SU850006A3 - Способ получени производных имидазолаили иХ СОлЕй, или ОпТичЕСКиХ изОМЕРОВ - Google Patents
Способ получени производных имидазолаили иХ СОлЕй, или ОпТичЕСКиХ изОМЕРОВ Download PDFInfo
- Publication number
- SU850006A3 SU850006A3 SU762312703A SU2312703A SU850006A3 SU 850006 A3 SU850006 A3 SU 850006A3 SU 762312703 A SU762312703 A SU 762312703A SU 2312703 A SU2312703 A SU 2312703A SU 850006 A3 SU850006 A3 SU 850006A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- phenyl
- imidazole
- parts
- group
- dioxolan
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 46
- 238000000034 method Methods 0.000 title claims description 27
- 230000003287 optical effect Effects 0.000 title claims description 5
- 150000002460 imidazoles Chemical class 0.000 title abstract description 24
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title description 3
- -1 2-propynyloxymethyl Chemical group 0.000 claims abstract description 50
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 33
- 125000001424 substituent group Chemical group 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 7
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 5
- 229910052751 metal Inorganic materials 0.000 claims abstract description 5
- 239000002184 metal Substances 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 4
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 4
- 125000004970 halomethyl group Chemical group 0.000 claims abstract description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract description 3
- 239000003960 organic solvent Substances 0.000 claims abstract description 3
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 3
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 4
- 229910001511 metal iodide Inorganic materials 0.000 claims abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 93
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
- 125000004849 alkoxymethyl group Chemical group 0.000 claims description 2
- 125000005002 aryl methyl group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 235000015497 potassium bicarbonate Nutrition 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- 235000011181 potassium carbonates Nutrition 0.000 claims description 2
- 235000015424 sodium Nutrition 0.000 claims description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims 1
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 1
- 108091022884 dihydropyrimidinase Proteins 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 238000010992 reflux Methods 0.000 abstract description 10
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract description 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000006331 halo benzoyl group Chemical group 0.000 abstract 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 48
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 27
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
- 239000003480 eluent Substances 0.000 description 25
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 24
- 239000000047 product Substances 0.000 description 24
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 description 23
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 20
- 239000004305 biphenyl Substances 0.000 description 20
- 229910017604 nitric acid Inorganic materials 0.000 description 19
- 239000011541 reaction mixture Substances 0.000 description 19
- 239000000284 extract Substances 0.000 description 18
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 16
- 229910002651 NO3 Inorganic materials 0.000 description 16
- 239000002253 acid Substances 0.000 description 13
- 150000007513 acids Chemical class 0.000 description 13
- 239000007858 starting material Substances 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 12
- 238000004440 column chromatography Methods 0.000 description 11
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 8
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 8
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 8
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 7
- 229940113088 dimethylacetamide Drugs 0.000 description 7
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 125000005997 bromomethyl group Chemical group 0.000 description 5
- 229940102396 methyl bromide Drugs 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 235000009518 sodium iodide Nutrition 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- JGLBPHDQOXRJRU-UHFFFAOYSA-N 3-(1,3-dioxolan-2-ylmethyl)-1,2-dihydroimidazole Chemical compound O1C(OCC1)CN1CNC=C1 JGLBPHDQOXRJRU-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 150000003891 oxalate salts Chemical class 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
- PTXMTZUUIOZOKF-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-1,3-dioxolane Chemical compound ClC1=CC(Cl)=CC=C1C1OCCO1 PTXMTZUUIOZOKF-UHFFFAOYSA-N 0.000 description 1
- NYXNQWTXUSTEGL-UHFFFAOYSA-N 2-(4-chlorophenyl)-1,3-dioxolane Chemical compound C1=CC(Cl)=CC=C1C1OCCO1 NYXNQWTXUSTEGL-UHFFFAOYSA-N 0.000 description 1
- IJFQVWIAHXOHTM-UHFFFAOYSA-N 2-(bromomethyl)-2-(2,4-dichlorophenyl)-4-[(4-phenylphenoxy)methyl]-1,3-dioxolane Chemical compound ClC1=CC(Cl)=CC=C1C1(CBr)OC(COC=2C=CC(=CC=2)C=2C=CC=CC=2)CO1 IJFQVWIAHXOHTM-UHFFFAOYSA-N 0.000 description 1
- OQLAYRXVDJTGHJ-UHFFFAOYSA-N 2-(bromomethyl)-2-(4-chlorophenyl)-4-phenyl-1,3-dioxolane Chemical compound C1=CC(Cl)=CC=C1C1(CBr)OC(C=2C=CC=CC=2)CO1 OQLAYRXVDJTGHJ-UHFFFAOYSA-N 0.000 description 1
- FZSFLABXZKPYRI-UHFFFAOYSA-N 2-(bromomethyl)-4-[(4-bromophenoxy)methyl]-2-(2,3-dichlorophenyl)-1,3-dioxolane Chemical compound ClC1=CC=CC(C2(CBr)OC(COC=3C=CC(Br)=CC=3)CO2)=C1Cl FZSFLABXZKPYRI-UHFFFAOYSA-N 0.000 description 1
- WEAGCQRXAUJTKK-UHFFFAOYSA-N 2-ethyl-2-(4-methoxyphenyl)-1,3-dioxolane Chemical compound C=1C=C(OC)C=CC=1C1(CC)OCCO1 WEAGCQRXAUJTKK-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- JYVLIDXNZAXMDK-UHFFFAOYSA-N 2-pentanol Substances CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000007791 liquid phase Substances 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
- 244000005700 microbiome Species 0.000 description 1
- AYKNHMWDRYAVBH-UHFFFAOYSA-N nitric acid;1h-pyrrole Chemical compound O[N+]([O-])=O.C=1C=CNC=1 AYKNHMWDRYAVBH-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/544,157 US3936470A (en) | 1975-01-27 | 1975-01-27 | 1,3-Dioxolan-2-ylmethylimidazoles |
| US61986375A | 1975-10-06 | 1975-10-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU850006A3 true SU850006A3 (ru) | 1981-07-23 |
Family
ID=27067525
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU762312703A SU850006A3 (ru) | 1975-01-27 | 1976-01-21 | Способ получени производных имидазолаили иХ СОлЕй, или ОпТичЕСКиХ изОМЕРОВ |
Country Status (14)
| Country | Link |
|---|---|
| CS (1) | CS202001B2 (OSRAM) |
| DK (1) | DK157300C (OSRAM) |
| ES (1) | ES444667A1 (OSRAM) |
| FI (1) | FI62081C (OSRAM) |
| HU (1) | HU174593B (OSRAM) |
| IE (1) | IE43157B1 (OSRAM) |
| IL (1) | IL48902A (OSRAM) |
| MX (1) | MX3143E (OSRAM) |
| NZ (1) | NZ179231A (OSRAM) |
| PH (1) | PH13605A (OSRAM) |
| PL (1) | PL101460B1 (OSRAM) |
| PT (1) | PT64741B (OSRAM) |
| SU (1) | SU850006A3 (OSRAM) |
| YU (1) | YU39956B (OSRAM) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3575999A (en) * | 1968-08-19 | 1971-04-20 | Janssen Pharmaceutica Nv | Ketal derivatives of imidazole |
-
1975
- 1975-11-12 NZ NZ17923175A patent/NZ179231A/xx unknown
- 1975-12-03 MX MX46175U patent/MX3143E/es unknown
- 1975-12-29 PH PH17929A patent/PH13605A/en unknown
-
1976
- 1976-01-15 YU YU11276A patent/YU39956B/xx unknown
- 1976-01-21 SU SU762312703A patent/SU850006A3/ru active
- 1976-01-26 IE IE13976A patent/IE43157B1/en unknown
- 1976-01-26 FI FI760175A patent/FI62081C/fi not_active IP Right Cessation
- 1976-01-26 PL PL18681476A patent/PL101460B1/pl unknown
- 1976-01-26 HU HU76JA748A patent/HU174593B/hu not_active IP Right Cessation
- 1976-01-26 DK DK30276A patent/DK157300C/da not_active IP Right Cessation
- 1976-01-26 IL IL48902A patent/IL48902A/xx unknown
- 1976-01-26 PT PT6474176A patent/PT64741B/pt unknown
- 1976-01-26 CS CS48576A patent/CS202001B2/cs unknown
- 1976-01-27 ES ES444667A patent/ES444667A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IE43157B1 (en) | 1980-12-31 |
| CS202001B2 (en) | 1980-12-31 |
| DK157300B (da) | 1989-12-04 |
| IL48902A0 (en) | 1976-03-31 |
| PL101460B1 (pl) | 1978-12-30 |
| MX3143E (es) | 1980-05-09 |
| YU11276A (en) | 1983-01-21 |
| DK30276A (da) | 1976-07-28 |
| PT64741B (fr) | 1978-01-04 |
| HU174593B (hu) | 1980-02-28 |
| YU39956B (en) | 1985-06-30 |
| NZ179231A (en) | 1978-03-06 |
| FI760175A7 (OSRAM) | 1976-07-28 |
| FI62081B (fi) | 1982-07-30 |
| FI62081C (fi) | 1982-11-10 |
| ES444667A1 (es) | 1977-11-16 |
| PT64741A (fr) | 1976-02-01 |
| PH13605A (en) | 1980-08-05 |
| IL48902A (en) | 1979-10-31 |
| IE43157L (en) | 1976-07-27 |
| DK157300C (da) | 1990-05-07 |
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