NO300633B1 - Nye amidinonaftylfurankarboksylatderivater og syreaddisjonssalter derav, samt farmasöytiske preparater inneholdende dem - Google Patents
Nye amidinonaftylfurankarboksylatderivater og syreaddisjonssalter derav, samt farmasöytiske preparater inneholdende dem Download PDFInfo
- Publication number
- NO300633B1 NO300633B1 NO924758A NO924758A NO300633B1 NO 300633 B1 NO300633 B1 NO 300633B1 NO 924758 A NO924758 A NO 924758A NO 924758 A NO924758 A NO 924758A NO 300633 B1 NO300633 B1 NO 300633B1
- Authority
- NO
- Norway
- Prior art keywords
- group
- added
- stirred
- amidino
- naphthyl
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims abstract description 12
- 150000003839 salts Chemical class 0.000 title claims abstract description 12
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 6
- VVZBIMWRNJKGNH-UHFFFAOYSA-N 4-carbamimidoyl-3-naphthalen-1-ylfuran-2-carboxylic acid Chemical class C(N)(=N)C=1C(=C(OC1)C(=O)O)C1=CC=CC2=CC=CC=C12 VVZBIMWRNJKGNH-UHFFFAOYSA-N 0.000 title description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 5
- 125000003277 amino group Chemical group 0.000 claims abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- 125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract 6
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 4
- -1 lower-alkoxy group Chemical group 0.000 claims description 44
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 208000023275 Autoimmune disease Diseases 0.000 claims description 7
- 229940012957 plasmin Drugs 0.000 claims description 7
- 230000000295 complement effect Effects 0.000 claims description 6
- 108060005987 Kallikrein Proteins 0.000 claims description 5
- 102000001399 Kallikrein Human genes 0.000 claims description 5
- 108090000190 Thrombin Proteins 0.000 claims description 5
- 108090000631 Trypsin Proteins 0.000 claims description 5
- 102000004142 Trypsin Human genes 0.000 claims description 5
- 229940088598 enzyme Drugs 0.000 claims description 5
- 229960004072 thrombin Drugs 0.000 claims description 5
- 239000012588 trypsin Substances 0.000 claims description 5
- 102000004190 Enzymes Human genes 0.000 claims description 4
- 108090000790 Enzymes Proteins 0.000 claims description 4
- 108010088842 Fibrinolysin Proteins 0.000 claims description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- 239000002532 enzyme inhibitor Substances 0.000 claims description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- BFIUWZZOXRAEBM-UHFFFAOYSA-N (2-carbamimidoylnaphthalen-1-yl) furan-2-carboxylate Chemical class NC(=N)C1=CC=C2C=CC=CC2=C1OC(=O)C1=CC=CO1 BFIUWZZOXRAEBM-UHFFFAOYSA-N 0.000 claims 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims 1
- 208000017169 kidney disease Diseases 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 abstract description 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical class OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000005037 alkyl phenyl group Chemical group 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 abstract 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 99
- 239000000203 mixture Substances 0.000 description 66
- 238000001816 cooling Methods 0.000 description 65
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 60
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 51
- 238000001914 filtration Methods 0.000 description 49
- 150000001875 compounds Chemical class 0.000 description 48
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 47
- 239000002244 precipitate Substances 0.000 description 42
- 239000000047 product Substances 0.000 description 32
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 28
- 239000000706 filtrate Substances 0.000 description 27
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
- 238000003756 stirring Methods 0.000 description 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 19
- 239000007858 starting material Substances 0.000 description 18
- 239000006228 supernatant Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000013078 crystal Substances 0.000 description 14
- JDMZIQFYXCXMNH-UHFFFAOYSA-N (6-carbamimidoylnaphthalen-2-yl) 5-(aminomethyl)furan-2-carboxylate;dihydrochloride Chemical compound Cl.Cl.O1C(CN)=CC=C1C(=O)OC1=CC=C(C=C(C=C2)C(N)=N)C2=C1 JDMZIQFYXCXMNH-UHFFFAOYSA-N 0.000 description 13
- 239000002198 insoluble material Substances 0.000 description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
- 230000000694 effects Effects 0.000 description 11
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 10
- 239000002775 capsule Substances 0.000 description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000010908 decantation Methods 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 201000008383 nephritis Diseases 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 208000009386 Experimental Arthritis Diseases 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 150000003431 steroids Chemical class 0.000 description 4
- 101710081722 Antitrypsin Proteins 0.000 description 3
- 241000416162 Astragalus gummifer Species 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229920001615 Tragacanth Polymers 0.000 description 3
- 230000000288 anti-kallikrein effect Effects 0.000 description 3
- 230000001475 anti-trypsic effect Effects 0.000 description 3
- 239000004019 antithrombin Substances 0.000 description 3
- 239000001768 carboxy methyl cellulose Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229940098779 methanesulfonic acid Drugs 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- 235000010356 sorbitol Nutrition 0.000 description 3
- 239000002753 trypsin inhibitor Substances 0.000 description 3
- 210000002700 urine Anatomy 0.000 description 3
- RFSOAUZQWFWFBY-UHFFFAOYSA-N (6-carbamimidoylnaphthalen-2-yl) 5-(aminomethyl)furan-2-carboxylate;dihydrobromide Chemical compound Br.Br.O1C(CN)=CC=C1C(=O)OC1=CC=C(C=C(C=C2)C(N)=N)C2=C1 RFSOAUZQWFWFBY-UHFFFAOYSA-N 0.000 description 2
- FLRXNSRJBDMDPB-UHFFFAOYSA-N (6-carbamimidoylnaphthalen-2-yl) 5-[[[2-[4-[(2-methylpropan-2-yl)oxycarbonyl]phenyl]acetyl]amino]methyl]furan-2-carboxylate;hydrochloride Chemical compound Cl.C1=CC(C(=O)OC(C)(C)C)=CC=C1CC(=O)NCC1=CC=C(C(=O)OC=2C=C3C=CC(=CC3=CC=2)C(N)=N)O1 FLRXNSRJBDMDPB-UHFFFAOYSA-N 0.000 description 2
- LGOYDIHSTZJVRA-UHFFFAOYSA-N (6-carbamimidoylnaphthalen-2-yl) 5-[[[4-(2-methoxy-2-oxoethyl)benzoyl]amino]methyl]furan-2-carboxylate;hydrochloride Chemical compound Cl.C1=CC(CC(=O)OC)=CC=C1C(=O)NCC1=CC=C(C(=O)OC=2C=C3C=CC(=CC3=CC=2)C(N)=N)O1 LGOYDIHSTZJVRA-UHFFFAOYSA-N 0.000 description 2
- XGCDBGRZEKYHNV-UHFFFAOYSA-N 1,1-bis(diphenylphosphino)methane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CP(C=1C=CC=CC=1)C1=CC=CC=C1 XGCDBGRZEKYHNV-UHFFFAOYSA-N 0.000 description 2
- SKAWDTAMLOJQNK-UHFFFAOYSA-N 2-acetamido-3-(4-hydroxyphenyl)propanoic acid ethyl ester Chemical compound CCOC(=O)C(NC(C)=O)CC1=CC=C(O)C=C1 SKAWDTAMLOJQNK-UHFFFAOYSA-N 0.000 description 2
- SMNDYUVBFMFKNZ-UHFFFAOYSA-M 2-furoate Chemical compound [O-]C(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-M 0.000 description 2
- MZOKTLMDMWFEOR-UHFFFAOYSA-N 3-[4-[[5-(6-carbamimidoylnaphthalen-2-yl)oxycarbonylfuran-2-yl]methylcarbamoyl]phenyl]prop-2-enoic acid;hydrochloride Chemical compound Cl.C1=CC2=CC(C(=N)N)=CC=C2C=C1OC(=O)C(O1)=CC=C1CNC(=O)C1=CC=C(C=CC(O)=O)C=C1 MZOKTLMDMWFEOR-UHFFFAOYSA-N 0.000 description 2
- CQSIKRACRPAYTR-UHFFFAOYSA-N 4-[[5-(6-carbamimidoylnaphthalen-2-yl)oxycarbonylfuran-2-yl]methylamino]-4-oxobutanoic acid;hydrochloride Chemical compound Cl.C1=CC2=CC(C(=N)N)=CC=C2C=C1OC(=O)C1=CC=C(CNC(=O)CCC(O)=O)O1 CQSIKRACRPAYTR-UHFFFAOYSA-N 0.000 description 2
- RCPINNSEDKEIIC-UHFFFAOYSA-N 5-[[5-(6-carbamimidoylnaphthalen-2-yl)oxycarbonylfuran-2-yl]methylamino]-5-oxopentanoic acid;hydrochloride Chemical compound Cl.C1=CC2=CC(C(=N)N)=CC=C2C=C1OC(=O)C1=CC=C(CNC(=O)CCCC(O)=O)O1 RCPINNSEDKEIIC-UHFFFAOYSA-N 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 2
- 229930195725 Mannitol Natural products 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 206010029120 Nephritis allergic Diseases 0.000 description 2
- 108091005804 Peptidases Proteins 0.000 description 2
- 239000004365 Protease Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- FKMJXALNHKIDOD-LBPRGKRZSA-N TAMe Chemical compound NC(=N)NCCC[C@@H](C(=O)OC)NS(=O)(=O)C1=CC=C(C)C=C1 FKMJXALNHKIDOD-LBPRGKRZSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 2
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 2
- 235000015243 ice cream Nutrition 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 210000003246 kidney medulla Anatomy 0.000 description 2
- 210000003141 lower extremity Anatomy 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000594 mannitol Substances 0.000 description 2
- 235000010355 mannitol Nutrition 0.000 description 2
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 235000010487 tragacanth Nutrition 0.000 description 2
- 239000000196 tragacanth Substances 0.000 description 2
- 229940116362 tragacanth Drugs 0.000 description 2
- 229960001322 trypsin Drugs 0.000 description 2
- ASJCSAKCMTWGAH-RFZPGFLSSA-N (1r,2r)-cyclopentane-1,2-dicarboxylic acid Chemical compound OC(=O)[C@@H]1CCC[C@H]1C(O)=O ASJCSAKCMTWGAH-RFZPGFLSSA-N 0.000 description 1
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- PLIPIVKOXLPPIO-UHFFFAOYSA-N (6-carbamimidoylnaphthalen-2-yl) 5-[[(4-methoxy-4-oxobutanoyl)amino]methyl]furan-2-carboxylate;hydrochloride Chemical compound Cl.O1C(CNC(=O)CCC(=O)OC)=CC=C1C(=O)OC1=CC=C(C=C(C=C2)C(N)=N)C2=C1 PLIPIVKOXLPPIO-UHFFFAOYSA-N 0.000 description 1
- XEPFHYYLRBBTFR-UHFFFAOYSA-N (6-carbamimidoylnaphthalen-2-yl) 5-[[[2-(diaminomethylideneamino)-5-[(2-methylpropan-2-yl)oxy]-5-oxopentanoyl]amino]methyl]furan-2-carboxylate;hydrobromide;hydrochloride Chemical compound Cl.Br.O1C(CNC(=O)C(NC(N)=N)CCC(=O)OC(C)(C)C)=CC=C1C(=O)OC1=CC=C(C=C(C=C2)C(N)=N)C2=C1 XEPFHYYLRBBTFR-UHFFFAOYSA-N 0.000 description 1
- RBFHTKGSJCFIKM-UHFFFAOYSA-N (6-carbamimidoylnaphthalen-2-yl) 5-[[[4-[(2-methylpropan-2-yl)oxy]-4-oxobutanoyl]amino]methyl]furan-2-carboxylate;hydrobromide Chemical compound Br.O1C(CNC(=O)CCC(=O)OC(C)(C)C)=CC=C1C(=O)OC1=CC=C(C=C(C=C2)C(N)=N)C2=C1 RBFHTKGSJCFIKM-UHFFFAOYSA-N 0.000 description 1
- YOCFLHKSZDLIKG-UHFFFAOYSA-N (6-carbamimidoylnaphthalen-2-yl) 5-[[[4-[3-[(2-methylpropan-2-yl)oxy]-3-oxoprop-1-enyl]benzoyl]amino]methyl]furan-2-carboxylate;hydrobromide Chemical compound Br.C1=CC(C=CC(=O)OC(C)(C)C)=CC=C1C(=O)NCC1=CC=C(C(=O)OC=2C=C3C=CC(=CC3=CC=2)C(N)=N)O1 YOCFLHKSZDLIKG-UHFFFAOYSA-N 0.000 description 1
- JYENLWRRHJEEJB-UHFFFAOYSA-N (6-carbamimidoylnaphthalen-2-yl) 5-[[[4-[3-[(2-methylpropan-2-yl)oxy]-3-oxoprop-1-enyl]benzoyl]amino]methyl]furan-2-carboxylate;hydrochloride Chemical compound Cl.C1=CC(C=CC(=O)OC(C)(C)C)=CC=C1C(=O)NCC1=CC=C(C(=O)OC=2C=C3C=CC(=CC3=CC=2)C(N)=N)O1 JYENLWRRHJEEJB-UHFFFAOYSA-N 0.000 description 1
- HPHPJSLKYXUEBJ-UHFFFAOYSA-N (6-carbamimidoylnaphthalen-2-yl) 5-[[[5-[(2-methylpropan-2-yl)oxy]-5-oxopentanoyl]amino]methyl]furan-2-carboxylate;hydrochloride Chemical compound Cl.O1C(CNC(=O)CCCC(=O)OC(C)(C)C)=CC=C1C(=O)OC1=CC=C(C=C(C=C2)C(N)=N)C2=C1 HPHPJSLKYXUEBJ-UHFFFAOYSA-N 0.000 description 1
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
- XNONHUBNQKPICE-UHFFFAOYSA-N 1-hydroxynaphthalene-2-carboximidamide Chemical group C1=CC=CC2=C(O)C(C(=N)N)=CC=C21 XNONHUBNQKPICE-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- KLZYRCVPDWTZLH-UHFFFAOYSA-N 2,3-dimethylsuccinic acid Chemical compound OC(=O)C(C)C(C)C(O)=O KLZYRCVPDWTZLH-UHFFFAOYSA-N 0.000 description 1
- XBBCTUBJONGLPC-UHFFFAOYSA-N 2-(diaminomethylideneamino)-5-[(2-methylpropan-2-yl)oxy]-5-oxopentanoic acid;hydrochloride Chemical compound Cl.CC(C)(C)OC(=O)CCC(C(O)=O)NC(N)=N XBBCTUBJONGLPC-UHFFFAOYSA-N 0.000 description 1
- XFORQVOFSGYRFZ-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxy]-2-oxoacetic acid Chemical compound CC(C)(C)OC(=O)C(O)=O XFORQVOFSGYRFZ-UHFFFAOYSA-N 0.000 description 1
- AKSVALRPYDVQBS-CABCVRRESA-N 2-[(3R)-3-[1-[1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-3-(trifluoromethyl)pyrazolo[3,4-b]pyrazin-6-yl]azetidin-3-yl]piperidin-1-yl]ethanol Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)N1CC(C1)[C@@H]1CN(CCC1)CCO)C(F)(F)F AKSVALRPYDVQBS-CABCVRRESA-N 0.000 description 1
- XTEXEHUFGYHISA-UHFFFAOYSA-N 2-[4-[[5-(6-carbamimidoylnaphthalen-2-yl)oxycarbonylfuran-2-yl]methylcarbamoyl]phenyl]acetic acid;hydrochloride Chemical compound Cl.C1=CC2=CC(C(=N)N)=CC=C2C=C1OC(=O)C(O1)=CC=C1CNC(=O)C1=CC=C(CC(O)=O)C=C1 XTEXEHUFGYHISA-UHFFFAOYSA-N 0.000 description 1
- FOYWCEUVVIHJKD-UHFFFAOYSA-N 2-methyl-5-(1h-pyrazol-5-yl)pyridine Chemical compound C1=NC(C)=CC=C1C1=CC=NN1 FOYWCEUVVIHJKD-UHFFFAOYSA-N 0.000 description 1
- WEHVICGKIFVXSR-UHFFFAOYSA-N 3-[[5-(6-carbamimidoylnaphthalen-2-yl)oxycarbonylfuran-2-yl]methylamino]-3-oxopropanoic acid;hydrochloride Chemical compound Cl.C1=CC2=CC(C(=N)N)=CC=C2C=C1OC(=O)C1=CC=C(CNC(=O)CC(O)=O)O1 WEHVICGKIFVXSR-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
- PCOCFIOYWNCGBM-UHFFFAOYSA-N 4-[(2-methylpropan-2-yl)oxy]-4-oxobutanoic acid Chemical compound CC(C)(C)OC(=O)CCC(O)=O PCOCFIOYWNCGBM-UHFFFAOYSA-N 0.000 description 1
- CPUILRNFVBCOAB-UHFFFAOYSA-N 4-[2-[[5-(6-carbamimidoylnaphthalen-2-yl)oxycarbonylfuran-2-yl]methylamino]-2-oxoethyl]benzoic acid;hydrochloride Chemical compound Cl.C1=CC2=CC(C(=N)N)=CC=C2C=C1OC(=O)C(O1)=CC=C1CNC(=O)CC1=CC=C(C(O)=O)C=C1 CPUILRNFVBCOAB-UHFFFAOYSA-N 0.000 description 1
- BZUPIVMMIUZGDI-UHFFFAOYSA-N 4-[3-[(2-methylpropan-2-yl)oxy]-3-oxoprop-1-enyl]benzoic acid Chemical compound CC(C)(C)OC(=O)C=CC1=CC=C(C(O)=O)C=C1 BZUPIVMMIUZGDI-UHFFFAOYSA-N 0.000 description 1
- UETGXUNOOZOAPG-UHFFFAOYSA-N 4-[[5-(6-carbamimidoylnaphthalen-2-yl)oxycarbonylfuran-2-yl]methylamino]-2,3-dimethyl-4-oxobutanoic acid;hydrochloride Chemical compound Cl.O1C(CNC(=O)C(C)C(C)C(O)=O)=CC=C1C(=O)OC1=CC=C(C=C(C=C2)C(N)=N)C2=C1 UETGXUNOOZOAPG-UHFFFAOYSA-N 0.000 description 1
- YKMUHJKOGKQQJL-UHFFFAOYSA-N 4-[[5-(6-carbamimidoylnaphthalen-2-yl)oxycarbonylfuran-2-yl]methylamino]-4-oxobutanoic acid;hydrobromide Chemical compound Br.C1=CC2=CC(C(=N)N)=CC=C2C=C1OC(=O)C1=CC=C(CNC(=O)CCC(O)=O)O1 YKMUHJKOGKQQJL-UHFFFAOYSA-N 0.000 description 1
- CEHUPFLZTXPWKI-UHFFFAOYSA-N 4-[[5-(6-carbamimidoylnaphthalen-2-yl)oxycarbonylfuran-2-yl]methylcarbamoyl]benzoic acid;hydrochloride Chemical compound Cl.C1=CC2=CC(C(=N)N)=CC=C2C=C1OC(=O)C(O1)=CC=C1CNC(=O)C1=CC=C(C(O)=O)C=C1 CEHUPFLZTXPWKI-UHFFFAOYSA-N 0.000 description 1
- OYDXXVFKUKFBBQ-UHFFFAOYSA-N 5-[[5-(6-carbamimidoylnaphthalen-2-yl)oxycarbonylfuran-2-yl]methylamino]-3-methyl-5-oxopentanoic acid;hydrochloride Chemical compound Cl.O1C(CNC(=O)CC(CC(O)=O)C)=CC=C1C(=O)OC1=CC=C(C=C(C=C2)C(N)=N)C2=C1 OYDXXVFKUKFBBQ-UHFFFAOYSA-N 0.000 description 1
- FTRGSQPFVJADAQ-UHFFFAOYSA-N 5-[[5-(6-carbamimidoylnaphthalen-2-yl)oxycarbonylfuran-2-yl]methylamino]-4-(diaminomethylideneamino)-5-oxopentanoic acid;dihydrobromide Chemical compound Br.Br.O1C(CNC(=O)C(CCC(O)=O)NC(=N)N)=CC=C1C(=O)OC1=CC=C(C=C(C=C2)C(N)=N)C2=C1 FTRGSQPFVJADAQ-UHFFFAOYSA-N 0.000 description 1
- VAOSLCZLXWQGKA-UHFFFAOYSA-N 5-[[5-(6-carbamimidoylnaphthalen-2-yl)oxycarbonylfuran-2-yl]methylamino]-5-oxopentanoic acid;methanesulfonic acid Chemical compound CS(O)(=O)=O.C1=CC2=CC(C(=N)N)=CC=C2C=C1OC(=O)C1=CC=C(CNC(=O)CCCC(O)=O)O1 VAOSLCZLXWQGKA-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 206010003694 Atrophy Diseases 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 108090000371 Esterases Proteins 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- GISRWBROCYNDME-PELMWDNLSA-N F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C Chemical compound F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C GISRWBROCYNDME-PELMWDNLSA-N 0.000 description 1
- 208000032843 Hemorrhage Diseases 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- ZDLDXNCMJBOYJV-YFKPBYRVSA-N L-arginine, methyl ester Chemical compound COC(=O)[C@@H](N)CCCN=C(N)N ZDLDXNCMJBOYJV-YFKPBYRVSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products 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 1
- 241000186359 Mycobacterium Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 206010033645 Pancreatitis Diseases 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 1
- 206010039710 Scleroderma Diseases 0.000 description 1
- 206010067868 Skin mass Diseases 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 241000212749 Zesius chrysomallus Species 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 210000004100 adrenal gland Anatomy 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 230000002391 anti-complement effect Effects 0.000 description 1
- 230000003260 anti-sepsis Effects 0.000 description 1
- 108010008730 anticomplement Proteins 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000037444 atrophy Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 208000034158 bleeding Diseases 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000023555 blood coagulation Effects 0.000 description 1
- 230000037396 body weight Effects 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
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 239000002350 fibrinopeptide Substances 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- CLEYBUZWXNEMSC-UHFFFAOYSA-N furan-2-carboxylic acid;hydrochloride Chemical compound Cl.OC(=O)C1=CC=CO1 CLEYBUZWXNEMSC-UHFFFAOYSA-N 0.000 description 1
- 229940014259 gelatin Drugs 0.000 description 1
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 230000036737 immune function Effects 0.000 description 1
- 230000003053 immunization Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229960003511 macrogol Drugs 0.000 description 1
- 235000019359 magnesium stearate 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
- PSGAAPLEWMOORI-PEINSRQWSA-N medroxyprogesterone acetate Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 PSGAAPLEWMOORI-PEINSRQWSA-N 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose 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
- 239000012053 oil suspension Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000020374 simple syrup Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 210000005239 tubule Anatomy 0.000 description 1
- 210000001364 upper extremity Anatomy 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Urology & Nephrology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Immunology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Detergent Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4023848A JPH05213927A (ja) | 1992-02-10 | 1992-02-10 | 新規フランカルボン酸アミジノナフチルエステル誘導体およびその酸付加塩 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO924758D0 NO924758D0 (no) | 1992-12-09 |
| NO924758L NO924758L (no) | 1993-08-11 |
| NO300633B1 true NO300633B1 (no) | 1997-06-30 |
Family
ID=12121832
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO924758A NO300633B1 (no) | 1992-02-10 | 1992-12-09 | Nye amidinonaftylfurankarboksylatderivater og syreaddisjonssalter derav, samt farmasöytiske preparater inneholdende dem |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP0556024B1 (es) |
| JP (1) | JPH05213927A (es) |
| KR (1) | KR100229254B1 (es) |
| AT (1) | ATE125806T1 (es) |
| AU (1) | AU652076B2 (es) |
| CA (1) | CA2079267A1 (es) |
| DE (1) | DE69300307T2 (es) |
| DK (1) | DK0556024T3 (es) |
| FI (1) | FI925311A (es) |
| HU (1) | HUT63841A (es) |
| MX (1) | MX9205914A (es) |
| NO (1) | NO300633B1 (es) |
| PL (1) | PL174421B1 (es) |
| RU (1) | RU2096410C1 (es) |
| TW (1) | TW232687B (es) |
| ZA (1) | ZA927646B (es) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU1208999A (en) * | 1997-11-10 | 1999-05-31 | Array Biopharma, Inc. | Compounds which inhibit tryptase activity |
| US6362216B1 (en) | 1998-10-27 | 2002-03-26 | Array Biopharma Inc. | Compounds which inhibit tryptase activity |
| JP3395061B2 (ja) | 2000-02-21 | 2003-04-07 | 学校法人金沢工業大学 | 図書館の蔵書自動出納システムと図書館の蔵書出納ロボットならびに図書館の蔵書出納ロボットのハンド機構 |
| GB0507577D0 (en) | 2005-04-14 | 2005-05-18 | Novartis Ag | Organic compounds |
| JP5959116B2 (ja) * | 2011-06-07 | 2016-08-02 | Ｅａファーマ株式会社 | ヘテロ環カルボン酸エステル誘導体 |
| US9024044B2 (en) * | 2012-06-14 | 2015-05-05 | Ajinomoto Co., Inc. | Heteroarylcarboxylic acid ester derivative |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59139357A (ja) * | 1983-01-28 | 1984-08-10 | Torii Yakuhin Kk | アミジン誘導体 |
| US4563527A (en) * | 1984-07-19 | 1986-01-07 | Torii & Co., Ltd. | Amidine compounds |
-
1992
- 1992-02-10 JP JP4023848A patent/JPH05213927A/ja active Pending
- 1992-09-25 TW TW081107606A patent/TW232687B/zh active
- 1992-09-28 CA CA002079267A patent/CA2079267A1/en not_active Abandoned
- 1992-09-28 AU AU25378/92A patent/AU652076B2/en not_active Ceased
- 1992-10-05 ZA ZA927646A patent/ZA927646B/xx unknown
- 1992-10-15 MX MX9205914A patent/MX9205914A/es not_active IP Right Cessation
- 1992-11-12 KR KR1019920021250A patent/KR100229254B1/ko not_active IP Right Cessation
- 1992-11-23 FI FI925311A patent/FI925311A/fi unknown
- 1992-12-09 RU RU9292004533A patent/RU2096410C1/ru active
- 1992-12-09 NO NO924758A patent/NO300633B1/no not_active IP Right Cessation
- 1992-12-10 HU HU9203908A patent/HUT63841A/hu unknown
-
1993
- 1993-02-02 PL PL93297964A patent/PL174421B1/pl unknown
- 1993-02-09 EP EP93300938A patent/EP0556024B1/en not_active Expired - Lifetime
- 1993-02-09 AT AT93300938T patent/ATE125806T1/de not_active IP Right Cessation
- 1993-02-09 DE DE69300307T patent/DE69300307T2/de not_active Expired - Fee Related
- 1993-02-09 DK DK93300938.3T patent/DK0556024T3/da active
Also Published As
| Publication number | Publication date |
|---|---|
| RU2096410C1 (ru) | 1997-11-20 |
| NO924758L (no) | 1993-08-11 |
| EP0556024A1 (en) | 1993-08-18 |
| PL297964A1 (en) | 1993-10-18 |
| KR100229254B1 (ko) | 1999-11-01 |
| CA2079267A1 (en) | 1993-08-11 |
| NO924758D0 (no) | 1992-12-09 |
| AU2537892A (en) | 1993-08-12 |
| ATE125806T1 (de) | 1995-08-15 |
| HUT63841A (en) | 1993-10-28 |
| ZA927646B (en) | 1993-04-13 |
| TW232687B (es) | 1994-10-21 |
| KR930017884A (ko) | 1993-09-20 |
| AU652076B2 (en) | 1994-08-11 |
| PL174421B1 (pl) | 1998-07-31 |
| DE69300307T2 (de) | 1996-01-25 |
| EP0556024B1 (en) | 1995-08-02 |
| HU9203908D0 (en) | 1993-04-28 |
| JPH05213927A (ja) | 1993-08-24 |
| DE69300307D1 (de) | 1995-09-07 |
| FI925311A (fi) | 1993-08-11 |
| MX9205914A (es) | 1993-09-01 |
| FI925311A0 (fi) | 1992-11-23 |
| DK0556024T3 (da) | 1995-09-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR100948278B1 (ko) | 방향족 아미노산 유도체 및 의약 조성물 | |
| DE3486354T2 (de) | Chroman- und Chromenderivate. | |
| KR20010033154A (ko) | 제약물로서의 신규한 아민 | |
| WO2007001335A2 (en) | Ramoplanin derivatives possessing antibacterial activity | |
| WO1993015047A1 (en) | Amino acid derivatives as paf antagonists | |
| BG100396A (bg) | Производни на n-(3-бензофуранил)карбамида,метод за получаване и използването им | |
| WO2009123241A1 (ja) | プラスミノーゲンアクチベーターインヒビター－１阻害剤 | |
| CA2965512A1 (en) | Trifluoromethyl alcohols as modulators of ror.gamma.t | |
| CA2098912A1 (en) | Benzoxa condensed ring compound, process for producing the same and pharmaceutical composition comprising the same | |
| CA2936467A1 (en) | Hydroxy formamide derivatives and their use | |
| US5462940A (en) | 4-oxocyclic ureas useful as antiarrhythmic and antifibrillatory agents | |
| US4914099A (en) | Hydantoin derivatives as aldose reductase inhibitors | |
| CN102811998A (zh) | 新的亲环素抑制剂及其用途 | |
| US5500427A (en) | Cyclic compounds and their use | |
| NO300633B1 (no) | Nye amidinonaftylfurankarboksylatderivater og syreaddisjonssalter derav, samt farmasöytiske preparater inneholdende dem | |
| SU1706389A3 (ru) | Способ получени [5(6)-(1Н-азол-1-ил-метил)-бензимидазол]карбаматов | |
| KR20170103803A (ko) | 요산 수준의 저감을 위한 이작용성 화합물 및 용도 | |
| US5532267A (en) | Amidinonaphthyl furancarboxylate derivatives and acid addition salts therof | |
| US5691369A (en) | Cyclic ureas useful as antiarrhythmic and antifibrillatory agents | |
| AU665367B2 (en) | Cyclic urethanes useful as antiarrhythmic and antifibrillatory agents | |
| CN104844533B (zh) | 含五元芳杂环的氨基丙二醇类化合物、其制备方法及其医药用途 | |
| HU196170B (en) | Process for preparing (/1,3-dioxi-1,3-propane-diil/-diimino)-bis-benzoic acid and its derivatives | |
| KR820002296B1 (ko) | 모라노린의 n-치환 유도체의 제조방법 | |
| KR100720045B1 (ko) | 신규 크로만온 옥심 카보닐구아니딘 유도체, 이의약학적으로 허용가능한 염, 이의 제조방법 및 이를유효성분으로 함유하는 허혈성 심장질환의 예방 및 치료용약학적 조성물 | |
| JP2005501090A (ja) | ヒドロキサム酸誘導体 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |
Free format text: LAPSED IN JUNE 2001 |