SU735166A3 - Способ получени производных амина или их солей - Google Patents
Способ получени производных амина или их солей Download PDFInfo
- Publication number
- SU735166A3 SU735166A3 SU772528198A SU2528198A SU735166A3 SU 735166 A3 SU735166 A3 SU 735166A3 SU 772528198 A SU772528198 A SU 772528198A SU 2528198 A SU2528198 A SU 2528198A SU 735166 A3 SU735166 A3 SU 735166A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- compounds
- methyl
- theory
- salts
- amine
- Prior art date
Links
- 150000001412 amines Chemical class 0.000 title claims abstract description 10
- 150000003839 salts Chemical class 0.000 title claims description 9
- 238000000034 method Methods 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- -1 hydroxy, methyl Chemical group 0.000 claims description 17
- 241000282472 Canis lupus familiaris Species 0.000 claims description 6
- 241000282326 Felis catus Species 0.000 claims description 4
- 238000002474 experimental method Methods 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000004593 Epoxy Substances 0.000 claims description 2
- 230000036772 blood pressure Effects 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 230000002792 vascular Effects 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 235000014443 Pyrus communis Nutrition 0.000 claims 1
- 230000000747 cardiac effect Effects 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 230000001077 hypotensive effect Effects 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 150000002923 oximes Chemical class 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000002464 receptor antagonist Substances 0.000 claims 1
- 229940044551 receptor antagonist Drugs 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 4
- 150000003141 primary amines Chemical class 0.000 abstract description 2
- 102000012740 beta Adrenergic Receptors Human genes 0.000 abstract 1
- 108010079452 beta Adrenergic Receptors Proteins 0.000 abstract 1
- 125000003700 epoxy group Chemical group 0.000 abstract 1
- 239000007858 starting material Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- XLHUBROMZOAQMV-UHFFFAOYSA-N 1,4-benzosemiquinone Chemical group [O]C1=CC=C(O)C=C1 XLHUBROMZOAQMV-UHFFFAOYSA-N 0.000 description 4
- IGBLYBKIOYVOIW-UHFFFAOYSA-N 6-propoxy-7-oxabicyclo[4.1.0]hepta-2,4-diene-1-carbonitrile Chemical compound C(#N)C12C(OCCC)(C=CC=C1)O2 IGBLYBKIOYVOIW-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000005557 antagonist Substances 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 229940095064 tartrate Drugs 0.000 description 3
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 2
- LTPVSOCPYWDIFU-UHFFFAOYSA-N 4-methoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1 LTPVSOCPYWDIFU-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 2
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000002146 bilateral effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 2
- 229960003147 reserpine Drugs 0.000 description 2
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 2
- WOQCKCKZJOUCNN-UHFFFAOYSA-N 1-chloro-3-(2-methylphenoxy)propan-2-ol Chemical compound CC1=CC=CC=C1OCC(O)CCl WOQCKCKZJOUCNN-UHFFFAOYSA-N 0.000 description 1
- XLHORNMWQFLFAF-UHFFFAOYSA-N 2-(2-aminoethoxy)phenol Chemical compound NCCOC1=CC=CC=C1O XLHORNMWQFLFAF-UHFFFAOYSA-N 0.000 description 1
- YHZOBQKNTYURDW-UHFFFAOYSA-N 2-(3,4-dimethoxyphenoxy)ethanamine Chemical compound COC1=CC=C(OCCN)C=C1OC YHZOBQKNTYURDW-UHFFFAOYSA-N 0.000 description 1
- RYMVEKOKZTZGFN-UHFFFAOYSA-N 2-(3,5-dimethoxyphenoxy)ethanamine Chemical compound COC1=CC(OC)=CC(OCCN)=C1 RYMVEKOKZTZGFN-UHFFFAOYSA-N 0.000 description 1
- JKNUOOAMZXVGBO-UHFFFAOYSA-N 4-(2-aminoethoxy)-2-methoxyphenol Chemical compound COC1=CC(OCCN)=CC=C1O JKNUOOAMZXVGBO-UHFFFAOYSA-N 0.000 description 1
- QSDOKFGRSJQNMX-UHFFFAOYSA-N 4-(2-aminoethoxy)phenol Chemical compound NCCOC1=CC=C(O)C=C1 QSDOKFGRSJQNMX-UHFFFAOYSA-N 0.000 description 1
- PXACTUVBBMDKRW-UHFFFAOYSA-N 4-bromobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Br)C=C1 PXACTUVBBMDKRW-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 208000001871 Tachycardia Diseases 0.000 description 1
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
- 206010047141 Vasodilatation Diseases 0.000 description 1
- GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000011717 all-trans-retinol Substances 0.000 description 1
- 235000019169 all-trans-retinol Nutrition 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 230000006793 arrhythmia Effects 0.000 description 1
- 230000004872 arterial blood pressure Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 210000001715 carotid artery Anatomy 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000010339 dilation Effects 0.000 description 1
- XGZRAKBCYZIBKP-UHFFFAOYSA-L disodium;dihydroxide Chemical compound [OH-].[OH-].[Na+].[Na+] XGZRAKBCYZIBKP-UHFFFAOYSA-L 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000011440 grout Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 125000001905 inorganic group Chemical group 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229940018435 isoproterenol sulfate Drugs 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- LZCOQTDXKCNBEE-IKIFYQGPSA-N methscopolamine Chemical compound C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3[N+]([C@H](C2)[C@@H]2[C@H]3O2)(C)C)=CC=CC=C1 LZCOQTDXKCNBEE-IKIFYQGPSA-N 0.000 description 1
- 229960001383 methylscopolamine Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 210000002464 muscle smooth vascular Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 210000005259 peripheral blood Anatomy 0.000 description 1
- 239000011886 peripheral blood Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 230000002889 sympathetic effect Effects 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 210000001364 upper extremity Anatomy 0.000 description 1
- 230000001515 vagal effect Effects 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- 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
- C07D295/096—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 separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (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)
- Pyrrole Compounds (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE7611125A SE416545B (sv) | 1976-10-07 | 1976-10-07 | Forfarande for framstellning av nya hjertaktiva 1-frnoxi-3-aminopropan-2-ol-derivat |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU735166A3 true SU735166A3 (ru) | 1980-05-15 |
Family
ID=20329066
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU772528198A SU735166A3 (ru) | 1976-10-07 | 1977-10-06 | Способ получени производных амина или их солей |
| SU782640402A SU784760A3 (ru) | 1976-10-07 | 1978-07-28 | Способ получени производных амина или их солей |
| SU782641105A SU959623A3 (ru) | 1976-10-07 | 1978-07-28 | Способ получени производных амина |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU782640402A SU784760A3 (ru) | 1976-10-07 | 1978-07-28 | Способ получени производных амина или их солей |
| SU782641105A SU959623A3 (ru) | 1976-10-07 | 1978-07-28 | Способ получени производных амина |
Country Status (22)
| Country | Link |
|---|---|
| JP (1) | JPS5346928A (cs) |
| AT (1) | AT351509B (cs) |
| AU (1) | AU516727B2 (cs) |
| BE (1) | BE859474A (cs) |
| CA (1) | CA1093096A (cs) |
| CH (1) | CH636337A5 (cs) |
| CS (5) | CS208734B2 (cs) |
| DD (1) | DD132195A5 (cs) |
| DE (1) | DE2743493A1 (cs) |
| DK (1) | DK145375C (cs) |
| FI (1) | FI772936A7 (cs) |
| FR (1) | FR2367054A1 (cs) |
| GB (1) | GB1589838A (cs) |
| HU (1) | HU177638B (cs) |
| IE (1) | IE45938B1 (cs) |
| LU (1) | LU78263A1 (cs) |
| NL (1) | NL7710941A (cs) |
| NO (1) | NO145436C (cs) |
| NZ (1) | NZ185318A (cs) |
| SE (1) | SE416545B (cs) |
| SU (3) | SU735166A3 (cs) |
| ZA (1) | ZA775603B (cs) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD150456A5 (de) * | 1979-03-01 | 1981-09-02 | Ciba Geigy Ag | Verfahren zur herstellung von derivaten des 3-amino-1,2-propandiols |
| GB8519154D0 (en) * | 1985-07-30 | 1985-09-04 | Ici Plc | Aromatic ethers |
| JPH0627370B2 (ja) * | 1985-08-23 | 1994-04-13 | 日本エステル株式会社 | ポリエステル異形断面太細糸 |
| GB8925032D0 (en) * | 1989-11-06 | 1989-12-28 | Ici Plc | Chemical compounds |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE590054A (fr) * | 1959-04-22 | 1960-10-24 | Pfizer | Alkylamines et leur préparation. |
| GB1264128A (cs) * | 1968-06-29 | 1972-02-16 | ||
| GB1433920A (en) * | 1973-10-01 | 1976-04-28 | Ici Ltd | Alkanolamine derivatives |
-
1976
- 1976-10-07 SE SE7611125A patent/SE416545B/xx unknown
-
1977
- 1977-09-19 ZA ZA00775603A patent/ZA775603B/xx unknown
- 1977-09-28 DE DE19772743493 patent/DE2743493A1/de not_active Withdrawn
- 1977-10-03 AT AT702177A patent/AT351509B/de not_active IP Right Cessation
- 1977-10-03 NZ NZ185318A patent/NZ185318A/xx unknown
- 1977-10-04 AU AU29300/77A patent/AU516727B2/en not_active Expired
- 1977-10-05 FI FI772936A patent/FI772936A7/fi not_active Application Discontinuation
- 1977-10-05 DD DD7700201371A patent/DD132195A5/xx unknown
- 1977-10-05 HU HU77HE752A patent/HU177638B/hu unknown
- 1977-10-05 NL NL7710941A patent/NL7710941A/xx not_active Application Discontinuation
- 1977-10-06 CA CA288,290A patent/CA1093096A/en not_active Expired
- 1977-10-06 IE IE2046/77A patent/IE45938B1/en unknown
- 1977-10-06 NO NO773406A patent/NO145436C/no unknown
- 1977-10-06 FR FR7730156A patent/FR2367054A1/fr active Granted
- 1977-10-06 CS CS776486A patent/CS208734B2/cs unknown
- 1977-10-06 CS CS776486A patent/CS208731B2/cs unknown
- 1977-10-06 LU LU78263A patent/LU78263A1/xx unknown
- 1977-10-06 SU SU772528198A patent/SU735166A3/ru active
- 1977-10-06 CS CS776486A patent/CS208733B2/cs unknown
- 1977-10-06 GB GB41699/77A patent/GB1589838A/en not_active Expired
- 1977-10-06 DK DK443177A patent/DK145375C/da active
- 1977-10-06 CS CS776486A patent/CS208732B2/cs unknown
- 1977-10-06 CS CS776486A patent/CS208730B2/cs unknown
- 1977-10-07 BE BE181531A patent/BE859474A/xx unknown
- 1977-10-07 JP JP12133477A patent/JPS5346928A/ja active Pending
- 1977-10-07 CH CH1230577A patent/CH636337A5/de not_active IP Right Cessation
-
1978
- 1978-07-28 SU SU782640402A patent/SU784760A3/ru active
- 1978-07-28 SU SU782641105A patent/SU959623A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| CS208732B2 (en) | 1981-09-15 |
| DK145375C (da) | 1983-04-11 |
| ATA702177A (de) | 1979-01-15 |
| AU516727B2 (en) | 1981-06-18 |
| FR2367054A1 (fr) | 1978-05-05 |
| JPS5346928A (en) | 1978-04-27 |
| SE416545B (sv) | 1981-01-19 |
| CS208731B2 (en) | 1981-09-15 |
| AU2930077A (en) | 1979-04-12 |
| HU177638B (en) | 1981-11-28 |
| DK145375B (da) | 1982-11-08 |
| NO145436C (no) | 1982-03-24 |
| BE859474A (fr) | 1978-04-07 |
| NZ185318A (en) | 1980-02-21 |
| SE7611125L (sv) | 1978-04-08 |
| CS208733B2 (en) | 1981-09-15 |
| CA1093096A (en) | 1981-01-06 |
| IE45938B1 (en) | 1983-01-12 |
| NO145436B (no) | 1981-12-14 |
| FI772936A7 (fi) | 1978-04-08 |
| SU784760A3 (ru) | 1980-11-30 |
| LU78263A1 (cs) | 1978-06-09 |
| AT351509B (de) | 1979-07-25 |
| NL7710941A (nl) | 1978-04-11 |
| DD132195A5 (de) | 1978-09-06 |
| NO773406L (no) | 1978-04-10 |
| CH636337A5 (en) | 1983-05-31 |
| DK443177A (da) | 1978-04-08 |
| ZA775603B (en) | 1978-06-28 |
| DE2743493A1 (de) | 1978-04-13 |
| SU959623A3 (ru) | 1982-09-15 |
| CS208730B2 (en) | 1981-09-15 |
| CS208734B2 (en) | 1981-09-15 |
| IE45938L (en) | 1978-04-07 |
| FR2367054B1 (cs) | 1981-11-06 |
| GB1589838A (en) | 1981-05-20 |
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