CH584209A5 - 3-amino-2-hydroxypropoxy substd. diazines and pyridines - with beta-adrenergic blocking or stimulating activity - Google Patents
3-amino-2-hydroxypropoxy substd. diazines and pyridines - with beta-adrenergic blocking or stimulating activityInfo
- Publication number
- CH584209A5 CH584209A5 CH244473A CH244473A CH584209A5 CH 584209 A5 CH584209 A5 CH 584209A5 CH 244473 A CH244473 A CH 244473A CH 244473 A CH244473 A CH 244473A CH 584209 A5 CH584209 A5 CH 584209A5
- Authority
- CH
- Switzerland
- Prior art keywords
- lower alkyl
- carbon atoms
- alkyl
- alkoxy
- compounds
- Prior art date
Links
- -1 3-amino-2-hydroxypropoxy Chemical group 0.000 title claims description 281
- 150000003222 pyridines Chemical class 0.000 title description 3
- 230000000903 blocking effect Effects 0.000 title description 2
- 150000004891 diazines Chemical class 0.000 title 1
- 230000004936 stimulating effect Effects 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 176
- 238000000034 method Methods 0.000 claims abstract description 22
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 13
- 238000002360 preparation method Methods 0.000 claims abstract description 10
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 6
- 125000003373 pyrazinyl group Chemical group 0.000 claims abstract description 5
- 125000002098 pyridazinyl group Chemical group 0.000 claims abstract description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 185
- 150000001875 compounds Chemical class 0.000 claims description 57
- 125000003545 alkoxy group Chemical group 0.000 claims description 43
- 125000003342 alkenyl group Chemical group 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 26
- 125000004442 acylamino group Chemical group 0.000 claims description 25
- 150000003254 radicals Chemical class 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical group 0.000 claims description 16
- 125000003282 alkyl amino group Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 10
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000003700 epoxy group Chemical group 0.000 claims description 5
- 125000006177 alkyl benzyl group Chemical group 0.000 claims description 4
- 125000006277 halobenzyl group Chemical group 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical class [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims description 4
- 125000006493 trifluoromethyl benzyl group Chemical group 0.000 claims description 4
- RUIZBQQGWNBRFH-UHFFFAOYSA-N 1-oxidopyrazin-1-ium Chemical class [O-][N+]1=CC=NC=C1 RUIZBQQGWNBRFH-UHFFFAOYSA-N 0.000 claims description 3
- GAJBWMUZVXJIBO-UHFFFAOYSA-N 1-oxidopyridazin-1-ium Chemical class [O-][N+]1=CC=CC=N1 GAJBWMUZVXJIBO-UHFFFAOYSA-N 0.000 claims description 3
- OQZGLXOADHKTDN-UHFFFAOYSA-N 1-oxidopyrimidin-1-ium Chemical class [O-][N+]1=CC=CN=C1 OQZGLXOADHKTDN-UHFFFAOYSA-N 0.000 claims description 3
- 125000006307 alkoxy benzyl group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 2
- 150000003216 pyrazines Chemical class 0.000 abstract description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 3
- 238000009833 condensation Methods 0.000 abstract description 3
- 230000005494 condensation Effects 0.000 abstract description 3
- 150000003230 pyrimidines Chemical class 0.000 abstract description 3
- 230000009471 action Effects 0.000 abstract description 2
- 102000012740 beta Adrenergic Receptors Human genes 0.000 abstract description 2
- 108010079452 beta Adrenergic Receptors Proteins 0.000 abstract description 2
- 230000000297 inotrophic effect Effects 0.000 abstract description 2
- JAQJVXKVDBRECS-UHFFFAOYSA-N Cl.BrC=1N=C(C(=NC1)OCC(CNC(C)C)O)N1CCOCC1 Chemical compound Cl.BrC=1N=C(C(=NC1)OCC(CNC(C)C)O)N1CCOCC1 JAQJVXKVDBRECS-UHFFFAOYSA-N 0.000 abstract 1
- 239000004593 Epoxy Substances 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 239000002876 beta blocker Substances 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 230000000747 cardiac effect Effects 0.000 abstract 1
- 125000005331 diazinyl group Chemical group N1=NC(=CC=C1)* 0.000 abstract 1
- 150000002009 diols Chemical class 0.000 abstract 1
- 230000009249 intrinsic sympathomimetic activity Effects 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 46
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 31
- 125000002947 alkylene group Chemical group 0.000 description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
- 239000011541 reaction mixture Substances 0.000 description 21
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 19
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 19
- 239000007858 starting material Substances 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 238000003756 stirring Methods 0.000 description 15
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- 238000009835 boiling Methods 0.000 description 12
- 229910052938 sodium sulfate Inorganic materials 0.000 description 12
- 235000011152 sodium sulphate Nutrition 0.000 description 12
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 11
- 239000012259 ether extract Substances 0.000 description 11
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 11
- 239000000155 melt Substances 0.000 description 11
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 10
- 229960004592 isopropanol Drugs 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Natural products OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 7
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 230000007935 neutral effect Effects 0.000 description 7
- 239000012312 sodium hydride Substances 0.000 description 7
- 229910000104 sodium hydride Inorganic materials 0.000 description 7
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 6
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 102000005962 receptors Human genes 0.000 description 6
- 108020003175 receptors Proteins 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 235000011181 potassium carbonates Nutrition 0.000 description 5
- MLCNOCRGSBCAGH-UHFFFAOYSA-N 2,3-dichloropyrazine Chemical compound ClC1=NC=CN=C1Cl MLCNOCRGSBCAGH-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- 241000700199 Cavia porcellus Species 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 125000005239 aroylamino group Chemical group 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 125000006626 methoxycarbonylamino group Chemical group 0.000 description 4
- 210000000056 organ Anatomy 0.000 description 4
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000003107 substituted aryl group Chemical group 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 210000003437 trachea Anatomy 0.000 description 4
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 3
- WPQMAEQVHGHGBK-UHFFFAOYSA-N 1-bromo-3-(3-chloropyrazin-2-yl)oxypropan-2-ol Chemical compound BrCC(O)COC1=NC=CN=C1Cl WPQMAEQVHGHGBK-UHFFFAOYSA-N 0.000 description 3
- CJBFQUQKMJGECJ-UHFFFAOYSA-N 2-methylsulfanyl-5-(oxiran-2-ylmethoxy)pyrimidine Chemical compound C1=NC(SC)=NC=C1OCC1OC1 CJBFQUQKMJGECJ-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- 241000282326 Felis catus Species 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Natural products C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
- 208000001871 Tachycardia Diseases 0.000 description 3
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 230000008602 contraction Effects 0.000 description 3
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000006627 ethoxycarbonylamino group Chemical group 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229940039009 isoproterenol Drugs 0.000 description 3
- 230000002107 myocardial effect Effects 0.000 description 3
- 235000006408 oxalic acid Nutrition 0.000 description 3
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- IFKPPSPIASUCKW-UHFFFAOYSA-N (2-hydroxy-3-pyrimidin-2-yloxypropyl) 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC(O)COC1=NC=CC=N1 IFKPPSPIASUCKW-UHFFFAOYSA-N 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
- LXAGZGFAXKNAON-UHFFFAOYSA-N 1-(propan-2-ylamino)-3-pyrimidin-2-yloxypropan-2-ol Chemical compound CC(C)NCC(O)COC1=NC=CC=N1 LXAGZGFAXKNAON-UHFFFAOYSA-N 0.000 description 2
- WSNPMOCQQHUICP-UHFFFAOYSA-N 1-bromo-3-[(5-bromo-2-morpholin-3-yl-1H-pyrazin-2-yl)oxy]propan-2-ol Chemical compound BrC=1N=CC(NC=1)(OCC(CBr)O)C1NCCOC1 WSNPMOCQQHUICP-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- SOOAQIWRVFCPAP-UHFFFAOYSA-N 2-chloro-3-prop-2-enoxypyrazine Chemical compound ClC1=NC=CN=C1OCC=C SOOAQIWRVFCPAP-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- OPLMEXKOTKLLHE-UHFFFAOYSA-N 2-methyl-5-(oxiran-2-ylmethoxy)pyridine Chemical compound C1=NC(C)=CC=C1OCC1OC1 OPLMEXKOTKLLHE-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- WWAOSMWRXUSCOZ-UHFFFAOYSA-N 3-(3-chloropyridin-2-yl)oxypropane-1,2-diol Chemical compound OCC(O)COC1=NC=CC=C1Cl WWAOSMWRXUSCOZ-UHFFFAOYSA-N 0.000 description 2
- OYOQJUBQXIJGFR-UHFFFAOYSA-N 3-chloro-n,n-dimethylpyrazin-2-amine Chemical compound CN(C)C1=NC=CN=C1Cl OYOQJUBQXIJGFR-UHFFFAOYSA-N 0.000 description 2
- VHCWENVIQSXOQV-UHFFFAOYSA-N 3-chloro-n-propan-2-ylpyrazin-2-amine Chemical compound CC(C)NC1=NC=CN=C1Cl VHCWENVIQSXOQV-UHFFFAOYSA-N 0.000 description 2
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 2
- YRDPGBRDUTZTFI-UHFFFAOYSA-N 3-pyrimidin-2-yloxypropane-1,2-diol Chemical compound OCC(O)COC1=NC=CC=N1 YRDPGBRDUTZTFI-UHFFFAOYSA-N 0.000 description 2
- DDTFLTGFVRRMBF-UHFFFAOYSA-N 4-(3-chloropyrazin-2-yl)morpholine Chemical compound ClC1=NC=CN=C1N1CCOCC1 DDTFLTGFVRRMBF-UHFFFAOYSA-N 0.000 description 2
- KBVRMHYXYDCRNR-UHFFFAOYSA-N 4-(3-prop-2-enoxypyrazin-2-yl)morpholine Chemical compound C=CCOC1=NC=CN=C1N1CCOCC1 KBVRMHYXYDCRNR-UHFFFAOYSA-N 0.000 description 2
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- NBOLSLBQJIAERP-UHFFFAOYSA-N 5-(oxiran-2-ylmethoxy)pyrimidine Chemical compound C1OC1COC1=CN=CN=C1 NBOLSLBQJIAERP-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 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 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
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- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
- ISQVBYGGNVVVHB-UHFFFAOYSA-N cyclopentylmethanol Chemical compound OCC1CCCC1 ISQVBYGGNVVVHB-UHFFFAOYSA-N 0.000 description 1
- YOXHCYXIAVIFCZ-UHFFFAOYSA-N cyclopropanol Chemical compound OC1CC1 YOXHCYXIAVIFCZ-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
- DLLJVQNYBYOKGS-UHFFFAOYSA-N ethoxyethane;pentane Chemical compound CCCCC.CCOCC DLLJVQNYBYOKGS-UHFFFAOYSA-N 0.000 description 1
- 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006351 ethylthiomethyl group Chemical group [H]C([H])([H])C([H])([H])SC([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 210000002837 heart atrium Anatomy 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
- 235000019359 magnesium stearate 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
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 1
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- ZIHTVOXSRAROFC-UHFFFAOYSA-N n,n-dimethyl-3-prop-2-enoxypyrazin-2-amine Chemical compound CN(C)C1=NC=CN=C1OCC=C ZIHTVOXSRAROFC-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient 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
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- LTXJLQINBYSQFU-UHFFFAOYSA-N pyrimidin-5-ol Chemical compound OC1=CN=CN=C1 LTXJLQINBYSQFU-UHFFFAOYSA-N 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- RNVYQYLELCKWAN-UHFFFAOYSA-N solketal Chemical compound CC1(C)OCC(CO)O1 RNVYQYLELCKWAN-UHFFFAOYSA-N 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229930002534 steroid glycoside Natural products 0.000 description 1
- 150000008143 steroidal glycosides Chemical class 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000002889 sympathetic effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 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
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 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
- 230000024883 vasodilation Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/69—Two or more oxygen atoms
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
Priority Applications (57)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH244473A CH584209A5 (en) | 1973-02-20 | 1973-02-20 | 3-amino-2-hydroxypropoxy substd. diazines and pyridines - with beta-adrenergic blocking or stimulating activity |
| AR257055A AR207133A1 (es) | 1973-02-20 | 1974-01-01 | Procedimiento para la elaboracion de derivados de 1-piridiloxi 1-pirimidiniloxi y 1-piraziniloxi-2-hidroxi-3-amino-propano |
| AR257058A AR206801A1 (es) | 1973-02-20 | 1974-01-01 | Procedimiento para la elaboracion de derivados del 1-pirid loxi-2-hidroxi-3-amino-propano |
| AR257054A AR208397A1 (es) | 1973-02-20 | 1974-01-01 | Procedimiento para la elaboracion de compuestos de 1-piridiloxi-2-hidroxi-3-amino-propano1-piraziniloxi-2-hidroxi-3-amino-propano y 1-pirimidiniloxi-2-hidroxi-3-amino-propan |
| FI193/74A FI60391C (fi) | 1973-02-20 | 1974-01-23 | Analogifoerfarande foer framstaellning av beta-reseptor-aktiva 1-heterocyklyloxi-3-amino-2-propanolfoereningar |
| SE7401114A SE420834B (sv) | 1973-02-20 | 1974-01-29 | Analogiforfarande for framstellning av beta-receptoraktiva derivat av 2-hydroxi-3-aminopropan |
| IE255/74A IE38839B1 (en) | 1973-02-20 | 1974-02-11 | Pyridazinyl,pyrimidinyl,pyrazinyl and pyridyl compounds and processes for their manufacture |
| CA192,292A CA1027131A (en) | 1973-02-20 | 1974-02-12 | Heterocyclic compounds and processes for their manufacture |
| GB651874A GB1465946A (en) | 1973-02-20 | 1974-02-13 | Pyridazinyl,pyrimidinyl,pyrazinyl and pyridyl compounds and processes for their manufacture |
| NO740486A NO139682C (no) | 1973-02-20 | 1974-02-13 | Analogifremgangsmaate til fremstilling av beta-reseptor-aktive forbindelser |
| IL44202A IL44202A (en) | 1973-02-20 | 1974-02-13 | (3-amino-2-hydroxy-propoxy)-diazines and -pyridine derivatives,their manufacture and pharmaceutical compositions containing them |
| DE19742406930 DE2406930A1 (de) | 1973-02-20 | 1974-02-14 | Neue heterocyclische verbindungen und verfahren zu ihrer herstellung |
| DK80774A DK143501C (da) | 1973-02-20 | 1974-02-15 | Analogifremgangsmaade til fremstilling af beta-receptorblokerende derivater af 2-hydroxy-3-aminopropan eller terapeutisk anvendelige salte deraf |
| SU741995950A SU659089A3 (ru) | 1973-02-20 | 1974-02-18 | Способ получени производных 2-окси-3-аминопропана или их -окисей или солей |
| AU65726/74A AU493478B2 (en) | 1974-02-18 | New heterocyclic compounds and processes for their manufacture | |
| ES423362A ES423362A1 (es) | 1973-02-20 | 1974-02-18 | Procedimiento para la obtencion de derivados de 2-hidroxi-3aminopropano de actividad beta-receptora. |
| FR7405391A FR2218101B1 (cs) | 1973-02-20 | 1974-02-18 | |
| LU69415A LU69415A1 (cs) | 1973-02-20 | 1974-02-18 | |
| DD176616A DD110041A5 (cs) | 1973-02-20 | 1974-02-18 | |
| MC1097A MC1013A1 (fr) | 1973-02-20 | 1974-02-19 | Nouveaux composés hétérocycliques et leurs procédés de préparation |
| PL1974189131A PL98964B1 (pl) | 1973-02-20 | 1974-02-19 | Sposob wytwarzania nowych pochodnych 1-pirazynyloksy-2-hydroksy-3-aminopropanu |
| PL1974184283A PL100171B1 (pl) | 1973-02-20 | 1974-02-19 | Sposob wytwarzania nowych pochodnych 1-pirazynyloksy-2-hydroksy-3-aminopropanu |
| MX700274U MX5291E (es) | 1973-02-20 | 1974-02-19 | Procedimiento para obtener derivados heterociclicos de 2-hidroxi-3-aminopropano |
| PL1974203732A PL101376B1 (pl) | 1973-02-20 | 1974-02-19 | Sposob wytwarzania nowych pochodnych 2-hydroksy-3-aminopropanu |
| BE141130A BE811274A (fr) | 1973-02-20 | 1974-02-19 | Nouveaux composes heterocycliques et leurs procedes de preparation |
| PL1974189132A PL98967B1 (pl) | 1973-02-20 | 1974-02-19 | Sposob wytwarzania nowych pochodnych 1-pirymidynyloksy-2-hydroksy-3-aminopropanu |
| PL1974184285A PL100172B1 (pl) | 1973-02-20 | 1974-02-19 | Sposob wytwarzania nowych pochodnych 2-hydroksy-3-aminopropanu |
| YU43674A YU37150B (en) | 1973-02-20 | 1974-02-19 | Process for preparing new pyridyloxy-, pyrazinyloxy-, pyrimidinyloxy- and pyridazinyloxy-2-hydroxy-3-aminopropanes |
| PL1974168938A PL94250B1 (cs) | 1973-02-20 | 1974-02-19 | |
| ZA00741070A ZA741070B (en) | 1973-02-20 | 1974-02-19 | New heterocyclic compounds and processes for their manufacture |
| AT133074A AT335455B (de) | 1973-02-20 | 1974-02-19 | Verfahren zur herstellung von neuen heterocyclischen verbindungen |
| HU74CI1447A HU173821B (hu) | 1973-02-20 | 1974-02-19 | Sposob poluchenija novykh proizvodnykh 2 - gidroksi - 3 - amino - propana |
| PL1974184284A PL100314B1 (pl) | 1973-02-20 | 1974-02-19 | Sposob wytwarzania nowych pochodnych 1-pirydyloksy-2-hydroksy-3-aminopropanu |
| NL7402332A NL7402332A (en) | 1973-02-20 | 1974-02-20 | 3-amino-2-hydroxypropoxy substd. diazines and pyridines |
| CS741252A CS203970B2 (en) | 1973-02-20 | 1974-02-20 | Method of producing novel heterocyclyl-oxy-hydroxy-amino-propanes |
| AR252438A AR214612A1 (es) | 1973-02-20 | 1974-02-20 | Procedimiento para preparar nuevos derivados de 1-piridiloxi-,1-piraziniloxi-,1-pirodaziniloxi o 1-pirimidiniloxi-2-hidroxi-3-amino-propano |
| AR257057A AR203878A1 (es) | 1973-02-20 | 1974-12-23 | Procedimiento para la elaboracion de compuestos del 1-piraziniloxi 2-hidroxi-3-aminopropano |
| SU7502137664A SU577978A3 (ru) | 1973-02-20 | 1975-05-27 | Способ получени производных 1пиразинил-окси-2-окси-3-аминопропана или их солей |
| SU752141281A SU593657A3 (ru) | 1973-02-20 | 1975-06-06 | Способ получени производных 1-пиридилокси-2-окси-3-аминопропана или их солей |
| AT948475A AT336617B (de) | 1973-02-20 | 1975-12-15 | Verfahren zur herstellung von neuen heterocyclischen verbindungen |
| AT948675A AT336628B (de) | 1973-02-20 | 1975-12-15 | Verfahren zur herstellung von beta-rezeptoren-aktiven derivaten des 2-hydroxy-3-aminopropan deren n-oxiden, optisch aktiven formen und isomeren und deren saureadditionssalzen |
| AT948975A AT338787B (de) | 1973-02-20 | 1975-12-15 | Verfahren zur herstellung von neuen heterocyclischen verbindungen |
| AT948875A AT336018B (de) | 1973-02-20 | 1975-12-15 | Verfahren zur herstellung von neuen heterocyclischen verbindungen |
| AT948775A AT336618B (de) | 1973-02-20 | 1975-12-15 | Verfahren zur herstellung von neuen heterocyclischen verbindungen |
| AR264155A AR208043A1 (es) | 1973-02-20 | 1976-01-01 | Procedimiento para la elaboracion de derivados de 1-piridiloxi 1-pirimidiniloxi y 1-piraziniloxi-2-hidroxi-3-amino propano |
| ES76446081A ES446081A1 (es) | 1973-02-20 | 1976-03-16 | Procedimiento para la obtencion de derivados del 2-hidroxi-3-aminopropano de actividad beta-receptora. |
| ES76446082A ES446082A1 (es) | 1973-02-20 | 1976-03-16 | Procedimiento para la obtencion de derivados de 1-pirazini- loxi-2-hidroxi-3-aminopropano. |
| ES446083A ES446083A1 (es) | 1973-02-20 | 1976-03-16 | Procedimiento para la obtencion de derivados del 2-hidroxi-3-aminopropano de actividad beta-receptora. |
| US05/757,529 US4115575A (en) | 1973-02-20 | 1977-01-07 | 2-(3-Amino-2-hydroxy-propoxy)-pyrazines |
| US05/883,434 US4195090A (en) | 1973-02-20 | 1978-03-03 | 2-(3-Amino-2-hydroxy-propoxy)pyridine derivatives and pharmaceutical compositions therewith |
| YU156980A YU156980A (en) | 1973-02-20 | 1980-06-12 | Process for preparing new 1-pyridyloxy-2-hydroxy-3-aminopropane derivatives |
| YU156880A YU156880A (en) | 1973-02-20 | 1980-06-12 | Process for preparing new heterocyclyloxy-2-hydroxy-3-aminopropanes |
| YU156780A YU156780A (en) | 1973-02-20 | 1980-06-12 | Process for preparing new heterocyclyloxy-2-hydroxy-3-aminopropanes |
| DK364180A DK364180A (da) | 1973-02-20 | 1980-08-25 | Analogifremgangsmaade til fremstilling af betareceptorstimulerende derivater af 2-hydroxy-3-amino-propan |
| US06/266,546 US4410530A (en) | 1973-02-20 | 1981-05-22 | 2-(3-Amino-2-hydroxy-propoxy)-mono-and diazines |
| JP57132301A JPS5823666A (ja) | 1973-02-20 | 1982-07-30 | 新規ピリミジン化合物の製法 |
| JP57132300A JPS603391B2 (ja) | 1973-02-20 | 1982-07-30 | 新規ピリミジン化合物の製法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH244473A CH584209A5 (en) | 1973-02-20 | 1973-02-20 | 3-amino-2-hydroxypropoxy substd. diazines and pyridines - with beta-adrenergic blocking or stimulating activity |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH584209A5 true CH584209A5 (en) | 1977-01-31 |
Family
ID=4233957
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH244473A CH584209A5 (en) | 1973-02-20 | 1973-02-20 | 3-amino-2-hydroxypropoxy substd. diazines and pyridines - with beta-adrenergic blocking or stimulating activity |
Country Status (9)
| Country | Link |
|---|---|
| JP (2) | JPS5823666A (cs) |
| CH (1) | CH584209A5 (cs) |
| FI (1) | FI60391C (cs) |
| HU (1) | HU173821B (cs) |
| MC (1) | MC1013A1 (cs) |
| NO (1) | NO139682C (cs) |
| PL (7) | PL100171B1 (cs) |
| SU (3) | SU659089A3 (cs) |
| ZA (1) | ZA741070B (cs) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4517188A (en) * | 1983-05-09 | 1985-05-14 | Mead Johnson & Company | 1-Pyrimidinyloxy-3-hetaryl-alkylamino-2-propanols |
| DE4421495A1 (de) * | 1994-06-20 | 1995-12-21 | Merck Patent Gmbh | Heterocyclyloxy-benzoylguanidine |
| DE4426346A1 (de) * | 1994-07-25 | 1996-02-01 | Basf Ag | Herbizide Pyrazinderivate |
-
1973
- 1973-02-20 CH CH244473A patent/CH584209A5/de not_active IP Right Cessation
-
1974
- 1974-01-23 FI FI193/74A patent/FI60391C/fi active
- 1974-02-13 NO NO740486A patent/NO139682C/no unknown
- 1974-02-18 SU SU741995950A patent/SU659089A3/ru active
- 1974-02-19 ZA ZA00741070A patent/ZA741070B/xx unknown
- 1974-02-19 HU HU74CI1447A patent/HU173821B/hu unknown
- 1974-02-19 PL PL1974184283A patent/PL100171B1/pl unknown
- 1974-02-19 PL PL1974189131A patent/PL98964B1/pl unknown
- 1974-02-19 PL PL1974189132A patent/PL98967B1/pl unknown
- 1974-02-19 PL PL1974203732A patent/PL101376B1/pl unknown
- 1974-02-19 MC MC1097A patent/MC1013A1/xx unknown
- 1974-02-19 PL PL1974184285A patent/PL100172B1/pl unknown
- 1974-02-19 PL PL1974184284A patent/PL100314B1/pl unknown
- 1974-02-19 PL PL1974168938A patent/PL94250B1/pl unknown
-
1975
- 1975-05-27 SU SU7502137664A patent/SU577978A3/ru active
- 1975-06-06 SU SU752141281A patent/SU593657A3/ru active
-
1982
- 1982-07-30 JP JP57132301A patent/JPS5823666A/ja active Pending
- 1982-07-30 JP JP57132300A patent/JPS603391B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FI60391C (fi) | 1982-01-11 |
| FI60391B (fi) | 1981-09-30 |
| SU659089A3 (ru) | 1979-04-25 |
| PL98964B1 (pl) | 1978-06-30 |
| PL100172B1 (pl) | 1978-09-30 |
| NO139682B (no) | 1979-01-15 |
| NO740486L (no) | 1974-08-21 |
| ZA741070B (en) | 1975-01-29 |
| JPS5823675A (ja) | 1983-02-12 |
| PL94250B1 (cs) | 1977-07-30 |
| SU577978A3 (ru) | 1977-10-25 |
| JPS603391B2 (ja) | 1985-01-28 |
| SU593657A3 (ru) | 1978-02-15 |
| NO139682C (no) | 1979-04-25 |
| PL101376B1 (pl) | 1978-12-30 |
| PL100314B1 (pl) | 1978-09-30 |
| PL98967B1 (pl) | 1978-06-30 |
| MC1013A1 (fr) | 1974-10-18 |
| JPS5823666A (ja) | 1983-02-12 |
| HU173821B (hu) | 1979-08-28 |
| PL100171B1 (pl) | 1978-09-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |