559510A Pending JP2005520805A (ja) | 2002-01-11 | 2002-12-24 | ２−オキソ−ベンズイミダゾリル置換型エタノールアミン誘導体およびβ３アゴニストとしてのその使用 |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US7009060B2 (https=) |
| EP (1) | EP1467733A1 (https=) |
| JP (1) | JP2005520805A (https=) |
| AU (1) | AU2002357084A1 (https=) |
| WO (1) | WO2003059348A1 (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080125403A1 (en) | 2004-04-02 | 2008-05-29 | Merck & Co., Inc. | Method of Treating Men with Metabolic and Anthropometric Disorders |
| CA2792407A1 (en) * | 2010-03-08 | 2011-09-15 | The University Of Tennessee Research Foundation | Beta-adrenergic receptor agonists and uses thereof |
| BR112020018094A2 (pt) | 2018-03-08 | 2020-12-22 | Incyte Corporation | Compostos de aminopirazina diol como inibidores de pi3k-¿ |
| US11046658B2 (en) | 2018-07-02 | 2021-06-29 | Incyte Corporation | Aminopyrazine derivatives as PI3K-γ inhibitors |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH624395A5 (https=) * | 1976-01-08 | 1981-07-31 | Ciba Geigy Ag | |
| CA1116598A (en) | 1977-07-13 | 1982-01-19 | William T. Comer | 3-indolyl-tertiary butylaminopropanols |
| JPS6010021B2 (ja) * | 1979-01-31 | 1985-03-14 | 田辺製薬株式会社 | 新規ベンジルアルコ−ル誘導体及びその製法 |
| DE3423429A1 (de) | 1984-06-26 | 1986-01-02 | Beiersdorf Ag, 2000 Hamburg | Substituierte phenoxyalkylaminopropanole, verfahren zu ihrer herstellung und ihre verwendung sowie diese verbindungen enthaltende zubereitungen |
| DE3426419A1 (de) * | 1984-07-18 | 1986-01-23 | Boehringer Mannheim Gmbh, 6800 Mannheim | Neue oxindol-derivate, verfahren zu ihrer herstellung, diese verbindungen enthaltende arzneimittel und zwischenprodukte |
| US4728651A (en) | 1985-10-24 | 1988-03-01 | Hoechst-Roussel Pharmaceuticals Inc. | Antihypertensive thieno-isoxazoles and -pyrazoles |
| GB8528633D0 (en) | 1985-11-21 | 1985-12-24 | Beecham Group Plc | Compounds |
| US5451677A (en) | 1993-02-09 | 1995-09-19 | Merck & Co., Inc. | Substituted phenyl sulfonamides as selective β 3 agonists for the treatment of diabetes and obesity |
| IL113084A (en) | 1994-03-23 | 1999-01-26 | Sankyo Co | Thiazolidine and oxazolidine derivatives processes for the preparation thereof and pharmaceutical compositions containing the same |
| US5705515A (en) | 1994-04-26 | 1998-01-06 | Merck & Co., Inc. | Substituted sulfonamides as selective β-3 agonists for the treatment of diabetes and obesity |
| IL113410A (en) | 1994-04-26 | 1999-11-30 | Merck & Co Inc | Substituted sulfonamides having an asymmetric center and pharmaceutical compositions containing them |
| US6075040A (en) * | 1996-09-05 | 2000-06-13 | Eli Lilly And Company | Selective β3 adrenergic agonists |
| ZA967892B (en) * | 1995-09-21 | 1998-03-18 | Lilly Co Eli | Selective β3 adrenergic agonists. |
| CA2257206A1 (en) | 1996-06-07 | 1997-12-11 | Gui-Bai Liang | Oxadiazole benzenesulfonamides as selective .beta.3 agonists for the treatment of diabetes and obesity |
| EP0827746B1 (en) | 1996-09-05 | 2002-04-03 | Eli Lilly And Company | Carbazole analogues as selective beta3 adrenergic agonists |
| KR20000070568A (ko) | 1997-01-28 | 2000-11-25 | 폴락 돈나 엘. | 당뇨병 및 비만 치료를 위한 β3 효능제로서의 티아졸 벤젠설폰아미드 |
| US6011048A (en) * | 1997-01-28 | 2000-01-04 | Merck & Co., Inc. | Thiazole benzenesulfonamides as β3 agonists for treatment of diabetes and obesity |
| AUPP796798A0 (en) | 1998-12-30 | 1999-01-28 | Fujisawa Pharmaceutical Co., Ltd. | New compound |
| JP2003055344A (ja) | 1999-01-29 | 2003-02-26 | Dainippon Pharmaceut Co Ltd | ３，７−ジ置換インドール誘導体及びそれを含有する医薬組成物 |
| WO2001007026A2 (en) | 1999-07-22 | 2001-02-01 | Eli Lilly And Company | Improved method of treating type ii diabetes and obesity |
| WO2001035947A2 (en) | 1999-11-15 | 2001-05-25 | Eli Lilly And Company | Treating wasting syndromes with aryloxy propanolamines |
| AU1580001A (en) * | 1999-11-15 | 2001-05-30 | Eli Lilly And Company | Process for the preparation of aryloxy propanolamines |
| US6420365B1 (en) | 2000-01-18 | 2002-07-16 | Neurogen Corporation | Imidazopyridines and related derivatives as selective modulators of bradykinin B2 receptors |
| ES2398097T3 (es) | 2000-07-13 | 2013-03-13 | Eli Lilly And Company | Agonistas adrenérgicos beta3 |
| EP1341759B1 (en) | 2000-11-10 | 2006-06-14 | Eli Lilly And Company | 3-substituted oxindole beta 3 agonists |
| EP1421078B1 (en) | 2001-08-14 | 2006-09-27 | Eli Lilly And Company | Indole derivatives as beta-3 adrenergic agonists for the treatment of type 2 diabetes |
| AU2002318206A1 (en) | 2001-08-14 | 2003-03-03 | Jolie Anne Bastian | 3-substituted oxindole beta-3 agonists |
-
2002
- 2002-12-24 JP JP2003559510A patent/JP2005520805A/ja active Pending
- 2002-12-24 AU AU2002357084A patent/AU2002357084A1/en not_active Abandoned
- 2002-12-24 EP EP02806449A patent/EP1467733A1/en not_active Withdrawn
- 2002-12-24 WO PCT/US2002/038982 patent/WO2003059348A1/en not_active Ceased
- 2002-12-24 US US10/498,261 patent/US7009060B2/en not_active Expired - Fee Related
-
2005
- 2005-09-16 US US11/228,620 patent/US7214697B2/en not_active Expired - Fee Related
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