CH621538A5 - - Google Patents
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- Publication number
- CH621538A5 CH621538A5 CH307975A CH307975A CH621538A5 CH 621538 A5 CH621538 A5 CH 621538A5 CH 307975 A CH307975 A CH 307975A CH 307975 A CH307975 A CH 307975A CH 621538 A5 CH621538 A5 CH 621538A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- methyl
- acid
- compound
- propyl ester
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 49
- 238000000034 method Methods 0.000 claims description 22
- 238000002360 preparation method Methods 0.000 claims description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- FZSPJBYOKQPKCD-UHFFFAOYSA-N 2-aminopropanoic acid [1-(4-chlorophenyl)-2-methylpropan-2-yl] ester Chemical compound CC(N)C(=O)OC(C)(C)CC1=CC=C(Cl)C=C1 FZSPJBYOKQPKCD-UHFFFAOYSA-N 0.000 claims description 5
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 3
- 150000001413 amino acids Chemical class 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- DBJMQQYTLQAQJG-UHFFFAOYSA-N (2-methyl-1-phenylpropan-2-yl) 2-aminopropanoate Chemical compound CC(N)C(=O)OC(C)(C)CC1=CC=CC=C1 DBJMQQYTLQAQJG-UHFFFAOYSA-N 0.000 claims description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- DAECLUXNZAVPAI-UHFFFAOYSA-N [1-(3,4-dichlorophenyl)-2-methylpropan-2-yl] 2-aminopropanoate Chemical compound CC(N)C(=O)OC(C)(C)CC1=CC=C(Cl)C(Cl)=C1 DAECLUXNZAVPAI-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 claims description 2
- 229940095064 tartrate Drugs 0.000 claims description 2
- USWINTIHFQKJTR-UHFFFAOYSA-N 3-hydroxynaphthalene-2,7-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(O)=CC2=C1 USWINTIHFQKJTR-UHFFFAOYSA-N 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- UDVPJXNJFWJNBK-UHFFFAOYSA-N [1-(3-chlorophenyl)-2-methylpropan-2-yl] 2-aminopropanoate Chemical compound CC(N)C(=O)OC(C)(C)CC1=CC=CC(Cl)=C1 UDVPJXNJFWJNBK-UHFFFAOYSA-N 0.000 claims 1
- KNRSHZXPVNZSEK-UHFFFAOYSA-N [2-methyl-1-(4-methylphenyl)propan-2-yl] 2-aminopropanoate Chemical compound CC(N)C(=O)OC(C)(C)CC1=CC=C(C)C=C1 KNRSHZXPVNZSEK-UHFFFAOYSA-N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 20
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 16
- 229960004801 imipramine Drugs 0.000 description 15
- 239000007858 starting material Substances 0.000 description 9
- 239000013543 active substance Substances 0.000 description 8
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N Alanine Chemical compound CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
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- LDCYZAJDBXYCGN-VIFPVBQESA-N 5-hydroxy-L-tryptophan Chemical compound C1=C(O)C=C2C(C[C@H](N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-VIFPVBQESA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 229960002748 norepinephrine Drugs 0.000 description 6
- LDCYZAJDBXYCGN-UHFFFAOYSA-N oxitriptan Natural products C1=C(O)C=C2C(CC(N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-UHFFFAOYSA-N 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 5
- 229940000681 5-hydroxytryptophan Drugs 0.000 description 5
- 108010010803 Gelatin Proteins 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 5
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- 239000008273 gelatin Substances 0.000 description 5
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- 235000011852 gelatine desserts Nutrition 0.000 description 5
- 238000007912 intraperitoneal administration Methods 0.000 description 5
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- -1 1- (3,4-dichlorophenyl) -2-methyl-2-propyl Chemical group 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- 230000006793 arrhythmia Effects 0.000 description 4
- 239000002585 base Substances 0.000 description 4
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- 238000001816 cooling Methods 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- MONMFXREYOKQTI-UHFFFAOYSA-N 2-bromopropanoic acid Chemical compound CC(Br)C(O)=O MONMFXREYOKQTI-UHFFFAOYSA-N 0.000 description 3
- 206010048610 Cardiotoxicity Diseases 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
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- 210000004556 brain Anatomy 0.000 description 3
- 231100000259 cardiotoxicity Toxicity 0.000 description 3
- 230000007681 cardiovascular toxicity Effects 0.000 description 3
- 239000012876 carrier material Substances 0.000 description 3
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- 239000007924 injection Substances 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
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- 230000004044 response Effects 0.000 description 3
- 208000011580 syndromic disease Diseases 0.000 description 3
- ILLHORFDXDLILE-UHFFFAOYSA-N 2-bromopropanoyl bromide Chemical compound CC(Br)C(Br)=O ILLHORFDXDLILE-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229920000945 Amylopectin Polymers 0.000 description 2
- 229920002261 Corn starch Polymers 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
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229930195725 Mannitol Natural products 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
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- 206010044565 Tremor Diseases 0.000 description 2
- VSAWLFXPCQWNOM-UHFFFAOYSA-N [1-(4-bromophenyl)-2-methylpropan-2-yl] 2-aminopropanoate Chemical compound CC(N)C(=O)OC(C)(C)CC1=CC=C(Br)C=C1 VSAWLFXPCQWNOM-UHFFFAOYSA-N 0.000 description 2
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- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 2
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- 238000000338 in vitro Methods 0.000 description 2
- 230000008517 inhibition of serotonin uptake Effects 0.000 description 2
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- 239000008101 lactose Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- YZIFVWOCPGPNHB-UHFFFAOYSA-N 1,2-dichloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C(Cl)=C1 YZIFVWOCPGPNHB-UHFFFAOYSA-N 0.000 description 1
- GXRFHTZJNUGYSI-UHFFFAOYSA-N 1-(4-bromophenyl)-2-methylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=C(Br)C=C1 GXRFHTZJNUGYSI-UHFFFAOYSA-N 0.000 description 1
- JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 1
- 125000004345 1-phenyl-2-propyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- KMGUEILFFWDGFV-UHFFFAOYSA-N 2-benzoyl-2-benzoyloxy-3-hydroxybutanedioic acid Chemical compound C=1C=CC=CC=1C(=O)C(C(C(O)=O)O)(C(O)=O)OC(=O)C1=CC=CC=C1 KMGUEILFFWDGFV-UHFFFAOYSA-N 0.000 description 1
- RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 description 1
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- OPAKSOWFKIUFNP-UHFFFAOYSA-N [1-(4-chlorophenyl)-2-methylpropan-2-yl] 2-aminopropanoate;hydrochloride Chemical compound Cl.CC(N)C(=O)OC(C)(C)CC1=CC=C(Cl)C=C1 OPAKSOWFKIUFNP-UHFFFAOYSA-N 0.000 description 1
- ISLQGQKHUXBBAQ-UHFFFAOYSA-N [1-(4-chlorophenyl)-2-methylpropan-2-yl] 2-bromopropanoate Chemical compound CC(Br)C(=O)OC(C)(C)CC1=CC=C(Cl)C=C1 ISLQGQKHUXBBAQ-UHFFFAOYSA-N 0.000 description 1
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- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
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- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
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- 239000000460 chlorine Substances 0.000 description 1
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- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229960003920 cocaine Drugs 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 208000028831 congenital heart disease Diseases 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- WOAZEKPXTXCPFZ-UHFFFAOYSA-N dimethyl(phenyl)azanium;chloride Chemical compound Cl.CN(C)C1=CC=CC=C1 WOAZEKPXTXCPFZ-UHFFFAOYSA-N 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 210000003128 head Anatomy 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 210000001259 mesencephalon Anatomy 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- DDLWFDZVDXCXEQ-UHFFFAOYSA-N n,n-dimethylaniline;hydrobromide Chemical compound Br.CN(C)C1=CC=CC=C1 DDLWFDZVDXCXEQ-UHFFFAOYSA-N 0.000 description 1
- 229940105631 nembutal Drugs 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 210000001747 pupil Anatomy 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 230000013275 serotonin uptake Effects 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000035900 sweating Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- 229940041597 tofranil Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000003029 tricyclic antidepressant agent Substances 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/44—Two oxygen atoms
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
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)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE7403176A SE394809B (sv) | 1974-03-11 | 1974-03-11 | Analogiforfarande for framstellning av antidepressivt verkande aralkylestrar av aminosyror |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH621538A5 true CH621538A5 (en, 2012) | 1981-02-13 |
Family
ID=20320469
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH307975A CH621538A5 (en, 2012) | 1974-03-11 | 1975-03-11 |
Country Status (26)
| Country | Link |
|---|---|
| US (2) | US4237311A (en, 2012) |
| JP (1) | JPS588385B2 (en, 2012) |
| AT (1) | AT339289B (en, 2012) |
| BE (1) | BE826350A (en, 2012) |
| CA (1) | CA1055044A (en, 2012) |
| CH (1) | CH621538A5 (en, 2012) |
| CS (1) | CS186796B2 (en, 2012) |
| DD (1) | DD119210A5 (en, 2012) |
| DE (1) | DE2507429C2 (en, 2012) |
| DK (1) | DK146256C (en, 2012) |
| ES (1) | ES435361A1 (en, 2012) |
| FI (1) | FI59242C (en, 2012) |
| FR (1) | FR2263757B1 (en, 2012) |
| GB (1) | GB1492622A (en, 2012) |
| HK (1) | HK281A (en, 2012) |
| HU (1) | HU173553B (en, 2012) |
| IE (1) | IE41219B1 (en, 2012) |
| IL (1) | IL46726A (en, 2012) |
| IT (1) | IT1045538B (en, 2012) |
| LU (1) | LU72024A1 (en, 2012) |
| MY (1) | MY8100241A (en, 2012) |
| NL (1) | NL7502879A (en, 2012) |
| NO (1) | NO138804C (en, 2012) |
| SE (1) | SE394809B (en, 2012) |
| SU (1) | SU569280A3 (en, 2012) |
| ZA (1) | ZA751010B (en, 2012) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE394809B (sv) * | 1974-03-11 | 1977-07-11 | Astra Laekemedel Ab | Analogiforfarande for framstellning av antidepressivt verkande aralkylestrar av aminosyror |
| SE412384B (sv) * | 1975-09-04 | 1980-03-03 | Astra Laekemedel Ab | Analogiforfarande for framstellning av antidepressivt verkande trifluormetylsubstituerade aralkylestrar av alanin |
| SE8302452D0 (sv) * | 1983-04-29 | 1983-04-29 | Astra Laekemedel Ab | Method for treatment of senile dementia |
| IE60455B1 (en) * | 1987-05-27 | 1994-07-13 | Astra Ab | New aralkyl esters and processes for their preparation |
| ATE211728T1 (de) | 1995-11-02 | 2002-01-15 | Procter & Gamble | Aminoester von parfümalkoholen und ihre verwendung in reinigungs- und waschmittelzusammensetzungen |
| WO2019139462A2 (ko) | 2019-02-21 | 2019-07-18 | 엘지전자 주식회사 | 하차 시점 알림 방법 및 사용자 단말 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2370015A (en) * | 1933-07-24 | 1945-02-20 | Merck & Co Inc | Derivatives of tertiary amino aliphatic acids |
| US2417773A (en) * | 1942-09-23 | 1947-03-18 | Geigy Ag J R | Alpha-substituted aralkyl esters of amino carboxylic acids |
| US2543764A (en) * | 1947-07-02 | 1951-03-06 | Searle & Co | Diaralkyl carbinyl esters of dialkylamino alkanoates and the production thereof |
| US3317584A (en) * | 1964-03-13 | 1967-05-02 | Monsanto Co | Esters of amidoxalic acid |
| US3541135A (en) * | 1967-02-02 | 1970-11-17 | Geigy Chem Corp | Lysine derivatives |
| SE394809B (sv) * | 1974-03-11 | 1977-07-11 | Astra Laekemedel Ab | Analogiforfarande for framstellning av antidepressivt verkande aralkylestrar av aminosyror |
-
1974
- 1974-03-11 SE SE7403176A patent/SE394809B/xx not_active IP Right Cessation
-
1975
- 1975-02-18 ZA ZA00751010A patent/ZA751010B/xx unknown
- 1975-02-21 DE DE2507429A patent/DE2507429C2/de not_active Expired
- 1975-02-27 FI FI750585A patent/FI59242C/fi not_active IP Right Cessation
- 1975-02-28 IL IL46726A patent/IL46726A/xx unknown
- 1975-03-05 AT AT168375A patent/AT339289B/de not_active IP Right Cessation
- 1975-03-06 BE BE154052A patent/BE826350A/xx not_active IP Right Cessation
- 1975-03-06 ES ES435361A patent/ES435361A1/es not_active Expired
- 1975-03-07 SU SU7502111328A patent/SU569280A3/ru active
- 1975-03-07 CA CA221,520A patent/CA1055044A/en not_active Expired
- 1975-03-10 CS CS7500001580A patent/CS186796B2/cs unknown
- 1975-03-10 NO NO750787A patent/NO138804C/no unknown
- 1975-03-10 IT IT48505/75A patent/IT1045538B/it active
- 1975-03-10 IE IE513/75A patent/IE41219B1/xx unknown
- 1975-03-10 DD DD184671A patent/DD119210A5/xx unknown
- 1975-03-10 GB GB9913/75A patent/GB1492622A/en not_active Expired
- 1975-03-10 DK DK95575A patent/DK146256C/da not_active IP Right Cessation
- 1975-03-10 FR FR7507445A patent/FR2263757B1/fr not_active Expired
- 1975-03-10 HU HU73AA805A patent/HU173553B/hu unknown
- 1975-03-11 JP JP50028719A patent/JPS588385B2/ja not_active Expired
- 1975-03-11 LU LU72024A patent/LU72024A1/xx unknown
- 1975-03-11 NL NL7502879A patent/NL7502879A/xx not_active Application Discontinuation
- 1975-03-11 CH CH307975A patent/CH621538A5/de not_active IP Right Cessation
-
1978
- 1978-08-10 US US05/932,669 patent/US4237311A/en not_active Expired - Lifetime
-
1980
- 1980-05-28 US US06/153,932 patent/US4331684A/en not_active Expired - Lifetime
-
1981
- 1981-01-08 HK HK2/81A patent/HK281A/xx unknown
- 1981-12-30 MY MY241/81A patent/MY8100241A/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |