SE463261B - Fenylisopropylaminderivat, foerfarande foer framstaellning daerav samt farmaceutiska beredningar - Google Patents
Fenylisopropylaminderivat, foerfarande foer framstaellning daerav samt farmaceutiska beredningarInfo
- Publication number
- SE463261B SE463261B SE8600413A SE8600413A SE463261B SE 463261 B SE463261 B SE 463261B SE 8600413 A SE8600413 A SE 8600413A SE 8600413 A SE8600413 A SE 8600413A SE 463261 B SE463261 B SE 463261B
- Authority
- SE
- Sweden
- Prior art keywords
- methyl
- group
- general formula
- known per
- manner known
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 29
- 239000000825 pharmaceutical preparation Substances 0.000 title claims 2
- FRCFWPVMFJMNDP-UHFFFAOYSA-N n-propan-2-ylaniline Chemical class CC(C)NC1=CC=CC=C1 FRCFWPVMFJMNDP-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 45
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 25
- 150000001412 amines Chemical class 0.000 claims description 18
- 230000000694 effects Effects 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- -1 phenylisopropyl Chemical class 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000011737 fluorine Substances 0.000 claims description 9
- DZGWFCGJZKJUFP-UHFFFAOYSA-N tyramine Chemical compound NCCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-N 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical group [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000012954 diazonium Chemical group 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 4
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002130 sulfonic acid ester group Chemical group 0.000 claims description 4
- 229960003732 tyramine Drugs 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
- 239000002253 acid Substances 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- UGQMRVRMYYASKQ-UHFFFAOYSA-N Hypoxanthine nucleoside Natural products OC1C(O)C(CO)OC1N1C(NC=NC2=O)=C2N=C1 UGQMRVRMYYASKQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 229960003638 dopamine Drugs 0.000 claims description 2
- 150000004658 ketimines Chemical class 0.000 claims description 2
- 150000004702 methyl esters Chemical class 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical class CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims 2
- JVNZUEVMRPWHLF-UHFFFAOYSA-N 1,2-dibromoprop-1-ene Chemical group CC(Br)=CBr JVNZUEVMRPWHLF-UHFFFAOYSA-N 0.000 claims 1
- 102100035861 Cytosolic 5'-nucleotidase 1A Human genes 0.000 claims 1
- 101000802744 Homo sapiens Cytosolic 5'-nucleotidase 1A Proteins 0.000 claims 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000006410 propenylene group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 63
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 63
- 239000000243 solution Substances 0.000 description 46
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 45
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
- 239000000203 mixture Substances 0.000 description 20
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 241000700159 Rattus Species 0.000 description 11
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 102000010909 Monoamine Oxidase Human genes 0.000 description 8
- 108010062431 Monoamine oxidase Proteins 0.000 description 8
- 210000004556 brain Anatomy 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000000284 extract Substances 0.000 description 7
- 229940117803 phenethylamine Drugs 0.000 description 7
- 239000011260 aqueous acid Substances 0.000 description 5
- 229940125890 compound Ia Drugs 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 4
- DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 4
- 210000004185 liver Anatomy 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
- 210000000056 organ Anatomy 0.000 description 4
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- 239000007858 starting material Substances 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- XWBDWHCCBGMXKG-UHFFFAOYSA-N ethanamine;hydron;chloride Chemical compound Cl.CCN XWBDWHCCBGMXKG-UHFFFAOYSA-N 0.000 description 3
- 230000037406 food intake Effects 0.000 description 3
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- 230000005764 inhibitory process Effects 0.000 description 3
- 229960002523 mercuric chloride Drugs 0.000 description 3
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 3
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- RILZRCJGXSFXNE-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)phenyl]ethanol Chemical compound OCCC1=CC=C(OC(F)(F)F)C=C1 RILZRCJGXSFXNE-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
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- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 239000002027 dichloromethane extract Substances 0.000 description 1
- 230000000916 dilatatory effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000003291 dopaminomimetic effect Effects 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 230000002896 effect on catalepsy Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 210000001320 hippocampus Anatomy 0.000 description 1
- 235000003642 hunger Nutrition 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 210000003016 hypothalamus Anatomy 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 230000037323 metabolic rate Effects 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-N methyl sulfate Chemical compound COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 description 1
- 239000012022 methylating agents Substances 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 230000036651 mood Effects 0.000 description 1
- 210000001577 neostriatum Anatomy 0.000 description 1
- 229960002748 norepinephrine Drugs 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000001242 postsynaptic effect Effects 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000036316 preload Effects 0.000 description 1
- JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 description 1
- IJNJLGFTSIAHEA-UHFFFAOYSA-N prop-2-ynal Chemical compound O=CC#C IJNJLGFTSIAHEA-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 210000001147 pulmonary artery Anatomy 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 230000037351 starvation Effects 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000563 toxic property Toxicity 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/29—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- 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
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Urology & Nephrology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU842124A HU207282B (en) | 1984-05-31 | 1984-05-31 | Process for producing phenyl-alkyl-amine derivatives and pharmaceutical compositions containing them |
| PCT/HU1985/000035 WO1985005617A1 (fr) | 1984-05-31 | 1985-05-31 | Derive de phenylisopropylamine et sa preparation |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE8600413D0 SE8600413D0 (sv) | 1986-01-30 |
| SE8600413L SE8600413L (sv) | 1986-01-30 |
| SE463261B true SE463261B (sv) | 1990-10-29 |
Family
ID=10957881
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8600413A SE463261B (sv) | 1984-05-31 | 1986-01-30 | Fenylisopropylaminderivat, foerfarande foer framstaellning daerav samt farmaceutiska beredningar |
Country Status (23)
| Country | Link |
|---|---|
| US (2) | US5008292A (fr) |
| EP (1) | EP0186680B1 (fr) |
| JP (2) | JPS61502259A (fr) |
| AT (1) | AT394552B (fr) |
| AU (1) | AU588757B2 (fr) |
| BG (1) | BG61318B2 (fr) |
| CH (1) | CH671574A5 (fr) |
| CS (1) | CS271313B2 (fr) |
| DD (1) | DD235065A5 (fr) |
| DE (2) | DE3590241T (fr) |
| DK (1) | DK166018C (fr) |
| ES (2) | ES8609204A1 (fr) |
| FI (1) | FI92053C (fr) |
| GB (1) | GB2171694B (fr) |
| GE (3) | GEP19970786B (fr) |
| HU (1) | HU207282B (fr) |
| IL (1) | IL75358A (fr) |
| MX (1) | MX9203090A (fr) |
| PL (2) | PL150477B1 (fr) |
| PT (1) | PT80574B (fr) |
| SE (1) | SE463261B (fr) |
| SU (3) | SU1487810A3 (fr) |
| WO (1) | WO1985005617A1 (fr) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0191269B1 (fr) * | 1984-11-22 | 1991-03-06 | Sandoz Ag | Homopropargylamines |
| US5225446A (en) * | 1990-08-31 | 1993-07-06 | Deprenyl Animal Health, Inc. | Use of 1-deprenyl for retention of specific physiological functions |
| US5444095A (en) * | 1991-04-04 | 1995-08-22 | University Of Toronto, Innovations Foundation | Use of deprenyl to rescue damaged nerve cells |
| US5844003A (en) * | 1991-04-04 | 1998-12-01 | Innovations Foundation | Use of deprenyl compounds to maintain, prevent loss, or recover nerve cell function |
| US5767164A (en) * | 1991-04-04 | 1998-06-16 | Innovations Foundation | Use of deprenyl to rescue damaged nerve cells |
| IL112819A (en) * | 1991-10-16 | 2001-11-25 | Teva Pharma | Fluorinated 1-aminoindan compounds and a process for their preparation |
| 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 |
| US5169536A (en) * | 1992-04-28 | 1992-12-08 | Betz Laboratories, Inc. | Detoxification agents for surfactant based biocides |
| IES61604B2 (en) * | 1993-12-16 | 1994-11-16 | Russinsky Ltd | A process for producing pharmaceutical compounds |
| US5516747A (en) * | 1994-04-18 | 1996-05-14 | Henkel Corporation | Pesticidal surfactant mixtures comprising alkyl polyglycosides and alkyl naphthalene sulfonates |
| US5587398A (en) * | 1994-06-03 | 1996-12-24 | David R. Elmaleh | Meta substituted arylalkylamines and therapeutic and diagnostic uses therefor |
| HU218927B (hu) * | 1994-11-22 | 2000-12-28 | Chinoin Gyógyszer és Vegyészeti Termékek Gyára Rt. | Eljárás propargil-ammónium-klorid-származékok előállítására |
| AU723047B2 (en) | 1995-02-10 | 2000-08-17 | University Of Toronto Innovations Foundation, The | Deprenyl compounds for treatment of glaucoma |
| JP3087891B2 (ja) | 1998-03-31 | 2000-09-11 | 東洋紡績株式会社 | 電解質測定用試薬組成物 |
| HUP9902482A2 (hu) * | 1999-07-22 | 2002-04-29 | Chinoin Gyógyszer és Vegyészeti Termékek Gyára Rt. | P-fluoro-selegilin alkalmazása neuroprotektív gyógyszerkészítmények előállítására |
| US7956220B2 (en) * | 2005-07-01 | 2011-06-07 | Jenrin Discovery | MAO-B inhibitors useful for treating obesity |
| EP2053033A1 (fr) * | 2007-10-26 | 2009-04-29 | Bayer Schering Pharma AG | Composants à utiliser dans l'imagerie, le diagnostic et/ou le traitement des maladies du système nerveux central ou des tumeurs |
| CN102180798B (zh) * | 2011-03-18 | 2013-11-06 | 湖北汉星化工新材料有限公司 | 一步法催化合成n,n-二乙基丙炔胺的方法 |
| WO2015087094A1 (fr) * | 2013-12-10 | 2015-06-18 | Semmelweis Egyetem | Nouveaux dérivés arylalcénylpropargylamine faisant preuve d'action neuroprotectrice pour le traitement des maladies neurodégénératives |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1311843A (fr) * | 1961-09-06 | 1962-12-14 | Abbott Lab | Procédé de préparation de nu-halobenzyl-nu-méthyl-2-propynylamines |
| US3142554A (en) * | 1961-10-10 | 1964-07-28 | Monsanto Co | Controlling vegetation with aryl thioalkylamines |
| GB1027611A (en) * | 1962-01-04 | 1966-04-27 | May & Baker Ltd | Phenoxy- and phenylthio-alkylamines and acid addition salts thereof |
| GB1031425A (en) * | 1962-03-30 | 1966-06-02 | Chinoin Gyogyszer Es Vegyeszet | New aralkylamines and their preparation |
| DE1227447B (de) * | 1962-03-30 | 1966-10-27 | Chinoin Gyogyszer Es Vegyeszet | Verfahren zur Herstellung von Phenylisopropylaminen |
| GB1121857A (en) * | 1965-01-05 | 1968-07-31 | Science Union & Cie | New phenylisopropylamine derivatives and process for their preparation and pharmaceutical preparations of such derivatives |
| CH551943A (en) * | 1965-02-08 | 1974-07-31 | Chinoin Gyogyszer Es Vegyeszet | N-(Lower alkyl)-phenylisopropylamines |
| US3485874A (en) * | 1966-05-04 | 1969-12-23 | Chinoin Gyogyszer Es Vegyeszet | Ortho and para bromophenyl isopropyl methylamines |
| US3496195A (en) * | 1966-05-11 | 1970-02-17 | Chinoin Gyogyszer Es Vegyeszet | D-o-bromo-phenyl-isopropyl-methylpropinylamine and its salts |
| US4137328A (en) * | 1970-07-18 | 1979-01-30 | Pfizer Inc. | Phenyl-alkanolamine, alkylamine and α-aminoalkyl ketone derivatives as heart stimulants |
| US3689504A (en) * | 1970-12-24 | 1972-09-05 | Abbott Lab | N-substituted -alpha-methyl-3,4-(methylenedioxy) phenethylamines |
| US4314081A (en) * | 1974-01-10 | 1982-02-02 | Eli Lilly And Company | Arloxyphenylpropylamines |
| US4105695A (en) * | 1975-12-11 | 1978-08-08 | Bristol-Myers Company | 2-Amino-1-(2,5-dimethoxyphenyl)-butanes |
| US4156017A (en) * | 1977-02-22 | 1979-05-22 | Schering Aktiengesellschaft | Pesticides |
| US4200654A (en) * | 1978-11-24 | 1980-04-29 | Abbott Laboratories | Ovicides |
| FR2486074A1 (fr) * | 1979-12-14 | 1982-01-08 | Lafon Labor | Derives de fluorophenacyl-amine, leur procede de preparation et leur application en therapeutique |
-
1984
- 1984-05-31 HU HU842124A patent/HU207282B/hu not_active IP Right Cessation
-
1985
- 1985-05-30 CS CS853895A patent/CS271313B2/cs not_active IP Right Cessation
- 1985-05-31 AU AU44375/85A patent/AU588757B2/en not_active Ceased
- 1985-05-31 JP JP60502561A patent/JPS61502259A/ja active Granted
- 1985-05-31 PL PL1985276231A patent/PL150477B1/pl unknown
- 1985-05-31 IL IL75358A patent/IL75358A/xx not_active IP Right Cessation
- 1985-05-31 AT AT0901585A patent/AT394552B/de not_active IP Right Cessation
- 1985-05-31 DD DD85276869A patent/DD235065A5/de not_active IP Right Cessation
- 1985-05-31 PL PL1985253737A patent/PL149288B1/pl unknown
- 1985-05-31 EP EP85902626A patent/EP0186680B1/fr not_active Expired
- 1985-05-31 PT PT80574A patent/PT80574B/pt not_active IP Right Cessation
- 1985-05-31 DE DE19853590241 patent/DE3590241T/de active Pending
- 1985-05-31 GB GB08602394A patent/GB2171694B/en not_active Expired
- 1985-05-31 ES ES544400A patent/ES8609204A1/es not_active Expired
- 1985-05-31 WO PCT/HU1985/000035 patent/WO1985005617A1/fr active IP Right Grant
- 1985-05-31 DE DE3590241A patent/DE3590241C2/de not_active Expired - Fee Related
-
1986
- 1986-01-09 FI FI860101A patent/FI92053C/fi not_active IP Right Cessation
- 1986-01-30 SE SE8600413A patent/SE463261B/sv not_active IP Right Cessation
- 1986-01-30 DK DK045786A patent/DK166018C/da not_active IP Right Cessation
- 1986-01-30 SU SU864015073A patent/SU1487810A3/ru active
- 1986-02-28 ES ES552827A patent/ES8704445A1/es not_active Expired
- 1986-05-31 CH CH209/86A patent/CH671574A5/fr not_active IP Right Cessation
- 1986-06-16 SU SU864027653A patent/SU1609443A3/ru active
- 1986-06-16 SU SU864027666A patent/SU1549477A3/ru active
-
1987
- 1987-11-25 US US07/129,342 patent/US5008292A/en not_active Expired - Fee Related
-
1989
- 1989-02-15 US US07/311,436 patent/US4960797A/en not_active Expired - Fee Related
-
1992
- 1992-06-22 MX MX9203090A patent/MX9203090A/es unknown
-
1993
- 1993-01-14 JP JP5005262A patent/JPH0819057B2/ja not_active Expired - Lifetime
- 1993-08-12 GE GEAP19931396A patent/GEP19970786B/en unknown
- 1993-08-12 GE GEAP19931392A patent/GEP19960459B/en unknown
- 1993-08-12 GE GEAP19931403A patent/GEP19970818B/en unknown
- 1993-12-02 BG BG098264A patent/BG61318B2/bg unknown
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