PL86937B1 - 1-(2'-cyano-phenoxy)-2-hydroxy-3-ethylamino-propane and salts thereof[us3732277a] - Google Patents
1-(2'-cyano-phenoxy)-2-hydroxy-3-ethylamino-propane and salts thereof[us3732277a] Download PDFInfo
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- PL86937B1 PL86937B1 PL1970174661A PL17466170A PL86937B1 PL 86937 B1 PL86937 B1 PL 86937B1 PL 1970174661 A PL1970174661 A PL 1970174661A PL 17466170 A PL17466170 A PL 17466170A PL 86937 B1 PL86937 B1 PL 86937B1
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- Prior art keywords
- hydroxy
- phenoxy
- salts
- us3732277a
- ethylamino
- Prior art date
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- 150000003839 salts Chemical class 0.000 title description 3
- MAXGKGLXEAPYGY-UHFFFAOYSA-N 2-[3-(ethylamino)-2-hydroxypropoxy]benzonitrile Chemical compound CCNCC(O)COC1=CC=CC=C1C#N MAXGKGLXEAPYGY-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 description 12
- 239000013543 active substance Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 230000002035 prolonged effect Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 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 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 3
- -1 disintegrating Substances 0.000 description 3
- 239000008298 dragée Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000007903 gelatin capsule Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000013355 food flavoring agent Nutrition 0.000 description 2
- 235000003599 food sweetener Nutrition 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000003765 sweetening agent Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- XUJHKPSBHDQIOD-UHFFFAOYSA-N (2-bromo-7,7-dimethyl-3-oxo-4-bicyclo[2.2.1]heptanyl)methanesulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)C(Br)C1C2(C)C XUJHKPSBHDQIOD-UHFFFAOYSA-N 0.000 description 1
- HFOAMOYLGQYKAQ-UHFFFAOYSA-N 1-(ethylamino)-3-phenoxypropan-2-ol Chemical compound CCNCC(O)COC1=CC=CC=C1 HFOAMOYLGQYKAQ-UHFFFAOYSA-N 0.000 description 1
- KMGUEILFFWDGFV-UHFFFAOYSA-N 2-benzoyl-2-benzoyloxy-3-hydroxybutanedioic acid Chemical compound C=1C=CC=CC=1C(=O)C(C(C(O)=O)O)(C(O)=O)OC(=O)C1=CC=CC=C1 KMGUEILFFWDGFV-UHFFFAOYSA-N 0.000 description 1
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- YIUIVFFUEVPRIU-UHFFFAOYSA-N 8-chlorotheophylline Chemical compound O=C1N(C)C(=O)N(C)C2=NC(Cl)=N[C]21 YIUIVFFUEVPRIU-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical group OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- DFJAVDXYHCJASO-UHFFFAOYSA-N Cl.C(#N)C1=C(OCC(CNCC)O)C=CC=C1 Chemical compound Cl.C(#N)C1=C(OCC(CNCC)O)C=CC=C1 DFJAVDXYHCJASO-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- RGBZRGUHFLARHS-UHFFFAOYSA-N NC1=C(OCC(CNCC)O)C=CC=C1 Chemical compound NC1=C(OCC(CNCC)O)C=CC=C1 RGBZRGUHFLARHS-UHFFFAOYSA-N 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical class C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229920001800 Shellac Polymers 0.000 description 1
- 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 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 208000001871 Tachycardia Diseases 0.000 description 1
- 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 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000002160 alpha blocker Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 229940096529 carboxypolymethylene Drugs 0.000 description 1
- 229940097217 cardiac glycoside Drugs 0.000 description 1
- 239000002368 cardiac glycoside Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000003218 coronary vasodilator agent Substances 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 229940109275 cyclamate Drugs 0.000 description 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229960005150 glycerol Drugs 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical class [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 229930002534 steroid glycoside Natural products 0.000 description 1
- 150000008143 steroidal glycosides Chemical class 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 210000002820 sympathetic nervous system Anatomy 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
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- 239000003826 tablet Substances 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/275—Nitriles; Isonitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/53—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and hydroxy groups bound to the carbon skeleton
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
Przedmiotem wynalazku jest sposób wytwarzania l72-cyjanofenoksy/-2-hydroksy-3-etyloaminopropanu o wzorze 1. Jest to zwiazek nowy i moze znalezc zastosowanie jako srodek leczniczy.Wedlug wynalazku nowy zwiazek otrzymuje sie przez dwuazowanie zwiazku o wzorze 2, w którym A oznacza grupe aminowa i nastepnie ogrzewanie otrzymanej soli dwuazoniowej z cyjankiem miedziawym.Zwiazki o wzorze 2 zawieraja gotowa juz strukture 1-fenoksy-2-hydroksy-3-etyloaminopropanu i korzys¬ tnie wytwarza sie przez reakcje odpowiednio podstawionego fenolu albo fenolanu z epichlorohydryna w alkali¬ cznym roztworze i reakcje otrzymanego podstawionego 1-fenoksy-2,3-epoksypropanu z etyloamina. 1-/2-Amino- fenoksy/-2-hydroksy-3-etyloaminopropan, który poddaje sie dwuazowaniu i reakcji z cyjankiem miedziawym, wytwarza sie korzystnie przez redukcje 1-/2-nitrofenoksy/-2-hydroksy-3-etyloaminopropanu, otrzymywanego zetyloaminy i 1-/2-nitrofenoksy/-2,3-epoksypropanu, który z kolei otrzymuje sie w reakcji o-nitrofenolu z epi¬ chlorohydryna w alkalicznym roztworze, ' Wytworzony sposobem wedlug wynalazku zwiazek posiada w ugrupowaniu -CHOH- asymetryczny atom wegla, wystepuje wiec zarówno w formie racematu, jak równiez optycznie czynnych antypodów. Optycznie czynne zwiazki mozna otrzymac albo wychodzac z optycznie czynnych produktów wyjsciowych, albo rozdzie¬ lajac otrzymany racemat na antypody optyczne w znany sposób, na przyklad za pomoca kwasu dwubenzoilowi- nowego lub bromokamforosulfonowego.Wytworzony sposobem wedlug wynalazku zwiazek mozna przeprowadzac w znany sposób w fizjologicznie tolerowane sole addycyjne z kwasami. Do tego celu nadaje sie, na przyklad kwas solny, bromowodorowy, siarkowy, metanosulfonowy, maleinowy, octowy, szczawiowy, mlekowy, winowy albo 8-chloroteofilina. r Wytworzony sposobem wedlug wynalazku zwiazek o wzorze 1, wzglednie jego fizjologicznie tolerowane sole addycyjne z kwasami, posiadaja cenne wlasciwosci terapeutyczne, szczególnie j8-adrenolityczne i mozna je podawac leczniczo lub profilaktycznie w schorzeniach naczyn wiencowych serca, w leczeniu arytmii serca, zwlaszcza czestoskurczu. Zwiazek ten wykazal w badaniach na swinkach morskich znacznie skuteczniejsze dzialanie zwalniajace akcje serca i antagonistyczne w stosunku do aludryny (aludryna - 1-/3,4-dwuhydroksyfe-2 86937 nylo/*1-hydroksy-2-izopropyloaminoetan) oraz mniejsza toksycznosc niz znany 1-/1-naftoksy/-2-hydroksy-3-izo- propyloaminopropan. « Jednorazowa dawka otrzymanego sposobem wedlug wynalazku zwiazku wynosi 1-150 mg, korzystnie -50 mg (doustnie), wzglednie 1-20 mg (pozajelitowo).Z otrzymanego'sposobem wedlug wynalazku zwiazku^ mozna sporzadzac zwykle stosowane postacie galenowe** takie jak roztwory, emulsje, tabletki, drazetki albo postacie o przedluzonym dzialaniu, w znany sposób przy uzyciu-srodków pomocniczych, nosników, srodków rozsadzajacych, wiazacych, powlekajacych albo poslizgowych, smakowych, slodzacych, srodków do osiagniecia przedluzonego dzialania albo ulatwiajacych rozpuszczanie. < Nowy zwiazek mozna równiez stosowac w polaczeniu z innymi, farmakodynamicznie czynnymi substan¬ cjami, takimi, jak substancje rozszerzajace naczynia wiencowe, pobudzajace uklad wspólczulny, glikozydy' nasercowe albo srodki uspokajajace.Tabletki mozna na przyklad otrzymywac przez mieszanie substancji czynnej ze znanymi substancjami pomocniczymi, na przyklad obojetnymi rozcienczalnikami, takimi jak weglan wapniowy, fosforan wapniowy albo cukier mlekowy, srodkami rozsadzajacymi, takimi jak skrobia albo zelatyna, srodkami poslizgowymi, takimi jak stearynian magnezowy albo talk i/lub srodkami do uzyskania przedluzonego dzialania, takimi jak karboksypolimetylen, karboksymetyloceluloza, ftalan acetylocelulozy albo octan poliwinylu.Tabletki moga równiez skladac sie z wielu warstw. Drazetki mozna otrzymywac odpowiednio przez powlekanie, otrzymanych .analogicznie do tabletek, rdzeni w znany sposób przy uzyciu srodków stosowanych zwykle do drazowania, takich jak kolidon, szelak, guma arabska, talk, dwutlenek albo cukier. Dla uzyskania efektu przedluzonego dzialania albo unikniecia niezgodnosci, rdzen moze skladac sie z kilku warstw. Podobnie, dla uzyskania przedluzonego dzialania powloki drazetek moga równiez zawierac kilka warstw, przy czym mozna stosowac wymienione przy tabletkach substancje pomocnicze.Dla wytwarzania miekkich kapsulek zelatynowych albo podobnych kapsulek zamykanych substancje czynna mozna mieszac z olejem roslinnym. Twarde kapsulki zelatynowe moga zawierac granulat substancji czynnej w polaczeniu ze stalymi sproszkowanymi nosnikami, takimi jak laktoza, sacharoza, sorbit, mannit, skrobia, na przyklad skrobia ziemniaczana, kukurydziana albo amylopektyha, pochodne celulozy albo*zelatyna.Syropy substancji czynnej lub tez kombinacji substancji czynnych moga zawierac jeszcze dodatkowo srodek slodzacy, taki jak sacharyna, cyklaminian, gliceryna albo cukier, jak równiez srodek poprawiajacy smak, na przyklad srodki zapachowe, jak wanilina albo ekstrakt pomaranczowy. Oprócz tego moga zawierac jeszcze, srodki ulatwiajace powstawanie zawiesiny, zagestniki, takie jak sól sodowa karboksymetylocelulozy, srodki zwilzajace, na przyklad produkty kondensacji alkoholi tluszczowych z tlenkiem etylenu, albo srodki konserwu¬ jace, jak 0-hydroksybenzoesany.Roztwory injekcyjne przygotowuje sie w znany sposób, na przyklad z dodatkiem srodków konserwuja¬ cych, takich jak 0-hydVoksybehzoesany albo stabilizatorów, takich jak kompleksony i rozlewa do fiolek injekcyjnych lub ampulek. Roztwory moga'zawierac równiez stabilizator i/lub srodek buforujacy.Czopki mozna przygotowywac przez zmieszanie substancji czynnej wzglednie kombinacji substancji czynnych ze zwyklymi nosnikami, jak tluszcze obojetne albo glikol polietylenowy, wzglednie jego pochodne.Mozna równiez wytwarzac doodbytniczo kapsulki zelatynowe zawierajace aktywna substancje zmieszana z olejem roslinnym lub parafinowym.Nastepujacy przyklad objasnia blizej spobów wedlug wynalazku, nie stanowiac jego ograniczenia.Przyklad. Chlorowodorek 1-/2-cyjanofenoksy/-2-hydroksy-3-etyloaminopropanu a) 2,2 g (0,01 mola) 1-/2-aminofenoksy/-2-hydroksy-3-etyloaminopropanu rozpuszcza sie w mieszaninie 6 ml stezonego kwasu solnego i 20 ml wody. Do tego roztworu wkrapla sie powoli, mieszajac 1,4 g (0,02 mola) NaN02 rozpuszczonego w 5 ml wody, utrzymujac temperature 0-5°. b) mieszanine 5 g (0,02 mola) CuS04* 5H20, 5,8 g (0,09. mola) KCN i 30 ml wody ogrzewa sie, mieszajac do temperatury 75°C. Roztwór dwuazoniowy a) wkrapla sie do goracego Roztworu cyjanku miedziawego b). Po zakonczeniu dodawania, miesza sie jeszcze wciagu 30 minut w temperaturze 75°C, alkalizuje wodorotlenkiem sodowym i ekstrahuje chloroformem. Nierozpuszczalne skladniki odsacza sie. Polaczone warstwy chlorofor¬ mowe przemywa sie woda, suszy siarczanem magnezowym i zateza. Pozostalosc rozpuszcza sie w aceton itrylu i zakwasza alkoholowym roztworem chlorowodoru. Po oziebieniu wytracaja sie krysztaly, które identyfikuje sie na drodze chromatografii cienkowarstwowej i za pomoca temperatury topnienia jako produkt uboczny. Czysty produkt otrzymuje sie przez zadanie lugów macierzystych eterem i przekrystalizowanie wytraconych krysztalów z alkoholu z dodatkiem eteru. Temperatura topnienia wynosi 129-132°C.86937 3 PL PL PL PL PL PL PL PL
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1940566A DE1940566C3 (de) | 1969-08-08 | 1969-08-08 | 1- (2-Nitrilophenoxy)-2-hydroxy-3äthylaminopropan, Verfahren zu dessen Herstellung und dieses enthaltende Arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL86937B1 true PL86937B1 (en) | 1976-06-30 |
Family
ID=5742361
Family Applications (8)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1970174660A PL84519B1 (en) | 1969-08-08 | 1970-08-07 | 1-(2'-cyano-phenoxy)-2-hydroxy-3-ethylamino-propane and salts thereof[us3732277a] |
| PL1970174661A PL86937B1 (en) | 1969-08-08 | 1970-08-07 | 1-(2'-cyano-phenoxy)-2-hydroxy-3-ethylamino-propane and salts thereof[us3732277a] |
| PL1970174658A PL84398B1 (en) | 1969-08-08 | 1970-08-07 | 1-(2'-cyano-phenoxy)-2-hydroxy-3-ethylamino-propane and salts thereof[us3732277a] |
| PL1970174657A PL84339B1 (en) | 1969-08-08 | 1970-08-07 | 1-(2'-cyano-phenoxy)-2-hydroxy-3-ethylamino-propane and salts thereof[us3732277a] |
| PL1970174659A PL84520B1 (en) | 1969-08-08 | 1970-08-07 | 1-(2'-cyano-phenoxy)-2-hydroxy-3-ethylamino-propane and salts thereof[us3732277a] |
| PL1970174662A PL84357B1 (en) | 1969-08-08 | 1970-08-07 | 1-(2'-cyano-phenoxy)-2-hydroxy-3-ethylamino-propane and salts thereof[us3732277a] |
| PL1970174656A PL84341B1 (en) | 1969-08-08 | 1970-08-07 | 1-(2'-cyano-phenoxy)-2-hydroxy-3-ethylamino-propane and salts thereof[us3732277a] |
| PL1970142704A PL80550B1 (en) | 1969-08-08 | 1970-08-07 | 1-(2'-cyano-phenoxy)-2-hydroxy-3-ethylamino-propane and salts thereof[us3732277a] |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1970174660A PL84519B1 (en) | 1969-08-08 | 1970-08-07 | 1-(2'-cyano-phenoxy)-2-hydroxy-3-ethylamino-propane and salts thereof[us3732277a] |
Family Applications After (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1970174658A PL84398B1 (en) | 1969-08-08 | 1970-08-07 | 1-(2'-cyano-phenoxy)-2-hydroxy-3-ethylamino-propane and salts thereof[us3732277a] |
| PL1970174657A PL84339B1 (en) | 1969-08-08 | 1970-08-07 | 1-(2'-cyano-phenoxy)-2-hydroxy-3-ethylamino-propane and salts thereof[us3732277a] |
| PL1970174659A PL84520B1 (en) | 1969-08-08 | 1970-08-07 | 1-(2'-cyano-phenoxy)-2-hydroxy-3-ethylamino-propane and salts thereof[us3732277a] |
| PL1970174662A PL84357B1 (en) | 1969-08-08 | 1970-08-07 | 1-(2'-cyano-phenoxy)-2-hydroxy-3-ethylamino-propane and salts thereof[us3732277a] |
| PL1970174656A PL84341B1 (en) | 1969-08-08 | 1970-08-07 | 1-(2'-cyano-phenoxy)-2-hydroxy-3-ethylamino-propane and salts thereof[us3732277a] |
| PL1970142704A PL80550B1 (en) | 1969-08-08 | 1970-08-07 | 1-(2'-cyano-phenoxy)-2-hydroxy-3-ethylamino-propane and salts thereof[us3732277a] |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3732277A (pl) |
| AT (9) | AT303013B (pl) |
| BE (1) | BE754604A (pl) |
| BG (8) | BG16739A3 (pl) |
| CH (1) | CH546223A (pl) |
| CS (8) | CS166734B2 (pl) |
| DE (1) | DE1940566C3 (pl) |
| DK (1) | DK125639B (pl) |
| ES (8) | ES382497A1 (pl) |
| FR (1) | FR2068479B1 (pl) |
| NL (1) | NL171702C (pl) |
| PL (8) | PL84519B1 (pl) |
| RO (8) | RO60083A (pl) |
| SE (1) | SE375303B (pl) |
| SU (1) | SU386506A3 (pl) |
| YU (1) | YU34515B (pl) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT323132B (de) * | 1935-11-15 | 1975-06-25 | Boehringer Sohn Ingelheim | Verfahren zur herstellung von neuen racemischen oder optisch aktiven n,n'-bis-(3-subst.phenoxy-2-hydroxy-1-propyl)-alpha,omega-diaminoalkanen sowie deren saureadditionssalzen |
| GB1231783A (en) * | 1967-05-16 | 1971-05-12 | May & Baker Ltd | Benzene derivatives |
| GB1415505A (en) * | 1972-06-01 | 1975-11-26 | Ici Ltd | Alkanolamine derivatives |
| US4171374A (en) * | 1972-12-15 | 1979-10-16 | Imperial Chemical Industries Limited | Alkanolamine derivatives |
| GB1455116A (en) * | 1972-12-15 | 1976-11-10 | Ici Ltd | Pharmaceutical compositions |
| US4167581A (en) * | 1972-12-15 | 1979-09-11 | Imperial Chemical Industries Limited | Alkanolamine derivatives and pharmaceutical compositions and uses thereof |
| US4083992A (en) * | 1972-12-15 | 1978-04-11 | Imperial Chemical Industries Limited | Alkanolamine derivatives |
| US4131685A (en) * | 1972-12-15 | 1978-12-26 | Imperial Chemical Industries Limited | Pharmaceutical compositions and uses of alkanolamine derivatives |
| GB1509527A (en) * | 1974-06-05 | 1978-05-04 | Ici Ltd | 1-(aryl-or heteroaryl)oxy-3-(substituted-amino)propan-2-ol derivatives processes for their manufacture and pharmaceutical compositions containing them |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL144926B (nl) * | 1963-08-26 | 1975-02-17 | Boehringer Sohn Ingelheim | Werkwijze ter bereiding van een beta-adrenolytisch werkzaam 1-(cyaanfenoxy)-2-hydroxy-3-isopropylaminopropaan en zouten daarvan. |
-
0
- BE BE754604D patent/BE754604A/xx not_active IP Right Cessation
-
1969
- 1969-08-08 DE DE1940566A patent/DE1940566C3/de not_active Expired
-
1970
- 1970-07-30 SU SU701469623D patent/SU386506A3/ru active
- 1970-08-03 US US00060749A patent/US3732277A/en not_active Expired - Lifetime
- 1970-08-04 CS CS703685A patent/CS166734B2/cs unknown
- 1970-08-04 CS CS3686*[A patent/CS166735B2/cs unknown
- 1970-08-04 CS CS3688*[A patent/CS166737B2/cs unknown
- 1970-08-04 CS CS5440A patent/CS166731B2/cs unknown
- 1970-08-04 CS CS3683*[A patent/CS166732B2/cs unknown
- 1970-08-04 CS CS3687*[A patent/CS166736B2/cs unknown
- 1970-08-04 CS CS3689*[A patent/CS166738B2/cs unknown
- 1970-08-04 CS CS3684*[A patent/CS166733B2/cs unknown
- 1970-08-05 BG BG18257A patent/BG16739A3/xx unknown
- 1970-08-05 CH CH1180070A patent/CH546223A/xx not_active IP Right Cessation
- 1970-08-06 RO RO69112A patent/RO60083A/ro unknown
- 1970-08-06 RO RO69108A patent/RO60644A/ro unknown
- 1970-08-06 SE SE7010830A patent/SE375303B/xx unknown
- 1970-08-06 RO RO69110A patent/RO60746A/ro unknown
- 1970-08-06 RO RO69109A patent/RO60645A/ro unknown
- 1970-08-06 RO RO64160A patent/RO55805A/ro unknown
- 1970-08-06 RO RO69115A patent/RO61039A/ro unknown
- 1970-08-06 RO RO69111A patent/RO60082A/ro unknown
- 1970-08-06 ES ES382497A patent/ES382497A1/es not_active Expired
- 1970-08-06 YU YU2007/70A patent/YU34515B/xx unknown
- 1970-08-06 RO RO69113A patent/RO60084A/ro unknown
- 1970-08-07 BG BG18258A patent/BG17762A3/xx unknown
- 1970-08-07 PL PL1970174660A patent/PL84519B1/pl unknown
- 1970-08-07 DK DK407670AA patent/DK125639B/da not_active IP Right Cessation
- 1970-08-07 PL PL1970174661A patent/PL86937B1/pl unknown
- 1970-08-07 PL PL1970174658A patent/PL84398B1/pl unknown
- 1970-08-07 BG BG18256A patent/BG18179A3/xx unknown
- 1970-08-07 BG BG18253A patent/BG17759A3/xx unknown
- 1970-08-07 AT AT1108071A patent/AT303013B/de not_active IP Right Cessation
- 1970-08-07 AT AT1107671A patent/AT302996B/de not_active IP Right Cessation
- 1970-08-07 PL PL1970174657A patent/PL84339B1/pl unknown
- 1970-08-07 AT AT1108171A patent/AT303014B/de not_active IP Right Cessation
- 1970-08-07 PL PL1970174659A patent/PL84520B1/pl unknown
- 1970-08-07 PL PL1970174662A patent/PL84357B1/pl unknown
- 1970-08-07 BG BG18255A patent/BG17761A3/xx unknown
- 1970-08-07 FR FR7029317A patent/FR2068479B1/fr not_active Expired
- 1970-08-07 BG BG15431A patent/BG18178A3/xx unknown
- 1970-08-07 AT AT723670A patent/AT303006B/de not_active IP Right Cessation
- 1970-08-07 BG BG18259A patent/BG17955A3/xx unknown
- 1970-08-07 AT AT1107771A patent/AT303010B/de not_active IP Right Cessation
- 1970-08-07 AT AT1107971A patent/AT303012B/de not_active IP Right Cessation
- 1970-08-07 AT AT1107471A patent/AT303008B/de not_active IP Right Cessation
- 1970-08-07 PL PL1970174656A patent/PL84341B1/pl unknown
- 1970-08-07 NL NLAANVRAGE7011735,A patent/NL171702C/xx not_active IP Right Cessation
- 1970-08-07 AT AT1107571A patent/AT303009B/de not_active IP Right Cessation
- 1970-08-07 AT AT1107871A patent/AT303011B/de not_active IP Right Cessation
- 1970-08-07 BG BG18254A patent/BG17760A3/xx unknown
- 1970-08-07 PL PL1970142704A patent/PL80550B1/pl unknown
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1971
- 1971-03-04 ES ES388884A patent/ES388884A1/es not_active Expired
- 1971-03-04 ES ES388881A patent/ES388881A1/es not_active Expired
- 1971-03-04 ES ES388885A patent/ES388885A1/es not_active Expired
- 1971-03-04 ES ES388880A patent/ES388880A1/es not_active Expired
- 1971-03-04 ES ES388883A patent/ES388883A1/es not_active Expired
- 1971-03-04 ES ES388882A patent/ES388882A1/es not_active Expired
- 1971-03-04 ES ES388879A patent/ES388879A1/es not_active Expired
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