SE448232B - Fenyletanolaminderivat samt farmaceutisk komposition innehallande nemnda derivat sasom aktiv bestandsdel - Google Patents
Fenyletanolaminderivat samt farmaceutisk komposition innehallande nemnda derivat sasom aktiv bestandsdelInfo
- Publication number
- SE448232B SE448232B SE7810613A SE7810613A SE448232B SE 448232 B SE448232 B SE 448232B SE 7810613 A SE7810613 A SE 7810613A SE 7810613 A SE7810613 A SE 7810613A SE 448232 B SE448232 B SE 448232B
- Authority
- SE
- Sweden
- Prior art keywords
- hydroxy
- ethyl
- ppm
- group
- nmr
- Prior art date
Links
- 239000004480 active ingredient Substances 0.000 title claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 title claims 2
- -1 3,4-methylenedioxy Chemical group 0.000 claims description 55
- 150000001875 compounds Chemical class 0.000 claims description 53
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 4
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- ULSIYEODSMZIPX-UHFFFAOYSA-N phenylethanolamine Chemical class NCC(O)C1=CC=CC=C1 ULSIYEODSMZIPX-UHFFFAOYSA-N 0.000 claims description 3
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- ZMBJCRTUSXDOJF-UHFFFAOYSA-N 5-[1-hydroxy-2-[2-(2-methoxyphenoxy)ethylamino]ethyl]-2-methoxybenzenesulfonamide Chemical group COC1=CC=CC=C1OCCNCC(O)C1=CC=C(OC)C(S(N)(=O)=O)=C1 ZMBJCRTUSXDOJF-UHFFFAOYSA-N 0.000 claims 1
- 125000005336 allyloxy group Chemical group 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 description 152
- 229910052799 carbon Inorganic materials 0.000 description 118
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 87
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 84
- 229910052757 nitrogen Inorganic materials 0.000 description 79
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 78
- 239000000126 substance Substances 0.000 description 74
- 238000005481 NMR spectroscopy Methods 0.000 description 66
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 58
- 239000000203 mixture Substances 0.000 description 57
- 239000000047 product Substances 0.000 description 51
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 40
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 39
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 38
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 38
- 101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 description 36
- 239000013078 crystal Substances 0.000 description 31
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 24
- 239000000243 solution Substances 0.000 description 24
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 23
- 239000011734 sodium Substances 0.000 description 23
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- 238000000921 elemental analysis Methods 0.000 description 18
- 125000004432 carbon atom Chemical group C* 0.000 description 17
- 239000001257 hydrogen Substances 0.000 description 17
- 229910052717 sulfur Inorganic materials 0.000 description 17
- 238000000034 method Methods 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 239000000706 filtrate Substances 0.000 description 15
- 238000001914 filtration Methods 0.000 description 15
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 15
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 15
- 239000000741 silica gel Substances 0.000 description 15
- 229910002027 silica gel Inorganic materials 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 238000002844 melting Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- 238000001816 cooling Methods 0.000 description 13
- 238000003756 stirring Methods 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 9
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 9
- 229910006074 SO2NH2 Inorganic materials 0.000 description 8
- 230000000903 blocking effect Effects 0.000 description 8
- YPPYOQYQJOKSGG-UHFFFAOYSA-N n-benzyl-1-(2,3-dihydro-1,4-benzodioxin-3-yl)ethanamine Chemical compound C1OC2=CC=CC=C2OC1C(C)NCC1=CC=CC=C1 YPPYOQYQJOKSGG-UHFFFAOYSA-N 0.000 description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 7
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000012279 sodium borohydride Substances 0.000 description 6
- 229910000033 sodium borohydride Inorganic materials 0.000 description 6
- 238000011282 treatment Methods 0.000 description 6
- FGEOVGGVMMKGDK-UHFFFAOYSA-N 5-[1-hydroxy-2-[1-(2-methoxyphenoxy)propan-2-ylamino]ethyl]-2-methylbenzenesulfonamide Chemical compound COC1=CC=CC=C1OCC(C)NCC(O)C1=CC=C(C)C(S(N)(=O)=O)=C1 FGEOVGGVMMKGDK-UHFFFAOYSA-N 0.000 description 5
- 101150065749 Churc1 gene Proteins 0.000 description 5
- 206010020772 Hypertension Diseases 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 238000010531 catalytic reduction reaction Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 4
- 102100038239 Protein Churchill Human genes 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 208000001871 Tachycardia Diseases 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000001476 alcoholic effect Effects 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- 230000036772 blood pressure Effects 0.000 description 4
- 230000001631 hypertensive effect Effects 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 230000035488 systolic blood pressure Effects 0.000 description 4
- AANTWDPFFAREMQ-UHFFFAOYSA-N 1-(2,3-dihydro-1,4-benzodioxin-3-yl)ethanamine Chemical compound C1=CC=C2OC(C(N)C)COC2=C1 AANTWDPFFAREMQ-UHFFFAOYSA-N 0.000 description 3
- SGUAFYQXFOLMHL-UHFFFAOYSA-N 2-hydroxy-5-{1-hydroxy-2-[(4-phenylbutan-2-yl)amino]ethyl}benzamide Chemical compound C=1C=C(O)C(C(N)=O)=CC=1C(O)CNC(C)CCC1=CC=CC=C1 SGUAFYQXFOLMHL-UHFFFAOYSA-N 0.000 description 3
- IIIJSOISJAIMKC-UHFFFAOYSA-N 5-(2-bromoacetyl)-2-methylbenzenesulfonamide Chemical compound CC1=CC=C(C(=O)CBr)C=C1S(N)(=O)=O IIIJSOISJAIMKC-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002220 antihypertensive agent Substances 0.000 description 3
- 229940030600 antihypertensive agent Drugs 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 150000002118 epoxides Chemical class 0.000 description 3
- 150000003944 halohydrins Chemical class 0.000 description 3
- 229960001632 labetalol Drugs 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-UHFFFAOYSA-N 0.000 description 2
- GNMVUBZCLZMGIL-UHFFFAOYSA-N 5-[1-hydroxy-2-[2-(2-methoxyphenoxy)ethylamino]ethyl]-2-methoxybenzenesulfonamide;hydrochloride Chemical compound Cl.COC1=CC=CC=C1OCCNCC(O)C1=CC=C(OC)C(S(N)(=O)=O)=C1 GNMVUBZCLZMGIL-UHFFFAOYSA-N 0.000 description 2
- FOBJXKVZKYRFOO-UHFFFAOYSA-N 5-acetyl-2-methylbenzenesulfonamide Chemical compound CC(=O)C1=CC=C(C)C(S(N)(=O)=O)=C1 FOBJXKVZKYRFOO-UHFFFAOYSA-N 0.000 description 2
- PBJJRKHLGVSRCV-UHFFFAOYSA-N 5-ethyl-6-methyl-7-oxabicyclo[4.1.0]hepta-2,4-diene-3-sulfonamide Chemical compound C(C)C=1C2(C(C=C(C=1)S(=O)(=O)N)O2)C PBJJRKHLGVSRCV-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 206010002383 Angina Pectoris Diseases 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- UUTXNEXOOCCJAH-UHFFFAOYSA-N [4-(2-bromoethoxy)-3-ethoxyphenyl]methanol Chemical compound CCOC1=CC(CO)=CC=C1OCCBr UUTXNEXOOCCJAH-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 230000003276 anti-hypertensive effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000006264 debenzylation reaction Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 238000010253 intravenous injection Methods 0.000 description 2
- WBASHEGKWPUTEO-UHFFFAOYSA-N n-benzyl-1-(2,3-dihydro-1,4-benzodioxin-3-yl)ethanamine;hydrochloride Chemical compound Cl.C1OC2=CC=CC=C2OC1C(C)NCC1=CC=CC=C1 WBASHEGKWPUTEO-UHFFFAOYSA-N 0.000 description 2
- ZASBYHZJHQFLGN-UHFFFAOYSA-N n-benzyl-4-phenylbutan-2-amine Chemical compound C=1C=CC=CC=1CNC(C)CCC1=CC=CC=C1 ZASBYHZJHQFLGN-UHFFFAOYSA-N 0.000 description 2
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 2
- 239000000810 peripheral vasodilating agent Substances 0.000 description 2
- 229960002116 peripheral vasodilator Drugs 0.000 description 2
- 229910003446 platinum oxide Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- 238000011699 spontaneously hypertensive rat Methods 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- VOLGAXAGEUPBDM-UHFFFAOYSA-N $l^{1}-oxidanylethane Chemical compound CC[O] VOLGAXAGEUPBDM-UHFFFAOYSA-N 0.000 description 1
- QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 description 1
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- KVCWAZWJLMNADA-UHFFFAOYSA-N 1-(2,3-dihydro-1,4-benzodioxin-3-yl)ethanone Chemical compound C1=CC=C2OC(C(=O)C)COC2=C1 KVCWAZWJLMNADA-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- CPUXOJVJEJZOSP-UHFFFAOYSA-N 2,4-difluoro-N-[2-methoxy-5-[4-methyl-8-[(3-methyloxetan-3-yl)methoxy]quinazolin-6-yl]pyridin-3-yl]benzenesulfonamide Chemical compound COc1ncc(cc1NS(=O)(=O)c1ccc(F)cc1F)-c1cc(OCC2(C)COC2)c2ncnc(C)c2c1 CPUXOJVJEJZOSP-UHFFFAOYSA-N 0.000 description 1
- BWSQKOKULIALEW-UHFFFAOYSA-N 2-[2-[4-fluoro-3-(trifluoromethyl)phenyl]-3-[2-(piperidin-3-ylamino)pyrimidin-4-yl]imidazol-4-yl]acetonitrile Chemical compound FC1=C(C=C(C=C1)C=1N(C(=CN=1)CC#N)C1=NC(=NC=C1)NC1CNCCC1)C(F)(F)F BWSQKOKULIALEW-UHFFFAOYSA-N 0.000 description 1
- SBRYFUVVWOMLLP-UHFFFAOYSA-N 2-azaniumyl-4-methoxy-4-oxobutanoate Chemical compound COC(=O)CC(N)C(O)=O SBRYFUVVWOMLLP-UHFFFAOYSA-N 0.000 description 1
- CWVPBLLPXAOWRI-UHFFFAOYSA-N 2-hydroxy-5-[1-hydroxy-2-[2-(2-methoxyphenoxy)ethylamino]ethyl]benzenesulfonamide Chemical compound COC1=CC=CC=C1OCCNCC(O)C1=CC=C(O)C(S(N)(=O)=O)=C1 CWVPBLLPXAOWRI-UHFFFAOYSA-N 0.000 description 1
- RHMRHGLMZBCOKT-UHFFFAOYSA-N 2-methylbenzenesulfonamide;hydrochloride Chemical compound Cl.CC1=CC=CC=C1S(N)(=O)=O RHMRHGLMZBCOKT-UHFFFAOYSA-N 0.000 description 1
- UBKQRASXZMLQRJ-UHFFFAOYSA-N 2-phenylsulfanylethanamine Chemical compound NCCSC1=CC=CC=C1 UBKQRASXZMLQRJ-UHFFFAOYSA-N 0.000 description 1
- GYUZCSFVRHOJLT-UHFFFAOYSA-N 3-(2-bromo-1-hydroxyethyl)benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(C(O)CBr)=C1 GYUZCSFVRHOJLT-UHFFFAOYSA-N 0.000 description 1
- KXKKFXQLYIFXDJ-UHFFFAOYSA-N 3-[1-hydroxy-2-(4-phenylbutan-2-ylamino)ethyl]-4-methoxybenzenesulfonamide;hydrochloride Chemical compound Cl.COC1=CC=C(S(N)(=O)=O)C=C1C(O)CNC(C)CCC1=CC=CC=C1 KXKKFXQLYIFXDJ-UHFFFAOYSA-N 0.000 description 1
- IWUPONIRCQNUQX-UHFFFAOYSA-N 3-[1-hydroxy-2-(4-phenylbutan-2-ylamino)ethyl]-5-methoxybenzenesulfonamide;hydrochloride Chemical compound Cl.NS(=O)(=O)C1=CC(OC)=CC(C(O)CNC(C)CCC=2C=CC=CC=2)=C1 IWUPONIRCQNUQX-UHFFFAOYSA-N 0.000 description 1
- WECUIGDEWBNQJJ-UHFFFAOYSA-N 4-phenylbutan-2-amine Chemical compound CC(N)CCC1=CC=CC=C1 WECUIGDEWBNQJJ-UHFFFAOYSA-N 0.000 description 1
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- GCOGQZKGFHBOLF-UHFFFAOYSA-N 5-(2-bromoacetyl)-2-phenylmethoxybenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC(C(=O)CBr)=CC=C1OCC1=CC=CC=C1 GCOGQZKGFHBOLF-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring 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 atoms of the carbocyclic ring
- C07D317/64—Oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/34—Compounds containing oxirane rings with hydrocarbon radicals, substituted by sulphur, selenium or tellurium atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/20—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring with substituents attached to the hetero ring
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Heart & Thoracic Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12203477A JPS5473751A (en) | 1977-10-12 | 1977-10-12 | Phenyl ethanolamine derivatives and their preparation |
| JP12843677A JPS5463048A (en) | 1977-10-26 | 1977-10-26 | Novel phenyl ethanolamine derivatives and their preparation |
| JP15535277A JPS5495544A (en) | 1977-12-23 | 1977-12-23 | Phenylethanolamine derivative and its preparation |
| JP7496478A JPS552639A (en) | 1978-06-21 | 1978-06-21 | Phenylethanolamine derivative and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7810613L SE7810613L (sv) | 1979-04-13 |
| SE448232B true SE448232B (sv) | 1987-02-02 |
Family
ID=27465764
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7810613A SE448232B (sv) | 1977-10-12 | 1978-10-11 | Fenyletanolaminderivat samt farmaceutisk komposition innehallande nemnda derivat sasom aktiv bestandsdel |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4217305A (OSRAM) |
| AT (1) | AT363457B (OSRAM) |
| AU (1) | AU526715B2 (OSRAM) |
| CA (1) | CA1147342A (OSRAM) |
| CH (1) | CH639948A5 (OSRAM) |
| DE (1) | DE2843016A1 (OSRAM) |
| DK (1) | DK168484B1 (OSRAM) |
| ES (2) | ES474149A1 (OSRAM) |
| FR (1) | FR2405931A1 (OSRAM) |
| GB (1) | GB2006772B (OSRAM) |
| GR (1) | GR65337B (OSRAM) |
| IT (1) | IT1160853B (OSRAM) |
| NO (1) | NO147148C (OSRAM) |
| PT (1) | PT68624A (OSRAM) |
| SE (1) | SE448232B (OSRAM) |
| SU (2) | SU982537A3 (OSRAM) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55124742A (en) * | 1979-03-20 | 1980-09-26 | Kyowa Hakko Kogyo Co Ltd | Novel aminoalcohol derivative |
| US4206125A (en) * | 1979-05-04 | 1980-06-03 | Richardson-Merrell Inc. | 5-[2-[(2,3-Dihydro-1,4-benzodioxan-2-ylmethyl)amino]-1-hydroxyethyl]-2-hydroxybenzoic acid derivatives |
| DD202692A5 (de) * | 1979-12-04 | 1983-09-28 | Ciba Geigy | Verfahren zur herstellung neuer derivate des 2-amino-aethanols |
| JPS56110665A (en) * | 1980-02-08 | 1981-09-01 | Yamanouchi Pharmaceut Co Ltd | Sulfamoyl-substituted phenetylamine derivative and its preparation |
| US5391825A (en) * | 1980-02-08 | 1995-02-21 | Yamanouchi Pharmaceutical Co., Ltd. | Sulfamoyl substituted phenethylamine intermediates |
| US4558156A (en) * | 1980-02-08 | 1985-12-10 | Yamanouchi Pharmaceutical Co., Ltd. | Sulfamoyl-substituted phenethylamine derivatives |
| DE3128117A1 (de) * | 1980-07-29 | 1982-03-11 | Yamanouchi Pharmaceutical Co., Ltd., Tokyo | Neue phenyl-aethylaminderivate, verfahren zu ihrer herstellung |
| CA1219865A (en) * | 1982-05-14 | 1987-03-31 | Leo Alig | Aziridine phenethanolamine derivatives |
| PT78388B (en) * | 1983-04-12 | 1986-09-15 | Smithkline Beckman Corp | Dopamine-beta-hydroxylase inhibitors |
| JPS6051106A (ja) * | 1983-08-31 | 1985-03-22 | Yamanouchi Pharmaceut Co Ltd | 塩酸アモスラロ−ル持続性製剤 |
| DE3564569D1 (en) * | 1984-05-15 | 1988-09-29 | Seitetsu Kagaku Co Ltd | Process for preparing 2-alkyl-5-haloacetylbenzenesulfonamide |
| US4678855A (en) * | 1985-10-09 | 1987-07-07 | Merck & Co., Inc. | Substituted benzenesulfonamides |
| JPS62114952A (ja) * | 1985-11-13 | 1987-05-26 | Yamanouchi Pharmaceut Co Ltd | 置換フエネチルアミン誘導体の製造法 |
| NZ226934A (en) * | 1987-11-13 | 1991-01-29 | Glaxo Group Ltd | Phenethanolamine derivatives and pharmaceutical compositions |
| KR100253515B1 (ko) * | 1992-05-22 | 2000-05-01 | 요시다 쇼지 | 녹내장 치료용 의약 조성물 |
| FR2737494B1 (fr) * | 1995-08-04 | 1997-08-29 | Synthelabo | Derives de benzenesulfonamide, leur preparation et leur application en therapeutique |
| KR100395280B1 (ko) * | 1996-01-10 | 2004-06-04 | 아사히 가세이 가부시키가이샤 | 신규한3환성화합물및그를함유하는의약조성물 |
| EP1075486A1 (en) * | 1998-05-06 | 2001-02-14 | Duke University | Method of treating bladder and lower urinary tract syndromes |
| FR2791675B1 (fr) * | 1999-03-30 | 2001-05-04 | Synthelabo | Derives de n-[2-(4-aminophenyl) ethyl] -2,3-dihydro-1,4- benzodioxinne-2-methanamine, leur preparation et leur application en therapeutique |
| US6835853B2 (en) * | 2001-10-31 | 2004-12-28 | Synthon Bv | Process for resolution of tamsulosin and compounds, compositions, and processes associated therewith |
| JP3835763B2 (ja) | 2002-08-19 | 2006-10-18 | ファイザー・プロダクツ・インク | 増殖亢進疾患のための組み合わせ治療 |
| MXPA05012900A (es) | 2003-05-30 | 2006-02-22 | Ranbaxy Lab Ltd | Derivados de pirrol sustituidos. |
| US7329780B2 (en) * | 2003-12-09 | 2008-02-12 | Cj Corporation | Method of preparing optically pure phenethylamine derivatives |
| MX2007005137A (es) * | 2004-11-23 | 2007-06-22 | Warner Lambert Co | Derivados del acido 7-(2h-pyrazol-3-il)-3, 5-dihidroxi-heptanoico como inhibidores de hmg co-a reductasa para el tratamiento de lipidemia. |
| CN100569745C (zh) * | 2005-05-27 | 2009-12-16 | 国际威林生化科技股份有限公司 | 制备坦舒乐欣的方法 |
| GT200600381A (es) | 2005-08-25 | 2007-03-28 | Compuestos organicos | |
| US7741317B2 (en) | 2005-10-21 | 2010-06-22 | Bristol-Myers Squibb Company | LXR modulators |
| KR101329112B1 (ko) | 2005-11-08 | 2013-11-14 | 랜박시 래보러터리스 리미티드 | (3ｒ,5ｒ)-7-〔2-(4-플루오로페닐)-5-이소프로필-3-페닐-4-〔(4-히드록시 메틸 페닐 아미노)카르보닐〕-피롤-1-일〕-3,5-디히드록시 헵탄산 헤미 칼슘염의 제조 방법 |
| US7888376B2 (en) | 2005-11-23 | 2011-02-15 | Bristol-Myers Squibb Company | Heterocyclic CETP inhibitors |
| WO2007131804A1 (en) | 2006-05-17 | 2007-11-22 | Synthon B.V. | Tablet composition with a prolonged release of tamsulosin |
| ATE547394T1 (de) | 2006-12-01 | 2012-03-15 | Bristol Myers Squibb Co | N-((3-benzyl)-2,2-(bis-phenyl)-propan-1- aminderivate als cetp-hemmer für die behandlung von atherosklerose und herz-kreislauf- erkrankungen |
| US8465770B2 (en) * | 2008-12-24 | 2013-06-18 | Synthon Bv | Low dose controlled release tablet |
| CN102050766B (zh) * | 2009-11-03 | 2013-08-07 | 安徽省新星药物开发有限责任公司 | 一种盐酸氨磺洛尔的合成方法 |
| JP2016516804A (ja) | 2013-04-17 | 2016-06-09 | ファイザー・インク | 心血管疾患を治療するためのｎ−ピペリジン−３−イルベンズアミド誘導体 |
| WO2016055901A1 (en) | 2014-10-08 | 2016-04-14 | Pfizer Inc. | Substituted amide compounds |
| HRP20241674T1 (hr) | 2019-01-18 | 2025-02-14 | Astrazeneca Ab | 6'-[[(1s,3s)-3-[[5-(difluormetoksi)-2-pirimidinil]amino]ciklopentil]amino][1(2h),3'-bipiridin]-2-on kao inhibitor pcsk9 i postupci njegove upotrebe |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3701808A (en) * | 1967-12-21 | 1972-10-31 | Allen & Hanburys Ltd | Phenylethanolamines |
| GB1266058A (OSRAM) | 1969-07-08 | 1972-03-08 | ||
| GB1321701A (en) | 1969-10-01 | 1973-06-27 | Continental Pharma | Amino-alcohols their salts and process for prepairing the same |
| US3711545A (en) * | 1971-02-23 | 1973-01-16 | Smith Kline French Lab | Alpha-aminoalkyl-4-hydroxy-3-sulfamoylaminobenzyl alcohols |
| DE2115926C3 (de) * | 1971-04-01 | 1978-05-03 | C.H. Boehringer Sohn, 6507 Ingelheim | 1 -(4-Hydroxy-3-dimethylaminosuIfamidophenyI)-2-aminoäthanderivate, Verfahren zu ihrer Herstellung und diese enthaltende Mittel |
| US4034112A (en) * | 1973-06-22 | 1977-07-05 | Imperial Chemical Industries Limited | Ethanolamine derivatives having β-adrenergic blocking activity |
| US3860647A (en) * | 1973-08-20 | 1975-01-14 | Smithkline Corp | {60 -Aminomethyl-4-hydroxy-3-sulfamyl-benzyl alcohols and 4-hydroxy-3-sulfamyl phenethylamines |
| GB1593651A (en) * | 1977-02-03 | 1981-07-22 | Allen & Hanburys Ltd | Amides |
| DK31578A (da) * | 1977-02-03 | 1978-08-04 | Allen & Hanburys Ltd | Fremgangsmaade til fremstilling af benzenderivater |
-
1978
- 1978-09-22 CA CA000311934A patent/CA1147342A/en not_active Expired
- 1978-09-25 GR GR57301A patent/GR65337B/el unknown
- 1978-09-27 US US05/946,192 patent/US4217305A/en not_active Expired - Lifetime
- 1978-10-02 CH CH1021878A patent/CH639948A5/de not_active IP Right Cessation
- 1978-10-03 DE DE19782843016 patent/DE2843016A1/de active Granted
- 1978-10-06 PT PT68624A patent/PT68624A/pt unknown
- 1978-10-09 FR FR7828743A patent/FR2405931A1/fr active Granted
- 1978-10-11 NO NO783442A patent/NO147148C/no unknown
- 1978-10-11 AT AT0731778A patent/AT363457B/de not_active IP Right Cessation
- 1978-10-11 DK DK452178A patent/DK168484B1/da active
- 1978-10-11 SE SE7810613A patent/SE448232B/sv not_active IP Right Cessation
- 1978-10-11 ES ES474149A patent/ES474149A1/es not_active Expired
- 1978-10-11 IT IT69350/78A patent/IT1160853B/it active
- 1978-10-11 SU SU782673556A patent/SU982537A3/ru active
- 1978-10-12 GB GB7840390A patent/GB2006772B/en not_active Expired
- 1978-10-12 AU AU40642/78A patent/AU526715B2/en not_active Expired
-
1979
- 1979-06-13 ES ES481549A patent/ES481549A1/es not_active Expired
- 1979-10-18 SU SU792835396A patent/SU932982A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| GR65337B (en) | 1980-08-18 |
| NO147148C (no) | 1983-02-09 |
| GB2006772A (en) | 1979-05-10 |
| SE7810613L (sv) | 1979-04-13 |
| ES481549A1 (es) | 1980-04-01 |
| CH639948A5 (de) | 1983-12-15 |
| GB2006772B (en) | 1982-02-03 |
| ES474149A1 (es) | 1979-10-16 |
| DE2843016C2 (OSRAM) | 1988-10-13 |
| NO783442L (no) | 1979-04-18 |
| DK168484B1 (da) | 1994-04-05 |
| DK452178A (da) | 1979-04-13 |
| AT363457B (de) | 1981-08-10 |
| IT1160853B (it) | 1987-03-11 |
| FR2405931B1 (OSRAM) | 1982-11-19 |
| IT7869350A0 (it) | 1978-10-11 |
| US4217305A (en) | 1980-08-12 |
| DE2843016A1 (de) | 1979-04-26 |
| ATA731778A (de) | 1981-01-15 |
| SU982537A3 (ru) | 1982-12-15 |
| AU4064278A (en) | 1980-04-17 |
| FR2405931A1 (fr) | 1979-05-11 |
| PT68624A (en) | 1978-11-01 |
| NO147148B (no) | 1982-11-01 |
| AU526715B2 (en) | 1983-01-27 |
| CA1147342A (en) | 1983-05-31 |
| SU932982A3 (ru) | 1982-05-30 |
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