JP2013525355A5 - - Google Patents
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- JP2013525355A5 JP2013525355A5 JP2013506202A JP2013506202A JP2013525355A5 JP 2013525355 A5 JP2013525355 A5 JP 2013525355A5 JP 2013506202 A JP2013506202 A JP 2013506202A JP 2013506202 A JP2013506202 A JP 2013506202A JP 2013525355 A5 JP2013525355 A5 JP 2013525355A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- optionally substituted
- alkyl
- halo
- 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
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- 150000001875 compounds Chemical class 0.000 claims description 98
- 238000000034 method Methods 0.000 claims description 68
- 125000005843 halogen group Chemical group 0.000 claims description 41
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 125000003545 alkoxy group Chemical group 0.000 claims description 25
- 125000001931 aliphatic group Chemical group 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
- 239000007818 Grignard reagent Substances 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- 150000004795 grignard reagents Chemical class 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 5
- 230000002140 halogenating effect Effects 0.000 claims description 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 claims description 4
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- LVKCSZQWLOVUGB-UHFFFAOYSA-M magnesium;propane;bromide Chemical compound [Mg+2].[Br-].C[CH-]C LVKCSZQWLOVUGB-UHFFFAOYSA-M 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 0 C*CC(O1)=C(N)OC1=O Chemical compound C*CC(O1)=C(N)OC1=O 0.000 description 81
- 239000001301 oxygen Substances 0.000 description 5
- DXSTXHWCNNXUIA-UHFFFAOYSA-N IN1CCSCC1 Chemical compound IN1CCSCC1 DXSTXHWCNNXUIA-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N c1ccncc1 Chemical compound c1ccncc1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- JGYHLKLMZWAYKN-UHFFFAOYSA-N CCc(cc1)cnc1C(CCl)=O Chemical compound CCc(cc1)cnc1C(CCl)=O JGYHLKLMZWAYKN-UHFFFAOYSA-N 0.000 description 3
- VWQYWKZKOVZIHE-UHFFFAOYSA-O C1C[NH2+]CSCC1 Chemical compound C1C[NH2+]CSCC1 VWQYWKZKOVZIHE-UHFFFAOYSA-O 0.000 description 2
- IMYCCGJUZBTONO-UHFFFAOYSA-N C=NN1CCCCC1 Chemical compound C=NN1CCCCC1 IMYCCGJUZBTONO-UHFFFAOYSA-N 0.000 description 2
- BXVAVXHPXVAUBU-UHFFFAOYSA-N CC(C)N1CCCCCC1 Chemical compound CC(C)N1CCCCCC1 BXVAVXHPXVAUBU-UHFFFAOYSA-N 0.000 description 2
- MFEIKQPHQINPRI-UHFFFAOYSA-N CCc1cccnc1 Chemical compound CCc1cccnc1 MFEIKQPHQINPRI-UHFFFAOYSA-N 0.000 description 2
- AVFZOVWCLRSYKC-UHFFFAOYSA-N CN1CCCC1 Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 2
- ZKUKXSWKWGHYKJ-UHFFFAOYSA-N CN1CCCCCC1 Chemical compound CN1CCCCCC1 ZKUKXSWKWGHYKJ-UHFFFAOYSA-N 0.000 description 2
- YPIYCXORPTWOIL-UHFFFAOYSA-N C[IH]N(c1c2cccc1)NN2O Chemical compound C[IH]N(c1c2cccc1)NN2O YPIYCXORPTWOIL-UHFFFAOYSA-N 0.000 description 2
- GWWMVGUEIDAXCB-UHFFFAOYSA-N C[N](C)(Nc1c2cccc1)N2O Chemical compound C[N](C)(Nc1c2cccc1)N2O GWWMVGUEIDAXCB-UHFFFAOYSA-N 0.000 description 2
- WIFJIKIOKWYURB-UHFFFAOYSA-N C[N]1(C)CCOCCC1 Chemical compound C[N]1(C)CCOCCC1 WIFJIKIOKWYURB-UHFFFAOYSA-N 0.000 description 2
- GAUKKFMRLMOULV-UHFFFAOYSA-N IN1CCCCC1 Chemical compound IN1CCCCC1 GAUKKFMRLMOULV-UHFFFAOYSA-N 0.000 description 2
- SPGPGBWICPNRSN-UHFFFAOYSA-N I[n]1cncc1 Chemical compound I[n]1cncc1 SPGPGBWICPNRSN-UHFFFAOYSA-N 0.000 description 2
- ZMMMAYLQQKMTBL-UHFFFAOYSA-N Oc1ccc(C=C2C=CC=C2)cc1 Chemical compound Oc1ccc(C=C2C=CC=C2)cc1 ZMMMAYLQQKMTBL-UHFFFAOYSA-N 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 2
- 125000004437 phosphorous atom Chemical group 0.000 description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 125000005415 substituted alkoxy group Chemical group 0.000 description 2
- QJEYNOFYGNLVFE-UHFFFAOYSA-O C=C(C(Cc(cc1)ccc1O)C([OH2+])=N1)C1=O Chemical compound C=C(C(Cc(cc1)ccc1O)C([OH2+])=N1)C1=O QJEYNOFYGNLVFE-UHFFFAOYSA-O 0.000 description 1
- WPOQSCFRWAQPKI-UHFFFAOYSA-N CC(N(C(C(Cc(cc1)ccc1O)S1)=O)C1=O)=O Chemical compound CC(N(C(C(Cc(cc1)ccc1O)S1)=O)C1=O)=O WPOQSCFRWAQPKI-UHFFFAOYSA-N 0.000 description 1
- HSPXULVKHRXNQE-UHFFFAOYSA-N CCC(N(C(C(Cc(cc1)ccc1O)S1)=O)C1=O)=O Chemical compound CCC(N(C(C(Cc(cc1)ccc1O)S1)=O)C1=O)=O HSPXULVKHRXNQE-UHFFFAOYSA-N 0.000 description 1
- PDUYDKDSVCFLEV-UHFFFAOYSA-N CC[IH]N1CCOCC1 Chemical compound CC[IH]N1CCOCC1 PDUYDKDSVCFLEV-UHFFFAOYSA-N 0.000 description 1
- JMNFLHLUKPBOQV-UHFFFAOYSA-N COCC(O1)=C(N)OC1=O Chemical compound COCC(O1)=C(N)OC1=O JMNFLHLUKPBOQV-UHFFFAOYSA-N 0.000 description 1
- RGHHSNMVTDWUBI-UHFFFAOYSA-N Oc1ccc(C=O)cc1 Chemical compound Oc1ccc(C=O)cc1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 1
- CUJIDZLHNDCTQL-UHFFFAOYSA-N Oc1ccc(CC(C(N2C(Oc3ccccc3)=O)=O)SC2=O)cc1 Chemical compound Oc1ccc(CC(C(N2C(Oc3ccccc3)=O)=O)SC2=O)cc1 CUJIDZLHNDCTQL-UHFFFAOYSA-N 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N c1ccccc1 Chemical compound c1ccccc1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- -1 methoxy, ethoxy Chemical group 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32550210P | 2010-04-19 | 2010-04-19 | |
| US61/325,502 | 2010-04-19 | ||
| US32749810P | 2010-04-23 | 2010-04-23 | |
| US61/327,498 | 2010-04-23 | ||
| PCT/US2011/032822 WO2011133442A1 (en) | 2010-04-19 | 2011-04-18 | Novel synthesis for thiazolidinedione compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2013525355A JP2013525355A (ja) | 2013-06-20 |
| JP2013525355A5 true JP2013525355A5 (enExample) | 2014-04-24 |
Family
ID=44148625
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013506202A Pending JP2013525355A (ja) | 2010-04-19 | 2011-04-18 | チアゾリジンジオン化合物の新規合成 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US8937182B2 (enExample) |
| EP (1) | EP2560956B1 (enExample) |
| JP (1) | JP2013525355A (enExample) |
| KR (1) | KR101781665B1 (enExample) |
| CN (1) | CN102947269B (enExample) |
| AU (1) | AU2011242956B2 (enExample) |
| CA (1) | CA2796437C (enExample) |
| DK (1) | DK2560956T3 (enExample) |
| ES (1) | ES2610623T3 (enExample) |
| HU (1) | HUE030263T2 (enExample) |
| MX (1) | MX2012012092A (enExample) |
| NZ (1) | NZ602883A (enExample) |
| PL (1) | PL2560956T3 (enExample) |
| RU (1) | RU2012148908A (enExample) |
| WO (1) | WO2011133442A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2585066B1 (en) * | 2010-06-24 | 2018-09-26 | Alkermes Pharma Ireland Limited | Prodrugs of nh-acidic compounds: ester, carbonate, carbamate and phosphonate derivatives |
| HUE031424T2 (en) | 2010-08-10 | 2017-07-28 | Octeta Therapeutics Llc | New synthesis of thiazolidinedione compounds |
| HUE029488T2 (en) | 2010-08-10 | 2017-02-28 | Metabolic Solutions Dev Co Llc | Synthesis of Thiazolidinedione Compounds |
| US12084472B2 (en) | 2015-12-18 | 2024-09-10 | Ardelyx, Inc. | Substituted 4-phenyl pyridine compounds as non-systemic TGR5 agonists |
| TWI773657B (zh) | 2015-12-18 | 2022-08-11 | 美商亞德利克斯公司 | 作爲非全身ｔｇｒ５促效劑之經取代之4-苯基吡啶化合物 |
| US20210038566A1 (en) | 2018-02-08 | 2021-02-11 | Enyo Pharma | Use of modulators of neet proteins for the treatment of infection |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1003445B (zh) | 1984-10-03 | 1989-03-01 | 武田药品工业株式会社 | 噻唑烷二酮衍生物，其制备方法和用途 |
| US5143930A (en) | 1990-02-07 | 1992-09-01 | Sankyo Company, Limited | Thiazolidine derivatives with anti-diabetic activity, their preparation and their use |
| CA2106967C (en) * | 1991-04-11 | 2003-12-09 | Takashi Sohda | Thiazolidinedione derivatives, production and use thereof |
| NO302471B1 (no) * | 1991-12-26 | 1998-03-09 | Sankyo Co | Tiazolidinforbindelser og farmasöytisk preparat |
| JPH07188227A (ja) * | 1993-12-24 | 1995-07-25 | Japan Tobacco Inc | チアゾリジン誘導体及びオキサゾール誘導体 |
| SE9702305D0 (sv) | 1997-06-17 | 1997-06-17 | Astra Ab | New thiazolidinedione, oxazolidinedione and oxadiazolidinedione derivatives |
| AP869A (en) * | 1998-01-05 | 2000-09-04 | Pfizer | 2,3-Substituted indole compounds as anti-inflammatory and analgesic agents. |
| US7407978B2 (en) | 1999-04-06 | 2008-08-05 | Theracos, Inc. | Heterocyclic analogs of diphenylethylene compounds |
| US6768008B2 (en) * | 2000-04-24 | 2004-07-27 | Aryx Therapeutics | Materials and methods for the treatment of diabetes, hyperlipidemia, hypercholesterolemia, and atherosclerosis |
| FR2817144B1 (fr) | 2000-11-29 | 2003-01-03 | Micro Mega Sa | Sequence d'instruments canalaires pour l'execution d'un protocole operatoire d'endodontie |
| WO2003029251A1 (en) * | 2001-09-28 | 2003-04-10 | Biocon Limited | Novel process for the synthesis of thiazolidinedione derivatives |
| FR2861069B1 (fr) | 2003-10-17 | 2005-12-09 | Galderma Res & Dev | NOUVEAUX LIGANDS ACTIVATEURS DES RECEPTEURS RARs, UTILISATION EN MEDECINE HUMAINE AINSI QU'EN COSMETIQUE |
| JP5149271B2 (ja) | 2006-03-16 | 2013-02-20 | メタボリック ソリューションズ ディベロップメント カンパニー， エルエルシー | 高血圧症を処置するためならびに脂質を下げるためのチアゾリジンジオン類似体 |
| CA2646170A1 (en) | 2006-03-16 | 2007-09-27 | Metabolic Solutions Development Company | Combination therapies of thiazolidinedione analogues and glucocorticoid agonists |
| RU2445957C2 (ru) | 2006-03-16 | 2012-03-27 | Метаболик Солюшнз Девелопмент Компани | Аналоги тиазолидиндиона |
| EP2098517B1 (en) * | 2006-12-01 | 2013-12-18 | Msd K.K. | Novel phenyl-isoxazol-3-ol derivative |
| US8435983B2 (en) * | 2007-03-23 | 2013-05-07 | The University Of Toledo | Conformationally restrained epothilone analogues as anti-leukemic agents |
| AU2008301905B2 (en) | 2007-09-14 | 2013-06-27 | Cirius Therapeutics, Inc. | Thiazolidinedione analogues for the treatment of hypertension |
| WO2009148195A1 (en) * | 2008-06-02 | 2009-12-10 | Daebong Ls, Ltd. | 5-(4-hydroxybenzyl)thiazolidine-2,4-dione as intermediate for synthesis of thiazolidinedione based compounds and process for preparing the same |
| CN103153972A (zh) | 2010-04-19 | 2013-06-12 | 新陈代谢解决方案开发公司 | 噻唑烷二酮化合物的新的合成方法 |
| HUE029488T2 (en) | 2010-08-10 | 2017-02-28 | Metabolic Solutions Dev Co Llc | Synthesis of Thiazolidinedione Compounds |
| HUE031424T2 (en) | 2010-08-10 | 2017-07-28 | Octeta Therapeutics Llc | New synthesis of thiazolidinedione compounds |
-
2011
- 2011-04-18 MX MX2012012092A patent/MX2012012092A/es active IP Right Grant
- 2011-04-18 KR KR1020127030070A patent/KR101781665B1/ko not_active Expired - Fee Related
- 2011-04-18 CN CN201180030253.8A patent/CN102947269B/zh not_active Expired - Fee Related
- 2011-04-18 PL PL11716155T patent/PL2560956T3/pl unknown
- 2011-04-18 ES ES11716155.4T patent/ES2610623T3/es active Active
- 2011-04-18 NZ NZ602883A patent/NZ602883A/en not_active IP Right Cessation
- 2011-04-18 RU RU2012148908/04A patent/RU2012148908A/ru not_active Application Discontinuation
- 2011-04-18 CA CA2796437A patent/CA2796437C/en active Active
- 2011-04-18 AU AU2011242956A patent/AU2011242956B2/en not_active Ceased
- 2011-04-18 DK DK11716155.4T patent/DK2560956T3/en active
- 2011-04-18 US US13/641,917 patent/US8937182B2/en active Active
- 2011-04-18 EP EP11716155.4A patent/EP2560956B1/en active Active
- 2011-04-18 WO PCT/US2011/032822 patent/WO2011133442A1/en not_active Ceased
- 2011-04-18 HU HUE11716155A patent/HUE030263T2/en unknown
- 2011-04-18 JP JP2013506202A patent/JP2013525355A/ja active Pending
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