SU940645A3 - Способ получени производных 1,1 @ -бифенил-2-илалкиламина - Google Patents
Способ получени производных 1,1 @ -бифенил-2-илалкиламина Download PDFInfo
- Publication number
- SU940645A3 SU940645A3 SU802892804A SU2892804A SU940645A3 SU 940645 A3 SU940645 A3 SU 940645A3 SU 802892804 A SU802892804 A SU 802892804A SU 2892804 A SU2892804 A SU 2892804A SU 940645 A3 SU940645 A3 SU 940645A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- hydrogen
- biphenyl
- normal heart
- dose
- heart activity
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- 206010003119 arrhythmia Diseases 0.000 claims abstract description 13
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 8
- 150000002431 hydrogen Chemical class 0.000 claims abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 2
- 230000000694 effects Effects 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 4
- 150000002825 nitriles Chemical class 0.000 claims description 4
- 241001465754 Metazoa Species 0.000 claims description 3
- 230000006793 arrhythmia Effects 0.000 claims description 2
- 238000001990 intravenous administration Methods 0.000 claims description 2
- 238000007911 parenteral administration Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 101100533230 Caenorhabditis elegans ser-2 gene Proteins 0.000 claims 1
- 241001331845 Equus asinus x caballus Species 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 230000000747 cardiac effect Effects 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 239000000243 solution Substances 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 241000282472 Canis lupus familiaris Species 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- -1 M-diisopropyl - -cyano- (1,1-biphenyl-2-yl) -butylamine Chemical compound 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000012259 ether extract Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 210000003462 vein Anatomy 0.000 description 3
- WVYPDPJNPRIPPW-UHFFFAOYSA-N 2-(2-phenylphenyl)acetonitrile Chemical compound N#CCC1=CC=CC=C1C1=CC=CC=C1 WVYPDPJNPRIPPW-UHFFFAOYSA-N 0.000 description 2
- MMNGVZMJMJPHDO-UHFFFAOYSA-N 6-chloro-2-(2-phenylphenyl)hexanenitrile Chemical compound ClCCCCC(C#N)C1=CC=CC=C1C1=CC=CC=C1 MMNGVZMJMJPHDO-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000010606 normalization Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- 239000008247 solid mixture Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 230000003313 weakening effect Effects 0.000 description 2
- DQHKCMPDSGCTHI-UHFFFAOYSA-N 1-bromo-1-chlorobutane Chemical compound CCCC(Cl)Br DQHKCMPDSGCTHI-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- BXKHUQUFHUNALE-UHFFFAOYSA-N 2-(2-phenylphenyl)-6-(propan-2-ylamino)hexanamide Chemical compound CC(C)NCCCCC(C(N)=O)C1=CC=CC=C1C1=CC=CC=C1 BXKHUQUFHUNALE-UHFFFAOYSA-N 0.000 description 1
- JOYZWXABRPLEOO-UHFFFAOYSA-N 5-(dimethylamino)-2-(2-phenylphenyl)pentanenitrile Chemical compound CN(C)CCCC(C#N)C1=CC=CC=C1C1=CC=CC=C1 JOYZWXABRPLEOO-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 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 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000004147 Sorbitan trioleate Substances 0.000 description 1
- PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 230000003113 alkalizing effect Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 239000003978 infusion fluid Substances 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000014380 magnesium carbonate Nutrition 0.000 description 1
- ACXCKRZOISAYHH-UHFFFAOYSA-N molecular chlorine hydrate Chemical compound O.ClCl ACXCKRZOISAYHH-UHFFFAOYSA-N 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- FMJXAYHLEUROOM-UHFFFAOYSA-N n-butyl-2-phenylaniline Chemical compound CCCCNC1=CC=CC=C1C1=CC=CC=C1 FMJXAYHLEUROOM-UHFFFAOYSA-N 0.000 description 1
- SLHWEIUZDKHQLH-UHFFFAOYSA-N n-pentyl-2-phenylaniline Chemical compound CCCCCNC1=CC=CC=C1C1=CC=CC=C1 SLHWEIUZDKHQLH-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229940060184 oil ingredients Drugs 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration 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
- C07C211/27—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 having amino groups linked to the six-membered aromatic ring by saturated carbon chains
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/092—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings with aromatic radicals attached to the chain
-
- 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
- A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Cardiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Heart & Thoracic Surgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1953479A | 1979-03-12 | 1979-03-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU940645A3 true SU940645A3 (ru) | 1982-06-30 |
Family
ID=21793713
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU802892804A SU940645A3 (ru) | 1979-03-12 | 1980-03-12 | Способ получени производных 1,1 @ -бифенил-2-илалкиламина |
| SU813229052A SU1022655A3 (ru) | 1979-03-12 | 1981-01-14 | Способ получени производных 1,1-бифенил-2-илалкиламина или их солей |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU813229052A SU1022655A3 (ru) | 1979-03-12 | 1981-01-14 | Способ получени производных 1,1-бифенил-2-илалкиламина или их солей |
Country Status (31)
| Country | Link |
|---|---|
| EP (1) | EP0015776B1 (OSRAM) |
| JP (1) | JPS55127347A (OSRAM) |
| KR (1) | KR840000103B1 (OSRAM) |
| AR (1) | AR228852A1 (OSRAM) |
| AT (1) | AT367395B (OSRAM) |
| AU (1) | AU528060B2 (OSRAM) |
| BE (1) | BE882167A (OSRAM) |
| CA (1) | CA1144926A (OSRAM) |
| CH (1) | CH644094A5 (OSRAM) |
| CS (1) | CS215052B2 (OSRAM) |
| DD (1) | DD149664A5 (OSRAM) |
| DE (1) | DE3060611D1 (OSRAM) |
| DK (1) | DK103480A (OSRAM) |
| ES (6) | ES489469A0 (OSRAM) |
| FI (1) | FI800736A7 (OSRAM) |
| FR (1) | FR2451363A1 (OSRAM) |
| GB (1) | GB2046256B (OSRAM) |
| GR (1) | GR68036B (OSRAM) |
| HU (1) | HU180334B (OSRAM) |
| IE (1) | IE49552B1 (OSRAM) |
| IL (1) | IL59557A (OSRAM) |
| IT (1) | IT1140773B (OSRAM) |
| LU (1) | LU82237A1 (OSRAM) |
| MX (1) | MX6219E (OSRAM) |
| NZ (1) | NZ193079A (OSRAM) |
| PH (1) | PH14749A (OSRAM) |
| PL (1) | PL121662B1 (OSRAM) |
| PT (1) | PT70928A (OSRAM) |
| RO (1) | RO79906A (OSRAM) |
| SU (2) | SU940645A3 (OSRAM) |
| ZA (1) | ZA801421B (OSRAM) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100470454B1 (ko) * | 2002-05-14 | 2005-02-05 | 대한민국 | 돼지 사료공급을 위한 자동조절급이기 |
| CA2573109A1 (en) * | 2004-06-17 | 2006-01-26 | Thomas A. Dix | Non-natural amino acids |
| ES2742261T3 (es) * | 2011-04-15 | 2020-02-13 | Hivih | Inhibidores de la replicación viral, su proceso de preparación y sus usos terapéuticos |
| EP2821104A1 (en) | 2013-07-05 | 2015-01-07 | Laboratoire Biodim | Inhibitors of viral replication, their process of preparation and their therapeutical uses |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES236010A1 (es) * | 1956-06-29 | 1957-12-16 | Lab Pharmaceutica Dr C Janssen | UN PROCEDIMIENTO PARA PREPARAR NUEVOS DERIVADOS PARASIMPATICOLiTICAMENTE ACTIVOS DE ALFAS-DEFENIL PROPANO |
| US3433836A (en) * | 1966-01-14 | 1969-03-18 | Rexall Drug Chemical | Alpha-diaryl alpha,omega-alkylene glycol-dilower-alkylamines |
| GB1475314A (en) * | 1973-11-02 | 1977-06-01 | Cm Ind | Phenyl-propylamine derivatives |
| IL48319A0 (en) * | 1974-10-26 | 1975-12-31 | Merck Patent Gmbh | Araliphatic nitrogen compounds and a process for their preparation |
| GB1523655A (en) * | 1975-02-10 | 1978-09-06 | Armour Pharma | 4-(4-biphenylyl) butylamines and treatment of the animal organism therewith |
-
1980
- 1980-03-09 IL IL59557A patent/IL59557A/xx unknown
- 1980-03-10 CA CA000347365A patent/CA1144926A/en not_active Expired
- 1980-03-10 PH PH23743A patent/PH14749A/en unknown
- 1980-03-10 HU HU8080563A patent/HU180334B/hu unknown
- 1980-03-10 NZ NZ193079A patent/NZ193079A/xx unknown
- 1980-03-10 AU AU56302/80A patent/AU528060B2/en not_active Ceased
- 1980-03-10 LU LU82237A patent/LU82237A1/fr unknown
- 1980-03-10 RO RO80100427A patent/RO79906A/ro unknown
- 1980-03-10 GR GR61387A patent/GR68036B/el unknown
- 1980-03-10 PT PT70928A patent/PT70928A/pt unknown
- 1980-03-10 FR FR8005311A patent/FR2451363A1/fr active Granted
- 1980-03-10 CH CH186880A patent/CH644094A5/fr not_active IP Right Cessation
- 1980-03-11 DE DE8080300744T patent/DE3060611D1/de not_active Expired
- 1980-03-11 IT IT20503/80A patent/IT1140773B/it active
- 1980-03-11 AT AT0134580A patent/AT367395B/de not_active IP Right Cessation
- 1980-03-11 IE IE493/80A patent/IE49552B1/en unknown
- 1980-03-11 EP EP80300744A patent/EP0015776B1/en not_active Expired
- 1980-03-11 ZA ZA00801421A patent/ZA801421B/xx unknown
- 1980-03-11 PL PL1980222601A patent/PL121662B1/pl unknown
- 1980-03-11 JP JP3256880A patent/JPS55127347A/ja active Pending
- 1980-03-11 CS CS801665A patent/CS215052B2/cs unknown
- 1980-03-11 FI FI800736A patent/FI800736A7/fi not_active Application Discontinuation
- 1980-03-11 DK DK103480A patent/DK103480A/da not_active Application Discontinuation
- 1980-03-11 GB GB8008170A patent/GB2046256B/en not_active Expired
- 1980-03-11 BE BE1/9747A patent/BE882167A/fr not_active IP Right Cessation
- 1980-03-12 AR AR280280A patent/AR228852A1/es active
- 1980-03-12 MX MX808706U patent/MX6219E/es unknown
- 1980-03-12 KR KR1019800001023A patent/KR840000103B1/ko not_active Expired
- 1980-03-12 SU SU802892804A patent/SU940645A3/ru active
- 1980-03-12 DD DD80219615A patent/DD149664A5/de unknown
- 1980-03-12 ES ES489469A patent/ES489469A0/es active Granted
- 1980-11-27 ES ES497209A patent/ES497209A0/es active Granted
- 1980-11-27 ES ES497207A patent/ES8201526A1/es not_active Expired
- 1980-11-27 ES ES497210A patent/ES497210A0/es active Granted
- 1980-11-27 ES ES497208A patent/ES497208A0/es active Granted
- 1980-11-27 ES ES497206A patent/ES8201525A1/es not_active Expired
-
1981
- 1981-01-14 SU SU813229052A patent/SU1022655A3/ru active
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