NO852814L - Acetyleniske fenoksypropanolderivater. - Google Patents
Acetyleniske fenoksypropanolderivater.Info
- Publication number
- NO852814L NO852814L NO852814A NO852814A NO852814L NO 852814 L NO852814 L NO 852814L NO 852814 A NO852814 A NO 852814A NO 852814 A NO852814 A NO 852814A NO 852814 L NO852814 L NO 852814L
- Authority
- NO
- Norway
- Prior art keywords
- amino
- phenyl
- propanol
- phenoxy
- dimethylethyl
- Prior art date
Links
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 29
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 58
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 49
- -1 bromo, hydroxy Chemical group 0.000 claims description 47
- 229960004592 isopropanol Drugs 0.000 claims description 38
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 32
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000005518 carboxamido group Chemical group 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 125000001589 carboacyl group Chemical group 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000004423 acyloxy group Chemical group 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 238000006467 substitution reaction Methods 0.000 claims description 5
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 4
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 4
- 125000005265 dialkylamine group Chemical group 0.000 claims description 4
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- JMAXVDBDYFOEFG-UHFFFAOYSA-N 1-(tert-butylamino)-3-[2-(2-phenylethynyl)phenoxy]propan-2-ol Chemical compound CC(C)(C)NCC(O)COC1=CC=CC=C1C#CC1=CC=CC=C1 JMAXVDBDYFOEFG-UHFFFAOYSA-N 0.000 claims description 3
- RMFRLDUXKLZOAX-UHFFFAOYSA-N 4-[2-[2-[3-(tert-butylamino)-2-hydroxypropoxy]phenyl]ethynyl]benzonitrile Chemical compound CC(C)(C)NCC(O)COC1=CC=CC=C1C#CC1=CC=C(C#N)C=C1 RMFRLDUXKLZOAX-UHFFFAOYSA-N 0.000 claims description 3
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 3
- 150000003973 alkyl amines Chemical class 0.000 claims description 3
- GHXXQFNRRSKDOP-UHFFFAOYSA-N 1-[1-(3,4-dimethoxyphenyl)propan-2-ylamino]-3-[5-methoxy-2-(2-phenylethynyl)phenoxy]propan-2-ol Chemical compound C=1C=C(OC)C(OC)=CC=1CC(C)NCC(O)COC1=CC(OC)=CC=C1C#CC1=CC=CC=C1 GHXXQFNRRSKDOP-UHFFFAOYSA-N 0.000 claims description 2
- JXGCAVLGCDWIBR-UHFFFAOYSA-N 1-[2-(2-phenylethynyl)phenoxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)COC1=CC=CC=C1C#CC1=CC=CC=C1 JXGCAVLGCDWIBR-UHFFFAOYSA-N 0.000 claims description 2
- RQWYCGVQEGLBBA-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenyl)ethylamino]-3-[5-methoxy-2-(2-phenylethynyl)phenoxy]propan-2-ol Chemical compound C=1C=C(Cl)C(Cl)=CC=1CCNCC(O)COC1=CC(OC)=CC=C1C#CC1=CC=CC=C1 RQWYCGVQEGLBBA-UHFFFAOYSA-N 0.000 claims description 2
- XYFPSWOVKSQNKR-UHFFFAOYSA-N 1-[2-(3,4-dimethoxyphenyl)ethylamino]-3-[2-[2-[4-(dimethylamino)phenyl]ethynyl]-5-methoxyphenoxy]propan-2-ol Chemical compound C=1C=C(OC)C(OC)=CC=1CCNCC(O)COC1=CC(OC)=CC=C1C#CC1=CC=C(N(C)C)C=C1 XYFPSWOVKSQNKR-UHFFFAOYSA-N 0.000 claims description 2
- AFKKLSXTJGIFQC-UHFFFAOYSA-N 1-[2-(3,4-dimethoxyphenyl)ethylamino]-3-[5-methoxy-2-(2-phenylethynyl)phenoxy]propan-2-ol Chemical compound C=1C=C(OC)C(OC)=CC=1CCNCC(O)COC1=CC(OC)=CC=C1C#CC1=CC=CC=C1 AFKKLSXTJGIFQC-UHFFFAOYSA-N 0.000 claims description 2
- UAYUONROUQDDGH-UHFFFAOYSA-N 1-[2-(3,4-dimethoxyphenyl)ethylamino]-3-[5-methoxy-2-[2-(4-methoxyphenyl)ethynyl]phenoxy]propan-2-ol Chemical compound C1=CC(OC)=CC=C1C#CC1=CC=C(OC)C=C1OCC(O)CNCCC1=CC=C(OC)C(OC)=C1 UAYUONROUQDDGH-UHFFFAOYSA-N 0.000 claims description 2
- AWKYIPSHMWQGIC-UHFFFAOYSA-N 4-[3-(tert-butylamino)-2-hydroxypropoxy]-3-(2-phenylethynyl)benzamide Chemical compound CC(C)(C)NCC(O)COC1=CC=C(C(N)=O)C=C1C#CC1=CC=CC=C1 AWKYIPSHMWQGIC-UHFFFAOYSA-N 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 2
- KTPYEESCBJLSRU-UHFFFAOYSA-N n-[3-[2-[2-[3-[2-(3,4-dimethoxyphenyl)ethylamino]-2-hydroxypropoxy]-4-methoxyphenyl]ethynyl]phenyl]acetamide Chemical compound C=1C=C(OC)C(OC)=CC=1CCNCC(O)COC1=CC(OC)=CC=C1C#CC1=CC=CC(NC(C)=O)=C1 KTPYEESCBJLSRU-UHFFFAOYSA-N 0.000 claims description 2
- NQZVVOXJKBAYLG-UHFFFAOYSA-N 1-(tert-butylamino)-3-(2-hex-1-ynylphenoxy)propan-2-ol Chemical compound CCCCC#CC1=CC=CC=C1OCC(O)CNC(C)(C)C NQZVVOXJKBAYLG-UHFFFAOYSA-N 0.000 claims 1
- DBUYAQXHGCEWCP-UHFFFAOYSA-N 1-[2-(3,4-dimethoxyphenyl)ethylamino]-3-[2-(2-phenylethynyl)phenoxy]propan-2-ol Chemical compound C1=C(OC)C(OC)=CC=C1CCNCC(O)COC1=CC=CC=C1C#CC1=CC=CC=C1 DBUYAQXHGCEWCP-UHFFFAOYSA-N 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 229940030600 antihypertensive agent Drugs 0.000 abstract description 6
- 239000002220 antihypertensive agent Substances 0.000 abstract description 6
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- OAAZUWWNSYWWHG-UHFFFAOYSA-N 1-phenoxypropan-1-ol Chemical class CCC(O)OC1=CC=CC=C1 OAAZUWWNSYWWHG-UHFFFAOYSA-N 0.000 abstract description 2
- 230000003276 anti-hypertensive effect Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000012450 pharmaceutical intermediate Substances 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 86
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 83
- 239000000243 solution Substances 0.000 description 54
- 150000001875 compounds Chemical class 0.000 description 52
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 229910001868 water Inorganic materials 0.000 description 33
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 32
- 238000002844 melting Methods 0.000 description 32
- 230000008018 melting Effects 0.000 description 32
- 239000002904 solvent Substances 0.000 description 32
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- 125000004432 carbon atom Chemical group C* 0.000 description 28
- 239000000203 mixture Substances 0.000 description 28
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
- 239000000047 product Substances 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000007787 solid Substances 0.000 description 21
- 238000012360 testing method Methods 0.000 description 20
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 19
- 239000012267 brine Substances 0.000 description 19
- 229910052802 copper Inorganic materials 0.000 description 19
- 239000010949 copper Substances 0.000 description 19
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 19
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical compound C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 18
- 230000000694 effects Effects 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- 239000003921 oil Substances 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000001914 filtration Methods 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 11
- 229910000104 sodium hydride Inorganic materials 0.000 description 11
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 11
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 229910052740 iodine Inorganic materials 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 8
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 7
- 206010020772 Hypertension Diseases 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- 239000011575 calcium Substances 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000001530 fumaric acid Substances 0.000 description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 7
- 239000011630 iodine Substances 0.000 description 7
- 235000015320 potassium carbonate Nutrition 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 230000009460 calcium influx Effects 0.000 description 6
- 229940039009 isoproterenol Drugs 0.000 description 6
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- MEWLUJUURQTTHH-UHFFFAOYSA-N 1-(tert-butylamino)-3-(2-iodophenoxy)propan-2-ol Chemical compound CC(C)(C)NCC(O)COC1=CC=CC=C1I MEWLUJUURQTTHH-UHFFFAOYSA-N 0.000 description 5
- NORYHCGEDFJNED-UHFFFAOYSA-N 2-[[2-(2-phenylethynyl)phenoxy]methyl]oxirane Chemical compound C1OC1COC1=CC=CC=C1C#CC1=CC=CC=C1 NORYHCGEDFJNED-UHFFFAOYSA-N 0.000 description 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 5
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 5
- 239000005557 antagonist Substances 0.000 description 5
- 210000000709 aorta Anatomy 0.000 description 5
- 229910052786 argon Inorganic materials 0.000 description 5
- 229910052791 calcium Inorganic materials 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 239000000825 pharmaceutical preparation Substances 0.000 description 5
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 5
- 210000001519 tissue Anatomy 0.000 description 5
- 239000003981 vehicle Substances 0.000 description 5
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 206010002383 Angina Pectoris Diseases 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 241000700199 Cavia porcellus Species 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- 239000007995 HEPES buffer Substances 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 230000004872 arterial blood pressure Effects 0.000 description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- KPCKMWGCLHYFCN-UHFFFAOYSA-N n-(3-ethynylphenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(C#C)=C1 KPCKMWGCLHYFCN-UHFFFAOYSA-N 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 230000036515 potency Effects 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 210000003437 trachea Anatomy 0.000 description 4
- CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 4
- HEROGCSJFZNHHL-UHFFFAOYSA-N 1-methoxy-2-(2-phenylethynyl)benzene Chemical compound COC1=CC=CC=C1C#CC1=CC=CC=C1 HEROGCSJFZNHHL-UHFFFAOYSA-N 0.000 description 3
- CEBKHWWANWSNTI-UHFFFAOYSA-N 2-methylbut-3-yn-2-ol Chemical compound CC(C)(O)C#C CEBKHWWANWSNTI-UHFFFAOYSA-N 0.000 description 3
- ANOUKFYBOAKOIR-UHFFFAOYSA-N 3,4-dimethoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1OC ANOUKFYBOAKOIR-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 3
- 229960004373 acetylcholine Drugs 0.000 description 3
- 150000000475 acetylene derivatives Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000007853 buffer solution Substances 0.000 description 3
- 230000003185 calcium uptake Effects 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 230000001413 cellular effect Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 230000001419 dependent effect Effects 0.000 description 3
- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- 150000002118 epoxides Chemical class 0.000 description 3
- 230000026030 halogenation Effects 0.000 description 3
- 238000005658 halogenation reaction Methods 0.000 description 3
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- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
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- MRBDMNSDAVCSSF-UHFFFAOYSA-N phentolamine Chemical compound C1=CC(C)=CC=C1N(C=1C=C(O)C=CC=1)CC1=NCCN1 MRBDMNSDAVCSSF-UHFFFAOYSA-N 0.000 description 1
- 229960001999 phentolamine Drugs 0.000 description 1
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- 239000012264 purified product Substances 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 210000001991 scapula Anatomy 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000012056 semi-solid material Substances 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000011699 spontaneously hypertensive rat Methods 0.000 description 1
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- 125000001424 substituent group Chemical group 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
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- 230000006442 vascular tone Effects 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
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/14—Preparation of carboxylic acid amides by formation of carboxamide groups together with reactions not involving the carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C233/07—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/40—Halogenated unsaturated alcohols
- C07C33/46—Halogenated unsaturated alcohols containing only six-membered aromatic rings as cyclic parts
- C07C33/48—Halogenated unsaturated alcohols containing only six-membered aromatic rings as cyclic parts with unsaturation outside the aromatic rings
- C07C33/483—Monocyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/27—Condensation of epihalohydrins or halohydrins with compounds containing active hydrogen atoms
- C07D301/28—Condensation of epihalohydrins or halohydrins with compounds containing active hydrogen atoms by reaction with hydroxyl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/36—Use of additives, e.g. for stabilisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/28—Ethers with hydroxy compounds containing oxirane rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/630,796 US4652584A (en) | 1984-07-13 | 1984-07-13 | Acetylenic phenoxypropanol derivatives and pharmaceutical compositions for the treatment of hypertension |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO852814L true NO852814L (no) | 1986-01-14 |
Family
ID=24528600
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO852814A NO852814L (no) | 1984-07-13 | 1985-07-12 | Acetyleniske fenoksypropanolderivater. |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4652584A (es) |
| EP (1) | EP0171209B1 (es) |
| KR (1) | KR860001050A (es) |
| AT (1) | ATE40987T1 (es) |
| AU (1) | AU580079B2 (es) |
| CA (1) | CA1248135A (es) |
| DE (1) | DE3568424D1 (es) |
| DK (1) | DK319785A (es) |
| ES (1) | ES8609211A1 (es) |
| FI (1) | FI852743L (es) |
| HU (1) | HUT39147A (es) |
| NO (1) | NO852814L (es) |
| NZ (1) | NZ212614A (es) |
| ZA (1) | ZA855288B (es) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5250546A (en) * | 1984-09-28 | 1993-10-05 | Nippon Chemiphar Co., Ltd. | Amino-alcohol derivatives and processes for their preparation |
| US4663334A (en) * | 1985-12-11 | 1987-05-05 | Mcneilab, Inc. | Heteroaromatic acetylenes useful as antihypertensive agents |
| US4772755A (en) * | 1987-03-19 | 1988-09-20 | Mcneilab, Inc. | 1,2-1,4 addition reaction sequence leading to disubstituted acelylenes |
| DE4210332C1 (es) * | 1992-03-30 | 1993-07-15 | Gruenenthal Gmbh, 5100 Aachen, De | |
| TW275614B (es) * | 1993-02-15 | 1996-05-11 | Senju Pharma Co | |
| AU1845395A (en) * | 1994-05-10 | 1995-11-29 | Bio-Technical Resources Lp | Formation of and dehydraton of hydroxylated diphenylacetylenes |
| WO2004009531A1 (en) * | 2002-07-24 | 2004-01-29 | Janssen Pharmaceutica N.V. | Acetylenic compounds useful in treating inflammatory disorders |
| US7022703B2 (en) * | 2003-07-24 | 2006-04-04 | Janssen Pharmaceutica, N.V. | Acetylenic compound useful in treating inflammatory disorders |
| KR102251850B1 (ko) * | 2019-05-22 | 2021-05-12 | 울산과학기술원 | 전기분해를 위한 촉매 코팅 전극, 촉매 페이스트 조성물 및 그들의 제조방법 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL6600177A (es) * | 1966-01-07 | 1967-07-10 | ||
| IE32354B1 (en) * | 1967-05-18 | 1973-07-11 | Boehringer Sohn Ingelheim | Propanolamine derivatives |
| US4010158A (en) * | 1967-05-18 | 1977-03-01 | Boehringer Ingelheim Gmbh | 1-(2'-Ethynyl-phenoxy)-2-hydroxy-3-butylamino-propanes and salts |
| US3914432A (en) * | 1967-12-13 | 1975-10-21 | Boehringer Sohn Ingelheim | Pharmaceutical compositions containing a 1-(cyano-phenoxy)-2-hydroxy-3-alkylamino-propane and method of use |
| DE1643262C3 (de) * | 1967-12-13 | 1975-06-26 | C.H. Boehringer Sohn, 6507 Ingelheim | i-Phenoxy^-hydroxy-S-alklyaminopropane, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| DE2048838A1 (de) * | 1970-10-05 | 1972-04-06 | C H Boehnnger Sohn, 6507 Ingel heim | Neue 1 Phenoxy 2 hydroxy 3 hydroxyal kylaminopropane und Verfahren zu ihrer Her stellung |
| US3959338A (en) * | 1970-10-05 | 1976-05-25 | Boehringer Ingelheim Gmbh | 1-(Cyano-phenoxy)-2-hydroxy-3-hydroxyalkylamino-propanes and salts thereof |
| DE2503222A1 (de) * | 1975-01-27 | 1976-07-29 | Boehringer Sohn Ingelheim | Verfahren zur herstellung von 1-aryl- oxy-3-n-substituierten aminopropanderivaten |
| DE3171475D1 (en) * | 1980-05-31 | 1985-08-29 | Ciba Geigy Ag | Aryl-phenyl-acetylene compounds |
-
1984
- 1984-07-13 US US06/630,796 patent/US4652584A/en not_active Expired - Lifetime
-
1985
- 1985-06-21 CA CA000484756A patent/CA1248135A/en not_active Expired
- 1985-07-01 NZ NZ212614A patent/NZ212614A/xx unknown
- 1985-07-09 ES ES545004A patent/ES8609211A1/es not_active Expired
- 1985-07-11 FI FI852743A patent/FI852743L/fi not_active Application Discontinuation
- 1985-07-12 NO NO852814A patent/NO852814L/no unknown
- 1985-07-12 DE DE8585304995T patent/DE3568424D1/de not_active Expired
- 1985-07-12 ZA ZA855288A patent/ZA855288B/xx unknown
- 1985-07-12 EP EP85304995A patent/EP0171209B1/en not_active Expired
- 1985-07-12 HU HU852695A patent/HUT39147A/hu unknown
- 1985-07-12 AU AU44871/85A patent/AU580079B2/en not_active Ceased
- 1985-07-12 AT AT85304995T patent/ATE40987T1/de active
- 1985-07-12 KR KR1019850004981A patent/KR860001050A/ko not_active Application Discontinuation
- 1985-07-12 DK DK319785A patent/DK319785A/da not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| FI852743L (fi) | 1986-01-14 |
| AU4487185A (en) | 1986-01-16 |
| KR860001050A (ko) | 1986-02-22 |
| FI852743A0 (fi) | 1985-07-11 |
| HUT39147A (en) | 1986-08-28 |
| ZA855288B (en) | 1987-02-25 |
| US4652584A (en) | 1987-03-24 |
| AU580079B2 (en) | 1988-12-22 |
| CA1248135A (en) | 1989-01-03 |
| ES545004A0 (es) | 1986-09-01 |
| ATE40987T1 (de) | 1989-03-15 |
| DK319785A (da) | 1986-01-14 |
| EP0171209B1 (en) | 1989-03-01 |
| DE3568424D1 (en) | 1989-04-06 |
| ES8609211A1 (es) | 1986-09-01 |
| NZ212614A (en) | 1989-01-06 |
| DK319785D0 (da) | 1985-07-12 |
| EP0171209A1 (en) | 1986-02-12 |
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