PL94027B1 - - Google Patents
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- PL94027B1 PL94027B1 PL17846771A PL17846771A PL94027B1 PL 94027 B1 PL94027 B1 PL 94027B1 PL 17846771 A PL17846771 A PL 17846771A PL 17846771 A PL17846771 A PL 17846771A PL 94027 B1 PL94027 B1 PL 94027B1
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- PL
- Poland
- Prior art keywords
- carbon atoms
- general formula
- formula
- group
- compound
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- -1 ureidophenyl Chemical class 0.000 claims description 66
- 150000001875 compounds Chemical class 0.000 claims description 54
- 125000004432 carbon atom Chemical group C* 0.000 claims description 36
- 150000001412 amines Chemical class 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 26
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 24
- 125000006239 protecting group Chemical group 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 150000007522 mineralic acids Chemical class 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 150000007524 organic acids Chemical class 0.000 claims description 10
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims description 8
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 235000005985 organic acids Nutrition 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 5
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 5
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 5
- 229910000510 noble metal Inorganic materials 0.000 claims description 5
- 229910052697 platinum Inorganic materials 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000007868 Raney catalyst Substances 0.000 claims description 4
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 125000005843 halogen group Chemical group 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 239000003701 inert diluent Substances 0.000 claims 3
- 239000012442 inert solvent Substances 0.000 claims 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 229910052740 iodine Inorganic materials 0.000 claims 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- 240000006661 Serenoa repens Species 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 230000007935 neutral effect Effects 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 33
- 238000002844 melting Methods 0.000 description 31
- 230000008018 melting Effects 0.000 description 31
- 239000000243 solution Substances 0.000 description 27
- 239000000155 melt Substances 0.000 description 26
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 25
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
- 238000001953 recrystallisation Methods 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000047 product Substances 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 9
- 229960001317 isoprenaline Drugs 0.000 description 9
- CWYZDPHNAGSFQB-UHFFFAOYSA-N n-propylbutan-1-amine Chemical compound CCCCNCCC CWYZDPHNAGSFQB-UHFFFAOYSA-N 0.000 description 9
- 230000009471 action Effects 0.000 description 8
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 7
- OWUOHIMJYZRAGE-UHFFFAOYSA-N 1-cyclohexyl-3-[4-(oxiran-2-ylmethoxy)phenyl]urea Chemical compound C=1C=C(OCC2OC2)C=CC=1NC(=O)NC1CCCCC1 OWUOHIMJYZRAGE-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 239000004202 carbamide Substances 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 4
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000001294 propane Substances 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000005711 Benzoic acid Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 241000282326 Felis catus Species 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- 230000036772 blood pressure Effects 0.000 description 3
- 230000008602 contraction Effects 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 230000000297 inotrophic effect Effects 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- RUPKEIHOXHDNNN-UHFFFAOYSA-N 1-[4-[3-(but-2-enylamino)-2-hydroxypropoxy]phenyl]-3-cyclohexylurea Chemical compound C1=CC(OCC(O)CNCC=CC)=CC=C1NC(=O)NC1CCCCC1 RUPKEIHOXHDNNN-UHFFFAOYSA-N 0.000 description 2
- OGHBPFBLTODNEK-UHFFFAOYSA-N 1-[4-[3-(cycloheptylamino)-2-hydroxypropoxy]phenyl]-3-cyclohexylurea Chemical compound C1(CCCCC1)NC(NC1=CC=C(OCC(CNC2CCCCCC2)O)C=C1)=O OGHBPFBLTODNEK-UHFFFAOYSA-N 0.000 description 2
- UGJCCJAWMRVCOV-UHFFFAOYSA-N 1-cyclohexyl-3-[4-[2-hydroxy-3-(3-methylbutylamino)propoxy]phenyl]urea Chemical compound C1(CCCCC1)NC(NC1=CC=C(OCC(CNCCC(C)C)O)C=C1)=O UGJCCJAWMRVCOV-UHFFFAOYSA-N 0.000 description 2
- MQVJCDXQDDHXED-UHFFFAOYSA-N 1-cyclohexyl-3-[4-[2-hydroxy-3-(methylamino)propoxy]phenyl]urea Chemical compound C1(CCCCC1)NC(NC1=CC=C(OCC(CNC)O)C=C1)=O MQVJCDXQDDHXED-UHFFFAOYSA-N 0.000 description 2
- XMUPYGCITCUYQP-UHFFFAOYSA-N 1-methyl-3-[4-(oxiran-2-ylmethoxy)phenyl]urea Chemical compound CNC(=O)NC1=CC=C(C=C1)OCC1CO1 XMUPYGCITCUYQP-UHFFFAOYSA-N 0.000 description 2
- XFSBVAOIAHNAPC-XTHSEXKGSA-N 16-Ethyl-1alpha,6alpha,19beta-trimethoxy-4-(methoxymethyl)-aconitane-3alpha,8,10alpha,11,18alpha-pentol, 8-acetate 10-benzoate Chemical compound O([C@H]1[C@]2(O)C[C@H]3[C@@]45C6[C@@H]([C@@]([C@H]31)(OC(C)=O)[C@@H](O)[C@@H]2OC)[C@H](OC)[C@@H]4[C@]([C@@H](C[C@@H]5OC)O)(COC)CN6CC)C(=O)C1=CC=CC=C1 XFSBVAOIAHNAPC-XTHSEXKGSA-N 0.000 description 2
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XFSBVAOIAHNAPC-UHFFFAOYSA-N Aconitin Natural products CCN1CC(C(CC2OC)O)(COC)C3C(OC)C(C(C45)(OC(C)=O)C(O)C6OC)C1C32C4CC6(O)C5OC(=O)C1=CC=CC=C1 XFSBVAOIAHNAPC-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229940039750 aconitine Drugs 0.000 description 2
- STDXGNLCJACLFY-UHFFFAOYSA-N aconitine Natural products CCN1CC2(COC)C(O)CC(O)C34C5CC6(O)C(OC)C(O)C(OC(=O)C)(C5C6OC(=O)c7ccccc7)C(C(OC)C23)C14 STDXGNLCJACLFY-UHFFFAOYSA-N 0.000 description 2
- 206010003119 arrhythmia Diseases 0.000 description 2
- 230000006793 arrhythmia Effects 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 230000002057 chronotropic effect Effects 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000006264 debenzylation reaction Methods 0.000 description 2
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 210000002837 heart atrium Anatomy 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- DURULFYMVIFBIR-UHFFFAOYSA-N practolol Chemical compound CC(C)NCC(O)COC1=CC=C(NC(C)=O)C=C1 DURULFYMVIFBIR-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 229960004889 salicylic acid Drugs 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- MXFWWQICDIZSOA-UHFFFAOYSA-N talinolol Chemical compound C1=CC(OCC(O)CNC(C)(C)C)=CC=C1NC(=O)NC1CCCCC1 MXFWWQICDIZSOA-UHFFFAOYSA-N 0.000 description 2
- 230000002792 vascular Effects 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- FREZYOGUJGWALW-UHFFFAOYSA-N 1-(4-hydroxyphenyl)-3-methylurea Chemical compound CNC(=O)NC1=CC=C(O)C=C1 FREZYOGUJGWALW-UHFFFAOYSA-N 0.000 description 1
- ZWMOWFJMDHZCNJ-UHFFFAOYSA-N 1-[4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]-3-methylurea Chemical compound CNC(=O)NC1=CC=C(OCC(O)CNC(C)C)C=C1 ZWMOWFJMDHZCNJ-UHFFFAOYSA-N 0.000 description 1
- VHJCBLXZVBTABV-UHFFFAOYSA-N 1-[4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]-3-propan-2-ylurea Chemical compound C(C)(C)NC(NC1=CC=C(OCC(CNC(C)C)O)C=C1)=O VHJCBLXZVBTABV-UHFFFAOYSA-N 0.000 description 1
- ZRUDGODGZAZHQY-UHFFFAOYSA-N 1-[4-[3-(butylamino)-2-hydroxypropoxy]phenyl]-3-cyclohexylurea Chemical compound C1(CCCCC1)NC(NC1=CC=C(OCC(CNCCCC)O)C=C1)=O ZRUDGODGZAZHQY-UHFFFAOYSA-N 0.000 description 1
- ZXICSJLSQAPYGB-UHFFFAOYSA-N 1-but-2-enyl-3-[4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]urea Chemical compound C(C=CC)NC(NC1=CC=C(OCC(CNC(C)C)O)C=C1)=O ZXICSJLSQAPYGB-UHFFFAOYSA-N 0.000 description 1
- RQLAWYIMRBTCHU-UHFFFAOYSA-N 1-cyclohexyl-3-(4-hydroxyphenyl)urea Chemical compound C1=CC(O)=CC=C1NC(=O)NC1CCCCC1 RQLAWYIMRBTCHU-UHFFFAOYSA-N 0.000 description 1
- ZVWSNXCTWJBKPV-UHFFFAOYSA-N 1-cyclohexyl-3-[2-(oxiran-2-ylmethoxy)phenyl]urea Chemical compound C1(CCCCC1)NC(=O)NC1=C(C=CC=C1)OCC1CO1 ZVWSNXCTWJBKPV-UHFFFAOYSA-N 0.000 description 1
- JYBJDVFUKCGOFM-UHFFFAOYSA-N 1-cyclohexyl-3-[3-(oxiran-2-ylmethoxy)phenyl]urea Chemical compound C1(CCCCC1)NC(=O)NC1=CC(=CC=C1)OCC1CO1 JYBJDVFUKCGOFM-UHFFFAOYSA-N 0.000 description 1
- KSQZLKFCBZMSKA-UHFFFAOYSA-N 1-cyclohexyl-3-[4-[3-(cyclohexylamino)-2-hydroxypropoxy]phenyl]urea Chemical compound C=1C=C(NC(=O)NC2CCCCC2)C=CC=1OCC(O)CNC1CCCCC1 KSQZLKFCBZMSKA-UHFFFAOYSA-N 0.000 description 1
- NYYSFOJJGVOLRP-UHFFFAOYSA-N 1-cyclohexyl-3-[4-[3-(cyclopentylamino)-2-hydroxypropoxy]phenyl]urea Chemical compound C=1C=C(NC(=O)NC2CCCCC2)C=CC=1OCC(O)CNC1CCCC1 NYYSFOJJGVOLRP-UHFFFAOYSA-N 0.000 description 1
- OLIFELJOFNMHRO-UHFFFAOYSA-N 1-cyclohexyl-3-[4-[3-(cyclopropylamino)-2-hydroxypropoxy]phenyl]urea Chemical compound C1(CCCCC1)NC(NC1=CC=C(OCC(CNC2CC2)O)C=C1)=O OLIFELJOFNMHRO-UHFFFAOYSA-N 0.000 description 1
- OSOJHWBJMSAAEJ-UHFFFAOYSA-N 1-cyclohexyl-3-[4-[3-(hexylamino)-2-hydroxypropoxy]phenyl]urea Chemical compound C1(CCCCC1)NC(NC1=CC=C(OCC(CNCCCCCC)O)C=C1)=O OSOJHWBJMSAAEJ-UHFFFAOYSA-N 0.000 description 1
- MVSQSTCYZTZEIE-UHFFFAOYSA-N 1-ethyl-3-[4-(oxiran-2-ylmethoxy)phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1OCC1OC1 MVSQSTCYZTZEIE-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- CFJMHEIWIQRQOI-UHFFFAOYSA-N 1-hexyl-3-[4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]urea Chemical compound CCCCCCNC(=O)NC1=CC=C(OCC(O)CNC(C)C)C=C1 CFJMHEIWIQRQOI-UHFFFAOYSA-N 0.000 description 1
- 125000005978 1-naphthyloxy group Chemical group 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 208000009079 Bronchial Spasm Diseases 0.000 description 1
- 208000014181 Bronchial disease Diseases 0.000 description 1
- 206010006482 Bronchospasm Diseases 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- OJANSDIGRNTINO-UHFFFAOYSA-N CC(C)(C)N(CC(COC(C=C1)=CC=C1NC(NC1CCCCC1)=O)O)CC1=CC=CC=C1 Chemical compound CC(C)(C)N(CC(COC(C=C1)=CC=C1NC(NC1CCCCC1)=O)O)CC1=CC=CC=C1 OJANSDIGRNTINO-UHFFFAOYSA-N 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 108091005960 Citrine Proteins 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis 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
- 241000353790 Doru Species 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- SRPBPKZUTGSHCS-UHFFFAOYSA-N [2-(oxiran-2-ylmethoxy)phenyl]urea Chemical compound NC(=O)NC1=CC=CC=C1OCC1OC1 SRPBPKZUTGSHCS-UHFFFAOYSA-N 0.000 description 1
- VNFHCSQMXQQNSL-UHFFFAOYSA-N [4-(oxiran-2-ylmethoxy)phenyl]urea Chemical compound C1=CC(NC(=O)N)=CC=C1OCC1OC1 VNFHCSQMXQQNSL-UHFFFAOYSA-N 0.000 description 1
- FGMUQNDVAWYYSW-UHFFFAOYSA-N [4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]urea Chemical compound CC(C)NCC(O)COC1=CC=C(NC(N)=O)C=C1 FGMUQNDVAWYYSW-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 230000003288 anthiarrhythmic effect Effects 0.000 description 1
- 239000003416 antiarrhythmic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- 102000012740 beta Adrenergic Receptors Human genes 0.000 description 1
- 108010079452 beta Adrenergic Receptors Proteins 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 208000006218 bradycardia Diseases 0.000 description 1
- 230000036471 bradycardia Effects 0.000 description 1
- QNBOYTNTNXHZKH-UHFFFAOYSA-N butan-1-amine propane Chemical group CCC.C(CCC)N QNBOYTNTNXHZKH-UHFFFAOYSA-N 0.000 description 1
- 125000006309 butyl amino group Chemical group 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- 150000003943 catecholamines Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000011035 citrine Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229960005215 dichloroacetic acid Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- SRMHHEPXZLWKOK-UHFFFAOYSA-N heptan-3-amine Chemical compound CCCCC(N)CC SRMHHEPXZLWKOK-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 210000005053 lamin Anatomy 0.000 description 1
- 210000005240 left ventricle Anatomy 0.000 description 1
- 230000002934 lysing effect Effects 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- VLSTXUUYLIALPB-UHFFFAOYSA-N n-propan-2-ylpropan-1-amine Chemical compound CCCNC(C)C VLSTXUUYLIALPB-UHFFFAOYSA-N 0.000 description 1
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 230000009090 positive inotropic effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- JBJWASZNUJCEKT-UHFFFAOYSA-M sodium;hydroxide;hydrate Chemical compound O.[OH-].[Na+] JBJWASZNUJCEKT-UHFFFAOYSA-M 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000035488 systolic blood pressure Effects 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- UMFCIIBZHQXRCJ-NSCUHMNNSA-N trans-anol Chemical compound C\C=C\C1=CC=C(O)C=C1 UMFCIIBZHQXRCJ-NSCUHMNNSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/32—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
- C07C275/34—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD15123670 | 1970-11-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL94027B1 true PL94027B1 (en, 2012) | 1977-07-30 |
Family
ID=5483145
Family Applications (7)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL17846571A PL95648B1 (pl) | 1970-11-13 | 1971-11-11 | Sposob wytwarzania nowych pochodnych ureidofe loamin |
| PL17846971A PL95743B1 (pl) | 1970-11-13 | 1971-11-11 | Sposob wytwarzania nowych pochodnych ureidofenoksyalkanoloamin |
| PL17846671A PL94028B1 (en, 2012) | 1970-11-13 | 1971-11-11 | |
| PL17846771A PL94027B1 (en, 2012) | 1970-11-13 | 1971-11-11 | |
| PL17847071A PL95744B1 (pl) | 1970-11-13 | 1971-11-11 | Sposob wytwarzania nowych pochodnych ureidofenoksyalkanoloamin |
| PL15149071A PL89374B1 (en, 2012) | 1970-11-13 | 1971-11-11 | |
| PL17846871A PL94076B1 (en, 2012) | 1970-11-13 | 1971-11-11 |
Family Applications Before (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL17846571A PL95648B1 (pl) | 1970-11-13 | 1971-11-11 | Sposob wytwarzania nowych pochodnych ureidofe loamin |
| PL17846971A PL95743B1 (pl) | 1970-11-13 | 1971-11-11 | Sposob wytwarzania nowych pochodnych ureidofenoksyalkanoloamin |
| PL17846671A PL94028B1 (en, 2012) | 1970-11-13 | 1971-11-11 |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL17847071A PL95744B1 (pl) | 1970-11-13 | 1971-11-11 | Sposob wytwarzania nowych pochodnych ureidofenoksyalkanoloamin |
| PL15149071A PL89374B1 (en, 2012) | 1970-11-13 | 1971-11-11 | |
| PL17846871A PL94076B1 (en, 2012) | 1970-11-13 | 1971-11-11 |
Country Status (13)
| Country | Link |
|---|---|
| BG (7) | BG18957A1 (en, 2012) |
| CH (1) | CH565750A5 (en, 2012) |
| CS (7) | CS177451B1 (en, 2012) |
| DE (1) | DE2153024C3 (en, 2012) |
| DK (1) | DK136712C (en, 2012) |
| FI (1) | FI56374C (en, 2012) |
| FR (1) | FR2113982A1 (en, 2012) |
| HU (1) | HU172438B (en, 2012) |
| PL (7) | PL95648B1 (en, 2012) |
| RO (7) | RO64200A (en, 2012) |
| SE (1) | SE373838B (en, 2012) |
| SU (7) | SU496268A1 (en, 2012) |
| YU (4) | YU36491B (en, 2012) |
-
1971
- 1971-10-25 DE DE19712153024 patent/DE2153024C3/de not_active Expired
- 1971-10-27 CH CH1564971A patent/CH565750A5/xx not_active IP Right Cessation
- 1971-11-06 BG BG2093871A patent/BG18957A1/xx unknown
- 1971-11-06 BG BG2093971A patent/BG18958A1/xx unknown
- 1971-11-06 BG BG2093671A patent/BG19907A1/xx unknown
- 1971-11-06 BG BG2093571A patent/BG20898A1/xx unknown
- 1971-11-06 BG BG2093471A patent/BG18955A1/xx unknown
- 1971-11-06 BG BG2093771A patent/BG18956A1/xx unknown
- 1971-11-06 BG BG1894571A patent/BG20897A1/xx unknown
- 1971-11-09 RO RO7487271A patent/RO64200A/ro unknown
- 1971-11-09 RO RO7522071A patent/RO63448A/ro unknown
- 1971-11-09 RO RO6869271A patent/RO62250A/ro unknown
- 1971-11-09 RO RO7521871A patent/RO62905A/ro unknown
- 1971-11-09 RO RO7486571A patent/RO64022A/ro unknown
- 1971-11-09 RO RO7521971A patent/RO62906A/ro unknown
- 1971-11-09 RO RO7522171A patent/RO62907A/ro unknown
- 1971-11-10 CS CS787871A patent/CS177451B1/cs unknown
- 1971-11-10 CS CS801174A patent/CS177496B1/cs unknown
- 1971-11-10 CS CS801374A patent/CS183020B1/cs unknown
- 1971-11-10 CS CS801274A patent/CS177497B1/cs unknown
- 1971-11-10 CS CS801071A patent/CS177495B1/cs unknown
- 1971-11-10 CS CS801574A patent/CS177499B1/cs unknown
- 1971-11-10 CS CS801471A patent/CS177498B1/cs unknown
- 1971-11-11 PL PL17846571A patent/PL95648B1/pl unknown
- 1971-11-11 YU YU283671A patent/YU36491B/xx unknown
- 1971-11-11 PL PL17846971A patent/PL95743B1/pl unknown
- 1971-11-11 PL PL17846671A patent/PL94028B1/pl unknown
- 1971-11-11 PL PL17846771A patent/PL94027B1/pl unknown
- 1971-11-11 DK DK551371A patent/DK136712C/da not_active IP Right Cessation
- 1971-11-11 PL PL17847071A patent/PL95744B1/pl unknown
- 1971-11-11 HU HU71AE00000345A patent/HU172438B/hu unknown
- 1971-11-11 PL PL15149071A patent/PL89374B1/pl unknown
- 1971-11-11 PL PL17846871A patent/PL94076B1/pl unknown
- 1971-11-12 SE SE1455471A patent/SE373838B/xx unknown
- 1971-11-12 SU SU1908723A patent/SU496268A1/ru active
- 1971-11-12 SU SU1908717A patent/SU510470A1/ru active
- 1971-11-12 SU SU1908721A patent/SU511316A1/ru active
- 1971-11-12 SU SU7101908715A patent/SU580207A1/ru active
- 1971-11-12 SU SU1714257A patent/SU521262A1/ru active
- 1971-11-15 FI FI325671A patent/FI56374C/fi active
- 1971-11-15 FR FR7140829A patent/FR2113982A1/fr active Granted
-
1973
- 1973-04-13 SU SU7301908722A patent/SU578304A1/ru active
- 1973-04-13 SU SU1908719A patent/SU504758A1/ru active
-
1979
- 1979-02-20 YU YU41079A patent/YU41079A/xx unknown
- 1979-03-08 YU YU56479A patent/YU56479A/xx unknown
- 1979-03-15 YU YU62579A patent/YU62579A/xx unknown
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