DD262226A5 - Verfahren zur herstellung von phenylalkylomin-derivaten - Google Patents
Verfahren zur herstellung von phenylalkylomin-derivaten Download PDFInfo
- Publication number
- DD262226A5 DD262226A5 DD87307094A DD30709487A DD262226A5 DD 262226 A5 DD262226 A5 DD 262226A5 DD 87307094 A DD87307094 A DD 87307094A DD 30709487 A DD30709487 A DD 30709487A DD 262226 A5 DD262226 A5 DD 262226A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- general formula
- carbon atoms
- acid
- compound
- phenyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 28
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 230000008569 process Effects 0.000 title claims abstract description 7
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 105
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 32
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- 125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 4
- 229940085239 selective calcium channel blockers with direct cardiac effects phenylalkylamine derivative Drugs 0.000 claims abstract description 3
- 125000005843 halogen group Chemical group 0.000 claims abstract 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 13
- 150000001412 amines Chemical class 0.000 claims description 9
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 6
- 229910052782 aluminium Inorganic materials 0.000 claims description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 5
- 239000011230 binding agent Substances 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
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 3
- 150000004658 ketimines Chemical class 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 230000001603 reducing effect Effects 0.000 claims description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 2
- IQNDVEUJIFBSFD-UHFFFAOYSA-N 1-phenyl-n-propylbutan-2-amine Chemical compound CCCNC(CC)CC1=CC=CC=C1 IQNDVEUJIFBSFD-UHFFFAOYSA-N 0.000 claims description 2
- PBENSVGEGPJNFJ-UHFFFAOYSA-N 1-phenyl-n-propylpentan-2-amine Chemical compound CCCNC(CCC)CC1=CC=CC=C1 PBENSVGEGPJNFJ-UHFFFAOYSA-N 0.000 claims description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 2
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims description 2
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
- 150000007529 inorganic bases Chemical class 0.000 claims description 2
- 239000003456 ion exchange resin Substances 0.000 claims description 2
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 230000001035 methylating effect Effects 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 235000006408 oxalic acid Nutrition 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 230000009467 reduction Effects 0.000 claims description 2
- 125000002130 sulfonic acid ester group Chemical group 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- JDWIAKLHBJDFAP-UHFFFAOYSA-N 1-phenyl-n-propylhexan-2-amine Chemical compound CCCCC(NCCC)CC1=CC=CC=C1 JDWIAKLHBJDFAP-UHFFFAOYSA-N 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- 235000011054 acetic acid Nutrition 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- 239000011976 maleic acid Substances 0.000 claims 1
- 235000011007 phosphoric acid Nutrition 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 35
- 230000013016 learning Effects 0.000 abstract description 11
- 238000003860 storage Methods 0.000 abstract description 4
- 150000003943 catecholamines Chemical class 0.000 abstract description 3
- 239000003368 psychostimulant agent Substances 0.000 abstract description 3
- 230000003340 mental effect Effects 0.000 abstract description 2
- 238000001228 spectrum Methods 0.000 abstract description 2
- 239000000021 stimulant Substances 0.000 abstract description 2
- 238000012360 testing method Methods 0.000 description 56
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 48
- 239000000243 solution Substances 0.000 description 47
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
- DZGWFCGJZKJUFP-UHFFFAOYSA-N tyramine Chemical compound NCCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-N 0.000 description 28
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 24
- 229940025084 amphetamine Drugs 0.000 description 24
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 24
- 241000700159 Rattus Species 0.000 description 21
- 239000000203 mixture Substances 0.000 description 20
- MKJIEFSOBYUXJB-HOCLYGCPSA-N (3S,11bS)-9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one Chemical compound C1CN2C[C@H](CC(C)C)C(=O)C[C@H]2C2=C1C=C(OC)C(OC)=C2 MKJIEFSOBYUXJB-HOCLYGCPSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 229960005333 tetrabenazine Drugs 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 229960002748 norepinephrine Drugs 0.000 description 15
- CFFZDZCDUFSOFZ-UHFFFAOYSA-N 3,4-Dihydroxy-phenylacetic acid Chemical compound OC(=O)CC1=CC=C(O)C(O)=C1 CFFZDZCDUFSOFZ-UHFFFAOYSA-N 0.000 description 14
- 229960003732 tyramine Drugs 0.000 description 14
- 241001465754 Metazoa Species 0.000 description 13
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 229960003638 dopamine Drugs 0.000 description 12
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 230000004899 motility Effects 0.000 description 11
- 239000004480 active ingredient Substances 0.000 description 9
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 229920002261 Corn starch Polymers 0.000 description 8
- HCYAFALTSJYZDH-UHFFFAOYSA-N Desimpramine Chemical compound C1CC2=CC=CC=C2N(CCCNC)C2=CC=CC=C21 HCYAFALTSJYZDH-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 230000008602 contraction Effects 0.000 description 8
- 239000008120 corn starch Substances 0.000 description 8
- 229940099112 cornstarch Drugs 0.000 description 8
- 210000000056 organ Anatomy 0.000 description 8
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 8
- 238000007920 subcutaneous administration Methods 0.000 description 8
- 239000000829 suppository Substances 0.000 description 8
- 238000009835 boiling Methods 0.000 description 7
- 229960003914 desipramine Drugs 0.000 description 7
- 230000005764 inhibitory process Effects 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 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 6
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- 231100000673 dose–response relationship Toxicity 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 6
- 239000008101 lactose Substances 0.000 description 6
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 6
- 230000011514 reflex Effects 0.000 description 6
- 239000000454 talc Substances 0.000 description 6
- 235000012222 talc Nutrition 0.000 description 6
- 229910052623 talc Inorganic materials 0.000 description 6
- 102000010909 Monoamine Oxidase Human genes 0.000 description 5
- 108010062431 Monoamine oxidase Proteins 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 238000000338 in vitro Methods 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 210000002569 neuron Anatomy 0.000 description 5
- 241000282326 Felis catus Species 0.000 description 4
- 239000011888 foil Substances 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 238000001727 in vivo Methods 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
- 230000004060 metabolic process Effects 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000006228 supernatant Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- QCJSIHKLYXENIM-UHFFFAOYSA-N 1-phenyl-n-propylpentan-2-amine;hydrochloride Chemical compound Cl.CCCNC(CCC)CC1=CC=CC=C1 QCJSIHKLYXENIM-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000000150 Sympathomimetic Substances 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 239000008298 dragée Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000002708 enhancing effect Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 235000021050 feed intake Nutrition 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000037406 food intake Effects 0.000 description 3
- 235000012631 food intake Nutrition 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- 230000001965 increasing effect Effects 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 238000012423 maintenance Methods 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- -1 sodium hydride borate Chemical compound 0.000 description 3
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- GKDLTXYXODKDEA-UHFFFAOYSA-N 1-phenylbutan-2-one Chemical compound CCC(=O)CC1=CC=CC=C1 GKDLTXYXODKDEA-UHFFFAOYSA-N 0.000 description 2
- NFKAWBGFIMBUMB-UHFFFAOYSA-N 1-phenylpentan-2-one Chemical compound CCCC(=O)CC1=CC=CC=C1 NFKAWBGFIMBUMB-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 239000001828 Gelatine Substances 0.000 description 2
- DCXXMTOCNZCJGO-UHFFFAOYSA-N Glycerol trioctadecanoate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 229930006000 Sucrose Natural products 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
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 230000008485 antagonism Effects 0.000 description 2
- 230000035045 associative learning Effects 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- UBAZGMLMVVQSCD-UHFFFAOYSA-N carbon dioxide;molecular oxygen Chemical compound O=O.O=C=O UBAZGMLMVVQSCD-UHFFFAOYSA-N 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000003001 depressive effect Effects 0.000 description 2
- 230000005611 electricity Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000010534 mechanism of action Effects 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000001537 neural effect Effects 0.000 description 2
- ITJNARMNRKSWTA-UHFFFAOYSA-N nisoxetine Chemical compound C=1C=CC=CC=1C(CCNC)OC1=CC=CC=C1OC ITJNARMNRKSWTA-UHFFFAOYSA-N 0.000 description 2
- 229950004211 nisoxetine Drugs 0.000 description 2
- 210000004940 nucleus Anatomy 0.000 description 2
- QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical compound CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000011533 pre-incubation Methods 0.000 description 2
- 210000001147 pulmonary artery Anatomy 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 230000000862 serotonergic effect Effects 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- OTKCEEWUXHVZQI-UHFFFAOYSA-N 1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(=O)CC1=CC=CC=C1 OTKCEEWUXHVZQI-UHFFFAOYSA-N 0.000 description 1
- YFKBXYGUSOXJGS-UHFFFAOYSA-N 1,3-Diphenyl-2-propanone Chemical compound C=1C=CC=CC=1CC(=O)CC1=CC=CC=C1 YFKBXYGUSOXJGS-UHFFFAOYSA-N 0.000 description 1
- LYZFHABRLUQZDO-UHFFFAOYSA-N 1,3-diphenyl-n-propylpropan-2-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1CC(NCCC)CC1=CC=CC=C1 LYZFHABRLUQZDO-UHFFFAOYSA-N 0.000 description 1
- OIWLZTNKGBUMNE-UHFFFAOYSA-N 1-phenyl-n-(2-phenylethyl)butan-2-amine Chemical compound C=1C=CC=CC=1CCNC(CC)CC1=CC=CC=C1 OIWLZTNKGBUMNE-UHFFFAOYSA-N 0.000 description 1
- KWTSXDURSIMDCE-UHFFFAOYSA-N 1-phenylpropan-2-amine Chemical compound CC(N)CC1=CC=CC=C1 KWTSXDURSIMDCE-UHFFFAOYSA-N 0.000 description 1
- TZXJJSAQSRHKCZ-UHFFFAOYSA-N 2-methoxyethyl 4-methylbenzenesulfonate Chemical compound COCCOS(=O)(=O)C1=CC=C(C)C=C1 TZXJJSAQSRHKCZ-UHFFFAOYSA-N 0.000 description 1
- PMDFTXLISTZCAF-UHFFFAOYSA-N 3-(1-phenylpentan-2-ylamino)propan-1-ol Chemical compound OCCCNC(CCC)CC1=CC=CC=C1 PMDFTXLISTZCAF-UHFFFAOYSA-N 0.000 description 1
- FKBKVVBSBXHGHP-UHFFFAOYSA-N 3-(1-phenylpropan-2-ylamino)propan-1-ol Chemical compound OCCCNC(C)CC1=CC=CC=C1 FKBKVVBSBXHGHP-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 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 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229940123445 Tricyclic antidepressant Drugs 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000002269 analeptic agent Substances 0.000 description 1
- 230000001539 anorectic effect Effects 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000000035 biogenic effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000000768 catecholaminergic effect Effects 0.000 description 1
- 210000003855 cell nucleus Anatomy 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000003467 diminishing effect Effects 0.000 description 1
- 230000003291 dopaminomimetic effect Effects 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000001729 effect on metabolism Effects 0.000 description 1
- 230000013283 epinephrine uptake Effects 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- XWBDWHCCBGMXKG-UHFFFAOYSA-N ethanamine;hydron;chloride Chemical compound Cl.CCN XWBDWHCCBGMXKG-UHFFFAOYSA-N 0.000 description 1
- XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229940116364 hard fat Drugs 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N hydrofluoric acid Substances F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 230000009191 jumping Effects 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- KIABFHXPDLBMLA-UHFFFAOYSA-N n-(2-methoxyethyl)-1-phenylpropan-2-amine Chemical compound COCCNC(C)CC1=CC=CC=C1 KIABFHXPDLBMLA-UHFFFAOYSA-N 0.000 description 1
- XACNSIDKBIUOBN-UHFFFAOYSA-N n-(3-bromopropyl)-1-phenylpropan-2-amine;hydrobromide Chemical compound Br.BrCCCNC(C)CC1=CC=CC=C1 XACNSIDKBIUOBN-UHFFFAOYSA-N 0.000 description 1
- HFBTZBOJTFIRAS-UHFFFAOYSA-N n-ethyl-1-phenylpropan-2-amine;hydron;chloride Chemical compound Cl.CCNC(C)CC1=CC=CC=C1 HFBTZBOJTFIRAS-UHFFFAOYSA-N 0.000 description 1
- 210000001577 neostriatum Anatomy 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 239000003029 tricyclic antidepressant agent Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Psychiatry (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- External Artificial Organs (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU864101A HU207280B (en) | 1986-09-25 | 1986-09-25 | Process for producing new phenyl-alkyl-amines and pharmaceutical compositions containing them |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD262226A5 true DD262226A5 (de) | 1988-11-23 |
Family
ID=10966901
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD87307094A DD262226A5 (de) | 1986-09-25 | 1987-09-21 | Verfahren zur herstellung von phenylalkylomin-derivaten |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US5075338A (pt) |
| EP (1) | EP0284621B1 (pt) |
| KR (1) | KR880701545A (pt) |
| AT (1) | ATE117204T1 (pt) |
| CS (1) | CS277418B6 (pt) |
| DD (1) | DD262226A5 (pt) |
| DE (1) | DE3751006T2 (pt) |
| DK (1) | DK282488D0 (pt) |
| ES (1) | ES2007411A6 (pt) |
| FI (1) | FI882474A0 (pt) |
| GE (1) | GEP19960656B (pt) |
| HU (1) | HU207280B (pt) |
| IL (1) | IL83905A (pt) |
| LT (2) | LT3530B (pt) |
| LV (2) | LV10709B (pt) |
| PL (1) | PL151642B1 (pt) |
| PT (1) | PT85799B (pt) |
| RU (1) | RU2007384C1 (pt) |
| SU (1) | SU1746882A3 (pt) |
| UA (3) | UA11100A (pt) |
| WO (1) | WO1988002254A1 (pt) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5430044A (en) * | 1987-02-06 | 1995-07-04 | Fisons Corporation | Arylalkyl-amines and -amides having anticonvulsant and neuroprotective properties |
| EP0648489A1 (en) * | 1988-08-12 | 1995-04-19 | Fisons Corporation | Arylalkylamides having neuroprotective properties |
| AU641394B2 (en) * | 1989-06-02 | 1993-09-23 | John Wyeth & Brother Limited | Amines |
| US6001884A (en) * | 1991-08-23 | 1999-12-14 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| US6313146B1 (en) | 1991-08-23 | 2001-11-06 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| US6011068A (en) * | 1991-08-23 | 2000-01-04 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| HUT63579A (en) * | 1991-12-20 | 1993-09-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing double-phase pharmaceutical compositions suitable for treating diseases occurring during neurodegenerative processes |
| CZ290670B6 (cs) | 1994-10-21 | 2002-09-11 | Nps Pharmaceuticals, Inc. | Sloučeniny modulující receptory anorganických iontů a farmaceutický prostředek, který je obsahuje |
| US6348208B1 (en) * | 1995-01-13 | 2002-02-19 | Somerset Pharmaceuticals, Inc. | Methods and pharmaceutical compositions employing desmethylselegiline |
| US6319954B1 (en) | 1995-01-13 | 2001-11-20 | Somerset Pharmaceuticals, Inc. | S-(+)-desmethylselegiline and its use in the therapeutic methods and pharmaceutical compositions |
| US6299901B1 (en) | 1995-01-13 | 2001-10-09 | Somerset Pharmaceuticals, Inc. | Methods and pharmaceutical compositions employing desmethylselegiline |
| US6033682A (en) * | 1995-01-13 | 2000-03-07 | Somerset Pharmaceuticals, Inc. | S(+) desmethylselegiline and its use in therapeutic methods and pharmaceutical compositions |
| US6316022B1 (en) | 1995-06-07 | 2001-11-13 | Noven Pharmaceuticals, Inc. | Transdermal compositions containing low molecular weight drugs which are liquid at room temperatures |
| WO1996040085A2 (en) | 1995-06-07 | 1996-12-19 | Noven Pharmaceuticals, Inc. | Transdermal compositions containing low molecular weight drugs which are liquid at room temperatures |
| PT907631E (pt) * | 1996-05-01 | 2003-10-31 | Nps Pharma Inc | Compostos inorganicos activos como receptores de ioes |
| KR100572900B1 (ko) * | 1997-08-07 | 2006-04-24 | 후지모토 쿄다이 가부시키가이샤 | 에틸아민 유도체 |
| JP4499208B2 (ja) * | 1998-10-29 | 2010-07-07 | 株式会社フジモト・コーポレーション | 新規な光学活性アミノペンタン誘導体 |
| WO2005000203A2 (en) | 2001-10-31 | 2005-01-06 | Sention, Inc. | Methods for treating cognitive impairment and improving cognition |
| US7619005B2 (en) * | 2000-11-01 | 2009-11-17 | Cognition Pharmaceuticals Llc | Methods for treating cognitive impairment in humans with Multiple Sclerosis |
| US20030232890A1 (en) * | 2000-11-01 | 2003-12-18 | Sention, Inc. | Methods for treating an impairment in memory consolidation |
| WO2002039998A2 (en) * | 2000-11-01 | 2002-05-23 | Sention, Inc. | Methods and compositions for regulating memory consolidation |
| US20070117869A1 (en) * | 2000-11-01 | 2007-05-24 | Cognition Pharmaceuticals Llc | Methods for treating coginitive impairment and improving cognition |
| US20030119884A1 (en) * | 2000-11-01 | 2003-06-26 | Epstein Mel H. | Methods and compositions for regulating memory consolidation |
| US20050059743A1 (en) * | 2000-11-01 | 2005-03-17 | Sention, Inc. | Methods for treating mild cognitive impairment and alzheimer's disease |
| US20040235889A1 (en) * | 2001-05-02 | 2004-11-25 | Miao-Kun Sun | Carbonic anhydrase activator for enhancing learning and memory |
| EP1935414A3 (en) * | 2001-05-02 | 2010-08-18 | Blanchette Rockefeller Neurosciences Institute | Carbonic anhydrase activators for enhancig learning and memory |
| TW201207390A (en) | 2004-05-18 | 2012-02-16 | Brni Neurosciences Inst | Method for screening agent for antidepressant activity |
| CA2758774C (en) | 2009-04-15 | 2015-02-03 | Research Triangle Institute | Monoamine reuptake inhibitors |
| WO2016088111A1 (en) | 2014-12-05 | 2016-06-09 | Semmelweis University | Arylalkylamine compounds for use in the prevention or treatment of cancer |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US485926A (en) | 1892-11-08 | Field | ||
| DE767263C (de) * | 1937-10-03 | 1952-03-31 | Theodor H Temmler | Verfahren zur Herstellung von ª-Aralkylaminen |
| DE893341C (de) * | 1950-08-23 | 1953-10-15 | Troponwerke Dinklage & Co | Verfahren zur Herstellung von N-Aralkyl-ª-phenyl-isopropylaminen |
| US2797242A (en) * | 1953-08-11 | 1957-06-25 | Parke Davis & Co | Substituted alpha-benzylphenethylamines and methods for producing the same |
| DE227447C (pt) | 1955-03-23 | 1910-10-21 | ||
| DE1210873B (de) * | 1959-03-18 | 1966-02-17 | Hoffmann La Roche | Verfahren zur Herstellung von Halogenalkylaminen |
| US3044932A (en) * | 1960-02-24 | 1962-07-17 | Upjohn Co | Appetite suppressant drugs |
| DE1133395B (de) * | 1960-11-12 | 1962-07-19 | Hoechst Ag | Verfahren zur Herstellung von herz- und kreislaufwirksamen Phenylalkylaminen |
| DE1227447B (de) * | 1962-03-30 | 1966-10-27 | Chinoin Gyogyszer Es Vegyeszet | Verfahren zur Herstellung von Phenylisopropylaminen |
| GB1031425A (en) * | 1962-03-30 | 1966-06-02 | Chinoin Gyogyszer Es Vegyeszet | New aralkylamines and their preparation |
| FR1478311A (fr) * | 1963-10-18 | 1967-04-28 | Koninklijke Pharma Fab Nv | Procédé de préparation d'aminoalcanes et produits en résultant |
| GB1218135A (en) * | 1967-07-28 | 1971-01-06 | Abbott Lab | Substituted phenethylamine derivatives |
| DE2143204C3 (de) * | 1971-08-28 | 1979-09-27 | Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler, 6000 Frankfurt | N-Fluoralkyl-phenylisopropylamin-Derivate und deren Salze, Verfahren zu deren Herstellung und Arzneimittel auf deren Basis |
| US4025624A (en) * | 1975-11-18 | 1977-05-24 | A. H. Robins Company, Incorporated | Phenylalkylamines and phenylalkylureas in combinations to suppress gastric bleeding in aspirin therapy |
| US4404222A (en) * | 1980-08-25 | 1983-09-13 | American Cyanamid Company | Phenylethanolamine derivatives and acid addition salts thereof for enhancing the growth rate of meat-producing animals and improving the efficiency of feed utilization thereby |
| DD145599A1 (de) * | 1979-08-23 | 1980-12-24 | Roswitha Toepfer | Mittel zur regulierung des pflanzenwachstums |
-
1986
- 1986-09-25 HU HU864101A patent/HU207280B/hu not_active IP Right Cessation
-
1987
- 1987-09-15 IL IL83905A patent/IL83905A/xx not_active IP Right Cessation
- 1987-09-21 DD DD87307094A patent/DD262226A5/de not_active IP Right Cessation
- 1987-09-23 ES ES8702717A patent/ES2007411A6/es not_active Expired
- 1987-09-25 WO PCT/HU1987/000040 patent/WO1988002254A1/en active IP Right Grant
- 1987-09-25 AT AT87906316T patent/ATE117204T1/de not_active IP Right Cessation
- 1987-09-25 CS CS876898A patent/CS277418B6/cs unknown
- 1987-09-25 EP EP87906316A patent/EP0284621B1/en not_active Expired - Lifetime
- 1987-09-25 UA UA4355858A patent/UA11100A/uk unknown
- 1987-09-25 PL PL1987267913A patent/PL151642B1/pl unknown
- 1987-09-25 PT PT85799A patent/PT85799B/pt not_active IP Right Cessation
- 1987-09-25 DE DE3751006T patent/DE3751006T2/de not_active Expired - Fee Related
- 1987-09-25 UA UA4742460A patent/UA19171A/uk unknown
-
1988
- 1988-05-24 KR KR1019880700574A patent/KR880701545A/ko not_active Application Discontinuation
- 1988-05-24 SU SU884355858A patent/SU1746882A3/ru active
- 1988-05-24 DK DK282488A patent/DK282488D0/da not_active Application Discontinuation
- 1988-05-25 FI FI882474A patent/FI882474A0/fi not_active IP Right Cessation
-
1989
- 1989-10-11 US US07/420,058 patent/US5075338A/en not_active Expired - Fee Related
- 1989-11-23 RU SU894742460A patent/RU2007384C1/ru active
-
1990
- 1990-09-10 UA UA4830945A patent/UA19808A/uk unknown
-
1993
- 1993-06-22 LV LVP-93-651A patent/LV10709B/lv unknown
- 1993-06-22 LV LVP-93-650A patent/LV10860B/lv unknown
- 1993-08-12 GE GEAP19931393A patent/GEP19960656B/en unknown
- 1993-08-19 LT LTIP878A patent/LT3530B/lt not_active IP Right Cessation
- 1993-08-19 LT LTIP879A patent/LT3531B/lt not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| LV10860A (lv) | 1995-10-20 |
| HUT45962A (en) | 1988-09-28 |
| ATE117204T1 (de) | 1995-02-15 |
| LT3531B (en) | 1995-11-27 |
| UA19171A (uk) | 1997-12-25 |
| EP0284621A1 (en) | 1988-10-05 |
| GEP19960656B (en) | 1996-12-24 |
| DK282488A (da) | 1988-05-24 |
| UA19808A (uk) | 1997-12-25 |
| LV10709A (lv) | 1995-06-20 |
| SU1746882A3 (ru) | 1992-07-07 |
| CS277418B6 (en) | 1993-03-17 |
| PL151642B1 (en) | 1990-09-28 |
| DE3751006T2 (de) | 1995-05-24 |
| ES2007411A6 (es) | 1989-06-16 |
| EP0284621B1 (en) | 1995-01-18 |
| CS689887A3 (en) | 1992-08-12 |
| LV10860B (en) | 1996-04-20 |
| KR880701545A (ko) | 1988-11-03 |
| RU2007384C1 (ru) | 1994-02-15 |
| UA11100A (uk) | 1996-12-25 |
| LTIP878A (en) | 1995-03-27 |
| LV10709B (en) | 1995-12-20 |
| DK282488D0 (da) | 1988-05-24 |
| HU207280B (en) | 1993-03-29 |
| US5075338A (en) | 1991-12-24 |
| IL83905A (en) | 1993-07-08 |
| PL267913A1 (en) | 1989-03-06 |
| PT85799A (en) | 1987-10-01 |
| FI882474A (fi) | 1988-05-25 |
| DE3751006D1 (de) | 1995-03-02 |
| LTIP879A (en) | 1995-03-27 |
| FI882474A0 (fi) | 1988-05-25 |
| PT85799B (pt) | 1990-08-31 |
| LT3530B (en) | 1995-11-27 |
| WO1988002254A1 (en) | 1988-04-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DD262226A5 (de) | Verfahren zur herstellung von phenylalkylomin-derivaten | |
| DE69317898T2 (de) | 3,3-diphenylpropylamine, ihre verwendung und herstellung | |
| DE2500110A1 (de) | 3-aryloxy-3-phenylpropylamine und verfahren zu ihrer herstellung | |
| DE1770153C3 (de) | Heterocyclische Aminoketone, deren pharmakologisch verträgliche Säureadditionssalze und Verfahren zu ihrer Herstellung | |
| DE2163911B2 (de) | 2-Aminomethyl-phenole, Verfahren zur Herstellung derselben und diese enthaltende Arzneimittel | |
| DD235065A5 (de) | Verfahren zur herstellung von n-(2-(4-fluorphenyl)-1-methyl)-n-methyl-n-propinylamin | |
| DE2115926B2 (de) | 1-(4-hydroxy-3-dimethylaminosulfamidophenyl)-2-aminoaethanderivate, verfahren zu ihrer herstellung und diese enthaltende mittel | |
| DE2501122C3 (de) | Amidoximderivate, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE1915230C3 (de) | Hydroxyphenylalkylaminderivate, Verfahren zu deren Herstellung und Arzneimittel auf deren Basis | |
| DE2638850C2 (de) | 2-Amino-N↑1↑-(1-phenyl-2-methyl-2-propyl)-propionsäureamide, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel | |
| DD139842A5 (de) | Verfahren zur herstellung quaternaerer ammoniumsalze von phenylpropylaminen und phenylbutylaminen | |
| DE2507429C2 (de) | Aminosäureester, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE2348577C2 (de) | 1-Amino-4-phenyl-1,2,3,4-tetrahydronaphthaline, deren pharmakologisch verträglichen Salze und diese enthaltende pharmazeutische Zubereitungen | |
| DE2522218C3 (de) | Zusammensetzung für die Human- oder Veterinärmedizin, Methylaminderivate und Verfahren zu deren Herstellung | |
| DE2527628C3 (de) | N-Vinyloxyäthyl-a-methyl-ß- phenäthylamine und Appetitzügler auf deren Basis | |
| DD259623A5 (de) | Verfahren zur herstellung von tetrahydro-benzothiazolen | |
| DE2738131A1 (de) | Aminoketone, verfahren zu ihrer herstellung und sie enthaltende arzneimittel | |
| CH579565A5 (en) | Imidazolin-2-ylamino-2,1,3-benzothiadiazoles prodn. - by cyclising corresp. beta aminoethyl (thio) ureas, active against muscle tremors and rigor | |
| DE2227842C3 (de) | Diphenylcyclopentane und diese enthaltende Arzneimittel | |
| AT344672B (de) | Verfahren zur herstellung von neuen 1,1-dialkyl-n-butylaminen und deren pharmazeutisch zulaessigen saeureadditionssalzen | |
| DE1768445C (de) | N substituierte beta Oxybutyramid semisuccinate, deren Salze und ihre Her stellung | |
| DE2206961A1 (de) | Verfahren zur Herstellung neuer Phenyläthylamin-Derivate | |
| DE3239610A1 (de) | Neue 1,1,2-triphenyl-but-l-en-derivate, sowie verfahren zu ihrer herstellung und ihre verwendung als arzneimittel | |
| DE2204989C3 (de) | 2-Phenyl-3-(beta-dlmethylaminopropionyl)benzoturan und dessen pharmakologisch verträgliche Säureadditionssalze sowie diese Verbindungen enthaltende Arzneimittel | |
| DE2109657C3 (de) | DL-m-Tyrosinester und L-m-Tyrosinester, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ENJ | Ceased due to non-payment of renewal fee |