LT3530B - Process for preparation of phenyl alkylamines - Google Patents
Process for preparation of phenyl alkylamines Download PDFInfo
- Publication number
- LT3530B LT3530B LTIP878A LTIP878A LT3530B LT 3530 B LT3530 B LT 3530B LT IP878 A LTIP878 A LT IP878A LT IP878 A LTIP878 A LT IP878A LT 3530 B LT3530 B LT 3530B
- Authority
- LT
- Lithuania
- Prior art keywords
- atoms
- general formula
- alkyl
- carbon atoms
- compounds
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 17
- 230000008569 process Effects 0.000 title claims abstract description 7
- 238000002360 preparation method Methods 0.000 title abstract description 4
- -1 phenyl alkylamines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 63
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 31
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- 125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 3
- 150000001412 amines Chemical class 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 150000007529 inorganic bases Chemical class 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 229910000761 Aluminium amalgam Inorganic materials 0.000 claims 1
- 150000001299 aldehydes Chemical class 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 150000002148 esters Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- FRCFWPVMFJMNDP-UHFFFAOYSA-N n-propan-2-ylaniline Chemical compound CC(C)NC1=CC=CC=C1 FRCFWPVMFJMNDP-UHFFFAOYSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 29
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 6
- 239000004480 active ingredient Substances 0.000 abstract description 4
- 230000014759 maintenance of location Effects 0.000 abstract description 4
- 150000003943 catecholamines Chemical class 0.000 abstract description 3
- 208000024827 Alzheimer disease Diseases 0.000 abstract description 2
- 238000001228 spectrum Methods 0.000 abstract description 2
- 239000000021 stimulant Substances 0.000 abstract description 2
- 230000006735 deficit Effects 0.000 abstract 1
- 239000003368 psychostimulant agent Substances 0.000 abstract 1
- 238000002560 therapeutic procedure Methods 0.000 abstract 1
- 239000011800 void material Substances 0.000 abstract 1
- 238000012360 testing method Methods 0.000 description 23
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 16
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 13
- 229940025084 amphetamine Drugs 0.000 description 13
- 229960002748 norepinephrine Drugs 0.000 description 11
- 241000700159 Rattus Species 0.000 description 10
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 9
- 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 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 9
- 229960005333 tetrabenazine Drugs 0.000 description 9
- 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
- 241001465754 Metazoa Species 0.000 description 8
- 229960003638 dopamine Drugs 0.000 description 8
- 238000012549 training Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 230000004899 motility Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- DZGWFCGJZKJUFP-UHFFFAOYSA-N tyramine Chemical compound NCCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-N 0.000 description 6
- 230000011514 reflex Effects 0.000 description 5
- 238000007920 subcutaneous administration Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 210000001685 thyroid gland Anatomy 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 4
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 4
- 229960001252 methamphetamine Drugs 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 102000010909 Monoamine Oxidase Human genes 0.000 description 3
- 108010062431 Monoamine oxidase Proteins 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 230000001143 conditioned effect Effects 0.000 description 3
- 230000008602 contraction Effects 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 230000037406 food intake Effects 0.000 description 3
- 235000012631 food intake Nutrition 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 230000010534 mechanism of action Effects 0.000 description 3
- 230000001537 neural effect Effects 0.000 description 3
- 230000003982 neuronal uptake Effects 0.000 description 3
- 210000000056 organ Anatomy 0.000 description 3
- 229960003732 tyramine Drugs 0.000 description 3
- 241000282326 Felis catus Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- 239000000150 Sympathomimetic Substances 0.000 description 2
- 230000004397 blinking Effects 0.000 description 2
- 206010061428 decreased appetite Diseases 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000002708 enhancing effect Effects 0.000 description 2
- 235000003642 hunger Nutrition 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 230000009191 jumping Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 230000002503 metabolic effect Effects 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 230000004044 response Effects 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
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 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 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 1
- 101100532451 Rattus norvegicus Slc22a17 gene Proteins 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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 208000007271 Substance Withdrawal Syndrome Diseases 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
- 229940123445 Tricyclic antidepressant Drugs 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000004913 activation Effects 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
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000002269 analeptic agent Substances 0.000 description 1
- 208000022531 anorexia Diseases 0.000 description 1
- 230000003042 antagnostic 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
- 238000003556 assay Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000000035 biogenic effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000012472 biological sample Substances 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- UBAZGMLMVVQSCD-UHFFFAOYSA-N carbon dioxide;molecular oxygen Chemical compound O=O.O=C=O UBAZGMLMVVQSCD-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 230000000768 catecholaminergic effect Effects 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 210000003710 cerebral cortex Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001054 cortical effect Effects 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000005462 in vivo assay Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 230000037323 metabolic rate Effects 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000003880 negative regulation of appetite Effects 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- UJRJCSCBZXLGKF-UHFFFAOYSA-N nickel rhenium Chemical compound [Ni].[Re] UJRJCSCBZXLGKF-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 210000001147 pulmonary artery Anatomy 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000003029 tricyclic antidepressant agent Substances 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)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Pain & Pain Management (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)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- External Artificial Organs (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 |
---|---|
LTIP878A LTIP878A (en) | 1995-03-27 |
LT3530B true LT3530B (en) | 1995-11-27 |
Family
ID=10966901
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
LTIP879A LT3531B (en) | 1986-09-25 | 1993-08-19 | Process for preparation of phenyl alkylamines |
LTIP878A LT3530B (en) | 1986-09-25 | 1993-08-19 | Process for preparation of phenyl alkylamines |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
LTIP879A LT3531B (en) | 1986-09-25 | 1993-08-19 | Process for preparation of phenyl alkylamines |
Country Status (21)
Country | Link |
---|---|
US (1) | US5075338A (cs) |
EP (1) | EP0284621B1 (cs) |
KR (1) | KR880701545A (cs) |
AT (1) | ATE117204T1 (cs) |
CS (1) | CS277418B6 (cs) |
DD (1) | DD262226A5 (cs) |
DE (1) | DE3751006T2 (cs) |
DK (1) | DK282488A (cs) |
ES (1) | ES2007411A6 (cs) |
FI (1) | FI882474A0 (cs) |
GE (1) | GEP19960656B (cs) |
HU (1) | HU207280B (cs) |
IL (1) | IL83905A (cs) |
LT (2) | LT3531B (cs) |
LV (2) | LV10860B (cs) |
PL (1) | PL151642B1 (cs) |
PT (1) | PT85799B (cs) |
RU (1) | RU2007384C1 (cs) |
SU (1) | SU1746882A3 (cs) |
UA (3) | UA11100A (cs) |
WO (1) | WO1988002254A1 (cs) |
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 |
EP0356035B1 (en) * | 1988-08-12 | 1996-03-13 | Astra Aktiebolag | Arylkalkyl-amines and -amides having anticonvulsant and neuroprotective properties |
HUT58270A (en) * | 1989-06-02 | 1992-02-28 | Wyeth John & Brother Ltd | Process for producing amine derivatives and pharmaceutical compositions containing them |
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 |
PL183499B1 (pl) | 1994-10-21 | 2002-06-28 | Nps Pharma Inc | Związki do modulowania receptorów wapniowych i kompozycje farmaceutyczne |
US6033682A (en) | 1995-01-13 | 2000-03-07 | Somerset Pharmaceuticals, Inc. | S(+) desmethylselegiline and its use in therapeutic methods and pharmaceutical compositions |
US6348208B1 (en) | 1995-01-13 | 2002-02-19 | Somerset Pharmaceuticals, Inc. | Methods and pharmaceutical compositions employing desmethylselegiline |
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 |
JPH11506744A (ja) | 1995-06-07 | 1999-06-15 | ノウブン ファーマシューティカルズ インク. | 室温で液体である低分子量薬を含む経皮組成物 |
US6316022B1 (en) | 1995-06-07 | 2001-11-13 | Noven Pharmaceuticals, Inc. | Transdermal compositions containing low molecular weight drugs which are liquid at room temperatures |
DK0907631T3 (da) | 1996-05-01 | 2003-09-22 | Nps Pharma Inc | Uorganiske ionreceptoraktive forbindelser |
DE69835004T2 (de) * | 1997-08-07 | 2007-03-01 | Fujimoto Brothers Co., Ltd., Matubara | Neue ethylaminderivate |
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 |
US20030232890A1 (en) * | 2000-11-01 | 2003-12-18 | Sention, Inc. | Methods for treating an impairment in memory consolidation |
EP1420768A2 (en) * | 2000-11-01 | 2004-05-26 | 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 |
US7619005B2 (en) * | 2000-11-01 | 2009-11-17 | Cognition Pharmaceuticals Llc | Methods for treating cognitive impairment in humans with Multiple Sclerosis |
WO2005000203A2 (en) | 2001-10-31 | 2005-01-06 | Sention, Inc. | Methods for treating cognitive impairment and improving cognition |
CA2446074C (en) * | 2001-05-02 | 2011-09-06 | Blanchette Rockefeller Neurosciences Institute | Carbonic anhydrase activators 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 |
WO2016088112A1 (en) | 2014-12-05 | 2016-06-09 | Semmelweis University | Arylalkylamine compounds for use in the prevention or treatment of cancer |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US485926A (en) | 1892-11-08 | Field | ||
DE227447C (cs) | 1955-03-23 | 1910-10-21 | ||
GB967871A (en) | 1960-02-24 | 1964-08-26 | Upjohn Co | Anorexigenic compositions comprising ª-phenylisopropylamine derivatives |
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 |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
DE1210873B (de) * | 1959-03-18 | 1966-02-17 | Hoffmann La Roche | Verfahren zur Herstellung von Halogenalkylaminen |
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 |
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 AT AT87906316T patent/ATE117204T1/de not_active IP Right Cessation
- 1987-09-25 PT PT85799A patent/PT85799B/pt not_active IP Right Cessation
- 1987-09-25 WO PCT/HU1987/000040 patent/WO1988002254A1/en active IP Right Grant
- 1987-09-25 EP EP87906316A patent/EP0284621B1/en not_active Expired - Lifetime
- 1987-09-25 UA UA4355858A patent/UA11100A/uk unknown
- 1987-09-25 UA UA4742460A patent/UA19171A/uk unknown
- 1987-09-25 PL PL1987267913A patent/PL151642B1/pl unknown
- 1987-09-25 CS CS876898A patent/CS277418B6/cs unknown
- 1987-09-25 DE DE3751006T patent/DE3751006T2/de not_active Expired - Fee Related
-
1988
- 1988-05-24 SU SU884355858A patent/SU1746882A3/ru active
- 1988-05-24 KR KR1019880700574A patent/KR880701545A/ko not_active Application Discontinuation
- 1988-05-24 DK DK282488A patent/DK282488A/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-93-650A 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 LTIP879A patent/LT3531B/lt not_active IP Right Cessation
- 1993-08-19 LT LTIP878A patent/LT3530B/lt not_active IP Right Cessation
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US485926A (en) | 1892-11-08 | Field | ||
DE227447C (cs) | 1955-03-23 | 1910-10-21 | ||
GB967871A (en) | 1960-02-24 | 1964-08-26 | Upjohn Co | Anorexigenic compositions comprising ª-phenylisopropylamine derivatives |
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 |
Non-Patent Citations (5)
Title |
---|
D. SEEBACH ET AL.: "Lithiierung und elektrophile Substitution an alpha-Methylengruppen von Nitrosaminen. Umpolung der Reaktivität sekundärer Amine", CHEM. BER., 1977, pages 1852 - 1865, XP002612310, DOI: doi:10.1002/cber.19771100529 |
DUNCAN JD ET AL.: "Effects of alpha-carbon substituents on the N-demethylation of N-methyl-2-phenethylamines by rat liver microsomes", DRUG METAB DISPOS, 1983, pages 15 - 20 |
KERECSEN ET AL.: "Cromattografy, the State of the Art" |
KNOLL B, KNOLL J.: "The selectivity of the anorectic effect of satietin. I. The ineffectiveness of satietin on behavioral tests", POL J PHARMACOL PHARM., 1982, pages 17 - 23 |
KNOLL J.: "The possible mechanisms of action of (-)deprenyl in Parkinsons desease", J. NEURAL. TRANSM., 1978, pages 177 - 198 |
Also Published As
Publication number | Publication date |
---|---|
HU207280B (en) | 1993-03-29 |
ES2007411A6 (es) | 1989-06-16 |
PL267913A1 (en) | 1989-03-06 |
LTIP879A (en) | 1995-03-27 |
GEP19960656B (en) | 1996-12-24 |
UA19808A (uk) | 1997-12-25 |
PT85799B (pt) | 1990-08-31 |
CS689887A3 (en) | 1992-08-12 |
LV10860B (en) | 1996-04-20 |
ATE117204T1 (de) | 1995-02-15 |
IL83905A (en) | 1993-07-08 |
KR880701545A (ko) | 1988-11-03 |
LV10860A (lv) | 1995-10-20 |
SU1746882A3 (ru) | 1992-07-07 |
LV10709B (en) | 1995-12-20 |
CS277418B6 (en) | 1993-03-17 |
DK282488D0 (da) | 1988-05-24 |
WO1988002254A1 (en) | 1988-04-07 |
DD262226A5 (de) | 1988-11-23 |
EP0284621B1 (en) | 1995-01-18 |
RU2007384C1 (ru) | 1994-02-15 |
FI882474A (fi) | 1988-05-25 |
DK282488A (da) | 1988-05-24 |
DE3751006D1 (de) | 1995-03-02 |
DE3751006T2 (de) | 1995-05-24 |
FI882474A0 (fi) | 1988-05-25 |
UA19171A (uk) | 1997-12-25 |
LV10709A (lv) | 1995-06-20 |
LTIP878A (en) | 1995-03-27 |
US5075338A (en) | 1991-12-24 |
EP0284621A1 (en) | 1988-10-05 |
PL151642B1 (en) | 1990-09-28 |
LT3531B (en) | 1995-11-27 |
PT85799A (en) | 1987-10-01 |
HUT45962A (en) | 1988-09-28 |
UA11100A (uk) | 1996-12-25 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
LT3530B (en) | Process for preparation of phenyl alkylamines | |
EP0831799B1 (en) | Compounds active at a novel site on receptor-operated calcium channels useful for treatment of neurological disorders | |
DE69032725T2 (de) | ZNS-wirksame 8-Heterocyclyl-2-aminotetralin Derivate | |
US5071875A (en) | Substituted 2-amidotetralins as melatonin agonists and antagonists | |
FI77018B (fi) | Analogifoerfarande foer framstaellning av antidepressivt aktiv (-)-enantiomer av n-metyl-n-/3-(2-metylfenoxi) -3-fenylpropyl/amin och dess farmaceutiskt godtagbara salt. | |
WO1992019581A1 (de) | Derivate der 4-hydroxy-buttersäure | |
CA2071897A1 (en) | Sigma receptor ligands and the use thereof | |
WO1981003491A1 (en) | Therapeutically useful tetralin derivatives | |
DE69935331T2 (de) | Verfahren und verbindungen zur behandlung der depression | |
US5220068A (en) | Psychostimulant agent | |
JP3839049B2 (ja) | メタ位置換のアリルアルキルアミン類ならびに治療および診断のためのその使用 | |
JP4156799B2 (ja) | フェニルアミノアルキルカルボン酸誘導体およびそれを含有する医薬組成物 | |
US7145037B2 (en) | Adamantane derivatives with neuroprotective, antidepressant and anti-ischaemic activities, and process for preparing them | |
PL97347B1 (pl) | Sposob wytwarzania nowych 2-fenylohydrazyno-tiazolin lub-tiazyn | |
US5096929A (en) | 2-amino-1,2,3,4-tetrahydronaphthalene derivatives with cardiovascular activity, process for their preparation and pharmaceutical compositions containing them | |
BRPI0712758A2 (pt) | composto e sais farmaceuticamente aceitáveis do mesmo, composição farmacêutica, método de tratamento de uma doença. e, uso do compsoto | |
RU2015960C1 (ru) | Способ получения фенилалкиламинов или солей этих соединений | |
EP0427605A1 (fr) | Nouveaux dérivés de la morpholine, leur procédé de préparation et les compositions pharmaceutiques les renfermant | |
EP0091437A1 (en) | Therapeutically useful tetralin derivatives iii, processes for preparation and pharmaceutical preparations for such compounds | |
O'DONNELL | RIGID AMINO ACIDS RELATED TO ALPHA-METHYLDOPA. | |
CN117024397A (zh) | 苯丙胺衍生物、其制备方法和应用 | |
EP1790337A2 (en) | Methods and compounds for treating depression and other disorders | |
FR2610931A1 (fr) | Application a titre de medicaments de derives de la dihydroquinidine, nouveaux derives et procede de preparation | |
AU7179781A (en) | Therapeutically useful tetralin derivatives | |
DD266797A5 (de) | Verfahren zur herstellung von amidderivaten |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
MM9A | Lapsed patents |
Effective date: 19970819 |