JPH0160019B2 - - Google Patents
Info
- Publication number
- JPH0160019B2 JPH0160019B2 JP13085681A JP13085681A JPH0160019B2 JP H0160019 B2 JPH0160019 B2 JP H0160019B2 JP 13085681 A JP13085681 A JP 13085681A JP 13085681 A JP13085681 A JP 13085681A JP H0160019 B2 JPH0160019 B2 JP H0160019B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- amidino
- ether
- acid
- ester hydrochloride
- 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
- 125000003118 aryl group Chemical group 0.000 claims description 54
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 14
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 7
- QUUYRYYUKNNNNS-UHFFFAOYSA-N piperidine-1-carboximidamide Chemical class NC(=N)N1CCCCC1 QUUYRYYUKNNNNS-UHFFFAOYSA-N 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 6
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 5
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 144
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 126
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 117
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 110
- 239000013078 crystal Substances 0.000 description 107
- 229910052739 hydrogen Inorganic materials 0.000 description 90
- 239000001257 hydrogen Substances 0.000 description 89
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 87
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 71
- FURFBEMWMQZGOF-UHFFFAOYSA-N 3-(1-carbamimidoylpiperidin-4-yl)propanoic acid Chemical compound NC(=N)N1CCC(CCC(O)=O)CC1 FURFBEMWMQZGOF-UHFFFAOYSA-N 0.000 description 66
- -1 benzylphenethyl Chemical group 0.000 description 65
- 239000000203 mixture Substances 0.000 description 60
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 55
- 238000002844 melting Methods 0.000 description 48
- 230000008018 melting Effects 0.000 description 48
- 239000002904 solvent Substances 0.000 description 47
- 150000002148 esters Chemical class 0.000 description 38
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
- 150000001875 compounds Chemical class 0.000 description 36
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 30
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 29
- 238000003756 stirring Methods 0.000 description 24
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- DCYAOXOBKROXKE-UHFFFAOYSA-N 1-carbamimidoylpiperidine-4-carboxylic acid Chemical compound NC(=N)N1CCC(C(O)=O)CC1 DCYAOXOBKROXKE-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 12
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 11
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 11
- RCWIHAZSVNHOEP-UHFFFAOYSA-N 1-carbamimidoylpiperidine-4-carboxylic acid;hydrochloride Chemical compound Cl.NC(=N)N1CCC(C(O)=O)CC1 RCWIHAZSVNHOEP-UHFFFAOYSA-N 0.000 description 10
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 10
- 229910052799 carbon Inorganic materials 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000005406 washing Methods 0.000 description 9
- KCFIAUSAJKFBOW-UHFFFAOYSA-N 3-(1-carbamimidoylpiperidin-4-yl)propanoic acid;hydrochloride Chemical compound Cl.NC(=N)N1CCC(CCC(O)=O)CC1 KCFIAUSAJKFBOW-UHFFFAOYSA-N 0.000 description 8
- YKWNUSJLICDQEO-UHFFFAOYSA-N ethoxyethane;propan-2-ol Chemical compound CC(C)O.CCOCC YKWNUSJLICDQEO-UHFFFAOYSA-N 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 7
- 230000002401 inhibitory effect Effects 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 230000009285 allergic inflammation Effects 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 4
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 3
- 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
- 208000000104 Arthus reaction Diseases 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 3
- 241000700199 Cavia porcellus Species 0.000 description 3
- 206010018910 Haemolysis Diseases 0.000 description 3
- 108091005804 Peptidases Proteins 0.000 description 3
- 102000035195 Peptidases Human genes 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
- 206010053614 Type III immune complex mediated reaction Diseases 0.000 description 3
- 206010053613 Type IV hypersensitivity reaction Diseases 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
- 210000003743 erythrocyte Anatomy 0.000 description 3
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 230000037361 pathway Effects 0.000 description 3
- 210000002966 serum Anatomy 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- 230000005951 type IV hypersensitivity Effects 0.000 description 3
- 208000027930 type IV hypersensitivity disease Diseases 0.000 description 3
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- GRFNBEZIAWKNCO-UHFFFAOYSA-N 3-pyridinol Chemical compound OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 description 2
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- YQUQWHNMBPIWGK-UHFFFAOYSA-N 4-isopropylphenol Chemical compound CC(C)C1=CC=C(O)C=C1 YQUQWHNMBPIWGK-UHFFFAOYSA-N 0.000 description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- FTOAOBMCPZCFFF-UHFFFAOYSA-N 5,5-diethylbarbituric acid Chemical compound CCC1(CC)C(=O)NC(=O)NC1=O FTOAOBMCPZCFFF-UHFFFAOYSA-N 0.000 description 2
- 108090000317 Chymotrypsin Proteins 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-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
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004365 Protease Substances 0.000 description 2
- 206010070834 Sensitisation Diseases 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 108090000631 Trypsin Proteins 0.000 description 2
- 102000004142 Trypsin Human genes 0.000 description 2
- 108090000435 Urokinase-type plasminogen activator Proteins 0.000 description 2
- 102000003990 Urokinase-type plasminogen activator Human genes 0.000 description 2
- 238000007605 air drying Methods 0.000 description 2
- 230000002391 anti-complement effect Effects 0.000 description 2
- 239000000427 antigen Substances 0.000 description 2
- 102000036639 antigens Human genes 0.000 description 2
- 108091007433 antigens Proteins 0.000 description 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
- QPYXDTXYDDXHQK-UHFFFAOYSA-N bis(2,4-dichlorophenyl) sulfite Chemical compound ClC1=CC(Cl)=CC=C1OS(=O)OC1=CC=C(Cl)C=C1Cl QPYXDTXYDDXHQK-UHFFFAOYSA-N 0.000 description 2
- FUIHKXIVWVZHDQ-UHFFFAOYSA-N bis(2,4-dimethylphenyl) sulfite Chemical compound CC1=CC(C)=CC=C1OS(=O)OC1=CC=C(C)C=C1C FUIHKXIVWVZHDQ-UHFFFAOYSA-N 0.000 description 2
- IOXATWUMLPKRDF-UHFFFAOYSA-N bis(4-cyclohexylphenyl) sulfite Chemical compound C=1C=C(C2CCCCC2)C=CC=1OS(=O)OC(C=C1)=CC=C1C1CCCCC1 IOXATWUMLPKRDF-UHFFFAOYSA-N 0.000 description 2
- 229960002376 chymotrypsin Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- PEHSSTUGJUBZBI-UHFFFAOYSA-N indan-5-ol Chemical compound OC1=CC=C2CCCC2=C1 PEHSSTUGJUBZBI-UHFFFAOYSA-N 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- QBDSZLJBMIMQRS-UHFFFAOYSA-N p-Cumylphenol Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=CC=C1 QBDSZLJBMIMQRS-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- SAALQYKUFCIMHR-UHFFFAOYSA-N propan-2-ol;2-propan-2-yloxypropane Chemical compound CC(C)O.CC(C)OC(C)C SAALQYKUFCIMHR-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000008313 sensitization Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 150000007970 thio esters Chemical class 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
- 239000012588 trypsin Substances 0.000 description 2
- 229960001322 trypsin Drugs 0.000 description 2
- 229960005356 urokinase Drugs 0.000 description 2
- LUWQTNBHVOCURM-UHFFFAOYSA-N (2-phenylmethoxycarbonylphenyl) 1-carbamimidoylpiperidine-4-carboxylate;hydrochloride Chemical compound Cl.C1CN(C(=N)N)CCC1C(=O)OC1=CC=CC=C1C(=O)OCC1=CC=CC=C1 LUWQTNBHVOCURM-UHFFFAOYSA-N 0.000 description 1
- BKOGTGYEZNJQMF-UHFFFAOYSA-N (4-acetamidophenyl) 3-(1-carbamimidoylpiperidin-4-yl)propanoate;hydrochloride Chemical compound Cl.C1=CC(NC(=O)C)=CC=C1OC(=O)CCC1CCN(C(N)=N)CC1 BKOGTGYEZNJQMF-UHFFFAOYSA-N 0.000 description 1
- OUYMRWFROLKJPG-UHFFFAOYSA-N (4-chlorophenyl) 1-carbamimidoylpiperidine-4-carboxylate;hydrochloride Chemical compound Cl.C1CN(C(=N)N)CCC1C(=O)OC1=CC=C(Cl)C=C1 OUYMRWFROLKJPG-UHFFFAOYSA-N 0.000 description 1
- PYTJUYUDUSDJKT-UHFFFAOYSA-N (4-methoxyphenyl) 1-carbamimidoylpiperidine-4-carboxylate;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1OC(=O)C1CCN(C(N)=N)CC1 PYTJUYUDUSDJKT-UHFFFAOYSA-N 0.000 description 1
- QBIMPNINGKUMPR-UHFFFAOYSA-N (4-methoxyphenyl) 3-(1-carbamimidoylpiperidin-4-yl)propanoate;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1OC(=O)CCC1CCN(C(N)=N)CC1 QBIMPNINGKUMPR-UHFFFAOYSA-N 0.000 description 1
- COTQVYFHEGTKFJ-UHFFFAOYSA-N (4-sulfamoylphenyl) 3-(1-carbamimidoylpiperidin-4-yl)propanoate;hydrochloride Chemical compound Cl.C1CN(C(=N)N)CCC1CCC(=O)OC1=CC=C(S(N)(=O)=O)C=C1 COTQVYFHEGTKFJ-UHFFFAOYSA-N 0.000 description 1
- BOUQBCCFJZYKBJ-UHFFFAOYSA-N (4-tert-butylphenyl) 1-carbamimidoylpiperidine-4-carboxylate;hydrochloride Chemical compound Cl.C1=CC(C(C)(C)C)=CC=C1OC(=O)C1CCN(C(N)=N)CC1 BOUQBCCFJZYKBJ-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- ADVGKWPZRIDURE-UHFFFAOYSA-N 2'-Hydroxyacetanilide Chemical compound CC(=O)NC1=CC=CC=C1O ADVGKWPZRIDURE-UHFFFAOYSA-N 0.000 description 1
- BPRYUXCVCCNUFE-UHFFFAOYSA-N 2,4,6-trimethylphenol Chemical compound CC1=CC(C)=C(O)C(C)=C1 BPRYUXCVCCNUFE-UHFFFAOYSA-N 0.000 description 1
- KUFFULVDNCHOFZ-UHFFFAOYSA-N 2,4-xylenol Chemical compound CC1=CC=C(O)C(C)=C1 KUFFULVDNCHOFZ-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- QIRNGVVZBINFMX-UHFFFAOYSA-N 2-allylphenol Chemical compound OC1=CC=CC=C1CC=C QIRNGVVZBINFMX-UHFFFAOYSA-N 0.000 description 1
- CHZCERSEMVWNHL-UHFFFAOYSA-N 2-hydroxybenzonitrile Chemical compound OC1=CC=CC=C1C#N CHZCERSEMVWNHL-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- UGEJOEBBMPOJMT-UHFFFAOYSA-N 3-(trifluoromethyl)phenol Chemical compound OC1=CC=CC(C(F)(F)F)=C1 UGEJOEBBMPOJMT-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
- AUYQMCCWFNSFGV-UHFFFAOYSA-N 3-piperidin-1-ium-4-ylpropanoate Chemical compound OC(=O)CCC1CCNCC1 AUYQMCCWFNSFGV-UHFFFAOYSA-N 0.000 description 1
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 1
- CVNOWLNNPYYEOH-UHFFFAOYSA-N 4-cyanophenol Chemical compound OC1=CC=C(C#N)C=C1 CVNOWLNNPYYEOH-UHFFFAOYSA-N 0.000 description 1
- OAHMVZYHIJQTQC-UHFFFAOYSA-N 4-cyclohexylphenol Chemical compound C1=CC(O)=CC=C1C1CCCCC1 OAHMVZYHIJQTQC-UHFFFAOYSA-N 0.000 description 1
- RHMPLDJJXGPMEX-UHFFFAOYSA-N 4-fluorophenol Chemical compound OC1=CC=C(F)C=C1 RHMPLDJJXGPMEX-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
- MNVMYTVDDOXZLS-UHFFFAOYSA-N 4-methoxyguaiacol Natural products COC1=CC=C(O)C(OC)=C1 MNVMYTVDDOXZLS-UHFFFAOYSA-N 0.000 description 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
- PRLINSMUYJWPBL-UHFFFAOYSA-N 4-tert-butyl-2-chlorophenol Chemical compound CC(C)(C)C1=CC=C(O)C(Cl)=C1 PRLINSMUYJWPBL-UHFFFAOYSA-N 0.000 description 1
- GNXBFFHXJDZGEK-UHFFFAOYSA-N 4-tert-butylbenzenethiol Chemical compound CC(C)(C)C1=CC=C(S)C=C1 GNXBFFHXJDZGEK-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-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
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 108010088842 Fibrinolysin Proteins 0.000 description 1
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- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
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- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
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- 229960002319 barbital Drugs 0.000 description 1
- LLGLBBVIYRBZFI-UHFFFAOYSA-N benzyl 2-(2-phenylmethoxycarbonylphenoxy)sulfinyloxybenzoate Chemical compound C=1C=CC=C(OS(=O)OC=2C(=CC=CC=2)C(=O)OCC=2C=CC=CC=2)C=1C(=O)OCC1=CC=CC=C1 LLGLBBVIYRBZFI-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
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- VCZFNYRQZBZLKR-UHFFFAOYSA-N bis(2,3-dihydro-1h-inden-5-yl) sulfite Chemical compound C1=C2CCCC2=CC(OS(OC=2C=C3CCCC3=CC=2)=O)=C1 VCZFNYRQZBZLKR-UHFFFAOYSA-N 0.000 description 1
- YZYKEEGKTYPQBB-UHFFFAOYSA-N bis(2,6-dimethylphenyl) sulfite Chemical compound CC1=CC=CC(C)=C1OS(=O)OC1=C(C)C=CC=C1C YZYKEEGKTYPQBB-UHFFFAOYSA-N 0.000 description 1
- DGQGZSKYUMJHBW-UHFFFAOYSA-N bis(2-methylphenyl) sulfite Chemical compound CC1=CC=CC=C1OS(=O)OC1=CC=CC=C1C DGQGZSKYUMJHBW-UHFFFAOYSA-N 0.000 description 1
- QAKMUGMNHBQSTA-UHFFFAOYSA-N bis(2-phenylphenyl) sulfite Chemical compound C=1C=CC=C(C=2C=CC=CC=2)C=1OS(=O)OC1=CC=CC=C1C1=CC=CC=C1 QAKMUGMNHBQSTA-UHFFFAOYSA-N 0.000 description 1
- VMHTVCWRLHHZJO-UHFFFAOYSA-N bis(4-chlorophenyl) sulfite Chemical compound C1=CC(Cl)=CC=C1OS(=O)OC1=CC=C(Cl)C=C1 VMHTVCWRLHHZJO-UHFFFAOYSA-N 0.000 description 1
- UVTCDOMXZCRQQS-UHFFFAOYSA-N bis(4-methylphenyl) sulfite Chemical compound C1=CC(C)=CC=C1OS(=O)OC1=CC=C(C)C=C1 UVTCDOMXZCRQQS-UHFFFAOYSA-N 0.000 description 1
- GRDMQWRBLJZFML-UHFFFAOYSA-N bis(4-nitrophenyl) sulfite Chemical compound C1=CC([N+](=O)[O-])=CC=C1OS(=O)OC1=CC=C([N+]([O-])=O)C=C1 GRDMQWRBLJZFML-UHFFFAOYSA-N 0.000 description 1
- OCRCSNFXXPWOSN-UHFFFAOYSA-N bis(4-phenylphenyl) sulfite Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1OS(=O)OC(C=C1)=CC=C1C1=CC=CC=C1 OCRCSNFXXPWOSN-UHFFFAOYSA-N 0.000 description 1
- VBHSJMZQKOGPOX-UHFFFAOYSA-N bis(4-propan-2-ylphenyl) sulfite Chemical compound C1=CC(C(C)C)=CC=C1OS(=O)OC1=CC=C(C(C)C)C=C1 VBHSJMZQKOGPOX-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- NRDQFWXVTPZZAZ-UHFFFAOYSA-N butyl carbonochloridate Chemical compound CCCCOC(Cl)=O NRDQFWXVTPZZAZ-UHFFFAOYSA-N 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
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- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- XOSZCAXAILAJHF-UHFFFAOYSA-N dinaphthalen-1-yl sulfite Chemical compound C1=CC=C2C(OS(OC=3C4=CC=CC=C4C=CC=3)=O)=CC=CC2=C1 XOSZCAXAILAJHF-UHFFFAOYSA-N 0.000 description 1
- YDMZVDQRXYPAFN-UHFFFAOYSA-N dinaphthalen-2-yl sulfite Chemical compound C1=CC=CC2=CC(OS(OC=3C=C4C=CC=CC4=CC=3)=O)=CC=C21 YDMZVDQRXYPAFN-UHFFFAOYSA-N 0.000 description 1
- AVGYVDOSBJFXFR-UHFFFAOYSA-N diphenyl sulfite Chemical compound C=1C=CC=CC=1OS(=O)OC1=CC=CC=C1 AVGYVDOSBJFXFR-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 210000003194 forelimb Anatomy 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
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- 230000006698 induction Effects 0.000 description 1
- SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 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
- 239000000463 material Substances 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- JSMQNTZJJSAQAB-UHFFFAOYSA-N methyl 4-[3-(1-carbamimidoylpiperidin-4-yl)propanoyloxy]benzoate;hydrochloride Chemical compound Cl.C1=CC(C(=O)OC)=CC=C1OC(=O)CCC1CCN(C(N)=N)CC1 JSMQNTZJJSAQAB-UHFFFAOYSA-N 0.000 description 1
- RMAHPRNLQIRHIJ-UHFFFAOYSA-N methyl carbamimidate Chemical compound COC(N)=N RMAHPRNLQIRHIJ-UHFFFAOYSA-N 0.000 description 1
- SDDKIZNHOCEXTF-UHFFFAOYSA-N methyl carbamimidothioate Chemical compound CSC(N)=N SDDKIZNHOCEXTF-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- 229940092253 ovalbumin Drugs 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- VOHWDPXHUIOXIW-UHFFFAOYSA-N phenyl 1-carbamimidoylpiperidine-4-carboxylate;hydrochloride Chemical compound Cl.C1CN(C(=N)N)CCC1C(=O)OC1=CC=CC=C1 VOHWDPXHUIOXIW-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- QHDUBNMGSDGCKZ-UHFFFAOYSA-N piperidin-1-ium;propanoate Chemical compound CCC(O)=O.C1CCNCC1 QHDUBNMGSDGCKZ-UHFFFAOYSA-N 0.000 description 1
- 229940023751 piperidinepropionic acid Drugs 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 229940012957 plasmin Drugs 0.000 description 1
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 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
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 229960004072 thrombin Drugs 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13085681A JPS5832865A (ja) | 1981-08-22 | 1981-08-22 | 新規なアミジノピペリジン誘導体およびその製造法 |
| US06/379,714 US4433152A (en) | 1981-05-25 | 1982-05-19 | Amidinopiperidine derivatives |
| CA000403483A CA1188302A (en) | 1981-05-25 | 1982-05-21 | Amidinopiperidine derivatives and a process for producing the same |
| AR82289478A AR242560A1 (es) | 1981-05-25 | 1982-05-21 | Un procedimiento para producir derivados de acidos 1-amidin-piperidin-alcanoicos y sus sales farmaceuticamente aceptables. |
| IT67668/82A IT1157014B (it) | 1981-05-25 | 1982-05-24 | Derivati dell'ammidinopiperidina particolarmente utili come medicamenti e procedimento per la loro produzione |
| NL8202109A NL8202109A (nl) | 1981-05-25 | 1982-05-24 | Nieuwe amidinopiperidinederivaten en werkwijzen voor het bereiden en toepassen van deze derivaten. |
| CH3188/82A CH654298A5 (fr) | 1981-05-25 | 1982-05-24 | Derives de l'amidinopiperidine et leur procede de fabrication. |
| BR8203060A BR8203060A (pt) | 1981-05-25 | 1982-05-25 | Processo para a producao de derivados de aminopiperidina |
| MX192853A MX158198A (es) | 1981-05-25 | 1982-05-25 | Procedimiento para preparar derivados de amidinopiperidina |
| KR8202310A KR880002273B1 (ko) | 1981-05-25 | 1982-05-25 | 아미디노 피페리딘 유도체의 제조방법 |
| ES512519A ES512519A0 (es) | 1981-05-25 | 1982-05-25 | Proceso de fabricacion de los nuevos derivados de la amidinopiperadina. |
| DE19823219614 DE3219614A1 (de) | 1981-05-25 | 1982-05-25 | Amidinopiperidinderivate, verfahren zu deren herstellung und diese enthaltende arzneimittel |
| FR8209056A FR2506306B1 (fr) | 1981-05-25 | 1982-05-25 | Nouveaux derives de l'amidinopiperidine, leur procede de preparation et leur application en therapeutique |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13085681A JPS5832865A (ja) | 1981-08-22 | 1981-08-22 | 新規なアミジノピペリジン誘導体およびその製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5832865A JPS5832865A (ja) | 1983-02-25 |
| JPH0160019B2 true JPH0160019B2 (de) | 1989-12-20 |
Family
ID=15044288
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13085681A Granted JPS5832865A (ja) | 1981-05-25 | 1981-08-22 | 新規なアミジノピペリジン誘導体およびその製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5832865A (de) |
-
1981
- 1981-08-22 JP JP13085681A patent/JPS5832865A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5832865A (ja) | 1983-02-25 |
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