NO135786B - - Google Patents
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- Publication number
- NO135786B NO135786B NO750902A NO750902A NO135786B NO 135786 B NO135786 B NO 135786B NO 750902 A NO750902 A NO 750902A NO 750902 A NO750902 A NO 750902A NO 135786 B NO135786 B NO 135786B
- Authority
- NO
- Norway
- Prior art keywords
- residue
- formula
- aroyl
- imidazoline
- compounds
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 26
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 24
- 125000003435 aroyl group Chemical group 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 150000007513 acids Chemical class 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
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 235000005985 organic acids Nutrition 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 150000001735 carboxylic acids Chemical group 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- -1 alkyl mercaptoimidazoline Chemical compound 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 235000011121 sodium hydroxide Nutrition 0.000 description 8
- 150000001448 anilines Chemical class 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000003776 cleavage reaction Methods 0.000 description 7
- 230000007017 scission Effects 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- JDMFXJULNGEPOI-UHFFFAOYSA-N 2,6-dichloroaniline Chemical compound NC1=C(Cl)C=CC=C1Cl JDMFXJULNGEPOI-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- GJSURZIOUXUGAL-UHFFFAOYSA-N Clonidine Chemical compound ClC1=CC=CC(Cl)=C1NC1=NCCN1 GJSURZIOUXUGAL-UHFFFAOYSA-N 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 230000001624 sedative effect Effects 0.000 description 5
- AJSFBSYWKIBTGP-UHFFFAOYSA-N 1-benzoylimidazolidin-2-one Chemical compound C=1C=CC=CC=1C(=O)N1CCNC1=O AJSFBSYWKIBTGP-UHFFFAOYSA-N 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000007127 saponification reaction Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- HKNSIVFWRXBWCK-UHFFFAOYSA-N [N].NC1=CC=CC=C1 Chemical compound [N].NC1=CC=CC=C1 HKNSIVFWRXBWCK-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000012491 analyte Substances 0.000 description 2
- 239000002220 antihypertensive agent Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 230000004531 blood pressure lowering effect Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000001077 hypotensive effect Effects 0.000 description 2
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 230000011514 reflex Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- HUEYSSLYFJVUIS-MRFSYGAJSA-N (2s,3r,11bs)-2-[[(1r)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl]-3-ethyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1h-benzo[a]quinolizine;hydron;chloride Chemical compound Cl.N1CCC2=CC(OC)=C(OC)C=C2[C@H]1C[C@H]1C[C@H]2C3=CC(OC)=C(OC)C=C3CCN2C[C@@H]1CC HUEYSSLYFJVUIS-MRFSYGAJSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OXEKMIHSBMWONF-UHFFFAOYSA-N 1-(2-oxoimidazolidin-1-yl)phosphanylimidazolidin-2-one hydrochloride Chemical compound Cl.O=C1NCCN1PN1C(=O)NCC1 OXEKMIHSBMWONF-UHFFFAOYSA-N 0.000 description 1
- PGTOGOCRLGQJNM-UHFFFAOYSA-N 1-(3-methylphenyl)imidazolidin-2-one Chemical compound CC1=CC=CC(N2C(NCC2)=O)=C1 PGTOGOCRLGQJNM-UHFFFAOYSA-N 0.000 description 1
- OSOUNOBYRMOXQQ-UHFFFAOYSA-N 1-chloro-3-methylbenzene Chemical compound CC1=CC=CC(Cl)=C1 OSOUNOBYRMOXQQ-UHFFFAOYSA-N 0.000 description 1
- XIRRDAWDNHRRLB-UHFFFAOYSA-N 2,6-dibromoaniline Chemical compound NC1=C(Br)C=CC=C1Br XIRRDAWDNHRRLB-UHFFFAOYSA-N 0.000 description 1
- WFNLHDJJZSJARK-UHFFFAOYSA-N 2-chloro-6-methylaniline Chemical compound CC1=CC=CC(Cl)=C1N WFNLHDJJZSJARK-UHFFFAOYSA-N 0.000 description 1
- NQUVCRCCRXRJCK-UHFFFAOYSA-N 4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1 NQUVCRCCRXRJCK-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- RYECOJGRJDOGPP-UHFFFAOYSA-N Ethylurea Chemical compound CCNC(N)=O RYECOJGRJDOGPP-UHFFFAOYSA-N 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 241001233242 Lontra Species 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229910019213 POCl3 Inorganic materials 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- UKIBUEVBTOXARC-UHFFFAOYSA-N [2-(2,6-dibromoanilino)-4,5-dihydroimidazol-1-yl]-phenylmethanone Chemical compound BrC1=CC=CC(Br)=C1NC1=NCCN1C(=O)C1=CC=CC=C1 UKIBUEVBTOXARC-UHFFFAOYSA-N 0.000 description 1
- YHEMKMZUJKPOCO-UHFFFAOYSA-N [2-(2,6-dichloroanilino)-4,5-dihydroimidazol-1-yl]-phenylmethanone Chemical compound ClC1=CC=CC(Cl)=C1NC1=NCCN1C(=O)C1=CC=CC=C1 YHEMKMZUJKPOCO-UHFFFAOYSA-N 0.000 description 1
- RPWIXZCUKBAUHZ-UHFFFAOYSA-N [2-(2-chloro-6-methylanilino)-4,5-dihydroimidazol-1-yl]-phenylmethanone Chemical compound CC1=CC=CC(Cl)=C1NC1=NCCN1C(=O)C1=CC=CC=C1 RPWIXZCUKBAUHZ-UHFFFAOYSA-N 0.000 description 1
- GYJDNTLCTPWPIK-UHFFFAOYSA-N [N].N1C=NCC1 Chemical compound [N].N1C=NCC1 GYJDNTLCTPWPIK-UHFFFAOYSA-N 0.000 description 1
- 230000009102 absorption Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- VEQOALNAAJBPNY-UHFFFAOYSA-N antipyrine Chemical compound CN1C(C)=CC(=O)N1C1=CC=CC=C1 VEQOALNAAJBPNY-UHFFFAOYSA-N 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 210000001326 carotid sinus Anatomy 0.000 description 1
- 239000003874 central nervous system depressant Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000004401 m-toluyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C(*)=O 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- LUYNKPLROYXIBK-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-1-(2-methylphenyl)-4,5-dihydroimidazol-2-amine Chemical compound CC1=CC=CC=C1N1C(NC=2C(=CC=CC=2Cl)Cl)=NCC1 LUYNKPLROYXIBK-UHFFFAOYSA-N 0.000 description 1
- WVBFELDKHPOQCL-UHFFFAOYSA-N n-(2,6-dichlorophenyl)-1-(4-methylphenyl)-4,5-dihydroimidazol-2-amine Chemical compound C1=CC(C)=CC=C1N1C(NC=2C(=CC=CC=2Cl)Cl)=NCC1 WVBFELDKHPOQCL-UHFFFAOYSA-N 0.000 description 1
- 150000003941 n-butylamines Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000005441 o-toluyl group Chemical group [H]C1=C([H])C(C(*)=O)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 125000005440 p-toluyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C(*)=O)C([H])([H])[H] 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- INDZTCRIYSRWOH-UHFFFAOYSA-N undec-10-enyl carbamimidothioate;hydroiodide Chemical compound I.NC(=N)SCCCCCCCCCC=C INDZTCRIYSRWOH-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
- C07D233/04—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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (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 |
|---|---|---|---|
| AT285474A AT330769B (de) | 1974-04-05 | 1974-04-05 | Verfahren zur herstellung von 2-arylamino- 2-imidazolin-derivaten und ihren salzen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO750902L NO750902L (fr) | 1975-10-07 |
| NO135786B true NO135786B (fr) | 1977-02-21 |
| NO135786C NO135786C (fr) | 1977-06-01 |
Family
ID=3541347
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO750902A NO135786C (fr) | 1974-04-05 | 1975-03-17 |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US3988345A (fr) |
| JP (1) | JPS524553B2 (fr) |
| AT (1) | AT330769B (fr) |
| BE (1) | BE827582A (fr) |
| BG (1) | BG25082A3 (fr) |
| CA (1) | CA1044241A (fr) |
| CH (1) | CH613695A5 (fr) |
| CS (1) | CS187466B2 (fr) |
| DD (1) | DD117230A5 (fr) |
| DE (2) | DE2559711C3 (fr) |
| DK (1) | DK146006C (fr) |
| ES (1) | ES436296A1 (fr) |
| FI (1) | FI64144C (fr) |
| FR (1) | FR2266504B1 (fr) |
| GB (1) | GB1506914A (fr) |
| HU (1) | HU171867B (fr) |
| IL (1) | IL46926A (fr) |
| NL (1) | NL176853C (fr) |
| NO (1) | NO135786C (fr) |
| PL (1) | PL97085B1 (fr) |
| RO (1) | RO70568A (fr) |
| SE (1) | SE417507B (fr) |
| SU (1) | SU548207A3 (fr) |
| YU (1) | YU39113B (fr) |
| ZA (1) | ZA751851B (fr) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2542702C2 (de) * | 1975-09-25 | 1983-11-10 | Lentia GmbH Chem. u. pharm. Erzeugnisse - Industriebedarf, 8000 München | Verfahren zur Herstellung von 1-Benzoyl-2-(2,6-dichlorphenylamino)-2-imidazolin |
| DE2652004C3 (de) * | 1976-11-15 | 1979-09-13 | Basf Ag, 6700 Ludwigshafen | l-Acyl-2-arylamino-2-imidazoline, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE2658808A1 (de) * | 1976-12-24 | 1978-07-06 | Boehringer Sohn Ingelheim | 2-brom-3-chlor-n-2-imidazolidinylen- benzamin, dessen saeureadditionssalze, diese enthaltende arzneimittel und verfahren zu deren herstellung |
| NL7711390A (nl) * | 1977-10-18 | 1979-04-20 | Philips Nv | Nieuwe 2-arylimino-hexahydopyrimidinen en - imi- dazolidinen, zouten en complexen daarvan, werk- wijze ter bereiding van de nieuwe verbindingen, alsmede fungicide preparaten op basis van de nieuwe verbindingen. |
| DE2811847A1 (de) | 1978-03-17 | 1979-09-20 | Lentia Gmbh | Neue arylaminoimidazolinderivate, deren herstellung und verwendung als arzneimittel |
| US4262005A (en) * | 1978-05-31 | 1981-04-14 | The Boots Company Limited | Compounds, compositions and methods for controlling pests |
| DE2854659A1 (de) * | 1978-12-18 | 1980-07-10 | Boehringer Sohn Ingelheim | Neue 3,4-disubstituierte 2-phenylimino-imidazolidine, deren saeureadditionssalze, diese enthaltende arzneimittel und verfahren zu deren herstellung |
| US4287201A (en) * | 1980-03-03 | 1981-09-01 | Merck & Co., Inc. | Anovulatory method and chicken feed compositions |
| DE3011327A1 (de) * | 1980-03-24 | 1981-10-01 | Basf Ag, 6700 Ludwigshafen | 1-aroyl-2-phenylamino-2-imidazoline, ihre herstellung und verwendung |
| US4363751A (en) * | 1980-08-04 | 1982-12-14 | Merck & Co., Inc. | Catalyst for the preparation of 4-cyanothiazole and process for preparing the catalyst |
| DE3200258A1 (de) * | 1982-01-07 | 1983-07-21 | Lentia GmbH Chem. u. pharm. Erzeugnisse - Industriebedarf, 8000 München | Substituierte 1-benzoyl-2-phenylimino-imidazolidine, deren saeureadditionssalze, verfahren zu deren herstellung und diese enthaltende arzneimittel |
| HU192986B (en) | 1984-05-23 | 1987-08-28 | Egyt Gyogyszervegyeszeti Gyar | Process for production of imidasodiline derivatives |
| BRPI0815500A2 (pt) * | 2007-08-15 | 2017-05-30 | Allergan Inc | compostos terapêuticos, bem como seus usos |
| US8426454B2 (en) * | 2007-08-15 | 2013-04-23 | Allergan, Inc. | Therapeutic compounds |
| RU2652125C1 (ru) * | 2017-10-02 | 2018-04-25 | Акционерное общество "Федеральный научно-производственный центр "Алтай" | Способ получения 2-(2,6-дихлорфениламино)-2-имидазолина гидрохлорида |
| JP2023519882A (ja) | 2020-03-27 | 2023-05-15 | ソム、イノベーション、バイオテック、ソシエダッド、アノニマ | シヌクレイノパチーの治療に有用な化合物 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE632578A (fr) * | 1963-05-22 | |||
| BE741947A (en) * | 1969-11-19 | 1970-05-04 | N-acyl-2-arylamino-imidazoline | |
| DE2316377C3 (de) * | 1973-04-02 | 1978-11-02 | Lentia Gmbh, Chem. U. Pharm. Erzeugnisse - Industriebedarf, 8000 Muenchen | Verfahren zur Herstellung von 2-Phenyl-amino-2-imidazolin-Derivaten und von deren Salzen |
-
1974
- 1974-04-05 AT AT285474A patent/AT330769B/de not_active IP Right Cessation
-
1975
- 1975-02-07 DE DE2559711A patent/DE2559711C3/de not_active Expired
- 1975-02-07 DE DE2505297A patent/DE2505297C3/de not_active Expired
- 1975-02-20 BG BG029028A patent/BG25082A3/xx unknown
- 1975-02-26 CH CH239175A patent/CH613695A5/xx not_active IP Right Cessation
- 1975-03-06 FI FI750653A patent/FI64144C/fi not_active IP Right Cessation
- 1975-03-07 YU YU00560/75A patent/YU39113B/xx unknown
- 1975-03-10 DK DK94175A patent/DK146006C/da not_active IP Right Cessation
- 1975-03-17 NO NO750902A patent/NO135786C/no unknown
- 1975-03-18 GB GB46657/76A patent/GB1506914A/en not_active Expired
- 1975-03-19 NL NLAANVRAGE7503267,A patent/NL176853C/xx not_active IP Right Cessation
- 1975-03-24 ZA ZA00751851A patent/ZA751851B/xx unknown
- 1975-03-24 RO RO7589483A patent/RO70568A/fr unknown
- 1975-03-25 IL IL46926A patent/IL46926A/xx unknown
- 1975-03-25 SU SU2116922A patent/SU548207A3/ru active
- 1975-03-26 SE SE7503514A patent/SE417507B/xx not_active IP Right Cessation
- 1975-03-26 FR FR7509445A patent/FR2266504B1/fr not_active Expired
- 1975-04-01 CA CA223,440A patent/CA1044241A/fr not_active Expired
- 1975-04-01 HU HU75CE00001037A patent/HU171867B/hu unknown
- 1975-04-03 DD DD185201A patent/DD117230A5/xx unknown
- 1975-04-03 JP JP50039893A patent/JPS524553B2/ja not_active Expired
- 1975-04-03 PL PL1975179322A patent/PL97085B1/pl unknown
- 1975-04-04 BE BE155108A patent/BE827582A/fr not_active IP Right Cessation
- 1975-04-04 CS CS752319A patent/CS187466B2/cs unknown
- 1975-04-04 ES ES436296A patent/ES436296A1/es not_active Expired
- 1975-04-07 US US05/565,762 patent/US3988345A/en not_active Expired - Lifetime
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