CS277418B6 - Novel psychostimulating substances of the phenylalkylamine derivatives type, process of their preparation and pharmaceuticalpreparation in which said erivatives are comprised - Google Patents
Novel psychostimulating substances of the phenylalkylamine derivatives type, process of their preparation and pharmaceuticalpreparation in which said erivatives are comprised Download PDFInfo
- Publication number
- CS277418B6 CS277418B6 CS876898A CS689887A CS277418B6 CS 277418 B6 CS277418 B6 CS 277418B6 CS 876898 A CS876898 A CS 876898A CS 689887 A CS689887 A CS 689887A CS 277418 B6 CS277418 B6 CS 277418B6
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- formula
- carbon atoms
- phenyl
- compound
- defined above
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 23
- 230000008569 process Effects 0.000 title claims abstract description 12
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 239000000126 substance Substances 0.000 title description 9
- 229940085239 selective calcium channel blockers with direct cardiac effects phenylalkylamine derivative Drugs 0.000 title description 3
- 239000000825 pharmaceutical preparation Substances 0.000 title 1
- 230000002582 psychostimulating effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 71
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 38
- 230000000694 effects Effects 0.000 claims abstract description 22
- 239000004480 active ingredient Substances 0.000 claims abstract description 11
- 125000005843 halogen group Chemical group 0.000 claims abstract description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 239000003368 psychostimulant agent Substances 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 3
- -1 alkyl radical Chemical class 0.000 claims description 24
- 150000001412 amines Chemical class 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 8
- 229910052782 aluminium Inorganic materials 0.000 claims description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 229910000497 Amalgam Inorganic materials 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052987 metal hydride Inorganic materials 0.000 claims description 3
- 150000004681 metal hydrides Chemical class 0.000 claims description 3
- FRCFWPVMFJMNDP-UHFFFAOYSA-N n-propan-2-ylaniline Chemical compound CC(C)NC1=CC=CC=C1 FRCFWPVMFJMNDP-UHFFFAOYSA-N 0.000 claims description 3
- KTOQRRDVVIDEAA-UHFFFAOYSA-N 2-methylpropane Chemical compound [CH2]C(C)C KTOQRRDVVIDEAA-UHFFFAOYSA-N 0.000 claims description 2
- 229910000761 Aluminium amalgam Inorganic materials 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000005984 hydrogenation reaction Methods 0.000 claims description 2
- 150000007529 inorganic bases Chemical class 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000002516 radical scavenger Substances 0.000 claims 1
- 125000002130 sulfonic acid ester group Chemical group 0.000 claims 1
- 230000013016 learning Effects 0.000 abstract description 6
- 150000003943 catecholamines Chemical class 0.000 abstract description 3
- 238000001228 spectrum Methods 0.000 abstract description 3
- 239000000021 stimulant Substances 0.000 abstract description 3
- 230000014759 maintenance of location Effects 0.000 abstract 2
- 208000024827 Alzheimer disease Diseases 0.000 abstract 1
- 230000006735 deficit Effects 0.000 abstract 1
- 238000002560 therapeutic procedure Methods 0.000 abstract 1
- 239000011800 void material Substances 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 48
- 239000000243 solution Substances 0.000 description 45
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
- 239000000203 mixture Substances 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- DZGWFCGJZKJUFP-UHFFFAOYSA-N tyramine Chemical compound NCCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-N 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000002474 experimental method Methods 0.000 description 14
- 238000012360 testing method Methods 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 11
- 241001465754 Metazoa Species 0.000 description 11
- 229940025084 amphetamine Drugs 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 241000700159 Rattus Species 0.000 description 10
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 10
- 229960002748 norepinephrine Drugs 0.000 description 10
- 229960003732 tyramine Drugs 0.000 description 10
- 238000001953 recrystallisation Methods 0.000 description 9
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 8
- 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 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 8
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 8
- 229920002261 Corn starch Polymers 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 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 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
- 239000002775 capsule Substances 0.000 description 6
- 239000008298 dragée Substances 0.000 description 6
- 239000008101 lactose Substances 0.000 description 6
- 239000000829 suppository Substances 0.000 description 6
- 229960005333 tetrabenazine Drugs 0.000 description 6
- 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 5
- 235000019759 Maize starch Nutrition 0.000 description 5
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 229960003638 dopamine Drugs 0.000 description 5
- 230000037406 food intake Effects 0.000 description 5
- 235000012631 food intake Nutrition 0.000 description 5
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 5
- 229960001252 methamphetamine Drugs 0.000 description 5
- 210000000056 organ Anatomy 0.000 description 5
- 239000000454 talc Substances 0.000 description 5
- 229910052623 talc Inorganic materials 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 230000008602 contraction Effects 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 230000004899 motility Effects 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- NFKAWBGFIMBUMB-UHFFFAOYSA-N 1-phenylpentan-2-one Chemical compound CCCC(=O)CC1=CC=CC=C1 NFKAWBGFIMBUMB-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 239000000150 Sympathomimetic Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 231100000673 dose–response relationship Toxicity 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000011888 foil Substances 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000006187 pill Substances 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 239000011780 sodium chloride Substances 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
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- 108010010803 Gelatin Proteins 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
- 102000010909 Monoamine Oxidase Human genes 0.000 description 2
- 108010062431 Monoamine oxidase Proteins 0.000 description 2
- 230000001133 acceleration Effects 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000001143 conditioned effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 150000004658 ketimines Chemical class 0.000 description 2
- 230000005923 long-lasting effect Effects 0.000 description 2
- 231100000053 low toxicity Toxicity 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
- 238000012423 maintenance Methods 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 230000010534 mechanism of action Effects 0.000 description 2
- 230000002503 metabolic effect Effects 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 230000001537 neural effect Effects 0.000 description 2
- 210000002569 neuron Anatomy 0.000 description 2
- 230000003982 neuronal uptake Effects 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical compound CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 230000011514 reflex Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 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
- 230000002295 serotoninergic effect Effects 0.000 description 2
- 230000004936 stimulating effect Effects 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 150000003459 sulfonic acid esters Chemical group 0.000 description 2
- 239000006228 supernatant Substances 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
- 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
- WCTYKSHSZOJYNP-UHFFFAOYSA-N 1-phenyl-n-propan-2-ylpentan-2-amine;hydrochloride Chemical compound Cl.CCCC(NC(C)C)CC1=CC=CC=C1 WCTYKSHSZOJYNP-UHFFFAOYSA-N 0.000 description 1
- IQNDVEUJIFBSFD-UHFFFAOYSA-N 1-phenyl-n-propylbutan-2-amine Chemical compound CCCNC(CC)CC1=CC=CC=C1 IQNDVEUJIFBSFD-UHFFFAOYSA-N 0.000 description 1
- PBENSVGEGPJNFJ-UHFFFAOYSA-N 1-phenyl-n-propylpentan-2-amine Chemical compound CCCNC(CCC)CC1=CC=CC=C1 PBENSVGEGPJNFJ-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
- CNRNYORZJGVOSY-UHFFFAOYSA-N 2,5-diphenyl-1,3-oxazole Chemical compound C=1N=C(C=2C=CC=CC=2)OC=1C1=CC=CC=C1 CNRNYORZJGVOSY-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
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 101100334117 Caenorhabditis elegans fah-1 gene Proteins 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 241000069665 Crenosoma striatum Species 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 102000004316 Oxidoreductases Human genes 0.000 description 1
- 108090000854 Oxidoreductases Proteins 0.000 description 1
- MASVCBBIUQRUKL-UHFFFAOYSA-N POPOP Chemical compound C=1N=C(C=2C=CC(=CC=2)C=2OC(=CN=2)C=2C=CC=CC=2)OC=1C1=CC=CC=C1 MASVCBBIUQRUKL-UHFFFAOYSA-N 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 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 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 239000002269 analeptic agent Substances 0.000 description 1
- 230000001539 anorectic effect Effects 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 230000035045 associative learning Effects 0.000 description 1
- 230000000721 bacterilogical effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000000035 biogenic effect Effects 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 230000000768 catecholaminergic effect Effects 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 210000003710 cerebral cortex Anatomy 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 230000028436 dopamine uptake Effects 0.000 description 1
- 230000003291 dopaminomimetic effect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- XWBDWHCCBGMXKG-UHFFFAOYSA-N ethanamine;hydron;chloride Chemical compound Cl.CCN XWBDWHCCBGMXKG-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000013284 inhibition of norepinephrine uptake Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- TWLUQYYWLRMIFH-UHFFFAOYSA-N n-(1,2-diphenylethyl)propan-1-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(NCCC)CC1=CC=CC=C1 TWLUQYYWLRMIFH-UHFFFAOYSA-N 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
- 230000007935 neutral effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920006316 polyvinylpyrrolidine 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
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000003236 psychic effect Effects 0.000 description 1
- 230000001003 psychopharmacologic effect Effects 0.000 description 1
- 210000001147 pulmonary artery Anatomy 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000005062 synaptic transmission Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 239000003029 tricyclic antidepressant agent Substances 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 238000005303 weighing Methods 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 (2)
| Publication Number | Publication Date |
|---|---|
| CS689887A3 CS689887A3 (en) | 1992-08-12 |
| CS277418B6 true CS277418B6 (en) | 1993-03-17 |
Family
ID=10966901
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS876898A CS277418B6 (en) | 1986-09-25 | 1987-09-25 | Novel psychostimulating substances of the phenylalkylamine derivatives type, process of their preparation and pharmaceuticalpreparation in which said erivatives are comprised |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US5075338A (lt) |
| EP (1) | EP0284621B1 (lt) |
| KR (1) | KR880701545A (lt) |
| AT (1) | ATE117204T1 (lt) |
| CS (1) | CS277418B6 (lt) |
| DD (1) | DD262226A5 (lt) |
| DE (1) | DE3751006T2 (lt) |
| DK (1) | DK282488D0 (lt) |
| ES (1) | ES2007411A6 (lt) |
| FI (1) | FI882474A0 (lt) |
| GE (1) | GEP19960656B (lt) |
| HU (1) | HU207280B (lt) |
| IL (1) | IL83905A (lt) |
| LT (2) | LT3530B (lt) |
| LV (2) | LV10860B (lt) |
| PL (1) | PL151642B1 (lt) |
| PT (1) | PT85799B (lt) |
| RU (1) | RU2007384C1 (lt) |
| SU (1) | SU1746882A3 (lt) |
| UA (3) | UA11100A (lt) |
| WO (1) | WO1988002254A1 (lt) |
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 |
| SG52662A1 (en) * | 1988-08-12 | 1998-09-28 | Astra Ab | Arylkalkyl-amines and -amides having anticonvulsant and neuroprotective properties |
| US5086073A (en) * | 1989-06-02 | 1992-02-04 | John Wyeth & Brother Limited | Composition for treating depression with aralkyl amines |
| US6313146B1 (en) | 1991-08-23 | 2001-11-06 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| US6001884A (en) * | 1991-08-23 | 1999-12-14 | 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 |
| UA55374C2 (uk) | 1994-10-21 | 2003-04-15 | Нпс Фармасьютікалз, Інк | Сполуки, що мають активність по відношенню до рецепторів кальцію |
| US6299901B1 (en) | 1995-01-13 | 2001-10-09 | 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 |
| US6348208B1 (en) | 1995-01-13 | 2002-02-19 | 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 |
| AU718096C (en) * | 1995-06-07 | 2001-11-22 | Noven Pharmaceuticals, Inc. | Transdermal compositions containing low molecular weight drugs which are liquid at room temperatures |
| US6316022B1 (en) | 1995-06-07 | 2001-11-13 | Noven Pharmaceuticals, Inc. | Transdermal compositions containing low molecular weight drugs which are liquid at room temperatures |
| EP0907631B1 (en) | 1996-05-01 | 2003-06-18 | Nps Pharmaceuticals, Inc. | Inorganic ion receptor-active compounds |
| AU747737B2 (en) * | 1997-08-07 | 2002-05-23 | Fujimoto Co., Ltd. | Novel ethylamine derivatives |
| 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 |
| US7619005B2 (en) * | 2000-11-01 | 2009-11-17 | Cognition Pharmaceuticals Llc | Methods for treating cognitive impairment in humans with Multiple Sclerosis |
| US20030119884A1 (en) * | 2000-11-01 | 2003-06-26 | Epstein Mel H. | Methods and compositions for regulating memory consolidation |
| TWI291871B (en) * | 2000-11-01 | 2008-01-01 | Cognition Pharmaceuticals Llc | Pharmaceutical compositions and use of amphetamine compounds for improving memory and learning |
| US20070117869A1 (en) * | 2000-11-01 | 2007-05-24 | Cognition Pharmaceuticals Llc | Methods for treating coginitive impairment and improving cognition |
| US20030232890A1 (en) * | 2000-11-01 | 2003-12-18 | Sention, Inc. | Methods for treating an impairment in memory consolidation |
| US20050059743A1 (en) * | 2000-11-01 | 2005-03-17 | Sention, Inc. | Methods for treating mild cognitive impairment and alzheimer's disease |
| WO2005000203A2 (en) | 2001-10-31 | 2005-01-06 | Sention, Inc. | Methods for treating cognitive impairment and improving cognition |
| DE60229371D1 (de) * | 2001-05-02 | 2008-11-27 | Brni Neurosciences Inst | Kohlensäureanhydrase-aktivatoren zur verbesserung der lern- und gedächtnisleistung |
| EP1935414A3 (en) * | 2001-05-02 | 2010-08-18 | Blanchette Rockefeller Neurosciences Institute | Carbonic anhydrase activators for enhancig learning and memory |
| TW201206425A (en) | 2004-05-18 | 2012-02-16 | Brni Neurosciences Inst | Treatment of depressive disorders |
| AU2010236404B2 (en) | 2009-04-15 | 2016-11-03 | Research Triangle Institute | Monoamine reuptake inhibitors |
| HUE050756T2 (hu) | 2014-12-05 | 2021-01-28 | Semmelweis Univ | Arilalkilamin vegyületek rák megelõzésében vagy kezelésében történõ alkalmazásra |
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 (lt) | 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 PT PT85799A patent/PT85799B/pt not_active IP Right Cessation
- 1987-09-25 PL PL1987267913A patent/PL151642B1/pl unknown
- 1987-09-25 WO PCT/HU1987/000040 patent/WO1988002254A1/en not_active Ceased
- 1987-09-25 UA UA4355858A patent/UA11100A/uk unknown
- 1987-09-25 CS CS876898A patent/CS277418B6/cs unknown
- 1987-09-25 EP EP87906316A patent/EP0284621B1/en not_active Expired - Lifetime
- 1987-09-25 DE DE3751006T patent/DE3751006T2/de not_active Expired - Fee Related
- 1987-09-25 AT AT87906316T patent/ATE117204T1/de not_active IP Right Cessation
- 1987-09-25 UA UA4742460A patent/UA19171A/uk unknown
-
1988
- 1988-05-24 KR KR1019880700574A patent/KR880701545A/ko not_active Ceased
- 1988-05-24 DK DK282488A patent/DK282488D0/da not_active Application Discontinuation
- 1988-05-24 SU SU884355858A patent/SU1746882A3/ru active
- 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-93-650A patent/LV10860B/lv unknown
- 1993-06-22 LV LVP-93-651A patent/LV10709B/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 |
|---|---|
| PL151642B1 (en) | 1990-09-28 |
| LV10860B (en) | 1996-04-20 |
| UA19171A (uk) | 1997-12-25 |
| DE3751006D1 (de) | 1995-03-02 |
| LTIP879A (en) | 1995-03-27 |
| PT85799A (en) | 1987-10-01 |
| ES2007411A6 (es) | 1989-06-16 |
| PT85799B (pt) | 1990-08-31 |
| DD262226A5 (de) | 1988-11-23 |
| LTIP878A (en) | 1995-03-27 |
| IL83905A (en) | 1993-07-08 |
| EP0284621B1 (en) | 1995-01-18 |
| LT3530B (en) | 1995-11-27 |
| LV10709A (lv) | 1995-06-20 |
| HU207280B (en) | 1993-03-29 |
| RU2007384C1 (ru) | 1994-02-15 |
| DK282488A (da) | 1988-05-24 |
| CS689887A3 (en) | 1992-08-12 |
| KR880701545A (ko) | 1988-11-03 |
| US5075338A (en) | 1991-12-24 |
| HUT45962A (en) | 1988-09-28 |
| UA19808A (uk) | 1997-12-25 |
| LV10709B (en) | 1995-12-20 |
| FI882474A7 (fi) | 1988-05-25 |
| ATE117204T1 (de) | 1995-02-15 |
| LT3531B (en) | 1995-11-27 |
| GEP19960656B (en) | 1996-12-24 |
| SU1746882A3 (ru) | 1992-07-07 |
| WO1988002254A1 (en) | 1988-04-07 |
| UA11100A (uk) | 1996-12-25 |
| PL267913A1 (en) | 1989-03-06 |
| EP0284621A1 (en) | 1988-10-05 |
| DE3751006T2 (de) | 1995-05-24 |
| FI882474A0 (fi) | 1988-05-25 |
| LV10860A (lv) | 1995-10-20 |
| DK282488D0 (da) | 1988-05-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CS277418B6 (en) | Novel psychostimulating substances of the phenylalkylamine derivatives type, process of their preparation and pharmaceuticalpreparation in which said erivatives are comprised | |
| FI77018C (fi) | Analogifoerfarande foer framstaellning av antidepressivt aktiv (-)-enantiomer av n-metyl-n-/3-(2-metylfenoxi) -3-fenylpropyl/amin och dess farmaceutiskt godtagbara salt. | |
| AU616907B2 (en) | Melatonin analogues | |
| US2997422A (en) | Monoamine oxidase inhibition | |
| CZ398191A3 (en) | Novel 4-amino alkyl-2(3h)-indolones and pharmaceutical compositions containing them | |
| US5220068A (en) | Psychostimulant agent | |
| CS208663B2 (en) | Method of making the new r,s-n-/2-phenyl-2-hydroxyethyl0 -1-alkyl-3-/4-substituted phenyl/propylamines | |
| CS225850B2 (en) | Process for preparing new r,r-n-(2-phenyl-2-hydroxyethyl)-1-methyl-3-phenylpropylamines | |
| EP4228655B1 (en) | Tetracycline derivatives for treating neurodegenerative or neuroinflammatory diseases | |
| US3910871A (en) | Novel glycylglycine amides | |
| SK152095A3 (en) | Crystalline (+) l-hydrogentartrate, preparation method thereof, pharmaceutical composition containing its and its use | |
| FI61182B (fi) | Foerfarande foer framstaellning av farmaceutiskt aktiva butylaminderivat | |
| EP0076669A1 (en) | Novel 3-phenyl-1-indanamines, pharmaceutical compositions and methods of preparation | |
| US4016280A (en) | 4,4-Diarylpiperidine compositions and use | |
| DE2348577C2 (de) | 1-Amino-4-phenyl-1,2,3,4-tetrahydronaphthaline, deren pharmakologisch verträglichen Salze und diese enthaltende pharmazeutische Zubereitungen | |
| US4419367A (en) | Stimulant | |
| US5270341A (en) | Method of treatment or prophylaxis of depression and stress | |
| US3457354A (en) | Treatment of hypertension with 2-hydroxy (or amino) - 4,5 - dihydroxyphenethylamine derivatives | |
| US6593340B1 (en) | Pharmaceutical compositions containing N-propargylphentermine and related analogs to treat neurodegeneration and/or depression | |
| US3868463A (en) | Method of treating arrhythmia | |
| US3379726A (en) | Tetrahydropyidazines | |
| JPH07252143A (ja) | 認知増強を誘導するベンラファキシン含有医薬組成物 | |
| RU2015960C1 (ru) | Способ получения фенилалкиламинов или солей этих соединений | |
| JP3681770B2 (ja) | 老年性痴呆症又はアルツハイマー病治療剤 | |
| JP3282827B2 (ja) | ３−アリール−２−（１−置換−４−ピペリジニル）−１（１−ジ）オキソ−３ｈ−ベンゾ〔ｄ〕−イソチアゾール誘導体、その製造および神経伝達物質機能のモジュレーターとしてのその使用 |