CH576438A5 - 1-Alkylthioalkoxy-4-(3-amino-2-hydroxypropoxy) benzenes - antagonists of beta receptor stimulants prepd. e.g. by reducing corresp. Schiff base - Google Patents
1-Alkylthioalkoxy-4-(3-amino-2-hydroxypropoxy) benzenes - antagonists of beta receptor stimulants prepd. e.g. by reducing corresp. Schiff baseInfo
- Publication number
- CH576438A5 CH576438A5 CH62173A CH62173A CH576438A5 CH 576438 A5 CH576438 A5 CH 576438A5 CH 62173 A CH62173 A CH 62173A CH 62173 A CH62173 A CH 62173A CH 576438 A5 CH576438 A5 CH 576438A5
- Authority
- CH
- Switzerland
- Prior art keywords
- hydroxy
- phenoxy
- alk2
- methylthioethoxy
- carbon atoms
- Prior art date
Links
- 239000002262 Schiff base Substances 0.000 title abstract 2
- 150000004753 Schiff bases Chemical class 0.000 title abstract 2
- 239000005557 antagonist Substances 0.000 title description 2
- 102000012740 beta Adrenergic Receptors Human genes 0.000 title description 2
- 108010079452 beta Adrenergic Receptors Proteins 0.000 title description 2
- 239000000021 stimulant Substances 0.000 title description 2
- 150000001555 benzenes Chemical class 0.000 title 1
- -1 aldehydes ketones Chemical class 0.000 claims abstract description 31
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 25
- 150000003839 salts Chemical class 0.000 claims abstract description 24
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 5
- 239000004593 Epoxy Substances 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 14
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000001589 carboacyl group Chemical group 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 125000005336 allyloxy group Chemical group 0.000 claims description 3
- 125000005394 methallyl group Chemical group 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- MYJOGYCKRILART-UHFFFAOYSA-N 1-[4-(2-methylsulfanylethoxy)phenoxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound CSCCOC1=CC=C(OCC(O)CNC(C)C)C=C1 MYJOGYCKRILART-UHFFFAOYSA-N 0.000 claims description 2
- IPQOOZPGPYVSFC-UHFFFAOYSA-N CSCCCOC1=CC=C(OCC(CNC(C)C)O)C=C1 Chemical compound CSCCCOC1=CC=C(OCC(CNC(C)C)O)C=C1 IPQOOZPGPYVSFC-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- RNFDZDMIFOFNMC-UHFFFAOYSA-N 1-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(C)O RNFDZDMIFOFNMC-UHFFFAOYSA-N 0.000 claims 1
- PQXGHEXKFAAWEJ-UHFFFAOYSA-N 1-[4-(1-methylsulfanylpropan-2-yloxy)phenoxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(CSC)OC1=CC=C(OCC(CNC(C)C)O)C=C1 PQXGHEXKFAAWEJ-UHFFFAOYSA-N 0.000 claims 1
- SGIOYGIUKGQCOO-UHFFFAOYSA-N CSCCOC1=CC=C(OCC(CNC(C)(C)C)O)C=C1 Chemical compound CSCCOC1=CC=C(OCC(CNC(C)(C)C)O)C=C1 SGIOYGIUKGQCOO-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 101100490437 Mus musculus Acvrl1 gene Proteins 0.000 abstract description 6
- 125000003118 aryl group Chemical group 0.000 abstract description 4
- 206010002383 Angina Pectoris Diseases 0.000 abstract description 2
- 206010003119 arrhythmia Diseases 0.000 abstract description 2
- 239000007859 condensation product Substances 0.000 abstract 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 abstract 1
- XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 230000003042 antagnostic effect Effects 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 23
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 239000007858 starting material Substances 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 229910000027 potassium carbonate Inorganic materials 0.000 description 10
- 235000011181 potassium carbonates Nutrition 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 9
- 230000008020 evaporation Effects 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 7
- 235000011121 sodium hydroxide Nutrition 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- MYFKLQFBFSHBPA-UHFFFAOYSA-N 1-chloro-2-methylsulfanylethane Chemical compound CSCCCl MYFKLQFBFSHBPA-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- JWZZKOKVBUJMES-NSHDSACASA-N L-isoprenaline Chemical compound CC(C)NC[C@H](O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-NSHDSACASA-N 0.000 description 6
- 229950008384 levisoprenaline Drugs 0.000 description 6
- 239000000155 melt Substances 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 5
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 5
- 102000005962 receptors Human genes 0.000 description 5
- 108020003175 receptors Proteins 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- AHUMZPBUIRUCNC-UHFFFAOYSA-N 4-(2-methylsulfanylethoxy)phenol Chemical compound CSCCOC1=CC=C(O)C=C1 AHUMZPBUIRUCNC-UHFFFAOYSA-N 0.000 description 4
- 241000282326 Felis catus Species 0.000 description 4
- 208000001871 Tachycardia Diseases 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 230000008485 antagonism Effects 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 230000000747 cardiac effect Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000001990 intravenous administration Methods 0.000 description 4
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 230000006794 tachycardia Effects 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- GFBCWCDNXDKFRH-UHFFFAOYSA-N 4-(oxan-2-yloxy)phenol Chemical compound C1=CC(O)=CC=C1OC1OCCCC1 GFBCWCDNXDKFRH-UHFFFAOYSA-N 0.000 description 3
- JWZZKOKVBUJMES-LLVKDONJSA-N 4-[(1S)-1-hydroxy-2-(propan-2-ylamino)ethyl]benzene-1,2-diol Chemical compound CC(C)NC[C@@H](O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-LLVKDONJSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- IYQXHHPQPMGQJX-UHFFFAOYSA-N 1-chloro-3-[4-(2-methylsulfanylethoxy)phenoxy]propan-2-ol Chemical compound CSCCOC1=CC=C(OCC(CCl)O)C=C1 IYQXHHPQPMGQJX-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- ZGNXVNMIJNVSTF-UHFFFAOYSA-N 2-[[2-methyl-4-(2-methylsulfanylethoxy)phenoxy]methyl]oxirane Chemical compound O1CC1COC1=C(C=C(C=C1)OCCSC)C ZGNXVNMIJNVSTF-UHFFFAOYSA-N 0.000 description 2
- BPUHADYDLABISX-UHFFFAOYSA-N 2-[[4-(2-methylsulfanylethoxy)phenoxy]methyl]oxirane Chemical compound C1=CC(OCCSC)=CC=C1OCC1OC1 BPUHADYDLABISX-UHFFFAOYSA-N 0.000 description 2
- KUXXTQIMOMHZQM-UHFFFAOYSA-N 2-methyl-4-(2-methylsulfanylethoxy)phenol Chemical compound CC1=C(C=CC(=C1)OCCSC)O KUXXTQIMOMHZQM-UHFFFAOYSA-N 0.000 description 2
- YJBKDUPJJYIHCU-UHFFFAOYSA-N 3-chloro-4-(2-methylsulfanylethoxy)phenol Chemical compound ClC=1C=C(C=CC1OCCSC)O YJBKDUPJJYIHCU-UHFFFAOYSA-N 0.000 description 2
- XFLHCWFOEPPVJT-UHFFFAOYSA-N 4-(3-methylsulfanylpropoxy)phenol Chemical compound CSCCCOC1=CC=C(C=C1)O XFLHCWFOEPPVJT-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OOXWTDUGEUMJLK-UHFFFAOYSA-N CC(C)NCC(COC(C=C1)=C(C)C=C1OCCSC)O Chemical compound CC(C)NCC(COC(C=C1)=C(C)C=C1OCCSC)O OOXWTDUGEUMJLK-UHFFFAOYSA-N 0.000 description 2
- WCTWSCZAUFWFMQ-UHFFFAOYSA-N CSCCOC(C=CC(OCC1OC1)=C1)=C1Cl Chemical compound CSCCOC(C=CC(OCC1OC1)=C1)=C1Cl WCTWSCZAUFWFMQ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
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- 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
- 239000003513 alkali Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
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- 229910052799 carbon Inorganic materials 0.000 description 2
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- HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
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- 229910052740 iodine Inorganic materials 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
- 239000000463 material Substances 0.000 description 2
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
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- 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
- 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
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
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- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 1
- 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 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- AAWZDTNXLSGCEK-ZHQZDSKASA-N Quinic acid Natural products O[C@H]1CC(O)(C(O)=O)C[C@H](O)C1O AAWZDTNXLSGCEK-ZHQZDSKASA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
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- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
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- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229960004909 aminosalicylic acid Drugs 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 230000006793 arrhythmia Effects 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 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
- 239000000872 buffer Substances 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- AJPXTSMULZANCB-UHFFFAOYSA-N chlorohydroquinone Chemical compound OC1=CC=C(O)C(Cl)=C1 AJPXTSMULZANCB-UHFFFAOYSA-N 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000001035 drying Methods 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
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- YKWNUSJLICDQEO-UHFFFAOYSA-N ethoxyethane;propan-2-ol Chemical compound CC(C)O.CCOCC YKWNUSJLICDQEO-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 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
- 239000000543 intermediate Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002500 ions Chemical class 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
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 1
- 229960000990 monobenzone Drugs 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
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-M oxalate(1-) Chemical compound OC(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-M 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
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 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
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (56)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH62173A CH576438A5 (en) | 1973-01-17 | 1973-01-17 | 1-Alkylthioalkoxy-4-(3-amino-2-hydroxypropoxy) benzenes - antagonists of beta receptor stimulants prepd. e.g. by reducing corresp. Schiff base |
| AR255899A AR204334A1 (es) | 1973-01-17 | 1974-01-01 | Procedimiento para la elaboracion de compuestos del 1-(4-(alquiltio-alcoxi)-fenoxi)-2-hidroxi-3-alquil-amino-propan |
| AR255900A AR204105A1 (es) | 1973-01-17 | 1974-01-01 | Procedimiento para la preparacion del 1-(4-(2-metiltioetoxi-fenoxi)-2-hidroxi-3-isipropilaminopropano |
| AR251941A AR205618A1 (es) | 1973-01-17 | 1974-01-01 | Procedimiento para la elaboracion de derivados del 1-(4-alquiltio-alcoxi)-fenoxi - 2 - hidroxi-3-alquilaminopropano |
| AR255898A AR204726A1 (es) | 1973-01-17 | 1974-01-01 | Procedimiento para la preparacion de 1-(4-(alquiltio-alcoxi)-fenoxil)-2-hidroxi-3-alquilaminopropano |
| DE2400693A DE2400693A1 (de) | 1973-01-17 | 1974-01-08 | Neue amine und verfahren zu ihrer herstellung |
| CS7700000293A CS184348B2 (en) | 1973-01-17 | 1974-01-11 | Method for producing derivatives of 1-phenoxy-2-hydroxy-3-aminopropane |
| CS7700000290A CS184345B2 (en) | 1973-01-17 | 1974-01-11 | Method for producing derivatives of 1-phenoxy-2-hydroxy-3-aminopropane |
| CS7700000292A CS184347B2 (en) | 1973-01-17 | 1974-01-11 | Method for producing derivatives of 1-phenoxy-2-hydroxy-3-aminopropane |
| CS7400000191A CS184336B2 (en) | 1973-01-17 | 1974-01-11 | Method of producing derivatives of 1-phenoxy-2-hydroxy-3-aminopropane |
| CS7700000289A CS184344B2 (en) | 1973-01-17 | 1974-01-11 | Method for producing derivatives of 1-phenoxy-2-hydroxy-3-aminopropane |
| CS7700000294A CS184349B2 (en) | 1973-01-17 | 1974-01-11 | Method for producing derivatives of 1-phenoxy-2-hydroxy-3-aminopropane |
| CS7700000291A CS184346B2 (en) | 1973-01-17 | 1974-01-11 | Method for producing derivatives of 1-phenoxy-2-hydroxy-3-aminopropane |
| IE66/74A IE38736B1 (en) | 1973-01-17 | 1974-01-11 | Amines and processes for their manufacture |
| FR7401149A FR2213771B1 (cs) | 1973-01-17 | 1974-01-14 | |
| IL44003A IL44003A (en) | 1973-01-17 | 1974-01-14 | 1-(p-(alkylthioalkoxy)phenoxy)-3-(substituted amino)-2-propanols their preparation and pharmaceutical compositions containing them |
| CA190,087A CA1050032A (en) | 1973-01-17 | 1974-01-14 | Amines and processes for their manufacture |
| SU1985268A SU520037A3 (ru) | 1973-01-17 | 1974-01-14 | Способ получени аминов, их солей, рацематов или оптически-активных антиподов |
| AU64524/74A AU481851B2 (en) | 1973-01-17 | 1974-01-15 | Amines and processes for their manufacture |
| DD176012A DD110656A5 (cs) | 1973-01-17 | 1974-01-15 | |
| DD180359A DD113364A5 (cs) | 1973-01-17 | 1974-01-15 | |
| LU69166A LU69166A1 (cs) | 1973-01-17 | 1974-01-15 | |
| ES422301A ES422301A1 (es) | 1973-01-17 | 1974-01-15 | Procedimiento para la obtencion de nuevas aminas. |
| AT397775A AT331241B (de) | 1973-01-17 | 1974-01-16 | Verfahren zur herstellung neuer 5-((4'(alkylthioathoxy)-phenoxy)-methyl)-oxazolidine und ihrer salze |
| AT127575A AT331227B (de) | 1973-01-17 | 1974-01-16 | Verfahren zur herstellung neuer 3-(p-alkylthioalkoxy-phenoxy)-2-hydroxy-aminopropane und deren saureadditionssalze |
| HUCI1435A HU168750B (cs) | 1973-01-17 | 1974-01-16 | |
| PL1974185368A PL98965B1 (pl) | 1973-01-17 | 1974-01-16 | Sposob wytwarzania nowych pochodnych 1-fenoksy-2-hydroksy-3-aminopropanu |
| AT127675A AT329540B (de) | 1973-01-17 | 1974-01-16 | Verfahren zur herstellung neuer 3-(p-alkylthioalkoxy-phenoxy)-2-hydroxy-aminopropane und deren saureadditionssalze |
| PL1974183007A PL98225B1 (pl) | 1973-01-17 | 1974-01-16 | Sposob wytwarzania nowych pochodnych 1-fenoksy-2-hydroksy-3-aminopropanu |
| PL1974168144A PL99161B1 (pl) | 1973-01-17 | 1974-01-16 | Sposob wytwarzania nowych pochodnych 1-fenoksy-2-hydroksy-3-aminopropanu |
| ZA740307A ZA74307B (en) | 1973-01-17 | 1974-01-16 | New amines and processes for their manufacture |
| PL1974183004A PL98966B1 (pl) | 1973-01-17 | 1974-01-16 | Sposob wytwarzania nowych pochodnych 1-fenoksy-2-hydroksy-3-aminopropanu |
| PL1974183005A PL97727B1 (pl) | 1973-01-17 | 1974-01-16 | Sposob wytwarzania nowych pochodnych 1-fenoksy-2-hydroksy-3-aminopropanu |
| AT34674*#A AT329538B (de) | 1973-01-17 | 1974-01-16 | Verfahren zur herstellung neuer 3-(p-alkylthioalkoxyphenoxy)-2-hydroxy-aminopropane |
| AT127275A AT329539B (de) | 1973-01-17 | 1974-01-16 | Verfahren zur herstellung neuer 3-(p-alkylthioalkoxy-phenoxy)-2-hydroxy-aminopropane und deren saureadditionssalze |
| BE139875A BE809820A (fr) | 1973-01-17 | 1974-01-16 | Nouvelles amines et procedes pour leur preparation |
| PL1974183006A PL98065B1 (pl) | 1973-01-17 | 1974-01-16 | Sposob wytwarzania nowych pochodnych 1-fenoksy-2-hydroksy-3-aminopropanu |
| GB218774A GB1423073A (en) | 1973-01-17 | 1974-01-17 | Amines and processes for their manufacture |
| JP49007590A JPS49101343A (cs) | 1973-01-17 | 1974-01-17 | |
| NL7400648A NL7400648A (cs) | 1973-01-17 | 1974-01-17 | |
| MC1083A MC1010A1 (fr) | 1973-01-17 | 1974-01-17 | Nouvelles amines et procédés pour leur préparation |
| AR255897A AR201518A1 (es) | 1973-01-17 | 1974-10-02 | Procedimiento para la preparacion de 1-<4-(2-metil-tioetoxi)-fenoxi>-2-hidroxi-3-isopropilamino-propano |
| AR255896A AR201704A1 (es) | 1973-01-17 | 1974-10-02 | Procedimiento para la preparacion del 1-<4-(2-metil-tioetoxi)-fenoxi> -2-hidroxi-3isopropilaminopropano |
| SU2078419A SU522795A3 (ru) | 1973-01-17 | 1974-11-26 | Способ получени 1-фенокси-2окси-3-аминопропана или его солей |
| SU2078416A SU558638A3 (ru) | 1973-01-17 | 1974-11-26 | Способ получени соединений 1-фенокси-2-окси-3-аминопропана или их солей в виде рацемата или оптическиактивного антипода |
| SU2078415A SU522794A3 (ru) | 1973-01-17 | 1974-11-26 | Способ получени производных -1-фенокси-2-окси-3-аминопропана или их солей |
| SU2078418A SU518125A3 (ru) | 1973-01-17 | 1974-11-26 | Способ получени 1-фенокси-2-окси-3аминопропана или его солей |
| SU2078417A SU518124A3 (ru) | 1973-01-17 | 1974-11-26 | Способ получени 1-фенокси-2-окси3-аминопропана или его солей |
| AT127375A AT331225B (de) | 1973-01-17 | 1975-02-20 | Verfahren zur herstellung neuer 3- (p-alkylthioalkoxy-phenoxy) -2-hydroxy-aminopropane und deren saureadditionssalze |
| AT127475A AT331226B (de) | 1973-01-17 | 1975-02-20 | Verfahren zur herstellung neuer 3-(p-alkylthioalkoxy-phenoxy)-2-hydroxy-aminopropane und deren saureadditionssalze |
| AT393675A AT331793B (de) | 1973-01-17 | 1975-05-23 | Verfahren zur herstellung neuer 5-(4-(alkylthioalkoxyphenoxy)-methyl)-oxazolidine und deren salzen |
| AT393575A AT331792B (de) | 1973-01-17 | 1975-05-23 | Verfahren zur herstellung neuer 5-(4-(alkylthioalkoxyphenoxy)-methyl)-oxazolidinone |
| AT397675A AT330771B (de) | 1973-01-17 | 1975-05-26 | Verfahren zur herstellung neuer 5- ((4'-(alkyltioathoxy) phenoxy) - methyl)-oxazolidinone |
| AT397975A AT330751B (de) | 1973-01-17 | 1975-05-26 | Verfahren zur herstellung neuer 3- (p-alkylthioalkoxy-phenoxy) -2-hydroxy-aminopropane und deren saureadditionssalze |
| AT397875A AT330750B (de) | 1973-01-17 | 1975-05-26 | Verfahren zur herstellung neuer 3- (p-alkylthioalkoxyphenoxy) -2-hydroxy-aminopropane und deren saureadditionssalze |
| SU7502168216A SU576916A3 (ru) | 1973-01-17 | 1975-09-04 | Способ получени производных 1-фенокси-2-окси-3-аминопропана, их солей, рацематов или оптически-активных антиподов |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH62173A CH576438A5 (en) | 1973-01-17 | 1973-01-17 | 1-Alkylthioalkoxy-4-(3-amino-2-hydroxypropoxy) benzenes - antagonists of beta receptor stimulants prepd. e.g. by reducing corresp. Schiff base |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH576438A5 true CH576438A5 (en) | 1976-06-15 |
Family
ID=4191269
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH62173A CH576438A5 (en) | 1973-01-17 | 1973-01-17 | 1-Alkylthioalkoxy-4-(3-amino-2-hydroxypropoxy) benzenes - antagonists of beta receptor stimulants prepd. e.g. by reducing corresp. Schiff base |
Country Status (7)
| Country | Link |
|---|---|
| AT (3) | AT331241B (cs) |
| CH (1) | CH576438A5 (cs) |
| CS (6) | CS184346B2 (cs) |
| MC (1) | MC1010A1 (cs) |
| PL (6) | PL99161B1 (cs) |
| SU (6) | SU518125A3 (cs) |
| ZA (1) | ZA74307B (cs) |
-
1973
- 1973-01-17 CH CH62173A patent/CH576438A5/de not_active IP Right Cessation
-
1974
- 1974-01-11 CS CS7700000291A patent/CS184346B2/cs unknown
- 1974-01-11 CS CS7700000289A patent/CS184344B2/cs unknown
- 1974-01-11 CS CS7700000294A patent/CS184349B2/cs unknown
- 1974-01-11 CS CS7700000293A patent/CS184348B2/cs unknown
- 1974-01-11 CS CS7400000191A patent/CS184336B2/cs unknown
- 1974-01-11 CS CS7700000290A patent/CS184345B2/cs unknown
- 1974-01-16 PL PL1974168144A patent/PL99161B1/pl unknown
- 1974-01-16 PL PL1974183005A patent/PL97727B1/pl unknown
- 1974-01-16 ZA ZA740307A patent/ZA74307B/xx unknown
- 1974-01-16 PL PL1974183007A patent/PL98225B1/pl unknown
- 1974-01-16 PL PL1974183006A patent/PL98065B1/pl unknown
- 1974-01-16 AT AT397775A patent/AT331241B/de not_active IP Right Cessation
- 1974-01-16 AT AT34674*#A patent/AT329538B/de not_active IP Right Cessation
- 1974-01-16 PL PL1974183004A patent/PL98966B1/pl unknown
- 1974-01-16 PL PL1974185368A patent/PL98965B1/pl unknown
- 1974-01-17 MC MC1083A patent/MC1010A1/xx unknown
- 1974-11-26 SU SU2078418A patent/SU518125A3/ru active
- 1974-11-26 SU SU2078419A patent/SU522795A3/ru active
- 1974-11-26 SU SU2078415A patent/SU522794A3/ru active
- 1974-11-26 SU SU2078416A patent/SU558638A3/ru active
- 1974-11-26 SU SU2078417A patent/SU518124A3/ru active
-
1975
- 1975-05-23 AT AT393675A patent/AT331793B/de not_active IP Right Cessation
- 1975-09-04 SU SU7502168216A patent/SU576916A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| SU518124A3 (ru) | 1976-06-15 |
| CS184336B2 (en) | 1978-08-31 |
| ATA397775A (de) | 1975-11-15 |
| CS184349B2 (en) | 1978-08-31 |
| AT331241B (de) | 1976-08-10 |
| SU522795A3 (ru) | 1976-07-25 |
| PL98225B1 (pl) | 1978-04-29 |
| ZA74307B (en) | 1974-11-27 |
| CS184345B2 (en) | 1978-08-31 |
| PL98965B1 (pl) | 1978-06-30 |
| SU576916A3 (ru) | 1977-10-15 |
| PL97727B1 (pl) | 1978-03-30 |
| PL99161B1 (pl) | 1978-06-30 |
| SU522794A3 (ru) | 1976-07-25 |
| SU558638A3 (ru) | 1977-05-15 |
| SU518125A3 (ru) | 1976-06-15 |
| PL98966B1 (pl) | 1978-06-30 |
| ATA393675A (de) | 1975-12-15 |
| CS184348B2 (en) | 1978-08-31 |
| CS184346B2 (en) | 1978-08-31 |
| MC1010A1 (fr) | 1974-10-18 |
| ATA34674A (de) | 1975-08-15 |
| CS184344B2 (en) | 1978-08-31 |
| AT331793B (de) | 1976-08-25 |
| PL98065B1 (pl) | 1978-04-29 |
| AT329538B (de) | 1976-05-10 |
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