GB1568543A - 2-amino-or acylamino)-1-sulphonyl-benzoimidazole derivativves - Google Patents
2-amino-or acylamino)-1-sulphonyl-benzoimidazole derivativves Download PDFInfo
- Publication number
- GB1568543A GB1568543A GB5254/77A GB525477A GB1568543A GB 1568543 A GB1568543 A GB 1568543A GB 5254/77 A GB5254/77 A GB 5254/77A GB 525477 A GB525477 A GB 525477A GB 1568543 A GB1568543 A GB 1568543A
- Authority
- GB
- United Kingdom
- Prior art keywords
- benzimidazole
- amino
- dimethylaminosulfonyl
- alkyl
- compounds
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 41
- 230000018044 dehydration Effects 0.000 claims abstract description 5
- 238000006297 dehydration reaction Methods 0.000 claims abstract description 5
- 229910052744 lithium Inorganic materials 0.000 claims abstract description 4
- 230000007062 hydrolysis Effects 0.000 claims abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract 2
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- -1 sulfonyl benzimidazole compound Chemical class 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
- 125000001118 alkylidene group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000005059 halophenyl group Chemical group 0.000 claims description 3
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 2
- 230000010933 acylation Effects 0.000 claims description 2
- 238000005917 acylation reaction Methods 0.000 claims description 2
- 150000004791 alkyl magnesium halides Chemical class 0.000 claims description 2
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- IYUBCLHILARKQB-UHFFFAOYSA-N 2-sulfonylbenzimidazole Chemical class C1=CC=CC2=NC(=S(=O)=O)N=C21 IYUBCLHILARKQB-UHFFFAOYSA-N 0.000 abstract description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 14
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- 239000000047 product Substances 0.000 description 12
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- SXUXQJLILGMLOR-UHFFFAOYSA-N (2-amino-3-propan-2-ylsulfonylbenzimidazol-5-yl)-phenylmethanone Chemical compound C1=C2N(S(=O)(=O)C(C)C)C(N)=NC2=CC=C1C(=O)C1=CC=CC=C1 SXUXQJLILGMLOR-UHFFFAOYSA-N 0.000 description 4
- KHPXETCHASHFOZ-UHFFFAOYSA-N 2-amino-6-benzoyl-n,n-dimethylbenzimidazole-1-sulfonamide Chemical compound C1=C2N(S(=O)(=O)N(C)C)C(N)=NC2=CC=C1C(=O)C1=CC=CC=C1 KHPXETCHASHFOZ-UHFFFAOYSA-N 0.000 description 4
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- 108091003079 Bovine Serum Albumin Proteins 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
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- 239000007818 Grignard reagent Substances 0.000 description 2
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- 229930182555 Penicillin Natural products 0.000 description 2
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 230000000840 anti-viral effect Effects 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- LWLPYZUDBNFNAH-UHFFFAOYSA-M magnesium;butane;bromide Chemical compound [Mg+2].[Br-].CCC[CH2-] LWLPYZUDBNFNAH-UHFFFAOYSA-M 0.000 description 2
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 2
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 2
- IUYHWZFSGMZEOG-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
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- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- XRGHQBXKSHAQRB-UHFFFAOYSA-N 1h-benzimidazole-2-sulfonamide Chemical compound C1=CC=C2NC(S(=O)(=O)N)=NC2=C1 XRGHQBXKSHAQRB-UHFFFAOYSA-N 0.000 description 1
- JBAOXNRYELBOKN-UHFFFAOYSA-N 2-amino-n,n-dimethylbenzimidazole-1-sulfonamide Chemical class C1=CC=C2N(S(=O)(=O)N(C)C)C(N)=NC2=C1 JBAOXNRYELBOKN-UHFFFAOYSA-N 0.000 description 1
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 229960005486 vaccine Drugs 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Communicable Diseases (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Virology (AREA)
- Oncology (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)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/750,991 US4118742A (en) | 1975-08-28 | 1976-12-15 | Carbonyl-substituted 1-sulfonylbenzimidazoles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1568543A true GB1568543A (en) | 1980-05-29 |
Family
ID=25019992
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5254/77A Expired GB1568543A (en) | 1976-12-15 | 1977-02-09 | 2-amino-or acylamino)-1-sulphonyl-benzoimidazole derivativves |
Country Status (26)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2119789A (en) * | 1982-04-08 | 1983-11-23 | Lilly Co Eli | Olefinic benzimidazoles |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2593177B1 (fr) * | 1986-01-20 | 1988-04-01 | Novapharme | Nouveaux benzimidazo |
| US5693661A (en) * | 1995-06-07 | 1997-12-02 | Eli Lilly And Company | Anti-viral compounds |
| JP7226480B2 (ja) | 2020-07-30 | 2023-02-21 | 大日本印刷株式会社 | 抗ウイルス性物品及び抗ウイルス性樹脂組成物 |
| CN116209572A (zh) | 2020-09-18 | 2023-06-02 | 大日本印刷株式会社 | 抗病毒性物品和抗病毒性树脂组合物 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51125078A (en) * | 1974-07-01 | 1976-11-01 | Lilly Co Eli | Production of substituted 11sulphonylbenzimidazole |
-
1977
- 1977-02-07 ZA ZA00770691A patent/ZA77691B/xx unknown
- 1977-02-07 GR GR52736A patent/GR66420B/el unknown
- 1977-02-08 IE IE259/77A patent/IE44863B1/en not_active IP Right Cessation
- 1977-02-08 CA CA271,307A patent/CA1079737A/en not_active Expired
- 1977-02-09 GB GB5254/77A patent/GB1568543A/en not_active Expired
- 1977-02-14 DE DE19772706227 patent/DE2706227A1/de active Granted
- 1977-02-14 IL IL51445A patent/IL51445A/xx unknown
- 1977-02-17 NL NLAANVRAGE7701715,A patent/NL187396C/xx not_active IP Right Cessation
- 1977-02-17 RO RO7789438A patent/RO71886A/ro unknown
- 1977-02-18 DD DD7700197445A patent/DD129445A6/xx unknown
- 1977-02-18 HU HU77EI729A patent/HU175361B/hu unknown
- 1977-02-18 MX MX775442U patent/MX4495E/es unknown
- 1977-02-18 SE SE7701845A patent/SE433351B/xx not_active IP Right Cessation
- 1977-02-18 CS CS771093A patent/CS190339B2/cs unknown
- 1977-02-18 CH CH207577A patent/CH630368A5/de not_active IP Right Cessation
- 1977-02-18 DK DK73277A patent/DK145645C/da not_active IP Right Cessation
- 1977-02-18 AU AU22440/77A patent/AU509374B2/en not_active Expired
- 1977-02-18 JP JP1769877A patent/JPS5377062A/ja active Granted
- 1977-02-18 BE BE1007954A patent/BE851630A/xx not_active IP Right Cessation
- 1977-02-18 AT AT111277A patent/AT347937B/de not_active IP Right Cessation
- 1977-02-18 ES ES456090A patent/ES456090A1/es not_active Expired
- 1977-02-18 BG BG035460A patent/BG27742A3/xx unknown
- 1977-02-18 SU SU772452269A patent/SU680645A3/ru active
- 1977-02-18 AR AR266611A patent/AR225397A1/es active
- 1977-02-18 FR FR7704799A patent/FR2374311A2/fr active Granted
- 1977-02-19 PL PL1977196131A patent/PL106887B1/pl unknown
-
1980
- 1980-11-18 SE SE8008090A patent/SE433352B/sv not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2119789A (en) * | 1982-04-08 | 1983-11-23 | Lilly Co Eli | Olefinic benzimidazoles |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| 704A | Declaration that licence is not available as of right for an excepted use (par. 4a/1977) | ||
| PE20 | Patent expired after termination of 20 years |
Effective date: 19960823 |