SU1169532A3 - Способ получени бензимидазолкарбаматов и его вариант - Google Patents
Способ получени бензимидазолкарбаматов и его вариант Download PDFInfo
- Publication number
- SU1169532A3 SU1169532A3 SU792847574A SU2847574A SU1169532A3 SU 1169532 A3 SU1169532 A3 SU 1169532A3 SU 792847574 A SU792847574 A SU 792847574A SU 2847574 A SU2847574 A SU 2847574A SU 1169532 A3 SU1169532 A3 SU 1169532A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- general formula
- compound
- compounds
- different
- methyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 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 title abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 13
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 13
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 9
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract 4
- 150000001875 compounds Chemical class 0.000 claims description 53
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 239000000460 chlorine Substances 0.000 claims description 14
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 239000011593 sulfur Chemical group 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims description 5
- BHFLSZOGGDDWQM-UHFFFAOYSA-N 1h-benzimidazole;carbamic acid Chemical class NC(O)=O.C1=CC=C2NC=NC2=C1 BHFLSZOGGDDWQM-UHFFFAOYSA-N 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 5
- 150000004965 peroxy acids Chemical class 0.000 claims description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 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
- 150000001879 copper Chemical class 0.000 claims description 3
- 230000003993 interaction Effects 0.000 claims description 3
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 6
- 125000004429 atom Chemical group 0.000 claims 2
- 238000006704 dehydrohalogenation reaction Methods 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 1
- CTFKOMUXSHQLLL-UHFFFAOYSA-N 2,6-ditert-butyl-4-[[1-(hydroxymethyl)cyclopentyl]methyl]phenol Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CC2(CO)CCCC2)=C1 CTFKOMUXSHQLLL-UHFFFAOYSA-N 0.000 claims 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 150000002391 heterocyclic compounds Chemical class 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 230000033116 oxidation-reduction process Effects 0.000 claims 1
- 150000003303 ruthenium Chemical class 0.000 claims 1
- 230000000507 anthelmentic effect Effects 0.000 abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 34
- 238000005481 NMR spectroscopy Methods 0.000 description 33
- 239000000243 solution Substances 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- -1 1, 5, 5-trichloro-3-methylpent-1, 3-diene Chemical compound 0.000 description 8
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 241001494479 Pecora Species 0.000 description 7
- HXHWSAZORRCQMX-UHFFFAOYSA-N albendazole Chemical compound CCCSC1=CC=C2NC(NC(=O)OC)=NC2=C1 HXHWSAZORRCQMX-UHFFFAOYSA-N 0.000 description 7
- 229960002669 albendazole Drugs 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 241000244206 Nematoda Species 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- RJDXPVXKAUSDFR-UHFFFAOYSA-N 1,5,5,5-tetrachloro-2-methylpent-2-ene Chemical compound ClCC(C)=CCC(Cl)(Cl)Cl RJDXPVXKAUSDFR-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 230000000968 intestinal effect Effects 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 230000002685 pulmonary effect Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000004611 spectroscopical analysis Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 241001147667 Dictyocaulus Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000013256 coordination polymer Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 description 1
- COXVPYKZDDKVRF-ULQDDVLXSA-N (4,4-difluorocyclohexyl)methyl N-[(2S)-4-methyl-1-oxo-1-[[(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]pentan-2-yl]carbamate Chemical compound CC(C)C[C@@H](C(=O)N[C@@H](C[C@@H]1CCNC1=O)C=O)NC(=O)OCC2CCC(CC2)(F)F COXVPYKZDDKVRF-ULQDDVLXSA-N 0.000 description 1
- XXGGQXPAPAXDFJ-UHFFFAOYSA-N 1,1,5-trichloro-3-methylpenta-1,3-diene Chemical compound ClCC=C(C)C=C(Cl)Cl XXGGQXPAPAXDFJ-UHFFFAOYSA-N 0.000 description 1
- DPLLDFXEYFSOAP-UHFFFAOYSA-N 1,1,5-trichloro-4-methylpenta-1,3-diene Chemical compound ClCC(C)=CC=C(Cl)Cl DPLLDFXEYFSOAP-UHFFFAOYSA-N 0.000 description 1
- SHFSVIOZPSUWFD-UHFFFAOYSA-N 1,1-dichloro-3-methylpentane Chemical compound [H]C([H])C([H])C(C([H])C(Cl)Cl)C([H])([H])[H] SHFSVIOZPSUWFD-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 241000243789 Metastrongyloidea Species 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- 241000935974 Paralichthys dentatus Species 0.000 description 1
- 241000218657 Picea Species 0.000 description 1
- 239000012327 Ruthenium complex Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241000242541 Trematoda Species 0.000 description 1
- 241000869417 Trematodes Species 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C21/00—Acyclic unsaturated compounds containing halogen atoms
- C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
- C07C21/04—Chloro-alkenes
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/272—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions
- C07C17/275—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of hydrocarbons and halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C21/00—Acyclic unsaturated compounds containing halogen atoms
- C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
- C07C21/14—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing bromine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C21/00—Acyclic unsaturated compounds containing halogen atoms
- C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
- C07C21/18—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT30618/78A IT1100788B (it) | 1978-12-06 | 1978-12-06 | Benzimidazol-carbammati |
| IT26734/79A IT1125577B (it) | 1979-10-24 | 1979-10-24 | Benzimidazol carbammati |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1169532A3 true SU1169532A3 (ru) | 1985-07-23 |
Family
ID=26328693
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU792847574A SU1169532A3 (ru) | 1978-12-06 | 1979-12-05 | Способ получени бензимидазолкарбаматов и его вариант |
Country Status (22)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU628671B2 (en) * | 1989-10-12 | 1992-09-17 | Michael John Crooks | Non-aqueous micellar solutions of various drugs |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3929821A (en) * | 1972-12-29 | 1975-12-30 | Syntex Inc | 5 (6)-Benzene ring substituted benzimidazole-2-carbamate derivatives |
| DE2334631A1 (de) * | 1973-07-07 | 1975-03-27 | Hoechst Ag | 5-phenylsulfinyl-2-benzimidazolcarbaminsaeureester und verfahren zu ihrer herstellung |
| US3915986A (en) * | 1974-06-19 | 1975-10-28 | Smithkline Corp | Methyl 5-propylthio-2-benzimidazolecarbamate |
| IT1076022B (it) * | 1977-04-20 | 1985-04-22 | Montedison Spa | Benzimidazolcarbammati antielmintici |
| HU177182B (hu) * | 1977-05-10 | 1981-08-28 | Chinoin Gyogyszer Es Vegyeszet | Eljárás tetraamino- difenil diszulfid származékok előállítására |
| AU4185678A (en) * | 1978-01-09 | 1979-07-19 | Squibb & Sons Inc | Derivatives of benzimidazoles |
-
1979
- 1979-12-03 DD DD79217331A patent/DD147539A5/de not_active IP Right Cessation
- 1979-12-03 DK DK512179A patent/DK157547C/da not_active IP Right Cessation
- 1979-12-03 NL NL7908719A patent/NL7908719A/xx not_active Application Discontinuation
- 1979-12-03 SE SE7909932A patent/SE445641B/sv not_active IP Right Cessation
- 1979-12-04 MX MX798521U patent/MX6197E/es unknown
- 1979-12-04 NZ NZ192311A patent/NZ192311A/xx unknown
- 1979-12-04 BR BR7907892A patent/BR7907892A/pt unknown
- 1979-12-04 CS CS798397A patent/CS242859B2/cs unknown
- 1979-12-04 AU AU53417/79A patent/AU536133B2/en not_active Ceased
- 1979-12-05 IE IE2347/79A patent/IE49976B1/en unknown
- 1979-12-05 DE DE19792948885 patent/DE2948885A1/de active Granted
- 1979-12-05 IL IL58885A patent/IL58885A/xx unknown
- 1979-12-05 ES ES486612A patent/ES8101560A1/es not_active Expired
- 1979-12-05 FR FR7929894A patent/FR2443461A1/fr active Granted
- 1979-12-05 GB GB7941960A patent/GB2037758B/en not_active Expired
- 1979-12-05 SU SU792847574A patent/SU1169532A3/ru active
- 1979-12-05 CA CA000341291A patent/CA1150280A/en not_active Expired
- 1979-12-05 HU HU79MO1070A patent/HU183093B/hu not_active IP Right Cessation
- 1979-12-05 AT AT0770279A patent/AT364832B/de not_active IP Right Cessation
- 1979-12-06 AR AR279174A patent/AR222847A1/es active
- 1979-12-06 PL PL1979220185A patent/PL126932B1/pl unknown
-
1980
- 1980-03-21 FR FR8006331A patent/FR2445306A1/fr active Granted
-
1983
- 1983-09-01 KE KE3326A patent/KE3326A/xx unknown
Non-Patent Citations (1)
| Title |
|---|
| Эльдерфильд Р. Гетероциклические Соединени , т. V.-M.: Иностранна литература, 1954,.с.225. * |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69630319T2 (de) | Neue trizyklische verbindungen und arzneimittelzusammensetzungen die diese enthalten | |
| EP0506532B1 (fr) | Nouveaux dérivés de l'indole, procédé de préparation et médicaments les contenant | |
| FR2607813A1 (fr) | Alkylamino-8 imidazo (1,2-a) pyrazines et derives, leur preparation et leur application en therapeutique | |
| LU81396A1 (fr) | Derives de phenylpiperazine | |
| EP0461986B1 (fr) | Dérivés d'hexahydroazépines, un procédé pour leur préparation et compositions pharmaceutiques les contenant | |
| EP0376850B1 (fr) | Dérivés du benzène, leur préparation et compositions pharmaceutiques les contenant | |
| SU1169532A3 (ru) | Способ получени бензимидазолкарбаматов и его вариант | |
| FR2471376A1 (fr) | Derives de thioethylamide, utiles comme bloqueurs d'histamine h2 | |
| CH630382A5 (fr) | Pyrroloquinoxalines et leurs sels. | |
| Reckhow et al. | Hexahydroindolo [2, 3-a] quinolizine1 | |
| EP0074121B1 (de) | 2,3,4,5-Tetrahydro-1-benzoxepin-3,5-dion-Derivate und Verfahren zu deren Herstellung | |
| BE1006226A3 (fr) | Derives de la benzofuranylimidazole, leur procede de preparation ainsi qu'une composition therapeutique les contenant. | |
| EP0220104B1 (fr) | Dérivés d'amino-5 pentanenitrile, leurs procédés de préparation et les compositions pharmaceutiques qui les contiennent | |
| US4299837A (en) | Anthelmintic benzimidazole-carbamates | |
| EP0311086A1 (de) | N-fluorierte Sulfonamide, Verfahren zu deren Herstellung und deren Verwendung | |
| DE2835439A1 (de) | 2-(o-hydroxyphenyl)-pyrrol | |
| EP0446140A1 (fr) | Nouvelles pyrrolo[1,2-a]thiéno[3,2-f]diazépines[1,4], leur procédé de préparation et les compositions pharmaceutiques qui les contiennent | |
| FR2475541A1 (fr) | Nouveaux intermediaires de synthese de colorants | |
| EP0323303B1 (fr) | Dérivés de nicotinoyl-pipérazine, procédé de préparation et utilisation en thérapeutique | |
| JPH0313231B2 (enrdf_load_stackoverflow) | ||
| US2501697A (en) | Dicyclopentadiene dithiocyanate | |
| SU335826A1 (ru) | Способ получения галоидбензилфенолов | |
| FR2553775A1 (fr) | Procede de preparation d'intermediaires utilisables pour la preparation de 7-oxabicycloheptane prostaglandines | |
| RU2024515C1 (ru) | Способ получения полициклических биоцидных соединений или их солей | |
| DE4308562A1 (de) | Verfahren zur Herstellung von aromatischen Brommethyl-Verbindungen |