JPS6237032B2 - - Google Patents
Info
- Publication number
- JPS6237032B2 JPS6237032B2 JP2257179A JP2257179A JPS6237032B2 JP S6237032 B2 JPS6237032 B2 JP S6237032B2 JP 2257179 A JP2257179 A JP 2257179A JP 2257179 A JP2257179 A JP 2257179A JP S6237032 B2 JPS6237032 B2 JP S6237032B2
- Authority
- JP
- Japan
- Prior art keywords
- guanidinobenzoyloxy
- acid
- addition salt
- acid addition
- guanidinobenzoic
- 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
- 239000002253 acid Substances 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 12
- FCEQRBOTYXIORK-UHFFFAOYSA-N 2-(diaminomethylideneamino)benzoic acid Chemical class NC(=N)NC1=CC=CC=C1C(O)=O FCEQRBOTYXIORK-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- YFUQTMNUQVFBBS-UHFFFAOYSA-N (4-sulfamoylphenyl) 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(N=C(N)N)=CC=C1C(=O)OC1=CC=C(S(N)(=O)=O)C=C1 YFUQTMNUQVFBBS-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- YCMLQMDWSXFTIF-UHFFFAOYSA-N 2-methylbenzenesulfonimidic acid Chemical compound CC1=CC=CC=C1S(N)(=O)=O YCMLQMDWSXFTIF-UHFFFAOYSA-N 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 239000013078 crystal Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- -1 That is Chemical group 0.000 description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- CGQXODYXKCGVJV-UHFFFAOYSA-N 4-(diaminomethylideneamino)benzoyl chloride Chemical compound NC(N)=NC1=CC=C(C(Cl)=O)C=C1 CGQXODYXKCGVJV-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 102000004142 Trypsin Human genes 0.000 description 4
- 108090000631 Trypsin Proteins 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 229940012957 plasmin Drugs 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-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
- 229940079593 drug Drugs 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000012588 trypsin Substances 0.000 description 3
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- JBSRWFDTGDGNLG-UHFFFAOYSA-N 4-(diaminomethylideneamino)benzoyl chloride;hydrochloride Chemical compound Cl.NC(=N)NC1=CC=C(C(Cl)=O)C=C1 JBSRWFDTGDGNLG-UHFFFAOYSA-N 0.000 description 2
- SXTSBZBQQRIYCU-UHFFFAOYSA-N 4-guanidinobenzoic acid Chemical compound NC(=N)NC1=CC=C(C(O)=O)C=C1 SXTSBZBQQRIYCU-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- AGJQVFDKHHNRRR-UHFFFAOYSA-N 2-(diaminomethylideneamino)benzoyl chloride;hydrochloride Chemical compound Cl.NC(N)=NC1=CC=CC=C1C(Cl)=O AGJQVFDKHHNRRR-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- RHPDIBUPEZIAAU-UHFFFAOYSA-N 4-hydroxy-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(O)C=C1 RHPDIBUPEZIAAU-UHFFFAOYSA-N 0.000 description 1
- DIRCLGLKRZLKHG-UHFFFAOYSA-N 4-hydroxybenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C(O)C=C1 DIRCLGLKRZLKHG-UHFFFAOYSA-N 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
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 206010033645 Pancreatitis Diseases 0.000 description 1
- 206010033647 Pancreatitis acute Diseases 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- AAYFRLMXUYDMMG-UHFFFAOYSA-N [4-(butan-2-ylsulfamoyl)phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(S(=O)(=O)NC(C)CC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 AAYFRLMXUYDMMG-UHFFFAOYSA-N 0.000 description 1
- JPGDBQMCMOHGJN-UHFFFAOYSA-N [4-(butylsulfamoyl)phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(S(=O)(=O)NCCCC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 JPGDBQMCMOHGJN-UHFFFAOYSA-N 0.000 description 1
- BWRCEBPVDSZVAY-UHFFFAOYSA-N [4-(ethylsulfamoyl)phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(S(=O)(=O)NCC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 BWRCEBPVDSZVAY-UHFFFAOYSA-N 0.000 description 1
- WCRUAZLSCNPINA-UHFFFAOYSA-N [4-(methylsulfamoyl)phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(S(=O)(=O)NC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 WCRUAZLSCNPINA-UHFFFAOYSA-N 0.000 description 1
- RFJPPSBLGGVRSR-UHFFFAOYSA-N [4-(propan-2-ylsulfamoyl)phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(S(=O)(=O)NC(C)C)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 RFJPPSBLGGVRSR-UHFFFAOYSA-N 0.000 description 1
- LGAKPCIDNADZFK-UHFFFAOYSA-N [4-(propylsulfamoyl)phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(S(=O)(=O)NCCC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 LGAKPCIDNADZFK-UHFFFAOYSA-N 0.000 description 1
- XDJGEDXMMDAWEY-UHFFFAOYSA-N [4-(tert-butylsulfamoyl)phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(S(=O)(=O)NC(C)(C)C)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 XDJGEDXMMDAWEY-UHFFFAOYSA-N 0.000 description 1
- BUNUZNQBNMBTOS-UHFFFAOYSA-N [4-[butyl(ethyl)sulfamoyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(S(=O)(=O)N(CC)CCCC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 BUNUZNQBNMBTOS-UHFFFAOYSA-N 0.000 description 1
- KFLPEURXZCBICA-UHFFFAOYSA-N [4-[butyl(methyl)sulfamoyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(S(=O)(=O)N(C)CCCC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 KFLPEURXZCBICA-UHFFFAOYSA-N 0.000 description 1
- FIUIYNYXJSAWSQ-UHFFFAOYSA-N [4-[butyl(propyl)sulfamoyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(S(=O)(=O)N(CCC)CCCC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 FIUIYNYXJSAWSQ-UHFFFAOYSA-N 0.000 description 1
- FPFWKTPKCHHPGK-UHFFFAOYSA-N [4-[ethyl(methyl)sulfamoyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(S(=O)(=O)N(C)CC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 FPFWKTPKCHHPGK-UHFFFAOYSA-N 0.000 description 1
- HETVLUQITRTHIO-UHFFFAOYSA-N [4-[ethyl(propan-2-yl)sulfamoyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(S(=O)(=O)N(C(C)C)CC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 HETVLUQITRTHIO-UHFFFAOYSA-N 0.000 description 1
- IILZPOAPVBXRBQ-UHFFFAOYSA-N [4-[ethyl(propyl)sulfamoyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(S(=O)(=O)N(CC)CCC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 IILZPOAPVBXRBQ-UHFFFAOYSA-N 0.000 description 1
- ZUMMMQAOCNLWOC-UHFFFAOYSA-N [4-[methyl(propan-2-yl)sulfamoyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(S(=O)(=O)N(C)C(C)C)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 ZUMMMQAOCNLWOC-UHFFFAOYSA-N 0.000 description 1
- PBOIUCAZZXTWGD-UHFFFAOYSA-N [4-[methyl(propyl)sulfamoyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(S(=O)(=O)N(C)CCC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 PBOIUCAZZXTWGD-UHFFFAOYSA-N 0.000 description 1
- XPBLLVZUOYHPCC-UHFFFAOYSA-N [4-[propan-2-yl(propyl)sulfamoyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(S(=O)(=O)N(C(C)C)CCC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 XPBLLVZUOYHPCC-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 201000003229 acute pancreatitis Diseases 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
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-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
- 239000003054 catalyst Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 208000031169 hemorrhagic disease Diseases 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2257179A JPS55115865A (en) | 1979-03-01 | 1979-03-01 | Guanidinobenzoic acid derivative and its preparation |
| GB8003854A GB2044760B (en) | 1979-03-01 | 1980-02-05 | Guanidinobenzoic acid derivatives |
| DE19803005580 DE3005580A1 (de) | 1979-03-01 | 1980-02-14 | Guanidinobenzoesaeurederivate, verfahren zu ihrer herstellung und diese derivate enthaltende arzneimittel |
| US06/123,609 US4283418A (en) | 1979-03-01 | 1980-02-22 | Guanidinobenzoic acid derivatives and process for their preparation |
| FR8004573A FR2450251A1 (fr) | 1979-03-01 | 1980-02-29 | Derives de l'acide guanidinobenzoique, procede pour leur preparation et compositions pharmaceutiques les contenant |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2257179A JPS55115865A (en) | 1979-03-01 | 1979-03-01 | Guanidinobenzoic acid derivative and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55115865A JPS55115865A (en) | 1980-09-06 |
| JPS6237032B2 true JPS6237032B2 (enrdf_load_stackoverflow) | 1987-08-10 |
Family
ID=12086555
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2257179A Granted JPS55115865A (en) | 1979-03-01 | 1979-03-01 | Guanidinobenzoic acid derivative and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS55115865A (enrdf_load_stackoverflow) |
-
1979
- 1979-03-01 JP JP2257179A patent/JPS55115865A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS55115865A (en) | 1980-09-06 |
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