CS196278B2 - Method of producing 2-alkoxycarbonylamino-5/6/-phenylsulphonyl oxybenzimidazoles - Google Patents
Method of producing 2-alkoxycarbonylamino-5/6/-phenylsulphonyl oxybenzimidazoles Download PDFInfo
- Publication number
- CS196278B2 CS196278B2 CS755619A CS561975A CS196278B2 CS 196278 B2 CS196278 B2 CS 196278B2 CS 755619 A CS755619 A CS 755619A CS 561975 A CS561975 A CS 561975A CS 196278 B2 CS196278 B2 CS 196278B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- acid
- ester
- benzimidazole
- formula
- methoxycarbonyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 2
- 150000004987 o-phenylenediamines Chemical class 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 17
- 125000000217 alkyl group Chemical group 0.000 abstract description 5
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- 230000000507 anthelmentic effect Effects 0.000 abstract description 3
- 125000005843 halogen group Chemical group 0.000 abstract description 2
- BHFLSZOGGDDWQM-UHFFFAOYSA-N 1h-benzimidazole;carbamic acid Chemical class NC(O)=O.C1=CC=C2NC=NC2=C1 BHFLSZOGGDDWQM-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
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- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
- ZYOLIVUFDMHHDP-UHFFFAOYSA-N (3,4-diaminophenyl) 3,5-dichlorobenzenesulfonate Chemical compound C1=C(N)C(N)=CC=C1OS(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 ZYOLIVUFDMHHDP-UHFFFAOYSA-N 0.000 description 1
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- 235000012222 talc Nutrition 0.000 description 1
- UJJDEOLXODWCGK-UHFFFAOYSA-N tert-butyl carbonochloridate Chemical compound CC(C)(C)OC(Cl)=O UJJDEOLXODWCGK-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Tropical Medicine & Parasitology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS786320A CS196279B2 (cs) | 1974-08-28 | 1978-08-29 | Způsob výroby 2-alkoxykarbonylámino-5(6)-fenylsulfonyloxybenzimidazolů |
| CS786321A CS196280B2 (cs) | 1974-08-28 | 1978-08-29 | Způsob výroby 2-alkoxykarbonylamÍJio-5(6)-íenylsulfonyloxybenziinidazolů |
| CS786322A CS196281B2 (cs) | 1974-08-28 | 1978-08-29 | Způsob výroby 2-alkoxykarbonylamino-5(6)-fenylsulfonyloxybenzimidazolů |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2441201A DE2441201C2 (de) | 1974-08-28 | 1974-08-28 | Anthelminthisch wirksame 2-Carbalkoxyamino-5(6)-phenyl-sulfonyloxy-benzimidazole und Verfahren zu ihrer Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS196278B2 true CS196278B2 (en) | 1980-03-31 |
Family
ID=5924287
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS755619A CS196278B2 (en) | 1974-08-28 | 1975-08-15 | Method of producing 2-alkoxycarbonylamino-5/6/-phenylsulphonyl oxybenzimidazoles |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US3996368A (de) |
| JP (1) | JPS5910350B2 (de) |
| AT (1) | AT347935B (de) |
| BE (1) | BE832859A (de) |
| BG (3) | BG27084A3 (de) |
| CA (1) | CA1059135A (de) |
| CH (1) | CH613195A5 (de) |
| CS (1) | CS196278B2 (de) |
| DD (1) | DD124978A5 (de) |
| DE (1) | DE2441201C2 (de) |
| DK (1) | DK136188C (de) |
| ES (1) | ES440386A1 (de) |
| FI (1) | FI60203C (de) |
| FR (1) | FR2282881A1 (de) |
| GB (1) | GB1472718A (de) |
| HU (1) | HU171120B (de) |
| IE (1) | IE41521B1 (de) |
| IL (1) | IL47997A (de) |
| IT (1) | IT1041926B (de) |
| KE (1) | KE3070A (de) |
| LU (1) | LU73255A1 (de) |
| MY (1) | MY8100147A (de) |
| NL (1) | NL187208C (de) |
| NO (1) | NO140591C (de) |
| SE (1) | SE417509B (de) |
| SU (3) | SU576044A3 (de) |
| ZA (1) | ZA755486B (de) |
| ZM (1) | ZM12575A1 (de) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3132167A1 (de) * | 1981-08-14 | 1983-03-03 | Hoechst Ag, 6000 Frankfurt | "5(6)-phenylsulfonyloxy-benzimidazolderivate, verfahren zu ihrer herstellung, sie enthaltende pharmazeutische zubereitungen und ihre verwendung gegen leberegel" |
| DE2608238A1 (de) * | 1976-02-28 | 1977-09-08 | Hoechst Ag | Substituierte phenylguanidine und verfahren zu ihrer herstellung |
| DE2653766A1 (de) * | 1976-11-26 | 1978-06-01 | Bayer Ag | Substituierte benzolsulfonsaeureester, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| DE2836385A1 (de) * | 1978-08-19 | 1980-03-06 | Hoechst Ag | Monocarboxylate von phenylguanidinsulfonsaeureestern, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| DE3232959A1 (de) * | 1982-09-04 | 1984-03-08 | Hoechst Ag, 6230 Frankfurt | Substituierte benzolsulfonsaeureester, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| DE3247615A1 (de) * | 1982-12-23 | 1984-07-05 | Hoechst Ag, 6230 Frankfurt | Substituierte phenylsulfonyloxybenzimidazolcarbaminate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| DE3705227A1 (de) * | 1987-02-19 | 1988-09-01 | Bayer Ag | Anthelminthische wirkstoffkombinationen |
| EP1298125A1 (de) * | 2001-09-26 | 2003-04-02 | Aventis Pharma S.A. | Substituierte Benzimidazolverbindungen und ihre Verwendung zur Behandlung von Krebs |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE666795A (de) * | 1964-08-04 | 1966-01-13 | ||
| US3562290A (en) * | 1967-11-07 | 1971-02-09 | Du Pont | Process for making 2-benzimidazolecarbamic acid alkyl esters |
| DE1932297C3 (de) * | 1969-06-26 | 1974-09-12 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Benzimidazol -2-carbaminsäureestern |
| BE793358A (fr) * | 1971-12-27 | 1973-06-27 | Hoechst Ag | Nouveaux derives de 2-carbalcoxy-amino-benzimidazole presentantune activite anthelmintique et leur procede de preparation |
| US3929824A (en) * | 1972-12-29 | 1975-12-30 | Syntex Inc | 5(6)-Benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity |
| ZA739219B (en) * | 1972-12-29 | 1975-07-30 | Syntex Inc | 5(6)-benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity |
| US3929821A (en) * | 1972-12-29 | 1975-12-30 | Syntex Inc | 5 (6)-Benzene ring substituted benzimidazole-2-carbamate derivatives |
-
1974
- 1974-08-28 DE DE2441201A patent/DE2441201C2/de not_active Expired
-
1975
- 1975-08-15 CS CS755619A patent/CS196278B2/cs unknown
- 1975-08-22 FR FR7526015A patent/FR2282881A1/fr active Granted
- 1975-08-22 ES ES440386A patent/ES440386A1/es not_active Expired
- 1975-08-22 NL NLAANVRAGE7509957,A patent/NL187208C/xx not_active IP Right Cessation
- 1975-08-23 BG BG030848A patent/BG27084A3/xx unknown
- 1975-08-23 BG BG031578A patent/BG27234A3/xx unknown
- 1975-08-25 SE SE7509442A patent/SE417509B/xx not_active IP Right Cessation
- 1975-08-26 IT IT26581/75A patent/IT1041926B/it active
- 1975-08-26 CH CH1106875A patent/CH613195A5/xx not_active IP Right Cessation
- 1975-08-26 DD DD188034A patent/DD124978A5/xx unknown
- 1975-08-26 US US05/607,928 patent/US3996368A/en not_active Expired - Lifetime
- 1975-08-26 IL IL47997A patent/IL47997A/xx unknown
- 1975-08-26 LU LU73255A patent/LU73255A1/xx unknown
- 1975-08-26 ZM ZM125/75A patent/ZM12575A1/xx unknown
- 1975-08-26 GB GB3521875A patent/GB1472718A/en not_active Expired
- 1975-08-26 FI FI752397A patent/FI60203C/fi not_active IP Right Cessation
- 1975-08-27 AT AT663775A patent/AT347935B/de not_active IP Right Cessation
- 1975-08-27 HU HU75HO00001830A patent/HU171120B/hu not_active IP Right Cessation
- 1975-08-27 SU SU7502167451A patent/SU576044A3/ru active
- 1975-08-27 IE IE1873/75A patent/IE41521B1/en unknown
- 1975-08-27 DK DK384875A patent/DK136188C/da active
- 1975-08-27 ZA ZA00755486A patent/ZA755486B/xx unknown
- 1975-08-27 CA CA234,272A patent/CA1059135A/en not_active Expired
- 1975-08-27 NO NO752944A patent/NO140591C/no unknown
- 1975-08-28 BE BE159560A patent/BE832859A/xx not_active IP Right Cessation
- 1975-08-28 JP JP50103563A patent/JPS5910350B2/ja not_active Expired
- 1975-11-25 BG BG031577A patent/BG27233A3/bg unknown
-
1976
- 1976-09-27 SU SU762404805A patent/SU592355A3/ru active
- 1976-09-29 SU SU762404894A patent/SU592356A3/ru active
-
1980
- 1980-07-30 KE KE3070A patent/KE3070A/xx unknown
-
1981
- 1981-12-30 MY MY147/81A patent/MY8100147A/xx unknown
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