NO120582B - - Google Patents
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- Publication number
- NO120582B NO120582B NO166120A NO16612066A NO120582B NO 120582 B NO120582 B NO 120582B NO 166120 A NO166120 A NO 166120A NO 16612066 A NO16612066 A NO 16612066A NO 120582 B NO120582 B NO 120582B
- Authority
- NO
- Norway
- Prior art keywords
- lower alkyl
- formula
- phenylenediamine
- substituted
- product
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- -1 4-n- butyl Chemical group 0.000 claims description 8
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 claims description 8
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 150000004987 o-phenylenediamines Chemical class 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 claims description 2
- 150000001556 benzimidazoles Chemical class 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
- 150000001875 compounds Chemical class 0.000 description 16
- 239000000047 product Substances 0.000 description 14
- 150000004985 diamines Chemical class 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 7
- 229960000583 acetic acid Drugs 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 6
- WEYSQARHSRZNTC-UHFFFAOYSA-N 1h-benzimidazol-2-ylcarbamic acid Chemical class C1=CC=C2NC(NC(=O)O)=NC2=C1 WEYSQARHSRZNTC-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000006396 nitration reaction Methods 0.000 description 6
- 230000003595 spectral effect Effects 0.000 description 6
- 239000001119 stannous chloride Substances 0.000 description 6
- 235000011150 stannous chloride Nutrition 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 238000006722 reduction reaction Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 150000004996 alkyl benzenes Chemical class 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229910017604 nitric acid Inorganic materials 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 4
- VZOPVKZLLGMDDG-UHFFFAOYSA-N 1-oxido-4-phenylpyridin-1-ium Chemical compound C1=C[N+]([O-])=CC=C1C1=CC=CC=C1 VZOPVKZLLGMDDG-UHFFFAOYSA-N 0.000 description 3
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- HSNWZBCBUUSSQD-UHFFFAOYSA-N amyl nitrate Chemical compound CCCCCO[N+]([O-])=O HSNWZBCBUUSSQD-UHFFFAOYSA-N 0.000 description 3
- 150000001448 anilines Chemical class 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000013067 intermediate product Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YEQKUNLRMROOGQ-UHFFFAOYSA-N 4-butoxybenzene-1,2-diamine Chemical compound CCCCOC1=CC=C(N)C(N)=C1 YEQKUNLRMROOGQ-UHFFFAOYSA-N 0.000 description 2
- LSRWUTOORAKKIE-UHFFFAOYSA-N 4-hexylbenzene-1,2-diamine Chemical compound CCCCCCC1=CC=C(N)C(N)=C1 LSRWUTOORAKKIE-UHFFFAOYSA-N 0.000 description 2
- UUAOMJOZLSTWIP-UHFFFAOYSA-N 4-propoxybenzene-1,2-diamine Chemical compound CCCOC1=CC=C(N)C(N)=C1 UUAOMJOZLSTWIP-UHFFFAOYSA-N 0.000 description 2
- ZPZZLBVKKPQYAK-UHFFFAOYSA-N 4-propylbenzene-1,2-diamine Chemical compound CCCC1=CC=C(N)C(N)=C1 ZPZZLBVKKPQYAK-UHFFFAOYSA-N 0.000 description 2
- LTEQMZWBSYACLV-UHFFFAOYSA-N Hexylbenzene Chemical compound CCCCCCC1=CC=CC=C1 LTEQMZWBSYACLV-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- RAOCRURYZCVHMG-UHFFFAOYSA-N N-(6-propoxy-1H-benzimidazol-2-yl)carbamic acid methyl ester Chemical compound CCCOC1=CC=C2N=C(NC(=O)OC)NC2=C1 RAOCRURYZCVHMG-UHFFFAOYSA-N 0.000 description 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
- 241000244206 Nematoda Species 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 150000001347 alkyl bromides Chemical class 0.000 description 2
- 150000003931 anilides Chemical class 0.000 description 2
- 230000000507 anthelmentic effect Effects 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- CFAUKBLKOCSPKB-UHFFFAOYSA-N methyl n-(6-butoxy-1h-benzimidazol-2-yl)carbamate Chemical compound CCCCOC1=CC=C2N=C(NC(=O)OC)NC2=C1 CFAUKBLKOCSPKB-UHFFFAOYSA-N 0.000 description 2
- JIRCNXLDBOJKBP-UHFFFAOYSA-N methyl n-(6-propyl-1h-benzimidazol-2-yl)carbamate Chemical compound CCCC1=CC=C2N=C(NC(=O)OC)NC2=C1 JIRCNXLDBOJKBP-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- IOIOILDYKMQXSF-UHFFFAOYSA-N sulfuric acid;thiourea Chemical compound NC(N)=S.OS(O)(=O)=O IOIOILDYKMQXSF-UHFFFAOYSA-N 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical class NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- SXQBFCVVZIYXHV-UHFFFAOYSA-N 1-nitro-4-propylbenzene Chemical compound CCCC1=CC=C([N+]([O-])=O)C=C1 SXQBFCVVZIYXHV-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- KEBUEWXZQBMCNB-UHFFFAOYSA-N 1h-benzimidazol-2-yl carbamate Chemical class C1=CC=C2NC(OC(=O)N)=NC2=C1 KEBUEWXZQBMCNB-UHFFFAOYSA-N 0.000 description 1
- VUMCVANUWQZNGD-UHFFFAOYSA-N 2-nitro-4-propoxyaniline Chemical compound CCCOC1=CC=C(N)C([N+]([O-])=O)=C1 VUMCVANUWQZNGD-UHFFFAOYSA-N 0.000 description 1
- UACSJWZBISFLIW-UHFFFAOYSA-N 2-nitro-4-propylaniline Chemical compound CCCC1=CC=C(N)C([N+]([O-])=O)=C1 UACSJWZBISFLIW-UHFFFAOYSA-N 0.000 description 1
- JFPJVTNYCURRAB-UHFFFAOYSA-N 2-nitro-n-phenylacetamide Chemical compound [O-][N+](=O)CC(=O)NC1=CC=CC=C1 JFPJVTNYCURRAB-UHFFFAOYSA-N 0.000 description 1
- IPZPZSUDOPUDPM-UHFFFAOYSA-N 3,4-dinitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C([N+]([O-])=O)=C1 IPZPZSUDOPUDPM-UHFFFAOYSA-N 0.000 description 1
- WQEGHHLKDKIWKM-UHFFFAOYSA-N 4-butylbenzene-1,2-diamine Chemical compound CCCCC1=CC=C(N)C(N)=C1 WQEGHHLKDKIWKM-UHFFFAOYSA-N 0.000 description 1
- OVEMTTZEBOCJDV-UHFFFAOYSA-N 4-hexylaniline Chemical compound CCCCCCC1=CC=C(N)C=C1 OVEMTTZEBOCJDV-UHFFFAOYSA-N 0.000 description 1
- OAPDPORYXWQVJE-UHFFFAOYSA-N 4-propylaniline Chemical compound CCCC1=CC=C(N)C=C1 OAPDPORYXWQVJE-UHFFFAOYSA-N 0.000 description 1
- 241000244188 Ascaris suum Species 0.000 description 1
- OFEYFCWZZYFXHU-UHFFFAOYSA-N C(=O)(OC)NC=1NC2=C(N=1)C=CC(=C2)CCCCCC Chemical compound C(=O)(OC)NC=1NC2=C(N=1)C=CC(=C2)CCCCCC OFEYFCWZZYFXHU-UHFFFAOYSA-N 0.000 description 1
- 206010061201 Helminthic infection Diseases 0.000 description 1
- 241000283903 Ovis aries Species 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 241000282849 Ruminantia Species 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- SSBRSHIQIANGKS-UHFFFAOYSA-N [amino(hydroxy)methylidene]azanium;hydrogen sulfate Chemical compound NC(N)=O.OS(O)(=O)=O SSBRSHIQIANGKS-UHFFFAOYSA-N 0.000 description 1
- 229960001413 acetanilide Drugs 0.000 description 1
- 150000008061 acetanilides Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- RUOKPLVTMFHRJE-UHFFFAOYSA-N benzene-1,2,3-triamine Chemical compound NC1=CC=CC(N)=C1N RUOKPLVTMFHRJE-UHFFFAOYSA-N 0.000 description 1
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000020176 deacylation Effects 0.000 description 1
- 238000005947 deacylation reaction Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 231100000057 systemic toxicity Toxicity 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
-
- 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)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38752464A | 1964-08-04 | 1964-08-04 | |
| US51612065A | 1965-12-23 | 1965-12-23 | |
| US56211766A | 1966-07-01 | 1966-07-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO120582B true NO120582B (pt) | 1970-11-09 |
Family
ID=27409808
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO166120A NO120582B (pt) | 1964-08-04 | 1966-12-22 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3574845A (pt) |
| BE (2) | BE666795A (pt) |
| BR (1) | BR6685587D0 (pt) |
| CH (1) | CH479590A (pt) |
| CY (1) | CY621A (pt) |
| DE (1) | DE1795799A1 (pt) |
| DK (1) | DK130586B (pt) |
| FI (1) | FI46962C (pt) |
| FR (3) | FR4648M (pt) |
| GB (3) | GB1096190A (pt) |
| IL (1) | IL27006A (pt) |
| IT (2) | IT1043764B (pt) |
| NL (1) | NL153535B (pt) |
| NO (1) | NO120582B (pt) |
| SE (1) | SE342819B (pt) |
Families Citing this family (55)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3541213A (en) * | 1966-05-06 | 1970-11-17 | Du Pont | Fungicidal and mite ovicidal substituted 2-aminobenzimidazoles |
| DK131821C (da) * | 1967-03-22 | 1976-03-08 | Smith Kline French Lab | Analogifremgangsmade til fremstilling af en 2-karbalkoksyaminobenzimidazol |
| US3997553A (en) * | 1969-06-25 | 1976-12-14 | E. I. Du Pont De Nemours And Company | 2-Benzimidazolecarbamic acid esters by the cyanamide process |
| US3694454A (en) * | 1970-07-17 | 1972-09-26 | Boehringer Sohn Ingelheim | 1-{8 1{40 -carboxylic acylamino-2{40 ,2{40 ,2{40 -trichloro)-ethyl{9 -2-(hydrocarbyloxycarbonyl-amino)-benzimidazoles |
| US3852460A (en) * | 1971-01-06 | 1974-12-03 | C Littler | Acid salts of 2-benzimidazolecarbamic acid, alkyl esters as fungicides |
| CA1032171A (en) * | 1972-12-29 | 1978-05-30 | Colin C. Beard | 5(6)-benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity |
| US3965113A (en) * | 1972-12-29 | 1976-06-22 | Syntex (U.S.A.) Inc. | 5(6)-Benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity |
| US3929824A (en) * | 1972-12-29 | 1975-12-30 | 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 |
| US3993769A (en) * | 1972-12-29 | 1976-11-23 | Syntex (U.S.A.) Inc. | 1,5(6)-Disubstituted benzimidazole-2-carbamate derivatives having anthelmintic activity |
| US4046906A (en) * | 1973-04-21 | 1977-09-06 | Hoechst Aktiengesellschaft | Salts of alkyl 2-benzimidazole-carbamate |
| US3969526A (en) * | 1973-05-29 | 1976-07-13 | Smithkline Corporation | Anthelmintic 5-heterocycliothio and oxy-2-carbalkoxyaminobenzimidazles |
| US4258198A (en) * | 1973-05-29 | 1981-03-24 | Smithkline Corporation | 5-Cycloalkyl thio- and oxy-2-carbalkoxyaminobenzimidazoles |
| US3962437A (en) * | 1973-06-19 | 1976-06-08 | Syntex (U.S.A.) Inc. | 5(6)-Benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity |
| US3901901A (en) * | 1973-06-19 | 1975-08-26 | Syntex Inc | 5(6)-benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity |
| DE2348104A1 (de) * | 1973-09-25 | 1975-04-03 | Hoechst Ag | Anthelmintisch wirksame 2-carbalkoxyamino-benzimidazolyl-5(6)-amino-phenylaether und verfahren zu ihrer herstellung |
| US3929823A (en) * | 1973-11-21 | 1975-12-30 | Syntex Inc | 5(6)-Benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity |
| HU169503B (pt) * | 1974-02-05 | 1976-12-28 | ||
| US3915986A (en) * | 1974-06-19 | 1975-10-28 | Smithkline Corp | Methyl 5-propylthio-2-benzimidazolecarbamate |
| DE2432631A1 (de) * | 1974-07-06 | 1976-01-22 | Hoechst Ag | 5-phenylsulfinyl-2-benzimidazol-carbaminsaeureester und verfahren zu ihrer herstellung |
| DE2441201C2 (de) * | 1974-08-28 | 1986-08-07 | Hoechst Ag, 6230 Frankfurt | Anthelminthisch wirksame 2-Carbalkoxyamino-5(6)-phenyl-sulfonyloxy-benzimidazole und Verfahren zu ihrer Herstellung |
| DE2441202C2 (de) * | 1974-08-28 | 1986-05-28 | Hoechst Ag, 6230 Frankfurt | 2-Carbalkoxyamino-benzimidazolyl-5(6)-sulfonsäure-phenylester, Verfahren zu ihrer Herstellung und diese enthaltende anthelmintische Mittel |
| US3993768A (en) * | 1974-11-25 | 1976-11-23 | Syntex (U.S.A.) Inc. | 5(6)-Benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity |
| US4025638A (en) * | 1975-03-10 | 1977-05-24 | Smithkline Corporation | Methods and compositions using 5-cycloalkylthio- and oxy-2-carbalkoxy-aminobenzimidazole |
| US4076825A (en) * | 1977-06-22 | 1978-02-28 | E. R. Squibb & Sons, Inc. | Method of treating helminthiasis by parenteral or topical administration of sulfoxide derivatives of benzimidazoles |
| US4076828A (en) * | 1977-02-17 | 1978-02-28 | E. R. Squibb & Sons, Inc. | Method of treating helminthiasis by parenteral administration of sulfoxide derivatives of benzimidazoles |
| US4076827A (en) * | 1977-04-28 | 1978-02-28 | E. R. Squibb & Sons, Inc. | Method of treating helminthiasis by parenteral administration of sulfoxide derivatives of benzimidazoles |
| SE443977B (sv) * | 1977-05-10 | 1986-03-17 | Chinoin Gyogyszer Es Vegyeszet | Forfarande for framstellning av 5(6)-tio-bensimidazolderivat |
| US4152522A (en) * | 1978-01-03 | 1979-05-01 | Ethyl Corporation | Process for the preparation of 2-benzimidazole carbamates |
| US4136174A (en) * | 1978-01-18 | 1979-01-23 | E. R. Squibb & Sons, Inc. | Benzimidazolecarbamates and method |
| US4156006A (en) * | 1978-01-09 | 1979-05-22 | E. R. Squibb & Sons, Inc. | Vinyl sulfide derivatives of benzimidazoles |
| US4154846A (en) * | 1978-06-16 | 1979-05-15 | E. R. Squibb & Sons, Inc. | Substituted thio-, sulfinyl-, and sulfonyl-alkyl benzimidazole carbamates |
| US4174400A (en) * | 1978-09-13 | 1979-11-13 | Merck & Co., Inc. | Anthelmintic benzimidazoles |
| DE2840927A1 (de) * | 1978-09-20 | 1980-04-10 | Bayer Ag | 3,4-dihydroisochinoline, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| US4487936A (en) * | 1979-12-04 | 1984-12-11 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt. | Preparation of alkylthiobenzimidazoles |
| US4299837A (en) | 1979-12-05 | 1981-11-10 | Montedison S.P.A. | Anthelmintic benzimidazole-carbamates |
| US4656276A (en) * | 1980-08-07 | 1987-04-07 | Angus Chemical Company | Quinoxaline adducts useful as anthelmintics |
| US4629790A (en) * | 1980-08-07 | 1986-12-16 | Angus Chemical Company | Quinoxaline adducts useful as anthelmintics |
| US4658028A (en) * | 1980-08-07 | 1987-04-14 | Angus Chemical Company | Quinoxaline adducts useful as anthelmintics |
| US4720548A (en) * | 1980-08-07 | 1988-01-19 | Angus Chemical Company | Quinoxaline adducts useful as anthelmintics |
| US4661593A (en) * | 1980-08-07 | 1987-04-28 | Angus Chemcial Company | Quinoxaline adducts useful as anthelmintics |
| US4348389A (en) * | 1980-08-07 | 1982-09-07 | International Minerals & Chemical Corp. | Quinoxaline adducts useful as anthelmintics |
| GB9124002D0 (en) * | 1991-11-12 | 1992-01-02 | Pfizer Ltd | Benzimidazole anthelmintic agents |
| US6262093B1 (en) | 1995-04-12 | 2001-07-17 | The Proctor & Gamble Company | Methods of treating cancer with benzimidazoles |
| US6479526B1 (en) | 1995-04-12 | 2002-11-12 | The Procter & Gamble Company | Pharmaceutical composition for inhibiting the growth of viruses and cancers |
| US6506783B1 (en) * | 1997-05-16 | 2003-01-14 | The Procter & Gamble Company | Cancer treatments and pharmaceutical compositions therefor |
| US6423734B1 (en) * | 1999-08-13 | 2002-07-23 | The Procter & Gamble Company | Method of preventing cancer |
| US6462062B1 (en) * | 2000-09-26 | 2002-10-08 | The Procter & Gamble Company | Compounds and methods for use thereof in the treatment of cancer or viral infections |
| US6380232B1 (en) | 2000-09-26 | 2002-04-30 | The Procter & Gamble Company | Benzimidazole urea derivatives, and pharmaceutical compositions and unit dosages thereof |
| US6608096B1 (en) * | 2000-09-26 | 2003-08-19 | University Of Arizona Foundation | Compounds and methods for use thereof in the treatment of cancer or viral infections |
| PL1913009T3 (pl) * | 2005-07-28 | 2010-10-29 | Intervet Int Bv | Nowe (tio)karbaminiany benzimidazolu o działaniu przeciwpasożytniczym i sposób ich wytwarzania |
| WO2008091358A1 (en) * | 2006-06-12 | 2008-07-31 | Smith And Nephew Inc | Systems, methods and devices for tibial resection |
| EP2037914B1 (en) | 2006-06-14 | 2013-10-23 | Intervet International BV | A suspension comprising benzimidazole carbamate and a polysorbate |
| CA3043549C (en) | 2015-11-30 | 2023-11-21 | Children's Medical Center Corporation | Compounds for treating proliferative diseases |
| US20230147129A1 (en) | 2020-03-27 | 2023-05-11 | Som Innovation Biotech, S.A. | Compounds for use in the treatment of synucleinopathies |
-
1965
- 1965-07-13 BE BE666795D patent/BE666795A/xx unknown
- 1965-07-30 GB GB32818/65A patent/GB1096190A/en not_active Expired
- 1965-08-04 FR FR27162A patent/FR4648M/fr not_active Expired
-
1966
- 1966-07-01 US US562117A patent/US3574845A/en not_active Expired - Lifetime
- 1966-07-06 GB GB30428/66A patent/GB1114069A/en not_active Expired
- 1966-12-04 IL IL27006A patent/IL27006A/xx unknown
- 1966-12-08 DK DK636566AA patent/DK130586B/da unknown
- 1966-12-19 CH CH1816466A patent/CH479590A/de not_active IP Right Cessation
- 1966-12-19 GB GB56839/66A patent/GB1123317A/en not_active Expired
- 1966-12-20 FI FI663382A patent/FI46962C/fi active
- 1966-12-21 BR BR185587/66A patent/BR6685587D0/pt unknown
- 1966-12-22 BE BE691611D patent/BE691611A/xx not_active IP Right Cessation
- 1966-12-22 DE DE19661795799 patent/DE1795799A1/de active Pending
- 1966-12-22 NO NO166120A patent/NO120582B/no unknown
- 1966-12-22 IT IT31439/66A patent/IT1043764B/it active
- 1966-12-22 FR FR88441A patent/FR1510235A/fr not_active Expired
- 1966-12-22 FR FR88435A patent/FR5840M/fr not_active Expired
- 1966-12-22 SE SE17580/66A patent/SE342819B/xx unknown
- 1966-12-23 NL NL666618109A patent/NL153535B/xx not_active IP Right Cessation
-
1967
- 1967-05-26 IT IT16552/67A patent/IT1056714B/it active
-
1971
- 1971-11-19 CY CY62171A patent/CY621A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CY621A (en) | 1971-11-19 |
| IL27006A (en) | 1971-04-28 |
| NL6618109A (pt) | 1967-06-26 |
| BE666795A (pt) | 1966-01-13 |
| IT1043764B (it) | 1980-02-29 |
| GB1096190A (en) | 1967-12-20 |
| DK130586B (da) | 1975-03-10 |
| NL153535B (nl) | 1977-06-15 |
| FR5840M (pt) | 1968-03-04 |
| GB1123317A (en) | 1968-08-14 |
| IT1056714B (it) | 1982-02-20 |
| FI46962B (pt) | 1973-05-02 |
| BE691611A (fr) | 1967-06-22 |
| FR4648M (pt) | 1966-12-05 |
| DK130586C (pt) | 1975-08-18 |
| GB1114069A (en) | 1968-05-15 |
| US3574845A (en) | 1971-04-13 |
| SE342819B (pt) | 1972-02-21 |
| DE1795799A1 (de) | 1975-10-02 |
| FI46962C (fi) | 1973-08-10 |
| CH479590A (de) | 1969-10-15 |
| DE1620439A1 (de) | 1970-04-23 |
| BR6685587D0 (pt) | 1973-12-27 |
| DE1620439B2 (de) | 1975-12-18 |
| FR1510235A (fr) | 1968-01-19 |
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