KR840006215A - 벤즈이미다졸 유도체의 제조방법 - Google Patents
벤즈이미다졸 유도체의 제조방법 Download PDFInfo
- Publication number
- KR840006215A KR840006215A KR1019830004492A KR830004492A KR840006215A KR 840006215 A KR840006215 A KR 840006215A KR 1019830004492 A KR1019830004492 A KR 1019830004492A KR 830004492 A KR830004492 A KR 830004492A KR 840006215 A KR840006215 A KR 840006215A
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- compound
- benzimidazole
- amino
- phenyl
- 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
- 238000000034 method Methods 0.000 title claims 4
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 title 1
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title 1
- -1 benzimidazole compound Chemical class 0.000 claims 29
- 150000001875 compounds Chemical class 0.000 claims 21
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims 8
- 238000004519 manufacturing process Methods 0.000 claims 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 8
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 4
- 230000002152 alkylating effect Effects 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 235000019253 formic acid Nutrition 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 125000004758 (C1-C4) alkoxyimino group Chemical group 0.000 claims 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000001118 alkylidene group Chemical group 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 150000008064 anhydrides Chemical class 0.000 claims 2
- 150000001556 benzimidazoles Chemical class 0.000 claims 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- WDFQXXPBMRCYAB-UHFFFAOYSA-N (2-amino-3-cyclohexylbenzimidazol-5-yl)-(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC=C(N=C(N)N2C3CCCCC3)C2=C1 WDFQXXPBMRCYAB-UHFFFAOYSA-N 0.000 claims 1
- BVTZZDVPZIFCPH-UHFFFAOYSA-N (2-amino-3-phenylbenzimidazol-5-yl)-phenylmethanone Chemical compound NC1=NC2=CC=C(C(=O)C=3C=CC=CC=3)C=C2N1C1=CC=CC=C1 BVTZZDVPZIFCPH-UHFFFAOYSA-N 0.000 claims 1
- RKKNQYDYMZQOFM-UHFFFAOYSA-N (2-amino-3-propan-2-ylbenzimidazol-5-yl)-phenylmethanone Chemical compound C1=C2N(C(C)C)C(N)=NC2=CC=C1C(=O)C1=CC=CC=C1 RKKNQYDYMZQOFM-UHFFFAOYSA-N 0.000 claims 1
- HXJYVTYNZXNYMV-UHFFFAOYSA-N (3-tert-butylbenzimidazol-5-yl)-phenylmethanone Chemical compound C1=C2N(C(C)(C)C)C=NC2=CC=C1C(=O)C1=CC=CC=C1 HXJYVTYNZXNYMV-UHFFFAOYSA-N 0.000 claims 1
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 claims 1
- BEYCBEUHPRVKOF-UHFFFAOYSA-N 2-(1-phenylprop-1-enyl)-1H-benzimidazole Chemical compound C(C)=C(C1=CC=CC=C1)C=1NC2=C(N=1)C=CC=C2 BEYCBEUHPRVKOF-UHFFFAOYSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- OLRFGUYHLSMJRO-UHFFFAOYSA-N 3-(2-amino-3-phenylbenzimidazol-5-yl)-3-hydroxy-3-phenylpropanenitrile Chemical compound NC1=NC2=CC=C(C(O)(CC#N)C=3C=CC=CC=3)C=C2N1C1=CC=CC=C1 OLRFGUYHLSMJRO-UHFFFAOYSA-N 0.000 claims 1
- BRKMJBQHPOTXHD-UHFFFAOYSA-N 6-(1-phenylethenyl)-1-propan-2-ylbenzimidazol-2-amine Chemical compound C1=C2N(C(C)C)C(N)=NC2=CC=C1C(=C)C1=CC=CC=C1 BRKMJBQHPOTXHD-UHFFFAOYSA-N 0.000 claims 1
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 1
- 241000243251 Hydra Species 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 1
- 150000001266 acyl halides Chemical class 0.000 claims 1
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 235000019270 ammonium chloride Nutrition 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- VGGRCVDNFAQIKO-UHFFFAOYSA-N formic anhydride Chemical compound O=COC=O VGGRCVDNFAQIKO-UHFFFAOYSA-N 0.000 claims 1
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims 1
- 125000005638 hydrazono group Chemical group 0.000 claims 1
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 claims 1
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 claims 1
- 239000004310 lactic acid Substances 0.000 claims 1
- 235000014655 lactic acid Nutrition 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- NYBWUHOMYZZKOR-UHFFFAOYSA-N tes-adt Chemical class C1=C2C(C#C[Si](CC)(CC)CC)=C(C=C3C(SC=C3)=C3)C3=C(C#C[Si](CC)(CC)CC)C2=CC2=C1SC=C2 NYBWUHOMYZZKOR-UHFFFAOYSA-N 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 210000003708 urethra Anatomy 0.000 claims 1
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
-
- 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
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- 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
-
- 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
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/12—Radicals substituted by oxygen 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
-
- 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
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
-
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Virology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/424,784 US4492708A (en) | 1982-09-27 | 1982-09-27 | Antiviral benzimidazoles |
| US424784 | 1995-04-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR840006215A true KR840006215A (ko) | 1984-11-22 |
Family
ID=23683858
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019830004492A Abandoned KR840006215A (ko) | 1982-09-27 | 1983-09-26 | 벤즈이미다졸 유도체의 제조방법 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4492708A (enExample) |
| EP (1) | EP0111993A3 (enExample) |
| JP (1) | JPS5980666A (enExample) |
| KR (1) | KR840006215A (enExample) |
| AU (1) | AU1956683A (enExample) |
| DD (1) | DD207714A5 (enExample) |
| DK (1) | DK438983D0 (enExample) |
| FI (1) | FI833424A7 (enExample) |
| GB (1) | GB2127408B (enExample) |
| GR (1) | GR79047B (enExample) |
| PL (1) | PL243905A1 (enExample) |
| PT (1) | PT77398B (enExample) |
| ZA (1) | ZA836958B (enExample) |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4728741A (en) * | 1985-01-08 | 1988-03-01 | Smithkline Beckman Corporation | 1-substituted-2-mercapto benzimidazole compounds and intermediates |
| HU193951B (en) * | 1985-03-11 | 1987-12-28 | Richter Gedeon Vegyeszet | Process for producing new sulfur-containing 5-substituted benzimidazol derivatives and pharmaceutical compositions containing them |
| FR2593177B1 (fr) * | 1986-01-20 | 1988-04-01 | Novapharme | Nouveaux benzimidazo |
| SE8604566D0 (sv) * | 1986-10-27 | 1986-10-27 | Haessle Ab | Novel compunds |
| FI91754C (fi) * | 1986-12-02 | 1994-08-10 | Tanabe Seiyaku Co | Analogiamenetelmä lääkeaineena käyttökelpoisen imidatsolijohdannaisen valmistamiseksi |
| US4851423A (en) * | 1986-12-10 | 1989-07-25 | Schering Corporation | Pharmaceutically active compounds |
| US5750532A (en) * | 1986-12-10 | 1998-05-12 | Schering Corporation | Pharmaceutically active compounds |
| US5272167A (en) * | 1986-12-10 | 1993-12-21 | Schering Corporation | Pharmaceutically active compounds |
| IE902465A1 (en) * | 1989-07-07 | 1991-02-13 | Schering Corp | Pharmaceutically active compounds |
| TW203049B (enExample) * | 1990-04-13 | 1993-04-01 | Yamanouchi Pharma Co Ltd | |
| US5591762A (en) * | 1991-02-06 | 1997-01-07 | Dr. Karl Thomae Gmbh | Benzimidazoles useful as angiotensin-11 antagonists |
| US5594003A (en) * | 1991-02-06 | 1997-01-14 | Dr. Karl Thomae Gmbh | Tetrahydroimidazo[1,2-a]pyridin-2-yl-(benzimidazol-1-yl)-methyl-biphenyls useful as angiotensin-II antagonists |
| US5602127A (en) * | 1991-02-06 | 1997-02-11 | Karl Thomae Gmbh | (Alkanesultam-1-yl)-benzimidazol-1-yl)-1yl)-methyl-biphenyls useful as angiotensin-II antagonists |
| US5210091A (en) * | 1991-06-24 | 1993-05-11 | Neurosearch A/S | Imidazole compounds and their use |
| EP0520200B1 (en) * | 1991-06-24 | 1998-02-18 | Neurosearch A/S | Imidazole compounds, their preparation and use |
| CA2085844A1 (en) * | 1991-12-27 | 1993-06-28 | Nobuyuki Hamanaka | Fused benzeneoxyacetic acid derivatives |
| GB9205071D0 (en) * | 1992-03-09 | 1992-04-22 | Wellcome Found | Therapeutic nucleosides |
| DK40192D0 (da) * | 1992-03-26 | 1992-03-26 | Neurosearch As | Imidazolforbindelser, deres fremstilling og anvendelse |
| US5399580A (en) * | 1993-03-08 | 1995-03-21 | Burroughs Wellcome Co. | Therapeutic nucleosides-uses |
| US5693661A (en) * | 1995-06-07 | 1997-12-02 | Eli Lilly And Company | Anti-viral compounds |
| US5545653A (en) * | 1995-06-07 | 1996-08-13 | Eli Lilly And Company | Anti-viral compounds |
| GB9600142D0 (en) * | 1996-01-05 | 1996-03-06 | Wellcome Found | Chemical compounds |
| EA001316B1 (ru) * | 1996-06-05 | 2001-02-26 | Эли Лилли Энд Компании | Соединения, обладающие антивирусной активностью |
| US5891874A (en) * | 1996-06-05 | 1999-04-06 | Eli Lilly And Company | Anti-viral compound |
| US5821242A (en) * | 1996-06-06 | 1998-10-13 | Eli Lilly And Company | Anti-viral compounds |
| ES2315435T3 (es) * | 1996-08-12 | 2009-04-01 | Celgene Corporation | Nuevos agentes inmunoterapeuticos y su uso para la reduccion de los niveles de citoquinas. |
| WO1998031363A1 (en) * | 1997-01-22 | 1998-07-23 | Eli Lilly And Company | Anti-viral compounds |
| CA2293508A1 (en) * | 1997-06-04 | 1998-12-10 | Louis Nickolaus Jungheim | Anti-viral compounds |
| US5990146A (en) * | 1997-08-20 | 1999-11-23 | Warner-Lambert Company | Benzimidazoles for inhibiting protein tyrosine kinase mediated cellular proliferation |
| ES2367422T3 (es) * | 2001-10-09 | 2011-11-03 | Amgen Inc. | Derivados de imidazol como agentes antiinflamatorios. |
| US7470723B2 (en) * | 2003-03-05 | 2008-12-30 | Celgene Corporation | Diphenylethylene compounds and uses thereof |
| ZA200507321B (en) * | 2003-03-05 | 2007-03-28 | Celgene Corp | Diphenylethylene compounds and uses thereof |
| ATE435222T1 (de) * | 2003-12-18 | 2009-07-15 | Tibotec Pharm Ltd | Aminobenzimidazole und benzimidazole als inhibitoren der replikation von respiratory syncytial virus |
| DK1704145T3 (da) * | 2004-01-12 | 2012-09-24 | Ym Biosciences Australia Pty | Selektive kinaseinhibitorer |
| BRPI0514857A (pt) * | 2004-09-03 | 2008-05-06 | Celgene Corp | composto ou um sal, solvato ou hidrato farmaceuticamente aceitável do mesmo, composição farmacêutica, e, métodos para inibir a angiogênese, para inibir ou reduzir a polimerização da tubulina ou a estabilidade da tubulina em uma célula, para inibir a atividade de pde4 em uma célula, para inibir atividade do fator-alfa de necrose de tumor (tnf-alfa) em uma célula, para tratar ou melhorar um distúrbio inflamatório, para tratar ou melhorar cáncer, para inibir a proliferação de célula cancerosa, para marcar, bloquear ou destruir a função de vasculatura tumoral, para marcar, bloquear ou destruir o endotélio de vasos tumor, para marcar, bloquear ou destruir a função de vasculatura tumoral e inibir a angiogênese em um tumor e para tratar ou melhorar um distúrbio do sistema nervoso central |
| EP2308852A1 (de) | 2005-08-21 | 2011-04-13 | Abbott GmbH & Co. KG | 5-Ring-Heteroaromaten-Verbindungen und ihre Verwendung als Bindungspartner für 5-HT5-Rezeptoren |
| FR2892719B3 (fr) * | 2005-11-02 | 2008-01-18 | Sep Innovaterm | Barriere physico-chimique anti-termites constituee par du beton dans lequel a ete incorpore dans toute la masse un insecticide contre les termites |
| US8871746B2 (en) | 2006-03-02 | 2014-10-28 | Kineta Four, LLC | Antiviral drugs for treatment of arenavirus infection |
| EP1988776B1 (en) * | 2006-03-02 | 2012-08-08 | Siga Technologies, Inc. | Antiviral drugs for treatment of arenavirus infection |
| US7977365B2 (en) * | 2006-03-02 | 2011-07-12 | Siga Technologies, Inc. | Antiviral drugs for treatment of arenavirus infection |
| ES2424214T3 (es) | 2007-08-27 | 2013-09-30 | Siga Technologies, Inc. | Medicamentos antivirales para el tratamiento de una infección por Arenavirus |
| US20130303782A1 (en) * | 2010-11-24 | 2013-11-14 | Sequent Scientific Limited | Process for preparation of albendazole |
| US20130303781A1 (en) * | 2010-11-24 | 2013-11-14 | Sequent Scientific Limited | Process for preparation of triclabendazole |
| US10562890B2 (en) | 2014-08-13 | 2020-02-18 | University Of Virginia Patent Foundation | Cancer therapeutics |
| KR102700664B1 (ko) * | 2017-08-07 | 2024-08-29 | 조인트 스탁 컴퍼니 “바이오케드” | Cdk8/19 저해제로서 새로운 헤테로사이클릭 화합물 |
| WO2021189080A1 (en) * | 2020-03-18 | 2021-09-23 | The Board Of Regents Of The University Of Texas System | Methods and compositions for the treatment of influenza |
| WO2022193030A1 (en) * | 2021-03-19 | 2022-09-22 | Ionomr Innovations, Inc. | Antiviral and antimicrobial coatings and methods thereof |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1045534A (en) * | 1963-02-09 | 1966-10-12 | Schering Ag | New 1-benzyl-5,6-dialkoxy benzimidazoles and a process for their manufacture |
| FR1384313A (fr) * | 1963-02-09 | 1965-01-04 | Schering Ag | Nouveaux dérivés du benzimidazole et leur préparation |
| US3336191A (en) * | 1966-03-11 | 1967-08-15 | Smith Kline French Lab | Anthelmintic 2-amidobenzimidazoles |
| FR1513160A (fr) * | 1966-03-24 | 1968-02-09 | Alfa Laval Ab | Centrifugeuse |
| US3936702A (en) * | 1972-02-24 | 1976-02-03 | Micro Devices Corporation | Electrical protection means |
| US3825537A (en) * | 1972-02-28 | 1974-07-23 | Squibb & Sons Inc | 1-thiazolin-2-yl(or thiazin-2-yl)-2-aminobenzimidazoles and derivatives thereof |
| US3813409A (en) * | 1972-07-31 | 1974-05-28 | Squibb & Sons Inc | Benzimidazolinone compounds |
| US4026936A (en) * | 1975-08-07 | 1977-05-31 | Hoffmann-La Roche Inc. | Anthelmintic pyridine and thiazole substituted benzimidazole carbamates |
| PT65486B (en) * | 1975-08-28 | 1978-03-24 | Lilly Co Eli | Process for the preparation of carbonil-substituted 1-sulfonylbenzimidazoles |
| US4174454A (en) * | 1975-08-28 | 1979-11-13 | Eli Lilly And Company | Alkylidenylmethyl-substituted 1-sulfonylbenzimidazoles |
| CA1076582A (en) * | 1975-10-28 | 1980-04-29 | Charles J. Paget | Antiviral thiazolinyl or thiazinyl ketobenzimidazoles |
| US4008243A (en) * | 1975-11-19 | 1977-02-15 | Eli Lilly And Company | Antiviral thiazolinyl or thiazinyl benzimidazole esters |
| LU75684A1 (enExample) * | 1976-08-27 | 1978-04-13 | ||
| US4191832A (en) * | 1979-03-12 | 1980-03-04 | Eli Lilly And Company | Separation of syn and anti oximes of 1-sulfonyl-2-aminobenzimidazoles |
| US4230868A (en) * | 1979-04-17 | 1980-10-28 | Eli Lilly And Company | α-Alkyl-α-hydroxybenzyl-substituted 1-sulfonylbenzimidazoles |
| US4316021A (en) * | 1979-08-13 | 1982-02-16 | Eli Lilly And Company | Substituted 1-sulfonylbenzimidazoles |
| US4338315A (en) * | 1979-11-14 | 1982-07-06 | Eli Lilly And Company | Antiviral method employing thiazinyl benzimidazole derivatives |
| US4338329A (en) * | 1979-11-14 | 1982-07-06 | Eli Lilly And Company | Antiviral method employing 1-sulfonylbenzimidazoles |
-
1982
- 1982-09-27 US US06/424,784 patent/US4492708A/en not_active Expired - Fee Related
-
1983
- 1983-09-19 ZA ZA836958A patent/ZA836958B/xx unknown
- 1983-09-19 GR GR72474A patent/GR79047B/el unknown
- 1983-09-22 EP EP83305611A patent/EP0111993A3/en not_active Ceased
- 1983-09-22 GB GB08325360A patent/GB2127408B/en not_active Expired
- 1983-09-23 FI FI833424A patent/FI833424A7/fi not_active Application Discontinuation
- 1983-09-26 PT PT77398A patent/PT77398B/pt unknown
- 1983-09-26 AU AU19566/83A patent/AU1956683A/en not_active Abandoned
- 1983-09-26 KR KR1019830004492A patent/KR840006215A/ko not_active Abandoned
- 1983-09-26 DK DK4389/83A patent/DK438983D0/da not_active Application Discontinuation
- 1983-09-26 PL PL24390583A patent/PL243905A1/xx unknown
- 1983-09-27 DD DD83255127A patent/DD207714A5/de unknown
- 1983-09-27 JP JP58181743A patent/JPS5980666A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| PT77398A (en) | 1983-10-01 |
| FI833424A0 (fi) | 1983-09-23 |
| GB2127408A (en) | 1984-04-11 |
| PL243905A1 (en) | 1985-01-30 |
| GR79047B (enExample) | 1984-10-02 |
| US4492708A (en) | 1985-01-08 |
| GB2127408B (en) | 1986-05-14 |
| GB8325360D0 (en) | 1983-10-26 |
| ZA836958B (en) | 1985-04-24 |
| JPS5980666A (ja) | 1984-05-10 |
| PT77398B (en) | 1986-03-20 |
| EP0111993A2 (en) | 1984-06-27 |
| EP0111993A3 (en) | 1984-07-25 |
| AU1956683A (en) | 1984-04-05 |
| DD207714A5 (de) | 1984-03-14 |
| DK438983D0 (da) | 1983-09-26 |
| FI833424A7 (fi) | 1984-03-28 |
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Patent event code: PA01091R01D Comment text: Patent Application Patent event date: 19830926 |
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