LT3952B - Substituted benzimidazoles, process for their preparation and their pharmaceutical use - Google Patents
Substituted benzimidazoles, process for their preparation and their pharmaceutical use Download PDFInfo
- Publication number
- LT3952B LT3952B LTIP1712A LTIP1712A LT3952B LT 3952 B LT3952 B LT 3952B LT IP1712 A LTIP1712 A LT IP1712A LT IP1712 A LTIP1712 A LT IP1712A LT 3952 B LT3952 B LT 3952B
- Authority
- LT
- Lithuania
- Prior art keywords
- methyl
- compound
- formula
- dimethoxy
- pyridinyl
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims description 19
- 238000000034 method Methods 0.000 title claims description 10
- 230000008569 process Effects 0.000 title claims description 5
- 150000001556 benzimidazoles Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 127
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 239000004480 active ingredient Substances 0.000 claims abstract description 5
- 239000003814 drug Substances 0.000 claims abstract description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 44
- -1 5-acetyl-6-methyl-2 - [[(3,4-dimethoxy-2-pyridinyl) methyl] sulfinyl] -1H-benzimidazol-1-ylmethyl Chemical group 0.000 claims description 21
- 210000004051 gastric juice Anatomy 0.000 claims description 11
- 238000011282 treatment Methods 0.000 claims description 11
- 241000124008 Mammalia Species 0.000 claims description 8
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 8
- 230000005764 inhibitory process Effects 0.000 claims description 7
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- PXGUKFHKLYJVLJ-UHFFFAOYSA-N [5-acetyl-2-[(3,4-dimethoxypyridin-2-yl)methylsulfinyl]-6-methylbenzimidazol-1-yl]methyl ethyl carbonate Chemical compound N=1C2=CC(C(C)=O)=C(C)C=C2N(COC(=O)OCC)C=1S(=O)CC1=NC=CC(OC)=C1OC PXGUKFHKLYJVLJ-UHFFFAOYSA-N 0.000 claims description 3
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- 229960004484 carbachol Drugs 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
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- 235000019441 ethanol Nutrition 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- BIIIXELDRBGRHL-UHFFFAOYSA-N ethyl 2-sulfanylidene-1,3-dihydrobenzimidazole-5-carboxylate Chemical compound CCOC(=O)C1=CC=C2N=C(S)NC2=C1 BIIIXELDRBGRHL-UHFFFAOYSA-N 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000001640 fractional crystallisation Methods 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
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- 239000007924 injection Substances 0.000 description 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
- 210000004731 jugular vein Anatomy 0.000 description 1
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- 239000010410 layer Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 208000030159 metabolic disease Diseases 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- UXZJSYHVRVJKTM-UHFFFAOYSA-N methyl 2-[(3,4-dimethoxypyridin-2-yl)methylsulfinyl]-3-(ethoxycarbonyloxymethyl)-6-methylbenzimidazole-5-carboxylate Chemical compound N=1C2=CC(C)=C(C(=O)OC)C=C2N(COC(=O)OCC)C=1S(=O)CC1=NC=CC(OC)=C1OC UXZJSYHVRVJKTM-UHFFFAOYSA-N 0.000 description 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
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- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
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- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 230000001590 oxidative effect Effects 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
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- 239000004014 plasticizer Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229920001592 potato starch Chemical class 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
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- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 229940113147 shellac Drugs 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
- 235000013874 shellac Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Chemical class 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229940071138 stearyl fumarate Drugs 0.000 description 1
- 150000008163 sugars Chemical class 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
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- 238000004448 titration Methods 0.000 description 1
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- 150000003682 vanadium compounds Chemical class 0.000 description 1
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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
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9002206A SE9002206D0 (sv) | 1990-06-20 | 1990-06-20 | New compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| LTIP1712A LTIP1712A (en) | 1995-08-25 |
| LT3952B true LT3952B (en) | 1996-05-27 |
Family
ID=20379831
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LTIP1712A LT3952B (en) | 1990-06-20 | 1993-12-30 | Substituted benzimidazoles, process for their preparation and their pharmaceutical use |
| LTIP1713A LT3977B (en) | 1990-06-20 | 1993-12-30 | Dialkoxy-pyridinyl-benzimidazole derivatives, process for their preparation and their pharmaceutical use |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LTIP1713A LT3977B (en) | 1990-06-20 | 1993-12-30 | Dialkoxy-pyridinyl-benzimidazole derivatives, process for their preparation and their pharmaceutical use |
Country Status (27)
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE9002043D0 (sv) * | 1990-06-07 | 1990-06-07 | Astra Ab | Improved method for synthesis |
| SE9103776D0 (sv) * | 1991-12-19 | 1991-12-19 | Astra Ab | New compounds |
| IS4232A (is) * | 1993-12-06 | 1995-06-07 | Astra Aktiebolag | Súbstitúerað bensimidasól, aðferðir við framleiðslu þess og lyfjafræðileg notkun |
| SE504459C2 (sv) * | 1994-07-15 | 1997-02-17 | Astra Ab | Förfarande för framställning av substituerade sulfoxider |
| 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 |
| SE9600070D0 (sv) | 1996-01-08 | 1996-01-08 | Astra Ab | New oral pharmaceutical dosage forms |
| ATE281164T1 (de) | 2000-02-24 | 2004-11-15 | Kopran Res Lab Ltd | Oral verabreichbare säurebeständige geschwürbehandelnde benzimidazolderivate |
| 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 |
| AU2003246792B2 (en) | 2002-04-09 | 2008-08-28 | Flamel Ireland Limited | Oral suspension of active principle microcapsules |
| SE0203065D0 (sv) | 2002-10-16 | 2002-10-16 | Diabact Ab | Gastric acid secretion inhibiting composition |
| AU2004314693B2 (en) | 2003-09-26 | 2011-04-07 | Alza Corporation | Drug coating providing high drug loading and methods for providing the same |
| TW200606163A (en) | 2004-04-22 | 2006-02-16 | Eisai Co Ltd | Imidazopyridine compound |
| US8541026B2 (en) | 2004-09-24 | 2013-09-24 | Abbvie Inc. | Sustained release formulations of opioid and nonopioid analgesics |
| US20070015782A1 (en) * | 2005-04-15 | 2007-01-18 | Eisai Co., Ltd. | Benzimidazole compound |
| US9040564B2 (en) | 2005-04-28 | 2015-05-26 | Eisai R&D Management Co., Ltd. | Stabilized composition |
| 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 |
| WO2007122686A1 (ja) * | 2006-04-14 | 2007-11-01 | Eisai R & D Management Co., Ltd. | ベンズイミダゾール化合物 |
| ES2511792T3 (es) | 2006-07-25 | 2014-10-23 | Vecta Ltd. | Composiciones y métodos para la inhibición de la secreción de ácido gástrico usando derivados de pequeños ácidos dicarboxílicos en combinación con IBP |
| EP2065379A4 (en) * | 2006-10-13 | 2011-01-19 | Eisai R&D Man Co Ltd | BENZIMIDAZOLE HAVING INHIBITORY ACTIVITY OF GASTRIC ACID SECRETION |
| EP2344139A1 (en) | 2008-09-09 | 2011-07-20 | AstraZeneca AB | Method for delivering a pharmaceutical composition to patient in need thereof |
| JP2012531409A (ja) | 2009-06-25 | 2012-12-10 | アストラゼネカ・アクチエボラーグ | Ｎｓａｉｄ関連潰瘍を発症するリスクがある患者の処置方法 |
| WO2011080501A2 (en) | 2009-12-29 | 2011-07-07 | Orexo Ab | New pharmaceutical dosage form for the treatment of gastric acid-related disorders |
| WO2011080502A2 (en) | 2009-12-29 | 2011-07-07 | Orexo Ab | New pharmaceutical dosage form for the treatment of gastric acid-related disorders |
| WO2011080500A2 (en) | 2009-12-29 | 2011-07-07 | Orexo Ab | New pharmaceutical dosage form for the treatment of gastric acid-related disorders |
| EP2601947A1 (en) | 2011-12-05 | 2013-06-12 | Abo Bakr Mohammed Ali Al-Mehdar | Fixed-dose combination for treatment of helicobacter pylori associated diseases |
| MX2014007935A (es) | 2011-12-28 | 2014-11-14 | Pozen Inc | Composiciones y metodos mejorados para el suministro de omeprazol y de acido acetilsalicilico. |
| CA3036250C (en) | 2016-09-14 | 2023-09-26 | Yufeng Jane Tseng | Novel substituted benzimidazole derivatives as d-amino acid oxidase (daao) inhibitors |
Citations (12)
| 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 |
| BE898880A (fr) | 1983-02-11 | 1984-08-10 | Haessle Ab | Nouveaux benzimidazoles, preparations pharmaceutiques qui les contiennent et leur preparation |
| EP0124495A2 (en) | 1983-03-04 | 1984-11-07 | Aktiebolaget Hässle | Omeprazole salts |
| EP0176308A2 (en) | 1984-09-24 | 1986-04-02 | The Upjohn Company | 2-(Pyridylalkylenesulfinyl) benzimidazoles |
| US4599347A (en) | 1980-08-21 | 1986-07-08 | Hoffmann-La Roche Inc. | Tetrahydro-naphth (2.3-d) imidazole derivatives |
| EP0208452A2 (en) | 1985-07-02 | 1987-01-14 | Takeda Chemical Industries, Ltd. | Pyridine derivatives, their production and use |
| EP0221041A2 (en) | 1985-10-29 | 1987-05-06 | Aktiebolaget Hässle | Benzimidazole derivatives, process for their preparation and their pharmaceutical use |
| EP0279149A2 (en) | 1986-11-21 | 1988-08-24 | Aktiebolaget Hässle | Benzimidazole derivatives, process for their production and a pharmaceutical composition containing the same |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| IL76839A (en) * | 1984-10-31 | 1988-08-31 | Byk Gulden Lomberg Chem Fab | Picoline derivatives,processes for the preparation thereof and pharmaceutical compositions containing the same |
| DE3722810A1 (de) * | 1987-07-10 | 1989-01-19 | Hoechst Ag | Substituierte benzimidazole, verfahren zu deren herstellung, diese enthaltende pharmazeutische zubereitungen und deren verwendung |
| KR890701580A (ko) * | 1987-10-30 | 1989-12-21 | 앤더스 베딘 | 골(骨)손실에 관련된 질병 치료용 2-피리디닐메틸(술피닐 또는 티오) 벤즈이미다졸 |
| WO1989005299A1 (en) * | 1987-12-11 | 1989-06-15 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Novel benzimidazole derivatives |
| JPH03504497A (ja) * | 1988-05-25 | 1991-10-03 | ビイク グルデン ロンベルク ヒエーミツシエ フアブリーク ゲゼルシヤフト ミツト ベシユレンクテル ハフツング | 新規フルオルアルコキシ化合物 |
-
1990
- 1990-06-20 SE SE9002206A patent/SE9002206D0/xx unknown
-
1991
- 1991-06-05 ZA ZA914297A patent/ZA914297B/xx unknown
- 1991-06-05 ZA ZA914296A patent/ZA914296B/xx unknown
- 1991-06-11 EP EP91911659A patent/EP0535081A1/en not_active Withdrawn
- 1991-06-11 CA CA002083714A patent/CA2083714A1/en not_active Abandoned
- 1991-06-11 WO PCT/SE1991/000415 patent/WO1991019711A1/en not_active Application Discontinuation
- 1991-06-11 HU HU924033A patent/HUT62881A/hu unknown
- 1991-06-11 JP JP91511435A patent/JPH05507713A/ja active Pending
- 1991-06-11 RO RO92-01581A patent/RO110493B1/ro unknown
- 1991-06-11 AU AU80097/91A patent/AU649453B2/en not_active Ceased
- 1991-06-12 YU YU104191A patent/YU104191A/sh unknown
- 1991-06-12 TW TW080104582A patent/TW216418B/zh active
- 1991-06-12 IL IL98470A patent/IL98470A0/xx unknown
- 1991-06-14 NZ NZ238546A patent/NZ238546A/en unknown
- 1991-06-14 IE IE202591A patent/IE912025A1/en unknown
- 1991-06-18 MA MA22462A patent/MA22199A1/fr unknown
- 1991-06-19 AP APAP/P/1991/000285A patent/AP215A/en active
- 1991-06-19 TN TNTNSN91049A patent/TNSN91049A1/fr unknown
- 1991-06-19 PT PT98035A patent/PT98035A/pt not_active Application Discontinuation
- 1991-06-20 CZ CS911894A patent/CZ279772B6/cs unknown
- 1991-06-20 CN CN91105024A patent/CN1058212A/zh active Pending
- 1991-06-20 IS IS3721A patent/IS3721A7/is unknown
-
1992
- 1992-11-27 OA OA60306A patent/OA09682A/en unknown
- 1992-12-10 NO NO92924775A patent/NO924775L/no unknown
- 1992-12-18 FI FI925766A patent/FI925766A7/fi not_active Application Discontinuation
- 1992-12-18 BG BG097200A patent/BG97200A/bg unknown
-
1993
- 1993-08-27 LV LV931045A patent/LV10953A/xx unknown
- 1993-12-30 LT LTIP1712A patent/LT3952B/lt not_active IP Right Cessation
- 1993-12-30 LT LTIP1713A patent/LT3977B/lt not_active IP Right Cessation
Patent Citations (12)
| 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 |
| BE898880A (fr) | 1983-02-11 | 1984-08-10 | Haessle Ab | Nouveaux benzimidazoles, preparations pharmaceutiques qui les contiennent et leur preparation |
| EP0124495A2 (en) | 1983-03-04 | 1984-11-07 | Aktiebolaget Hässle | Omeprazole salts |
| EP0176308A2 (en) | 1984-09-24 | 1986-04-02 | The Upjohn Company | 2-(Pyridylalkylenesulfinyl) benzimidazoles |
| EP0208452A2 (en) | 1985-07-02 | 1987-01-14 | Takeda Chemical Industries, Ltd. | Pyridine derivatives, their production and use |
| EP0221041A2 (en) | 1985-10-29 | 1987-05-06 | Aktiebolaget Hässle | Benzimidazole derivatives, process for their preparation and their pharmaceutical use |
| EP0279149A2 (en) | 1986-11-21 | 1988-08-24 | Aktiebolaget Hässle | Benzimidazole derivatives, process for their production and a pharmaceutical composition containing the same |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM9A | Lapsed patents |
Effective date: 19961230 |