JPS637179B2 - - Google Patents
Info
- Publication number
- JPS637179B2 JPS637179B2 JP55051615A JP5161580A JPS637179B2 JP S637179 B2 JPS637179 B2 JP S637179B2 JP 55051615 A JP55051615 A JP 55051615A JP 5161580 A JP5161580 A JP 5161580A JP S637179 B2 JPS637179 B2 JP S637179B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- benzyloxy
- formula
- represented
- methoxy
- 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 76
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical class NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 167
- 239000000243 solution Substances 0.000 description 58
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 57
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 55
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 38
- 239000010410 layer Substances 0.000 description 37
- 239000002904 solvent Substances 0.000 description 31
- 238000001816 cooling Methods 0.000 description 28
- 238000005406 washing Methods 0.000 description 28
- 238000003756 stirring Methods 0.000 description 27
- 238000001035 drying Methods 0.000 description 26
- 238000000862 absorption spectrum Methods 0.000 description 25
- 239000007788 liquid Substances 0.000 description 23
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 23
- 239000000126 substance Substances 0.000 description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 19
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 19
- 235000017557 sodium bicarbonate Nutrition 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- SCZVXVGZMZRGRU-UHFFFAOYSA-N n'-ethylethane-1,2-diamine Chemical compound CCNCCN SCZVXVGZMZRGRU-UHFFFAOYSA-N 0.000 description 14
- 238000000921 elemental analysis Methods 0.000 description 13
- 229910052739 hydrogen Inorganic materials 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 12
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 230000003197 catalytic effect Effects 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 238000005984 hydrogenation reaction Methods 0.000 description 9
- 238000010992 reflux Methods 0.000 description 8
- 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 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000000202 analgesic effect Effects 0.000 description 6
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 4
- WXWWJUKMWNYILA-UHFFFAOYSA-N 2-(4-methoxy-3-phenylmethoxyphenyl)acetic acid Chemical compound COC1=CC=C(CC(O)=O)C=C1OCC1=CC=CC=C1 WXWWJUKMWNYILA-UHFFFAOYSA-N 0.000 description 3
- DOZZSWAOPDYVLH-UHFFFAOYSA-N 2-phenylpropanamide Chemical compound NC(=O)C(C)C1=CC=CC=C1 DOZZSWAOPDYVLH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- XOKSFWXNWWRRAF-UHFFFAOYSA-N 2-(4-methoxy-2-phenylmethoxyphenyl)acetic acid Chemical compound COC1=CC=C(CC(O)=O)C(OCC=2C=CC=CC=2)=C1 XOKSFWXNWWRRAF-UHFFFAOYSA-N 0.000 description 2
- SXICKTXWIPUULA-UHFFFAOYSA-N 2-(4-methoxyphenyl)-2-phenylmethoxyacetamide Chemical compound C1=CC(OC)=CC=C1C(C(N)=O)OCC1=CC=CC=C1 SXICKTXWIPUULA-UHFFFAOYSA-N 0.000 description 2
- QSIDMIUHTJZNJL-UHFFFAOYSA-N 2-(5-methoxy-2-phenylmethoxyphenyl)acetic acid Chemical compound COc1ccc(OCc2ccccc2)c(CC(O)=O)c1 QSIDMIUHTJZNJL-UHFFFAOYSA-N 0.000 description 2
- 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 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-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
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 238000007112 amidation reaction Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 150000004682 monohydrates Chemical class 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
- 239000011541 reaction mixture Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- JWPSFGPOYDDVKX-UHFFFAOYSA-N 2-(2-acetyloxy-3-methoxyphenyl)acetic acid Chemical compound COC1=CC=CC(CC(O)=O)=C1OC(C)=O JWPSFGPOYDDVKX-UHFFFAOYSA-N 0.000 description 1
- KJDKYXFNTLVSTN-UHFFFAOYSA-N 2-(3-methoxy-2-phenylmethoxyphenyl)acetic acid Chemical compound COC1=CC=CC(CC(O)=O)=C1OCC1=CC=CC=C1 KJDKYXFNTLVSTN-UHFFFAOYSA-N 0.000 description 1
- AYCIHUSEBJLTBF-UHFFFAOYSA-N 2-(3-methoxy-4-phenylmethoxyphenyl)acetic acid Chemical compound COC1=CC(CC(O)=O)=CC=C1OCC1=CC=CC=C1 AYCIHUSEBJLTBF-UHFFFAOYSA-N 0.000 description 1
- WOKIXVCKEQWAGT-UHFFFAOYSA-N 2-(3-methoxy-4-phenylmethoxyphenyl)propanoic acid Chemical compound COC1=CC(C(C)C(O)=O)=CC=C1OCC1=CC=CC=C1 WOKIXVCKEQWAGT-UHFFFAOYSA-N 0.000 description 1
- OLWASSNQLAKLLD-UHFFFAOYSA-N 2-(4-acetyloxy-3-ethoxyphenyl)acetic acid Chemical compound CCOC1=CC(CC(O)=O)=CC=C1OC(C)=O OLWASSNQLAKLLD-UHFFFAOYSA-N 0.000 description 1
- QLJMBAXRCXCSGZ-UHFFFAOYSA-N 2-(4-acetyloxy-3-methoxyphenyl)acetic acid Chemical compound COC1=CC(CC(O)=O)=CC=C1OC(C)=O QLJMBAXRCXCSGZ-UHFFFAOYSA-N 0.000 description 1
- OUWYQMVFJMJAJG-UHFFFAOYSA-N 2-(4-ethoxy-3-phenylmethoxyphenyl)acetic acid Chemical compound CCOC1=CC=C(CC(O)=O)C=C1OCC1=CC=CC=C1 OUWYQMVFJMJAJG-UHFFFAOYSA-N 0.000 description 1
- LNWWGHNQLOXRTF-UHFFFAOYSA-N 2-chloro-n-(2-phenylethyl)acetamide Chemical compound ClCC(=O)NCCC1=CC=CC=C1 LNWWGHNQLOXRTF-UHFFFAOYSA-N 0.000 description 1
- KZHUULABPNPTEO-UHFFFAOYSA-N 2-methoxy-2-phenylacetamide Chemical compound COC(C(N)=O)C1=CC=CC=C1 KZHUULABPNPTEO-UHFFFAOYSA-N 0.000 description 1
- KUKSPRRZVLBAEX-UHFFFAOYSA-N 2-methoxy-2-phenylacetyl chloride Chemical compound COC(C(Cl)=O)C1=CC=CC=C1 KUKSPRRZVLBAEX-UHFFFAOYSA-N 0.000 description 1
- FOTITZRWZUAVPH-UHFFFAOYSA-N 2-phenylpropanoyl chloride Chemical compound ClC(=O)C(C)C1=CC=CC=C1 FOTITZRWZUAVPH-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
- XMDRIXFLMHBVFA-UHFFFAOYSA-N COc1ccc(cc1OCc1ccccc1)C(C)C(O)=O Chemical compound COc1ccc(cc1OCc1ccccc1)C(C)C(O)=O XMDRIXFLMHBVFA-UHFFFAOYSA-N 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-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
- 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
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003874 central nervous system depressant Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 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
- 150000002148 esters Chemical class 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 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
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- OHZZTXYKLXZFSZ-UHFFFAOYSA-I manganese(3+) 5,10,15-tris(1-methylpyridin-1-ium-4-yl)-20-(1-methylpyridin-4-ylidene)porphyrin-22-ide pentachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mn+3].C1=CN(C)C=CC1=C1C(C=C2)=NC2=C(C=2C=C[N+](C)=CC=2)C([N-]2)=CC=C2C(C=2C=C[N+](C)=CC=2)=C(C=C2)N=C2C(C=2C=C[N+](C)=CC=2)=C2N=C1C=C2 OHZZTXYKLXZFSZ-UHFFFAOYSA-I 0.000 description 1
- 238000004519 manufacturing process 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
- MNGSQDPALGOGAA-UHFFFAOYSA-N n'-(cyclopropylmethyl)-n-(2-phenylethyl)-n'-propylethane-1,2-diamine Chemical compound C1CC1CN(CCC)CCNCCC1=CC=CC=C1 MNGSQDPALGOGAA-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
- NKQVVWKVCXJXFR-UHFFFAOYSA-N n'-[2-(4-methoxyphenyl)ethyl]ethane-1,2-diamine Chemical compound COC1=CC=C(CCNCCN)C=C1 NKQVVWKVCXJXFR-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
- 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 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
- 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 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 210000002966 serum Anatomy 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
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5161580A JPS56147752A (en) | 1980-04-21 | 1980-04-21 | Novel phenylacetamide derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5161580A JPS56147752A (en) | 1980-04-21 | 1980-04-21 | Novel phenylacetamide derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56147752A JPS56147752A (en) | 1981-11-16 |
| JPS637179B2 true JPS637179B2 (enrdf_load_stackoverflow) | 1988-02-15 |
Family
ID=12891792
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5161580A Granted JPS56147752A (en) | 1980-04-21 | 1980-04-21 | Novel phenylacetamide derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS56147752A (enrdf_load_stackoverflow) |
-
1980
- 1980-04-21 JP JP5161580A patent/JPS56147752A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56147752A (en) | 1981-11-16 |
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