CH641168A5 - Separation d'oximes syn et anti. - Google Patents
Separation d'oximes syn et anti. Download PDFInfo
- Publication number
- CH641168A5 CH641168A5 CH959479A CH959479A CH641168A5 CH 641168 A5 CH641168 A5 CH 641168A5 CH 959479 A CH959479 A CH 959479A CH 959479 A CH959479 A CH 959479A CH 641168 A5 CH641168 A5 CH 641168A5
- Authority
- CH
- Switzerland
- Prior art keywords
- syn
- amino
- benzimidazole
- isomer
- mixture
- Prior art date
Links
- 150000002923 oximes Chemical class 0.000 title claims description 24
- 238000000926 separation method Methods 0.000 title claims description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 24
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 19
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- 239000003960 organic solvent Substances 0.000 claims description 12
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- NYBWUHOMYZZKOR-UHFFFAOYSA-N tes-adt Chemical class C1=C2C(C#C[Si](CC)(CC)CC)=C(C=C3C(SC=C3)=C3)C3=C(C#C[Si](CC)(CC)CC)C2=CC2=C1SC=C2 NYBWUHOMYZZKOR-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 238000002425 crystallisation Methods 0.000 claims description 5
- 230000008025 crystallization Effects 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- -1 chloro, bromo, iodo Chemical group 0.000 claims description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- 239000003443 antiviral agent Substances 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- 125000004442 acylamino group Chemical group 0.000 claims 2
- 230000000840 anti-viral effect Effects 0.000 claims 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- 150000001556 benzimidazoles Chemical class 0.000 claims 1
- 238000013375 chromatographic separation Methods 0.000 claims 1
- 239000003480 eluent Substances 0.000 claims 1
- 238000011031 large-scale manufacturing process Methods 0.000 claims 1
- 230000003389 potentiating effect Effects 0.000 claims 1
- 238000010956 selective crystallization Methods 0.000 claims 1
- 239000000706 filtrate Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 4
- 230000005484 gravity Effects 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 241001466953 Echovirus Species 0.000 description 1
- 241000709661 Enterovirus Species 0.000 description 1
- 241000991587 Enterovirus C Species 0.000 description 1
- 241000710185 Mengo virus Species 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/019,526 US4191832A (en) | 1979-03-12 | 1979-03-12 | Separation of syn and anti oximes of 1-sulfonyl-2-aminobenzimidazoles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH641168A5 true CH641168A5 (fr) | 1984-02-15 |
Family
ID=21793673
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH959479A CH641168A5 (fr) | 1979-03-12 | 1979-10-25 | Separation d'oximes syn et anti. |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4191832A (enExample) |
| EP (1) | EP0015339A1 (enExample) |
| JP (1) | JPS55120569A (enExample) |
| KR (1) | KR830002350B1 (enExample) |
| AR (1) | AR228845A1 (enExample) |
| BE (1) | BE879551A (enExample) |
| CA (1) | CA1118428A (enExample) |
| CH (1) | CH641168A5 (enExample) |
| FR (1) | FR2451369A1 (enExample) |
| GB (1) | GB2044249B (enExample) |
| HU (1) | HU180233B (enExample) |
| IE (1) | IE49094B1 (enExample) |
| IL (1) | IL58531A (enExample) |
| LU (1) | LU81815A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4492708A (en) * | 1982-09-27 | 1985-01-08 | Eli Lilly And Company | Antiviral benzimidazoles |
| FR2593177B1 (fr) * | 1986-01-20 | 1988-04-01 | Novapharme | Nouveaux benzimidazo |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE795098A (fr) * | 1972-02-09 | 1973-08-07 | Bayer Ag | Nouveaux 1-aminosulfonyl-2-amino-benzimidazoles, leur procede de preparation et leur application comme fongicides |
| PT65486B (en) * | 1975-08-28 | 1978-03-24 | Lilly Co Eli | Process for the preparation of carbonil-substituted 1-sulfonylbenzimidazoles |
| US4008243A (en) * | 1975-11-19 | 1977-02-15 | Eli Lilly And Company | Antiviral thiazolinyl or thiazinyl benzimidazole esters |
| US4118573A (en) * | 1975-11-24 | 1978-10-03 | Eli Lilly And Company | Substituted 1-sulfonylbenzimidazoles |
-
1979
- 1979-03-12 US US06/019,526 patent/US4191832A/en not_active Expired - Lifetime
- 1979-10-19 EP EP79302272A patent/EP0015339A1/en not_active Withdrawn
- 1979-10-19 GB GB7936425A patent/GB2044249B/en not_active Expired
- 1979-10-19 HU HU79EI886A patent/HU180233B/hu unknown
- 1979-10-22 BE BE1/9579A patent/BE879551A/fr not_active IP Right Cessation
- 1979-10-22 FR FR7926164A patent/FR2451369A1/fr active Granted
- 1979-10-23 AR AR278590A patent/AR228845A1/es active
- 1979-10-23 CA CA000338192A patent/CA1118428A/en not_active Expired
- 1979-10-23 IL IL58531A patent/IL58531A/xx unknown
- 1979-10-24 LU LU81815A patent/LU81815A1/fr unknown
- 1979-10-25 KR KR1019790003713A patent/KR830002350B1/ko not_active Expired
- 1979-10-25 CH CH959479A patent/CH641168A5/fr not_active IP Right Cessation
- 1979-10-25 IE IE2046/79A patent/IE49094B1/en unknown
- 1979-10-25 JP JP13861779A patent/JPS55120569A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| IL58531A0 (en) | 1980-01-31 |
| CA1118428A (en) | 1982-02-16 |
| GB2044249B (en) | 1983-02-09 |
| KR830001245A (ko) | 1983-04-29 |
| IL58531A (en) | 1984-11-30 |
| IE792046L (en) | 1980-09-12 |
| US4191832A (en) | 1980-03-04 |
| FR2451369A1 (fr) | 1980-10-10 |
| GB2044249A (en) | 1980-10-15 |
| EP0015339A1 (en) | 1980-09-17 |
| BE879551A (fr) | 1980-04-22 |
| IE49094B1 (en) | 1985-07-24 |
| AR228845A1 (es) | 1983-04-29 |
| LU81815A1 (fr) | 1980-01-25 |
| JPS55120569A (en) | 1980-09-17 |
| HU180233B (en) | 1983-02-28 |
| KR830002350B1 (ko) | 1983-10-24 |
| FR2451369B1 (enExample) | 1983-05-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |