JP2010502715A5 - - Google Patents
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- Publication number
- JP2010502715A5 JP2010502715A5 JP2009527430A JP2009527430A JP2010502715A5 JP 2010502715 A5 JP2010502715 A5 JP 2010502715A5 JP 2009527430 A JP2009527430 A JP 2009527430A JP 2009527430 A JP2009527430 A JP 2009527430A JP 2010502715 A5 JP2010502715 A5 JP 2010502715A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- butanol
- tert
- pharmaceutically acceptable
- acceptable salt
- 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
- 238000000034 method Methods 0.000 claims 24
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical group CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 7
- 230000007062 hydrolysis Effects 0.000 claims 5
- 238000006460 hydrolysis reaction Methods 0.000 claims 5
- 239000003960 organic solvent Substances 0.000 claims 5
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 239000000543 intermediate Substances 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- RAAGZOYMEQDCTD-UHFFFAOYSA-N 2-fluorobenzoyl chloride Chemical group FC1=CC=CC=C1C(Cl)=O RAAGZOYMEQDCTD-UHFFFAOYSA-N 0.000 claims 3
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 230000010933 acylation Effects 0.000 claims 3
- 238000005917 acylation reaction Methods 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- -1 halobenzoyl chloride Chemical compound 0.000 claims 3
- RAMPDACRJWTXEV-UHFFFAOYSA-N methyl 2-cyanobenzoate Chemical compound COC(=O)C1=CC=CC=C1C#N RAMPDACRJWTXEV-UHFFFAOYSA-N 0.000 claims 3
- 150000004702 methyl esters Chemical class 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- SNGNHEIIYFNIIL-UHFFFAOYSA-N benzoic acid;1,2,4-oxadiazole Chemical compound C=1N=CON=1.OC(=O)C1=CC=CC=C1 SNGNHEIIYFNIIL-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- XJKKCLQTZOSEDY-UHFFFAOYSA-N cyano benzoate Chemical compound N#COC(=O)C1=CC=CC=C1 XJKKCLQTZOSEDY-UHFFFAOYSA-N 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 claims 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims 1
- 229940011051 isopropyl acetate Drugs 0.000 claims 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 claims 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 0 N#Cc1cc(*I)ccc1 Chemical compound N#Cc1cc(*I)ccc1 0.000 description 2
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US84359506P | 2006-09-08 | 2006-09-08 | |
| US60/843,595 | 2006-09-08 | ||
| PCT/US2007/019561 WO2008030570A1 (en) | 2006-09-08 | 2007-09-06 | Processes for the preparation of 1,2,4-oxadiazole benzoic acids |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014103966A Division JP2014193896A (ja) | 2006-09-08 | 2014-05-20 | １，２，４−オキサジアゾール安息香酸の製造方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010502715A JP2010502715A (ja) | 2010-01-28 |
| JP2010502715A5 true JP2010502715A5 (enExample) | 2010-10-21 |
| JP5955494B2 JP5955494B2 (ja) | 2016-07-20 |
Family
ID=38935880
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009527430A Active JP5955494B2 (ja) | 2006-09-08 | 2007-09-06 | １，２，４−オキサジアゾール安息香酸の製造方法 |
| JP2014103966A Pending JP2014193896A (ja) | 2006-09-08 | 2014-05-20 | １，２，４−オキサジアゾール安息香酸の製造方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014103966A Pending JP2014193896A (ja) | 2006-09-08 | 2014-05-20 | １，２，４−オキサジアゾール安息香酸の製造方法 |
Country Status (24)
| Country | Link |
|---|---|
| US (2) | US7678922B2 (enExample) |
| EP (1) | EP2059513B1 (enExample) |
| JP (2) | JP5955494B2 (enExample) |
| KR (1) | KR101466368B1 (enExample) |
| CN (1) | CN101535284B (enExample) |
| AR (3) | AR062715A1 (enExample) |
| AU (1) | AU2007292915B2 (enExample) |
| BR (1) | BRPI0716996B8 (enExample) |
| CA (2) | CA2842625C (enExample) |
| CL (1) | CL2007002606A1 (enExample) |
| DK (1) | DK2059513T3 (enExample) |
| ES (1) | ES2404348T3 (enExample) |
| IL (1) | IL197445A (enExample) |
| MX (1) | MX2009002439A (enExample) |
| MY (1) | MY148598A (enExample) |
| NZ (2) | NZ575511A (enExample) |
| PE (2) | PE20080771A1 (enExample) |
| PL (1) | PL2059513T3 (enExample) |
| PT (1) | PT2059513E (enExample) |
| RU (1) | RU2495030C2 (enExample) |
| TW (1) | TWI482761B (enExample) |
| UA (1) | UA99265C2 (enExample) |
| WO (1) | WO2008030570A1 (enExample) |
| ZA (1) | ZA200901782B (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK3549936T3 (da) | 2003-04-11 | 2021-07-12 | Ptc Therapeutics Inc | 1,2,4-oxadiazol-benzoesyreforbindelse og dens anvendelse til nonsense-undertrykkelse og behandlingen af sygdom |
| ES2683359T3 (es) | 2005-04-08 | 2018-09-26 | Ptc Therapeutics, Inc. | Composiciones que comprenden un 1,2,4-oxadiazol y usos de las mismas para tratar enfermedades asociadas con un codón de parada prematura |
| RU2462246C2 (ru) * | 2006-03-30 | 2012-09-27 | ПиТиСи ТЕРАПЬЮТИКС, ИНК. | Способы получения функционального белка из днк, имеющей нонсенс-мутацию, и лечения нарушений, ассоциированных с ней |
| MX2009002439A (es) * | 2006-09-08 | 2009-03-27 | Ptc Therapeutics Inc | Procesos para la preparacion de acidos 1,2,4-oxadiazolbenzoicos. |
| EP2068871B1 (en) | 2006-09-25 | 2013-12-25 | PTC Therapeutics, Inc. | Hydroxylated 1,2,4-oxadiazole benzoic acid compounds, compositions thereof and the use for nonsense suppression |
| PL2076501T3 (pl) | 2006-09-25 | 2016-06-30 | Ptc Therapeutics Inc | Postacie krystaliczne kwasu 3-[5-(2-fluorofenylo)[1,2,4]oksadiazol-3-ilo]-benzoesowego |
| ES2538359T3 (es) | 2006-10-12 | 2015-06-19 | Ptc Therapeutics, Inc. | Métodos para administrar un 1,2,4-oxadiazol activo por vía oral para terapia de supresión de mutación sin sentido |
| CN101714009A (zh) * | 2009-05-14 | 2010-05-26 | 翁印嵩 | 集成通用电话功能的计算机 |
| WO2012101292A1 (es) | 2011-01-25 | 2012-08-02 | Viviabiotech, S.L. | Derivados de 1,2,4-oxadiazol como fármacos moduladores del receptor para el péptido glp-1 |
| AU2013286860B2 (en) | 2012-07-02 | 2017-10-26 | Monsanto Technology Llc | Processes for the preparation of 3,5-disubstituted-1,2,4-oxadiazoles |
| CA3174516A1 (en) | 2014-03-06 | 2015-09-11 | Ptc Therapeutics, Inc. | Pharmaceutical compositions and salts of a 1,2,4-oxadiazole benzoic acid |
| CN105461650B (zh) * | 2014-09-12 | 2018-04-13 | 杭州普晒医药科技有限公司 | 一种噁二唑化合物的溶剂化物及其制备方法 |
| CN106316885B (zh) * | 2015-07-03 | 2019-02-12 | 普济生物科技（台州）有限公司 | 一种3-[5-(2-氟苯基)-1,2,4-噁二唑-3-基]苯甲酸的制备方法 |
| TW201729807A (zh) | 2015-10-30 | 2017-09-01 | Ｐｔｃ治療公司 | 用於治療癲癇的方法 |
| TW201808922A (zh) | 2016-06-20 | 2018-03-16 | 台灣神隆股份有限公司 | 製備阿塔魯仁及其中間體的方法 |
| WO2020128816A2 (en) | 2018-12-20 | 2020-06-25 | Pfizer Inc. | Pharmaceutical compositions and methods comprising a combination of a benzoxazole transthyretin stabilizer and an additional therapeutic agent |
| MX2021012428A (es) | 2019-04-10 | 2022-01-19 | Ptc Therapeutics Inc | Metodo para el tratamiento de distrofia muscular de duchenne mediada por mutacion sin sentido en pacientes pediatricos. |
| WO2022112919A1 (en) | 2020-11-25 | 2022-06-02 | Pfizer Inc. | (aza)benzothiazolyl substituted pyrazole compounds |
| CN113045510B (zh) * | 2021-03-31 | 2022-05-27 | 北京大学生命科学华东产业研究院 | 一种阿塔鲁伦的制备方法 |
| CN114920667B (zh) * | 2022-06-30 | 2024-06-21 | 湖南大学 | 一种阿塔鲁伦酯的电化学制备方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2801509A1 (de) * | 1978-01-12 | 1979-07-19 | Schering Ag | 1,2,4-oxadiazolderivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltende selektive herbizide mittel |
| DE3905242A1 (de) * | 1989-02-21 | 1990-08-23 | Basf Ag | Verfahren zur herstellung von phenyloxdiazolylanilinen |
| NZ234760A (en) * | 1989-08-18 | 1991-09-25 | Sterling Drug Inc | Antiviral oxazole compounds and compositions |
| DE4425794A1 (de) * | 1994-07-21 | 1996-01-25 | Basf Ag | Nitrofarbstoffe |
| US6660753B2 (en) | 1999-08-19 | 2003-12-09 | Nps Pharmaceuticals, Inc. | Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists |
| CN1638776A (zh) | 2001-06-08 | 2005-07-13 | 西托维亚公司 | 取代的3－芳基－5－芳基－[1,2,4]－噁二唑和类似物 |
| MY151199A (en) | 2001-11-02 | 2014-04-30 | Rigel Pharmaceuticals Inc | Substituted diphenyl heterocycles useful for treating hcv infection |
| TW200812986A (en) | 2002-08-09 | 2008-03-16 | Nps Pharma Inc | New compounds |
| GB0303503D0 (en) | 2003-02-14 | 2003-03-19 | Novartis Ag | Organic compounds |
| DK3549936T3 (da) | 2003-04-11 | 2021-07-12 | Ptc Therapeutics Inc | 1,2,4-oxadiazol-benzoesyreforbindelse og dens anvendelse til nonsense-undertrykkelse og behandlingen af sygdom |
| US20050075375A1 (en) | 2003-05-14 | 2005-04-07 | Anadys Pharmaceuticals, Inc. | Heterocyclic compounds for treating hepatitis C virus |
| ES2683359T3 (es) | 2005-04-08 | 2018-09-26 | Ptc Therapeutics, Inc. | Composiciones que comprenden un 1,2,4-oxadiazol y usos de las mismas para tratar enfermedades asociadas con un codón de parada prematura |
| MX2009002439A (es) * | 2006-09-08 | 2009-03-27 | Ptc Therapeutics Inc | Procesos para la preparacion de acidos 1,2,4-oxadiazolbenzoicos. |
-
2007
- 2007-09-06 MX MX2009002439A patent/MX2009002439A/es active IP Right Grant
- 2007-09-06 JP JP2009527430A patent/JP5955494B2/ja active Active
- 2007-09-06 KR KR1020097007202A patent/KR101466368B1/ko not_active Expired - Fee Related
- 2007-09-06 RU RU2009113019/04A patent/RU2495030C2/ru active
- 2007-09-06 CA CA2842625A patent/CA2842625C/en active Active
- 2007-09-06 NZ NZ575511A patent/NZ575511A/en unknown
- 2007-09-06 PT PT78378999T patent/PT2059513E/pt unknown
- 2007-09-06 PL PL07837899T patent/PL2059513T3/pl unknown
- 2007-09-06 MY MYPI20090941A patent/MY148598A/en unknown
- 2007-09-06 EP EP07837899A patent/EP2059513B1/en active Active
- 2007-09-06 ZA ZA200901782A patent/ZA200901782B/xx unknown
- 2007-09-06 ES ES07837899T patent/ES2404348T3/es active Active
- 2007-09-06 AU AU2007292915A patent/AU2007292915B2/en active Active
- 2007-09-06 WO PCT/US2007/019561 patent/WO2008030570A1/en not_active Ceased
- 2007-09-06 DK DK07837899.9T patent/DK2059513T3/da active
- 2007-09-06 US US11/899,813 patent/US7678922B2/en active Active - Reinstated
- 2007-09-06 UA UAA200903350A patent/UA99265C2/ru unknown
- 2007-09-06 NZ NZ598012A patent/NZ598012A/xx unknown
- 2007-09-06 CN CN200780041169.XA patent/CN101535284B/zh active Active
- 2007-09-06 BR BRPI0716996A patent/BRPI0716996B8/pt active IP Right Grant
- 2007-09-06 CA CA2662749A patent/CA2662749C/en active Active
- 2007-09-07 PE PE2007001203A patent/PE20080771A1/es active IP Right Grant
- 2007-09-07 TW TW096133607A patent/TWI482761B/zh active
- 2007-09-07 PE PE2011001405A patent/PE20120669A1/es active IP Right Grant
- 2007-09-07 AR ARP070103975A patent/AR062715A1/es not_active Application Discontinuation
- 2007-09-07 CL CL200702606A patent/CL2007002606A1/es unknown
-
2009
- 2009-03-05 IL IL197445A patent/IL197445A/en active IP Right Grant
- 2009-11-13 US US12/617,757 patent/US8367841B2/en active Active
-
2014
- 2014-05-20 JP JP2014103966A patent/JP2014193896A/ja active Pending
-
2017
- 2017-01-27 AR ARP170100223A patent/AR107474A2/es not_active Application Discontinuation
-
2020
- 2020-05-12 AR ARP200101362A patent/AR118922A2/es unknown
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