CH573443A5 - Amino-propanes - useful for heart muscle deficiency treatment 1-phenoxy-2-hydroxy-3-amino-propanes - Google Patents

Amino-propanes - useful for heart muscle deficiency treatment 1-phenoxy-2-hydroxy-3-amino-propanes

Info

Publication number: CH573443A5
Authority: CH; Switzerland
Prior art keywords: hydroxy; amino; phenyl; phenoxy; glucopyranoside
Prior art date: 1972-12-22

Application number

CH1873172A

Other languages

German (de)

English (en)

Original Assignee

Ciba Geigy Ag

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.)

1972-12-22

Filing date

1972-12-22

Publication date

1976-03-15

1972-12-22 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1972-12-22 Priority to CH1873172A priority Critical patent/CH573443A5/de

1973-11-26 Priority to SE7315965A priority patent/SE411673B/xx

1973-12-03 Priority to IL43742A priority patent/IL43742A/en

1973-12-04 Priority to IE2191/73A priority patent/IE38607B1/xx

1973-12-04 Priority to CA187,308A priority patent/CA1041491A/fr

1973-12-06 Priority to ZA739291A priority patent/ZA739291B/xx

1973-12-07 Priority to NO4690/73A priority patent/NO139168C/no

1973-12-10 Priority to DE2361355A priority patent/DE2361355A1/de

1973-12-11 Priority to NL7316948A priority patent/NL7316948A/xx

1973-12-12 Priority to GB5758373A priority patent/GB1447558A/en

1973-12-17 Priority to FR7344999A priority patent/FR2211228B1/fr

1973-12-20 Priority to LU69046A priority patent/LU69046A1/xx

1973-12-20 Priority to DD175546A priority patent/DD110260A5/xx

1973-12-20 Priority to AU63817/73A priority patent/AU483343B2/en

1973-12-21 Priority to AR251664A priority patent/AR203835A1/es

1973-12-21 Priority to HUCI1426A priority patent/HU167254B/hu

1973-12-21 Priority to BE139198A priority patent/BE809012A/fr

1973-12-21 Priority to AT1074773A priority patent/AT330369B/de

1973-12-22 Priority to ES421739A priority patent/ES421739A1/es

1973-12-22 Priority to JP48143007A priority patent/JPS4988833A/ja

1974-01-01 Priority to AR256894A priority patent/AR206799A1/es

1975-02-03 Priority to US05/546,648 priority patent/US3978041A/en

1975-05-23 Priority to AT393275A priority patent/AT331424B/de

1976-03-15 Publication of CH573443A5 publication Critical patent/CH573443A5/de

Links

JZEHWMUIAKALDN-UHFFFAOYSA-N 1-amino-3-phenoxypropan-2-ol Chemical class NCC(O)COC1=CC=CC=C1 JZEHWMUIAKALDN-UHFFFAOYSA-N 0.000 title claims description 6
230000007812 deficiency Effects 0.000 title abstract 2
210000004165 myocardium Anatomy 0.000 title abstract 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical class CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 title 1
-1 alpha-methyl-phenethyl Chemical group 0.000 claims abstract description 24
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 8
150000003839 salts Chemical class 0.000 claims description 25
150000001875 compounds Chemical class 0.000 claims description 19
238000000034 method Methods 0.000 claims description 16
239000000203 mixture Substances 0.000 claims description 16
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 4
229910052740 iodine Inorganic materials 0.000 claims description 4
230000003287 optical effect Effects 0.000 claims description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
239000004593 Epoxy Substances 0.000 abstract description 4
239000003814 drug Substances 0.000 abstract description 2
239000004480 active ingredient Substances 0.000 abstract 1
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 abstract 1
230000000297 inotrophic effect Effects 0.000 abstract 1
125000001424 substituent group Chemical group 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 52
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
239000000741 silica gel Substances 0.000 description 16
229910002027 silica gel Inorganic materials 0.000 description 16
239000002904 solvent 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 14
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
239000002253 acid Substances 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
239000007858 starting material Substances 0.000 description 8
238000003756 stirring Methods 0.000 description 8
239000007795 chemical reaction product Substances 0.000 description 7
229910052943 magnesium sulfate Inorganic materials 0.000 description 7
235000019341 magnesium sulphate Nutrition 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
239000005457 ice water Substances 0.000 description 6
239000003208 petroleum Substances 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
239000002585 base Substances 0.000 description 5
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 5
230000007935 neutral effect Effects 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 4
239000000047 product Substances 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 3
230000007717 exclusion Effects 0.000 description 3
BJRNKVDFDLYUGJ-RMPHRYRLSA-N hydroquinone O-beta-D-glucopyranoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=C(O)C=C1 BJRNKVDFDLYUGJ-RMPHRYRLSA-N 0.000 description 3
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
239000003921 oil Substances 0.000 description 3
235000019198 oils Nutrition 0.000 description 3
BJRNKVDFDLYUGJ-UHFFFAOYSA-N p-hydroxyphenyl beta-D-alloside Natural products OC1C(O)C(O)C(CO)OC1OC1=CC=C(O)C=C1 BJRNKVDFDLYUGJ-UHFFFAOYSA-N 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
SUSRLLXAXAIZPH-OBPIAQAESA-N hydroquinone beta-D-glucopyranoside Natural products OC[C@H]1O[C@@H](Cc2ccc(O)cc2)[C@H](O)[C@@H](O)[C@@H]1O SUSRLLXAXAIZPH-OBPIAQAESA-N 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
239000007788 liquid 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
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
230000002107 myocardial effect Effects 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
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229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
AAWZDTNXLSGCEK-LNVDRNJUSA-N (3r,5r)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical compound O[C@@H]1CC(O)(C(O)=O)C[C@@H](O)C1O AAWZDTNXLSGCEK-LNVDRNJUSA-N 0.000 description 1
MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
UWYVPFMHMJIBHE-OWOJBTEDSA-N (e)-2-hydroxybut-2-enedioic acid Chemical compound OC(=O)\C=C(\O)C(O)=O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
QXQAPNSHUJORMC-UHFFFAOYSA-N 1-chloro-4-propylbenzene Chemical compound CCCC1=CC=C(Cl)C=C1 QXQAPNSHUJORMC-UHFFFAOYSA-N 0.000 description 1
WLXGQMVCYPUOLM-UHFFFAOYSA-N 1-hydroxyethanesulfonic acid Chemical compound CC(O)S(O)(=O)=O WLXGQMVCYPUOLM-UHFFFAOYSA-N 0.000 description 1
FZKCAHQKNJXICB-UHFFFAOYSA-N 2,1-benzoxazole Chemical compound C1=CC=CC2=CON=C21 FZKCAHQKNJXICB-UHFFFAOYSA-N 0.000 description 1
LNSCNEJNLACZPA-UHFFFAOYSA-N 2,3-dihydroxy-2,3-bis(2-methylphenyl)butanedioic acid Chemical compound CC1=CC=CC=C1C(O)(C(O)=O)C(O)(C(O)=O)C1=CC=CC=C1C LNSCNEJNLACZPA-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-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
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 1
ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 1
WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
QISOBCMNUJQOJU-UHFFFAOYSA-N 4-bromo-1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1NN=CC=1Br QISOBCMNUJQOJU-UHFFFAOYSA-N 0.000 description 1
PXACTUVBBMDKRW-UHFFFAOYSA-N 4-bromobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Br)C=C1 PXACTUVBBMDKRW-UHFFFAOYSA-N 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
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239000004475 Arginine Substances 0.000 description 1
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WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
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ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
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125000002723 alicyclic group Chemical group 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
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150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
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WXBLLCUINBKULX-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1 WXBLLCUINBKULX-UHFFFAOYSA-N 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
150000003938 benzyl alcohols Chemical class 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
229940073608 benzyl chloride Drugs 0.000 description 1
230000017531 blood circulation Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
229920001429 chelating resin Polymers 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
235000012000 cholesterol Nutrition 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
230000002057 chronotropic effect Effects 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
239000000470 constituent Substances 0.000 description 1
229960001270 d- tartaric acid Drugs 0.000 description 1
150000004683 dihydrates Chemical class 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
AINBZKYUNWUTRE-UHFFFAOYSA-N ethanol;propan-2-ol Chemical compound CCO.CC(C)O AINBZKYUNWUTRE-UHFFFAOYSA-N 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
YKWNUSJLICDQEO-UHFFFAOYSA-N ethoxyethane;propan-2-ol Chemical compound CC(C)O.CCOCC YKWNUSJLICDQEO-UHFFFAOYSA-N 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229940071870 hydroiodic acid Drugs 0.000 description 1
239000004041 inotropic agent Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
239000011630 iodine Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
229960002510 mandelic acid Drugs 0.000 description 1
DGEYTDCFMQMLTH-UHFFFAOYSA-N methanol;propan-2-ol Chemical compound OC.CC(C)O DGEYTDCFMQMLTH-UHFFFAOYSA-N 0.000 description 1
229930182817 methionine Natural products 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
244000005700 microbiome Species 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
125000006606 n-butoxy group Chemical group 0.000 description 1
125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
229940066842 petrolatum Drugs 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
230000009090 positive inotropic effect Effects 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
239000001294 propane Substances 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
229940107700 pyruvic acid Drugs 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
125000005920 sec-butoxy group Chemical group 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229960001367 tartaric acid Drugs 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical group CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Saccharide Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH1873172A 1972-12-22 1972-12-22 Amino-propanes - useful for heart muscle deficiency treatment 1-phenoxy-2-hydroxy-3-amino-propanes CH573443A5 (en)

Priority Applications (23)

Application Number	Priority Date	Filing Date	Title
CH1873172A CH573443A5 (en)	1972-12-22	1972-12-22	Amino-propanes - useful for heart muscle deficiency treatment 1-phenoxy-2-hydroxy-3-amino-propanes
SE7315965A SE411673B (sv)	1972-12-22	1973-11-26	Forfarande for framstellning av 1-fenoxi-2-hydroxi-3-aminopropaner samt syraadditionssalter derav
IL43742A IL43742A (en)	1972-12-22	1973-12-03	Derivatives of phenoxy-propanolamine sugar ethers and their manufacture
IE2191/73A IE38607B1 (en)	1972-12-22	1973-12-04	Amines
CA187,308A CA1041491A (fr)	1972-12-22	1973-12-04	Fabrication de nouvelles amines
ZA739291A ZA739291B (en)	1972-12-22	1973-12-06	New amines
NO4690/73A NO139168C (no)	1972-12-22	1973-12-07	Analogifremgangsmaate til fremstilling av derivater av 1-fenoksy-2-hydroksy-3-amino-propan
DE2361355A DE2361355A1 (de)	1972-12-22	1973-12-10	Neue amine und verfahren zu ihrer herstellung
NL7316948A NL7316948A (fr)	1972-12-22	1973-12-11
GB5758373A GB1447558A (en)	1972-12-22	1973-12-12	Amines
FR7344999A FR2211228B1 (fr)	1972-12-22	1973-12-17
LU69046A LU69046A1 (fr)	1972-12-22	1973-12-20
DD175546A DD110260A5 (fr)	1972-12-22	1973-12-20
AU63817/73A AU483343B2 (en)	1972-12-22	1973-12-20	New amines
AR251664A AR203835A1 (es)	1972-12-22	1973-12-21	Procedimiento para la elaboracion de nuevos derivados del 2-hidroxi-3-aminopropano
HUCI1426A HU167254B (fr)	1972-12-22	1973-12-21
BE139198A BE809012A (fr)	1972-12-22	1973-12-21	Nouvelles amines et leurs procedes de preparation
AT1074773A AT330369B (de)	1972-12-22	1973-12-21	Verfahren zur herstellung von neuen 1-phenoxy-2-hydroxy -3- amino-propanen
ES421739A ES421739A1 (es)	1972-12-22	1973-12-22	Procedimiento para la obtencion de 1-fenoxi-2-hidroxi-3- amino-propanos.
JP48143007A JPS4988833A (fr)	1972-12-22	1973-12-22
AR256894A AR206799A1 (es)	1972-12-22	1974-01-01	Procedimiento para la elaboracion de nuevos derivados del 1-(p-(1-glucopiranosidil))-fenoxi-2-hidroxi-3-aminopropan
US05/546,648 US3978041A (en)	1972-12-22	1975-02-03	Phenoxy substituted glycosides
AT393275A AT331424B (de)	1972-12-22	1975-05-23	Verfahren zur herstellung von neuen 1-phenoxy-2-hydroxy-3-amino-propanen

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1873172A CH573443A5 (en)	1972-12-22	1972-12-22	Amino-propanes - useful for heart muscle deficiency treatment 1-phenoxy-2-hydroxy-3-amino-propanes

Publications (1)

Publication Number	Publication Date
CH573443A5 true CH573443A5 (en)	1976-03-15

Family

ID=4434954

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1873172A CH573443A5 (en)	1972-12-22	1972-12-22	Amino-propanes - useful for heart muscle deficiency treatment 1-phenoxy-2-hydroxy-3-amino-propanes

Country Status (5)

Country	Link
AT (1)	AT330369B (fr)
BE (1)	BE809012A (fr)
CH (1)	CH573443A5 (fr)
HU (1)	HU167254B (fr)
ZA (1)	ZA739291B (fr)

1972
- 1972-12-22 CH CH1873172A patent/CH573443A5/de not_active IP Right Cessation
1973
- 1973-12-06 ZA ZA739291A patent/ZA739291B/xx unknown
- 1973-12-21 HU HUCI1426A patent/HU167254B/hu unknown
- 1973-12-21 BE BE139198A patent/BE809012A/fr unknown
- 1973-12-21 AT AT1074773A patent/AT330369B/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
HU167254B (fr)	1975-09-27
AT330369B (de)	1976-06-25
ZA739291B (en)	1974-10-30
ATA1074773A (de)	1975-09-15
BE809012A (fr)	1974-06-21

Legal Events

Date	Code	Title	Description
1981-08-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
EP0042593B1 (fr)	1985-04-03	Aryloxypropanolamines, procédé pour leur préparation et médicament les contenant
DE69531242T2 (de)	2004-05-27	Verfahren zur herstellung von azabicyclische derivaten
DE2658401A1 (de)	1978-07-06	Cyclopentan-1-amine, verfahren zu ihrer herstellung und diese verbindungen enthaltende mittel
EP0074014B1 (fr)	1984-06-27	2-(2'-hydroxy-3'-(1,1-diméthylpropylamino)-propoxy)-bêta-propiophénone, ses sels d'addition, procédé de sa préparation et médicament
EP0374095A2 (fr)	1990-06-20	Dérivés de pipéridine
EP0189370A2 (fr)	1986-07-30	Spiro-dioxolanes, -dithiolanes et -oxothiolanes
EP0208932A2 (fr)	1987-01-21	Dérivés de glycérine
EP0155518B1 (fr)	1989-08-30	S(-) celiprolol, sels pharmaceutiquement acceptables, préparation et compositions pharmaceutiques
DE2632118A1 (de)	1977-01-20	Apovincaminolester und verfahren zu deren herstellung
DE3223877C2 (fr)	1990-08-30
CH573443A5 (en)	1976-03-15	Amino-propanes - useful for heart muscle deficiency treatment 1-phenoxy-2-hydroxy-3-amino-propanes
DE2503751C2 (de)	1986-05-22	(L)-1-Phenoxy-3-isopropylamino-2-propanol und dessen Salze, Verfahren zur Herstellung und Verwendung
EP0030688B1 (fr)	1983-09-28	Dérivés de pipéridine d'esters de l'acide 3-hydroxy-thiophène-2-carboxylique, leur préparation et préparations pharmaceutiques les contenant
EP0107208B1 (fr)	1986-01-22	Dérivés du triphényl-1,1,2 butène-1, procédé pour leur préparation et leur application comme médicaments
DE3703633A1 (de)	1987-08-20	Purin-derivate, ihre herstellung und sie enthaltende arzneimittel
DE1182245B (de)	1964-11-26	Verfahren zur Herstellung eines uterospasmolytisch wirksamen linksdrehenden 1-(4'-Hy-droxyphenyl)-2-(1"-methyl-3"phenylpropylamino)-propanols
EP0481253B1 (fr)	1994-12-28	Dérivés d'acides p-oxybenzoiques, procédés pour leur préparation et leur utilisation comme médicaments
DE2053192C3 (de)	1974-02-28	l-Amino-3-phenoxy-propanol-(2)derivate, deren therapeutisch verträgliche Salze und diese enthaltende Arzneimittel
EP0244713B1 (fr)	1990-08-16	3-Amino-dihydropyridines, leur procédé de préparation et leur application comme médicaments
EP0462150B1 (fr)	1994-09-07	Nouvelles aryloxy-alkylamines, leur fabrication et medicaments les contenant
DE1618160C3 (de)	1974-04-25	l-(2-Äthinylphenoxy)-2-hydroxy-3alkylaminopropane, ihre physiologisch verträglichen Säureadditionssalze, Verfahren zu ihrer Herstellung, sowie diese Verbindungen enthaltende Arzneimittel
AT336018B (de)	1977-04-12	Verfahren zur herstellung von neuen heterocyclischen verbindungen
CH579099A5 (en)	1976-08-31	Amino-propanes - useful for heart muscle deficiency treatment 1-phenoxy-2-hydroxy-3-amino-propanes
CH579100A5 (en)	1976-08-31	Amino-propanes - useful for heart muscle deficiency treatment 1-phenoxy-2-hydroxy-3-amino-propanes
DE1227462B (de)	1966-10-27	Verfahren zur Herstellung von Chinolinderivaten