NO763196L - Fremgangsm}te til fremstilling av antelmintisk virksomme 2-karbalkoksyamino-5(6)-fenyl-sulfonyloksy-benzimidazoler. - Google Patents
Fremgangsm}te til fremstilling av antelmintisk virksomme 2-karbalkoksyamino-5(6)-fenyl-sulfonyloksy-benzimidazoler.Info
- Publication number
- NO763196L NO763196L NO763196A NO763196A NO763196L NO 763196 L NO763196 L NO 763196L NO 763196 A NO763196 A NO 763196A NO 763196 A NO763196 A NO 763196A NO 763196 L NO763196 L NO 763196L
- Authority
- NO
- Norway
- Prior art keywords
- benzimidazole
- carbomethoxyamino
- phenylsulfonyloxy
- acid chloride
- benzenesulfonic acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 4
- -1 benzenesulfonic acid halide Chemical class 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- 238000002844 melting Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 238000000354 decomposition reaction Methods 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- 229960000583 acetic acid Drugs 0.000 description 7
- 239000012362 glacial acetic acid Substances 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
- 239000013543 active substance Substances 0.000 description 5
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
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- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
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- ONCAZCNPWWQQMW-UHFFFAOYSA-N 3-(trifluoromethyl)benzenesulfonyl chloride Chemical compound FC(F)(F)C1=CC=CC(S(Cl)(=O)=O)=C1 ONCAZCNPWWQQMW-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
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- JHJKSEKUZNJKGO-UHFFFAOYSA-N 3-methoxybenzenesulfonyl chloride Chemical compound COC1=CC=CC(S(Cl)(=O)=O)=C1 JHJKSEKUZNJKGO-UHFFFAOYSA-N 0.000 description 2
- KFPMLWUKHQMEBU-UHFFFAOYSA-N 3-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC(S(Cl)(=O)=O)=C1 KFPMLWUKHQMEBU-UHFFFAOYSA-N 0.000 description 2
- ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 4-chlorobenzenesulfonyl chloride Chemical compound ClC1=CC=C(S(Cl)(=O)=O)C=C1 ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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- 239000007868 Raney catalyst Substances 0.000 description 2
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- 229910000564 Raney nickel Inorganic materials 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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- 244000000013 helminth Species 0.000 description 2
- 150000002431 hydrogen Chemical class 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- VIODWHADHIMZJO-UHFFFAOYSA-N (4-amino-3-nitrophenyl) benzoate Chemical compound C1=C([N+]([O-])=O)C(N)=CC=C1OC(=O)C1=CC=CC=C1 VIODWHADHIMZJO-UHFFFAOYSA-N 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-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
- C07D235/32—Benzimidazole-2-carbamic acids, unsubstituted or substituted; Esters thereof; Thio-analogues thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752541752 DE2541752A1 (de) | 1975-09-19 | 1975-09-19 | Anthelminthisch wirksame 2-carbalkoxyamino-5(6)-phenyl-sulfonyloxy- benzimidazole und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO763196L true NO763196L (no) | 1977-03-22 |
Family
ID=5956862
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO763196A NO763196L (no) | 1975-09-19 | 1976-09-17 | Fremgangsm}te til fremstilling av antelmintisk virksomme 2-karbalkoksyamino-5(6)-fenyl-sulfonyloksy-benzimidazoler. |
Country Status (12)
| Country | Link |
|---|---|
| AT (1) | AT358575B (sv) |
| CA (1) | CA1069909A (sv) |
| CH (1) | CH619938A5 (sv) |
| DE (1) | DE2541752A1 (sv) |
| DK (1) | DK141550C (sv) |
| ES (1) | ES451497A2 (sv) |
| FI (1) | FI762653A (sv) |
| GR (1) | GR60799B (sv) |
| HU (1) | HU172484B (sv) |
| NO (1) | NO763196L (sv) |
| PT (1) | PT65607B (sv) |
| SE (1) | SE7610310L (sv) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4435418A (en) * | 1982-12-13 | 1984-03-06 | Smithkline Beckman Corporation | 5-Phenylethenylbenzimidazoles |
| EP1298125A1 (en) * | 2001-09-26 | 2003-04-02 | Aventis Pharma S.A. | Substituted benzimidazole compounds and their use for the treatment of cancer |
| FR2868421B1 (fr) | 2004-04-01 | 2008-08-01 | Aventis Pharma Sa | Nouveaux benzothiazoles et leur utilisation comme medicaments |
| FR2891273B1 (fr) | 2005-09-27 | 2007-11-23 | Aventis Pharma Sa | NOUVEAUX DERIVES BENZIMIDAZOLES ET BENZOTHIAZOLES, LEUR PREPARATION ET LEUR UTILISATION PHARMACEUTIQUE NOTAMMENT COMME INHIBITEURS DE CMet |
-
1975
- 1975-09-19 DE DE19752541752 patent/DE2541752A1/de active Pending
-
1976
- 1976-09-14 ES ES451497A patent/ES451497A2/es not_active Expired
- 1976-09-16 HU HU76HO00001929A patent/HU172484B/hu unknown
- 1976-09-16 SE SE7610310A patent/SE7610310L/sv unknown
- 1976-09-16 FI FI762653A patent/FI762653A/fi not_active Application Discontinuation
- 1976-09-17 CA CA261,425A patent/CA1069909A/en not_active Expired
- 1976-09-17 AT AT690876A patent/AT358575B/de active
- 1976-09-17 NO NO763196A patent/NO763196L/no unknown
- 1976-09-17 PT PT65607A patent/PT65607B/pt unknown
- 1976-09-17 DK DK419876A patent/DK141550C/da active
- 1976-09-17 CH CH1182076A patent/CH619938A5/de not_active IP Right Cessation
- 1976-09-18 GR GR51724A patent/GR60799B/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ATA690876A (de) | 1980-02-15 |
| DK141550B (da) | 1980-04-21 |
| DK141550C (da) | 1980-10-06 |
| PT65607A (de) | 1976-10-01 |
| ES451497A2 (es) | 1977-12-01 |
| CA1069909A (en) | 1980-01-15 |
| DE2541752A1 (de) | 1977-03-24 |
| CH619938A5 (en) | 1980-10-31 |
| GR60799B (en) | 1978-08-30 |
| HU172484B (hu) | 1978-09-28 |
| SE7610310L (sv) | 1977-03-20 |
| PT65607B (de) | 1978-05-10 |
| FI762653A (sv) | 1977-03-20 |
| AT358575B (de) | 1980-09-25 |
| DK419876A (da) | 1977-03-20 |
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