UA73107C2 - Derivatives of 6-azaurcyle inhibiting il-5 - Google Patents
Derivatives of 6-azaurcyle inhibiting il-5 Download PDFInfo
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- UA73107C2 UA73107C2 UA2001075132A UA2001075132A UA73107C2 UA 73107 C2 UA73107 C2 UA 73107C2 UA 2001075132 A UA2001075132 A UA 2001075132A UA 2001075132 A UA2001075132 A UA 2001075132A UA 73107 C2 UA73107 C2 UA 73107C2
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- UA
- Ukraine
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- alkyl
- substituted
- necessary
- formula
- independently
- Prior art date
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- 230000002401 inhibitory effect Effects 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 211
- -1 C1-6alkylO Chemical group 0.000 claims abstract description 184
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 58
- 125000003118 aryl group Chemical group 0.000 claims abstract description 44
- 239000000203 mixture Substances 0.000 claims abstract description 42
- 238000000034 method Methods 0.000 claims abstract description 37
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 35
- 150000003839 salts Chemical class 0.000 claims abstract description 30
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 22
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 17
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract description 16
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims abstract description 15
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 7
- 125000003277 amino group Chemical group 0.000 claims abstract description 6
- 239000003814 drug Substances 0.000 claims abstract description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 104
- 125000001424 substituent group Chemical group 0.000 claims description 60
- 229910052739 hydrogen Inorganic materials 0.000 claims description 46
- 239000001257 hydrogen Substances 0.000 claims description 46
- 150000002431 hydrogen Chemical class 0.000 claims description 33
- 125000005843 halogen group Chemical group 0.000 claims description 32
- 125000000335 thiazolyl group Chemical group 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 125000003386 piperidinyl group Chemical group 0.000 claims description 24
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 21
- 125000004076 pyridyl group Chemical group 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 125000002883 imidazolyl group Chemical group 0.000 claims description 19
- 125000002541 furyl group Chemical group 0.000 claims description 18
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 18
- 230000002285 radioactive effect Effects 0.000 claims description 18
- 125000001544 thienyl group Chemical group 0.000 claims description 17
- 125000001425 triazolyl group Chemical group 0.000 claims description 17
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 16
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 15
- 239000012442 inert solvent Substances 0.000 claims description 15
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 15
- 239000002585 base Substances 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 14
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 14
- 125000002971 oxazolyl group Chemical group 0.000 claims description 14
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 13
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 13
- 125000004104 aryloxy group Chemical group 0.000 claims description 12
- 125000002757 morpholinyl group Chemical group 0.000 claims description 12
- 125000004193 piperazinyl group Chemical group 0.000 claims description 12
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 12
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 12
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 125000005968 oxazolinyl group Chemical group 0.000 claims description 11
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 11
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 11
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
- 125000004682 aminothiocarbonyl group Chemical group NC(=S)* 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 10
- 125000005879 dioxolanyl group Chemical group 0.000 claims description 10
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 10
- 125000002636 imidazolinyl group Chemical group 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 125000002755 pyrazolinyl group Chemical group 0.000 claims description 10
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 10
- 125000001422 pyrrolinyl group Chemical group 0.000 claims description 10
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 10
- 125000001166 thiolanyl group Chemical group 0.000 claims description 10
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 10
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 9
- 239000003153 chemical reaction reagent Substances 0.000 claims description 9
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 8
- 231100000252 nontoxic Toxicity 0.000 claims description 8
- 230000003000 nontoxic effect Effects 0.000 claims description 8
- 125000005110 aryl thio group Chemical group 0.000 claims description 7
- 208000006673 asthma Diseases 0.000 claims description 7
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 7
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 125000000532 dioxanyl group Chemical group 0.000 claims description 7
- 125000005883 dithianyl group Chemical group 0.000 claims description 7
- 208000030603 inherited susceptibility to asthma Diseases 0.000 claims description 7
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 7
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 7
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 7
- 125000004306 triazinyl group Chemical group 0.000 claims description 7
- 239000003513 alkali Substances 0.000 claims description 6
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 6
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 6
- 125000005455 trithianyl group Chemical group 0.000 claims description 6
- 238000010306 acid treatment Methods 0.000 claims description 5
- 239000000654 additive Substances 0.000 claims description 5
- 230000000996 additive effect Effects 0.000 claims description 5
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 claims description 5
- 125000005990 isobenzothienyl group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000002393 azetidinyl group Chemical group 0.000 claims description 4
- 239000012620 biological material Substances 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 239000012458 free base Substances 0.000 claims description 4
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 4
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 4
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 4
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 4
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 4
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 4
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 3
- 238000002372 labelling Methods 0.000 claims description 3
- 125000005493 quinolyl group Chemical group 0.000 claims description 3
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 3
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 2
- 238000004891 communication Methods 0.000 claims description 2
- 238000001514 detection method Methods 0.000 claims description 2
- 230000008030 elimination Effects 0.000 claims description 2
- 238000003379 elimination reaction Methods 0.000 claims description 2
- 229910052720 vanadium Inorganic materials 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 18
- 125000001041 indolyl group Chemical group 0.000 claims 3
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000004691 alkyl thio carbonyl group Chemical group 0.000 claims 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims 2
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
- 125000004990 dihydroxyalkyl group Chemical group 0.000 claims 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 8
- 230000008569 process Effects 0.000 abstract description 5
- 229910052717 sulfur Inorganic materials 0.000 abstract description 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 abstract 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 abstract 1
- 150000001204 N-oxides Chemical class 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
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- 239000000543 intermediate Substances 0.000 description 95
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- 239000002904 solvent Substances 0.000 description 43
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 210000003979 eosinophil Anatomy 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 239000012044 organic layer Substances 0.000 description 12
- 239000003480 eluent Substances 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 150000003254 radicals Chemical class 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 150000002576 ketones Chemical class 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
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- 238000004587 chromatography analysis Methods 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
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- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
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- 230000001419 dependent effect Effects 0.000 description 6
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- 241001465754 Metazoa Species 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
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- 150000002367 halogens Chemical class 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 239000008194 pharmaceutical composition Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 102000019034 Chemokines Human genes 0.000 description 4
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- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 4
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
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- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical class C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 3
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- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical class C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 description 2
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- 125000000000 cycloalkoxy group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 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 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
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
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- 230000006378 damage Effects 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 1
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- 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
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- 230000003993 interaction Effects 0.000 description 1
- 229940079322 interferon Drugs 0.000 description 1
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000013507 mapping Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- RPZHFKHTXCZXQV-UHFFFAOYSA-N mercury(I) oxide Inorganic materials O1[Hg][Hg]1 RPZHFKHTXCZXQV-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 210000001616 monocyte Anatomy 0.000 description 1
- 238000010172 mouse model Methods 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007922 nasal spray Substances 0.000 description 1
- 229940097496 nasal spray Drugs 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000001196 nonadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 235000019371 penicillin G benzathine Nutrition 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
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- 150000004965 peroxy acids Chemical class 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
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- 238000002600 positron emission tomography Methods 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 201000009732 pulmonary eosinophilia Diseases 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 238000002603 single-photon emission computed tomography Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 230000003393 splenic effect Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 238000003325 tomography Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- PRXNKYBFWAWBNZ-UHFFFAOYSA-N trimethylphenylammonium tribromide Chemical compound Br[Br-]Br.C[N+](C)(C)C1=CC=CC=C1 PRXNKYBFWAWBNZ-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000001835 viscera Anatomy 0.000 description 1
- 208000002003 vulvitis Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
- C07D253/07—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members with hetero atoms, or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D253/075—Two hetero atoms, in positions 3 and 5
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98204336 | 1998-12-18 | ||
| PCT/EP1999/010169 WO2000037451A1 (en) | 1998-12-18 | 1999-12-16 | Il-5 inhibiting 6-azauracil derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA73107C2 true UA73107C2 (en) | 2005-06-15 |
Family
ID=8234494
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA2001075132A UA73107C2 (en) | 1998-12-18 | 1999-12-16 | Derivatives of 6-azaurcyle inhibiting il-5 |
Country Status (35)
| Country | Link |
|---|---|
| US (1) | US6803364B1 (ru) |
| EP (1) | EP1140873B1 (ru) |
| JP (1) | JP2002533331A (ru) |
| KR (1) | KR100635721B1 (ru) |
| CN (1) | CN100343239C (ru) |
| AR (1) | AR021887A1 (ru) |
| AT (1) | ATE365723T1 (ru) |
| AU (1) | AU773780B2 (ru) |
| BG (1) | BG105602A (ru) |
| BR (1) | BR9916366A (ru) |
| CA (1) | CA2354511A1 (ru) |
| CO (1) | CO5150147A1 (ru) |
| CZ (1) | CZ20012062A3 (ru) |
| DE (1) | DE69936396T2 (ru) |
| DK (1) | DK1140873T3 (ru) |
| EA (1) | EA004806B1 (ru) |
| EE (1) | EE200100320A (ru) |
| ES (1) | ES2289835T3 (ru) |
| HK (1) | HK1042491A1 (ru) |
| HR (1) | HRP20010455A2 (ru) |
| HU (1) | HUP0104641A3 (ru) |
| ID (1) | ID28880A (ru) |
| IL (1) | IL143766A (ru) |
| MY (1) | MY125808A (ru) |
| NO (1) | NO319814B1 (ru) |
| NZ (1) | NZ512748A (ru) |
| PL (1) | PL198205B1 (ru) |
| PT (1) | PT1140873E (ru) |
| SA (1) | SA00201030B1 (ru) |
| SK (1) | SK8152001A3 (ru) |
| TR (1) | TR200101729T2 (ru) |
| TW (1) | TWI249530B (ru) |
| UA (1) | UA73107C2 (ru) |
| WO (1) | WO2000037451A1 (ru) |
| ZA (1) | ZA200104942B (ru) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8466096B2 (en) * | 2007-04-26 | 2013-06-18 | Afton Chemical Corporation | 1,3,2-dioxaphosphorinane, 2-sulfide derivatives for use as anti-wear additives in lubricant compositions |
| RU2523651C2 (ru) * | 2012-05-22 | 2014-07-20 | Государственное бюджетное образовательное учреждение высшего профессионального образования "Владивостокский государственный медицинский университет" Министерства здравоохранения и социального развития Российской Федерации (ГБОУ ВПО ВГМУ Минздравсоцразвития России) | Способ дифференцированного контроля базисного противовоспалительного лечения бронхиальной астмы у детей и подростков |
| RU2506045C1 (ru) * | 2012-09-05 | 2014-02-10 | Федеральное государственное бюджетное учреждение "Дальневосточный научный центр физиологии и патологии дыхания" Сибирского отделения РАМН | Способ прогнозирования достижения контроля бронхиальной астмы |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2149645A1 (de) | 1970-10-07 | 1972-09-14 | Pfizer | 2-Phenyl-as-triazin-3.5-(2H,4H)-dione und die Verwendung dieser Verbindungen zur Bekaempfung der Coccidiose |
| US3912723A (en) | 1971-03-29 | 1975-10-14 | Pfizer | 2-Phenyl-as-triazine-3,5(2H,4H)diones |
| US3883528A (en) | 1974-04-19 | 1975-05-13 | Pfizer | Preparation of 2(aryl)-as-triazine-3,5(2H,4H)-dione coccidiostats |
| CA1244024A (en) | 1984-08-01 | 1988-11-01 | Gustaaf M. Boeckx | .alpha.- ARYL-4-(4,5-DIHYDRO-3,5-DIOXO-1,2,4-TRIAZIN- 2(3H)-YL)BENZENEACETONITRILES |
| US4631278A (en) | 1984-08-01 | 1986-12-23 | Janssen Pharmaceutica N.V. | Anti-protozoal α-aryl-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)-benzeneacetonitrile derivatives, pharmaceutical compositions, and method of use therefor |
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| EP0476439A1 (de) | 1990-09-18 | 1992-03-25 | Bayer Ag | Substituierte 1,2,4-Triazindione, Verfahren zu ihrer Herstellung, Zwischenprodukte dafür und ihre Verwendung |
| DE4120138A1 (de) | 1991-06-19 | 1992-12-24 | Bayer Ag | Substituierte hexahydro-1,2,4-triazindione, verfahren zu ihrer herstellung, zwischenprodukte dafuer und ihre verwendung |
| TW263495B (ru) | 1992-12-23 | 1995-11-21 | Celltech Ltd | |
| GB9304920D0 (en) | 1993-03-10 | 1993-04-28 | Celltech Ltd | Chemical compounds |
| RU2146674C1 (ru) | 1993-10-15 | 2000-03-20 | Такеда Кемикал Индастриз, Лтд. | Производные триазина, способы их получения, антипротозойная композиция, добавка в пищу животных, способ ингибирования протозои у животных |
| TW332201B (en) | 1995-04-06 | 1998-05-21 | Janssen Pharmaceutica Nv | 1,3-Dihydro-1-(phenylalkyl)-2H-imidazol-2-one derivatives |
| EP0737672B1 (en) | 1995-04-14 | 2001-10-04 | Takeda Schering-Plough Animal Health K.K. | Method of producing triazine derivatives |
| CN1128141C (zh) * | 1996-08-30 | 2003-11-19 | 武田舍林-普劳动物保健株式会社 | 1,2,4－三嗪－3,5－二酮衍生物,其制备和用途 |
| NZ501627A (en) * | 1997-07-10 | 2002-02-01 | Janssen Pharmaceutica Nv | 3,5-dioxo-2(3H)-triazine derivatives substituted by 4-(phenylmethyl)phenyl useful as IL-5 inhibitors |
| WO1999002505A1 (en) * | 1997-07-10 | 1999-01-21 | Janssen Pharmaceutica N.V. | Il-5 inhibiting 6-azauracil derivatives |
-
1999
- 1999-12-16 IL IL14376699A patent/IL143766A/xx not_active IP Right Cessation
- 1999-12-16 CA CA002354511A patent/CA2354511A1/en not_active Abandoned
- 1999-12-16 HU HU0104641A patent/HUP0104641A3/hu unknown
- 1999-12-16 AU AU21001/00A patent/AU773780B2/en not_active Ceased
- 1999-12-16 EP EP99965509A patent/EP1140873B1/en not_active Expired - Lifetime
- 1999-12-16 TR TR2001/01729T patent/TR200101729T2/xx unknown
- 1999-12-16 ES ES99965509T patent/ES2289835T3/es not_active Expired - Lifetime
- 1999-12-16 CN CNB998146110A patent/CN100343239C/zh not_active Expired - Fee Related
- 1999-12-16 EA EA200100677A patent/EA004806B1/ru not_active IP Right Cessation
- 1999-12-16 UA UA2001075132A patent/UA73107C2/uk unknown
- 1999-12-16 PL PL349526A patent/PL198205B1/pl not_active IP Right Cessation
- 1999-12-16 US US09/868,384 patent/US6803364B1/en not_active Expired - Fee Related
- 1999-12-16 WO PCT/EP1999/010169 patent/WO2000037451A1/en active IP Right Grant
- 1999-12-16 PT PT99965509T patent/PT1140873E/pt unknown
- 1999-12-16 ID IDW00200101295A patent/ID28880A/id unknown
- 1999-12-16 SK SK815-2001A patent/SK8152001A3/sk unknown
- 1999-12-16 CZ CZ20012062A patent/CZ20012062A3/cs unknown
- 1999-12-16 BR BR9916366-7A patent/BR9916366A/pt not_active Application Discontinuation
- 1999-12-16 JP JP2000589523A patent/JP2002533331A/ja not_active Withdrawn
- 1999-12-16 DK DK99965509T patent/DK1140873T3/da active
- 1999-12-16 DE DE69936396T patent/DE69936396T2/de not_active Expired - Fee Related
- 1999-12-16 EE EEP200100320A patent/EE200100320A/xx unknown
- 1999-12-16 NZ NZ512748A patent/NZ512748A/en unknown
- 1999-12-16 KR KR1020017006666A patent/KR100635721B1/ko not_active IP Right Cessation
- 1999-12-16 AT AT99965509T patent/ATE365723T1/de not_active IP Right Cessation
- 1999-12-17 MY MYPI99005536A patent/MY125808A/en unknown
- 1999-12-17 TW TW088122197A patent/TWI249530B/zh not_active IP Right Cessation
- 1999-12-17 AR ARP990106512A patent/AR021887A1/es not_active Application Discontinuation
- 1999-12-17 CO CO99079022A patent/CO5150147A1/es unknown
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2000
- 2000-03-05 SA SA00201030A patent/SA00201030B1/ar unknown
-
2001
- 2001-06-14 BG BG105602A patent/BG105602A/xx unknown
- 2001-06-15 HR HR20010455A patent/HRP20010455A2/hr not_active Application Discontinuation
- 2001-06-15 NO NO20012987A patent/NO319814B1/no unknown
- 2001-06-15 ZA ZA200104942A patent/ZA200104942B/en unknown
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2002
- 2002-06-03 HK HK02104206.0A patent/HK1042491A1/zh unknown
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