MX2012005518A - Derivados de pirazol amina triciclica. - Google Patents
Derivados de pirazol amina triciclica.Info
- Publication number
- MX2012005518A MX2012005518A MX2012005518A MX2012005518A MX2012005518A MX 2012005518 A MX2012005518 A MX 2012005518A MX 2012005518 A MX2012005518 A MX 2012005518A MX 2012005518 A MX2012005518 A MX 2012005518A MX 2012005518 A MX2012005518 A MX 2012005518A
- Authority
- MX
- Mexico
- Prior art keywords
- denotes
- compounds
- formula
- het2
- pyrazole
- Prior art date
Links
- -1 pyrazol amine Chemical class 0.000 title description 353
- 150000001875 compounds Chemical class 0.000 claims abstract description 514
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 32
- 201000010099 disease Diseases 0.000 claims abstract description 22
- 201000006417 multiple sclerosis Diseases 0.000 claims abstract description 13
- 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 12
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 10
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims description 240
- 239000000203 mixture Substances 0.000 claims description 69
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 64
- 125000004432 carbon atom Chemical group C* 0.000 claims description 53
- 150000003839 salts Chemical class 0.000 claims description 51
- 238000006243 chemical reaction Methods 0.000 claims description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims description 49
- 229910052757 nitrogen Inorganic materials 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 101100134925 Gallus gallus COR6 gene Proteins 0.000 claims description 29
- 229910052727 yttrium Inorganic materials 0.000 claims description 29
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 27
- 239000004480 active ingredient Substances 0.000 claims description 26
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 26
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 26
- 239000003814 drug Substances 0.000 claims description 23
- 229910052786 argon Inorganic materials 0.000 claims description 22
- 239000008194 pharmaceutical composition Substances 0.000 claims description 21
- 239000012453 solvate Substances 0.000 claims description 21
- 229920006395 saturated elastomer Polymers 0.000 claims description 19
- 150000004677 hydrates Chemical class 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 229940079593 drug Drugs 0.000 claims description 13
- 208000006673 asthma Diseases 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 125000002619 bicyclic group Chemical group 0.000 claims description 10
- 208000035475 disorder Diseases 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 125000002837 carbocyclic group Chemical group 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 125000002950 monocyclic group Chemical group 0.000 claims description 9
- 230000002265 prevention Effects 0.000 claims description 9
- 208000035895 Guillain-Barré syndrome Diseases 0.000 claims description 7
- 206010049567 Miller Fisher syndrome Diseases 0.000 claims description 7
- 201000011510 cancer Diseases 0.000 claims description 7
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 7
- 125000004434 sulfur atom Chemical group 0.000 claims description 7
- 208000003343 Antiphospholipid Syndrome Diseases 0.000 claims description 6
- 201000004681 Psoriasis Diseases 0.000 claims description 6
- 230000001363 autoimmune Effects 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 206010003827 Autoimmune hepatitis Diseases 0.000 claims description 5
- 208000009137 Behcet syndrome Diseases 0.000 claims description 5
- 208000008439 Biliary Liver Cirrhosis Diseases 0.000 claims description 5
- 208000033222 Biliary cirrhosis primary Diseases 0.000 claims description 5
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 5
- 208000011231 Crohn disease Diseases 0.000 claims description 5
- 208000030836 Hashimoto thyroiditis Diseases 0.000 claims description 5
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 5
- 201000001981 dermatomyositis Diseases 0.000 claims description 5
- 206010025135 lupus erythematosus Diseases 0.000 claims description 5
- 206010028417 myasthenia gravis Diseases 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 208000026872 Addison Disease Diseases 0.000 claims description 4
- 208000015943 Coeliac disease Diseases 0.000 claims description 4
- 208000024869 Goodpasture syndrome Diseases 0.000 claims description 4
- 208000031845 Pernicious anaemia Diseases 0.000 claims description 4
- 208000012654 Primary biliary cholangitis Diseases 0.000 claims description 4
- 206010039710 Scleroderma Diseases 0.000 claims description 4
- 208000021386 Sjogren Syndrome Diseases 0.000 claims description 4
- 206010047115 Vasculitis Diseases 0.000 claims description 4
- 208000004631 alopecia areata Diseases 0.000 claims description 4
- 208000025302 chronic primary adrenal insufficiency Diseases 0.000 claims description 4
- 208000005987 polymyositis Diseases 0.000 claims description 4
- 208000011580 syndromic disease Diseases 0.000 claims description 4
- 206010001935 American trypanosomiasis Diseases 0.000 claims description 3
- 208000024699 Chagas disease Diseases 0.000 claims description 3
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 3
- 201000009273 Endometriosis Diseases 0.000 claims description 3
- 208000007465 Giant cell arteritis Diseases 0.000 claims description 3
- 208000015023 Graves' disease Diseases 0.000 claims description 3
- 208000001204 Hashimoto Disease Diseases 0.000 claims description 3
- 208000000209 Isaacs syndrome Diseases 0.000 claims description 3
- 208000000185 Localized scleroderma Diseases 0.000 claims description 3
- 208000003250 Mixed connective tissue disease Diseases 0.000 claims description 3
- 206010027982 Morphoea Diseases 0.000 claims description 3
- 206010072359 Neuromyotonia Diseases 0.000 claims description 3
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims description 3
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims description 3
- 241000223109 Trypanosoma cruzi Species 0.000 claims description 3
- 206010047642 Vitiligo Diseases 0.000 claims description 3
- 230000001154 acute effect Effects 0.000 claims description 3
- 208000027625 autoimmune inner ear disease Diseases 0.000 claims description 3
- 206010012601 diabetes mellitus Diseases 0.000 claims description 3
- 208000002557 hidradenitis Diseases 0.000 claims description 3
- 230000002519 immonomodulatory effect Effects 0.000 claims description 3
- 208000026278 immune system disease Diseases 0.000 claims description 3
- 201000003631 narcolepsy Diseases 0.000 claims description 3
- 201000000980 schizophrenia Diseases 0.000 claims description 3
- 206010043207 temporal arteritis Diseases 0.000 claims description 3
- 208000003807 Graves Disease Diseases 0.000 claims description 2
- 208000005615 Interstitial Cystitis Diseases 0.000 claims description 2
- 241000721454 Pemphigus Species 0.000 claims description 2
- 201000001119 neuropathy Diseases 0.000 claims description 2
- 230000007823 neuropathy Effects 0.000 claims description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 2
- 201000011152 Pemphigus Diseases 0.000 claims 1
- 206010043561 Thrombocytopenic purpura Diseases 0.000 claims 1
- 108060008539 Transglutaminase Proteins 0.000 claims 1
- 208000007502 anemia Diseases 0.000 claims 1
- 201000002491 encephalomyelitis Diseases 0.000 claims 1
- 230000002949 hemolytic effect Effects 0.000 claims 1
- 201000001976 pemphigus vulgaris Diseases 0.000 claims 1
- 208000033808 peripheral neuropathy Diseases 0.000 claims 1
- 102000003601 transglutaminase Human genes 0.000 claims 1
- 239000012828 PI3K inhibitor Substances 0.000 abstract description 4
- 229940043441 phosphoinositide 3-kinase inhibitor Drugs 0.000 abstract description 4
- KOPFEFZSAMLEHK-UHFFFAOYSA-N 1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1C=CNN=1 KOPFEFZSAMLEHK-UHFFFAOYSA-N 0.000 description 233
- 239000000543 intermediate Substances 0.000 description 225
- 238000004949 mass spectrometry Methods 0.000 description 223
- 238000005481 NMR spectroscopy Methods 0.000 description 207
- 238000004128 high performance liquid chromatography Methods 0.000 description 185
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 165
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 144
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 115
- 230000014759 maintenance of location Effects 0.000 description 100
- 239000007787 solid Substances 0.000 description 98
- 239000011541 reaction mixture Substances 0.000 description 96
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 83
- 239000000243 solution Substances 0.000 description 83
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 81
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 79
- 239000002904 solvent Substances 0.000 description 76
- 229910001868 water Inorganic materials 0.000 description 75
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 74
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 64
- 235000019439 ethyl acetate Nutrition 0.000 description 62
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 57
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- MSPOSRHJXMILNK-UHFFFAOYSA-N ethyl 1h-pyrazole-5-carboxylate Chemical compound CCOC(=O)C1=CC=NN1 MSPOSRHJXMILNK-UHFFFAOYSA-N 0.000 description 54
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 53
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 46
- 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 description 46
- 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 description 46
- 235000002639 sodium chloride Nutrition 0.000 description 44
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 43
- 108091007960 PI3Ks Proteins 0.000 description 42
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical group CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 40
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 40
- 239000012044 organic layer Substances 0.000 description 39
- 230000002829 reductive effect Effects 0.000 description 38
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 37
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 32
- 239000011734 sodium Substances 0.000 description 31
- 239000002585 base Substances 0.000 description 27
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 26
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 239000002253 acid Substances 0.000 description 24
- 239000012267 brine Substances 0.000 description 24
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 24
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 22
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- 229910052938 sodium sulfate Inorganic materials 0.000 description 20
- 235000011152 sodium sulphate Nutrition 0.000 description 20
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 19
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
- 238000004440 column chromatography Methods 0.000 description 18
- CPRRHERYRRXBRZ-SRVKXCTJSA-N methyl n-[(2s)-1-[[(2s)-1-hydroxy-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CO)C[C@@H]1CCNC1=O CPRRHERYRRXBRZ-SRVKXCTJSA-N 0.000 description 18
- 229960000583 acetic acid Drugs 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 16
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 16
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
- 239000007788 liquid Substances 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 239000000843 powder Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 238000009472 formulation Methods 0.000 description 14
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 13
- 235000019341 magnesium sulphate Nutrition 0.000 description 13
- 239000000725 suspension Substances 0.000 description 13
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 108010029485 Protein Isoforms Proteins 0.000 description 12
- 102000001708 Protein Isoforms Human genes 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 11
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 11
- 150000001412 amines Chemical class 0.000 description 11
- 210000004027 cell Anatomy 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 239000003208 petroleum Substances 0.000 description 11
- 229910000027 potassium carbonate Inorganic materials 0.000 description 11
- 235000015424 sodium Nutrition 0.000 description 11
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 11
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
- PAQZWJGSJMLPMG-UHFFFAOYSA-N 2,4,6-tripropyl-1,3,5,2$l^{5},4$l^{5},6$l^{5}-trioxatriphosphinane 2,4,6-trioxide Chemical compound CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1 PAQZWJGSJMLPMG-UHFFFAOYSA-N 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 10
- 229910052708 sodium Inorganic materials 0.000 description 10
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- 238000003786 synthesis reaction Methods 0.000 description 10
- 239000003643 water by type Substances 0.000 description 10
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 9
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 9
- 239000003153 chemical reaction reagent Substances 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 235000017557 sodium bicarbonate Nutrition 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 239000006196 drop Substances 0.000 description 8
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 8
- 229910052736 halogen Inorganic materials 0.000 description 8
- 150000002429 hydrazines Chemical class 0.000 description 8
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
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- 229910000033 sodium borohydride Inorganic materials 0.000 description 8
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- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 7
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 7
- 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 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 7
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 7
- 125000002252 acyl group Chemical group 0.000 description 7
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 7
- 229910000024 caesium carbonate Inorganic materials 0.000 description 7
- 239000013058 crude material Substances 0.000 description 7
- 210000000265 leukocyte Anatomy 0.000 description 7
- 239000003446 ligand Substances 0.000 description 7
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 7
- 229940067157 phenylhydrazine Drugs 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
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- 239000000758 substrate Substances 0.000 description 7
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 7
- QDLHCMPXEPAAMD-QAIWCSMKSA-N wortmannin Chemical compound C1([C@]2(C)C3=C(C4=O)OC=C3C(=O)O[C@@H]2COC)=C4[C@@H]2CCC(=O)[C@@]2(C)C[C@H]1OC(C)=O QDLHCMPXEPAAMD-QAIWCSMKSA-N 0.000 description 7
- QDLHCMPXEPAAMD-UHFFFAOYSA-N wortmannin Natural products COCC1OC(=O)C2=COC(C3=O)=C2C1(C)C1=C3C2CCC(=O)C2(C)CC1OC(C)=O QDLHCMPXEPAAMD-UHFFFAOYSA-N 0.000 description 7
- CVQSWZMJOGOPAV-UHFFFAOYSA-N 2,3-dihydrothiochromen-4-one Chemical compound C1=CC=C2C(=O)CCSC2=C1 CVQSWZMJOGOPAV-UHFFFAOYSA-N 0.000 description 6
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 6
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 6
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 6
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 6
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- 239000007832 Na2SO4 Substances 0.000 description 6
- 108091000080 Phosphotransferase Proteins 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 150000001350 alkyl halides Chemical class 0.000 description 6
- 238000005804 alkylation reaction Methods 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- A—HUMAN NECESSITIES
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| DE102011055815A1 (de) | 2011-11-29 | 2013-05-29 | Aicuris Gmbh & Co. Kg | Carboxamid-substituierte Heteroaryl-Pyrazole und ihre Verwendung |
| ES2661510T3 (es) | 2011-12-15 | 2018-04-02 | Novartis Ag | Uso de inhibidores de la actividad o función de PI3K |
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| JP6367211B2 (ja) * | 2012-11-16 | 2018-08-01 | ザ ユナイテッド ステイツ オブ アメリカ， アズ リプレゼンテッド バイ ザ セクレタリー， デパートメント オブ ヘルス アンド ヒューマン サービシーズ | リソソーム蓄積症の改善物質としてのトコフェロール誘導体およびトコフェリルキノン誘導体 |
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| TW201837026A (zh) | 2017-01-10 | 2018-10-16 | 德商拜耳廠股份有限公司 | 作為除害劑之雜環衍生物（二） |
| KR102515694B1 (ko) | 2017-01-10 | 2023-03-29 | 바이엘 악티엔게젤샤프트 | 해충 방제제로서의 헤테로사이클 유도체 |
| CN108434150B (zh) * | 2018-02-09 | 2020-03-10 | 天津医科大学总医院 | Zstk474用于制备ean治疗药物的应用 |
| EP3608326A1 (en) * | 2018-08-10 | 2020-02-12 | Irbm S.P.A. | Tricyclic inhibitors of hepatitis b virus |
| CN113754678B (zh) * | 2020-06-02 | 2023-03-10 | 江苏恒瑞医药股份有限公司 | 二氢硫代色烯并吡唑类衍生物、其制备方法及其在医药上的应用 |
| CN113754685B (zh) * | 2020-06-02 | 2023-06-16 | 江苏恒瑞医药股份有限公司 | 二氢硫代色烯并吡唑类衍生物、其制备方法及其在医药上的应用 |
| BR112022026904A2 (pt) | 2020-07-02 | 2023-01-24 | Bayer Ag | Derivados de heterocicleno como agentes de controle de pragas |
| WO2022007924A1 (zh) * | 2020-07-09 | 2022-01-13 | 江苏恒瑞医药股份有限公司 | 氧杂氮杂双环类衍生物、其制备方法及其在医药上的应用 |
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| JP2024511836A (ja) * | 2021-03-29 | 2024-03-15 | アイオンクチュラ・ソシエテ・アノニム | 膵臓癌の治療のためのｐｉ３ｋ－デルタ阻害剤 |
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| CN115491252B (zh) * | 2022-09-29 | 2023-05-02 | 江苏四新界面剂科技有限公司 | 一种宝石切割用低泡润湿剂及其制备方法 |
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| TWI926701B (zh) * | 2024-03-22 | 2026-05-21 | 復旦大學附屬中山醫院 | 三環骨架化合物及其在製備抗腫瘤藥物的應用 |
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| US4816467A (en) | 1987-01-09 | 1989-03-28 | Farmitalia Carlo Erba S.R.L | Heteroaryl 3-oxo-propanenitrile derivatives, pharmaceutical compositions and use |
| GB8814586D0 (en) * | 1988-06-20 | 1988-07-27 | Erba Carlo Spa | Tricyclic 3-oxo-propanenitrile derivatives & process for their preparation |
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| GB8916290D0 (en) * | 1989-07-17 | 1989-08-31 | Erba Carlo Spa | Heteroaryl-3-oxo-propanenitrile derivatives useful in stimulating myelopoiesis |
| JP3542826B2 (ja) | 1994-07-11 | 2004-07-14 | 帝国臓器製薬株式会社 | 新規な二環式化合物縮合［２，１−ｄ］イソキサゾール−３−カルボン酸誘導体 |
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| ES2480994T3 (es) | 2008-03-31 | 2014-07-29 | Genentech, Inc. | Compuestos de tipo benzopirano y benzoxepina inhibidores de PI3K y métodos de uso |
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| US9073940B2 (en) | 2015-07-07 |
| JP5735526B2 (ja) | 2015-06-17 |
| CA2778174A1 (en) | 2011-05-19 |
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| JP2013510825A (ja) | 2013-03-28 |
| ES2607952T3 (es) | 2017-04-04 |
| US20120238545A1 (en) | 2012-09-20 |
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| IL219602A0 (en) | 2012-07-31 |
| KR20130049766A (ko) | 2013-05-14 |
| EP2499146B1 (en) | 2016-09-21 |
| CN102695710A (zh) | 2012-09-26 |
| AU2010317883B2 (en) | 2015-08-06 |
| WO2011058149A1 (en) | 2011-05-19 |
| CN102695710B (zh) | 2015-08-19 |
| IL219602A (en) | 2017-04-30 |
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