IL29242A - 1-) 2-Cyanophenoxy (-2-hydroxy-3-isopropylaminopropane and its preparation - Google Patents

1-) 2-Cyanophenoxy (-2-hydroxy-3-isopropylaminopropane and its preparation

Info

Publication number: IL29242A
Authority: IL; Israel
Prior art keywords: hydroxy; cyanophenoxy; acid; isopropylaminopropane; formula
Prior art date: 1966-12-30

Application number

IL2924267A

Other languages

English (en)

Hebrew (he)

Original Assignee

Boehringer Sohn Ingelheim

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1966-12-30

Filing date

1967-12-29

Publication date

1971-05-26

1967-12-29 Application filed by Boehringer Sohn Ingelheim filed Critical Boehringer Sohn Ingelheim

1971-05-26 Publication of IL29242A publication Critical patent/IL29242A/en

Links

238000002360 preparation method Methods 0.000 title claims description 14
YTTFGUYTPJYRBQ-UHFFFAOYSA-N 2-[2-hydroxy-3-(propan-2-ylamino)propoxy]benzonitrile Chemical compound CC(C)NCC(O)COC1=CC=CC=C1C#N YTTFGUYTPJYRBQ-UHFFFAOYSA-N 0.000 title 1
238000000034 method Methods 0.000 claims description 39
150000001875 compounds Chemical class 0.000 claims description 32
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 29
238000006243 chemical reaction Methods 0.000 claims description 24
239000000203 mixture Substances 0.000 claims description 22
150000003839 salts Chemical class 0.000 claims description 16
239000002253 acid Substances 0.000 claims description 15
239000004480 active ingredient Substances 0.000 claims description 13
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 9
230000007062 hydrolysis Effects 0.000 claims description 9
238000006460 hydrolysis reaction Methods 0.000 claims description 9
125000006239 protecting group Chemical group 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 7
231100000252 nontoxic Toxicity 0.000 claims description 7
230000003000 nontoxic effect Effects 0.000 claims description 7
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 5
239000003795 chemical substances by application Substances 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
-1 isopropyl halide Chemical class 0.000 claims description 5
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 5
239000000546 pharmaceutical excipient Substances 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
238000007911 parenteral administration Methods 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 3
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 claims description 3
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 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 claims description 3
235000011054 acetic acid Nutrition 0.000 claims description 3
238000009835 boiling Methods 0.000 claims description 3
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
239000004310 lactic acid Substances 0.000 claims description 3
235000014655 lactic acid Nutrition 0.000 claims description 3
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 3
239000011976 maleic acid Substances 0.000 claims description 3
235000006408 oxalic acid Nutrition 0.000 claims description 3
238000000197 pyrolysis Methods 0.000 claims description 3
239000001117 sulphuric acid Substances 0.000 claims description 3
235000011149 sulphuric acid Nutrition 0.000 claims description 3
239000011975 tartaric acid Substances 0.000 claims description 3
235000002906 tartaric acid Nutrition 0.000 claims description 3
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 3
150000003672 ureas Chemical class 0.000 claims description 3
239000003377 acid catalyst Substances 0.000 claims description 2
150000001412 amines Chemical class 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
238000010438 heat treatment Methods 0.000 claims description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
239000000376 reactant Substances 0.000 claims description 2
238000005932 reductive alkylation reaction Methods 0.000 claims description 2
150000003512 tertiary amines Chemical class 0.000 claims description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 2
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 claims 2
125000004036 acetal group Chemical group 0.000 claims 1
150000007513 acids Chemical class 0.000 claims 1
239000003513 alkali Substances 0.000 claims 1
CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 claims 1
150000008049 diazo compounds Chemical class 0.000 claims 1
150000002118 epoxides Chemical class 0.000 claims 1
238000007327 hydrogenolysis reaction Methods 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 24
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
239000000243 solution Substances 0.000 description 15
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
239000002585 base Substances 0.000 description 8
230000000694 effects Effects 0.000 description 8
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
239000003826 tablet Substances 0.000 description 8
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000002775 capsule Substances 0.000 description 6
229910052943 magnesium sulfate Inorganic materials 0.000 description 6
235000019341 magnesium sulphate Nutrition 0.000 description 6
235000011121 sodium hydroxide Nutrition 0.000 description 6
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 6
239000012074 organic phase Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
229920002261 Corn starch Polymers 0.000 description 4
235000019759 Maize starch Nutrition 0.000 description 4
239000013543 active substance Substances 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
238000001816 cooling Methods 0.000 description 4
239000013078 crystal Substances 0.000 description 4
239000008298 dragée Substances 0.000 description 4
238000001035 drying Methods 0.000 description 4
239000008187 granular material Substances 0.000 description 4
235000019359 magnesium stearate Nutrition 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
150000003944 halohydrins Chemical class 0.000 description 3
239000008101 lactose Substances 0.000 description 3
150000002924 oxiranes Chemical class 0.000 description 3
229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
239000001267 polyvinylpyrrolidone Substances 0.000 description 3
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
231100000419 toxicity Toxicity 0.000 description 3
230000001988 toxicity Effects 0.000 description 3
238000011282 treatment Methods 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
BGRWYRAHAFMIBJ-UHFFFAOYSA-N 1,3-di(propan-2-yl)urea Chemical compound CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
239000004593 Epoxy Substances 0.000 description 2
239000001828 Gelatine Substances 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
235000021355 Stearic acid Nutrition 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
230000003042 antagnostic effect Effects 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000008119 colloidal silica Substances 0.000 description 2
229960001484 edetic acid Drugs 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
238000002955 isolation Methods 0.000 description 2
229940039009 isoproterenol Drugs 0.000 description 2
239000007788 liquid Substances 0.000 description 2
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
239000012071 phase Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000001294 propane Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000008117 stearic acid Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
230000001225 therapeutic effect Effects 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
XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 1
LFRHMTZYADABJZ-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)butan-2-amine;hydron;chloride Chemical compound Cl.CCC(N)CC1=CC=C2OCOC2=C1 LFRHMTZYADABJZ-UHFFFAOYSA-N 0.000 description 1
RNFDZDMIFOFNMC-UHFFFAOYSA-N 1-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(C)O RNFDZDMIFOFNMC-UHFFFAOYSA-N 0.000 description 1
JCERKCRUSDOWLT-UHFFFAOYSA-N 1-bromopropan-1-ol Chemical compound CCC(O)Br JCERKCRUSDOWLT-UHFFFAOYSA-N 0.000 description 1
IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 1
WUNINWXWLZRTKO-UHFFFAOYSA-N 2-[2-hydroxy-3-(propan-2-ylamino)propoxy]benzonitrile;hydrochloride Chemical compound Cl.CC(C)NCC(O)COC1=CC=CC=C1C#N WUNINWXWLZRTKO-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
NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
CHZCERSEMVWNHL-UHFFFAOYSA-N 2-hydroxybenzonitrile Chemical compound OC1=CC=CC=C1C#N CHZCERSEMVWNHL-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
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical class N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 1
239000005662 Paraffin oil Substances 0.000 description 1
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
244000061456 Solanum tuberosum Species 0.000 description 1
235000002595 Solanum tuberosum Nutrition 0.000 description 1
208000001871 Tachycardia Diseases 0.000 description 1
QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
229910001413 alkali metal ion Inorganic materials 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000003708 ampul Substances 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
230000003288 anthiarrhythmic effect Effects 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
206010003119 arrhythmia Diseases 0.000 description 1
230000006793 arrhythmia Effects 0.000 description 1
150000007514 bases Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 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
239000004202 carbamide Substances 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
230000001778 cardiodepressive effect Effects 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
210000004351 coronary vessel Anatomy 0.000 description 1
125000003963 dichloro group Chemical group Cl* 0.000 description 1
ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 1
WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000006196 drop Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
JGRPZAGOYKNIAC-UHFFFAOYSA-N ethyl n-propan-2-ylcarbamate Chemical compound CCOC(=O)NC(C)C JGRPZAGOYKNIAC-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
230000001077 hypotensive effect Effects 0.000 description 1
229940102223 injectable solution Drugs 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
230000001050 lubricating effect Effects 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000002245 particle Substances 0.000 description 1
231100000572 poisoning Toxicity 0.000 description 1
230000000607 poisoning effect Effects 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
230000006794 tachycardia Effects 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
238000005406 washing Methods 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
- 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
- A61K31/13—Amines
- A61K31/14—Quaternary ammonium compounds, e.g. edrophonium, choline

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material 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)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

IL2924267A 1966-12-30 1967-12-29 1-) 2-Cyanophenoxy (-2-hydroxy-3-isopropylaminopropane and its preparation IL29242A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DEB0090543		1966-12-30
DEB0093026		1967-06-15

Publications (1)

Publication Number	Publication Date
IL29242A true IL29242A (en)	1971-05-26

Family

ID=25968272

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL2924267A IL29242A (en)	1966-12-30	1967-12-29	1-) 2-Cyanophenoxy (-2-hydroxy-3-isopropylaminopropane and its preparation

Country Status (12)

Country	Link
JP (1)	JPS5123495B1 (da)
BE (1)	BE708815A (da)
CH (1)	CH496658A (da)
DE (1)	DE1593783A1 (da)
DK (1)	DK133094C (da)
ES (1)	ES348542A1 (da)
FI (1)	FI48345C (da)
FR (2)	FR1560399A (da)
GB (1)	GB1206420A (da)
IL (1)	IL29242A (da)
SE (1)	SE351845B (da)
YU (6)	YU33278B (da)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3937834A (en)	1970-10-02	1976-02-10	Ciba-Geigy Corporation	Pharmaceutical preparations
US4060601A (en)	1976-06-15	1977-11-29	Merck & Co., Inc.	Certain lower-alkyl amino-2'-hydroxy-propoxy pyridines

1967
- 1967-06-15 DE DE19671593783 patent/DE1593783A1/de active Pending
- 1967-12-18 CH CH1768567A patent/CH496658A/de not_active IP Right Cessation
- 1967-12-22 ES ES348542A patent/ES348542A1/es not_active Expired
- 1967-12-22 YU YU251167A patent/YU33278B/xx unknown
- 1967-12-28 SE SE1794067A patent/SE351845B/xx unknown
- 1967-12-29 FI FI350667A patent/FI48345C/fi active
- 1967-12-29 IL IL2924267A patent/IL29242A/en unknown
- 1967-12-29 GB GB5922467A patent/GB1206420A/en not_active Expired
- 1967-12-29 BE BE708815D patent/BE708815A/xx not_active IP Right Cessation
- 1967-12-29 DK DK659967A patent/DK133094C/da active
- 1967-12-29 FR FR1560399D patent/FR1560399A/fr not_active Expired
1968
- 1968-03-28 FR FR145900A patent/FR7850M/fr not_active Expired
- 1968-12-13 JP JP9102068A patent/JPS5123495B1/ja active Pending
1974
- 1974-04-10 YU YU100974A patent/YU100974A/xx unknown
- 1974-04-10 YU YU101374A patent/YU33282B/xx unknown
- 1974-04-10 YU YU101174A patent/YU33281B/xx unknown
- 1974-04-10 YU YU101074A patent/YU33279B/xx unknown
- 1974-04-10 YU YU101274A patent/YU33280B/xx unknown

Also Published As

Publication number	Publication date
ES348542A1 (es)	1969-11-01
YU33278B (en)	1976-08-31
GB1206420A (en)	1970-09-23
DK133094B (da)	1976-03-22
FI48345B (da)	1974-05-31
CH496658A (de)	1970-09-30
DK133094C (da)	1976-08-23
YU251167A (en)	1976-03-31
YU100974A (en)	1982-06-30
YU33281B (en)	1976-08-31
DE1593783A1 (de)	1972-05-25
YU101274A (en)	1976-03-31
FR7850M (da)	1970-06-01
FR1560399A (da)	1969-03-21
YU33279B (en)	1976-08-31
YU33280B (en)	1976-08-31
JPS5123495B1 (da)	1976-07-17
YU101174A (en)	1976-03-31
SE351845B (da)	1972-12-11
BE708815A (da)	1968-07-01
YU101074A (en)	1976-03-31
YU101374A (en)	1976-03-31
YU33282B (en)	1976-08-31
FI48345C (fi)	1974-09-10

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