BG65497B1 - Стент с полимерно покритие, съдържащо средства заинхибиране на рестеноза - Google Patents
Стент с полимерно покритие, съдържащо средства заинхибиране на рестеноза Download PDFInfo
- Publication number
- BG65497B1 BG65497B1 BG105625A BG10562501A BG65497B1 BG 65497 B1 BG65497 B1 BG 65497B1 BG 105625 A BG105625 A BG 105625A BG 10562501 A BG10562501 A BG 10562501A BG 65497 B1 BG65497 B1 BG 65497B1
- Authority
- BG
- Bulgaria
- Prior art keywords
- dimethoxy
- amine
- quinoxalin
- stent
- poly
- Prior art date
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 67
- 238000000576 coating method Methods 0.000 title claims abstract description 36
- 239000011248 coating agent Substances 0.000 title claims abstract description 32
- 208000037803 restenosis Diseases 0.000 title claims abstract description 20
- 230000002401 inhibitory effect Effects 0.000 title claims description 16
- 239000003795 chemical substances by application Substances 0.000 title description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 104
- -1 hydroxy, carboxy Chemical group 0.000 claims description 82
- 239000000203 mixture Substances 0.000 claims description 71
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 50
- 150000003839 salts Chemical class 0.000 claims description 37
- 239000011780 sodium chloride Substances 0.000 claims description 25
- 239000012528 membrane Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000002202 Polyethylene glycol Substances 0.000 claims description 11
- 150000001412 amines Chemical class 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 239000000178 monomer Substances 0.000 claims description 11
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- 229920001223 polyethylene glycol Polymers 0.000 claims description 10
- 229920001577 copolymer Polymers 0.000 claims description 9
- 229920001296 polysiloxane Polymers 0.000 claims description 9
- 229940002612 prodrug Drugs 0.000 claims description 9
- 239000000651 prodrug Substances 0.000 claims description 9
- 239000012453 solvate Substances 0.000 claims description 9
- 239000004952 Polyamide Substances 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 229920002647 polyamide Polymers 0.000 claims description 8
- 229920000669 heparin Polymers 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- VBXDPTHXXPWTNC-UHFFFAOYSA-N n-heptan-2-yl-6,7-dimethoxyquinoxalin-2-amine Chemical compound C1=C(OC)C(OC)=CC2=NC(NC(C)CCCCC)=CN=C21 VBXDPTHXXPWTNC-UHFFFAOYSA-N 0.000 claims description 7
- 229920001432 poly(L-lactide) Polymers 0.000 claims description 7
- 229920000052 poly(p-xylylene) Polymers 0.000 claims description 7
- 239000004417 polycarbonate Substances 0.000 claims description 7
- 229920000515 polycarbonate Polymers 0.000 claims description 7
- 229920001451 polypropylene glycol Polymers 0.000 claims description 7
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical group C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 claims description 6
- 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 claims description 6
- 150000001204 N-oxides Chemical class 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 230000000975 bioactive effect Effects 0.000 claims description 6
- 229920002678 cellulose Polymers 0.000 claims description 6
- 239000001913 cellulose Substances 0.000 claims description 6
- ZFGMDIBRIDKWMY-PASTXAENSA-N heparin Chemical compound CC(O)=N[C@@H]1[C@@H](O)[C@H](O)[C@@H](COS(O)(=O)=O)O[C@@H]1O[C@@H]1[C@@H](C(O)=O)O[C@@H](O[C@H]2[C@@H]([C@@H](OS(O)(=O)=O)[C@@H](O[C@@H]3[C@@H](OC(O)[C@H](OS(O)(=O)=O)[C@H]3O)C(O)=O)O[C@@H]2O)CS(O)(=O)=O)[C@H](O)[C@H]1O ZFGMDIBRIDKWMY-PASTXAENSA-N 0.000 claims description 6
- 239000008101 lactose Substances 0.000 claims description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 6
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 claims description 6
- 229920002635 polyurethane Polymers 0.000 claims description 6
- 239000004814 polyurethane Substances 0.000 claims description 6
- 229920002554 vinyl polymer Polymers 0.000 claims description 6
- 229920001710 Polyorthoester Polymers 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 230000008021 deposition Effects 0.000 claims description 5
- 229910052736 halogen Chemical group 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- 229920002627 poly(phosphazenes) Polymers 0.000 claims description 5
- 229920002689 polyvinyl acetate Polymers 0.000 claims description 5
- 239000011118 polyvinyl acetate Substances 0.000 claims description 5
- 229920005989 resin Polymers 0.000 claims description 5
- 239000011347 resin Substances 0.000 claims description 5
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 claims description 4
- BEFUAVPFBGOHKT-UHFFFAOYSA-N 2-cyclohexyloxy-6,7-dimethoxyquinoxaline Chemical compound N1=C2C=C(OC)C(OC)=CC2=NC=C1OC1CCCCC1 BEFUAVPFBGOHKT-UHFFFAOYSA-N 0.000 claims description 4
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 4
- 102000008186 Collagen Human genes 0.000 claims description 4
- 108010035532 Collagen Proteins 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 229920001436 collagen Polymers 0.000 claims description 4
- 229960001008 heparin sodium Drugs 0.000 claims description 4
- NNCUETCKTZPULT-UHFFFAOYSA-N n-cyclohex-3-en-1-yl-6,7-dimethoxyquinoxalin-2-amine Chemical compound N1=C2C=C(OC)C(OC)=CC2=NC=C1NC1CCC=CC1 NNCUETCKTZPULT-UHFFFAOYSA-N 0.000 claims description 4
- FBCVQPSZSMHQGK-UHFFFAOYSA-N n-cyclopentyl-6,7-dimethoxyquinoxalin-2-amine Chemical compound N1=C2C=C(OC)C(OC)=CC2=NC=C1NC1CCCC1 FBCVQPSZSMHQGK-UHFFFAOYSA-N 0.000 claims description 4
- 229920001610 polycaprolactone Polymers 0.000 claims description 4
- 239000004632 polycaprolactone Substances 0.000 claims description 4
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 claims description 3
- JYDYHSHPBDZRPU-ULUSZKPHSA-N (3r)-3-methylcyclohexan-1-amine Chemical compound C[C@@H]1CCCC(N)C1 JYDYHSHPBDZRPU-ULUSZKPHSA-N 0.000 claims description 3
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 claims description 3
- ICGQLNMKJVHCIR-UHFFFAOYSA-N 1,3,2-dioxazetidin-4-one Chemical compound O=C1ONO1 ICGQLNMKJVHCIR-UHFFFAOYSA-N 0.000 claims description 3
- GDOBGDUGIFUCJV-UHFFFAOYSA-N 2,2-dimethylbutane;2-methylprop-2-enoic acid Chemical compound CCC(C)(C)C.CC(=C)C(O)=O.CC(=C)C(O)=O.CC(=C)C(O)=O GDOBGDUGIFUCJV-UHFFFAOYSA-N 0.000 claims description 3
- OYKPJMYWPYIXGG-UHFFFAOYSA-N 2,2-dimethylbutane;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.CCC(C)(C)C OYKPJMYWPYIXGG-UHFFFAOYSA-N 0.000 claims description 3
- UBIZPJMDFPWKAR-UHFFFAOYSA-N 2-(5-bicyclo[2.2.1]hept-2-enyloxy)-6,7-dimethoxyquinoxaline Chemical compound N1=C2C=C(OC)C(OC)=CC2=NC=C1OC1C(C=C2)CC2C1 UBIZPJMDFPWKAR-UHFFFAOYSA-N 0.000 claims description 3
- GRBVFGKKVXWZII-UHFFFAOYSA-N 2-(cyclopentylmethoxy)-6,7-dimethoxyquinoxaline Chemical compound N1=C2C=C(OC)C(OC)=CC2=NC=C1OCC1CCCC1 GRBVFGKKVXWZII-UHFFFAOYSA-N 0.000 claims description 3
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims description 3
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 claims description 3
- ZECSITHIZNOWKL-UHFFFAOYSA-N 3-cyclohexyloxy-6,7-dimethoxyquinoline Chemical compound C=1N=C2C=C(OC)C(OC)=CC2=CC=1OC1CCCCC1 ZECSITHIZNOWKL-UHFFFAOYSA-N 0.000 claims description 3
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims description 3
- LXZQIENFRLLTPA-UHFFFAOYSA-N 6,7-dimethoxy-n-(2-methylpropyl)quinolin-3-amine Chemical compound CC(C)CNC1=CN=C2C=C(OC)C(OC)=CC2=C1 LXZQIENFRLLTPA-UHFFFAOYSA-N 0.000 claims description 3
- YSXVDGDYVJMBPG-UHFFFAOYSA-N 7-bromo-n-cyclohexyl-6-methoxyquinoxalin-2-amine;hydrochloride Chemical compound Cl.N1=C2C=C(Br)C(OC)=CC2=NC=C1NC1CCCCC1 YSXVDGDYVJMBPG-UHFFFAOYSA-N 0.000 claims description 3
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 3
- 229920000298 Cellophane Polymers 0.000 claims description 3
- DQEFEBPAPFSJLV-UHFFFAOYSA-N Cellulose propionate Chemical compound CCC(=O)OCC1OC(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C1OC1C(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C(COC(=O)CC)O1 DQEFEBPAPFSJLV-UHFFFAOYSA-N 0.000 claims description 3
- 229920001651 Cyanoacrylate Polymers 0.000 claims description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 3
- 102000009123 Fibrin Human genes 0.000 claims description 3
- 108010073385 Fibrin Proteins 0.000 claims description 3
- BWGVNKXGVNDBDI-UHFFFAOYSA-N Fibrin monomer Chemical compound CNC(=O)CNC(=O)CN BWGVNKXGVNDBDI-UHFFFAOYSA-N 0.000 claims description 3
- 108010049003 Fibrinogen Proteins 0.000 claims description 3
- 102000008946 Fibrinogen Human genes 0.000 claims description 3
- 239000000020 Nitrocellulose Substances 0.000 claims description 3
- 229920002292 Nylon 6 Polymers 0.000 claims description 3
- 229920002302 Nylon 6,6 Polymers 0.000 claims description 3
- 239000002033 PVDF binder Substances 0.000 claims description 3
- 239000004698 Polyethylene Substances 0.000 claims description 3
- 229920000331 Polyhydroxybutyrate Polymers 0.000 claims description 3
- 229920002367 Polyisobutene Polymers 0.000 claims description 3
- 239000004793 Polystyrene Substances 0.000 claims description 3
- 229920001328 Polyvinylidene chloride Polymers 0.000 claims description 3
- 229920000297 Rayon Polymers 0.000 claims description 3
- 229920002472 Starch Polymers 0.000 claims description 3
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 claims description 3
- 125000005396 acrylic acid ester group Chemical group 0.000 claims description 3
- 229920006243 acrylic copolymer Polymers 0.000 claims description 3
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 claims description 3
- 229920001893 acrylonitrile styrene Polymers 0.000 claims description 3
- 150000001336 alkenes Chemical class 0.000 claims description 3
- 238000002399 angioplasty Methods 0.000 claims description 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical group CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 3
- 239000001768 carboxy methyl cellulose Substances 0.000 claims description 3
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims description 3
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims description 3
- 229920002301 cellulose acetate Polymers 0.000 claims description 3
- 229920006217 cellulose acetate butyrate Polymers 0.000 claims description 3
- 229920001727 cellulose butyrate Polymers 0.000 claims description 3
- 229920003086 cellulose ether Polymers 0.000 claims description 3
- 229920006218 cellulose propionate Polymers 0.000 claims description 3
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 3
- 239000005038 ethylene vinyl acetate Substances 0.000 claims description 3
- 229920006213 ethylene-alphaolefin copolymer Polymers 0.000 claims description 3
- 229920005680 ethylene-methyl methacrylate copolymer Polymers 0.000 claims description 3
- 229950003499 fibrin Drugs 0.000 claims description 3
- 229940012952 fibrinogen Drugs 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 3
- 229920002674 hyaluronan Polymers 0.000 claims description 3
- 229960003160 hyaluronic acid Drugs 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 claims description 3
- 125000005397 methacrylic acid ester group Chemical group 0.000 claims description 3
- 125000002757 morpholinyl group Chemical group 0.000 claims description 3
- YFZQPHGDRHSTGB-UHFFFAOYSA-N n-cycloheptyl-6,7-dimethoxyquinoxalin-2-amine Chemical compound N1=C2C=C(OC)C(OC)=CC2=NC=C1NC1CCCCCC1 YFZQPHGDRHSTGB-UHFFFAOYSA-N 0.000 claims description 3
- VEHQMEZRSRNAAH-UHFFFAOYSA-N n-cyclohexyl-6,7-dimethoxyquinoxalin-2-amine Chemical compound N1=C2C=C(OC)C(OC)=CC2=NC=C1NC1CCCCC1 VEHQMEZRSRNAAH-UHFFFAOYSA-N 0.000 claims description 3
- RHZYQTPCJHEBKB-UHFFFAOYSA-N n-cyclohexyl-6-methoxy-7-morpholin-4-ylquinoxalin-2-amine Chemical compound N1=C2C=C(N3CCOCC3)C(OC)=CC2=NC=C1NC1CCCCC1 RHZYQTPCJHEBKB-UHFFFAOYSA-N 0.000 claims description 3
- CFAAOOAZIREBHB-UHFFFAOYSA-N n-cyclohexyl-6-methoxyquinoxalin-2-amine Chemical compound C1=NC2=CC(OC)=CC=C2N=C1NC1CCCCC1 CFAAOOAZIREBHB-UHFFFAOYSA-N 0.000 claims description 3
- 229920001220 nitrocellulos Polymers 0.000 claims description 3
- 150000003891 oxalate salts Chemical class 0.000 claims description 3
- 229920001308 poly(aminoacid) Polymers 0.000 claims description 3
- 239000005015 poly(hydroxybutyrate) Substances 0.000 claims description 3
- 229920001849 poly(hydroxybutyrate-co-valerate) Polymers 0.000 claims description 3
- 239000002745 poly(ortho ester) Substances 0.000 claims description 3
- 229920002463 poly(p-dioxanone) polymer Polymers 0.000 claims description 3
- 229920002432 poly(vinyl methyl ether) polymer Polymers 0.000 claims description 3
- 229920000058 polyacrylate Polymers 0.000 claims description 3
- 229920002239 polyacrylonitrile Polymers 0.000 claims description 3
- 229920001281 polyalkylene Polymers 0.000 claims description 3
- 239000000622 polydioxanone Substances 0.000 claims description 3
- 229920000647 polyepoxide Polymers 0.000 claims description 3
- 229920000728 polyester Polymers 0.000 claims description 3
- 229920000570 polyether Polymers 0.000 claims description 3
- 229920000573 polyethylene Polymers 0.000 claims description 3
- 239000002861 polymer material Substances 0.000 claims description 3
- 229920000098 polyolefin Polymers 0.000 claims description 3
- 229920006324 polyoxymethylene Polymers 0.000 claims description 3
- 229920002223 polystyrene Polymers 0.000 claims description 3
- 229920006216 polyvinyl aromatic Polymers 0.000 claims description 3
- 229920001290 polyvinyl ester Polymers 0.000 claims description 3
- 229920001289 polyvinyl ether Polymers 0.000 claims description 3
- 229920006215 polyvinyl ketone Polymers 0.000 claims description 3
- 239000005033 polyvinylidene chloride Substances 0.000 claims description 3
- 229920002981 polyvinylidene fluoride Polymers 0.000 claims description 3
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 claims description 3
- 239000008107 starch Substances 0.000 claims description 3
- 235000019698 starch Nutrition 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 150000003673 urethanes Chemical class 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- QYCGBAJADAGLLK-UHFFFAOYSA-N 1-(cyclohepten-1-yl)cycloheptene Chemical group C1CCCCC=C1C1=CCCCCC1 QYCGBAJADAGLLK-UHFFFAOYSA-N 0.000 claims description 2
- PDYLXMCEYVFXEF-UHFFFAOYSA-N 2-(3-bicyclo[2.2.2]octanyloxy)-6,7-dimethoxyquinoxaline Chemical compound C1C(CC2)CCC2C1OC1=CN=C2C=C(OC)C(OC)=CC2=N1 PDYLXMCEYVFXEF-UHFFFAOYSA-N 0.000 claims description 2
- ZHAMQTUXCPUZFN-UHFFFAOYSA-N 2-cyclopentylsulfanyl-6,7-dimethoxyquinoxaline Chemical compound N1=C2C=C(OC)C(OC)=CC2=NC=C1SC1CCCC1 ZHAMQTUXCPUZFN-UHFFFAOYSA-N 0.000 claims description 2
- BCNNPNXBUFWMLE-UHFFFAOYSA-N 4-(6,7-dimethoxyquinoxalin-2-yl)-3-azabicyclo[2.2.2]octan-2-one Chemical compound C1CC(C(=O)N2)CCC12C1=CN=C2C=C(OC)C(OC)=CC2=N1 BCNNPNXBUFWMLE-UHFFFAOYSA-N 0.000 claims description 2
- OMHPHFWGEQHURJ-UHFFFAOYSA-N 6,7-dimethoxy-2-(4-methoxycyclohexyl)oxyquinoxaline Chemical compound C1CC(OC)CCC1OC1=CN=C(C=C(OC)C(OC)=C2)C2=N1 OMHPHFWGEQHURJ-UHFFFAOYSA-N 0.000 claims description 2
- BXIVNNOVMZKTJO-UHFFFAOYSA-N 6,7-dimethoxy-n-(3-methylcyclopentyl)quinolin-3-amine Chemical compound C=1N=C2C=C(OC)C(OC)=CC2=CC=1NC1CCC(C)C1 BXIVNNOVMZKTJO-UHFFFAOYSA-N 0.000 claims description 2
- YEAUGSGQDBWJFI-UHFFFAOYSA-N 6,7-dimethoxy-n-(4-methoxycyclohexyl)quinoxalin-2-amine Chemical compound C1CC(OC)CCC1NC1=CN=C(C=C(OC)C(OC)=C2)C2=N1 YEAUGSGQDBWJFI-UHFFFAOYSA-N 0.000 claims description 2
- SAPGBCWOQLHKKZ-UHFFFAOYSA-N 6-(2-methylprop-2-enoyloxy)hexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCOC(=O)C(C)=C SAPGBCWOQLHKKZ-UHFFFAOYSA-N 0.000 claims description 2
- PGZIXJPIEHMSEP-UHFFFAOYSA-N 7-chloro-N-heptan-2-yl-6-methoxyquinoxalin-2-amine Chemical compound CCCCCC(C)Nc1cnc2cc(OC)c(Cl)cc2n1 PGZIXJPIEHMSEP-UHFFFAOYSA-N 0.000 claims description 2
- LZEAKVJEHLYTJO-UHFFFAOYSA-N N-hept-5-en-2-yl-6,7-dimethoxyquinoxalin-2-amine Chemical compound COc1cc2ncc(NC(C)CCC=CC)nc2cc1OC LZEAKVJEHLYTJO-UHFFFAOYSA-N 0.000 claims description 2
- PGBKZLDCRXBFRW-UHFFFAOYSA-N N-heptan-2-yl-6-methoxyquinoxalin-2-amine Chemical compound C1=C(OC)C=CC2=NC(NC(C)CCCCC)=CN=C21 PGBKZLDCRXBFRW-UHFFFAOYSA-N 0.000 claims description 2
- ONXGUVURJXXMCA-UHFFFAOYSA-N NC1CC(CCC1)C1=NC2=CC(=C(C=C2N=C1)OC)OC Chemical compound NC1CC(CCC1)C1=NC2=CC(=C(C=C2N=C1)OC)OC ONXGUVURJXXMCA-UHFFFAOYSA-N 0.000 claims description 2
- 229920002732 Polyanhydride Polymers 0.000 claims description 2
- 229920000954 Polyglycolide Polymers 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- 230000003143 atherosclerotic effect Effects 0.000 claims description 2
- 229920001400 block copolymer Polymers 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 2
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 2
- 125000003700 epoxy group Chemical group 0.000 claims description 2
- 239000003822 epoxy resin Substances 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 230000003902 lesion Effects 0.000 claims description 2
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 claims description 2
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 2
- FVMOLSMWWNSWLX-UHFFFAOYSA-N n-(3-bicyclo[2.2.1]heptanyl)-6,7-dimethylquinoxalin-2-amine Chemical compound N1=C2C=C(C)C(C)=CC2=NC=C1NC1C(C2)CCC2C1 FVMOLSMWWNSWLX-UHFFFAOYSA-N 0.000 claims description 2
- NXGYOWSWPPHJLL-UHFFFAOYSA-N n-[(6,7-dimethoxyquinoxalin-2-yl)methyl]cyclohexanamine Chemical compound N1=C2C=C(OC)C(OC)=CC2=NC=C1CNC1CCCCC1 NXGYOWSWPPHJLL-UHFFFAOYSA-N 0.000 claims description 2
- HFYHDNNINOTPHW-UHFFFAOYSA-N n-cyclohexyl-6,8-dimethylquinoxalin-2-amine Chemical compound C1=NC2=CC(C)=CC(C)=C2N=C1NC1CCCCC1 HFYHDNNINOTPHW-UHFFFAOYSA-N 0.000 claims description 2
- 229920001693 poly(ether-ester) Polymers 0.000 claims description 2
- 229920006211 poly(glycolic acid-co-trimethylene carbonate) Polymers 0.000 claims description 2
- 229920005996 polystyrene-poly(ethylene-butylene)-polystyrene Polymers 0.000 claims description 2
- 239000004800 polyvinyl chloride Substances 0.000 claims description 2
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 2
- 229920002379 silicone rubber Polymers 0.000 claims description 2
- 239000004945 silicone rubber Substances 0.000 claims description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
- QFLVFZWHHOGCDI-UHFFFAOYSA-N 6-chloro-N-heptan-2-yl-7-methoxyquinoxalin-2-amine Chemical compound C1=C(Cl)C(OC)=CC2=NC(NC(C)CCCCC)=CN=C21 QFLVFZWHHOGCDI-UHFFFAOYSA-N 0.000 claims 1
- MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 claims 1
- WDTKJTQWHUMMDU-UHFFFAOYSA-N n-(3-bicyclo[2.2.1]heptanyl)-6,7-dimethoxyquinoxalin-2-amine Chemical compound N1=C2C=C(OC)C(OC)=CC2=NC=C1NC1C(C2)CCC2C1 WDTKJTQWHUMMDU-UHFFFAOYSA-N 0.000 claims 1
- 239000002952 polymeric resin Substances 0.000 claims 1
- 229920003002 synthetic resin Polymers 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 abstract description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 136
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 102
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 97
- 235000019439 ethyl acetate Nutrition 0.000 description 59
- 239000000243 solution Substances 0.000 description 56
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- 238000000034 method Methods 0.000 description 44
- 238000004458 analytical method Methods 0.000 description 43
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- 210000004027 cell Anatomy 0.000 description 41
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
- 239000007787 solid Substances 0.000 description 33
- 239000000047 product Substances 0.000 description 32
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 30
- 239000011541 reaction mixture Substances 0.000 description 25
- 239000000543 intermediate Substances 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
- 239000002253 acid Substances 0.000 description 22
- 239000000741 silica gel Substances 0.000 description 19
- 229910002027 silica gel Inorganic materials 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 18
- 239000000126 substance Substances 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 229910052786 argon Inorganic materials 0.000 description 15
- 239000010410 layer Substances 0.000 description 15
- 239000012458 free base Substances 0.000 description 14
- 102000011653 Platelet-Derived Growth Factor Receptors Human genes 0.000 description 13
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 13
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 13
- 230000000694 effects Effects 0.000 description 13
- KJGOYBHXJBMXIL-UHFFFAOYSA-N 2-chloro-6,7-dimethoxyquinoxaline Chemical compound C1=C(Cl)N=C2C=C(OC)C(OC)=CC2=N1 KJGOYBHXJBMXIL-UHFFFAOYSA-N 0.000 description 12
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 12
- 239000003112 inhibitor Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 239000002585 base Substances 0.000 description 11
- 239000000872 buffer Substances 0.000 description 11
- 239000012044 organic layer Substances 0.000 description 11
- 239000000843 powder Substances 0.000 description 11
- 239000007858 starting material Substances 0.000 description 11
- 102000001301 EGF receptor Human genes 0.000 description 10
- 108060006698 EGF receptor Proteins 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 108091008606 PDGF receptors Proteins 0.000 description 10
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 10
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 10
- 239000003814 drug Substances 0.000 description 10
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 229940079593 drug Drugs 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 229910000104 sodium hydride Inorganic materials 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 230000001276 controlling effect Effects 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 230000000144 pharmacologic effect Effects 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 239000005483 tyrosine kinase inhibitor Substances 0.000 description 8
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 102000004190 Enzymes Human genes 0.000 description 7
- 108090000790 Enzymes Proteins 0.000 description 7
- 201000010099 disease Diseases 0.000 description 7
- 229940088598 enzyme Drugs 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 description 7
- GKKZBRQHUWQKMA-UHFFFAOYSA-N 6,7-dimethoxyquinoxaline Chemical compound C1=CN=C2C=C(OC)C(OC)=CC2=N1 GKKZBRQHUWQKMA-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 230000006978 adaptation Effects 0.000 description 6
- 239000003146 anticoagulant agent Substances 0.000 description 6
- 239000011159 matrix material Substances 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 239000011148 porous material Substances 0.000 description 6
- 150000003248 quinolines Chemical class 0.000 description 6
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 206010028980 Neoplasm Diseases 0.000 description 5
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
- 239000000538 analytical sample Substances 0.000 description 5
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical group C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 5
- 230000035605 chemotaxis Effects 0.000 description 5
- 238000010168 coupling process Methods 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 210000002966 serum Anatomy 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- CYVRFHRDWQAJGA-UHFFFAOYSA-N 4-[(6,7-dimethoxyquinoxalin-2-yl)amino]cyclohexan-1-ol Chemical compound N1=C2C=C(OC)C(OC)=CC2=NC=C1NC1CCC(O)CC1 CYVRFHRDWQAJGA-UHFFFAOYSA-N 0.000 description 4
- 201000001320 Atherosclerosis Diseases 0.000 description 4
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 239000003125 aqueous solvent Substances 0.000 description 4
- 230000035578 autophosphorylation Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 230000004663 cell proliferation Effects 0.000 description 4
- 230000001413 cellular effect Effects 0.000 description 4
- 230000000875 corresponding effect Effects 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical compound [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 4
- 150000003840 hydrochlorides Chemical class 0.000 description 4
- 238000000338 in vitro Methods 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 4
- 239000000347 magnesium hydroxide Substances 0.000 description 4
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- YBYRMVIVWMBXKQ-UHFFFAOYSA-N phenylmethanesulfonyl fluoride Chemical compound FS(=O)(=O)CC1=CC=CC=C1 YBYRMVIVWMBXKQ-UHFFFAOYSA-N 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 150000003252 quinoxalines Chemical class 0.000 description 4
- 102000005962 receptors Human genes 0.000 description 4
- 108020003175 receptors Proteins 0.000 description 4
- 229940126585 therapeutic drug Drugs 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- UKSZBOKPHAQOMP-UHFFFAOYSA-N 1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1.C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1 UKSZBOKPHAQOMP-UHFFFAOYSA-N 0.000 description 3
- KBCQTOJROUVLQI-UHFFFAOYSA-N 2,7-dichloro-6-methoxyquinoxaline Chemical compound C1=C(Cl)N=C2C=C(Cl)C(OC)=CC2=N1 KBCQTOJROUVLQI-UHFFFAOYSA-N 0.000 description 3
- TYEYBOSBBBHJIV-UHFFFAOYSA-M 2-oxobutanoate Chemical compound CCC(=O)C([O-])=O TYEYBOSBBBHJIV-UHFFFAOYSA-M 0.000 description 3
- KUURJKFCQSUOFM-UHFFFAOYSA-N 6,7-dimethoxyquinolin-3-amine Chemical compound NC1=CN=C2C=C(OC)C(OC)=CC2=C1 KUURJKFCQSUOFM-UHFFFAOYSA-N 0.000 description 3
- NVAJNMBPUCLEHN-UHFFFAOYSA-N 6-bromo-7-methoxy-1h-quinoxalin-2-one Chemical compound OC1=CN=C2C=C(Br)C(OC)=CC2=N1 NVAJNMBPUCLEHN-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 102000003923 Protein Kinase C Human genes 0.000 description 3
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 3
- 229920004890 Triton X-100 Polymers 0.000 description 3
- 239000013504 Triton X-100 Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- 230000006907 apoptotic process Effects 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 210000001124 body fluid Anatomy 0.000 description 3
- 239000010839 body fluid Substances 0.000 description 3
- 201000011510 cancer Diseases 0.000 description 3
- 238000004113 cell culture Methods 0.000 description 3
- 230000005754 cellular signaling Effects 0.000 description 3
- 238000004296 chiral HPLC 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
- 150000002148 esters Chemical class 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 210000005119 human aortic smooth muscle cell Anatomy 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 3
- 229920000747 poly(lactic acid) Polymers 0.000 description 3
- 239000004626 polylactic acid Substances 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- QJDUDPQVDAASMV-UHFFFAOYSA-M sodium;ethanethiolate Chemical compound [Na+].CC[S-] QJDUDPQVDAASMV-UHFFFAOYSA-M 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000011975 tartaric acid Substances 0.000 description 3
- 235000002906 tartaric acid Nutrition 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- 230000004614 tumor growth Effects 0.000 description 3
- DSSYKIVIOFKYAU-XVKPBYJWSA-N (1s,4r)-4,7,7-trimethylbicyclo[2.2.1]heptan-3-one Chemical compound C1C[C@@]2(C)C(=O)C[C@H]1C2(C)C DSSYKIVIOFKYAU-XVKPBYJWSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 2
- MRESHQMRFRLVTF-UHFFFAOYSA-N 2,6-dichloro-7-methoxyquinoxaline Chemical compound ClC1=CN=C2C=C(Cl)C(OC)=CC2=N1 MRESHQMRFRLVTF-UHFFFAOYSA-N 0.000 description 2
- VJIOUBTXSNPMNO-UHFFFAOYSA-N 2,7-dicyclohexyloxy-6-methoxyquinoxaline Chemical compound N1=C2C=C(OC3CCCCC3)C(OC)=CC2=NC=C1OC1CCCCC1 VJIOUBTXSNPMNO-UHFFFAOYSA-N 0.000 description 2
- KKFDCBRMNNSAAW-UHFFFAOYSA-N 2-(morpholin-4-yl)ethanol Chemical compound OCCN1CCOCC1 KKFDCBRMNNSAAW-UHFFFAOYSA-N 0.000 description 2
- YPJQKEPUBYOUTC-UHFFFAOYSA-N 2-anilinoquinoxalin-6-ol Chemical compound C1=NC2=CC(O)=CC=C2N=C1NC1=CC=CC=C1 YPJQKEPUBYOUTC-UHFFFAOYSA-N 0.000 description 2
- VMANDPDDSZSQCR-UHFFFAOYSA-N 2-chloro-7-methoxyquinoxalin-6-ol Chemical compound ClC1=CN=C2C=C(O)C(OC)=CC2=N1 VMANDPDDSZSQCR-UHFFFAOYSA-N 0.000 description 2
- QTJOJAJAJFVICY-UHFFFAOYSA-N 3-(6,7-dimethoxyquinoxalin-2-yl)-3-azabicyclo[2.2.2]octan-2-one Chemical compound C1CC(C2=O)CCC1N2C1=CN=C2C=C(OC)C(OC)=CC2=N1 QTJOJAJAJFVICY-UHFFFAOYSA-N 0.000 description 2
- 150000005014 3-aminoquinolines Chemical class 0.000 description 2
- ASFZQCLAQPBWDN-UHFFFAOYSA-N 3-hydroxy-2-(hydroxymethyl)-1-methoxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=C(O)C(CO)=C2OC ASFZQCLAQPBWDN-UHFFFAOYSA-N 0.000 description 2
- NOOROGYJKGNQGI-UHFFFAOYSA-N 4,5-diamino-2-methoxyphenol;dihydrochloride Chemical compound Cl.Cl.COC1=CC(N)=C(N)C=C1O NOOROGYJKGNQGI-UHFFFAOYSA-N 0.000 description 2
- HCFRWBBJISAZNK-UHFFFAOYSA-N 4-Hydroxycyclohexylcarboxylic acid Chemical compound OC1CCC(C(O)=O)CC1 HCFRWBBJISAZNK-UHFFFAOYSA-N 0.000 description 2
- PFTDKXXUTDNMKL-UHFFFAOYSA-N 4-[2-(3-chloro-7-methoxyquinoxalin-6-yl)oxyethyl]morpholine Chemical compound COC1=CC2=NC=C(Cl)N=C2C=C1OCCN1CCOCC1 PFTDKXXUTDNMKL-UHFFFAOYSA-N 0.000 description 2
- IMLXLGZJLAOKJN-UHFFFAOYSA-N 4-aminocyclohexan-1-ol Chemical compound NC1CCC(O)CC1 IMLXLGZJLAOKJN-UHFFFAOYSA-N 0.000 description 2
- ZQLCLMUXVDGVAP-UHFFFAOYSA-N 5-chloro-4-methoxy-2-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=C(N)C=C1Cl ZQLCLMUXVDGVAP-UHFFFAOYSA-N 0.000 description 2
- BGWJSTZPSPZPFY-UHFFFAOYSA-N 6,7-dimethoxy-2-methylquinoxaline Chemical compound C1=C(C)N=C2C=C(OC)C(OC)=CC2=N1 BGWJSTZPSPZPFY-UHFFFAOYSA-N 0.000 description 2
- UGSFYRBLRAJIQR-UHFFFAOYSA-N 6,7-dimethoxyquinoxaline-2-carbaldehyde Chemical compound C1=C(C=O)N=C2C=C(OC)C(OC)=CC2=N1 UGSFYRBLRAJIQR-UHFFFAOYSA-N 0.000 description 2
- BZTXYVHMINQXFP-UHFFFAOYSA-N 6-chloro-7-methoxy-1h-quinoxalin-2-one Chemical compound OC1=CN=C2C=C(Cl)C(OC)=CC2=N1 BZTXYVHMINQXFP-UHFFFAOYSA-N 0.000 description 2
- BZTZVPITWDTWAW-UHFFFAOYSA-N 6-hydroxy-7-methoxy-1h-quinoxalin-2-one Chemical compound OC1=CN=C2C=C(O)C(OC)=CC2=N1 BZTZVPITWDTWAW-UHFFFAOYSA-N 0.000 description 2
- OYYZLRIVSNMJEU-UHFFFAOYSA-N 7-bromo-2-chloro-6-methoxyquinoxaline Chemical compound C1=C(Cl)N=C2C=C(Br)C(OC)=CC2=N1 OYYZLRIVSNMJEU-UHFFFAOYSA-N 0.000 description 2
- VSQWIHBDQMFEIS-UHFFFAOYSA-N 7-bromo-6-methoxy-1h-quinoxalin-2-one Chemical compound C1=C(O)N=C2C=C(Br)C(OC)=CC2=N1 VSQWIHBDQMFEIS-UHFFFAOYSA-N 0.000 description 2
- NBUVRDBKTVPTTA-UHFFFAOYSA-N 7-chloro-6-methoxy-1h-quinoxalin-2-one Chemical compound C1=C(O)N=C2C=C(Cl)C(OC)=CC2=N1 NBUVRDBKTVPTTA-UHFFFAOYSA-N 0.000 description 2
- SHNHYPRTBHCEHW-UHFFFAOYSA-N 7-hydroxy-6-methoxy-1h-quinoxalin-2-one Chemical compound C1=C(O)N=C2C=C(O)C(OC)=CC2=N1 SHNHYPRTBHCEHW-UHFFFAOYSA-N 0.000 description 2
- 108010039627 Aprotinin Proteins 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 2
- CXDLBBXKTJPGRV-MGCOHNPYSA-N C=1N=C2C=C(Cl)C(OC)=CC2=NC=1N[C@H]1CC[C@H](O)CC1 Chemical compound C=1N=C2C=C(Cl)C(OC)=CC2=NC=1N[C@H]1CC[C@H](O)CC1 CXDLBBXKTJPGRV-MGCOHNPYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- 102000009024 Epidermal Growth Factor Human genes 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 206010016654 Fibrosis Diseases 0.000 description 2
- 208000032612 Glial tumor Diseases 0.000 description 2
- 206010018338 Glioma Diseases 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- 108010001127 Insulin Receptor Proteins 0.000 description 2
- 102000003746 Insulin Receptor Human genes 0.000 description 2
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 2
- GDBQQVLCIARPGH-UHFFFAOYSA-N Leupeptin Natural products CC(C)CC(NC(C)=O)C(=O)NC(CC(C)C)C(=O)NC(C=O)CCCN=C(N)N GDBQQVLCIARPGH-UHFFFAOYSA-N 0.000 description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 201000004681 Psoriasis Diseases 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 108010090804 Streptavidin Proteins 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000006044 T cell activation Effects 0.000 description 2
- 230000006052 T cell proliferation Effects 0.000 description 2
- IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 description 2
- 108090000631 Trypsin Proteins 0.000 description 2
- 102000004142 Trypsin Human genes 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 208000026935 allergic disease Diseases 0.000 description 2
- 108010004469 allophycocyanin Proteins 0.000 description 2
- 230000000702 anti-platelet effect Effects 0.000 description 2
- 230000002785 anti-thrombosis Effects 0.000 description 2
- 229940127219 anticoagulant drug Drugs 0.000 description 2
- 238000003782 apoptosis assay Methods 0.000 description 2
- 229960004405 aprotinin Drugs 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000003149 assay kit Methods 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
- 244000309466 calf Species 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 230000012292 cell migration Effects 0.000 description 2
- 230000009087 cell motility Effects 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- NLCKLZIHJQEMCU-UHFFFAOYSA-N cyano prop-2-enoate Chemical class C=CC(=O)OC#N NLCKLZIHJQEMCU-UHFFFAOYSA-N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 2
- 230000020335 dealkylation Effects 0.000 description 2
- 238000006900 dealkylation reaction Methods 0.000 description 2
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 2
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
- DEFVIWRASFVYLL-UHFFFAOYSA-N ethylene glycol bis(2-aminoethyl)tetraacetic acid Chemical compound OC(=O)CN(CC(O)=O)CCOCCOCCN(CC(O)=O)CC(O)=O DEFVIWRASFVYLL-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 230000004761 fibrosis Effects 0.000 description 2
- 208000005017 glioblastoma Diseases 0.000 description 2
- DPOVASGZNDBULR-UHFFFAOYSA-N hept-5-en-2-amine Chemical compound CC=CCCC(C)N DPOVASGZNDBULR-UHFFFAOYSA-N 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 150000002466 imines Chemical class 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 230000004968 inflammatory condition Effects 0.000 description 2
- ZPNFWUPYTFPOJU-LPYSRVMUSA-N iniprol Chemical compound C([C@H]1C(=O)NCC(=O)NCC(=O)N[C@H]2CSSC[C@H]3C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@H](C(N[C@H](C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=4C=CC(O)=CC=4)C(=O)N[C@@H](CC=4C=CC=CC=4)C(=O)N[C@@H](CC=4C=CC(O)=CC=4)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC=4C=CC=CC=4)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC2=O)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H]2N(CCC2)C(=O)[C@@H](N)CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N2[C@@H](CCC2)C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N2[C@@H](CCC2)C(=O)N3)C(=O)NCC(=O)NCC(=O)N[C@@H](C)C(O)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@H](C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H](C(=O)N1)C(C)C)[C@@H](C)O)[C@@H](C)CC)=O)[C@@H](C)CC)C1=CC=C(O)C=C1 ZPNFWUPYTFPOJU-LPYSRVMUSA-N 0.000 description 2
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
- 210000003734 kidney Anatomy 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- GDBQQVLCIARPGH-ULQDDVLXSA-N leupeptin Chemical compound CC(C)C[C@H](NC(C)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C=O)CCCN=C(N)N GDBQQVLCIARPGH-ULQDDVLXSA-N 0.000 description 2
- 108010052968 leupeptin Proteins 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 238000012261 overproduction Methods 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 150000004965 peroxy acids Chemical class 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 230000000019 pro-fibrinolytic effect Effects 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- 230000005522 programmed cell death Effects 0.000 description 2
- 230000002062 proliferating effect Effects 0.000 description 2
- 230000035755 proliferation Effects 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 238000004007 reversed phase HPLC Methods 0.000 description 2
- 238000012552 review Methods 0.000 description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 229920006132 styrene block copolymer Polymers 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 239000012588 trypsin Substances 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- UJBOOUHRTQVGRU-ZCFIWIBFSA-N (3r)-3-methylcyclohexan-1-one Chemical compound C[C@@H]1CCCC(=O)C1 UJBOOUHRTQVGRU-ZCFIWIBFSA-N 0.000 description 1
- AAWZDTNXLSGCEK-LNVDRNJUSA-N (3r,5r)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical compound O[C@@H]1CC(O)(C(O)=O)C[C@@H](O)C1O AAWZDTNXLSGCEK-LNVDRNJUSA-N 0.000 description 1
- MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 description 1
- XDPCNPCKDGQBAN-BYPYZUCNSA-N (3s)-oxolan-3-ol Chemical compound O[C@H]1CCOC1 XDPCNPCKDGQBAN-BYPYZUCNSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- IOEPOEDBBPRAEI-UHFFFAOYSA-N 1,2-dihydroisoquinoline Chemical class C1=CC=C2CNC=CC2=C1 IOEPOEDBBPRAEI-UHFFFAOYSA-N 0.000 description 1
- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-Bis(diphenylphosphino)propane Substances C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 1
- QGRPVMLBTFGQDQ-UHFFFAOYSA-N 1-chloro-2-methoxybenzene Chemical compound COC1=CC=CC=C1Cl QGRPVMLBTFGQDQ-UHFFFAOYSA-N 0.000 description 1
- RLRINNKRRPQIGW-UHFFFAOYSA-N 1-ethenyl-2-[4-(2-ethenylphenyl)butyl]benzene Chemical compound C=CC1=CC=CC=C1CCCCC1=CC=CC=C1C=C RLRINNKRRPQIGW-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- SRMSHAQAUGUZAR-UHFFFAOYSA-N 2-aminoquinoxalin-6-ol Chemical compound C1=C(O)C=CC2=NC(N)=CN=C21 SRMSHAQAUGUZAR-UHFFFAOYSA-N 0.000 description 1
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- FFOSGJSASFGRSA-UHFFFAOYSA-N 2-methoxy-4,5-dinitrophenol Chemical compound COC1=CC([N+]([O-])=O)=C([N+]([O-])=O)C=C1O FFOSGJSASFGRSA-UHFFFAOYSA-N 0.000 description 1
- SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 1
- JKRSQNBRNIYETC-UHFFFAOYSA-N 3-(4-methylpiperazin-1-yl)propan-1-ol Chemical compound CN1CCN(CCCO)CC1 JKRSQNBRNIYETC-UHFFFAOYSA-N 0.000 description 1
- LZKQFCCBVWQXPE-UHFFFAOYSA-N 3-(6,7-dimethoxyquinolin-2-yl)cyclohexan-1-amine Chemical compound N1=C2C=C(OC)C(OC)=CC2=CC=C1C1CCCC(N)C1 LZKQFCCBVWQXPE-UHFFFAOYSA-N 0.000 description 1
- INUDVYXQIHBPDM-UHFFFAOYSA-N 3-[(6,7-dimethoxyquinolin-3-yl)amino]-2,2-dimethylpropan-1-ol Chemical compound OCC(C)(C)CNC1=CN=C2C=C(OC)C(OC)=CC2=C1 INUDVYXQIHBPDM-UHFFFAOYSA-N 0.000 description 1
- CZVSOFLNEUYJRJ-UHFFFAOYSA-N 3-azabicyclo[2.2.2]octan-2-one Chemical compound C1CC2C(=O)NC1CC2 CZVSOFLNEUYJRJ-UHFFFAOYSA-N 0.000 description 1
- XHBNFOVKHJHYRW-UHFFFAOYSA-N 3-chloro-7-methoxyquinoxalin-6-ol Chemical compound C1=C(Cl)N=C2C=C(O)C(OC)=CC2=N1 XHBNFOVKHJHYRW-UHFFFAOYSA-N 0.000 description 1
- IBGWJSNKHGIWJK-UHFFFAOYSA-N 3-cyclohexyloxy-6,7-dimethoxy-1-oxidoquinoxalin-1-ium Chemical compound C=1[N+]([O-])=C2C=C(OC)C(OC)=CC2=NC=1OC1CCCCC1 IBGWJSNKHGIWJK-UHFFFAOYSA-N 0.000 description 1
- JJMOMMLADQPZNY-UHFFFAOYSA-N 3-hydroxy-2,2-dimethylpropanal Chemical compound OCC(C)(C)C=O JJMOMMLADQPZNY-UHFFFAOYSA-N 0.000 description 1
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 1
- PUADOPXQTWHCCY-UHFFFAOYSA-N 4-(6,7-dimethoxyquinoxalin-2-yl)oxycyclohexan-1-ol Chemical compound N1=C2C=C(OC)C(OC)=CC2=NC=C1OC1CCC(O)CC1 PUADOPXQTWHCCY-UHFFFAOYSA-N 0.000 description 1
- VLNIWQYOKHAJKU-UHFFFAOYSA-N 4-[2-(2-chloro-7-methoxyquinoxalin-6-yl)oxyethyl]morpholine Chemical compound COC1=CC2=NC(Cl)=CN=C2C=C1OCCN1CCOCC1 VLNIWQYOKHAJKU-UHFFFAOYSA-N 0.000 description 1
- IMUYKRPMHLQLRO-UHFFFAOYSA-N 4-bromo-5-methoxybenzene-1,2-diamine;dihydrochloride Chemical compound Cl.Cl.COC1=CC(N)=C(N)C=C1Br IMUYKRPMHLQLRO-UHFFFAOYSA-N 0.000 description 1
- RNRPNVNDYWBWGS-UHFFFAOYSA-N 4-chloro-5-methoxybenzene-1,2-diamine;dihydrochloride Chemical compound Cl.Cl.COC1=CC(N)=C(N)C=C1Cl RNRPNVNDYWBWGS-UHFFFAOYSA-N 0.000 description 1
- CDLCHACBLCSWBT-UHFFFAOYSA-N 4-hept-5-en-2-ylisoindole-1,3-dione Chemical compound CC=CCCC(C)c1cccc2C(=O)NC(=O)c12 CDLCHACBLCSWBT-UHFFFAOYSA-N 0.000 description 1
- QFMJFXFXQAFGBO-UHFFFAOYSA-N 4-methoxy-2-nitroaniline Chemical compound COC1=CC=C(N)C([N+]([O-])=O)=C1 QFMJFXFXQAFGBO-UHFFFAOYSA-N 0.000 description 1
- OTLNPYWUJOZPPA-UHFFFAOYSA-N 4-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1 OTLNPYWUJOZPPA-UHFFFAOYSA-N 0.000 description 1
- VUTVKXUAPAJONV-UHFFFAOYSA-N 5-aminobicyclo[2.2.1]heptan-2-ol Chemical compound C1C2C(N)CC1C(O)C2 VUTVKXUAPAJONV-UHFFFAOYSA-N 0.000 description 1
- RPXUPJQZWLWDKX-UHFFFAOYSA-N 6,7-dichloro-2-phenylquinoxaline Chemical compound N1=C2C=C(Cl)C(Cl)=CC2=NC=C1C1=CC=CC=C1 RPXUPJQZWLWDKX-UHFFFAOYSA-N 0.000 description 1
- MUGRTDRRMKHNTM-UHFFFAOYSA-N 6,7-dimethoxy-2-(4-methoxyphenyl)quinoxaline Chemical compound C1=CC(OC)=CC=C1C1=CN=C(C=C(OC)C(OC)=C2)C2=N1 MUGRTDRRMKHNTM-UHFFFAOYSA-N 0.000 description 1
- UNALZVYBWFUPTL-UHFFFAOYSA-N 6,7-dimethoxy-3-(4-methoxyphenyl)quinoline Chemical compound C1=CC(OC)=CC=C1C1=CN=C(C=C(OC)C(OC)=C2)C2=C1 UNALZVYBWFUPTL-UHFFFAOYSA-N 0.000 description 1
- KRVGGZGDTISBDI-UHFFFAOYSA-N 6,7-dimethoxyquinolin-3-amine;hydrochloride Chemical compound Cl.NC1=CN=C2C=C(OC)C(OC)=CC2=C1 KRVGGZGDTISBDI-UHFFFAOYSA-N 0.000 description 1
- PJTFIXLKCMSEAD-UHFFFAOYSA-N 6,7-dimethoxyquinolin-3-ol Chemical compound OC1=CN=C2C=C(OC)C(OC)=CC2=C1 PJTFIXLKCMSEAD-UHFFFAOYSA-N 0.000 description 1
- PCDPMVJGEGAJBI-UHFFFAOYSA-N 6,7-dimethoxyquinoline Chemical compound C1=CN=C2C=C(OC)C(OC)=CC2=C1 PCDPMVJGEGAJBI-UHFFFAOYSA-N 0.000 description 1
- FQNCLVJEQCJWSU-UHFFFAOYSA-N 6,7-dimethyl-2-phenylquinoxaline Chemical compound N1=C2C=C(C)C(C)=CC2=NC=C1C1=CC=CC=C1 FQNCLVJEQCJWSU-UHFFFAOYSA-N 0.000 description 1
- ZYUVSXGRRLWXNM-UHFFFAOYSA-N 6-bromo-2-chloro-7-methoxyquinoxaline Chemical compound ClC1=CN=C2C=C(Br)C(OC)=CC2=N1 ZYUVSXGRRLWXNM-UHFFFAOYSA-N 0.000 description 1
- BOKDQVMCPVBXNJ-UHFFFAOYSA-N 6-bromo-7-methoxyquinoxaline Chemical compound BrC=1C=C2N=CC=NC2=CC=1OC BOKDQVMCPVBXNJ-UHFFFAOYSA-N 0.000 description 1
- KEWRTGBMJSDQAU-UHFFFAOYSA-N 7-bromo-n-cyclohexyl-6-methoxyquinoxalin-2-amine Chemical compound N1=C2C=C(Br)C(OC)=CC2=NC=C1NC1CCCCC1 KEWRTGBMJSDQAU-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 239000005541 ACE inhibitor Substances 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- DWRXFEITVBNRMK-UHFFFAOYSA-N Beta-D-1-Arabinofuranosylthymine Natural products O=C1NC(=O)C(C)=CN1C1C(O)C(O)C(CO)O1 DWRXFEITVBNRMK-UHFFFAOYSA-N 0.000 description 1
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 1
- 208000020084 Bone disease Diseases 0.000 description 1
- 102100028672 C-type lectin domain family 4 member D Human genes 0.000 description 1
- MWJKQSALRAZFQR-WKILWMFISA-N C=1N=C2C=C(OCCN3CCOCC3)C(OC)=CC2=NC=1N[C@H]1CC[C@H](O)CC1 Chemical compound C=1N=C2C=C(OCCN3CCOCC3)C(OC)=CC2=NC=1N[C@H]1CC[C@H](O)CC1 MWJKQSALRAZFQR-WKILWMFISA-N 0.000 description 1
- JDHYKJFPZBYRDS-XYPYZODXSA-N COc1cc2ncc(N[C@H]3CC[C@@H](CC3)C(O)=O)nc2cc1OC Chemical compound COc1cc2ncc(N[C@H]3CC[C@@H](CC3)C(O)=O)nc2cc1OC JDHYKJFPZBYRDS-XYPYZODXSA-N 0.000 description 1
- VLGMELKIRGCWAA-XYPYZODXSA-N COc1cc2ncc(O[C@H]3CC[C@@H](CC3)C(O)=O)nc2cc1OC Chemical compound COc1cc2ncc(O[C@H]3CC[C@@H](CC3)C(O)=O)nc2cc1OC VLGMELKIRGCWAA-XYPYZODXSA-N 0.000 description 1
- 229940127291 Calcium channel antagonist Drugs 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- AAWZDTNXLSGCEK-UHFFFAOYSA-N Cordycepinsaeure Natural products OC1CC(O)(C(O)=O)CC(O)C1O AAWZDTNXLSGCEK-UHFFFAOYSA-N 0.000 description 1
- 102000004127 Cytokines Human genes 0.000 description 1
- 108090000695 Cytokines Proteins 0.000 description 1
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 1
- 238000002965 ELISA Methods 0.000 description 1
- 206010014476 Elevated cholesterol Diseases 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 206010018364 Glomerulonephritis Diseases 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 239000007995 HEPES buffer Substances 0.000 description 1
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 1
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
- 101000766905 Homo sapiens C-type lectin domain family 4 member D Proteins 0.000 description 1
- 101001027128 Homo sapiens Fibronectin Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 208000035150 Hypercholesterolemia Diseases 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 102000004877 Insulin Human genes 0.000 description 1
- 108090001061 Insulin Proteins 0.000 description 1
- 208000007766 Kaposi sarcoma Diseases 0.000 description 1
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- 229930182816 L-glutamine Natural products 0.000 description 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 208000019693 Lung disease Diseases 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- LRLFXAITFXQGES-ILOXCIGCSA-N N[C@@H]1CC[C@H](CC1)O.COC=1C=C2N=CC(=NC2=CC1OC)N[C@@H]1CC[C@H](CC1)O Chemical compound N[C@@H]1CC[C@H](CC1)O.COC=1C=C2N=CC(=NC2=CC1OC)N[C@@H]1CC[C@H](CC1)O LRLFXAITFXQGES-ILOXCIGCSA-N 0.000 description 1
- 102000001775 Neurogranin Human genes 0.000 description 1
- 108010015301 Neurogranin Proteins 0.000 description 1
- HWBWPQJFPHMBHE-UHFFFAOYSA-N OCC(O)=O.O=C1OCCCO1 Chemical compound OCC(O)=O.O=C1OCCCO1 HWBWPQJFPHMBHE-UHFFFAOYSA-N 0.000 description 1
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 1
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- AAWZDTNXLSGCEK-ZHQZDSKASA-N Quinic acid Natural products O[C@H]1CC(O)(C(O)=O)C[C@H](O)C1O AAWZDTNXLSGCEK-ZHQZDSKASA-N 0.000 description 1
- 208000001647 Renal Insufficiency Diseases 0.000 description 1
- 102000001332 SRC Human genes 0.000 description 1
- 108060006706 SRC Proteins 0.000 description 1
- 229940124639 Selective inhibitor Drugs 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229940122388 Thrombin inhibitor Drugs 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 206010052779 Transplant rejections Diseases 0.000 description 1
- 229940122618 Trypsin inhibitor Drugs 0.000 description 1
- 101710162629 Trypsin inhibitor Proteins 0.000 description 1
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 1
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- MIOPJNTWMNEORI-OMNKOJBGSA-N [(4s)-7,7-dimethyl-3-oxo-4-bicyclo[2.2.1]heptanyl]methanesulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-OMNKOJBGSA-N 0.000 description 1
- BSIMOFOAANTRKE-UHFFFAOYSA-N [Mg].CN(C)C Chemical compound [Mg].CN(C)C BSIMOFOAANTRKE-UHFFFAOYSA-N 0.000 description 1
- ZWIJWDCFGVKPGY-RTRLPJTCSA-N [[(3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]amino] acetate Chemical compound C(C)(=O)ON[C@H]1C(O)O[C@@H]([C@H]([C@@H]1O)O)CO ZWIJWDCFGVKPGY-RTRLPJTCSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 238000007098 aminolysis reaction Methods 0.000 description 1
- 229940058934 aminoquinoline antimalarials Drugs 0.000 description 1
- 150000005010 aminoquinolines Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 230000003698 anagen phase Effects 0.000 description 1
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 230000001028 anti-proliverative effect Effects 0.000 description 1
- 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 description 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
- 210000000709 aorta Anatomy 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 229960003121 arginine Drugs 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 230000003305 autocrine Effects 0.000 description 1
- 238000000376 autoradiography Methods 0.000 description 1
- SJSWRKNSCWKNIR-UHFFFAOYSA-N azane;dihydrochloride Chemical compound N.Cl.Cl SJSWRKNSCWKNIR-UHFFFAOYSA-N 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 239000002876 beta blocker Substances 0.000 description 1
- 229940097320 beta blocking agent Drugs 0.000 description 1
- IQFYYKKMVGJFEH-UHFFFAOYSA-N beta-L-thymidine Natural products O=C1NC(=O)C(C)=CN1C1OC(CO)C(O)C1 IQFYYKKMVGJFEH-UHFFFAOYSA-N 0.000 description 1
- 239000012496 blank sample Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- NNTOJPXOCKCMKR-UHFFFAOYSA-N boron;pyridine Chemical compound [B].C1=CC=NC=C1 NNTOJPXOCKCMKR-UHFFFAOYSA-N 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004799 bromophenyl group Chemical group 0.000 description 1
- 239000007975 buffered saline Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- BQRGNLJZBFXNCZ-UHFFFAOYSA-N calcein am Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC(CN(CC(=O)OCOC(C)=O)CC(=O)OCOC(C)=O)=C(OC(C)=O)C=C1OC1=C2C=C(CN(CC(=O)OCOC(C)=O)CC(=O)OCOC(=O)C)C(OC(C)=O)=C1 BQRGNLJZBFXNCZ-UHFFFAOYSA-N 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 230000005907 cancer growth Effects 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical group C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000024245 cell differentiation Effects 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 239000013592 cell lysate Substances 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- VDANGULDQQJODZ-UHFFFAOYSA-N chloroprocaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1Cl VDANGULDQQJODZ-UHFFFAOYSA-N 0.000 description 1
- 229960002023 chloroprocaine Drugs 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000002299 complementary DNA Substances 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 230000001086 cytosolic effect Effects 0.000 description 1
- 229920006237 degradable polymer Polymers 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 230000002074 deregulated effect Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229940043237 diethanolamine Drugs 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 238000009510 drug design Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000001962 electrophoresis Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- HKSZLNNOFSGOKW-UHFFFAOYSA-N ent-staurosporine Natural products C12=C3N4C5=CC=CC=C5C3=C3CNC(=O)C3=C2C2=CC=CC=C2N1C1CC(NC)C(OC)C4(C)O1 HKSZLNNOFSGOKW-UHFFFAOYSA-N 0.000 description 1
- LPUZTLKYAOOFDX-QXMHVHEDSA-N ethenyl (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC=C LPUZTLKYAOOFDX-QXMHVHEDSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 230000001605 fetal effect Effects 0.000 description 1
- 229940125753 fibrate Drugs 0.000 description 1
- 239000002319 fibrinogen receptor antagonist Substances 0.000 description 1
- 230000003176 fibrotic effect Effects 0.000 description 1
- 229930003944 flavone Natural products 0.000 description 1
- 150000002213 flavones Chemical class 0.000 description 1
- 235000011949 flavones Nutrition 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 229940045109 genistein Drugs 0.000 description 1
- TZBJGXHYKVUXJN-UHFFFAOYSA-N genistein Natural products C1=CC(O)=CC=C1C1=COC2=CC(O)=CC(O)=C2C1=O TZBJGXHYKVUXJN-UHFFFAOYSA-N 0.000 description 1
- 235000006539 genistein Nutrition 0.000 description 1
- ZCOLJUOHXJRHDI-CMWLGVBASA-N genistein 7-O-beta-D-glucoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 ZCOLJUOHXJRHDI-CMWLGVBASA-N 0.000 description 1
- 229940114119 gentisate Drugs 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 239000003102 growth factor Substances 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 229960002897 heparin Drugs 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 239000007970 homogeneous dispersion Substances 0.000 description 1
- 102000043827 human Smooth muscle Human genes 0.000 description 1
- 108700038605 human Smooth muscle Proteins 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000033444 hydroxylation Effects 0.000 description 1
- 238000005805 hydroxylation reaction Methods 0.000 description 1
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 1
- 238000001114 immunoprecipitation Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 230000028709 inflammatory response Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 229940125396 insulin Drugs 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
- 201000006370 kidney failure Diseases 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 229940127215 low-molecular weight heparin Drugs 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 229960003646 lysine Drugs 0.000 description 1
- 239000012139 lysis buffer Substances 0.000 description 1
- UJBOOUHRTQVGRU-UHFFFAOYSA-N m-methylcyclohexanone Natural products CC1CCCC(=O)C1 UJBOOUHRTQVGRU-UHFFFAOYSA-N 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 210000003584 mesangial cell Anatomy 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000003226 mitogen Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- UDVMKRHMXJOWQA-UHFFFAOYSA-N n-(5-chloro-4-methoxy-2-nitrophenyl)acetamide Chemical compound COC1=CC([N+]([O-])=O)=C(NC(C)=O)C=C1Cl UDVMKRHMXJOWQA-UHFFFAOYSA-N 0.000 description 1
- IUIGGMIZFFNIQW-UHFFFAOYSA-N n-butyl-n-(hydroxymethyl)-2-methylprop-2-enamide Chemical compound CCCCN(CO)C(=O)C(C)=C IUIGGMIZFFNIQW-UHFFFAOYSA-N 0.000 description 1
- YNKZNUYHPDEFMC-UHFFFAOYSA-N n-phenyl-6-propan-2-yloxyquinoxalin-2-amine;hydrochloride Chemical compound Cl.C1=NC2=CC(OC(C)C)=CC=C2N=C1NC1=CC=CC=C1 YNKZNUYHPDEFMC-UHFFFAOYSA-N 0.000 description 1
- HUDSSSKDWYXKGP-UHFFFAOYSA-N n-phenylpyridin-2-amine Chemical class C=1C=CC=NC=1NC1=CC=CC=C1 HUDSSSKDWYXKGP-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 102000037979 non-receptor tyrosine kinases Human genes 0.000 description 1
- 108091008046 non-receptor tyrosine kinases Proteins 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229960003104 ornithine Drugs 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- OOERMIUBGQEKAF-UHFFFAOYSA-N oxireno[2,3-b]quinoline Chemical class C1=CC=C2N=C3OC3=CC2=C1 OOERMIUBGQEKAF-UHFFFAOYSA-N 0.000 description 1
- 230000036407 pain Effects 0.000 description 1
- 230000003076 paracrine Effects 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
- 238000006366 phosphorylation reaction Methods 0.000 description 1
- DCWXELXMIBXGTH-UHFFFAOYSA-N phosphotyrosine Chemical compound OC(=O)C(N)CC1=CC=C(OP(O)(O)=O)C=C1 DCWXELXMIBXGTH-UHFFFAOYSA-N 0.000 description 1
- 229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 description 1
- 229920001606 poly(lactic acid-co-glycolic acid) Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920005597 polymer membrane Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920006214 polyvinylidene halide Polymers 0.000 description 1
- 231100000683 possible toxicity Toxicity 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000011533 pre-incubation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000003909 protein kinase inhibitor Substances 0.000 description 1
- ZHNFLHYOFXQIOW-LPYZJUEESA-N quinine sulfate dihydrate Chemical compound [H+].[H+].O.O.[O-]S([O-])(=O)=O.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 ZHNFLHYOFXQIOW-LPYZJUEESA-N 0.000 description 1
- FFRYUAVNPBUEIC-UHFFFAOYSA-N quinoxalin-2-ol Chemical class C1=CC=CC2=NC(O)=CN=C21 FFRYUAVNPBUEIC-UHFFFAOYSA-N 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 102000027426 receptor tyrosine kinases Human genes 0.000 description 1
- 108091008598 receptor tyrosine kinases Proteins 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 239000012723 sample buffer Substances 0.000 description 1
- 239000004017 serum-free culture medium Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 210000000329 smooth muscle myocyte Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011537 solubilization buffer Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- HKSZLNNOFSGOKW-FYTWVXJKSA-N staurosporine Chemical compound C12=C3N4C5=CC=CC=C5C3=C3CNC(=O)C3=C2C2=CC=CC=C2N1[C@H]1C[C@@H](NC)[C@@H](OC)[C@]4(C)O1 HKSZLNNOFSGOKW-FYTWVXJKSA-N 0.000 description 1
- CGPUWJWCVCFERF-UHFFFAOYSA-N staurosporine Natural products C12=C3N4C5=CC=CC=C5C3=C3CNC(=O)C3=C2C2=CC=CC=C2N1C1CC(NC)C(OC)C4(OC)O1 CGPUWJWCVCFERF-UHFFFAOYSA-N 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 210000002437 synoviocyte Anatomy 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 239000003868 thrombin inhibitor Substances 0.000 description 1
- 229940104230 thymidine Drugs 0.000 description 1
- 238000001890 transfection Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000002753 trypsin inhibitor Substances 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 150000004917 tyrosine kinase inhibitor derivatives Chemical class 0.000 description 1
- 150000003668 tyrosines Chemical class 0.000 description 1
- 125000001493 tyrosinyl group Chemical group [H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/38—Nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
-
- 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
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/20—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/42—Benzopyrazines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines 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 carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/50—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to ring nitrogen atoms
- C07D241/52—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/50—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to ring nitrogen atoms
- C07D241/54—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/06—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing isoquinuclidine ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Pain & Pain Management (AREA)
- Vascular Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Urology & Nephrology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/198,718 US6180632B1 (en) | 1997-05-28 | 1998-11-24 | Quinoline and quinoxaline compounds which inhibit platelet-derived growth factor and/or p56lck tyrosine kinases |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BG105625A BG105625A (en) | 2002-01-31 |
| BG65497B1 true BG65497B1 (bg) | 2008-10-31 |
Family
ID=22734514
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG105625A BG65497B1 (bg) | 1998-11-24 | 2001-06-20 | Стент с полимерно покритие, съдържащо средства заинхибиране на рестеноза |
Country Status (22)
| Country | Link |
|---|---|
| US (5) | US6180632B1 (enExample) |
| EP (1) | EP1133480A1 (enExample) |
| JP (1) | JP2002530389A (enExample) |
| KR (1) | KR100784291B1 (enExample) |
| CN (1) | CN100390154C (enExample) |
| AU (1) | AU777256B2 (enExample) |
| BG (1) | BG65497B1 (enExample) |
| BR (1) | BR9915653A (enExample) |
| CA (1) | CA2352261A1 (enExample) |
| CZ (1) | CZ20012276A3 (enExample) |
| EA (1) | EA007534B1 (enExample) |
| EE (1) | EE200100280A (enExample) |
| HU (1) | HUP0104605A3 (enExample) |
| ID (1) | ID29611A (enExample) |
| IL (1) | IL143406A0 (enExample) |
| MX (1) | MXPA01005317A (enExample) |
| NO (1) | NO319801B1 (enExample) |
| NZ (1) | NZ512096A (enExample) |
| PL (1) | PL348979A1 (enExample) |
| SK (1) | SK9062001A3 (enExample) |
| UA (1) | UA76935C2 (enExample) |
| WO (1) | WO2000031051A1 (enExample) |
Families Citing this family (186)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6776792B1 (en) * | 1997-04-24 | 2004-08-17 | Advanced Cardiovascular Systems Inc. | Coated endovascular stent |
| US6180632B1 (en) | 1997-05-28 | 2001-01-30 | Aventis Pharmaceuticals Products Inc. | Quinoline and quinoxaline compounds which inhibit platelet-derived growth factor and/or p56lck tyrosine kinases |
| AU751772C (en) * | 1998-04-01 | 2006-09-07 | Correvio International Sàrl | Aminocyclohexyl ether compounds and uses thereof |
| US6455734B1 (en) | 2000-08-09 | 2002-09-24 | Magnesium Diagnostics, Inc. | Antagonists of the magnesium binding defect as therapeutic agents and methods for treatment of abnormal physiological states |
| US7507545B2 (en) | 1999-03-31 | 2009-03-24 | Cardiome Pharma Corp. | Ion channel modulating activity method |
| US6790228B2 (en) * | 1999-12-23 | 2004-09-14 | Advanced Cardiovascular Systems, Inc. | Coating for implantable devices and a method of forming the same |
| US7807211B2 (en) * | 1999-09-03 | 2010-10-05 | Advanced Cardiovascular Systems, Inc. | Thermal treatment of an implantable medical device |
| US20070032853A1 (en) * | 2002-03-27 | 2007-02-08 | Hossainy Syed F | 40-O-(2-hydroxy)ethyl-rapamycin coated stent |
| US20050238686A1 (en) * | 1999-12-23 | 2005-10-27 | Advanced Cardiovascular Systems, Inc. | Coating for implantable devices and a method of forming the same |
| US20160287708A9 (en) * | 2000-03-15 | 2016-10-06 | Orbusneich Medical, Inc. | Progenitor Endothelial Cell Capturing with a Drug Eluting Implantable Medical Device |
| US20050271701A1 (en) * | 2000-03-15 | 2005-12-08 | Orbus Medical Technologies, Inc. | Progenitor endothelial cell capturing with a drug eluting implantable medical device |
| US8088060B2 (en) * | 2000-03-15 | 2012-01-03 | Orbusneich Medical, Inc. | Progenitor endothelial cell capturing with a drug eluting implantable medical device |
| US9522217B2 (en) | 2000-03-15 | 2016-12-20 | Orbusneich Medical, Inc. | Medical device with coating for capturing genetically-altered cells and methods for using same |
| US6953560B1 (en) | 2000-09-28 | 2005-10-11 | Advanced Cardiovascular Systems, Inc. | Barriers for polymer-coated implantable medical devices and methods for making the same |
| US7057053B2 (en) * | 2000-10-06 | 2006-06-06 | Cardiome Pharma Corp. | Ion channel modulating compounds and uses thereof |
| US7524879B2 (en) * | 2000-10-06 | 2009-04-28 | Cardiome Pharma Corp. | Ion channel modulating compounds and uses thereof |
| US6783793B1 (en) * | 2000-10-26 | 2004-08-31 | Advanced Cardiovascular Systems, Inc. | Selective coating of medical devices |
| US7807210B1 (en) * | 2000-10-31 | 2010-10-05 | Advanced Cardiovascular Systems, Inc. | Hemocompatible polymers on hydrophobic porous polymers |
| GB0100761D0 (en) | 2001-01-11 | 2001-02-21 | Biocompatibles Ltd | Drug delivery from stents |
| US6780424B2 (en) * | 2001-03-30 | 2004-08-24 | Charles David Claude | Controlled morphologies in polymer drug for release of drugs from polymer films |
| SK287686B6 (sk) * | 2001-04-10 | 2011-06-06 | Ciba Specialty Chemicals Holding Inc. | Izolačná kompozícia na strednonapäťové a vysokonapäťové káble a spôsob jej výroby |
| US6743462B1 (en) * | 2001-05-31 | 2004-06-01 | Advanced Cardiovascular Systems, Inc. | Apparatus and method for coating implantable devices |
| US8741378B1 (en) | 2001-06-27 | 2014-06-03 | Advanced Cardiovascular Systems, Inc. | Methods of coating an implantable device |
| US6695920B1 (en) * | 2001-06-27 | 2004-02-24 | Advanced Cardiovascular Systems, Inc. | Mandrel for supporting a stent and a method of using the mandrel to coat a stent |
| US6565659B1 (en) * | 2001-06-28 | 2003-05-20 | Advanced Cardiovascular Systems, Inc. | Stent mounting assembly and a method of using the same to coat a stent |
| US7682669B1 (en) | 2001-07-30 | 2010-03-23 | Advanced Cardiovascular Systems, Inc. | Methods for covalently immobilizing anti-thrombogenic material into a coating on a medical device |
| US8303651B1 (en) * | 2001-09-07 | 2012-11-06 | Advanced Cardiovascular Systems, Inc. | Polymeric coating for reducing the rate of release of a therapeutic substance from a stent |
| US6753071B1 (en) * | 2001-09-27 | 2004-06-22 | Advanced Cardiovascular Systems, Inc. | Rate-reducing membrane for release of an agent |
| US7621907B2 (en) * | 2002-03-11 | 2009-11-24 | Alcon, Inc. | Implantable drug delivery system |
| AUPS275302A0 (en) * | 2002-05-31 | 2002-06-27 | Khouri, Anthony | Vehicle mounted concrete mixing drum and method of manufacture thereof |
| US7033602B1 (en) | 2002-06-21 | 2006-04-25 | Advanced Cardiovascular Systems, Inc. | Polycationic peptide coatings and methods of coating implantable medical devices |
| US7011842B1 (en) | 2002-06-21 | 2006-03-14 | Advanced Cardiovascular Systems, Inc. | Polycationic peptide coatings and methods of making the same |
| US7056523B1 (en) | 2002-06-21 | 2006-06-06 | Advanced Cardiovascular Systems, Inc. | Implantable medical devices incorporating chemically conjugated polymers and oligomers of L-arginine |
| US7794743B2 (en) * | 2002-06-21 | 2010-09-14 | Advanced Cardiovascular Systems, Inc. | Polycationic peptide coatings and methods of making the same |
| US7217426B1 (en) | 2002-06-21 | 2007-05-15 | Advanced Cardiovascular Systems, Inc. | Coatings containing polycationic peptides for cardiovascular therapy |
| US8506617B1 (en) | 2002-06-21 | 2013-08-13 | Advanced Cardiovascular Systems, Inc. | Micronized peptide coated stent |
| US6994867B1 (en) | 2002-06-21 | 2006-02-07 | Advanced Cardiovascular Systems, Inc. | Biocompatible carrier containing L-arginine |
| US7070798B1 (en) | 2002-06-21 | 2006-07-04 | Advanced Cardiovascular Systems, Inc. | Coatings for implantable medical devices incorporating chemically-bound polymers and oligomers of L-arginine |
| US6896965B1 (en) * | 2002-11-12 | 2005-05-24 | Advanced Cardiovascular Systems, Inc. | Rate limiting barriers for implantable devices |
| US7776926B1 (en) | 2002-12-11 | 2010-08-17 | Advanced Cardiovascular Systems, Inc. | Biocompatible coating for implantable medical devices |
| US7758880B2 (en) * | 2002-12-11 | 2010-07-20 | Advanced Cardiovascular Systems, Inc. | Biocompatible polyacrylate compositions for medical applications |
| US7074276B1 (en) * | 2002-12-12 | 2006-07-11 | Advanced Cardiovascular Systems, Inc. | Clamp mandrel fixture and a method of using the same to minimize coating defects |
| US20060002968A1 (en) * | 2004-06-30 | 2006-01-05 | Gordon Stewart | Anti-proliferative and anti-inflammatory agent combination for treatment of vascular disorders |
| US7758881B2 (en) * | 2004-06-30 | 2010-07-20 | Advanced Cardiovascular Systems, Inc. | Anti-proliferative and anti-inflammatory agent combination for treatment of vascular disorders with an implantable medical device |
| US7094256B1 (en) | 2002-12-16 | 2006-08-22 | Advanced Cardiovascular Systems, Inc. | Coatings for implantable medical device containing polycationic peptides |
| US8435550B2 (en) * | 2002-12-16 | 2013-05-07 | Abbot Cardiovascular Systems Inc. | Anti-proliferative and anti-inflammatory agent combination for treatment of vascular disorders with an implantable medical device |
| US7144419B2 (en) * | 2003-01-24 | 2006-12-05 | Medtronic Vascular, Inc. | Drug-polymer coated stent with blended phenoxy and styrenic block copolymers |
| US7063884B2 (en) * | 2003-02-26 | 2006-06-20 | Advanced Cardiovascular Systems, Inc. | Stent coating |
| US20040220656A1 (en) * | 2003-04-30 | 2004-11-04 | Epstein Samuel J. | Coated medical devices and methods of making the same |
| US20080215137A1 (en) * | 2003-04-30 | 2008-09-04 | Boston Scientific Scimed, Inc. | Therapeutic driving layer for a medical device |
| AU2003287378B2 (en) * | 2003-05-02 | 2010-12-16 | Correvio International Sàrl | Aminocyclohexyl ether compounds and uses thereof |
| US7345086B2 (en) * | 2003-05-02 | 2008-03-18 | Cardiome Pharma Corp. | Uses of ion channel modulating compounds |
| US20090041841A1 (en) * | 2003-05-02 | 2009-02-12 | Cardiome Pharma Corp. | Controlled release tablet formulations for the prevention of arrhythmias |
| US7279174B2 (en) * | 2003-05-08 | 2007-10-09 | Advanced Cardiovascular Systems, Inc. | Stent coatings comprising hydrophilic additives |
| US20050118344A1 (en) | 2003-12-01 | 2005-06-02 | Pacetti Stephen D. | Temperature controlled crimping |
| US20050021127A1 (en) * | 2003-07-21 | 2005-01-27 | Kawula Paul John | Porous glass fused onto stent for drug retention |
| CA2445420A1 (en) * | 2003-07-29 | 2005-01-29 | Invitrogen Corporation | Kinase and phosphatase assays |
| US7727752B2 (en) * | 2003-07-29 | 2010-06-01 | Life Technologies Corporation | Kinase and phosphatase assays |
| US7619059B2 (en) * | 2003-07-29 | 2009-11-17 | Life Technologies Corporation | Bimolecular optical probes |
| US7785512B1 (en) | 2003-07-31 | 2010-08-31 | Advanced Cardiovascular Systems, Inc. | Method and system of controlled temperature mixing and molding of polymers with active agents for implantable medical devices |
| WO2005018635A2 (en) * | 2003-08-07 | 2005-03-03 | Cardiome Pharma Corp. | Ion channel modulating activity i |
| NZ592039A (en) | 2003-08-27 | 2013-03-28 | Ophthotech Corp | Combination therapy for the treatment of ocular neovascular disorders |
| JP2007505315A (ja) * | 2003-09-12 | 2007-03-08 | インヴィトロジェン コーポレーション | 多重結合および活性アッセイ |
| US7198675B2 (en) * | 2003-09-30 | 2007-04-03 | Advanced Cardiovascular Systems | Stent mandrel fixture and method for selectively coating surfaces of a stent |
| DK1687642T3 (da) * | 2003-10-07 | 2009-05-11 | Centelion | Screeningsfremgangsmåder til kombinationer af biologiske forbindelser |
| US7345087B2 (en) * | 2003-10-31 | 2008-03-18 | Cardiome Pharma Corp. | Aminocyclohexyl ether compounds and uses thereof |
| US7261946B2 (en) * | 2003-11-14 | 2007-08-28 | Advanced Cardiovascular Systems, Inc. | Block copolymers of acrylates and methacrylates with fluoroalkenes |
| US9114198B2 (en) * | 2003-11-19 | 2015-08-25 | Advanced Cardiovascular Systems, Inc. | Biologically beneficial coatings for implantable devices containing fluorinated polymers and methods for fabricating the same |
| US8192752B2 (en) * | 2003-11-21 | 2012-06-05 | Advanced Cardiovascular Systems, Inc. | Coatings for implantable devices including biologically erodable polyesters and methods for fabricating the same |
| US7220816B2 (en) * | 2003-12-16 | 2007-05-22 | Advanced Cardiovascular Systems, Inc. | Biologically absorbable coatings for implantable devices based on poly(ester amides) and methods for fabricating the same |
| US7435788B2 (en) * | 2003-12-19 | 2008-10-14 | Advanced Cardiovascular Systems, Inc. | Biobeneficial polyamide/polyethylene glycol polymers for use with drug eluting stents |
| US7563324B1 (en) | 2003-12-29 | 2009-07-21 | Advanced Cardiovascular Systems Inc. | System and method for coating an implantable medical device |
| TWI332003B (en) * | 2004-01-30 | 2010-10-21 | Lilly Co Eli | Kinase inhibitors |
| US8685431B2 (en) * | 2004-03-16 | 2014-04-01 | Advanced Cardiovascular Systems, Inc. | Biologically absorbable coatings for implantable devices based on copolymers having ester bonds and methods for fabricating the same |
| US8778014B1 (en) | 2004-03-31 | 2014-07-15 | Advanced Cardiovascular Systems, Inc. | Coatings for preventing balloon damage to polymer coated stents |
| EP1729815A2 (en) | 2004-04-01 | 2006-12-13 | Cardiome Pharma Corp. | Pegylated ion channel modulating compounds |
| US8058304B2 (en) * | 2004-04-01 | 2011-11-15 | Cardiome Pharma Corp. | Merged ion channel modulating compounds and uses thereof |
| US7553377B1 (en) | 2004-04-27 | 2009-06-30 | Advanced Cardiovascular Systems, Inc. | Apparatus and method for electrostatic coating of an abluminal stent surface |
| US8293890B2 (en) * | 2004-04-30 | 2012-10-23 | Advanced Cardiovascular Systems, Inc. | Hyaluronic acid based copolymers |
| US20050265960A1 (en) * | 2004-05-26 | 2005-12-01 | Pacetti Stephen D | Polymers containing poly(ester amides) and agents for use with medical articles and methods of fabricating the same |
| US7820732B2 (en) * | 2004-04-30 | 2010-10-26 | Advanced Cardiovascular Systems, Inc. | Methods for modulating thermal and mechanical properties of coatings on implantable devices |
| US20050288481A1 (en) * | 2004-04-30 | 2005-12-29 | Desnoyer Jessica R | Design of poly(ester amides) for the control of agent-release from polymeric compositions |
| US9561309B2 (en) * | 2004-05-27 | 2017-02-07 | Advanced Cardiovascular Systems, Inc. | Antifouling heparin coatings |
| US20050271700A1 (en) * | 2004-06-03 | 2005-12-08 | Desnoyer Jessica R | Poly(ester amide) coating composition for implantable devices |
| US7563780B1 (en) | 2004-06-18 | 2009-07-21 | Advanced Cardiovascular Systems, Inc. | Heparin prodrugs and drug delivery stents formed therefrom |
| US20050287184A1 (en) * | 2004-06-29 | 2005-12-29 | Hossainy Syed F A | Drug-delivery stent formulations for restenosis and vulnerable plaque |
| US7494665B1 (en) * | 2004-07-30 | 2009-02-24 | Advanced Cardiovascular Systems, Inc. | Polymers containing siloxane monomers |
| US8357391B2 (en) * | 2004-07-30 | 2013-01-22 | Advanced Cardiovascular Systems, Inc. | Coatings for implantable devices comprising poly (hydroxy-alkanoates) and diacid linkages |
| US7311980B1 (en) | 2004-08-02 | 2007-12-25 | Advanced Cardiovascular Systems, Inc. | Polyactive/polylactic acid coatings for an implantable device |
| US7648727B2 (en) * | 2004-08-26 | 2010-01-19 | Advanced Cardiovascular Systems, Inc. | Methods for manufacturing a coated stent-balloon assembly |
| US7244443B2 (en) * | 2004-08-31 | 2007-07-17 | Advanced Cardiovascular Systems, Inc. | Polymers of fluorinated monomers and hydrophilic monomers |
| US8110211B2 (en) * | 2004-09-22 | 2012-02-07 | Advanced Cardiovascular Systems, Inc. | Medicated coatings for implantable medical devices including polyacrylates |
| US9011831B2 (en) * | 2004-09-30 | 2015-04-21 | Advanced Cardiovascular Systems, Inc. | Methacrylate copolymers for medical devices |
| US7166680B2 (en) * | 2004-10-06 | 2007-01-23 | Advanced Cardiovascular Systems, Inc. | Blends of poly(ester amide) polymers |
| US20060083770A1 (en) * | 2004-10-15 | 2006-04-20 | Specialty Coating Systems, Inc. | Medical devices and methods of preparation and use |
| US20060089485A1 (en) * | 2004-10-27 | 2006-04-27 | Desnoyer Jessica R | End-capped poly(ester amide) copolymers |
| US8603634B2 (en) | 2004-10-27 | 2013-12-10 | Abbott Cardiovascular Systems Inc. | End-capped poly(ester amide) copolymers |
| US7862835B2 (en) * | 2004-10-27 | 2011-01-04 | Boston Scientific Scimed, Inc. | Method of manufacturing a medical device having a porous coating thereon |
| US20060095122A1 (en) * | 2004-10-29 | 2006-05-04 | Advanced Cardiovascular Systems, Inc. | Implantable devices comprising biologically absorbable star polymers and methods for fabricating the same |
| US7390497B2 (en) * | 2004-10-29 | 2008-06-24 | Advanced Cardiovascular Systems, Inc. | Poly(ester amide) filler blends for modulation of coating properties |
| US7481835B1 (en) | 2004-10-29 | 2009-01-27 | Advanced Cardiovascular Systems, Inc. | Encapsulated covered stent |
| ES2483940T3 (es) * | 2004-11-08 | 2014-08-08 | Cardiome Pharma Corp. | Un nuevo régimen de dosificación para compuestos moduladores del canal iónico para el tratamiento de la fibrilación auricular aguda en un ser humano |
| US7214759B2 (en) | 2004-11-24 | 2007-05-08 | Advanced Cardiovascular Systems, Inc. | Biologically absorbable coatings for implantable devices based on polyesters and methods for fabricating the same |
| US8609123B2 (en) * | 2004-11-29 | 2013-12-17 | Advanced Cardiovascular Systems, Inc. | Derivatized poly(ester amide) as a biobeneficial coating |
| US20060115449A1 (en) * | 2004-11-30 | 2006-06-01 | Advanced Cardiovascular Systems, Inc. | Bioabsorbable, biobeneficial, tyrosine-based polymers for use in drug eluting stent coatings |
| US7892592B1 (en) | 2004-11-30 | 2011-02-22 | Advanced Cardiovascular Systems, Inc. | Coating abluminal surfaces of stents and other implantable medical devices |
| US7632307B2 (en) | 2004-12-16 | 2009-12-15 | Advanced Cardiovascular Systems, Inc. | Abluminal, multilayer coating constructs for drug-delivery stents |
| US7604818B2 (en) * | 2004-12-22 | 2009-10-20 | Advanced Cardiovascular Systems, Inc. | Polymers of fluorinated monomers and hydrocarbon monomers |
| US7419504B2 (en) * | 2004-12-27 | 2008-09-02 | Advanced Cardiovascular Systems, Inc. | Poly(ester amide) block copolymers |
| US8007775B2 (en) * | 2004-12-30 | 2011-08-30 | Advanced Cardiovascular Systems, Inc. | Polymers containing poly(hydroxyalkanoates) and agents for use with medical articles and methods of fabricating the same |
| US7202325B2 (en) * | 2005-01-14 | 2007-04-10 | Advanced Cardiovascular Systems, Inc. | Poly(hydroxyalkanoate-co-ester amides) and agents for use with medical articles |
| US9381279B2 (en) | 2005-03-24 | 2016-07-05 | Abbott Cardiovascular Systems Inc. | Implantable devices formed on non-fouling methacrylate or acrylate polymers |
| US7700659B2 (en) * | 2005-03-24 | 2010-04-20 | Advanced Cardiovascular Systems, Inc. | Implantable devices formed of non-fouling methacrylate or acrylate polymers |
| US20060216431A1 (en) * | 2005-03-28 | 2006-09-28 | Kerrigan Cameron K | Electrostatic abluminal coating of a stent crimped on a balloon catheter |
| US7795467B1 (en) | 2005-04-26 | 2010-09-14 | Advanced Cardiovascular Systems, Inc. | Bioabsorbable, biobeneficial polyurethanes for use in medical devices |
| US8778375B2 (en) | 2005-04-29 | 2014-07-15 | Advanced Cardiovascular Systems, Inc. | Amorphous poly(D,L-lactide) coating |
| US7637941B1 (en) | 2005-05-11 | 2009-12-29 | Advanced Cardiovascular Systems, Inc. | Endothelial cell binding coatings for rapid encapsulation of bioerodable stents |
| US7622070B2 (en) * | 2005-06-20 | 2009-11-24 | Advanced Cardiovascular Systems, Inc. | Method of manufacturing an implantable polymeric medical device |
| US7823533B2 (en) * | 2005-06-30 | 2010-11-02 | Advanced Cardiovascular Systems, Inc. | Stent fixture and method for reducing coating defects |
| US8021676B2 (en) | 2005-07-08 | 2011-09-20 | Advanced Cardiovascular Systems, Inc. | Functionalized chemically inert polymers for coatings |
| US7785647B2 (en) * | 2005-07-25 | 2010-08-31 | Advanced Cardiovascular Systems, Inc. | Methods of providing antioxidants to a drug containing product |
| US7735449B1 (en) | 2005-07-28 | 2010-06-15 | Advanced Cardiovascular Systems, Inc. | Stent fixture having rounded support structures and method for use thereof |
| US20070128246A1 (en) * | 2005-12-06 | 2007-06-07 | Hossainy Syed F A | Solventless method for forming a coating |
| US20070135909A1 (en) * | 2005-12-08 | 2007-06-14 | Desnoyer Jessica R | Adhesion polymers to improve stent retention |
| US7591841B2 (en) | 2005-12-16 | 2009-09-22 | Advanced Cardiovascular Systems, Inc. | Implantable devices for accelerated healing |
| US7976891B1 (en) | 2005-12-16 | 2011-07-12 | Advanced Cardiovascular Systems, Inc. | Abluminal stent coating apparatus and method of using focused acoustic energy |
| US7638156B1 (en) | 2005-12-19 | 2009-12-29 | Advanced Cardiovascular Systems, Inc. | Apparatus and method for selectively coating a medical article |
| US7867547B2 (en) | 2005-12-19 | 2011-01-11 | Advanced Cardiovascular Systems, Inc. | Selectively coating luminal surfaces of stents |
| US20070148390A1 (en) * | 2005-12-27 | 2007-06-28 | Specialty Coating Systems, Inc. | Fluorinated coatings |
| US20070196428A1 (en) * | 2006-02-17 | 2007-08-23 | Thierry Glauser | Nitric oxide generating medical devices |
| US7601383B2 (en) * | 2006-02-28 | 2009-10-13 | Advanced Cardiovascular Systems, Inc. | Coating construct containing poly (vinyl alcohol) |
| US7713637B2 (en) * | 2006-03-03 | 2010-05-11 | Advanced Cardiovascular Systems, Inc. | Coating containing PEGylated hyaluronic acid and a PEGylated non-hyaluronic acid polymer |
| US20070231363A1 (en) * | 2006-03-29 | 2007-10-04 | Yung-Ming Chen | Coatings formed from stimulus-sensitive material |
| US20070259101A1 (en) * | 2006-05-02 | 2007-11-08 | Kleiner Lothar W | Microporous coating on medical devices |
| US7985441B1 (en) | 2006-05-04 | 2011-07-26 | Yiwen Tang | Purification of polymers for coating applications |
| US8069814B2 (en) | 2006-05-04 | 2011-12-06 | Advanced Cardiovascular Systems, Inc. | Stent support devices |
| US8304012B2 (en) * | 2006-05-04 | 2012-11-06 | Advanced Cardiovascular Systems, Inc. | Method for drying a stent |
| US7775178B2 (en) * | 2006-05-26 | 2010-08-17 | Advanced Cardiovascular Systems, Inc. | Stent coating apparatus and method |
| US8568764B2 (en) * | 2006-05-31 | 2013-10-29 | Advanced Cardiovascular Systems, Inc. | Methods of forming coating layers for medical devices utilizing flash vaporization |
| US9561351B2 (en) * | 2006-05-31 | 2017-02-07 | Advanced Cardiovascular Systems, Inc. | Drug delivery spiral coil construct |
| US8703167B2 (en) | 2006-06-05 | 2014-04-22 | Advanced Cardiovascular Systems, Inc. | Coatings for implantable medical devices for controlled release of a hydrophilic drug and a hydrophobic drug |
| US20080124372A1 (en) * | 2006-06-06 | 2008-05-29 | Hossainy Syed F A | Morphology profiles for control of agent release rates from polymer matrices |
| US8778376B2 (en) | 2006-06-09 | 2014-07-15 | Advanced Cardiovascular Systems, Inc. | Copolymer comprising elastin pentapeptide block and hydrophilic block, and medical device and method of treating |
| US20070286882A1 (en) * | 2006-06-09 | 2007-12-13 | Yiwen Tang | Solvent systems for coating medical devices |
| US20080095918A1 (en) * | 2006-06-14 | 2008-04-24 | Kleiner Lothar W | Coating construct with enhanced interfacial compatibility |
| US8114150B2 (en) | 2006-06-14 | 2012-02-14 | Advanced Cardiovascular Systems, Inc. | RGD peptide attached to bioabsorbable stents |
| US8603530B2 (en) | 2006-06-14 | 2013-12-10 | Abbott Cardiovascular Systems Inc. | Nanoshell therapy |
| US8048448B2 (en) * | 2006-06-15 | 2011-11-01 | Abbott Cardiovascular Systems Inc. | Nanoshells for drug delivery |
| US8017237B2 (en) | 2006-06-23 | 2011-09-13 | Abbott Cardiovascular Systems, Inc. | Nanoshells on polymers |
| US8956640B2 (en) * | 2006-06-29 | 2015-02-17 | Advanced Cardiovascular Systems, Inc. | Block copolymers including a methoxyethyl methacrylate midblock |
| US20080008736A1 (en) * | 2006-07-06 | 2008-01-10 | Thierry Glauser | Random copolymers of methacrylates and acrylates |
| US9028859B2 (en) * | 2006-07-07 | 2015-05-12 | Advanced Cardiovascular Systems, Inc. | Phase-separated block copolymer coatings for implantable medical devices |
| US8703169B1 (en) | 2006-08-15 | 2014-04-22 | Abbott Cardiovascular Systems Inc. | Implantable device having a coating comprising carrageenan and a biostable polymer |
| US20080085293A1 (en) * | 2006-08-22 | 2008-04-10 | Jenchen Yang | Drug eluting stent and therapeutic methods using c-Jun N-terminal kinase inhibitor |
| US20080118541A1 (en) * | 2006-11-21 | 2008-05-22 | Abbott Laboratories | Use of a terpolymer of tetrafluoroethylene, hexafluoropropylene, and vinylidene fluoride in drug eluting coatings on medical devices |
| EP2097119A4 (en) * | 2006-11-21 | 2012-10-17 | Abbott Lab | USE OF A TERPOLYMER OF TETRAFLUOROETHYLENE, HEXAFLUORPROPYLENE AND VINYLIDENE FLUORIDE IN MEDICAMENTAL COATINGS |
| US7713541B1 (en) * | 2006-11-21 | 2010-05-11 | Abbott Cardiovascular Systems Inc. | Zwitterionic terpolymers, method of making and use on medical devices |
| US8597673B2 (en) * | 2006-12-13 | 2013-12-03 | Advanced Cardiovascular Systems, Inc. | Coating of fast absorption or dissolution |
| US8017141B2 (en) | 2006-12-15 | 2011-09-13 | Advanced Cardiovascular Systems, Inc. | Coatings of acrylamide-based copolymers |
| US7592342B2 (en) * | 2007-05-10 | 2009-09-22 | Smithkline Beecham Corporation | Quinoxaline derivatives as PI3 kinase inhibitors |
| US20080286332A1 (en) | 2007-05-14 | 2008-11-20 | Pacetti Stephen D | Implantable medical devices with a topcoat layer of phosphoryl choline acrylate polymer for reduced thrombosis, and improved mechanical properties |
| US8147769B1 (en) | 2007-05-16 | 2012-04-03 | Abbott Cardiovascular Systems Inc. | Stent and delivery system with reduced chemical degradation |
| US9056155B1 (en) | 2007-05-29 | 2015-06-16 | Abbott Cardiovascular Systems Inc. | Coatings having an elastic primer layer |
| US8048441B2 (en) | 2007-06-25 | 2011-11-01 | Abbott Cardiovascular Systems, Inc. | Nanobead releasing medical devices |
| US8109904B1 (en) | 2007-06-25 | 2012-02-07 | Abbott Cardiovascular Systems Inc. | Drug delivery medical devices |
| US20090041845A1 (en) * | 2007-08-08 | 2009-02-12 | Lothar Walter Kleiner | Implantable medical devices having thin absorbable coatings |
| US10301265B2 (en) * | 2008-05-28 | 2019-05-28 | Virginia I. Roxas-Duncan | Small molecule inhibitors of botulinum neurotoxins |
| US20120189641A1 (en) | 2009-02-25 | 2012-07-26 | OSI Pharmaceuticals, LLC | Combination anti-cancer therapy |
| EP2401614A1 (en) | 2009-02-27 | 2012-01-04 | OSI Pharmaceuticals, LLC | Methods for the identification of agents that inhibit mesenchymal-like tumor cells or their formation |
| WO2010099138A2 (en) | 2009-02-27 | 2010-09-02 | Osi Pharmaceuticals, Inc. | Methods for the identification of agents that inhibit mesenchymal-like tumor cells or their formation |
| JP2012519282A (ja) | 2009-02-27 | 2012-08-23 | オーエスアイ・ファーマシューティカルズ,エルエルシー | 間葉様腫瘍細胞またはその生成を阻害する薬剤を同定するための方法 |
| EP2241557A1 (de) | 2009-04-02 | 2010-10-20 | Æterna Zentaris GmbH | Chinoxalin-Derivate und deren Anwendung zur Behandlung gutartiger und bösartiger Tumorerkrankungen |
| GB0908905D0 (en) | 2009-05-26 | 2009-07-01 | Sentinel Oncology Ltd | Pharmaceutical compounds |
| US10253020B2 (en) | 2009-06-12 | 2019-04-09 | Abivax | Compounds for preventing, inhibiting, or treating cancer, AIDS and/or premature aging |
| US8685433B2 (en) | 2010-03-31 | 2014-04-01 | Abbott Cardiovascular Systems Inc. | Absorbable coating for implantable device |
| KR101886459B1 (ko) | 2010-10-08 | 2018-08-07 | 니발리스 테라퓨틱스, 인코포레이티드 | S-나이트로소글루타티온 리덕타제 억제제로서의 신규한 치환된 퀴놀린 화합물 |
| CA2821412A1 (en) | 2010-12-16 | 2012-06-21 | N30 Pharmaceuticals, Inc. | Novel substituted bicyclic aromatic compounds as s-nitrosoglutathione reductase inhibitors |
| WO2012149014A1 (en) | 2011-04-25 | 2012-11-01 | OSI Pharmaceuticals, LLC | Use of emt gene signatures in cancer drug discovery, diagnostics, and treatment |
| WO2013152252A1 (en) | 2012-04-06 | 2013-10-10 | OSI Pharmaceuticals, LLC | Combination anti-cancer therapy |
| EP2757161A1 (en) | 2013-01-17 | 2014-07-23 | Splicos | miRNA-124 as a biomarker of viral infection |
| US9969911B2 (en) | 2013-10-25 | 2018-05-15 | Kuraray Co., Ltd. | Hot-melt adhesive composition |
| US20170027940A1 (en) | 2014-04-10 | 2017-02-02 | Stichting Het Nederlands Kanker Instituut | Method for treating cancer |
| EP2974729A1 (en) | 2014-07-17 | 2016-01-20 | Abivax | Quinoline derivatives for use in the treatment of inflammatory diseases |
| WO2016121607A1 (ja) | 2015-01-27 | 2016-08-04 | 株式会社クラレ | アクリル系ブロック共重合体および粘接着剤組成物 |
| US10399946B2 (en) | 2015-09-10 | 2019-09-03 | Laurel Therapeutics Ltd. | Solid forms of an S-Nitrosoglutathione reductase inhibitor |
| EP3669873A1 (en) | 2018-12-20 | 2020-06-24 | Abivax | Quinoline derivatives for use ine the traeatment of inflammation diseases |
Family Cites Families (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3272824A (en) | 1962-12-06 | 1966-09-13 | Norwich Pharma Co | 4-amino-6, 7-di(lower) alkoxyquinolines |
| DE2913728A1 (de) * | 1979-04-05 | 1980-10-16 | Bayer Ag | 2-sulfonyl-chinoxaline, verfahren zu ihrer herstellung sowie ihre verwendung als mikrobizide |
| NZ194196A (en) * | 1979-07-17 | 1983-07-15 | Ici Australia Ltd | -(quinoxalin-2-yl(oxy or thio) phen (oxy or ylthio)-alkanoic acid derivatives or precursors |
| US4358307A (en) | 1979-10-02 | 1982-11-09 | Ici Australia Limited | Herbicidal quinoxaline carboxylic acid derivatives |
| US4462994A (en) | 1981-05-19 | 1984-07-31 | Nissan Chemical Industries, Inc. | N-Containing heterocyclic ring-substituted O-arylphosphate derivatives, preparation thereof, and insecticides, acaricides and nematocides containing said derivatives |
| IT1226045B (it) * | 1981-07-29 | 1990-12-10 | Simes | Derivati tetraidrochinolici |
| US4661499A (en) | 1985-06-18 | 1987-04-28 | Merck Frosst Canada, Inc. | 2-[(substituted)-phenoxymethyl]quinolines |
| US4888427A (en) | 1987-04-07 | 1989-12-19 | University Of Florida | Amino acids containing dihydropyridine ring systems for site-specific delivery of peptides to the brain |
| US5120348A (en) | 1988-01-06 | 1992-06-09 | Uniroyal Chemical Company, Inc. | Heterocyclic-alkylene quinoxalinyloxyphenoxypropanoate herbicides |
| US5319102A (en) | 1988-01-06 | 1994-06-07 | Uniroyal Chemical Company, Inc. | Heterocyclic-alkylene quinoxalinyloxyphenoxypropanoate herbicides |
| GB8907865D0 (en) * | 1989-04-07 | 1989-05-24 | Wyeth John & Brother Ltd | Tetrahydroquinoline derivatives |
| GB9004483D0 (en) | 1990-02-28 | 1990-04-25 | Erba Carlo Spa | New aryl-and heteroarylethenylene derivatives and process for their preparation |
| CA2049973C (en) * | 1990-02-28 | 2002-12-24 | Rodney G. Wolff | Intralumenal drug eluting prosthesis |
| WO1992020642A1 (en) | 1991-05-10 | 1992-11-26 | Rhone-Poulenc Rorer International (Holdings) Inc. | Bis mono-and bicyclic aryl and heteroaryl compounds which inhibit egf and/or pdgf receptor tyrosine kinase |
| US5480883A (en) | 1991-05-10 | 1996-01-02 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Bis mono- and bicyclic aryl and heteroaryl compounds which inhibit EGF and/or PDGF receptor tyrosine kinase |
| US5710158A (en) | 1991-05-10 | 1998-01-20 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Aryl and heteroaryl quinazoline compounds which inhibit EGF and/or PDGF receptor tyrosine kinase |
| US5823853A (en) * | 1996-07-18 | 1998-10-20 | Speedfam Corporation | Apparatus for the in-process detection of workpieces with a monochromatic light source |
| US6177401B1 (en) | 1992-11-13 | 2001-01-23 | Max-Planck-Gesellschaft Zur Forderung Der Wissenschaften | Use of organic compounds for the inhibition of Flk-1 mediated vasculogenesis and angiogenesis |
| US5336518A (en) | 1992-12-11 | 1994-08-09 | Cordis Corporation | Treatment of metallic surfaces using radiofrequency plasma deposition and chemical attachment of bioactive agents |
| US5700823A (en) | 1994-01-07 | 1997-12-23 | Sugen, Inc. | Treatment of platelet derived growth factor related disorders such as cancers |
| AU2096895A (en) | 1994-03-07 | 1995-09-25 | Sugen, Incorporated | Receptor tyrosine kinase inhibitors for inhibiting cell proliferative disorders and compositions thereof |
| DE4426373A1 (de) | 1994-07-26 | 1996-02-01 | Bayer Ag | 3-Substituierte Chinolin-5-carbonsäurederivate und Verfahren zu ihrer Herstellung |
| US5637113A (en) | 1994-12-13 | 1997-06-10 | Advanced Cardiovascular Systems, Inc. | Polymer film for wrapping a stent structure |
| AU4355296A (en) | 1994-12-28 | 1996-07-19 | Sankyo Company Limited | Indole derivatives |
| US5605696A (en) | 1995-03-30 | 1997-02-25 | Advanced Cardiovascular Systems, Inc. | Drug loaded polymeric material and method of manufacture |
| US5721277A (en) | 1995-04-21 | 1998-02-24 | Sugen, Inc. | Compounds and methods for inhibiting hyper-proliferative cell growth |
| CA2178541C (en) | 1995-06-07 | 2009-11-24 | Neal E. Fearnot | Implantable medical device |
| JP3476604B2 (ja) * | 1995-08-22 | 2003-12-10 | 鐘淵化学工業株式会社 | 薬剤を付着・コーティングしたステントの製造方法 |
| KR20000065227A (ko) | 1996-07-19 | 2000-11-06 | 다께다 구니오 | 복소환 화합물, 그의 제조방법 및 용도 |
| NZ336826A (en) * | 1997-01-21 | 2000-06-23 | Nissan Chemical Ind Ltd | Industrial antimicrobial/mildew-proofing agents, algicides and antifouling agents containing N-quinoxalylanilines |
| CA2278586C (en) * | 1997-02-20 | 2009-09-22 | Cook Incorporated | Coated implantable medical device |
| US6180632B1 (en) * | 1997-05-28 | 2001-01-30 | Aventis Pharmaceuticals Products Inc. | Quinoline and quinoxaline compounds which inhibit platelet-derived growth factor and/or p56lck tyrosine kinases |
| US6245760B1 (en) * | 1997-05-28 | 2001-06-12 | Aventis Pharmaceuticals Products, Inc | Quinoline and quinoxaline compounds which inhibit platelet-derived growth factor and/or p56lck tyrosine kinases |
| SI0991628T1 (en) | 1997-05-28 | 2005-06-30 | Aventis Pharmaceuticals Inc | QUINOLINE AND QUINOXALINE COMPOUNDS WHICH INHIBIT PLATELET-DERIVED GROWTH FACTOR AND/OR P56lck TYROSINE KINASES |
-
1998
- 1998-11-24 US US09/198,718 patent/US6180632B1/en not_active Expired - Fee Related
-
1999
- 1999-11-23 AU AU18294/00A patent/AU777256B2/en not_active Ceased
- 1999-11-23 BR BR9915653-9A patent/BR9915653A/pt not_active Application Discontinuation
- 1999-11-23 PL PL99348979A patent/PL348979A1/xx unknown
- 1999-11-23 KR KR1020017006536A patent/KR100784291B1/ko not_active Expired - Fee Related
- 1999-11-23 MX MXPA01005317A patent/MXPA01005317A/es active IP Right Grant
- 1999-11-23 NZ NZ512096A patent/NZ512096A/xx unknown
- 1999-11-23 EE EEP200100280A patent/EE200100280A/xx unknown
- 1999-11-23 CA CA002352261A patent/CA2352261A1/en not_active Abandoned
- 1999-11-23 JP JP2000583879A patent/JP2002530389A/ja active Pending
- 1999-11-23 UA UA2001064347A patent/UA76935C2/uk unknown
- 1999-11-23 WO PCT/US1999/027825 patent/WO2000031051A1/en not_active Ceased
- 1999-11-23 ID IDW00200101350A patent/ID29611A/id unknown
- 1999-11-23 EP EP99961784A patent/EP1133480A1/en not_active Withdrawn
- 1999-11-23 HU HU0104605A patent/HUP0104605A3/hu unknown
- 1999-11-23 CZ CZ20012276A patent/CZ20012276A3/cs unknown
- 1999-11-23 SK SK906-2001A patent/SK9062001A3/sk unknown
- 1999-11-23 EA EA200100579A patent/EA007534B1/ru not_active IP Right Cessation
- 1999-11-23 IL IL14340699A patent/IL143406A0/xx unknown
- 1999-11-23 CN CNB998157880A patent/CN100390154C/zh not_active Expired - Fee Related
-
2000
- 2000-09-29 US US09/675,746 patent/US6528526B1/en not_active Expired - Fee Related
-
2001
- 2001-05-25 NO NO20012582A patent/NO319801B1/no unknown
- 2001-06-20 BG BG105625A patent/BG65497B1/bg unknown
-
2002
- 2002-12-12 US US10/317,464 patent/US6696434B2/en not_active Expired - Fee Related
-
2003
- 2003-02-04 US US10/357,882 patent/US6852712B2/en not_active Expired - Fee Related
- 2003-02-06 US US10/359,983 patent/US6821962B2/en not_active Expired - Fee Related
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| BG65497B1 (bg) | Стент с полимерно покритие, съдържащо средства заинхибиране на рестеноза | |
| BG65482B1 (bg) | Стенд с полимерно покритие, съдържащо средства заинхибиране на рестеноза | |
| US6524347B1 (en) | Quinoline and quinoxaline compounds which inhibit platelet-derived growth factor and/or p56lck tyrosine kinases | |
| EP1001946B1 (en) | QUINOXALINE COMPOUNDS WHICH INHIBIT PLATELET-DERIVED GROWTH FACTOR AND/OR p56lck TYROSINE KINASES | |
| MXPA01005319A (en) | Quinoline and quinoxaline compounds | |
| MXPA01005318A (en) | Quinoline and quinoxaline compounds as pdgf-r and/or lck tyrosine kinase inhibitors |