JP2011510029A5 - - Google Patents
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- Publication number
- JP2011510029A5 JP2011510029A5 JP2010543387A JP2010543387A JP2011510029A5 JP 2011510029 A5 JP2011510029 A5 JP 2011510029A5 JP 2010543387 A JP2010543387 A JP 2010543387A JP 2010543387 A JP2010543387 A JP 2010543387A JP 2011510029 A5 JP2011510029 A5 JP 2011510029A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- isoindol
- dihydro
- oxo
- pyridin
- 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
- 150000001875 compounds Chemical class 0.000 claims 37
- 150000003839 salts Chemical class 0.000 claims 28
- 239000000203 mixture Substances 0.000 claims 26
- -1 5-chloro-pyridin-2-yl Chemical group 0.000 claims 13
- 125000004432 carbon atom Chemical group C* 0.000 claims 12
- 239000003814 drug Substances 0.000 claims 12
- 239000002671 adjuvant Substances 0.000 claims 10
- 239000000546 pharmaceutical excipient Substances 0.000 claims 10
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 125000002619 bicyclic group Chemical group 0.000 claims 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 8
- 125000002950 monocyclic group Chemical group 0.000 claims 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 125000004434 sulfur atom Chemical group 0.000 claims 8
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 4
- 150000001408 amides Chemical class 0.000 claims 4
- 235000010290 biphenyl Nutrition 0.000 claims 4
- 239000004305 biphenyl Substances 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 125000001624 naphthyl group Chemical group 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 229920006395 saturated elastomer Polymers 0.000 claims 4
- APRATTNDLORJFG-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-3-(3-oxo-1h-isoindol-2-yl)-n-pyridin-2-ylpropanamide Chemical compound C1=C(OC)C(OC)=CC=C1C(N1C(C2=CC=CC=C2C1)=O)CC(=O)NC1=CC=CC=N1 APRATTNDLORJFG-UHFFFAOYSA-N 0.000 claims 2
- RMUULXHVYNHZBF-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-n-(5-methylpyridin-2-yl)-3-(3-oxo-1h-isoindol-2-yl)propanamide Chemical compound C1=C(OC)C(OC)=CC=C1C(N1C(C2=CC=CC=C2C1)=O)CC(=O)NC1=CC=C(C)C=N1 RMUULXHVYNHZBF-UHFFFAOYSA-N 0.000 claims 2
- OEJXYAKMUUFPMI-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-n-(6-methylpyridin-2-yl)-3-(3-oxo-1h-isoindol-2-yl)propanamide Chemical compound C1=C(OC)C(OC)=CC=C1C(N1C(C2=CC=CC=C2C1)=O)CC(=O)NC1=CC=CC(C)=N1 OEJXYAKMUUFPMI-UHFFFAOYSA-N 0.000 claims 2
- SBVFNYIOAWKDSB-UHFFFAOYSA-N 3-(3-oxo-1h-isoindol-2-yl)-n-(1,3-thiazol-2-yl)-3-(3,4,5-trimethoxyphenyl)propanamide Chemical compound COC1=C(OC)C(OC)=CC(C(CC(=O)NC=2SC=CN=2)N2C(C3=CC=CC=C3C2)=O)=C1 SBVFNYIOAWKDSB-UHFFFAOYSA-N 0.000 claims 2
- DZIWVUSUJHPTIN-UHFFFAOYSA-N 3-(3-oxo-1h-isoindol-2-yl)-n-pyridin-2-yl-3-(3,4,5-trimethoxyphenyl)propanamide Chemical compound COC1=C(OC)C(OC)=CC(C(CC(=O)NC=2N=CC=CC=2)N2C(C3=CC=CC=C3C2)=O)=C1 DZIWVUSUJHPTIN-UHFFFAOYSA-N 0.000 claims 2
- IPSFXCHUNUDSKS-UHFFFAOYSA-N 3-(3-oxo-1h-isoindol-2-yl)-n-pyridin-2-yl-3-thiophen-2-ylpropanamide Chemical compound C=1C=CC=NC=1NC(=O)CC(N1C(C2=CC=CC=C2C1)=O)C1=CC=CS1 IPSFXCHUNUDSKS-UHFFFAOYSA-N 0.000 claims 2
- XRUMTIMHZVQDQA-UHFFFAOYSA-N 3-(4-methoxyphenyl)-3-(3-oxo-1h-isoindol-2-yl)-n-pyridin-2-ylpropanamide Chemical compound C1=CC(OC)=CC=C1C(N1C(C2=CC=CC=C2C1)=O)CC(=O)NC1=CC=CC=N1 XRUMTIMHZVQDQA-UHFFFAOYSA-N 0.000 claims 2
- ITRSBXAOJQVEOW-UHFFFAOYSA-N 3-(4-methoxyphenyl)-n-(4-methylpyridin-2-yl)-3-(3-oxo-1h-isoindol-2-yl)propanamide Chemical compound C1=CC(OC)=CC=C1C(N1C(C2=CC=CC=C2C1)=O)CC(=O)NC1=CC(C)=CC=N1 ITRSBXAOJQVEOW-UHFFFAOYSA-N 0.000 claims 2
- QXIJITNYCCMZDI-UHFFFAOYSA-N 3-(4-methoxyphenyl)-n-(5-methylpyridin-2-yl)-3-(3-oxo-1h-isoindol-2-yl)propanamide Chemical compound C1=CC(OC)=CC=C1C(N1C(C2=CC=CC=C2C1)=O)CC(=O)NC1=CC=C(C)C=N1 QXIJITNYCCMZDI-UHFFFAOYSA-N 0.000 claims 2
- PMYSKYMHOVWMAB-UHFFFAOYSA-N 3-(4-methoxyphenyl)-n-(6-methylpyridin-2-yl)-3-(3-oxo-1h-isoindol-2-yl)propanamide Chemical compound C1=CC(OC)=CC=C1C(N1C(C2=CC=CC=C2C1)=O)CC(=O)NC1=CC=CC(C)=N1 PMYSKYMHOVWMAB-UHFFFAOYSA-N 0.000 claims 2
- 102000030595 Glucokinase Human genes 0.000 claims 2
- 108010021582 Glucokinase Proteins 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 2
- 125000001041 indolyl group Chemical group 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- IBRUVOZFXCYUPN-UHFFFAOYSA-N n-(5-bromopyridin-2-yl)-3-(3,4-dimethoxyphenyl)-3-(3-oxo-1h-isoindol-2-yl)propanamide Chemical compound C1=C(OC)C(OC)=CC=C1C(N1C(C2=CC=CC=C2C1)=O)CC(=O)NC1=CC=C(Br)C=N1 IBRUVOZFXCYUPN-UHFFFAOYSA-N 0.000 claims 2
- BPWWAPBGDABIHH-UHFFFAOYSA-N n-(5-bromopyridin-2-yl)-3-(3-oxo-1h-isoindol-2-yl)-3-(3,4,5-trimethoxyphenyl)propanamide Chemical compound COC1=C(OC)C(OC)=CC(C(CC(=O)NC=2N=CC(Br)=CC=2)N2C(C3=CC=CC=C3C2)=O)=C1 BPWWAPBGDABIHH-UHFFFAOYSA-N 0.000 claims 2
- KTMPTXPTUBHTDC-UHFFFAOYSA-N n-(5-bromopyridin-2-yl)-3-(4-methylphenyl)-3-(3-oxo-1h-isoindol-2-yl)propanamide Chemical compound C1=CC(C)=CC=C1C(N1C(C2=CC=CC=C2C1)=O)CC(=O)NC1=CC=C(Br)C=N1 KTMPTXPTUBHTDC-UHFFFAOYSA-N 0.000 claims 2
- KMDDPCCZBHXPDA-UHFFFAOYSA-N n-(5-chloropyridin-2-yl)-3-(3,4-dimethoxyphenyl)-3-(3-oxo-1h-isoindol-2-yl)propanamide Chemical compound C1=C(OC)C(OC)=CC=C1C(N1C(C2=CC=CC=C2C1)=O)CC(=O)NC1=CC=C(Cl)C=N1 KMDDPCCZBHXPDA-UHFFFAOYSA-N 0.000 claims 2
- HQANKEHGKYKJBR-UHFFFAOYSA-N n-(5-chloropyridin-2-yl)-3-(4-fluorophenyl)-3-(3-oxo-1h-isoindol-2-yl)propanamide Chemical compound C1=CC(F)=CC=C1C(N1C(C2=CC=CC=C2C1)=O)CC(=O)NC1=CC=C(Cl)C=N1 HQANKEHGKYKJBR-UHFFFAOYSA-N 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 125000001425 triazolyl group Chemical group 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000003213 activating effect Effects 0.000 claims 1
- 125000005605 benzo group Chemical group 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 208000017169 kidney disease Diseases 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- STOZBSVDJISXRI-UHFFFAOYSA-N n-(4-methyl-1,3-thiazol-2-yl)-3-(3-oxo-1h-isoindol-2-yl)-3-(3,4,5-trimethoxyphenyl)propanamide Chemical compound COC1=C(OC)C(OC)=CC(C(CC(=O)NC=2SC=C(C)N=2)N2C(C3=CC=CC=C3C2)=O)=C1 STOZBSVDJISXRI-UHFFFAOYSA-N 0.000 claims 1
- CYEJTXYXGQXFTD-UHFFFAOYSA-N n-(5-methylpyridin-2-yl)-3-(3-oxo-1h-isoindol-2-yl)-3-(3,4,5-trimethoxyphenyl)propanamide Chemical compound COC1=C(OC)C(OC)=CC(C(CC(=O)NC=2N=CC(C)=CC=2)N2C(C3=CC=CC=C3C2)=O)=C1 CYEJTXYXGQXFTD-UHFFFAOYSA-N 0.000 claims 1
- BXKIVTINPIYLNI-UHFFFAOYSA-N n-(6-methylpyridin-2-yl)-3-(3-oxo-1h-isoindol-2-yl)-3-(3,4,5-trimethoxyphenyl)propanamide Chemical compound COC1=C(OC)C(OC)=CC(C(CC(=O)NC=2N=C(C)C=CC=2)N2C(C3=CC=CC=C3C2)=O)=C1 BXKIVTINPIYLNI-UHFFFAOYSA-N 0.000 claims 1
- 201000001119 neuropathy Diseases 0.000 claims 1
- 230000007823 neuropathy Effects 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 208000033808 peripheral neuropathy Diseases 0.000 claims 1
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 1
- 208000035408 type 1 diabetes mellitus 1 Diseases 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08001305.5 | 2008-01-24 | ||
| EP08001305 | 2008-01-24 | ||
| PCT/EP2008/011099 WO2009092432A1 (en) | 2008-01-24 | 2008-12-23 | Beta-amino acid derivatives for treatment of diabetes |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011510029A JP2011510029A (ja) | 2011-03-31 |
| JP2011510029A5 true JP2011510029A5 (https=) | 2012-02-16 |
| JP5623914B2 JP5623914B2 (ja) | 2014-11-12 |
Family
ID=40386192
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010543387A Expired - Fee Related JP5623914B2 (ja) | 2008-01-24 | 2008-12-23 | 糖尿病を処置するためのβアミノ酸誘導体 |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US8431602B2 (https=) |
| EP (1) | EP2231640B1 (https=) |
| JP (1) | JP5623914B2 (https=) |
| KR (1) | KR20100110367A (https=) |
| CN (1) | CN101925596B (https=) |
| AR (1) | AR070232A1 (https=) |
| AU (1) | AU2008348817B2 (https=) |
| BR (1) | BRPI0821827A2 (https=) |
| CA (1) | CA2712998A1 (https=) |
| CY (1) | CY1112919T1 (https=) |
| DK (1) | DK2231640T3 (https=) |
| EA (1) | EA017775B1 (https=) |
| ES (1) | ES2388475T3 (https=) |
| HR (1) | HRP20120510T1 (https=) |
| IL (1) | IL206904A0 (https=) |
| MX (1) | MX2010007926A (https=) |
| PL (1) | PL2231640T3 (https=) |
| PT (1) | PT2231640E (https=) |
| SI (1) | SI2231640T1 (https=) |
| WO (1) | WO2009092432A1 (https=) |
| ZA (1) | ZA201006002B (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| EP2760862B1 (en) | 2011-09-27 | 2015-10-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| EP3365334B1 (en) | 2015-10-21 | 2024-07-17 | Otsuka Pharmaceutical Co., Ltd. | Benzolactam compounds as protein kinase inhibitors |
| GB201706327D0 (en) | 2017-04-20 | 2017-06-07 | Otsuka Pharma Co Ltd | A pharmaceutical compound |
| WO2024229228A2 (en) * | 2023-05-02 | 2024-11-07 | The Rockefeller University | 1-oxoisoindolin-2-yl amide activators of vcp and derivatives thereof |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5698579A (en) * | 1993-07-02 | 1997-12-16 | Celgene Corporation | Cyclic amides |
| US6482951B2 (en) | 2000-12-13 | 2002-11-19 | Hoffmann-La Roche Inc. | Isoindolin-1-one glucokinase activators |
| JP2006510606A (ja) * | 2002-10-15 | 2006-03-30 | セルジーン・コーポレーション | 骨髄異形成症候群を治療および管理するための選択的サイトカイン阻害剤の使用方法およびそれを含む組成物 |
| DE60330187D1 (de) * | 2002-12-30 | 2009-12-31 | Celgene Corp | Fluoralkoxy-substituierte 1, 3-dihydro-isoindolyl-verbindungen und ihre pharmazeutischen verwendungen |
| ZA200704251B (en) * | 2004-10-28 | 2008-11-26 | Celgene Corp | Methods and compositions using PDE4 modulators for treatment and management of central nervous injury |
| EP2049518B1 (en) | 2006-05-31 | 2011-08-31 | Takeda San Diego, Inc. | Indazole and isoindole derivatives as glucokinase activating agents. |
-
2008
- 2008-12-23 KR KR1020107018265A patent/KR20100110367A/ko not_active Ceased
- 2008-12-23 WO PCT/EP2008/011099 patent/WO2009092432A1/en not_active Ceased
- 2008-12-23 ES ES08871581T patent/ES2388475T3/es active Active
- 2008-12-23 AU AU2008348817A patent/AU2008348817B2/en not_active Ceased
- 2008-12-23 EP EP08871581A patent/EP2231640B1/en not_active Not-in-force
- 2008-12-23 HR HRP20120510AT patent/HRP20120510T1/hr unknown
- 2008-12-23 CN CN200880125427.7A patent/CN101925596B/zh not_active Expired - Fee Related
- 2008-12-23 DK DK08871581.8T patent/DK2231640T3/da active
- 2008-12-23 PL PL08871581T patent/PL2231640T3/pl unknown
- 2008-12-23 BR BRPI0821827-7A patent/BRPI0821827A2/pt not_active IP Right Cessation
- 2008-12-23 US US12/864,348 patent/US8431602B2/en not_active Expired - Fee Related
- 2008-12-23 PT PT08871581T patent/PT2231640E/pt unknown
- 2008-12-23 JP JP2010543387A patent/JP5623914B2/ja not_active Expired - Fee Related
- 2008-12-23 SI SI200830736T patent/SI2231640T1/sl unknown
- 2008-12-23 CA CA2712998A patent/CA2712998A1/en not_active Abandoned
- 2008-12-23 EA EA201001174A patent/EA017775B1/ru not_active IP Right Cessation
- 2008-12-23 MX MX2010007926A patent/MX2010007926A/es active IP Right Grant
-
2009
- 2009-01-23 AR ARP090100201A patent/AR070232A1/es unknown
-
2010
- 2010-07-08 IL IL206904A patent/IL206904A0/en unknown
- 2010-08-23 ZA ZA2010/06002A patent/ZA201006002B/en unknown
-
2012
- 2012-07-24 CY CY20121100656T patent/CY1112919T1/el unknown
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