SE444679B - Sett att framstella 5(6)-substituerad bensimidazol-(2)-metylkarbamat med antihelmintisk verkan - Google Patents
Sett att framstella 5(6)-substituerad bensimidazol-(2)-metylkarbamat med antihelmintisk verkanInfo
- Publication number
- SE444679B SE444679B SE7804305A SE7804305A SE444679B SE 444679 B SE444679 B SE 444679B SE 7804305 A SE7804305 A SE 7804305A SE 7804305 A SE7804305 A SE 7804305A SE 444679 B SE444679 B SE 444679B
- Authority
- SE
- Sweden
- Prior art keywords
- general formula
- give
- substituted benzimidazole
- antihelmintic
- make
- Prior art date
Links
- 230000000507 anthelmentic effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 8
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims description 2
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 150000003573 thiols Chemical class 0.000 claims 2
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 244000000013 helminth Species 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- 241001494479 Pecora Species 0.000 description 5
- BHFLSZOGGDDWQM-UHFFFAOYSA-N 1h-benzimidazole;carbamic acid Chemical class NC(O)=O.C1=CC=C2NC=NC2=C1 BHFLSZOGGDDWQM-UHFFFAOYSA-N 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- -1 4 - [(3,3-dichlorophenyl) -thio] -2-nitroaniline Chemical compound 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000002685 pulmonary effect Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- UQYKZBVOGVSJNG-UHFFFAOYSA-N 4-(7,7-dichlorohept-6-enylsulfanyl)-2-nitroaniline Chemical compound ClC(=CCCCCCSC1=CC(=C(N)C=C1)[N+](=O)[O-])Cl UQYKZBVOGVSJNG-UHFFFAOYSA-N 0.000 description 2
- 241000242722 Cestoda Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- 241000510960 Oesophagostomum Species 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- QUWHIBBGKKRYFW-UHFFFAOYSA-N (4-amino-3-nitrophenyl) thiocyanate Chemical compound NC1=CC=C(SC#N)C=C1[N+]([O-])=O QUWHIBBGKKRYFW-UHFFFAOYSA-N 0.000 description 1
- JFEVIPGMXQNRRF-UHFFFAOYSA-N 1,1,3-trichloroprop-1-ene Chemical group ClCC=C(Cl)Cl JFEVIPGMXQNRRF-UHFFFAOYSA-N 0.000 description 1
- ZCWBZRBJSPWUPG-UHFFFAOYSA-N 4-bromo-2-nitroaniline Chemical compound NC1=CC=C(Br)C=C1[N+]([O-])=O ZCWBZRBJSPWUPG-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 208000005577 Gastroenteritis Diseases 0.000 description 1
- 206010061201 Helminthic infection Diseases 0.000 description 1
- 206010056522 Hepatic infection Diseases 0.000 description 1
- 206010022678 Intestinal infections Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical class SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- 241001137878 Moniezia Species 0.000 description 1
- 241000244206 Nematoda Species 0.000 description 1
- 241000243795 Ostertagia Species 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 241000282849 Ruminantia Species 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 244000144980 herd Species 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- NXTCWSIFQLEOLL-UHFFFAOYSA-N methyl N-carbamothioyl-N-methylcarbamate Chemical compound COC(=O)N(C(S)=N)C NXTCWSIFQLEOLL-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000000384 rearing effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- GVCGWXSZNUOTDW-UHFFFAOYSA-N sulfo cyanate Chemical compound OS(=O)(=O)OC#N GVCGWXSZNUOTDW-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- 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)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT22645/77A IT1076022B (it) | 1977-04-20 | 1977-04-20 | Benzimidazolcarbammati antielmintici |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7804305L SE7804305L (sv) | 1978-10-21 |
| SE444679B true SE444679B (sv) | 1986-04-28 |
Family
ID=11198787
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7804305A SE444679B (sv) | 1977-04-20 | 1978-04-17 | Sett att framstella 5(6)-substituerad bensimidazol-(2)-metylkarbamat med antihelmintisk verkan |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4182893A (de) |
| AR (1) | AR219526A1 (de) |
| AT (1) | AT356672B (de) |
| AU (1) | AU520133B2 (de) |
| BE (1) | BE866195A (de) |
| BR (1) | BR7802445A (de) |
| CA (1) | CA1104142A (de) |
| CH (1) | CH639077A5 (de) |
| DE (1) | DE2816694C2 (de) |
| DK (1) | DK154076C (de) |
| FR (1) | FR2387965A1 (de) |
| GB (1) | GB1581517A (de) |
| IE (1) | IE46869B1 (de) |
| IT (1) | IT1076022B (de) |
| NL (1) | NL7804049A (de) |
| NZ (1) | NZ187003A (de) |
| SE (1) | SE444679B (de) |
| SU (1) | SU764609A3 (de) |
| ZA (1) | ZA782250B (de) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4174400A (en) * | 1978-09-13 | 1979-11-13 | Merck & Co., Inc. | Anthelmintic benzimidazoles |
| DE2845537A1 (de) * | 1978-10-19 | 1980-04-30 | Bayer Ag | Benzimidazolylcarbamidsaeureester, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| NL7908719A (nl) * | 1978-12-06 | 1980-06-10 | Montedison Spa | Benzimidazoolcarbamaten. |
| US4299837A (en) | 1979-12-05 | 1981-11-10 | Montedison S.P.A. | Anthelmintic benzimidazole-carbamates |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK131821C (da) * | 1967-03-22 | 1976-03-08 | Smith Kline French Lab | Analogifremgangsmade til fremstilling af en 2-karbalkoksyaminobenzimidazol |
| US3657267A (en) * | 1969-06-20 | 1972-04-18 | Janssen Pharmaceutica Nv | Benzimidazole carbamates |
| 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 |
| US3929821A (en) * | 1972-12-29 | 1975-12-30 | Syntex Inc | 5 (6)-Benzene ring substituted benzimidazole-2-carbamate derivatives |
| US3929824A (en) * | 1972-12-29 | 1975-12-30 | Syntex Inc | 5(6)-Benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity |
| US3929823A (en) * | 1973-11-21 | 1975-12-30 | Syntex Inc | 5(6)-Benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity |
| US3915986A (en) * | 1974-06-19 | 1975-10-28 | Smithkline Corp | Methyl 5-propylthio-2-benzimidazolecarbamate |
-
1977
- 1977-04-20 IT IT22645/77A patent/IT1076022B/it active
-
1978
- 1978-04-17 SE SE7804305A patent/SE444679B/sv not_active IP Right Cessation
- 1978-04-17 NL NL7804049A patent/NL7804049A/xx not_active Application Discontinuation
- 1978-04-17 DK DK166278A patent/DK154076C/da not_active IP Right Cessation
- 1978-04-17 CH CH410378A patent/CH639077A5/it not_active IP Right Cessation
- 1978-04-18 AT AT272878A patent/AT356672B/de not_active IP Right Cessation
- 1978-04-18 NZ NZ187003A patent/NZ187003A/xx unknown
- 1978-04-18 DE DE2816694A patent/DE2816694C2/de not_active Expired
- 1978-04-18 AU AU35193/78A patent/AU520133B2/en not_active Expired
- 1978-04-18 AR AR271814A patent/AR219526A1/es active
- 1978-04-19 SU SU782608100A patent/SU764609A3/ru active
- 1978-04-19 BR BR7802445A patent/BR7802445A/pt unknown
- 1978-04-19 IE IE769/78A patent/IE46869B1/en unknown
- 1978-04-19 GB GB15476/78A patent/GB1581517A/en not_active Expired
- 1978-04-19 FR FR7811486A patent/FR2387965A1/fr active Granted
- 1978-04-19 ZA ZA00782250A patent/ZA782250B/xx unknown
- 1978-04-19 US US05/897,853 patent/US4182893A/en not_active Expired - Lifetime
- 1978-04-20 CA CA301,605A patent/CA1104142A/en not_active Expired
- 1978-04-20 BE BE186963A patent/BE866195A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| US4182893A (en) | 1980-01-08 |
| DE2816694A1 (de) | 1978-10-26 |
| AR219526A1 (es) | 1980-08-29 |
| DK154076B (da) | 1988-10-10 |
| IE46869B1 (en) | 1983-10-19 |
| IT1076022B (it) | 1985-04-22 |
| ATA272878A (de) | 1979-10-15 |
| BR7802445A (pt) | 1978-12-19 |
| SE7804305L (sv) | 1978-10-21 |
| DK154076C (da) | 1989-02-27 |
| NZ187003A (en) | 1981-03-16 |
| AT356672B (de) | 1980-05-12 |
| NL7804049A (nl) | 1978-10-24 |
| AU520133B2 (en) | 1982-01-14 |
| BE866195A (fr) | 1978-10-20 |
| SU764609A3 (ru) | 1980-09-15 |
| GB1581517A (en) | 1980-12-17 |
| CH639077A5 (it) | 1983-10-31 |
| IE780769L (en) | 1978-10-20 |
| CA1104142A (en) | 1981-06-30 |
| AU3519378A (en) | 1979-10-25 |
| ZA782250B (en) | 1979-04-25 |
| FR2387965A1 (fr) | 1978-11-17 |
| FR2387965B1 (de) | 1980-10-10 |
| DK166278A (da) | 1978-10-21 |
| DE2816694C2 (de) | 1986-02-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NUG | Patent has lapsed |
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