JP2014527026A5 - - Google Patents
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- JP2014527026A5 JP2014527026A5 JP2014513258A JP2014513258A JP2014527026A5 JP 2014527026 A5 JP2014527026 A5 JP 2014527026A5 JP 2014513258 A JP2014513258 A JP 2014513258A JP 2014513258 A JP2014513258 A JP 2014513258A JP 2014527026 A5 JP2014527026 A5 JP 2014527026A5
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- JP
- Japan
- Prior art keywords
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- compound
- 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.)
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- 150000001875 compounds Chemical class 0.000 claims description 18
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 5
- PFYXSUNOLOJMDX-UHFFFAOYSA-N bis(2,5-dioxopyrrolidin-1-yl) carbonate Chemical compound O=C1CCC(=O)N1OC(=O)ON1C(=O)CCC1=O PFYXSUNOLOJMDX-UHFFFAOYSA-N 0.000 claims description 4
- -1 prostaglandin amide Chemical class 0.000 claims description 4
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 claims description 2
- CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 claims description 2
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 claims description 2
- OMAHFYGHUQSIEF-UHFFFAOYSA-N bis(2,5-dioxopyrrolidin-1-yl) oxalate Chemical compound O=C1CCC(=O)N1OC(=O)C(=O)ON1C(=O)CCC1=O OMAHFYGHUQSIEF-UHFFFAOYSA-N 0.000 claims description 2
- RAFNCPHFRHZCPS-UHFFFAOYSA-N di(imidazol-1-yl)methanethione Chemical compound C1=CN=CN1C(=S)N1C=CN=C1 RAFNCPHFRHZCPS-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 40
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 23
- 239000002904 solvent Substances 0.000 claims 10
- 125000005843 halogen group Chemical group 0.000 claims 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
- 238000006243 chemical reaction Methods 0.000 claims 7
- 125000002877 alkyl aryl group Chemical group 0.000 claims 6
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 229920006395 saturated elastomer Polymers 0.000 claims 6
- 125000004434 sulfur atom Chemical group 0.000 claims 6
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims 4
- 239000013078 crystal Substances 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- 125000004043 oxo group Chemical group O=* 0.000 claims 4
- 239000003586 protic polar solvent Substances 0.000 claims 4
- 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
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims 3
- 239000003849 aromatic solvent Substances 0.000 claims 3
- AQOKCDNYWBIDND-FTOWTWDKSA-N bimatoprost Chemical compound CCNC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\[C@@H](O)CCC1=CC=CC=C1 AQOKCDNYWBIDND-FTOWTWDKSA-N 0.000 claims 3
- 229960002470 bimatoprost Drugs 0.000 claims 3
- 238000001035 drying Methods 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 239000003880 polar aprotic solvent Substances 0.000 claims 3
- BNGPVKSKKYIJCR-UHFFFAOYSA-N 2-chloro-1,3-dimethylimidazolidine;hydrochloride Chemical compound [Cl-].CN1CC[NH+](C)C1Cl BNGPVKSKKYIJCR-UHFFFAOYSA-N 0.000 claims 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 239000012190 activator Substances 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 238000002425 crystallisation Methods 0.000 claims 2
- 230000008025 crystallization Effects 0.000 claims 2
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims 2
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims 2
- 229940011051 isopropyl acetate Drugs 0.000 claims 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims 2
- 239000000725 suspension Substances 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 claims 1
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims 1
- 238000007239 Wittig reaction Methods 0.000 claims 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 238000004587 chromatography analysis Methods 0.000 claims 1
- 238000000113 differential scanning calorimetry Methods 0.000 claims 1
- 229910001873 dinitrogen Inorganic materials 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 239000004210 ether based solvent Substances 0.000 claims 1
- 230000004927 fusion Effects 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 150000002596 lactones Chemical class 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- 238000005580 one pot reaction Methods 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 238000010626 work up procedure Methods 0.000 claims 1
- XRJVYJWBCXLMGG-LZQGHVKJSA-N CCCCC(CCC/C=C\C[C@@H]([C@H](C[C@H]1O)O)[C@H]1/C=C/[C@H](CCc1ccccc1)O)=O Chemical compound CCCCC(CCC/C=C\C[C@@H]([C@H](C[C@H]1O)O)[C@H]1/C=C/[C@H](CCc1ccccc1)O)=O XRJVYJWBCXLMGG-LZQGHVKJSA-N 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUP1100291 | 2011-06-02 | ||
| HUP1100292 | 2011-06-02 | ||
| HU1100292A HU231134B1 (hu) | 2011-06-02 | 2011-06-02 | Eljárás a bimatoprost kémiailag stabil új kristályformájának előállítására |
| HU1100291A HU230703B1 (hu) | 2011-06-02 | 2011-06-02 | Új eljárás prosztaglandin amidok előállítására |
| PCT/HU2012/000045 WO2012164324A1 (en) | 2011-06-02 | 2012-05-25 | Novel processes for the preparation of prostaglandin amides |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016234694A Division JP6693859B2 (ja) | 2011-06-02 | 2016-12-02 | プロスタグランジンアミドの新規製造方法 |
| JP2016234693A Division JP6487410B2 (ja) | 2011-06-02 | 2016-12-02 | プロスタグランジンアミドの新規製造方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014527026A JP2014527026A (ja) | 2014-10-09 |
| JP2014527026A5 true JP2014527026A5 (enExample) | 2015-03-12 |
| JP6212485B2 JP6212485B2 (ja) | 2017-10-11 |
Family
ID=89990312
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014513258A Active JP6212485B2 (ja) | 2011-06-02 | 2012-05-25 | プロスタグランジンアミドの新規製造方法 |
| JP2016234694A Active JP6693859B2 (ja) | 2011-06-02 | 2016-12-02 | プロスタグランジンアミドの新規製造方法 |
| JP2016234693A Active JP6487410B2 (ja) | 2011-06-02 | 2016-12-02 | プロスタグランジンアミドの新規製造方法 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016234694A Active JP6693859B2 (ja) | 2011-06-02 | 2016-12-02 | プロスタグランジンアミドの新規製造方法 |
| JP2016234693A Active JP6487410B2 (ja) | 2011-06-02 | 2016-12-02 | プロスタグランジンアミドの新規製造方法 |
Country Status (17)
| Country | Link |
|---|---|
| US (3) | US9238621B2 (enExample) |
| EP (1) | EP2723714B1 (enExample) |
| JP (3) | JP6212485B2 (enExample) |
| KR (3) | KR102038048B1 (enExample) |
| CN (4) | CN106316910A (enExample) |
| BR (3) | BR112013030973B1 (enExample) |
| CA (3) | CA3209613A1 (enExample) |
| ES (1) | ES2636756T3 (enExample) |
| HU (1) | HUE033642T2 (enExample) |
| IL (1) | IL229647A (enExample) |
| MX (1) | MX341839B (enExample) |
| PL (1) | PL2723714T3 (enExample) |
| PT (1) | PT2723714T (enExample) |
| RU (1) | RU2618223C2 (enExample) |
| TW (3) | TWI632131B (enExample) |
| WO (1) | WO2012164324A1 (enExample) |
| ZA (1) | ZA201309357B (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU231203B1 (hu) | 2011-12-21 | 2021-10-28 | CHINOIN Gyógyszer és Vegyészeti Termékek Gyára Zrt. | Új eljárás travoprost előállítására |
| CN104884006B (zh) | 2012-10-26 | 2017-12-15 | 弗赛特影像5股份有限公司 | 用于持续释放药物到眼睛的眼科系统 |
| US9120738B2 (en) * | 2012-12-28 | 2015-09-01 | Allergan, Inc. | Crystalline forms of bimatoprost acid, methods for preparation, and methods for use thereof |
| US9447014B2 (en) | 2012-12-28 | 2016-09-20 | Allergan, Inc. | Tromethamine salt of bimatoprost acid in crystalline form, methods for preparation, and methods for use thereof |
| HU231214B1 (hu) * | 2014-03-13 | 2021-11-29 | CHINOIN Gyógyszer és Vegyészeti Termékek Gyára Zrt. | Új eljárás nagytisztaságú prosztaglandinok előállítására |
| US10273206B2 (en) | 2014-06-27 | 2019-04-30 | Allergan, Inc. | Tromethamine salt of bimatoprost acid in crystalline form 1, methods for preparation, and methods for use thereof |
| WO2015199729A1 (en) * | 2014-06-27 | 2015-12-30 | Allergan, Inc. | Tromethamine salt of bimatoprost acid in crystalline form 1, methods for preparation, and methods for use thereof |
| WO2016168141A1 (en) | 2015-04-13 | 2016-10-20 | Forsight Vision5, Inc. | Ocular insert composition of semi-crystalline or crystalline pharmaceutically active agent |
| HU231185B1 (hu) * | 2017-07-11 | 2021-07-28 | CHINOIN Gyógyszer és Vegyészeti Termékek Gyára Zrt. | Eljárás Misoprostol előállítására és tisztítására |
| CN113548993B (zh) * | 2021-09-01 | 2022-05-27 | 河北化工医药职业技术学院 | 一种卡前列素的制备方法 |
Family Cites Families (37)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US3954741A (en) * | 1972-06-07 | 1976-05-04 | Pfizer Inc. | N-substituted prostaglandin carboxamides |
| US3984424A (en) * | 1972-11-08 | 1976-10-05 | Pfizer Inc. | P-biphenyl esters of 15-substituted-ω-pentanorprostaglandins |
| HU171155B (hu) * | 1973-04-30 | 1977-11-28 | Pfizer | Sposob poluchenija oksa-prostaglandinov |
| HU175889B (en) | 1976-04-08 | 1980-11-28 | Chinoin Gyogyszer Es Vegyeszet | New process for preparing lactol-alcohol derivatives |
| HU175217B (hu) * | 1977-08-03 | 1980-06-28 | Chinoin Gyogyszer Es Vegyeszet | Novyj sposob poluchenija biciklicheskikh laktol-metil-ehfirov |
| HU178202B (en) | 1977-09-26 | 1982-03-28 | Chinoin Gyogyszer Es Vegyeszet | Process for preparing new,optically active and racemic bicyclic acetals and merkaptals |
| FR2550799B1 (fr) * | 1983-08-17 | 1986-02-21 | Commissariat Energie Atomique | Compose marque par une enzyme, son procede de preparation et son utilisation en enzymoimmunologie |
| ATE420857T1 (de) * | 1988-09-06 | 2009-01-15 | Pfizer Health Ab | Prostaglandin-derivate zur behandlung von glaukom und ocularer hypertension |
| US5359095A (en) | 1990-08-08 | 1994-10-25 | Pharmacia Ab | Method for synthesis of prostaglandin derivatives |
| SE9002596D0 (sv) * | 1990-08-08 | 1990-08-08 | Pharmacia Ab | A method for synthesis of prostaglandin derivatives |
| GB9025509D0 (en) * | 1990-11-23 | 1991-01-09 | Fujisawa Pharmaceutical Co | New amide derivatives,processes for the preparation thereof and pharmaceutical composition comprising the same |
| HU212570B (en) * | 1991-06-24 | 1996-08-29 | Chinoin Gyogyszer Es Vegyeszet | Process for producing 13,14-dihydro-15(r)-17-phenyl-18,19,20-trinor-pgf2alfa-isopropylester |
| US5409911A (en) | 1992-09-11 | 1995-04-25 | Merck & Co., Inc. | Prostaglandin analog for treating osteoporosis |
| US5352708A (en) | 1992-09-21 | 1994-10-04 | Allergan, Inc. | Non-acidic cyclopentane heptanoic acid, 2-cycloalkyl or arylalkyl derivatives as therapeutic agents |
| JPH10298446A (ja) * | 1997-04-25 | 1998-11-10 | Mitsui Chem Inc | 黄色建染染料の製造方法 |
| US7166730B2 (en) * | 2000-01-27 | 2007-01-23 | Fine Tech Laboratories, Ltd | Process for the preparation of prostaglandin derivatives |
| IL143477A (en) * | 2001-05-31 | 2009-07-20 | Finetech Pharmaceutical Ltd | Process for the preparation of 17-phenyl-18,19,20-trinor-pgf2?? and its derivatives |
| KR100581647B1 (ko) * | 2001-07-17 | 2006-05-22 | 파마시아 앤드 업존 캄파니 엘엘씨 | 라타노프로스트 제조를 위한 방법 및 중간체 |
| DE10226942A1 (de) * | 2002-06-17 | 2003-12-24 | Symrise Gmbh & Co Kg | Verwendung von Mandelsäurealkylamiden als Aromastoffe |
| MXPA05009059A (es) * | 2003-02-26 | 2005-10-19 | Banyu Pharma Co Ltd | Derivados de heteroarilcarbamoilbenceno. |
| GB0329379D0 (en) * | 2003-12-19 | 2004-01-21 | Johnson Matthey Plc | Prostaglandin synthesis |
| FR2889523B1 (fr) * | 2005-08-03 | 2007-12-28 | Servier Lab | Nouvelle forme cristalline v de l'agomelatine, son procede de preparation et les compositions pharmaceutiques qui la contiennent |
| IL177762A0 (en) | 2006-08-29 | 2006-12-31 | Arieh Gutman | Bimatoprost crystalline form i |
| AR071312A1 (es) * | 2008-04-09 | 2010-06-09 | Scinopharm Taiwan Ltd | Proceso para la preparacion de analogos de prostaglandina y sus intermediarios |
| EP2135860A1 (en) * | 2008-06-20 | 2009-12-23 | Sandoz AG | Improved process for the production of bimatoprost |
| GB0819182D0 (en) * | 2008-10-20 | 2008-11-26 | Actelion Pharmaceuticals Ltd | Crystalline forms |
| WO2010096123A2 (en) * | 2008-10-29 | 2010-08-26 | Aerie Pharmaceuticals, Inc. | Amino acid salts of prostaglandins |
| US8722739B2 (en) * | 2008-10-29 | 2014-05-13 | Novaer Holdings, Inc. | Amino acid salts of prostaglandins |
| KR101736169B1 (ko) * | 2009-03-16 | 2017-05-16 | 닛산 가가쿠 고교 가부시키 가이샤 | 저분자 겔화제로 이루어진 스프레이용 기재 |
| US8519178B2 (en) * | 2009-06-22 | 2013-08-27 | Johnson Matthey Public Limited Company | Method for the purification of prostaglandins |
| GB0911000D0 (en) * | 2009-06-25 | 2009-08-12 | Givaudan Sa | Compounds |
| CA2777290C (en) * | 2009-10-16 | 2016-06-28 | Cayman Chemical Company, Incorporated | Process for the preparation of f-series prostaglandins |
| WO2011050638A1 (zh) | 2009-11-02 | 2011-05-05 | 上海天伟生物制药有限公司 | 一种比马前列素晶体及其制备方法和用途 |
| WO2011055377A1 (en) | 2009-11-05 | 2011-05-12 | Biocon Limited | A novel process for the preparation of prostaglandins and intermediates thereof |
| PH12012501098A1 (en) | 2009-11-23 | 2014-10-14 | Allergan Inc | 7-[3,5-dihydroxy-2- (3-hydroxy-5-phenyl-pent-1-enyl)- cyclopentyl]-n-ethyl-hept-5-enamide (bimatoprost) in crystalline form ii, methods for preparation, and methods for use thereof |
| EP2495235B1 (en) * | 2011-03-04 | 2015-08-05 | Newchem S.p.A. | Process for the synthesis of prostaglandins and intermediates thereof |
| HU231203B1 (hu) * | 2011-12-21 | 2021-10-28 | CHINOIN Gyógyszer és Vegyészeti Termékek Gyára Zrt. | Új eljárás travoprost előállítására |
-
2012
- 2012-05-25 PL PL12730027T patent/PL2723714T3/pl unknown
- 2012-05-25 BR BR112013030973-3A patent/BR112013030973B1/pt active IP Right Grant
- 2012-05-25 US US14/123,497 patent/US9238621B2/en active Active
- 2012-05-25 MX MX2013014034A patent/MX341839B/es active IP Right Grant
- 2012-05-25 CA CA3209613A patent/CA3209613A1/en active Pending
- 2012-05-25 CN CN201610603047.6A patent/CN106316910A/zh active Pending
- 2012-05-25 ES ES12730027.5T patent/ES2636756T3/es active Active
- 2012-05-25 KR KR1020147000085A patent/KR102038048B1/ko active Active
- 2012-05-25 CN CN201610657048.9A patent/CN106278982B/zh active Active
- 2012-05-25 JP JP2014513258A patent/JP6212485B2/ja active Active
- 2012-05-25 CN CN201280027006.7A patent/CN103649047B/zh active Active
- 2012-05-25 HU HUE12730027A patent/HUE033642T2/en unknown
- 2012-05-25 CA CA3094762A patent/CA3094762C/en active Active
- 2012-05-25 KR KR1020197031340A patent/KR102135550B1/ko active Active
- 2012-05-25 PT PT127300275T patent/PT2723714T/pt unknown
- 2012-05-25 BR BR122021008946-9A patent/BR122021008946B1/pt active IP Right Grant
- 2012-05-25 WO PCT/HU2012/000045 patent/WO2012164324A1/en not_active Ceased
- 2012-05-25 CA CA2837261A patent/CA2837261C/en active Active
- 2012-05-25 BR BR122021008918-3A patent/BR122021008918B1/pt active IP Right Grant
- 2012-05-25 EP EP12730027.5A patent/EP2723714B1/en active Active
- 2012-05-25 RU RU2013158952A patent/RU2618223C2/ru active
- 2012-05-25 CN CN201610630836.9A patent/CN106349138A/zh active Pending
- 2012-05-25 KR KR1020207019850A patent/KR102277188B1/ko active Active
- 2012-06-01 TW TW101119665A patent/TWI632131B/zh active
- 2012-06-01 TW TW105137756A patent/TWI653223B/zh active
- 2012-06-01 TW TW105137755A patent/TWI653222B/zh active
-
2013
- 2013-11-26 IL IL229647A patent/IL229647A/en active IP Right Grant
- 2013-12-11 ZA ZA2013/09357A patent/ZA201309357B/en unknown
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2015
- 2015-12-10 US US14/965,515 patent/US9856213B2/en active Active
- 2015-12-10 US US14/965,489 patent/US9573892B2/en active Active
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2016
- 2016-12-02 JP JP2016234694A patent/JP6693859B2/ja active Active
- 2016-12-02 JP JP2016234693A patent/JP6487410B2/ja active Active
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