NO810083L - PROCEDURE FOR THE PREPARATION OF IMIDAZOLD DERIVATIVES - Google Patents
PROCEDURE FOR THE PREPARATION OF IMIDAZOLD DERIVATIVESInfo
- Publication number
- NO810083L NO810083L NO810083A NO810083A NO810083L NO 810083 L NO810083 L NO 810083L NO 810083 A NO810083 A NO 810083A NO 810083 A NO810083 A NO 810083A NO 810083 L NO810083 L NO 810083L
- Authority
- NO
- Norway
- Prior art keywords
- reaction
- thiomethyl
- formula
- carried out
- chloride
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 15
- 238000002360 preparation method Methods 0.000 title description 2
- 238000006243 chemical reaction Methods 0.000 claims description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000000243 solution Substances 0.000 claims description 6
- JEOZNMMOIBLWLV-UHFFFAOYSA-N 2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethanamine Chemical compound CC=1N=CNC=1CSCCN JEOZNMMOIBLWLV-UHFFFAOYSA-N 0.000 claims description 5
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 claims description 4
- 150000004714 phosphonium salts Chemical group 0.000 claims description 3
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 239000012074 organic phase Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000003444 phase transfer catalyst Substances 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- RYVBINGWVJJDPU-UHFFFAOYSA-M tributyl(hexadecyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC RYVBINGWVJJDPU-UHFFFAOYSA-M 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- VKPPFDPXZWFDFA-UHFFFAOYSA-N 2-chloroethanamine Chemical compound NCCCl VKPPFDPXZWFDFA-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 3
- 229960003151 mercaptamine Drugs 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- -1 3-[(2-aminoethyl)thiomethyl]-5-methyl imidazole Chemical compound 0.000 description 1
- ZOHLKTFCEUOOOQ-UHFFFAOYSA-N 4-(methoxymethyl)-5-methyl-1h-imidazole Chemical class COCC=1N=CNC=1C ZOHLKTFCEUOOOQ-UHFFFAOYSA-N 0.000 description 1
- 102000003710 Histamine H2 Receptors Human genes 0.000 description 1
- 108090000050 Histamine H2 Receptors Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- USFRYJRPHFMVBZ-UHFFFAOYSA-M benzyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 USFRYJRPHFMVBZ-UHFFFAOYSA-M 0.000 description 1
- AQIXAKUUQRKLND-UHFFFAOYSA-N cimetidine Chemical compound N#C/N=C(/NC)NCCSCC=1N=CNC=1C AQIXAKUUQRKLND-UHFFFAOYSA-N 0.000 description 1
- VNFPBHJOKIVQEB-UHFFFAOYSA-N clotrimazole Chemical compound ClC1=CC=CC=C1C(N1C=NC=C1)(C=1C=CC=CC=1)C1=CC=CC=C1 VNFPBHJOKIVQEB-UHFFFAOYSA-N 0.000 description 1
- ALEXXDVDDISNDU-JZYPGELDSA-N cortisol 21-acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)C[C@@H]2O ALEXXDVDDISNDU-JZYPGELDSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000006698 hydrazinolysis reaction Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- PMOIAJVKYNVHQE-UHFFFAOYSA-N phosphanium;bromide Chemical compound [PH4+].[Br-] PMOIAJVKYNVHQE-UHFFFAOYSA-N 0.000 description 1
- 125000005543 phthalimide group Chemical group 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- NNENFOSYDBTCBO-UHFFFAOYSA-M tributyl(hexadecyl)phosphanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC NNENFOSYDBTCBO-UHFFFAOYSA-M 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Description
Oppfinnelsen vedrører en ny fremgangsmåte for fremstilling av 4-[(2-aminoetyl)tiometyl]-5-metyl imidazol med formel: The invention relates to a new process for the production of 4-[(2-aminoethyl)thiomethyl]-5-methyl imidazole with the formula:
og dets sure addisjonssalter. and its acid addition salts.
4—[(2-aminoetyl)tiometyl]-5-metyl imidazol 4-[(2-aminoethyl)thiomethyl]-5-methyl imidazole
er et viktig mellomprodukt ved fremstillingen av farma-kologisk aktive forbindelser, som N-cyano-N'-metyl-N"-[ 2-[(5-metyl-4-imidazolyl)-metyltio]etyl)-guanidin, som virker som en aktiv histaminantagonist på H2~reseptorer, og er kjent under generiske navn.; "cimitidin" . Mellom-produktet og fremgangsmåte for fremstilling herav, ble første gang omtalt i britisk patent 1,338,169. is an important intermediate in the production of pharmacologically active compounds, such as N-cyano-N'-methyl-N"-[ 2-[(5-methyl-4-imidazolyl)-methylthio]ethyl)-guanidine, which acts as an active histamine antagonist on H2-receptors, and is known under the generic name: "cimitidine". The intermediate product and process for its preparation were first described in British patent 1,338,169.
Den kjente og de omtalte prosesser er basert på omsetning av 4-halometyl-, 4-hydroksymetyl- eller 4-metoksymetyl-5-metyl imidazoler eller dets hydrokal-gelid ved formel: The known and the mentioned processes are based on the reaction of 4-halomethyl-, 4-hydroxymethyl- or 4-methoxymethyl-5-methyl imidazoles or their hydrocal gelide by formula:
hvori Q betyr et halogen, hydroksy aven metoksygruppe, med cysteamin eller dets hydrohålogenider. wherein Q represents a halogen, hydroxy or methoxy group, with cysteamine or its hydrohalogenides.
Når Q betyr halogen, utføres reaksjonen et basisk medium f.eks. i nærvær av, natrium-etoksyd eller natriumhydroksyd. Da cysteamin er et primært amin, er det nødvendig å beskytte aminogruppen, f.eks. en phtali-mid-gruppe fjernes etter avslutning'reaksjon, sur hydro-lyse eller hydrazinolyse. Når Q betyr en hydroksy- eller metoksy-gruppe, føres reaksjonen i et surt medium i nærvær av en 48%.vanndig HBr oppløsning :eller i iseddik/ Utbyttet av disse reaksjoner ligger mellom 70 og 90%, og reaksjons-tiden fra 10 til 18 timer, og reaksjonstemperaturen fra When Q means halogen, the reaction is carried out in a basic medium, e.g. in the presence of sodium ethoxide or sodium hydroxide. As cysteamine is a primary amine, it is necessary to protect the amino group, e.g. a phthalimide group is removed after termination reaction, acid hydrolysis or hydrazinolysis. When Q means a hydroxy or methoxy group, the reaction is carried out in an acidic medium in the presence of a 48% aqueous HBr solution :or in glacial acetic acid/ The yield of these reactions is between 70 and 90%, and the reaction time from 10 to 18 hours, and the reaction temperature from
■ 100 til 120°C. ■ 100 to 120°C.
Hensikten med oppfinnelsen er å tilveiebringe The purpose of the invention is to provide
en fremgangsmåte for fremstilling av 4-[(2-aminoetyl)-tiometyl]-5-metyl imidazol med høye .utbytter, kortere reaksjonstid og ved værelsestemperatur som vil muliggjøre at sluttproduktet I lett isoleres, ved høy renhet. a process for the production of 4-[(2-aminoethyl)-thiomethyl]-5-methyl imidazole with high yields, shorter reaction time and at room temperature which will enable the final product I to be easily isolated, at high purity.
Formålet oppnås ved selektiv alkylering av 4(5)-tiometyl-5 ( 4) -metyl- imidazol ved formel: The purpose is achieved by selective alkylation of 4(5)-thiomethyl-5(4)-methylimidazole by formula:
med et 2-haloetylamin, hvori halo, betyr klor eller brom, ved værelsestemperatur i et systém bestående av en 50% vanndig oppløsning av en sterk base og en organiske fase ble det benyttet quatenært ammonium eller quatenært fosfoniumsalter som faseoverføringskatalysatorer. Som katalysatorer kan det bli benyttet f.eks. metyltricaprylyl-ammoniumklorid, benzyltrietyl ammoniumklorid, benzyltrifenyl fosfoniumklorid, hexadicyltributyl fosfoniumbromid etc. with a 2-haloethylamine, in which halo means chlorine or bromine, at room temperature in a system consisting of a 50% aqueous solution of a strong base and an organic phase, quaternary ammonium or quaternary phosphonium salts were used as phase transfer catalysts. Catalysts can be used e.g. methyltricaprylyl ammonium chloride, benzyltriethyl ammonium chloride, benzyltriphenyl phosphonium chloride, hexadicyltributyl phosphonium bromide, etc.
Andre fordeler med fremgangsmåten ifølge oppfinnelsen, i forhold til kjente fremgangsmåter for fremstilling av 4-[(2aminoetyl)-tiometyl]-5-metyl imidazol, Other advantages of the method according to the invention, in relation to known methods for the production of 4-[(2aminoethyl)-thiomethyl]-5-methyl imidazole,
er at bruken av cysteamin-hydrohalogenid er unngått. Istedenfor dette dyre kjemikalie, benyttes et 2-halogenetylamin, fortrinnsvis 2-kloretylamin', som er billigere og lett tilgjengelig forbindelse. Videre er det ikke behov for en preliminær beskyttelse av aminogruppen i den forbindelse. is that the use of cysteamine hydrohalide is avoided. Instead of this expensive chemical, a 2-haloethylamine, preferably 2-chloroethylamine, is used, which is a cheaper and easily available compound. Furthermore, there is no need for a preliminary protection of the amino group in that connection.
Som organisk oppløsningsmiddel kan det benyttes polare organiske oppløsningemidler, hvor utgangsreaksjons-deltageren er oppløslig,som lavere alkoholer, acetonitril o.l. Utbyttene av sluttforbindelsen- med formel I er ekstraordinære høye og går opp til 85 til 90% av det teoretiske utbytte. As an organic solvent, polar organic solvents can be used, where the starting reaction participant is soluble, such as lower alcohols, acetonitrile, etc. The yields of the final compound of formula I are extraordinarily high and go up to 85 to 90% of the theoretical yield.
Utgangsforbindelsen 4(5)-tiometyl-5(4)-metyl imidazol og. fremgangsmåten for fremstilling av dette om-tales i belgisk patent 875 845. The starting compound 4(5)-thiomethyl-5(4)-methyl imidazole and. the method for producing this is mentioned in Belgian patent 875 845.
Da tioler ikke er meget stabile forbindelser, utføres reaksjonene fortrinnsvis i en inert atmosfære. As thiols are not very stable compounds, the reactions are preferably carried out in an inert atmosphere.
I en alternativ fremgangsmåte benyttes et alkali-merkaptid av 5 (4)-metyl-4,(5)-tiometyl imidazol som er en stabil forbindelse som: utgangsstoff. Reaksjons-betingelsene er svarende til de'ovennevnte. In an alternative method, an alkali mercaptide of 5 (4)-methyl-4,(5)-thiomethyl imidazole is used which is a stable compound as starting material. The reaction conditions are similar to those mentioned above.
Oppfinnelsen skal forklares ved noen eksempler. The invention will be explained by some examples.
Eksempel 1. 5-metyl-4-tiometyl imidazol (6,4 g, 0,05 mol) oppløses i etanol (80ml.). Der t.ilsetttes en 50% vanndig NaOH-oppløsning (10 ml.), etterfulgt av tilsetning av heksadecyltributylfosfoniumklorid (l,16g, 0,0025 mol), Example 1. 5-methyl-4-thiomethyl imidazole (6.4 g, 0.05 mol) is dissolved in ethanol (80 ml.). A 50% aqueous NaOH solution (10 ml.) was added, followed by the addition of hexadecyltributylphosphonium chloride (1.16 g, 0.0025 mol),
og omrøring i 10 minutter i en inert atmosfære ved værelsestemperatur. Etter en periode på 15 minutter tilsettes en oppløsning av 2-kloretylamin ;'(4,0g) i etanol (30 ml), and stirring for 10 minutes in an inert atmosphere at room temperature. After a period of 15 minutes, a solution of 2-chloroethylamine (4.0 g) in ethanol (30 ml) is added,
og den resulterende blanding omrørés' i 30 minutter ved værelsestemperatur, og deretter, 30 ytterligere minutter ved 50OC. Oppløsningsmiddelet fjernes ved fordampning og residet extraheres med isopropanol. and the resulting mixture is stirred for 30 minutes at room temperature, and then, 30 more minutes at 50°C. The solvent is removed by evaporation and the residue is extracted with isopropanol.
De organiske salter frafiltreres og hydrogen-klorid føres i den isopropanoliske oppløsning inntil nådd pH 1. The organic salts are filtered off and hydrogen chloride is introduced into the isopropanol solution until pH 1 is reached.
Reaksjonsblandingen fordampes til tørrhet og residet pmkrystalliserer fra etanol.'■ Det oppnås 3-[(2-aminoetyl)tiometyl]-5-metyl imidazol (10,9g, 89,3%) The reaction mixture is evaporated to dryness and the residue crystallizes from ethanol. 3-[(2-aminoethyl)thiomethyl]-5-methyl imidazole (10.9g, 89.3%) is obtained
i form av de hydroklorider, smeltepunkt 189-191°C. in the form of the hydrochlorides, melting point 189-191°C.
Eksempel 2. Example 2.
Fremgangsmåte ifølge det foregående eksempel gjentas idet det benyttes benzyltrietyl-ammoniumkTorid (TEBA, 580 mg, 2,5 mol) som katalysator. Det oppnås 10,8 g (88%) av den ønskede forbindelse. The procedure according to the previous example is repeated using benzyltriethylammonium chloride (TEBA, 580 mg, 2.5 mol) as catalyst. 10.8 g (88%) of the desired compound are obtained.
Eksempel 3. Example 3.
Fremgangsmåte ifølge eksempel 1 gjentas idet The procedure according to example 1 is then repeated
det imidlertid anvendes trikaprylmetyl-ammoniumklorid (Aliquat 336, 1,04 g, 2,5 mmol) som katalysator. Det oppnås 10,9 g (89,3%) av den ønskede forbindelse. however, tricaprylmethyl ammonium chloride (Aliquat 336, 1.04 g, 2.5 mmol) is used as catalyst. 10.9 g (89.3%) of the desired compound are obtained.
Eksempel 4. Example 4.
5-metyl-4-tiometyl imidazol (l,5g, 0,01 mol) 5-methyl-4-thiomethyl imidazole (1.5g, 0.01 mol)
i form av natrium-merkaptide oppløses i vann (20 ml). in the form of sodium mercaptide is dissolved in water (20 ml).
Der tilsettes benzyltrietyl-ammoriiumklorid (70 mg, 0,3 mol). Den resulterende oppløsning omrøres i 10 minutter ved værelsestemperatur. I løpet av en periode på 10 minutter tilsettes 2-kloretylamin (8,0 g): i etanol (8 ml) dråpevis til reaksjonsblandingen. Reaksjonsblandingen omrøres i ±h time ved værelsestemperatur, fordampes i tørrhet, og resten av fremgangsmåten ifølge eksempel 1 følges. Benzyltriethylammonium chloride (70 mg, 0.3 mol) is added there. The resulting solution is stirred for 10 minutes at room temperature. Over a period of 10 minutes, 2-chloroethylamine (8.0 g): in ethanol (8 ml) is added dropwise to the reaction mixture. The reaction mixture is stirred for ±h hour at room temperature, evaporated to dryness, and the rest of the procedure according to example 1 is followed.
Det oppnås 2,2 g (90,3%) av den ønskede forbindelse, med smeltepunkt 190-192°C. 2.2 g (90.3%) of the desired compound is obtained, with a melting point of 190-192°C.
Claims (4)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| YU80/80A YU41689B (en) | 1980-01-14 | 1980-01-14 | Process for preparing imidazole derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO810083L true NO810083L (en) | 1981-07-15 |
Family
ID=25548243
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO810083A NO810083L (en) | 1980-01-14 | 1981-01-12 | PROCEDURE FOR THE PREPARATION OF IMIDAZOLD DERIVATIVES |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS56127361A (en) |
| CA (1) | CA1154023A (en) |
| CS (1) | CS214847B2 (en) |
| FI (1) | FI804056L (en) |
| HU (1) | HU187289B (en) |
| NO (1) | NO810083L (en) |
| PL (1) | PL129291B1 (en) |
| SE (1) | SE8100127L (en) |
| SU (1) | SU969159A3 (en) |
| YU (1) | YU41689B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58188860A (en) * | 1982-04-27 | 1983-11-04 | Fujimoto Seiyaku Kk | Preparation of imidazole derivative |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5440547A (en) * | 1977-09-07 | 1979-03-30 | Seikosha Kk | Device for adjusting output frequency of frequency divider |
| IL56265A (en) * | 1977-12-28 | 1982-08-31 | Om Lab Sa | Process for preparing imidazolyl methylthio guanidine derivatives and a novel intermediate therefor |
-
1980
- 1980-01-14 YU YU80/80A patent/YU41689B/en unknown
- 1980-12-30 FI FI804056A patent/FI804056L/en not_active Application Discontinuation
-
1981
- 1981-01-12 PL PL1981229185A patent/PL129291B1/en unknown
- 1981-01-12 SE SE8100127A patent/SE8100127L/en not_active Application Discontinuation
- 1981-01-12 NO NO810083A patent/NO810083L/en unknown
- 1981-01-12 CS CS81233A patent/CS214847B2/en unknown
- 1981-01-12 CA CA000368285A patent/CA1154023A/en not_active Expired
- 1981-01-13 SU SU813230706A patent/SU969159A3/en active
- 1981-01-13 HU HU8171A patent/HU187289B/en unknown
- 1981-01-13 JP JP275181A patent/JPS56127361A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CA1154023A (en) | 1983-09-20 |
| YU8080A (en) | 1983-10-31 |
| PL129291B1 (en) | 1984-04-30 |
| SU969159A3 (en) | 1982-10-23 |
| YU41689B (en) | 1987-12-31 |
| SE8100127L (en) | 1981-07-15 |
| PL229185A1 (en) | 1981-09-18 |
| JPS56127361A (en) | 1981-10-06 |
| FI804056L (en) | 1981-07-15 |
| HU187289B (en) | 1985-12-28 |
| CS214847B2 (en) | 1982-06-25 |
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