JPS637180B2 - - Google Patents
Info
- Publication number
- JPS637180B2 JPS637180B2 JP6757380A JP6757380A JPS637180B2 JP S637180 B2 JPS637180 B2 JP S637180B2 JP 6757380 A JP6757380 A JP 6757380A JP 6757380 A JP6757380 A JP 6757380A JP S637180 B2 JPS637180 B2 JP S637180B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- oxyphenylacetamide
- derivative
- solution
- reduced pressure
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- -1 tetrahydrofurfuryl group Chemical group 0.000 claims description 80
- 150000001875 compounds Chemical class 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 239000013543 active substance Substances 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 488
- 239000000243 solution Substances 0.000 description 176
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 141
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 108
- 239000010410 layer Substances 0.000 description 101
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 93
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 72
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 68
- 238000005406 washing Methods 0.000 description 64
- 239000002904 solvent Substances 0.000 description 63
- 238000003756 stirring Methods 0.000 description 58
- 238000000862 absorption spectrum Methods 0.000 description 53
- 238000001035 drying Methods 0.000 description 53
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 51
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 51
- 238000001816 cooling Methods 0.000 description 50
- 239000007788 liquid Substances 0.000 description 48
- 239000000126 substance Substances 0.000 description 48
- 238000006243 chemical reaction Methods 0.000 description 47
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 41
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 34
- 235000017557 sodium bicarbonate Nutrition 0.000 description 34
- 238000000921 elemental analysis Methods 0.000 description 31
- 229910052739 hydrogen Inorganic materials 0.000 description 31
- 229910052757 nitrogen Inorganic materials 0.000 description 29
- YASYEJJMZJALEJ-UHFFFAOYSA-N Citric acid monohydrate Chemical compound O.OC(=O)CC(O)(C(O)=O)CC(O)=O YASYEJJMZJALEJ-UHFFFAOYSA-N 0.000 description 26
- 239000000203 mixture Substances 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000002253 acid Substances 0.000 description 24
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 22
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 18
- SCZVXVGZMZRGRU-UHFFFAOYSA-N n'-ethylethane-1,2-diamine Chemical compound CCNCCN SCZVXVGZMZRGRU-UHFFFAOYSA-N 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 14
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical class NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 11
- 239000013078 crystal Substances 0.000 description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 9
- KZHUULABPNPTEO-UHFFFAOYSA-N 2-methoxy-2-phenylacetamide Chemical compound COC(C(N)=O)C1=CC=CC=C1 KZHUULABPNPTEO-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 230000000202 analgesic effect Effects 0.000 description 8
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- ZKQHTZSGNLANQM-UHFFFAOYSA-N 2-phenyl-2-propoxyacetamide Chemical compound CCCOC(C(N)=O)C1=CC=CC=C1 ZKQHTZSGNLANQM-UHFFFAOYSA-N 0.000 description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 229960002179 ephedrine Drugs 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- FCZWNTWSYOQRRZ-UHFFFAOYSA-N (2-amino-2-oxo-1-phenylethyl) acetate Chemical compound CC(=O)OC(C(N)=O)C1=CC=CC=C1 FCZWNTWSYOQRRZ-UHFFFAOYSA-N 0.000 description 3
- BERNQQVIUAZUHY-UHFFFAOYSA-N (2-chloro-2-oxo-1-phenylethyl) acetate Chemical compound CC(=O)OC(C(Cl)=O)C1=CC=CC=C1 BERNQQVIUAZUHY-UHFFFAOYSA-N 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 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
- 239000012141 concentrate Substances 0.000 description 3
- 230000000254 damaging effect Effects 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- MTEDGCWFXFZDAW-UHFFFAOYSA-N n'-methyl-n'-(oxolan-2-ylmethyl)-n-(2-phenylethyl)ethane-1,2-diamine Chemical compound C1CCOC1CN(C)CCNCCC1=CC=CC=C1 MTEDGCWFXFZDAW-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- OLKQIWCQICCYQS-UHFFFAOYSA-N 2-(4-methoxyphenyl)acetamide Chemical compound COC1=CC=C(CC(N)=O)C=C1 OLKQIWCQICCYQS-UHFFFAOYSA-N 0.000 description 2
- LNWWGHNQLOXRTF-UHFFFAOYSA-N 2-chloro-n-(2-phenylethyl)acetamide Chemical compound ClCC(=O)NCCC1=CC=CC=C1 LNWWGHNQLOXRTF-UHFFFAOYSA-N 0.000 description 2
- TYCLTFHVSLLNIM-UHFFFAOYSA-N 2-ethoxy-2-(4-methoxyphenyl)acetic acid Chemical compound CCOC(C(O)=O)C1=CC=C(OC)C=C1 TYCLTFHVSLLNIM-UHFFFAOYSA-N 0.000 description 2
- UTXDFAIVUCLQER-UHFFFAOYSA-N 2-hydroxy-2-(4-methoxyphenyl)acetamide Chemical compound COC1=CC=C(C(O)C(N)=O)C=C1 UTXDFAIVUCLQER-UHFFFAOYSA-N 0.000 description 2
- ITECRQOOEQWFPE-UHFFFAOYSA-N 2-hydroxy-2-(4-methoxyphenyl)acetic acid Chemical compound COC1=CC=C(C(O)C(O)=O)C=C1 ITECRQOOEQWFPE-UHFFFAOYSA-N 0.000 description 2
- KUKSPRRZVLBAEX-UHFFFAOYSA-N 2-methoxy-2-phenylacetyl chloride Chemical compound COC(C(Cl)=O)C1=CC=CC=C1 KUKSPRRZVLBAEX-UHFFFAOYSA-N 0.000 description 2
- SYVQJLVWLPTGJH-UHFFFAOYSA-N 2-phenyl-2-propoxyacetic acid Chemical compound CCCOC(C(O)=O)C1=CC=CC=C1 SYVQJLVWLPTGJH-UHFFFAOYSA-N 0.000 description 2
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 2
- 102000004420 Creatine Kinase Human genes 0.000 description 2
- 108010042126 Creatine kinase Proteins 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 2
- BLAKAEFIFWAFGH-UHFFFAOYSA-N acetyl acetate;pyridine Chemical compound C1=CC=NC=C1.CC(=O)OC(C)=O BLAKAEFIFWAFGH-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 238000007112 amidation reaction Methods 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- IWYDHOAUDWTVEP-UHFFFAOYSA-N mandelic acid Chemical compound OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- ILJXHCMEQDJHBT-UHFFFAOYSA-N n'-(cyclopropylmethyl)-n'-methyl-n-(2-phenylethyl)ethane-1,2-diamine Chemical compound C1CC1CN(C)CCNCCC1=CC=CC=C1 ILJXHCMEQDJHBT-UHFFFAOYSA-N 0.000 description 2
- JPTIDUOYXJPZEM-UHFFFAOYSA-N n-[2-(4-methoxyphenyl)ethyl]-n'-methyl-n'-(oxolan-2-ylmethyl)ethane-1,2-diamine Chemical compound C1=CC(OC)=CC=C1CCNCCN(C)CC1OCCC1 JPTIDUOYXJPZEM-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- KWGRBVOPPLSCSI-PSASIEDQSA-N (1s,2r)-2-(methylamino)-1-phenylpropan-1-ol Chemical compound CN[C@H](C)[C@@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-PSASIEDQSA-N 0.000 description 1
- RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 description 1
- CQNIKSXVOOXRSR-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetamide Chemical compound COC(OC)(C(N)=O)C1=CC=CC=C1 CQNIKSXVOOXRSR-UHFFFAOYSA-N 0.000 description 1
- KWOMTIVNNYNALW-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-2-methoxyacetic acid Chemical compound COC(C(O)=O)C1=CC=C2OCOC2=C1 KWOMTIVNNYNALW-UHFFFAOYSA-N 0.000 description 1
- GIRXKOJKVUCAIB-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)acetamide Chemical compound NC(=O)CC1=CC=C2OCOC2=C1 GIRXKOJKVUCAIB-UHFFFAOYSA-N 0.000 description 1
- ARLMZLOJPBMKDL-UHFFFAOYSA-N 2-(3,5-dimethoxyphenyl)-2-ethoxyacetic acid Chemical compound CCOC(C(O)=O)C1=CC(OC)=CC(OC)=C1 ARLMZLOJPBMKDL-UHFFFAOYSA-N 0.000 description 1
- WVZWBFAZRSHDQA-UHFFFAOYSA-N 2-(3,5-dimethoxyphenyl)-2-hydroxyacetic acid Chemical compound COC1=CC(OC)=CC(C(O)C(O)=O)=C1 WVZWBFAZRSHDQA-UHFFFAOYSA-N 0.000 description 1
- MEWFVBGJPWIEQL-UHFFFAOYSA-N 2-(4-ethoxy-3-methoxyphenyl)-2-hydroxyacetic acid Chemical compound CCOC1=CC=C(C(O)C(O)=O)C=C1OC MEWFVBGJPWIEQL-UHFFFAOYSA-N 0.000 description 1
- QWCRGALPJIRGTD-UHFFFAOYSA-N 2-(4-ethoxyphenyl)-2-hydroxyacetic acid Chemical compound CCOC1=CC=C(C(O)C(O)=O)C=C1 QWCRGALPJIRGTD-UHFFFAOYSA-N 0.000 description 1
- UHWCKIPLXDQZMD-UHFFFAOYSA-N 2-(4-hydroxyphenyl)-2-methoxyacetic acid Chemical compound COC(C(O)=O)C1=CC=C(O)C=C1 UHWCKIPLXDQZMD-UHFFFAOYSA-N 0.000 description 1
- GKRUGKLQIHGWAM-UHFFFAOYSA-N 2-ethoxy-2-(3-hydroxy-4-methoxyphenyl)acetic acid Chemical compound CCOC(C(O)=O)C1=CC=C(OC)C(O)=C1 GKRUGKLQIHGWAM-UHFFFAOYSA-N 0.000 description 1
- AMVSTQCMPAXYSQ-UHFFFAOYSA-N 2-ethoxy-2-(4-hydroxyphenyl)acetic acid Chemical compound CCOC(C(O)=O)C1=CC=C(O)C=C1 AMVSTQCMPAXYSQ-UHFFFAOYSA-N 0.000 description 1
- VDMSJBDZBGKULL-UHFFFAOYSA-N 2-ethoxy-2-phenylacetamide Chemical compound CCOC(C(N)=O)C1=CC=CC=C1 VDMSJBDZBGKULL-UHFFFAOYSA-N 0.000 description 1
- XBLYVSAKBBNYDO-UHFFFAOYSA-N 2-ethoxy-2-phenylacetic acid Chemical compound CCOC(C(O)=O)C1=CC=CC=C1 XBLYVSAKBBNYDO-UHFFFAOYSA-N 0.000 description 1
- JMBPBGJXFSBHEE-UHFFFAOYSA-N 2-hydroxy-2-(3-methoxyphenyl)acetamide Chemical compound COC1=CC=CC(C(O)C(N)=O)=C1 JMBPBGJXFSBHEE-UHFFFAOYSA-N 0.000 description 1
- UBHMYNPCDNGWBM-UHFFFAOYSA-N 2-hydroxy-2-(4-propoxyphenyl)acetic acid Chemical compound CCCOC1=CC=C(C(O)C(O)=O)C=C1 UBHMYNPCDNGWBM-UHFFFAOYSA-N 0.000 description 1
- YTAXBENGUQQEEQ-UHFFFAOYSA-N 2-hydroxy-2-phenyl-n-(2-phenylethyl)butanamide Chemical compound C=1C=CC=CC=1C(O)(CC)C(=O)NCCC1=CC=CC=C1 YTAXBENGUQQEEQ-UHFFFAOYSA-N 0.000 description 1
- KHJLUGZFVDFOKZ-UHFFFAOYSA-N 2-hydroxy-2-phenylbutanamide Chemical compound CCC(O)(C(N)=O)C1=CC=CC=C1 KHJLUGZFVDFOKZ-UHFFFAOYSA-N 0.000 description 1
- CLUJFRCEPFNVHW-UHFFFAOYSA-N 3,4-methylenedioxymandelic acid Chemical compound OC(=O)C(O)C1=CC=C2OCOC2=C1 CLUJFRCEPFNVHW-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- RGUKYNXWOWSRET-UHFFFAOYSA-N 4-pyrrolidin-1-ylpyridine Chemical compound C1CCCN1C1=CC=NC=C1 RGUKYNXWOWSRET-UHFFFAOYSA-N 0.000 description 1
- 101800004538 Bradykinin Proteins 0.000 description 1
- BYNPFVZNGBARNN-UHFFFAOYSA-N C(C1=CC=CC=C1)OC(C(=O)N)C1=CC(=CC=C1)OC Chemical compound C(C1=CC=CC=C1)OC(C(=O)N)C1=CC(=CC=C1)OC BYNPFVZNGBARNN-UHFFFAOYSA-N 0.000 description 1
- DZJMXHNNKNXBLJ-UHFFFAOYSA-N Cl.COC(C(=O)N)C1=CC=CC=C1 Chemical compound Cl.COC(C(=O)N)C1=CC=CC=C1 DZJMXHNNKNXBLJ-UHFFFAOYSA-N 0.000 description 1
- DIWVBIXQCNRCFE-UHFFFAOYSA-N DL-alpha-Methoxyphenylacetic acid Chemical compound COC(C(O)=O)C1=CC=CC=C1 DIWVBIXQCNRCFE-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- QXZGBUJJYSLZLT-UHFFFAOYSA-N H-Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg-OH Natural products NC(N)=NCCCC(N)C(=O)N1CCCC1C(=O)N1C(C(=O)NCC(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CO)C(=O)N2C(CCC2)C(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CCCN=C(N)N)C(O)=O)CCC1 QXZGBUJJYSLZLT-UHFFFAOYSA-N 0.000 description 1
- 102100035792 Kininogen-1 Human genes 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- NVBOEGNMVKLHOS-UHFFFAOYSA-N [2-oxo-1-phenyl-2-(2-phenylethylamino)ethyl] acetate Chemical compound C=1C=CC=CC=1C(OC(=O)C)C(=O)NCCC1=CC=CC=C1 NVBOEGNMVKLHOS-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 230000002238 attenuated effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- SKZBHTOTTJKKDY-UHFFFAOYSA-N benzene;butanoic acid Chemical compound CCCC(O)=O.C1=CC=CC=C1 SKZBHTOTTJKKDY-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- QXZGBUJJYSLZLT-FDISYFBBSA-N bradykinin Chemical compound NC(=N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1[C@H](C(=O)NCC(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CO)C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)CCC1 QXZGBUJJYSLZLT-FDISYFBBSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- OQNGCCWBHLEQFN-UHFFFAOYSA-N chloroform;hexane Chemical compound ClC(Cl)Cl.CCCCCC OQNGCCWBHLEQFN-UHFFFAOYSA-N 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 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
- WDCDAAMJNUHOIY-UHFFFAOYSA-N ethyl acetate;2-propan-2-yloxypropane Chemical compound CCOC(C)=O.CC(C)OC(C)C WDCDAAMJNUHOIY-UHFFFAOYSA-N 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- SKHIBNDAFWIOPB-UHFFFAOYSA-N hydron;2-phenylethanamine;chloride Chemical compound Cl.NCCC1=CC=CC=C1 SKHIBNDAFWIOPB-UHFFFAOYSA-N 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- CPCHVLBDLZEKTD-UHFFFAOYSA-N n'-(2-phenylethyl)ethane-1,2-diamine Chemical compound NCCNCCC1=CC=CC=C1 CPCHVLBDLZEKTD-UHFFFAOYSA-N 0.000 description 1
- KJLCRHAWLXTUFG-UHFFFAOYSA-N n'-(cyclopropylmethyl)-n'-ethyl-n-(2-phenylethyl)ethane-1,2-diamine Chemical compound C1CC1CN(CC)CCNCCC1=CC=CC=C1 KJLCRHAWLXTUFG-UHFFFAOYSA-N 0.000 description 1
- GOIPUSWXLNKTTE-UHFFFAOYSA-N n'-(cyclopropylmethyl)-n'-ethyl-n-[2-(4-methoxyphenyl)ethyl]ethane-1,2-diamine Chemical compound C1CC1CN(CC)CCNCCC1=CC=C(OC)C=C1 GOIPUSWXLNKTTE-UHFFFAOYSA-N 0.000 description 1
- PEUZQYALMDKFMZ-UHFFFAOYSA-N n'-(cyclopropylmethyl)-n-[2-(4-ethoxyphenyl)ethyl]-n'-methylethane-1,2-diamine Chemical compound C1=CC(OCC)=CC=C1CCNCCN(C)CC1CC1 PEUZQYALMDKFMZ-UHFFFAOYSA-N 0.000 description 1
- MZGRQKHCEVWXMK-UHFFFAOYSA-N n'-(cyclopropylmethyl)-n-[2-(4-methoxyphenyl)ethyl]-n'-propylethane-1,2-diamine Chemical compound C1CC1CN(CCC)CCNCCC1=CC=C(OC)C=C1 MZGRQKHCEVWXMK-UHFFFAOYSA-N 0.000 description 1
- BQOOXZZNPIJRAN-UHFFFAOYSA-N n'-(oxolan-2-ylmethyl)-n-(2-phenylethyl)-n'-propylethane-1,2-diamine Chemical compound C1CCOC1CN(CCC)CCNCCC1=CC=CC=C1 BQOOXZZNPIJRAN-UHFFFAOYSA-N 0.000 description 1
- ARQQAMRDNYNXMH-UHFFFAOYSA-N n'-ethyl-n'-(oxolan-2-ylmethyl)-n-(2-phenylethyl)ethane-1,2-diamine Chemical compound C1CCOC1CN(CC)CCNCCC1=CC=CC=C1 ARQQAMRDNYNXMH-UHFFFAOYSA-N 0.000 description 1
- CJBHBXRPFIQUTH-UHFFFAOYSA-N n'-ethyl-n-[2-(4-methoxyphenyl)ethyl]-n'-(oxolan-2-ylmethyl)ethane-1,2-diamine Chemical compound C1CCOC1CN(CC)CCNCCC1=CC=C(OC)C=C1 CJBHBXRPFIQUTH-UHFFFAOYSA-N 0.000 description 1
- JMXUJUQOHFDHMC-UHFFFAOYSA-N n-[2-(4-ethoxyphenyl)ethyl]-n'-methyl-n'-(oxolan-2-ylmethyl)ethane-1,2-diamine Chemical compound C1=CC(OCC)=CC=C1CCNCCN(C)CC1OCCC1 JMXUJUQOHFDHMC-UHFFFAOYSA-N 0.000 description 1
- WDDYPHUOAHGAKR-UHFFFAOYSA-N n-[2-(4-methoxyphenyl)ethyl]-n'-(oxolan-2-ylmethyl)-n'-propylethane-1,2-diamine Chemical compound C1CCOC1CN(CCC)CCNCCC1=CC=C(OC)C=C1 WDDYPHUOAHGAKR-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Furan Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6757380A JPS56164157A (en) | 1980-05-20 | 1980-05-20 | Novel-alpha-oxyphenylacetamide derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6757380A JPS56164157A (en) | 1980-05-20 | 1980-05-20 | Novel-alpha-oxyphenylacetamide derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56164157A JPS56164157A (en) | 1981-12-17 |
| JPS637180B2 true JPS637180B2 (enrdf_load_stackoverflow) | 1988-02-15 |
Family
ID=13348819
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6757380A Granted JPS56164157A (en) | 1980-05-20 | 1980-05-20 | Novel-alpha-oxyphenylacetamide derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS56164157A (enrdf_load_stackoverflow) |
-
1980
- 1980-05-20 JP JP6757380A patent/JPS56164157A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56164157A (en) | 1981-12-17 |
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