JPS6141510B2 - - Google Patents
Info
- Publication number
- JPS6141510B2 JPS6141510B2 JP2257279A JP2257279A JPS6141510B2 JP S6141510 B2 JPS6141510 B2 JP S6141510B2 JP 2257279 A JP2257279 A JP 2257279A JP 2257279 A JP2257279 A JP 2257279A JP S6141510 B2 JPS6141510 B2 JP S6141510B2
- Authority
- JP
- Japan
- Prior art keywords
- guanidinobenzoyloxy
- phenyl
- acid
- general formula
- 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
- 150000001875 compounds Chemical class 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 8
- FCEQRBOTYXIORK-UHFFFAOYSA-N 2-(diaminomethylideneamino)benzoic acid Chemical class NC(=N)NC1=CC=CC=C1C(O)=O FCEQRBOTYXIORK-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- LUJRZCRNVQVAJL-UHFFFAOYSA-N [4-[2-(dimethylamino)-2-oxoethyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(CC(=O)N(C)C)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 LUJRZCRNVQVAJL-UHFFFAOYSA-N 0.000 claims description 2
- RHSKWNYWYHHLCN-UHFFFAOYSA-N [4-[2-(methylamino)-2-oxoethyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(CC(=O)NC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 RHSKWNYWYHHLCN-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 2
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- IMNDHOCGZLYMRO-UHFFFAOYSA-N n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=CC=C1 IMNDHOCGZLYMRO-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- -1 etc. Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229940012957 plasmin Drugs 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 102000004142 Trypsin Human genes 0.000 description 5
- 108090000631 Trypsin Proteins 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 239000012588 trypsin Substances 0.000 description 4
- 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 3
- SXTSBZBQQRIYCU-UHFFFAOYSA-N 4-guanidinobenzoic acid Chemical compound NC(=N)NC1=CC=C(C(O)=O)C=C1 SXTSBZBQQRIYCU-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 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
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-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
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 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
- 239000007788 liquid Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QFKUAWGKUZXVPH-UHFFFAOYSA-N (4-carbamoylphenyl) 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(NC(=N)N)=CC=C1C(=O)OC1=CC=C(C(N)=O)C=C1 QFKUAWGKUZXVPH-UHFFFAOYSA-N 0.000 description 1
- 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
- BLUITXBEAKYQKE-UHFFFAOYSA-N 2-(4-hydroxyphenyl)-n,n-dimethylacetamide Chemical compound CN(C)C(=O)CC1=CC=C(O)C=C1 BLUITXBEAKYQKE-UHFFFAOYSA-N 0.000 description 1
- DVYKQANXDBJSGF-UHFFFAOYSA-N 2-(4-hydroxyphenyl)-n-methylacetamide Chemical compound CNC(=O)CC1=CC=C(O)C=C1 DVYKQANXDBJSGF-UHFFFAOYSA-N 0.000 description 1
- RVVOUCISDHTCFM-UHFFFAOYSA-N 2-(diaminomethylideneamino)benzoyl chloride Chemical compound NC(N)=NC1=CC=CC=C1C(Cl)=O RVVOUCISDHTCFM-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
- 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 1
- UREWDFSPQSEPQJ-UHFFFAOYSA-N 4-hydroxy-2,3-dimethylbenzamide Chemical compound CC1=C(C)C(C(N)=O)=CC=C1O UREWDFSPQSEPQJ-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 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
- 102000008946 Fibrinogen Human genes 0.000 description 1
- 108010049003 Fibrinogen Proteins 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
- QDHFDXDMKYJPSC-UHFFFAOYSA-N N-ethylphenylacetamide Chemical compound CCNC(=O)CC1=CC=CC=C1 QDHFDXDMKYJPSC-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
- 102000005686 Serum Globulins Human genes 0.000 description 1
- 108010045362 Serum Globulins Proteins 0.000 description 1
- 108010023197 Streptokinase Proteins 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
- BBJCATVAWXEZKO-UHFFFAOYSA-N [4-(1-amino-1-oxopropan-2-yl)phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C(C(N)=O)C)=CC=C1OC(=O)C1=CC=C(N=C(N)N)C=C1 BBJCATVAWXEZKO-UHFFFAOYSA-N 0.000 description 1
- PVEWKZXLSXHCMX-UHFFFAOYSA-N [4-(2-amino-2-oxoethyl)phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(CC(=O)N)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 PVEWKZXLSXHCMX-UHFFFAOYSA-N 0.000 description 1
- QOQKWBCCRLYBQR-UHFFFAOYSA-N [4-(3-amino-3-oxoprop-1-enyl)phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(N=C(N)N)=CC=C1C(=O)OC1=CC=C(C=CC(N)=O)C=C1 QOQKWBCCRLYBQR-UHFFFAOYSA-N 0.000 description 1
- SPMRLPLIMFHNLM-UHFFFAOYSA-N [4-(butan-2-ylcarbamoyl)phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C(=O)NC(C)CC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 SPMRLPLIMFHNLM-UHFFFAOYSA-N 0.000 description 1
- MXDXMVRFRLEHHR-UHFFFAOYSA-N [4-(butylcarbamoyl)phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C(=O)NCCCC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 MXDXMVRFRLEHHR-UHFFFAOYSA-N 0.000 description 1
- NTNIXAJBXFEHFS-UHFFFAOYSA-N [4-(dibutylcarbamoyl)phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C(=O)N(CCCC)CCCC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 NTNIXAJBXFEHFS-UHFFFAOYSA-N 0.000 description 1
- MPIGIBZWPLXXDW-UHFFFAOYSA-N [4-(diethylcarbamoyl)phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 MPIGIBZWPLXXDW-UHFFFAOYSA-N 0.000 description 1
- AAUROPLRWFXHDH-UHFFFAOYSA-N [4-(dimethylcarbamoyl)phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C(=O)N(C)C)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 AAUROPLRWFXHDH-UHFFFAOYSA-N 0.000 description 1
- OHMDUXIKWZMGHO-UHFFFAOYSA-N [4-(dipropylcarbamoyl)phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C(=O)N(CCC)CCC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 OHMDUXIKWZMGHO-UHFFFAOYSA-N 0.000 description 1
- KYGBNTHQTNBOBY-UHFFFAOYSA-N [4-(ethylcarbamoyl)phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C(=O)NCC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 KYGBNTHQTNBOBY-UHFFFAOYSA-N 0.000 description 1
- VJJPOFQRODXRQX-UHFFFAOYSA-N [4-(methylcarbamoyl)phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C(=O)NC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 VJJPOFQRODXRQX-UHFFFAOYSA-N 0.000 description 1
- WFZUKOGRDFWKFV-UHFFFAOYSA-N [4-(propan-2-ylcarbamoyl)phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C(=O)NC(C)C)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 WFZUKOGRDFWKFV-UHFFFAOYSA-N 0.000 description 1
- GOLXZISWTSFYFY-UHFFFAOYSA-N [4-(propylcarbamoyl)phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C(=O)NCCC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 GOLXZISWTSFYFY-UHFFFAOYSA-N 0.000 description 1
- FYYNXYPPNUVDHO-UHFFFAOYSA-N [4-(tert-butylcarbamoyl)phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C(=O)NC(C)(C)C)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 FYYNXYPPNUVDHO-UHFFFAOYSA-N 0.000 description 1
- FVCFFPSSJQCPGK-UHFFFAOYSA-N [4-[1-(dibutylamino)-1-oxopropan-2-yl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C(C)C(=O)N(CCCC)CCCC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 FVCFFPSSJQCPGK-UHFFFAOYSA-N 0.000 description 1
- CHMPDNLENJBGMF-UHFFFAOYSA-N [4-[1-(diethylamino)-1-oxopropan-2-yl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C(C)C(=O)N(CC)CC)=CC=C1OC(=O)C1=CC=C(N=C(N)N)C=C1 CHMPDNLENJBGMF-UHFFFAOYSA-N 0.000 description 1
- DCJKCPQAIURNEP-UHFFFAOYSA-N [4-[1-(dipropylamino)-1-oxopropan-2-yl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C(C)C(=O)N(CCC)CCC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 DCJKCPQAIURNEP-UHFFFAOYSA-N 0.000 description 1
- JRCDXMKUZXTIFZ-UHFFFAOYSA-N [4-[1-(ethylamino)-1-oxopropan-2-yl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C(C)C(=O)NCC)=CC=C1OC(=O)C1=CC=C(N=C(N)N)C=C1 JRCDXMKUZXTIFZ-UHFFFAOYSA-N 0.000 description 1
- YECUKQZBNJMSMI-UHFFFAOYSA-N [4-[1-(methylamino)-1-oxopropan-2-yl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C(C)C(=O)NC)=CC=C1OC(=O)C1=CC=C(N=C(N)N)C=C1 YECUKQZBNJMSMI-UHFFFAOYSA-N 0.000 description 1
- XWMPNGLODMURLF-UHFFFAOYSA-N [4-[1-[di(propan-2-yl)amino]-1-oxopropan-2-yl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C(C)C(=O)N(C(C)C)C(C)C)=CC=C1OC(=O)C1=CC=C(N=C(N)N)C=C1 XWMPNGLODMURLF-UHFFFAOYSA-N 0.000 description 1
- VEBXBQOACFTSEP-UHFFFAOYSA-N [4-[1-[methyl(propyl)amino]-1-oxopropan-2-yl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C(C)C(=O)N(C)CCC)=CC=C1OC(=O)C1=CC=C(N=C(N)N)C=C1 VEBXBQOACFTSEP-UHFFFAOYSA-N 0.000 description 1
- WDGHQLJBSFOGQL-UHFFFAOYSA-N [4-[1-oxo-1-(propan-2-ylamino)propan-2-yl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C(C)C(=O)NC(C)C)=CC=C1OC(=O)C1=CC=C(N=C(N)N)C=C1 WDGHQLJBSFOGQL-UHFFFAOYSA-N 0.000 description 1
- RNQZEARLCIARGL-UHFFFAOYSA-N [4-[1-oxo-1-(propylamino)propan-2-yl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C(C)C(=O)NCCC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 RNQZEARLCIARGL-UHFFFAOYSA-N 0.000 description 1
- CVAUWBXEPVHOGC-UHFFFAOYSA-N [4-[2-(butan-2-ylamino)-2-oxoethyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(CC(=O)NC(C)CC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 CVAUWBXEPVHOGC-UHFFFAOYSA-N 0.000 description 1
- TYFANUNRPCECFR-UHFFFAOYSA-N [4-[2-(diethylamino)-2-oxoethyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(CC(=O)N(CC)CC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 TYFANUNRPCECFR-UHFFFAOYSA-N 0.000 description 1
- WFIWKHDUCWDKSA-UHFFFAOYSA-N [4-[2-(dimethylamino)-2-oxoethyl]phenyl] 4-(diaminomethylideneamino)benzoate;methanesulfonic acid Chemical compound CS(O)(=O)=O.C1=CC(CC(=O)N(C)C)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 WFIWKHDUCWDKSA-UHFFFAOYSA-N 0.000 description 1
- MDKUPXMCDAUASG-UHFFFAOYSA-N [4-[2-(dipropylamino)-2-oxoethyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(CC(=O)N(CCC)CCC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 MDKUPXMCDAUASG-UHFFFAOYSA-N 0.000 description 1
- VIJXFYHRDHAETN-UHFFFAOYSA-N [4-[2-[bis(2-methylpropyl)amino]-2-oxoethyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(CC(=O)N(CC(C)C)CC(C)C)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 VIJXFYHRDHAETN-UHFFFAOYSA-N 0.000 description 1
- LFTFYABUEUVGDG-UHFFFAOYSA-N [4-[2-[butan-2-yl(butyl)amino]-2-oxoethyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(CC(=O)N(C(C)CC)CCCC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 LFTFYABUEUVGDG-UHFFFAOYSA-N 0.000 description 1
- VCBYCYJRZUZZRL-UHFFFAOYSA-N [4-[2-[butan-2-yl(ethyl)amino]-2-oxoethyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(CC(=O)N(CC)C(C)CC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 VCBYCYJRZUZZRL-UHFFFAOYSA-N 0.000 description 1
- OHSSNYTXJBBMOY-UHFFFAOYSA-N [4-[2-[butan-2-yl(propyl)amino]-2-oxoethyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(CC(=O)N(C(C)CC)CCC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 OHSSNYTXJBBMOY-UHFFFAOYSA-N 0.000 description 1
- JHHVJQULUBTKOU-UHFFFAOYSA-N [4-[2-[butyl(propyl)amino]-2-oxoethyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(CC(=O)N(CCC)CCCC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 JHHVJQULUBTKOU-UHFFFAOYSA-N 0.000 description 1
- UNOHKNRGAUABAB-UHFFFAOYSA-N [4-[2-[ethyl(methyl)amino]-2-oxoethyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(CC(=O)N(C)CC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 UNOHKNRGAUABAB-UHFFFAOYSA-N 0.000 description 1
- GGUXLPSJQABEBY-UHFFFAOYSA-N [4-[2-[ethyl(propan-2-yl)amino]-2-oxoethyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(CC(=O)N(C(C)C)CC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 GGUXLPSJQABEBY-UHFFFAOYSA-N 0.000 description 1
- SAZVSKKBJWJLJR-UHFFFAOYSA-N [4-[2-[ethyl(propyl)amino]-2-oxoethyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(CC(=O)N(CC)CCC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 SAZVSKKBJWJLJR-UHFFFAOYSA-N 0.000 description 1
- SQOKROSDGDXZOV-UHFFFAOYSA-N [4-[2-[methyl(propan-2-yl)amino]-2-oxoethyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(CC(=O)N(C)C(C)C)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 SQOKROSDGDXZOV-UHFFFAOYSA-N 0.000 description 1
- GPDWGTVTLNYCOB-UHFFFAOYSA-N [4-[2-[methyl(propyl)amino]-2-oxoethyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(CC(=O)N(C)CCC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 GPDWGTVTLNYCOB-UHFFFAOYSA-N 0.000 description 1
- WGQYKXZNRGBLKR-UHFFFAOYSA-N [4-[2-oxo-2-(propylamino)ethyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(CC(=O)NCCC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 WGQYKXZNRGBLKR-UHFFFAOYSA-N 0.000 description 1
- UMMCDCYUSKYAKN-UHFFFAOYSA-N [4-[2-oxo-2-[propan-2-yl(propyl)amino]ethyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(CC(=O)N(C(C)C)CCC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 UMMCDCYUSKYAKN-UHFFFAOYSA-N 0.000 description 1
- NOZBWFDLGXGXNE-UHFFFAOYSA-N [4-[3-(butan-2-ylamino)-3-oxoprop-1-enyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C=CC(=O)NC(C)CC)=CC=C1OC(=O)C1=CC=C(N=C(N)N)C=C1 NOZBWFDLGXGXNE-UHFFFAOYSA-N 0.000 description 1
- NTCQIHPGSHFILA-UHFFFAOYSA-N [4-[3-(butylamino)-3-oxoprop-1-enyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C=CC(=O)NCCCC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 NTCQIHPGSHFILA-UHFFFAOYSA-N 0.000 description 1
- RNXXZUGQHKULDC-UHFFFAOYSA-N [4-[3-(dibutylamino)-3-oxoprop-1-enyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C=CC(=O)N(CCCC)CCCC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 RNXXZUGQHKULDC-UHFFFAOYSA-N 0.000 description 1
- UCXQVVFWNRRJTR-UHFFFAOYSA-N [4-[3-(diethylamino)-3-oxoprop-1-enyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C=CC(=O)N(CC)CC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 UCXQVVFWNRRJTR-UHFFFAOYSA-N 0.000 description 1
- MUORVLYMMKZJCO-UHFFFAOYSA-N [4-[3-(dimethylamino)-3-oxoprop-1-enyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C=CC(=O)N(C)C)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 MUORVLYMMKZJCO-UHFFFAOYSA-N 0.000 description 1
- RWCKWBOLJXVMSA-UHFFFAOYSA-N [4-[3-(dipropylamino)-3-oxoprop-1-enyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C=CC(=O)N(CCC)CCC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 RWCKWBOLJXVMSA-UHFFFAOYSA-N 0.000 description 1
- DEYWSZPMLXIRRC-UHFFFAOYSA-N [4-[3-(ethylamino)-3-oxoprop-1-enyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C=CC(=O)NCC)=CC=C1OC(=O)C1=CC=C(N=C(N)N)C=C1 DEYWSZPMLXIRRC-UHFFFAOYSA-N 0.000 description 1
- GXACVWZTFRXCGU-UHFFFAOYSA-N [4-[3-(methylamino)-3-oxoprop-1-enyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C=CC(=O)NC)=CC=C1OC(=O)C1=CC=C(N=C(N)N)C=C1 GXACVWZTFRXCGU-UHFFFAOYSA-N 0.000 description 1
- CIJHJOUWSFHJNU-UHFFFAOYSA-N [4-[3-[butan-2-yl(ethyl)amino]-3-oxoprop-1-enyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C=CC(=O)N(CC)C(C)CC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 CIJHJOUWSFHJNU-UHFFFAOYSA-N 0.000 description 1
- GJXDLESFRAAZIX-UHFFFAOYSA-N [4-[3-[butyl(methyl)amino]-3-oxoprop-1-enyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C=CC(=O)N(C)CCCC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 GJXDLESFRAAZIX-UHFFFAOYSA-N 0.000 description 1
- RHGXFLDTAXRYMM-UHFFFAOYSA-N [4-[3-[di(propan-2-yl)amino]-3-oxoprop-1-enyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C=CC(=O)N(C(C)C)C(C)C)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 RHGXFLDTAXRYMM-UHFFFAOYSA-N 0.000 description 1
- PARHSQQKOFVDEA-UHFFFAOYSA-N [4-[3-[ethyl(methyl)amino]-3-oxoprop-1-enyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C=CC(=O)N(C)CC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 PARHSQQKOFVDEA-UHFFFAOYSA-N 0.000 description 1
- RWEDIMBZSBTSGP-UHFFFAOYSA-N [4-[3-[ethyl(propyl)amino]-3-oxoprop-1-enyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C=CC(=O)N(CC)CCC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 RWEDIMBZSBTSGP-UHFFFAOYSA-N 0.000 description 1
- WIDVJEXLMHKWTJ-UHFFFAOYSA-N [4-[3-oxo-3-(propan-2-ylamino)prop-1-enyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C=CC(=O)NC(C)C)=CC=C1OC(=O)C1=CC=C(N=C(N)N)C=C1 WIDVJEXLMHKWTJ-UHFFFAOYSA-N 0.000 description 1
- FALJONKUEFMZDU-UHFFFAOYSA-N [4-[3-oxo-3-(propylamino)prop-1-enyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C=CC(=O)NCCC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 FALJONKUEFMZDU-UHFFFAOYSA-N 0.000 description 1
- GWBIKQHBEQDGOA-UHFFFAOYSA-N [4-[bis(2-methylpropyl)carbamoyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C(=O)N(CC(C)C)CC(C)C)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 GWBIKQHBEQDGOA-UHFFFAOYSA-N 0.000 description 1
- PZQCBFYFMIKZJS-UHFFFAOYSA-N [4-[butan-2-yl(butyl)carbamoyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C(=O)N(C(C)CC)CCCC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 PZQCBFYFMIKZJS-UHFFFAOYSA-N 0.000 description 1
- HCYATSPJRRRTLN-UHFFFAOYSA-N [4-[butan-2-yl(methyl)carbamoyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C(=O)N(C)C(C)CC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 HCYATSPJRRRTLN-UHFFFAOYSA-N 0.000 description 1
- CUPGAJYACLJIAN-UHFFFAOYSA-N [4-[butan-2-yl(propyl)carbamoyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C(=O)N(C(C)CC)CCC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 CUPGAJYACLJIAN-UHFFFAOYSA-N 0.000 description 1
- KPFUOQSGCNWAHK-UHFFFAOYSA-N [4-[butyl(ethyl)carbamoyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C(=O)N(CC)CCCC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 KPFUOQSGCNWAHK-UHFFFAOYSA-N 0.000 description 1
- JVRJWHOUVVHETN-UHFFFAOYSA-N [4-[butyl(methyl)carbamoyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C(=O)N(C)CCCC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 JVRJWHOUVVHETN-UHFFFAOYSA-N 0.000 description 1
- VKYXXAJKYZAZRB-UHFFFAOYSA-N [4-[butyl(propyl)carbamoyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C(=O)N(CCC)CCCC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 VKYXXAJKYZAZRB-UHFFFAOYSA-N 0.000 description 1
- ONGOAJREAOEQHH-UHFFFAOYSA-N [4-[di(propan-2-yl)carbamoyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C(=O)N(C(C)C)C(C)C)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 ONGOAJREAOEQHH-UHFFFAOYSA-N 0.000 description 1
- IYAOQJWYWXOOMM-UHFFFAOYSA-N [4-[ethyl(methyl)carbamoyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C(=O)N(C)CC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 IYAOQJWYWXOOMM-UHFFFAOYSA-N 0.000 description 1
- DBDWLUCBLBPLEO-UHFFFAOYSA-N [4-[ethyl(propan-2-yl)carbamoyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C(=O)N(C(C)C)CC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 DBDWLUCBLBPLEO-UHFFFAOYSA-N 0.000 description 1
- YCYOYPKSLDNHFR-UHFFFAOYSA-N [4-[ethyl(propyl)carbamoyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C(=O)N(CC)CCC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 YCYOYPKSLDNHFR-UHFFFAOYSA-N 0.000 description 1
- JJHUKUOWZDUZQO-UHFFFAOYSA-N [4-[methyl(propan-2-yl)carbamoyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C(=O)N(C)C(C)C)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 JJHUKUOWZDUZQO-UHFFFAOYSA-N 0.000 description 1
- HAZPWSSIQYCFAS-UHFFFAOYSA-N [4-[methyl(propyl)carbamoyl]phenyl] 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(C(=O)N(C)CCC)=CC=C1OC(=O)C1=CC=C(NC(N)=N)C=C1 HAZPWSSIQYCFAS-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 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
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia 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
- 239000000872 buffer Substances 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
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229940012952 fibrinogen Drugs 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 208000031169 hemorrhagic disease Diseases 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 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
- 229940098779 methanesulfonic acid Drugs 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
- 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
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229960005202 streptokinase Drugs 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 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 |
|---|---|---|---|
| JP2257279A JPS55115863A (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 |
|---|---|---|---|
| JP2257279A JPS55115863A (en) | 1979-03-01 | 1979-03-01 | Guanidinobenzoic acid derivative and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55115863A JPS55115863A (en) | 1980-09-06 |
| JPS6141510B2 true JPS6141510B2 (enrdf_load_stackoverflow) | 1986-09-16 |
Family
ID=12086580
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2257279A Granted JPS55115863A (en) | 1979-03-01 | 1979-03-01 | Guanidinobenzoic acid derivative and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS55115863A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02183730A (ja) * | 1989-01-09 | 1990-07-18 | Sanyo Electric Co Ltd | 調理器 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008088159A (ja) * | 2006-07-26 | 2008-04-17 | Teva Pharmaceutical Industries Ltd | Ｏ−デスメチルベンラファキシンの合成方法 |
| JP5010713B2 (ja) * | 2010-05-19 | 2012-08-29 | 住友化学株式会社 | 塩酸カモスタットの製造方法 |
| JP2018080109A (ja) * | 2015-03-16 | 2018-05-24 | 武田薬品工業株式会社 | 治療剤 |
-
1979
- 1979-03-01 JP JP2257279A patent/JPS55115863A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02183730A (ja) * | 1989-01-09 | 1990-07-18 | Sanyo Electric Co Ltd | 調理器 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS55115863A (en) | 1980-09-06 |
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