NO842348L - Analogifremgangsmaate for fremstilling av terapeutiske aktive 1-acetonyl-2-(fenylimino)-imidazolidin-derivater - Google Patents
Analogifremgangsmaate for fremstilling av terapeutiske aktive 1-acetonyl-2-(fenylimino)-imidazolidin-derivaterInfo
- Publication number
- NO842348L NO842348L NO842348A NO842348A NO842348L NO 842348 L NO842348 L NO 842348L NO 842348 A NO842348 A NO 842348A NO 842348 A NO842348 A NO 842348A NO 842348 L NO842348 L NO 842348L
- Authority
- NO
- Norway
- Prior art keywords
- acetonyl
- phenylimino
- imidazolidine
- general formula
- acid
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims 3
- PSVWUIFNJAXZQT-UHFFFAOYSA-N 1-(2-anilino-4,5-dihydroimidazol-1-yl)propan-2-one Chemical class CC(=O)CN1CCNC1=NC1=CC=CC=C1 PSVWUIFNJAXZQT-UHFFFAOYSA-N 0.000 title description 2
- 230000001225 therapeutic effect Effects 0.000 title description 2
- 239000002253 acid Substances 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- -1 methoxy- Chemical class 0.000 claims description 22
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910001385 heavy metal Inorganic materials 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 238000006555 catalytic reaction Methods 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical class [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 claims description 2
- GOKQPLIQRFOOJR-UHFFFAOYSA-N n-phenyl-1-prop-2-ynyl-4,5-dihydroimidazol-2-amine Chemical class C#CCN1CCNC1=NC1=CC=CC=C1 GOKQPLIQRFOOJR-UHFFFAOYSA-N 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- FIARMZDBEGVMLV-UHFFFAOYSA-N 1,1,2,2,2-pentafluoroethanolate Chemical group [O-]C(F)(F)C(F)(F)F FIARMZDBEGVMLV-UHFFFAOYSA-N 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 abstract description 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 3
- 125000000446 sulfanediyl group Chemical group *S* 0.000 abstract 2
- 125000005530 alkylenedioxy group Chemical group 0.000 abstract 1
- 229940035676 analgesics Drugs 0.000 abstract 1
- 239000000730 antalgic agent Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 239000012458 free base Substances 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- IABXFFOXFXDZLM-UHFFFAOYSA-N 1-[2-(2,4-dichloroanilino)-4,5-dihydroimidazol-1-yl]propan-2-one;hydrobromide Chemical compound Br.CC(=O)CN1CCNC1=NC1=CC=C(Cl)C=C1Cl IABXFFOXFXDZLM-UHFFFAOYSA-N 0.000 description 1
- UDZMSGJVLKAIJS-UHFFFAOYSA-N 1-[2-(2,6-dichloroanilino)-4,5-dihydroimidazol-1-yl]propan-2-one Chemical compound CC(=O)CN1CCNC1=NC1=C(Cl)C=CC=C1Cl UDZMSGJVLKAIJS-UHFFFAOYSA-N 0.000 description 1
- PBRFNQDIRFIPKX-UHFFFAOYSA-N 1-[2-(2-bromo-5-chloroanilino)-4,5-dihydroimidazol-1-yl]propan-2-one Chemical compound CC(=O)CN1CCNC1=NC1=CC(Cl)=CC=C1Br PBRFNQDIRFIPKX-UHFFFAOYSA-N 0.000 description 1
- YPTPUAFVKPFCKU-UHFFFAOYSA-N 1-[2-(4-chloro-2-methoxyanilino)-4,5-dihydroimidazol-1-yl]propan-2-one Chemical compound COC1=CC(Cl)=CC=C1N=C1N(CC(C)=O)CCN1 YPTPUAFVKPFCKU-UHFFFAOYSA-N 0.000 description 1
- FHAZPPJNDWTOCX-UHFFFAOYSA-N 1-[2-(4-chloroanilino)-4,5-dihydroimidazol-1-yl]propan-2-one;hydrobromide Chemical compound Br.CC(=O)CN1CCNC1=NC1=CC=C(Cl)C=C1 FHAZPPJNDWTOCX-UHFFFAOYSA-N 0.000 description 1
- JYGLSWQFDWKFOS-UHFFFAOYSA-N 1-[2-(5-bromo-2-methylanilino)-4,5-dihydroimidazol-1-yl]propan-2-one Chemical compound CC(=O)CN1CCNC1=NC1=CC(Br)=CC=C1C JYGLSWQFDWKFOS-UHFFFAOYSA-N 0.000 description 1
- PMWROFMHEGIJJS-UHFFFAOYSA-N 1-[2-[2-chloro-5-(trifluoromethyl)anilino]-4,5-dihydroimidazol-1-yl]propan-2-one Chemical compound CC(=O)CN1CCNC1=NC1=CC(C(F)(F)F)=CC=C1Cl PMWROFMHEGIJJS-UHFFFAOYSA-N 0.000 description 1
- SEQBPQVWPSOFQP-UHFFFAOYSA-N 1-[2-[5-chloro-2-(trifluoromethoxy)anilino]-4,5-dihydroimidazol-1-yl]propan-2-one Chemical compound CC(=O)CN1CCNC1=NC1=CC(Cl)=CC=C1OC(F)(F)F SEQBPQVWPSOFQP-UHFFFAOYSA-N 0.000 description 1
- STRPCRJGBWAMHQ-UHFFFAOYSA-N 1-[2-[5-fluoro-2-(1,1,2,2,2-pentafluoroethoxy)anilino]-4,5-dihydroimidazol-1-yl]propan-2-one Chemical compound CC(=O)CN1CCNC1=NC1=CC(F)=CC=C1OC(F)(F)C(F)(F)F STRPCRJGBWAMHQ-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- YIUIVFFUEVPRIU-UHFFFAOYSA-N 8-chlorotheophylline Chemical compound O=C1N(C)C(=O)N(C)C2=NC(Cl)=N[C]21 YIUIVFFUEVPRIU-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- GATNOFPXSDHULC-UHFFFAOYSA-N ethylphosphonic acid Chemical compound CCP(O)(O)=O GATNOFPXSDHULC-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- IQXFQTQAXAPESE-UHFFFAOYSA-N imidazolidine;hydrobromide Chemical compound Br.C1CNCN1 IQXFQTQAXAPESE-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229910000372 mercury(II) sulfate Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- JOTHFYFJNQJWKG-UHFFFAOYSA-N n-(3-fluoro-4-methylphenyl)-1-prop-2-ynyl-4,5-dihydroimidazol-2-amine Chemical compound C1=C(F)C(C)=CC=C1N=C1N(CC#C)CCN1 JOTHFYFJNQJWKG-UHFFFAOYSA-N 0.000 description 1
- QJENRGOSUPKLKG-UHFFFAOYSA-N n-(4-chloro-2-methoxyphenyl)-1-prop-2-ynyl-4,5-dihydroimidazol-2-amine Chemical compound COC1=CC(Cl)=CC=C1N=C1N(CC#C)CCN1 QJENRGOSUPKLKG-UHFFFAOYSA-N 0.000 description 1
- MGNVWQWWESMBRW-UHFFFAOYSA-N n-(4-chlorophenyl)-1-prop-2-ynyl-4,5-dihydroimidazol-2-amine Chemical compound C1=CC(Cl)=CC=C1N=C1N(CC#C)CCN1 MGNVWQWWESMBRW-UHFFFAOYSA-N 0.000 description 1
- JDFHPYNEYAFVMZ-UHFFFAOYSA-N n-(6-bromo-2,3-dihydro-1,4-benzodioxin-7-yl)-1-prop-2-ynyl-4,5-dihydroimidazol-2-amine Chemical compound BrC1=CC=2OCCOC=2C=C1N=C1NCCN1CC#C JDFHPYNEYAFVMZ-UHFFFAOYSA-N 0.000 description 1
- PDXWWYPBXWKPEZ-UHFFFAOYSA-N n-[5-chloro-2-(trifluoromethoxy)phenyl]-1-prop-2-ynyl-4,5-dihydroimidazol-2-amine Chemical compound FC(F)(F)OC1=CC=C(Cl)C=C1N=C1N(CC#C)CCN1 PDXWWYPBXWKPEZ-UHFFFAOYSA-N 0.000 description 1
- WGJBSTIDYXYQLW-UHFFFAOYSA-N n-[5-fluoro-2-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1-prop-2-ynyl-4,5-dihydroimidazol-2-amine Chemical compound FC1=CC=C(OC(F)(F)C(F)(F)F)C(N=C2N(CCN2)CC#C)=C1 WGJBSTIDYXYQLW-UHFFFAOYSA-N 0.000 description 1
- JCOPITWIWLFFPC-UHFFFAOYSA-N n-phenyl-4,5-dihydro-1h-imidazol-2-amine Chemical class N1CCN=C1NC1=CC=CC=C1 JCOPITWIWLFFPC-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 229940005605 valeric acid Drugs 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
- C07D233/66—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 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 to ring carbon atoms
- C07D233/88—Nitrogen atoms, e.g. allantoin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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 to ring carbon atoms
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
- C07D233/50—Nitrogen atoms not forming part of a nitro radical with carbocyclic radicals directly attached to said nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Pain & Pain Management (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Luminescent Compositions (AREA)
- Developing Agents For Electrophotography (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Fats And Perfumes (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19833321282 DE3321282A1 (de) | 1983-06-13 | 1983-06-13 | Neue 1-acetonyl-2-(phenylimino)-imidazolidine, deren saeureadditionssalze, diese enthaltende arzneimittel und verfahren zu deren herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO842348L true NO842348L (no) | 1984-12-14 |
Family
ID=6201353
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO842348A NO842348L (no) | 1983-06-13 | 1984-06-12 | Analogifremgangsmaate for fremstilling av terapeutiske aktive 1-acetonyl-2-(fenylimino)-imidazolidin-derivater |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4588736A (da) |
| EP (1) | EP0129153B1 (da) |
| JP (1) | JPS608268A (da) |
| KR (1) | KR850000409A (da) |
| AT (1) | ATE23715T1 (da) |
| AU (1) | AU2934484A (da) |
| CA (1) | CA1226580A (da) |
| DE (2) | DE3321282A1 (da) |
| DK (1) | DK286984A (da) |
| ES (1) | ES533320A0 (da) |
| FI (1) | FI842360A (da) |
| GB (1) | GB2142627B (da) |
| GR (1) | GR82365B (da) |
| IL (1) | IL72076A0 (da) |
| NO (1) | NO842348L (da) |
| PH (1) | PH20505A (da) |
| PT (1) | PT78717B (da) |
| ZA (1) | ZA844411B (da) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0618909B2 (ja) | 1984-11-06 | 1994-03-16 | 東レ株式会社 | 複合材料の製造法 |
| US5192778A (en) * | 1990-04-03 | 1993-03-09 | Mitsui Toatsu Chemicals, Inc. | Dialkoxymethylimidazolidine derivatives, preparation thereof, insecticides containing same as an effective ingredient and intermediates therefor |
| US5663189A (en) * | 1993-07-01 | 1997-09-02 | The Procter & Gamble Company | 2-imidazolinylamino heterocyclic compounds useful as alpha-2 adrenoceptor agonists |
| WO1996004270A1 (en) | 1994-08-04 | 1996-02-15 | Synaptic Pharmaceutical Corporation | Novel benzimidazole derivatives |
| US5914342A (en) * | 1995-06-07 | 1999-06-22 | The Procter & Gamble Company | 2-imidazolinylamino heterocyclic compounds useful as alpha-2 adrenoceptor agonists |
| US6495583B1 (en) | 1997-03-25 | 2002-12-17 | Synaptic Pharmaceutical Corporation | Benzimidazole derivatives |
| JP5075064B2 (ja) * | 2008-08-28 | 2012-11-14 | 株式会社吉野工業所 | 液体噴出容器 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2523103C3 (de) * | 1975-05-24 | 1979-11-29 | C.H. Boehringer Sohn, 6507 Ingelheim | Substituierte 2-[N-Progargyl-N-(2-chlorphenyl)amino] -imidazoline-^), deren Säureadditionssalze, Verfahren zu ihrer Herstellung und deren Verwendung |
| US4262005A (en) * | 1978-05-31 | 1981-04-14 | The Boots Company Limited | Compounds, compositions and methods for controlling pests |
| US4461904A (en) * | 1981-11-20 | 1984-07-24 | Alcon Laboratories, Inc. | 2-(Trisubstituted phenylimino)-imidazolines |
-
1983
- 1983-06-13 DE DE19833321282 patent/DE3321282A1/de not_active Withdrawn
-
1984
- 1984-05-21 US US06/612,340 patent/US4588736A/en not_active Expired - Fee Related
- 1984-06-06 DE DE8484106487T patent/DE3461375D1/de not_active Expired
- 1984-06-06 AT AT84106487T patent/ATE23715T1/de not_active IP Right Cessation
- 1984-06-06 EP EP84106487A patent/EP0129153B1/de not_active Expired
- 1984-06-11 KR KR1019840003270A patent/KR850000409A/ko not_active Application Discontinuation
- 1984-06-12 ZA ZA844411A patent/ZA844411B/xx unknown
- 1984-06-12 GR GR74991A patent/GR82365B/el unknown
- 1984-06-12 IL IL72076A patent/IL72076A0/xx unknown
- 1984-06-12 CA CA000456405A patent/CA1226580A/en not_active Expired
- 1984-06-12 ES ES533320A patent/ES533320A0/es active Granted
- 1984-06-12 DK DK286984A patent/DK286984A/da not_active Application Discontinuation
- 1984-06-12 PT PT78717A patent/PT78717B/pt unknown
- 1984-06-12 JP JP59119251A patent/JPS608268A/ja active Pending
- 1984-06-12 FI FI842360A patent/FI842360A/fi not_active Application Discontinuation
- 1984-06-12 NO NO842348A patent/NO842348L/no unknown
- 1984-06-13 AU AU29344/84A patent/AU2934484A/en not_active Abandoned
- 1984-06-13 GB GB08415087A patent/GB2142627B/en not_active Expired
- 1984-06-13 PH PH30807A patent/PH20505A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES8506641A1 (es) | 1985-08-01 |
| EP0129153B1 (de) | 1986-11-20 |
| DE3321282A1 (de) | 1984-12-13 |
| FI842360A (fi) | 1984-12-14 |
| PH20505A (en) | 1987-01-21 |
| JPS608268A (ja) | 1985-01-17 |
| GB2142627A (en) | 1985-01-23 |
| DK286984D0 (da) | 1984-06-12 |
| AU2934484A (en) | 1984-12-20 |
| GR82365B (da) | 1984-12-13 |
| PT78717B (de) | 1986-10-21 |
| GB8415087D0 (en) | 1984-07-18 |
| US4588736A (en) | 1986-05-13 |
| DK286984A (da) | 1984-12-14 |
| PT78717A (de) | 1984-07-01 |
| IL72076A0 (en) | 1984-10-31 |
| ES533320A0 (es) | 1985-08-01 |
| FI842360A0 (fi) | 1984-06-12 |
| KR850000409A (ko) | 1985-02-27 |
| DE3461375D1 (en) | 1987-01-08 |
| ZA844411B (en) | 1986-02-26 |
| ATE23715T1 (de) | 1986-12-15 |
| GB2142627B (en) | 1986-11-12 |
| CA1226580A (en) | 1987-09-08 |
| EP0129153A1 (de) | 1984-12-27 |
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