UA72789C2 - Heterocyclic amide derivatives - Google Patents
Heterocyclic amide derivatives Download PDFInfo
- Publication number
- UA72789C2 UA72789C2 UA2002086471A UA2002086471A UA72789C2 UA 72789 C2 UA72789 C2 UA 72789C2 UA 2002086471 A UA2002086471 A UA 2002086471A UA 2002086471 A UA2002086471 A UA 2002086471A UA 72789 C2 UA72789 C2 UA 72789C2
- Authority
- UA
- Ukraine
- Prior art keywords
- alkyl
- optionally substituted
- hydroxy
- compound according
- differs
- Prior art date
Links
- -1 Heterocyclic amide Chemical class 0.000 title claims description 127
- 150000001875 compounds Chemical class 0.000 claims abstract description 181
- 150000003839 salts Chemical class 0.000 claims abstract description 41
- 206010061218 Inflammation Diseases 0.000 claims abstract description 13
- 230000004054 inflammatory process Effects 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 710
- UPUZGXILYFKSGE-UHFFFAOYSA-N quinoxaline-2-carboxylic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CN=C21 UPUZGXILYFKSGE-UHFFFAOYSA-N 0.000 claims description 64
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 57
- 125000001153 fluoro group Chemical group F* 0.000 claims description 51
- 229910002514 Co–Co Inorganic materials 0.000 claims description 48
- 125000003282 alkyl amino group Chemical group 0.000 claims description 43
- 238000011282 treatment Methods 0.000 claims description 41
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 37
- 125000001072 heteroaryl group Chemical group 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 34
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 30
- 150000002431 hydrogen Chemical class 0.000 claims description 29
- 230000002265 prevention Effects 0.000 claims description 29
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 26
- 229910052805 deuterium Inorganic materials 0.000 claims description 26
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 25
- 229910052736 halogen Inorganic materials 0.000 claims description 24
- 150000002367 halogens Chemical class 0.000 claims description 24
- 201000010099 disease Diseases 0.000 claims description 23
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 23
- 125000001424 substituent group Chemical group 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 241000124008 Mammalia Species 0.000 claims description 17
- 150000001408 amides Chemical class 0.000 claims description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- 125000001624 naphthyl group Chemical group 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 206010027654 Allergic conditions Diseases 0.000 claims description 9
- 201000001320 Atherosclerosis Diseases 0.000 claims description 9
- 208000023275 Autoimmune disease Diseases 0.000 claims description 9
- 206010006458 Bronchitis chronic Diseases 0.000 claims description 9
- 208000031886 HIV Infections Diseases 0.000 claims description 9
- 208000037357 HIV infectious disease Diseases 0.000 claims description 9
- 230000003042 antagnostic effect Effects 0.000 claims description 9
- 206010006451 bronchitis Diseases 0.000 claims description 9
- 208000007451 chronic bronchitis Diseases 0.000 claims description 9
- 239000003937 drug carrier Substances 0.000 claims description 9
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims description 9
- 208000015181 infectious disease Diseases 0.000 claims description 9
- 238000002689 xenotransplantation Methods 0.000 claims description 9
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 8
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 208000037803 restenosis Diseases 0.000 claims description 8
- 208000036142 Viral infection Diseases 0.000 claims description 7
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Substances [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 7
- 230000009385 viral infection Effects 0.000 claims description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 125000005605 benzo group Chemical group 0.000 claims description 6
- 125000002837 carbocyclic group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 235000007715 potassium iodide Nutrition 0.000 claims description 6
- 125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 claims description 6
- 125000005916 2-methylpentyl group Chemical group 0.000 claims description 5
- 150000001721 carbon Chemical group 0.000 claims description 5
- 125000001041 indolyl group Chemical group 0.000 claims description 5
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000004549 quinolin-4-yl group Chemical group N1=CC=C(C2=CC=CC=C12)* 0.000 claims description 5
- 125000004262 quinoxalin-2-yl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N=C1* 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
- 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000006413 ring segment Chemical group 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 101000794228 Homo sapiens Mitotic checkpoint serine/threonine-protein kinase BUB1 beta Proteins 0.000 claims description 3
- 102100030144 Mitotic checkpoint serine/threonine-protein kinase BUB1 beta Human genes 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 3
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- CGJMVNVWQHPASW-UHFFFAOYSA-N quinoxaline-2-carboxamide Chemical compound C1=CC=CC2=NC(C(=O)N)=CN=C21 CGJMVNVWQHPASW-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 25
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 4
- 208000038016 acute inflammation Diseases 0.000 claims 3
- 230000006022 acute inflammation Effects 0.000 claims 3
- 208000037976 chronic inflammation Diseases 0.000 claims 3
- 230000006020 chronic inflammation Effects 0.000 claims 3
- 125000006713 (C5-C10) cycloalkyl group Chemical group 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims 2
- 125000004552 isoquinolin-4-yl group Chemical group C1=NC=C(C2=CC=CC=C12)* 0.000 claims 2
- 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 claims 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims 1
- 125000004254 isoquinolin-1-yl group Chemical group [H]C1=C([H])C2=C([H])C([H])=C([H])C([H])=C2C(*)=N1 0.000 claims 1
- 108091028606 miR-1 stem-loop Proteins 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- 208000026278 immune system disease Diseases 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 description 61
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
- 239000000243 solution Substances 0.000 description 49
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 239000011541 reaction mixture Substances 0.000 description 31
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
- 239000000203 mixture Substances 0.000 description 29
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
- 239000000741 silica gel Substances 0.000 description 22
- 229910002027 silica gel Inorganic materials 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 238000004587 chromatography analysis Methods 0.000 description 20
- 239000002253 acid Substances 0.000 description 19
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 18
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
- 210000004027 cell Anatomy 0.000 description 16
- 229920006395 saturated elastomer Polymers 0.000 description 15
- 239000012044 organic layer Substances 0.000 description 13
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 12
- 239000002585 base Substances 0.000 description 12
- 108020003175 receptors Proteins 0.000 description 12
- 102000005962 receptors Human genes 0.000 description 12
- 229910052938 sodium sulfate Inorganic materials 0.000 description 12
- 235000011152 sodium sulphate Nutrition 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 9
- 230000001684 chronic effect Effects 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 206010039073 rheumatoid arthritis Diseases 0.000 description 9
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 8
- 230000001154 acute effect Effects 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 8
- 239000011780 sodium chloride Substances 0.000 description 8
- 210000001519 tissue Anatomy 0.000 description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- 208000011580 syndromic disease Diseases 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
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- 206010018364 Glomerulonephritis Diseases 0.000 description 6
- 206010018691 Granuloma Diseases 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 208000032571 Infant acute respiratory distress syndrome Diseases 0.000 description 6
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 6
- 206010024229 Leprosy Diseases 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- 206010028974 Neonatal respiratory distress syndrome Diseases 0.000 description 6
- 208000003435 Optic Neuritis Diseases 0.000 description 6
- 201000004681 Psoriasis Diseases 0.000 description 6
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
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- 238000000605 extraction Methods 0.000 description 5
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical class CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 5
- 208000037906 ischaemic injury Diseases 0.000 description 5
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 235000011181 potassium carbonates Nutrition 0.000 description 5
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- 239000000725 suspension Substances 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
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- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
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- VHHHONWQHHHLTI-UHFFFAOYSA-N hexachloroethane Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)Cl VHHHONWQHHHLTI-UHFFFAOYSA-N 0.000 description 4
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- 238000002360 preparation method Methods 0.000 description 4
- 239000003586 protic polar solvent Substances 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
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- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 239000005557 antagonist Substances 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 3
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 150000002168 ethanoic acid esters Chemical class 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
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- SRLIJFQVJAPOAD-UHFFFAOYSA-N n-[8-fluoro-3-hydroxy-8-methyl-5-(1,3-oxazol-2-yl)-1-phenylnonan-2-yl]quinoxaline-2-carboxamide Chemical group N=1C=COC=1C(CCC(C)(F)C)CC(O)C(NC(=O)C=1N=C2C=CC=CC2=NC=1)CC1=CC=CC=C1 SRLIJFQVJAPOAD-UHFFFAOYSA-N 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 230000010410 reperfusion Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pulmonology (AREA)
- Virology (AREA)
- Urology & Nephrology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Vascular Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Transplantation (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Ophthalmology & Optometry (AREA)
- AIDS & HIV (AREA)
- Hospice & Palliative Care (AREA)
- Molecular Biology (AREA)
- Cardiology (AREA)
- Psychiatry (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18015900P | 2000-02-04 | 2000-02-04 | |
| PCT/IB2001/000107 WO2001057023A1 (en) | 2000-02-04 | 2001-01-26 | Heterocyclic amide derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA72789C2 true UA72789C2 (en) | 2005-04-15 |
Family
ID=22659425
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA2002086471A UA72789C2 (en) | 2000-02-04 | 2001-01-26 | Heterocyclic amide derivatives |
Country Status (37)
| Country | Link |
|---|---|
| US (2) | US6548671B2 (zh) |
| EP (1) | EP1252154A1 (zh) |
| JP (1) | JP2003522164A (zh) |
| KR (2) | KR20020072304A (zh) |
| CN (1) | CN1398265A (zh) |
| AP (1) | AP2002002595A0 (zh) |
| AR (1) | AR027349A1 (zh) |
| AU (1) | AU2699701A (zh) |
| BG (1) | BG106922A (zh) |
| BR (1) | BR0108002A (zh) |
| CA (1) | CA2399214A1 (zh) |
| CZ (1) | CZ20022542A3 (zh) |
| EA (2) | EA200401099A1 (zh) |
| EE (1) | EE200200432A (zh) |
| GE (1) | GEP20043301B (zh) |
| GT (1) | GT200100021A (zh) |
| HK (1) | HK1050006A1 (zh) |
| HN (1) | HN2001000021A (zh) |
| HR (1) | HRP20020638A2 (zh) |
| HU (1) | HUP0204560A3 (zh) |
| IL (1) | IL150862A0 (zh) |
| IS (1) | IS6468A (zh) |
| MA (1) | MA25653A1 (zh) |
| NO (1) | NO20023675L (zh) |
| NZ (1) | NZ520075A (zh) |
| OA (1) | OA12174A (zh) |
| PA (1) | PA8511401A1 (zh) |
| PE (1) | PE20011057A1 (zh) |
| PL (1) | PL357094A1 (zh) |
| SK (1) | SK10882002A3 (zh) |
| SV (1) | SV2002000302A (zh) |
| TN (1) | TNSN01021A1 (zh) |
| TW (1) | TW200804311A (zh) |
| UA (1) | UA72789C2 (zh) |
| UY (1) | UY26568A1 (zh) |
| WO (1) | WO2001057023A1 (zh) |
| ZA (1) | ZA200206140B (zh) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1448538A1 (en) | 2001-11-15 | 2004-08-25 | Eli Lilly And Company | Peroxisome proliferator activated receptor alpha agonists |
| SE0201980D0 (sv) * | 2002-06-24 | 2002-06-24 | Astrazeneca Ab | Novel compounds |
| US20040087571A1 (en) * | 2002-10-30 | 2004-05-06 | Pfizer Inc | Methods of using CCR1 antagonists as immunomodulatory agents |
| US20040097554A1 (en) * | 2002-10-30 | 2004-05-20 | Pfizer Inc | Heteroaryl-hexanoic acid amide derivatives as immonomodulatory agents |
| CN101365700A (zh) | 2005-11-15 | 2009-02-11 | 沃泰克斯药物股份有限公司 | 可用作激酶抑制剂的氮杂吲唑 |
| CN1971279B (zh) * | 2006-12-06 | 2011-05-18 | 华中农业大学 | 喹噁啉-2-羧酸残留的酶联免疫检测方法及试剂盒 |
| KR102285817B1 (ko) | 2017-03-13 | 2021-08-05 | 라퀄리아 파마 인코포레이티드 | P2x7 수용체 길항제로서 테트라히드로퀴놀린 유도체 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL88619A0 (en) * | 1987-12-15 | 1989-07-31 | Pfizer | Non-peptidic renin inhibitors |
| EP0374098A3 (de) * | 1988-12-15 | 1991-05-02 | Ciba-Geigy Ag | Retrovirale Proteasehemmer |
| JPH06510766A (ja) | 1991-09-11 | 1994-12-01 | スミスクライン・ビーチャム・コーポレイション | Ｈ．ｉ．ｖ．阻害剤としてのヘテロ環含有ペプチド同配体 |
| JPH07504417A (ja) * | 1992-02-26 | 1995-05-18 | スミスクライン・ビーチャム・コーポレイション | レトロウイルスプロテアーゼ拮抗薬 |
| PT708085E (pt) * | 1994-10-19 | 2002-11-29 | Novartis Ag | Eteres antivirais de isosteros de substrato de aspartato protease |
| CN1248968A (zh) * | 1997-02-26 | 2000-03-29 | 辉瑞大药厂 | 杂芳基－己酸酰胺衍生物、其制备方法及其作为MIP－1α与其CCRI受体结合的选择性抑制剂的用途 |
| KR100385529B1 (ko) * | 1998-02-05 | 2003-05-27 | 화이자 프로덕츠 인코포레이티드 | 신규 디하이드록시헥산산 유도체 |
-
2001
- 2001-01-26 NZ NZ520075A patent/NZ520075A/en unknown
- 2001-01-26 OA OA1200200235A patent/OA12174A/en unknown
- 2001-01-26 WO PCT/IB2001/000107 patent/WO2001057023A1/en not_active Application Discontinuation
- 2001-01-26 BR BR0108002-4A patent/BR0108002A/pt not_active IP Right Cessation
- 2001-01-26 GE GE4875A patent/GEP20043301B/en unknown
- 2001-01-26 KR KR1020027010005A patent/KR20020072304A/ko not_active Application Discontinuation
- 2001-01-26 AP APAP/P/2002/002595A patent/AP2002002595A0/en unknown
- 2001-01-26 EA EA200401099A patent/EA200401099A1/ru unknown
- 2001-01-26 EP EP01901328A patent/EP1252154A1/en not_active Withdrawn
- 2001-01-26 EA EA200200749A patent/EA005320B1/ru not_active IP Right Cessation
- 2001-01-26 PL PL01357094A patent/PL357094A1/xx not_active Application Discontinuation
- 2001-01-26 HU HU0204560A patent/HUP0204560A3/hu unknown
- 2001-01-26 CA CA002399214A patent/CA2399214A1/en not_active Abandoned
- 2001-01-26 SK SK1088-2002A patent/SK10882002A3/sk not_active Application Discontinuation
- 2001-01-26 UA UA2002086471A patent/UA72789C2/uk unknown
- 2001-01-26 EE EEP200200432A patent/EE200200432A/xx unknown
- 2001-01-26 IL IL15086201A patent/IL150862A0/xx unknown
- 2001-01-26 KR KR10-2005-7000487A patent/KR20050009776A/ko not_active Application Discontinuation
- 2001-01-26 JP JP2001557855A patent/JP2003522164A/ja not_active Withdrawn
- 2001-01-26 CN CN01804508A patent/CN1398265A/zh active Pending
- 2001-01-26 AU AU26997/01A patent/AU2699701A/en not_active Abandoned
- 2001-01-26 CZ CZ20022542A patent/CZ20022542A3/cs unknown
- 2001-01-30 PE PE2001000102A patent/PE20011057A1/es not_active Application Discontinuation
- 2001-01-30 TW TW093137061A patent/TW200804311A/zh unknown
- 2001-01-31 GT GT200100021A patent/GT200100021A/es unknown
- 2001-01-31 HN HN2001000021A patent/HN2001000021A/es unknown
- 2001-01-31 UY UY26568A patent/UY26568A1/es not_active Application Discontinuation
- 2001-01-31 US US09/774,871 patent/US6548671B2/en not_active Expired - Fee Related
- 2001-02-01 AR ARP010100483A patent/AR027349A1/es unknown
- 2001-02-02 SV SV2001000302A patent/SV2002000302A/es not_active Application Discontinuation
- 2001-02-02 TN TNTNSN01021A patent/TNSN01021A1/fr unknown
- 2001-02-05 PA PA20018511401A patent/PA8511401A1/es unknown
-
2002
- 2002-07-11 IS IS6468A patent/IS6468A/is unknown
- 2002-07-15 BG BG106922A patent/BG106922A/xx unknown
- 2002-07-26 HR HRP20020638 patent/HRP20020638A2/hr not_active Application Discontinuation
- 2002-08-01 MA MA26757A patent/MA25653A1/fr unknown
- 2002-08-01 ZA ZA200206140A patent/ZA200206140B/xx unknown
- 2002-08-02 NO NO20023675A patent/NO20023675L/no not_active Application Discontinuation
-
2003
- 2003-02-06 US US10/360,059 patent/US6689886B2/en not_active Expired - Fee Related
- 2003-03-28 HK HK03102236.7A patent/HK1050006A1/zh unknown
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