JP2011520915A5 - - Google Patents
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- Publication number
- JP2011520915A5 JP2011520915A5 JP2011509762A JP2011509762A JP2011520915A5 JP 2011520915 A5 JP2011520915 A5 JP 2011520915A5 JP 2011509762 A JP2011509762 A JP 2011509762A JP 2011509762 A JP2011509762 A JP 2011509762A JP 2011520915 A5 JP2011520915 A5 JP 2011520915A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- pyran
- tetrahydro
- cyclopropylsulfonyl
- propanamide
- 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 aryl (C 1-10 ) alkyl Chemical group 0.000 claims description 283
- 150000001875 compounds Chemical class 0.000 claims description 35
- HAMZIZRSAJARRH-UHFFFAOYSA-N 4-cyclopropylsulfonyl-1-[1-[(5-fluoro-1,3-thiazol-2-yl)amino]-3-(oxan-4-yl)-1-oxopropan-2-yl]indazole-6-carboxylic acid Chemical compound C12=CC(C(=O)O)=CC(S(=O)(=O)C3CC3)=C2C=NN1C(C(=O)NC=1SC(F)=CN=1)CC1CCOCC1 HAMZIZRSAJARRH-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 132
- 125000005842 heteroatom Chemical group 0.000 claims 102
- 125000000753 cycloalkyl group Chemical group 0.000 claims 60
- 125000003118 aryl group Chemical group 0.000 claims 38
- 150000001602 bicycloalkyls Chemical group 0.000 claims 29
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 25
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 25
- 229910052739 hydrogen Inorganic materials 0.000 claims 23
- 239000001257 hydrogen Substances 0.000 claims 23
- 125000004104 aryloxy group Chemical group 0.000 claims 22
- 150000002431 hydrogen Chemical class 0.000 claims 21
- 125000001072 heteroaryl group Chemical group 0.000 claims 20
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 17
- 125000003282 alkyl amino group Chemical group 0.000 claims 16
- 125000005843 halogen group Chemical group 0.000 claims 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 16
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 12
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 12
- 239000003814 drug Substances 0.000 claims 11
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 11
- 238000004519 manufacturing process Methods 0.000 claims 10
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 9
- 229940124530 sulfonamide Drugs 0.000 claims 9
- 150000003456 sulfonamides Chemical class 0.000 claims 9
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 8
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims 8
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 7
- 150000001408 amides Chemical class 0.000 claims 7
- 125000005188 oxoalkyl group Chemical group 0.000 claims 7
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims 7
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 150000003857 carboxamides Chemical class 0.000 claims 2
- KUFXUEYIWPFSHN-HNNXBMFYSA-N (2s)-2-(4-cyclopropylsulfonylpyrazolo[3,4-c]pyridin-1-yl)-n-(5-fluoro-1,3-thiazol-2-yl)-3-(oxan-4-yl)propanamide Chemical compound S1C(F)=CN=C1NC(=O)[C@@H](N1C2=CN=CC(=C2C=N1)S(=O)(=O)C1CC1)CC1CCOCC1 KUFXUEYIWPFSHN-HNNXBMFYSA-N 0.000 claims 1
- QAVCBIQSDBRVDD-UHFFFAOYSA-N 4-chloro-1-[1-[(5-chloro-1,3-thiazol-2-yl)amino]-3-(oxan-4-yl)-1-oxopropan-2-yl]-n-cyclopropylpyrazole-3-carboxamide Chemical compound S1C(Cl)=CN=C1NC(=O)C(N1N=C(C(Cl)=C1)C(=O)NC1CC1)CC1CCOCC1 QAVCBIQSDBRVDD-UHFFFAOYSA-N 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 208000032928 Dyslipidaemia Diseases 0.000 claims 1
- 102000030595 Glucokinase Human genes 0.000 claims 1
- 108010021582 Glucokinase Proteins 0.000 claims 1
- 208000002705 Glucose Intolerance Diseases 0.000 claims 1
- 206010022489 Insulin Resistance Diseases 0.000 claims 1
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 1
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 201000010390 abdominal obesity-metabolic syndrome 1 Diseases 0.000 claims 1
- 230000003213 activating effect Effects 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000004691 alkyl thio carbonyl group Chemical group 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 201000001421 hyperglycemia Diseases 0.000 claims 1
- 125000004536 indazol-1-yl group Chemical group N1(N=CC2=CC=CC=C12)* 0.000 claims 1
- 208000011661 metabolic syndrome X Diseases 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- NPMMXKUVLURCMA-UHFFFAOYSA-N n-(oxan-4-yl)propanamide Chemical compound CCC(=O)NC1CCOCC1 NPMMXKUVLURCMA-UHFFFAOYSA-N 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 201000010065 polycystic ovary syndrome Diseases 0.000 claims 1
- 201000009104 prediabetes syndrome Diseases 0.000 claims 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- SORGEQQSQGNZFI-UHFFFAOYSA-N [azido(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(N=[N+]=[N-])OC1=CC=CC=C1 SORGEQQSQGNZFI-UHFFFAOYSA-N 0.000 description 1
- KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 description 1
- 229940126208 compound 22 Drugs 0.000 description 1
- 229940125833 compound 23 Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5405208P | 2008-05-16 | 2008-05-16 | |
| US61/054,052 | 2008-05-16 | ||
| US10837008P | 2008-10-24 | 2008-10-24 | |
| US61/108,370 | 2008-10-24 | ||
| PCT/US2009/044190 WO2009140624A2 (en) | 2008-05-16 | 2009-05-15 | Glucokinase activators |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011520915A JP2011520915A (ja) | 2011-07-21 |
| JP2011520915A5 true JP2011520915A5 (OSRAM) | 2012-07-12 |
| JP5513492B2 JP5513492B2 (ja) | 2014-06-04 |
Family
ID=41076813
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011509762A Expired - Fee Related JP5513492B2 (ja) | 2008-05-16 | 2009-05-15 | グルコキナーゼ活性剤 |
Country Status (27)
| Country | Link |
|---|---|
| US (4) | US8563730B2 (OSRAM) |
| EP (1) | EP2294053B1 (OSRAM) |
| JP (1) | JP5513492B2 (OSRAM) |
| KR (1) | KR20110018366A (OSRAM) |
| CN (1) | CN102105451B (OSRAM) |
| AR (1) | AR071811A1 (OSRAM) |
| AU (1) | AU2009246167B2 (OSRAM) |
| BR (1) | BRPI0912802A2 (OSRAM) |
| CA (1) | CA2724116A1 (OSRAM) |
| CL (1) | CL2009001203A1 (OSRAM) |
| CO (1) | CO6321274A2 (OSRAM) |
| CR (1) | CR11827A (OSRAM) |
| DO (1) | DOP2010000351A (OSRAM) |
| EA (1) | EA018988B1 (OSRAM) |
| EC (1) | ECSP10010688A (OSRAM) |
| GE (1) | GEP20135783B (OSRAM) |
| IL (1) | IL209062A (OSRAM) |
| MA (1) | MA32391B1 (OSRAM) |
| MX (1) | MX2010012298A (OSRAM) |
| MY (1) | MY152749A (OSRAM) |
| NZ (1) | NZ589084A (OSRAM) |
| PE (2) | PE20091901A1 (OSRAM) |
| SG (1) | SG190625A1 (OSRAM) |
| TW (1) | TWI445707B (OSRAM) |
| UY (1) | UY31830A (OSRAM) |
| WO (1) | WO2009140624A2 (OSRAM) |
| ZA (1) | ZA201007975B (OSRAM) |
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| AR068063A1 (es) | 2007-08-27 | 2009-11-04 | Basf Plant Science Gmbh | Co mpuestos de pirazol para controlar plagas de invertebrados |
| AU2009210641A1 (en) * | 2008-02-05 | 2009-08-13 | Merck Sharp & Dohme Corp. | Pharmaceutical compositions of a combination of metformin and a dipeptidyl peptidase-IV inhibitor |
| US8563730B2 (en) | 2008-05-16 | 2013-10-22 | Takeda San Diego, Inc. | Pyrazole and fused pyrazole glucokinase activators |
| US8592597B2 (en) | 2008-08-27 | 2013-11-26 | Takeda Pharmaceutical Company Limited | Pyrrole compounds |
| PE20110303A1 (es) * | 2008-09-11 | 2011-05-21 | Pfizer | Derivados de heteroaril acetamidas como activadores de glucoquinasa |
| AU2009295936B2 (en) | 2008-09-24 | 2014-07-17 | Basf Se | Pyrazole compounds for controlling invertebrate pests |
| CN102471330A (zh) | 2009-07-06 | 2012-05-23 | 巴斯夫欧洲公司 | 用于防治无脊椎动物害虫的哒嗪化合物 |
| CN102471321A (zh) | 2009-07-06 | 2012-05-23 | 巴斯夫欧洲公司 | 用于防治无脊椎动物害虫的哒嗪化合物 |
| EP2456308A2 (en) | 2009-07-24 | 2012-05-30 | Basf Se | Pyridine derivatives for controlling invertrebate pests |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP3199623B1 (en) | 2010-03-31 | 2021-07-28 | The Scripps Research Institute | Reprogramming cells |
| KR101878252B1 (ko) * | 2010-05-26 | 2018-07-13 | 브이티브이 테라퓨틱스 엘엘씨 | 글루코키나아제 활성화제와 병용되는 메트포르민의 용도, 및 메트포르민과 글루코키나아제 활성화제를 포함하는 조성물 |
| 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 |
| 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 |
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| EP2627654A1 (en) * | 2010-10-13 | 2013-08-21 | Takeda California, Inc. | Method of making azaindazole derivatives |
| 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 |
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| CN118453592A (zh) | 2012-05-17 | 2024-08-09 | Vtv治疗有限责任公司 | 用于治疗糖尿病的葡萄糖激酶活化剂组合物 |
| AU2014226290B2 (en) * | 2013-03-04 | 2018-11-15 | Vtv Therapeutics Llc | Stable glucokinase activator compositions |
| EP2878339A1 (en) | 2013-12-02 | 2015-06-03 | Siena Biotech S.p.A. | SIP3 antagonists |
| TWI667233B (zh) | 2013-12-19 | 2019-08-01 | 德商拜耳製藥公司 | 新穎吲唑羧醯胺，其製備方法、含彼等之醫藥製劑及其製造醫藥之用途 |
| DK3372585T3 (da) * | 2014-12-19 | 2022-05-30 | Aragon Pharmaceuticals Inc | Fremgangsmåde til fremstillingen af en diarylthiohydantoinforbindelse |
| CN105092770B (zh) * | 2015-01-12 | 2017-03-29 | 上海中医药大学 | 一种筛选二肽基肽酶四抑制剂的方法 |
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| HRP20202011T1 (hr) | 2015-06-15 | 2021-04-02 | Syngenta Crop Protection Ag | Halogen-supstituirani fenoksifenilamidini i njihova upotreba kao fungicidi |
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| GB201714777D0 (en) | 2017-09-14 | 2017-11-01 | Univ London Queen Mary | Agent |
| CN114209694A (zh) | 2018-05-31 | 2022-03-22 | 华领医药技术（上海）有限公司 | 含有葡萄糖激酶激活剂和ppar受体激活剂的药物组合及其制备方法和用途 |
| WO2019241089A1 (en) | 2018-06-12 | 2019-12-19 | Vtv Therapeutics Llc | Therapeutic uses of glucokinase activators in combination with insulin or insulin analogs |
| WO2021167840A1 (en) | 2020-02-18 | 2021-08-26 | Vtv Therapeutics Llc | Sulfoxide and sulfone glucokinase activators and methods of use thereof |
| CA3181722A1 (en) | 2020-06-08 | 2021-12-16 | Jing TENG | Salts or co-crystals of {2-[3-cyclohexyl-3-(trans-4-propoxy-cyclohexyl)-ureido]-thiazol-5-ylsulfanyl}-acetic acid and uses thereof |
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2009
- 2009-05-15 US US12/467,041 patent/US8563730B2/en not_active Expired - Fee Related
- 2009-05-15 KR KR20107028256A patent/KR20110018366A/ko not_active Ceased
- 2009-05-15 CL CL2009001203A patent/CL2009001203A1/es unknown
- 2009-05-15 PE PE2009000690A patent/PE20091901A1/es not_active Application Discontinuation
- 2009-05-15 CN CN2009801273588A patent/CN102105451B/zh not_active Expired - Fee Related
- 2009-05-15 SG SG2013034012A patent/SG190625A1/en unknown
- 2009-05-15 WO PCT/US2009/044190 patent/WO2009140624A2/en not_active Ceased
- 2009-05-15 MY MYPI20105245 patent/MY152749A/en unknown
- 2009-05-15 JP JP2011509762A patent/JP5513492B2/ja not_active Expired - Fee Related
- 2009-05-15 CA CA 2724116 patent/CA2724116A1/en not_active Abandoned
- 2009-05-15 NZ NZ589084A patent/NZ589084A/en not_active IP Right Cessation
- 2009-05-15 TW TW98116300A patent/TWI445707B/zh not_active IP Right Cessation
- 2009-05-15 UY UY31830A patent/UY31830A/es not_active Application Discontinuation
- 2009-05-15 GE GEAP2009012029 patent/GEP20135783B/en unknown
- 2009-05-15 MX MX2010012298A patent/MX2010012298A/es active IP Right Grant
- 2009-05-15 AR ARP090101763 patent/AR071811A1/es unknown
- 2009-05-15 AU AU2009246167A patent/AU2009246167B2/en not_active Ceased
- 2009-05-15 PE PE2014000756A patent/PE20141375A1/es not_active Application Discontinuation
- 2009-05-15 EP EP09747705.3A patent/EP2294053B1/en not_active Not-in-force
- 2009-05-15 EA EA201071320A patent/EA018988B1/ru not_active IP Right Cessation
- 2009-05-15 BR BRPI0912802A patent/BRPI0912802A2/pt not_active IP Right Cessation
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2010
- 2010-11-01 IL IL209062A patent/IL209062A/en not_active IP Right Cessation
- 2010-11-08 ZA ZA2010/07975A patent/ZA201007975B/en unknown
- 2010-11-15 DO DO2010000351A patent/DOP2010000351A/es unknown
- 2010-12-07 CO CO10154094A patent/CO6321274A2/es not_active Application Discontinuation
- 2010-12-07 CR CR11827A patent/CR11827A/es unknown
- 2010-12-10 MA MA33420A patent/MA32391B1/fr unknown
- 2010-12-16 EC ECSP10010688 patent/ECSP10010688A/es unknown
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2012
- 2012-04-10 US US13/443,774 patent/US20120225887A1/en not_active Abandoned
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2013
- 2013-10-02 US US14/044,687 patent/US9139598B2/en not_active Expired - Fee Related
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2015
- 2015-09-21 US US14/860,573 patent/US20160009735A1/en not_active Abandoned
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