JP2011511054A5 - - Google Patents
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- Publication number
- JP2011511054A5 JP2011511054A5 JP2010545563A JP2010545563A JP2011511054A5 JP 2011511054 A5 JP2011511054 A5 JP 2011511054A5 JP 2010545563 A JP2010545563 A JP 2010545563A JP 2010545563 A JP2010545563 A JP 2010545563A JP 2011511054 A5 JP2011511054 A5 JP 2011511054A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- compound
- salts
- formula
- iii
- 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 15
- 238000000034 method Methods 0.000 claims 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 12
- 150000001875 compounds Chemical class 0.000 claims 9
- GJPICJJJRGTNOD-UHFFFAOYSA-N bosentan Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2N=CC=CN=2)OCCO)=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 GJPICJJJRGTNOD-UHFFFAOYSA-N 0.000 claims 8
- 229960003065 bosentan Drugs 0.000 claims 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 6
- 230000006806 disease prevention Effects 0.000 claims 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- 230000002378 acidificating effect Effects 0.000 claims 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 239000002585 base Substances 0.000 claims 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 4
- -1 dichloro compound Chemical class 0.000 claims 4
- 239000003960 organic solvent Substances 0.000 claims 4
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 4
- 229950010765 pivalate Drugs 0.000 claims 4
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 claims 4
- 206010002383 Angina Pectoris Diseases 0.000 claims 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims 3
- 102000010180 Endothelin receptor Human genes 0.000 claims 3
- 108050001739 Endothelin receptor Proteins 0.000 claims 3
- 206010020772 Hypertension Diseases 0.000 claims 3
- 206010047163 Vasospasm Diseases 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 230000002526 effect on cardiovascular system Effects 0.000 claims 3
- 208000028867 ischemia Diseases 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 230000001404 mediated effect Effects 0.000 claims 3
- 125000006239 protecting group Chemical group 0.000 claims 3
- 208000002815 pulmonary hypertension Diseases 0.000 claims 3
- 239000011541 reaction mixture Substances 0.000 claims 3
- 150000003839 salts Chemical group 0.000 claims 3
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 claims 2
- YOYAIZYFCNQIRF-UHFFFAOYSA-N 2,6-dichlorobenzonitrile Chemical compound ClC1=CC=CC(Cl)=C1C#N YOYAIZYFCNQIRF-UHFFFAOYSA-N 0.000 claims 2
- 229960000549 4-dimethylaminophenol Drugs 0.000 claims 2
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 claims 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- 239000008096 xylene Substances 0.000 claims 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 1
- KYDZEZNYRFJCSA-UHFFFAOYSA-N 4-tert-butylbenzenesulfonamide Chemical compound CC(C)(C)C1=CC=C(S(N)(=O)=O)C=C1 KYDZEZNYRFJCSA-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 claims 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical class [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims 1
- 150000001860 citric acid derivatives Chemical class 0.000 claims 1
- 239000013078 crystal Chemical group 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical class OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims 1
- 150000003840 hydrochlorides Chemical class 0.000 claims 1
- 229940049920 malate Drugs 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical class [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 claims 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 claims 1
- 229960001860 salicylate Drugs 0.000 claims 1
- TYFQFVWCELRYAO-UHFFFAOYSA-L suberate(2-) Chemical compound [O-]C(=O)CCCCCCC([O-])=O TYFQFVWCELRYAO-UHFFFAOYSA-L 0.000 claims 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims 1
- 229940095064 tartrate Drugs 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN228/KOL/2008 | 2008-02-08 | ||
| IN228KO2008 | 2008-02-08 | ||
| PCT/GB2009/050120 WO2009098517A1 (en) | 2008-02-08 | 2009-02-06 | Process for preparing bosentan |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011511054A JP2011511054A (ja) | 2011-04-07 |
| JP2011511054A5 true JP2011511054A5 (enExample) | 2012-03-22 |
| JP5683276B2 JP5683276B2 (ja) | 2015-03-11 |
Family
ID=40467334
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010545563A Expired - Fee Related JP5683276B2 (ja) | 2008-02-08 | 2009-02-06 | ボセンタンの製造方法 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8785461B2 (enExample) |
| EP (1) | EP2245018B1 (enExample) |
| JP (1) | JP5683276B2 (enExample) |
| CN (1) | CN101939301B (enExample) |
| AU (1) | AU2009211159B2 (enExample) |
| CA (1) | CA2712860C (enExample) |
| ES (1) | ES2650247T3 (enExample) |
| NZ (1) | NZ587793A (enExample) |
| PT (1) | PT2245018T (enExample) |
| WO (1) | WO2009098517A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2694242C (en) | 2007-06-29 | 2013-10-01 | Generics [Uk] Limited | Process for introduction of hydroxyethoxy side chain in bosentan |
| US8530488B2 (en) | 2007-10-24 | 2013-09-10 | Generics [Uk] Limited | Crystalline forms of bosentan |
| NZ593117A (en) | 2008-11-03 | 2013-03-28 | Generics Uk Ltd | HPLC METHOD FOR THE ANALYSIS OF BOSENTAN AND RELATED SUBSTANCES AND USE OF THESE SUBSTANCES AS REFERENCE STANDARDS AND MARKERS Chromatography mass spectrometry fragmentation |
| WO2013098577A1 (en) * | 2011-12-31 | 2013-07-04 | Abdi Ibrahim Ilac Sanayi Ve Ticaret Anonim Sirketi | Pharmaceutical compositions of bosentan |
| CN104487057A (zh) * | 2012-05-11 | 2015-04-01 | 韩诺生物制药株式会社 | 波生坦控释口服制剂 |
| CN112457259B (zh) * | 2020-12-08 | 2024-02-20 | 重庆康乐制药有限公司 | 一种磺胺多辛的制备方法 |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2086544C1 (ru) * | 1991-06-13 | 1997-08-10 | Хоффманн-Ля Рош АГ | Бензолсульфонамидные производные пиримидина или их соли, фармацевтическая композиция для лечения заболеваний, связанных с активностью эндотелина |
| US5739333A (en) * | 1995-05-16 | 1998-04-14 | Tanabe Seiyaku Co., Ltd. | Sulfonamide derivative and process for preparing the same |
| US6136971A (en) * | 1998-07-17 | 2000-10-24 | Roche Colorado Corporation | Preparation of sulfonamides |
| SI1535613T1 (sl) | 1999-11-17 | 2010-12-31 | Teva Pharma | Postopek za pripravo polimorfne oblike atorvastatin kalcija |
| CN1411373A (zh) | 1999-12-16 | 2003-04-16 | 特瓦制药工业有限公司 | 制备来氟米特的新方法和新晶形的来氟米特 |
| ES2255973T3 (es) | 2000-01-25 | 2006-07-16 | F. Hoffmann-La Roche Ag | Preparacion de sulfonamidas. |
| US6479692B1 (en) | 2001-05-02 | 2002-11-12 | Nobex Corporation | Methods of synthesizing acylanilides including bicalutamide and derivatives thereof |
| AU2003209669A1 (en) | 2003-02-25 | 2004-09-17 | Hetero Drugs Limited | Amorphous form of losartan potassium |
| EP1603920A1 (en) | 2003-03-12 | 2005-12-14 | Cadila Healthcare Ltd. | Polymorph and amorphous form of (s)-(+)-clopidogrel bisulfate |
| AU2003230195A1 (en) | 2003-04-02 | 2004-10-25 | Hetero Drugs Limited | A novel process for amorphous form of donepezil hydrochloride |
| PL1883397T3 (pl) | 2005-05-17 | 2010-05-31 | Actelion Pharmaceuticals Ltd | Dyspergowalna tabletka bosertanu |
| US20080188663A1 (en) | 2007-01-29 | 2008-08-07 | Ashok Kumar | Process for the preparation of crystalline clopidogrel hydrogen sulphate Form I |
| WO2008122020A1 (en) | 2007-04-02 | 2008-10-09 | Auspex Pharmaceuticals, Inc. | Substituted pyrimidines |
| CA2686457A1 (en) | 2007-05-08 | 2008-11-13 | Generics [Uk] Limited | Novel polymorphic forms |
| CA2694242C (en) | 2007-06-29 | 2013-10-01 | Generics [Uk] Limited | Process for introduction of hydroxyethoxy side chain in bosentan |
| WO2009047637A1 (en) | 2007-10-11 | 2009-04-16 | Actavis Group Ptc Ehf | Novel polymorphs of bosentan |
| US8530488B2 (en) | 2007-10-24 | 2013-09-10 | Generics [Uk] Limited | Crystalline forms of bosentan |
| ATE530531T1 (de) * | 2007-12-18 | 2011-11-15 | Dipharma Francis Srl | Verfahren zur herstellung von bosentan |
| WO2009095933A2 (en) | 2008-01-10 | 2009-08-06 | Msn Laboratories Limited | Improved and novel process for the preparation of bosentan |
| WO2009093127A2 (en) | 2008-01-24 | 2009-07-30 | Actavis Group Ptc Ehf | Substantially pure and a stable crystalline form of bosentan |
| EP2268634A2 (en) | 2008-03-13 | 2011-01-05 | Actavis Group PTC EHF | Processes for the preparation of bosentan and related compounds using novel intermediates |
| EP2294056A1 (en) * | 2008-05-23 | 2011-03-16 | Synthon B.V. | Bosentan salts |
| NZ593117A (en) | 2008-11-03 | 2013-03-28 | Generics Uk Ltd | HPLC METHOD FOR THE ANALYSIS OF BOSENTAN AND RELATED SUBSTANCES AND USE OF THESE SUBSTANCES AS REFERENCE STANDARDS AND MARKERS Chromatography mass spectrometry fragmentation |
| IT1393136B1 (it) | 2009-03-11 | 2012-04-11 | Sifa Vitor S R L | Procedimento per la preparazione del bosentan |
-
2009
- 2009-02-06 AU AU2009211159A patent/AU2009211159B2/en not_active Ceased
- 2009-02-06 NZ NZ587793A patent/NZ587793A/en not_active IP Right Cessation
- 2009-02-06 JP JP2010545563A patent/JP5683276B2/ja not_active Expired - Fee Related
- 2009-02-06 PT PT97092829T patent/PT2245018T/pt unknown
- 2009-02-06 US US12/866,373 patent/US8785461B2/en active Active
- 2009-02-06 CN CN200980104551.XA patent/CN101939301B/zh not_active Expired - Fee Related
- 2009-02-06 CA CA2712860A patent/CA2712860C/en not_active Expired - Fee Related
- 2009-02-06 EP EP09709282.9A patent/EP2245018B1/en not_active Not-in-force
- 2009-02-06 ES ES09709282.9T patent/ES2650247T3/es active Active
- 2009-02-06 WO PCT/GB2009/050120 patent/WO2009098517A1/en not_active Ceased
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