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 (show.php) | 2017-07-27 |
| JP6494633B2 JP6494633B2 (ja) | 2019-04-03 |
Family
ID=52689330
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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 |
| 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 |
Family Applications After (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 (show.php) |
| EP (2) | EP3046563B1 (show.php) |
| JP (2) | JP6494633B2 (show.php) |
| KR (2) | KR20160058889A (show.php) |
| AU (2) | AU2014321419B2 (show.php) |
| BR (1) | BR112016003229A8 (show.php) |
| CA (2) | CA2920059A1 (show.php) |
| MX (2) | MX2016003457A (show.php) |
| MY (2) | MY184292A (show.php) |
| RU (2) | RU2683793C2 (show.php) |
| SG (2) | SG11201600707QA (show.php) |
| WO (3) | WO2015042078A2 (show.php) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY184292A (en) * | 2013-09-22 | 2021-03-30 | Sunshine Lake Pharma Co Ltd | Substituted aminopyrimidine compounds and methods of use |
| ES2763104T3 (es) | 2014-06-13 | 2020-05-27 | Gilead Sciences Inc | Derivados de quinazolinona como inhibidores de fosfatidilinositol 3-quinasa |
| CA2952025A1 (en) | 2014-06-13 | 2015-12-17 | Gilead Sciences, Inc. | Phosphatidylinositol 3-kinase inhibitors |
| US11021467B2 (en) * | 2014-06-13 | 2021-06-01 | Gilead Sciences, Inc. | Phosphatidylinositol 3-kinase inhibitors |
| WO2015191752A1 (en) | 2014-06-13 | 2015-12-17 | Gilead Sciences, Inc. | Phosphatidylinositol 3-kinase inhibitors |
| BR112017000132A2 (en) | 2014-07-04 | 2018-01-09 | Lupin Limited | compound, pharmaceutical composition and method of treating or preventing a disease responsive to inhibition of pi3k activity |
| 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 |
| 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 |
| 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 |
| 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 |
| WO2017044434A1 (en) | 2015-09-11 | 2017-03-16 | Sunshine Lake Pharma Co., Ltd. | Substituted heteroaryl compounds and methods of use |
| AU2016349584B9 (en) * | 2015-11-04 | 2021-06-03 | Merck Patent Gmbh | Methods for treating cancer using pyrimidine and pyridine compounds with BTK inhibitory activity |
| EP3377484B1 (en) | 2015-11-17 | 2023-09-06 | Merck Patent GmbH | Methods for treating multiple sclerosis using pyrimidine and pyridine compounds with btk inhibitory activity |
| JP7114076B2 (ja) | 2015-12-22 | 2022-08-08 | シャイ・セラピューティクス・エルエルシー | がん及び炎症性疾患の処置のための化合物 |
| 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 |
| US20190040066A1 (en) * | 2016-02-03 | 2019-02-07 | Lupin Limited | 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 |
| IL271230B2 (en) | 2017-06-21 | 2024-06-01 | 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 |
| CA3083040A1 (en) * | 2018-01-20 | 2019-07-25 | Sunshine Lake Pharma Co., Ltd. | Substituted aminopyrimidine compounds and methods of use |
| JP7407461B2 (ja) | 2018-12-19 | 2024-01-04 | シャイ・セラピューティクス・エルエルシー | がん、炎症性疾患、ｒａｓ病、及び線維性疾患の処置のためのｒａｓスーパーファミリーと相互作用する化合物 |
| CN113874015B (zh) | 2018-12-21 | 2024-05-24 | 细胞基因公司 | Ripk2的噻吩并吡啶抑制剂 |
| WO2021242859A1 (en) * | 2020-05-27 | 2021-12-02 | 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 |
| EP0100172B1 (en) | 1982-07-23 | 1987-08-12 | Imperial Chemical Industries Plc | Amide derivatives |
| 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 |
| GB9300059D0 (en) | 1992-01-20 | 1993-03-03 | Zeneca Ltd | Quinazoline derivatives |
| FI944549A7 (fi) | 1992-04-02 | 1994-11-30 | Smithkline Beecham Corp | Allergisten ja tulehdussairauksien hoidossa käyttökelpoiset yhdisteet |
| TW225528B (show.php) | 1992-04-03 | 1994-06-21 | Ciba Geigy Ag | |
| GB9314893D0 (en) | 1993-07-19 | 1993-09-01 | Zeneca Ltd | Quinazoline derivatives |
| AU692892B2 (en) | 1994-06-15 | 1998-06-18 | Wellcome Foundation Limited, The | Enzyme inhibitors |
| PT817775E (pt) | 1995-03-30 | 2002-01-30 | Pfizer | Derivados de quinazolina |
| AP791A (en) | 1995-04-14 | 1999-12-17 | Glaxo Wellcome Inc | Metered dose inhaler for albuterol. |
| 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 |
| IL122855A (en) | 1995-07-06 | 2004-08-31 | Novartis Ag | History of N-Phenyl (Alkyl) - 7H-Pyrolo [-3,2d] Pyrimidine - 4 Amine, their preparation and pharmaceutical preparations containing them |
| 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 |
| CZ295468B6 (cs) | 1996-04-12 | 2005-08-17 | Warner-Lambert Company | Polycyklické sloučeniny |
| ATE308527T1 (de) | 1996-06-24 | 2005-11-15 | Pfizer | Phenylamino-substituierte triicyclische derivate zur behandlung hyperproliferativer krankheiten |
| WO1998008849A1 (de) | 1996-08-30 | 1998-03-05 | Novartis Aktiengesellschaft | Verfahren zur herstellung von epothilonen und zwischenprodukte innerhalb des verfahrens |
| CA2264908C (en) | 1996-09-06 | 2006-04-25 | Obducat Ab | Method for anisotropic etching of structures in conducting materials |
| 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 |
| DE59712968D1 (de) | 1996-11-18 | 2008-10-30 | Biotechnolog Forschung Gmbh | Epothilone E und 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 |
| MXPA00008365A (es) | 1998-02-25 | 2002-11-07 | Sloan Kettering Inst Cancer | Sintesis de epotilonas, intermediarios y analogos de las mismas. |
| GB9811599D0 (en) | 1998-05-30 | 1998-07-29 | Glaxo Group Ltd | Nitric oxide synthase inhibitors |
| EP1107964B8 (en) | 1998-08-11 | 2010-04-07 | Novartis AG | Isoquinoline derivatives with angiogenesis inhibiting activity |
| KR100851418B1 (ko) | 1998-11-20 | 2008-08-08 | 코산 바이오사이언시즈, 인코포레이티드 | 에포틸론 및 에포틸론 유도체의 생산을 위한 재조합 방법 및 물질 |
| US6390291B1 (en) | 1998-12-18 | 2002-05-21 | 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 |
| US6119853A (en) | 1998-12-18 | 2000-09-19 | Glaxo Wellcome Inc. | Method and package for storing a pressurized container containing a drug |
| US6352152B1 (en) | 1998-12-18 | 2002-03-05 | Smithkline Beecham Corporation | 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 |
| PT1278748E (pt) | 2000-04-25 | 2011-03-31 | Icos Corp | Inibidores de delta 3-cinase humana de fosfatidilinositol |
| PE20020354A1 (es) | 2000-09-01 | 2002-06-12 | Novartis Ag | Compuestos de hidroxamato como inhibidores de histona-desacetilasa (hda) |
| IL155093A0 (en) | 2000-09-29 | 2003-10-31 | Glaxo Group Ltd | Morpholin-acetamide derivatives for the treatment on inflammatory diseases |
| KR20080014934A (ko) | 2000-11-07 | 2008-02-14 | 노파르티스 아게 | 단백질 키나제 ｃ 억제제로서의 인돌릴말레이미드 유도체 |
| 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 |
| DE60309829T2 (de) | 2002-01-14 | 2007-09-13 | Boehringer Ingelheim Pharmaceuticals, Inc., Ridgefield | Glucocorticoidmimetika, verfahren zu ihrer herstellung, diese enthaltende pharmazeutische formulierungen und ihre verwendungen |
| AU2003214879B2 (en) | 2002-01-22 | 2008-02-07 | The Regents Of The University Of California | Non-steroidal ligands for the glucocorticoid receptor, compositions and uses thereof |
| HRP20040887A2 (en) | 2002-03-26 | 2005-04-30 | Boehringer Ingelheim Pharmaceuticals Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
| JP2005521717A (ja) | 2002-03-26 | 2005-07-21 | 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 |
| DE10215316C1 (de) | 2002-04-02 | 2003-12-18 | Schering Ag | Chinolin- und Isochinolin-Derivate, ein pharmazeutisches Mittel und ihre Verwendung als Entzündungshemmer |
| TWI324064B (en) | 2002-04-03 | 2010-05-01 | Novartis Ag | Indolylmaleimide derivatives |
| DE60335869D1 (de) | 2002-04-11 | 2011-03-10 | Merck Sharp & Dohme | 1h-benzo(f)indazol-5-yl-derivate als selektive glucocorticoid-rezeptor-modulatoren |
| 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 |
| MXPA05000345A (es) | 2002-07-08 | 2005-03-31 | Pfizer Prod Inc | Moduladores del receptor de glucocorticoides. |
| WO2004009017A2 (en) | 2002-07-18 | 2004-01-29 | 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 |
| HUP0500844A2 (en) | 2002-12-09 | 2007-08-28 | Univ Texas | Methods for selectively inhibiting janus tyrosine kinase 3(jak3) |
| WO2005044354A1 (en) | 2003-11-03 | 2005-05-19 | Glaxo Group Limited | A fluid dispensing device |
| MXPA06007640A (es) | 2004-01-12 | 2007-04-17 | Cytopia Res Pty Ltd | Inhibidores de quinasa selectivos. |
| JPWO2005095382A1 (ja) | 2004-03-30 | 2007-08-16 | 協和醗酵工業株式会社 | 抗腫瘍剤 |
| JP2007537291A (ja) | 2004-05-13 | 2007-12-20 | イコス・コーポレイション | ヒトホスファチジルイノシトール３−キナーゼデルタの阻害剤としてのキナゾリノン |
| 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 |
| RU2391338C2 (ru) | 2004-10-19 | 2010-06-10 | Ф.Хоффманн-Ля Рош Аг | Производные хинолина |
| 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 |
| JP2011503193A (ja) | 2007-11-13 | 2011-01-27 | アイコス、コーポレーション | ヒトホスファチジルイノシトール３−キナーゼδの阻害剤 |
| AU2009204487C1 (en) | 2008-01-04 | 2014-10-16 | Intellikine, Llc | Certain chemical entities, compositions and methods |
| US8193182B2 (en) | 2008-01-04 | 2012-06-05 | Intellikine, Inc. | Substituted isoquinolin-1(2H)-ones, and methods of use thereof |
| KR20120002995A (ko) * | 2009-03-24 | 2012-01-09 | 길리아드 칼리스토가 엘엘씨 | ２―퓨리닐―３―톨릴―퀴나졸리논 유도체의 회전장애 이성질체 및 사용 방법 |
| 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 |
| ES2593256T3 (es) | 2010-05-21 | 2016-12-07 | Infinity Pharmaceuticals, Inc. | Compuestos químicos, composiciones y métodos para las modulaciones de cinasas |
| CN106831732B (zh) * | 2011-06-10 | 2019-12-24 | 默克专利有限公司 | 生产具有btk抑制活性的嘧啶和吡啶化合物的组合物和方法 |
| HK1198443A1 (en) | 2011-07-19 | 2015-04-24 | 无限药品股份有限公司 | Heterocyclic compounds and uses thereof |
| AU2012284091B2 (en) | 2011-07-19 | 2015-11-12 | Infinity Pharmaceuticals Inc. | Heterocyclic compounds and uses thereof |
| EP2751093A1 (en) | 2011-08-29 | 2014-07-09 | 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 |
| KR20150068953A (ko) | 2012-10-16 | 2015-06-22 | 알미랄, 에스.에이. | Ｐｉ３ｋ 저해제로서의 피롤로트리아지논 유도체 |
| WO2014100765A1 (en) | 2012-12-21 | 2014-06-26 | Gilead Calistoga Llc | Substituted pyrimidine aminoalkyl-quinazolones as phosphatidylinositol 3-kinase inhibitors |
| US9029384B2 (en) | 2012-12-21 | 2015-05-12 | Gilead Calistoga, LLC. | Phosphatidylinositol 3-kinase inhibitors |
| WO2014106800A2 (en) | 2013-01-04 | 2014-07-10 | Aurigene Discovery Technologies Limited | Substituted 2-amino pyrimidine derivatives as kinase inhibitors |
| TW201446767A (zh) | 2013-02-15 | 2014-12-16 | Almirall Sa | 作為磷脂肌醇3-激酶抑製劑之吡咯並三嗪衍生物 |
| US9216985B2 (en) | 2013-03-28 | 2015-12-22 | Scifluor Life Sciences, Inc. | 3-aryl-2-((arylamino)methyl)quinazolin-4-(3H)-ones |
| EA028319B1 (ru) | 2013-06-14 | 2017-11-30 | Джилид Калистога Ллс | Ингибиторы фосфатидилинозитол-3-киназы |
| MY184292A (en) * | 2013-09-22 | 2021-03-30 | Sunshine Lake Pharma Co Ltd | Substituted aminopyrimidine compounds and methods of use |
-
2014
- 2014-09-17 MY MYPI2016700874A patent/MY184292A/en unknown
- 2014-09-17 SG SG11201600707QA patent/SG11201600707QA/en unknown
- 2014-09-17 MX MX2016003457A patent/MX2016003457A/es unknown
- 2014-09-17 AU AU2014321419A patent/AU2014321419B2/en active Active
- 2014-09-17 JP JP2016543959A patent/JP6494633B2/ja active Active
- 2014-09-17 RU RU2016115082A patent/RU2683793C2/ru active
- 2014-09-17 MY MYPI2016700882A patent/MY176421A/en unknown
- 2014-09-17 RU RU2016114866A patent/RU2675105C9/ru active
- 2014-09-17 SG SG11201600028YA patent/SG11201600028YA/en unknown
- 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 KR KR1020167010188A patent/KR20160058889A/ko not_active Ceased
- 2014-09-17 JP JP2016543960A patent/JP6494634B2/ja active Active
- 2014-09-17 CA CA2920059A patent/CA2920059A1/en not_active Abandoned
- 2014-09-17 US US14/488,294 patent/US9670194B2/en active Active
- 2014-09-17 US US14/488,296 patent/US9657007B2/en active Active
- 2014-09-17 BR BR112016003229A patent/BR112016003229A8/pt active Search and Examination
- 2014-09-17 KR KR1020167010190A patent/KR20160060100A/ko not_active Ceased
- 2014-09-17 CA CA2918938A patent/CA2918938C/en active Active
- 2014-09-17 MX MX2016003456A patent/MX2016003456A/es unknown
- 2014-09-17 WO PCT/US2014/055966 patent/WO2015042077A1/en not_active Ceased
- 2014-09-17 EP EP14846242.7A patent/EP3046563B1/en active Active
- 2014-09-17 EP EP14845629.6A patent/EP3046921A4/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 (show.php) | ||
| JP2016534146A5 (show.php) | ||
| 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 (show.php) | ||
| JP2016507581A5 (show.php) | ||
| EP3515887A1 (en) | Trpv4 antagonists | |
| EP3515888A1 (en) | Trpv4 antagonists | |
| JP2013522316A5 (show.php) | ||
| 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 (show.php) | ||
| JP2013543512A5 (show.php) | ||
| CN105924434A (zh) | 取代的氨基嘧啶类化合物及其使用方法和用途 | |
| JP2016539993A5 (show.php) | ||
| ES2517265T3 (es) | Derivados de oxadiazol piridina | |
| BR122025015788A2 (pt) | Compostos de aminopirazina diol, seus usos como inibidores de pi3k- gama e composição farmacêutica dos mesmos |