JP2016530338A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2016530338A5 JP2016530338A5 JP2016543959A JP2016543959A JP2016530338A5 JP 2016530338 A5 JP2016530338 A5 JP 2016530338A5 JP 2016543959 A JP2016543959 A JP 2016543959A JP 2016543959 A JP2016543959 A JP 2016543959A JP 2016530338 A5 JP2016530338 A5 JP 2016530338A5
- Authority
- JP
- Japan
- Prior art keywords
- alkylene
- heterocyclyl
- cycloalkyl
- alkyl
- membered heteroaryl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- -1 wherein Chemical group 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 40
- 125000002947 alkylene group Chemical group 0.000 claims 24
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 14
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 13
- 150000003839 salts Chemical class 0.000 claims 13
- 239000002207 metabolite Substances 0.000 claims 12
- 239000000651 prodrug Substances 0.000 claims 12
- 229940002612 prodrug Drugs 0.000 claims 12
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 11
- 150000001204 N-oxides Chemical class 0.000 claims 11
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 10
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 10
- 239000012453 solvate Substances 0.000 claims 10
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 9
- 125000001424 substituent group Chemical group 0.000 claims 9
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 7
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 6
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 4
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 claims 2
- 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 claims 2
- 206010052779 Transplant rejections Diseases 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 1
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
- 125000006587 (C5-C10) heteroarylene group Chemical group 0.000 claims 1
- 125000003627 8 membered carbocyclic group Chemical group 0.000 claims 1
- 125000005330 8 membered heterocyclic group Chemical group 0.000 claims 1
- 201000002909 Aspergillosis Diseases 0.000 claims 1
- 208000036641 Aspergillus infections Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 208000008035 Back Pain Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 206010012438 Dermatitis atopic Diseases 0.000 claims 1
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims 1
- 241000239366 Euphausiacea Species 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 206010065390 Inflammatory pain Diseases 0.000 claims 1
- 208000004554 Leishmaniasis Diseases 0.000 claims 1
- 208000004852 Lung Injury Diseases 0.000 claims 1
- 208000034486 Multi-organ failure Diseases 0.000 claims 1
- 208000010718 Multiple Organ Failure Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 206010033645 Pancreatitis Diseases 0.000 claims 1
- 206010036376 Postherpetic Neuralgia Diseases 0.000 claims 1
- 102000001253 Protein Kinase Human genes 0.000 claims 1
- 206010062106 Respiratory tract infection viral Diseases 0.000 claims 1
- 206010039085 Rhinitis allergic Diseases 0.000 claims 1
- 208000007536 Thrombosis Diseases 0.000 claims 1
- 206010069363 Traumatic lung injury Diseases 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 201000010105 allergic rhinitis Diseases 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 201000008937 atopic dermatitis Diseases 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000005713 exacerbation Effects 0.000 claims 1
- 208000019691 hematopoietic and lymphoid cell neoplasm Diseases 0.000 claims 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 208000014674 injury Diseases 0.000 claims 1
- 208000017169 kidney disease Diseases 0.000 claims 1
- 231100000515 lung injury Toxicity 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 208000029744 multiple organ dysfunction syndrome Diseases 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 208000004296 neuralgia Diseases 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 208000021722 neuropathic pain Diseases 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 108060006633 protein kinase Proteins 0.000 claims 1
- 208000023504 respiratory system disease Diseases 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 230000019100 sperm motility Effects 0.000 claims 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 230000008733 trauma Effects 0.000 claims 1
- 206010044652 trigeminal neuralgia Diseases 0.000 claims 1
- 239000003981 vehicle Substances 0.000 claims 1
- 230000003612 virological effect Effects 0.000 claims 1
- 0 *C(*)(*)Nc1ncnc(N)c1* Chemical compound *C(*)(*)Nc1ncnc(N)c1* 0.000 description 25
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- 241000282472 Canis lupus familiaris Species 0.000 description 4
- 241000282693 Cercopithecidae Species 0.000 description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- YKRSBVHDNZDXAU-UHFFFAOYSA-N CCCC(N1c2ccccc2)=Nc(cccc2Cl)c2C1=O Chemical compound CCCC(N1c2ccccc2)=Nc(cccc2Cl)c2C1=O YKRSBVHDNZDXAU-UHFFFAOYSA-N 0.000 description 3
- PXFIFCKFSWPYNS-UHFFFAOYSA-N Cc1nnc(-c2c(NC)ncnc2N)[o]1 Chemical compound Cc1nnc(-c2c(NC)ncnc2N)[o]1 PXFIFCKFSWPYNS-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Substances IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 3
- XJHCXCQVJFPJIK-UHFFFAOYSA-M cesium fluoride Substances [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 3
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 3
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 3
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 2
- DVLFYONBTKHTER-UHFFFAOYSA-N 3-(N-morpholino)propanesulfonic acid Chemical compound OS(=O)(=O)CCCN1CCOCC1 DVLFYONBTKHTER-UHFFFAOYSA-N 0.000 description 2
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- FVWLOYHPTXJUOB-NSHDSACASA-N CC(C)c1n[o]c(-c2c(N)ncnc2N[C@@H](C)C(N2C3CC3)=Nc3cccc(Cl)c3C2=O)n1 Chemical compound CC(C)c1n[o]c(-c2c(N)ncnc2N[C@@H](C)C(N2C3CC3)=Nc3cccc(Cl)c3C2=O)n1 FVWLOYHPTXJUOB-NSHDSACASA-N 0.000 description 2
- RWNQSVFONHIAJY-NSHDSACASA-N CC(C)c1nc(-c2c(N)ncnc2N[C@@H](C)C(N2C3CC3)=Nc(cccc3Cl)c3C2=O)n[o]1 Chemical compound CC(C)c1nc(-c2c(N)ncnc2N[C@@H](C)C(N2C3CC3)=Nc(cccc3Cl)c3C2=O)n[o]1 RWNQSVFONHIAJY-NSHDSACASA-N 0.000 description 2
- GSTFOVILIDDZER-UHFFFAOYSA-N CC(N1c(cccc2)c2F)=Nc2ccccc2C1=O Chemical compound CC(N1c(cccc2)c2F)=Nc2ccccc2C1=O GSTFOVILIDDZER-UHFFFAOYSA-N 0.000 description 2
- RBZSYNGUXQXIOD-UHFFFAOYSA-N CCC(N1C2CC2)=Nc2cccc(Cl)c2C1=O Chemical compound CCC(N1C2CC2)=Nc2cccc(Cl)c2C1=O RBZSYNGUXQXIOD-UHFFFAOYSA-N 0.000 description 2
- GVGFGDCQGZBSQX-UHFFFAOYSA-N CCCC(N1C2CC2)=Nc2cccc(Cl)c2C1=O Chemical compound CCCC(N1C2CC2)=Nc2cccc(Cl)c2C1=O GVGFGDCQGZBSQX-UHFFFAOYSA-N 0.000 description 2
- ZYQTURWDBPYARS-HNNXBMFYSA-N CC[C@@H](C(N1C2CC2)=Nc(cccc2Cl)c2C1=O)Nc1c(-c2ncccc2)c(N)ncn1 Chemical compound CC[C@@H](C(N1C2CC2)=Nc(cccc2Cl)c2C1=O)Nc1c(-c2ncccc2)c(N)ncn1 ZYQTURWDBPYARS-HNNXBMFYSA-N 0.000 description 2
- HCQYGHUSCVSXJL-ZDUSSCGKSA-N CC[C@@H](C(N1C2CC2)=Nc(cccc2Cl)c2C1=O)Nc1ncnc(N)c1-c1ncn[n]1C Chemical compound CC[C@@H](C(N1C2CC2)=Nc(cccc2Cl)c2C1=O)Nc1ncnc(N)c1-c1ncn[n]1C HCQYGHUSCVSXJL-ZDUSSCGKSA-N 0.000 description 2
- MYMYFEDEQPGMLG-KRWDZBQOSA-N CC[C@@H](C(N1C2CC2)=Nc2cccc(-c3c[n](C)nc3)c2C1=O)Nc1c(-c2n[o]c(C)n2)c(N)ncn1 Chemical compound CC[C@@H](C(N1C2CC2)=Nc2cccc(-c3c[n](C)nc3)c2C1=O)Nc1c(-c2n[o]c(C)n2)c(N)ncn1 MYMYFEDEQPGMLG-KRWDZBQOSA-N 0.000 description 2
- QKADUNPNWYXUTJ-AWEZNQCLSA-N CC[C@@H](C(N1C2CC2)=Nc2cccc(C)c2C1=O)Nc1c(-c2n[o]c(C)n2)c(N)ncn1 Chemical compound CC[C@@H](C(N1C2CC2)=Nc2cccc(C)c2C1=O)Nc1c(-c2n[o]c(C)n2)c(N)ncn1 QKADUNPNWYXUTJ-AWEZNQCLSA-N 0.000 description 2
- HKBDRQURLRRLSE-AWEZNQCLSA-N CC[C@@H](C(N1C2CC2)=Nc2cccc(C)c2C1=O)Nc1c(-c2nnc(C)[o]2)c(N)ncn1 Chemical compound CC[C@@H](C(N1C2CC2)=Nc2cccc(C)c2C1=O)Nc1c(-c2nnc(C)[o]2)c(N)ncn1 HKBDRQURLRRLSE-AWEZNQCLSA-N 0.000 description 2
- JRKNECOQAMYIIE-AWEZNQCLSA-N CC[C@@H](C(N1C2CC2)=Nc2cccc(C)c2C1=O)Nc1ncnc(N)c1-c1n[n](C)cn1 Chemical compound CC[C@@H](C(N1C2CC2)=Nc2cccc(C)c2C1=O)Nc1ncnc(N)c1-c1n[n](C)cn1 JRKNECOQAMYIIE-AWEZNQCLSA-N 0.000 description 2
- NVKXMZYUOHLPEI-AWEZNQCLSA-N CC[C@@H](C(N1C2CC2)=Nc2cccc(C)c2C1=O)Nc1ncnc(N)c1-c1n[o]cc1 Chemical compound CC[C@@H](C(N1C2CC2)=Nc2cccc(C)c2C1=O)Nc1ncnc(N)c1-c1n[o]cc1 NVKXMZYUOHLPEI-AWEZNQCLSA-N 0.000 description 2
- DZEHMFQCLVOMOK-LBPRGKRZSA-N CC[C@@H](C(N1C2CC2)=Nc2cccc(Cl)c2C1=O)Nc1c(-c2n[n](C)c(C(N)=O)n2)c(N)ncn1 Chemical compound CC[C@@H](C(N1C2CC2)=Nc2cccc(Cl)c2C1=O)Nc1c(-c2n[n](C)c(C(N)=O)n2)c(N)ncn1 DZEHMFQCLVOMOK-LBPRGKRZSA-N 0.000 description 2
- XHQKEWGONWROCR-ZDUSSCGKSA-N CC[C@@H](C(N1C2CC2)=Nc2cccc(Cl)c2C1=O)Nc1c(-c2nc(C)n[o]2)c(N)ncn1 Chemical compound CC[C@@H](C(N1C2CC2)=Nc2cccc(Cl)c2C1=O)Nc1c(-c2nc(C)n[o]2)c(N)ncn1 XHQKEWGONWROCR-ZDUSSCGKSA-N 0.000 description 2
- NWHRVZPHHWMATN-LBPRGKRZSA-N CC[C@@H](C(N1C2CC2)=Nc2cccc(Cl)c2C1=O)Nc1ncnc(N)c1-c1n[n](C)nn1 Chemical compound CC[C@@H](C(N1C2CC2)=Nc2cccc(Cl)c2C1=O)Nc1ncnc(N)c1-c1n[n](C)nn1 NWHRVZPHHWMATN-LBPRGKRZSA-N 0.000 description 2
- BMWNMOJLMFGFLM-ZDUSSCGKSA-N CC[C@@H](C(N1C2CC2)=Nc2cccc(Cl)c2C1=O)Nc1ncnc(N)c1-c1n[o]c(C)n1 Chemical compound CC[C@@H](C(N1C2CC2)=Nc2cccc(Cl)c2C1=O)Nc1ncnc(N)c1-c1n[o]c(C)n1 BMWNMOJLMFGFLM-ZDUSSCGKSA-N 0.000 description 2
- UWEAHZHSIRFDKN-ZDUSSCGKSA-N CC[C@@H](C(N1C2CC2)=Nc2cccc(Cl)c2C1=O)Nc1ncnc(N)c1-c1nnc(C)[o]1 Chemical compound CC[C@@H](C(N1C2CC2)=Nc2cccc(Cl)c2C1=O)Nc1ncnc(N)c1-c1nnc(C)[o]1 UWEAHZHSIRFDKN-ZDUSSCGKSA-N 0.000 description 2
- RTBANXMWEKEZPR-ZDUSSCGKSA-N CC[C@@H](C(N1C2CC2)=Nc2cccc(F)c2C1=O)Nc1c(-c2nnc(C)[o]2)c(N)ncn1 Chemical compound CC[C@@H](C(N1C2CC2)=Nc2cccc(F)c2C1=O)Nc1c(-c2nnc(C)[o]2)c(N)ncn1 RTBANXMWEKEZPR-ZDUSSCGKSA-N 0.000 description 2
- XKFDSZFYFPEEMB-ZDUSSCGKSA-N CC[C@@H](C(N1C2CC2)=Nc2cccc(F)c2C1=O)Nc1ncnc(N)c1-c1n[o]cc1 Chemical compound CC[C@@H](C(N1C2CC2)=Nc2cccc(F)c2C1=O)Nc1ncnc(N)c1-c1n[o]cc1 XKFDSZFYFPEEMB-ZDUSSCGKSA-N 0.000 description 2
- GAELXURZTAIMHJ-ZDUSSCGKSA-N CC[C@@H](C(N1C2CC2)=Nc2cccc(F)c2C1=O)Nc1ncnc(N)c1-c1nc(C)n[o]1 Chemical compound CC[C@@H](C(N1C2CC2)=Nc2cccc(F)c2C1=O)Nc1ncnc(N)c1-c1nc(C)n[o]1 GAELXURZTAIMHJ-ZDUSSCGKSA-N 0.000 description 2
- MARDRRMXZDSLJS-SGMGOOAPSA-N CC[C@@H](C(N1[C@H](C2)[C@H]2F)=Nc2cccc(Cl)c2C1=O)Nc1ncnc(N)c1-c1nc(C)n[o]1 Chemical compound CC[C@@H](C(N1[C@H](C2)[C@H]2F)=Nc2cccc(Cl)c2C1=O)Nc1ncnc(N)c1-c1nc(C)n[o]1 MARDRRMXZDSLJS-SGMGOOAPSA-N 0.000 description 2
- GEFHERTXXZZVJI-KRWDZBQOSA-N CC[C@@H](C(N1c2ccccc2)=Nc(cccc2C)c2C1=O)Nc1c(-c2nc(C)n[o]2)c(N)ncn1 Chemical compound CC[C@@H](C(N1c2ccccc2)=Nc(cccc2C)c2C1=O)Nc1c(-c2nc(C)n[o]2)c(N)ncn1 GEFHERTXXZZVJI-KRWDZBQOSA-N 0.000 description 2
- RMXVUNGBBSUPQR-INIZCTEOSA-N CC[C@@H](C(N1c2ccccc2)=Nc(cccc2Cl)c2C1=O)Nc1c(-c2n[o]c(C)n2)c(N)ncn1 Chemical compound CC[C@@H](C(N1c2ccccc2)=Nc(cccc2Cl)c2C1=O)Nc1c(-c2n[o]c(C)n2)c(N)ncn1 RMXVUNGBBSUPQR-INIZCTEOSA-N 0.000 description 2
- WCCXGUWMDHTEII-INIZCTEOSA-N CC[C@@H](C(N1c2ccccc2)=Nc(cccc2Cl)c2C1=O)Nc1c(-c2nc(C)n[o]2)c(N)ncn1 Chemical compound CC[C@@H](C(N1c2ccccc2)=Nc(cccc2Cl)c2C1=O)Nc1c(-c2nc(C)n[o]2)c(N)ncn1 WCCXGUWMDHTEII-INIZCTEOSA-N 0.000 description 2
- ILEKDDLNABRBKB-INIZCTEOSA-N CC[C@@H](C(N1c2ccccc2)=Nc(cccc2Cl)c2C1=O)Nc1c(-c2nnc(C)[o]2)c(N)ncn1 Chemical compound CC[C@@H](C(N1c2ccccc2)=Nc(cccc2Cl)c2C1=O)Nc1c(-c2nnc(C)[o]2)c(N)ncn1 ILEKDDLNABRBKB-INIZCTEOSA-N 0.000 description 2
- CLFSAFUGSRYFOK-INIZCTEOSA-N CC[C@@H](C(N1c2ccccc2)=Nc(cccc2Cl)c2C1=O)Nc1ncnc(N)c1-c1ncn[n]1C Chemical compound CC[C@@H](C(N1c2ccccc2)=Nc(cccc2Cl)c2C1=O)Nc1ncnc(N)c1-c1ncn[n]1C CLFSAFUGSRYFOK-INIZCTEOSA-N 0.000 description 2
- ZGFXXKVXXBUMPQ-KRWDZBQOSA-N CC[C@@H](C(N1c2ccccc2)=Nc(cccc2F)c2C1=O)Nc1ncnc(N)c1-c1nc(C2CC2)n[o]1 Chemical compound CC[C@@H](C(N1c2ccccc2)=Nc(cccc2F)c2C1=O)Nc1ncnc(N)c1-c1nc(C2CC2)n[o]1 ZGFXXKVXXBUMPQ-KRWDZBQOSA-N 0.000 description 2
- YHECXFBUVNLEEW-KRWDZBQOSA-N CC[C@@H](C(N1c2ccccc2)=Nc2cccc(Cl)c2C1=O)Nc1ncnc(N)c1-c1nnc(C2CC2)[o]1 Chemical compound CC[C@@H](C(N1c2ccccc2)=Nc2cccc(Cl)c2C1=O)Nc1ncnc(N)c1-c1nnc(C2CC2)[o]1 YHECXFBUVNLEEW-KRWDZBQOSA-N 0.000 description 2
- URUUQNCJRXMHHX-YOEHRIQHSA-N CC[C@@H](C(N1c2ccccc2)=Nc2cccc(Cl)c2C1=O)Nc1ncnc(N)c1C1=N[C@@H](C)CO1 Chemical compound CC[C@@H](C(N1c2ccccc2)=Nc2cccc(Cl)c2C1=O)Nc1ncnc(N)c1C1=N[C@@H](C)CO1 URUUQNCJRXMHHX-YOEHRIQHSA-N 0.000 description 2
- JOSYLTOEHFLOLW-KRWDZBQOSA-N CC[C@@H](C(N1c2ccccc2)=Nc2cccc(F)c2C1=O)Nc1c(-c2nc(C)c[o]2)c(N)ncn1 Chemical compound CC[C@@H](C(N1c2ccccc2)=Nc2cccc(F)c2C1=O)Nc1c(-c2nc(C)c[o]2)c(N)ncn1 JOSYLTOEHFLOLW-KRWDZBQOSA-N 0.000 description 2
- MJORCRPQWCUGJG-INIZCTEOSA-N CC[C@@H](C(N1c2ccccc2)=Nc2cccc(F)c2C1=O)Nc1c(-c2nc(C)n[o]2)c(N)ncn1 Chemical compound CC[C@@H](C(N1c2ccccc2)=Nc2cccc(F)c2C1=O)Nc1c(-c2nc(C)n[o]2)c(N)ncn1 MJORCRPQWCUGJG-INIZCTEOSA-N 0.000 description 2
- UYHSJYGKPZAHLB-KRWDZBQOSA-N CC[C@@H](C(N1c2ccccc2)=Nc2cccc(F)c2C1=O)Nc1ncnc(N)c1-c1nnc(C2CC2)[o]1 Chemical compound CC[C@@H](C(N1c2ccccc2)=Nc2cccc(F)c2C1=O)Nc1ncnc(N)c1-c1nnc(C2CC2)[o]1 UYHSJYGKPZAHLB-KRWDZBQOSA-N 0.000 description 2
- YIPYJPRXBPGRSE-SFHVURJKSA-N CC[C@@H](C(N1c2ccccc2C)=Nc2cccc(C)c2C1=O)Nc1c(-c2nc(C)c[o]2)c(N)ncn1 Chemical compound CC[C@@H](C(N1c2ccccc2C)=Nc2cccc(C)c2C1=O)Nc1c(-c2nc(C)c[o]2)c(N)ncn1 YIPYJPRXBPGRSE-SFHVURJKSA-N 0.000 description 2
- MBJFTVCXERNWQH-KRWDZBQOSA-N CC[C@@H](C(N1c2ccccc2C)=Nc2cccc(C)c2C1=O)Nc1ncnc(N)c1-c1n[o]c(C)n1 Chemical compound CC[C@@H](C(N1c2ccccc2C)=Nc2cccc(C)c2C1=O)Nc1ncnc(N)c1-c1n[o]c(C)n1 MBJFTVCXERNWQH-KRWDZBQOSA-N 0.000 description 2
- RWZSZLMQENMEGZ-KRWDZBQOSA-N CC[C@@H](C(N1c2ccccc2C)=Nc2cccc(C)c2C1=O)Nc1ncnc(N)c1-c1nc(C)n[o]1 Chemical compound CC[C@@H](C(N1c2ccccc2C)=Nc2cccc(C)c2C1=O)Nc1ncnc(N)c1-c1nc(C)n[o]1 RWZSZLMQENMEGZ-KRWDZBQOSA-N 0.000 description 2
- ZOQPXXJLEHMVOM-INIZCTEOSA-N CC[C@@H](C(N1c2ccccc2F)=Nc(cccc2)c2C1=O)Nc1ncnc(N)c1-c1n[n](C)cn1 Chemical compound CC[C@@H](C(N1c2ccccc2F)=Nc(cccc2)c2C1=O)Nc1ncnc(N)c1-c1n[n](C)cn1 ZOQPXXJLEHMVOM-INIZCTEOSA-N 0.000 description 2
- PQQBPPSOCJFQEM-INIZCTEOSA-N CC[C@@H](C(N1c2ccccc2F)=Nc2ccccc2C1=O)Nc1c(-c2n[o]c(C)n2)c(N)ncn1 Chemical compound CC[C@@H](C(N1c2ccccc2F)=Nc2ccccc2C1=O)Nc1c(-c2n[o]c(C)n2)c(N)ncn1 PQQBPPSOCJFQEM-INIZCTEOSA-N 0.000 description 2
- MRZSSZGDKDBNFF-JTQLQIEISA-N CCc1nc(-c2c(N[C@@H](C)C(N3C4CC4)=Nc4cccc(Cl)c4C3=O)ncnc2N)n[o]1 Chemical compound CCc1nc(-c2c(N[C@@H](C)C(N3C4CC4)=Nc4cccc(Cl)c4C3=O)ncnc2N)n[o]1 MRZSSZGDKDBNFF-JTQLQIEISA-N 0.000 description 2
- HCMWBXRHNIWOAT-JTQLQIEISA-N C[C@@H](C(N1C2CC2)=Nc(cccc2Cl)c2C1=O)Nc1c(-c2n[n](C)cn2)c(N)ncn1 Chemical compound C[C@@H](C(N1C2CC2)=Nc(cccc2Cl)c2C1=O)Nc1c(-c2n[n](C)cn2)c(N)ncn1 HCMWBXRHNIWOAT-JTQLQIEISA-N 0.000 description 2
- WFPNTMMMIFTFGW-HNNXBMFYSA-N C[C@@H](C(N1c2ccccc2)=Nc(cccc2-c3c[n](C)nc3)c2C1=O)Nc1c(-c2n[o]c(C)n2)c(N)ncn1 Chemical compound C[C@@H](C(N1c2ccccc2)=Nc(cccc2-c3c[n](C)nc3)c2C1=O)Nc1c(-c2n[o]c(C)n2)c(N)ncn1 WFPNTMMMIFTFGW-HNNXBMFYSA-N 0.000 description 2
- NWLCDUBIMMOPIR-ZDUSSCGKSA-N C[C@@H](C(N1c2ccccc2)=Nc2cccc(Cl)c2C1=O)Nc1c(-c2nc(C3CC3)n[o]2)c(N)ncn1 Chemical compound C[C@@H](C(N1c2ccccc2)=Nc2cccc(Cl)c2C1=O)Nc1c(-c2nc(C3CC3)n[o]2)c(N)ncn1 NWLCDUBIMMOPIR-ZDUSSCGKSA-N 0.000 description 2
- XLPQUBPSCCBYDH-LBPRGKRZSA-N C[C@@H](C(N1c2ccccc2)=Nc2cccc(Cl)c2C1=O)Nc1ncnc(N)c1-c1nc(C)n[o]1 Chemical compound C[C@@H](C(N1c2ccccc2)=Nc2cccc(Cl)c2C1=O)Nc1ncnc(N)c1-c1nc(C)n[o]1 XLPQUBPSCCBYDH-LBPRGKRZSA-N 0.000 description 2
- CWSWAZPOLYMHDL-ZDUSSCGKSA-N C[C@@H](C(N1c2ccccc2)=Nc2cccc(F)c2C1=O)Nc1ncnc(N)c1-c1nc(C2CC2)n[o]1 Chemical compound C[C@@H](C(N1c2ccccc2)=Nc2cccc(F)c2C1=O)Nc1ncnc(N)c1-c1nc(C2CC2)n[o]1 CWSWAZPOLYMHDL-ZDUSSCGKSA-N 0.000 description 2
- DOFNIOSQIKJLFP-UHFFFAOYSA-N Cc1n[o]c(-c2c(NC)ncnc2N)n1 Chemical compound Cc1n[o]c(-c2c(NC)ncnc2N)n1 DOFNIOSQIKJLFP-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- YSHOWEKUVWPFNR-UHFFFAOYSA-N burgess reagent Chemical compound CC[N+](CC)(CC)S(=O)(=O)N=C([O-])OC YSHOWEKUVWPFNR-UHFFFAOYSA-N 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 239000012091 fetal bovine serum Substances 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 2
- BCVXHSPFUWZLGQ-UHFFFAOYSA-N mecn acetonitrile Chemical compound CC#N.CC#N BCVXHSPFUWZLGQ-UHFFFAOYSA-N 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- 239000002953 phosphate buffered saline Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- WFIZEGIEIOHZCP-UHFFFAOYSA-M potassium formate Chemical compound [K+].[O-]C=O WFIZEGIEIOHZCP-UHFFFAOYSA-M 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000003656 tris buffered saline Substances 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- UKSZBOKPHAQOMP-SVLSSHOZSA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 UKSZBOKPHAQOMP-SVLSSHOZSA-N 0.000 description 1
- 229910000667 (NH4)2Ce(NO3)6 Inorganic materials 0.000 description 1
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- MICMHFIQSAMEJG-UHFFFAOYSA-N 1-bromopyrrolidine-2,5-dione Chemical compound BrN1C(=O)CCC1=O.BrN1C(=O)CCC1=O MICMHFIQSAMEJG-UHFFFAOYSA-N 0.000 description 1
- JZUMPNUYDJBTNO-UHFFFAOYSA-N 1-hydroxybenzotriazole;hydrate Chemical compound O.C1=CC=C2N(O)N=NC2=C1.C1=CC=C2N(O)N=NC2=C1 JZUMPNUYDJBTNO-UHFFFAOYSA-N 0.000 description 1
- KISWVXRQTGLFGD-UHFFFAOYSA-N 2-[[2-[[6-amino-2-[[2-[[2-[[5-amino-2-[[2-[[1-[2-[[6-amino-2-[(2,5-diamino-5-oxopentanoyl)amino]hexanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]pyrrolidine-2-carbonyl]amino]-3-hydroxypropanoyl]amino]-5-oxopentanoyl]amino]-5-(diaminomethylideneamino)p Chemical compound C1CCN(C(=O)C(CCCN=C(N)N)NC(=O)C(CCCCN)NC(=O)C(N)CCC(N)=O)C1C(=O)NC(CO)C(=O)NC(CCC(N)=O)C(=O)NC(CCCN=C(N)N)C(=O)NC(CO)C(=O)NC(CCCCN)C(=O)NC(C(=O)NC(CC(C)C)C(O)=O)CC1=CC=C(O)C=C1 KISWVXRQTGLFGD-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- RRRCPCOJPQLWEP-UHFFFAOYSA-N 3-hydroxytriazolo[4,5-b]pyridine Chemical compound C1=CN=C2N(O)N=NC2=C1.C1=CN=C2N(O)N=NC2=C1 RRRCPCOJPQLWEP-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
- ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 description 1
- GLUUGHFHXGJENI-UHFFFAOYSA-N C1NCCNC1 Chemical compound C1NCCNC1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N C1NCCOC1 Chemical compound C1NCCOC1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N C1OCCOC1 Chemical compound C1OCCOC1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- JDLVLEVQVLBQDI-UHFFFAOYSA-N CC(C)C(N1c(c(F)ccc2)c2F)=Nc2cccc(C)c2C1=O Chemical compound CC(C)C(N1c(c(F)ccc2)c2F)=Nc2cccc(C)c2C1=O JDLVLEVQVLBQDI-UHFFFAOYSA-N 0.000 description 1
- OPCLDTPJKQVIFW-UHFFFAOYSA-N CC(C)C(N1c2ccccc2)=Nc2cccc(C)c2C1=O Chemical compound CC(C)C(N1c2ccccc2)=Nc2cccc(C)c2C1=O OPCLDTPJKQVIFW-UHFFFAOYSA-N 0.000 description 1
- FIEYHAAMDAPVCH-UHFFFAOYSA-N CC(N1)=Nc2ccccc2C1=O Chemical compound CC(N1)=Nc2ccccc2C1=O FIEYHAAMDAPVCH-UHFFFAOYSA-N 0.000 description 1
- DYRGWKLHLJSECO-UHFFFAOYSA-N CC(N1C2CC2)=Nc2cccc(Cl)c2C1=O Chemical compound CC(N1C2CC2)=Nc2cccc(Cl)c2C1=O DYRGWKLHLJSECO-UHFFFAOYSA-N 0.000 description 1
- YYQWGBMPKFTIEI-UHFFFAOYSA-N CC(N1C2CC2)=Nc2cccc(F)c2C1=O Chemical compound CC(N1C2CC2)=Nc2cccc(F)c2C1=O YYQWGBMPKFTIEI-UHFFFAOYSA-N 0.000 description 1
- MFQBFSKSBDRUKH-UHFFFAOYSA-N CC(N1c(cc2)ccc2C#N)=Nc2cccc(F)c2C1=O Chemical compound CC(N1c(cc2)ccc2C#N)=Nc2cccc(F)c2C1=O MFQBFSKSBDRUKH-UHFFFAOYSA-N 0.000 description 1
- IPPYDZVPNOMMDK-UHFFFAOYSA-N CC(N1c(cccc2)c2F)=Nc2cccc(Cl)c2C1=O Chemical compound CC(N1c(cccc2)c2F)=Nc2cccc(Cl)c2C1=O IPPYDZVPNOMMDK-UHFFFAOYSA-N 0.000 description 1
- BHGQUHKPKXBUOL-UHFFFAOYSA-N CC(N1c(cccc2)c2OC)=Nc2cccc(F)c2C1=O Chemical compound CC(N1c(cccc2)c2OC)=Nc2cccc(F)c2C1=O BHGQUHKPKXBUOL-UHFFFAOYSA-N 0.000 description 1
- ZSYHBXHBCPLOEY-UHFFFAOYSA-N CC(N1c2cc(F)cc(F)c2)=Nc2cccc(Cl)c2C1=O Chemical compound CC(N1c2cc(F)cc(F)c2)=Nc2cccc(Cl)c2C1=O ZSYHBXHBCPLOEY-UHFFFAOYSA-N 0.000 description 1
- HPZCOJUQVXDPPS-UHFFFAOYSA-N CC(N1c2cccc(F)c2)=Nc2cccc(Cl)c2C1=O Chemical compound CC(N1c2cccc(F)c2)=Nc2cccc(Cl)c2C1=O HPZCOJUQVXDPPS-UHFFFAOYSA-N 0.000 description 1
- BHJFOIVDGPKWBX-UHFFFAOYSA-N CC(N1c2ccccc2)=Nc(cccc2Cl)c2C1=O Chemical compound CC(N1c2ccccc2)=Nc(cccc2Cl)c2C1=O BHJFOIVDGPKWBX-UHFFFAOYSA-N 0.000 description 1
- LUDZXFRILZOVJX-UHFFFAOYSA-N CC(N1c2ccccc2)=Nc2cccc(F)c2C1=O Chemical compound CC(N1c2ccccc2)=Nc2cccc(F)c2C1=O LUDZXFRILZOVJX-UHFFFAOYSA-N 0.000 description 1
- RWVWXBRLVPTKIW-UHFFFAOYSA-N CC(N1c2n[o]cc2)=Nc2cccc(F)c2C1=O Chemical compound CC(N1c2n[o]cc2)=Nc2cccc(F)c2C1=O RWVWXBRLVPTKIW-UHFFFAOYSA-N 0.000 description 1
- HAHXUMSESSHCJV-UHFFFAOYSA-P CC(OC(c1c(N)ncnc1[NH3+])=[NH2+])=N Chemical compound CC(OC(c1c(N)ncnc1[NH3+])=[NH2+])=N HAHXUMSESSHCJV-UHFFFAOYSA-P 0.000 description 1
- JUMBUGPUCBBIBP-UHFFFAOYSA-N CCC(/C=[NH]/c1c(-c2ncc(C)[o]2)c(N)ncn1)C(N1c2ccccc2)=Nc2cccc(F)c2C1=O Chemical compound CCC(/C=[NH]/c1c(-c2ncc(C)[o]2)c(N)ncn1)C(N1c2ccccc2)=Nc2cccc(F)c2C1=O JUMBUGPUCBBIBP-UHFFFAOYSA-N 0.000 description 1
- KVBLHOKVMVPVND-UHFFFAOYSA-N CCC(N1C2CC2)=Nc2cccc(-c3c[n](C)nc3)c2C1=O Chemical compound CCC(N1C2CC2)=Nc2cccc(-c3c[n](C)nc3)c2C1=O KVBLHOKVMVPVND-UHFFFAOYSA-N 0.000 description 1
- CMZSYVUOBOXPBQ-UHFFFAOYSA-N CCC(N1c2ccccc2)=Nc(cccc2F)c2C1=O Chemical compound CCC(N1c2ccccc2)=Nc(cccc2F)c2C1=O CMZSYVUOBOXPBQ-UHFFFAOYSA-N 0.000 description 1
- VUWVNJFWVRHJSM-UHFFFAOYSA-N CCC(N1c2ccccc2)=Nc2cccc(-c3c[n](C)nc3)c2C1=O Chemical compound CCC(N1c2ccccc2)=Nc2cccc(-c3c[n](C)nc3)c2C1=O VUWVNJFWVRHJSM-UHFFFAOYSA-N 0.000 description 1
- CWIMJKVIYPTZMH-UHFFFAOYSA-N CCC(N1c2ccccc2)=Nc2cccc(Cl)c2C1=O Chemical compound CCC(N1c2ccccc2)=Nc2cccc(Cl)c2C1=O CWIMJKVIYPTZMH-UHFFFAOYSA-N 0.000 description 1
- UDDNBNZHUNHNTI-IBIXRBPDSA-O CCCC(N1C2CC2)=Nc(cccc2/C(/C=[NH2+])=C/NC)c2C1=O Chemical compound CCCC(N1C2CC2)=Nc(cccc2/C(/C=[NH2+])=C/NC)c2C1=O UDDNBNZHUNHNTI-IBIXRBPDSA-O 0.000 description 1
- UUDXEQVCZLDNKP-UHFFFAOYSA-N CCCC(N1C2CC2)=Nc2cccc(F)c2C1=O Chemical compound CCCC(N1C2CC2)=Nc2cccc(F)c2C1=O UUDXEQVCZLDNKP-UHFFFAOYSA-N 0.000 description 1
- LOCSNHDILCTKDH-UHFFFAOYSA-N CCCC(N1c2ccccc2)=Nc2cccc(C)c2C1=O Chemical compound CCCC(N1c2ccccc2)=Nc2cccc(C)c2C1=O LOCSNHDILCTKDH-UHFFFAOYSA-N 0.000 description 1
- JSSJLNINOWZJTM-UHFFFAOYSA-N CCCC(N1c2ccccc2)=Nc2cccc(F)c2C1=O Chemical compound CCCC(N1c2ccccc2)=Nc2cccc(F)c2C1=O JSSJLNINOWZJTM-UHFFFAOYSA-N 0.000 description 1
- FYKKEQXDMPGSTE-UHFFFAOYSA-N CCCC(N1c2ccccc2F)=Nc2ccccc2C1=O Chemical compound CCCC(N1c2ccccc2F)=Nc2ccccc2C1=O FYKKEQXDMPGSTE-UHFFFAOYSA-N 0.000 description 1
- BSQKVBPNQNXVFH-KRWDZBQOSA-N CC[C@@H](C(N1C2CC2)=Nc(cccc2-c3c[n](C)nc3)c2C1=O)Nc1c(-c2nc(C)n[o]2)c(N)ncn1 Chemical compound CC[C@@H](C(N1C2CC2)=Nc(cccc2-c3c[n](C)nc3)c2C1=O)Nc1c(-c2nc(C)n[o]2)c(N)ncn1 BSQKVBPNQNXVFH-KRWDZBQOSA-N 0.000 description 1
- DZZVAACVJPATCS-AWEZNQCLSA-N CC[C@@H](C(N1C2CC2)=Nc(cccc2Cl)c2C1=O)Nc1c(-c2n[n](C)c(COC)n2)c(N)ncn1 Chemical compound CC[C@@H](C(N1C2CC2)=Nc(cccc2Cl)c2C1=O)Nc1c(-c2n[n](C)c(COC)n2)c(N)ncn1 DZZVAACVJPATCS-AWEZNQCLSA-N 0.000 description 1
- QRGGVMROWJFYDK-LBPRGKRZSA-N CC[C@@H](C(N1C2CC2)=Nc(cccc2Cl)c2C1=O)Nc1c(-c2nnc[o]2)c(N)ncn1 Chemical compound CC[C@@H](C(N1C2CC2)=Nc(cccc2Cl)c2C1=O)Nc1c(-c2nnc[o]2)c(N)ncn1 QRGGVMROWJFYDK-LBPRGKRZSA-N 0.000 description 1
- HRAOPBOFBQTNTF-ZDUSSCGKSA-N CC[C@@H](C(N1C2CC2)=Nc(cccc2Cl)c2C1=O)Nc1ncnc(N)c1-c1n[o]cc1 Chemical compound CC[C@@H](C(N1C2CC2)=Nc(cccc2Cl)c2C1=O)Nc1ncnc(N)c1-c1n[o]cc1 HRAOPBOFBQTNTF-ZDUSSCGKSA-N 0.000 description 1
- SBUOLWIFHXGUAY-ZDUSSCGKSA-N CC[C@@H](C(N1C2CC2)=Nc(cccc2Cl)c2C1=O)Nc1ncnc(N)c1-c1nc(CC)n[o]1 Chemical compound CC[C@@H](C(N1C2CC2)=Nc(cccc2Cl)c2C1=O)Nc1ncnc(N)c1-c1nc(CC)n[o]1 SBUOLWIFHXGUAY-ZDUSSCGKSA-N 0.000 description 1
- TWKTVDQMLSWSSY-ZDUSSCGKSA-N CC[C@@H](C(N1C2CC2)=Nc(cccc2F)c2C1=O)Nc1c(-c2n[o]c(C)n2)c(N)ncn1 Chemical compound CC[C@@H](C(N1C2CC2)=Nc(cccc2F)c2C1=O)Nc1c(-c2n[o]c(C)n2)c(N)ncn1 TWKTVDQMLSWSSY-ZDUSSCGKSA-N 0.000 description 1
- TYBBWGOUGVBCRY-ZDUSSCGKSA-N CC[C@@H](C(N1C2CC2)=Nc(cccc2F)c2C1=O)Nc1ncnc(N)c1-c1n[n](C)cn1 Chemical compound CC[C@@H](C(N1C2CC2)=Nc(cccc2F)c2C1=O)Nc1ncnc(N)c1-c1n[n](C)cn1 TYBBWGOUGVBCRY-ZDUSSCGKSA-N 0.000 description 1
- WXUWDLHGCQIFHN-KRWDZBQOSA-N CC[C@@H](C(N1C2CC2)=Nc2cccc(-c3c[n](C)nc3)c2C1=O)Nc1c(-c2nnc(C)[o]2)c(N)ncn1 Chemical compound CC[C@@H](C(N1C2CC2)=Nc2cccc(-c3c[n](C)nc3)c2C1=O)Nc1c(-c2nnc(C)[o]2)c(N)ncn1 WXUWDLHGCQIFHN-KRWDZBQOSA-N 0.000 description 1
- YWLLMLPIFZQEHJ-LVUMDSSZSA-O CC[C@@H](C(N1C2CC2)=Nc2cccc(/C(/C=[NH2+])=C/NC)c2C1=O)Nc1ncnc(N)c1-c1nc(C)n[o]1 Chemical compound CC[C@@H](C(N1C2CC2)=Nc2cccc(/C(/C=[NH2+])=C/NC)c2C1=O)Nc1ncnc(N)c1-c1nc(C)n[o]1 YWLLMLPIFZQEHJ-LVUMDSSZSA-O 0.000 description 1
- XTRGHZGHSYZOMB-ZDUSSCGKSA-N CC[C@@H](C(N1C2CC2)=Nc2cccc(Cl)c2C1=O)Nc1c(-c2n[n](C)cn2)c(N)ncn1 Chemical compound CC[C@@H](C(N1C2CC2)=Nc2cccc(Cl)c2C1=O)Nc1c(-c2n[n](C)cn2)c(N)ncn1 XTRGHZGHSYZOMB-ZDUSSCGKSA-N 0.000 description 1
- MVFPDBPZLUHHTE-AWEZNQCLSA-N CC[C@@H](C(N1C2CC2)=Nc2cccc(Cl)c2C1=O)Nc1c(-c2nc(C)c[o]2)c(N)ncn1 Chemical compound CC[C@@H](C(N1C2CC2)=Nc2cccc(Cl)c2C1=O)Nc1c(-c2nc(C)c[o]2)c(N)ncn1 MVFPDBPZLUHHTE-AWEZNQCLSA-N 0.000 description 1
- MOECKSFLSLFSOU-JRTLGTJJSA-N CC[C@@H](C(N1C2CC2)=Nc2cccc(Cl)c2C1=O)Nc1c(C2ON=C(CC)N2)c(N)ncn1 Chemical compound CC[C@@H](C(N1C2CC2)=Nc2cccc(Cl)c2C1=O)Nc1c(C2ON=C(CC)N2)c(N)ncn1 MOECKSFLSLFSOU-JRTLGTJJSA-N 0.000 description 1
- IQMMBFLAPZGERP-AWEZNQCLSA-N CC[C@@H](C(N1C2CC2)=Nc2cccc(Cl)c2C1=O)Nc1ncnc(N)c1-c1n[n](C)cc1 Chemical compound CC[C@@H](C(N1C2CC2)=Nc2cccc(Cl)c2C1=O)Nc1ncnc(N)c1-c1n[n](C)cc1 IQMMBFLAPZGERP-AWEZNQCLSA-N 0.000 description 1
- AJEZNZPPJZSQHU-FZMZJTMJSA-N CC[C@@H](C(N1C2CC2)=Nc2cccc(Cl)c2C1=O)Nc1ncnc(N)c1C1=N[C@@H](C)CO1 Chemical compound CC[C@@H](C(N1C2CC2)=Nc2cccc(Cl)c2C1=O)Nc1ncnc(N)c1C1=N[C@@H](C)CO1 AJEZNZPPJZSQHU-FZMZJTMJSA-N 0.000 description 1
- JNARHMFDSWRAQN-INIZCTEOSA-N CC[C@@H](C(N1c(cc2)ccc2F)=Nc(cccc2Cl)c2C1=O)Nc1ncnc(N)c1-c1n[n](C)cn1 Chemical compound CC[C@@H](C(N1c(cc2)ccc2F)=Nc(cccc2Cl)c2C1=O)Nc1ncnc(N)c1-c1n[n](C)cn1 JNARHMFDSWRAQN-INIZCTEOSA-N 0.000 description 1
- FTAMGVHKRKINBA-KRWDZBQOSA-N CC[C@@H](C(N1c2c(C)cccc2)=Nc2cccc(C)c2C1=O)Nc1ncnc(N)c1-c1nnc(C)[o]1 Chemical compound CC[C@@H](C(N1c2c(C)cccc2)=Nc2cccc(C)c2C1=O)Nc1ncnc(N)c1-c1nnc(C)[o]1 FTAMGVHKRKINBA-KRWDZBQOSA-N 0.000 description 1
- YNTRQVRTKBEXHP-FQEVSTJZSA-N CC[C@@H](C(N1c2ccccc2)=Nc2cccc(-c3c[n](C)nc3)c2C1=O)Nc1ncnc(N)c1-c1nc(C)n[o]1 Chemical compound CC[C@@H](C(N1c2ccccc2)=Nc2cccc(-c3c[n](C)nc3)c2C1=O)Nc1ncnc(N)c1-c1nc(C)n[o]1 YNTRQVRTKBEXHP-FQEVSTJZSA-N 0.000 description 1
- OVSHIUKLOYOBKB-FQEVSTJZSA-N CC[C@@H](C(N1c2ccccc2)=Nc2cccc(-c3c[n](C)nc3)c2C1=O)Nc1ncnc(N)c1-c1nnc(C)[o]1 Chemical compound CC[C@@H](C(N1c2ccccc2)=Nc2cccc(-c3c[n](C)nc3)c2C1=O)Nc1ncnc(N)c1-c1nnc(C)[o]1 OVSHIUKLOYOBKB-FQEVSTJZSA-N 0.000 description 1
- BHHZRKZWEYTCEJ-KRWDZBQOSA-N CC[C@@H](C(N1c2ccccc2)=Nc2cccc(Cl)c2C1=O)Nc1ncnc(N)c1-c1nc(C2CC2)n[o]1 Chemical compound CC[C@@H](C(N1c2ccccc2)=Nc2cccc(Cl)c2C1=O)Nc1ncnc(N)c1-c1nc(C2CC2)n[o]1 BHHZRKZWEYTCEJ-KRWDZBQOSA-N 0.000 description 1
- BNHFCJIPTCIVMZ-CJAHMYNBSA-N CC[C@@H](C(N1c2ccccc2)=Nc2cccc(F)c2C1=O)Nc(nc[n](C1CC1)(=C)c1N)c1-[n]1nc(C)cc1 Chemical compound CC[C@@H](C(N1c2ccccc2)=Nc2cccc(F)c2C1=O)Nc(nc[n](C1CC1)(=C)c1N)c1-[n]1nc(C)cc1 BNHFCJIPTCIVMZ-CJAHMYNBSA-N 0.000 description 1
- BJACNSIFBCXESR-IERUPTGBSA-N CC[C@@H](C(N1c2ccccc2)=Nc2cccc(F)c2C1=O)Nc(nc[n](C1CCC1)(=C)c1N)c1-[n]1nc(C)cc1 Chemical compound CC[C@@H](C(N1c2ccccc2)=Nc2cccc(F)c2C1=O)Nc(nc[n](C1CCC1)(=C)c1N)c1-[n]1nc(C)cc1 BJACNSIFBCXESR-IERUPTGBSA-N 0.000 description 1
- BTGAIZVSUUOPDF-INIZCTEOSA-N CC[C@@H](C(N1c2ccccc2)=Nc2cccc(F)c2C1=O)Nc1c(-c2nnc(C)[o]2)c(N)ncn1 Chemical compound CC[C@@H](C(N1c2ccccc2)=Nc2cccc(F)c2C1=O)Nc1c(-c2nnc(C)[o]2)c(N)ncn1 BTGAIZVSUUOPDF-INIZCTEOSA-N 0.000 description 1
- OKZKFMYHGRJYPM-INIZCTEOSA-O CC[C@@H](C(N1c2ccccc2)=Nc2cccc(F)c2C1=O)Nc1c(C(OC(C)=N)=[NH2+])c(N)ncn1 Chemical compound CC[C@@H](C(N1c2ccccc2)=Nc2cccc(F)c2C1=O)Nc1c(C(OC(C)=N)=[NH2+])c(N)ncn1 OKZKFMYHGRJYPM-INIZCTEOSA-O 0.000 description 1
- BRFFKJFRGJGUEP-HNNXBMFYSA-N CC[C@@H](C(N1c2ccccc2)=Nc2cccc(F)c2C1=O)Nc1ncnc(N)c1-c1n[n](C)nn1 Chemical compound CC[C@@H](C(N1c2ccccc2)=Nc2cccc(F)c2C1=O)Nc1ncnc(N)c1-c1n[n](C)nn1 BRFFKJFRGJGUEP-HNNXBMFYSA-N 0.000 description 1
- ZIPBBHWZYNWMJW-KRWDZBQOSA-N CC[C@@H](C(N1c2ccccc2C)=Nc(cccc2C)c2C1=O)Nc(ncnc1N)c1N(N)/N=C(/C)\N Chemical compound CC[C@@H](C(N1c2ccccc2C)=Nc(cccc2C)c2C1=O)Nc(ncnc1N)c1N(N)/N=C(/C)\N ZIPBBHWZYNWMJW-KRWDZBQOSA-N 0.000 description 1
- BSAXEXPBCVWGCF-KRWDZBQOSA-N CC[C@@H](C(N1c2ccccc2C)=Nc(cccc2C)c2C1=O)Nc1ncnc(N)c1-c1n[n](C)cn1 Chemical compound CC[C@@H](C(N1c2ccccc2C)=Nc(cccc2C)c2C1=O)Nc1ncnc(N)c1-c1n[n](C)cn1 BSAXEXPBCVWGCF-KRWDZBQOSA-N 0.000 description 1
- ZLDCILJHSATLTL-HNNXBMFYSA-N CC[C@@H](C(N1c2ccccc2C)=Nc2cccc(C)c2C1=O)Nc1ncnc(N)c1N(N)N Chemical compound CC[C@@H](C(N1c2ccccc2C)=Nc2cccc(C)c2C1=O)Nc1ncnc(N)c1N(N)N ZLDCILJHSATLTL-HNNXBMFYSA-N 0.000 description 1
- FYBQZUOIXANMIC-INIZCTEOSA-N CC[C@@H](C(N1c2ccccc2F)=Nc(cccc2)c2C1=O)Nc1c(-c2nnc(C)[o]2)c(N)ncn1 Chemical compound CC[C@@H](C(N1c2ccccc2F)=Nc(cccc2)c2C1=O)Nc1c(-c2nnc(C)[o]2)c(N)ncn1 FYBQZUOIXANMIC-INIZCTEOSA-N 0.000 description 1
- JFWYOHNOQLEFMO-HNNXBMFYSA-N CC[C@@H](C(N1c2ccccc2F)=Nc2cccc(Cl)c2C1=O)Nc1ncnc(N)c1-c1n[n](C)cn1 Chemical compound CC[C@@H](C(N1c2ccccc2F)=Nc2cccc(Cl)c2C1=O)Nc1ncnc(N)c1-c1n[n](C)cn1 JFWYOHNOQLEFMO-HNNXBMFYSA-N 0.000 description 1
- KKYDBHYWGIRPCB-INIZCTEOSA-N CC[C@@H](C(N1c2ccccc2F)=Nc2ccccc2C1=O)Nc1c(-c2nc(C)n[o]2)c(N)ncn1 Chemical compound CC[C@@H](C(N1c2ccccc2F)=Nc2ccccc2C1=O)Nc1c(-c2nc(C)n[o]2)c(N)ncn1 KKYDBHYWGIRPCB-INIZCTEOSA-N 0.000 description 1
- GXXBIIYFLNHBGX-INIZCTEOSA-N CC[C@@H](C(N1c2ccccc2OC)=Nc2cccc(F)c2C1=O)Nc(ncnc1N)c1-[n]1nc(C)cn1 Chemical compound CC[C@@H](C(N1c2ccccc2OC)=Nc2cccc(F)c2C1=O)Nc(ncnc1N)c1-[n]1nc(C)cn1 GXXBIIYFLNHBGX-INIZCTEOSA-N 0.000 description 1
- HRAOPBOFBQTNTF-CYBMUJFWSA-N CC[C@H](C(N1C2CC2)=Nc(cccc2Cl)c2C1=O)Nc1ncnc(N)c1-c1n[o]cc1 Chemical compound CC[C@H](C(N1C2CC2)=Nc(cccc2Cl)c2C1=O)Nc1ncnc(N)c1-c1n[o]cc1 HRAOPBOFBQTNTF-CYBMUJFWSA-N 0.000 description 1
- XHQKEWGONWROCR-CYBMUJFWSA-N CC[C@H](C(N1C2CC2)=Nc(cccc2Cl)c2C1=O)Nc1ncnc(N)c1-c1nc(C)n[o]1 Chemical compound CC[C@H](C(N1C2CC2)=Nc(cccc2Cl)c2C1=O)Nc1ncnc(N)c1-c1nc(C)n[o]1 XHQKEWGONWROCR-CYBMUJFWSA-N 0.000 description 1
- IAKSDUJCQNSGRH-MRXNPFEDSA-N CC[C@H](CNc1ncnc(N)c1-c1ncc(C)[o]1)C(N1c2ccccc2)=Nc2cccc(F)c2C1=O Chemical compound CC[C@H](CNc1ncnc(N)c1-c1ncc(C)[o]1)C(N1c2ccccc2)=Nc2cccc(F)c2C1=O IAKSDUJCQNSGRH-MRXNPFEDSA-N 0.000 description 1
- SGFLIJNRRRZHBM-UHFFFAOYSA-N CNc1c(-c2nc(C3CC3)n[o]2)c(N)ncn1 Chemical compound CNc1c(-c2nc(C3CC3)n[o]2)c(N)ncn1 SGFLIJNRRRZHBM-UHFFFAOYSA-N 0.000 description 1
- DOKPAQSYSZQCLV-UHFFFAOYSA-N CNc1c(-c2nnc(C3CC3)[o]2)c(N)ncn1 Chemical compound CNc1c(-c2nnc(C3CC3)[o]2)c(N)ncn1 DOKPAQSYSZQCLV-UHFFFAOYSA-N 0.000 description 1
- LJDOXDBFVRCTDS-UHFFFAOYSA-N CNc1ncnc(N)c1-c1nnc[o]1 Chemical compound CNc1ncnc(N)c1-c1nnc[o]1 LJDOXDBFVRCTDS-UHFFFAOYSA-N 0.000 description 1
- GMGVCDXJCHBWBR-LBPRGKRZSA-N C[C@@H](C(N1C2CC2)=Nc(cccc2-c3c[n](C)nc3)c2C1=O)Nc1ncnc(N)c1-c1nc(C)n[o]1 Chemical compound C[C@@H](C(N1C2CC2)=Nc(cccc2-c3c[n](C)nc3)c2C1=O)Nc1ncnc(N)c1-c1nc(C)n[o]1 GMGVCDXJCHBWBR-LBPRGKRZSA-N 0.000 description 1
- NTJCRWNWHMJBQN-SQYUSJTMSA-O C[C@@H](C(N1C2CC2)=Nc(cccc2/C(/C=[NH2+])=C/NC)c2C1=O)Nc1c(-c2n[o]c(C)n2)c(N)ncn1 Chemical compound C[C@@H](C(N1C2CC2)=Nc(cccc2/C(/C=[NH2+])=C/NC)c2C1=O)Nc1c(-c2n[o]c(C)n2)c(N)ncn1 NTJCRWNWHMJBQN-SQYUSJTMSA-O 0.000 description 1
- UJPKJELMEMATFF-VIFPVBQESA-N C[C@@H](C(N1C2CC2)=Nc(cccc2Cl)c2C1=O)Nc1c(-c2nnc(C)[o]2)c(N)ncn1 Chemical compound C[C@@H](C(N1C2CC2)=Nc(cccc2Cl)c2C1=O)Nc1c(-c2nnc(C)[o]2)c(N)ncn1 UJPKJELMEMATFF-VIFPVBQESA-N 0.000 description 1
- ZAFBJAQKRLPWFE-VIFPVBQESA-N C[C@@H](C(N1C2CC2)=Nc(cccc2Cl)c2C1=O)Nc1ncnc(N)c1-c1n[n](C)nn1 Chemical compound C[C@@H](C(N1C2CC2)=Nc(cccc2Cl)c2C1=O)Nc1ncnc(N)c1-c1n[n](C)nn1 ZAFBJAQKRLPWFE-VIFPVBQESA-N 0.000 description 1
- VDZUVKSEZOCQDT-VIFPVBQESA-N C[C@@H](C(N1C2CC2)=Nc(cccc2Cl)c2C1=O)Nc1ncnc(N)c1C1=NN(C)NN1 Chemical compound C[C@@H](C(N1C2CC2)=Nc(cccc2Cl)c2C1=O)Nc1ncnc(N)c1C1=NN(C)NN1 VDZUVKSEZOCQDT-VIFPVBQESA-N 0.000 description 1
- GYYYYQHCZOWNKE-LBPRGKRZSA-N C[C@@H](C(N1C2CC2)=Nc2cccc(-c3c[n](C)nc3)c2C1=O)Nc1ncnc(N)c1-c1nnc(C)[o]1 Chemical compound C[C@@H](C(N1C2CC2)=Nc2cccc(-c3c[n](C)nc3)c2C1=O)Nc1ncnc(N)c1-c1nnc(C)[o]1 GYYYYQHCZOWNKE-LBPRGKRZSA-N 0.000 description 1
- YGZSPHAHHZBDKP-LBPRGKRZSA-N C[C@@H](C(N1c2ccccc2)=Nc(cccc2Cl)c2C1=O)Nc1ncnc(N)c1-c1nnc(C)[o]1 Chemical compound C[C@@H](C(N1c2ccccc2)=Nc(cccc2Cl)c2C1=O)Nc1ncnc(N)c1-c1nnc(C)[o]1 YGZSPHAHHZBDKP-LBPRGKRZSA-N 0.000 description 1
- ILWDELIRXJAKEL-LHEVGVJMSA-O C[C@@H](C(N1c2ccccc2)=Nc2cccc(/C(/C=[NH2+])=C/NC)c2C1=O)Nc1c(-c2nnc(C)[o]2)c(N)ncn1 Chemical compound C[C@@H](C(N1c2ccccc2)=Nc2cccc(/C(/C=[NH2+])=C/NC)c2C1=O)Nc1c(-c2nnc(C)[o]2)c(N)ncn1 ILWDELIRXJAKEL-LHEVGVJMSA-O 0.000 description 1
- IHKVXSZBAUPREY-ZDUSSCGKSA-N C[C@@H](C(N1c2ccccc2)=Nc2cccc(Cl)c2C1=O)Nc1c(-c2nnc(C3CC3)[o]2)c(N)ncn1 Chemical compound C[C@@H](C(N1c2ccccc2)=Nc2cccc(Cl)c2C1=O)Nc1c(-c2nnc(C3CC3)[o]2)c(N)ncn1 IHKVXSZBAUPREY-ZDUSSCGKSA-N 0.000 description 1
- OPELBMIIXMNHHI-LBPRGKRZSA-N C[C@@H](C(N1c2ccccc2)=Nc2cccc(F)c2C1=O)Nc1c(-c2nc(C)n[o]2)c(N)ncn1 Chemical compound C[C@@H](C(N1c2ccccc2)=Nc2cccc(F)c2C1=O)Nc1c(-c2nc(C)n[o]2)c(N)ncn1 OPELBMIIXMNHHI-LBPRGKRZSA-N 0.000 description 1
- PITQFHMXEPLNMJ-ZDUSSCGKSA-N C[C@@H](C(N1c2ccccc2)=Nc2cccc(F)c2C1=O)Nc1ncnc(N)c1-c1nnc(C2CC2)[o]1 Chemical compound C[C@@H](C(N1c2ccccc2)=Nc2cccc(F)c2C1=O)Nc1ncnc(N)c1-c1nnc(C2CC2)[o]1 PITQFHMXEPLNMJ-ZDUSSCGKSA-N 0.000 description 1
- WZDFUJFNNXCESZ-ZDUSSCGKSA-N C[C@@H](C(N1c2ccccc2)=Nc2cccc(F)c2C1=O)Nc1ncnc(N)c1C(OC(C1CC1)=N)=N Chemical compound C[C@@H](C(N1c2ccccc2)=Nc2cccc(F)c2C1=O)Nc1ncnc(N)c1C(OC(C1CC1)=N)=N WZDFUJFNNXCESZ-ZDUSSCGKSA-N 0.000 description 1
- PKZLGRAVRZRTAO-UHFFFAOYSA-N C[n]1nc(-c2c(N)ncnc2N)nc1C(N)=O Chemical compound C[n]1nc(-c2c(N)ncnc2N)nc1C(N)=O PKZLGRAVRZRTAO-UHFFFAOYSA-N 0.000 description 1
- WCDSCEUKMOWEMW-UHFFFAOYSA-O C[n]1nc(-c2c(N)ncnc2[NH3+])nc1 Chemical compound C[n]1nc(-c2c(N)ncnc2[NH3+])nc1 WCDSCEUKMOWEMW-UHFFFAOYSA-O 0.000 description 1
- BPYDTPBOEQGXFN-UHFFFAOYSA-N C[n]1nc(-c2c([NH]=C)ncnc2N)nc1 Chemical compound C[n]1nc(-c2c([NH]=C)ncnc2N)nc1 BPYDTPBOEQGXFN-UHFFFAOYSA-N 0.000 description 1
- LPUWWWVDDWBAKB-UHFFFAOYSA-N Cc(cccc1N=C(C)N2C3CC3)c1C2=O Chemical compound Cc(cccc1N=C(C)N2C3CC3)c1C2=O LPUWWWVDDWBAKB-UHFFFAOYSA-N 0.000 description 1
- QICZPRJBSQQEPE-UHFFFAOYSA-N Cc(cccc1N=C(C)N2c(c(F)ccc3)c3F)c1C2=O Chemical compound Cc(cccc1N=C(C)N2c(c(F)ccc3)c3F)c1C2=O QICZPRJBSQQEPE-UHFFFAOYSA-N 0.000 description 1
- MLKNETGAWOCVHI-UHFFFAOYSA-N Cc1nc(-c2c(N)ncnc2NC)n[o]1 Chemical compound Cc1nc(-c2c(N)ncnc2NC)n[o]1 MLKNETGAWOCVHI-UHFFFAOYSA-N 0.000 description 1
- DNRDDFOHXBUJBM-UHFFFAOYSA-N Cc1nnc(-c2c(N)ncnc2N)[o]1 Chemical compound Cc1nnc(-c2c(N)ncnc2N)[o]1 DNRDDFOHXBUJBM-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 1
- 239000007821 HATU Substances 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 239000007993 MOPS buffer Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- 102000047918 Myelin Basic Human genes 0.000 description 1
- 101710107068 Myelin basic protein Proteins 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- XXCOSLJQAJMHQD-UHFFFAOYSA-N O=C1N(c(cccc2)c2F)C(I)=Nc2c1c(Cl)ccc2 Chemical compound O=C1N(c(cccc2)c2F)C(I)=Nc2c1c(Cl)ccc2 XXCOSLJQAJMHQD-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 239000012317 TBTU Substances 0.000 description 1
- GCTFWCDSFPMHHS-UHFFFAOYSA-M Tributyltin chloride Chemical compound CCCC[Sn](Cl)(CCCC)CCCC GCTFWCDSFPMHHS-UHFFFAOYSA-M 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- CTCBPRXHVPZNHB-VQFZJOCSSA-N [[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate;(2r,3r,4s,5r)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O.C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O CTCBPRXHVPZNHB-VQFZJOCSSA-N 0.000 description 1
- SORGEQQSQGNZFI-UHFFFAOYSA-N [azido(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(N=[N+]=[N-])OC1=CC=CC=C1 SORGEQQSQGNZFI-UHFFFAOYSA-N 0.000 description 1
- CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 1
- XEFCWBLINXJUIV-UHFFFAOYSA-N acetic acid;iodobenzene Chemical compound CC(O)=O.CC(O)=O.IC1=CC=CC=C1 XEFCWBLINXJUIV-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 229940098773 bovine serum albumin Drugs 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N c1ccncc1 Chemical compound c1ccncc1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- KYQCOXFCLRTKLS-UHFFFAOYSA-N c1cnccn1 Chemical compound c1cnccn1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N c1cncnc1 Chemical compound c1cncnc1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N c1cnncc1 Chemical compound c1cnncc1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- FYADHXFMURLYQI-UHFFFAOYSA-N c1cnncn1 Chemical compound c1cnncn1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N c1ncncn1 Chemical compound c1ncncn1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- PUQLFUHLKNBKQQ-UHFFFAOYSA-L calcium;trifluoromethanesulfonate Chemical compound [Ca+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F PUQLFUHLKNBKQQ-UHFFFAOYSA-L 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- XBSNNCXHZVUZBT-UHFFFAOYSA-N carboxysulfamoyl(triethyl)azanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)S(=O)(=O)NC(O)=O XBSNNCXHZVUZBT-UHFFFAOYSA-N 0.000 description 1
- XMPZTFVPEKAKFH-UHFFFAOYSA-P ceric ammonium nitrate Chemical compound [NH4+].[NH4+].[Ce+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O XMPZTFVPEKAKFH-UHFFFAOYSA-P 0.000 description 1
- ARQRPTNYUOLOGH-UHFFFAOYSA-N chcl3 chloroform Chemical compound ClC(Cl)Cl.ClC(Cl)Cl ARQRPTNYUOLOGH-UHFFFAOYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- JMRYOSQOYJBDOI-UHFFFAOYSA-N dilithium;di(propan-2-yl)azanide Chemical compound [Li+].CC(C)[N-]C(C)C.CC(C)N([Li])C(C)C JMRYOSQOYJBDOI-UHFFFAOYSA-N 0.000 description 1
- NCBFTYFOPLPRBX-UHFFFAOYSA-N dimethyl azodicarboxylate Substances COC(=O)N=NC(=O)OC NCBFTYFOPLPRBX-UHFFFAOYSA-N 0.000 description 1
- UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 0.000 description 1
- JMQGGPRJQOQKRT-UHFFFAOYSA-N diphenyl hydrogen phosphate;azide Chemical compound [N-]=[N+]=[N-].C=1C=CC=CC=1OP(=O)(O)OC1=CC=CC=C1 JMQGGPRJQOQKRT-UHFFFAOYSA-N 0.000 description 1
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
- VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 description 1
- CETRZFQIITUQQL-UHFFFAOYSA-N dmso dimethylsulfoxide Chemical compound CS(C)=O.CS(C)=O CETRZFQIITUQQL-UHFFFAOYSA-N 0.000 description 1
- OLAMWIPURJGSKE-UHFFFAOYSA-N et2o diethylether Chemical compound CCOCC.CCOCC OLAMWIPURJGSKE-UHFFFAOYSA-N 0.000 description 1
- LHWWETDBWVTKJO-UHFFFAOYSA-N et3n triethylamine Chemical compound CCN(CC)CC.CCN(CC)CC LHWWETDBWVTKJO-UHFFFAOYSA-N 0.000 description 1
- OCLXJTCGWSSVOE-UHFFFAOYSA-N ethanol etoh Chemical compound CCO.CCO OCLXJTCGWSSVOE-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
- NCBFTYFOPLPRBX-AATRIKPKSA-N methyl (ne)-n-methoxycarbonyliminocarbamate Chemical compound COC(=O)\N=N\C(=O)OC NCBFTYFOPLPRBX-AATRIKPKSA-N 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- FYFFGSSZFBZTAH-UHFFFAOYSA-N methylaminomethanetriol Chemical compound CNC(O)(O)O FYFFGSSZFBZTAH-UHFFFAOYSA-N 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- PEECTLLHENGOKU-UHFFFAOYSA-N n,n-dimethylpyridin-4-amine Chemical compound CN(C)C1=CC=NC=C1.CN(C)C1=CC=NC=C1 PEECTLLHENGOKU-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- VVWRJUBEIPHGQF-MDZDMXLPSA-N propan-2-yl (ne)-n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)\N=N\C(=O)OC(C)C VVWRJUBEIPHGQF-MDZDMXLPSA-N 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 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
- UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 1
- 229960002218 sodium chlorite Drugs 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- WGRULTCAYDOGQK-UHFFFAOYSA-M sodium;sodium;hydroxide Chemical compound [OH-].[Na].[Na+] WGRULTCAYDOGQK-UHFFFAOYSA-M 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 description 1
- APBDREXAUGXCCV-UHFFFAOYSA-L tetraethylazanium;carbonate Chemical compound [O-]C([O-])=O.CC[N+](CC)(CC)CC.CC[N+](CC)(CC)CC APBDREXAUGXCCV-UHFFFAOYSA-L 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- PHCBRBWANGJMHS-UHFFFAOYSA-J tetrasodium;disulfate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O PHCBRBWANGJMHS-UHFFFAOYSA-J 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361880974P | 2013-09-22 | 2013-09-22 | |
| US61/880,974 | 2013-09-22 | ||
| US201461983444P | 2014-04-23 | 2014-04-23 | |
| US61/983,444 | 2014-04-23 | ||
| PCT/US2014/055966 WO2015042077A1 (en) | 2013-09-22 | 2014-09-17 | Substituted aminopyrimidine compounds and methods of use |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016530338A JP2016530338A (ja) | 2016-09-29 |
| JP2016530338A5 true JP2016530338A5 (enExample) | 2017-07-27 |
| JP6494633B2 JP6494633B2 (ja) | 2019-04-03 |
Family
ID=52689330
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016543960A Active JP6494634B2 (ja) | 2013-09-22 | 2014-09-17 | 置換されているアミノピリミジン化合物および使用方法 |
| JP2016543959A Active JP6494633B2 (ja) | 2013-09-22 | 2014-09-17 | 置換されているアミノピリミジン化合物および使用方法 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016543960A Active JP6494634B2 (ja) | 2013-09-22 | 2014-09-17 | 置換されているアミノピリミジン化合物および使用方法 |
Country Status (12)
| Country | Link |
|---|---|
| US (4) | US9670194B2 (enExample) |
| EP (2) | EP3046563B1 (enExample) |
| JP (2) | JP6494634B2 (enExample) |
| KR (2) | KR20160060100A (enExample) |
| AU (2) | AU2014321420B2 (enExample) |
| BR (1) | BR112016003229A8 (enExample) |
| CA (2) | CA2918938C (enExample) |
| MX (2) | MX2016003456A (enExample) |
| MY (2) | MY176421A (enExample) |
| RU (2) | RU2675105C9 (enExample) |
| SG (2) | SG11201600707QA (enExample) |
| WO (3) | WO2015042078A2 (enExample) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR112016003229A8 (pt) * | 2013-09-22 | 2020-02-04 | Calitor Sciences Llc | composto, composição farmacêutica, e, uso de um composto ou de uma composição farmacêutica |
| NZ726608A (en) | 2014-06-13 | 2018-04-27 | Gilead Sciences Inc | Phosphatidylinositol 3-kinase inhibitors |
| CA2952025A1 (en) | 2014-06-13 | 2015-12-17 | Gilead Sciences, Inc. | Phosphatidylinositol 3-kinase inhibitors |
| NZ726360A (en) * | 2014-06-13 | 2018-04-27 | Gilead Sciences Inc | Phosphatidylinositol 3-kinase inhibitors |
| EA201692266A1 (ru) | 2014-06-13 | 2017-06-30 | Джилид Сайэнс, Инк. | Ингибиторы фосфатидилинозитол-3-киназы |
| CU24428B1 (es) | 2014-07-04 | 2019-06-04 | Lupin Ltd | Derivados de quinolizinona como inhibidores de pi3k |
| CN105924433B (zh) * | 2015-02-28 | 2020-12-22 | 广东东阳光药业有限公司 | 取代的氨基嘧啶类化合物及其使用方法和用途 |
| WO2016149160A1 (en) * | 2015-03-15 | 2016-09-22 | Sunshine Lake Pharma Co., Ltd. | Substituted aminopyrimidine compounds and methods of use |
| US9981965B2 (en) * | 2015-03-31 | 2018-05-29 | Synthon B.V. | Process for preparing idelalisib |
| CN106146502B (zh) * | 2015-04-09 | 2019-01-04 | 上海医药工业研究院 | 艾代拉里斯的合成方法及制备中间体 |
| CN106146352A (zh) * | 2015-04-16 | 2016-11-23 | 上海医药工业研究院 | Idelalisib中间体及其制备方法 |
| CN106146411A (zh) * | 2015-04-16 | 2016-11-23 | 上海医药工业研究院 | (s)-2-(1-氨基-丙基)-5-氟-3-苯基-3h-喹唑啉-4-酮的制备方法 |
| CN106279171A (zh) * | 2015-06-09 | 2017-01-04 | 南京安源生物医药科技有限公司 | 一种Idelalisib的制备方法 |
| EP3347097B1 (en) * | 2015-09-11 | 2021-02-24 | Sunshine Lake Pharma Co., Ltd. | Substituted aminopyrimidine derivatives as modulators of the kinases jak, flt3 and aurora |
| JP6913100B2 (ja) * | 2015-11-04 | 2021-08-04 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | Ｂｔｋ阻害活性を有するピリミジン及びピリジン化合物を用いた癌の治療方法 |
| NZ741294A (en) * | 2015-11-17 | 2023-07-28 | Merck Patent Gmbh | Methods for treating multiple sclerosis using pyrimidine and pyridine compounds with btk inhibitory activity |
| AU2016378723B2 (en) | 2015-12-22 | 2021-09-30 | SHY Therapeutics LLC | Compounds for the treatment of cancer and inflammatory disease |
| CN105669733A (zh) * | 2016-01-29 | 2016-06-15 | 上海毕路得医药科技有限公司 | 一种1-甲基-1h-吡唑-3-硼酸频哪醇酯的合成方法 |
| WO2017130221A1 (en) * | 2016-01-29 | 2017-08-03 | Sun Pharmaceutical Industries Limited | Improved process for the preparation of idelalisib |
| EP3411376A1 (en) * | 2016-02-03 | 2018-12-12 | Lupin Limited | A process for the preparation of phosphatidylinositol 3-kinase inhibitor |
| WO2017191608A1 (en) * | 2016-05-05 | 2017-11-09 | Laurus Labs Limited | Novel process for preparation of idelalisib |
| KR101932146B1 (ko) * | 2016-07-14 | 2018-12-24 | 주식회사 바이오웨이 | Pi3k를 억제하는 신규한 퀴나졸리논 유도체 및 이를 포함하는 약학적 조성물 |
| CN107648237B (zh) * | 2016-07-26 | 2022-03-04 | 江苏豪森药业集团有限公司 | 氨基嘧啶类化合物的药物组合物及其制备方法 |
| CN108017641B (zh) * | 2016-11-02 | 2021-01-05 | 深圳铂立健医药有限公司 | 吡唑并嘧啶化合物作为pi3k抑制剂及其应用 |
| CN107056810B (zh) * | 2017-02-09 | 2019-04-26 | 广东省中医院 | 一种喹诺酮羧酸衍生物的制备方法 |
| AU2018288841B2 (en) | 2017-06-21 | 2022-09-29 | SHY Therapeutics LLC | Compounds that interact with the Ras superfamily for the treatment of cancers, inflammatory diseases, Rasopathies, and fibrotic disease |
| CN110003192A (zh) * | 2018-01-04 | 2019-07-12 | 广东东阳光药业有限公司 | 取代的氨基嘧啶类化合物及其使用方法和用途 |
| US10751339B2 (en) | 2018-01-20 | 2020-08-25 | Sunshine Lake Pharma Co., Ltd. | Substituted aminopyrimidine compounds and methods of use |
| EP3898609A1 (en) | 2018-12-19 | 2021-10-27 | Shy Therapeutics LLC | Compounds that interact with the ras superfamily for the treatment of cancers, inflammatory diseases, rasopathies, and fibrotic disease |
| TW202039481A (zh) | 2018-12-21 | 2020-11-01 | 美商西建公司 | Ripk2之噻吩并吡啶抑制劑 |
| US20230201202A1 (en) * | 2020-05-27 | 2023-06-29 | Duke University | Compositions and methods for sensitizing acute myeloid leukemias to chemotherapy |
| CN115785084B (zh) * | 2022-08-26 | 2024-01-16 | 广东东阳光药业股份有限公司 | 嘧啶衍生物及其在药物中的应用 |
| WO2025021943A1 (en) * | 2023-07-26 | 2025-01-30 | Neuralis | Quinazolinone, benzoxazinone and benzoxazepinone derivatives as protein kinase inhibitors |
Family Cites Families (102)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1524747A (en) | 1976-05-11 | 1978-09-13 | Ici Ltd | Polypeptide |
| LU88769I2 (fr) | 1982-07-23 | 1996-11-05 | Zeneca Ltd | Bicalutamide et ses sels et esters pharmaceutiquement acceptables (Casodex (R)) |
| GB8327256D0 (en) | 1983-10-12 | 1983-11-16 | Ici Plc | Steroid derivatives |
| US5093330A (en) | 1987-06-15 | 1992-03-03 | Ciba-Geigy Corporation | Staurosporine derivatives substituted at methylamino nitrogen |
| US5010099A (en) | 1989-08-11 | 1991-04-23 | Harbor Branch Oceanographic Institution, Inc. | Discodermolide compounds, compositions containing same and method of preparation and use |
| NZ243082A (en) | 1991-06-28 | 1995-02-24 | Ici Plc | 4-anilino-quinazoline derivatives; pharmaceutical compositions, preparatory processes, and use thereof |
| GB9127376D0 (en) | 1991-12-24 | 1992-02-19 | Wellcome Found | Amidino derivatives |
| AU661533B2 (en) | 1992-01-20 | 1995-07-27 | Astrazeneca Ab | Quinazoline derivatives |
| EP0633776B1 (en) | 1992-04-02 | 2001-05-09 | Smithkline Beecham Corporation | Compounds useful for treating allergic and inflammatory diseases |
| TW225528B (enExample) | 1992-04-03 | 1994-06-21 | Ciba Geigy Ag | |
| GB9314893D0 (en) | 1993-07-19 | 1993-09-01 | Zeneca Ltd | Quinazoline derivatives |
| SI0957087T1 (en) | 1994-06-15 | 2003-04-30 | The Wellcome Foundation Limited | Intermediates useful in the preparation of enzyme inhibitors |
| ES2332984T3 (es) | 1995-03-30 | 2010-02-16 | Pfizer Products Inc. | Derivados de quinazolinas. |
| EA000890B1 (ru) | 1995-04-14 | 2000-06-26 | Глаксо Веллкам Инк. | Дозирующий ингалятор для албутерола |
| GB9508538D0 (en) | 1995-04-27 | 1995-06-14 | Zeneca Ltd | Quinazoline derivatives |
| US5747498A (en) | 1996-05-28 | 1998-05-05 | Pfizer Inc. | Alkynyl and azido-substituted 4-anilinoquinazolines |
| US5843901A (en) | 1995-06-07 | 1998-12-01 | Advanced Research & Technology Institute | LHRH antagonist peptides |
| WO1997002266A1 (en) | 1995-07-06 | 1997-01-23 | Novartis Ag | Pyrrolopyrimidines and processes for the preparation thereof |
| US5760041A (en) | 1996-02-05 | 1998-06-02 | American Cyanamid Company | 4-aminoquinazoline EGFR Inhibitors |
| GB9603095D0 (en) | 1996-02-14 | 1996-04-10 | Zeneca Ltd | Quinazoline derivatives |
| CN1923818A (zh) | 1996-04-12 | 2007-03-07 | 沃尼尔·朗伯公司 | 酪氨酸激酶的不可逆抑制剂 |
| WO1997049688A1 (en) | 1996-06-24 | 1997-12-31 | Pfizer Inc. | Phenylamino-substituted tricyclic derivatives for treatment of hyperproliferative diseases |
| AU716610B2 (en) | 1996-08-30 | 2000-03-02 | Novartis Ag | Method for producing epothilones, and intermediate products obtained during the production process |
| DE69724269T2 (de) | 1996-09-06 | 2004-06-09 | Obducat Ab | Verfahren für das anisotrope ätzen von strukturen in leitende materialien |
| WO1998010767A2 (en) | 1996-09-13 | 1998-03-19 | Sugen, Inc. | Use of quinazoline derivatives for the manufacture of a medicament in the treatment of hyperproliferative skin disorders |
| EP0837063A1 (en) | 1996-10-17 | 1998-04-22 | Pfizer Inc. | 4-Aminoquinazoline derivatives |
| DK1367057T3 (da) | 1996-11-18 | 2009-01-19 | Biotechnolog Forschung Gmbh | Epothiloner E og F |
| US6441186B1 (en) | 1996-12-13 | 2002-08-27 | The Scripps Research Institute | Epothilone analogs |
| MY117948A (en) | 1997-01-13 | 2004-08-30 | Glaxo Group Ltd | Nitride oxide synthase inhibitors. |
| DE19723722A1 (de) | 1997-05-30 | 1998-12-10 | Schering Ag | Nichtsteroidale Gestagene |
| TW533865U (en) | 1997-06-10 | 2003-05-21 | Glaxo Group Ltd | Dispenser for dispensing medicament and actuation indicating device |
| CO4940418A1 (es) | 1997-07-18 | 2000-07-24 | Novartis Ag | Modificacion de cristal de un derivado de n-fenil-2- pirimidinamina, procesos para su fabricacion y su uso |
| GB9721069D0 (en) | 1997-10-03 | 1997-12-03 | Pharmacia & Upjohn Spa | Polymeric derivatives of camptothecin |
| US6506766B1 (en) | 1998-02-13 | 2003-01-14 | Abbott Laboratories | Glucocortiocoid-selective antinflammatory agents |
| US6194181B1 (en) | 1998-02-19 | 2001-02-27 | Novartis Ag | Fermentative preparation process for and crystal forms of cytostatics |
| CA2322157C (en) | 1998-02-25 | 2012-05-29 | Sloan-Kettering Institute For Cancer Research | Synthesis of epothilones, intermediates thereto and analogues thereof |
| GB9811599D0 (en) | 1998-05-30 | 1998-07-29 | Glaxo Group Ltd | Nitric oxide synthase inhibitors |
| DE69942097D1 (de) | 1998-08-11 | 2010-04-15 | Novartis Ag | Isochinoline derivate mit angiogenesis-hemmender wirkung |
| EP1135470A2 (en) | 1998-11-20 | 2001-09-26 | Kosan Biosciences, Inc. | Recombinant methods and materials for producing epothilone and epothilone derivatives |
| US6352152B1 (en) | 1998-12-18 | 2002-03-05 | Smithkline Beecham Corporation | Method and package for storing a pressurized container containing a drug |
| US6315112B1 (en) | 1998-12-18 | 2001-11-13 | Smithkline Beecham Corporation | Method and package for storing a pressurized container containing a drug |
| US6390291B1 (en) | 1998-12-18 | 2002-05-21 | Smithkline Beecham Corporation | Method and package for storing a pressurized container containing a drug |
| US6119853A (en) | 1998-12-18 | 2000-09-19 | Glaxo Wellcome Inc. | Method and package for storing a pressurized container containing a drug |
| HK1043788A1 (zh) | 1999-05-04 | 2002-09-27 | American Home Products Corporation | 四環黃體酮受體調節劑化合物及方法 |
| ES2165768B1 (es) | 1999-07-14 | 2003-04-01 | Almirall Prodesfarma Sa | Nuevos derivados de quinuclidina y composiciones farmaceuticas que los contienen. |
| CO5180649A1 (es) | 1999-09-01 | 2002-07-30 | Abbott Lab | Antagonistas de los receptores de los glucocorticoides para el tratamiento de la diabetes para el tratamiento de la diabetes |
| US6667300B2 (en) | 2000-04-25 | 2003-12-23 | Icos Corporation | Inhibitors of human phosphatidylinositol 3-kinase delta |
| EP1278748B1 (en) | 2000-04-25 | 2011-03-23 | ICOS Corporation | Inhibitors of human phosphatidyl-inositol 3-kinase delta |
| PE20020354A1 (es) | 2000-09-01 | 2002-06-12 | Novartis Ag | Compuestos de hidroxamato como inhibidores de histona-desacetilasa (hda) |
| BR0114323A (pt) | 2000-09-29 | 2003-07-01 | Glaxo Group Ltd | Composto ou um seu sal ou solvato farmaceuticamente aceitável, composição farmacêutica, uso do composto ou de um seu sal ou solvato farmaceuticamente aceitável, método de tratamento ou profilaxia de doenças inflamatórias, e, processo para preparar o composto |
| DK1337527T3 (da) | 2000-11-07 | 2010-01-04 | Novartis Ag | Indolylmaleinimidderivater som proteinkinase C-inhibitorer |
| GB0031179D0 (en) | 2000-12-21 | 2001-01-31 | Glaxo Group Ltd | Nitric oxide synthase inhibitors |
| US6484903B2 (en) | 2001-01-09 | 2002-11-26 | Riverwood International Corporation | Carton with an improved dispensing feature in combination with a unique handle |
| AR035885A1 (es) | 2001-05-14 | 2004-07-21 | Novartis Ag | Derivados de 4-amino-5-fenil-7-ciclobutilpirrolo (2,3-d)pirimidina, un proceso para su preparacion, una composicion farmaceutica y el uso de dichos derivados para la preparacion de una composicion farmaceutica |
| GB0119249D0 (en) | 2001-08-07 | 2001-10-03 | Novartis Ag | Organic compounds |
| WO2003059899A1 (en) | 2002-01-14 | 2003-07-24 | Boehringer Ingelheim Pharmaceuticals, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical formulations containing them and uses thereof |
| CA2473886C (en) | 2002-01-22 | 2012-08-21 | The Regents Of The University Of California | Non-steroidal ligands for the glucocorticoid receptor, compositions and uses thereof |
| EP1490317A1 (en) | 2002-03-26 | 2004-12-29 | Boehringer Ingelheim Pharmaceuticals Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
| PT1490062E (pt) | 2002-03-26 | 2008-01-30 | Boehringer Ingelheim Pharma | Miméticos de glucocorticóides, métodos para a sua preparação, composições farmacêuticas e suas utilizações |
| DE10215316C1 (de) | 2002-04-02 | 2003-12-18 | Schering Ag | Chinolin- und Isochinolin-Derivate, ein pharmazeutisches Mittel und ihre Verwendung als Entzündungshemmer |
| AR039209A1 (es) | 2002-04-03 | 2005-02-09 | Novartis Ag | Derivados de indolilmaleimida |
| WO2003086294A2 (en) | 2002-04-11 | 2003-10-23 | Merck & Co., Inc. | 1h-benzo[f]indazol-5-yl derivatives as selective glucocorticoid receptor modulators |
| US7186864B2 (en) | 2002-05-29 | 2007-03-06 | Boehringer Ingelheim Pharmaceuticals, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
| US7074806B2 (en) | 2002-06-06 | 2006-07-11 | Boehringer Ingelheim Pharmaceuticals, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
| BR0312575A (pt) | 2002-07-08 | 2005-05-03 | Pfizer Prod Inc | Moduladores do receptor de glicocorticóides |
| AU2003251970A1 (en) | 2002-07-18 | 2004-02-09 | Bristol-Myers Squibb Company | Modulators of the glucocorticoid receptor and method |
| JP2006504678A (ja) | 2002-08-21 | 2006-02-09 | ベーリンガー インゲルハイム ファーマシューティカルズ インコーポレイテッド | グルココルチコイドミメチックス、その製造方法、その医薬組成物、及び使用 |
| US20050245588A1 (en) | 2002-09-20 | 2005-11-03 | Amjad Ali | Octahydro-2-h-naphtho[1,2-f]indole-4-carboxamide derivatives as selective glucocorticoid receptor modulators |
| GB0224084D0 (en) | 2002-10-16 | 2002-11-27 | Glaxo Group Ltd | Novel compounds |
| EP1578411A4 (en) | 2002-12-09 | 2007-05-02 | Univ Texas | PROCESS FOR THE SELECTIVE INHIBITION OF JANUS TYROSINE KINASE3 (JAK3) |
| PT1699512E (pt) | 2003-11-03 | 2012-09-11 | Glaxo Group Ltd | Dispositivo distribuidor de fluido |
| KR101164541B1 (ko) | 2004-01-12 | 2012-07-10 | 와이엠 바이오사이언시즈 오스트레일리아 피티와이 엘티디 | 선택적 키나제 저해제 |
| EP1749827A4 (en) | 2004-03-30 | 2010-04-21 | Kyowa Hakko Kirin Co Ltd | ANTITUMOR AGENTS |
| CN102229609A (zh) | 2004-05-13 | 2011-11-02 | 艾科斯有限公司 | 作为人磷脂酰肌醇3-激酶δ抑制剂的喹唑啉酮 |
| WO2006000401A1 (en) | 2004-06-28 | 2006-01-05 | Glaxo Group Limited | Substituted oxazines as glucocorticoid receptor modulators |
| WO2006000398A1 (en) | 2004-06-28 | 2006-01-05 | Glaxo Group Limited | 2,3-benzoxazin derivatives as non-steroidal glucocorticoid receptor modulators |
| GB0418045D0 (en) | 2004-08-12 | 2004-09-15 | Glaxo Group Ltd | Compounds |
| ATE517882T1 (de) | 2004-10-19 | 2011-08-15 | Hoffmann La Roche | Chinolinderivate |
| JP2010513567A (ja) * | 2006-12-19 | 2010-04-30 | バーテックス ファーマシューティカルズ インコーポレイテッド | プロテインキナーゼの阻害剤として有用なアミノピリミジン |
| PE20090717A1 (es) | 2007-05-18 | 2009-07-18 | Smithkline Beecham Corp | Derivados de quinolina como inhibidores de la pi3 quinasa |
| CN101952292A (zh) | 2007-11-13 | 2011-01-19 | 艾科斯有限公司 | 人磷脂酰肌醇3-激酶δ的抑制剂 |
| KR101660050B1 (ko) | 2008-01-04 | 2016-09-26 | 인텔리카인, 엘엘씨 | 특정 화학 물질, 조성물 및 방법 |
| US8193182B2 (en) | 2008-01-04 | 2012-06-05 | Intellikine, Inc. | Substituted isoquinolin-1(2H)-ones, and methods of use thereof |
| CN102439012A (zh) | 2009-03-24 | 2012-05-02 | 吉里德卡利斯托加公司 | 2-嘌呤基-3-甲苯基-喹唑啉酮衍生物的阻转异构体和使用方法 |
| CA2760791C (en) | 2009-05-07 | 2017-06-20 | Intellikine, Inc. | Heterocyclic compounds and uses thereof |
| UY33304A (es) * | 2010-04-02 | 2011-10-31 | Amgen Inc | Compuestos heterocíclicos y sus usos |
| EP2571357B1 (en) | 2010-05-21 | 2016-07-06 | Infinity Pharmaceuticals, Inc. | Chemical compounds, compositions and methods for kinase modulation |
| KR20150144817A (ko) * | 2011-06-10 | 2015-12-28 | 메르크 파텐트 게엠베하 | Btk 억제 활성을 갖는 피리미딘 및 피리딘 화합물의 조성물 및 제조방법 |
| CN103930422A (zh) | 2011-07-19 | 2014-07-16 | 无限药品股份有限公司 | 杂环化合物及其用途 |
| AR088218A1 (es) | 2011-07-19 | 2014-05-21 | Infinity Pharmaceuticals Inc | Compuestos heterociclicos utiles como inhibidores de pi3k |
| AU2012302197B2 (en) | 2011-08-29 | 2016-01-07 | Infinity Pharmaceuticals Inc. | Heterocyclic compounds and uses thereof |
| US20130143902A1 (en) | 2011-12-02 | 2013-06-06 | Gilead Calistoga Llc | Compositions and methods of treating a proliferative disease with a quinazolinone derivative |
| WO2013116562A1 (en) | 2012-02-03 | 2013-08-08 | Gilead Calistoga Llc | Compositions and methods of treating a disease with (s)-4 amino-6-((1-(5-chloro-4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)ethyl)amino)pyrimidine-5-carbonitrile |
| CN104768952B (zh) | 2012-08-08 | 2016-10-19 | 山东亨利医药科技有限责任公司 | PI3Kδ抑制剂 |
| PE20150637A1 (es) | 2012-10-16 | 2015-05-08 | Almirall Sa | Derivados de pirrolotriazinona como inhibidores de pi3k |
| CA2895782C (en) | 2012-12-21 | 2017-08-22 | Gilead Calistoga Llc | Substituted pyrimidine aminoalkyl-quinazolones as phosphatidylinositol 3-kinase inhibitors |
| BR112015014592A2 (pt) | 2012-12-21 | 2017-07-11 | Gilead Calistoga Llc | composto, composição farmacêutica, e, método para o tratamento de um humano |
| WO2014106800A2 (en) | 2013-01-04 | 2014-07-10 | Aurigene Discovery Technologies Limited | Substituted 2-amino pyrimidine derivatives as kinase inhibitors |
| UY35332A (es) | 2013-02-15 | 2014-11-28 | Almirall Sa | Derivados de pirrolotriazina como inhibidores de pi3k |
| US9216985B2 (en) | 2013-03-28 | 2015-12-22 | Scifluor Life Sciences, Inc. | 3-aryl-2-((arylamino)methyl)quinazolin-4-(3H)-ones |
| EP3008053B1 (en) | 2013-06-14 | 2018-03-21 | Gilead Calistoga LLC | Phosphatidylinositol 3-kinase inhibitors |
| BR112016003229A8 (pt) * | 2013-09-22 | 2020-02-04 | Calitor Sciences Llc | composto, composição farmacêutica, e, uso de um composto ou de uma composição farmacêutica |
-
2014
- 2014-09-17 BR BR112016003229A patent/BR112016003229A8/pt active Search and Examination
- 2014-09-17 JP JP2016543960A patent/JP6494634B2/ja active Active
- 2014-09-17 CA CA2918938A patent/CA2918938C/en active Active
- 2014-09-17 KR KR1020167010190A patent/KR20160060100A/ko not_active Ceased
- 2014-09-17 RU RU2016114866A patent/RU2675105C9/ru active
- 2014-09-17 WO PCT/US2014/055967 patent/WO2015042078A2/en not_active Ceased
- 2014-09-17 AU AU2014321420A patent/AU2014321420B2/en active Active
- 2014-09-17 CA CA2920059A patent/CA2920059A1/en not_active Abandoned
- 2014-09-17 SG SG11201600707QA patent/SG11201600707QA/en unknown
- 2014-09-17 MY MYPI2016700882A patent/MY176421A/en unknown
- 2014-09-17 AU AU2014321419A patent/AU2014321419B2/en active Active
- 2014-09-17 RU RU2016115082A patent/RU2683793C2/ru active
- 2014-09-17 US US14/488,294 patent/US9670194B2/en active Active
- 2014-09-17 SG SG11201600028YA patent/SG11201600028YA/en unknown
- 2014-09-17 US US14/488,296 patent/US9657007B2/en active Active
- 2014-09-17 MX MX2016003456A patent/MX2016003456A/es unknown
- 2014-09-17 EP EP14846242.7A patent/EP3046563B1/en active Active
- 2014-09-17 MX MX2016003457A patent/MX2016003457A/es unknown
- 2014-09-17 KR KR1020167010188A patent/KR20160058889A/ko not_active Ceased
- 2014-09-17 EP EP14845629.6A patent/EP3046921A4/en not_active Ceased
- 2014-09-17 JP JP2016543959A patent/JP6494633B2/ja active Active
- 2014-09-17 MY MYPI2016700874A patent/MY184292A/en unknown
- 2014-09-17 WO PCT/US2014/055966 patent/WO2015042077A1/en not_active Ceased
- 2014-09-21 WO PCT/US2014/056702 patent/WO2015042497A2/en not_active Ceased
-
2015
- 2015-03-15 US US14/658,189 patent/US9518046B2/en active Active
- 2015-03-15 US US14/658,190 patent/US9512114B2/en active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2016530338A5 (enExample) | ||
| JP2016534146A5 (enExample) | ||
| ES2549862T3 (es) | Derivados de triazol como inhibidores de quinasa | |
| KR102012268B1 (ko) | 염증성 질환의 치료를 위한 신규의 다이하이드로피리미디노아이소퀴놀리논 및 그의 약학 조성물 | |
| ES2708211T3 (es) | 3-amino-1,5,6,7-tetrahidro-4H-indol-4-onas | |
| JP7558334B2 (ja) | ＰＩ３Ｋ－γ阻害剤としてのアミノピラジンジオール化合物 | |
| US10590077B2 (en) | TRPV4 antagonists | |
| ES2505290T3 (es) | Derivados de 3,4,4A,10B-tetrahidro-1H-tiopirano[4,3-c]isoquinolina | |
| ES2807221T3 (es) | Derivados de 4-azaindol | |
| BRPI0720043A2 (pt) | Composto oxadiazol | |
| JP7244504B2 (ja) | ＰＩ３Ｋ－γ阻害剤としての三級ヒドロキシ基で置換された縮合イミダゾール誘導体 | |
| KR20180132806A (ko) | 단백질 조정제로서 유용한 헤테로시클릭 아미드 | |
| JP2012140432A5 (enExample) | ||
| JP2016507581A5 (enExample) | ||
| EP3515887A1 (en) | Trpv4 antagonists | |
| EP3515888A1 (en) | Trpv4 antagonists | |
| JP2013522316A5 (enExample) | ||
| WO2020010003A1 (en) | AMINOPYRAZINE DERIVATIVES AS PI3K-γ INHIBITORS | |
| TW202229273A (zh) | 稠合雜芳基化合物及其作為CaMKII抑制劑之用途 | |
| JP2010537994A5 (enExample) | ||
| JP2013543512A5 (enExample) | ||
| CN105924434A (zh) | 取代的氨基嘧啶类化合物及其使用方法和用途 | |
| JP2016539993A5 (enExample) | ||
| BR122025015788A2 (pt) | Compostos de aminopirazina diol, seus usos como inibidores de pi3k- gama e composição farmacêutica dos mesmos | |
| EA045434B1 (ru) | СОЕДИНЕНИЯ АМИНОПИРАЗИНДИОЛА КАК ИНГИБИТОРЫ PI3Kγ |