JP2015110607A5 - - Google Patents
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- Publication number
- JP2015110607A5 JP2015110607A5 JP2015003265A JP2015003265A JP2015110607A5 JP 2015110607 A5 JP2015110607 A5 JP 2015110607A5 JP 2015003265 A JP2015003265 A JP 2015003265A JP 2015003265 A JP2015003265 A JP 2015003265A JP 2015110607 A5 JP2015110607 A5 JP 2015110607A5
- Authority
- JP
- Japan
- Prior art keywords
- oxadiazol
- fluorophenyl
- benzoic acid
- water
- crystallizing
- 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
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 8
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 8
- OOUGLTULBSNHNF-UHFFFAOYSA-N 3-[5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC(C=2N=C(ON=2)C=2C(=CC=CC=2)F)=C1 OOUGLTULBSNHNF-UHFFFAOYSA-N 0.000 claims description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 6
- 238000001704 evaporation Methods 0.000 claims description 6
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 5
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 5
- 230000008020 evaporation Effects 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 4
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 15
- 239000013078 crystal Substances 0.000 claims 14
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- OFXSXYCSPVKZPF-UHFFFAOYSA-N methoxyperoxymethane Chemical compound COOOC OFXSXYCSPVKZPF-UHFFFAOYSA-N 0.000 claims 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims 2
- 235000019439 ethyl acetate Nutrition 0.000 claims 2
- 238000001757 thermogravimetry curve Methods 0.000 claims 2
- 239000005711 Benzoic acid Substances 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- 238000000113 differential scanning calorimetry Methods 0.000 claims 1
- 238000010438 heat treatment 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
- 230000005855 radiation Effects 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- 238000004090 dissolution Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US84732606P | 2006-09-25 | 2006-09-25 | |
| US60/847,326 | 2006-09-25 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009529270A Division JP5714228B2 (ja) | 2006-09-25 | 2007-09-24 | ３−［５−（２−フルオロフェニル）−［１，２，４］オキサジアゾール−３−イル］−安息香酸の結晶形 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017106030A Division JP6495375B2 (ja) | 2006-09-25 | 2017-05-29 | ３−［５−（２−フルオロフェニル）−［１，２，４］オキサジアゾール−３−イル］−安息香酸の結晶形 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015110607A JP2015110607A (ja) | 2015-06-18 |
| JP2015110607A5 true JP2015110607A5 (https=) | 2017-07-27 |
| JP6407733B2 JP6407733B2 (ja) | 2018-10-17 |
Family
ID=39123850
Family Applications (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009529270A Active JP5714228B2 (ja) | 2006-09-25 | 2007-09-24 | ３−［５−（２−フルオロフェニル）−［１，２，４］オキサジアゾール−３−イル］−安息香酸の結晶形 |
| JP2015003265A Active JP6407733B2 (ja) | 2006-09-25 | 2015-01-09 | ３−［５−（２−フルオロフェニル）−［１，２，４］オキサジアゾール−３−イル］−安息香酸の結晶形 |
| JP2017106030A Active JP6495375B2 (ja) | 2006-09-25 | 2017-05-29 | ３−［５−（２−フルオロフェニル）−［１，２，４］オキサジアゾール−３−イル］−安息香酸の結晶形 |
| JP2019040137A Withdrawn JP2019104752A (ja) | 2006-09-25 | 2019-03-06 | ３−［５−（２−フルオロフェニル）−［１，２，４］オキサジアゾール−３−イル］−安息香酸の結晶形 |
| JP2021090763A Active JP7245868B2 (ja) | 2006-09-25 | 2021-05-31 | ３－［５－（２－フルオロフェニル）－［１，２，４］オキサジアゾール－３－イル］－安息香酸の結晶形 |
| JP2023038770A Pending JP2023078271A (ja) | 2006-09-25 | 2023-03-13 | ３－［５－（２－フルオロフェニル）－［１，２，４］オキサジアゾール－３－イル］－安息香酸の結晶形 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009529270A Active JP5714228B2 (ja) | 2006-09-25 | 2007-09-24 | ３−［５−（２−フルオロフェニル）−［１，２，４］オキサジアゾール−３−イル］−安息香酸の結晶形 |
Family Applications After (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017106030A Active JP6495375B2 (ja) | 2006-09-25 | 2017-05-29 | ３−［５−（２−フルオロフェニル）−［１，２，４］オキサジアゾール−３−イル］−安息香酸の結晶形 |
| JP2019040137A Withdrawn JP2019104752A (ja) | 2006-09-25 | 2019-03-06 | ３−［５−（２−フルオロフェニル）−［１，２，４］オキサジアゾール−３−イル］−安息香酸の結晶形 |
| JP2021090763A Active JP7245868B2 (ja) | 2006-09-25 | 2021-05-31 | ３－［５－（２－フルオロフェニル）－［１，２，４］オキサジアゾール－３－イル］－安息香酸の結晶形 |
| JP2023038770A Pending JP2023078271A (ja) | 2006-09-25 | 2023-03-13 | ３－［５－（２－フルオロフェニル）－［１，２，４］オキサジアゾール－３－イル］－安息香酸の結晶形 |
Country Status (29)
| Country | Link |
|---|---|
| US (10) | US7863456B2 (https=) |
| EP (2) | EP2076501B8 (https=) |
| JP (6) | JP5714228B2 (https=) |
| KR (1) | KR101430144B1 (https=) |
| CN (3) | CN104341371A (https=) |
| AR (2) | AR062963A1 (https=) |
| AU (1) | AU2007300542B2 (https=) |
| BR (1) | BRPI0717107A2 (https=) |
| CA (1) | CA2663574C (https=) |
| CL (1) | CL2007002743A1 (https=) |
| DK (1) | DK2076501T3 (https=) |
| ES (2) | ES2655338T3 (https=) |
| HK (1) | HK1207070A1 (https=) |
| HU (1) | HUE028503T2 (https=) |
| IL (1) | IL197717A (https=) |
| LT (1) | LTC2076501I2 (https=) |
| MX (2) | MX344418B (https=) |
| MY (1) | MY191209A (https=) |
| NO (1) | NO341858B1 (https=) |
| NZ (1) | NZ575795A (https=) |
| PE (3) | PE20151445A1 (https=) |
| PL (2) | PL2076501T3 (https=) |
| PT (1) | PT2076501E (https=) |
| SG (2) | SG185979A1 (https=) |
| SI (1) | SI2076501T1 (https=) |
| TW (2) | TWI452038B (https=) |
| UA (1) | UA99600C2 (https=) |
| WO (1) | WO2008039431A2 (https=) |
| ZA (1) | ZA200901949B (https=) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUE047569T2 (hu) | 2003-04-11 | 2020-04-28 | Ptc Therapeutics Inc | 1,2,4-oxadiazol-benzoesav vegyület és nonszensz szupresszióra történõ alkalmazása |
| PT2402002T (pt) * | 2005-04-08 | 2018-10-08 | Ptc Therapeutics Inc | Composições de 1,2,4-oxadiazole oralmente activo para terapia de supressão de mutações nonsense |
| 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 |
| 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 |
| RS54025B1 (sr) | 2006-10-12 | 2015-10-30 | Ptc Therapeutics Inc. | Postupci doziranja oralno aktivnog 1,2,4-oksadiazola za supresionu terapiju nonsens mutacije |
| KR101713453B1 (ko) | 2010-03-12 | 2017-03-07 | 오메로스 코포레이션 | Pde10 억제제 및 관련 조성물 및 방법 |
| WO2014153643A1 (en) * | 2013-03-26 | 2014-10-02 | The University Of British Columbia | Compositions and methods for use thereof in the treatment of aniridia |
| US9347014B2 (en) | 2013-04-03 | 2016-05-24 | Gfo Oil Llc | Methods and systems for generating aldehydes from organic seed oils |
| HUE038169T2 (hu) | 2013-09-06 | 2018-09-28 | Aurigene Discovery Tech Ltd | 1,2,4-Oxadiazol származékok mint immunomodulátorok |
| KR102497273B1 (ko) | 2014-03-06 | 2023-02-07 | 피티씨 테라퓨틱스, 인크. | 1,2,4-옥사디아졸 벤조산의 약학 조성물 및 염 |
| NZ716494A (en) | 2014-04-28 | 2017-07-28 | Omeros Corp | Processes and intermediates for the preparation of a pde10 inhibitor |
| NZ630803A (en) * | 2014-04-28 | 2016-03-31 | Omeros Corp | Optically active pde10 inhibitor |
| KR101703137B1 (ko) | 2014-05-30 | 2017-02-07 | 선문대학교 산학협력단 | 당 부가 아미노글리코사이드 화합물, 이의 제조방법 및 이를 유효성분으로 함유하는 약학적 조성물 |
| 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 |
| KR102894264B1 (ko) | 2015-03-10 | 2025-12-02 | 오리진 온콜로지 리미티드 | 면역조절제로서의 1,2,4-옥사다이아졸 및 티아다이아졸 화합물 |
| KR20170139074A (ko) | 2015-04-24 | 2017-12-18 | 오메로스 코포레이션 | Pde10 억제제 및 관련 조성물 및 방법 |
| JP2018531975A (ja) | 2015-10-30 | 2018-11-01 | ピーティーシー セラピューティクス，インコーポレーテッド | てんかんの治療方法 |
| WO2017079678A1 (en) | 2015-11-04 | 2017-05-11 | Omeros Corporation | Solid state forms of a pde10 inhibitor |
| EP3442512A4 (en) * | 2016-04-15 | 2020-07-22 | The UAB Research Foundation | METHODS AND COMPOUNDS FOR STIMULATING THE TRANSLECTURE OF PREMATURE TERMINATION CODONS |
| WO2018050706A1 (en) * | 2016-09-13 | 2018-03-22 | Marco Cipolli | Method of treatment of shwachman-diamond syndrome |
| WO2019061324A1 (en) * | 2017-09-29 | 2019-04-04 | Curis Inc. | CRYSTALLINE FORMS OF IMMUNOMODULATORS |
| EP3694841A1 (en) | 2017-10-11 | 2020-08-19 | Aurigene Discovery Technologies Limited | Crystalline forms of 3-substituted 1,2,4-oxadiazole |
| MY206121A (en) | 2017-11-03 | 2024-11-29 | Aurigene Discovery Tech Ltd | Dual inhibitors of tim-3 and pd-1 pathways |
| AU2018360389B2 (en) | 2017-11-06 | 2024-09-19 | Aurigene Oncology Limited | Conjoint therapies for immunomodulation |
| EP3952867A4 (en) | 2019-04-10 | 2023-01-11 | PTC Therapeutics, Inc. | METHODS OF TREATMENT OF NONSENSE MUTATION MEDIATED DUCHENNE MUSCULAR DYSTROPHY IN PEDIATRIC PATIENTS |
| JP7339900B2 (ja) * | 2020-02-26 | 2023-09-06 | 新 井上 | 視野異常診断方法、視野異常診断装置 |
| KR102665711B1 (ko) * | 2021-12-21 | 2024-05-14 | 재단법인 아산사회복지재단 | Ras 활성도를 이용한 신경섬유종증 치료제에 대한 감수성 예측용 바이오마커 조성물 및 Ras 활성 억제제를 포함하는 신경섬유종증 예방 또는 치료용 약학적 조성물 |
| WO2025110781A1 (ko) * | 2023-11-24 | 2025-05-30 | 재단법인 아산사회복지재단 | Ampd3를 포함하는 신경섬유종증 치료제에 대한 감수성 예측용 바이오마커 조성물 및 ampd3 저해제를 포함하는 신경섬유종증 예방 또는 치료용 약학 조성물 |
| CN118178408A (zh) * | 2024-03-22 | 2024-06-14 | 核工业总医院 | Ptc124在制备治疗血小板无力症的药物中的应用 |
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| TW264475B (https=) | 1991-09-20 | 1995-12-01 | Takeda Pharm Industry Co Ltd | |
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| JP2005504014A (ja) * | 2001-06-08 | 2005-02-10 | サイトビア インコーポレイテッド | カスパーゼの活性化因子およびアポトーシスの誘導因子としての置換された３−アリール−５−アリール−［１，２，４］−オキサジアゾール類および類似体、並びにその使用法 |
| MY151199A (en) * | 2001-11-02 | 2014-04-30 | Rigel Pharmaceuticals Inc | Substituted diphenyl heterocycles useful for treating hcv infection |
| AU2003247610A1 (en) * | 2002-06-21 | 2004-01-06 | Ptc Therapeutics, Inc. | METHODS FOR IDENTIFYING SMALL MOLECULES THAT MODULATE PREMATURE TRANSLATION TERMINATION AND NONSENSE MEDIATED mRNA DECAY |
| US8374966B1 (en) * | 2002-08-01 | 2013-02-12 | Oracle International Corporation | In memory streaming with disk backup and recovery of messages captured from a database redo stream |
| TW200424183A (en) * | 2002-08-09 | 2004-11-16 | Nps Pharma Inc | New compounds |
| GB0303503D0 (en) * | 2003-02-14 | 2003-03-19 | Novartis Ag | Organic compounds |
| US7135575B2 (en) * | 2003-03-03 | 2006-11-14 | Array Biopharma, Inc. | P38 inhibitors and methods of use thereof |
| HUE047569T2 (hu) * | 2003-04-11 | 2020-04-28 | Ptc Therapeutics Inc | 1,2,4-oxadiazol-benzoesav vegyület és nonszensz szupresszióra történõ alkalmazása |
| WO2004110351A2 (en) * | 2003-05-14 | 2004-12-23 | Anadys Pharmaceuticals, Inc. | Heterocyclic compounds for treating hepatitis c virus |
| EP2402323A3 (en) * | 2004-10-13 | 2012-05-30 | PTC Therapeutics, Inc. | Pyrazole or triazole compounds and their use for the manufacture of a medicament for treating somatic mutation-related diseases |
| JP2008523090A (ja) * | 2004-12-08 | 2008-07-03 | バイオマリン ファーマシューティカル インコーポレイテッド | 新生児肺高血圧症の治療のための方法および組成物 |
| PT2402002T (pt) | 2005-04-08 | 2018-10-08 | Ptc Therapeutics Inc | Composições de 1,2,4-oxadiazole oralmente activo para terapia de supressão de mutações nonsense |
| MX2009002439A (es) | 2006-09-08 | 2009-03-27 | Ptc Therapeutics Inc | Procesos para la preparacion de acidos 1,2,4-oxadiazolbenzoicos. |
| 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 |
| KR102497273B1 (ko) * | 2014-03-06 | 2023-02-07 | 피티씨 테라퓨틱스, 인크. | 1,2,4-옥사디아졸 벤조산의 약학 조성물 및 염 |
-
2007
- 2007-09-24 PL PL07838770T patent/PL2076501T3/pl unknown
- 2007-09-24 KR KR1020097008202A patent/KR101430144B1/ko active Active
- 2007-09-24 MX MX2011007120A patent/MX344418B/es unknown
- 2007-09-24 EP EP07838770.1A patent/EP2076501B8/en active Active
- 2007-09-24 SG SG2012082715A patent/SG185979A1/en unknown
- 2007-09-24 SG SG10201609581TA patent/SG10201609581TA/en unknown
- 2007-09-24 HU HUE07838770A patent/HUE028503T2/en unknown
- 2007-09-24 PT PT78387701T patent/PT2076501E/pt unknown
- 2007-09-24 MX MX2009003160A patent/MX2009003160A/es active IP Right Grant
- 2007-09-24 AU AU2007300542A patent/AU2007300542B2/en active Active
- 2007-09-24 CN CN201410561812.3A patent/CN104341371A/zh active Pending
- 2007-09-24 ES ES12185448.3T patent/ES2655338T3/es active Active
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