HU189209B - Process for production of new 1-/amino-alkoxi-phenil/-1-phenil propanols, of their acide additioned and quaternary salts and medical preparatives consisting of such compounds - Google Patents
Process for production of new 1-/amino-alkoxi-phenil/-1-phenil propanols, of their acide additioned and quaternary salts and medical preparatives consisting of such compounds Download PDFInfo
- Publication number
- HU189209B HU189209B HU824190A HU419082A HU189209B HU 189209 B HU189209 B HU 189209B HU 824190 A HU824190 A HU 824190A HU 419082 A HU419082 A HU 419082A HU 189209 B HU189209 B HU 189209B
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- HU
- Hungary
- Prior art keywords
- formula
- defined above
- acid
- compound
- halogen
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 44
- 238000000034 method Methods 0.000 title claims description 17
- 150000003839 salts Chemical group 0.000 title claims description 12
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical class CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 title description 2
- 239000002253 acid Substances 0.000 claims description 21
- -1 ethyl magnesium halide Chemical class 0.000 claims description 20
- 239000002585 base Substances 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 150000001340 alkali metals Chemical class 0.000 claims description 6
- 239000011230 binding agent Substances 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 4
- 239000012965 benzophenone Substances 0.000 claims description 4
- 150000003512 tertiary amines Chemical class 0.000 claims description 4
- BLHLJVCOVBYQQS-UHFFFAOYSA-N ethyllithium Chemical compound [Li]CC BLHLJVCOVBYQQS-UHFFFAOYSA-N 0.000 claims description 3
- 239000012458 free base Substances 0.000 claims description 3
- 150000002736 metal compounds Chemical class 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 229940031826 phenolate Drugs 0.000 claims description 3
- 125000001453 quaternary ammonium group Chemical class 0.000 claims description 3
- 150000003335 secondary amines Chemical class 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- MXZROAOUCUVNHX-UHFFFAOYSA-N 2-Aminopropanol Chemical class CCC(N)O MXZROAOUCUVNHX-UHFFFAOYSA-N 0.000 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 2
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 2
- 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 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 53
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 48
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- 235000019441 ethanol Nutrition 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 19
- 239000000203 mixture Substances 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000004480 active ingredient Substances 0.000 description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 11
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 10
- 239000003960 organic solvent Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 239000003826 tablet Substances 0.000 description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 230000007935 neutral effect Effects 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 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 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 150000004795 grignard reagents Chemical class 0.000 description 5
- 239000008101 lactose Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 230000004622 sleep time Effects 0.000 description 5
- 239000000829 suppository Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- 239000007818 Grignard reagent Substances 0.000 description 4
- 239000004201 L-cysteine Substances 0.000 description 4
- 235000013878 L-cysteine Nutrition 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 235000019270 ammonium chloride Nutrition 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 239000008298 dragée Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 150000002576 ketones Chemical class 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
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 239000000454 talc Substances 0.000 description 4
- 229910052623 talc Inorganic materials 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- FRBZAZQRVYHJQS-UHFFFAOYSA-N 1-(2-methoxyphenyl)-1-[4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]propan-1-ol Chemical compound C=1C=CC=C(OC)C=1C(O)(CC)C(C=C1)=CC=C1OCCCN1CCN(C)CC1 FRBZAZQRVYHJQS-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 206010001605 Alcohol poisoning Diseases 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000001154 acute effect Effects 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000007884 disintegrant Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 3
- 150000007530 organic bases Chemical group 0.000 description 3
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 3
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
- 229920001592 potato starch Polymers 0.000 description 3
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-M 3-carboxy-2-(carboxymethyl)-2-hydroxypropanoate Chemical compound OC(=O)CC(O)(C(O)=O)CC([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-M 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 206010003591 Ataxia Diseases 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical class [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 239000001692 EU approved anti-caking agent Substances 0.000 description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 2
- 238000003747 Grignard reaction Methods 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 208000007101 Muscle Cramp Diseases 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229920001213 Polysorbate 20 Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 240000007651 Rubus glaucus Species 0.000 description 2
- 235000011034 Rubus glaucus Nutrition 0.000 description 2
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 208000010513 Stupor Diseases 0.000 description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Chemical group 0.000 description 2
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
- 229920003123 carboxymethyl cellulose sodium Polymers 0.000 description 2
- 229940063834 carboxymethylcellulose sodium Drugs 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
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- 210000003169 central nervous system Anatomy 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 231100000566 intoxication Toxicity 0.000 description 2
- 230000035987 intoxication Effects 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 150000002902 organometallic compounds Chemical class 0.000 description 2
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 239000002516 radical scavenger Substances 0.000 description 2
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- 239000007858 starting material Substances 0.000 description 2
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- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 2
- 238000005550 wet granulation Methods 0.000 description 2
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- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 1
- VSJSGBAHXJAQIV-UHFFFAOYSA-N 1-(3-chlorophenyl)-1-[4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]propan-1-ol Chemical compound C=1C=CC(Cl)=CC=1C(O)(CC)C(C=C1)=CC=C1OCCCN1CCN(C)CC1 VSJSGBAHXJAQIV-UHFFFAOYSA-N 0.000 description 1
- LCIOHRUBTXZTOF-UHFFFAOYSA-N 1-(4-chlorophenyl)-1-[4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]propan-1-ol Chemical compound C=1C=C(OCCCN2CCN(C)CC2)C=CC=1C(O)(CC)C1=CC=C(Cl)C=C1 LCIOHRUBTXZTOF-UHFFFAOYSA-N 0.000 description 1
- ADCYRBXQAJXJTD-UHFFFAOYSA-N 1-(4-chlorophenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(Cl)C=C1 ADCYRBXQAJXJTD-UHFFFAOYSA-N 0.000 description 1
- PXHBXILFGDMYCG-UHFFFAOYSA-N 1-[3-(4-bromophenoxy)propyl]-4-methylpiperazine Chemical compound C1CN(C)CCN1CCCOC1=CC=C(Br)C=C1 PXHBXILFGDMYCG-UHFFFAOYSA-N 0.000 description 1
- ZRACKJHRBFTFNR-UHFFFAOYSA-N 1-[4-(3-chloropropoxy)phenyl]-1-[3-(trifluoromethyl)phenyl]propan-1-ol Chemical compound C=1C=CC(C(F)(F)F)=CC=1C(O)(CC)C1=CC=C(OCCCCl)C=C1 ZRACKJHRBFTFNR-UHFFFAOYSA-N 0.000 description 1
- SFVRSRUKRBANPE-UHFFFAOYSA-N 1-[4-[3-(4-benzylpiperazin-1-yl)propoxy]phenyl]-1-(2-methoxyphenyl)propan-1-ol Chemical compound C=1C=CC=C(OC)C=1C(O)(CC)C(C=C1)=CC=C1OCCCN(CC1)CCN1CC1=CC=CC=C1 SFVRSRUKRBANPE-UHFFFAOYSA-N 0.000 description 1
- QXJBGAHQGGWLPT-UHFFFAOYSA-N 1-[4-[3-(4-benzylpiperazin-1-yl)propoxy]phenyl]-1-(3-chlorophenyl)propan-1-ol Chemical compound C=1C=CC(Cl)=CC=1C(O)(CC)C(C=C1)=CC=C1OCCCN(CC1)CCN1CC1=CC=CC=C1 QXJBGAHQGGWLPT-UHFFFAOYSA-N 0.000 description 1
- JQZUTMDOCHOHJJ-UHFFFAOYSA-N 1-[4-[3-(4-benzylpiperazin-1-yl)propoxy]phenyl]-1-(4-fluorophenyl)propan-1-ol Chemical compound C=1C=C(OCCCN2CCN(CC=3C=CC=CC=3)CC2)C=CC=1C(O)(CC)C1=CC=C(F)C=C1 JQZUTMDOCHOHJJ-UHFFFAOYSA-N 0.000 description 1
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- BLGXFZZNTVWLAY-SCYLSFHTSA-N yohimbine Chemical compound C1=CC=C2C(CCN3C[C@@H]4CC[C@H](O)[C@@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-SCYLSFHTSA-N 0.000 description 1
- 229960000317 yohimbine Drugs 0.000 description 1
- AADVZSXPNRLYLV-UHFFFAOYSA-N yohimbine carboxylic acid Natural products C1=CC=C2C(CCN3CC4CCC(C(C4CC33)C(O)=O)O)=C3NC2=C1 AADVZSXPNRLYLV-UHFFFAOYSA-N 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU824190A HU189209B (en) | 1982-12-28 | 1982-12-28 | Process for production of new 1-/amino-alkoxi-phenil/-1-phenil propanols, of their acide additioned and quaternary salts and medical preparatives consisting of such compounds |
| AU22913/83A AU558033B2 (en) | 1982-12-28 | 1983-12-23 | 1-(amino-alkoxy-phenyl)-1-phenyl propanols |
| CA000444259A CA1211443A (en) | 1982-12-28 | 1983-12-23 | 1-(amino-alkoxy-fenyl)-1-phenyl-propanol derivatives, process for their preparation and pharmaceutical compositions containing them |
| US06/565,901 US4618611A (en) | 1982-12-28 | 1983-12-27 | 1-(aminoalkoxyphenyl)-1-phenyl-propanols, process for their preparation and pharmaceutical compositions containing them |
| IL70558A IL70558A (en) | 1982-12-28 | 1983-12-27 | 1-(aminoalkoxyphenyl)-1-phenylpropanols,their preparation and pharmaceutical compositions containing them |
| FI834798A FI78913C (fi) | 1982-12-28 | 1983-12-27 | Foerfarande foer framstaellning av nya, terapeutiskt anvaendbara 1-(aminoalkoxifenyl)-1-fenylpropanoler. |
| DK601883A DK163237C (da) | 1982-12-28 | 1983-12-27 | Phenyl-propanolderivater og farmaceutisk acceptable syreadditionssalte og kvaternaere ammoniumsalte deraf, fremgangsmaade til fremstilling heraf, farmaceutisk praeparat og fremgangsmaade til fremstilling heraf |
| ES528460A ES8600204A1 (es) | 1982-12-28 | 1983-12-27 | Procedimiento de preparacion de nuevos deridados de alfa-etibenzol con un grupo amino propanolico sustituido y sus sales de adicion acidas y amonicas cuaternarias. |
| ZA839616A ZA839616B (en) | 1982-12-28 | 1983-12-27 | 1-(amino-alkoxy-phenyl)-1-phenyl-propanol derivatives,process for their preparation and pharmaceutical compositions containing them |
| JP58244950A JPS59134755A (ja) | 1982-12-28 | 1983-12-27 | １−（アミノアルコキシフエニル）−１−フエニル−プロパノ−ル類 |
| AT83113172T ATE25976T1 (de) | 1982-12-28 | 1983-12-28 | Substituierte 1-((3-(amino)-propoxy)-phenyl)-1(phenyl)-propan-1-ole, ihre saeureadditionssalze und quaternaeren salze, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel. |
| EP83113172A EP0115079B1 (de) | 1982-12-28 | 1983-12-28 | Substituierte 1-((3-(Amino)-propoxy)-phenyl)-1-(phenyl)-propan-1-ole, ihre Säureadditionssalze und quaternären Salze, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| DE8383113172T DE3370326D1 (en) | 1982-12-28 | 1983-12-28 | Substituted 1-((3-(amino)-propoxy)-phenyl)-1-(phenyl)-propan-1-ols, their acid addition salts and quaternary salts, process for their preparation and medicines containing these compounds |
| GR73371A GR78773B (en, 2012) | 1982-12-28 | 1983-12-28 | |
| ES543801A ES8604101A1 (es) | 1982-12-28 | 1985-06-01 | Procedimiento de preparacion de nuevos derivados a-etilben- zol con un grupo aminopropanolico sustituido y sus sales de adicion acidas y amonicas cuaternarias |
| ES543800A ES543800A0 (es) | 1982-12-28 | 1985-06-01 | Procedimiento de preparacion de nuevos derivados -etilben- zol con un grupo aminopropanolico sustituido y sus sales de adicion acidas y amonicas cuaternarias |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU824190A HU189209B (en) | 1982-12-28 | 1982-12-28 | Process for production of new 1-/amino-alkoxi-phenil/-1-phenil propanols, of their acide additioned and quaternary salts and medical preparatives consisting of such compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT36081A HUT36081A (en) | 1985-08-28 |
| HU189209B true HU189209B (en) | 1986-06-30 |
Family
ID=10967268
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU824190A HU189209B (en) | 1982-12-28 | 1982-12-28 | Process for production of new 1-/amino-alkoxi-phenil/-1-phenil propanols, of their acide additioned and quaternary salts and medical preparatives consisting of such compounds |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4618611A (en, 2012) |
| EP (1) | EP0115079B1 (en, 2012) |
| JP (1) | JPS59134755A (en, 2012) |
| AT (1) | ATE25976T1 (en, 2012) |
| AU (1) | AU558033B2 (en, 2012) |
| CA (1) | CA1211443A (en, 2012) |
| DE (1) | DE3370326D1 (en, 2012) |
| DK (1) | DK163237C (en, 2012) |
| ES (3) | ES8600204A1 (en, 2012) |
| FI (1) | FI78913C (en, 2012) |
| GR (1) | GR78773B (en, 2012) |
| HU (1) | HU189209B (en, 2012) |
| IL (1) | IL70558A (en, 2012) |
| ZA (1) | ZA839616B (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9303210D0 (en) * | 1993-02-17 | 1993-03-31 | Univ Manitoba | Cancer treatment |
| US7858825B2 (en) * | 2007-02-15 | 2010-12-28 | Colorado State University Research Foundation | Acid and base stable diphenylmethanol derivatives and methods of use |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3075014A (en) * | 1960-06-14 | 1963-01-22 | Richardson Merrell Inc | Basic substituted alkoxy diphenylalkanols, diphenylalkenes and diphenylalkanes |
| US3494961A (en) * | 1965-03-12 | 1970-02-10 | Hoffmann La Roche | 1,4-bis-(p-(dialkylaminoalkoxy)aryl)-1,4-bis-(aryl)-2-b-1,4-diols |
| US4094908A (en) * | 1973-08-15 | 1978-06-13 | Richter Gedeon Vegyeszeti Gyar Rt. | Alpha-substituted benzhydrol derivatives |
| HU168432B (en, 2012) * | 1973-08-15 | 1976-04-28 |
-
1982
- 1982-12-28 HU HU824190A patent/HU189209B/hu not_active IP Right Cessation
-
1983
- 1983-12-23 CA CA000444259A patent/CA1211443A/en not_active Expired
- 1983-12-23 AU AU22913/83A patent/AU558033B2/en not_active Ceased
- 1983-12-27 ZA ZA839616A patent/ZA839616B/xx unknown
- 1983-12-27 DK DK601883A patent/DK163237C/da not_active IP Right Cessation
- 1983-12-27 ES ES528460A patent/ES8600204A1/es not_active Expired
- 1983-12-27 FI FI834798A patent/FI78913C/fi not_active IP Right Cessation
- 1983-12-27 IL IL70558A patent/IL70558A/xx unknown
- 1983-12-27 US US06/565,901 patent/US4618611A/en not_active Expired - Fee Related
- 1983-12-27 JP JP58244950A patent/JPS59134755A/ja active Granted
- 1983-12-28 DE DE8383113172T patent/DE3370326D1/de not_active Expired
- 1983-12-28 AT AT83113172T patent/ATE25976T1/de not_active IP Right Cessation
- 1983-12-28 GR GR73371A patent/GR78773B/el unknown
- 1983-12-28 EP EP83113172A patent/EP0115079B1/de not_active Expired
-
1985
- 1985-06-01 ES ES543800A patent/ES543800A0/es active Granted
- 1985-06-01 ES ES543801A patent/ES8604101A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FI78913C (fi) | 1989-10-10 |
| ES8603811A1 (es) | 1986-01-01 |
| AU2291383A (en) | 1984-07-05 |
| JPS59134755A (ja) | 1984-08-02 |
| FI834798A0 (fi) | 1983-12-27 |
| ZA839616B (en) | 1984-08-29 |
| FI78913B (fi) | 1989-06-30 |
| CA1211443A (en) | 1986-09-16 |
| DK163237B (da) | 1992-02-10 |
| IL70558A0 (en) | 1984-03-30 |
| DK601883A (da) | 1984-06-29 |
| DK163237C (da) | 1992-06-29 |
| DE3370326D1 (en) | 1987-04-23 |
| US4618611A (en) | 1986-10-21 |
| ES543801A0 (es) | 1986-01-16 |
| ES528460A0 (es) | 1985-10-01 |
| HUT36081A (en) | 1985-08-28 |
| ES543800A0 (es) | 1986-01-01 |
| ES8600204A1 (es) | 1985-10-01 |
| GR78773B (en, 2012) | 1984-10-02 |
| EP0115079A1 (de) | 1984-08-08 |
| EP0115079B1 (de) | 1987-03-18 |
| FI834798L (fi) | 1984-06-29 |
| ATE25976T1 (de) | 1987-04-15 |
| DK601883D0 (da) | 1983-12-27 |
| AU558033B2 (en) | 1987-01-15 |
| IL70558A (en) | 1987-03-31 |
| ES8604101A1 (es) | 1986-01-16 |
| JPH0159264B2 (en, 2012) | 1989-12-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |