CA2124689A1 - Substituted benzimidazoles, process for their preparation as well as their use - Google Patents
Substituted benzimidazoles, process for their preparation as well as their useInfo
- Publication number
- CA2124689A1 CA2124689A1 CA002124689A CA2124689A CA2124689A1 CA 2124689 A1 CA2124689 A1 CA 2124689A1 CA 002124689 A CA002124689 A CA 002124689A CA 2124689 A CA2124689 A CA 2124689A CA 2124689 A1 CA2124689 A1 CA 2124689A1
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- compound
- formula
- pyridinyl
- dimethoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 20
- 238000000034 method Methods 0.000 title claims abstract description 12
- 150000001556 benzimidazoles Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 95
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 42
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 7
- 239000008194 pharmaceutical composition Substances 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
- 150000001768 cations Chemical class 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 30
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 29
- -1 3,4-dimethoxy 2-pyridinyl Chemical group 0.000 claims description 18
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 15
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 14
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 12
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- 238000011282 treatment Methods 0.000 claims description 8
- 230000002401 inhibitory effect Effects 0.000 claims description 6
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- 230000027119 gastric acid secretion Effects 0.000 claims description 5
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- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000005208 trialkylammonium group Chemical group 0.000 claims 2
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 27
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 7
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- ATADHKWKHYVBTJ-UHFFFAOYSA-N hydron;4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol;chloride Chemical compound Cl.CNCC(O)C1=CC=C(O)C(O)=C1 ATADHKWKHYVBTJ-UHFFFAOYSA-N 0.000 description 2
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- 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
- 229940045902 sodium stearyl fumarate Drugs 0.000 description 1
- CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 231100000967 thyroidotoxicity Toxicity 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- 230000036269 ulceration Effects 0.000 description 1
- 150000003682 vanadium compounds Chemical class 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
-
- 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
- A61K31/66—Phosphorus compounds
- A61K31/675—Phosphorus compounds having nitrogen as a ring hetero atom, e.g. pyridoxal phosphate
-
- 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
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9103776-2 | 1991-12-19 | ||
| SE9103776A SE9103776D0 (sv) | 1991-12-19 | 1991-12-19 | New compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2124689A1 true CA2124689A1 (en) | 1993-06-24 |
Family
ID=20384667
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002124689A Abandoned CA2124689A1 (en) | 1991-12-19 | 1992-12-08 | Substituted benzimidazoles, process for their preparation as well as their use |
Country Status (25)
| Country | Link |
|---|---|
| EP (1) | EP0628049A1 (ko) |
| JP (1) | JPH07502503A (ko) |
| KR (1) | KR940703840A (ko) |
| CN (1) | CN1031827C (ko) |
| AP (1) | AP397A (ko) |
| AU (1) | AU665043B2 (ko) |
| CA (1) | CA2124689A1 (ko) |
| CZ (1) | CZ146794A3 (ko) |
| FI (1) | FI942912A0 (ko) |
| HR (1) | HRP921400A2 (ko) |
| HU (1) | HUT68270A (ko) |
| IL (1) | IL104025A0 (ko) |
| IS (2) | IS4079A (ko) |
| MA (1) | MA22746A1 (ko) |
| MX (1) | MX9207269A (ko) |
| NO (1) | NO942230D0 (ko) |
| NZ (1) | NZ246220A (ko) |
| SE (1) | SE9103776D0 (ko) |
| SI (1) | SI9200402A (ko) |
| SK (1) | SK73594A3 (ko) |
| TN (1) | TNSN92115A1 (ko) |
| TW (1) | TW224100B (ko) |
| WO (1) | WO1993012124A1 (ko) |
| YU (1) | YU101692A (ko) |
| ZA (1) | ZA928836B (ko) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19645974C1 (de) * | 1996-11-07 | 1998-08-13 | Andreas Johannes Kesel | (Z)-5-[[3-Hydroxy-2-methyl-5-[(phosphonooxy)methyl]-4-pyridinyl]methylen]-2-thioxo-4- thiazolidinon, Verfahren zu dessen Herstellung und Verwendung |
| US5985856A (en) * | 1997-12-31 | 1999-11-16 | University Of Kansas | Water soluble prodrugs of secondary and tertiary amine containing drugs and methods of making thereof |
| PL1913009T3 (pl) | 2005-07-28 | 2010-10-29 | Intervet Int Bv | Nowe (tio)karbaminiany benzimidazolu o działaniu przeciwpasożytniczym i sposób ich wytwarzania |
| TWI385169B (zh) | 2005-10-31 | 2013-02-11 | Eisai R&D Man Co Ltd | 經雜環取代之吡啶衍生物及含有彼之抗真菌劑 |
| EP2037914B1 (en) | 2006-06-14 | 2013-10-23 | Intervet International BV | A suspension comprising benzimidazole carbamate and a polysorbate |
| TW200841879A (en) | 2007-04-27 | 2008-11-01 | Eisai R&D Man Co Ltd | Pyridine derivatives substituted by heterocyclic ring and phosphonoamino group, and anti-fungal agent containing same |
| US8513287B2 (en) * | 2007-12-27 | 2013-08-20 | Eisai R&D Management Co., Ltd. | Heterocyclic ring and phosphonoxymethyl group substituted pyridine derivatives and antifungal agent containing same |
| US8188119B2 (en) | 2008-10-24 | 2012-05-29 | Eisai R&D Management Co., Ltd | Pyridine derivatives substituted with heterocyclic ring and γ-glutamylamino group, and antifungal agents containing same |
| MX365051B (es) | 2014-11-26 | 2019-05-09 | Univ Mexico Nac Autonoma | Nuevos compuestos hidrosolubles derivados del bencimidazol, utiles para el tratamiento de la fasciolosis. |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ222495A (en) * | 1986-11-21 | 1991-04-26 | Haessle Ab | Benzimidazole derivatives and pharmaceutical compositions |
| SE8801907D0 (sv) * | 1988-05-20 | 1988-05-20 | Haessle Ab | Novel pharmacological compounds |
| CA2083606C (en) * | 1990-06-20 | 2001-08-21 | Arne Elof Brandstrom | Dialkoxy-pyridinyl-benzimidazole derivatives, process for their preparation and their pharmaceutical use |
| SE9002206D0 (sv) * | 1990-06-20 | 1990-06-20 | Haessle Ab | New compounds |
-
1991
- 1991-12-19 SE SE9103776A patent/SE9103776D0/xx unknown
-
1992
- 1992-10-06 IS IS4079A patent/IS4079A/is unknown
- 1992-11-11 TW TW081109053A patent/TW224100B/zh active
- 1992-11-16 ZA ZA928836A patent/ZA928836B/xx unknown
- 1992-11-25 YU YU101692A patent/YU101692A/sh unknown
- 1992-12-07 HR HR921400A patent/HRP921400A2/hr not_active Application Discontinuation
- 1992-12-08 CA CA002124689A patent/CA2124689A1/en not_active Abandoned
- 1992-12-08 WO PCT/SE1992/000844 patent/WO1993012124A1/en not_active Application Discontinuation
- 1992-12-08 EP EP93900477A patent/EP0628049A1/en not_active Withdrawn
- 1992-12-08 HU HU9401840A patent/HUT68270A/hu unknown
- 1992-12-08 CZ CZ941467A patent/CZ146794A3/cs unknown
- 1992-12-08 SK SK735-94A patent/SK73594A3/sk unknown
- 1992-12-08 KR KR1019940702131A patent/KR940703840A/ko not_active Application Discontinuation
- 1992-12-08 IL IL104025A patent/IL104025A0/xx unknown
- 1992-12-08 AU AU31752/93A patent/AU665043B2/en not_active Ceased
- 1992-12-08 NZ NZ246220A patent/NZ246220A/en unknown
- 1992-12-08 JP JP5510832A patent/JPH07502503A/ja active Pending
- 1992-12-14 AP APAP/P/1992/000463A patent/AP397A/en active
- 1992-12-15 MX MX9207269A patent/MX9207269A/es unknown
- 1992-12-16 MA MA23036A patent/MA22746A1/fr unknown
- 1992-12-18 TN TNTNSN92115A patent/TNSN92115A1/fr unknown
- 1992-12-18 SI SI19929200402A patent/SI9200402A/sl unknown
- 1992-12-18 CN CN92114364A patent/CN1031827C/zh not_active Expired - Fee Related
- 1992-12-18 IS IS3960A patent/IS3960A/is unknown
-
1994
- 1994-06-14 NO NO942230A patent/NO942230D0/no unknown
- 1994-06-17 FI FI942912A patent/FI942912A0/fi not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| IS4079A (is) | 1993-06-20 |
| AP397A (en) | 1995-08-14 |
| ZA928836B (en) | 1993-07-05 |
| NZ246220A (en) | 1996-02-27 |
| AU665043B2 (en) | 1995-12-14 |
| IL104025A0 (en) | 1993-05-13 |
| YU101692A (sh) | 1995-10-03 |
| CZ146794A3 (en) | 1996-02-14 |
| FI942912A (fi) | 1994-06-17 |
| AU3175293A (en) | 1993-07-19 |
| IS3960A (is) | 1993-06-20 |
| SI9200402A (en) | 1993-06-30 |
| SK73594A3 (en) | 1995-02-08 |
| HRP921400A2 (en) | 1994-08-31 |
| EP0628049A1 (en) | 1994-12-14 |
| WO1993012124A1 (en) | 1993-06-24 |
| TW224100B (ko) | 1994-05-21 |
| HUT68270A (en) | 1995-06-28 |
| KR940703840A (ko) | 1994-12-12 |
| MA22746A1 (fr) | 1993-07-01 |
| AP9200463A0 (en) | 1993-01-31 |
| NO942230L (no) | 1994-06-14 |
| FI942912A0 (fi) | 1994-06-17 |
| TNSN92115A1 (fr) | 1993-06-08 |
| SE9103776D0 (sv) | 1991-12-19 |
| CN1073446A (zh) | 1993-06-23 |
| JPH07502503A (ja) | 1995-03-16 |
| CN1031827C (zh) | 1996-05-22 |
| MX9207269A (es) | 1993-06-01 |
| HU9401840D0 (en) | 1994-09-28 |
| NO942230D0 (no) | 1994-06-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |