JPS605599B2 - アミノベンゾフエノン誘導体の製造法 - Google Patents
アミノベンゾフエノン誘導体の製造法Info
- Publication number
- JPS605599B2 JPS605599B2 JP49090566A JP9056674A JPS605599B2 JP S605599 B2 JPS605599 B2 JP S605599B2 JP 49090566 A JP49090566 A JP 49090566A JP 9056674 A JP9056674 A JP 9056674A JP S605599 B2 JPS605599 B2 JP S605599B2
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- acid
- group
- hydrogen
- formula
- 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
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical class NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 7
- 125000006239 protecting group Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- 125000005543 phthalimide group Chemical group 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 150000002475 indoles Chemical class 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 229940054051 antipsychotic indole derivative Drugs 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 239000013078 crystal Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- -1 carbobenzoxy, trityl Chemical group 0.000 description 9
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 8
- QRKJNCRCYBKANP-UHFFFAOYSA-N 2-amino-n-phenylacetamide Chemical compound NCC(=O)NC1=CC=CC=C1 QRKJNCRCYBKANP-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 229940043257 glycylglycine Drugs 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000013076 target substance Substances 0.000 description 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000001773 anti-convulsant effect Effects 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000001961 anticonvulsive agent Substances 0.000 description 2
- 229960003965 antiepileptics Drugs 0.000 description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 235000009508 confectionery Nutrition 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000004682 monohydrates Chemical class 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- BHNHHSOHWZKFOX-UHFFFAOYSA-N 2-methyl-1H-indole Chemical class C1=CC=C2NC(C)=CC2=C1 BHNHHSOHWZKFOX-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 235000017166 Bambusa arundinacea Nutrition 0.000 description 1
- 235000017491 Bambusa tulda Nutrition 0.000 description 1
- 244000241257 Cucumis melo Species 0.000 description 1
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 1
- 206010052804 Drug tolerance Diseases 0.000 description 1
- 125000002435 L-phenylalanyl group Chemical group O=C([*])[C@](N([H])[H])([H])C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 241000234435 Lilium Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 1
- 244000082204 Phyllostachys viridis Species 0.000 description 1
- 235000015334 Phyllostachys viridis Nutrition 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000011425 bamboo Substances 0.000 description 1
- IIFXYGSVEXILOC-UHFFFAOYSA-N benzyl n-[2-[[5-chloro-3-(2-chlorophenyl)-1-methylindol-2-yl]methylamino]-2-oxoethyl]carbamate Chemical compound C=1C=CC=C(Cl)C=1C=1C2=CC(Cl)=CC=C2N(C)C=1CNC(=O)CNC(=O)OCC1=CC=CC=C1 IIFXYGSVEXILOC-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 239000007952 growth promoter Substances 0.000 description 1
- 230000026781 habituation Effects 0.000 description 1
- GVLGAFRNYJVHBC-UHFFFAOYSA-N hydrate;hydrobromide Chemical compound O.Br GVLGAFRNYJVHBC-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 239000003326 hypnotic agent Substances 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- POZVCKRIQCBRBZ-UHFFFAOYSA-N n-[[5-chloro-3-(2-chlorophenyl)-1-methylindol-2-yl]methyl]-2-(tritylamino)acetamide Chemical compound C=1C=CC=C(Cl)C=1C=1C2=CC(Cl)=CC=C2N(C)C=1CNC(=O)CNC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 POZVCKRIQCBRBZ-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229960005152 pentetrazol Drugs 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000001557 phthalyl group Chemical group C(=O)(O)C1=C(C(=O)*)C=CC=C1 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 239000004089 psychotropic agent Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
Priority Applications (33)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP49090566A JPS605599B2 (ja) | 1974-08-06 | 1974-08-06 | アミノベンゾフエノン誘導体の製造法 |
| CA000232782A CA1181065A (en) | 1974-08-06 | 1975-07-31 | Dipeptide derivatives and their production |
| NLAANVRAGE7509258,A NL175789C (nl) | 1974-08-06 | 1975-08-04 | Werkwijze voor het bereiden van een farmaceutisch preparaat met kalmerende werking en werkwijze voor het bereiden van geneeskrachtige aminozuur-aniliden. |
| SE7508829A SE427030B (sv) | 1974-08-06 | 1975-08-05 | Forfarande for framstellning av bensofenonderivat med antikonvulsiv verkan |
| MX000859U MX3332E (es) | 1974-08-06 | 1975-08-05 | Procedimiento para la preparacion de derivados de dipeptido |
| HU75SI1485A HU176016B (en) | 1974-08-06 | 1975-08-05 | Process for producing dipeptide derivatives |
| AR259900A AR213076A1 (es) | 1974-08-06 | 1975-08-05 | Procedimiento para la produccion de derivados de la glicilglicilanilida sustituida |
| DK356475A DK155088C (da) | 1974-08-06 | 1975-08-05 | Analogifremgangsmaade til fremstilling af benzophenonsubstituerede dipeptidderivater eller syreadditionssalte deraf |
| ES440032A ES440032A1 (es) | 1974-08-06 | 1975-08-05 | Procedimiento para preparar derivados de dipeptido. |
| CH1020275A CH617668A5 (enrdf_load_stackoverflow) | 1974-08-06 | 1975-08-05 | |
| DE2535171A DE2535171C3 (de) | 1974-08-06 | 1975-08-06 | Benzophenon-Derivate und diese Verbindungen enthaltende Arzneimittel |
| FR7524559A FR2281131A1 (fr) | 1974-08-06 | 1975-08-06 | Derives de dipeptide et leur preparation |
| GB32916/75A GB1511669A (en) | 1974-08-06 | 1975-08-06 | Dipeptide derivatives and their production |
| DD187724A DD119213A5 (enrdf_load_stackoverflow) | 1974-08-06 | 1975-08-06 | |
| AU83734/75A AU491928B2 (en) | 1974-08-06 | 1975-08-06 | Dipeptide derivatives and their production |
| US05/716,267 US4076704A (en) | 1974-08-06 | 1976-08-20 | Dipeptide derivatives and their production |
| US05/716,266 US4076703A (en) | 1974-08-06 | 1976-08-20 | Dipeptide derivatives and their production |
| US05/716,265 US4076702A (en) | 1974-08-06 | 1976-08-20 | Dipeptide derivatives and their production |
| US05/716,268 US4076705A (en) | 1974-08-06 | 1976-08-20 | Dipeptide derivatives and their production |
| ES455506A ES455506A1 (es) | 1974-08-06 | 1977-01-31 | Procedimiento para preparar derivados de dipeptido. |
| ES455507A ES455507A1 (es) | 1974-08-06 | 1977-01-31 | Procedimiento para preparar derivados de dipeptido. |
| ES455504A ES455504A1 (es) | 1974-08-06 | 1977-01-31 | Procedimiento para preparar derivados de dipeptido. |
| ES455505A ES455505A1 (es) | 1974-08-06 | 1977-01-31 | Procedimiento para preparar derivados de dipeptido. |
| US05/775,646 US4240957A (en) | 1974-08-06 | 1977-03-07 | Dipeptide derivatives and their production |
| AR270152A AR215035A1 (es) | 1974-08-06 | 1977-11-28 | Procedimiento para la preparacion de derivados de 2-benzoil-n-alquilo(c1-c6)-n-a-(glicil)glicinanilida |
| AR270154A AR219307A1 (es) | 1974-08-06 | 1977-11-28 | Procedimiento para la preparacion de derivados de 2-benxoil-n alpha-glicil-glicil o n alpha-a-fenilalanilglicilanilida |
| AR270151A AR213453A1 (es) | 1974-08-06 | 1977-11-28 | Procedimiento para la preparacion de derivados de la glicilglicilanilida sustituida |
| AR270153A AR220325A1 (es) | 1974-08-06 | 1977-11-28 | Procedimiento para la preparacion de derivados de la glicil-glicil-2-benzoil-5-haloanilida y sus sales |
| US05/867,605 US4154727A (en) | 1974-08-06 | 1978-01-06 | Dipeptide derivatives and their production |
| CH461879A CH627439A5 (de) | 1974-08-06 | 1979-05-17 | Verfahren zur herstellung von dipeptid-derivaten. |
| CH461779A CH627438A5 (de) | 1974-08-06 | 1979-05-17 | Verfahren zur herstellung von dipeptid-derivaten. |
| CH827079A CH627440A5 (de) | 1974-08-06 | 1979-09-12 | Verfahren zur herstellung von dipeptid-derivaten. |
| CA339,232A CA1091652A (en) | 1974-08-06 | 1979-11-06 | Dipeptide derivatives and their production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP49090566A JPS605599B2 (ja) | 1974-08-06 | 1974-08-06 | アミノベンゾフエノン誘導体の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5126854A JPS5126854A (enrdf_load_stackoverflow) | 1976-03-05 |
| JPS605599B2 true JPS605599B2 (ja) | 1985-02-12 |
Family
ID=14001969
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP49090566A Expired JPS605599B2 (ja) | 1974-08-06 | 1974-08-06 | アミノベンゾフエノン誘導体の製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS605599B2 (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63148389U (enrdf_load_stackoverflow) * | 1987-03-20 | 1988-09-29 | ||
| JPS63148387U (enrdf_load_stackoverflow) * | 1987-03-20 | 1988-09-29 |
-
1974
- 1974-08-06 JP JP49090566A patent/JPS605599B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5126854A (enrdf_load_stackoverflow) | 1976-03-05 |
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