ZA200510221B - Process for preparing isomerically pure prodrugs of proton pump inhibitors - Google Patents
Process for preparing isomerically pure prodrugs of proton pump inhibitors Download PDFInfo
- Publication number
- ZA200510221B ZA200510221B ZA200510221A ZA200510221A ZA200510221B ZA 200510221 B ZA200510221 B ZA 200510221B ZA 200510221 A ZA200510221 A ZA 200510221A ZA 200510221 A ZA200510221 A ZA 200510221A ZA 200510221 B ZA200510221 B ZA 200510221B
- Authority
- ZA
- South Africa
- Prior art keywords
- formula
- group
- compound
- carbons
- groups
- Prior art date
Links
- 229940002612 prodrug Drugs 0.000 title description 19
- 239000000651 prodrug Substances 0.000 title description 19
- 229940126409 proton pump inhibitor Drugs 0.000 title description 7
- 239000000612 proton pump inhibitor Substances 0.000 title description 7
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 32
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000003153 chemical reaction reagent Substances 0.000 claims description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 9
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims description 6
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 6
- RAFNCPHFRHZCPS-UHFFFAOYSA-N di(imidazol-1-yl)methanethione Chemical compound C1=CN=CN1C(=S)N1C=CN=C1 RAFNCPHFRHZCPS-UHFFFAOYSA-N 0.000 claims description 6
- 150000003536 tetrazoles Chemical group 0.000 claims description 6
- 230000002194 synthesizing effect Effects 0.000 claims description 5
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 4
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 3
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 claims description 3
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 3
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 6
- 230000001590 oxidative effect Effects 0.000 claims 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 3
- 241000269435 Rana <genus> Species 0.000 claims 1
- 125000002843 carboxylic acid group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- IQPSEEYGBUAQFF-UHFFFAOYSA-N Pantoprazole Chemical compound COC1=CC=NC(CS(=O)C=2NC3=CC=C(OC(F)F)C=C3N=2)=C1OC IQPSEEYGBUAQFF-UHFFFAOYSA-N 0.000 description 9
- SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 description 8
- 229960000381 omeprazole Drugs 0.000 description 8
- 229960005019 pantoprazole Drugs 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000003814 drug Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical class C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 2
- 150000001556 benzimidazoles Chemical class 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- MJIHNNLFOKEZEW-UHFFFAOYSA-N lansoprazole Chemical compound CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC=CC=C2N1 MJIHNNLFOKEZEW-UHFFFAOYSA-N 0.000 description 2
- 229960003174 lansoprazole Drugs 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- YREYEVIYCVEVJK-UHFFFAOYSA-N rabeprazole Chemical compound COCCCOC1=CC=NC(CS(=O)C=2NC3=CC=CC=C3N=2)=C1C YREYEVIYCVEVJK-UHFFFAOYSA-N 0.000 description 2
- 229960004157 rabeprazole Drugs 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- NJWIMFZLESWFIM-UHFFFAOYSA-N 2-(chloromethyl)pyridine Chemical class ClCC1=CC=CC=N1 NJWIMFZLESWFIM-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 108091006112 ATPases Proteins 0.000 description 1
- 102000057290 Adenosine Triphosphatases Human genes 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241000590002 Helicobacter pylori Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 201000008197 Laryngitis Diseases 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 206010030216 Oesophagitis Diseases 0.000 description 1
- 208000008469 Peptic Ulcer Diseases 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 201000006549 dyspepsia Diseases 0.000 description 1
- 208000006881 esophagitis Diseases 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 208000021302 gastroesophageal reflux disease Diseases 0.000 description 1
- 208000024798 heartburn Diseases 0.000 description 1
- 229940037467 helicobacter pylori Drugs 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 208000000689 peptic esophagitis Diseases 0.000 description 1
- 208000011906 peptic ulcer disease Diseases 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/06—Anti-spasmodics, e.g. drugs for colics, esophagic dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/622—Forming processes; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/626—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B
- C04B35/63—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B using additives specially adapted for forming the products, e.g.. binder binders
- C04B35/632—Organic additives
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US48734003P | 2003-07-15 | 2003-07-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200510221B true ZA200510221B (en) | 2006-12-27 |
Family
ID=34193068
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200510221A ZA200510221B (en) | 2003-07-15 | 2005-12-15 | Process for preparing isomerically pure prodrugs of proton pump inhibitors |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US7294716B2 (ja) |
| EP (1) | EP1644352A1 (ja) |
| JP (1) | JP2007521314A (ja) |
| KR (1) | KR20060041224A (ja) |
| CN (1) | CN1823058A (ja) |
| AR (1) | AR042950A1 (ja) |
| AU (1) | AU2004264401A1 (ja) |
| BR (1) | BRPI0412590A (ja) |
| CA (1) | CA2532104A1 (ja) |
| IL (1) | IL172623A0 (ja) |
| MX (1) | MXPA06000410A (ja) |
| NZ (1) | NZ544173A (ja) |
| PL (1) | PL379542A1 (ja) |
| TW (1) | TW200502232A (ja) |
| WO (1) | WO2005016917A1 (ja) |
| ZA (1) | ZA200510221B (ja) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004111029A2 (en) * | 2003-06-10 | 2004-12-23 | Teva Pharmaceutical Industries Ltd. | Process for preparing 2-[(pyridinyl)methyl]sulfinyl-substituted benzimidazoles and novel chlorinated derivatives of pantoprazole |
| US20050075371A1 (en) * | 2003-10-03 | 2005-04-07 | Allergan, Inc. | Methods and compositions for the oral administration of prodrugs of proton pump inhibitors |
| CA2557471A1 (en) * | 2004-02-18 | 2005-09-09 | Allergan, Inc. | Methods and compositions for the intravenous administration of compounds related to proton pump inhibitors |
| US7914681B2 (en) * | 2004-05-28 | 2011-03-29 | Jms Co. | Hemodialyzer capable of intermittent repetition of infusion and water removal operation |
| WO2007073301A1 (en) * | 2005-12-23 | 2007-06-28 | Astrazeneca Ab | Benzoimidazole derivatives as prodrugs of proton pump inhibitors |
| US20070265311A1 (en) * | 2006-01-10 | 2007-11-15 | Rubino Mark P | Therapeutic Salt Compositions and Methods |
| EP2294064A4 (en) * | 2008-07-07 | 2011-10-05 | Hetero Research Foundation | PROCESS FOR PURIFYING RABEPRAZOLE-SODIUM |
| US8927559B2 (en) | 2010-10-11 | 2015-01-06 | Merck Sharp & Dohme Corp. | Quinazolinone-type compounds as CRTH2 antagonists |
| JP5952829B2 (ja) | 2010-12-23 | 2016-07-13 | メルク・シャープ・アンド・ドーム・コーポレーションＭｅｒｃｋ Ｓｈａｒｐ ＆ Ｄｏｈｍｅ Ｃｏｒｐ． | Ｃｒｔｈ２受容体調節剤としてのキノキサリン類およびアザ−キノキサリン類 |
| US9290453B2 (en) | 2010-12-23 | 2016-03-22 | Merck Sharp & Dohme Corp. | Quinolines and aza-quinolines as CRTH2 receptor modulators |
| CN103232389A (zh) * | 2013-05-08 | 2013-08-07 | 浙江新三和医药化工股份有限公司 | 2-氯甲基-4-甲氧基-3,5-二甲基吡啶盐酸盐的制备方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE7804231L (sv) * | 1978-04-14 | 1979-10-15 | Haessle Ab | Magsyrasekretionsmedel |
| SE8300736D0 (sv) * | 1983-02-11 | 1983-02-11 | Haessle Ab | Novel pharmacologically active compounds |
| IL75400A (en) * | 1984-06-16 | 1988-10-31 | Byk Gulden Lomberg Chem Fab | Dialkoxypyridine methyl(sulfinyl or sulfonyl)benzimidazoles,processes for the preparation thereof and pharmaceutical compositions containing the same |
| JPS6150978A (ja) * | 1984-08-16 | 1986-03-13 | Takeda Chem Ind Ltd | ピリジン誘導体およびその製造法 |
| FI90544C (fi) * | 1986-11-13 | 1994-02-25 | Eisai Co Ltd | Menetelmä lääkeaineina käyttökelpoisten 2-pyridin-2-yyli-metyylitio- ja sulfinyyli-1H-bensimidatsolijohdannaisten valmistamiseksi |
| SE9301830D0 (sv) * | 1993-05-28 | 1993-05-28 | Ab Astra | New compounds |
| NZ510180A (en) * | 1998-08-10 | 2002-11-26 | Univ California | Prodrugs of the pyridyl-methylsulphonyl-benzimidazole type proton pump inhibitors |
| US6093734A (en) * | 1998-08-10 | 2000-07-25 | Partnership Of Michael E. Garst, George Sachs, And Jai Moo Shin | Prodrugs of proton pump inhibitors |
| US6348032B1 (en) * | 1998-11-23 | 2002-02-19 | Cell Pathways, Inc. | Method of inhibiting neoplastic cells with benzimidazole derivatives |
| US6599167B2 (en) * | 2000-09-27 | 2003-07-29 | Glenn Waltz | Game call holder and amplifying device |
| CA2492718C (en) * | 2002-07-19 | 2010-12-21 | Michael E. Garst | Prodrugs of proton pump inhibitors |
-
2004
- 2004-01-15 BR BRPI0412590-8A patent/BRPI0412590A/pt not_active IP Right Cessation
- 2004-01-15 PL PL379542A patent/PL379542A1/pl unknown
- 2004-01-15 KR KR1020067000776A patent/KR20060041224A/ko not_active Application Discontinuation
- 2004-01-15 EP EP04702576A patent/EP1644352A1/en not_active Withdrawn
- 2004-01-15 JP JP2006520146A patent/JP2007521314A/ja active Pending
- 2004-01-15 WO PCT/US2004/001154 patent/WO2005016917A1/en active Application Filing
- 2004-01-15 MX MXPA06000410A patent/MXPA06000410A/es unknown
- 2004-01-15 NZ NZ544173A patent/NZ544173A/en unknown
- 2004-01-15 AU AU2004264401A patent/AU2004264401A1/en not_active Abandoned
- 2004-01-15 CN CNA2004800204889A patent/CN1823058A/zh active Pending
- 2004-01-15 CA CA002532104A patent/CA2532104A1/en not_active Abandoned
- 2004-01-27 TW TW093101731A patent/TW200502232A/zh unknown
- 2004-01-28 AR ARP040100251A patent/AR042950A1/es unknown
- 2004-07-13 US US10/891,317 patent/US7294716B2/en not_active Expired - Fee Related
-
2005
- 2005-12-15 IL IL172623A patent/IL172623A0/en unknown
- 2005-12-15 ZA ZA200510221A patent/ZA200510221B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2005016917A1 (en) | 2005-02-24 |
| AU2004264401A1 (en) | 2005-02-24 |
| KR20060041224A (ko) | 2006-05-11 |
| JP2007521314A (ja) | 2007-08-02 |
| BRPI0412590A (pt) | 2006-09-19 |
| CN1823058A (zh) | 2006-08-23 |
| EP1644352A1 (en) | 2006-04-12 |
| PL379542A1 (pl) | 2006-10-02 |
| US20050038076A1 (en) | 2005-02-17 |
| MXPA06000410A (es) | 2006-03-17 |
| US7294716B2 (en) | 2007-11-13 |
| AR042950A1 (es) | 2005-07-06 |
| TW200502232A (en) | 2005-01-16 |
| CA2532104A1 (en) | 2005-02-24 |
| IL172623A0 (en) | 2006-04-10 |
| NZ544173A (en) | 2009-04-30 |
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