LT3980B - New therapeutically active compound and a process for its preparation - Google Patents
New therapeutically active compound and a process for its preparation Download PDFInfo
- Publication number
- LT3980B LT3980B LTIP1721A LTIP1721A LT3980B LT 3980 B LT3980 B LT 3980B LT IP1721 A LTIP1721 A LT IP1721A LT IP1721 A LTIP1721 A LT IP1721A LT 3980 B LT3980 B LT 3980B
- Authority
- LT
- Lithuania
- Prior art keywords
- compound
- cyclopropylmethoxy
- compound according
- preparation
- benzimidazole
- Prior art date
Links
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- MVPICKVDHDWCJQ-UHFFFAOYSA-N ethyl 3-pyrrolidin-1-ylpropanoate Chemical compound CCOC(=O)CCN1CCCC1 MVPICKVDHDWCJQ-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000003890 fistula Effects 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
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- 235000013305 food Nutrition 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 210000004211 gastric acid Anatomy 0.000 description 1
- 201000005917 gastric ulcer Diseases 0.000 description 1
- 201000000052 gastrinoma Diseases 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000010224 hepatic metabolism Effects 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 229960004931 histamine dihydrochloride Drugs 0.000 description 1
- PPZMYIBUHIPZOS-UHFFFAOYSA-N histamine dihydrochloride Chemical compound Cl.Cl.NCCC1=CN=CN1 PPZMYIBUHIPZOS-UHFFFAOYSA-N 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
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- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
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- 230000000968 intestinal effect Effects 0.000 description 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical class [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 235000011160 magnesium carbonates Nutrition 0.000 description 1
- 235000012254 magnesium hydroxide Nutrition 0.000 description 1
- 235000012245 magnesium oxide Nutrition 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 206010063344 microscopic polyangiitis Diseases 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
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- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- ANRIQLNBZQLTFV-DZUOILHNSA-N pentagastrin Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1[C]2C=CC=CC2=NC=1)NC(=O)CCNC(=O)OC(C)(C)C)CCSC)C(N)=O)C1=CC=CC=C1 ANRIQLNBZQLTFV-DZUOILHNSA-N 0.000 description 1
- 229960000444 pentagastrin Drugs 0.000 description 1
- 208000011906 peptic ulcer disease Diseases 0.000 description 1
- 150000002976 peresters Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000007686 potassium Nutrition 0.000 description 1
- 229920001592 potato starch Chemical class 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
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- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
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- 230000003248 secreting effect Effects 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229940045902 sodium stearyl fumarate Drugs 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000008107 starch Chemical class 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 210000001685 thyroid gland Anatomy 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 150000003682 vanadium compounds Chemical class 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 239000001993 wax Substances 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
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE19888804629A SE8804629D0 (sv) | 1988-12-22 | 1988-12-22 | New therapeutically active compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| LTIP1721A LTIP1721A (en) | 1995-07-25 |
| LT3980B true LT3980B (en) | 1996-06-25 |
Family
ID=20374310
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LTIP1721A LT3980B (en) | 1988-12-22 | 1993-12-30 | New therapeutically active compound and a process for its preparation |
| LTIP1726A LT3914B (en) | 1988-12-22 | 1993-12-30 | Compound with gastric acid inhibitory effect and process for its preparation |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LTIP1726A LT3914B (en) | 1988-12-22 | 1993-12-30 | Compound with gastric acid inhibitory effect and process for its preparation |
Country Status (32)
| Country | Link |
|---|---|
| US (2) | US5008278A (fr) |
| EP (1) | EP0449940B1 (fr) |
| JP (1) | JP2793906B2 (fr) |
| KR (1) | KR910700249A (fr) |
| CN (1) | CN1028231C (fr) |
| AR (1) | AR248136A1 (fr) |
| AT (1) | ATE127799T1 (fr) |
| AU (1) | AU634741B2 (fr) |
| BG (1) | BG60102B2 (fr) |
| CA (1) | CA2005986C (fr) |
| DD (2) | DD296078A5 (fr) |
| DE (1) | DE68924273T2 (fr) |
| DK (1) | DK170800B1 (fr) |
| EG (1) | EG19303A (fr) |
| FI (2) | FI913035A0 (fr) |
| GR (1) | GR1002252B (fr) |
| HR (1) | HRP920831A2 (fr) |
| HU (2) | HU205927B (fr) |
| IE (1) | IE894048L (fr) |
| IL (1) | IL92798A0 (fr) |
| LT (2) | LT3980B (fr) |
| LV (1) | LV10187B (fr) |
| NZ (1) | NZ231872A (fr) |
| PH (1) | PH27400A (fr) |
| PL (1) | PL161150B1 (fr) |
| PT (1) | PT92648B (fr) |
| RO (1) | RO110494B1 (fr) |
| RU (2) | RU2073676C1 (fr) |
| SE (1) | SE8804629D0 (fr) |
| WO (1) | WO1990006925A1 (fr) |
| YU (1) | YU46806B (fr) |
| ZA (2) | ZA899794B (fr) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ244301A (en) * | 1991-09-20 | 1994-08-26 | Merck & Co Inc | Preparation of 2-pyridylmethylsulphinylbenzimidazole and pyridoimidazole derivatives from the corresponding sulphenyl compounds |
| TNSN95063A1 (fr) * | 1994-05-27 | 1996-02-06 | Astra Ab | Nouveaux benzimidazoles substitues |
| EP0723436B1 (fr) * | 1994-07-08 | 2001-09-26 | AstraZeneca AB | Forme posologique sous forme de comprime composite (i) |
| SE9402431D0 (sv) * | 1994-07-08 | 1994-07-08 | Astra Ab | New tablet formulation |
| SE9500422D0 (sv) * | 1995-02-06 | 1995-02-06 | Astra Ab | New oral pharmaceutical dosage forms |
| SE9500478D0 (sv) * | 1995-02-09 | 1995-02-09 | Astra Ab | New pharmaceutical formulation and process |
| 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 |
| US6699885B2 (en) | 1996-01-04 | 2004-03-02 | The Curators Of The University Of Missouri | Substituted benzimidazole dosage forms and methods of 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 |
| SE9600070D0 (sv) | 1996-01-08 | 1996-01-08 | Astra Ab | New oral pharmaceutical dosage forms |
| DE19758573C2 (de) * | 1997-11-26 | 2001-03-01 | Implex Hear Tech Ag | Fixationselement für ein implantierbares Mikrofon |
| WO1999053918A1 (fr) * | 1998-04-20 | 1999-10-28 | Eisai Co., Ltd. | Compositions stabilisees contenant des composes du type benzimidazole |
| TWI243672B (en) | 1999-06-01 | 2005-11-21 | Astrazeneca Ab | New use of compounds as antibacterial agents |
| WO2001028559A1 (fr) | 1999-10-20 | 2001-04-26 | Eisai Co., Ltd. | Procede de stabilisation de composes benzimidazoles |
| SE0000774D0 (sv) | 2000-03-08 | 2000-03-08 | Astrazeneca Ab | New formulation |
| SE0101379D0 (sv) | 2001-04-18 | 2001-04-18 | Diabact Ab | Komposition som hämmar utsöndring av magsyra |
| US8206741B2 (en) | 2001-06-01 | 2012-06-26 | Pozen Inc. | Pharmaceutical compositions for the coordinated delivery of NSAIDs |
| SE0102993D0 (sv) | 2001-09-07 | 2001-09-07 | Astrazeneca Ab | New self emulsifying drug delivery system |
| MXPA04007169A (es) * | 2002-01-25 | 2004-10-29 | Santarus Inc | Suministro transmucosal de inhibidores de bomba de protones. |
| US20050234103A1 (en) * | 2002-03-26 | 2005-10-20 | Reddy Manne S | Crystalline forms of rabeprazole sodium |
| SE0203065D0 (sv) | 2002-10-16 | 2002-10-16 | Diabact Ab | Gastric acid secretion inhibiting composition |
| CA2517005A1 (fr) * | 2003-02-20 | 2004-09-02 | Santarus, Inc. | Liberation immediate d'un complexe antacide d'omeprazole presentant une nouvelle formulation pour une elimination rapide et prolongee d'acide gastrique |
| US8993599B2 (en) * | 2003-07-18 | 2015-03-31 | Santarus, Inc. | Pharmaceutical formulations useful for inhibiting acid secretion and methods for making and using them |
| WO2005007115A2 (fr) * | 2003-07-18 | 2005-01-27 | Santarus, Inc. | Formulations pharmaceutiques utilisees pour inhiber une secretion acide et procede de fabrication associe |
| AR045061A1 (es) * | 2003-07-18 | 2005-10-12 | Santarus Inc | Formulacion farmaceutica y metodo para tratar trastornos gastrointestinales causados por acido |
| ATE544447T1 (de) | 2003-09-26 | 2012-02-15 | Alza Corp | Arzneistoffcoating mit hohem wirkstoffanteil sowie methoden zu dessen herstellung |
| US20070292498A1 (en) * | 2003-11-05 | 2007-12-20 | Warren Hall | Combinations of proton pump inhibitors, sleep aids, buffers and pain relievers |
| US8815916B2 (en) * | 2004-05-25 | 2014-08-26 | Santarus, Inc. | Pharmaceutical formulations useful for inhibiting acid secretion and methods for making and using them |
| US8906940B2 (en) * | 2004-05-25 | 2014-12-09 | Santarus, Inc. | Pharmaceutical formulations useful for inhibiting acid secretion and methods for making and using them |
| US8541026B2 (en) | 2004-09-24 | 2013-09-24 | Abbvie Inc. | Sustained release formulations of opioid and nonopioid analgesics |
| US7981908B2 (en) | 2005-05-11 | 2011-07-19 | Vecta, Ltd. | Compositions and methods for inhibiting gastric acid secretion |
| US7803817B2 (en) | 2005-05-11 | 2010-09-28 | Vecta, Ltd. | Composition and methods for inhibiting gastric acid secretion |
| RU2467747C2 (ru) | 2006-07-25 | 2012-11-27 | Векта Лтд. | Композиции и способы для ингибирования секреции желудочной кислоты с использованием производных малых дикарбоновых кислот в сочетании с ppi |
| US20090092658A1 (en) * | 2007-10-05 | 2009-04-09 | Santarus, Inc. | Novel formulations of proton pump inhibitors and methods of using these formulations |
| CA2736547C (fr) | 2008-09-09 | 2016-11-01 | Pozen Inc. | Procede d'administration d'une composition pharmaceutique a un patient en ayant besoin |
| AU2010263304A1 (en) | 2009-06-25 | 2012-02-02 | Astrazeneca Ab | Method for treating a patient at risk for developing an NSAID-associated ulcer |
| WO2011080501A2 (fr) | 2009-12-29 | 2011-07-07 | Orexo Ab | Nouvelle forme pharmaceutique destinée au traitement de troubles liés à l'acide gastrique |
| WO2011080500A2 (fr) | 2009-12-29 | 2011-07-07 | Orexo Ab | Nouvelle forme pharmaceutique destinée au traitement de troubles liés à l'acide gastrique |
| WO2011080502A2 (fr) | 2009-12-29 | 2011-07-07 | Orexo Ab | Nouvelle forme pharmaceutique destinée au traitement de troubles liés à l'acide gastrique |
| EP2601947A1 (fr) | 2011-12-05 | 2013-06-12 | Abo Bakr Mohammed Ali Al-Mehdar | Combinaison à dose fixe pour le traitement de maladies associées à Hélicobacter pylori |
| MX2014007935A (es) | 2011-12-28 | 2014-11-14 | Pozen Inc | Composiciones y metodos mejorados para el suministro de omeprazol y de acido acetilsalicilico. |
Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1500043A (en) | 1974-02-18 | 1978-02-08 | Haessle Ab | Benzimidazole derivatives their preparation and their use in affecting gastric acid secretion |
| GB1525958A (en) | 1974-05-16 | 1978-09-27 | Haessle Ab | 2-(heterocyclic substituted alkylsulphinyl)-benzimidazoles and their pharmaceutical compositions |
| US4182766A (en) | 1977-09-19 | 1980-01-08 | Hoffmann-La Roche Inc. | Naphth[2,3-d]imidazoles |
| US4255431A (en) | 1978-04-14 | 1981-03-10 | Aktiebolaget Hassle | Gastric acid secretion inhibiting substituted 2-(2-benzimidazolyl)-pyridines, pharmaceutical preparations containing same, and method for inhibiting gastric acid secretion |
| US4359465A (en) | 1980-07-28 | 1982-11-16 | The Upjohn Company | Methods for treating gastrointestinal inflammation |
| EP0124495A2 (fr) | 1983-03-04 | 1984-11-07 | Aktiebolaget Hässle | Sels d'oméprazole |
| US4555518A (en) | 1983-05-03 | 1985-11-26 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Fluoroalkoxy substituted benzimidazoles useful as gastric acid secretion inhibitors |
| US4599347A (en) | 1980-08-21 | 1986-07-08 | Hoffmann-La Roche Inc. | Tetrahydro-naphth (2.3-d) imidazole derivatives |
| US4628098A (en) | 1984-08-16 | 1986-12-09 | Takeda Chemical Industries, Ltd. | 2-[2-pyridylmethylthio-(sulfinyl)]benzimidazoles |
| EP0208452A2 (fr) | 1985-07-02 | 1987-01-14 | Takeda Chemical Industries, Ltd. | Dérivés de pyridine, leur préparation et utilisation |
| US4727150A (en) | 1984-08-16 | 1988-02-23 | Takeda Chemical Industries, Ltd. | Pyridyl methylsulfinyl benzimidazole derivatives |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US428098A (en) | 1890-05-20 | Electric railway | ||
| US727150A (en) | 1902-06-18 | 1903-05-05 | Peter Paul Keller | Adjustable hanger for incandescent lamps. |
| DE3215503A1 (de) | 1982-04-26 | 1983-11-03 | Zängl GmbH, 8000 München | Elektrisch beheiztes schneidgeraet |
| AU568441B2 (en) * | 1984-09-24 | 1987-12-24 | Upjohn Company, The | 2-(pyridylalkenesulfinyl) benzimidazole derivatives |
| JPS6261978A (ja) * | 1985-09-12 | 1987-03-18 | Otsuka Pharmaceut Co Ltd | ５−フルオロ−１ｈ−ベンズイミダゾ−ル誘導体 |
| SE8505112D0 (sv) * | 1985-10-29 | 1985-10-29 | Haessle Ab | Novel pharmacological compounds |
| JPS62201884A (ja) * | 1986-02-28 | 1987-09-05 | Tokyo Tanabe Co Ltd | ベンズイミダゾール誘導体及びその製造法 |
| FI90544C (fi) * | 1986-11-13 | 1994-02-25 | Eisai Co Ltd | Menetelmä lääkeaineina käyttökelpoisten 2-pyridin-2-yyli-metyylitio- ja sulfinyyli-1H-bensimidatsolijohdannaisten valmistamiseksi |
| NZ234564A (en) * | 1986-11-21 | 1991-04-26 | Haessle Ab | 1-substituted benzimidazoles and pharmaceutical compositions |
| FI96860C (fi) * | 1987-06-17 | 1996-09-10 | Eisai Co Ltd | Analogiamenetelmä lääkeaineena käytettävän pyridiinijohdannaisen valmistamiseksi |
| DE3722810A1 (de) * | 1987-07-10 | 1989-01-19 | Hoechst Ag | Substituierte benzimidazole, verfahren zu deren herstellung, diese enthaltende pharmazeutische zubereitungen und deren verwendung |
| DK171989B1 (da) * | 1987-08-04 | 1997-09-08 | Takeda Chemical Industries Ltd | Fremgangsmåde til fremstilling af 2-(2-pyridylmethylsulfinyl)-benzimidazoler |
| JPH0676323B2 (ja) * | 1987-08-28 | 1994-09-28 | 東京田辺製薬株式会社 | 抗潰瘍剤 |
-
1988
- 1988-12-22 SE SE19888804629A patent/SE8804629D0/xx unknown
-
1989
- 1989-12-18 AR AR89315705A patent/AR248136A1/es active
- 1989-12-18 IE IE894048A patent/IE894048L/xx unknown
- 1989-12-18 EG EG62189A patent/EG19303A/xx active
- 1989-12-19 IL IL92798A patent/IL92798A0/xx not_active IP Right Cessation
- 1989-12-19 CA CA002005986A patent/CA2005986C/fr not_active Expired - Lifetime
- 1989-12-19 NZ NZ231872A patent/NZ231872A/en unknown
- 1989-12-19 GR GR890100838A patent/GR1002252B/el unknown
- 1989-12-19 PH PH39732A patent/PH27400A/en unknown
- 1989-12-20 DD DD89335980A patent/DD296078A5/de not_active IP Right Cessation
- 1989-12-20 EP EP90901079A patent/EP0449940B1/fr not_active Expired - Lifetime
- 1989-12-20 ZA ZA899794A patent/ZA899794B/xx unknown
- 1989-12-20 HU HU901095A patent/HU205927B/hu not_active IP Right Cessation
- 1989-12-20 WO PCT/SE1989/000740 patent/WO1990006925A1/fr active Application Filing
- 1989-12-20 HU HU901084A patent/HU205926B/hu not_active IP Right Cessation
- 1989-12-20 ZA ZA899795A patent/ZA899795B/xx unknown
- 1989-12-20 DE DE68924273T patent/DE68924273T2/de not_active Expired - Fee Related
- 1989-12-20 DD DD89335981A patent/DD296079A5/de not_active IP Right Cessation
- 1989-12-20 RU SU894895789A patent/RU2073676C1/ru active
- 1989-12-20 AT AT90901079T patent/ATE127799T1/de not_active IP Right Cessation
- 1989-12-20 AU AU48175/90A patent/AU634741B2/en not_active Ceased
- 1989-12-20 JP JP2501537A patent/JP2793906B2/ja not_active Expired - Fee Related
- 1989-12-20 US US07/454,047 patent/US5008278A/en not_active Expired - Lifetime
- 1989-12-20 RO RO147866A patent/RO110494B1/ro unknown
- 1989-12-21 YU YU242689A patent/YU46806B/sh unknown
- 1989-12-21 PT PT92648A patent/PT92648B/pt not_active IP Right Cessation
- 1989-12-21 CN CN89109587A patent/CN1028231C/zh not_active Expired - Fee Related
- 1989-12-22 PL PL1989282923A patent/PL161150B1/pl unknown
-
1990
- 1990-08-21 KR KR1019900701828A patent/KR910700249A/ko not_active Application Discontinuation
- 1990-12-20 US US07/633,007 patent/US5039808A/en not_active Expired - Lifetime
-
1991
- 1991-06-19 BG BG094659A patent/BG60102B2/bg unknown
- 1991-06-20 FI FI913035A patent/FI913035A0/fi not_active Application Discontinuation
- 1991-06-21 DK DK122291A patent/DK170800B1/da not_active IP Right Cessation
- 1991-06-21 RU SU914895805A patent/RU2042673C1/ru active
-
1992
- 1992-10-02 HR HR920831A patent/HRP920831A2/hr not_active Application Discontinuation
-
1993
- 1993-06-30 LV LVP-93-860A patent/LV10187B/en unknown
- 1993-12-30 LT LTIP1721A patent/LT3980B/lt not_active IP Right Cessation
- 1993-12-30 LT LTIP1726A patent/LT3914B/lt not_active IP Right Cessation
-
1995
- 1995-10-06 FI FI954768A patent/FI954768A0/fi not_active Application Discontinuation
Patent Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1500043A (en) | 1974-02-18 | 1978-02-08 | Haessle Ab | Benzimidazole derivatives their preparation and their use in affecting gastric acid secretion |
| GB1525958A (en) | 1974-05-16 | 1978-09-27 | Haessle Ab | 2-(heterocyclic substituted alkylsulphinyl)-benzimidazoles and their pharmaceutical compositions |
| US4182766A (en) | 1977-09-19 | 1980-01-08 | Hoffmann-La Roche Inc. | Naphth[2,3-d]imidazoles |
| US4255431A (en) | 1978-04-14 | 1981-03-10 | Aktiebolaget Hassle | Gastric acid secretion inhibiting substituted 2-(2-benzimidazolyl)-pyridines, pharmaceutical preparations containing same, and method for inhibiting gastric acid secretion |
| US4359465A (en) | 1980-07-28 | 1982-11-16 | The Upjohn Company | Methods for treating gastrointestinal inflammation |
| US4599347A (en) | 1980-08-21 | 1986-07-08 | Hoffmann-La Roche Inc. | Tetrahydro-naphth (2.3-d) imidazole derivatives |
| EP0124495A2 (fr) | 1983-03-04 | 1984-11-07 | Aktiebolaget Hässle | Sels d'oméprazole |
| US4555518A (en) | 1983-05-03 | 1985-11-26 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Fluoroalkoxy substituted benzimidazoles useful as gastric acid secretion inhibitors |
| US4628098A (en) | 1984-08-16 | 1986-12-09 | Takeda Chemical Industries, Ltd. | 2-[2-pyridylmethylthio-(sulfinyl)]benzimidazoles |
| US4727150A (en) | 1984-08-16 | 1988-02-23 | Takeda Chemical Industries, Ltd. | Pyridyl methylsulfinyl benzimidazole derivatives |
| EP0208452A2 (fr) | 1985-07-02 | 1987-01-14 | Takeda Chemical Industries, Ltd. | Dérivés de pyridine, leur préparation et utilisation |
Non-Patent Citations (1)
| Title |
|---|
| A. GOTH: "Medical Pharmacology, 7th ed.", pages: 19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM9A | Lapsed patents |
Effective date: 19961230 |