CA1085404A - Process for the manufacture of new 1-(azacyclic aralkoxyphenyl)-2- or -3-(bis-arylalkylamino)-alkanes - Google Patents
Process for the manufacture of new 1-(azacyclic aralkoxyphenyl)-2- or -3-(bis-arylalkylamino)-alkanesInfo
- Publication number
- CA1085404A CA1085404A CA281,031A CA281031A CA1085404A CA 1085404 A CA1085404 A CA 1085404A CA 281031 A CA281031 A CA 281031A CA 1085404 A CA1085404 A CA 1085404A
- Authority
- CA
- Canada
- Prior art keywords
- hydrogen
- phenyl
- general formula
- unsubstituted
- integer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 31
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 42
- 150000003839 salts Chemical group 0.000 claims abstract description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 22
- 239000001257 hydrogen Substances 0.000 claims abstract description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
- 125000005843 halogen group Chemical group 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 5
- 239000000203 mixture Substances 0.000 claims description 39
- 239000002253 acid Substances 0.000 claims description 25
- 239000007858 starting material Chemical group 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 229910052987 metal hydride Inorganic materials 0.000 claims description 4
- 150000004681 metal hydrides Chemical class 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000005493 quinolyl group Chemical group 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 2
- 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 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- OJQSOVQCWVDWDZ-UHFFFAOYSA-N 3,3-diphenyl-n-[1-[4-(pyridin-2-ylmethoxy)phenyl]propan-2-yl]propan-1-amine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)CCNC(C)CC(C=C1)=CC=C1OCC1=CC=CC=N1 OJQSOVQCWVDWDZ-UHFFFAOYSA-N 0.000 claims 1
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 claims 1
- 208000001953 Hypotension Diseases 0.000 abstract description 3
- 230000000059 bradycardiac effect Effects 0.000 abstract description 3
- 208000021822 hypotensive Diseases 0.000 abstract description 3
- 230000001077 hypotensive effect Effects 0.000 abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000002950 monocyclic group Chemical group 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 60
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 23
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 22
- 238000002844 melting Methods 0.000 description 21
- 230000008018 melting Effects 0.000 description 21
- 239000001294 propane Substances 0.000 description 21
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 20
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 18
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 14
- -1 4-quinolyl Chemical group 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 229960004592 isopropanol Drugs 0.000 description 10
- 229920006395 saturated elastomer Polymers 0.000 description 10
- 230000000875 corresponding effect Effects 0.000 description 9
- 239000011780 sodium chloride Substances 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
- 239000011976 maleic acid Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- JPMRGPPMXHGKRO-UHFFFAOYSA-N 2-(chloromethyl)pyridine hydrochloride Chemical compound Cl.ClCC1=CC=CC=N1 JPMRGPPMXHGKRO-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical class B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 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 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000008101 lactose Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 235000015424 sodium Nutrition 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 230000003276 anti-hypertensive effect Effects 0.000 description 4
- 229910000085 borane Inorganic materials 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 229940073584 methylene chloride Drugs 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 206010020772 Hypertension Diseases 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 229940025084 amphetamine Drugs 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 230000001631 hypertensive effect Effects 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 235000012222 talc Nutrition 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- QDWTXRWOKORYQH-UHFFFAOYSA-N 3-bromobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(Br)=C1 QDWTXRWOKORYQH-UHFFFAOYSA-N 0.000 description 2
- ZDHKVKPZQKYREU-UHFFFAOYSA-N 4-(chloromethyl)pyridine;hydron;chloride Chemical compound Cl.ClCC1=CC=NC=C1 ZDHKVKPZQKYREU-UHFFFAOYSA-N 0.000 description 2
- KWWMETRUZQSXMH-UHFFFAOYSA-N 4-[2-(2,2-diphenylethylamino)propyl]phenol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)CNC(C)CC1=CC=C(O)C=C1 KWWMETRUZQSXMH-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- 241000282693 Cercopithecidae Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 206010039897 Sedation Diseases 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- 239000008186 active pharmaceutical agent Substances 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
- 229910000091 aluminium hydride Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 2
- 229940088679 drug related substance Drugs 0.000 description 2
- 238000001640 fractional crystallisation Methods 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 159000000001 potassium salts Chemical class 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000036280 sedation Effects 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- SLHSRCBFPHCSGL-UHFFFAOYSA-N (3-bromo-1-phenylpropyl)benzene Chemical compound C=1C=CC=CC=1C(CCBr)C1=CC=CC=C1 SLHSRCBFPHCSGL-UHFFFAOYSA-N 0.000 description 1
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- LIAWCVKDHUSSQM-UHFFFAOYSA-N 1-[4-(pyridin-2-ylmethoxy)phenyl]propan-2-one Chemical compound C1=CC(CC(=O)C)=CC=C1OCC1=CC=CC=N1 LIAWCVKDHUSSQM-UHFFFAOYSA-N 0.000 description 1
- MXOPKPMEGUYUCV-UHFFFAOYSA-N 2-(chloromethyl)-5-methylpyridine Chemical compound CC1=CC=C(CCl)N=C1 MXOPKPMEGUYUCV-UHFFFAOYSA-N 0.000 description 1
- NJWIMFZLESWFIM-UHFFFAOYSA-N 2-(chloromethyl)pyridine Chemical compound ClCC1=CC=CC=N1 NJWIMFZLESWFIM-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- GJJFXHVNSIXCKD-UHFFFAOYSA-N 3,3-diphenyl-n-[1-[4-(pyridin-2-ylmethoxy)phenyl]propan-2-yl]propanamide Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)CC(=O)NC(C)CC(C=C1)=CC=C1OCC1=CC=CC=N1 GJJFXHVNSIXCKD-UHFFFAOYSA-N 0.000 description 1
- YYLLEPGPRKWDBR-UHFFFAOYSA-N 3,3-diphenyl-n-[2-(4-phenylmethoxyphenyl)ethyl]propan-1-amine Chemical compound C=1C=C(OCC=2C=CC=CC=2)C=CC=1CCNCCC(C=1C=CC=CC=1)C1=CC=CC=C1 YYLLEPGPRKWDBR-UHFFFAOYSA-N 0.000 description 1
- MWAFWBDWAWZJGK-UHFFFAOYSA-N 3,3-diphenylprop-2-enal Chemical compound C=1C=CC=CC=1C(=CC=O)C1=CC=CC=C1 MWAFWBDWAWZJGK-UHFFFAOYSA-N 0.000 description 1
- RQGYWNQRYMKJQM-UHFFFAOYSA-N 3,3-diphenylpropanoyl 3,3-diphenylpropanoate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)CC(=O)OC(=O)CC(C=1C=CC=CC=1)C1=CC=CC=C1 RQGYWNQRYMKJQM-UHFFFAOYSA-N 0.000 description 1
- KISZTEOELCMZPY-UHFFFAOYSA-N 3,3-diphenylpropylamine Chemical compound C=1C=CC=CC=1C(CCN)C1=CC=CC=C1 KISZTEOELCMZPY-UHFFFAOYSA-N 0.000 description 1
- UZGLOGCJCWBBIV-UHFFFAOYSA-N 3-(chloromethyl)pyridin-1-ium;chloride Chemical compound Cl.ClCC1=CC=CN=C1 UZGLOGCJCWBBIV-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- BUVAKOPYJWOKBN-UHFFFAOYSA-N 4-[2-(3,3-diphenylpropylamino)propyl]-2-fluorophenol;hydrobromide Chemical compound Br.C=1C=CC=CC=1C(C=1C=CC=CC=1)CCNC(C)CC1=CC=C(O)C(F)=C1 BUVAKOPYJWOKBN-UHFFFAOYSA-N 0.000 description 1
- HWHFKPLTCPWOKX-UHFFFAOYSA-N 4-[2-(3,3-diphenylpropylamino)propyl]-2-methylphenol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)CCNC(C)CC1=CC=C(O)C(C)=C1 HWHFKPLTCPWOKX-UHFFFAOYSA-N 0.000 description 1
- LNJZMYPDNAJXBE-UHFFFAOYSA-N 4-[2-(3,3-diphenylpropylamino)propyl]phenol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)CCNC(C)CC1=CC=C(O)C=C1 LNJZMYPDNAJXBE-UHFFFAOYSA-N 0.000 description 1
- DKIQYVJSWCGNQZ-UHFFFAOYSA-N 4-[2-(3,3-diphenylpropylamino)propyl]phenol;hydrobromide Chemical compound Br.C=1C=CC=CC=1C(C=1C=CC=CC=1)CCNC(C)CC1=CC=C(O)C=C1 DKIQYVJSWCGNQZ-UHFFFAOYSA-N 0.000 description 1
- PYSQGUGELWTMPU-UHFFFAOYSA-N 4-[3-(3,3-diphenylpropylamino)butyl]phenol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)CCNC(C)CCC1=CC=C(O)C=C1 PYSQGUGELWTMPU-UHFFFAOYSA-N 0.000 description 1
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 1
- 125000005274 4-hydroxybenzoic acid group Chemical group 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
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- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
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- UMSVPCYSAUKCAZ-UHFFFAOYSA-N propane;hydrochloride Chemical compound Cl.CCC UMSVPCYSAUKCAZ-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D215/14—Radicals substituted by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/699,017 US4091103A (en) | 1976-06-23 | 1976-06-23 | Quinolyl or isoquinolyl-lower-alkoxy-phenylene-amino derivatives |
| US699,017 | 1976-06-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1085404A true CA1085404A (en) | 1980-09-09 |
Family
ID=24807584
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA281,031A Expired CA1085404A (en) | 1976-06-23 | 1977-06-21 | Process for the manufacture of new 1-(azacyclic aralkoxyphenyl)-2- or -3-(bis-arylalkylamino)-alkanes |
Country Status (25)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7487986B2 (en) * | 2002-10-16 | 2009-02-10 | 89908, Inc. | Retractable vehicle step |
| US9212127B2 (en) | 2004-08-20 | 2015-12-15 | University Of Virginia Patent Foundation | T type calcium channel inhibitors |
| WO2011109262A2 (en) | 2010-03-01 | 2011-09-09 | Tau Therapeutics Llc | Cancer diagnosis and imaging |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3906110A (en) * | 1973-02-07 | 1975-09-16 | Ciba Geigy Corp | Antihypertensive {60 -(1-aralkylaminoalkyl)-aralkoxybenzyl alcohols |
-
1976
- 1976-06-23 US US05/699,017 patent/US4091103A/en not_active Expired - Lifetime
-
1977
- 1977-03-31 ZA ZA00771962A patent/ZA771962B/xx unknown
- 1977-04-25 US US05/790,530 patent/US4110457A/en not_active Expired - Lifetime
- 1977-06-15 CY CY1167A patent/CY1167A/xx unknown
- 1977-06-15 GB GB25007/77A patent/GB1561516A/en not_active Expired
- 1977-06-18 DE DE19772727387 patent/DE2727387A1/de not_active Withdrawn
- 1977-06-20 GR GR53746A patent/GR82332B/el unknown
- 1977-06-20 NL NL7706780A patent/NL7706780A/xx unknown
- 1977-06-21 FR FR7718973A patent/FR2355833A1/fr active Granted
- 1977-06-21 IL IL52359A patent/IL52359A/xx unknown
- 1977-06-21 CA CA281,031A patent/CA1085404A/en not_active Expired
- 1977-06-21 ES ES459963A patent/ES459963A1/es not_active Expired
- 1977-06-21 PT PT66689A patent/PT66689B/pt unknown
- 1977-06-22 IE IE1277/77A patent/IE45151B1/en unknown
- 1977-06-22 BE BE178665A patent/BE855975A/xx not_active IP Right Cessation
- 1977-06-22 AU AU26327/77A patent/AU513828B2/en not_active Expired
- 1977-06-22 FI FI771960A patent/FI771960A7/fi not_active Application Discontinuation
- 1977-06-22 SE SE7707245A patent/SE7707245A0/sv not_active Application Discontinuation
- 1977-06-22 AT AT439577A patent/AT355575B/de not_active IP Right Cessation
- 1977-06-22 ZA ZA00773744A patent/ZA773744B/xx unknown
- 1977-06-22 NO NO772211A patent/NO148554B/no unknown
- 1977-06-22 JP JP7340477A patent/JPS52156871A/ja active Pending
- 1977-06-22 NZ NZ184457A patent/NZ184457A/xx unknown
- 1977-06-22 DK DK276877A patent/DK276877A/da not_active Application Discontinuation
- 1977-06-23 HU HU77CI1752A patent/HU176501B/hu unknown
-
1982
- 1982-11-26 KE KE3247A patent/KE3247A/xx unknown
-
1984
- 1984-12-30 MY MY31/84A patent/MY8400031A/xx unknown
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