BG62805B1 - Заместени 4-биарилбутанови или 5-биарилпентанови киселини итехни производни като инхибитори на матрична металопротеаза - Google Patents
Заместени 4-биарилбутанови или 5-биарилпентанови киселини итехни производни като инхибитори на матрична металопротеаза Download PDFInfo
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- BG62805B1 BG62805B1 BG101482A BG10148297A BG62805B1 BG 62805 B1 BG62805 B1 BG 62805B1 BG 101482 A BG101482 A BG 101482A BG 10148297 A BG10148297 A BG 10148297A BG 62805 B1 BG62805 B1 BG 62805B1
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- Prior art keywords
- carbon atoms
- phenyl
- moiety contains
- compound
- alkyl
- Prior art date
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- 102000005741 Metalloproteases Human genes 0.000 title claims abstract description 18
- 108010006035 Metalloproteases Proteins 0.000 title claims abstract description 18
- 239000011159 matrix material Substances 0.000 title claims abstract description 17
- 239000002253 acid Substances 0.000 title claims description 51
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- 150000007513 acids Chemical class 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 359
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 180
- 238000000034 method Methods 0.000 claims abstract description 138
- 125000003118 aryl group Chemical group 0.000 claims abstract description 96
- 125000001424 substituent group Chemical group 0.000 claims abstract description 59
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 55
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 150000001413 amino acids Chemical class 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims description 158
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 116
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 107
- 125000000217 alkyl group Chemical group 0.000 claims description 85
- -1 4-Pentyloxyphenyl Chemical group 0.000 claims description 77
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 70
- 238000002360 preparation method Methods 0.000 claims description 69
- 229910052760 oxygen Inorganic materials 0.000 claims description 44
- 229910052717 sulfur Inorganic materials 0.000 claims description 43
- 125000005842 heteroatom Chemical group 0.000 claims description 37
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 33
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 32
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 28
- 125000003342 alkenyl group Chemical group 0.000 claims description 22
- 125000000304 alkynyl group Chemical group 0.000 claims description 22
- 125000004429 atom Chemical group 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- 230000000694 effects Effects 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 16
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 14
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- 125000003003 spiro group Chemical group 0.000 claims description 12
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- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 10
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 9
- 150000001721 carbon Chemical group 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
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- 229910052763 palladium Inorganic materials 0.000 claims description 9
- 201000008482 osteoarthritis Diseases 0.000 claims description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
- 210000000845 cartilage Anatomy 0.000 claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 150000002576 ketones Chemical class 0.000 claims description 7
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical group [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 7
- 206010027476 Metastases Diseases 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 210000001503 joint Anatomy 0.000 claims description 5
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- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 5
- 206010053555 Arthritis bacterial Diseases 0.000 claims description 4
- 208000004575 Infectious Arthritis Diseases 0.000 claims description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 230000006378 damage Effects 0.000 claims description 4
- 201000001223 septic arthritis Diseases 0.000 claims description 4
- 208000016192 Demyelinating disease Diseases 0.000 claims description 3
- 206010053177 Epidermolysis Diseases 0.000 claims description 3
- 125000005015 aryl alkynyl group Chemical group 0.000 claims description 3
- 230000008878 coupling Effects 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- 238000005859 coupling reaction Methods 0.000 claims description 3
- 238000006114 decarboxylation reaction Methods 0.000 claims description 3
- 230000003412 degenerative effect Effects 0.000 claims description 3
- 230000003111 delayed effect Effects 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000004447 heteroarylalkenyl group Chemical group 0.000 claims description 3
- 125000005312 heteroarylalkynyl group Chemical group 0.000 claims description 3
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- 201000001474 proteinuria Diseases 0.000 claims description 3
- 230000000472 traumatic effect Effects 0.000 claims description 3
- KUVIMPZFYIJJGK-UHFFFAOYSA-N 2-[2-[4-(4-chlorophenyl)phenyl]-2-oxoethyl]-5-phenylpentanoic acid Chemical compound C=1C=C(C=2C=CC(Cl)=CC=2)C=CC=1C(=O)CC(C(=O)O)CCCC1=CC=CC=C1 KUVIMPZFYIJJGK-UHFFFAOYSA-N 0.000 claims description 2
- 206010012305 Demyelination Diseases 0.000 claims description 2
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- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 230000021615 conjugation Effects 0.000 claims description 2
- 150000003949 imides Chemical class 0.000 claims description 2
- JXAGDPXECXQWBC-UHFFFAOYSA-N tanomastat Chemical compound C=1C=C(C=2C=CC(Cl)=CC=2)C=CC=1C(=O)CC(C(=O)O)CSC1=CC=CC=C1 JXAGDPXECXQWBC-UHFFFAOYSA-N 0.000 claims description 2
- 230000002123 temporal effect Effects 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 6
- 208000012659 Joint disease Diseases 0.000 claims 2
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 claims 2
- 125000001033 ether group Chemical group 0.000 claims 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical group C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims 1
- XGKVFGNLDIKNNQ-UHFFFAOYSA-N 2-[2-oxo-2-[4-(4-pentoxyphenyl)phenyl]ethyl]-5-phenylpentanoic acid Chemical compound C1=CC(OCCCCC)=CC=C1C1=CC=C(C(=O)CC(CCCC=2C=CC=CC=2)C(O)=O)C=C1 XGKVFGNLDIKNNQ-UHFFFAOYSA-N 0.000 claims 1
- WMVFDRMOZOTALK-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)phenyl]-2-[2-(1,3-dioxoisoindol-2-yl)ethyl]-4-oxobutanoic acid Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCC(C(=O)O)CC(=O)C(C=C1)=CC=C1C1=CC=C(Cl)C=C1 WMVFDRMOZOTALK-UHFFFAOYSA-N 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 206010028813 Nausea Diseases 0.000 claims 1
- 208000007536 Thrombosis Diseases 0.000 claims 1
- 208000025865 Ulcer Diseases 0.000 claims 1
- 125000002015 acyclic group Chemical group 0.000 claims 1
- 229920000180 alkyd Polymers 0.000 claims 1
- 150000001491 aromatic compounds Chemical class 0.000 claims 1
- 125000000732 arylene group Chemical group 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 229910052742 iron Inorganic materials 0.000 claims 1
- 230000009401 metastasis Effects 0.000 claims 1
- 150000002902 organometallic compounds Chemical class 0.000 claims 1
- 230000036269 ulceration Effects 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 8
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 4
- 230000004962 physiological condition Effects 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 418
- 239000000243 solution Substances 0.000 description 257
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 221
- 239000000047 product Substances 0.000 description 196
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 172
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 153
- 235000019439 ethyl acetate Nutrition 0.000 description 148
- 239000007787 solid Substances 0.000 description 145
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 134
- 239000011541 reaction mixture Substances 0.000 description 126
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 112
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 105
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 88
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 86
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 84
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 82
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 81
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 78
- 238000006243 chemical reaction Methods 0.000 description 72
- 238000004809 thin layer chromatography Methods 0.000 description 72
- 229910052786 argon Inorganic materials 0.000 description 67
- 239000000543 intermediate Substances 0.000 description 57
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 57
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 52
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 52
- 239000003921 oil Substances 0.000 description 51
- 235000019198 oils Nutrition 0.000 description 51
- 239000002904 solvent Substances 0.000 description 50
- 239000012043 crude product Substances 0.000 description 48
- 238000003756 stirring Methods 0.000 description 47
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 46
- 235000019441 ethanol Nutrition 0.000 description 44
- 239000011734 sodium Substances 0.000 description 43
- 239000012044 organic layer Substances 0.000 description 42
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 40
- 230000002829 reductive effect Effects 0.000 description 40
- 238000003818 flash chromatography Methods 0.000 description 38
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 36
- 239000010410 layer Substances 0.000 description 35
- 229960000583 acetic acid Drugs 0.000 description 34
- 239000000460 chlorine Substances 0.000 description 34
- 238000002844 melting Methods 0.000 description 34
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- 239000011780 sodium chloride Substances 0.000 description 33
- 238000005160 1H NMR spectroscopy Methods 0.000 description 29
- 235000010290 biphenyl Nutrition 0.000 description 29
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 28
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- 238000001914 filtration Methods 0.000 description 28
- 238000010828 elution Methods 0.000 description 26
- 238000007429 general method Methods 0.000 description 25
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 24
- 238000004458 analytical method Methods 0.000 description 24
- 150000008064 anhydrides Chemical class 0.000 description 24
- 238000010992 reflux Methods 0.000 description 24
- 239000002585 base Substances 0.000 description 23
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 23
- 239000008346 aqueous phase Substances 0.000 description 22
- 239000000284 extract Substances 0.000 description 22
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 21
- 238000000746 purification Methods 0.000 description 21
- 239000000741 silica gel Substances 0.000 description 21
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- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 21
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 20
- 235000019341 magnesium sulphate Nutrition 0.000 description 20
- 239000013078 crystal Substances 0.000 description 19
- 238000004128 high performance liquid chromatography Methods 0.000 description 19
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 18
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 18
- 229910000104 sodium hydride Inorganic materials 0.000 description 17
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 16
- 238000004587 chromatography analysis Methods 0.000 description 16
- 229920006395 saturated elastomer Polymers 0.000 description 16
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 15
- QJPQVXSHYBGQGM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QJPQVXSHYBGQGM-UHFFFAOYSA-N 0.000 description 15
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 14
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- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 13
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 12
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 12
- 239000000377 silicon dioxide Substances 0.000 description 12
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 12
- 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 11
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
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- 238000001953 recrystallisation Methods 0.000 description 11
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- 238000005727 Friedel-Crafts reaction Methods 0.000 description 10
- 102000002274 Matrix Metalloproteinases Human genes 0.000 description 10
- 108010000684 Matrix Metalloproteinases Proteins 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 10
- 238000002425 crystallisation Methods 0.000 description 10
- 230000008025 crystallization Effects 0.000 description 10
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 10
- 150000004702 methyl esters Chemical class 0.000 description 10
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 10
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- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 9
- AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 9
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- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 8
- 238000003820 Medium-pressure liquid chromatography Methods 0.000 description 8
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
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- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 235000011152 sodium sulphate Nutrition 0.000 description 8
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 8
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- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000009290 primary effect Effects 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 235000019833 protease Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000017854 proteolysis Effects 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 238000007634 remodeling Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000011894 semi-preparative HPLC Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
- PODWXQQNRWNDGD-UHFFFAOYSA-L sodium thiosulfate pentahydrate Chemical compound O.O.O.O.O.[Na+].[Na+].[O-]S([S-])(=O)=O PODWXQQNRWNDGD-UHFFFAOYSA-L 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 108091007196 stromelysin Proteins 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical class O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- OMHOTPHULFOYPL-UHFFFAOYSA-N tert-butyl 2-amino-5-bromobenzoate Chemical compound CC(C)(C)OC(=O)C1=CC(Br)=CC=C1N OMHOTPHULFOYPL-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- VLGPDTPSKUUHKR-UHFFFAOYSA-N tert-butyl n-(4-bromophenyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(Br)C=C1 VLGPDTPSKUUHKR-UHFFFAOYSA-N 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- MZIYQMVHASXABC-UHFFFAOYSA-N tetrakis(ethenyl)stannane Chemical compound C=C[Sn](C=C)(C=C)C=C MZIYQMVHASXABC-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 150000003568 thioethers Chemical group 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000001890 transfection Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000009261 transgenic effect Effects 0.000 description 1
- VZOSESAUMUACGR-UHFFFAOYSA-K trichlorotin;trimethylsilicon Chemical compound C[Si](C)C.Cl[Sn](Cl)Cl VZOSESAUMUACGR-UHFFFAOYSA-K 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- JGWFUSVYECJQDT-UHFFFAOYSA-N trimethyl(2-trimethylsilyloxyethoxy)silane Chemical compound C[Si](C)(C)OCCO[Si](C)(C)C JGWFUSVYECJQDT-UHFFFAOYSA-N 0.000 description 1
- XPFBMKHQJJNXFZ-UHFFFAOYSA-N trimethyl(2h-tetrazol-5-yl)stannane Chemical compound C[Sn](C)(C)C1=NN=NN1 XPFBMKHQJJNXFZ-UHFFFAOYSA-N 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/4035—Isoindoles, e.g. phthalimide
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
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- C07C205/34—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups bound to carbon atoms of six-membered aromatic rings and etherified hydroxy groups bound to acyclic carbon atoms of the carbon skeleton
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- C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
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- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/53—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
- C07C233/54—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of a saturated carbon skeleton
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- C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/84—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
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- C07C255/19—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and carboxyl groups, other than cyano groups, bound to the same saturated acyclic carbon skeleton
- C07C255/21—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and carboxyl groups, other than cyano groups, bound to the same saturated acyclic carbon skeleton the carbon skeleton being further substituted by doubly-bound oxygen atoms
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- C07F9/4056—Esters of arylalkanephosphonic acids
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BG101482A BG101482A (en) | 1998-01-30 |
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Families Citing this family (91)
Publication number | Priority date | Publication date | Assignee | Title |
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HRP950558A2 (en) * | 1994-11-15 | 1997-12-31 | Scott M. Wilhelm | Substituted 4-biarylbutric or biarylpentanoic acids and derivatives as matrix metalloprotease inhibitors |
ES2183905T3 (es) * | 1995-12-20 | 2003-04-01 | Hoffmann La Roche | Inhibidores de metaloproteasa de matriz. |
CZ298814B6 (cs) | 1996-01-23 | 2008-02-13 | Shionogi & Co., Ltd. | Sulfonované deriváty aminokyselin a metaloproteasové inhibitory obsahující tyto deriváty |
US6919375B1 (en) | 1996-01-23 | 2005-07-19 | Shionogi & Co., Ltd. | Sulfonated amino acid derivatives and metalloproteinase inhibitors containing the same |
US5925637A (en) | 1997-05-15 | 1999-07-20 | Bayer Corporation | Inhibition of matrix metalloproteases by substituted biaryl oxobutyric acids |
US5968795A (en) * | 1996-05-15 | 1999-10-19 | Bayer Corporation | Biaryl acetylenes as inhibitors of matrix metalloproteases |
TNSN97081A1 (fr) * | 1996-05-15 | 2005-03-15 | Bayer Corp | Inhibition des matrices metalloproteinases par 2- (w-aroylkyl) -4-biaryl-4-des acides oxubutyriques |
ZA974029B (en) * | 1996-05-15 | 1998-02-19 | Bayer Ag | Inhibition of matrix metalloproteinases by substituted phenethyl compounds. |
CO5080759A1 (es) * | 1996-05-15 | 2001-09-25 | Bayer Corp | Biarilacetilenos como inhibidores de la metaloproteasa de matriz |
DK0933993T3 (da) | 1996-06-14 | 2006-08-14 | Biocryst Pharm Inc | Substituerede cyclopentanforbindelser, der er egnede som neuraminidaseinhibitorer |
JP2002514179A (ja) * | 1996-09-04 | 2002-05-14 | ワーナー―ランバート・コンパニー | マトリックスメタロプロテイナーゼの阻害剤としてのビフェニル酪酸およびその誘導体 |
MY117687A (en) * | 1996-10-31 | 2004-07-31 | Bayer Corp | Substituted 4-biphenyl-4-hydroxybutric acid derivatives as matrix metalloprotease inhibitors |
DE19649827A1 (de) * | 1996-12-02 | 1998-06-04 | Bayer Ag | Verfahren zur Racemisierung von substituierten 4-Ketocarbonsäuren |
NZ334897A (en) * | 1996-12-09 | 2001-02-23 | Warner Lambert Co | Medicaments for treating and preventing heart failure and ventricular dilatation |
SI0946166T1 (en) * | 1996-12-17 | 2004-06-30 | Warner-Lambert Company Llc | Use of matrix metalloproteinase inhibitors for promoting wound healing |
ES2212142T3 (es) | 1996-12-17 | 2004-07-16 | Warner-Lambert Company Llc | Uso de inhibidores de metaloproteinasas de la matriz para promover la curacion de heridas. |
KR20000075955A (ko) * | 1997-03-04 | 2000-12-26 | 죤 에이치. 뷰센 | 방향족 술포닐 알파-히드록시 히드록삼산 화합물 |
US5756545A (en) * | 1997-04-21 | 1998-05-26 | Warner-Lambert Company | Biphenysulfonamide matrix metal alloproteinase inhibitors |
DE19717429A1 (de) * | 1997-04-25 | 1998-12-24 | Bayer Ag | Herstellung enantiomerenreiner Biarylketocarbonsäuren |
US5932763A (en) * | 1997-05-15 | 1999-08-03 | Bayer Corporation | Inhibition of matrix metalloproteases by 2-(ω-arolalkyl)-4-biaryl-4-oxobutyric acids |
US6300514B1 (en) | 1997-06-25 | 2001-10-09 | Ono Pharmaceutical Co., Ltd. | Aryl (sulfide, sulfoxide and sulfone) derivatives and drugs containing the same as the active ingredient |
US5883131A (en) * | 1997-07-09 | 1999-03-16 | Pfizer Inc. | Cyclic sulfone derivatives |
US6399612B1 (en) | 1997-10-06 | 2002-06-04 | Warner-Lambert Company | Heteroaryl butyric acids and their derivatives as inhibitors of matrix metalloproteinases |
BR9813480A (pt) * | 1997-12-17 | 2000-10-10 | Biocryst Pharm Inc | Compostos inibidores de neuraminidase de ciclopentano substituìdo, composição e métodos de inibição da neuraminidase do vìrus da influenza- e de tratamento de infecção por vìrus da influenza- |
US6288063B1 (en) * | 1998-05-27 | 2001-09-11 | Bayer Corporation | Substituted 4-biarylbutyric and 5-biarylpentanoic acid derivatives as matrix metalloprotease inhibitors |
FR2780402B1 (fr) * | 1998-06-30 | 2001-04-27 | Adir | Nouveaux composes acides carboxyliques et hydroxamiques inhibiteurs de metalloproteases, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
DE19835359A1 (de) * | 1998-08-05 | 2000-02-10 | Clariant Gmbh | Verfahren zur Herstellung von 4-(4'-Chlorbiphenyl-4-yl)-4-keto-2-methylenbuttersäure |
DE19850695A1 (de) * | 1998-11-04 | 2000-05-11 | Bayer Ag | Verfahren zur technischen Herstellung von 4'-Chlor-alpha-methylen-gamma-oxo-(1.1'-biphenyl)-4'-butansäure |
US6503745B1 (en) | 1998-11-05 | 2003-01-07 | Biocryst Pharmaceuticals, Inc. | Cyclopentane and cyclopentene compounds and use for detecting influenza virus |
US6288261B1 (en) | 1998-12-18 | 2001-09-11 | Abbott Laboratories | Inhibitors of matrix metalloproteinases |
US6858598B1 (en) | 1998-12-23 | 2005-02-22 | G. D. Searle & Co. | Method of using a matrix metalloproteinase inhibitor and one or more antineoplastic agents as a combination therapy in the treatment of neoplasia |
EP1140768A1 (en) * | 1998-12-30 | 2001-10-10 | Bayer Aktiengesellschaft | Use of substituted 4-biarylbutyric and 5-biarylpentanoic acid derivatives as matrix metalloprotease inhibitors for the treatment of respiratory diseases |
EP1031349A1 (en) * | 1999-02-25 | 2000-08-30 | Bayer Aktiengesellschaft | Use of substituted 4-biarylbutyric and 5-biarylpentanoic acid derivatives for the treatment of cerebral diseases |
US6541521B1 (en) | 1999-07-12 | 2003-04-01 | Warner-Lambert Company | Benzene butyric acids and their derivatives as inhibitors of matrix metalloproteinases |
GB9922710D0 (en) * | 1999-09-24 | 1999-11-24 | Bayer Ag | Use of substituted 4-biarylbutyric and 5-biarylpentanoic acid derivatatives for the treatment of multiple sclerosis |
CO5210860A1 (es) | 1999-10-01 | 2002-10-30 | Hoffmann La Roche | Nuevos derivados de pirimidina-2,4,6-triona |
GB9924057D0 (en) * | 1999-10-11 | 1999-12-15 | Novartis Ag | Organic compounds |
CA2401728A1 (en) * | 2000-03-21 | 2001-09-27 | The Procter & Gamble Company | Difluorobutyric acid metalloprotease inhibitors |
KR100405913B1 (ko) * | 2000-04-25 | 2003-11-14 | 삼성전자주식회사 | 메트릭스 메탈로프로테이나제의 저해제로서의 비페닐부티릭산 유도체 |
KR100405914B1 (ko) * | 2000-04-25 | 2003-11-15 | 삼성전자주식회사 | 메트릭스 메탈로프로테이나제의 저해제로서의 비페닐부티릭산 유도체 |
US6545029B2 (en) * | 2000-06-12 | 2003-04-08 | Bayer Aktiengesellschaft | Phenylserine derivatives as integrin antagonists |
US6376524B1 (en) | 2000-06-21 | 2002-04-23 | Sunesis Pharmaceuticals, Inc. | Triphenyl compounds as interleukin-4 antagonists |
KR100347765B1 (ko) | 2000-10-18 | 2002-08-09 | 삼성전자 주식회사 | 웨이퍼의 전기적 특성을 검사하는 방법 및 장치 |
JP4361273B2 (ja) * | 2001-02-27 | 2009-11-11 | アメリカ合衆国 | 潜在的な血管形成阻害剤としてのサリドマイド類似体 |
US6716845B2 (en) | 2001-03-30 | 2004-04-06 | Hoffmann-La Roche Inc. | Barbituric acid derivatives |
JP4660024B2 (ja) * | 2001-06-26 | 2011-03-30 | 帝人株式会社 | Mmp活性低下装置及び方法 |
WO2003010135A1 (fr) * | 2001-07-26 | 2003-02-06 | Ajinomoto Co., Inc. | Nouveaux derives de l'acide phenylpropionique |
KR100432283B1 (ko) * | 2001-10-27 | 2004-05-22 | 한국과학기술연구원 | 무스카린성 아세틸콜린 수용체에 작용하는테트라하이드로피리딘 유도체 |
FR2832925B1 (fr) * | 2001-12-03 | 2006-07-14 | Lipha | Utilisation de derives de l'acide 4-oxobutanoique dans le traitement de l'inflammation |
CN1732023A (zh) * | 2002-12-27 | 2006-02-08 | 血管技术国际股份公司 | 组合物和使用collajolie的方法 |
WO2004060346A2 (en) | 2002-12-30 | 2004-07-22 | Angiotech International Ag | Drug delivery from rapid gelling polymer composition |
KR20060006953A (ko) * | 2003-04-30 | 2006-01-20 | 디 인스티튜트스 포 파마슈티컬 디스커버리, 엘엘씨 | 치환된 카르복실산 |
WO2004098582A2 (en) * | 2003-05-07 | 2004-11-18 | The University Court Of The University Of Aberdeen | Ketones and reduced ketones as therapeutic agents for the treatment of bone conditions |
AR044152A1 (es) * | 2003-05-09 | 2005-08-24 | Bayer Corp | Derivados de alquilarilo, metodo de preparacion y uso para el tratamiento de la obesidad |
WO2005016326A2 (en) * | 2003-07-11 | 2005-02-24 | The Government Of The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services | Analogs of thalidomide as potential angiogenesis inhibitors |
US7320992B2 (en) * | 2003-08-25 | 2008-01-22 | Amgen Inc. | Substituted 2,3-dihydro-1h-isoindol-1-one derivatives and methods of use |
CN1867331B (zh) * | 2003-09-17 | 2010-05-26 | 美国政府健康及人类服务部 | 作为TNF-α调节剂的沙利度胺类似物 |
US8952895B2 (en) | 2011-06-03 | 2015-02-10 | Apple Inc. | Motion-based device operations |
DE10351448A1 (de) | 2003-11-04 | 2005-06-09 | Bayer Healthcare Ag | Geschmackstoffhaltige Arzneimittelformulierungen mit verbesserten pharmazeutischen Eigenschaften |
CA2561530C (en) | 2004-03-31 | 2014-04-22 | Kazuwa Nakao | Therapeutic or prophylactic agent for arthritis |
BRPI0512988A (pt) * | 2004-07-08 | 2008-04-22 | Novo Nordisk As | método para aumentar a meia-vida plasmática de uma molécula, composto, uso do mesmo, e, composição farmacêutica |
GB0419850D0 (en) * | 2004-09-07 | 2004-10-13 | Angeletti P Ist Richerche Bio | Therapeutic agents |
EA013539B1 (ru) | 2005-02-22 | 2010-06-30 | Рэнбакси Лабораториз Лимитед | Производные 5-фенилпентановой кислоты в качестве ингибиторов матричной металлопротеиназы для лечения астмы и других заболеваний |
MX2007013049A (es) * | 2005-04-19 | 2008-01-11 | Bayer Pharmaceuticals Corp | Preparacion y uso de derivados de aril alquil acido para el tratamiento de la obesidad. |
JP2009501236A (ja) | 2005-07-14 | 2009-01-15 | タケダ サン ディエゴ インコーポレイテッド | ヒストンデアセチラーゼ阻害剤 |
US20090118519A1 (en) * | 2006-04-17 | 2009-05-07 | Sumitomo Chemical Company, Limited | Production Method of Polycyclic Lactams |
JP5338035B2 (ja) * | 2006-04-17 | 2013-11-13 | 住友化学株式会社 | 多環式ラクタム類の製造方法 |
SI2074093T1 (sl) | 2006-08-22 | 2012-12-31 | Ranbaxy Laboratories Limited | Postopek za pridobitev inhibitorjev matrične metalproteinaze in kiralni pomožnik zanj |
EP2080758A3 (de) | 2007-11-29 | 2009-08-26 | Bayer CropScience AG | Halogen substituierte delta-1-Pyrroline |
WO2009080722A2 (en) * | 2007-12-21 | 2009-07-02 | Crystax Pharmaceuticals, S.L. | Carboxylic derivatives for use in the treatment of cancer |
WO2010070076A1 (en) * | 2008-12-19 | 2010-06-24 | Crystax Pharmaceuticals, S.L. | Alkanoic acid derivatives and their therapeutic use as hdac inhibitors |
JP5580544B2 (ja) * | 2009-03-25 | 2014-08-27 | 国立大学法人群馬大学 | がん治療用の遊走阻害剤 |
DE202010018378U1 (de) | 2009-04-10 | 2016-04-07 | Tufts Medical Center, Inc. | PAR-1-Aktivierung durch Metalloproteinase-1 (MMP-1) |
KR101512548B1 (ko) | 2010-03-12 | 2015-04-15 | 오메로스 코포레이션 | Pde10 억제제 및 관련 조성물 및 방법 |
HU1000676D0 (en) | 2010-12-17 | 2011-02-28 | Pharmahungary 2000 Kft | Inhibitors of matrix metalloproteinase, pharmaceutical compositions thereof and use of them for preventing and treating diseases where the activation of mmp is involved |
US10941109B2 (en) * | 2011-06-13 | 2021-03-09 | Ergon Pharmaceuticals Llc | Compositions and methods of treatment using a BCAT1 inhibitor |
US8927725B2 (en) | 2011-12-02 | 2015-01-06 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Thio compounds |
PT2800738T (pt) | 2012-01-06 | 2020-06-23 | Novartis Ag | Compostos heterocíclicos e métodos para a utilização dos mesmos |
CN105164100B (zh) | 2013-03-14 | 2017-09-15 | 维斯塔津治疗公司 | 用于合成手性犬尿氨酸化合物的方法 |
CN106458938A (zh) | 2014-04-03 | 2017-02-22 | 拜耳制药股份公司 | 手性2,5‑二取代的环戊烷甲酸衍生物及其用途 |
EP3126339A1 (de) | 2014-04-03 | 2017-02-08 | Bayer Pharma Aktiengesellschaft | 2,5-disubstituierte cyclopentancarbonsäuren und ihre verwendung |
CN106661008A (zh) | 2014-04-03 | 2017-05-10 | 拜耳制药股份公司 | 用于治疗呼吸道疾病的2,5‑二取代的环戊烷甲酸 |
NZ630810A (en) | 2014-04-28 | 2016-03-31 | Omeros Corp | Processes and intermediates for the preparation of a pde10 inhibitor |
NZ716462A (en) | 2014-04-28 | 2017-11-24 | Omeros Corp | Optically active pde10 inhibitor |
CN104230923A (zh) * | 2014-07-05 | 2014-12-24 | 湖南华腾制药有限公司 | 制备2,3-二氢-1h-吡咯并吡啶盐酸盐的方法 |
PL3245198T3 (pl) | 2015-01-13 | 2020-10-05 | Novartis Ag | Pochodne pirolidyny jako antagonisty angiotensyny ii typu 2 |
CN104649882A (zh) * | 2015-02-11 | 2015-05-27 | 南通恒盛精细化工有限公司 | 一种磷酸二酯酶抑制剂的中间体制备工艺 |
JP2018513153A (ja) | 2015-04-24 | 2018-05-24 | オメロス コーポレーション | Pde10インヒビターならびに関連する組成物および方法 |
WO2017079678A1 (en) | 2015-11-04 | 2017-05-11 | Omeros Corporation | Solid state forms of a pde10 inhibitor |
US10435423B2 (en) | 2016-08-17 | 2019-10-08 | The Board Of Regents Of The Nevada System Of Higher Education On Behalf Of The University Of Nevada, Las Vegas | Functionalized phosphonates via Michael addition |
JP7256509B2 (ja) * | 2016-08-22 | 2023-04-12 | エルゴン ファーマシューティカルズ エルエルシー | Bcat1阻害剤を使用する組成物及び治療方法 |
Family Cites Families (53)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3182061A (en) * | 1961-03-20 | 1965-05-04 | Warner Lambert Pharmaceutical | 5-[4-(p-hydroxyphenoxy)phenyl]-5-oxo-3-methylvaleric acid |
FR5035M (cs) * | 1964-07-28 | 1967-05-02 | ||
US3624142A (en) * | 1964-09-10 | 1971-11-30 | Merck & Co Inc | Substituted biphenyl acetic acid derivatives |
GB1121722A (en) * | 1966-03-31 | 1968-07-31 | Ici Ltd | New carboxylic acid derivatives |
US3707549A (en) * | 1967-12-05 | 1972-12-26 | Lilly Co Eli | Alpha-substituted hydrocinnamic acids and derivatives thereof |
US3754021A (en) * | 1968-05-29 | 1973-08-21 | Merck & Co Inc | 4-keto-4-(3-chloro-4'-cyclohexyl)phenylbutyric acid and related compounds |
US3876800A (en) * | 1969-05-12 | 1975-04-08 | Clin Midy | Pharmaceutical compositions and methods for treating inflammation and pain |
FR2104632A1 (en) * | 1969-09-03 | 1972-04-21 | Aries Robert | Salicyloyloxy substd aralkanoic acids - analgesics, anticonvulsants antiinflammatories antipyretics, antirheumatics |
US3917846A (en) * | 1970-05-05 | 1975-11-04 | William H Roher Inc | Phenylacetic acids in reducing pain, fever and inflammation |
US3867434A (en) * | 1971-11-04 | 1975-02-18 | Rorer Inc William H | Phenyl butyric acids and derivatives thereof |
US3784701A (en) * | 1970-09-21 | 1974-01-08 | American Cyanamid Co | Compositions containing substituted benzoylpropionic acids and method of use to treat inflammation and pain |
US3997589A (en) * | 1971-03-17 | 1976-12-14 | Boehringer Ingelheim Gmbh | 4-(2'-Fluoro-4-biphenylylr-4-oxo-butyric acid and esters and salts thereof |
US4021479A (en) * | 1971-03-17 | 1977-05-03 | Boehringer Ingelheim Gmbh | Derivatives of 4-(4-biphenylyl)-butyric acid |
US3749750A (en) * | 1971-06-25 | 1973-07-31 | American Home Prod | Alkyl esters of substituted phenylsulfonyl alkanoic acids |
BE787782A (fr) * | 1971-08-20 | 1973-02-19 | Thomae Gmbh Dr K | Nouveaux 4-(4-biphenylyl)-butyramides |
CS187460B2 (en) * | 1974-03-01 | 1979-01-31 | Merck Patent Gmbh | Process for preparing new derivatives of phenylbutanole |
US3962228A (en) * | 1974-03-18 | 1976-06-08 | American Home Products Corporation | 3-benzoylpropionamido cephalosporanic derivatives |
GB1498903A (en) * | 1974-03-25 | 1978-01-25 | Fabre Sa Pierre | Aromatic keto-acids and their derivatives |
FR2300551A2 (fr) * | 1975-02-17 | 1976-09-10 | Fabre Sa Pierre | Nouveaux |
AT336589B (de) * | 1974-05-20 | 1977-05-10 | Thomae Gmbh Dr K | Verfahren zur herstellung von neuen biphenylderivaten |
US4151302A (en) * | 1975-06-28 | 1979-04-24 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Araliphatic dihalogen compounds composition and method of use |
US4168385A (en) * | 1975-09-25 | 1979-09-18 | American Cyanamid Company | Hypolipemic phenylacetic acid derivatives |
FR2378741A1 (fr) * | 1977-02-01 | 1978-08-25 | Fabre Sa Pierre | Acides garyl goxo isovaleriques doues de proprietes antiphlogistiques et antalgiques |
EP0009306B1 (en) * | 1978-09-08 | 1982-11-24 | Imperial Chemical Industries Plc | Anti-arthritic hydroxyacetic acid derivatives, pharmaceutical compositions thereof, and processes for their manufacture |
DE2854475A1 (de) * | 1978-12-16 | 1980-07-03 | Basf Ag | Neue 3,4-diaza-bicyclo eckige klammer auf 4.1.0 eckige klammer zu hepten-(2)- one-(5), verfahren zu ihrer herstellung und diese verbindungen enthaltende therapeutische mittel |
US4247466A (en) * | 1979-07-05 | 1981-01-27 | American Cyanamid Company | Lactone metabolites of 3-(4-biphenylylcarbonyl)propionic acid |
US4219668A (en) * | 1979-07-05 | 1980-08-26 | American Cyanamid Company | 4-Hydroxy,4-biphenylbutyric acid |
US4271191A (en) * | 1979-12-19 | 1981-06-02 | Pierre Fabre S.A. | Method of treating hyperuricemia and gout |
FR2503140A1 (fr) * | 1981-03-31 | 1982-10-08 | Fabre Sa Pierre | Acides biphenyl-4 oxo-4 methylene-3 butyriques, leur procede de preparation et leur utilisation comme medicaments |
US4577025A (en) * | 1981-12-21 | 1986-03-18 | Nissan Chemical Industries, Ltd. | Method of preparing α-aromatic propionic acids and intermediates thereof |
JPS58150563A (ja) * | 1982-03-04 | 1983-09-07 | Taisho Pharmaceut Co Ltd | 3−ベンゾイル−2−メルカプトプロピオン酸誘導体 |
JPS6054356A (ja) * | 1983-09-03 | 1985-03-28 | Taisho Pharmaceut Co Ltd | 3−ベンゾイル−2−メルカプトプロピオン酸誘導体 |
JPS60209539A (ja) * | 1984-04-04 | 1985-10-22 | Hitachi Ltd | ネマチツク液晶化合物並びに液晶組成物 |
CS243570B1 (en) * | 1984-08-31 | 1986-06-12 | Miroslav Kuchar | Omega-aryloxoalkane acids |
JPS61200964A (ja) * | 1985-02-28 | 1986-09-05 | Taisho Pharmaceut Co Ltd | 3−ベンゾイル−3−メルカプトプロピオン酸誘導体 |
JPS61200963A (ja) * | 1985-02-28 | 1986-09-05 | Taisho Pharmaceut Co Ltd | ジフエニルスルフイド誘導体 |
DE3525284A1 (de) * | 1985-07-16 | 1987-01-29 | Boehringer Mannheim Gmbh | Neue carbonsaeurederivate, verfahren zu ihrer herstellung, ihre verwendung sowie arzneimittel, die diese verbindungen enthalten |
JPH0228579B2 (ja) * | 1985-12-03 | 1990-06-25 | Taisho Pharma Co Ltd | Menekikinofuzenchiryozai |
JPS6388168A (ja) * | 1986-10-01 | 1988-04-19 | Taisho Pharmaceut Co Ltd | 3−ベンゾイルプロピオン酸誘導体 |
DE3774858D1 (de) * | 1986-12-24 | 1992-01-09 | Beecham Group Plc | Derivate von n-(2-alkyl-3-mercaptoglutaryl)-alpha-aminosaeuren und deren verwendung als collagenase-inhibitoren. |
US5098613A (en) * | 1987-01-12 | 1992-03-24 | Eli Lilly And Company | Anti-inflammatory agents |
DE3700732A1 (de) * | 1987-01-13 | 1988-07-21 | Boehringer Mannheim Gmbh | Neue carbonsaeurederivate, verfahren zu ihrer herstellung sowie arzneimittel, die diese verbindungen enthalten |
GB8814813D0 (en) * | 1988-06-22 | 1988-07-27 | Beecham Group Plc | Novel compounds |
CS276833B6 (en) * | 1990-06-18 | 1992-08-12 | Vyzk Ustav Farm Biochem Sp | Functional derivatives of 4-(2,4-difluorobiphenylyl)-2-methyl -4- oxobutanoic acid |
JP2602575B2 (ja) * | 1990-07-06 | 1997-04-23 | シャープ株式会社 | 不揮発性半導体記憶装置 |
JPH0488682A (ja) * | 1990-08-01 | 1992-03-23 | Fujitsu Ltd | 半導体装置の製造方法 |
JPH04128262A (ja) * | 1990-09-18 | 1992-04-28 | Taisho Pharmaceut Co Ltd | 3―ベンゾイルプロピオン酸誘導体 |
JP3031701B2 (ja) * | 1990-11-27 | 2000-04-10 | チッソ株式会社 | ラクトン化合物および組成物 |
FR2679564A1 (fr) * | 1991-07-23 | 1993-01-29 | Inst Nat Sante Rech Med | Nouveaux acylmercaptoalcanoldipeptides, leur preparation et les compositions qui les contiennent. |
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 |
PH30449A (en) * | 1991-11-25 | 1997-05-28 | Lilly Co Eli | Substituted phenyl phenol leukotriene antagonists |
WO1993020047A1 (en) * | 1992-04-07 | 1993-10-14 | British Bio-Technology Limited | Hydroxamic acid based collagenase and cytokine inhibitors |
JPH06234754A (ja) * | 1993-02-10 | 1994-08-23 | Dai Ichi Seiyaku Co Ltd | 複素環式カルボン酸誘導体 |
-
1995
- 1995-11-06 US US08/539,409 patent/US5789434A/en not_active Expired - Lifetime
- 1995-11-09 KR KR1019970703273A patent/KR100412971B1/ko not_active IP Right Cessation
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- 1995-11-09 AT AT95940572T patent/ATE222230T1/de not_active IP Right Cessation
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- 1995-11-09 NZ NZ297174A patent/NZ297174A/en not_active IP Right Cessation
- 1995-11-09 PL PL95320285A patent/PL183549B1/pl not_active IP Right Cessation
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- 1995-11-09 WO PCT/US1995/014002 patent/WO1996015096A1/en not_active Application Discontinuation
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- 1995-11-09 BR BR9509686A patent/BR9509686A/pt not_active IP Right Cessation
- 1995-11-09 JP JP8516097A patent/JPH10509146A/ja not_active Ceased
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- 1995-11-09 ES ES95940572T patent/ES2181803T3/es not_active Expired - Lifetime
- 1995-11-13 DZ DZ950125A patent/DZ1943A1/fr active
- 1995-11-14 YU YU71295A patent/YU71295A/sh unknown
- 1995-11-14 MY MYPI95003457A patent/MY114686A/en unknown
- 1995-11-14 MA MA24066A patent/MA26357A1/fr unknown
- 1995-11-14 ZA ZA9509647A patent/ZA959647B/xx unknown
- 1995-11-14 SV SV1995000074A patent/SV1995000074A/es not_active Application Discontinuation
- 1995-11-15 TN TNTNSN95117A patent/TNSN95117A1/fr unknown
- 1995-11-15 CO CO95053945A patent/CO4650182A1/es unknown
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- 1997-05-12 IS IS4480A patent/IS4480A/is unknown
- 1997-05-13 BG BG101482A patent/BG62805B1/bg unknown
- 1997-05-14 NO NO972220A patent/NO309523B1/no not_active IP Right Cessation
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