DE2507429C2 - Aminosäureester, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel - Google Patents
Aminosäureester, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende ArzneimittelInfo
- Publication number
- DE2507429C2 DE2507429C2 DE2507429A DE2507429A DE2507429C2 DE 2507429 C2 DE2507429 C2 DE 2507429C2 DE 2507429 A DE2507429 A DE 2507429A DE 2507429 A DE2507429 A DE 2507429A DE 2507429 C2 DE2507429 C2 DE 2507429C2
- Authority
- DE
- Germany
- Prior art keywords
- compounds
- methyl
- acid
- compound
- solution
- 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
- -1 Amino acid esters Chemical class 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 title description 34
- 238000000034 method Methods 0.000 title description 8
- 238000002360 preparation method Methods 0.000 title description 4
- 239000003814 drug Substances 0.000 title description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 12
- 229960004801 imipramine Drugs 0.000 description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 11
- 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 8
- 230000000694 effects Effects 0.000 description 7
- LDCYZAJDBXYCGN-UHFFFAOYSA-N oxitriptan Natural products C1=C(O)C=C2C(CC(N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-UHFFFAOYSA-N 0.000 description 7
- 229940000681 5-hydroxytryptophan Drugs 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 206010003119 arrhythmia Diseases 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 238000001727 in vivo Methods 0.000 description 5
- 238000007912 intraperitoneal administration Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N Alanine Chemical compound CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 230000006793 arrhythmia Effects 0.000 description 4
- 210000004556 brain Anatomy 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000001078 anti-cholinergic effect Effects 0.000 description 3
- 230000001430 anti-depressive effect Effects 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229960002748 norepinephrine Drugs 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 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 description 2
- 206010048610 Cardiotoxicity Diseases 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- 206010044565 Tremor Diseases 0.000 description 2
- NLRXXJKDJNCLFK-UHFFFAOYSA-N [1-(3,4-dichlorophenyl)-2-methylpropan-2-yl] 2-bromopropanoate Chemical compound CC(Br)C(=O)OC(C)(C)CC1=CC=C(Cl)C(Cl)=C1 NLRXXJKDJNCLFK-UHFFFAOYSA-N 0.000 description 2
- DSTLUOVNIIEKEN-UHFFFAOYSA-N [1-(4-bromophenyl)-2-methylpropan-2-yl] 2-bromopropanoate Chemical compound CC(Br)C(=O)OC(C)(C)CC1=CC=C(Br)C=C1 DSTLUOVNIIEKEN-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000003542 behavioural effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 231100000259 cardiotoxicity Toxicity 0.000 description 2
- 230000007681 cardiovascular toxicity Effects 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 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
- 239000003937 drug carrier Substances 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 208000011580 syndromic disease Diseases 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 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
- WAAJRPRSQXYYAA-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-methylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=C(Cl)C=C1 WAAJRPRSQXYYAA-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
- 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
- ILLHORFDXDLILE-UHFFFAOYSA-N 2-bromopropanoyl bromide Chemical compound CC(Br)C(Br)=O ILLHORFDXDLILE-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-NJFSPNSNSA-N Carbon-14 Chemical compound [14C] OKTJSMMVPCPJKN-NJFSPNSNSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 208000008454 Hyperhidrosis Diseases 0.000 description 1
- 239000012839 Krebs-Henseleit buffer Substances 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 208000007623 Lordosis Diseases 0.000 description 1
- 208000006550 Mydriasis Diseases 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 208000001871 Tachycardia Diseases 0.000 description 1
- 229940123445 Tricyclic antidepressant Drugs 0.000 description 1
- 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 description 1
- HCHLQKJFWPXHCT-UHFFFAOYSA-N [1-(3,4-dichlorophenyl)-2-methylpropan-2-yl] 2-aminopropanoate;hydrobromide Chemical compound Br.CC(N)C(=O)OC(C)(C)CC1=CC=C(Cl)C(Cl)=C1 HCHLQKJFWPXHCT-UHFFFAOYSA-N 0.000 description 1
- KDFUHMJTXGCJSP-UHFFFAOYSA-N [1-(3-chlorophenyl)-2-methylpropan-2-yl] 2-aminopropanoate;hydrochloride Chemical compound Cl.CC(N)C(=O)OC(C)(C)CC1=CC=CC(Cl)=C1 KDFUHMJTXGCJSP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 238000010009 beating Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 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
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000001364 causal effect Effects 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229960003920 cocaine Drugs 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 208000028831 congenital heart disease Diseases 0.000 description 1
- 239000013078 crystal Substances 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
- 229940079593 drug Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 210000003128 head Anatomy 0.000 description 1
- AUONNNVJUCSETH-UHFFFAOYSA-N icosanoyl icosanoate Chemical compound CCCCCCCCCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCCCCCCCCC AUONNNVJUCSETH-UHFFFAOYSA-N 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000008517 inhibition of serotonin uptake Effects 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
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007246 mechanism Effects 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
- 210000002569 neuron Anatomy 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
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 210000001747 pupil Anatomy 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 159000000000 sodium salts 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
- 239000000126 substance Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
- 230000035900 sweating Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 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
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
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- 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 (2)
| Publication Number | Publication Date |
|---|---|
| DE2507429A1 DE2507429A1 (de) | 1975-09-18 |
| DE2507429C2 true DE2507429C2 (de) | 1982-10-07 |
Family
ID=20320469
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2507429A Expired DE2507429C2 (de) | 1974-03-11 | 1975-02-21 | Aminosäureester, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
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
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8339 | Ceased/non-payment of the annual fee |