PL84398B1 - 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
- Publication number
- PL84398B1 PL84398B1 PL1970174658A PL17465870A PL84398B1 PL 84398 B1 PL84398 B1 PL 84398B1 PL 1970174658 A PL1970174658 A PL 1970174658A PL 17465870 A PL17465870 A PL 17465870A PL 84398 B1 PL84398 B1 PL 84398B1
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- Poland
- Prior art keywords
- hydroxy
- formula
- cyanophenoxy
- salts
- agents
- Prior art date
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- 150000003839 salts Chemical class 0.000 title claims description 8
- MAXGKGLXEAPYGY-UHFFFAOYSA-N 2-[3-(ethylamino)-2-hydroxypropoxy]benzonitrile Chemical compound CCNCC(O)COC1=CC=CC=C1C#N MAXGKGLXEAPYGY-UHFFFAOYSA-N 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 239000013543 active substance Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000002035 prolonged effect Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000007903 gelatin capsule 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
- 229920002261 Corn starch Polymers 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
- 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
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
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- 239000008120 corn starch 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
- 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
- 238000002156 mixing Methods 0.000 description 2
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- 239000003381 stabilizer Substances 0.000 description 2
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- 235000019698 starch Nutrition 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 239000003765 sweetening agent Substances 0.000 description 2
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- 235000012222 talc Nutrition 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 239000008158 vegetable oil Substances 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
- BIJYXIOVXFBJEP-UHFFFAOYSA-N 2-(oxiran-2-ylmethoxy)benzonitrile Chemical compound N#CC1=CC=CC=C1OCC1OC1 BIJYXIOVXFBJEP-UHFFFAOYSA-N 0.000 description 1
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-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
- 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
- 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
- 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
- 241000196324 Embryophyta Species 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 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
- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 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
- 229940081735 acetylcellulose Drugs 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 239000006172 buffering agent 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
- 229940105329 carboxymethylcellulose Drugs 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
- -1 collidone Substances 0.000 description 1
- 239000007859 condensation product 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
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- GZXSDYYWLZERLF-UHFFFAOYSA-N ethyl n-ethylcarbamate Chemical compound CCNC(=O)OCC GZXSDYYWLZERLF-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 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
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000012731 long-acting form Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 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
- 239000000203 mixture 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
- 239000000546 pharmaceutical excipient Substances 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
- 239000000047 product 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
- 238000010992 reflux Methods 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
- 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
- 235000013874 shellac Nutrition 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent 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
- 238000003756 stirring Methods 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
- 239000006188 syrup Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 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
- 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
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Przedmiotem wynalazku jest sposób wytwarza¬ nia 1-(2-cyjanofenoksy) -2-hydroksy-3-etyloamino- propanu o wzorze 1, jak równiez jego soli addy¬ cyjnych z kwasami. Jest to zwiazek nowy i moze znalezc zastosowanie jako srodek leczniczy.Wedlug wynalazku nowy zwiazek wytwarza sie przez hydrolize 3-etylo-5-(2-cyjanofenoksymetylo)- -oksazolidynonu-(2) o wzorze 2, na przyklad za pomoca mocnych alkaliów.Oksazolidynon o wzorze 2 wytwarza sie, na przyklad przez reakcje 1-(2-cyjanofenoksy)-2,3-epo- ksypropanu z N-etylouretanem (otrzymanym z chlo- romrówczanu etylu i etyloaminy) w obecnosci wo¬ dorotlenku litowego.Wytworzony sposobem wedlug wynalazku zwia¬ zek posiada w ugrupowaniu -CHJOH- asymetryczny atom wegla; wystepuje wiec zarówno w formie racematu, jak równiez optycznie czynnych anty¬ podów. Optycznie czynne zwiazki mozna otrzymac albo wychodzac z optycznie czynnych produktów wyjsciowych, albo rozdzielajac otrzymany racemat w znany sposób, na przyklad za pomoca kwasu dwubenzoilowinowego lub bromokamforosulfono- wego, na antypody optyczne.Wytworzony sposobem wedlug wynalazku zwia¬ zek mozna przeprowadzac w znany sposób w fizjo¬ logicznie tolerowane sole addycyjne z kwasami.Do tego celu nadaje sie na przyklad kwas solny, bromowodorowy, siarkowy, metanosulfonowy, ma¬ il leinowy, octowy, . szczawiowy, mlekowy, winowy albo 8-chloroteofilina.Wytworzony sposobem wedlug wynalazku zwia¬ zek o wzorze 1, wzglednie jego fizjologicznie tole¬ rowane sole addycyjne z kwasami posiadaja cenne wlasciwosci terapeutyczne, szczególnie /?-adrenoli- tyczne i mozna je podawac leczniczo lub profi¬ laktycznie w schorzeniach naczyn wiencowych ser¬ ca, w leczeniu arytmii serca, zwlaszcza czestoskur¬ czu. Zwiazek ten wykazuje w badaniach na swin¬ kach morskich znacznie skuteczniejsze dzialanie, zwalniajace akcje serca i antagonistyczne w sto¬ sunku do aludryny [aludryna = l-(3,4-dwuhydro- ksyfenylo)-l-hydroksy-2-izopropyloaminoetan] oraz mniejsza toksycznosc niz znany l-(l-naftoksy)-2- -hydroksy-3-izopropyloaminopropan.Jednorazowa dawka otrzymanego sposobem wed¬ lug wynalazku zwiazku wynosi 1—150 img, ko¬ rzystnie 5—'50 mig (doustnie), wzglednie 1—20 mg (ipozajelitowo).Z otrzymanego sposobem wedlug wynalazku zwiazku mozna sporzadzic zwykle stosowane po¬ stacie galenowe, takie jak roztwory, emulsje, ta¬ bletki, drazetki albo postacie o przedluzonym dzia¬ laniu, w znany sposób przy uzyciu srodków po¬ mocniczych, nosników, srodków rozsadzajacych, wiazacych, .powlekajacych albo poslizgowych, sma¬ kowych, slodzacych, srodków do osiagniecia prze¬ dluzonego dzialania albo ulatwiajacych rozpusz¬ czanie. Nowy zwiazek moze (byc równiez stoso- 84 3983 wany w polaczeniu z innymi farmakodynamicznie czynnymi substancjami, takimi jak substancje roz¬ szerzajace naczynia wiencowe,v pobudzajace uklad wspólczulny, glikozydy nasercowe albo srodki uspo¬ kajajace.Tabletki mozna na przyklad otrzymywac przez mieszanie substancji czynnej ze znanymi substan¬ cjami pomocniczymi, na iprzyklad obojetnymi roz¬ cienczalnikami, takimi jak weglan wapniowy, fos¬ foran wapniowy albo cukier mlekowy, srodkami rozsadzajacymi, takimi jak skrobia kukurydziana lub kwas alginowy, Isrodkami. wiazacymi, takimi jak skrobia albo zelatyna, srodkami poslizgowymi, takimi jak stearynian magnezowy albo. talk i/lub srodkami do uzyskania przedluzonego dzialania, takimi jak karboksypolimetylen, karboksymetylo- celuloza, ftalan acetylocelulozy albo octan poliwi- nylu. r Tabletki moga* równiez skladac sie z wielu warstw. iDrazetki mozna otrzymywac odpowiednio przez powlekanie otrzymanych analogicznie do tabletek rdzeni w znany sposób przy uzyciu srod¬ ków stosowanych zwykle do drazowania, takich jak kolidon, szelak, iguma arabska, talk, dwutlenek tytanu albo cukier. Dla uzyskania efektu przedlu¬ zonego 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 ta¬ bletkach substancje pomocnicze.Do wytwarzania miekkich kapsulek zelatyno¬ wych albo podobnych kapsulek zamykanych sub¬ stancje czynna mozna mieszac z olejem roslin¬ nym. Twarde kapsulki zelatynowe moga zawierac granulat substancji czynnej w polaczeniu ze sta¬ lymi sproszkowanymi nosnikami, takimi jak lakto¬ za, sacharoza, sorbit, mannit, skrobia, na przyklad Bkrobia ziemniaczana, kukurydziana albo amyli- pektyna, pochodne celulozy albo zelatyna.Syropy substancji czynnej lub tez kombinacji substancji czynnych moga zawierac dodatkowo je¬ szcze srodek slodzacy, taki jak sacharyna, cykla- minian, gliceryne albo cukier, jak równiez srodek poprawiajacy smak, na przyklad srodki zapacho¬ we, jak wanilina albo ekstrakt pomaranczowy.Oprócz tego rnoga zawierac jeszcze srodki ulatwia¬ jace powstawanie zawiesiny, zagestniki, takie jak sól sodowa karboksymetylocelulozy, srodki zwliza- jace, na przyklad produkty kondensacji alkoholi tluszczowych z tlenkiem etylenu, albo srodki kon¬ serwujace, jak /?-hydroksybenzoesany.Roztwory iniekcyjne przygotowuje sie w znany sposób, na przyklad z dodatkiem srodków kon- 1398 4 gerwujacych, takich jak /?-hydroksybenzoesany albo stabilizatorów, takich jak kompleksony i rozlewa do fiolek iniekcyjnych lub ampulek. Roztwory moga zawierac równiez stabilizator i/lub srodek buforujacy.Czopki mozna sporzadzac przez zmieszanie sub¬ stancji czynnej wzglednie kombinacji substancji czynnych ze znanymi nosnikami, takimi jak tlusz¬ cze obojetne albo glikol polietylenowy wzglednie jego pochodne. Mozna równiez wytwarzac doodbyt- nicze kapsulki zelatynowe zawierajace aktywna substancje zmieszana z olejem roslinnym lub pa¬ rafinowym.Nastepujacy przyklad objasnia blizej sposób wedlug wynalazku, nie stanowiac jego ogranicze¬ nia.Przyklad. Chlorowodorek l-(2-cyjanofenoksy)- - 2jhydroksy-2-etyloaminopropanu Mieszanine 4,92 g (0,02 mola) 3-etylo-5-(2-cyjano- fenoksymetylo)-oksazolidynonu-2, 5,6 g (0,1 mola) wodorotlenku potasowego1, 12 ml wody i 30 ml etanolu utrzymuje sie, mieszajac, w ciagu 3 go¬ dzin w stanie wrzenia pod chlodnica zwrotna.Nastepnie rozpuszczalnik oddestylowuje sie pod obnizonym cisnieniem, pozostalosc rozpuszcza w rozcienczonym kwasie solnym i przemywa dwu¬ krotnie eterem. Faze kwasu solnego aikalizuje sie, a wydzielony olej ekstrahuje eterem. Po przemy¬ ciu, wysuszeniu i odparowaniu eteru pozostala zasade rozpuszcza sie w alkoholu, zakwasza alko¬ holowym roztworem chlorowodoru i przez dodanie eteru wytraca krystaliczny chlorowodorek. Wydaj¬ nosc wynosi 2,1 g, temperatura topnienia 130— —133°C. PL PL PL PL PL PL PL PL
Claims (2)
1. Zastr zezenia patentowe 1. Sposób wytwarzania l-(2-cyjanofenoksy)-2- -hydroksy-3-etyloaminopropanu o wzorze 1, w po¬ staci racemicznej lub optycznie czynnej, jak rów¬ niez jego soli addycyjnych z kwasami, znamienny tym, ze 3-etylo-5-(2-cyjanofenoksy-metylo)-oksazo- lidynon-2 o wzorze 2 hydrolizuje sie i ewentualnie uzyskany racemat ewentualnie rozszczepia sie na postacie optycznie czynne i/lub zwiazek o wzorze 1 45 przeprowadza sie w fizjologicznie tolerowane sole addycyjne z kwasem.
2. Sposób wedlug zastrz. 1, znamienny tym, ze w przypadku wytwarzania optycznie czynnego 50 l-(2-cyjanofenoksy)- 2-hydroksy- 3-etyloaminopro^ panu i jego soli, racemiczny l-(2-cyjanofenoksy)- -2-hydroksy-3-etyloaminopropan przeprowadza sie za pomoca kwasów pomocniczych w diastereoizo- meryczne sole, które nastepnie rozklada sie.84 398 CN 0CH2~CH0H-CH2-NHC2H5 Wzór 1 CN Q-0CH2-CH O \ / c ChL i L N C2H5 II O Wzór 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 |
|---|---|
| PL84398B1 true PL84398B1 (en) | 1976-03-31 |
Family
ID=5742361
Family Applications (8)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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] |
| PL1970142704A PL80550B1 (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] |
| PL1970174660A PL84519B1 (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] |
| PL1970174662A PL84357B1 (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] |
Family Applications Before (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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] |
| PL1970142704A PL80550B1 (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] |
| 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 (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1970174662A PL84357B1 (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] |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3732277A (pl) |
| AT (9) | AT303006B (pl) |
| BE (1) | BE754604A (pl) |
| BG (8) | BG16739A3 (pl) |
| CH (1) | CH546223A (pl) |
| CS (8) | CS166732B2 (pl) |
| DE (1) | DE1940566C3 (pl) |
| DK (1) | DK125639B (pl) |
| ES (8) | ES382497A1 (pl) |
| FR (1) | FR2068479B1 (pl) |
| NL (1) | NL171702C (pl) |
| PL (8) | PL84339B1 (pl) |
| RO (8) | RO60084A (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 |
| GB1455116A (en) * | 1972-12-15 | 1976-11-10 | Ici Ltd | Pharmaceutical compositions |
| US4083992A (en) * | 1972-12-15 | 1978-04-11 | Imperial Chemical Industries Limited | Alkanolamine derivatives |
| US4171374A (en) * | 1972-12-15 | 1979-10-16 | 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 |
| US4167581A (en) * | 1972-12-15 | 1979-09-11 | Imperial Chemical Industries Limited | Alkanolamine derivatives and pharmaceutical compositions and uses thereof |
| 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 CS3683*[A patent/CS166732B2/cs unknown
- 1970-08-04 CS CS5440A patent/CS166731B2/cs unknown
- 1970-08-04 CS CS703685A patent/CS166734B2/cs unknown
- 1970-08-04 CS CS3687*[A patent/CS166736B2/cs unknown
- 1970-08-04 CS CS3686*[A patent/CS166735B2/cs unknown
- 1970-08-04 CS CS3689*[A patent/CS166738B2/cs unknown
- 1970-08-04 CS CS3684*[A patent/CS166733B2/cs unknown
- 1970-08-04 CS CS3688*[A patent/CS166737B2/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 SE SE7010830A patent/SE375303B/xx unknown
- 1970-08-06 RO RO69113A patent/RO60084A/ro unknown
- 1970-08-06 RO RO69110A patent/RO60746A/ro unknown
- 1970-08-06 RO RO69115A patent/RO61039A/ro unknown
- 1970-08-06 RO RO69111A patent/RO60082A/ro unknown
- 1970-08-06 RO RO69112A patent/RO60083A/ro unknown
- 1970-08-06 RO RO64160A patent/RO55805A/ro unknown
- 1970-08-06 RO RO69109A patent/RO60645A/ro unknown
- 1970-08-06 RO RO69108A patent/RO60644A/ro unknown
- 1970-08-06 ES ES382497A patent/ES382497A1/es not_active Expired
- 1970-08-06 YU YU2007/70A patent/YU34515B/xx unknown
- 1970-08-07 AT AT723670A patent/AT303006B/de not_active IP Right Cessation
- 1970-08-07 AT AT1107971A patent/AT303012B/de not_active IP Right Cessation
- 1970-08-07 NL NLAANVRAGE7011735,A patent/NL171702C/xx not_active IP Right Cessation
- 1970-08-07 AT AT1108171A patent/AT303014B/de not_active IP Right Cessation
- 1970-08-07 AT AT1108071A patent/AT303013B/de not_active IP Right Cessation
- 1970-08-07 BG BG18253A patent/BG17759A3/xx unknown
- 1970-08-07 DK DK407670AA patent/DK125639B/da not_active IP Right Cessation
- 1970-08-07 PL PL1970174657A patent/PL84339B1/pl unknown
- 1970-08-07 PL PL1970174659A patent/PL84520B1/pl unknown
- 1970-08-07 AT AT1107771A patent/AT303010B/de not_active IP Right Cessation
- 1970-08-07 FR FR7029317A patent/FR2068479B1/fr not_active Expired
- 1970-08-07 AT AT1107471A patent/AT303008B/de not_active IP Right Cessation
- 1970-08-07 PL PL1970142704A patent/PL80550B1/pl unknown
- 1970-08-07 BG BG18256A patent/BG18179A3/xx unknown
- 1970-08-07 BG BG18255A patent/BG17761A3/xx unknown
- 1970-08-07 PL PL1970174656A patent/PL84341B1/pl unknown
- 1970-08-07 AT AT1107671A patent/AT302996B/de not_active IP Right Cessation
- 1970-08-07 PL PL1970174660A patent/PL84519B1/pl unknown
- 1970-08-07 PL PL1970174658A patent/PL84398B1/pl unknown
- 1970-08-07 AT AT1107871A patent/AT303011B/de not_active IP Right Cessation
- 1970-08-07 PL PL1970174662A patent/PL84357B1/pl unknown
- 1970-08-07 BG BG18254A patent/BG17760A3/xx unknown
- 1970-08-07 BG BG15431A patent/BG18178A3/xx unknown
- 1970-08-07 BG BG18258A patent/BG17762A3/xx unknown
- 1970-08-07 BG BG18259A patent/BG17955A3/xx unknown
- 1970-08-07 PL PL1970174661A patent/PL86937B1/pl unknown
- 1970-08-07 AT AT1107571A patent/AT303009B/de not_active IP Right Cessation
-
1971
- 1971-03-04 ES ES388881A patent/ES388881A1/es not_active Expired
- 1971-03-04 ES ES388880A patent/ES388880A1/es not_active Expired
- 1971-03-04 ES ES388882A patent/ES388882A1/es not_active Expired
- 1971-03-04 ES ES388884A patent/ES388884A1/es not_active Expired
- 1971-03-04 ES ES388879A patent/ES388879A1/es not_active Expired
- 1971-03-04 ES ES388883A patent/ES388883A1/es not_active Expired
- 1971-03-04 ES ES388885A patent/ES388885A1/es not_active Expired
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