JPS6155498B2 - - Google Patents
Info
- Publication number
- JPS6155498B2 JPS6155498B2 JP54040735A JP4073579A JPS6155498B2 JP S6155498 B2 JPS6155498 B2 JP S6155498B2 JP 54040735 A JP54040735 A JP 54040735A JP 4073579 A JP4073579 A JP 4073579A JP S6155498 B2 JPS6155498 B2 JP S6155498B2
- Authority
- JP
- Japan
- Prior art keywords
- represented
- formula
- benzene
- derivative according
- methyl
- 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
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical class NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 claims description 22
- -1 tetrahydrofurfuryl group Chemical group 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 92
- 239000000243 solution Substances 0.000 description 52
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 238000001816 cooling Methods 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 18
- NRPFNQUDKRYCNX-UHFFFAOYSA-N 4-methoxyphenylacetic acid Chemical compound COC1=CC=C(CC(O)=O)C=C1 NRPFNQUDKRYCNX-UHFFFAOYSA-N 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 14
- 238000000862 absorption spectrum Methods 0.000 description 13
- 238000000921 elemental analysis Methods 0.000 description 13
- 229910052739 hydrogen Inorganic materials 0.000 description 13
- 239000010410 layer Substances 0.000 description 13
- 239000007788 liquid Substances 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- 239000000203 mixture Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 238000004440 column chromatography Methods 0.000 description 9
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 9
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 8
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 8
- MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 230000000202 analgesic effect Effects 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- QFGBDACEUAGHQU-UHFFFAOYSA-N n'-(cyclopropylmethyl)-n-(2,3-dihydro-1h-inden-2-yl)-n'-methylethane-1,2-diamine Chemical compound C1C2=CC=CC=C2CC1NCCN(C)CC1CC1 QFGBDACEUAGHQU-UHFFFAOYSA-N 0.000 description 4
- XFPJLBSJSDCJMU-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-n'-methyl-n'-(oxolan-2-ylmethyl)ethane-1,2-diamine Chemical compound C1C2=CC=CC=C2CC1NCCN(C)CC1CCCO1 XFPJLBSJSDCJMU-UHFFFAOYSA-N 0.000 description 4
- 229960003424 phenylacetic acid Drugs 0.000 description 4
- 239000003279 phenylacetic acid Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- ZVVWZNFSMIFGEP-UHFFFAOYSA-N 2-(4-ethoxyphenyl)acetic acid Chemical compound CCOC1=CC=C(CC(O)=O)C=C1 ZVVWZNFSMIFGEP-UHFFFAOYSA-N 0.000 description 2
- LEGPZHPSIPPYIO-UHFFFAOYSA-N 3-Methoxyphenylacetic acid Chemical compound COC1=CC=CC(CC(O)=O)=C1 LEGPZHPSIPPYIO-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- QDHFDXDMKYJPSC-UHFFFAOYSA-N N-ethylphenylacetamide Chemical compound CCNC(=O)CC1=CC=CC=C1 QDHFDXDMKYJPSC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 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
- RAPIPBRHRYSAHQ-UHFFFAOYSA-N 2-(2,5-dimethoxyphenyl)acetyl chloride Chemical compound COC1=CC=C(OC)C(CC(Cl)=O)=C1 RAPIPBRHRYSAHQ-UHFFFAOYSA-N 0.000 description 1
- ABROWERIMKBDEW-UHFFFAOYSA-N 2-(2-ethoxyphenyl)acetic acid Chemical compound CCOC1=CC=CC=C1CC(O)=O ABROWERIMKBDEW-UHFFFAOYSA-N 0.000 description 1
- IVEWTCACRDEAOB-UHFFFAOYSA-N 2-(2-methoxyphenyl)acetic acid Chemical compound COC1=CC=CC=C1CC(O)=O IVEWTCACRDEAOB-UHFFFAOYSA-N 0.000 description 1
- UPEWDRCXLROYOF-UHFFFAOYSA-N 2-(2-methoxyphenyl)acetyl chloride Chemical compound COC1=CC=CC=C1CC(Cl)=O UPEWDRCXLROYOF-UHFFFAOYSA-N 0.000 description 1
- QBJIMTPENIGDOG-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)acetyl chloride Chemical compound COC1=CC=C(CC(Cl)=O)C=C1OC QBJIMTPENIGDOG-UHFFFAOYSA-N 0.000 description 1
- JTSHPHZFTSLRTL-UHFFFAOYSA-N 2-(3,5-diethoxyphenyl)acetic acid Chemical compound CCOC1=CC(CC(O)=O)=CC(OCC)=C1 JTSHPHZFTSLRTL-UHFFFAOYSA-N 0.000 description 1
- FFPAFDDLAGTGPQ-UHFFFAOYSA-N 2-(3,5-dimethoxyphenyl)acetic acid Chemical compound COC1=CC(CC(O)=O)=CC(OC)=C1 FFPAFDDLAGTGPQ-UHFFFAOYSA-N 0.000 description 1
- HRFLULLBPLPBSW-UHFFFAOYSA-N 2-(3-ethoxyphenyl)acetic acid Chemical compound CCOC1=CC=CC(CC(O)=O)=C1 HRFLULLBPLPBSW-UHFFFAOYSA-N 0.000 description 1
- ULLCOWORODEDBK-UHFFFAOYSA-N 2-(4-propoxyphenyl)acetic acid Chemical compound CCCOC1=CC=C(CC(O)=O)C=C1 ULLCOWORODEDBK-UHFFFAOYSA-N 0.000 description 1
- YJEFUGPGWXNGTO-UHFFFAOYSA-N 2-(4-propoxyphenyl)acetyl chloride Chemical compound CCCOC1=CC=C(CC(Cl)=O)C=C1 YJEFUGPGWXNGTO-UHFFFAOYSA-N 0.000 description 1
- VXWYQEYFYNAZOD-UHFFFAOYSA-N 2-[3-[(4,4-difluoropiperidin-1-yl)methyl]-4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound FC1(F)CCN(CC2=NN(CC(=O)N3CCC4=C(C3)N=NN4)C=C2C2=CN=C(NC3CC4=C(C3)C=CC=C4)N=C2)CC1 VXWYQEYFYNAZOD-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
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-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
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 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
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 1
- OQNGCCWBHLEQFN-UHFFFAOYSA-N chloroform;hexane Chemical compound ClC(Cl)Cl.CCCCCC OQNGCCWBHLEQFN-UHFFFAOYSA-N 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- GJANTPSJGSXSDO-UHFFFAOYSA-N n',n'-diethyl-n-(1,2,3,4-tetrahydronaphthalen-1-ylmethyl)ethane-1,2-diamine Chemical compound C1=CC=C2C(CNCCN(CC)CC)CCCC2=C1 GJANTPSJGSXSDO-UHFFFAOYSA-N 0.000 description 1
- XMHWCFGQDSVSOI-UHFFFAOYSA-N n'-(cyclopropylmethyl)-n-(2,3-dihydro-1h-inden-1-ylmethyl)-n'-methylethane-1,2-diamine Chemical compound C1CC2=CC=CC=C2C1CNCCN(C)CC1CC1 XMHWCFGQDSVSOI-UHFFFAOYSA-N 0.000 description 1
- WITWIBORFDYHHP-UHFFFAOYSA-N n'-methyl-n'-(oxolan-2-ylmethyl)ethane-1,2-diamine Chemical compound NCCN(C)CC1CCCO1 WITWIBORFDYHHP-UHFFFAOYSA-N 0.000 description 1
- AIDBTLZTSFVXDH-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-1-ylmethyl)-n'-methyl-n'-(oxolan-2-ylmethyl)ethane-1,2-diamine Chemical compound C1CC2=CC=CC=C2C1CNCCN(C)CC1CCCO1 AIDBTLZTSFVXDH-UHFFFAOYSA-N 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- IFXDDAVRUDKPBW-UHFFFAOYSA-N phenyl acetate;hydrochloride Chemical compound Cl.CC(=O)OC1=CC=CC=C1 IFXDDAVRUDKPBW-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Landscapes
- Furan Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4073579A JPS55162760A (en) | 1979-04-04 | 1979-04-04 | Phenylacetamide derivative |
| EP80300817A EP0017376A1 (en) | 1979-03-30 | 1980-03-18 | Phenylacetamide compounds and an analgesic composition containing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4073579A JPS55162760A (en) | 1979-04-04 | 1979-04-04 | Phenylacetamide derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55162760A JPS55162760A (en) | 1980-12-18 |
| JPS6155498B2 true JPS6155498B2 (enrdf_load_stackoverflow) | 1986-11-28 |
Family
ID=12588883
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4073579A Granted JPS55162760A (en) | 1979-03-30 | 1979-04-04 | Phenylacetamide derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS55162760A (enrdf_load_stackoverflow) |
-
1979
- 1979-04-04 JP JP4073579A patent/JPS55162760A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS55162760A (en) | 1980-12-18 |
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