JPS5841855A - アミジン化合物 - Google Patents
アミジン化合物Info
- Publication number
- JPS5841855A JPS5841855A JP14065081A JP14065081A JPS5841855A JP S5841855 A JPS5841855 A JP S5841855A JP 14065081 A JP14065081 A JP 14065081A JP 14065081 A JP14065081 A JP 14065081A JP S5841855 A JPS5841855 A JP S5841855A
- Authority
- JP
- Japan
- Prior art keywords
- group
- carbon atoms
- alkyl group
- branched alkyl
- hydrogen
- 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.)
- Granted
Links
- -1 Amidine compound Chemical class 0.000 title claims abstract description 70
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 48
- 239000002253 acid Substances 0.000 claims abstract description 36
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 19
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 8
- 230000002391 anti-complement effect Effects 0.000 claims abstract description 7
- 108010008730 anticomplement Proteins 0.000 claims abstract description 7
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
- 239000012048 reactive intermediate Substances 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 47
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 26
- 150000002431 hydrogen Chemical class 0.000 claims description 20
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 13
- 125000003277 amino group Chemical group 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 125000006239 protecting group Chemical group 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 239000004480 active ingredient Substances 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine group Chemical group NC(=N)N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 82
- 238000000034 method Methods 0.000 abstract description 31
- IYELGEUXPAPULN-UHFFFAOYSA-N 2-hydroxybenzenecarboximidamide Chemical class NC(=N)C1=CC=CC=C1O IYELGEUXPAPULN-UHFFFAOYSA-N 0.000 abstract description 12
- 239000002753 trypsin inhibitor Substances 0.000 abstract description 6
- 101710081722 Antitrypsin Proteins 0.000 abstract description 5
- 230000000288 anti-kallikrein effect Effects 0.000 abstract description 5
- 230000001475 anti-trypsic effect Effects 0.000 abstract description 5
- 239000004019 antithrombin Substances 0.000 abstract description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 101
- 239000013078 crystal Substances 0.000 description 87
- 238000003756 stirring Methods 0.000 description 81
- 239000000243 solution Substances 0.000 description 77
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 72
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 62
- 230000015572 biosynthetic process Effects 0.000 description 56
- 238000003786 synthesis reaction Methods 0.000 description 56
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 50
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 46
- 238000001816 cooling Methods 0.000 description 44
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
- 238000006243 chemical reaction Methods 0.000 description 42
- 239000002244 precipitate Substances 0.000 description 38
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 37
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 31
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 239000002904 solvent Substances 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 229940098779 methanesulfonic acid Drugs 0.000 description 24
- 239000000203 mixture Substances 0.000 description 22
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 20
- 239000007787 solid Substances 0.000 description 20
- 230000000295 complement effect Effects 0.000 description 19
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 15
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 15
- 239000000126 substance Substances 0.000 description 15
- 239000003921 oil Substances 0.000 description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
- 102000004190 Enzymes Human genes 0.000 description 12
- 108090000790 Enzymes Proteins 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 229940088598 enzyme Drugs 0.000 description 12
- 230000002401 inhibitory effect Effects 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- 229920006395 saturated elastomer Polymers 0.000 description 11
- 239000007788 liquid Substances 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 201000010099 disease Diseases 0.000 description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
- 206010018910 Haemolysis Diseases 0.000 description 8
- 238000001994 activation Methods 0.000 description 8
- 230000008588 hemolysis Effects 0.000 description 8
- 230000004913 activation Effects 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 229940124597 therapeutic agent Drugs 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 108090000631 Trypsin Proteins 0.000 description 6
- 102000004142 Trypsin Human genes 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000012456 homogeneous solution Substances 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 108060005987 Kallikrein Proteins 0.000 description 5
- 102000001399 Kallikrein Human genes 0.000 description 5
- 206010029120 Nephritis allergic Diseases 0.000 description 5
- 108090000190 Thrombin Proteins 0.000 description 5
- 210000004369 blood Anatomy 0.000 description 5
- 239000008280 blood Substances 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 229960004072 thrombin Drugs 0.000 description 5
- 239000012588 trypsin Substances 0.000 description 5
- 208000023275 Autoimmune disease Diseases 0.000 description 4
- 206010061218 Inflammation Diseases 0.000 description 4
- 206010033645 Pancreatitis Diseases 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Substances CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 230000036772 blood pressure Effects 0.000 description 4
- 239000012230 colorless oil Substances 0.000 description 4
- 230000004154 complement system Effects 0.000 description 4
- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 4
- 239000006260 foam Substances 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 230000004054 inflammatory process Effects 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 239000006228 supernatant Substances 0.000 description 4
- KWBVYNWLMFXTAY-UHFFFAOYSA-N (4-carbamimidoyl-2-methoxyphenyl) methanesulfonate Chemical compound COC1=CC(C(N)=N)=CC=C1OS(C)(=O)=O KWBVYNWLMFXTAY-UHFFFAOYSA-N 0.000 description 3
- JALQQPYRBFTUOH-UHFFFAOYSA-N (4-carbamimidoyl-2-nitrophenyl) methanesulfonate Chemical compound CS(=O)(=O)OC1=CC=C(C(N)=N)C=C1[N+]([O-])=O JALQQPYRBFTUOH-UHFFFAOYSA-N 0.000 description 3
- CQVKMVQRSNNAGO-UHFFFAOYSA-N 2-[4-formyl-3-methyl-n-(2-methylsulfonyloxyethyl)anilino]ethyl methanesulfonate Chemical compound CC1=CC(N(CCOS(C)(=O)=O)CCOS(C)(=O)=O)=CC=C1C=O CQVKMVQRSNNAGO-UHFFFAOYSA-N 0.000 description 3
- IWWJWSAHSAJRNL-UHFFFAOYSA-N 4-acetyloxy-2-methylbenzoic acid Chemical compound CC(=O)OC1=CC=C(C(O)=O)C(C)=C1 IWWJWSAHSAJRNL-UHFFFAOYSA-N 0.000 description 3
- QPNAXWVQSCWLGD-UHFFFAOYSA-N 5-carbamimidoyl-2-hydroxybenzoic acid Chemical compound NC(=N)C1=CC=C(O)C(C(O)=O)=C1 QPNAXWVQSCWLGD-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 102000009123 Fibrin Human genes 0.000 description 3
- 108010073385 Fibrin Proteins 0.000 description 3
- BWGVNKXGVNDBDI-UHFFFAOYSA-N Fibrin monomer Chemical compound CNC(=O)CNC(=O)CN BWGVNKXGVNDBDI-UHFFFAOYSA-N 0.000 description 3
- 206010018364 Glomerulonephritis Diseases 0.000 description 3
- 101000579646 Penaeus vannamei Penaeidin-1 Proteins 0.000 description 3
- 230000002159 abnormal effect Effects 0.000 description 3
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 3
- 210000004204 blood vessel Anatomy 0.000 description 3
- 238000009835 boiling Methods 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
- 235000008504 concentrate Nutrition 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 238000001647 drug administration Methods 0.000 description 3
- 229950003499 fibrin Drugs 0.000 description 3
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 3
- 208000031169 hemorrhagic disease Diseases 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- GUMOYVLLEOGGMJ-UHFFFAOYSA-N methyl 5-carbamimidoyl-2-hydroxybenzoate Chemical compound COC(=O)C1=CC(C(N)=N)=CC=C1O GUMOYVLLEOGGMJ-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229940012957 plasmin Drugs 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- 239000003053 toxin Substances 0.000 description 3
- 231100000765 toxin Toxicity 0.000 description 3
- 230000002485 urinary effect Effects 0.000 description 3
- MCILSJGATWOXGD-UHFFFAOYSA-N (2-benzoyl-4-carbamimidoylphenyl) 4-hydroxybenzoate Chemical compound C=1C=CC=CC=1C(=O)C1=CC(C(=N)N)=CC=C1OC(=O)C1=CC=C(O)C=C1 MCILSJGATWOXGD-UHFFFAOYSA-N 0.000 description 2
- IOYFOZCHGMPWSM-UHFFFAOYSA-N (4-carbonochloridoyl-3-methylphenyl) acetate Chemical compound CC(=O)OC1=CC=C(C(Cl)=O)C(C)=C1 IOYFOZCHGMPWSM-UHFFFAOYSA-N 0.000 description 2
- IPMPVLAASRKHRW-UHFFFAOYSA-N 3-amino-4-hydroxybenzenecarboximidamide Chemical compound NC(=N)C1=CC=C(O)C(N)=C1 IPMPVLAASRKHRW-UHFFFAOYSA-N 0.000 description 2
- GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 2
- QJRWLNLUIAJTAD-UHFFFAOYSA-N 4-hydroxy-3-methoxybenzonitrile Chemical compound COC1=CC(C#N)=CC=C1O QJRWLNLUIAJTAD-UHFFFAOYSA-N 0.000 description 2
- BNDMHAXTNRDKHP-UHFFFAOYSA-N 4-hydroxy-3-nitrobenzenecarboximidamide Chemical compound NC(=N)C1=CC=C(O)C([N+]([O-])=O)=C1 BNDMHAXTNRDKHP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- HQTAEVTXSCKTPM-UHFFFAOYSA-N COC1=CC(C(N)=N)=CC=C1O Chemical compound COC1=CC(C(N)=N)=CC=C1O HQTAEVTXSCKTPM-UHFFFAOYSA-N 0.000 description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 206010020751 Hypersensitivity Diseases 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 102000035195 Peptidases Human genes 0.000 description 2
- 108091005804 Peptidases Proteins 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 102000018690 Trypsinogen Human genes 0.000 description 2
- 108010027252 Trypsinogen Proteins 0.000 description 2
- 208000025865 Ulcer Diseases 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 208000026935 allergic disease Diseases 0.000 description 2
- 230000007815 allergy Effects 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- 230000004087 circulation Effects 0.000 description 2
- 230000015271 coagulation Effects 0.000 description 2
- 238000005345 coagulation Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000009089 cytolysis Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229960001867 guaiacol Drugs 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- FJWBZEPQUSGUIS-UHFFFAOYSA-N methanesulfonic acid methyl 5-carbamimidoyl-2-hydroxybenzoate Chemical compound CS(=O)(=O)O.C(N)(=N)C1=CC=C(C(C(=O)OC)=C1)O FJWBZEPQUSGUIS-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000001575 pathological effect Effects 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 230000003248 secreting effect Effects 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- XHFLOLLMZOTPSM-UHFFFAOYSA-M sodium;hydrogen carbonate;hydrate Chemical class [OH-].[Na+].OC(O)=O XHFLOLLMZOTPSM-UHFFFAOYSA-M 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 231100000397 ulcer Toxicity 0.000 description 2
- SCPVLVCTHWLXIP-UHFFFAOYSA-N (2,6-dibromo-4-carbamimidoylphenyl) methanesulfonate Chemical compound CS(=O)(=O)OC1=C(Br)C=C(C(N)=N)C=C1Br SCPVLVCTHWLXIP-UHFFFAOYSA-N 0.000 description 1
- VJJBIPMAPQNVOY-UHFFFAOYSA-N (2-benzamido-4-carbamimidoylphenyl) benzoate;carbonic acid Chemical compound OC(O)=O.C=1C=CC=CC=1C(=O)NC1=CC(C(=N)N)=CC=C1OC(=O)C1=CC=CC=C1 VJJBIPMAPQNVOY-UHFFFAOYSA-N 0.000 description 1
- HPMVIZKFXDSZSO-UHFFFAOYSA-N (2-benzoyl-4-carbamimidoylphenyl) 2-(4-acetyloxyphenyl)-3-phenylprop-2-enoate;methanesulfonic acid Chemical compound CS(O)(=O)=O.C1=CC(OC(=O)C)=CC=C1C(C(=O)OC=1C(=CC(=CC=1)C(N)=N)C(=O)C=1C=CC=CC=1)=CC1=CC=CC=C1 HPMVIZKFXDSZSO-UHFFFAOYSA-N 0.000 description 1
- DSUDZIGVVAOGAZ-UHFFFAOYSA-N (2-benzoyl-4-carbamimidoylphenyl) 3-(4-acetyloxyphenyl)prop-2-enoate Chemical compound C1=CC(OC(=O)C)=CC=C1C=CC(=O)OC1=CC=C(C(N)=N)C=C1C(=O)C1=CC=CC=C1 DSUDZIGVVAOGAZ-UHFFFAOYSA-N 0.000 description 1
- MZINMLWWFPTBSR-UHFFFAOYSA-N (2-benzoyl-4-carbamimidoylphenyl) methanesulfonate Chemical compound CS(=O)(=O)OC1=CC=C(C(N)=N)C=C1C(=O)C1=CC=CC=C1 MZINMLWWFPTBSR-UHFFFAOYSA-N 0.000 description 1
- FGJIIDKAOVAZDK-UHFFFAOYSA-N (2-chlorophenyl) methanesulfonate Chemical compound CS(=O)(=O)OC1=CC=CC=C1Cl FGJIIDKAOVAZDK-UHFFFAOYSA-N 0.000 description 1
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 1
- CSPLGDDGIJDAJS-UHFFFAOYSA-N (2-methoxyphenyl) methanesulfonate Chemical compound COC1=CC=CC=C1OS(C)(=O)=O CSPLGDDGIJDAJS-UHFFFAOYSA-N 0.000 description 1
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- OJAYWPCMRDAPBX-UHFFFAOYSA-N methyl 2-hydroxy-5-(methoxyiminomethyl)benzoate hydrochloride Chemical compound Cl.CON=CC1=CC=C(O)C(C(=O)OC)=C1 OJAYWPCMRDAPBX-UHFFFAOYSA-N 0.000 description 1
- LZXXNPOYQCLXRS-UHFFFAOYSA-N methyl 4-aminobenzoate Chemical compound COC(=O)C1=CC=C(N)C=C1 LZXXNPOYQCLXRS-UHFFFAOYSA-N 0.000 description 1
- WNLGGSGBOQGUHV-UHFFFAOYSA-N methyl 5-cyano-2-hydroxybenzoate Chemical compound COC(=O)C1=CC(C#N)=CC=C1O WNLGGSGBOQGUHV-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 210000004088 microvessel Anatomy 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 201000008383 nephritis Diseases 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 210000004923 pancreatic tissue Anatomy 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- WXVUCMFEGJUVTN-UHFFFAOYSA-N phenyl methanesulfonate Chemical compound CS(=O)(=O)OC1=CC=CC=C1 WXVUCMFEGJUVTN-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- 229940024999 proteolytic enzymes for treatment of wounds and ulcers Drugs 0.000 description 1
- OENLEHTYJXMVBG-UHFFFAOYSA-N pyridine;hydrate Chemical compound [OH-].C1=CC=[NH+]C=C1 OENLEHTYJXMVBG-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 230000036454 renin-angiotensin system Effects 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 206010040400 serum sickness Diseases 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000008685 targeting Effects 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
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- CAYKLJBSARHIDI-UHFFFAOYSA-K trichloroalumane;hydrate Chemical compound O.Cl[Al](Cl)Cl CAYKLJBSARHIDI-UHFFFAOYSA-K 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 229960005356 urokinase Drugs 0.000 description 1
- 230000008728 vascular permeability Effects 0.000 description 1
- 210000001835 viscera Anatomy 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Landscapes
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (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 (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14065081A JPS5841855A (ja) | 1981-09-07 | 1981-09-07 | アミジン化合物 |
| GB8205699A GB2095239B (en) | 1981-02-27 | 1982-02-26 | Novel amidine compounds |
| FR8203258A FR2500825B1 (fr) | 1981-02-27 | 1982-02-26 | Nouveau carboxylate de 4-amidino-phenyle substitue, son procede de preparation et agent anti-complement en comprenant |
| DE3207033A DE3207033C2 (de) | 1981-02-27 | 1982-02-26 | Amidinverbindungen, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Mittel |
| US06/611,937 US4514416A (en) | 1981-02-27 | 1984-05-21 | Amidine compound, process for producing same and anti-complement agent comprising same |
| US06/664,261 US4570006A (en) | 1981-02-27 | 1984-10-24 | Amidine compound, process for producing same and anti-complement agent comprising same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14065081A JPS5841855A (ja) | 1981-09-07 | 1981-09-07 | アミジン化合物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5841855A true JPS5841855A (ja) | 1983-03-11 |
| JPH0210823B2 JPH0210823B2 (enrdf_load_stackoverflow) | 1990-03-09 |
Family
ID=15273579
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14065081A Granted JPS5841855A (ja) | 1981-02-27 | 1981-09-07 | アミジン化合物 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5841855A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0360653A (ja) * | 1989-07-27 | 1991-03-15 | Howmedica Internatl Inc | 交換義膝用脛骨要素 |
| JPH05279315A (ja) * | 1992-04-01 | 1993-10-26 | Nitto Boseki Co Ltd | 安息香酸アミジノフェニルエステル誘導体 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5225740A (en) * | 1975-08-21 | 1977-02-25 | Yuichi Kaneoka | Preparation of o-acyl-amidinophenols or acid addition salts thereof |
| JPS55154952A (en) * | 1979-05-23 | 1980-12-02 | Kowa Co | Amidinophenol derivative |
| JPS565451A (en) * | 1979-06-27 | 1981-01-20 | Kowa Co | Acylamidinophenol derivative |
-
1981
- 1981-09-07 JP JP14065081A patent/JPS5841855A/ja active Granted
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5225740A (en) * | 1975-08-21 | 1977-02-25 | Yuichi Kaneoka | Preparation of o-acyl-amidinophenols or acid addition salts thereof |
| JPS55154952A (en) * | 1979-05-23 | 1980-12-02 | Kowa Co | Amidinophenol derivative |
| JPS565451A (en) * | 1979-06-27 | 1981-01-20 | Kowa Co | Acylamidinophenol derivative |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0360653A (ja) * | 1989-07-27 | 1991-03-15 | Howmedica Internatl Inc | 交換義膝用脛骨要素 |
| JPH05279315A (ja) * | 1992-04-01 | 1993-10-26 | Nitto Boseki Co Ltd | 安息香酸アミジノフェニルエステル誘導体 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0210823B2 (enrdf_load_stackoverflow) | 1990-03-09 |
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