BE903128A - BENZIMIDAZOLE DERIVATIVES PROCESS FOR THEIR PREPARATION AND ANTI-ULCER AGENTS CONTAINING THEM - Google Patents
BENZIMIDAZOLE DERIVATIVES PROCESS FOR THEIR PREPARATION AND ANTI-ULCER AGENTS CONTAINING THEMInfo
- Publication number
- BE903128A BE903128A BE0/215506A BE215506A BE903128A BE 903128 A BE903128 A BE 903128A BE 0/215506 A BE0/215506 A BE 0/215506A BE 215506 A BE215506 A BE 215506A BE 903128 A BE903128 A BE 903128A
- Authority
- BE
- Belgium
- Prior art keywords
- group
- preparation
- agents containing
- benzimidazole derivatives
- hydrogen atom
- Prior art date
Links
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 title 1
- 239000003699 antiulcer agent Substances 0.000 title 1
- 150000001556 benzimidazoles Chemical class 0.000 title 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
- 208000025865 Ulcer Diseases 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- 231100000397 ulcer Toxicity 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
-
- 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
-
- 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
- C07D235/26—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
Des dérives de benzimodazole de formule (I) dans laquelle R1 représente un atome d'hydrogène, un groupe alkyle en C1-C8, un groupe cycloalkyle, un groupe phényle ou un groupe aralkyle, R2 représente un atome d'hydrogène ou un groupe alkyle en C1-C8, ou encore R1 et R2 forment un noyau ensemble avec l'atome d'azote adjacent, tandis que R3 et R4 représentent chacun un atome d'hydrogène, un atome d'halogène, un groupe trifluorométhyle, un groupe alkyle inférieur, un groupe alcoxy inférieur, un groupe alcoxy inférieur-carbonyle ou un groupe amino, ces dérivés étant efficaces contre les ulcères.Benzimodazole derivatives of formula (I) in which R1 represents a hydrogen atom, a C1-C8 alkyl group, a cycloalkyl group, a phenyl group or an aralkyl group, R2 represents a hydrogen atom or an alkyl group in C1-C8, or R1 and R2 form a nucleus together with the adjacent nitrogen atom, while R3 and R4 each represent a hydrogen atom, a halogen atom, a trifluoromethyl group, a lower alkyl group , a lower alkoxy group, a lower alkoxy-carbonyl group or an amino group, these derivatives being effective against ulcers.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59182400A JPS6160660A (en) | 1984-08-31 | 1984-08-31 | Benzimidazole derivative, its preparation, and antitumor agent containing it |
| JP60061194A JPH068283B2 (en) | 1985-03-26 | 1985-03-26 | Benzimidazole derivative, method for producing the same, and antiulcer agent containing the same |
| JP60061195A JPH0764826B2 (en) | 1985-03-26 | 1985-03-26 | Benzimidazole derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE903128A true BE903128A (en) | 1985-12-16 |
Family
ID=27297422
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE0/215506A BE903128A (en) | 1984-08-31 | 1985-08-27 | BENZIMIDAZOLE DERIVATIVES PROCESS FOR THEIR PREPARATION AND ANTI-ULCER AGENTS CONTAINING THEM |
Country Status (14)
| Country | Link |
|---|---|
| KR (1) | KR920004936B1 (en) |
| AR (1) | AR242195A1 (en) |
| AU (3) | AU4640985A (en) |
| BE (1) | BE903128A (en) |
| BR (1) | BR8504252A (en) |
| CH (1) | CH665417A5 (en) |
| DE (1) | DE3531487C2 (en) |
| ES (1) | ES8703142A1 (en) |
| FR (1) | FR2569691B1 (en) |
| GB (1) | GB2163747B (en) |
| IT (1) | IT1189601B (en) |
| MX (1) | MX159807A (en) |
| NL (1) | NL8502384A (en) |
| SE (1) | SE500669C2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4687775A (en) * | 1986-07-17 | 1987-08-18 | G. D. Searle & Co. | 2-[(Imidazo[1,2-a]pyridinylmethyl)sulfinyl]-1H-benzimidazoles |
| US4721718A (en) * | 1986-08-18 | 1988-01-26 | G. D. Searle & Co. | 2-[(imidazo[1,2-a]pyridin-3-ylmethyl)sulfinyl]-1H-benzimidazoles useful in the treatment and prevention of ulcers |
| US4772619A (en) * | 1986-07-17 | 1988-09-20 | G. D. Searle & Co. | [(1H-benzimidazol-2-ylsulfinyl)methyl]-2-pyridinamines |
Families Citing this family (64)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8417194D0 (en) * | 1984-07-05 | 1984-08-08 | Boots Co Plc | Therapeutic agents |
| EP0174717B1 (en) | 1984-07-06 | 1992-01-22 | FISONS plc | Benzimidazoles, and their production formulation and use as gastric acid secretion inhibitors |
| GB2161160B (en) * | 1984-07-06 | 1989-05-24 | Fisons Plc | Heterocyclic sulphinyl compounds |
| US5869513A (en) * | 1985-05-24 | 1999-02-09 | G. D. Searle & Co. | 2- (1H-benzimidazol-2-ylsulfinyl)methyl!benzenamines |
| AU5768886A (en) * | 1985-05-24 | 1986-11-27 | G.D. Searle & Co. | 2-((1-h-benzimidazol-2-ylsulfinyl)methyl)benzenamines |
| US4824856A (en) * | 1985-08-14 | 1989-04-25 | Nippon Chemiphar Co., Ltd. | Method of protecting gastrointestinal tract |
| EP0232399A1 (en) * | 1985-08-21 | 1987-08-19 | Byk Gulden Lomberg Chemische Fabrik GmbH | New amines, process for their manufacture, their use and medicines containing them |
| AR243167A1 (en) | 1985-08-24 | 1993-07-30 | Hoechst Ag | Substituted toluidines, process for their preparation, pharmaceutical compositions containing them and their use as gastric secretion inhibitors |
| AU619444B2 (en) * | 1986-06-02 | 1992-01-30 | Nippon Chemiphar Co. Ltd. | 2-(2-aminobenzylsulfinyl)- benzimidazole derivatives |
| EP0251536A1 (en) * | 1986-06-24 | 1988-01-07 | FISONS plc | Benzimidazoles, their production, formulation and use as gastric acid secretion inhibitors |
| DE3639926A1 (en) * | 1986-11-22 | 1988-06-01 | Hoechst Ag | SUBSTITUTED THIENOIMIDAZOLTOLUIDINE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF, PHARMACEUTICAL PREPARATIONS CONTAINING IT AND THEIR USE AS AN INGESTIC ACID INHIBITOR |
| IT1222412B (en) * | 1987-07-31 | 1990-09-05 | Chiesi Farma Spa | THYOMETHYL AND SULFINYL METHYL DERIVED WITH ANTI-SECRET ACID GASTRIC ACTION, THEIR PREPARATION PROCEDURE AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
| JP2614756B2 (en) * | 1988-08-10 | 1997-05-28 | 日本ケミファ株式会社 | Imidazole derivative, method for producing the same, and anti-ulcer agent containing the same |
| JPH06298611A (en) * | 1993-04-16 | 1994-10-25 | Nippon Chemiphar Co Ltd | Antibacterial agent |
| SE9301489D0 (en) | 1993-04-30 | 1993-04-30 | Ab Astra | VETERINARY COMPOSITION |
| SE9402431D0 (en) * | 1994-07-08 | 1994-07-08 | Astra Ab | New tablet formulation |
| SE9500422D0 (en) * | 1995-02-06 | 1995-02-06 | Astra Ab | New oral pharmaceutical dosage forms |
| SE9500478D0 (en) * | 1995-02-09 | 1995-02-09 | Astra Ab | New pharmaceutical formulation and process |
| US5708017A (en) * | 1995-04-04 | 1998-01-13 | Merck & Co., Inc. | Stable, ready-to-use pharmaceutical paste composition containing proton pump inhibitors |
| HRP960232A2 (en) * | 1995-07-03 | 1998-02-28 | Astra Ab | A process for the optical purification of compounds |
| CN1093855C (en) * | 1995-09-21 | 2002-11-06 | 帕斯医药股份有限公司 | Novel compositions containing acid-labile omeprazole and processes for their preparation |
| SE9600070D0 (en) | 1996-01-08 | 1996-01-08 | Astra Ab | New oral pharmaceutical dosage forms |
| US6380222B2 (en) | 1996-10-11 | 2002-04-30 | Astrazeneca Ab | Use of an H+, K+-atpase inhibitor in the treatment of nasal polyps |
| US6303644B1 (en) | 1997-07-25 | 2001-10-16 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Proton pump inhibitor in therapeutic combination with antibacterial substances |
| SE9704870D0 (en) | 1997-12-22 | 1997-12-22 | Astra Ab | New pharmaceutical formulation I |
| SE9704869D0 (en) * | 1997-12-22 | 1997-12-22 | Astra Ab | New pharmaceutical formulaton II |
| WO2000009092A1 (en) | 1998-08-12 | 2000-02-24 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Oral administration form for pyridin-2-ylmethylsulfinyl-1h-benzimidazoles |
| WO2000027841A1 (en) * | 1998-11-06 | 2000-05-18 | Dong-A Pharmaceutical Co., Ltd. | Method of preparing sulfide derivatives |
| TWI243672B (en) | 1999-06-01 | 2005-11-21 | Astrazeneca Ab | New use of compounds as antibacterial agents |
| JP4980527B2 (en) | 1999-06-07 | 2012-07-18 | ニコメッド ゲゼルシャフト ミット ベシュレンクテル ハフツング | Novel formulations and dosage forms containing acid labile active compounds |
| SE9903831D0 (en) | 1999-10-22 | 1999-10-22 | Astra Ab | Formulation of substituted benzimidazoles |
| SE0000774D0 (en) | 2000-03-08 | 2000-03-08 | Astrazeneca Ab | New formulation |
| US6544556B1 (en) | 2000-09-11 | 2003-04-08 | Andrx Corporation | Pharmaceutical formulations containing a non-steroidal antiinflammatory drug and a proton pump inhibitor |
| SE0101379D0 (en) | 2001-04-18 | 2001-04-18 | Diabact Ab | Composition that inhibits gastric acid secretion |
| US8206741B2 (en) | 2001-06-01 | 2012-06-26 | Pozen Inc. | Pharmaceutical compositions for the coordinated delivery of NSAIDs |
| SE0102993D0 (en) | 2001-09-07 | 2001-09-07 | Astrazeneca Ab | New self emulsifying drug delivery system |
| US8101209B2 (en) | 2001-10-09 | 2012-01-24 | Flamel Technologies | Microparticulate oral galenical form for the delayed and controlled release of pharmaceutical active principles |
| MXPA04009968A (en) | 2002-04-09 | 2004-12-13 | Flamel Tech Sa | Oral suspension of active principle microcapsules. |
| DE60323474D1 (en) | 2002-04-09 | 2008-10-23 | Flamel Tech Sa | ORAL PHARMACEUTICAL FORMULATION IN THE FORM OF AQUEOUS SUSPENSION OF MICRO-CAPSULES FOR THE MODIFIED RELEASE OF AMOXICILLIN |
| SE0203065D0 (en) | 2002-10-16 | 2002-10-16 | Diabact Ab | Gastric acid secretion inhibiting composition |
| EP2112920B1 (en) | 2003-06-26 | 2018-07-25 | Intellipharmaceutics Corp. | Proton pump-inhibitor-containing capsules which comprise subunits differently structured for a delayed release of the active ingredient |
| US8246986B2 (en) | 2003-09-26 | 2012-08-21 | Alza Corporation | Drug coating providing high drug loading |
| US8394409B2 (en) | 2004-07-01 | 2013-03-12 | Intellipharmaceutics Corp. | Controlled extended drug release technology |
| US20060024362A1 (en) | 2004-07-29 | 2006-02-02 | Pawan Seth | Composition comprising a benzimidazole and process for its manufacture |
| US10624858B2 (en) | 2004-08-23 | 2020-04-21 | Intellipharmaceutics Corp | Controlled release composition using transition coating, and method of preparing same |
| 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 |
| US10064828B1 (en) | 2005-12-23 | 2018-09-04 | Intellipharmaceutics Corp. | Pulsed extended-pulsed and extended-pulsed pulsed drug delivery systems |
| WO2007112581A1 (en) | 2006-04-03 | 2007-10-11 | Isa Odidi | Controlled release delivery device comprising an organosol coat |
| US10960077B2 (en) | 2006-05-12 | 2021-03-30 | Intellipharmaceutics Corp. | Abuse and alcohol resistant drug composition |
| US9233092B2 (en) | 2006-07-25 | 2016-01-12 | Vecta, Ltd. | Compositions and methods for inhibiting gastric acid secretion using derivatives of small dicarboxylic acids in combination with PPI |
| NZ598728A (en) | 2006-12-22 | 2013-09-27 | Ironwood Pharmaceuticals Inc | Compositions comprising bile acid sequestrants for treating esophageal disorders |
| EA201100313A1 (en) | 2008-09-09 | 2011-10-31 | Астразенека Аб | METHOD OF DELIVERY OF THE PHARMACEUTICAL COMPOSITION TO THE PATIENT NEEDING THIS |
| CA2764963C (en) | 2009-06-25 | 2016-11-01 | Astrazeneca Ab | Method for treating a patient at risk for developing an nsaid-associated ulcer |
| WO2011080500A2 (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 |
| WO2011080501A2 (en) | 2009-12-29 | 2011-07-07 | Orexo Ab | New pharmaceutical dosage form for the treatment of gastric acid-related disorders |
| US20130156720A1 (en) | 2010-08-27 | 2013-06-20 | Ironwood Pharmaceuticals, Inc. | Compositions and methods for treating or preventing metabolic syndrome and related diseases and 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 |
| BR112014016085A8 (en) | 2011-12-28 | 2017-07-04 | Pozen Inc | Enhanced compositions and methods for delivery of omeprazole plus acetylsalicylic acid |
| CA2898362C (en) | 2013-01-15 | 2020-09-01 | Ironwood Pharmaceuticals, Inc. | Gastro-retentive sustained-release oral dosage form of a bile acid sequestrant |
| EP2801565B1 (en) | 2013-05-06 | 2015-07-22 | King Saud University | Compounds for use as anti-ulcer agent and/or anti-Helicobacter pylori agent and pharmaceutical compositions thereof |
| US20180015118A1 (en) | 2015-02-03 | 2018-01-18 | Ironwood Pharmaceuticals, Inc. | Methods of treating upper gastrointestinal disorders in ppi refractory gerd |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4359465A (en) * | 1980-07-28 | 1982-11-16 | The Upjohn Company | Methods for treating gastrointestinal inflammation |
| EP0174717B1 (en) * | 1984-07-06 | 1992-01-22 | FISONS plc | Benzimidazoles, and their production formulation and use as gastric acid secretion inhibitors |
-
1985
- 1985-08-19 AU AU46409/85A patent/AU4640985A/en not_active Abandoned
- 1985-08-27 ES ES546445A patent/ES8703142A1/en not_active Expired
- 1985-08-27 BE BE0/215506A patent/BE903128A/en not_active IP Right Cessation
- 1985-08-29 CH CH3709/85A patent/CH665417A5/en not_active IP Right Cessation
- 1985-08-29 GB GB08521493A patent/GB2163747B/en not_active Expired
- 1985-08-30 NL NL8502384A patent/NL8502384A/en not_active Application Discontinuation
- 1985-08-30 IT IT67743/85A patent/IT1189601B/en active
- 1985-08-30 MX MX206462A patent/MX159807A/en unknown
- 1985-08-30 BR BR8504252A patent/BR8504252A/en unknown
- 1985-08-30 KR KR1019850006307A patent/KR920004936B1/en not_active Expired
- 1985-08-30 FR FR858512961A patent/FR2569691B1/en not_active Expired
- 1985-08-30 AR AR85301474A patent/AR242195A1/en active
- 1985-08-30 SE SE8504048A patent/SE500669C2/en unknown
- 1985-08-30 DE DE3531487A patent/DE3531487C2/en not_active Expired - Fee Related
-
1989
- 1989-09-11 AU AU41271/89A patent/AU4127189A/en not_active Abandoned
-
1992
- 1992-11-27 AU AU29750/92A patent/AU647978B2/en not_active Ceased
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4687775A (en) * | 1986-07-17 | 1987-08-18 | G. D. Searle & Co. | 2-[(Imidazo[1,2-a]pyridinylmethyl)sulfinyl]-1H-benzimidazoles |
| US4772619A (en) * | 1986-07-17 | 1988-09-20 | G. D. Searle & Co. | [(1H-benzimidazol-2-ylsulfinyl)methyl]-2-pyridinamines |
| US4721718A (en) * | 1986-08-18 | 1988-01-26 | G. D. Searle & Co. | 2-[(imidazo[1,2-a]pyridin-3-ylmethyl)sulfinyl]-1H-benzimidazoles useful in the treatment and prevention of ulcers |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2975092A (en) | 1993-01-28 |
| GB2163747A (en) | 1986-03-05 |
| FR2569691A1 (en) | 1986-03-07 |
| GB8521493D0 (en) | 1985-10-02 |
| BR8504252A (en) | 1986-06-17 |
| AU4640985A (en) | 1986-03-06 |
| GB2163747B (en) | 1989-02-08 |
| AU4127189A (en) | 1989-12-21 |
| DE3531487C2 (en) | 1995-08-17 |
| SE8504048L (en) | 1986-03-01 |
| KR860001793A (en) | 1986-03-22 |
| ES546445A0 (en) | 1986-11-16 |
| AR242195A1 (en) | 1993-03-31 |
| KR920004936B1 (en) | 1992-06-22 |
| IT8567743A0 (en) | 1985-08-30 |
| FR2569691B1 (en) | 1989-08-04 |
| NL8502384A (en) | 1986-03-17 |
| AU647978B2 (en) | 1994-03-31 |
| SE8504048D0 (en) | 1985-08-30 |
| SE500669C2 (en) | 1994-08-08 |
| MX159807A (en) | 1989-08-31 |
| ES8703142A1 (en) | 1986-11-16 |
| CH665417A5 (en) | 1988-05-13 |
| IT1189601B (en) | 1988-02-04 |
| DE3531487A1 (en) | 1986-03-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RE | Patent lapsed |
Owner name: NIPPON CHEMIPHAR CO. LTD Effective date: 20000831 |