SK25499A3 - Phosphinic acid amides as matrix metalloprotease inhibitors - Google Patents
Phosphinic acid amides as matrix metalloprotease inhibitors Download PDFInfo
- Publication number
- SK25499A3 SK25499A3 SK254-99A SK25499A SK25499A3 SK 25499 A3 SK25499 A3 SK 25499A3 SK 25499 A SK25499 A SK 25499A SK 25499 A3 SK25499 A3 SK 25499A3
- Authority
- SK
- Slovakia
- Prior art keywords
- alkyl
- hydroxy
- methylphenylphosphinyl
- compound
- compounds
- Prior art date
Links
- 239000011159 matrix material Substances 0.000 title abstract description 7
- 239000003475 metalloproteinase inhibitor Substances 0.000 title description 6
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 107
- 102000005741 Metalloproteases Human genes 0.000 claims abstract description 75
- 108010006035 Metalloproteases Proteins 0.000 claims abstract description 75
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 55
- 238000000034 method Methods 0.000 claims abstract description 53
- 230000000694 effects Effects 0.000 claims abstract description 40
- 201000010099 disease Diseases 0.000 claims abstract description 34
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 150000003949 imides Chemical class 0.000 claims abstract description 7
- -1 cycloheteroalkyl Chemical group 0.000 claims description 54
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 238000002360 preparation method Methods 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 14
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 14
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 14
- 125000002837 carbocyclic group Chemical group 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 229940080818 propionamide Drugs 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 230000003287 optical effect Effects 0.000 claims description 9
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 8
- 125000005127 aryl alkoxy alkyl group Chemical group 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- OWBJNSLROHEGOK-UHFFFAOYSA-N 2-[diphenylphosphoryl(2-phenylethyl)amino]-n-hydroxyacetamide Chemical compound C=1C=CC=CC=1P(=O)(C=1C=CC=CC=1)N(CC(=O)NO)CCC1=CC=CC=C1 OWBJNSLROHEGOK-UHFFFAOYSA-N 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000004474 heteroalkylene group Chemical group 0.000 claims description 3
- LMQSRMOBSSJUST-UHFFFAOYSA-N n-hydroxy-2-[[methyl(phenyl)phosphoryl]-(2-phenylethyl)amino]acetamide Chemical compound C=1C=CC=CC=1P(=O)(C)N(CC(=O)NO)CCC1=CC=CC=C1 LMQSRMOBSSJUST-UHFFFAOYSA-N 0.000 claims description 3
- BGYCEGKSSQJQNQ-CQSZACIVSA-N (2r)-2-[benzyl(dimethylphosphoryl)amino]-n-hydroxy-4-methylpentanamide Chemical compound CC(C)C[C@H](C(=O)NO)N(P(C)(C)=O)CC1=CC=CC=C1 BGYCEGKSSQJQNQ-CQSZACIVSA-N 0.000 claims description 2
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 2
- GABGNLCOMBJPQO-VVVCHXIZSA-N (2r)-2-[[ethyl(phenyl)phosphoryl]amino]-n-hydroxypropanamide Chemical compound ONC(=O)[C@@H](C)N[P@@](=O)(CC)C1=CC=CC=C1 GABGNLCOMBJPQO-VVVCHXIZSA-N 0.000 claims 1
- RNNMDWQPJWMEIA-GOSISDBHSA-N (2r)-2-[benzyl(diphenylphosphoryl)amino]-n-hydroxypropanamide Chemical compound C=1C=CC=CC=1P(=O)(C=1C=CC=CC=1)N([C@H](C)C(=O)NO)CC1=CC=CC=C1 RNNMDWQPJWMEIA-GOSISDBHSA-N 0.000 claims 1
- DEWGAQGFIIEVGA-JLCFBVMHSA-N (2r)-n-hydroxy-2-[6-[methyl(phenyl)phosphoryl]hexylamino]propanamide Chemical compound ONC(=O)[C@@H](C)NCCCCCC[P@@](C)(=O)C1=CC=CC=C1 DEWGAQGFIIEVGA-JLCFBVMHSA-N 0.000 claims 1
- 125000004945 acylaminoalkyl group Chemical group 0.000 claims 1
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims 1
- 125000004946 alkenylalkyl group Chemical group 0.000 claims 1
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims 1
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000005038 alkynylalkyl group Chemical group 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 1
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 abstract description 22
- 102000004190 Enzymes Human genes 0.000 abstract description 13
- 108090000790 Enzymes Proteins 0.000 abstract description 13
- 150000002148 esters Chemical class 0.000 abstract description 6
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 111
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 105
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
- 239000000203 mixture Substances 0.000 description 52
- 239000000243 solution Substances 0.000 description 51
- 239000000126 substance Substances 0.000 description 45
- 238000011282 treatment Methods 0.000 description 45
- 238000006243 chemical reaction Methods 0.000 description 43
- 238000003756 stirring Methods 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- 239000000047 product Substances 0.000 description 26
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 24
- 239000007787 solid Substances 0.000 description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
- 208000035475 disorder Diseases 0.000 description 21
- 210000001519 tissue Anatomy 0.000 description 20
- 241000282414 Homo sapiens Species 0.000 description 18
- 125000003118 aryl group Chemical group 0.000 description 18
- 239000003795 chemical substances by application Substances 0.000 description 18
- 239000000741 silica gel Substances 0.000 description 18
- 229910002027 silica gel Inorganic materials 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- 238000004809 thin layer chromatography Methods 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 16
- 239000003937 drug carrier Substances 0.000 description 16
- 125000004432 carbon atom Chemical group C* 0.000 description 15
- 238000003818 flash chromatography Methods 0.000 description 15
- 239000003921 oil Substances 0.000 description 15
- 235000019198 oils Nutrition 0.000 description 15
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 14
- 230000006378 damage Effects 0.000 description 13
- 125000000623 heterocyclic group Chemical group 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
- 229940088598 enzyme Drugs 0.000 description 12
- 235000019441 ethanol Nutrition 0.000 description 12
- 238000009472 formulation Methods 0.000 description 11
- 241001465754 Metazoa Species 0.000 description 10
- 125000004429 atom Chemical group 0.000 description 10
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- 229910052938 sodium sulfate Inorganic materials 0.000 description 10
- 235000011152 sodium sulphate Nutrition 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 9
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 9
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 125000005842 heteroatom Chemical group 0.000 description 9
- 230000005764 inhibitory process Effects 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 9
- 235000010356 sorbitol Nutrition 0.000 description 9
- 239000000600 sorbitol Substances 0.000 description 9
- 206010028980 Neoplasm Diseases 0.000 description 8
- 229920002472 Starch Polymers 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 230000002401 inhibitory effect Effects 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 235000019698 starch Nutrition 0.000 description 8
- 208000024891 symptom Diseases 0.000 description 8
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 7
- 229930006000 Sucrose Natural products 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 230000003197 catalytic effect Effects 0.000 description 7
- 235000011187 glycerol Nutrition 0.000 description 7
- 125000001072 heteroaryl group Chemical group 0.000 description 7
- 230000002829 reductive effect Effects 0.000 description 7
- 206010039073 rheumatoid arthritis Diseases 0.000 description 7
- 239000005720 sucrose Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000001413 amino acids Chemical class 0.000 description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
- 239000012267 brine Substances 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000003086 colorant Substances 0.000 description 6
- 239000012230 colorless oil Substances 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 235000013355 food flavoring agent Nutrition 0.000 description 6
- 235000003599 food sweetener Nutrition 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 201000008482 osteoarthritis Diseases 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 239000003765 sweetening agent Substances 0.000 description 6
- 230000000699 topical effect Effects 0.000 description 6
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 5
- 102000029816 Collagenase Human genes 0.000 description 5
- 108060005980 Collagenase Proteins 0.000 description 5
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 5
- 108010010803 Gelatin Proteins 0.000 description 5
- 229930195725 Mannitol Natural products 0.000 description 5
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
- 206010064996 Ulcerative keratitis Diseases 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000001768 carboxy methyl cellulose Substances 0.000 description 5
- 239000000796 flavoring agent Substances 0.000 description 5
- 229920000159 gelatin Polymers 0.000 description 5
- 239000008273 gelatin Substances 0.000 description 5
- 235000019322 gelatine Nutrition 0.000 description 5
- 235000011852 gelatine desserts Nutrition 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 238000001727 in vivo Methods 0.000 description 5
- 238000002372 labelling Methods 0.000 description 5
- 235000010355 mannitol Nutrition 0.000 description 5
- 239000000594 mannitol Substances 0.000 description 5
- DODCBMODXGJOKD-FYZOBXCZSA-N methyl (2r)-2-amino-4-methylpentanoate;hydrochloride Chemical compound Cl.COC(=O)[C@H](N)CC(C)C DODCBMODXGJOKD-FYZOBXCZSA-N 0.000 description 5
- 238000007911 parenteral administration Methods 0.000 description 5
- 230000002265 prevention Effects 0.000 description 5
- 102000004169 proteins and genes Human genes 0.000 description 5
- 108090000623 proteins and genes Proteins 0.000 description 5
- 239000001632 sodium acetate Substances 0.000 description 5
- 235000017281 sodium acetate Nutrition 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 5
- 239000008107 starch Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- 230000008685 targeting Effects 0.000 description 5
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 4
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 4
- 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 4
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
- 102000000422 Matrix Metalloproteinase 3 Human genes 0.000 description 4
- 206010027476 Metastases Diseases 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- 101710172711 Structural protein Proteins 0.000 description 4
- 208000025865 Ulcer Diseases 0.000 description 4
- 235000010443 alginic acid Nutrition 0.000 description 4
- 239000000783 alginic acid Substances 0.000 description 4
- 229920000615 alginic acid Polymers 0.000 description 4
- 229960001126 alginic acid Drugs 0.000 description 4
- 150000004781 alginic acids Chemical class 0.000 description 4
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 4
- 206010003246 arthritis Diseases 0.000 description 4
- 230000033228 biological regulation Effects 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 235000010980 cellulose Nutrition 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
- 239000001913 cellulose Substances 0.000 description 4
- 238000004040 coloring Methods 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 208000015181 infectious disease Diseases 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- 230000000670 limiting effect Effects 0.000 description 4
- 230000009401 metastasis Effects 0.000 description 4
- LITWZVHRFAQHQA-CYBMUJFWSA-N methyl (2r)-2-(benzylamino)-4-methylpentanoate Chemical compound COC(=O)[C@@H](CC(C)C)NCC1=CC=CC=C1 LITWZVHRFAQHQA-CYBMUJFWSA-N 0.000 description 4
- HIVDOHPKFIBYPZ-SECBINFHSA-N methyl (2r)-2-(benzylamino)propanoate Chemical compound COC(=O)[C@@H](C)NCC1=CC=CC=C1 HIVDOHPKFIBYPZ-SECBINFHSA-N 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 239000003755 preservative agent Substances 0.000 description 4
- 235000013772 propylene glycol Nutrition 0.000 description 4
- 108091007196 stromelysin Proteins 0.000 description 4
- 235000000346 sugar Nutrition 0.000 description 4
- 238000007910 systemic administration Methods 0.000 description 4
- 239000000454 talc Substances 0.000 description 4
- 235000012222 talc Nutrition 0.000 description 4
- 229910052623 talc Inorganic materials 0.000 description 4
- 238000011200 topical administration Methods 0.000 description 4
- 238000005303 weighing Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229920002261 Corn starch Polymers 0.000 description 3
- ROHFNLRQFUQHCH-RXMQYKEDSA-N D-leucine Chemical compound CC(C)C[C@@H](N)C(O)=O ROHFNLRQFUQHCH-RXMQYKEDSA-N 0.000 description 3
- 229930182819 D-leucine Natural products 0.000 description 3
- 239000001856 Ethyl cellulose Substances 0.000 description 3
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 3
- 108010026132 Gelatinases Proteins 0.000 description 3
- 102000013382 Gelatinases Human genes 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 241000124008 Mammalia Species 0.000 description 3
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 3
- 229920001615 Tragacanth Polymers 0.000 description 3
- GXJPMBQLUDQIAV-NKWVEPMBSA-N [(4r,5s)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]methanol Chemical compound CC1(C)O[C@H](CO)[C@H](C=C)O1 GXJPMBQLUDQIAV-NKWVEPMBSA-N 0.000 description 3
- IHJRCKILKAJAQT-UHFFFAOYSA-N [chloro(ethyl)phosphoryl]benzene Chemical compound CCP(Cl)(=O)C1=CC=CC=C1 IHJRCKILKAJAQT-UHFFFAOYSA-N 0.000 description 3
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 238000002399 angioplasty Methods 0.000 description 3
- 239000000427 antigen Substances 0.000 description 3
- 102000036639 antigens Human genes 0.000 description 3
- 108091007433 antigens Proteins 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 3
- 239000000305 astragalus gummifer gum Substances 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 3
- 235000019445 benzyl alcohol Nutrition 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- JGIATAMCQXIDNZ-UHFFFAOYSA-N calcium sulfide Chemical compound [Ca]=S JGIATAMCQXIDNZ-UHFFFAOYSA-N 0.000 description 3
- 201000011510 cancer Diseases 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 229940112822 chewing gum Drugs 0.000 description 3
- 235000015218 chewing gum Nutrition 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 229960002424 collagenase Drugs 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 235000019325 ethyl cellulose Nutrition 0.000 description 3
- 229920001249 ethyl cellulose Polymers 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 230000035876 healing Effects 0.000 description 3
- 230000001900 immune effect Effects 0.000 description 3
- 230000003053 immunization Effects 0.000 description 3
- 238000002649 immunization Methods 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- JSZMNUNRBZQOIV-SECBINFHSA-N methyl (2r)-2-(hexylamino)propanoate Chemical compound CCCCCCN[C@H](C)C(=O)OC JSZMNUNRBZQOIV-SECBINFHSA-N 0.000 description 3
- WLSPJGVWVCMSLB-OAHLLOKOSA-N methyl (2r)-2-[benzyl(dimethylphosphoryl)amino]-4-methylpentanoate Chemical compound COC(=O)[C@@H](CC(C)C)N(P(C)(C)=O)CC1=CC=CC=C1 WLSPJGVWVCMSLB-OAHLLOKOSA-N 0.000 description 3
- CSRBFSIUGNYKNI-GYCJOSAFSA-N methyl (2r)-2-[benzyl-[ethyl(phenyl)phosphoryl]amino]propanoate Chemical compound COC(=O)[C@@H](C)N([P@](=O)(CC)C=1C=CC=CC=1)CC1=CC=CC=C1 CSRBFSIUGNYKNI-GYCJOSAFSA-N 0.000 description 3
- ZOEWDHWTSZWTLW-IVZQSRNASA-N methyl (2r)-2-[hexyl-[methyl(phenyl)phosphoryl]amino]propanoate Chemical compound CCCCCCN([C@H](C)C(=O)OC)[P@](C)(=O)C1=CC=CC=C1 ZOEWDHWTSZWTLW-IVZQSRNASA-N 0.000 description 3
- WXNOFARQXPEOOC-GFCCVEGCSA-N methyl (2r)-4-methyl-2-(pyridin-3-ylmethylamino)pentanoate Chemical compound COC(=O)[C@@H](CC(C)C)NCC1=CC=CN=C1 WXNOFARQXPEOOC-GFCCVEGCSA-N 0.000 description 3
- FKJSXPOVNNAAMJ-BFUOFWGJSA-N methyl (2r)-4-methyl-2-[[methyl(phenyl)phosphoryl]amino]pentanoate Chemical compound COC(=O)[C@@H](CC(C)C)N[P@](C)(=O)C1=CC=CC=C1 FKJSXPOVNNAAMJ-BFUOFWGJSA-N 0.000 description 3
- FFLFRDWHMSXSTB-UHFFFAOYSA-N methyl 2-[[methyl(phenyl)phosphoryl]-(2-phenylethyl)amino]acetate Chemical compound C=1C=CC=CC=1P(C)(=O)N(CC(=O)OC)CCC1=CC=CC=C1 FFLFRDWHMSXSTB-UHFFFAOYSA-N 0.000 description 3
- 229920000609 methyl cellulose Polymers 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- KQSSATDQUYCRGS-UHFFFAOYSA-N methyl glycinate Chemical compound COC(=O)CN KQSSATDQUYCRGS-UHFFFAOYSA-N 0.000 description 3
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 3
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 3
- 239000001923 methylcellulose Substances 0.000 description 3
- 235000010981 methylcellulose Nutrition 0.000 description 3
- 229960002216 methylparaben Drugs 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
- 208000028169 periodontal disease Diseases 0.000 description 3
- 230000003389 potentiating effect Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 231100000241 scar Toxicity 0.000 description 3
- 210000002966 serum Anatomy 0.000 description 3
- 239000008159 sesame oil Substances 0.000 description 3
- 235000011803 sesame oil Nutrition 0.000 description 3
- 210000001626 skin fibroblast Anatomy 0.000 description 3
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 3
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 3
- 238000010561 standard procedure Methods 0.000 description 3
- 239000008117 stearic acid Substances 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 150000008163 sugars Chemical class 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 230000004614 tumor growth Effects 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- 239000008158 vegetable oil Substances 0.000 description 3
- NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 2
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- 208000032544 Cicatrix Diseases 0.000 description 2
- 102000008186 Collagen Human genes 0.000 description 2
- 108010035532 Collagen Proteins 0.000 description 2
- 241000701022 Cytomegalovirus Species 0.000 description 2
- 201000004624 Dermatitis Diseases 0.000 description 2
- 206010014989 Epidermolysis bullosa Diseases 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 108090000288 Glycoproteins Proteins 0.000 description 2
- 102000003886 Glycoproteins Human genes 0.000 description 2
- 229920002907 Guar gum Polymers 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 235000019483 Peanut oil Nutrition 0.000 description 2
- 102000035195 Peptidases Human genes 0.000 description 2
- 108091005804 Peptidases Proteins 0.000 description 2
- 239000004365 Protease Substances 0.000 description 2
- 201000002154 Pterygium Diseases 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 244000299461 Theobroma cacao Species 0.000 description 2
- 235000009470 Theobroma cacao Nutrition 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- BTMQENOUJJKBGT-UHFFFAOYSA-N [chloro(methyl)phosphoryl]benzene Chemical compound CP(Cl)(=O)C1=CC=CC=C1 BTMQENOUJJKBGT-UHFFFAOYSA-N 0.000 description 2
- BHYBJNSQCWMPAJ-UHFFFAOYSA-N [ethoxy(ethyl)phosphoryl]benzene Chemical compound CCOP(=O)(CC)C1=CC=CC=C1 BHYBJNSQCWMPAJ-UHFFFAOYSA-N 0.000 description 2
- 230000002159 abnormal effect Effects 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 108010003059 aggrecanase Proteins 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 125000000266 alpha-aminoacyl group Chemical group 0.000 description 2
- QWCKQJZIFLGMSD-UHFFFAOYSA-N alpha-aminobutyric acid Chemical compound CCC(N)C(O)=O QWCKQJZIFLGMSD-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000003146 anticoagulant agent Substances 0.000 description 2
- 229940127219 anticoagulant drug Drugs 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 229960000686 benzalkonium chloride Drugs 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- DMEDJHBMUUIKEU-LJQANCHMSA-N benzyl (2R)-2-(benzylamino)-4-methylpentanoate Chemical compound CC(C)C[C@@H](NCc1ccccc1)C(=O)OCc1ccccc1 DMEDJHBMUUIKEU-LJQANCHMSA-N 0.000 description 2
- MBRRYUQWSOODEO-GFCCVEGCSA-N benzyl (2r)-2-amino-4-methylpentanoate Chemical compound CC(C)C[C@@H](N)C(=O)OCC1=CC=CC=C1 MBRRYUQWSOODEO-GFCCVEGCSA-N 0.000 description 2
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 210000000988 bone and bone Anatomy 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 229920001436 collagen Polymers 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 235000005687 corn oil Nutrition 0.000 description 2
- 239000002285 corn oil Substances 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 210000004087 cornea Anatomy 0.000 description 2
- 235000012343 cottonseed oil Nutrition 0.000 description 2
- 239000002385 cottonseed oil Substances 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 239000002274 desiccant Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000006196 drop Substances 0.000 description 2
- 239000003623 enhancer Substances 0.000 description 2
- 208000030533 eye disease Diseases 0.000 description 2
- 230000003176 fibrotic effect Effects 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 208000024693 gingival disease Diseases 0.000 description 2
- 208000007565 gingivitis Diseases 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000000665 guar gum Substances 0.000 description 2
- 235000010417 guar gum Nutrition 0.000 description 2
- 229960002154 guar gum Drugs 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 2
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 2
- 125000001245 hexylamino group Chemical group [H]N([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 230000002163 immunogen Effects 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 208000014674 injury Diseases 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 230000003834 intracellular effect Effects 0.000 description 2
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
- 235000010445 lecithin Nutrition 0.000 description 2
- 239000000787 lecithin Substances 0.000 description 2
- 229940067606 lecithin Drugs 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 208000002780 macular degeneration Diseases 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 210000004379 membrane Anatomy 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- ZDAGDEWIEYJONI-LJQANCHMSA-N methyl (2r)-2-[benzyl(diphenylphosphoryl)amino]propanoate Chemical compound C=1C=CC=CC=1P(=O)(C=1C=CC=CC=1)N([C@H](C)C(=O)OC)CC1=CC=CC=C1 ZDAGDEWIEYJONI-LJQANCHMSA-N 0.000 description 2
- WKDNMQNJMIEHKQ-FQRUVTKNSA-N methyl (2r)-2-[benzyl-[methyl(phenyl)phosphoryl]amino]-4-methylpentanoate Chemical compound COC(=O)[C@@H](CC(C)C)N([P@](C)(=O)C=1C=CC=CC=1)CC1=CC=CC=C1 WKDNMQNJMIEHKQ-FQRUVTKNSA-N 0.000 description 2
- DWKPPFQULDPWHX-GSVOUGTGSA-N methyl (2r)-2-aminopropanoate Chemical compound COC(=O)[C@@H](C)N DWKPPFQULDPWHX-GSVOUGTGSA-N 0.000 description 2
- JXGFKVWTMPAMLL-UHFFFAOYSA-N methyl(phenyl)phosphane;hydrochloride Chemical compound Cl.CPC1=CC=CC=C1 JXGFKVWTMPAMLL-UHFFFAOYSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- 125000002757 morpholinyl group Chemical group 0.000 description 2
- 201000006417 multiple sclerosis Diseases 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 239000004006 olive oil Substances 0.000 description 2
- 235000008390 olive oil Nutrition 0.000 description 2
- 239000006186 oral dosage form Substances 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 125000004043 oxo group Chemical group O=* 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000000312 peanut oil Substances 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 201000001245 periodontitis Diseases 0.000 description 2
- 125000004344 phenylpropyl group Chemical group 0.000 description 2
- 239000008363 phosphate buffer Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 125000003386 piperidinyl group Chemical group 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 238000012746 preparative thin layer chromatography Methods 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 239000003507 refrigerant Substances 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 2
- 210000003296 saliva Anatomy 0.000 description 2
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 2
- 230000037390 scarring Effects 0.000 description 2
- 230000037387 scars Effects 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 238000007493 shaping process Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 208000017520 skin disease Diseases 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 238000001356 surgical procedure Methods 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 230000036269 ulceration Effects 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- 239000000230 xanthan gum Substances 0.000 description 2
- 235000010493 xanthan gum Nutrition 0.000 description 2
- 229920001285 xanthan gum Polymers 0.000 description 2
- 229940082509 xanthan gum Drugs 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- OHYLYCNVLFJBFI-OEPVSBQMSA-N (2r)-2-[benzyl-[methyl(phenyl)phosphoryl]amino]-4-methylpentanoic acid Chemical compound C=1C=CC=CC=1P(C)(=O)N([C@H](CC(C)C)C(O)=O)CC1=CC=CC=C1 OHYLYCNVLFJBFI-OEPVSBQMSA-N 0.000 description 1
- XZCVMNQLRNHDOD-SNVBAGLBSA-N (2r)-5,6-dihydroxy-9-methyl-2-prop-1-en-2-yl-1,2,3,4-tetrahydrobenzo[7]annulen-7-one Chemical compound CC1=CC(=O)C(O)=C(O)C2=C1C[C@H](C(=C)C)CC2 XZCVMNQLRNHDOD-SNVBAGLBSA-N 0.000 description 1
- FNGJTABQXBMNQC-VIFPVBQESA-N (2s)-2-(2-phenylethylamino)propanoic acid Chemical compound OC(=O)[C@H](C)NCCC1=CC=CC=C1 FNGJTABQXBMNQC-VIFPVBQESA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- PNDPGZBMCMUPRI-HVTJNCQCSA-N 10043-66-0 Chemical compound [131I][131I] PNDPGZBMCMUPRI-HVTJNCQCSA-N 0.000 description 1
- SOOXGYAIUAHLKC-UHFFFAOYSA-N 2-(2,3-difluoro-4-hydroxyphenyl)acetic acid Chemical compound OC(=O)CC1=CC=C(O)C(F)=C1F SOOXGYAIUAHLKC-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- ZJSQZQMVXKZAGW-UHFFFAOYSA-N 2H-benzotriazol-4-ol hydrate Chemical compound O.OC1=CC=CC2=C1N=NN2 ZJSQZQMVXKZAGW-UHFFFAOYSA-N 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- DNTDOBSIBZKFCP-UHFFFAOYSA-N 5-[3-(tert-butylamino)-2-hydroxypropoxy]-3,4-dihydro-2h-naphthalen-1-one;hydron;chloride Chemical compound [Cl-].O=C1CCCC2=C1C=CC=C2OCC(O)C[NH2+]C(C)(C)C DNTDOBSIBZKFCP-UHFFFAOYSA-N 0.000 description 1
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 208000030507 AIDS Diseases 0.000 description 1
- 241000224422 Acanthamoeba Species 0.000 description 1
- ORILYTVJVMAKLC-UHFFFAOYSA-N Adamantane Natural products C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 102000015427 Angiotensins Human genes 0.000 description 1
- 108010064733 Angiotensins Proteins 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 108010011485 Aspartame Proteins 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- YFQFTFQTMXBZCT-UHFFFAOYSA-N CP(=O)Cl Chemical compound CP(=O)Cl YFQFTFQTMXBZCT-UHFFFAOYSA-N 0.000 description 1
- OITORCFCJAQZDV-JLCFBVMHSA-N C[P@](=O)(N([C@H](C)C(=O)O)CC1=CC=CC=C1)C1=CC=CC=C1 Chemical compound C[P@](=O)(N([C@H](C)C(=O)O)CC1=CC=CC=C1)C1=CC=CC=C1 OITORCFCJAQZDV-JLCFBVMHSA-N 0.000 description 1
- 206010006895 Cachexia Diseases 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920000623 Cellulose acetate phthalate Polymers 0.000 description 1
- 208000009043 Chemical Burns Diseases 0.000 description 1
- 208000018380 Chemical injury Diseases 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 206010056370 Congestive cardiomyopathy Diseases 0.000 description 1
- 206010010984 Corneal abrasion Diseases 0.000 description 1
- 208000028006 Corneal injury Diseases 0.000 description 1
- 229920002785 Croscarmellose sodium Polymers 0.000 description 1
- 102000004127 Cytokines Human genes 0.000 description 1
- 108090000695 Cytokines Proteins 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- 102100024452 DNA-directed RNA polymerase III subunit RPC1 Human genes 0.000 description 1
- 206010012438 Dermatitis atopic Diseases 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- 201000010046 Dilated cardiomyopathy Diseases 0.000 description 1
- 101800001224 Disintegrin Proteins 0.000 description 1
- 108700021041 Disintegrin Proteins 0.000 description 1
- 101100520660 Drosophila melanogaster Poc1 gene Proteins 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- 241001125671 Eretmochelys imbricata Species 0.000 description 1
- 229920003134 Eudragit® polymer Polymers 0.000 description 1
- 108050001049 Extracellular proteins Proteins 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 208000009329 Graft vs Host Disease Diseases 0.000 description 1
- 108060003393 Granulin Proteins 0.000 description 1
- 208000031886 HIV Infections Diseases 0.000 description 1
- 208000037357 HIV infectious disease Diseases 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 101000689002 Homo sapiens DNA-directed RNA polymerase III subunit RPC1 Proteins 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 208000019693 Lung disease Diseases 0.000 description 1
- 235000019759 Maize starch Nutrition 0.000 description 1
- XZCVMNQLRNHDOD-UHFFFAOYSA-N Manicol Natural products CC1=CC(=O)C(O)=C(O)C2=C1CC(C(=C)C)CC2 XZCVMNQLRNHDOD-UHFFFAOYSA-N 0.000 description 1
- 102000000380 Matrix Metalloproteinase 1 Human genes 0.000 description 1
- 108010016113 Matrix Metalloproteinase 1 Proteins 0.000 description 1
- 102000002274 Matrix Metalloproteinases Human genes 0.000 description 1
- 108010000684 Matrix Metalloproteinases Proteins 0.000 description 1
- 244000246386 Mentha pulegium Species 0.000 description 1
- 235000016257 Mentha pulegium Nutrition 0.000 description 1
- 235000004357 Mentha x piperita Nutrition 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010028604 Myocardial rupture Diseases 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- 102000003729 Neprilysin Human genes 0.000 description 1
- 108090000028 Neprilysin Proteins 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 108010067787 Proteoglycans Proteins 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 241000220010 Rhode Species 0.000 description 1
- 101100520662 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) PBA1 gene Proteins 0.000 description 1
- 108010077895 Sarcosine Proteins 0.000 description 1
- 206010039705 Scleritis Diseases 0.000 description 1
- 102000007562 Serum Albumin Human genes 0.000 description 1
- 108010071390 Serum Albumin Proteins 0.000 description 1
- 229920001800 Shellac Polymers 0.000 description 1
- 241000700584 Simplexvirus Species 0.000 description 1
- 208000028990 Skin injury Diseases 0.000 description 1
- GKLVYJBZJHMRIY-OUBTZVSYSA-N Technetium-99 Chemical compound [99Tc] GKLVYJBZJHMRIY-OUBTZVSYSA-N 0.000 description 1
- 208000026062 Tissue disease Diseases 0.000 description 1
- 241000700618 Vaccinia virus Species 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 101710204001 Zinc metalloprotease Proteins 0.000 description 1
- VJHCJDRQFCCTHL-UHFFFAOYSA-N acetic acid 2,3,4,5,6-pentahydroxyhexanal Chemical compound CC(O)=O.OCC(O)C(O)C(O)C(O)C=O VJHCJDRQFCCTHL-UHFFFAOYSA-N 0.000 description 1
- 125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 208000030961 allergic reaction Diseases 0.000 description 1
- 125000005336 allyloxy group Chemical group 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 208000022531 anorexia Diseases 0.000 description 1
- 210000000628 antibody-producing cell Anatomy 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 208000007474 aortic aneurysm Diseases 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 238000007080 aromatic substitution reaction Methods 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- 210000001188 articular cartilage Anatomy 0.000 description 1
- 125000001691 aryl alkyl amino group Chemical group 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 239000000605 aspartame Substances 0.000 description 1
- IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 description 1
- 235000010357 aspartame Nutrition 0.000 description 1
- 229960003438 aspartame Drugs 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 201000008937 atopic dermatitis Diseases 0.000 description 1
- 230000001363 autoimmune Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 210000002469 basement membrane Anatomy 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 230000010072 bone remodeling Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004181 carboxyalkyl group Chemical group 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 206010061592 cardiac fibrillation Diseases 0.000 description 1
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 229940081734 cellulose acetate phthalate Drugs 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000007910 chewable tablet Substances 0.000 description 1
- 229940068682 chewable tablet Drugs 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- XGRJZXREYAXTGV-UHFFFAOYSA-N chlorodiphenylphosphine Chemical compound C=1C=CC=CC=1P(Cl)C1=CC=CC=C1 XGRJZXREYAXTGV-UHFFFAOYSA-N 0.000 description 1
- 210000001612 chondrocyte Anatomy 0.000 description 1
- 208000019425 cirrhosis of liver Diseases 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 1
- 229960004126 codeine Drugs 0.000 description 1
- 206010009887 colitis Diseases 0.000 description 1
- 210000000795 conjunctiva Anatomy 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000010219 correlation analysis Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 229960005168 croscarmellose Drugs 0.000 description 1
- 239000001767 crosslinked sodium carboxy methyl cellulose Substances 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 125000002592 cumenyl group Chemical group C1(=C(C=CC=C1)*)C(C)C 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000016396 cytokine production Effects 0.000 description 1
- 206010061428 decreased appetite Diseases 0.000 description 1
- 239000013530 defoamer Substances 0.000 description 1
- 230000007850 degeneration Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000001066 destructive effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- MLCHBQKMVKNBOV-UHFFFAOYSA-M dioxido(phenyl)phosphanium Chemical compound [O-]P(=O)C1=CC=CC=C1 MLCHBQKMVKNBOV-UHFFFAOYSA-M 0.000 description 1
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 231100000676 disease causative agent Toxicity 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- 238000003821 enantio-separation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 210000000981 epithelium Anatomy 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 229960004667 ethyl cellulose Drugs 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 210000003414 extremity Anatomy 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- 230000004720 fertilization Effects 0.000 description 1
- 230000002600 fibrillogenic effect Effects 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- FATAVLOOLIRUNA-UHFFFAOYSA-N formylmethyl Chemical group [CH2]C=O FATAVLOOLIRUNA-UHFFFAOYSA-N 0.000 description 1
- 239000008369 fruit flavor Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 208000024908 graft versus host disease Diseases 0.000 description 1
- 230000003779 hair growth Effects 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 230000036074 healthy skin Effects 0.000 description 1
- 235000001050 hortel pimenta Nutrition 0.000 description 1
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- 229920001477 hydrophilic polymer Polymers 0.000 description 1
- 239000003752 hydrotrope Substances 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 229960002591 hydroxyproline Drugs 0.000 description 1
- 229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 description 1
- 229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 description 1
- 206010020718 hyperplasia Diseases 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
- 230000002637 immunotoxin Effects 0.000 description 1
- 229940051026 immunotoxin Drugs 0.000 description 1
- 239000002596 immunotoxin Substances 0.000 description 1
- 231100000608 immunotoxin Toxicity 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000012606 in vitro cell culture Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000035990 intercellular signaling Effects 0.000 description 1
- 230000004068 intracellular signaling Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000007913 intrathecal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 208000028867 ischemia Diseases 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000644 isotonic solution Substances 0.000 description 1
- 210000005067 joint tissue Anatomy 0.000 description 1
- BWHLPLXXIDYSNW-UHFFFAOYSA-N ketorolac tromethamine Chemical compound OCC(N)(CO)CO.OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 BWHLPLXXIDYSNW-UHFFFAOYSA-N 0.000 description 1
- 108010045069 keyhole-limpet hemocyanin Proteins 0.000 description 1
- 210000003127 knee Anatomy 0.000 description 1
- 238000002430 laser surgery Methods 0.000 description 1
- 201000010901 lateral sclerosis Diseases 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 238000012153 long-term therapy Methods 0.000 description 1
- 238000011866 long-term treatment Methods 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 210000004698 lymphocyte Anatomy 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 208000037819 metastatic cancer Diseases 0.000 description 1
- 208000011575 metastatic malignant neoplasm Diseases 0.000 description 1
- 206010061289 metastatic neoplasm Diseases 0.000 description 1
- FKJSXPOVNNAAMJ-YJYMSZOUSA-N methyl (2r)-4-methyl-2-[[methyl(phenyl)phosphoryl]amino]pentanoate Chemical compound COC(=O)[C@@H](CC(C)C)N[P@@](C)(=O)C1=CC=CC=C1 FKJSXPOVNNAAMJ-YJYMSZOUSA-N 0.000 description 1
- JRHJGNASVCSYMA-UHFFFAOYSA-N methyl 2-[diphenylphosphoryl(2-phenylethyl)amino]acetate Chemical compound C=1C=CC=CC=1P(=O)(C=1C=CC=CC=1)N(CC(=O)OC)CCC1=CC=CC=C1 JRHJGNASVCSYMA-UHFFFAOYSA-N 0.000 description 1
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 1
- SMYHRJOQEVSCKS-UHFFFAOYSA-N methyl 4-hydroxybenzoate;propyl 4-hydroxybenzoate Chemical compound COC(=O)C1=CC=C(O)C=C1.CCCOC(=O)C1=CC=C(O)C=C1 SMYHRJOQEVSCKS-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 1
- 208000005264 motor neuron disease Diseases 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- 229940051866 mouthwash Drugs 0.000 description 1
- 201000006938 muscular dystrophy Diseases 0.000 description 1
- 210000003007 myelin sheath Anatomy 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- HYDZPXNVHXJHBG-UHFFFAOYSA-N o-benzylhydroxylamine;hydron;chloride Chemical compound Cl.NOCC1=CC=CC=C1 HYDZPXNVHXJHBG-UHFFFAOYSA-N 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 206010033103 otosclerosis Diseases 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000005704 oxymethylene group Chemical group [H]C([H])([*:2])O[*:1] 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000007967 peppermint flavor Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000002953 phosphate buffered saline Substances 0.000 description 1
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 description 1
- 125000005541 phosphonamide group Chemical group 0.000 description 1
- 125000005499 phosphonyl group Chemical group 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229940100467 polyvinyl acetate phthalate Drugs 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000007634 remodeling Methods 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 208000037803 restenosis Diseases 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229940043230 sarcosine Drugs 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000037380 skin damage Effects 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 210000004988 splenocyte Anatomy 0.000 description 1
- 229940032147 starch Drugs 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
- 230000008354 tissue degradation Effects 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/36—Amides thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/66—Phosphorus compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
-
- 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
-
- 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
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- 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
- A61P19/04—Drugs for skeletal disorders for non-specific disorders of the connective tissue
-
- 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
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/58—Pyridine rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms
- C07F9/655345—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a five-membered ring
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Immunology (AREA)
- Ophthalmology & Optometry (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Dermatology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2476596P | 1996-08-28 | 1996-08-28 | |
| PCT/US1997/014556 WO1998008853A1 (en) | 1996-08-28 | 1997-08-22 | Phosphinic acid amides as matrix metalloprotease inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK25499A3 true SK25499A3 (en) | 2000-03-13 |
Family
ID=21822291
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK254-99A SK25499A3 (en) | 1996-08-28 | 1997-08-22 | Phosphinic acid amides as matrix metalloprotease inhibitors |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US5830915A (ja) |
| EP (1) | EP0925303B1 (ja) |
| JP (1) | JP3539736B2 (ja) |
| KR (1) | KR20000035925A (ja) |
| CN (1) | CN1228780A (ja) |
| AR (1) | AR009357A1 (ja) |
| AT (1) | ATE226590T1 (ja) |
| AU (1) | AU732653B2 (ja) |
| BR (1) | BR9713182A (ja) |
| CA (1) | CA2264254C (ja) |
| CO (1) | CO4900033A1 (ja) |
| CZ (1) | CZ63699A3 (ja) |
| DE (1) | DE69716619T2 (ja) |
| DK (1) | DK0925303T3 (ja) |
| HU (1) | HUP9903916A3 (ja) |
| ID (1) | ID18145A (ja) |
| IL (1) | IL128668A (ja) |
| NO (1) | NO990857L (ja) |
| NZ (1) | NZ334258A (ja) |
| PE (1) | PE107698A1 (ja) |
| PL (1) | PL331854A1 (ja) |
| RU (1) | RU2170232C2 (ja) |
| SK (1) | SK25499A3 (ja) |
| TR (1) | TR199900399T2 (ja) |
| TW (1) | TW518338B (ja) |
| WO (1) | WO1998008853A1 (ja) |
| ZA (1) | ZA977700B (ja) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030206874A1 (en) * | 1996-11-21 | 2003-11-06 | The Proctor & Gamble Company | Promoting whole body health |
| IL134273A0 (en) | 1997-07-31 | 2001-04-30 | Procter & Gamble | Acyclic metalloprotease inhibitors |
| US6846478B1 (en) | 1998-02-27 | 2005-01-25 | The Procter & Gamble Company | Promoting whole body health |
| DE19850072A1 (de) | 1998-10-30 | 2000-05-04 | Bayer Ag | Phosphinat-Peptidanaloga zur Behandlung von fibrotischen Erkrankungen |
| US6762178B2 (en) | 1999-01-27 | 2004-07-13 | Wyeth Holdings Corporation | Acetylenic aryl sulfonamide and phosphinic acid amide hydroxamic acid TACE inhibitors |
| US6200996B1 (en) | 1999-01-27 | 2001-03-13 | American Cyanamid Company | Heteroaryl acetylenic sulfonamide and phosphinic acid amide hydroxamic acid tace inhibitors |
| US6946473B2 (en) | 1999-01-27 | 2005-09-20 | Wyeth Holdings Corporation | Preparation and use of acetylenic ortho-sulfonamido and phosphinic acid amido bicyclic heteroaryl hydroxamic acids as TACE inhibitors |
| US6313123B1 (en) | 1999-01-27 | 2001-11-06 | American Cyanamid Company | Acetylenic sulfonamide thiol tace inhibitors |
| US6225311B1 (en) | 1999-01-27 | 2001-05-01 | American Cyanamid Company | Acetylenic α-amino acid-based sulfonamide hydroxamic acid tace inhibitors |
| US6753337B2 (en) | 1999-01-27 | 2004-06-22 | Wyeth Holdings Corporation | Alkynyl containing hydroxamic acid compounds as matrix metalloproteinase/tace inhibitors |
| WO2000044710A2 (en) * | 1999-01-27 | 2000-08-03 | American Cyanamid Company | Acetylenic aryl sulfonamide and phosphinic acid amide hydroxamic acid tace inhibitors |
| US6277885B1 (en) | 1999-01-27 | 2001-08-21 | American Cyanamid Company | Acetylenic aryl sulfonamide and phosphinic acid amide hydroxamic acid TACE inhibitors |
| US6340691B1 (en) | 1999-01-27 | 2002-01-22 | American Cyanamid Company | Alkynyl containing hydroxamic acid compounds as matrix metalloproteinase and tace inhibitors |
| BR0007784A (pt) | 1999-01-27 | 2002-02-05 | American Cyanamid Co | Composto, método para inibir mudanças patológicas mediadas pela enzima que converte o tnf-alfa (tace) em um mamìfero, composição farmacêutica, e, processo para preparar um composto |
| AR035313A1 (es) * | 1999-01-27 | 2004-05-12 | Wyeth Corp | Inhibidores de tace acetilenicos de acido hidroxamico de sulfonamida a base de alfa-aminoacidos, composiciones farmaceuticas y el uso de los mismos para la manufactura de medicamentos. |
| US6326516B1 (en) | 1999-01-27 | 2001-12-04 | American Cyanamid Company | Acetylenic β-sulfonamido and phosphinic acid amide hydroxamic acid TACE inhibitors |
| WO2000051975A1 (en) | 1999-03-03 | 2000-09-08 | The Procter & Gamble Company | Alkenyl- and alkynyl-containing metalloprotease inhibitors |
| US6297337B1 (en) | 1999-05-19 | 2001-10-02 | Pmd Holdings Corp. | Bioadhesive polymer compositions |
| US6312474B1 (en) * | 1999-09-15 | 2001-11-06 | Bio-Vascular, Inc. | Resorbable implant materials |
| US8283135B2 (en) | 2000-06-30 | 2012-10-09 | The Procter & Gamble Company | Oral care compositions containing combinations of anti-bacterial and host-response modulating agents |
| CA2415068C (en) * | 2000-06-30 | 2009-03-10 | The Procter & Gamble Company | Oral compositions comprising antimicrobial agents |
| MXPA03000043A (es) * | 2000-06-30 | 2003-10-15 | Procter & Gamble | Promocion de la salud en todo el cuerpo. |
| SI1303527T1 (en) * | 2000-07-18 | 2005-04-30 | Leo Pharma A/S | Matrix metalloproteinase inhibitors |
| FR2814950B1 (fr) * | 2000-10-05 | 2003-08-08 | Oreal | Utilisation d'au moins un extrait d'au moins un vegetal de la famille des ericaceae, dans des compositions destinees a traiter les signes cutanes du vieillissement |
| US6693099B2 (en) * | 2000-10-17 | 2004-02-17 | The Procter & Gamble Company | Substituted piperazine compounds optionally containing a quinolyl moiety for treating multidrug resistance |
| US6376514B1 (en) | 2000-10-17 | 2002-04-23 | The Procter & Gamble Co. | Substituted six-membered heterocyclic compounds useful for treating multidrug resistance and compositions and methods thereof |
| EP1440057A1 (en) | 2001-11-01 | 2004-07-28 | Wyeth Holdings Corporation | Allenic aryl sulfonamide hydroxamic acids as matrix metalloproteinase and tace inhibitors |
| PE20030701A1 (es) * | 2001-12-20 | 2003-08-21 | Schering Corp | Compuestos para el tratamiento de trastornos inflamatorios |
| ATE316090T1 (de) * | 2002-01-18 | 2006-02-15 | Leo Pharma As | Mmp-inhibitoren |
| US7199155B2 (en) | 2002-12-23 | 2007-04-03 | Wyeth Holdings Corporation | Acetylenic aryl sulfonate hydroxamic acid TACE and matrix metalloproteinase inhibitors |
| JP2006516548A (ja) | 2002-12-30 | 2006-07-06 | アンジオテック インターナショナル アクツィエン ゲゼルシャフト | 迅速ゲル化ポリマー組成物からの薬物送達法 |
| US7144588B2 (en) | 2003-01-17 | 2006-12-05 | Synovis Life Technologies, Inc. | Method of preventing surgical adhesions |
| EP1449538A1 (en) | 2003-02-21 | 2004-08-25 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | Inhibition of TACE or amphiregulin for the modulation of EGF receptor signal transactivation |
| WO2008111371A1 (ja) * | 2007-03-09 | 2008-09-18 | National University Corporation Nagoya University | ホスホロアミド化合物及びその製造方法、配位子、錯体、触媒、及び光学活性アルコールの製造方法 |
| TW201141536A (en) * | 2009-12-21 | 2011-12-01 | Colgate Palmolive Co | Oral care compositions and methods |
| JP6002764B2 (ja) * | 2011-06-29 | 2016-10-05 | ヤンセン ファーマシューティカ エヌ．ベー． | マトリックスメタロプロテアーゼのアロステリックなプロセシング阻害因子を使用する処置方法 |
| RU2488587C1 (ru) * | 2012-05-23 | 2013-07-27 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Казанский национальный исследовательский технологический университет" | Анилид гидроксиметиланилинометилфосфиновой кислоты (амидофос) в качестве биостимулятора активного ила в процессе очистки сточных вод и способ его получения |
| CA3234750A1 (en) | 2015-10-23 | 2017-04-27 | Navitor Pharmaceuticals, Inc. | Modulators of sestrin-gator2 interaction and uses thereof |
| WO2017117130A1 (en) | 2015-12-28 | 2017-07-06 | The United States Of America, As Represented By The Secretary, Department Of Health & Human Services | Methods for inhibiting human immunodeficiency virus (hiv) release from infected cells |
| CN107709288A (zh) * | 2016-02-03 | 2018-02-16 | 四川海思科制药有限公司 | 一种磷酰胺衍生物及制备方法和用途 |
| US20210220332A1 (en) * | 2016-04-29 | 2021-07-22 | Ophirex, Inc. | Pla2 and hmg-coa inhibitors for treatment of pathological conditions causing hemolysis, cerebral edema, and acute kidney injury |
| CN106905183B (zh) * | 2017-02-24 | 2018-07-31 | 三峡大学 | 一类含氨基的ɑ-酰氧基羰基酰胺类衍生物，制备方法及其应用 |
| CN116370448A (zh) * | 2017-04-26 | 2023-07-04 | 纳维托制药有限公司 | Sestrin-gator2相互作用的调节剂及其用途 |
| US11345654B2 (en) | 2018-10-24 | 2022-05-31 | Navitor Pharmaceuticals, Inc. | Polymorphic compounds and uses thereof |
| WO2021087432A1 (en) | 2019-11-01 | 2021-05-06 | Navitor Pharmaceuticals, Inc. | Methods of treatment using an mtorc1 modulator |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8601368D0 (en) * | 1986-01-21 | 1986-02-26 | Ici America Inc | Hydroxamic acids |
| DK77487A (da) * | 1986-03-11 | 1987-09-12 | Hoffmann La Roche | Hydroxylaminderivater |
| FR2609289B1 (fr) * | 1987-01-06 | 1991-03-29 | Bellon Labor Sa Roger | Nouveaux composes a activite d'inhibiteurs de collagenase, procede pour les preparer et compositions pharmaceutiques contenant ces composes |
| GB8827305D0 (en) * | 1988-11-23 | 1988-12-29 | British Bio Technology | Compounds |
| GB8919251D0 (en) * | 1989-08-24 | 1989-10-04 | British Bio Technology | Compounds |
| DE4011172A1 (de) * | 1990-04-06 | 1991-10-10 | Degussa | Verbindungen zur bekaempfung von pflanzenkrankheiten |
| US5189178A (en) * | 1990-11-21 | 1993-02-23 | Galardy Richard E | Matrix metalloprotease inhibitors |
| US5183900A (en) * | 1990-11-21 | 1993-02-02 | Galardy Richard E | Matrix metalloprotease inhibitors |
| GB9102635D0 (en) * | 1991-02-07 | 1991-03-27 | British Bio Technology | Compounds |
| GB9107368D0 (en) * | 1991-04-08 | 1991-05-22 | Smithkline Beecham Plc | Novel compounds |
| IL98681A (en) * | 1991-06-30 | 1997-06-10 | Yeda Rehovot And Dev Company L | Pharmaceutical compositions comprising hydroxamate derivatives for iron removal from mammalian cells and from pathogenic organisms and some novel hydroxamate derivatives |
| DE4127842A1 (de) * | 1991-08-22 | 1993-02-25 | Rhone Poulenc Rorer Gmbh | 5-((omega)-arylalky)-2-thienyl alkansaeuren, ihre salze und/oder ihre derivate |
| JPH05125029A (ja) * | 1991-11-06 | 1993-05-21 | Yamanouchi Pharmaceut Co Ltd | 新規なアミド化合物又はその塩 |
| DE69309047T2 (de) * | 1992-04-07 | 1997-09-11 | British Biotech Pharm | Hydroxamsäure enthaltende collagenase-inhibitoren und cytokinaktivitätsinhibitoren |
| AU4267293A (en) * | 1992-05-01 | 1993-11-29 | British Biotech Pharmaceuticals Limited | Use of MMP inhibitors |
| AU666727B2 (en) * | 1992-06-25 | 1996-02-22 | F. Hoffmann-La Roche Ag | Hydroxamic acid derivatives |
| GB9215665D0 (en) * | 1992-07-23 | 1992-09-09 | British Bio Technology | Compounds |
| GB9223904D0 (en) * | 1992-11-13 | 1993-01-06 | British Bio Technology | Inhibition of cytokine production |
| US5455258A (en) * | 1993-01-06 | 1995-10-03 | Ciba-Geigy Corporation | Arylsulfonamido-substituted hydroxamic acids |
| US5514716A (en) * | 1994-02-25 | 1996-05-07 | Sterling Winthrop, Inc. | Hydroxamic acid and carboxylic acid derivatives, process for their preparation and use thereof |
| US5962529A (en) * | 1994-06-22 | 1999-10-05 | British Biotech Pharmaceuticals Limited | Metalloproteinase inhibitors |
-
1997
- 1997-08-22 EP EP97939444A patent/EP0925303B1/en not_active Expired - Lifetime
- 1997-08-22 JP JP51171698A patent/JP3539736B2/ja not_active Expired - Fee Related
- 1997-08-22 DK DK97939444T patent/DK0925303T3/da active
- 1997-08-22 CZ CZ99636A patent/CZ63699A3/cs unknown
- 1997-08-22 IL IL12866897A patent/IL128668A/en not_active IP Right Cessation
- 1997-08-22 NZ NZ334258A patent/NZ334258A/xx unknown
- 1997-08-22 AU AU41531/97A patent/AU732653B2/en not_active Ceased
- 1997-08-22 CA CA002264254A patent/CA2264254C/en not_active Expired - Fee Related
- 1997-08-22 DE DE69716619T patent/DE69716619T2/de not_active Expired - Fee Related
- 1997-08-22 HU HU9903916A patent/HUP9903916A3/hu unknown
- 1997-08-22 RU RU99106245/04A patent/RU2170232C2/ru active
- 1997-08-22 BR BR9713182-2A patent/BR9713182A/pt unknown
- 1997-08-22 CN CN97197546A patent/CN1228780A/zh active Pending
- 1997-08-22 PL PL97331854A patent/PL331854A1/xx unknown
- 1997-08-22 SK SK254-99A patent/SK25499A3/sk unknown
- 1997-08-22 AT AT97939444T patent/ATE226590T1/de not_active IP Right Cessation
- 1997-08-22 KR KR1019997001661A patent/KR20000035925A/ko active IP Right Grant
- 1997-08-22 TR TR1999/00399T patent/TR199900399T2/xx unknown
- 1997-08-22 WO PCT/US1997/014556 patent/WO1998008853A1/en not_active Application Discontinuation
- 1997-08-26 US US08/918,950 patent/US5830915A/en not_active Expired - Fee Related
- 1997-08-27 CO CO97049512A patent/CO4900033A1/es unknown
- 1997-08-27 ZA ZA9707700A patent/ZA977700B/xx unknown
- 1997-08-27 AR ARP970103898A patent/AR009357A1/es unknown
- 1997-08-28 PE PE1997000765A patent/PE107698A1/es not_active Application Discontinuation
- 1997-08-28 ID IDP972999A patent/ID18145A/id unknown
-
1998
- 1998-02-03 TW TW087101222A patent/TW518338B/zh active
-
1999
- 1999-02-23 NO NO990857A patent/NO990857L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| ATE226590T1 (de) | 2002-11-15 |
| AU732653B2 (en) | 2001-04-26 |
| NO990857D0 (no) | 1999-02-23 |
| DK0925303T3 (da) | 2003-02-24 |
| CA2264254A1 (en) | 1998-03-05 |
| RU2170232C2 (ru) | 2001-07-10 |
| NO990857L (no) | 1999-04-28 |
| EP0925303A1 (en) | 1999-06-30 |
| TW518338B (en) | 2003-01-21 |
| PL331854A1 (en) | 1999-08-16 |
| CA2264254C (en) | 2003-03-11 |
| AU4153197A (en) | 1998-03-19 |
| JP2000515167A (ja) | 2000-11-14 |
| IL128668A (en) | 2002-02-10 |
| BR9713182A (pt) | 1999-11-03 |
| DE69716619T2 (de) | 2003-06-26 |
| PE107698A1 (es) | 1999-02-11 |
| TR199900399T2 (xx) | 1999-06-21 |
| CZ63699A3 (cs) | 1999-07-14 |
| HUP9903916A2 (hu) | 2001-05-28 |
| AR009357A1 (es) | 2000-04-12 |
| CN1228780A (zh) | 1999-09-15 |
| US5830915A (en) | 1998-11-03 |
| HUP9903916A3 (en) | 2001-06-28 |
| DE69716619D1 (en) | 2002-11-28 |
| EP0925303B1 (en) | 2002-10-23 |
| WO1998008853A1 (en) | 1998-03-05 |
| KR20000035925A (ko) | 2000-06-26 |
| JP3539736B2 (ja) | 2004-07-07 |
| NZ334258A (en) | 2000-11-24 |
| ZA977700B (en) | 1998-02-23 |
| IL128668A0 (en) | 2000-01-31 |
| ID18145A (id) | 1998-03-05 |
| CO4900033A1 (es) | 2000-03-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SK25499A3 (en) | Phosphinic acid amides as matrix metalloprotease inhibitors | |
| US6469000B1 (en) | 1,3-diheterocyclic metalloprotease inhibitors | |
| JP3347331B2 (ja) | 複素環式メタロプロテアーゼ阻害剤 | |
| AU731319B2 (en) | Heterocyclic metalloprotease inhibitors | |
| WO1998008853A9 (en) | Phosphinic acid amides as matrix metalloprotease inhibitors | |
| KR100352316B1 (ko) | 메탈로프로테아제억제제로서사용되는술포닐아미노치환히드록삼산유도체 | |
| AU4074097A (en) | Bidentate metalloprotease inhibitors | |
| MXPA99002064A (en) | Heterocyclic metalloprotease inhibitors | |
| MXPA99002067A (en) | Heterocyclic metalloprotease inhibitors | |
| MXPA99002065A (en) | Bidentate metalloprotease inhibitors | |
| MXPA99002066A (en) | 1,3-diheterocyclic metalloprotease inhibitors |