NO115660B - - Google Patents
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- Publication number
- NO115660B NO115660B NO154352A NO15435264A NO115660B NO 115660 B NO115660 B NO 115660B NO 154352 A NO154352 A NO 154352A NO 15435264 A NO15435264 A NO 15435264A NO 115660 B NO115660 B NO 115660B
- Authority
- NO
- Norway
- Prior art keywords
- phenyl
- lower alkyl
- group
- substituted
- residue
- Prior art date
Links
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 45
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 38
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 36
- -1 hydroxy- Chemical class 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 19
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 18
- 235000019253 formic acid Nutrition 0.000 claims description 18
- 239000012445 acidic reagent Substances 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- JSGGRYKYWNCXKA-UHFFFAOYSA-N 2-amino-n-(3,4-dimethoxyphenyl)acetamide Chemical compound COC1=CC=C(NC(=O)CN)C=C1OC JSGGRYKYWNCXKA-UHFFFAOYSA-N 0.000 claims description 9
- 239000007858 starting material Substances 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
- GVONPBONFIJAHJ-UHFFFAOYSA-N imidazolidin-4-one Chemical class O=C1CNCN1 GVONPBONFIJAHJ-UHFFFAOYSA-N 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- GIBRATRQHFFRHE-UHFFFAOYSA-N 2-amino-n-(2-benzoyl-4-chlorophenyl)acetamide Chemical compound NCC(=O)NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 GIBRATRQHFFRHE-UHFFFAOYSA-N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 2
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- RMAVZDYKICXJHO-UHFFFAOYSA-N 2-amino-n-(3-chlorophenyl)acetamide Chemical compound NCC(=O)NC1=CC=CC(Cl)=C1 RMAVZDYKICXJHO-UHFFFAOYSA-N 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 238000002844 melting Methods 0.000 description 25
- 230000008018 melting Effects 0.000 description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 229960004279 formaldehyde Drugs 0.000 description 13
- 235000019256 formaldehyde Nutrition 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000000155 melt Substances 0.000 description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 8
- ILTLMURTHWTWNJ-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)imidazolidin-4-one Chemical compound C1=C(OC)C(OC)=CC=C1N1C(=O)CNC1 ILTLMURTHWTWNJ-UHFFFAOYSA-N 0.000 description 7
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000002585 base Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 150000002431 hydrogen Chemical group 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 230000001476 alcoholic effect Effects 0.000 description 4
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 4
- 239000013067 intermediate product Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- KAKNBEGIEWLLKL-UHFFFAOYSA-N C(C1=CC=CC=C1)NCC(=O)NC1=CC(=C(C=C1)OC)OC Chemical compound C(C1=CC=CC=C1)NCC(=O)NC1=CC(=C(C=C1)OC)OC KAKNBEGIEWLLKL-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- SLJSUFZDKZAKHO-UHFFFAOYSA-N benzyl n-[2-(3,4-dimethoxyanilino)-2-oxoethyl]carbamate Chemical compound C1=C(OC)C(OC)=CC=C1NC(=O)CNC(=O)OCC1=CC=CC=C1 SLJSUFZDKZAKHO-UHFFFAOYSA-N 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
- 230000000694 effects Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000008098 formaldehyde solution Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 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 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- QZERQIUDKAQIFM-UHFFFAOYSA-N (2-methoxyphenoxy)methanamine Chemical compound COC1=CC=CC=C1OCN QZERQIUDKAQIFM-UHFFFAOYSA-N 0.000 description 2
- VJHZNRWCZGUFBT-UHFFFAOYSA-N 3-(4-nitrophenyl)imidazolidin-4-one Chemical compound [N+](=O)([O-])C1=CC=C(C=C1)N1CNCC1=O VJHZNRWCZGUFBT-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 150000008043 acidic salts Chemical class 0.000 description 2
- 230000003356 anti-rheumatic effect Effects 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 229940102396 methyl bromide Drugs 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 229940072033 potash Drugs 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- ATBIAJXSKNPHEI-UHFFFAOYSA-N pyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=CN=C1 ATBIAJXSKNPHEI-UHFFFAOYSA-N 0.000 description 2
- 238000006467 substitution reaction Methods 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
- NMYWMOZOCYAHNC-LBPRGKRZSA-N (2s)-2-(phenylmethoxycarbonylamino)hexanoic acid Chemical compound CCCC[C@@H](C(O)=O)NC(=O)OCC1=CC=CC=C1 NMYWMOZOCYAHNC-LBPRGKRZSA-N 0.000 description 1
- HIOFHWTUAOODBJ-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)oxirane Chemical compound C1=C(Cl)C(Cl)=CC=C1C1OC1 HIOFHWTUAOODBJ-UHFFFAOYSA-N 0.000 description 1
- KGSVNOLLROCJQM-UHFFFAOYSA-N 2-(benzylamino)acetic acid Chemical compound OC(=O)CNCC1=CC=CC=C1 KGSVNOLLROCJQM-UHFFFAOYSA-N 0.000 description 1
- BIFJQDWBDOUUSC-UHFFFAOYSA-N 2-methyl-3-(2-methylphenoxy)oxirane Chemical compound CC1OC1OC1=C(C)C=CC=C1 BIFJQDWBDOUUSC-UHFFFAOYSA-N 0.000 description 1
- LGDHZCLREKIGKJ-UHFFFAOYSA-N 3,4-dimethoxyaniline Chemical compound COC1=CC=C(N)C=C1OC LGDHZCLREKIGKJ-UHFFFAOYSA-N 0.000 description 1
- GIIFEEANMNOEFL-UHFFFAOYSA-N 3-(4-aminophenyl)imidazolidin-4-one Chemical compound NC1=CC=C(C=C1)N1CNCC1=O GIIFEEANMNOEFL-UHFFFAOYSA-N 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
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 1
- 241001432959 Chernes Species 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
- CJUMAFVKTCBCJK-UHFFFAOYSA-N N-benzyloxycarbonylglycine Chemical compound OC(=O)CNC(=O)OCC1=CC=CC=C1 CJUMAFVKTCBCJK-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- DUCNKBZIKNAQOS-UHFFFAOYSA-N O=[C]C1=CC=CN=C1 Chemical compound O=[C]C1=CC=CN=C1 DUCNKBZIKNAQOS-UHFFFAOYSA-N 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-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
- 238000010521 absorption reaction Methods 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 239000003435 antirheumatic agent Substances 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000006264 debenzylation reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 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
- C07D233/04—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
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1848466A CH470396A (de) | 1963-08-12 | 1963-08-12 | Verfahren zur Herstellung von 4-Imidazolidon-Verbindungen |
| CH993163A CH449029A (de) | 1963-08-12 | 1963-08-12 | Verfahren zur Herstellung von 4-Imidazolidon-Verbindungen |
| CH73764A CH465621A (de) | 1963-08-12 | 1964-01-22 | Verfahren zur Herstellung von 4-Imidazolidon-Verbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO115660B true NO115660B (fr) | 1968-11-11 |
Family
ID=27172369
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO154352A NO115660B (fr) | 1963-08-12 | 1964-08-11 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3428646A (fr) |
| BE (1) | BE651670A (fr) |
| BR (1) | BR6461671D0 (fr) |
| CH (3) | CH470396A (fr) |
| DE (1) | DE1445904A1 (fr) |
| ES (1) | ES303009A1 (fr) |
| FR (2) | FR1413943A (fr) |
| GB (1) | GB1036280A (fr) |
| IL (1) | IL21827A (fr) |
| NL (1) | NL6409088A (fr) |
| NO (1) | NO115660B (fr) |
| SE (1) | SE327204B (fr) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3442892A (en) * | 1965-06-11 | 1969-05-06 | Nippon Shinyaku Co Ltd | Imidazolidinone derivatives |
| US3975443A (en) * | 1972-06-06 | 1976-08-17 | Allen & Hanburys Limited | 1-(3,4-dichlorobenzamidomethyl)-cyclohexyldimethylamine |
| CH579117A5 (fr) * | 1973-06-22 | 1976-08-31 | Ciba Geigy Ag | |
| US4280008A (en) * | 1976-12-24 | 1981-07-21 | Basf Aktiengesellschaft | Chirally substituted 2-imidazolin-5-ones |
| US4170462A (en) * | 1978-01-23 | 1979-10-09 | American Cyanamid Company | Method for controlling the relative stem growth of plants |
| US4310429A (en) * | 1978-06-19 | 1982-01-12 | The B. F. Goodrich Company | Stabilized polymers, novel stabilizers, and synthesis thereof |
| US4601839A (en) * | 1978-06-19 | 1986-07-22 | The B. F. Goodrich Company | Stabilized polymers, novel stabilizers, and synthesis thereof |
| IT1209644B (it) * | 1985-06-21 | 1989-08-30 | Isf Spa | Composti farmacologicamente attivi. |
| IT1222367B (it) * | 1985-06-21 | 1990-09-05 | Isf Spa | Amminoacil derivati di 4(5)-imidazolodinoni adattivita' nootropica:loro preparazione ed uso farmaceutico |
| IT1190378B (it) * | 1985-06-21 | 1988-02-16 | Isf Spa | Derivati pirrolidonici |
| FR2677984B1 (fr) * | 1991-06-21 | 1994-02-25 | Elf Sanofi | Derives d'imidazoline n-substitues, leur preparation, les compositions pharmaceutiques en contenant. |
| US5399706A (en) * | 1993-03-02 | 1995-03-21 | H. B. Fuller Licensing & Financing, Inc. | Imidazolidinone diamine and derivatives thereof |
| WO2008132139A2 (fr) * | 2007-04-27 | 2008-11-06 | Ucb Pharma S.A. | Nouveaux dérivés hétérocycliques utiles pour le traitement des troubles du système nerveux central |
| WO2009004430A1 (fr) * | 2007-06-29 | 2009-01-08 | Pfizer Inc. | N-benzyl oxazolidinones et composés hétérocycliques apparentés comme potentialisateurs de récepteurs du glutamate |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2877179A (en) * | 1956-03-26 | 1959-03-10 | Cities Service Res & Dev Co | Composition for and method of inhibiting corrosion of metals |
-
1963
- 1963-08-12 CH CH1848466A patent/CH470396A/de not_active IP Right Cessation
- 1963-08-12 CH CH993163A patent/CH449029A/de unknown
-
1964
- 1964-01-22 CH CH73764A patent/CH465621A/de unknown
- 1964-07-18 DE DE19641445904 patent/DE1445904A1/de active Pending
- 1964-08-03 IL IL21827A patent/IL21827A/xx unknown
- 1964-08-05 US US387807A patent/US3428646A/en not_active Expired - Lifetime
- 1964-08-07 NL NL6409088A patent/NL6409088A/xx unknown
- 1964-08-10 GB GB32426/64A patent/GB1036280A/en not_active Expired
- 1964-08-11 BR BR161671/64A patent/BR6461671D0/pt unknown
- 1964-08-11 BE BE651670D patent/BE651670A/xx unknown
- 1964-08-11 ES ES0303009A patent/ES303009A1/es not_active Expired
- 1964-08-11 NO NO154352A patent/NO115660B/no unknown
- 1964-08-12 SE SE09736/64A patent/SE327204B/xx unknown
- 1964-08-12 FR FR984912A patent/FR1413943A/fr not_active Expired
- 1964-08-12 FR FR984913A patent/FR3769M/fr active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CH470396A (de) | 1969-03-31 |
| FR3769M (fr) | 1965-12-20 |
| CH465621A (de) | 1968-11-30 |
| NL6409088A (fr) | 1965-02-15 |
| ES303009A1 (es) | 1965-03-16 |
| GB1036280A (en) | 1966-07-20 |
| BE651670A (fr) | 1965-02-11 |
| FR1413943A (fr) | 1965-10-15 |
| SE327204B (fr) | 1970-08-17 |
| BR6461671D0 (pt) | 1973-07-17 |
| IL21827A (en) | 1968-03-28 |
| DE1445904A1 (de) | 1969-03-20 |
| CH449029A (de) | 1967-12-31 |
| US3428646A (en) | 1969-02-18 |
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