IL114492A - Benzimidazole derivatives, their preparation and pharmaceutical compositions containing them - Google Patents
Benzimidazole derivatives, their preparation and pharmaceutical compositions containing themInfo
- Publication number
- IL114492A IL114492A IL11449295A IL11449295A IL114492A IL 114492 A IL114492 A IL 114492A IL 11449295 A IL11449295 A IL 11449295A IL 11449295 A IL11449295 A IL 11449295A IL 114492 A IL114492 A IL 114492A
- Authority
- IL
- Israel
- Prior art keywords
- formula
- compound
- mmol
- benzimidazole
- dichloro
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 7
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 title description 4
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 120
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 22
- 239000001257 hydrogen Substances 0.000 claims abstract description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 20
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 125000005843 halogen group Chemical group 0.000 claims abstract description 15
- 125000003118 aryl group Chemical group 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract description 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 3
- 125000004429 atom Chemical group 0.000 claims abstract 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims description 58
- 238000009472 formulation Methods 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 28
- -1 arylCi^alkyl Chemical group 0.000 claims description 22
- 239000003795 chemical substances by application Substances 0.000 claims description 18
- 150000002148 esters Chemical class 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- 238000011282 treatment Methods 0.000 claims description 18
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- 238000011321 prophylaxis Methods 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
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- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 4
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 4
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- 230000002140 halogenating effect Effects 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
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- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 2
- 150000001413 amino acids Chemical class 0.000 claims 1
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- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims 1
- 230000000840 anti-viral effect Effects 0.000 abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 156
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 149
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- 239000007787 solid Substances 0.000 description 54
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- 239000000243 solution Substances 0.000 description 41
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 32
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- 235000019439 ethyl acetate Nutrition 0.000 description 25
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 23
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- 239000003826 tablet Substances 0.000 description 15
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- 238000006243 chemical reaction Methods 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 8
- 235000019359 magnesium stearate Nutrition 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 8
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 8
- 229940069328 povidone Drugs 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
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- 241000700605 Viruses Species 0.000 description 7
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- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 7
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 7
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 6
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- 241000282414 Homo sapiens Species 0.000 description 6
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- 239000012535 impurity Substances 0.000 description 5
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- VHBFEIBMZHEWSX-UHFFFAOYSA-N 2-isothiocyanatopropane Chemical compound CC(C)N=C=S VHBFEIBMZHEWSX-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
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- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
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- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
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- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical class OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/052—Imidazole radicals
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- General Chemical & Material Sciences (AREA)
- Communicable Diseases (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9413724A GB9413724D0 (en) | 1994-07-07 | 1994-07-07 | Therapeutic nucleosides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL114492A0 IL114492A0 (en) | 1995-11-27 |
| IL114492A true IL114492A (en) | 2002-05-23 |
Family
ID=10757983
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL11449295A IL114492A (en) | 1994-07-07 | 1995-07-06 | Benzimidazole derivatives, their preparation and pharmaceutical compositions containing them |
Country Status (43)
| Country | Link |
|---|---|
| US (4) | US6077832A (cs) |
| EP (1) | EP0769017B1 (cs) |
| JP (1) | JP3225045B2 (cs) |
| KR (1) | KR100376075B1 (cs) |
| CN (2) | CN1052010C (cs) |
| AP (1) | AP736A (cs) |
| AT (1) | ATE193298T1 (cs) |
| AU (1) | AU702248B2 (cs) |
| BG (1) | BG63435B1 (cs) |
| BR (1) | BR9508237A (cs) |
| CY (1) | CY2249B1 (cs) |
| CZ (1) | CZ290800B6 (cs) |
| DE (1) | DE69517172T2 (cs) |
| DK (1) | DK0769017T3 (cs) |
| EE (1) | EE03568B1 (cs) |
| ES (1) | ES2147294T3 (cs) |
| FI (1) | FI117629B (cs) |
| GB (1) | GB9413724D0 (cs) |
| GE (1) | GEP20002298B (cs) |
| GR (1) | GR3033744T3 (cs) |
| HR (1) | HRP950382B1 (cs) |
| HU (1) | HU227679B1 (cs) |
| IL (1) | IL114492A (cs) |
| IS (1) | IS1812B (cs) |
| MD (1) | MD1838G2 (cs) |
| MX (1) | MX9606732A (cs) |
| MY (1) | MY117892A (cs) |
| NO (1) | NO308854B1 (cs) |
| NZ (1) | NZ288722A (cs) |
| OA (1) | OA10339A (cs) |
| PL (1) | PL181136B1 (cs) |
| PT (1) | PT769017E (cs) |
| RO (1) | RO117699B1 (cs) |
| RU (1) | RU2145963C1 (cs) |
| SA (1) | SA95160202B1 (cs) |
| SK (1) | SK282046B6 (cs) |
| TJ (1) | TJ270B (cs) |
| TR (1) | TR199500832A2 (cs) |
| TW (1) | TW418196B (cs) |
| UA (1) | UA66744C2 (cs) |
| WO (1) | WO1996001833A1 (cs) |
| YU (1) | YU49443B (cs) |
| ZA (1) | ZA955644B (cs) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9413724D0 (en) * | 1994-07-07 | 1994-08-24 | Wellcome Found | Therapeutic nucleosides |
| WO1997007125A1 (en) * | 1995-08-18 | 1997-02-27 | The Regents Of The University Of Michigan | 5'-substituted-ribofuranosyl benzimidazoles as antiviral agents |
| GB9518465D0 (en) * | 1995-09-09 | 1995-11-08 | Smithkline Beecham Seiyaku Kk | Pharmaceuticals |
| GB9600143D0 (en) | 1996-01-05 | 1996-03-06 | Wellcome Found | Therapeutic compounds |
| GB9600142D0 (en) * | 1996-01-05 | 1996-03-06 | Wellcome Found | Chemical compounds |
| US6214801B1 (en) | 1996-01-23 | 2001-04-10 | The Regents Of The University Of Michigan | Imidazo[1,2-a]pyridine C-nucleosides as antiviral agents |
| US6576133B2 (en) | 1996-11-13 | 2003-06-10 | Transgenomic, Inc | Method and system for RNA analysis by matched ion polynucleotide chromatography |
| US6475388B1 (en) | 1996-11-13 | 2002-11-05 | Transgenomic, Inc. | Method and system for RNA analysis by matched ion polynucleotide chromatography |
| GB2319961A (en) * | 1996-12-07 | 1998-06-10 | Glaxo Group Ltd | Pharmaceutical composition for treatment of restenosis |
| WO1998035977A1 (en) | 1997-02-13 | 1998-08-20 | Glaxo Group Limited | Benzimidazole derivatives |
| KR20010020465A (ko) | 1997-06-10 | 2001-03-15 | 그레이엄 브레레톤, 레슬리 에드워즈 | 벤즈이미다졸 유도체 |
| CN1272113A (zh) | 1997-07-30 | 2000-11-01 | 密歇根大学董事会 | 作为抗病毒剂的来苏呋喃糖基苯并咪唑类化合物 |
| US6258264B1 (en) | 1998-04-10 | 2001-07-10 | Transgenomic, Inc. | Non-polar media for polynucleotide separations |
| GB9807354D0 (en) | 1998-04-07 | 1998-06-03 | Glaxo Group Ltd | Antiviral compound |
| GB9807355D0 (en) | 1998-04-07 | 1998-06-03 | Glaxo Group Ltd | Antiviral compound |
| US6277830B1 (en) * | 1998-10-16 | 2001-08-21 | Schering Corporation | 5′-amino acid esters of ribavirin and the use of same to treat hepatitis C with interferon |
| US6576265B1 (en) | 1999-12-22 | 2003-06-10 | Acell, Inc. | Tissue regenerative composition, method of making, and method of use thereof |
| GB0008939D0 (en) | 2000-04-11 | 2000-05-31 | Glaxo Group Ltd | Process for preparing substituted benzimidazole compounds |
| RU2262344C2 (ru) * | 2001-07-25 | 2005-10-20 | Дж.Б.Кемикалс Энд Фармасьютикалс Лтд. | Фармацевтическая композиция для лечения кожных инфекций и способ ее получения |
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