RU2163238C2 - Способ получения магниевой соли замещенного сульфинил-гетероциклического соединения - Google Patents
Способ получения магниевой соли замещенного сульфинил-гетероциклического соединения Download PDFInfo
- Publication number
- RU2163238C2 RU2163238C2 RU98121016/04A RU98121016A RU2163238C2 RU 2163238 C2 RU2163238 C2 RU 2163238C2 RU 98121016/04 A RU98121016/04 A RU 98121016/04A RU 98121016 A RU98121016 A RU 98121016A RU 2163238 C2 RU2163238 C2 RU 2163238C2
- Authority
- RU
- Russia
- Prior art keywords
- alkyl
- magnesium
- alkoxy
- hydrogen
- groups
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 36
- 159000000003 magnesium salts Chemical class 0.000 title claims abstract description 26
- 150000001875 compounds Chemical class 0.000 title claims description 9
- 239000011777 magnesium Substances 0.000 claims abstract description 28
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 22
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
- 239000001257 hydrogen Substances 0.000 claims abstract description 18
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 15
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 12
- 150000002367 halogens Chemical group 0.000 claims abstract description 12
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 12
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims abstract description 10
- -1 piperidino, morpholino Chemical group 0.000 claims abstract description 10
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract description 9
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims abstract description 6
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 6
- YIXJRHPUWRPCBB-UHFFFAOYSA-N magnesium nitrate Chemical compound [Mg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O YIXJRHPUWRPCBB-UHFFFAOYSA-N 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000001412 amines Chemical class 0.000 claims abstract description 5
- 125000006165 cyclic alkyl group Chemical group 0.000 claims abstract description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims abstract description 5
- 235000019341 magnesium sulphate Nutrition 0.000 claims abstract description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims abstract description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 3
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims abstract description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 3
- UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 claims abstract description 3
- 239000011654 magnesium acetate Substances 0.000 claims abstract description 3
- 235000011285 magnesium acetate Nutrition 0.000 claims abstract description 3
- 229940069446 magnesium acetate Drugs 0.000 claims abstract description 3
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical class [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 claims abstract description 3
- 239000001095 magnesium carbonate Substances 0.000 claims abstract description 3
- 235000011160 magnesium carbonates Nutrition 0.000 claims abstract description 3
- 229910001629 magnesium chloride Inorganic materials 0.000 claims abstract description 3
- 235000011147 magnesium chloride Nutrition 0.000 claims abstract description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- 125000002071 phenylalkoxy group Chemical group 0.000 claims abstract description 3
- 125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 3
- 125000001424 substituent group Chemical group 0.000 claims abstract description 3
- 125000004950 trifluoroalkyl group Chemical group 0.000 claims abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
- 229910052731 fluorine Inorganic materials 0.000 claims abstract 2
- 239000011737 fluorine Substances 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 238000001914 filtration Methods 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 4
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 5
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract 2
- 230000000694 effects Effects 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 78
- 239000000047 product Substances 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- 239000000203 mixture Substances 0.000 description 25
- SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical class N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 description 17
- 150000003839 salts Chemical class 0.000 description 11
- 229960000381 omeprazole Drugs 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 8
- MQEUGMWHWPYFDD-UHFFFAOYSA-N magnesium;6-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-1h-benzimidazole Chemical class [Mg].N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C MQEUGMWHWPYFDD-UHFFFAOYSA-N 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 150000001556 benzimidazoles Chemical class 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 5
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 5
- 239000000347 magnesium hydroxide Substances 0.000 description 5
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 5
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- 229940126409 proton pump inhibitor Drugs 0.000 description 3
- 239000000612 proton pump inhibitor Substances 0.000 description 3
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- DIUOJMLXZJHNDR-UHFFFAOYSA-N 2-[[4-(cyclopropylmethoxy)pyridin-2-yl]methylsulfinyl]-6-fluoro-1h-benzimidazole Chemical compound N=1C2=CC(F)=CC=C2NC=1S(=O)CC(N=CC=1)=CC=1OCC1CC1 DIUOJMLXZJHNDR-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 0 Cc(c(C*)c1*)ccc1I Chemical compound Cc(c(C*)c1*)ccc1I 0.000 description 2
- 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 2
- GSDOHHSVOZCVHW-UHFFFAOYSA-N [Mg].FC1=CC=C2NC(=NC2=C1)S(=O)CC1=NC=CC(OCC2CC2)=C1 Chemical compound [Mg].FC1=CC=C2NC(=NC2=C1)S(=O)CC1=NC=CC(OCC2CC2)=C1 GSDOHHSVOZCVHW-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- PSIREIZGKQBEEO-UHFFFAOYSA-N 2-(1h-benzimidazol-2-ylsulfinylmethyl)-n-methyl-n-(2-methylpropyl)aniline Chemical compound CC(C)CN(C)C1=CC=CC=C1CS(=O)C1=NC2=CC=CC=C2N1 PSIREIZGKQBEEO-UHFFFAOYSA-N 0.000 description 1
- LCBVHJCXYRFNPC-UHFFFAOYSA-N 6-(difluoromethoxy)-2-[(3,4-dimethoxypyridin-2-yl)methylsulfinyl]-1h-benzimidazole;magnesium Chemical compound [Mg].COC1=CC=NC(CS(=O)C=2NC3=CC(OC(F)F)=CC=C3N=2)=C1OC LCBVHJCXYRFNPC-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- VBNJZMQPFNLZDC-WYMLVPIESA-N CC1C(C/C(/C)=C(\C)/C(C=O)=C)=CCC2=C1C=C=C2 Chemical compound CC1C(C/C(/C)=C(\C)/C(C=O)=C)=CCC2=C1C=C=C2 VBNJZMQPFNLZDC-WYMLVPIESA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000362 adenosine triphosphatase inhibitor Substances 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 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 1
- 229960003174 lansoprazole Drugs 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229950007395 leminoprazole Drugs 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229960005019 pantoprazole Drugs 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- YREYEVIYCVEVJK-UHFFFAOYSA-N rabeprazole Chemical compound COCCCOC1=CC=NC(CS(=O)C=2NC3=CC=CC=C3N=2)=C1C YREYEVIYCVEVJK-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002731 stomach secretion inhibitor Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000759 toxicological effect 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/28—Sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9601598-7 | 1996-04-26 | ||
| SE9601598A SE508669C2 (sv) | 1996-04-26 | 1996-04-26 | Nytt förfarande |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU98121016A RU98121016A (ru) | 2000-10-20 |
| RU2163238C2 true RU2163238C2 (ru) | 2001-02-20 |
Family
ID=20402358
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU98121016/04A RU2163238C2 (ru) | 1996-04-26 | 1997-04-22 | Способ получения магниевой соли замещенного сульфинил-гетероциклического соединения |
Country Status (39)
Families Citing this family (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6875872B1 (en) * | 1993-05-28 | 2005-04-05 | Astrazeneca | Compounds |
| SE9301830D0 (sv) * | 1993-05-28 | 1993-05-28 | Ab Astra | New compounds |
| US6699885B2 (en) * | 1996-01-04 | 2004-03-02 | The Curators Of The University Of Missouri | Substituted benzimidazole dosage forms and methods of using same |
| US6489346B1 (en) * | 1996-01-04 | 2002-12-03 | The Curators Of The University Of Missouri | Substituted benzimidazole dosage forms and method of using same |
| US5840737A (en) | 1996-01-04 | 1998-11-24 | The Curators Of The University Of Missouri | Omeprazole solution and method for using same |
| US6645988B2 (en) * | 1996-01-04 | 2003-11-11 | Curators Of The University Of Missouri | Substituted benzimidazole dosage forms and method of using same |
| DE19843413C1 (de) * | 1998-08-18 | 2000-03-30 | Byk Gulden Lomberg Chem Fab | Neue Salzform von Pantoprazol |
| US6403616B1 (en) * | 1998-11-18 | 2002-06-11 | Astrazeneca Ab | Chemical process and pharmaceutical formulation |
| CA2290893C (en) | 1999-11-16 | 2007-05-01 | Bernard Charles Sherman | Magnesium omeprazole |
| AU2001276721A1 (en) * | 2000-08-04 | 2002-02-18 | Takeda Chemical Industries Ltd. | Salts of benzimidazole compound and use thereof |
| WO2003063840A2 (en) * | 2002-01-25 | 2003-08-07 | Santarus, Inc. | Transmucosal delivery of proton pump inhibitors |
| ES2286408T3 (es) * | 2002-03-05 | 2007-12-01 | Astrazeneca Ab | Sales de alquilamonio de omeprazol e esomeprazol. |
| TW200410955A (en) * | 2002-07-29 | 2004-07-01 | Altana Pharma Ag | Novel salt of (S)-PANTOPRAZOLE |
| DE10234617B4 (de) * | 2002-07-29 | 2013-04-04 | Nycomed Gmbh | Neues Salz von (S)-Pantoprazol |
| EA200500673A1 (ru) * | 2002-10-22 | 2005-12-29 | Рэнбакси Лабораториз Лимитед | Аморфная форма соли эзомепразола, способ ее получения и фармацевтическая композиция на её основе |
| US20040242642A1 (en) * | 2002-11-18 | 2004-12-02 | Dr. Reddy's Laboratories Limited | Crystalline esomeprazole compounds and process for the preparation thereof |
| EP1572680A2 (en) * | 2002-12-19 | 2005-09-14 | Eva Pharmaceutical Industries Ltd. | Solid states of pantoprazole sodium, known pantoprazole sodium hydrates, processes for their preparation. |
| US20060247277A1 (en) * | 2003-02-28 | 2006-11-02 | Yatendra Kumar | Polymorphs of s-omeprazole |
| PE20050150A1 (es) | 2003-05-08 | 2005-03-22 | Altana Pharma Ag | Una forma de dosificacion que contiene (s)-pantoprazol como ingrediente activo |
| CL2004000983A1 (es) | 2003-05-08 | 2005-03-04 | Altana Pharma Ag | Composicion farmaceutica oral en forma de tableta que comprende a pantoprazol magnetico dihidratado, en donde la forma de tableta esta compuesto por un nucleo, una capa intermedia y una capa exterior; y uso de la composicion farmaceutica en ulceras y |
| WO2005012289A1 (en) * | 2003-07-17 | 2005-02-10 | Altana Pharma Ag | Novel salt of (r) - pantoprazole |
| US8993599B2 (en) | 2003-07-18 | 2015-03-31 | Santarus, Inc. | Pharmaceutical formulations useful for inhibiting acid secretion and methods for making and using them |
| SE0302382D0 (sv) * | 2003-09-04 | 2003-09-04 | Astrazeneca Ab | New salts II |
| SE0302381D0 (sv) | 2003-09-04 | 2003-09-04 | Astrazeneca Ab | New salts I |
| ITMI20031813A1 (it) * | 2003-09-23 | 2005-03-24 | Dinamite Dipharma S P A In Forma A Bbreviata Diph | Procedimento per la preparazione di pantoprazolo e suoi sali. |
| WO2005082888A1 (en) * | 2004-03-01 | 2005-09-09 | Milen Merkez Ilac Endustrisi A.S. | Process for the preparation of magnesium salt of omeprazole |
| US8906940B2 (en) | 2004-05-25 | 2014-12-09 | Santarus, Inc. | Pharmaceutical formulations useful for inhibiting acid secretion and methods for making and using them |
| US8815916B2 (en) | 2004-05-25 | 2014-08-26 | Santarus, Inc. | Pharmaceutical formulations useful for inhibiting acid secretion and methods for making and using them |
| ES2246149B1 (es) * | 2004-07-02 | 2007-06-01 | Esteve Quimica, S.A. | Formas solidas de la sal magnesica de s-omeprazol y procedimientos para su preparacion. |
| US8779175B2 (en) * | 2004-10-25 | 2014-07-15 | Synthonics, Inc. | Coordination complexes, pharmaceutical solutions comprising coordination complexes, and methods of treating patients |
| US7799937B2 (en) | 2004-10-25 | 2010-09-21 | Synthonics, Inc. | Metal coordinated compositions |
| US20060141054A1 (en) * | 2004-10-25 | 2006-06-29 | Thomas Piccariello | Metal coordinated compositions |
| EP1801110A1 (en) | 2005-12-22 | 2007-06-27 | KRKA, tovarna zdravil, d.d., Novo mesto | Esomeprazole arginine salt |
| US7553857B2 (en) * | 2005-12-23 | 2009-06-30 | Lek Pharmaceuticals D.D. | S-omeprazole magnesium |
| US20080139623A1 (en) | 2006-06-12 | 2008-06-12 | Lilach Hedvati | Amorphous and crystalline forms of pantoprazole magnesium salt |
| EP1947099A1 (en) | 2007-01-18 | 2008-07-23 | LEK Pharmaceuticals D.D. | Process for solvent removal from omeprazole salts |
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| CN103467453A (zh) * | 2013-09-13 | 2013-12-25 | 上海海虹实业(集团)巢湖今辰药业有限公司 | 一种奥美拉唑镁原料药制备方法 |
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