CA1093096A - Heart active derivatives of 1-amino-2,3-dihydroxy propane - Google Patents
Heart active derivatives of 1-amino-2,3-dihydroxy propaneInfo
- Publication number
- CA1093096A CA1093096A CA288,290A CA288290A CA1093096A CA 1093096 A CA1093096 A CA 1093096A CA 288290 A CA288290 A CA 288290A CA 1093096 A CA1093096 A CA 1093096A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- group
- propanol
- compound
- ethylamino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- KQIGMPWTAHJUMN-UHFFFAOYSA-N 3-aminopropane-1,2-diol Chemical class NCC(O)CO KQIGMPWTAHJUMN-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 89
- 239000001257 hydrogen Substances 0.000 claims abstract description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
- -1 methoxy, propargyloxy Chemical group 0.000 claims abstract description 19
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 56
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 48
- 230000008569 process Effects 0.000 claims description 43
- 150000003839 salts Chemical class 0.000 claims description 25
- 238000002360 preparation method Methods 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 22
- 239000000126 substance Substances 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 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 claims description 11
- 230000009467 reduction Effects 0.000 claims description 10
- 238000006722 reduction reaction Methods 0.000 claims description 10
- QSDOKFGRSJQNMX-UHFFFAOYSA-N 4-(2-aminoethoxy)phenol Chemical compound NCCOC1=CC=C(O)C=C1 QSDOKFGRSJQNMX-UHFFFAOYSA-N 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- OZVSEDOWHGRSMN-UHFFFAOYSA-N 1-methyl-6-propoxy-7-oxabicyclo[4.1.0]hepta-2,4-diene Chemical compound C1=CC=CC2(OCCC)C1(C)O2 OZVSEDOWHGRSMN-UHFFFAOYSA-N 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000004043 oxo group Chemical group O=* 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 5
- 229940095064 tartrate Drugs 0.000 claims description 5
- 238000000855 fermentation Methods 0.000 claims description 4
- 230000004151 fermentation Effects 0.000 claims description 4
- 238000000197 pyrolysis Methods 0.000 claims description 4
- XLHORNMWQFLFAF-UHFFFAOYSA-N 2-(2-aminoethoxy)phenol Chemical compound NCCOC1=CC=CC=C1O XLHORNMWQFLFAF-UHFFFAOYSA-N 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- 238000003797 solvolysis reaction Methods 0.000 claims description 3
- JKCMVLNUYZQNAE-UHFFFAOYSA-N 1-ethyl-6-propoxy-7-oxabicyclo[4.1.0]hepta-2,4-diene Chemical compound C(C)C12C(OCCC)(C=CC=C1)O2 JKCMVLNUYZQNAE-UHFFFAOYSA-N 0.000 claims description 2
- RYMVEKOKZTZGFN-UHFFFAOYSA-N 2-(3,5-dimethoxyphenoxy)ethanamine Chemical compound COC1=CC(OC)=CC(OCCN)=C1 RYMVEKOKZTZGFN-UHFFFAOYSA-N 0.000 claims description 2
- LGHNHPRURDSNNK-UHFFFAOYSA-N 4-(2-aminoethylsulfanyl)phenol Chemical compound NCCSC1=CC=C(O)C=C1 LGHNHPRURDSNNK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000003700 epoxy group Chemical group 0.000 claims description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 6
- YXRCDWIZAGWUBL-UHFFFAOYSA-N 2-(4-methoxyphenoxy)ethanamine Chemical compound COC1=CC=C(OCCN)C=C1 YXRCDWIZAGWUBL-UHFFFAOYSA-N 0.000 claims 1
- JKNUOOAMZXVGBO-UHFFFAOYSA-N 4-(2-aminoethoxy)-2-methoxyphenol Chemical compound COC1=CC(OCCN)=CC=C1O JKNUOOAMZXVGBO-UHFFFAOYSA-N 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 150000003892 tartrate salts Chemical class 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 abstract description 4
- 208000024172 Cardiovascular disease Diseases 0.000 abstract description 3
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000005336 allyloxy group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000000168 pyrrolyl group Chemical group 0.000 abstract 1
- 239000007858 starting material Substances 0.000 description 29
- 239000002253 acid Substances 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- 235000002639 sodium chloride Nutrition 0.000 description 23
- 239000000243 solution Substances 0.000 description 20
- 239000003795 chemical substances by application Substances 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 13
- 150000007513 acids Chemical class 0.000 description 10
- 230000007062 hydrolysis Effects 0.000 description 10
- 238000006460 hydrolysis reaction Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 9
- 239000001828 Gelatine Substances 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 239000013543 active substance Substances 0.000 description 8
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 8
- 229920000159 gelatin Polymers 0.000 description 8
- 235000019322 gelatine Nutrition 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 7
- 229920002472 Starch Polymers 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 239000008107 starch Substances 0.000 description 7
- 235000019698 starch Nutrition 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- XLHUBROMZOAQMV-UHFFFAOYSA-N 1,4-benzosemiquinone Chemical group [O]C1=CC=C(O)C=C1 XLHUBROMZOAQMV-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- 241000282472 Canis lupus familiaris Species 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229910021529 ammonia Inorganic materials 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 235000000346 sugar Nutrition 0.000 description 6
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 239000001294 propane Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 4
- 241000282326 Felis catus Species 0.000 description 4
- 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 4
- 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 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 244000061456 Solanum tuberosum Species 0.000 description 4
- 235000002595 Solanum tuberosum Nutrition 0.000 description 4
- 239000005557 antagonist Substances 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- 229960002748 norepinephrine Drugs 0.000 description 4
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 4
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 235000012015 potatoes Nutrition 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000454 talc Substances 0.000 description 4
- 229910052623 talc Inorganic materials 0.000 description 4
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229930006000 Sucrose Natural products 0.000 description 3
- 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 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 3
- 230000036772 blood pressure Effects 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 230000006835 compression Effects 0.000 description 3
- 238000007906 compression Methods 0.000 description 3
- 235000013681 dietary sucrose Nutrition 0.000 description 3
- 229940093499 ethyl acetate Drugs 0.000 description 3
- 235000019439 ethyl acetate Nutrition 0.000 description 3
- 238000007327 hydrogenolysis reaction Methods 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 229960004793 sucrose 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
- 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 2
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- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 2
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- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-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
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
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- 239000007868 Raney catalyst Substances 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
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- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 2
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- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 2
- 239000006035 Tryptophane Substances 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 238000005915 ammonolysis reaction Methods 0.000 description 2
- 230000008485 antagonism Effects 0.000 description 2
- 239000003831 antifriction material Substances 0.000 description 2
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- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 2
- 229960003121 arginine Drugs 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 229960004217 benzyl alcohol Drugs 0.000 description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 230000000747 cardiac effect Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
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- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002889 sympathetic effect Effects 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 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
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 210000001364 upper extremity Anatomy 0.000 description 1
- 230000001515 vagal effect Effects 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 239000001993 wax Substances 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)
- Epoxy Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (2)
| 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 |
| SE7611125-1 | 1976-10-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1093096A true CA1093096A (en) | 1981-01-06 |
Family
ID=20329066
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA288,290A Expired CA1093096A (en) | 1976-10-07 | 1977-10-06 | Heart active derivatives of 1-amino-2,3-dihydroxy propane |
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) | CS208731B2 (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 HU HU77HE752A patent/HU177638B/hu unknown
- 1977-10-05 DD DD7700201371A patent/DD132195A5/xx 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 DK DK443177A patent/DK145375C/da active
- 1977-10-06 CS CS776486A patent/CS208731B2/cs unknown
- 1977-10-06 CS CS776486A patent/CS208734B2/cs unknown
- 1977-10-06 LU LU78263A patent/LU78263A1/xx unknown
- 1977-10-06 IE IE2046/77A patent/IE45938B1/en unknown
- 1977-10-06 CS CS776486A patent/CS208733B2/cs unknown
- 1977-10-06 CS CS776486A patent/CS208732B2/cs unknown
- 1977-10-06 SU SU772528198A patent/SU735166A3/ru active
- 1977-10-06 GB GB41699/77A patent/GB1589838A/en not_active Expired
- 1977-10-06 CS CS776486A patent/CS208730B2/cs unknown
- 1977-10-06 FR FR7730156A patent/FR2367054A1/fr active Granted
- 1977-10-06 NO NO773406A patent/NO145436C/no unknown
- 1977-10-07 BE BE181531A patent/BE859474A/xx unknown
- 1977-10-07 CH CH1230577A patent/CH636337A5/de not_active IP Right Cessation
- 1977-10-07 JP JP12133477A patent/JPS5346928A/ja active Pending
-
1978
- 1978-07-28 SU SU782641105A patent/SU959623A3/ru active
- 1978-07-28 SU SU782640402A patent/SU784760A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| CS208733B2 (en) | 1981-09-15 |
| CS208732B2 (en) | 1981-09-15 |
| ATA702177A (de) | 1979-01-15 |
| CS208730B2 (en) | 1981-09-15 |
| HU177638B (en) | 1981-11-28 |
| JPS5346928A (en) | 1978-04-27 |
| CH636337A5 (en) | 1983-05-31 |
| NL7710941A (nl) | 1978-04-11 |
| FR2367054A1 (fr) | 1978-05-05 |
| NO145436C (no) | 1982-03-24 |
| SE7611125L (sv) | 1978-04-08 |
| CS208731B2 (en) | 1981-09-15 |
| AT351509B (de) | 1979-07-25 |
| NZ185318A (en) | 1980-02-21 |
| AU2930077A (en) | 1979-04-12 |
| GB1589838A (en) | 1981-05-20 |
| CS208734B2 (en) | 1981-09-15 |
| SU735166A3 (ru) | 1980-05-15 |
| SU959623A3 (ru) | 1982-09-15 |
| SE416545B (sv) | 1981-01-19 |
| DK145375C (da) | 1983-04-11 |
| DE2743493A1 (de) | 1978-04-13 |
| NO145436B (no) | 1981-12-14 |
| DD132195A5 (de) | 1978-09-06 |
| FR2367054B1 (cs) | 1981-11-06 |
| SU784760A3 (ru) | 1980-11-30 |
| LU78263A1 (cs) | 1978-06-09 |
| IE45938B1 (en) | 1983-01-12 |
| DK443177A (da) | 1978-04-08 |
| FI772936A7 (fi) | 1978-04-08 |
| BE859474A (fr) | 1978-04-07 |
| DK145375B (da) | 1982-11-08 |
| NO773406L (no) | 1978-04-10 |
| AU516727B2 (en) | 1981-06-18 |
| ZA775603B (en) | 1978-06-28 |
| IE45938L (en) | 1978-04-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |