JPS6151580B2 - - Google Patents
Info
- Publication number
- JPS6151580B2 JPS6151580B2 JP10365278A JP10365278A JPS6151580B2 JP S6151580 B2 JPS6151580 B2 JP S6151580B2 JP 10365278 A JP10365278 A JP 10365278A JP 10365278 A JP10365278 A JP 10365278A JP S6151580 B2 JPS6151580 B2 JP S6151580B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- lower alkoxy
- carbamoyl
- formula
- acetamide
- 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
- 150000001875 compounds Chemical class 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 208000025865 Ulcer Diseases 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 11
- 231100000397 ulcer Toxicity 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- HIFIMKOUMQSRKJ-UHFFFAOYSA-N 4-chloro-2-[[2-[2-(3,4-dimethoxyphenyl)ethylamino]-2-oxoethyl]amino]benzamide Chemical compound C1=C(OC)C(OC)=CC=C1CCNC(=O)CNC1=CC(Cl)=CC=C1C(N)=O HIFIMKOUMQSRKJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- WEQRLEDPPGQGOP-UHFFFAOYSA-N N-Acetylhomoveratrylamine Chemical compound COC1=CC=C(CCNC(C)=O)C=C1OC WEQRLEDPPGQGOP-UHFFFAOYSA-N 0.000 claims 4
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- 239000013078 crystal Substances 0.000 description 12
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- ANOUKFYBOAKOIR-UHFFFAOYSA-N 3,4-dimethoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1OC ANOUKFYBOAKOIR-UHFFFAOYSA-N 0.000 description 10
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 10
- 230000000694 effects Effects 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 8
- 238000000921 elemental analysis Methods 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 230000009858 acid secretion Effects 0.000 description 7
- -1 amine compound Chemical class 0.000 description 7
- 230000000767 anti-ulcer Effects 0.000 description 7
- 238000000354 decomposition reaction Methods 0.000 description 7
- 229940079593 drug Drugs 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- 210000002784 stomach Anatomy 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 238000001647 drug administration Methods 0.000 description 5
- QNEJYHVIYJFNHC-UHFFFAOYSA-N 2-amino-4-chlorobenzamide Chemical compound NC(=O)C1=CC=C(Cl)C=C1N QNEJYHVIYJFNHC-UHFFFAOYSA-N 0.000 description 4
- KZOFCELNVLSKGC-UHFFFAOYSA-N 3-[[2-[2-(3,4-dimethoxyphenyl)ethylamino]-2-oxoethyl]amino]benzamide Chemical compound C1=C(OC)C(OC)=CC=C1CCNC(=O)CNC1=CC=CC(C(N)=O)=C1 KZOFCELNVLSKGC-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000003699 antiulcer agent Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 230000027119 gastric acid secretion Effects 0.000 description 4
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 4
- 235000009518 sodium iodide Nutrition 0.000 description 4
- SKOXCZCFHALHMY-UHFFFAOYSA-N 2-(3-carbamoylanilino)acetic acid Chemical compound NC(=O)C1=CC=CC(NCC(O)=O)=C1 SKOXCZCFHALHMY-UHFFFAOYSA-N 0.000 description 3
- 239000004471 Glycine Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 229960003638 dopamine Drugs 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- PVGJEFCALWNVLV-UHFFFAOYSA-N methyl 2-(3-carbamoylanilino)acetate Chemical compound COC(=O)CNC1=CC=CC(C(N)=O)=C1 PVGJEFCALWNVLV-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- GSCPDZHWVNUUFI-UHFFFAOYSA-N 3-aminobenzamide Chemical compound NC(=O)C1=CC=CC(N)=C1 GSCPDZHWVNUUFI-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 102000004877 Insulin Human genes 0.000 description 2
- 108090001061 Insulin Proteins 0.000 description 2
- 206010042220 Stress ulcer Diseases 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 208000000718 duodenal ulcer Diseases 0.000 description 2
- 210000001198 duodenum Anatomy 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 229940125396 insulin Drugs 0.000 description 2
- 239000007928 intraperitoneal injection Substances 0.000 description 2
- 238000010253 intravenous injection Methods 0.000 description 2
- 230000003902 lesion Effects 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- BGRJTUBHPOOWDU-NSHDSACASA-N (S)-(-)-sulpiride Chemical compound CCN1CCC[C@H]1CNC(=O)C1=CC(S(N)(=O)=O)=CC=C1OC BGRJTUBHPOOWDU-NSHDSACASA-N 0.000 description 1
- LWWZZAIYYGROKY-UHFFFAOYSA-N 2-(2-carbamoyl-5-chloroanilino)acetic acid Chemical compound NC(=O)C1=CC=C(Cl)C=C1NCC(O)=O LWWZZAIYYGROKY-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- WWBJEBQJHYKQHM-UHFFFAOYSA-N 2-chloro-n-[2-(3,4-dimethoxyphenyl)ethyl]acetamide Chemical compound COC1=CC=C(CCNC(=O)CCl)C=C1OC WWBJEBQJHYKQHM-UHFFFAOYSA-N 0.000 description 1
- DUIWVCASVUBFSH-UHFFFAOYSA-N 4-(3,4-dimethoxyphenyl)butanamide Chemical compound COC1=CC=C(CCCC(N)=O)C=C1OC DUIWVCASVUBFSH-UHFFFAOYSA-N 0.000 description 1
- KKADPXVIOXHVKN-UHFFFAOYSA-N 4-hydroxyphenylpyruvic acid Chemical compound OC(=O)C(=O)CC1=CC=C(O)C=C1 KKADPXVIOXHVKN-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 description 1
- MODKMHXGCGKTLE-UHFFFAOYSA-N N-acetylphenylethylamine Chemical class CC(=O)NCCC1=CC=CC=C1 MODKMHXGCGKTLE-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 238000000692 Student's t-test Methods 0.000 description 1
- 231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 1
- 238000011047 acute toxicity test Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229940069428 antacid Drugs 0.000 description 1
- 239000003159 antacid agent Substances 0.000 description 1
- 230000002467 anti-pepsin effect Effects 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000008499 blood brain barrier function Effects 0.000 description 1
- 210000001218 blood-brain barrier Anatomy 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 210000002318 cardia Anatomy 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 210000003238 esophagus Anatomy 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002332 glycine derivatives Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 150000002497 iodine compounds Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- QABLOFMHHSOFRJ-UHFFFAOYSA-N methyl 2-chloroacetate Chemical compound COC(=O)CCl QABLOFMHHSOFRJ-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 210000001187 pylorus Anatomy 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229960004940 sulpiride Drugs 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000012353 t test Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 210000002417 xiphoid bone Anatomy 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
- 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)
Priority Applications (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP10365278A JPS5531027A (en) | 1978-08-25 | 1978-08-25 | N-phenetyl acetamide derivative |
ZA00794245A ZA794245B (en) | 1978-08-25 | 1979-08-14 | N-phenethylacetamide compounds and process for preparation thereof |
DK343479A DK149748C (da) | 1978-08-25 | 1979-08-16 | Analogifremgangsmaade til fremstilling af n-phenethylacetamidforbindelser |
CA000333939A CA1110628A (en) | 1978-08-25 | 1979-08-16 | N-phenethylacetamide compounds and process for preparation thereof |
ES483484A ES483484A1 (es) | 1978-08-25 | 1979-08-20 | Procedimiento para la produccion de compuestos de n-feneti- lacetamida |
EP79103116A EP0009608B1 (en) | 1978-08-25 | 1979-08-23 | N-phenethylacetamide compounds, processes for their preparation and therapeutic compositions containing them |
DE7979103116T DE2962567D1 (en) | 1978-08-25 | 1979-08-23 | N-phenethylacetamide compounds, processes for their preparation and therapeutic compositions containing them |
AT0570879A AT367397B (de) | 1978-08-25 | 1979-08-24 | Verfahren zur herstellung von neuen n-phenaethyl- glycinamiden |
US06/070,085 US4297357A (en) | 1978-08-25 | 1979-08-27 | N-Phenethylacetamide compounds and process for preparation thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP10365278A JPS5531027A (en) | 1978-08-25 | 1978-08-25 | N-phenetyl acetamide derivative |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5531027A JPS5531027A (en) | 1980-03-05 |
JPS6151580B2 true JPS6151580B2 (pt) | 1986-11-10 |
Family
ID=14359701
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP10365278A Granted JPS5531027A (en) | 1978-08-25 | 1978-08-25 | N-phenetyl acetamide derivative |
Country Status (2)
Country | Link |
---|---|
JP (1) | JPS5531027A (pt) |
ZA (1) | ZA794245B (pt) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2810667B2 (ja) * | 1988-03-08 | 1998-10-15 | 第一製薬株式会社 | アミノ安息香酸誘導体 |
JP2612417B2 (ja) * | 1993-04-28 | 1997-05-21 | 第一製薬株式会社 | 消化器症状改善剤 |
EP0697215A1 (en) * | 1993-04-28 | 1996-02-21 | Daiichi Pharmaceutical Co., Ltd. | Digestive symptom ameliorant |
-
1978
- 1978-08-25 JP JP10365278A patent/JPS5531027A/ja active Granted
-
1979
- 1979-08-14 ZA ZA00794245A patent/ZA794245B/xx unknown
Also Published As
Publication number | Publication date |
---|---|
ZA794245B (en) | 1980-12-31 |
JPS5531027A (en) | 1980-03-05 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
SU820659A3 (ru) | Способ получени производных 4-амино- 5-АлКилСульфОНилОАНизАМидОВ, иХ СОлЕй,ОКиСЕй, лЕВО- и пРАВОВРАщАющиХизОМЕРОВ /иХ ВАРиАНТы/ | |
JPH04235149A (ja) | アシル化合物 | |
AU657498B2 (en) | Biphenylyl compounds | |
JPH0557983B2 (pt) | ||
JPS6229566A (ja) | 新規グアニジノメチル安息香酸誘導体 | |
KR100457240B1 (ko) | 치환 벤조일아미노티아졸 유도체 및 그것을 함유하는 의약 | |
SU1635899A3 (ru) | Способ получени 3-[(1Н-имидазол-4-ил)метил]-2-оксибензолметанолов | |
JPH0460597B2 (pt) | ||
JPS6151580B2 (pt) | ||
EP0009608B1 (en) | N-phenethylacetamide compounds, processes for their preparation and therapeutic compositions containing them | |
JPH0433793B2 (pt) | ||
JPH05310745A (ja) | ジエラジラクトンおよび抗炎症剤 | |
JPS6312063B2 (pt) | ||
JPH0692948A (ja) | 新規なアセタミド誘導体及びその用途 | |
CA2006728A1 (en) | Carboxylic acid derivatives | |
JP2589245B2 (ja) | N−(3−アルキル(またはアルケニル)−4−ヒドロキシベンゾイル)グリシン亜鉛錯体 | |
JPS63218652A (ja) | 新規グアニジノメチル安息香酸誘導体およびこれを含有する消化性潰瘍治療剤 | |
JPS631938B2 (pt) | ||
JPS62108863A (ja) | 2−ピリジル酢酸誘導体、その製法およびそれを含む医薬 | |
JPH025755B2 (pt) | ||
JPH052675B2 (pt) | ||
KR820001614B1 (ko) | N-펜에틸 아세트아미드 화합물의 제조방법 | |
JPS6330462A (ja) | 新規グアニジノメチルベンツアミド誘導体およびそれを有効成分とする抗潰瘍剤 | |
JP2524752B2 (ja) | フリルメチルチオエ−テル誘導体 | |
CA1198734A (en) | Three polyumorphic forms of 5-[3-(2,2,2- trifluoroethyl]guanidino)-pyrazol-1-yl)-valeramide |