NZ578162A - Phosphoinositide 3-kinase inhibitor compounds and methods of use - Google Patents

Info

Publication number

NZ578162A

NZ578162A NZ578162A NZ57816207A NZ578162A NZ 578162 A NZ578162 A NZ 578162A NZ 578162 A NZ578162 A NZ 578162A NZ 57816207 A NZ57816207 A NZ 57816207A NZ 578162 A NZ578162 A NZ 578162A

Authority

NZ

New Zealand

Prior art keywords

methyl

pyrimidin

morpholinothieno

amine

thieno

Prior art date

2006-12-07

Links

• Espacenet
• Global Dossier
• Discuss

• 150000001875 compounds Chemical class 0.000 title claims abstract description 231
• 238000000034 method Methods 0.000 title claims description 335
• 239000002935 phosphatidylinositol 3 kinase inhibitor Substances 0.000 title description 6
• 229940043441 phosphoinositide 3-kinase inhibitor Drugs 0.000 title description 4
• 150000003839 salts Chemical class 0.000 claims abstract description 38
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 37
• 201000011510 cancer Diseases 0.000 claims abstract description 28
• 239000012453 solvate Substances 0.000 claims abstract description 19
• 229910052739 hydrogen Inorganic materials 0.000 claims description 180
• -1 C1-C20 heteroaryl Chemical group 0.000 claims description 143
• 239000000203 mixture Substances 0.000 claims description 139
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 128
• 125000000623 heterocyclic group Chemical group 0.000 claims description 55
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 45
• 125000001072 heteroaryl group Chemical group 0.000 claims description 42
• 238000011282 treatment Methods 0.000 claims description 40
• ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 36
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 35
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 32
• 239000008194 pharmaceutical composition Substances 0.000 claims description 31
• 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 claims description 30
• 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 claims description 30
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 30
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 30
• 125000000217 alkyl group Chemical group 0.000 claims description 28
• 229920006395 saturated elastomer Polymers 0.000 claims description 28
• 229910052794 bromium Inorganic materials 0.000 claims description 27
• 125000003118 aryl group Chemical group 0.000 claims description 26
• 229910052760 oxygen Inorganic materials 0.000 claims description 26
• 229910052740 iodine Inorganic materials 0.000 claims description 25
• 239000003795 chemical substances by application Substances 0.000 claims description 23
• 239000003814 drug Substances 0.000 claims description 23
• 229910052717 sulfur Inorganic materials 0.000 claims description 23
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 21
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 21
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 20
• 229910052757 nitrogen Inorganic materials 0.000 claims description 20
• 230000000694 effects Effects 0.000 claims description 19
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
• BCIIMDOZSUCSEN-UHFFFAOYSA-N piperidin-4-amine Chemical compound NC1CCNCC1 BCIIMDOZSUCSEN-UHFFFAOYSA-N 0.000 claims description 18
• 125000004429 atom Chemical group 0.000 claims description 17
• 125000004076 pyridyl group Chemical group 0.000 claims description 17
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 17
• 125000000304 alkynyl group Chemical group 0.000 claims description 14
• RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical compound C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 claims description 14
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 13
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 13
• 125000003342 alkenyl group Chemical group 0.000 claims description 13
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 12
• 108091007960 PI3Ks Proteins 0.000 claims description 12
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
• 125000002950 monocyclic group Chemical group 0.000 claims description 12
• 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 11
• 150000002632 lipids Chemical class 0.000 claims description 11
• 238000004519 manufacturing process Methods 0.000 claims description 11
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 11
• 239000002246 antineoplastic agent Substances 0.000 claims description 10
• 229940127089 cytotoxic agent Drugs 0.000 claims description 10
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 10
• 230000001225 therapeutic effect Effects 0.000 claims description 10
• 239000003937 drug carrier Substances 0.000 claims description 9
• 125000002883 imidazolyl group Chemical group 0.000 claims description 9
• 125000006413 ring segment Chemical group 0.000 claims description 9
• FIRWUSRFSSPHFG-UHFFFAOYSA-N 2-sulfonylpyran Chemical compound O=S(=O)=C1C=CC=CO1 FIRWUSRFSSPHFG-UHFFFAOYSA-N 0.000 claims description 8
• MUSKXFQCWPMBII-UHFFFAOYSA-N 5-[4-morpholin-4-yl-6-(piperazin-1-ylmethyl)thieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCNCC2)=C2)C2=N1 MUSKXFQCWPMBII-UHFFFAOYSA-N 0.000 claims description 8
• 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims description 8
• 230000002401 inhibitory effect Effects 0.000 claims description 7
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
• HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 claims description 7
• 230000008569 process Effects 0.000 claims description 7
• 239000003981 vehicle Substances 0.000 claims description 7
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 6
• 108091000080 Phosphotransferase Proteins 0.000 claims description 6
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 6
• 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 6
• 125000002971 oxazolyl group Chemical group 0.000 claims description 6
• 102000020233 phosphotransferase Human genes 0.000 claims description 6
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 6
• 125000001425 triazolyl group Chemical group 0.000 claims description 6
• IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 5
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 5
• 206010012601 diabetes mellitus Diseases 0.000 claims description 5
• AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 claims description 5
• 229910052731 fluorine Inorganic materials 0.000 claims description 5
• 125000002541 furyl group Chemical group 0.000 claims description 5
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
• 125000004193 piperazinyl group Chemical group 0.000 claims description 5
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 5
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
• 206010041823 squamous cell carcinoma Diseases 0.000 claims description 5
• UXAWXZDXVOYLII-UHFFFAOYSA-N tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate Chemical compound C1C2N(C(=O)OC(C)(C)C)CC1NC2 UXAWXZDXVOYLII-UHFFFAOYSA-N 0.000 claims description 5
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
• 229940124597 therapeutic agent Drugs 0.000 claims description 5
• 125000000335 thiazolyl group Chemical group 0.000 claims description 5
• 125000001544 thienyl group Chemical group 0.000 claims description 5
• WQVHGYBGLRAIKN-UHFFFAOYSA-N 4-[2-(2-methylpyrimidin-5-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1=NC(C)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)S(C)(=O)=O)=C2)C2=N1 WQVHGYBGLRAIKN-UHFFFAOYSA-N 0.000 claims description 4
• RRHMAEWUQQZXRW-UHFFFAOYSA-N 4-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyridine-2,6-diamine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3C=C(N)N=C(N)C=3)=NC(N3CCOCC3)=C2S1 RRHMAEWUQQZXRW-UHFFFAOYSA-N 0.000 claims description 4
• AVCJIFBJUREYDX-UHFFFAOYSA-N 5-[4-morpholin-4-yl-6-(piperazin-1-ylmethyl)thieno[3,2-d]pyrimidin-2-yl]pyridin-2-amine Chemical compound C1=NC(N)=CC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCNCC2)=C2)C2=N1 AVCJIFBJUREYDX-UHFFFAOYSA-N 0.000 claims description 4
• RZDHSETVTNFKSF-UHFFFAOYSA-N 6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-yl-2-pyrimidin-5-ylfuro[3,2-d]pyrimidine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3C=NC=NC=3)=NC(N3CCOCC3)=C2O1 RZDHSETVTNFKSF-UHFFFAOYSA-N 0.000 claims description 4
• 208000029462 Immunodeficiency disease Diseases 0.000 claims description 4
• 239000002671 adjuvant Substances 0.000 claims description 4
• 125000002837 carbocyclic group Chemical group 0.000 claims description 4
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
• 208000019423 liver disease Diseases 0.000 claims description 4
• XXADJQIXIXWQNZ-UHFFFAOYSA-N n-methyl-5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyridin-2-amine Chemical compound C1=NC(NC)=CC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)S(C)(=O)=O)=C2)C2=N1 XXADJQIXIXWQNZ-UHFFFAOYSA-N 0.000 claims description 4
• BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 4
• KFYZNHXSAWBVIE-HOTGVXAUSA-N (2s)-1-[(3s)-4-[[2-(6-aminopyridin-3-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-3-methylpiperazin-1-yl]-2-hydroxypropan-1-one Chemical compound C[C@H]1CN(C(=O)[C@@H](O)C)CCN1CC1=CC2=NC(C=3C=NC(N)=CC=3)=NC(N3CCOCC3)=C2S1 KFYZNHXSAWBVIE-HOTGVXAUSA-N 0.000 claims description 3
• MGJSBPBSENBWNX-AWEZNQCLSA-N (2s)-1-[4-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-hydroxypropan-1-one Chemical compound C1CN(C(=O)[C@@H](O)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=NC(N)=NC=3)N=C2S1 MGJSBPBSENBWNX-AWEZNQCLSA-N 0.000 claims description 3
• ZZRLHKDABGJXHM-AWEZNQCLSA-N (2s)-1-[4-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-hydroxypropan-1-one Chemical compound C1CN(C(=O)[C@@H](O)C)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 ZZRLHKDABGJXHM-AWEZNQCLSA-N 0.000 claims description 3
• YOVVNQKCSKSHKT-HNNXBMFYSA-N (2s)-1-[4-[[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-hydroxypropan-1-one Chemical compound C1CN(C(=O)[C@@H](O)C)CCN1CC1=C(C)C2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 YOVVNQKCSKSHKT-HNNXBMFYSA-N 0.000 claims description 3
• GDAOFGJPAWFAOG-HNNXBMFYSA-N (2s)-1-[4-[[2-(6-aminopyridin-3-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-hydroxypropan-1-one Chemical compound C1CN(C(=O)[C@@H](O)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=NC(N)=CC=3)N=C2S1 GDAOFGJPAWFAOG-HNNXBMFYSA-N 0.000 claims description 3
• ULXAHCRHGKOQFJ-AWEZNQCLSA-N (2s)-2-amino-1-[4-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]propan-1-one Chemical compound C1CN(C(=O)[C@@H](N)C)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 ULXAHCRHGKOQFJ-AWEZNQCLSA-N 0.000 claims description 3
• NZXUDOZLBWGVLI-KRWDZBQOSA-N (2s)-2-hydroxy-1-[4-[(7-methyl-4-morpholin-4-yl-2-pyridin-3-ylthieno[3,2-d]pyrimidin-6-yl)methyl]piperazin-1-yl]propan-1-one Chemical compound C1CN(C(=O)[C@@H](O)C)CCN1CC1=C(C)C2=NC(C=3C=NC=CC=3)=NC(N3CCOCC3)=C2S1 NZXUDOZLBWGVLI-KRWDZBQOSA-N 0.000 claims description 3
• WTTHUCMKPFJUBB-INIZCTEOSA-N (2s)-2-hydroxy-1-[4-[[2-(2-methoxypyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]propan-1-one Chemical compound C1=NC(OC)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)C(=O)[C@H](C)O)=C2C)C2=N1 WTTHUCMKPFJUBB-INIZCTEOSA-N 0.000 claims description 3
• KNPOYYSMPUNDRT-KRWDZBQOSA-N (2s)-2-hydroxy-1-[4-[[2-(6-methoxypyridin-3-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]propan-1-one Chemical compound C1=NC(OC)=CC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)C(=O)[C@H](C)O)=C2C)C2=N1 KNPOYYSMPUNDRT-KRWDZBQOSA-N 0.000 claims description 3
• XIWKCPGWKOFCFH-CQSZACIVSA-N (3r)-1-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperidin-3-ol Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2C[C@H](O)CCC2)=C2)C2=N1 XIWKCPGWKOFCFH-CQSZACIVSA-N 0.000 claims description 3
• QVOSHIFBEUZNLN-CYBMUJFWSA-N (3r)-1-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]pyrrolidin-3-ol Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2C[C@H](O)CC2)=C2)C2=N1 QVOSHIFBEUZNLN-CYBMUJFWSA-N 0.000 claims description 3
• HGWXCIFBYQHGBF-UHFFFAOYSA-N 2-(5-methoxypyridin-3-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylfuro[3,2-d]pyrimidine Chemical compound COC1=CN=CC(C=2N=C3C=C(CN4CCN(CC4)S(C)(=O)=O)OC3=C(N3CCOCC3)N=2)=C1 HGWXCIFBYQHGBF-UHFFFAOYSA-N 0.000 claims description 3
• LWYDLVVUGDVCAV-UHFFFAOYSA-N 2-[1-[(4-morpholin-4-yl-2-pyridin-3-ylthieno[3,2-d]pyrimidin-6-yl)methyl]piperidin-4-yl]ethanol Chemical compound C1CC(CCO)CCN1CC1=CC2=NC(C=3C=NC=CC=3)=NC(N3CCOCC3)=C2S1 LWYDLVVUGDVCAV-UHFFFAOYSA-N 0.000 claims description 3
• ULZSSABCROOAPR-UHFFFAOYSA-N 2-[4-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-n,2-dimethylpropanamide Chemical compound C1CN(C(C)(C)C(=O)NC)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 ULZSSABCROOAPR-UHFFFAOYSA-N 0.000 claims description 3
• UARUXLCKYYGGRR-UHFFFAOYSA-N 2-[4-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-n,n-dimethylacetamide Chemical compound C1CN(CC(=O)N(C)C)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 UARUXLCKYYGGRR-UHFFFAOYSA-N 0.000 claims description 3
• WZLIWPAFBLTQAC-UHFFFAOYSA-N 2-[4-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]ethanol Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CCO)CC2)=C2)C2=N1 WZLIWPAFBLTQAC-UHFFFAOYSA-N 0.000 claims description 3
• OIUAUQDHOHXBMJ-UHFFFAOYSA-N 2-[4-[[2-(6-aminopyridin-3-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-n,2-dimethylpropanamide Chemical compound C1CN(C(C)(C)C(=O)NC)CCN1CC1=CC2=NC(C=3C=NC(N)=CC=3)=NC(N3CCOCC3)=C2S1 OIUAUQDHOHXBMJ-UHFFFAOYSA-N 0.000 claims description 3
• UZYHCKYMPAEGBW-UHFFFAOYSA-N 2-[4-[[2-(6-aminopyridin-3-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-n,n-dimethylacetamide Chemical compound C1CN(CC(=O)N(C)C)CCN1CC1=CC2=NC(C=3C=NC(N)=CC=3)=NC(N3CCOCC3)=C2S1 UZYHCKYMPAEGBW-UHFFFAOYSA-N 0.000 claims description 3
• HBNVOIGEWZVHCB-UHFFFAOYSA-N 2-[4-[[2-(6-aminopyridin-3-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]ethanol Chemical compound C1=NC(N)=CC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CCO)CC2)=C2)C2=N1 HBNVOIGEWZVHCB-UHFFFAOYSA-N 0.000 claims description 3
• JBVDQAPQHIKIKX-UHFFFAOYSA-N 2-[[5-[4-morpholin-4-yl-6-(piperazin-1-ylmethyl)thieno[3,2-d]pyrimidin-2-yl]pyridin-2-yl]amino]ethanol Chemical compound C1=NC(NCCO)=CC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCNCC2)=C2)C2=N1 JBVDQAPQHIKIKX-UHFFFAOYSA-N 0.000 claims description 3
• KEQQXXKVAMIDJA-UHFFFAOYSA-N 2-amino-1-[4-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-methylpropan-1-one Chemical compound C1CN(C(=O)C(C)(N)C)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 KEQQXXKVAMIDJA-UHFFFAOYSA-N 0.000 claims description 3
• WPQVRPJKRLJRFD-UHFFFAOYSA-N 2-amino-1-[4-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)CN)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 WPQVRPJKRLJRFD-UHFFFAOYSA-N 0.000 claims description 3
• GIJHJAVPKRWPOL-UHFFFAOYSA-N 4-[2-(2,4-dimethoxypyrimidin-5-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[2,3-d]pyrimidin-4-yl]morpholine Chemical compound COC1=NC(OC)=NC=C1C1=NC(N2CCOCC2)=C(C=C(CN2CCN(CC2)S(C)(=O)=O)S2)C2=N1 GIJHJAVPKRWPOL-UHFFFAOYSA-N 0.000 claims description 3
• IHMUZMAUSSWGBN-UHFFFAOYSA-N 4-[2-(2,4-dimethoxypyrimidin-5-yl)-6-[(4-methylsulfonylpiperidin-1-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound COC1=NC(OC)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCC(CC2)S(C)(=O)=O)=C2)C2=N1 IHMUZMAUSSWGBN-UHFFFAOYSA-N 0.000 claims description 3
• RMWGJAFXJZVMMY-UHFFFAOYSA-N 4-[2-(2,4-dimethoxypyrimidin-5-yl)-6-[(4-piperidin-1-ylpiperidin-1-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound COC1=NC(OC)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCC(CC2)N2CCCCC2)=C2)C2=N1 RMWGJAFXJZVMMY-UHFFFAOYSA-N 0.000 claims description 3
• PJVOYUWADIMQGS-UHFFFAOYSA-N 4-[2-(2-methoxypyrimidin-5-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1=NC(OC)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)S(C)(=O)=O)=C2)C2=N1 PJVOYUWADIMQGS-UHFFFAOYSA-N 0.000 claims description 3
• ROBOHVCWTXKHPA-UHFFFAOYSA-N 4-[2-(4-methoxypyridin-3-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound COC1=CC=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)S(C)(=O)=O)=C2)C2=N1 ROBOHVCWTXKHPA-UHFFFAOYSA-N 0.000 claims description 3
• ZQNSBNNBKUAHQY-UHFFFAOYSA-N 4-[2-(5-methoxypyridin-3-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[2,3-d]pyrimidin-4-yl]morpholine Chemical compound COC1=CN=CC(C=2N=C3SC(CN4CCN(CC4)S(C)(=O)=O)=CC3=C(N3CCOCC3)N=2)=C1 ZQNSBNNBKUAHQY-UHFFFAOYSA-N 0.000 claims description 3
• PQPDIEJGAJTKCA-UHFFFAOYSA-N 4-[2-(6-methoxypyridin-3-yl)-6-(piperazin-1-ylmethyl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1=NC(OC)=CC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCNCC2)=C2)C2=N1 PQPDIEJGAJTKCA-UHFFFAOYSA-N 0.000 claims description 3
• VUVVTPJFRGJXNC-UHFFFAOYSA-N 4-[2-(6-methylpyridin-3-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[2,3-d]pyrimidin-4-yl]morpholine Chemical compound C1=NC(C)=CC=C1C1=NC(N2CCOCC2)=C(C=C(CN2CCN(CC2)S(C)(=O)=O)S2)C2=N1 VUVVTPJFRGJXNC-UHFFFAOYSA-N 0.000 claims description 3
• IQFSJRGDAKCWRU-UHFFFAOYSA-N 4-[2-(6-methylpyridin-3-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1=NC(C)=CC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)S(C)(=O)=O)=C2)C2=N1 IQFSJRGDAKCWRU-UHFFFAOYSA-N 0.000 claims description 3
• NJTGIYXYNQGPGK-UHFFFAOYSA-N 4-[2-(6-methylpyridin-3-yl)-6-[(4-piperidin-1-ylpiperidin-1-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1=NC(C)=CC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCC(CC2)N2CCCCC2)=C2)C2=N1 NJTGIYXYNQGPGK-UHFFFAOYSA-N 0.000 claims description 3
• NUSKUCOIXWODFL-UHFFFAOYSA-N 4-[2-(furan-3-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(C3=COC=C3)=NC(N3CCOCC3)=C2S1 NUSKUCOIXWODFL-UHFFFAOYSA-N 0.000 claims description 3
• HCNVPRLUBQHBEE-UHFFFAOYSA-N 4-[2-pyridin-3-yl-6-[(4-pyrrolidin-1-ylpiperidin-1-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C=1C2=NC(C=3C=NC=CC=3)=NC(N3CCOCC3)=C2SC=1CN(CC1)CCC1N1CCCC1 HCNVPRLUBQHBEE-UHFFFAOYSA-N 0.000 claims description 3
• WNSHWFIWDBSVRK-UHFFFAOYSA-N 4-[6-[(3-methylsulfonylpyrrolidin-1-yl)methyl]-2-pyridin-3-ylthieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1C(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3C=NC=CC=3)=NC(N3CCOCC3)=C2S1 WNSHWFIWDBSVRK-UHFFFAOYSA-N 0.000 claims description 3
• UTMALWLPHKIDJL-UHFFFAOYSA-N 4-[6-[(4-cyclopropylsulfonylpiperazin-1-yl)methyl]-2-(2,4-dimethoxypyrimidin-5-yl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound COC1=NC(OC)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)S(=O)(=O)C2CC2)=C2)C2=N1 UTMALWLPHKIDJL-UHFFFAOYSA-N 0.000 claims description 3
• PHKGASRBZCIRNM-UHFFFAOYSA-N 4-[6-[(4-methylpiperazin-1-yl)methyl]-2-pyridin-3-ylthieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(C)CCN1CC1=CC2=NC(C=3C=NC=CC=3)=NC(N3CCOCC3)=C2S1 PHKGASRBZCIRNM-UHFFFAOYSA-N 0.000 claims description 3
• MVKHQXRMYFALFZ-UHFFFAOYSA-N 4-[6-[(4-methylpiperazin-1-yl)methyl]-2-pyrimidin-5-ylthieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(C)CCN1CC1=CC2=NC(C=3C=NC=NC=3)=NC(N3CCOCC3)=C2S1 MVKHQXRMYFALFZ-UHFFFAOYSA-N 0.000 claims description 3
• KEUBYNSPCAXXAQ-UHFFFAOYSA-N 4-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-2-(1,3-thiazol-5-yl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3SC=NC=3)=NC(N3CCOCC3)=C2S1 KEUBYNSPCAXXAQ-UHFFFAOYSA-N 0.000 claims description 3
• GFHJARDRYPZJCJ-UHFFFAOYSA-N 4-[6-[[4-(benzenesulfonyl)piperazin-1-yl]methyl]-2-(2,4-dimethoxypyrimidin-5-yl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound COC1=NC(OC)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)S(=O)(=O)C=2C=CC=CC=2)=C2)C2=N1 GFHJARDRYPZJCJ-UHFFFAOYSA-N 0.000 claims description 3
• MYQJAHDGCGXUSC-UHFFFAOYSA-N 4-[7-methyl-6-[(4-methylsulfonylpiperazin-1-yl)methyl]-2-pyrimidin-5-ylthieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound S1C2=C(N3CCOCC3)N=C(C=3C=NC=NC=3)N=C2C(C)=C1CN1CCN(S(C)(=O)=O)CC1 MYQJAHDGCGXUSC-UHFFFAOYSA-N 0.000 claims description 3
• FJDUBAONUKWCOM-UHFFFAOYSA-N 4-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl]methyl]-n,n-dimethylpiperazine-1-carboxamide Chemical compound C1CN(C(=O)N(C)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=NC(N)=NC=3)N=C2S1 FJDUBAONUKWCOM-UHFFFAOYSA-N 0.000 claims description 3
• QUHQRCBLMCILHT-UHFFFAOYSA-N 4-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-n,n-dimethylpiperazine-1-carboxamide Chemical compound C1CN(C(=O)N(C)C)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 QUHQRCBLMCILHT-UHFFFAOYSA-N 0.000 claims description 3
• KZCYIRBTWPWLDP-UHFFFAOYSA-N 4-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-n-(2-methoxyethyl)-n-methylpiperazine-1-carboxamide Chemical compound C1CN(C(=O)N(C)CCOC)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 KZCYIRBTWPWLDP-UHFFFAOYSA-N 0.000 claims description 3
• OEZDMRPXEPUYML-UHFFFAOYSA-N 4-[[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-n,n-dimethylpiperazine-1-carboxamide Chemical compound C1CN(C(=O)N(C)C)CCN1CC1=C(C)C2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 OEZDMRPXEPUYML-UHFFFAOYSA-N 0.000 claims description 3
• UKRUOQNFXYOKIM-UHFFFAOYSA-N 4-[[2-(6-aminopyridin-3-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-n,n-dimethylpiperazine-1-carboxamide Chemical compound C1CN(C(=O)N(C)C)CCN1CC1=CC2=NC(C=3C=NC(N)=CC=3)=NC(N3CCOCC3)=C2S1 UKRUOQNFXYOKIM-UHFFFAOYSA-N 0.000 claims description 3
• CJLWJGPEYMSBOZ-UHFFFAOYSA-N 4-[[2-(6-aminopyridin-3-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-n-(2-methoxyethyl)-n-methylpiperazine-1-carboxamide Chemical compound C1CN(C(=O)N(C)CCOC)CCN1CC1=CC2=NC(C=3C=NC(N)=CC=3)=NC(N3CCOCC3)=C2S1 CJLWJGPEYMSBOZ-UHFFFAOYSA-N 0.000 claims description 3
• SQSSIGUUBPZKBQ-UHFFFAOYSA-N 5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylfuro[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2O1 SQSSIGUUBPZKBQ-UHFFFAOYSA-N 0.000 claims description 3
• JEHTXQHLTKVUGY-UHFFFAOYSA-N 5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyridin-2-amine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3C=NC(N)=CC=3)=NC(N3CCOCC3)=C2S1 JEHTXQHLTKVUGY-UHFFFAOYSA-N 0.000 claims description 3
• IBPRXQQHWAHCHO-UHFFFAOYSA-N 5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyridine-3-carbaldehyde Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3C=C(C=O)C=NC=3)=NC(N3CCOCC3)=C2S1 IBPRXQQHWAHCHO-UHFFFAOYSA-N 0.000 claims description 3
• XNARCGJSKLNICV-UHFFFAOYSA-N 6-methyl-5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyridin-2-amine Chemical compound CC1=NC(N)=CC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)S(C)(=O)=O)=C2)C2=N1 XNARCGJSKLNICV-UHFFFAOYSA-N 0.000 claims description 3
• 206010039491 Sarcoma Diseases 0.000 claims description 3
• NBGOGDLJUJPVFA-UHFFFAOYSA-N [5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]pyridin-3-yl]methanol Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=C(CO)C=NC=3)N=C2S1 NBGOGDLJUJPVFA-UHFFFAOYSA-N 0.000 claims description 3
• IOEZYIGNBNDLKX-UHFFFAOYSA-N [5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyridin-3-yl]methanol Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3C=C(CO)C=NC=3)=NC(N3CCOCC3)=C2S1 IOEZYIGNBNDLKX-UHFFFAOYSA-N 0.000 claims description 3
• KGHRVBQLCNPPKV-UHFFFAOYSA-N [5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]thiophen-2-yl]methanol Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3SC(CO)=CC=3)=NC(N3CCOCC3)=C2S1 KGHRVBQLCNPPKV-UHFFFAOYSA-N 0.000 claims description 3
• 208000005017 glioblastoma Diseases 0.000 claims description 3
• 208000032839 leukemia Diseases 0.000 claims description 3
• 210000004072 lung Anatomy 0.000 claims description 3
• 201000005249 lung adenocarcinoma Diseases 0.000 claims description 3
• 230000001404 mediated effect Effects 0.000 claims description 3
• 201000001441 melanoma Diseases 0.000 claims description 3
• ODWWFLGZIUIGMU-UHFFFAOYSA-N n,2-dimethyl-2-[4-[[2-(6-methylpyridin-3-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]propanamide Chemical compound C1CN(C(C)(C)C(=O)NC)CCN1CC1=CC2=NC(C=3C=NC(C)=CC=3)=NC(N3CCOCC3)=C2S1 ODWWFLGZIUIGMU-UHFFFAOYSA-N 0.000 claims description 3
• RJASFAIUNGIQNR-UHFFFAOYSA-N n,n-dimethyl-1-[(4-morpholin-4-yl-2-pyrimidin-5-ylthieno[2,3-d]pyrimidin-6-yl)methyl]piperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=NC=NC=3)N=C2S1 RJASFAIUNGIQNR-UHFFFAOYSA-N 0.000 claims description 3
• XQSACXPYRGSBTG-UHFFFAOYSA-N n,n-dimethyl-2-[4-[[2-(6-methylpyridin-3-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]acetamide Chemical compound C1CN(CC(=O)N(C)C)CCN1CC1=CC2=NC(C=3C=NC(C)=CC=3)=NC(N3CCOCC3)=C2S1 XQSACXPYRGSBTG-UHFFFAOYSA-N 0.000 claims description 3
• FFOGBWCOFNTQES-UHFFFAOYSA-N n,n-dimethyl-4-[(4-morpholin-4-yl-2-pyrimidin-5-ylthieno[2,3-d]pyrimidin-6-yl)methyl]piperazine-1-carboxamide Chemical compound C1CN(C(=O)N(C)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=NC=NC=3)N=C2S1 FFOGBWCOFNTQES-UHFFFAOYSA-N 0.000 claims description 3
• NNADJEZOQSDHLN-UHFFFAOYSA-N n,n-dimethyl-5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N(C)C)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)S(C)(=O)=O)=C2)C2=N1 NNADJEZOQSDHLN-UHFFFAOYSA-N 0.000 claims description 3
• VEDKUKJQZBBWEP-UHFFFAOYSA-N n-(2-methoxyethyl)-n-methyl-4-[[2-(6-methylpyridin-3-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazine-1-carboxamide Chemical compound C1CN(C(=O)N(C)CCOC)CCN1CC1=CC2=NC(C=3C=NC(C)=CC=3)=NC(N3CCOCC3)=C2S1 VEDKUKJQZBBWEP-UHFFFAOYSA-N 0.000 claims description 3
• XWZNJUFZXSYWCD-UHFFFAOYSA-N n-[5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylfuro[3,2-d]pyrimidin-2-yl]pyridin-2-yl]formamide Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3C=NC(NC=O)=CC=3)=NC(N3CCOCC3)=C2O1 XWZNJUFZXSYWCD-UHFFFAOYSA-N 0.000 claims description 3
• AOUWLUSFHMEWLB-UHFFFAOYSA-N n-[5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyridin-2-yl]acetamide Chemical compound C1=NC(NC(=O)C)=CC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)S(C)(=O)=O)=C2)C2=N1 AOUWLUSFHMEWLB-UHFFFAOYSA-N 0.000 claims description 3
• OLMXMMQHJHAQRV-UHFFFAOYSA-N n-[5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-yl]formamide Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3C=NC(NC=O)=NC=3)=NC(N3CCOCC3)=C2S1 OLMXMMQHJHAQRV-UHFFFAOYSA-N 0.000 claims description 3
• DAHZZEQXFARYNJ-UHFFFAOYSA-N n-[5-[6-[[4-(2-hydroxyacetyl)piperazin-1-yl]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyridin-2-yl]acetamide Chemical compound C1=NC(NC(=O)C)=CC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)C(=O)CO)=C2)C2=N1 DAHZZEQXFARYNJ-UHFFFAOYSA-N 0.000 claims description 3
• SZUJQDTZOAKIFZ-UHFFFAOYSA-N n-methyl-n-[5-[4-morpholin-4-yl-6-(piperazin-1-ylmethyl)thieno[3,2-d]pyrimidin-2-yl]pyridin-2-yl]acetamide Chemical compound C1=NC(N(C(C)=O)C)=CC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCNCC2)=C2)C2=N1 SZUJQDTZOAKIFZ-UHFFFAOYSA-N 0.000 claims description 3
• ZZRLHKDABGJXHM-CQSZACIVSA-N (2r)-1-[4-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-hydroxypropan-1-one Chemical compound C1CN(C(=O)[C@H](O)C)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 ZZRLHKDABGJXHM-CQSZACIVSA-N 0.000 claims description 2
• YOVVNQKCSKSHKT-OAHLLOKOSA-N (2r)-1-[4-[[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-hydroxypropan-1-one Chemical compound C1CN(C(=O)[C@H](O)C)CCN1CC1=C(C)C2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 YOVVNQKCSKSHKT-OAHLLOKOSA-N 0.000 claims description 2
• ZDFMRAPKKVSTHV-INIZCTEOSA-N (2s)-1-[4-[[2-(2,4-dimethoxypyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-hydroxypropan-1-one Chemical compound COC1=NC(OC)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)C(=O)[C@H](C)O)=C2C)C2=N1 ZDFMRAPKKVSTHV-INIZCTEOSA-N 0.000 claims description 2
• RFZOZQKSNFMYMG-INIZCTEOSA-N (2s)-1-[4-[[2-(2-amino-4-methylpyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-hydroxypropan-1-one Chemical compound C1CN(C(=O)[C@@H](O)C)CCN1CC1=C(C)C2=NC(C=3C(=NC(N)=NC=3)C)=NC(N3CCOCC3)=C2S1 RFZOZQKSNFMYMG-INIZCTEOSA-N 0.000 claims description 2
• WFMIYLYADUVRLJ-KRWDZBQOSA-N (2s)-1-[4-[[2-[2-(dimethylamino)pyrimidin-5-yl]-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-hydroxypropan-1-one Chemical compound C1CN(C(=O)[C@@H](O)C)CCN1CC1=C(C)C2=NC(C=3C=NC(=NC=3)N(C)C)=NC(N3CCOCC3)=C2S1 WFMIYLYADUVRLJ-KRWDZBQOSA-N 0.000 claims description 2
• JNQXUZUFISKMSQ-AWEZNQCLSA-N (2s)-1-[4-[[2-[2-amino-4-(trifluoromethyl)pyrimidin-5-yl]-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-hydroxypropan-1-one Chemical compound C1CN(C(=O)[C@@H](O)C)CCN1CC1=C(C)C2=NC(C=3C(=NC(N)=NC=3)C(F)(F)F)=NC(N3CCOCC3)=C2S1 JNQXUZUFISKMSQ-AWEZNQCLSA-N 0.000 claims description 2
• UJWHVVJSUAISGV-INIZCTEOSA-N (2s)-2-hydroxy-1-[4-[(4-morpholin-4-yl-2-pyridin-3-ylthieno[3,2-d]pyrimidin-6-yl)methyl]piperazin-1-yl]propan-1-one Chemical compound C1CN(C(=O)[C@@H](O)C)CCN1CC1=CC2=NC(C=3C=NC=CC=3)=NC(N3CCOCC3)=C2S1 UJWHVVJSUAISGV-INIZCTEOSA-N 0.000 claims description 2
• HGFSTSLZRPTYRH-HNNXBMFYSA-N (2s)-2-hydroxy-1-[4-[(4-morpholin-4-yl-2-pyrimidin-5-ylthieno[3,2-d]pyrimidin-6-yl)methyl]piperazin-1-yl]propan-1-one Chemical compound C1CN(C(=O)[C@@H](O)C)CCN1CC1=CC2=NC(C=3C=NC=NC=3)=NC(N3CCOCC3)=C2S1 HGFSTSLZRPTYRH-HNNXBMFYSA-N 0.000 claims description 2
• IGMLEPWZACCRCX-INIZCTEOSA-N (2s)-2-hydroxy-1-[4-[(7-methyl-4-morpholin-4-yl-2-pyrimidin-5-ylthieno[3,2-d]pyrimidin-6-yl)methyl]piperazin-1-yl]propan-1-one Chemical compound C1CN(C(=O)[C@@H](O)C)CCN1CC1=C(C)C2=NC(C=3C=NC=NC=3)=NC(N3CCOCC3)=C2S1 IGMLEPWZACCRCX-INIZCTEOSA-N 0.000 claims description 2
• SQLXGVDEYHYONY-HNNXBMFYSA-N (2s)-2-hydroxy-1-[4-[[2-(2-methoxypyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]propan-1-one Chemical compound C1=NC(OC)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)C(=O)[C@H](C)O)=C2)C2=N1 SQLXGVDEYHYONY-HNNXBMFYSA-N 0.000 claims description 2
• RDDMDXOXILPHJV-INIZCTEOSA-N (2s)-2-hydroxy-1-[4-[[2-(6-methoxypyridin-3-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]propan-1-one Chemical compound C1=NC(OC)=CC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)C(=O)[C@H](C)O)=C2)C2=N1 RDDMDXOXILPHJV-INIZCTEOSA-N 0.000 claims description 2
• LZLNVMDKKOSSFX-INIZCTEOSA-N (2s)-2-hydroxy-1-[4-[[2-[6-(methylamino)pyridin-3-yl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl]methyl]piperazin-1-yl]propan-1-one Chemical compound C1=NC(NC)=CC=C1C1=NC(N2CCOCC2)=C(C=C(CN2CCN(CC2)C(=O)[C@H](C)O)S2)C2=N1 LZLNVMDKKOSSFX-INIZCTEOSA-N 0.000 claims description 2
• YZMPELRGXARNME-INIZCTEOSA-N (2s)-2-hydroxy-1-[4-[[2-[6-(methylamino)pyridin-3-yl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]propan-1-one Chemical compound C1=NC(NC)=CC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)C(=O)[C@H](C)O)=C2)C2=N1 YZMPELRGXARNME-INIZCTEOSA-N 0.000 claims description 2
• OHCOSSPVMOFYJK-KRWDZBQOSA-N (2s)-2-hydroxy-1-[4-[[7-methyl-2-[6-(methylamino)pyridin-3-yl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]propan-1-one Chemical compound C1=NC(NC)=CC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)C(=O)[C@H](C)O)=C2C)C2=N1 OHCOSSPVMOFYJK-KRWDZBQOSA-N 0.000 claims description 2
• GJVMTGNJBWBGQH-CQSZACIVSA-N (3r)-1-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl]methyl]piperidin-3-ol Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(C=C(CN2C[C@H](O)CCC2)S2)C2=N1 GJVMTGNJBWBGQH-CQSZACIVSA-N 0.000 claims description 2
• WAUZARFQARQRSG-HNNXBMFYSA-N (3s)-3-methyl-4-[6-[(4-methylpiperazin-1-yl)methyl]-2-pyrimidin-5-ylthieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C[C@H]1COCCN1C1=NC(C=2C=NC=NC=2)=NC2=C1SC(CN1CCN(C)CC1)=C2 WAUZARFQARQRSG-HNNXBMFYSA-N 0.000 claims description 2
• RIYQFVAOFLPASA-UHFFFAOYSA-N 1-[(4-morpholin-4-yl-2-pyridin-3-ylthieno[3,2-d]pyrimidin-6-yl)methyl]piperidin-4-ol Chemical compound C1CC(O)CCN1CC1=CC2=NC(C=3C=NC=CC=3)=NC(N3CCOCC3)=C2S1 RIYQFVAOFLPASA-UHFFFAOYSA-N 0.000 claims description 2
• CEZYORZQHDIFJJ-UHFFFAOYSA-N 1-[2-(6-aminopyridin-3-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]-n-methyl-n'-(1-methylpiperidin-4-yl)methanediamine Chemical compound S1C2=C(N3CCOCC3)N=C(C=3C=NC(N)=CC=3)N=C2C(C)=C1C(NC)NC1CCN(C)CC1 CEZYORZQHDIFJJ-UHFFFAOYSA-N 0.000 claims description 2
• AMXDBKGEOYUNJL-HNNXBMFYSA-N 1-[4-[[2-(2-aminopyrimidin-5-yl)-4-[(3s)-3-methylmorpholin-4-yl]thieno[3,2-d]pyrimidin-6-yl]methyl]-1,4-diazepan-1-yl]ethanone Chemical compound C[C@H]1COCCN1C1=NC(C=2C=NC(N)=NC=2)=NC2=C1SC(CN1CCN(CCC1)C(C)=O)=C2 AMXDBKGEOYUNJL-HNNXBMFYSA-N 0.000 claims description 2
• NHFUBRSUKOMNKW-UHFFFAOYSA-N 1-[4-[[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-methylsulfonylethanone Chemical compound S1C2=C(N3CCOCC3)N=C(C=3C=NC(N)=NC=3)N=C2C(C)=C1CN1CCN(C(=O)CS(C)(=O)=O)CC1 NHFUBRSUKOMNKW-UHFFFAOYSA-N 0.000 claims description 2
• WLOVYGNZZGBRRW-UHFFFAOYSA-N 1-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl]methyl]piperidin-4-ol Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(C=C(CN2CCC(O)CC2)S2)C2=N1 WLOVYGNZZGBRRW-UHFFFAOYSA-N 0.000 claims description 2
• SIDYNERHAYWAOY-UHFFFAOYSA-N 1-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-n,n-dimethylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 SIDYNERHAYWAOY-UHFFFAOYSA-N 0.000 claims description 2
• NLPRUSAMPUFZQG-UHFFFAOYSA-N 2-(2-methoxypyrimidin-5-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylfuro[3,2-d]pyrimidine Chemical compound C1=NC(OC)=NC=C1C1=NC(N2CCOCC2)=C(OC(CN2CCN(CC2)S(C)(=O)=O)=C2)C2=N1 NLPRUSAMPUFZQG-UHFFFAOYSA-N 0.000 claims description 2
• XKBXIXCALUVYKP-UHFFFAOYSA-N 2-(2-methylpyrimidin-5-yl)-4-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[2,3-d]pyrimidin-2-yl]morpholine Chemical compound C1=NC(C)=NC=C1C1OCCN(C=2N=C3SC(CN4CCN(CC4)S(C)(=O)=O)=CC3=CN=2)C1 XKBXIXCALUVYKP-UHFFFAOYSA-N 0.000 claims description 2
• HVMMLODZMIQTDB-UHFFFAOYSA-N 3,4-dimethyl-5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]pyridin-2-amine Chemical compound CC1=C(N)N=CC(C=2N=C3SC(CN4CCN(CC4)S(C)(=O)=O)=CC3=C(N3CCOCC3)N=2)=C1C HVMMLODZMIQTDB-UHFFFAOYSA-N 0.000 claims description 2
• ZXAGAZHYFWSIRZ-UHFFFAOYSA-N 3-chloro-5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]pyridin-2-amine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=C(Cl)C(N)=NC=3)N=C2S1 ZXAGAZHYFWSIRZ-UHFFFAOYSA-N 0.000 claims description 2
• CVQXBOLQJRFAEH-UHFFFAOYSA-N 3-chloro-5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyridin-2-amine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3C=C(Cl)C(N)=NC=3)=NC(N3CCOCC3)=C2S1 CVQXBOLQJRFAEH-UHFFFAOYSA-N 0.000 claims description 2
• AICYXEKASNWGCO-UHFFFAOYSA-N 3-methyl-5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]pyridin-2-amine Chemical compound N1=C(N)C(C)=CC(C=2N=C3SC(CN4CCN(CC4)S(C)(=O)=O)=CC3=C(N3CCOCC3)N=2)=C1 AICYXEKASNWGCO-UHFFFAOYSA-N 0.000 claims description 2
• MVOZNHCFXWOPKC-UHFFFAOYSA-N 4-[2-(2,4-dimethoxypyrimidin-5-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound COC1=NC(OC)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)S(C)(=O)=O)=C2)C2=N1 MVOZNHCFXWOPKC-UHFFFAOYSA-N 0.000 claims description 2
• SMUWUMKBYKUINP-UHFFFAOYSA-N 4-[2-(2,4-dimethoxypyrimidin-5-yl)-7-methyl-6-[(4-methylsulfonylpiperidin-1-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound COC1=NC(OC)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCC(CC2)S(C)(=O)=O)=C2C)C2=N1 SMUWUMKBYKUINP-UHFFFAOYSA-N 0.000 claims description 2
• JDHZJLDVSMDUMA-UHFFFAOYSA-N 4-[2-(2-methylpyrimidin-5-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[2,3-d]pyrimidin-4-yl]morpholine Chemical compound C1=NC(C)=NC=C1C1=NC(N2CCOCC2)=C(C=C(CN2CCN(CC2)S(C)(=O)=O)S2)C2=N1 JDHZJLDVSMDUMA-UHFFFAOYSA-N 0.000 claims description 2
• XUAJNFXMNSKIHI-UHFFFAOYSA-N 4-[2-(2-methylsulfanylpyrimidin-5-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1=NC(SC)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)S(C)(=O)=O)=C2)C2=N1 XUAJNFXMNSKIHI-UHFFFAOYSA-N 0.000 claims description 2
• KMTZYTVFLBKQQK-UHFFFAOYSA-N 4-[2-(5,6-dimethylpyridin-3-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[2,3-d]pyrimidin-4-yl]morpholine Chemical compound N1=C(C)C(C)=CC(C=2N=C3SC(CN4CCN(CC4)S(C)(=O)=O)=CC3=C(N3CCOCC3)N=2)=C1 KMTZYTVFLBKQQK-UHFFFAOYSA-N 0.000 claims description 2
• FQBRBHJXPDPTMX-UHFFFAOYSA-N 4-[2-(5-methoxypyridin-3-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound COC1=CN=CC(C=2N=C3C=C(CN4CCN(CC4)S(C)(=O)=O)SC3=C(N3CCOCC3)N=2)=C1 FQBRBHJXPDPTMX-UHFFFAOYSA-N 0.000 claims description 2
• JJCBDPDTQFUJRN-UHFFFAOYSA-N 4-[6-(piperazin-1-ylmethyl)-2-(2-propan-2-ylimidazol-1-yl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound CC(C)C1=NC=CN1C1=NC(N2CCOCC2)=C(SC(CN2CCNCC2)=C2)C2=N1 JJCBDPDTQFUJRN-UHFFFAOYSA-N 0.000 claims description 2
• AIIRVAMJYVIOSH-UHFFFAOYSA-N 4-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-2-(5-phenylpyridin-3-yl)thieno[2,3-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=C(C=NC=3)C=3C=CC=CC=3)N=C2S1 AIIRVAMJYVIOSH-UHFFFAOYSA-N 0.000 claims description 2
• KPKGXPGKYSNSLV-UHFFFAOYSA-N 4-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyridin-2-amine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3C=C(N)N=CC=3)=NC(N3CCOCC3)=C2S1 KPKGXPGKYSNSLV-UHFFFAOYSA-N 0.000 claims description 2
• JPZXRQGJYOJDFA-UHFFFAOYSA-N 4-[7-methyl-6-[(4-methylsulfonylpiperazin-1-yl)methyl]-2-pyridin-3-ylthieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound S1C2=C(N3CCOCC3)N=C(C=3C=NC=CC=3)N=C2C(C)=C1CN1CCN(S(C)(=O)=O)CC1 JPZXRQGJYOJDFA-UHFFFAOYSA-N 0.000 claims description 2
• VXLUOMZPIYNTSE-UHFFFAOYSA-N 4-[[2-(2,4-dimethoxypyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-n,n-dimethylpiperazine-1-carboxamide Chemical compound COC1=NC(OC)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)C(=O)N(C)C)=C2)C2=N1 VXLUOMZPIYNTSE-UHFFFAOYSA-N 0.000 claims description 2
• NLZYLYWNXTXELX-UHFFFAOYSA-N 4-[[2-(2,4-dimethoxypyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-n-(2-methoxyethyl)-n-methylpiperazine-1-carboxamide Chemical compound C1CN(C(=O)N(C)CCOC)CCN1CC1=CC2=NC(C=3C(=NC(OC)=NC=3)OC)=NC(N3CCOCC3)=C2S1 NLZYLYWNXTXELX-UHFFFAOYSA-N 0.000 claims description 2
• KVUGKSFPGCRSDK-UHFFFAOYSA-N 4-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-n,n-dimethylpiperazine-1-sulfonamide Chemical compound C1CN(S(=O)(=O)N(C)C)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 KVUGKSFPGCRSDK-UHFFFAOYSA-N 0.000 claims description 2
• WLCJLHRHOKEZKM-UHFFFAOYSA-N 4-[[2-(6-aminopyridin-3-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-n,n-dimethylpiperazine-1-sulfonamide Chemical compound C1CN(S(=O)(=O)N(C)C)CCN1CC1=CC2=NC(C=3C=NC(N)=CC=3)=NC(N3CCOCC3)=C2S1 WLCJLHRHOKEZKM-UHFFFAOYSA-N 0.000 claims description 2
• RGMUGYGAAFQRTP-UHFFFAOYSA-N 4-methoxy-5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)S(C)(=O)=O)=C2)C2=N1 RGMUGYGAAFQRTP-UHFFFAOYSA-N 0.000 claims description 2
• XDZAIBHTQIWKGR-UHFFFAOYSA-N 4-methyl-5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound CC1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(C=C(CN2CCN(CC2)S(C)(=O)=O)S2)C2=N1 XDZAIBHTQIWKGR-UHFFFAOYSA-N 0.000 claims description 2
• XAZDYPNMXGDMSA-UHFFFAOYSA-N 4-methyl-5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound CC1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)S(C)(=O)=O)=C2)C2=N1 XAZDYPNMXGDMSA-UHFFFAOYSA-N 0.000 claims description 2
• DLXNRTLGDLCEIM-AWEZNQCLSA-N 5-[4-[(3s)-3-methylmorpholin-4-yl]-6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C[C@H]1COCCN1C1=NC(C=2C=NC(N)=NC=2)=NC2=C1SC(CN1CCN(CC1)S(C)(=O)=O)=C2 DLXNRTLGDLCEIM-AWEZNQCLSA-N 0.000 claims description 2
• JCLCFBVSDXIERH-UHFFFAOYSA-N 5-[4-morpholin-4-yl-6-(piperazin-1-ylmethyl)thieno[3,2-d]pyrimidin-2-yl]pyrazin-2-amine Chemical compound C1=NC(N)=CN=C1C1=NC(N2CCOCC2)=C(SC(CN2CCNCC2)=C2)C2=N1 JCLCFBVSDXIERH-UHFFFAOYSA-N 0.000 claims description 2
• PTDAGMVRTISBAZ-UHFFFAOYSA-N 5-[4-morpholin-4-yl-6-(piperazin-1-ylmethyl)thieno[3,2-d]pyrimidin-2-yl]pyridine-3-carbonitrile Chemical compound N#CC1=CN=CC(C=2N=C3C=C(CN4CCNCC4)SC3=C(N3CCOCC3)N=2)=C1 PTDAGMVRTISBAZ-UHFFFAOYSA-N 0.000 claims description 2
• VWQNOPIEXMLCCH-UHFFFAOYSA-N 5-[4-morpholin-4-yl-6-[(4-piperidin-1-ylpiperidin-1-yl)methyl]thieno[3,2-d]pyrimidin-2-yl]pyridin-2-amine Chemical compound C1=NC(N)=CC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCC(CC2)N2CCCCC2)=C2)C2=N1 VWQNOPIEXMLCCH-UHFFFAOYSA-N 0.000 claims description 2
• MVNMFQSLHVGANO-UHFFFAOYSA-N 5-[4-morpholin-4-yl-6-[(4-piperidin-1-ylpiperidin-1-yl)methyl]thieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCC(CC2)N2CCCCC2)=C2)C2=N1 MVNMFQSLHVGANO-UHFFFAOYSA-N 0.000 claims description 2
• YZNMFMDZYWMPQU-UHFFFAOYSA-N 5-[4-morpholin-4-yl-6-[(4-propan-2-ylsulfonylpiperazin-1-yl)methyl]thieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1CN(S(=O)(=O)C(C)C)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 YZNMFMDZYWMPQU-UHFFFAOYSA-N 0.000 claims description 2
• FMJLULYWZDADCT-UHFFFAOYSA-N 5-[4-morpholin-4-yl-6-[(4-pyrimidin-2-ylpiperazin-1-yl)methyl]thieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)C=2N=CC=CN=2)=C2)C2=N1 FMJLULYWZDADCT-UHFFFAOYSA-N 0.000 claims description 2
• XNLIDFYIRVBPRF-UHFFFAOYSA-N 5-[4-morpholin-4-yl-6-[(4-pyrrolidin-1-ylpiperidin-1-yl)methyl]thieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCC(CC2)N2CCCC2)=C2)C2=N1 XNLIDFYIRVBPRF-UHFFFAOYSA-N 0.000 claims description 2
• YSNNEYMJMCSISB-UHFFFAOYSA-N 5-[6-[(3-methylsulfonylpyrrolidin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1C(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 YSNNEYMJMCSISB-UHFFFAOYSA-N 0.000 claims description 2
• MLNJKUAQEMJPSY-UHFFFAOYSA-N 5-[6-[(4-cyclopropylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyridin-2-amine Chemical compound C1=NC(N)=CC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)S(=O)(=O)C2CC2)=C2)C2=N1 MLNJKUAQEMJPSY-UHFFFAOYSA-N 0.000 claims description 2
• HHGAXITTWXKDTE-UHFFFAOYSA-N 5-[6-[(4-cyclopropylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)S(=O)(=O)C2CC2)=C2)C2=N1 HHGAXITTWXKDTE-UHFFFAOYSA-N 0.000 claims description 2
• VDTFEDYCLBLXSK-UHFFFAOYSA-N 5-[6-[(4-cyclopropylsulfonylpiperazin-1-yl)methyl]-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound S1C2=C(N3CCOCC3)N=C(C=3C=NC(N)=NC=3)N=C2C(C)=C1CN(CC1)CCN1S(=O)(=O)C1CC1 VDTFEDYCLBLXSK-UHFFFAOYSA-N 0.000 claims description 2
• WLUSAFPHFDJDAJ-UHFFFAOYSA-N 5-[6-[(4-methylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1CN(C)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 WLUSAFPHFDJDAJ-UHFFFAOYSA-N 0.000 claims description 2
• RGWXDWONBDVNLY-UHFFFAOYSA-N 5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylfuro[2,3-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=NC(N)=NC=3)N=C2O1 RGWXDWONBDVNLY-UHFFFAOYSA-N 0.000 claims description 2
• DLSAIIMDFODBRE-UHFFFAOYSA-N 5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylfuro[3,2-d]pyrimidin-2-yl]pyridine-3-carbaldehyde Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3C=C(C=O)C=NC=3)=NC(N3CCOCC3)=C2O1 DLSAIIMDFODBRE-UHFFFAOYSA-N 0.000 claims description 2
• PRIOTMDPKGFUHG-UHFFFAOYSA-N 5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]-1,3-thiazol-2-amine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3SC(N)=NC=3)N=C2S1 PRIOTMDPKGFUHG-UHFFFAOYSA-N 0.000 claims description 2
• RRPHWEBVDSYTJM-UHFFFAOYSA-N 5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]pyridin-2-amine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=NC(N)=CC=3)N=C2S1 RRPHWEBVDSYTJM-UHFFFAOYSA-N 0.000 claims description 2
• WPLCPVNQQBBJBA-UHFFFAOYSA-N 5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=NC(N)=NC=3)N=C2S1 WPLCPVNQQBBJBA-UHFFFAOYSA-N 0.000 claims description 2
• WCRHPBQKBBRYSS-UHFFFAOYSA-N 5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]-1,3-thiazol-2-amine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3SC(N)=NC=3)=NC(N3CCOCC3)=C2S1 WCRHPBQKBBRYSS-UHFFFAOYSA-N 0.000 claims description 2
• NOPWVNDYQHHTSA-UHFFFAOYSA-N 5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]-1h-pyridin-2-one Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3C=NC(O)=CC=3)=NC(N3CCOCC3)=C2S1 NOPWVNDYQHHTSA-UHFFFAOYSA-N 0.000 claims description 2
• DHPDTFZJJGWXTK-UHFFFAOYSA-N 5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyridine-2-carboxamide Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3C=NC(=CC=3)C(N)=O)=NC(N3CCOCC3)=C2S1 DHPDTFZJJGWXTK-UHFFFAOYSA-N 0.000 claims description 2
• DKVYWIZHXFHHNQ-UHFFFAOYSA-N 5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 DKVYWIZHXFHHNQ-UHFFFAOYSA-N 0.000 claims description 2
• LCFOZHOQVZDEJG-UHFFFAOYSA-N 5-[6-[(4-methylsulfonylpiperidin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyridin-2-amine Chemical compound C1CC(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3C=NC(N)=CC=3)=NC(N3CCOCC3)=C2S1 LCFOZHOQVZDEJG-UHFFFAOYSA-N 0.000 claims description 2
• LIJBOMOMUPVXCX-UHFFFAOYSA-N 5-[6-[(4-methylsulfonylpiperidin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1CC(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 LIJBOMOMUPVXCX-UHFFFAOYSA-N 0.000 claims description 2
• OFVRMEMADVERMW-UHFFFAOYSA-N 5-[6-[[4-(2-methoxyethyl)piperazin-1-yl]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1CN(CCOC)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 OFVRMEMADVERMW-UHFFFAOYSA-N 0.000 claims description 2
• FICMEFQGKXPZGZ-UHFFFAOYSA-N 5-[6-[[4-(2-methylpropylsulfonyl)piperazin-1-yl]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyridin-2-amine Chemical compound C1CN(S(=O)(=O)CC(C)C)CCN1CC1=CC2=NC(C=3C=NC(N)=CC=3)=NC(N3CCOCC3)=C2S1 FICMEFQGKXPZGZ-UHFFFAOYSA-N 0.000 claims description 2
• KMIUWCIFVPEEGN-UHFFFAOYSA-N 5-[6-[[4-(benzenesulfonyl)piperazin-1-yl]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)S(=O)(=O)C=2C=CC=CC=2)=C2)C2=N1 KMIUWCIFVPEEGN-UHFFFAOYSA-N 0.000 claims description 2
• JMXGQZSBZQOUII-UHFFFAOYSA-N 5-[6-[[4-(benzenesulfonyl)piperazin-1-yl]methyl]-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound S1C2=C(N3CCOCC3)N=C(C=3C=NC(N)=NC=3)N=C2C(C)=C1CN(CC1)CCN1S(=O)(=O)C1=CC=CC=C1 JMXGQZSBZQOUII-UHFFFAOYSA-N 0.000 claims description 2
• BVYXLHAJABVQID-INIZCTEOSA-N 5-[6-[[4-[(2s)-2-hydroxypropanoyl]piperazin-1-yl]methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]pyridine-2-carbonitrile Chemical compound C1CN(C(=O)[C@@H](O)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=NC(=CC=3)C#N)N=C2S1 BVYXLHAJABVQID-INIZCTEOSA-N 0.000 claims description 2
• GXCDYWNDIOWCQC-KRWDZBQOSA-N 5-[6-[[4-[(2s)-2-hydroxypropanoyl]piperazin-1-yl]methyl]-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyridine-2-carbonitrile Chemical compound C1CN(C(=O)[C@@H](O)C)CCN1CC1=C(C)C2=NC(C=3C=NC(=CC=3)C#N)=NC(N3CCOCC3)=C2S1 GXCDYWNDIOWCQC-KRWDZBQOSA-N 0.000 claims description 2
• KBKSUYGXPNXSEA-HNNXBMFYSA-N 5-[6-[[methyl-(1-methylpiperidin-4-yl)amino]methyl]-4-[(3s)-3-methylmorpholin-4-yl]thieno[2,3-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C[C@H]1COCCN1C1=NC(C=2C=NC(N)=NC=2)=NC2=C1C=C(CN(C)C1CCN(C)CC1)S2 KBKSUYGXPNXSEA-HNNXBMFYSA-N 0.000 claims description 2
• FASUJQTVTMPCJJ-UHFFFAOYSA-N 5-[7-methyl-4-morpholin-4-yl-6-[(4-propan-2-ylsulfonylpiperazin-1-yl)methyl]thieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1CN(S(=O)(=O)C(C)C)CCN1CC1=C(C)C2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 FASUJQTVTMPCJJ-UHFFFAOYSA-N 0.000 claims description 2
• KZLVKDFCKIZZSI-UHFFFAOYSA-N 5-[7-methyl-6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyridin-2-amine Chemical compound S1C2=C(N3CCOCC3)N=C(C=3C=NC(N)=CC=3)N=C2C(C)=C1CN1CCN(S(C)(=O)=O)CC1 KZLVKDFCKIZZSI-UHFFFAOYSA-N 0.000 claims description 2
• AKKCGLXULFRAET-UHFFFAOYSA-N 5-[7-methyl-6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound S1C2=C(N3CCOCC3)N=C(C=3C=NC(N)=NC=3)N=C2C(C)=C1CN1CCN(S(C)(=O)=O)CC1 AKKCGLXULFRAET-UHFFFAOYSA-N 0.000 claims description 2
• DYGSZXAXESBXSQ-UHFFFAOYSA-N 5-[7-methyl-6-[(4-methylsulfonylpiperidin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyridin-2-amine Chemical compound S1C2=C(N3CCOCC3)N=C(C=3C=NC(N)=CC=3)N=C2C(C)=C1CN1CCC(S(C)(=O)=O)CC1 DYGSZXAXESBXSQ-UHFFFAOYSA-N 0.000 claims description 2
• IMRYORLGGZQIPF-UHFFFAOYSA-N 5-[7-methyl-6-[(4-methylsulfonylpiperidin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound S1C2=C(N3CCOCC3)N=C(C=3C=NC(N)=NC=3)N=C2C(C)=C1CN1CCC(S(C)(=O)=O)CC1 IMRYORLGGZQIPF-UHFFFAOYSA-N 0.000 claims description 2
• HFGFKWBWYGOHDQ-UHFFFAOYSA-N 5-[7-methyl-6-[[methyl-(1-methylpiperidin-4-yl)amino]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1CN(C)CCC1N(C)CC(=C(C1=N2)C)SC1=C(N1CCOCC1)N=C2C1=CN=C(N)N=C1 HFGFKWBWYGOHDQ-UHFFFAOYSA-N 0.000 claims description 2
• IYGRAZIIZZQMTN-UHFFFAOYSA-N 6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-yl-2-pyridin-3-ylfuro[3,2-d]pyrimidine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3C=NC=CC=3)=NC(N3CCOCC3)=C2O1 IYGRAZIIZZQMTN-UHFFFAOYSA-N 0.000 claims description 2
• CYVUWPPSBPVUMM-UHFFFAOYSA-N 6-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]pyridin-2-amine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3N=C(N)C=CC=3)N=C2S1 CYVUWPPSBPVUMM-UHFFFAOYSA-N 0.000 claims description 2
• 208000010507 Adenocarcinoma of Lung Diseases 0.000 claims description 2
• 208000003200 Adenoma Diseases 0.000 claims description 2
• 206010001233 Adenoma benign Diseases 0.000 claims description 2
• 208000019838 Blood disease Diseases 0.000 claims description 2
• 208000017604 Hodgkin disease Diseases 0.000 claims description 2
• 206010023347 Keratoacanthoma Diseases 0.000 claims description 2
• 206010029260 Neuroblastoma Diseases 0.000 claims description 2
• LUMXAAHMIKLZPO-UHFFFAOYSA-N [5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylfuro[3,2-d]pyrimidin-2-yl]pyridin-2-yl]urea Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3C=NC(NC(N)=O)=CC=3)=NC(N3CCOCC3)=C2O1 LUMXAAHMIKLZPO-UHFFFAOYSA-N 0.000 claims description 2
• QKXDXRHTCXKJTI-UHFFFAOYSA-N [5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]furan-2-yl]methanol Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3OC(CO)=CC=3)=NC(N3CCOCC3)=C2S1 QKXDXRHTCXKJTI-UHFFFAOYSA-N 0.000 claims description 2
• 208000009956 adenocarcinoma Diseases 0.000 claims description 2
• 239000002260 anti-inflammatory agent Substances 0.000 claims description 2
• 229940121363 anti-inflammatory agent Drugs 0.000 claims description 2
• 239000003443 antiviral agent Substances 0.000 claims description 2
• 210000000988 bone and bone Anatomy 0.000 claims description 2
• 210000000133 brain stem Anatomy 0.000 claims description 2
• 210000000481 breast Anatomy 0.000 claims description 2
• 210000003169 central nervous system Anatomy 0.000 claims description 2
• 210000003679 cervix uteri Anatomy 0.000 claims description 2
• 210000001072 colon Anatomy 0.000 claims description 2
• 230000002357 endometrial effect Effects 0.000 claims description 2
• 210000003238 esophagus Anatomy 0.000 claims description 2
• 230000002496 gastric effect Effects 0.000 claims description 2
• 208000014951 hematologic disease Diseases 0.000 claims description 2
• 208000018706 hematopoietic system disease Diseases 0.000 claims description 2
• 230000002519 immonomodulatory effect Effects 0.000 claims description 2
• 210000003734 kidney Anatomy 0.000 claims description 2
• 208000003849 large cell carcinoma Diseases 0.000 claims description 2
• 210000000867 larynx Anatomy 0.000 claims description 2
• BRTHKNNYPIMMIY-UHFFFAOYSA-N n-(2-methoxyethyl)-n-methyl-1-[(4-morpholin-4-yl-2-pyrimidin-5-ylthieno[2,3-d]pyrimidin-6-yl)methyl]piperidin-4-amine Chemical compound C1CC(N(C)CCOC)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=NC=NC=3)N=C2S1 BRTHKNNYPIMMIY-UHFFFAOYSA-N 0.000 claims description 2
• SKQJTLBKCOYJDE-UHFFFAOYSA-N n-[5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylfuro[3,2-d]pyrimidin-2-yl]pyridin-2-yl]acetamide Chemical compound C1=NC(NC(=O)C)=CC=C1C1=NC(N2CCOCC2)=C(OC(CN2CCN(CC2)S(C)(=O)=O)=C2)C2=N1 SKQJTLBKCOYJDE-UHFFFAOYSA-N 0.000 claims description 2
• ZOMKMIPXWPTTBU-UHFFFAOYSA-N n-[5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]-1,3-thiazol-2-yl]acetamide Chemical compound S1C(NC(=O)C)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)S(C)(=O)=O)=C2)C2=N1 ZOMKMIPXWPTTBU-UHFFFAOYSA-N 0.000 claims description 2
• KFXPGFBZQHHQHJ-UHFFFAOYSA-N n-[5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-yl]acetamide Chemical compound C1=NC(NC(=O)C)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)S(C)(=O)=O)=C2)C2=N1 KFXPGFBZQHHQHJ-UHFFFAOYSA-N 0.000 claims description 2
• SEGOKQZQZKBBIF-UHFFFAOYSA-N n-methyl-1-[(4-morpholin-4-yl-2-pyrimidin-5-ylthieno[2,3-d]pyrimidin-6-yl)methyl]piperidine-4-carboxamide Chemical compound C1CC(C(=O)NC)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=NC=NC=3)N=C2S1 SEGOKQZQZKBBIF-UHFFFAOYSA-N 0.000 claims description 2
• WWZMBQUZHQNGFI-UHFFFAOYSA-N n-methyl-5-[4-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[2,3-d]pyrimidin-2-yl]morpholin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(NC)=NC=C1C1OCCN(C=2N=C3SC(CN4CCN(CC4)S(C)(=O)=O)=CC3=CN=2)C1 WWZMBQUZHQNGFI-UHFFFAOYSA-N 0.000 claims description 2
• IDZCQVQESQLLFI-UHFFFAOYSA-N n-methyl-5-[4-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[3,2-d]pyrimidin-2-yl]morpholin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(NC)=NC=C1C1OCCN(C=2N=C3C=C(CN4CCN(CC4)S(C)(=O)=O)SC3=CN=2)C1 IDZCQVQESQLLFI-UHFFFAOYSA-N 0.000 claims description 2
• COXLQTANNNSTLK-UHFFFAOYSA-N n-methyl-5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(NC)=NC=C1C1=NC(N2CCOCC2)=C(C=C(CN2CCN(CC2)S(C)(=O)=O)S2)C2=N1 COXLQTANNNSTLK-UHFFFAOYSA-N 0.000 claims description 2
• 239000003076 neurotropic agent Substances 0.000 claims description 2
• 210000001672 ovary Anatomy 0.000 claims description 2
• 210000000496 pancreas Anatomy 0.000 claims description 2
• 230000000069 prophylactic effect Effects 0.000 claims description 2
• 210000002307 prostate Anatomy 0.000 claims description 2
• 208000000649 small cell carcinoma Diseases 0.000 claims description 2
• 210000002784 stomach Anatomy 0.000 claims description 2
• QWTAZVZBGPOSDO-UHFFFAOYSA-N tert-butyl 4-[[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazine-1-carboxylate Chemical compound S1C2=C(N3CCOCC3)N=C(C=3C=NC(N)=NC=3)N=C2C(C)=C1CN1CCN(C(=O)OC(C)(C)C)CC1 QWTAZVZBGPOSDO-UHFFFAOYSA-N 0.000 claims description 2
• 210000001550 testis Anatomy 0.000 claims description 2
• 210000001685 thyroid gland Anatomy 0.000 claims description 2
• 229910052720 vanadium Inorganic materials 0.000 claims description 2
• LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 claims 7
• 102000038030 PI3Ks Human genes 0.000 claims 4
• OHZLGNYWJIBNQL-UHFFFAOYSA-N 2-[1-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperidin-4-yl]sulfonyl-n,n-dimethylacetamide Chemical compound C1CC(S(=O)(=O)CC(=O)N(C)C)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 OHZLGNYWJIBNQL-UHFFFAOYSA-N 0.000 claims 2
• SKMIQINGCMDHAW-UHFFFAOYSA-N 5-[4-morpholin-4-yl-6-[(4-thiophen-2-ylsulfonylpiperazin-1-yl)methyl]thieno[2,3-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(C=C(CN2CCN(CC2)S(=O)(=O)C=2SC=CC=2)S2)C2=N1 SKMIQINGCMDHAW-UHFFFAOYSA-N 0.000 claims 2
• CCGSJDZORYRNJY-UHFFFAOYSA-N 5-[4-morpholin-4-yl-6-[[4-(1,3-thiazol-2-ylsulfonyl)piperidin-1-yl]methyl]thieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCC(CC2)S(=O)(=O)C=2SC=CN=2)=C2)C2=N1 CCGSJDZORYRNJY-UHFFFAOYSA-N 0.000 claims 2
• JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 claims 2
• JEEZQGFAASQUPA-UHFFFAOYSA-N (1-aminocyclopropyl)-[4-[[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]methanone Chemical compound S1C2=C(N3CCOCC3)N=C(C=3C=NC(N)=NC=3)N=C2C(C)=C1CN(CC1)CCN1C(=O)C1(N)CC1 JEEZQGFAASQUPA-UHFFFAOYSA-N 0.000 claims 1
• NOXQEXHGLFKCLC-OAHLLOKOSA-N (2r)-2-amino-1-[4-[[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]propan-1-one Chemical compound C1CN(C(=O)[C@H](N)C)CCN1CC1=C(C)C2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 NOXQEXHGLFKCLC-OAHLLOKOSA-N 0.000 claims 1
• NOXQEXHGLFKCLC-HNNXBMFYSA-N (2s)-2-amino-1-[4-[[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]propan-1-one Chemical compound C1CN(C(=O)[C@@H](N)C)CCN1CC1=C(C)C2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 NOXQEXHGLFKCLC-HNNXBMFYSA-N 0.000 claims 1
• AXIJTVFNTHERFP-HNNXBMFYSA-N (2s)-2-hydroxy-1-[4-[[2-[2-(methylamino)pyrimidin-5-yl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl]methyl]piperazin-1-yl]propan-1-one Chemical compound C1=NC(NC)=NC=C1C1=NC(N2CCOCC2)=C(C=C(CN2CCN(CC2)C(=O)[C@H](C)O)S2)C2=N1 AXIJTVFNTHERFP-HNNXBMFYSA-N 0.000 claims 1
• QKCYVJBUWNBHJA-INIZCTEOSA-N (2s)-2-hydroxy-1-[4-[[7-methyl-2-[2-(methylamino)pyrimidin-5-yl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]propan-1-one Chemical compound C1=NC(NC)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)C(=O)[C@H](C)O)=C2C)C2=N1 QKCYVJBUWNBHJA-INIZCTEOSA-N 0.000 claims 1
• PLIAPZHBJWSKGH-UHFFFAOYSA-N 1-[4-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-hydroxyethanone Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(C=C(CN2CCN(CC2)C(=O)CO)S2)C2=N1 PLIAPZHBJWSKGH-UHFFFAOYSA-N 0.000 claims 1
• GTVUTNRKYBQWNW-UHFFFAOYSA-N 1-[4-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-(dimethylamino)ethanone Chemical compound C1CN(C(=O)CN(C)C)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 GTVUTNRKYBQWNW-UHFFFAOYSA-N 0.000 claims 1
• MRNJOYWRCWTXIR-UHFFFAOYSA-N 1-[4-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-hydroxy-2-methylpropan-1-one Chemical compound C1CN(C(=O)C(C)(O)C)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 MRNJOYWRCWTXIR-UHFFFAOYSA-N 0.000 claims 1
• HCSQBCGHQKUDMP-UHFFFAOYSA-N 1-[4-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-methylsulfonylethanone Chemical compound C1CN(C(=O)CS(=O)(=O)C)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 HCSQBCGHQKUDMP-UHFFFAOYSA-N 0.000 claims 1
• TXGXEBFRWQJBOG-UHFFFAOYSA-N 1-[4-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]sulfonyl-2-methylpropan-1-one Chemical compound C1CN(S(=O)(=O)C(=O)C(C)C)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 TXGXEBFRWQJBOG-UHFFFAOYSA-N 0.000 claims 1
• WKIDEPKQBNVVJE-UHFFFAOYSA-N 1-[4-[[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-(dimethylamino)ethanone Chemical compound C1CN(C(=O)CN(C)C)CCN1CC1=C(C)C2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 WKIDEPKQBNVVJE-UHFFFAOYSA-N 0.000 claims 1
• YPFFPBKNPHCNIF-UHFFFAOYSA-N 1-[4-[[2-(6-aminopyridin-3-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-hydroxyethanone Chemical compound C1=NC(N)=CC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)C(=O)CO)=C2)C2=N1 YPFFPBKNPHCNIF-UHFFFAOYSA-N 0.000 claims 1
• ZYSOOUVFIHTRPL-UHFFFAOYSA-N 1-[[2-(2,4-dimethoxypyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-n-methylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)NC)CCN1CC1=CC2=NC(C=3C(=NC(OC)=NC=3)OC)=NC(N3CCOCC3)=C2S1 ZYSOOUVFIHTRPL-UHFFFAOYSA-N 0.000 claims 1
• HBNUHUVUGYDLJB-UHFFFAOYSA-N 1-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-4-(4-chlorophenyl)piperidin-4-ol Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCC(O)(CC2)C=2C=CC(Cl)=CC=2)=C2)C2=N1 HBNUHUVUGYDLJB-UHFFFAOYSA-N 0.000 claims 1
• UCIZLKQSYOUNBE-UHFFFAOYSA-N 1-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-n,n-dimethylpiperidine-4-sulfonamide Chemical compound C1CC(S(=O)(=O)N(C)C)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 UCIZLKQSYOUNBE-UHFFFAOYSA-N 0.000 claims 1
• AXPOMZYFYHYHGM-UHFFFAOYSA-N 1-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-n-methylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)NC)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 AXPOMZYFYHYHGM-UHFFFAOYSA-N 0.000 claims 1
• LJKAYKGKAQGNPE-UHFFFAOYSA-N 1-[[2-(6-aminopyridin-3-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-n,n-dimethylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)CCN1CC1=CC2=NC(C=3C=NC(N)=CC=3)=NC(N3CCOCC3)=C2S1 LJKAYKGKAQGNPE-UHFFFAOYSA-N 0.000 claims 1
• RIUVPGXSHFRBHU-UHFFFAOYSA-N 2-[4-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl]methyl]piperazin-1-yl]ethanol Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(C=C(CN2CCN(CCO)CC2)S2)C2=N1 RIUVPGXSHFRBHU-UHFFFAOYSA-N 0.000 claims 1
• IRYPRNBFNRSBFQ-UHFFFAOYSA-N 2-amino-1-[4-[[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-methylpropan-1-one Chemical compound S1C2=C(N3CCOCC3)N=C(C=3C=NC(N)=NC=3)N=C2C(C)=C1CN1CCN(C(=O)C(C)(C)N)CC1 IRYPRNBFNRSBFQ-UHFFFAOYSA-N 0.000 claims 1
• ULKIEJUPHQMXQN-UHFFFAOYSA-N 2-amino-1-[4-[[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]ethanone Chemical compound S1C2=C(N3CCOCC3)N=C(C=3C=NC(N)=NC=3)N=C2C(C)=C1CN1CCN(C(=O)CN)CC1 ULKIEJUPHQMXQN-UHFFFAOYSA-N 0.000 claims 1
• JFNOGKTYWXBQGY-UHFFFAOYSA-N 4-[2-(4-methylpyridin-3-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[2,3-d]pyrimidin-4-yl]morpholine Chemical compound CC1=CC=NC=C1C1=NC(N2CCOCC2)=C(C=C(CN2CCN(CC2)S(C)(=O)=O)S2)C2=N1 JFNOGKTYWXBQGY-UHFFFAOYSA-N 0.000 claims 1
• RXPGTCGBAIHVGH-UHFFFAOYSA-N 4-[2-(5-methylpyridin-3-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[2,3-d]pyrimidin-4-yl]morpholine Chemical compound CC1=CN=CC(C=2N=C3SC(CN4CCN(CC4)S(C)(=O)=O)=CC3=C(N3CCOCC3)N=2)=C1 RXPGTCGBAIHVGH-UHFFFAOYSA-N 0.000 claims 1
• JAKBHHSTZDBLEK-UHFFFAOYSA-N 4-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-2-(6-phenylpyridin-3-yl)thieno[2,3-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=NC(=CC=3)C=3C=CC=CC=3)N=C2S1 JAKBHHSTZDBLEK-UHFFFAOYSA-N 0.000 claims 1
• BBUYLOWGHXSUAL-UHFFFAOYSA-N 4-methyl-5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]pyridin-2-amine Chemical compound CC1=CC(N)=NC=C1C1=NC(N2CCOCC2)=C(C=C(CN2CCN(CC2)S(C)(=O)=O)S2)C2=N1 BBUYLOWGHXSUAL-UHFFFAOYSA-N 0.000 claims 1
• MYVFDCQGKGXZCT-UHFFFAOYSA-N 5-[4-morpholin-4-yl-6-[(4-morpholin-4-ylpiperidin-1-yl)methyl]thieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCC(CC2)N2CCOCC2)=C2)C2=N1 MYVFDCQGKGXZCT-UHFFFAOYSA-N 0.000 claims 1
• HAKHICFQWUJUER-UHFFFAOYSA-N 5-[4-morpholin-4-yl-6-[(4-piperidin-1-ylpiperidin-1-yl)methyl]thieno[2,3-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(C=C(CN2CCC(CC2)N2CCCCC2)S2)C2=N1 HAKHICFQWUJUER-UHFFFAOYSA-N 0.000 claims 1
• GLTYAIKNDHECEG-UHFFFAOYSA-N 5-[4-morpholin-4-yl-6-[[4-(morpholin-4-ylmethyl)piperidin-1-yl]methyl]thieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCC(CN3CCOCC3)CC2)=C2)C2=N1 GLTYAIKNDHECEG-UHFFFAOYSA-N 0.000 claims 1
• LONYAZSIXKELDN-UHFFFAOYSA-N 5-[4-morpholin-4-yl-6-[[4-(piperidin-1-ylmethyl)piperidin-1-yl]methyl]thieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCC(CN3CCCCC3)CC2)=C2)C2=N1 LONYAZSIXKELDN-UHFFFAOYSA-N 0.000 claims 1
• VATXPWUSMHYFAO-UHFFFAOYSA-N 5-[4-morpholin-4-yl-6-[[4-(pyrrolidin-1-ylmethyl)piperidin-1-yl]methyl]thieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCC(CN3CCCC3)CC2)=C2)C2=N1 VATXPWUSMHYFAO-UHFFFAOYSA-N 0.000 claims 1
• XAKDBNRKMHTIQJ-UHFFFAOYSA-N 5-[6-[(3-methylsulfonylpyrrolidin-1-yl)methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1C(S(=O)(=O)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=NC(N)=NC=3)N=C2S1 XAKDBNRKMHTIQJ-UHFFFAOYSA-N 0.000 claims 1
• AGAMOTDTIREVOD-UHFFFAOYSA-N 5-[6-[(4-aminopiperidin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1CC(N)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 AGAMOTDTIREVOD-UHFFFAOYSA-N 0.000 claims 1
• IMRSXTQXQKBCAA-UHFFFAOYSA-N 5-[6-[(4-cyclopropylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(C=C(CN2CCN(CC2)S(=O)(=O)C2CC2)S2)C2=N1 IMRSXTQXQKBCAA-UHFFFAOYSA-N 0.000 claims 1
• BENDHOSIDINEPF-UHFFFAOYSA-N 5-[6-[(4-ethylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1CN(S(=O)(=O)CC)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 BENDHOSIDINEPF-UHFFFAOYSA-N 0.000 claims 1
• QNAXBDCTZPSFNK-UHFFFAOYSA-N 5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]-3-nitropyridin-2-amine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=C(C(N)=NC=3)[N+]([O-])=O)N=C2S1 QNAXBDCTZPSFNK-UHFFFAOYSA-N 0.000 claims 1
• GKYHFVUKIYFTPC-UHFFFAOYSA-N 5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]-4-(trifluoromethyl)pyrimidin-2-amine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C(=NC(N)=NC=3)C(F)(F)F)N=C2S1 GKYHFVUKIYFTPC-UHFFFAOYSA-N 0.000 claims 1
• XIOIAXABIAUOGX-UHFFFAOYSA-N 5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]-n-propan-2-ylpyrimidin-2-amine Chemical compound C1=NC(NC(C)C)=NC=C1C1=NC(N2CCOCC2)=C(C=C(CN2CCN(CC2)S(C)(=O)=O)S2)C2=N1 XIOIAXABIAUOGX-UHFFFAOYSA-N 0.000 claims 1
• YIWVVQLJSFLOHM-UHFFFAOYSA-N 5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]pyridin-3-amine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=C(N)C=NC=3)N=C2S1 YIWVVQLJSFLOHM-UHFFFAOYSA-N 0.000 claims 1
• PPCQFSHMYVOBGA-UHFFFAOYSA-N 5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]-4-(trifluoromethyl)pyrimidin-2-amine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3C(=NC(N)=NC=3)C(F)(F)F)=NC(N3CCOCC3)=C2S1 PPCQFSHMYVOBGA-UHFFFAOYSA-N 0.000 claims 1
• ARWPKQOWZCGWIH-UHFFFAOYSA-N 5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]-n-propan-2-ylpyrimidin-2-amine Chemical compound C1=NC(NC(C)C)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)S(C)(=O)=O)=C2)C2=N1 ARWPKQOWZCGWIH-UHFFFAOYSA-N 0.000 claims 1
• QJGPVKUDSVMVMX-UHFFFAOYSA-N 5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyridine-2-carbonitrile Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3C=NC(=CC=3)C#N)=NC(N3CCOCC3)=C2S1 QJGPVKUDSVMVMX-UHFFFAOYSA-N 0.000 claims 1
• KLXMMRLIIXNDSN-UHFFFAOYSA-N 5-[6-[(4-methylsulfonylpiperidin-1-yl)methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1CC(S(=O)(=O)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=NC(N)=NC=3)N=C2S1 KLXMMRLIIXNDSN-UHFFFAOYSA-N 0.000 claims 1
• LXMMDYVJBRLVMA-UHFFFAOYSA-N 5-[6-[1-(4-methylsulfonylpiperazin-1-yl)ethyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyridin-2-amine Chemical compound C=1C2=NC(C=3C=NC(N)=CC=3)=NC(N3CCOCC3)=C2SC=1C(C)N1CCN(S(C)(=O)=O)CC1 LXMMDYVJBRLVMA-UHFFFAOYSA-N 0.000 claims 1
• MSQKBCBWQOJOOP-UHFFFAOYSA-N 5-[6-[1-(4-methylsulfonylpiperazin-1-yl)ethyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C=1C2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2SC=1C(C)N1CCN(S(C)(=O)=O)CC1 MSQKBCBWQOJOOP-UHFFFAOYSA-N 0.000 claims 1
• GXUKMJRZDYTFCK-UHFFFAOYSA-N 5-[6-[[(1-cyclohexylpiperidin-4-yl)-methylamino]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1CN(C2CCCCC2)CCC1N(C)CC(SC1=2)=CC1=NC(C=1C=NC(N)=NC=1)=NC=2N1CCOCC1 GXUKMJRZDYTFCK-UHFFFAOYSA-N 0.000 claims 1
• VBQOVUBFWCRVTR-UHFFFAOYSA-N 5-[6-[[(1-cyclopropylpiperidin-4-yl)-methylamino]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1CN(C2CC2)CCC1N(C)CC(SC1=2)=CC1=NC(C=1C=NC(N)=NC=1)=NC=2N1CCOCC1 VBQOVUBFWCRVTR-UHFFFAOYSA-N 0.000 claims 1
• OUIMVIGCCHFMQH-UHFFFAOYSA-N 5-[6-[[(1-ethylpiperidin-4-yl)-methylamino]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1CN(CC)CCC1N(C)CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 OUIMVIGCCHFMQH-UHFFFAOYSA-N 0.000 claims 1
• INKCZPNCPOGEGV-UHFFFAOYSA-N 5-[6-[[(1-methylpiperidin-4-yl)amino]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1CN(C)CCC1NCC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 INKCZPNCPOGEGV-UHFFFAOYSA-N 0.000 claims 1
• FCVZQRZJTXGWFG-GASCZTMLSA-N 5-[6-[[(2r,6s)-2,6-dimethyl-4-methylsulfonylpiperazin-1-yl]methyl]-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C[C@H]1CN(S(C)(=O)=O)C[C@@H](C)N1CC1=C(C)C2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 FCVZQRZJTXGWFG-GASCZTMLSA-N 0.000 claims 1
• MLBAAPJFDOCXBN-UHFFFAOYSA-N 5-[6-[[2-methoxyethyl-(1-propan-2-ylpiperidin-4-yl)amino]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1CN(C(C)C)CCC1N(CCOC)CC(SC1=2)=CC1=NC(C=1C=NC(N)=NC=1)=NC=2N1CCOCC1 MLBAAPJFDOCXBN-UHFFFAOYSA-N 0.000 claims 1
• OCGWHYISYLSYHR-UHFFFAOYSA-N 5-[6-[[3-(dimethylamino)pyrrolidin-1-yl]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1C(N(C)C)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 OCGWHYISYLSYHR-UHFFFAOYSA-N 0.000 claims 1
• YSDTZSHLIDUVAR-UHFFFAOYSA-N 5-[6-[[4-(1-methylimidazol-4-yl)piperazin-1-yl]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound CN1C=NC(N2CCN(CC=3SC4=C(N5CCOCC5)N=C(N=C4C=3)C=3C=NC(N)=NC=3)CC2)=C1 YSDTZSHLIDUVAR-UHFFFAOYSA-N 0.000 claims 1
• DHXQTPJWQFUCQO-UHFFFAOYSA-N 5-[6-[[4-(1-methylpiperidin-4-yl)piperazin-1-yl]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1CN(C)CCC1N1CCN(CC=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=NC(N)=NC=2)CC1 DHXQTPJWQFUCQO-UHFFFAOYSA-N 0.000 claims 1
• HLMPRTQAPWALRQ-UHFFFAOYSA-N 5-[6-[[4-(2-fluorophenyl)sulfonylpiperazin-1-yl]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)S(=O)(=O)C=2C(=CC=CC=2)F)=C2)C2=N1 HLMPRTQAPWALRQ-UHFFFAOYSA-N 0.000 claims 1
• GBPYWUWBMVSNOW-UHFFFAOYSA-N 5-[6-[[4-(3-fluorophenyl)sulfonylpiperazin-1-yl]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)S(=O)(=O)C=2C=C(F)C=CC=2)=C2)C2=N1 GBPYWUWBMVSNOW-UHFFFAOYSA-N 0.000 claims 1
• CVDAHJKPBXYZQA-UHFFFAOYSA-N 5-[6-[[4-(4-fluorophenyl)sulfonylpiperazin-1-yl]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)S(=O)(=O)C=2C=CC(F)=CC=2)=C2)C2=N1 CVDAHJKPBXYZQA-UHFFFAOYSA-N 0.000 claims 1
• IGLWKUBDMFFSTC-UHFFFAOYSA-N 5-[6-[[4-(dimethylamino)piperidin-1-yl]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1CC(N(C)C)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 IGLWKUBDMFFSTC-UHFFFAOYSA-N 0.000 claims 1
• NAJCYIQZNNQLCB-UHFFFAOYSA-N 5-[6-[[4-(methylsulfonylmethylsulfonyl)piperazin-1-yl]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1CN(S(=O)(=O)CS(=O)(=O)C)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 NAJCYIQZNNQLCB-UHFFFAOYSA-N 0.000 claims 1
• DGLGCGPYLBJRJL-UHFFFAOYSA-N 5-[6-[[4-(methylsulfonylmethylsulfonyl)piperidin-1-yl]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1CC(S(=O)(=O)CS(=O)(=O)C)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 DGLGCGPYLBJRJL-UHFFFAOYSA-N 0.000 claims 1
• XXXDXUAYTCKDGU-UHFFFAOYSA-N 5-[6-[[4-[(2-methylimidazol-1-yl)methyl]piperidin-1-yl]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound CC1=NC=CN1CC1CCN(CC=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=NC(N)=NC=2)CC1 XXXDXUAYTCKDGU-UHFFFAOYSA-N 0.000 claims 1
• SLMUEYZNQYLTMG-UHFFFAOYSA-N 5-[6-[[4-[(dimethylamino)methyl]piperidin-1-yl]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1CC(CN(C)C)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 SLMUEYZNQYLTMG-UHFFFAOYSA-N 0.000 claims 1
• MGJWLSYXZOXKKR-UHFFFAOYSA-N 5-[6-[[4-[2-methoxyethyl(methyl)amino]piperidin-1-yl]methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]-n-methylpyridin-2-amine Chemical compound C1=NC(NC)=CC=C1C1=NC(N2CCOCC2)=C(C=C(CN2CCC(CC2)N(C)CCOC)S2)C2=N1 MGJWLSYXZOXKKR-UHFFFAOYSA-N 0.000 claims 1
• ZOXZHRXUZMKVHK-UHFFFAOYSA-N 5-[6-[[4-[2-methoxyethyl(methyl)amino]piperidin-1-yl]methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]-n-methylpyrimidin-2-amine Chemical compound C1=NC(NC)=NC=C1C1=NC(N2CCOCC2)=C(C=C(CN2CCC(CC2)N(C)CCOC)S2)C2=N1 ZOXZHRXUZMKVHK-UHFFFAOYSA-N 0.000 claims 1
• XPMGSADFXIYUEJ-UHFFFAOYSA-N 5-[6-[[4-[2-methoxyethyl(methyl)amino]piperidin-1-yl]methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]pyridin-2-amine Chemical compound C1CC(N(C)CCOC)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=NC(N)=CC=3)N=C2S1 XPMGSADFXIYUEJ-UHFFFAOYSA-N 0.000 claims 1
• AKCJZNUYQJPJET-UHFFFAOYSA-N 5-[6-[[4-[2-methoxyethyl(methyl)amino]piperidin-1-yl]methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1CC(N(C)CCOC)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=NC(N)=NC=3)N=C2S1 AKCJZNUYQJPJET-UHFFFAOYSA-N 0.000 claims 1
• NWRPUTGZMAYZGC-UHFFFAOYSA-N 5-[6-[[4-[2-methoxyethyl(methyl)amino]piperidin-1-yl]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1CC(N(C)CCOC)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 NWRPUTGZMAYZGC-UHFFFAOYSA-N 0.000 claims 1
• IFTUGLUOCRVCAE-UHFFFAOYSA-N 5-[6-[[4-[benzyl(methyl)amino]piperidin-1-yl]methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1CN(CC=2SC3=NC(=NC(=C3C=2)N2CCOCC2)C=2C=NC(N)=NC=2)CCC1N(C)CC1=CC=CC=C1 IFTUGLUOCRVCAE-UHFFFAOYSA-N 0.000 claims 1
• FDAMCHBDJLWOAW-UHFFFAOYSA-N 5-[6-[[[1-(2-methoxyethyl)piperidin-4-yl]-methylamino]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1CN(CCOC)CCC1N(C)CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 FDAMCHBDJLWOAW-UHFFFAOYSA-N 0.000 claims 1
• LRAHIOGZOXJIGP-UHFFFAOYSA-N 5-[6-[[methyl(piperidin-4-yl)amino]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1CNCCC1N(C)CC(SC1=2)=CC1=NC(C=1C=NC(N)=NC=1)=NC=2N1CCOCC1 LRAHIOGZOXJIGP-UHFFFAOYSA-N 0.000 claims 1
• IQZKBTPLGLATAJ-UHFFFAOYSA-N 5-[6-[[methyl(piperidin-4-ylmethyl)amino]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C=1C2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2SC=1CN(C)CC1CCNCC1 IQZKBTPLGLATAJ-UHFFFAOYSA-N 0.000 claims 1
• BBVWFPRCNQEVMT-UHFFFAOYSA-N 5-[6-[[methyl(pyridin-2-ylmethyl)amino]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C=1C=CC=NC=1CN(C)CC(SC1=2)=CC1=NC(C=1C=NC(N)=NC=1)=NC=2N1CCOCC1 BBVWFPRCNQEVMT-UHFFFAOYSA-N 0.000 claims 1
• QVIFOIKLNCXIMH-UHFFFAOYSA-N 5-[6-[[methyl(pyridin-3-ylmethyl)amino]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C=1C=CN=CC=1CN(C)CC(SC1=2)=CC1=NC(C=1C=NC(N)=NC=1)=NC=2N1CCOCC1 QVIFOIKLNCXIMH-UHFFFAOYSA-N 0.000 claims 1
• OZAIPKAIQIVIMQ-UHFFFAOYSA-N 5-[6-[[methyl(pyridin-4-ylmethyl)amino]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C=1C=NC=CC=1CN(C)CC(SC1=2)=CC1=NC(C=1C=NC(N)=NC=1)=NC=2N1CCOCC1 OZAIPKAIQIVIMQ-UHFFFAOYSA-N 0.000 claims 1
• NBENDCRTHVJWBD-UHFFFAOYSA-N 5-[6-[[methyl-(1-methylpiperidin-4-yl)amino]methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]-4-(trifluoromethyl)pyrimidin-2-amine Chemical compound C1CN(C)CCC1N(C)CC(SC1=N2)=CC1=C(N1CCOCC1)N=C2C1=CN=C(N)N=C1C(F)(F)F NBENDCRTHVJWBD-UHFFFAOYSA-N 0.000 claims 1
• XOZQQLYORRLNOO-UHFFFAOYSA-N 5-[6-[[methyl-(1-methylpiperidin-4-yl)amino]methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1CN(C)CCC1N(C)CC(SC1=N2)=CC1=C(N1CCOCC1)N=C2C1=CN=C(N)N=C1 XOZQQLYORRLNOO-UHFFFAOYSA-N 0.000 claims 1
• UVAPRNZXZIPNRF-UHFFFAOYSA-N 5-[6-[[methyl-(1-methylpyrrolidin-3-yl)amino]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1CN(C)CC1N(C)CC(SC1=2)=CC1=NC(C=1C=NC(N)=NC=1)=NC=2N1CCOCC1 UVAPRNZXZIPNRF-UHFFFAOYSA-N 0.000 claims 1
• MSFRPRLBBAMOIY-UHFFFAOYSA-N 5-[6-[[methyl-(1-propan-2-ylpiperidin-4-yl)amino]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1CN(C(C)C)CCC1N(C)CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 MSFRPRLBBAMOIY-UHFFFAOYSA-N 0.000 claims 1
• IFYNXMRHLZTROX-UHFFFAOYSA-N 5-[6-[[methyl-(1-propylpiperidin-4-yl)amino]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1CN(CCC)CCC1N(C)CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 IFYNXMRHLZTROX-UHFFFAOYSA-N 0.000 claims 1
• JHBGDWWLFOTFQI-UHFFFAOYSA-N 5-[6-[[methyl-[(1-methylimidazol-4-yl)methyl]amino]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C=1C2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2SC=1CN(C)CC1=CN(C)C=N1 JHBGDWWLFOTFQI-UHFFFAOYSA-N 0.000 claims 1
• WIRKQLSAZZVZQK-UHFFFAOYSA-N 5-[6-[[methyl-[(1-methylpiperidin-4-yl)methyl]amino]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C=1C2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2SC=1CN(C)CC1CCN(C)CC1 WIRKQLSAZZVZQK-UHFFFAOYSA-N 0.000 claims 1
• GUABJXDAOMDLDO-UHFFFAOYSA-N 5-[6-[[methyl-[(4-methyl-1,3-thiazol-2-yl)methyl]amino]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound N=1C(C)=CSC=1CN(C)CC(SC1=2)=CC1=NC(C=1C=NC(N)=NC=1)=NC=2N1CCOCC1 GUABJXDAOMDLDO-UHFFFAOYSA-N 0.000 claims 1
• LZQIJBHNVVBQDJ-UHFFFAOYSA-N 5-[6-[[methyl-[1-(2-methylpropyl)piperidin-4-yl]amino]methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1CN(CC(C)C)CCC1N(C)CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 LZQIJBHNVVBQDJ-UHFFFAOYSA-N 0.000 claims 1
• JQNGCUWDYOVBGX-UHFFFAOYSA-N 5-[7-methyl-4-morpholin-4-yl-6-(piperazin-1-ylmethyl)thieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound S1C2=C(N3CCOCC3)N=C(C=3C=NC(N)=NC=3)N=C2C(C)=C1CN1CCNCC1 JQNGCUWDYOVBGX-UHFFFAOYSA-N 0.000 claims 1
• PDRXSDUOMBZZGV-UHFFFAOYSA-N [5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]pyridin-2-yl]methanol Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=NC(CO)=CC=3)N=C2S1 PDRXSDUOMBZZGV-UHFFFAOYSA-N 0.000 claims 1
• 210000004556 brain Anatomy 0.000 claims 1
• 210000003128 head Anatomy 0.000 claims 1
• 210000004185 liver Anatomy 0.000 claims 1
• AKYVXELTDYNHGJ-UHFFFAOYSA-N n,1-dimethyl-n-[(4-morpholin-4-yl-2-pyridin-3-ylthieno[3,2-d]pyrimidin-6-yl)methyl]piperidin-4-amine Chemical compound C1CN(C)CCC1N(C)CC(SC1=2)=CC1=NC(C=1C=NC=CC=1)=NC=2N1CCOCC1 AKYVXELTDYNHGJ-UHFFFAOYSA-N 0.000 claims 1
• SFZYCWWCUPKMLZ-UHFFFAOYSA-N n,3-dimethyl-5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]pyridin-2-amine Chemical compound C1=C(C)C(NC)=NC=C1C1=NC(N2CCOCC2)=C(C=C(CN2CCN(CC2)S(C)(=O)=O)S2)C2=N1 SFZYCWWCUPKMLZ-UHFFFAOYSA-N 0.000 claims 1
• PKAKSJNDACLARP-UHFFFAOYSA-N n,n-dimethyl-2-[5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]pyrimidin-2-yl]oxyethanamine Chemical compound C1=NC(OCCN(C)C)=NC=C1C1=NC(N2CCOCC2)=C(C=C(CN2CCN(CC2)S(C)(=O)=O)S2)C2=N1 PKAKSJNDACLARP-UHFFFAOYSA-N 0.000 claims 1
• OVGAOZHAOVZSBT-UHFFFAOYSA-N n-[1-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperidin-4-yl]-n-methylmethanesulfonamide Chemical compound C1CC(N(C)S(C)(=O)=O)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 OVGAOZHAOVZSBT-UHFFFAOYSA-N 0.000 claims 1
• ZEGZHJMRIYDSFW-UHFFFAOYSA-N n-[1-[[2-(6-aminopyridin-3-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperidin-4-yl]-n-methylmethanesulfonamide Chemical compound C1CC(N(C)S(C)(=O)=O)CCN1CC1=CC2=NC(C=3C=NC(N)=CC=3)=NC(N3CCOCC3)=C2S1 ZEGZHJMRIYDSFW-UHFFFAOYSA-N 0.000 claims 1
• ZYJQHZWDLRWJBR-UHFFFAOYSA-N n-[5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]pyridin-2-yl]acetamide Chemical compound C1=NC(NC(=O)C)=CC=C1C1=NC(N2CCOCC2)=C(C=C(CN2CCN(CC2)S(C)(=O)=O)S2)C2=N1 ZYJQHZWDLRWJBR-UHFFFAOYSA-N 0.000 claims 1
• NNPDROGKGWWRFU-UHFFFAOYSA-N n-ethyl-5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]pyridin-2-amine Chemical compound C1=NC(NCC)=CC=C1C1=NC(N2CCOCC2)=C(C=C(CN2CCN(CC2)S(C)(=O)=O)S2)C2=N1 NNPDROGKGWWRFU-UHFFFAOYSA-N 0.000 claims 1
• YLPSVINZFCAYDR-UHFFFAOYSA-N n-ethyl-5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(NCC)=NC=C1C1=NC(N2CCOCC2)=C(C=C(CN2CCN(CC2)S(C)(=O)=O)S2)C2=N1 YLPSVINZFCAYDR-UHFFFAOYSA-N 0.000 claims 1
• HZAVNTBYLNBVSQ-UHFFFAOYSA-N n-ethyl-5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(NCC)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)S(C)(=O)=O)=C2)C2=N1 HZAVNTBYLNBVSQ-UHFFFAOYSA-N 0.000 claims 1
• AKCSFRKEYPFSFZ-UHFFFAOYSA-N n-methyl-5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]pyridin-2-amine Chemical compound C1=NC(NC)=CC=C1C1=NC(N2CCOCC2)=C(C=C(CN2CCN(CC2)S(C)(=O)=O)S2)C2=N1 AKCSFRKEYPFSFZ-UHFFFAOYSA-N 0.000 claims 1
• WXUGMQXGZJXDSL-UHFFFAOYSA-N n-methyl-5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(NC)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)S(C)(=O)=O)=C2)C2=N1 WXUGMQXGZJXDSL-UHFFFAOYSA-N 0.000 claims 1
• VLQUJDFYPDPKQK-UHFFFAOYSA-N n-methyl-5-[6-[[methyl-(1-methylpiperidin-4-yl)amino]methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(NC)=NC=C1C1=NC(N2CCOCC2)=C(C=C(CN(C)C2CCN(C)CC2)S2)C2=N1 VLQUJDFYPDPKQK-UHFFFAOYSA-N 0.000 claims 1
• 210000003739 neck Anatomy 0.000 claims 1
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 1
• 210000003491 skin Anatomy 0.000 claims 1
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 59
• 201000010099 disease Diseases 0.000 abstract description 26
• 230000003463 hyperproliferative effect Effects 0.000 abstract description 9
• 208000035473 Communicable disease Diseases 0.000 abstract description 3
• 230000030833 cell death Effects 0.000 abstract description 3
• 208000015114 central nervous system disease Diseases 0.000 abstract description 3
• 229940043355 kinase inhibitor Drugs 0.000 abstract description 2
• 239000003757 phosphotransferase inhibitor Substances 0.000 abstract description 2
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 215
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 163
• 238000000746 purification Methods 0.000 description 156
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 108
• 239000000377 silicon dioxide Substances 0.000 description 106
• 238000005481 NMR spectroscopy Methods 0.000 description 91
• GQIXFHWAAHPMSO-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=C=C[N]1 GQIXFHWAAHPMSO-UHFFFAOYSA-N 0.000 description 81
• 239000011541 reaction mixture Substances 0.000 description 75
• 101150041968 CDC13 gene Proteins 0.000 description 73
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 73
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 72
• 238000006243 chemical reaction Methods 0.000 description 68
• 239000000243 solution Substances 0.000 description 62
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 61
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
• 229910001868 water Inorganic materials 0.000 description 42
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 41
• 229940002612 prodrug Drugs 0.000 description 40
• 239000000651 prodrug Substances 0.000 description 40
• 238000004007 reversed phase HPLC Methods 0.000 description 40
• 238000009472 formulation Methods 0.000 description 39
• 208000035475 disorder Diseases 0.000 description 33
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 32
• 239000002904 solvent Substances 0.000 description 32
• PFAKZIZFIXKDFP-UHFFFAOYSA-N 2-chloro-4-morpholin-4-ylthieno[3,2-d]pyrimidine-6-carbaldehyde Chemical compound C=12SC(C=O)=CC2=NC(Cl)=NC=1N1CCOCC1 PFAKZIZFIXKDFP-UHFFFAOYSA-N 0.000 description 31
• FELGNOOJSGQIPV-UHFFFAOYSA-N 4-[2-chloro-6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(Cl)=NC(N3CCOCC3)=C2S1 FELGNOOJSGQIPV-UHFFFAOYSA-N 0.000 description 30
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
• 229910052786 argon Inorganic materials 0.000 description 28
• 239000004480 active ingredient Substances 0.000 description 27
• 235000019439 ethyl acetate Nutrition 0.000 description 27
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 25
• 238000003756 stirring Methods 0.000 description 25
• 239000003153 chemical reaction reagent Substances 0.000 description 23
• 239000000543 intermediate Substances 0.000 description 23
• 239000007787 solid Substances 0.000 description 23
• 239000002207 metabolite Substances 0.000 description 22
• 239000000047 product Substances 0.000 description 22
• 210000004027 cell Anatomy 0.000 description 20
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 19
• 239000000463 material Substances 0.000 description 19
• 239000012044 organic layer Substances 0.000 description 19
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
• 239000012267 brine Substances 0.000 description 18
• 229940093499 ethyl acetate Drugs 0.000 description 18
• 238000003818 flash chromatography Methods 0.000 description 18
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 18
• 241000124008 Mammalia Species 0.000 description 17
• 239000013058 crude material Substances 0.000 description 17
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 16
• VKLMKOIHALMULJ-UHFFFAOYSA-N 4-[2-chloro-6-[(4-methylsulfonylpiperidin-1-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1CC(S(=O)(=O)C)CCN1CC1=CC2=NC(Cl)=NC(N3CCOCC3)=C2S1 VKLMKOIHALMULJ-UHFFFAOYSA-N 0.000 description 13
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
• 238000006069 Suzuki reaction reaction Methods 0.000 description 13
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 13
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 12
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 12
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
• 125000001424 substituent group Chemical group 0.000 description 12
• 238000001665 trituration Methods 0.000 description 12
• 125000004432 carbon atom Chemical group C* 0.000 description 11
• 239000010410 layer Substances 0.000 description 11
• 239000000546 pharmaceutical excipient Substances 0.000 description 11
• 238000000926 separation method Methods 0.000 description 11
• BPQVMIDUTRJYSC-UHFFFAOYSA-N 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine Chemical compound O1C(C)(C)C(C)(C)OB1C1=CN=C(N)N=C1 BPQVMIDUTRJYSC-UHFFFAOYSA-N 0.000 description 10
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 10
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 10
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
• 239000002253 acid Substances 0.000 description 10
• 230000015572 biosynthetic process Effects 0.000 description 10
• 239000003085 diluting agent Substances 0.000 description 10
• 229940079593 drug Drugs 0.000 description 10
• JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 10
• 238000002360 preparation method Methods 0.000 description 10
• 239000011734 sodium Substances 0.000 description 10
• 239000012321 sodium triacetoxyborohydride Substances 0.000 description 10
• 239000000725 suspension Substances 0.000 description 10
• 239000003826 tablet Substances 0.000 description 10
• UGXRFSNHOCGNDO-UHFFFAOYSA-N 2-chloro-4-morpholin-4-ylthieno[2,3-d]pyrimidine-6-carbaldehyde Chemical compound C=12C=C(C=O)SC2=NC(Cl)=NC=1N1CCOCC1 UGXRFSNHOCGNDO-UHFFFAOYSA-N 0.000 description 9
• TUXXFGMVVDCPCM-UHFFFAOYSA-N 4-[(2-chloro-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl)methyl]-n,n-dimethylpiperazine-1-carboxamide Chemical compound C1CN(C(=O)N(C)C)CCN1CC1=CC2=NC(Cl)=NC(N3CCOCC3)=C2S1 TUXXFGMVVDCPCM-UHFFFAOYSA-N 0.000 description 9
• QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 9
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 9
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• 239000002585 base Substances 0.000 description 9
• 229910052799 carbon Inorganic materials 0.000 description 9
• 239000000969 carrier Substances 0.000 description 9
• 238000000605 extraction Methods 0.000 description 9
• 238000001914 filtration Methods 0.000 description 9
• 238000004128 high performance liquid chromatography Methods 0.000 description 9
• 230000002441 reversible effect Effects 0.000 description 9
• 239000000126 substance Substances 0.000 description 9
• 238000010626 work up procedure Methods 0.000 description 9
• OXDJZXRKIXPRBA-UHFFFAOYSA-N 2-[4-[(2-chloro-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl)methyl]piperazin-1-yl]-n,n-dimethylacetamide Chemical compound C1CN(CC(=O)N(C)C)CCN1CC1=CC2=NC(Cl)=NC(N3CCOCC3)=C2S1 OXDJZXRKIXPRBA-UHFFFAOYSA-N 0.000 description 8
• APRISEPDSPZJHH-UHFFFAOYSA-N 4-[(2-chloro-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl)methyl]-n-(2-methoxyethyl)-n-methylpiperazine-1-carboxamide Chemical compound C1CN(C(=O)N(C)CCOC)CCN1CC1=CC2=NC(Cl)=NC(N3CCOCC3)=C2S1 APRISEPDSPZJHH-UHFFFAOYSA-N 0.000 description 8
• DQYPNHSXNKBXMW-UHFFFAOYSA-N 4-[2-chloro-6-[(4-cyclopropylsulfonylpiperazin-1-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C=12SC(CN3CCN(CC3)S(=O)(=O)C3CC3)=CC2=NC(Cl)=NC=1N1CCOCC1 DQYPNHSXNKBXMW-UHFFFAOYSA-N 0.000 description 8
• AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 8
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 8
• KLKWZMKGTIQLOG-UHFFFAOYSA-N [3-fluoro-5-(2-methylpropoxy)phenyl]boronic acid Chemical compound CC(C)COC1=CC(F)=CC(B(O)O)=C1 KLKWZMKGTIQLOG-UHFFFAOYSA-N 0.000 description 8
• 230000027455 binding Effects 0.000 description 8
• 238000004587 chromatography analysis Methods 0.000 description 8
• 239000012043 crude product Substances 0.000 description 8
• XMFYMWXCIWIHAC-UHFFFAOYSA-N n,n-dimethylpiperazine-1-carboxamide Chemical compound CN(C)C(=O)N1CCNCC1 XMFYMWXCIWIHAC-UHFFFAOYSA-N 0.000 description 8
• 125000006239 protecting group Chemical group 0.000 description 8
• ABMYEXAYWZJVOV-UHFFFAOYSA-N pyridin-3-ylboronic acid Chemical compound OB(O)C1=CC=CN=C1 ABMYEXAYWZJVOV-UHFFFAOYSA-N 0.000 description 8
• 238000010992 reflux Methods 0.000 description 8
• PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 8
• DCRKUEFAUFQTAF-LBPRGKRZSA-N (2s)-1-[4-[(2-chloro-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl)methyl]piperazin-1-yl]-2-hydroxypropan-1-one Chemical compound C1CN(C(=O)[C@@H](O)C)CCN1CC1=CC2=NC(Cl)=NC(N3CCOCC3)=C2S1 DCRKUEFAUFQTAF-LBPRGKRZSA-N 0.000 description 7
• YVPBSLIVIGORID-ZDUSSCGKSA-N (2s)-1-[4-[(2-chloro-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl)methyl]piperazin-1-yl]-2-hydroxypropan-1-one Chemical compound C1CN(C(=O)[C@@H](O)C)CCN1CC1=C(C)C2=NC(Cl)=NC(N3CCOCC3)=C2S1 YVPBSLIVIGORID-ZDUSSCGKSA-N 0.000 description 7
• UGODXWGUIIBBMW-UHFFFAOYSA-N 2-[4-[(2-chloro-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl)methyl]piperazin-1-yl]-n,2-dimethylpropanamide Chemical compound C1CN(C(C)(C)C(=O)NC)CCN1CC1=CC2=NC(Cl)=NC(N3CCOCC3)=C2S1 UGODXWGUIIBBMW-UHFFFAOYSA-N 0.000 description 7
• WEPPIPLKAFJEFV-UHFFFAOYSA-N 2-chloro-6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylfuro[3,2-d]pyrimidine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(Cl)=NC(N3CCOCC3)=C2O1 WEPPIPLKAFJEFV-UHFFFAOYSA-N 0.000 description 7
• BFCDGFSODLNYMB-UHFFFAOYSA-N 4-[(2-chloro-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl)methyl]-n,n-dimethylpiperazine-1-sulfonamide Chemical compound C1CN(S(=O)(=O)N(C)C)CCN1CC1=CC2=NC(Cl)=NC(N3CCOCC3)=C2S1 BFCDGFSODLNYMB-UHFFFAOYSA-N 0.000 description 7
• XRCUWYHURKQUIX-UHFFFAOYSA-N 4-[2-chloro-6-(piperazin-1-ylmethyl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C=12SC(CN3CCNCC3)=CC2=NC(Cl)=NC=1N1CCOCC1 XRCUWYHURKQUIX-UHFFFAOYSA-N 0.000 description 7
• WTYPNNPYTXIHIA-UHFFFAOYSA-N 4-[2-chloro-6-[(4-methylsulfonylpiperidin-1-yl)methyl]thieno[2,3-d]pyrimidin-4-yl]morpholine Chemical compound C1CC(S(=O)(=O)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(Cl)N=C2S1 WTYPNNPYTXIHIA-UHFFFAOYSA-N 0.000 description 7
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
• IDRGFNPZDVBSSE-UHFFFAOYSA-N OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F Chemical compound OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F IDRGFNPZDVBSSE-UHFFFAOYSA-N 0.000 description 7
• 238000003556 assay Methods 0.000 description 7
• 239000000872 buffer Substances 0.000 description 7
• 239000003995 emulsifying agent Substances 0.000 description 7
• 150000002148 esters Chemical class 0.000 description 7
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
• 239000007788 liquid Substances 0.000 description 7
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 7
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
• 239000012279 sodium borohydride Substances 0.000 description 7
• 229910000033 sodium borohydride Inorganic materials 0.000 description 7
• 238000003786 synthesis reaction Methods 0.000 description 7
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
• XVFLEWBSGQQJNS-UHFFFAOYSA-N 4-morpholin-4-ylfuro[3,2-d]pyrimidine Chemical class C1COCCN1C1=NC=NC2=C1OC=C2 XVFLEWBSGQQJNS-UHFFFAOYSA-N 0.000 description 6
• XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 6
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
• 241000282414 Homo sapiens Species 0.000 description 6
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
• 238000002648 combination therapy Methods 0.000 description 6
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
• 238000001727 in vivo Methods 0.000 description 6
• LFCIZCDKCVMSRZ-UHFFFAOYSA-N n-[(2-chloro-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl)methyl]-n-methyl-1-methylsulfonylpiperidin-4-amine Chemical compound C1CN(S(C)(=O)=O)CCC1N(C)CC(SC1=2)=CC1=NC(Cl)=NC=2N1CCOCC1 LFCIZCDKCVMSRZ-UHFFFAOYSA-N 0.000 description 6
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
• 231100000252 nontoxic Toxicity 0.000 description 6
• 230000003000 nontoxic effect Effects 0.000 description 6
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
• 239000012071 phase Substances 0.000 description 6
• 235000017557 sodium bicarbonate Nutrition 0.000 description 6
• 239000003381 stabilizer Substances 0.000 description 6
• 239000007858 starting material Substances 0.000 description 6
• FTUGDRKBXMMROC-UHFFFAOYSA-N tert-butyl 4-[(2-chloro-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl)methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1CC1=CC2=NC(Cl)=NC(N3CCOCC3)=C2S1 FTUGDRKBXMMROC-UHFFFAOYSA-N 0.000 description 6
• CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 6
• LKGKUACPLXCVOF-UHFFFAOYSA-N (2,4-dimethoxypyrimidin-5-yl)boronic acid Chemical compound COC1=NC=C(B(O)O)C(OC)=N1 LKGKUACPLXCVOF-UHFFFAOYSA-N 0.000 description 5
• CGHYQZASLKERLV-UHFFFAOYSA-N (2-aminopyrimidin-5-yl)boronic acid Chemical compound NC1=NC=C(B(O)O)C=N1 CGHYQZASLKERLV-UHFFFAOYSA-N 0.000 description 5
• VADJMGWMEAHTJS-BETUJISGSA-N 4-[2-chloro-6-[[(2r,6s)-2,6-dimethyl-4-methylsulfonylpiperazin-1-yl]methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C[C@H]1CN(S(C)(=O)=O)C[C@@H](C)N1CC1=CC2=NC(Cl)=NC(N3CCOCC3)=C2S1 VADJMGWMEAHTJS-BETUJISGSA-N 0.000 description 5
• RYRGJOZXJQJSIT-UHFFFAOYSA-N 4-[2-chloro-7-methyl-6-(piperazin-1-ylmethyl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound S1C2=C(N3CCOCC3)N=C(Cl)N=C2C(C)=C1CN1CCNCC1 RYRGJOZXJQJSIT-UHFFFAOYSA-N 0.000 description 5
• YFTAUNOLAHRUIE-UHFFFAOYSA-N 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(N)N=C1 YFTAUNOLAHRUIE-UHFFFAOYSA-N 0.000 description 5
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
• WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 5
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 5
• 229910019142 PO4 Inorganic materials 0.000 description 5
• NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [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 5
• 150000001408 amides Chemical class 0.000 description 5
• 229940024606 amino acid Drugs 0.000 description 5
• 235000001014 amino acid Nutrition 0.000 description 5
• 239000007864 aqueous solution Substances 0.000 description 5
• 239000002775 capsule Substances 0.000 description 5
• 239000003054 catalyst Substances 0.000 description 5
• 239000006071 cream Substances 0.000 description 5
• 231100000433 cytotoxic Toxicity 0.000 description 5
• 230000001472 cytotoxic effect Effects 0.000 description 5
• 239000002552 dosage form Substances 0.000 description 5
• JUQAECQBUNODQP-UHFFFAOYSA-N furo[3,2-d]pyrimidine Chemical class C1=NC=C2OC=CC2=N1 JUQAECQBUNODQP-UHFFFAOYSA-N 0.000 description 5
• 238000007429 general method Methods 0.000 description 5
• 125000005842 heteroatom Chemical group 0.000 description 5
• 238000000338 in vitro Methods 0.000 description 5
• 239000003112 inhibitor Substances 0.000 description 5
• 238000002347 injection Methods 0.000 description 5
• 239000007924 injection Substances 0.000 description 5
• 150000002500 ions Chemical class 0.000 description 5
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
• 239000004310 lactic acid Substances 0.000 description 5
• 235000014655 lactic acid Nutrition 0.000 description 5
• 239000002609 medium Substances 0.000 description 5
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
• 239000003921 oil Substances 0.000 description 5
• 239000010452 phosphate Substances 0.000 description 5
• 150000003905 phosphatidylinositols Chemical class 0.000 description 5
• 150000003904 phospholipids Chemical class 0.000 description 5
• 239000000843 powder Substances 0.000 description 5
• 239000002244 precipitate Substances 0.000 description 5
• 239000002243 precursor Substances 0.000 description 5
• 239000003755 preservative agent Substances 0.000 description 5
• 239000000758 substrate Substances 0.000 description 5
• PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
• YPWAJLGHACDYQS-UHFFFAOYSA-N (2-methoxypyrimidin-5-yl)boronic acid Chemical compound COC1=NC=C(B(O)O)C=N1 YPWAJLGHACDYQS-UHFFFAOYSA-N 0.000 description 4
• DHADXDMPEUWEAS-UHFFFAOYSA-N (6-methoxypyridin-3-yl)boronic acid Chemical compound COC1=CC=C(B(O)O)C=N1 DHADXDMPEUWEAS-UHFFFAOYSA-N 0.000 description 4
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
• UPOSLUZZOWHWOZ-UHFFFAOYSA-N 1-[(2-chloro-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl)methyl]-n,n-dimethylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)CCN1CC1=CC2=NC(Cl)=NC(N3CCOCC3)=C2S1 UPOSLUZZOWHWOZ-UHFFFAOYSA-N 0.000 description 4
• VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 4
• RXUMUQZCQPUOSM-UHFFFAOYSA-N 2-chloro-4-morpholin-4-ylfuro[3,2-d]pyrimidine Chemical compound C=12OC=CC2=NC(Cl)=NC=1N1CCOCC1 RXUMUQZCQPUOSM-UHFFFAOYSA-N 0.000 description 4
• HKQMXHKNXRNUCF-UHFFFAOYSA-N 4-(2-chlorothieno[3,2-d]pyrimidin-4-yl)morpholine Chemical class C=12SC=CC2=NC(Cl)=NC=1N1CCOCC1 HKQMXHKNXRNUCF-UHFFFAOYSA-N 0.000 description 4
• GDGKZILNLANCNU-UHFFFAOYSA-N 4-[(2-chloro-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl)methyl]-n,n-dimethylpiperazine-1-carboxamide Chemical compound C1CN(C(=O)N(C)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(Cl)N=C2S1 GDGKZILNLANCNU-UHFFFAOYSA-N 0.000 description 4
• NHNMAZDUEYGYAW-GFCCVEGCSA-N 4-[2-chloro-6-[[(3r)-3-methyl-4-methylsulfonylpiperazin-1-yl]methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(S(C)(=O)=O)[C@H](C)CN1CC1=CC2=NC(Cl)=NC(N3CCOCC3)=C2S1 NHNMAZDUEYGYAW-GFCCVEGCSA-N 0.000 description 4
• NHNMAZDUEYGYAW-LBPRGKRZSA-N 4-[2-chloro-6-[[(3s)-3-methyl-4-methylsulfonylpiperazin-1-yl]methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(S(C)(=O)=O)[C@@H](C)CN1CC1=CC2=NC(Cl)=NC(N3CCOCC3)=C2S1 NHNMAZDUEYGYAW-LBPRGKRZSA-N 0.000 description 4
• FCROFGARBITAQF-UHFFFAOYSA-N 4-[6-[[4-(benzenesulfonyl)piperazin-1-yl]methyl]-2-chlorothieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C=12SC(CN3CCN(CC3)S(=O)(=O)C=3C=CC=CC=3)=CC2=NC(Cl)=NC=1N1CCOCC1 FCROFGARBITAQF-UHFFFAOYSA-N 0.000 description 4
• ZEWWLZDNTOZATC-UHFFFAOYSA-N 4-thieno[3,2-d]pyrimidin-4-ylmorpholine Chemical compound C1COCCN1C1=NC=NC2=C1SC=C2 ZEWWLZDNTOZATC-UHFFFAOYSA-N 0.000 description 4
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
• KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 4
• AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 4
• GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 4
• 108010010803 Gelatin Proteins 0.000 description 4
• DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
• 206010061218 Inflammation Diseases 0.000 description 4
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
• 239000012359 Methanesulfonyl chloride Substances 0.000 description 4
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 4
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
• 229930006000 Sucrose Natural products 0.000 description 4
• CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 4
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
• LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 description 4
• 125000002252 acyl group Chemical group 0.000 description 4
• 125000004423 acyloxy group Chemical group 0.000 description 4
• 150000001413 amino acids Chemical class 0.000 description 4
• 239000007900 aqueous suspension Substances 0.000 description 4
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
• 239000008228 bacteriostatic water for injection Substances 0.000 description 4
• 230000008901 benefit Effects 0.000 description 4
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
• 238000012054 celltiter-glo Methods 0.000 description 4
• 238000005859 coupling reaction Methods 0.000 description 4
• 235000019197 fats Nutrition 0.000 description 4
• 229960002949 fluorouracil Drugs 0.000 description 4
• 239000008273 gelatin Substances 0.000 description 4
• 229920000159 gelatin Polymers 0.000 description 4
• 235000019322 gelatine Nutrition 0.000 description 4
• 235000011852 gelatine desserts Nutrition 0.000 description 4
• 229960004275 glycolic acid Drugs 0.000 description 4
• 125000001475 halogen functional group Chemical group 0.000 description 4
• 230000004054 inflammatory process Effects 0.000 description 4
• HPJKCIUCZWXJDR-UHFFFAOYSA-N letrozole Chemical compound C1=CC(C#N)=CC=C1C(N1N=CN=C1)C1=CC=C(C#N)C=C1 HPJKCIUCZWXJDR-UHFFFAOYSA-N 0.000 description 4
• 230000002503 metabolic effect Effects 0.000 description 4
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 4
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
• OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 4
• 239000003094 microcapsule Substances 0.000 description 4
• 238000002156 mixing Methods 0.000 description 4
• 210000000214 mouth Anatomy 0.000 description 4
• XGABIOSYJHFORX-UHFFFAOYSA-N n,n-dimethylpiperidine-4-carboxamide Chemical compound CN(C)C(=O)C1CCNCC1 XGABIOSYJHFORX-UHFFFAOYSA-N 0.000 description 4
• QAJOLLVGOSCKGP-UHFFFAOYSA-N n-methylpiperidine-4-carboxamide Chemical compound CNC(=O)C1CCNCC1 QAJOLLVGOSCKGP-UHFFFAOYSA-N 0.000 description 4
• 230000004770 neurodegeneration Effects 0.000 description 4
• 230000003287 optical effect Effects 0.000 description 4
• 150000002894 organic compounds Chemical class 0.000 description 4
• 230000001575 pathological effect Effects 0.000 description 4
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
• 229910052698 phosphorus Inorganic materials 0.000 description 4
• 239000006187 pill Substances 0.000 description 4
• 229920001223 polyethylene glycol Polymers 0.000 description 4
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
• QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 4
• UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 4
• 150000003254 radicals Chemical class 0.000 description 4
• 102200160920 rs35304565 Human genes 0.000 description 4
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
• 239000005720 sucrose Substances 0.000 description 4
• 239000011593 sulfur Chemical group 0.000 description 4
• 239000000375 suspending agent Substances 0.000 description 4
• 208000024891 symptom Diseases 0.000 description 4
• RBSTYDJFVDTJPH-UHFFFAOYSA-N tert-butyl 4-methylsulfanylpiperidine-1-carboxylate Chemical compound CSC1CCN(C(=O)OC(C)(C)C)CC1 RBSTYDJFVDTJPH-UHFFFAOYSA-N 0.000 description 4
• 238000002560 therapeutic procedure Methods 0.000 description 4
• WYWHKKSPHMUBEB-UHFFFAOYSA-N tioguanine Chemical compound N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 description 4
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
• 210000004881 tumor cell Anatomy 0.000 description 4
• UJOJBFAUAVIWPP-UHFFFAOYSA-N (2-chloro-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl)methanol Chemical compound C=12SC(CO)=CC2=NC(Cl)=NC=1N1CCOCC1 UJOJBFAUAVIWPP-UHFFFAOYSA-N 0.000 description 3
• LZXGYNMILFBBFA-LBPRGKRZSA-N (2s)-1-[4-[(2-chloro-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl)methyl]piperazin-1-yl]-2-hydroxypropan-1-one Chemical compound C1CN(C(=O)[C@@H](O)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(Cl)N=C2S1 LZXGYNMILFBBFA-LBPRGKRZSA-N 0.000 description 3
• PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 3
• ZZAKLGGGMWORRT-UHFFFAOYSA-N 1-methylsulfonylpiperazine Chemical compound CS(=O)(=O)N1CCNCC1 ZZAKLGGGMWORRT-UHFFFAOYSA-N 0.000 description 3
• UEICIOHAOMRQDE-UHFFFAOYSA-N 1h-furo[3,2-d]pyrimidine-2,4-dione Chemical compound OC1=NC(O)=C2OC=CC2=N1 UEICIOHAOMRQDE-UHFFFAOYSA-N 0.000 description 3
• OTFDNOQBJWBJJM-UHFFFAOYSA-N 2,4-dichlorofuro[3,2-d]pyrimidine Chemical compound ClC1=NC(Cl)=C2OC=CC2=N1 OTFDNOQBJWBJJM-UHFFFAOYSA-N 0.000 description 3
• AQECFYPZMBRCIA-UHFFFAOYSA-N 2,4-dichlorothieno[3,2-d]pyrimidine Chemical compound ClC1=NC(Cl)=C2SC=CC2=N1 AQECFYPZMBRCIA-UHFFFAOYSA-N 0.000 description 3
• YDNDOBWOBUARCV-UHFFFAOYSA-N 2-chloro-4-morpholin-4-ylfuro[3,2-d]pyrimidine-6-carbaldehyde Chemical compound C=12OC(C=O)=CC2=NC(Cl)=NC=1N1CCOCC1 YDNDOBWOBUARCV-UHFFFAOYSA-N 0.000 description 3
• XLVAIDDXTOELNS-UHFFFAOYSA-N 4-[2-chloro-6-(piperazin-1-ylmethyl)thieno[2,3-d]pyrimidin-4-yl]morpholine Chemical compound C=12C=C(CN3CCNCC3)SC2=NC(Cl)=NC=1N1CCOCC1 XLVAIDDXTOELNS-UHFFFAOYSA-N 0.000 description 3
• DDGJOTNSVPHXNT-UHFFFAOYSA-N 4-[6-(bromomethyl)-2-chlorothieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C=12SC(CBr)=CC2=NC(Cl)=NC=1N1CCOCC1 DDGJOTNSVPHXNT-UHFFFAOYSA-N 0.000 description 3
• 208000024827 Alzheimer disease Diseases 0.000 description 3
• 201000001320 Atherosclerosis Diseases 0.000 description 3
• WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
• 239000004215 Carbon black (E152) Substances 0.000 description 3
• 201000009030 Carcinoma Diseases 0.000 description 3
• 208000006029 Cardiomegaly Diseases 0.000 description 3
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 3
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
• 241000282412 Homo Species 0.000 description 3
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical group C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 3
• FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 description 3
• 235000010643 Leucaena leucocephala Nutrition 0.000 description 3
• 240000007472 Leucaena leucocephala Species 0.000 description 3
• 108010000817 Leuprolide Proteins 0.000 description 3
• YNHIGQDRGKUECZ-UHFFFAOYSA-L PdCl2(PPh3)2 Substances [Cl-].[Cl-].[Pd+2].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 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 3
• 239000002202 Polyethylene glycol Substances 0.000 description 3
• OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
• 201000004681 Psoriasis Diseases 0.000 description 3
• 206010038389 Renal cancer Diseases 0.000 description 3
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
• FOCVUCIESVLUNU-UHFFFAOYSA-N Thiotepa Chemical compound C1CN1P(N1CC1)(=S)N1CC1 FOCVUCIESVLUNU-UHFFFAOYSA-N 0.000 description 3
• WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
• 239000012346 acetyl chloride Substances 0.000 description 3
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
• 230000002378 acidificating effect Effects 0.000 description 3
• 150000007513 acids Chemical class 0.000 description 3
• 150000001412 amines Chemical class 0.000 description 3
• 125000000539 amino acid group Chemical group 0.000 description 3
• 229910021529 ammonia Inorganic materials 0.000 description 3
• 238000004458 analytical method Methods 0.000 description 3
• 239000003963 antioxidant agent Substances 0.000 description 3
• 235000006708 antioxidants Nutrition 0.000 description 3
• 239000003125 aqueous solvent Substances 0.000 description 3
• 125000002619 bicyclic group Chemical group 0.000 description 3
• HXCHCVDVKSCDHU-LULTVBGHSA-N calicheamicin Chemical compound C1[C@H](OC)[C@@H](NCC)CO[C@H]1O[C@H]1[C@H](O[C@@H]2C\3=C(NC(=O)OC)C(=O)C[C@](C/3=C/CSSSC)(O)C#C\C=C/C#C2)O[C@H](C)[C@@H](NO[C@@H]2O[C@H](C)[C@@H](SC(=O)C=3C(=C(OC)C(O[C@H]4[C@@H]([C@H](OC)[C@@H](O)[C@H](C)O4)O)=C(I)C=3C)OC)[C@@H](O)C2)[C@@H]1O HXCHCVDVKSCDHU-LULTVBGHSA-N 0.000 description 3
• 229930195731 calicheamicin Natural products 0.000 description 3
• 235000013877 carbamide Nutrition 0.000 description 3
• 150000001720 carbohydrates Chemical class 0.000 description 3
• 235000014633 carbohydrates Nutrition 0.000 description 3
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
• 238000003776 cleavage reaction Methods 0.000 description 3
• 239000003086 colorant Substances 0.000 description 3
• 239000007859 condensation product Substances 0.000 description 3
• 229920001577 copolymer Polymers 0.000 description 3
• 230000008878 coupling Effects 0.000 description 3
• 238000010168 coupling process Methods 0.000 description 3
• 235000014113 dietary fatty acids Nutrition 0.000 description 3
• 239000002270 dispersing agent Substances 0.000 description 3
• 238000012377 drug delivery Methods 0.000 description 3
• 239000003480 eluent Substances 0.000 description 3
• 239000000839 emulsion Substances 0.000 description 3
• BAFFCPLWZWCGNV-UHFFFAOYSA-N ethyl 3-(carbamoylamino)furan-2-carboxylate Chemical compound CCOC(=O)C=1OC=CC=1NC(N)=O BAFFCPLWZWCGNV-UHFFFAOYSA-N 0.000 description 3
• 229930195729 fatty acid Natural products 0.000 description 3
• 239000000194 fatty acid Substances 0.000 description 3
• 150000004665 fatty acids Chemical class 0.000 description 3
• 239000000796 flavoring agent Substances 0.000 description 3
• 235000013355 food flavoring agent Nutrition 0.000 description 3
• 235000003599 food sweetener Nutrition 0.000 description 3
• 238000001640 fractional crystallisation Methods 0.000 description 3
• 230000014509 gene expression Effects 0.000 description 3
• 239000008187 granular material Substances 0.000 description 3
• 238000010438 heat treatment Methods 0.000 description 3
• 206010073071 hepatocellular carcinoma Diseases 0.000 description 3
• 229940088597 hormone Drugs 0.000 description 3
• 239000005556 hormone Substances 0.000 description 3
• 229930195733 hydrocarbon Natural products 0.000 description 3
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
• 230000007062 hydrolysis Effects 0.000 description 3
• 238000006460 hydrolysis reaction Methods 0.000 description 3
• 238000001802 infusion Methods 0.000 description 3
• 239000004615 ingredient Substances 0.000 description 3
• 238000001990 intravenous administration Methods 0.000 description 3
• BCFGMOOMADDAQU-UHFFFAOYSA-N lapatinib Chemical compound O1C(CNCCS(=O)(=O)C)=CC=C1C1=CC=C(N=CN=C2NC=3C=C(Cl)C(OCC=4C=C(F)C=CC=4)=CC=3)C2=C1 BCFGMOOMADDAQU-UHFFFAOYSA-N 0.000 description 3
• 239000002502 liposome Substances 0.000 description 3
• 239000000314 lubricant Substances 0.000 description 3
• 239000012528 membrane Substances 0.000 description 3
• 210000004379 membrane Anatomy 0.000 description 3
• GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 description 3
• 230000004060 metabolic process Effects 0.000 description 3
• 229960000485 methotrexate Drugs 0.000 description 3
• OFSPCMNPGVKHEL-UHFFFAOYSA-N methyl 3-[(2-methylpropan-2-yl)oxycarbonylamino]furan-2-carboxylate Chemical compound COC(=O)C=1OC=CC=1NC(=O)OC(C)(C)C OFSPCMNPGVKHEL-UHFFFAOYSA-N 0.000 description 3
• UTLPWTWCOSOPMX-UHFFFAOYSA-N methyl 3-aminofuran-2-carboxylate Chemical compound COC(=O)C=1OC=CC=1N UTLPWTWCOSOPMX-UHFFFAOYSA-N 0.000 description 3
• KKZJGLLVHKMTCM-UHFFFAOYSA-N mitoxantrone Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO KKZJGLLVHKMTCM-UHFFFAOYSA-N 0.000 description 3
• 230000004048 modification Effects 0.000 description 3
• 238000012986 modification Methods 0.000 description 3
• 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 3
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
• 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
• 210000000056 organ Anatomy 0.000 description 3
• 239000001301 oxygen Chemical group 0.000 description 3
• 229920003023 plastic Polymers 0.000 description 3
• 239000004033 plastic Substances 0.000 description 3
• 229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
• 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
• 108090000765 processed proteins & peptides Proteins 0.000 description 3
• 230000035755 proliferation Effects 0.000 description 3
• 108090000623 proteins and genes Proteins 0.000 description 3
• OKULHRWWYCFJAB-UHFFFAOYSA-N pyrimidine-4-carbaldehyde Chemical compound O=CC1=CC=NC=N1 OKULHRWWYCFJAB-UHFFFAOYSA-N 0.000 description 3
• 238000001953 recrystallisation Methods 0.000 description 3
• 238000006268 reductive amination reaction Methods 0.000 description 3
• 230000002829 reductive effect Effects 0.000 description 3
• 208000037803 restenosis Diseases 0.000 description 3
• 238000012552 review Methods 0.000 description 3
• 230000007017 scission Effects 0.000 description 3
• QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 description 3
• 229910000029 sodium carbonate Inorganic materials 0.000 description 3
• 239000004094 surface-active agent Substances 0.000 description 3
• 230000004083 survival effect Effects 0.000 description 3
• 239000003765 sweetening agent Substances 0.000 description 3
• 230000002195 synergetic effect Effects 0.000 description 3
• SBFLPNJYWRKWFT-UHFFFAOYSA-N tert-butyl n-(furan-3-yl)carbamate Chemical compound CC(C)(C)OC(=O)NC=1C=COC=1 SBFLPNJYWRKWFT-UHFFFAOYSA-N 0.000 description 3
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
• 229930192474 thiophene Chemical group 0.000 description 3
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
• 238000002054 transplantation Methods 0.000 description 3
• 230000003612 virological effect Effects 0.000 description 3
• 238000005406 washing Methods 0.000 description 3
• 239000001993 wax Substances 0.000 description 3
• 239000000080 wetting agent Substances 0.000 description 3
• KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
• QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 2
• LKGXACWDLPJKHG-HNNXBMFYSA-N (2s)-1-[4-[[2-(6-aminopyridin-3-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-hydroxypropan-1-one Chemical compound C1CN(C(=O)[C@@H](O)C)CCN1CC1=CC2=NC(C=3C=NC(N)=CC=3)=NC(N3CCOCC3)=C2S1 LKGXACWDLPJKHG-HNNXBMFYSA-N 0.000 description 2
• FJDJDYQNCUOLSQ-INIZCTEOSA-N (2s)-1-[4-[[2-(6-aminopyridin-3-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-hydroxypropan-1-one Chemical compound C1CN(C(=O)[C@@H](O)C)CCN1CC1=C(C)C2=NC(C=3C=NC(N)=CC=3)=NC(N3CCOCC3)=C2S1 FJDJDYQNCUOLSQ-INIZCTEOSA-N 0.000 description 2
• ISTPJJDMCAZLOO-RGMNGODLSA-N (2s)-2-methyl-1-methylsulfonylpiperazine;hydrochloride Chemical compound Cl.C[C@H]1CNCCN1S(C)(=O)=O ISTPJJDMCAZLOO-RGMNGODLSA-N 0.000 description 2
• CMJFVJZYTQPKDI-KNVOCYPGSA-N (3r,5s)-3,5-dimethyl-1-methylsulfonylpiperazine Chemical compound C[C@H]1CN(S(C)(=O)=O)C[C@@H](C)N1 CMJFVJZYTQPKDI-KNVOCYPGSA-N 0.000 description 2
• 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 2
• SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
• RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 2
• APWRZPQBPCAXFP-UHFFFAOYSA-N 1-(1-oxo-2H-isoquinolin-5-yl)-5-(trifluoromethyl)-N-[2-(trifluoromethyl)pyridin-4-yl]pyrazole-4-carboxamide Chemical compound O=C1NC=CC2=C(C=CC=C12)N1N=CC(=C1C(F)(F)F)C(=O)NC1=CC(=NC=C1)C(F)(F)F APWRZPQBPCAXFP-UHFFFAOYSA-N 0.000 description 2
• JWOHBPPVVDQMKB-UHFFFAOYSA-N 1-[(2-methylpropan-2-yl)oxycarbonyl]piperidine-4-carboxylic acid Chemical compound CC(C)(C)OC(=O)N1CCC(C(O)=O)CC1 JWOHBPPVVDQMKB-UHFFFAOYSA-N 0.000 description 2
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
• MRHDCTNTTCVSRM-UHFFFAOYSA-N 2-[1-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperidin-4-yl]ethanol Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCC(CCO)CC2)=C2)C2=N1 MRHDCTNTTCVSRM-UHFFFAOYSA-N 0.000 description 2
• JJDUHFSDEPSCOX-UHFFFAOYSA-N 2-bromo-n,2-dimethylpropanamide Chemical compound CNC(=O)C(C)(C)Br JJDUHFSDEPSCOX-UHFFFAOYSA-N 0.000 description 2
• PNFPJVXECCRKQD-UHFFFAOYSA-N 2-chloro-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidine-6-carbaldehyde Chemical compound N1=C(Cl)N=C2C(C)=C(C=O)SC2=C1N1CCOCC1 PNFPJVXECCRKQD-UHFFFAOYSA-N 0.000 description 2
• IZHVBANLECCAGF-UHFFFAOYSA-N 2-hydroxy-3-(octadecanoyloxy)propyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCC IZHVBANLECCAGF-UHFFFAOYSA-N 0.000 description 2
• BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 description 2
• KOHBEDRJXKOYHL-UHFFFAOYSA-N 2-methoxy-n-methylethanamine Chemical compound CNCCOC KOHBEDRJXKOYHL-UHFFFAOYSA-N 0.000 description 2
• 125000004398 2-methyl-2-butyl group Chemical group CC(C)(CC)* 0.000 description 2
• 125000004918 2-methyl-2-pentyl group Chemical group CC(C)(CCC)* 0.000 description 2
• 125000004922 2-methyl-3-pentyl group Chemical group CC(C)C(CC)* 0.000 description 2
• LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical class NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 2
• LDSQQXKSEFZAPE-UHFFFAOYSA-N 2-piperidin-4-ylethanol Chemical compound OCCC1CCNCC1 LDSQQXKSEFZAPE-UHFFFAOYSA-N 0.000 description 2
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
• RRSCCSFOIRVDMJ-UHFFFAOYSA-N 2-pyrrolidin-1-ylpiperidine Chemical compound C1CCCN1C1NCCCC1 RRSCCSFOIRVDMJ-UHFFFAOYSA-N 0.000 description 2
• IHCCAYCGZOLTEU-UHFFFAOYSA-N 3-furoic acid Chemical compound OC(=O)C=1C=COC=1 IHCCAYCGZOLTEU-UHFFFAOYSA-N 0.000 description 2
• HENXUFOAGXNWKH-UHFFFAOYSA-N 3-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Chemical compound COC1=CN=CC(B2OC(C)(C)C(C)(C)O2)=C1 HENXUFOAGXNWKH-UHFFFAOYSA-N 0.000 description 2
• 125000004917 3-methyl-2-butyl group Chemical group CC(C(C)*)C 0.000 description 2
• 125000004919 3-methyl-2-pentyl group Chemical group CC(C(C)*)CC 0.000 description 2
• 125000004921 3-methyl-3-pentyl group Chemical group CC(CC)(CC)* 0.000 description 2
• XCEGFNRUBBVHJT-UHFFFAOYSA-N 3-methylsulfonylpyrrolidine Chemical compound CS(=O)(=O)C1CCNC1 XCEGFNRUBBVHJT-UHFFFAOYSA-N 0.000 description 2
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
• WQVWNGNIWWURTQ-UHFFFAOYSA-N 4-[(2-chloro-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl)methyl]-n,n-dimethylpiperazine-1-carboxamide Chemical compound C1CN(C(=O)N(C)C)CCN1CC1=C(C)C2=NC(Cl)=NC(N3CCOCC3)=C2S1 WQVWNGNIWWURTQ-UHFFFAOYSA-N 0.000 description 2
• VDUPVBJHAMPFSO-UHFFFAOYSA-N 4-[2-chloro-6-[(4-cyclopropylsulfonylpiperazin-1-yl)methyl]-7-methylthieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound S1C2=C(N3CCOCC3)N=C(Cl)N=C2C(C)=C1CN(CC1)CCN1S(=O)(=O)C1CC1 VDUPVBJHAMPFSO-UHFFFAOYSA-N 0.000 description 2
• GLNIDPYGCNWEMX-UHFFFAOYSA-N 4-[2-chloro-6-[(4-methylpiperazin-1-yl)methyl]thieno[2,3-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(C)CCN1CC1=CC2=C(N3CCOCC3)N=C(Cl)N=C2S1 GLNIDPYGCNWEMX-UHFFFAOYSA-N 0.000 description 2
• GWDOSUBCAWZOOE-UHFFFAOYSA-N 4-[2-chloro-6-[(4-propan-2-ylsulfonylpiperazin-1-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(S(=O)(=O)C(C)C)CCN1CC1=CC2=NC(Cl)=NC(N3CCOCC3)=C2S1 GWDOSUBCAWZOOE-UHFFFAOYSA-N 0.000 description 2
• TUMMHVWIJZBCBH-UHFFFAOYSA-N 4-[2-chloro-7-methyl-6-[(4-propan-2-ylsulfonylpiperazin-1-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(S(=O)(=O)C(C)C)CCN1CC1=C(C)C2=NC(Cl)=NC(N3CCOCC3)=C2S1 TUMMHVWIJZBCBH-UHFFFAOYSA-N 0.000 description 2
• HMAZVRLQZNSGFG-UHFFFAOYSA-N 4-[6-[(4-methylpiperazin-1-yl)methyl]-2-pyrimidin-5-ylthieno[2,3-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=NC=NC=3)N=C2S1 HMAZVRLQZNSGFG-UHFFFAOYSA-N 0.000 description 2
• FSWYEOZXHOYAMH-UHFFFAOYSA-N 4-[6-[[4-(benzenesulfonyl)piperazin-1-yl]methyl]-2-chloro-7-methylthieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound S1C2=C(N3CCOCC3)N=C(Cl)N=C2C(C)=C1CN(CC1)CCN1S(=O)(=O)C1=CC=CC=C1 FSWYEOZXHOYAMH-UHFFFAOYSA-N 0.000 description 2
• 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 2
• XKWZLZLVNFUCBL-UHFFFAOYSA-N 4-methylsulfonylpiperidine Chemical compound CS(=O)(=O)C1CCNCC1 XKWZLZLVNFUCBL-UHFFFAOYSA-N 0.000 description 2
• AWQASGVMXFSQQI-UHFFFAOYSA-N 4-o-tert-butyl 1-o-(4-nitrophenyl) piperazine-1,4-dicarboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C(=O)OC1=CC=C([N+]([O-])=O)C=C1 AWQASGVMXFSQQI-UHFFFAOYSA-N 0.000 description 2
• ZQQFWKMWLPEJQP-UHFFFAOYSA-N 5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]pyridine-3-carbaldehyde Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=C(C=O)C=NC=3)N=C2S1 ZQQFWKMWLPEJQP-UHFFFAOYSA-N 0.000 description 2
• ZTGBGDUZWUVYIB-UHFFFAOYSA-N 5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]furan-2-carbaldehyde Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3OC(C=O)=CC=3)=NC(N3CCOCC3)=C2S1 ZTGBGDUZWUVYIB-UHFFFAOYSA-N 0.000 description 2
• NOAHGXASVHHTEO-UHFFFAOYSA-N 5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]thiophene-2-carbaldehyde Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3SC(C=O)=CC=3)=NC(N3CCOCC3)=C2S1 NOAHGXASVHHTEO-UHFFFAOYSA-N 0.000 description 2
• STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 description 2
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
• UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
• 239000004475 Arginine Substances 0.000 description 2
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
• BFYIZQONLCFLEV-DAELLWKTSA-N Aromasine Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC(=C)C2=C1 BFYIZQONLCFLEV-DAELLWKTSA-N 0.000 description 2
• 241000416162 Astragalus gummifer Species 0.000 description 2
• 208000023275 Autoimmune disease Diseases 0.000 description 2
• MLDQJTXFUGDVEO-UHFFFAOYSA-N BAY-43-9006 Chemical compound C1=NC(C(=O)NC)=CC(OC=2C=CC(NC(=O)NC=3C=C(C(Cl)=CC=3)C(F)(F)F)=CC=2)=C1 MLDQJTXFUGDVEO-UHFFFAOYSA-N 0.000 description 2
• 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 description 2
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
• 206010005003 Bladder cancer Diseases 0.000 description 2
• 208000020084 Bone disease Diseases 0.000 description 2
• GAGWJHPBXLXJQN-UORFTKCHSA-N Capecitabine Chemical compound C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1[C@H]1[C@H](O)[C@H](O)[C@@H](C)O1 GAGWJHPBXLXJQN-UORFTKCHSA-N 0.000 description 2
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
• OKTJSMMVPCPJKN-NJFSPNSNSA-N Carbon-14 Chemical compound [14C] OKTJSMMVPCPJKN-NJFSPNSNSA-N 0.000 description 2
• 206010007572 Cardiac hypertrophy Diseases 0.000 description 2
• 241000282693 Cercopithecidae Species 0.000 description 2
• 241000254173 Coleoptera Species 0.000 description 2
• 206010009944 Colon cancer Diseases 0.000 description 2
• 229940126062 Compound A Drugs 0.000 description 2
• CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 2
• 201000003883 Cystic fibrosis Diseases 0.000 description 2
• UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 description 2
• 102000002004 Cytochrome P-450 Enzyme System Human genes 0.000 description 2
• 108010015742 Cytochrome P-450 Enzyme System Proteins 0.000 description 2
• FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
• FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
• FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
• AEMOLEFTQBMNLQ-AQKNRBDQSA-N D-glucopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-AQKNRBDQSA-N 0.000 description 2
• WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 2
• 108010092160 Dactinomycin Proteins 0.000 description 2
• 206010061818 Disease progression Diseases 0.000 description 2
• IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
• IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 2
• 239000004471 Glycine Substances 0.000 description 2
• 239000007821 HATU Substances 0.000 description 2
• 206010019842 Hepatomegaly Diseases 0.000 description 2
• NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
• 208000008839 Kidney Neoplasms Diseases 0.000 description 2
• ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 2
• 239000005551 L01XE03 - Erlotinib Substances 0.000 description 2
• 239000005511 L01XE05 - Sorafenib Substances 0.000 description 2
• 239000002136 L01XE07 - Lapatinib Substances 0.000 description 2
• 108060001084 Luciferase Proteins 0.000 description 2
• 239000005089 Luciferase Substances 0.000 description 2
• 229930195725 Mannitol Natural products 0.000 description 2
• 241001465754 Metazoa Species 0.000 description 2
• 208000019695 Migraine disease Diseases 0.000 description 2
• NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 description 2
• FFDGPVCHZBVARC-UHFFFAOYSA-N N,N-dimethylglycine Chemical compound CN(C)CC(O)=O FFDGPVCHZBVARC-UHFFFAOYSA-N 0.000 description 2
• QIAFMBKCNZACKA-UHFFFAOYSA-N N-benzoylglycine Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 description 2
• ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 description 2
• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical class C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
• 208000012902 Nervous system disease Diseases 0.000 description 2
• 208000025966 Neurological disease Diseases 0.000 description 2
• 102000014160 PTEN Phosphohydrolase Human genes 0.000 description 2
• 108010011536 PTEN Phosphohydrolase Proteins 0.000 description 2
• 229930012538 Paclitaxel Natural products 0.000 description 2
• 208000002193 Pain Diseases 0.000 description 2
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
• 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 2
• 102000001708 Protein Isoforms Human genes 0.000 description 2
• 108010029485 Protein Isoforms Proteins 0.000 description 2
• 102000001253 Protein Kinase Human genes 0.000 description 2
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
• LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
• LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
• IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 2
• 241000700159 Rattus Species 0.000 description 2
• 208000005718 Stomach Neoplasms Diseases 0.000 description 2
• 208000006011 Stroke Diseases 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
• 230000006044 T cell activation Effects 0.000 description 2
• NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 description 2
• FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
• 108090000190 Thrombin Proteins 0.000 description 2
• 229920001615 Tragacanth Polymers 0.000 description 2
• 238000010521 absorption reaction Methods 0.000 description 2
• RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 description 2
• 230000009471 action Effects 0.000 description 2
• 230000004913 activation Effects 0.000 description 2
• 239000011149 active material Substances 0.000 description 2
• 239000013543 active substance Substances 0.000 description 2
• 238000012382 advanced drug delivery Methods 0.000 description 2
• 125000005907 alkyl ester group Chemical group 0.000 description 2
• 230000000172 allergic effect Effects 0.000 description 2
• 230000009435 amidation Effects 0.000 description 2
• 238000007112 amidation reaction Methods 0.000 description 2
• 125000003277 amino group Chemical group 0.000 description 2
• ROBVIMPUHSLWNV-UHFFFAOYSA-N aminoglutethimide Chemical compound C=1C=C(N)C=CC=1C1(CC)CCC(=O)NC1=O ROBVIMPUHSLWNV-UHFFFAOYSA-N 0.000 description 2
• 229960003437 aminoglutethimide Drugs 0.000 description 2
• YBBLVLTVTVSKRW-UHFFFAOYSA-N anastrozole Chemical compound N#CC(C)(C)C1=CC(C(C)(C#N)C)=CC(CN2N=CN=C2)=C1 YBBLVLTVTVSKRW-UHFFFAOYSA-N 0.000 description 2
• MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical class C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
• 239000003242 anti bacterial agent Substances 0.000 description 2
• 230000001093 anti-cancer Effects 0.000 description 2
• 230000001028 anti-proliverative effect Effects 0.000 description 2
• 229940088710 antibiotic agent Drugs 0.000 description 2
• 230000006907 apoptotic process Effects 0.000 description 2
• 238000013459 approach Methods 0.000 description 2
• ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 2
• 235000010323 ascorbic acid Nutrition 0.000 description 2
• 239000011668 ascorbic acid Substances 0.000 description 2
• 208000010668 atopic eczema Diseases 0.000 description 2
• HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 2
• 125000004069 aziridinyl group Chemical group 0.000 description 2
• 230000004888 barrier function Effects 0.000 description 2
• CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 2
• UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 2
• 239000011230 binding agent Substances 0.000 description 2
• 210000004369 blood Anatomy 0.000 description 2
• 239000008280 blood Substances 0.000 description 2
• 238000009835 boiling Methods 0.000 description 2
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 2
• GXJABQQUPOEUTA-RDJZCZTQSA-N bortezomib Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)B(O)O)NC(=O)C=1N=CC=NC=1)C1=CC=CC=C1 GXJABQQUPOEUTA-RDJZCZTQSA-N 0.000 description 2
• 235000019437 butane-1,3-diol Nutrition 0.000 description 2
• 239000004202 carbamide Substances 0.000 description 2
• CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 2
• 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
• YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
• 230000010261 cell growth Effects 0.000 description 2
• 210000000170 cell membrane Anatomy 0.000 description 2
• 238000001516 cell proliferation assay Methods 0.000 description 2
• 230000033077 cellular process Effects 0.000 description 2
• 239000002738 chelating agent Substances 0.000 description 2
• WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 2
• LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 2
• 238000004440 column chromatography Methods 0.000 description 2
• 238000001816 cooling Methods 0.000 description 2
• 238000006880 cross-coupling reaction Methods 0.000 description 2
• PFWWSGFPICCWGU-UHFFFAOYSA-N cyclopropanesulfonyl chloride Chemical compound ClS(=O)(=O)C1CC1 PFWWSGFPICCWGU-UHFFFAOYSA-N 0.000 description 2
• OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 description 2
• 230000001085 cytostatic effect Effects 0.000 description 2
• STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 description 2
• 230000006240 deamidation Effects 0.000 description 2
• 238000007257 deesterification reaction Methods 0.000 description 2
• 239000003405 delayed action preparation Substances 0.000 description 2
• 238000013461 design Methods 0.000 description 2
• 230000001066 destructive effect Effects 0.000 description 2
• 238000003745 diagnosis Methods 0.000 description 2
• 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 description 2
• 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 description 2
• 229940113088 dimethylacetamide Drugs 0.000 description 2
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
• 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 2
• 230000005750 disease progression Effects 0.000 description 2
• 238000004821 distillation Methods 0.000 description 2
• 238000009826 distribution Methods 0.000 description 2
• 238000009509 drug development Methods 0.000 description 2
• 238000001035 drying Methods 0.000 description 2
• 230000002255 enzymatic effect Effects 0.000 description 2
• AAKJLRGGTJKAMG-UHFFFAOYSA-N erlotinib Chemical compound C=12C=C(OCCOC)C(OCCOC)=CC2=NC=NC=1NC1=CC=CC(C#C)=C1 AAKJLRGGTJKAMG-UHFFFAOYSA-N 0.000 description 2
• 230000032050 esterification Effects 0.000 description 2
• 238000005886 esterification reaction Methods 0.000 description 2
• CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 2
• 238000001704 evaporation Methods 0.000 description 2
• 230000008020 evaporation Effects 0.000 description 2
• 239000000284 extract Substances 0.000 description 2
• 229940087476 femara Drugs 0.000 description 2
• OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 description 2
• 235000019253 formic acid Nutrition 0.000 description 2
• 125000000524 functional group Chemical group 0.000 description 2
• CHPZKNULDCNCBW-UHFFFAOYSA-N gallium nitrate Chemical compound [Ga+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O CHPZKNULDCNCBW-UHFFFAOYSA-N 0.000 description 2
• BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 2
• 206010017758 gastric cancer Diseases 0.000 description 2
• XGALLCVXEZPNRQ-UHFFFAOYSA-N gefitinib Chemical compound C=12C=C(OCCCN3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 XGALLCVXEZPNRQ-UHFFFAOYSA-N 0.000 description 2
• 239000011521 glass Substances 0.000 description 2
• 229930195712 glutamate Natural products 0.000 description 2
• 229940049906 glutamate Drugs 0.000 description 2
• 229960002989 glutamic acid Drugs 0.000 description 2
• 235000011187 glycerol Nutrition 0.000 description 2
• 229940075507 glyceryl monostearate Drugs 0.000 description 2
• 238000013537 high throughput screening Methods 0.000 description 2
• 239000001257 hydrogen Substances 0.000 description 2
• 229960001101 ifosfamide Drugs 0.000 description 2
• HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 0.000 description 2
• YLMAHDNUQAMNNX-UHFFFAOYSA-N imatinib methanesulfonate Chemical compound CS(O)(=O)=O.C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 YLMAHDNUQAMNNX-UHFFFAOYSA-N 0.000 description 2
• 238000011065 in-situ storage Methods 0.000 description 2
• 239000003701 inert diluent Substances 0.000 description 2
• 208000027866 inflammatory disease Diseases 0.000 description 2
• 239000011630 iodine Substances 0.000 description 2
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 2
• 238000006317 isomerization reaction Methods 0.000 description 2
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 2
• 201000010982 kidney cancer Diseases 0.000 description 2
• 229960003881 letrozole Drugs 0.000 description 2
• GFIJNRVAKGFPGQ-LIJARHBVSA-N leuprolide Chemical compound CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H]1NC(=O)CC1)CC1=CC=C(O)C=C1 GFIJNRVAKGFPGQ-LIJARHBVSA-N 0.000 description 2
• 229960004338 leuprorelin Drugs 0.000 description 2
• DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 2
• 208000014018 liver neoplasm Diseases 0.000 description 2
• 239000007937 lozenge Substances 0.000 description 2
• 238000004020 luminiscence type Methods 0.000 description 2
• 239000012931 lyophilized formulation Substances 0.000 description 2
• RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
• 210000004962 mammalian cell Anatomy 0.000 description 2
• 229960002510 mandelic acid Drugs 0.000 description 2
• 235000010355 mannitol Nutrition 0.000 description 2
• 239000000594 mannitol Substances 0.000 description 2
• 229960001428 mercaptopurine Drugs 0.000 description 2
• 229910052751 metal Inorganic materials 0.000 description 2
• 239000002184 metal Substances 0.000 description 2
• NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 2
• 239000004005 microsphere Substances 0.000 description 2
• 206010027599 migraine Diseases 0.000 description 2
• 230000005012 migration Effects 0.000 description 2
• 238000013508 migration Methods 0.000 description 2
• 229960001156 mitoxantrone Drugs 0.000 description 2
• XRYGCVVVDCEPRL-UHFFFAOYSA-N n,1-dimethylpiperidin-4-amine Chemical compound CNC1CCN(C)CC1 XRYGCVVVDCEPRL-UHFFFAOYSA-N 0.000 description 2
• JJEMPZXXGBIJIX-UHFFFAOYSA-N n,n-dimethyl-2-piperazin-1-ylacetamide Chemical compound CN(C)C(=O)CN1CCNCC1 JJEMPZXXGBIJIX-UHFFFAOYSA-N 0.000 description 2
• ZGAMXARHJKUHGE-UHFFFAOYSA-N n-(2-methoxyethyl)-n-methylpiperazine-1-carboxamide Chemical compound COCCN(C)C(=O)N1CCNCC1 ZGAMXARHJKUHGE-UHFFFAOYSA-N 0.000 description 2
• UOZUNDRVESAZLS-UHFFFAOYSA-N n-(2-methoxyethyl)-n-methylpiperidin-4-amine Chemical compound COCCN(C)C1CCNCC1 UOZUNDRVESAZLS-UHFFFAOYSA-N 0.000 description 2
• GIWIFLNVUUMSPG-UHFFFAOYSA-N n-[(2-chloro-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl)methyl]-n,1-dimethylpiperidin-4-amine Chemical compound C1CN(C)CCC1N(C)CC(SC1=NC(Cl)=N2)=CC1=C2N1CCOCC1 GIWIFLNVUUMSPG-UHFFFAOYSA-N 0.000 description 2
• WUTBHWNICXUPRS-UHFFFAOYSA-N n-[(2-chloro-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl)methyl]-n,1-dimethylpiperidin-4-amine Chemical compound C1CN(C)CCC1N(C)CC(SC1=2)=CC1=NC(Cl)=NC=2N1CCOCC1 WUTBHWNICXUPRS-UHFFFAOYSA-N 0.000 description 2
• 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
• 239000002105 nanoparticle Substances 0.000 description 2
• QZGIWPZCWHMVQL-UIYAJPBUSA-N neocarzinostatin chromophore Chemical compound O1[C@H](C)[C@H](O)[C@H](O)[C@@H](NC)[C@H]1O[C@@H]1C/2=C/C#C[C@H]3O[C@@]3([C@@H]3OC(=O)OC3)C#CC\2=C[C@H]1OC(=O)C1=C(O)C=CC2=C(C)C=C(OC)C=C12 QZGIWPZCWHMVQL-UIYAJPBUSA-N 0.000 description 2
• 208000015122 neurodegenerative disease Diseases 0.000 description 2
• 229910000069 nitrogen hydride Inorganic materials 0.000 description 2
• 239000000346 nonvolatile oil Substances 0.000 description 2
• 239000003883 ointment base Substances 0.000 description 2
• ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
• 150000007524 organic acids Chemical class 0.000 description 2
• 230000002018 overexpression Effects 0.000 description 2
• 230000003647 oxidation Effects 0.000 description 2
• 238000007254 oxidation reaction Methods 0.000 description 2
• 238000004806 packaging method and process Methods 0.000 description 2
• 229960001592 paclitaxel Drugs 0.000 description 2
• 230000036961 partial effect Effects 0.000 description 2
• 239000002245 particle Substances 0.000 description 2
• AQIXEPGDORPWBJ-UHFFFAOYSA-N pentan-3-ol Chemical compound CCC(O)CC AQIXEPGDORPWBJ-UHFFFAOYSA-N 0.000 description 2
• 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 2
• 210000003800 pharynx Anatomy 0.000 description 2
• 239000002953 phosphate buffered saline Substances 0.000 description 2
• 150000003906 phosphoinositides Chemical class 0.000 description 2
• 239000011574 phosphorus Chemical group 0.000 description 2
• IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 description 2
• BZQFBWGGLXLEPQ-REOHCLBHSA-N phosphoserine Chemical compound OC(=O)[C@@H](N)COP(O)(O)=O BZQFBWGGLXLEPQ-REOHCLBHSA-N 0.000 description 2
• XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 2
• 229920001184 polypeptide Polymers 0.000 description 2
• 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
• 229910000027 potassium carbonate Inorganic materials 0.000 description 2
• 150000003141 primary amines Chemical class 0.000 description 2
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
• 102000004196 processed proteins & peptides Human genes 0.000 description 2
• 230000002062 proliferating effect Effects 0.000 description 2
• UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 description 2
• DRINJBFRTLBHNF-UHFFFAOYSA-N propane-2-sulfonyl chloride Chemical compound CC(C)S(Cl)(=O)=O DRINJBFRTLBHNF-UHFFFAOYSA-N 0.000 description 2
• 238000011321 prophylaxis Methods 0.000 description 2
• 108060006633 protein kinase Proteins 0.000 description 2
• 235000018102 proteins Nutrition 0.000 description 2
• 102000004169 proteins and genes Human genes 0.000 description 2
• RXWNCPJZOCPEPQ-NVWDDTSBSA-N puromycin Chemical compound C1=CC(OC)=CC=C1C[C@H](N)C(=O)N[C@H]1[C@@H](O)[C@H](N2C3=NC=NC(=C3N=C2)N(C)C)O[C@@H]1CO RXWNCPJZOCPEPQ-NVWDDTSBSA-N 0.000 description 2
• 125000003226 pyrazolyl group Chemical group 0.000 description 2
• QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 2
• 150000003230 pyrimidines Chemical class 0.000 description 2
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
• GZUITABIAKMVPG-UHFFFAOYSA-N raloxifene Chemical compound C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(O)C=C2S1 GZUITABIAKMVPG-UHFFFAOYSA-N 0.000 description 2
• 229960004622 raloxifene Drugs 0.000 description 2
• ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Natural products COCC(O)C(=C/C(C)C(=O)CC(OC(=O)C1CCCCN1C(=O)C(=O)C2(O)OC(CC(OC)C(=CC=CC=CC(C)CC(C)C(=O)C)C)CCC2C)C(C)CC3CCC(O)C(C3)OC)C ZAHRKKWIAAJSAO-UHFFFAOYSA-N 0.000 description 2
• 230000009467 reduction Effects 0.000 description 2
• 238000006722 reduction reaction Methods 0.000 description 2
• 230000008521 reorganization Effects 0.000 description 2
• GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
• 229960001860 salicylate Drugs 0.000 description 2
• YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 2
• YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
• FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 2
• 150000003335 secondary amines Chemical class 0.000 description 2
• 229940095743 selective estrogen receptor modulator Drugs 0.000 description 2
• 239000000333 selective estrogen receptor modulator Substances 0.000 description 2
• 230000011664 signaling Effects 0.000 description 2
• 239000000741 silica gel Substances 0.000 description 2
• 229910002027 silica gel Inorganic materials 0.000 description 2
• 238000010898 silica gel chromatography Methods 0.000 description 2
• 229960001866 silicon dioxide Drugs 0.000 description 2
• NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
• 229960002930 sirolimus Drugs 0.000 description 2
• 229910052708 sodium Inorganic materials 0.000 description 2
• RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 2
• 239000000600 sorbitol Substances 0.000 description 2
• 235000010356 sorbitol Nutrition 0.000 description 2
• 208000010110 spontaneous platelet aggregation Diseases 0.000 description 2
• 208000017572 squamous cell neoplasm Diseases 0.000 description 2
• 201000011549 stomach cancer Diseases 0.000 description 2
• PVYJZLYGTZKPJE-UHFFFAOYSA-N streptonigrin Chemical compound C=1C=C2C(=O)C(OC)=C(N)C(=O)C2=NC=1C(C=1N)=NC(C(O)=O)=C(C)C=1C1=CC=C(OC)C(OC)=C1O PVYJZLYGTZKPJE-UHFFFAOYSA-N 0.000 description 2
• 238000000859 sublimation Methods 0.000 description 2
• 230000008022 sublimation Effects 0.000 description 2
• KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 2
• FQZYTYWMLGAPFJ-OQKDUQJOSA-N tamoxifen citrate Chemical compound [H+].[H+].[H+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 FQZYTYWMLGAPFJ-OQKDUQJOSA-N 0.000 description 2
• 239000011975 tartaric acid Substances 0.000 description 2
• 235000002906 tartaric acid Nutrition 0.000 description 2
• RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 2
• DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
• GVJMJGZGQPIRRM-VIFPVBQESA-N tert-butyl (3s)-3-methyl-4-methylsulfonylpiperazine-1-carboxylate Chemical compound C[C@H]1CN(C(=O)OC(C)(C)C)CCN1S(C)(=O)=O GVJMJGZGQPIRRM-VIFPVBQESA-N 0.000 description 2
• HEGCGYQZUGNZJO-UHFFFAOYSA-N tert-butyl 4-[(2-chloro-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl)methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(Cl)N=C2S1 HEGCGYQZUGNZJO-UHFFFAOYSA-N 0.000 description 2
• QNKVCXJZMUTEPJ-UHFFFAOYSA-N tert-butyl 4-[(2-chloro-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl)methyl]piperazine-1-carboxylate Chemical compound S1C2=C(N3CCOCC3)N=C(Cl)N=C2C(C)=C1CN1CCN(C(=O)OC(C)(C)C)CC1 QNKVCXJZMUTEPJ-UHFFFAOYSA-N 0.000 description 2
• WOEQSXAIPTXOPY-UHFFFAOYSA-N tert-butyl 4-methylsulfonyloxypiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(OS(C)(=O)=O)CC1 WOEQSXAIPTXOPY-UHFFFAOYSA-N 0.000 description 2
• IBDXIJWCSGQNAR-UHFFFAOYSA-N tert-butyl 4-methylsulfonylpiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(S(C)(=O)=O)CC1 IBDXIJWCSGQNAR-UHFFFAOYSA-N 0.000 description 2
• LLBKAAHFDNMGNG-UHFFFAOYSA-N tert-butyl n-(5-bromo-6-methylpyridin-2-yl)carbamate Chemical compound CC1=NC(NC(=O)OC(C)(C)C)=CC=C1Br LLBKAAHFDNMGNG-UHFFFAOYSA-N 0.000 description 2
• WBQYLGCBVADFPD-UHFFFAOYSA-N tert-butyl n-(5-tributylstannyl-1,3-thiazol-2-yl)carbamate Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CN=C(NC(=O)OC(C)(C)C)S1 WBQYLGCBVADFPD-UHFFFAOYSA-N 0.000 description 2
• HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
• 125000001113 thiadiazolyl group Chemical group 0.000 description 2
• 229960001196 thiotepa Drugs 0.000 description 2
• 229960004072 thrombin Drugs 0.000 description 2
• 229960003087 tioguanine Drugs 0.000 description 2
• 238000011200 topical administration Methods 0.000 description 2
• 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 2
• 230000004614 tumor growth Effects 0.000 description 2
• 229960005486 vaccine Drugs 0.000 description 2
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
• HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 description 1
• OGNSCSPNOLGXSM-UHFFFAOYSA-N (+/-)-DABA Natural products NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 description 1
• NNJPGOLRFBJNIW-HNNXBMFYSA-N (-)-demecolcine Chemical compound C1=C(OC)C(=O)C=C2[C@@H](NC)CCC3=CC(OC)=C(OC)C(OC)=C3C2=C1 NNJPGOLRFBJNIW-HNNXBMFYSA-N 0.000 description 1
• VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
• SPLBPPMPKQJGSP-UHFFFAOYSA-N (2-chloro-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl)methanamine Chemical compound C=12SC(CN)=CC2=NC(Cl)=NC=1N1CCOCC1 SPLBPPMPKQJGSP-UHFFFAOYSA-N 0.000 description 1
• MGJSBPBSENBWNX-CQSZACIVSA-N (2r)-1-[4-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-hydroxypropan-1-one Chemical compound C1CN(C(=O)[C@H](O)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=NC(N)=NC=3)N=C2S1 MGJSBPBSENBWNX-CQSZACIVSA-N 0.000 description 1
• WDQLRUYAYXDIFW-RWKIJVEZSA-N (2r,3r,4s,5r,6r)-4-[(2s,3r,4s,5r,6r)-3,5-dihydroxy-4-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-6-(hydroxymethyl)oxane-2,3,5-triol Chemical compound O[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)[C@H](O)[C@@H](CO[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)O1 WDQLRUYAYXDIFW-RWKIJVEZSA-N 0.000 description 1
• LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
• MTQJGELYWGLHDT-HNNXBMFYSA-N (2s)-1-[4-[[2-(2-amino-4-methylpyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-hydroxypropan-1-one Chemical compound C1CN(C(=O)[C@@H](O)C)CCN1CC1=CC2=NC(C=3C(=NC(N)=NC=3)C)=NC(N3CCOCC3)=C2S1 MTQJGELYWGLHDT-HNNXBMFYSA-N 0.000 description 1
• FLWWDYNPWOSLEO-HQVZTVAUSA-N (2s)-2-[[4-[1-(2-amino-4-oxo-1h-pteridin-6-yl)ethyl-methylamino]benzoyl]amino]pentanedioic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1C(C)N(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FLWWDYNPWOSLEO-HQVZTVAUSA-N 0.000 description 1
• XMQUEQJCYRFIQS-YFKPBYRVSA-N (2s)-2-amino-5-ethoxy-5-oxopentanoic acid Chemical compound CCOC(=O)CC[C@H](N)C(O)=O XMQUEQJCYRFIQS-YFKPBYRVSA-N 0.000 description 1
• PAORVUMOXXAMPL-SECBINFHSA-N (2s)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl chloride Chemical compound CO[C@](C(Cl)=O)(C(F)(F)F)C1=CC=CC=C1 PAORVUMOXXAMPL-SECBINFHSA-N 0.000 description 1
• LJRDOKAZOAKLDU-UDXJMMFXSA-N (2s,3s,4r,5r,6r)-5-amino-2-(aminomethyl)-6-[(2r,3s,4r,5s)-5-[(1r,2r,3s,5r,6s)-3,5-diamino-2-[(2s,3r,4r,5s,6r)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxycyclohexyl]oxy-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxyoxane-3,4-diol;sulfuric ac Chemical compound OS(O)(=O)=O.N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)O[C@@H]1CO LJRDOKAZOAKLDU-UDXJMMFXSA-N 0.000 description 1
• IFNWESYYDINUHV-OLQVQODUSA-N (2s,6r)-2,6-dimethylpiperazine Chemical compound C[C@H]1CNC[C@@H](C)N1 IFNWESYYDINUHV-OLQVQODUSA-N 0.000 description 1
• CGMTUJFWROPELF-YPAAEMCBSA-N (3E,5S)-5-[(2S)-butan-2-yl]-3-(1-hydroxyethylidene)pyrrolidine-2,4-dione Chemical compound CC[C@H](C)[C@@H]1NC(=O)\C(=C(/C)O)C1=O CGMTUJFWROPELF-YPAAEMCBSA-N 0.000 description 1
• BIWOSRSKDCZIFM-RXMQYKEDSA-N (3r)-piperidin-3-ol Chemical compound O[C@@H]1CCCNC1 BIWOSRSKDCZIFM-RXMQYKEDSA-N 0.000 description 1
• MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 description 1
• VYUQPZHRDKLOPX-FQEVSTJZSA-N (3s)-3-methyl-1-tritylpiperazine Chemical compound C1CN[C@@H](C)CN1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 VYUQPZHRDKLOPX-FQEVSTJZSA-N 0.000 description 1
• SSEJSSNDPMMWBQ-YFKPBYRVSA-N (3s)-3-methylpiperazine-1-carboxylic acid Chemical compound C[C@H]1CN(C(O)=O)CCN1 SSEJSSNDPMMWBQ-YFKPBYRVSA-N 0.000 description 1
• JHHZLHWJQPUNKB-BYPYZUCNSA-N (3s)-pyrrolidin-3-ol Chemical compound O[C@H]1CCNC1 JHHZLHWJQPUNKB-BYPYZUCNSA-N 0.000 description 1
• TVIRNGFXQVMMGB-OFWIHYRESA-N (3s,6r,10r,13e,16s)-16-[(2r,3r,4s)-4-chloro-3-hydroxy-4-phenylbutan-2-yl]-10-[(3-chloro-4-methoxyphenyl)methyl]-6-methyl-3-(2-methylpropyl)-1,4-dioxa-8,11-diazacyclohexadec-13-ene-2,5,9,12-tetrone Chemical compound C1=C(Cl)C(OC)=CC=C1C[C@@H]1C(=O)NC[C@@H](C)C(=O)O[C@@H](CC(C)C)C(=O)O[C@H]([C@H](C)[C@@H](O)[C@@H](Cl)C=2C=CC=CC=2)C/C=C/C(=O)N1 TVIRNGFXQVMMGB-OFWIHYRESA-N 0.000 description 1
• YUTPAZKVEOJQCY-UHFFFAOYSA-N (4-methoxypyridin-3-yl)boronic acid Chemical compound COC1=CC=NC=C1B(O)O YUTPAZKVEOJQCY-UHFFFAOYSA-N 0.000 description 1
• NXLNNXIXOYSCMB-UHFFFAOYSA-N (4-nitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(OC(Cl)=O)C=C1 NXLNNXIXOYSCMB-UHFFFAOYSA-N 0.000 description 1
• JUWYQISLQJRRNT-UHFFFAOYSA-N (5-formylfuran-2-yl)boronic acid Chemical compound OB(O)C1=CC=C(C=O)O1 JUWYQISLQJRRNT-UHFFFAOYSA-N 0.000 description 1
• GGOXLPCTWDZMCE-UHFFFAOYSA-N (5-formylpyridin-2-yl)boronic acid Chemical compound OB(O)C1=CC=C(C=O)C=N1 GGOXLPCTWDZMCE-UHFFFAOYSA-N 0.000 description 1
• DEQOVKFWRPOPQP-UHFFFAOYSA-N (5-formylthiophen-2-yl)boronic acid Chemical compound OB(O)C1=CC=C(C=O)S1 DEQOVKFWRPOPQP-UHFFFAOYSA-N 0.000 description 1
• KIUPCUCGVCGPPA-UHFFFAOYSA-N (5-methyl-2-propan-2-ylcyclohexyl) carbonochloridate Chemical compound CC(C)C1CCC(C)CC1OC(Cl)=O KIUPCUCGVCGPPA-UHFFFAOYSA-N 0.000 description 1
• XRBSKUSTLXISAB-XVVDYKMHSA-N (5r,6r,7r,8r)-8-hydroxy-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydrobenzo[f][1,3]benzodioxole-6-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@H](O)[C@@H](CO)[C@@H]2C(O)=O)=C1 XRBSKUSTLXISAB-XVVDYKMHSA-N 0.000 description 1
• OMJKFYKNWZZKTK-POHAHGRESA-N (5z)-5-(dimethylaminohydrazinylidene)imidazole-4-carboxamide Chemical compound CN(C)N\N=C1/N=CN=C1C(N)=O OMJKFYKNWZZKTK-POHAHGRESA-N 0.000 description 1
• OJBYZWHAPXIJID-UHFFFAOYSA-N (6-fluoropyridin-3-yl)boronic acid Chemical compound OB(O)C1=CC=C(F)N=C1 OJBYZWHAPXIJID-UHFFFAOYSA-N 0.000 description 1
• XRBSKUSTLXISAB-UHFFFAOYSA-N (7R,7'R,8R,8'R)-form-Podophyllic acid Natural products COC1=C(OC)C(OC)=CC(C2C3=CC=4OCOC=4C=C3C(O)C(CO)C2C(O)=O)=C1 XRBSKUSTLXISAB-UHFFFAOYSA-N 0.000 description 1
• AESVUZLWRXEGEX-DKCAWCKPSA-N (7S,9R)-7-[(2S,4R,5R,6R)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione iron(3+) Chemical compound [Fe+3].COc1cccc2C(=O)c3c(O)c4C[C@@](O)(C[C@H](O[C@@H]5C[C@@H](N)[C@@H](O)[C@@H](C)O5)c4c(O)c3C(=O)c12)C(=O)CO AESVUZLWRXEGEX-DKCAWCKPSA-N 0.000 description 1
• JXVAMODRWBNUSF-KZQKBALLSA-N (7s,9r,10r)-7-[(2r,4s,5s,6s)-5-[[(2s,4as,5as,7s,9s,9ar,10ar)-2,9-dimethyl-3-oxo-4,4a,5a,6,7,9,9a,10a-octahydrodipyrano[4,2-a:4',3'-e][1,4]dioxin-7-yl]oxy]-4-(dimethylamino)-6-methyloxan-2-yl]oxy-10-[(2s,4s,5s,6s)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2 Chemical compound O([C@@H]1C2=C(O)C=3C(=O)C4=CC=CC(O)=C4C(=O)C=3C(O)=C2[C@@H](O[C@@H]2O[C@@H](C)[C@@H](O[C@@H]3O[C@@H](C)[C@H]4O[C@@H]5O[C@@H](C)C(=O)C[C@@H]5O[C@H]4C3)[C@H](C2)N(C)C)C[C@]1(O)CC)[C@H]1C[C@H](N(C)C)[C@H](O)[C@H](C)O1 JXVAMODRWBNUSF-KZQKBALLSA-N 0.000 description 1
• INAUWOVKEZHHDM-PEDBPRJASA-N (7s,9s)-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-7-[(2r,4s,5s,6s)-5-hydroxy-6-methyl-4-morpholin-4-yloxan-2-yl]oxy-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione;hydrochloride Chemical compound Cl.N1([C@H]2C[C@@H](O[C@@H](C)[C@H]2O)O[C@H]2C[C@@](O)(CC=3C(O)=C4C(=O)C=5C=CC=C(C=5C(=O)C4=C(O)C=32)OC)C(=O)CO)CCOCC1 INAUWOVKEZHHDM-PEDBPRJASA-N 0.000 description 1
• RCFNNLSZHVHCEK-IMHLAKCZSA-N (7s,9s)-7-(4-amino-6-methyloxan-2-yl)oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione;hydrochloride Chemical compound [Cl-].O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)C1CC([NH3+])CC(C)O1 RCFNNLSZHVHCEK-IMHLAKCZSA-N 0.000 description 1
• NOPNWHSMQOXAEI-PUCKCBAPSA-N (7s,9s)-7-[(2r,4s,5s,6s)-4-(2,3-dihydropyrrol-1-yl)-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione Chemical compound N1([C@H]2C[C@@H](O[C@@H](C)[C@H]2O)O[C@H]2C[C@@](O)(CC=3C(O)=C4C(=O)C=5C=CC=C(C=5C(=O)C4=C(O)C=32)OC)C(=O)CO)CCC=C1 NOPNWHSMQOXAEI-PUCKCBAPSA-N 0.000 description 1
• FPVKHBSQESCIEP-UHFFFAOYSA-N (8S)-3-(2-deoxy-beta-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol Natural products C1C(O)C(CO)OC1N1C(NC=NCC2O)=C2N=C1 FPVKHBSQESCIEP-UHFFFAOYSA-N 0.000 description 1
• IEXUMDBQLIVNHZ-YOUGDJEHSA-N (8s,11r,13r,14s,17s)-11-[4-(dimethylamino)phenyl]-17-hydroxy-17-(3-hydroxypropyl)-13-methyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one Chemical compound C1=CC(N(C)C)=CC=C1[C@@H]1C2=C3CCC(=O)C=C3CC[C@H]2[C@H](CC[C@]2(O)CCCO)[C@@]2(C)C1 IEXUMDBQLIVNHZ-YOUGDJEHSA-N 0.000 description 1
• GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 1
• WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
• DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
• LKJPYSCBVHEWIU-KRWDZBQOSA-N (R)-bicalutamide Chemical compound C([C@@](O)(C)C(=O)NC=1C=C(C(C#N)=CC=1)C(F)(F)F)S(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-KRWDZBQOSA-N 0.000 description 1
• KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 1
• MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
• AGNGYMCLFWQVGX-AGFFZDDWSA-N (e)-1-[(2s)-2-amino-2-carboxyethoxy]-2-diazonioethenolate Chemical compound OC(=O)[C@@H](N)CO\C([O-])=C\[N+]#N AGNGYMCLFWQVGX-AGFFZDDWSA-N 0.000 description 1
• ZGYIXVSQHOKQRZ-COIATFDQSA-N (e)-n-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-3-cyano-7-[(3s)-oxolan-3-yl]oxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N#CC1=CN=C2C=C(O[C@@H]3COCC3)C(NC(=O)/C=C/CN(C)C)=CC2=C1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 ZGYIXVSQHOKQRZ-COIATFDQSA-N 0.000 description 1
• MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 1
• UKAUYVFTDYCKQA-UHFFFAOYSA-N -2-Amino-4-hydroxybutanoic acid Natural products OC(=O)C(N)CCO UKAUYVFTDYCKQA-UHFFFAOYSA-N 0.000 description 1
• WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 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
• 125000005988 1,1-dioxo-thiomorpholinyl group Chemical group 0.000 description 1
• BWKMGYQJPOAASG-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid Chemical compound C1=CC=C2CNC(C(=O)O)CC2=C1 BWKMGYQJPOAASG-UHFFFAOYSA-N 0.000 description 1
• KEIFWROAQVVDBN-UHFFFAOYSA-N 1,2-dihydronaphthalene Chemical class C1=CC=C2C=CCCC2=C1 KEIFWROAQVVDBN-UHFFFAOYSA-N 0.000 description 1
• BVVHNDKLDKPYCI-UHFFFAOYSA-N 1,2-dimethylpiperidin-4-amine Chemical compound CC1CC(N)CCN1C BVVHNDKLDKPYCI-UHFFFAOYSA-N 0.000 description 1
• FONKWHRXTPJODV-DNQXCXABSA-N 1,3-bis[2-[(8s)-8-(chloromethyl)-4-hydroxy-1-methyl-7,8-dihydro-3h-pyrrolo[3,2-e]indole-6-carbonyl]-1h-indol-5-yl]urea Chemical compound C1([C@H](CCl)CN2C(=O)C=3NC4=CC=C(C=C4C=3)NC(=O)NC=3C=C4C=C(NC4=CC=3)C(=O)N3C4=CC(O)=C5NC=C(C5=C4[C@H](CCl)C3)C)=C2C=C(O)C2=C1C(C)=CN2 FONKWHRXTPJODV-DNQXCXABSA-N 0.000 description 1
• WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
• JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 description 1
• QDVBKXJMLILLLB-UHFFFAOYSA-N 1,4'-bipiperidine Chemical compound C1CCCCN1C1CCNCC1 QDVBKXJMLILLLB-UHFFFAOYSA-N 0.000 description 1
• WORJRXHJTUTINR-UHFFFAOYSA-N 1,4-dioxane;hydron;chloride Chemical compound Cl.C1COCCO1 WORJRXHJTUTINR-UHFFFAOYSA-N 0.000 description 1
• NDOVLWQBFFJETK-UHFFFAOYSA-N 1,4-thiazinane 1,1-dioxide Chemical compound O=S1(=O)CCNCC1 NDOVLWQBFFJETK-UHFFFAOYSA-N 0.000 description 1
• GRCQWXIJVHIXEB-UHFFFAOYSA-N 1-(2-chloro-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl)-n-methylmethanamine Chemical compound N1=C(Cl)N=C2SC(CNC)=CC2=C1N1CCOCC1 GRCQWXIJVHIXEB-UHFFFAOYSA-N 0.000 description 1
• FGYOBHBOPXDZMF-UHFFFAOYSA-N 1-(2-chloro-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl)-n-methylmethanamine Chemical compound C=12SC(CNC)=CC2=NC(Cl)=NC=1N1CCOCC1 FGYOBHBOPXDZMF-UHFFFAOYSA-N 0.000 description 1
• MYBLAOJMRYYKMS-RTRLPJTCSA-N 1-(2-chloroethyl)-1-nitroso-3-[(3r,4r,5s,6r)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]urea Chemical compound OC[C@H]1OC(O)[C@H](NC(=O)N(CCCl)N=O)[C@@H](O)[C@@H]1O MYBLAOJMRYYKMS-RTRLPJTCSA-N 0.000 description 1
• VGEQUMWEQWWIJT-UHFFFAOYSA-N 1-[(1-methylpiperidin-4-yl)methyl]piperazine Chemical compound C1CN(C)CCC1CN1CCNCC1 VGEQUMWEQWWIJT-UHFFFAOYSA-N 0.000 description 1
• MXYVDMOATFRPMH-UHFFFAOYSA-N 1-[(2-chloro-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl)methyl]-n-methylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)NC)CCN1CC1=CC2=NC(Cl)=NC(N3CCOCC3)=C2S1 MXYVDMOATFRPMH-UHFFFAOYSA-N 0.000 description 1
• ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 1
• ZKYAJBFVXSFAJV-UHFFFAOYSA-N 1-[4-[(2-chloro-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl)methyl]piperazin-1-yl]-2-hydroxyethanone Chemical compound C1CN(C(=O)CO)CCN1CC1=CC2=C(N3CCOCC3)N=C(Cl)N=C2S1 ZKYAJBFVXSFAJV-UHFFFAOYSA-N 0.000 description 1
• KMZOFGHCXFGGSN-UHFFFAOYSA-N 1-[4-[(2-chloro-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl)methyl]piperazin-1-yl]-2-(oxan-2-yloxy)ethanone Chemical compound C=12SC(CN3CCN(CC3)C(=O)COC3OCCCC3)=CC2=NC(Cl)=NC=1N1CCOCC1 KMZOFGHCXFGGSN-UHFFFAOYSA-N 0.000 description 1
• JIJYAEVVCJSHHT-UHFFFAOYSA-N 1-[4-[(2-chloro-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl)methyl]piperazin-1-yl]-2-hydroxyethanone Chemical compound C1CN(C(=O)CO)CCN1CC1=CC2=NC(Cl)=NC(N3CCOCC3)=C2S1 JIJYAEVVCJSHHT-UHFFFAOYSA-N 0.000 description 1
• JAJIGEGBWOJVTR-UHFFFAOYSA-N 1-[4-[[2-(6-aminopyridin-3-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-hydroxyethanone Chemical compound C1=NC(N)=CC=C1C1=NC(N2CCOCC2)=C(C=C(CN2CCN(CC2)C(=O)CO)S2)C2=N1 JAJIGEGBWOJVTR-UHFFFAOYSA-N 0.000 description 1
• WXVYOOBGBIIUOI-UHFFFAOYSA-N 1-[4-[[2-(6-aminopyridin-3-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-hydroxyethanone Chemical compound S1C2=C(N3CCOCC3)N=C(C=3C=NC(N)=CC=3)N=C2C(C)=C1CN1CCN(C(=O)CO)CC1 WXVYOOBGBIIUOI-UHFFFAOYSA-N 0.000 description 1
• ZADGMYRZLVMGHW-UHFFFAOYSA-N 1-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl]methyl]pyrrolidin-3-ol Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(C=C(CN2CC(O)CC2)S2)C2=N1 ZADGMYRZLVMGHW-UHFFFAOYSA-N 0.000 description 1
• TXQKXSAXELIEIB-UHFFFAOYSA-N 1-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-4-(1,3-thiazol-2-yl)piperidin-4-ol Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCC(O)(CC2)C=2SC=CN=2)=C2)C2=N1 TXQKXSAXELIEIB-UHFFFAOYSA-N 0.000 description 1
• BKFILAUDJFLCAK-UHFFFAOYSA-N 1-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-4-phenylpiperidin-4-ol Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCC(O)(CC2)C=2C=CC=CC=2)=C2)C2=N1 BKFILAUDJFLCAK-UHFFFAOYSA-N 0.000 description 1
• BNOQDEYUBWIGLP-UHFFFAOYSA-N 1-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-4-pyridin-2-ylpiperidin-4-ol Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCC(O)(CC2)C=2N=CC=CC=2)=C2)C2=N1 BNOQDEYUBWIGLP-UHFFFAOYSA-N 0.000 description 1
• IJOCIJHNWGYUGQ-UHFFFAOYSA-N 1-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperidin-4-ol Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCC(O)CC2)=C2)C2=N1 IJOCIJHNWGYUGQ-UHFFFAOYSA-N 0.000 description 1
• IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
• IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical class C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
• BTOTXLJHDSNXMW-POYBYMJQSA-N 2,3-dideoxyuridine Chemical compound O1[C@H](CO)CC[C@@H]1N1C(=O)NC(=O)C=C1 BTOTXLJHDSNXMW-POYBYMJQSA-N 0.000 description 1
• KEQTWHPMSVAFDA-UHFFFAOYSA-N 2,3-dihydro-1h-pyrazole Chemical group C1NNC=C1 KEQTWHPMSVAFDA-UHFFFAOYSA-N 0.000 description 1
• RKHZHTLJEUBARP-UHFFFAOYSA-N 2,4-dimethoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine Chemical compound COC1=NC(OC)=NC=C1B1OC(C)(C)C(C)(C)O1 RKHZHTLJEUBARP-UHFFFAOYSA-N 0.000 description 1
• BOMZMNZEXMAQQW-UHFFFAOYSA-N 2,5,11-trimethyl-6h-pyrido[4,3-b]carbazol-2-ium-9-ol;acetate Chemical compound CC([O-])=O.C[N+]1=CC=C2C(C)=C(NC=3C4=CC(O)=CC=3)C4=C(C)C2=C1 BOMZMNZEXMAQQW-UHFFFAOYSA-N 0.000 description 1
• FFMBYMANYCDCMK-UHFFFAOYSA-N 2,5-dihydro-1h-imidazole Chemical group C1NCN=C1 FFMBYMANYCDCMK-UHFFFAOYSA-N 0.000 description 1
• WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 1
• XVCYODCCYCPADG-UHFFFAOYSA-N 2-(2-aminoethyldisulfanyl)ethanamine;sulfuric acid Chemical compound OS(O)(=O)=O.NCCSSCCN XVCYODCCYCPADG-UHFFFAOYSA-N 0.000 description 1
• TXHAHOVNFDVCCC-UHFFFAOYSA-N 2-(tert-butylazaniumyl)acetate Chemical compound CC(C)(C)NCC(O)=O TXHAHOVNFDVCCC-UHFFFAOYSA-N 0.000 description 1
• 125000003821 2-(trimethylsilyl)ethoxymethyl group Chemical group [H]C([H])([H])[Si](C([H])([H])[H])(C([H])([H])[H])C([H])([H])C(OC([H])([H])[*])([H])[H] 0.000 description 1
• VRPJIFMKZZEXLR-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid Chemical compound CC(C)(C)OC(=O)NCC(O)=O VRPJIFMKZZEXLR-UHFFFAOYSA-N 0.000 description 1
• QVHJQCGUWFKTSE-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound OC(=O)C(C)NC(=O)OC(C)(C)C QVHJQCGUWFKTSE-UHFFFAOYSA-N 0.000 description 1
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
• QCXJFISCRQIYID-IAEPZHFASA-N 2-amino-1-n-[(3s,6s,7r,10s,16s)-3-[(2s)-butan-2-yl]-7,11,14-trimethyl-2,5,9,12,15-pentaoxo-10-propan-2-yl-8-oxa-1,4,11,14-tetrazabicyclo[14.3.0]nonadecan-6-yl]-4,6-dimethyl-3-oxo-9-n-[(3s,6s,7r,10s,16s)-7,11,14-trimethyl-2,5,9,12,15-pentaoxo-3,10-di(propa Chemical compound C[C@H]1OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@@H]2CCCN2C(=O)[C@H](C(C)C)NC(=O)[C@H]1NC(=O)C1=C(N=C2C(C(=O)N[C@@H]3C(=O)N[C@H](C(N4CCC[C@H]4C(=O)N(C)CC(=O)N(C)[C@@H](C(C)C)C(=O)O[C@@H]3C)=O)[C@@H](C)CC)=C(N)C(=O)C(C)=C2O2)C2=C(C)C=C1 QCXJFISCRQIYID-IAEPZHFASA-N 0.000 description 1
• GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
• YOCIJWAHRAJQFT-UHFFFAOYSA-N 2-bromo-2-methylpropanoyl bromide Chemical compound CC(C)(Br)C(Br)=O YOCIJWAHRAJQFT-UHFFFAOYSA-N 0.000 description 1
• GYZUUBHCHNCFSL-UHFFFAOYSA-N 2-chloro-6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylfuro[2,3-d]pyrimidine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(Cl)N=C2O1 GYZUUBHCHNCFSL-UHFFFAOYSA-N 0.000 description 1
• MGWTZOGAKDMWDU-UHFFFAOYSA-N 2-chloro-6-iodo-4-morpholin-4-ylfuro[3,2-d]pyrimidine Chemical compound C=12OC(I)=CC2=NC(Cl)=NC=1N1CCOCC1 MGWTZOGAKDMWDU-UHFFFAOYSA-N 0.000 description 1
• VEJDXWXFEZCONI-UHFFFAOYSA-N 2-chloro-7-methyl-4-(oxan-4-yl)thieno[3,2-d]pyrimidine-6-carbaldehyde Chemical compound N1=C(Cl)N=C2C(C)=C(C=O)SC2=C1C1CCOCC1 VEJDXWXFEZCONI-UHFFFAOYSA-N 0.000 description 1
• VNBAOSVONFJBKP-UHFFFAOYSA-N 2-chloro-n,n-bis(2-chloroethyl)propan-1-amine;hydrochloride Chemical compound Cl.CC(Cl)CN(CCCl)CCCl VNBAOSVONFJBKP-UHFFFAOYSA-N 0.000 description 1
• XBPPLECAZBTMMK-UHFFFAOYSA-N 2-chloro-n,n-dimethylacetamide Chemical compound CN(C)C(=O)CCl XBPPLECAZBTMMK-UHFFFAOYSA-N 0.000 description 1
• 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
• 150000005695 2-halopyrimidines Chemical class 0.000 description 1
• MFNXWZGIFWJHMI-UHFFFAOYSA-N 2-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)NC(C)(C)C(O)=O MFNXWZGIFWJHMI-UHFFFAOYSA-N 0.000 description 1
• JEECGGXGHJUYMN-UHFFFAOYSA-N 2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Chemical compound C1=NC(C)=CC=C1B1OC(C)(C)C(C)(C)O1 JEECGGXGHJUYMN-UHFFFAOYSA-N 0.000 description 1
• NYEHUAQIJXERLP-UHFFFAOYSA-N 2-methylsulfonylacetic acid Chemical compound CS(=O)(=O)CC(O)=O NYEHUAQIJXERLP-UHFFFAOYSA-N 0.000 description 1
• AOPRXJXHLWYPQR-UHFFFAOYSA-N 2-phenoxyacetamide Chemical class NC(=O)COC1=CC=CC=C1 AOPRXJXHLWYPQR-UHFFFAOYSA-N 0.000 description 1
• FUOZJYASZOSONT-UHFFFAOYSA-N 2-propan-2-yl-1h-imidazole Chemical compound CC(C)C1=NC=CN1 FUOZJYASZOSONT-UHFFFAOYSA-N 0.000 description 1
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
• RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical group C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 1
• 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
• LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
• 125000001698 2H-pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
• YIMDLWDNDGKDTJ-QLKYHASDSA-N 3'-deamino-3'-(3-cyanomorpholin-4-yl)doxorubicin Chemical compound N1([C@H]2C[C@@H](O[C@@H](C)[C@H]2O)O[C@H]2C[C@@](O)(CC=3C(O)=C4C(=O)C=5C=CC=C(C=5C(=O)C4=C(O)C=32)OC)C(=O)CO)CCOCC1C#N YIMDLWDNDGKDTJ-QLKYHASDSA-N 0.000 description 1
• NDMPLJNOPCLANR-UHFFFAOYSA-N 3,4-dihydroxy-15-(4-hydroxy-18-methoxycarbonyl-5,18-seco-ibogamin-18-yl)-16-methoxy-1-methyl-6,7-didehydro-aspidospermidine-3-carboxylic acid methyl ester Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 NDMPLJNOPCLANR-UHFFFAOYSA-N 0.000 description 1
• HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
• BYHQTRFJOGIQAO-GOSISDBHSA-N 3-(4-bromophenyl)-8-[(2R)-2-hydroxypropyl]-1-[(3-methoxyphenyl)methyl]-1,3,8-triazaspiro[4.5]decan-2-one Chemical compound C[C@H](CN1CCC2(CC1)CN(C(=O)N2CC3=CC(=CC=C3)OC)C4=CC=C(C=C4)Br)O BYHQTRFJOGIQAO-GOSISDBHSA-N 0.000 description 1
• PWMYMKOUNYTVQN-UHFFFAOYSA-N 3-(8,8-diethyl-2-aza-8-germaspiro[4.5]decan-2-yl)-n,n-dimethylpropan-1-amine Chemical compound C1C[Ge](CC)(CC)CCC11CN(CCCN(C)C)CC1 PWMYMKOUNYTVQN-UHFFFAOYSA-N 0.000 description 1
• BRMWTNUJHUMWMS-UHFFFAOYSA-N 3-Methylhistidine Natural products CN1C=NC(CC(N)C(O)=O)=C1 BRMWTNUJHUMWMS-UHFFFAOYSA-N 0.000 description 1
• WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-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
• FEWJPZIEWOKRBE-UHFFFAOYSA-M 3-carboxy-2,3-dihydroxypropanoate Chemical compound OC(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-M 0.000 description 1
• BXRLWGXPSRYJDZ-UHFFFAOYSA-N 3-cyanoalanine Chemical compound OC(=O)C(N)CC#N BXRLWGXPSRYJDZ-UHFFFAOYSA-N 0.000 description 1
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
• JVQIKJMSUIMUDI-UHFFFAOYSA-N 3-pyrroline Chemical group C1NCC=C1 JVQIKJMSUIMUDI-UHFFFAOYSA-N 0.000 description 1
• 125000004364 3-pyrrolinyl group Chemical group [H]C1=C([H])C([H])([H])N(*)C1([H])[H] 0.000 description 1
• 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
• AOJJSUZBOXZQNB-VTZDEGQISA-N 4'-epidoxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-VTZDEGQISA-N 0.000 description 1
• MCGBIXXDQFWVDW-UHFFFAOYSA-N 4,5-dihydro-1h-pyrazole Chemical group C1CC=NN1 MCGBIXXDQFWVDW-UHFFFAOYSA-N 0.000 description 1
• CLPFFLWZZBQMAO-UHFFFAOYSA-N 4-(5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl)benzonitrile Chemical compound C1=CC(C#N)=CC=C1C1N2C=NC=C2CCC1 CLPFFLWZZBQMAO-UHFFFAOYSA-N 0.000 description 1
• DODQJNMQWMSYGS-QPLCGJKRSA-N 4-[(z)-1-[4-[2-(dimethylamino)ethoxy]phenyl]-1-phenylbut-1-en-2-yl]phenol Chemical compound C=1C=C(O)C=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 DODQJNMQWMSYGS-QPLCGJKRSA-N 0.000 description 1
• MFRGFJVZAMAGTF-UHFFFAOYSA-N 4-[2-(2-fluoropyridin-3-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3C(=NC=CC=3)F)=NC(N3CCOCC3)=C2S1 MFRGFJVZAMAGTF-UHFFFAOYSA-N 0.000 description 1
• NLMFRVKNYWWMPO-UHFFFAOYSA-N 4-[2-(2-methoxypyrimidin-5-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[2,3-d]pyrimidin-4-yl]morpholine Chemical compound C1=NC(OC)=NC=C1C1=NC(N2CCOCC2)=C(C=C(CN2CCN(CC2)S(C)(=O)=O)S2)C2=N1 NLMFRVKNYWWMPO-UHFFFAOYSA-N 0.000 description 1
• UQWALWDJDYSTHK-UHFFFAOYSA-N 4-[2-(2-methylimidazol-1-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound CC1=NC=CN1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)S(C)(=O)=O)=C2)C2=N1 UQWALWDJDYSTHK-UHFFFAOYSA-N 0.000 description 1
• VOZZXBJEEDMMKT-UHFFFAOYSA-N 4-[2-(6-fluoropyridin-3-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3C=NC(F)=CC=3)=NC(N3CCOCC3)=C2S1 VOZZXBJEEDMMKT-UHFFFAOYSA-N 0.000 description 1
• CSSMUQJAIFGVTR-UHFFFAOYSA-N 4-[2-chloro-6-[(4-methylpiperazin-1-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(C)CCN1CC1=CC2=NC(Cl)=NC(N3CCOCC3)=C2S1 CSSMUQJAIFGVTR-UHFFFAOYSA-N 0.000 description 1
• QLICOIOSNRVJPV-UHFFFAOYSA-N 4-[2-imidazol-1-yl-6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(N3C=NC=C3)=NC(N3CCOCC3)=C2S1 QLICOIOSNRVJPV-UHFFFAOYSA-N 0.000 description 1
• YFCIFWOJYYFDQP-PTWZRHHISA-N 4-[3-amino-6-[(1S,3S,4S)-3-fluoro-4-hydroxycyclohexyl]pyrazin-2-yl]-N-[(1S)-1-(3-bromo-5-fluorophenyl)-2-(methylamino)ethyl]-2-fluorobenzamide Chemical compound CNC[C@@H](NC(=O)c1ccc(cc1F)-c1nc(cnc1N)[C@H]1CC[C@H](O)[C@@H](F)C1)c1cc(F)cc(Br)c1 YFCIFWOJYYFDQP-PTWZRHHISA-N 0.000 description 1
• ULYRLEZOUCZWLX-UHFFFAOYSA-N 4-[6-[(4-methylpiperazin-1-yl)methyl]-2-(1h-pyrazol-4-yl)thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(C)CCN1CC1=CC2=NC(C3=CNN=C3)=NC(N3CCOCC3)=C2S1 ULYRLEZOUCZWLX-UHFFFAOYSA-N 0.000 description 1
• XCLINYXMULJADC-UHFFFAOYSA-N 4-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-2-pyridin-3-ylthieno[2,3-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=NC=CC=3)N=C2S1 XCLINYXMULJADC-UHFFFAOYSA-N 0.000 description 1
• XHYCVVZBZFPLDA-UHFFFAOYSA-N 4-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-2-pyridin-3-ylthieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3C=NC=CC=3)=NC(N3CCOCC3)=C2S1 XHYCVVZBZFPLDA-UHFFFAOYSA-N 0.000 description 1
• IVPHXJBIRULKPM-UHFFFAOYSA-N 4-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-2-pyrimidin-5-ylthieno[2,3-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=NC=NC=3)N=C2S1 IVPHXJBIRULKPM-UHFFFAOYSA-N 0.000 description 1
• PODCPEQVUJBIKR-UHFFFAOYSA-N 4-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-2-pyrimidin-5-ylthieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3C=NC=NC=3)=NC(N3CCOCC3)=C2S1 PODCPEQVUJBIKR-UHFFFAOYSA-N 0.000 description 1
• QCHQMXYRZYEEFG-UHFFFAOYSA-N 4-[[2-(2,4-dimethoxypyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-n,n-dimethylpiperazine-1-sulfonamide Chemical compound COC1=NC(OC)=NC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)S(=O)(=O)N(C)C)=C2)C2=N1 QCHQMXYRZYEEFG-UHFFFAOYSA-N 0.000 description 1
• KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
• TVZGACDUOSZQKY-LBPRGKRZSA-N 4-aminofolic acid Chemical compound C1=NC2=NC(N)=NC(N)=C2N=C1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 TVZGACDUOSZQKY-LBPRGKRZSA-N 0.000 description 1
• 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
• WAMYVXDXUNMQDP-UHFFFAOYSA-N 4-methylsulfonylpiperidine;hydrochloride Chemical compound Cl.CS(=O)(=O)C1CCNCC1 WAMYVXDXUNMQDP-UHFFFAOYSA-N 0.000 description 1
• TVAQTCHYXHOFAZ-UHFFFAOYSA-N 4-morpholin-4-yl-2-pyridin-3-ylthieno[2,3-d]pyrimidine-6-carboxylic acid Chemical compound N1=C2SC(C(=O)O)=CC2=C(N2CCOCC2)N=C1C1=CC=CN=C1 TVAQTCHYXHOFAZ-UHFFFAOYSA-N 0.000 description 1
• WWMBQULJDIYBFO-UHFFFAOYSA-N 4-morpholin-4-yl-2-pyridin-3-ylthieno[3,2-d]pyrimidine-6-carboxylic acid Chemical compound C=12SC(C(=O)O)=CC2=NC(C=2C=NC=CC=2)=NC=1N1CCOCC1 WWMBQULJDIYBFO-UHFFFAOYSA-N 0.000 description 1
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
• KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 description 1
• 125000001826 4H-pyranyl group Chemical group O1C(=CCC=C1)* 0.000 description 1
• CBNIRWXQQRNRJY-UHFFFAOYSA-N 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazin-2-amine Chemical compound O1C(C)(C)C(C)(C)OB1C1=CN=C(N)C=N1 CBNIRWXQQRNRJY-UHFFFAOYSA-N 0.000 description 1
• IXTBQKLZPOYJFJ-UHFFFAOYSA-N 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carbonitrile Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(C#N)N=C1 IXTBQKLZPOYJFJ-UHFFFAOYSA-N 0.000 description 1
• WVIMCYHOZKNOCS-UHFFFAOYSA-N 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-carbaldehyde Chemical compound O1C(C)(C)C(C)(C)OB1C1=CN=CC(C=O)=C1 WVIMCYHOZKNOCS-UHFFFAOYSA-N 0.000 description 1
• IRPVABHDSJVBNZ-RTHVDDQRSA-N 5-[1-(cyclopropylmethyl)-5-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=NN(CC2CC2)C(C2[C@@H]3CN(C[C@@H]32)C2COC2)=C1 IRPVABHDSJVBNZ-RTHVDDQRSA-N 0.000 description 1
• GSMLHTIBFAOGTA-UHFFFAOYSA-N 5-[6-[(4-methylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]pyridin-3-ol Chemical compound C1CN(C)CCN1CC1=CC2=NC(C=3C=C(O)C=NC=3)=NC(N3CCOCC3)=C2S1 GSMLHTIBFAOGTA-UHFFFAOYSA-N 0.000 description 1
• UARBEABWOFNGCQ-UHFFFAOYSA-N 5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylfuro[3,2-d]pyrimidin-2-yl]pyridin-2-amine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3C=NC(N)=CC=3)=NC(N3CCOCC3)=C2O1 UARBEABWOFNGCQ-UHFFFAOYSA-N 0.000 description 1
• IDPUKCWIGUEADI-UHFFFAOYSA-N 5-[bis(2-chloroethyl)amino]uracil Chemical compound ClCCN(CCCl)C1=CNC(=O)NC1=O IDPUKCWIGUEADI-UHFFFAOYSA-N 0.000 description 1
• NMUSYJAQQFHJEW-KVTDHHQDSA-N 5-azacytidine Chemical compound O=C1N=C(N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 NMUSYJAQQFHJEW-KVTDHHQDSA-N 0.000 description 1
• SEOZHXRTVJPQPZ-UHFFFAOYSA-N 5-bromo-6-methylpyridin-2-amine Chemical compound CC1=NC(N)=CC=C1Br SEOZHXRTVJPQPZ-UHFFFAOYSA-N 0.000 description 1
• FHIDNBAQOFJWCA-UAKXSSHOSA-N 5-fluorouridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(F)=C1 FHIDNBAQOFJWCA-UAKXSSHOSA-N 0.000 description 1
• CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 description 1
• KCBWAFJCKVKYHO-UHFFFAOYSA-N 6-(4-cyclopropyl-6-methoxypyrimidin-5-yl)-1-[[4-[1-propan-2-yl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]pyrazolo[3,4-d]pyrimidine Chemical compound C1(CC1)C1=NC=NC(=C1C1=NC=C2C(=N1)N(N=C2)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C(C)C)OC KCBWAFJCKVKYHO-UHFFFAOYSA-N 0.000 description 1
• WYXSYVWAUAUWLD-SHUUEZRQSA-N 6-azauridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=N1 WYXSYVWAUAUWLD-SHUUEZRQSA-N 0.000 description 1
• 229960005538 6-diazo-5-oxo-L-norleucine Drugs 0.000 description 1
• YCWQAMGASJSUIP-YFKPBYRVSA-N 6-diazo-5-oxo-L-norleucine Chemical compound OC(=O)[C@@H](N)CCC(=O)C=[N+]=[N-] YCWQAMGASJSUIP-YFKPBYRVSA-N 0.000 description 1
• VVIAGPKUTFNRDU-UHFFFAOYSA-N 6S-folinic acid Natural products C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-UHFFFAOYSA-N 0.000 description 1
• CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 1
• ZGXJTSGNIOSYLO-UHFFFAOYSA-N 88755TAZ87 Chemical compound NCC(=O)CCC(O)=O ZGXJTSGNIOSYLO-UHFFFAOYSA-N 0.000 description 1
• QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
• BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-UHFFFAOYSA-N 0.000 description 1
• HDZZVAMISRMYHH-UHFFFAOYSA-N 9beta-Ribofuranosyl-7-deazaadenin Natural products C1=CC=2C(N)=NC=NC=2N1C1OC(CO)C(O)C1O HDZZVAMISRMYHH-UHFFFAOYSA-N 0.000 description 1
• 230000035502 ADME Effects 0.000 description 1
• 244000215068 Acacia senegal Species 0.000 description 1
• 235000006491 Acacia senegal Nutrition 0.000 description 1
• 102000009027 Albumins Human genes 0.000 description 1
• 108010088751 Albumins Proteins 0.000 description 1
• GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
• CEIZFXOZIQNICU-UHFFFAOYSA-N Alternaria alternata Crofton-weed toxin Natural products CCC(C)C1NC(=O)C(C(C)=O)=C1O CEIZFXOZIQNICU-UHFFFAOYSA-N 0.000 description 1
• 206010061424 Anal cancer Diseases 0.000 description 1
• 108090000644 Angiozyme Proteins 0.000 description 1
• 108020000948 Antisense Oligonucleotides Proteins 0.000 description 1
• 101100297694 Arabidopsis thaliana PIP2-7 gene Proteins 0.000 description 1
• 102000014654 Aromatase Human genes 0.000 description 1
• 108010078554 Aromatase Proteins 0.000 description 1
• DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 1
• NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical class C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
• 125000006847 BOC protecting group Chemical group 0.000 description 1
• 239000005711 Benzoic acid Substances 0.000 description 1
• VGGGPCQERPFHOB-MCIONIFRSA-N Bestatin Chemical compound CC(C)C[C@H](C(O)=O)NC(=O)[C@@H](O)[C@H](N)CC1=CC=CC=C1 VGGGPCQERPFHOB-MCIONIFRSA-N 0.000 description 1
• 229940122361 Bisphosphonate Drugs 0.000 description 1
• 108010006654 Bleomycin Proteins 0.000 description 1
• 108010039209 Blood Coagulation Factors Proteins 0.000 description 1
• 102000015081 Blood Coagulation Factors Human genes 0.000 description 1
• 108010017384 Blood Proteins Proteins 0.000 description 1
• 102000004506 Blood Proteins Human genes 0.000 description 1
• 241000283690 Bos taurus Species 0.000 description 1
• 201000006474 Brain Ischemia Diseases 0.000 description 1
• 206010006187 Breast cancer Diseases 0.000 description 1
• 208000026310 Breast neoplasm Diseases 0.000 description 1
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
• MBABCNBNDNGODA-LTGLSHGVSA-N Bullatacin Natural products O=C1C(C[C@H](O)CCCCCCCCCC[C@@H](O)[C@@H]2O[C@@H]([C@@H]3O[C@H]([C@@H](O)CCCCCCCCCC)CC3)CC2)=C[C@H](C)O1 MBABCNBNDNGODA-LTGLSHGVSA-N 0.000 description 1
• KGGVWMAPBXIMEM-ZRTAFWODSA-N Bullatacinone Chemical compound O1[C@@H]([C@@H](O)CCCCCCCCCC)CC[C@@H]1[C@@H]1O[C@@H]([C@H](O)CCCCCCCCCC[C@H]2OC(=O)[C@H](CC(C)=O)C2)CC1 KGGVWMAPBXIMEM-ZRTAFWODSA-N 0.000 description 1
• KGGVWMAPBXIMEM-JQFCFGFHSA-N Bullatacinone Natural products O=C(C[C@H]1C(=O)O[C@H](CCCCCCCCCC[C@H](O)[C@@H]2O[C@@H]([C@@H]3O[C@@H]([C@@H](O)CCCCCCCCCC)CC3)CC2)C1)C KGGVWMAPBXIMEM-JQFCFGFHSA-N 0.000 description 1
• COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
• 239000004358 Butane-1, 3-diol Substances 0.000 description 1
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
• KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 description 1
• 241000282472 Canis lupus familiaris Species 0.000 description 1
• GAGWJHPBXLXJQN-UHFFFAOYSA-N Capecitabine Natural products C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1C1C(O)C(O)C(C)O1 GAGWJHPBXLXJQN-UHFFFAOYSA-N 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
• SHHKQEUPHAENFK-UHFFFAOYSA-N Carboquone Chemical compound O=C1C(C)=C(N2CC2)C(=O)C(C(COC(N)=O)OC)=C1N1CC1 SHHKQEUPHAENFK-UHFFFAOYSA-N 0.000 description 1
• 208000010667 Carcinoma of liver and intrahepatic biliary tract Diseases 0.000 description 1
• 206010007559 Cardiac failure congestive Diseases 0.000 description 1
• AOCCBINRVIKJHY-UHFFFAOYSA-N Carmofur Chemical compound CCCCCCNC(=O)N1C=C(F)C(=O)NC1=O AOCCBINRVIKJHY-UHFFFAOYSA-N 0.000 description 1
• DLGOEMSEDOSKAD-UHFFFAOYSA-N Carmustine Chemical compound ClCCNC(=O)N(N=O)CCCl DLGOEMSEDOSKAD-UHFFFAOYSA-N 0.000 description 1
• 102000014914 Carrier Proteins Human genes 0.000 description 1
• 102000011727 Caspases Human genes 0.000 description 1
• 108010076667 Caspases Proteins 0.000 description 1
• 108090000994 Catalytic RNA Proteins 0.000 description 1
• 102000053642 Catalytic RNA Human genes 0.000 description 1
• 241000700198 Cavia Species 0.000 description 1
• 241000700199 Cavia porcellus Species 0.000 description 1
• 238000003734 CellTiter-Glo Luminescent Cell Viability Assay Methods 0.000 description 1
• 206010008120 Cerebral ischaemia Diseases 0.000 description 1
• 206010008342 Cervix carcinoma Diseases 0.000 description 1
• 108091006146 Channels Proteins 0.000 description 1
• JWBOIMRXGHLCPP-UHFFFAOYSA-N Chloditan Chemical compound C=1C=CC=C(Cl)C=1C(C(Cl)Cl)C1=CC=C(Cl)C=C1 JWBOIMRXGHLCPP-UHFFFAOYSA-N 0.000 description 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
• XCDXSSFOJZZGQC-UHFFFAOYSA-N Chlornaphazine Chemical compound C1=CC=CC2=CC(N(CCCl)CCCl)=CC=C21 XCDXSSFOJZZGQC-UHFFFAOYSA-N 0.000 description 1
• 235000001258 Cinchona calisaya Nutrition 0.000 description 1
• WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
• 208000001333 Colorectal Neoplasms Diseases 0.000 description 1
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
• 229920002261 Corn starch Polymers 0.000 description 1
• 229920002785 Croscarmellose sodium Polymers 0.000 description 1
• 229930188224 Cryptophycin Natural products 0.000 description 1
• IGXWBGJHJZYPQS-SSDOTTSWSA-N D-Luciferin Chemical compound OC(=O)[C@H]1CSC(C=2SC3=CC=C(O)C=C3N=2)=N1 IGXWBGJHJZYPQS-SSDOTTSWSA-N 0.000 description 1
• AEMOLEFTQBMNLQ-YMDCURPLSA-N D-galactopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-YMDCURPLSA-N 0.000 description 1
• DSLZVSRJTYRBFB-LLEIAEIESA-N D-glucaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O DSLZVSRJTYRBFB-LLEIAEIESA-N 0.000 description 1
• RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
• WEAHRLBPCANXCN-UHFFFAOYSA-N Daunomycin Natural products CCC1(O)CC(OC2CC(N)C(O)C(C)O2)c3cc4C(=O)c5c(OC)cccc5C(=O)c4c(O)c3C1 WEAHRLBPCANXCN-UHFFFAOYSA-N 0.000 description 1
• CYCGRDQQIOGCKX-UHFFFAOYSA-N Dehydro-luciferin Natural products OC(=O)C1=CSC(C=2SC3=CC(O)=CC=C3N=2)=N1 CYCGRDQQIOGCKX-UHFFFAOYSA-N 0.000 description 1
• NNJPGOLRFBJNIW-UHFFFAOYSA-N Demecolcine Natural products C1=C(OC)C(=O)C=C2C(NC)CCC3=CC(OC)=C(OC)C(OC)=C3C2=C1 NNJPGOLRFBJNIW-UHFFFAOYSA-N 0.000 description 1
• 108010002156 Depsipeptides Proteins 0.000 description 1
• 206010012442 Dermatitis contact Diseases 0.000 description 1
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
• 239000004375 Dextrin Substances 0.000 description 1
• 229920001353 Dextrin Polymers 0.000 description 1
• AUGQEEXBDZWUJY-ZLJUKNTDSA-N Diacetoxyscirpenol Chemical compound C([C@]12[C@]3(C)[C@H](OC(C)=O)[C@@H](O)[C@H]1O[C@@H]1C=C(C)CC[C@@]13COC(=O)C)O2 AUGQEEXBDZWUJY-ZLJUKNTDSA-N 0.000 description 1
• AUGQEEXBDZWUJY-UHFFFAOYSA-N Diacetoxyscirpenol Natural products CC(=O)OCC12CCC(C)=CC1OC1C(O)C(OC(C)=O)C2(C)C11CO1 AUGQEEXBDZWUJY-UHFFFAOYSA-N 0.000 description 1
• BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
• YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 1
• ZQZFYGIXNQKOAV-OCEACIFDSA-N Droloxifene Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=C(O)C=CC=1)\C1=CC=C(OCCN(C)C)C=C1 ZQZFYGIXNQKOAV-OCEACIFDSA-N 0.000 description 1
• 229930193152 Dynemicin Natural products 0.000 description 1
• 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 1
• 206010014733 Endometrial cancer Diseases 0.000 description 1
• 206010014759 Endometrial neoplasm Diseases 0.000 description 1
• AFMYMMXSQGUCBK-UHFFFAOYSA-N Endynamicin A Natural products C1#CC=CC#CC2NC(C=3C(=O)C4=C(O)C=CC(O)=C4C(=O)C=3C(O)=C3)=C3C34OC32C(C)C(C(O)=O)=C(OC)C41 AFMYMMXSQGUCBK-UHFFFAOYSA-N 0.000 description 1
• SAMRUMKYXPVKPA-VFKOLLTISA-N Enocitabine Chemical compound O=C1N=C(NC(=O)CCCCCCCCCCCCCCCCCCCCC)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 SAMRUMKYXPVKPA-VFKOLLTISA-N 0.000 description 1
• 102000004190 Enzymes Human genes 0.000 description 1
• 108090000790 Enzymes Proteins 0.000 description 1
• HTIJFSOGRVMCQR-UHFFFAOYSA-N Epirubicin Natural products COc1cccc2C(=O)c3c(O)c4CC(O)(CC(OC5CC(N)C(=O)C(C)O5)c4c(O)c3C(=O)c12)C(=O)CO HTIJFSOGRVMCQR-UHFFFAOYSA-N 0.000 description 1
• OBMLHUPNRURLOK-XGRAFVIBSA-N Epitiostanol Chemical compound C1[C@@H]2S[C@@H]2C[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CC[C@H]21 OBMLHUPNRURLOK-XGRAFVIBSA-N 0.000 description 1
• 241000283086 Equidae Species 0.000 description 1
• 229930189413 Esperamicin Natural products 0.000 description 1
• JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
• GISRWBROCYNDME-PELMWDNLSA-N F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C Chemical compound F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C GISRWBROCYNDME-PELMWDNLSA-N 0.000 description 1
• 241000282326 Felis catus Species 0.000 description 1
• 108090000331 Firefly luciferases Proteins 0.000 description 1
• BJGNCJDXODQBOB-UHFFFAOYSA-N Fivefly Luciferin Natural products OC(=O)C1CSC(C=2SC3=CC(O)=CC=C3N=2)=N1 BJGNCJDXODQBOB-UHFFFAOYSA-N 0.000 description 1
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
• BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
• VWUXBMIQPBEWFH-WCCTWKNTSA-N Fulvestrant Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3[C@H](CCCCCCCCCS(=O)CCCC(F)(F)C(F)(F)F)CC2=C1 VWUXBMIQPBEWFH-WCCTWKNTSA-N 0.000 description 1
• 230000005526 G1 to G0 transition Effects 0.000 description 1
• 206010017993 Gastrointestinal neoplasms Diseases 0.000 description 1
• WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
• 108010069236 Goserelin Proteins 0.000 description 1
• BLCLNMBMMGCOAS-URPVMXJPSA-N Goserelin Chemical compound C([C@@H](C(=O)N[C@H](COC(C)(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N1[C@@H](CCC1)C(=O)NNC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H]1NC(=O)CC1)C1=CC=C(O)C=C1 BLCLNMBMMGCOAS-URPVMXJPSA-N 0.000 description 1
• 102000009465 Growth Factor Receptors Human genes 0.000 description 1
• 108010009202 Growth Factor Receptors Proteins 0.000 description 1
• 229920000084 Gum arabic Polymers 0.000 description 1
• 206010019280 Heart failures Diseases 0.000 description 1
• 206010073069 Hepatic cancer Diseases 0.000 description 1
• 101001012157 Homo sapiens Receptor tyrosine-protein kinase erbB-2 Proteins 0.000 description 1
• 208000023105 Huntington disease Diseases 0.000 description 1
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
• LCWXJXMHJVIJFK-UHFFFAOYSA-N Hydroxylysine Natural products NCC(O)CC(N)CC(O)=O LCWXJXMHJVIJFK-UHFFFAOYSA-N 0.000 description 1
• PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 description 1
• VSNHCAURESNICA-UHFFFAOYSA-N Hydroxyurea Chemical compound NC(=O)NO VSNHCAURESNICA-UHFFFAOYSA-N 0.000 description 1
• 206010021143 Hypoxia Diseases 0.000 description 1
• MPBVHIBUJCELCL-UHFFFAOYSA-N Ibandronate Chemical compound CCCCCN(C)CCC(O)(P(O)(O)=O)P(O)(O)=O MPBVHIBUJCELCL-UHFFFAOYSA-N 0.000 description 1
• XDXDZDZNSLXDNA-TZNDIEGXSA-N Idarubicin Chemical compound C1[C@H](N)[C@H](O)[C@H](C)O[C@H]1O[C@@H]1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2C[C@@](O)(C(C)=O)C1 XDXDZDZNSLXDNA-TZNDIEGXSA-N 0.000 description 1
• XDXDZDZNSLXDNA-UHFFFAOYSA-N Idarubicin Natural products C1C(N)C(O)C(C)OC1OC1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2CC(O)(C(C)=O)C1 XDXDZDZNSLXDNA-UHFFFAOYSA-N 0.000 description 1
• WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical group C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
• 108060003951 Immunoglobulin Proteins 0.000 description 1
• 238000012695 Interfacial polymerization Methods 0.000 description 1
• SNDPXSYFESPGGJ-BYPYZUCNSA-N L-2-aminopentanoic acid Chemical compound CCC[C@H](N)C(O)=O SNDPXSYFESPGGJ-BYPYZUCNSA-N 0.000 description 1
• AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 1
• ZGUNAGUHMKGQNY-ZETCQYMHSA-N L-alpha-phenylglycine zwitterion Chemical compound OC(=O)[C@@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-ZETCQYMHSA-N 0.000 description 1
• 150000008575 L-amino acids Chemical class 0.000 description 1
• DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 1
• CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
• RHGKLRLOHDJJDR-BYPYZUCNSA-N L-citrulline Chemical compound NC(=O)NCCC[C@H]([NH3+])C([O-])=O RHGKLRLOHDJJDR-BYPYZUCNSA-N 0.000 description 1
• ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
• HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 1
• FFFHZYDWPBMWHY-VKHMYHEASA-N L-homocysteine Chemical compound OC(=O)[C@@H](N)CCS FFFHZYDWPBMWHY-VKHMYHEASA-N 0.000 description 1
• UKAUYVFTDYCKQA-VKHMYHEASA-N L-homoserine Chemical compound OC(=O)[C@@H](N)CCO UKAUYVFTDYCKQA-VKHMYHEASA-N 0.000 description 1
• KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
• FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
• UCUNFLYVYCGDHP-BYPYZUCNSA-N L-methionine sulfone Chemical compound CS(=O)(=O)CC[C@H](N)C(O)=O UCUNFLYVYCGDHP-BYPYZUCNSA-N 0.000 description 1
• SNDPXSYFESPGGJ-UHFFFAOYSA-N L-norVal-OH Natural products CCCC(N)C(O)=O SNDPXSYFESPGGJ-UHFFFAOYSA-N 0.000 description 1
• DGYHPLMPMRKMPD-UHFFFAOYSA-N L-propargyl glycine Natural products OC(=O)C(N)CC#C DGYHPLMPMRKMPD-UHFFFAOYSA-N 0.000 description 1
• 239000005517 L01XE01 - Imatinib Substances 0.000 description 1
• 239000005411 L01XE02 - Gefitinib Substances 0.000 description 1
• 239000002147 L01XE04 - Sunitinib Substances 0.000 description 1
• JLERVPBPJHKRBJ-UHFFFAOYSA-N LY 117018 Chemical compound C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCC3)=CC=2)C2=CC=C(O)C=C2S1 JLERVPBPJHKRBJ-UHFFFAOYSA-N 0.000 description 1
• JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
• 229920001491 Lentinan Polymers 0.000 description 1
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
• GQYIWUVLTXOXAJ-UHFFFAOYSA-N Lomustine Chemical compound ClCCN(N=O)C(=O)NC1CCCCC1 GQYIWUVLTXOXAJ-UHFFFAOYSA-N 0.000 description 1
• DDWFXDSYGUXRAY-UHFFFAOYSA-N Luciferin Natural products CCc1c(C)c(CC2NC(=O)C(=C2C=C)C)[nH]c1Cc3[nH]c4C(=C5/NC(CC(=O)O)C(C)C5CC(=O)O)CC(=O)c4c3C DDWFXDSYGUXRAY-UHFFFAOYSA-N 0.000 description 1
• 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
• 206010025323 Lymphomas Diseases 0.000 description 1
• KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
• 239000004472 Lysine Substances 0.000 description 1
• 239000004907 Macro-emulsion Substances 0.000 description 1
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
• 235000019759 Maize starch Nutrition 0.000 description 1
• 206010064912 Malignant transformation Diseases 0.000 description 1
• VJRAUFKOOPNFIQ-UHFFFAOYSA-N Marcellomycin Natural products C12=C(O)C=3C(=O)C4=C(O)C=CC(O)=C4C(=O)C=3C=C2C(C(=O)OC)C(CC)(O)CC1OC(OC1C)CC(N(C)C)C1OC(OC1C)CC(O)C1OC1CC(O)C(O)C(C)O1 VJRAUFKOOPNFIQ-UHFFFAOYSA-N 0.000 description 1
• 229930126263 Maytansine Natural products 0.000 description 1
• 238000003820 Medium-pressure liquid chromatography Methods 0.000 description 1
• IVDYZAAPOLNZKG-KWHRADDSSA-N Mepitiostane Chemical compound O([C@@H]1[C@]2(CC[C@@H]3[C@@]4(C)C[C@H]5S[C@H]5C[C@@H]4CC[C@H]3[C@@H]2CC1)C)C1(OC)CCCC1 IVDYZAAPOLNZKG-KWHRADDSSA-N 0.000 description 1
• 206010027476 Metastases Diseases 0.000 description 1
• VFKZTMPDYBFSTM-KVTDHHQDSA-N Mitobronitol Chemical compound BrC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CBr VFKZTMPDYBFSTM-KVTDHHQDSA-N 0.000 description 1
• 229930192392 Mitomycin Natural products 0.000 description 1
• HRHKSTOGXBBQCB-UHFFFAOYSA-N Mitomycin E Natural products O=C1C(N)=C(C)C(=O)C2=C1C(COC(N)=O)C1(OC)C3N(C)C3CN12 HRHKSTOGXBBQCB-UHFFFAOYSA-N 0.000 description 1
• 241000699666 Mus <mouse, genus> Species 0.000 description 1
• 241000699670 Mus sp. Species 0.000 description 1
• HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 1
• JDHILDINMRGULE-LURJTMIESA-N N(pros)-methyl-L-histidine Chemical compound CN1C=NC=C1C[C@H](N)C(O)=O JDHILDINMRGULE-LURJTMIESA-N 0.000 description 1
• KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
• OVBPIULPVIDEAO-UHFFFAOYSA-N N-Pteroyl-L-glutaminsaeure Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-UHFFFAOYSA-N 0.000 description 1
• WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
• AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
• GDFAOVXKHJXLEI-VKHMYHEASA-N N-methyl-L-alanine Chemical compound C[NH2+][C@@H](C)C([O-])=O GDFAOVXKHJXLEI-VKHMYHEASA-N 0.000 description 1
• 229910002651 NO3 Inorganic materials 0.000 description 1
• RHGKLRLOHDJJDR-UHFFFAOYSA-N Ndelta-carbamoyl-DL-ornithine Natural products OC(=O)C(N)CCCNC(N)=O RHGKLRLOHDJJDR-UHFFFAOYSA-N 0.000 description 1
• 206010029350 Neurotoxicity Diseases 0.000 description 1
• NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
• SYNHCENRCUAUNM-UHFFFAOYSA-N Nitrogen mustard N-oxide hydrochloride Chemical compound Cl.ClCC[N+]([O-])(C)CCCl SYNHCENRCUAUNM-UHFFFAOYSA-N 0.000 description 1
• KGTDRFCXGRULNK-UHFFFAOYSA-N Nogalamycin Natural products COC1C(OC)(C)C(OC)C(C)OC1OC1C2=C(O)C(C(=O)C3=C(O)C=C4C5(C)OC(C(C(C5O)N(C)C)O)OC4=C3C3=O)=C3C=C2C(C(=O)OC)C(C)(O)C1 KGTDRFCXGRULNK-UHFFFAOYSA-N 0.000 description 1
• 239000006057 Non-nutritive feed additive Substances 0.000 description 1
• QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 description 1
• BZQFBWGGLXLEPQ-UHFFFAOYSA-N O-phosphoryl-L-serine Natural products OC(=O)C(N)COP(O)(O)=O BZQFBWGGLXLEPQ-UHFFFAOYSA-N 0.000 description 1
• 239000005642 Oleic acid Substances 0.000 description 1
• ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
• 229930187135 Olivomycin Natural products 0.000 description 1
• AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 1
• UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 description 1
• 206010033128 Ovarian cancer Diseases 0.000 description 1
• 206010061535 Ovarian neoplasm Diseases 0.000 description 1
• 229910020667 PBr3 Inorganic materials 0.000 description 1
• 229940116355 PI3 kinase inhibitor Drugs 0.000 description 1
• 239000012828 PI3K inhibitor Substances 0.000 description 1
• VREZDOWOLGNDPW-ALTGWBOUSA-N Pancratistatin Chemical compound C1=C2[C@H]3[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)[C@@H]3NC(=O)C2=C(O)C2=C1OCO2 VREZDOWOLGNDPW-ALTGWBOUSA-N 0.000 description 1
• VREZDOWOLGNDPW-MYVCAWNPSA-N Pancratistatin Natural products O=C1N[C@H]2[C@H](O)[C@H](O)[C@H](O)[C@H](O)[C@@H]2c2c1c(O)c1OCOc1c2 VREZDOWOLGNDPW-MYVCAWNPSA-N 0.000 description 1
• 206010061902 Pancreatic neoplasm Diseases 0.000 description 1
• 208000018737 Parkinson disease Diseases 0.000 description 1
• 229910002666 PdCl2 Inorganic materials 0.000 description 1
• 241001494479 Pecora Species 0.000 description 1
• 108010057150 Peplomycin Proteins 0.000 description 1
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
• KMSKQZKKOZQFFG-HSUXVGOQSA-N Pirarubicin Chemical compound O([C@H]1[C@@H](N)C[C@@H](O[C@H]1C)O[C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1CCCCO1 KMSKQZKKOZQFFG-HSUXVGOQSA-N 0.000 description 1
• 229920002556 Polyethylene Glycol 300 Polymers 0.000 description 1
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
• HFVNWDWLWUCIHC-GUPDPFMOSA-N Prednimustine Chemical compound O=C([C@@]1(O)CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)[C@@H](O)C[C@@]21C)COC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 HFVNWDWLWUCIHC-GUPDPFMOSA-N 0.000 description 1
• 206010060862 Prostate cancer Diseases 0.000 description 1
• 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
• 102100024924 Protein kinase C alpha type Human genes 0.000 description 1
• 101710109947 Protein kinase C alpha type Proteins 0.000 description 1
• 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 1
• 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 1
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Natural products C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 1
• 102100030086 Receptor tyrosine-protein kinase erbB-2 Human genes 0.000 description 1
• 208000015634 Rectal Neoplasms Diseases 0.000 description 1
• OWPCHSCAPHNHAV-UHFFFAOYSA-N Rhizoxin Natural products C1C(O)C2(C)OC2C=CC(C)C(OC(=O)C2)CC2CC2OC2C(=O)OC1C(C)C(OC)C(C)=CC=CC(C)=CC1=COC(C)=N1 OWPCHSCAPHNHAV-UHFFFAOYSA-N 0.000 description 1
• NSFWWJIQIKBZMJ-YKNYLIOZSA-N Roridin A Chemical compound C([C@]12[C@]3(C)[C@H]4C[C@H]1O[C@@H]1C=C(C)CC[C@@]13COC(=O)[C@@H](O)[C@H](C)CCO[C@H](\C=C\C=C/C(=O)O4)[C@H](O)C)O2 NSFWWJIQIKBZMJ-YKNYLIOZSA-N 0.000 description 1
• 101100456541 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) MEC3 gene Proteins 0.000 description 1
• 101100483663 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) UFD1 gene Proteins 0.000 description 1
• 206010061934 Salivary gland cancer Diseases 0.000 description 1
• 108010077895 Sarcosine Proteins 0.000 description 1
• 201000010208 Seminoma Diseases 0.000 description 1
• 102000007562 Serum Albumin Human genes 0.000 description 1
• 108010071390 Serum Albumin Proteins 0.000 description 1
• 229920000519 Sizofiran Polymers 0.000 description 1
• 206010041067 Small cell lung cancer Diseases 0.000 description 1
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
• VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
• DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
• 229920002472 Starch Polymers 0.000 description 1
• 235000021355 Stearic acid Nutrition 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
• 241000282887 Suidae Species 0.000 description 1
• BXFOFFBJRFZBQZ-QYWOHJEZSA-N T-2 toxin Chemical compound C([C@@]12[C@]3(C)[C@H](OC(C)=O)[C@@H](O)[C@H]1O[C@H]1[C@]3(COC(C)=O)C[C@@H](C(=C1)C)OC(=O)CC(C)C)O2 BXFOFFBJRFZBQZ-QYWOHJEZSA-N 0.000 description 1
• 229920002253 Tannate Polymers 0.000 description 1
• CGMTUJFWROPELF-UHFFFAOYSA-N Tenuazonic acid Natural products CCC(C)C1NC(=O)C(=C(C)/O)C1=O CGMTUJFWROPELF-UHFFFAOYSA-N 0.000 description 1
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
• 208000024770 Thyroid neoplasm Diseases 0.000 description 1
• 101710183280 Topoisomerase Proteins 0.000 description 1
• IWEQQRMGNVVKQW-OQKDUQJOSA-N Toremifene citrate Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C1=CC(OCCN(C)C)=CC=C1C(\C=1C=CC=CC=1)=C(\CCCl)C1=CC=CC=C1 IWEQQRMGNVVKQW-OQKDUQJOSA-N 0.000 description 1
• 206010044221 Toxic encephalopathy Diseases 0.000 description 1
• HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 description 1
• UMILHIMHKXVDGH-UHFFFAOYSA-N Triethylene glycol diglycidyl ether Chemical compound C1OC1COCCOCCOCCOCC1CO1 UMILHIMHKXVDGH-UHFFFAOYSA-N 0.000 description 1
• FYAMXEPQQLNQDM-UHFFFAOYSA-N Tris(1-aziridinyl)phosphine oxide Chemical compound C1CN1P(N1CC1)(=O)N1CC1 FYAMXEPQQLNQDM-UHFFFAOYSA-N 0.000 description 1
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 1
• 208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 1
• 102000005789 Vascular Endothelial Growth Factors Human genes 0.000 description 1
• 108010019530 Vascular Endothelial Growth Factors Proteins 0.000 description 1
• JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 description 1
• 206010047741 Vulval cancer Diseases 0.000 description 1
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
• SPJCRMJCFSJKDE-ZWBUGVOYSA-N [(3s,8s,9s,10r,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-yl] 2-[4-[bis(2-chloroethyl)amino]phenyl]acetate Chemical compound O([C@@H]1CC2=CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)C(=O)CC1=CC=C(N(CCCl)CCCl)C=C1 SPJCRMJCFSJKDE-ZWBUGVOYSA-N 0.000 description 1
• IFJUINDAXYAPTO-UUBSBJJBSA-N [(8r,9s,13s,14s,17s)-17-[2-[4-[4-[bis(2-chloroethyl)amino]phenyl]butanoyloxy]acetyl]oxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] benzoate Chemical compound C([C@@H]1[C@@H](C2=CC=3)CC[C@]4([C@H]1CC[C@@H]4OC(=O)COC(=O)CCCC=1C=CC(=CC=1)N(CCCl)CCCl)C)CC2=CC=3OC(=O)C1=CC=CC=C1 IFJUINDAXYAPTO-UUBSBJJBSA-N 0.000 description 1
• IHGLINDYFMDHJG-UHFFFAOYSA-N [2-(4-methoxyphenyl)-3,4-dihydronaphthalen-1-yl]-[4-(2-pyrrolidin-1-ylethoxy)phenyl]methanone Chemical compound C1=CC(OC)=CC=C1C(CCC1=CC=CC=C11)=C1C(=O)C(C=C1)=CC=C1OCCN1CCCC1 IHGLINDYFMDHJG-UHFFFAOYSA-N 0.000 description 1
• XZSRRNFBEIOBDA-CFNBKWCHSA-N [2-[(2s,4s)-4-[(2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1h-tetracen-2-yl]-2-oxoethyl] 2,2-diethoxyacetate Chemical compound O([C@H]1C[C@](CC2=C(O)C=3C(=O)C4=CC=CC(OC)=C4C(=O)C=3C(O)=C21)(O)C(=O)COC(=O)C(OCC)OCC)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 XZSRRNFBEIOBDA-CFNBKWCHSA-N 0.000 description 1
• AIWRTTMUVOZGPW-HSPKUQOVSA-N abarelix Chemical compound C([C@@H](C(=O)N[C@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCNC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N[C@H](C)C(N)=O)N(C)C(=O)[C@H](CO)NC(=O)[C@@H](CC=1C=NC=CC=1)NC(=O)[C@@H](CC=1C=CC(Cl)=CC=1)NC(=O)[C@@H](CC=1C=C2C=CC=CC2=CC=1)NC(C)=O)C1=CC=C(O)C=C1 AIWRTTMUVOZGPW-HSPKUQOVSA-N 0.000 description 1
• 108010023617 abarelix Proteins 0.000 description 1
• 229960002184 abarelix Drugs 0.000 description 1
• 230000001594 aberrant effect Effects 0.000 description 1
• 230000002159 abnormal effect Effects 0.000 description 1
• 239000002250 absorbent Substances 0.000 description 1
• 230000002745 absorbent Effects 0.000 description 1
• 235000010489 acacia gum Nutrition 0.000 description 1
• ZOZKYEHVNDEUCO-XUTVFYLZSA-N aceglatone Chemical compound O1C(=O)[C@H](OC(C)=O)[C@@H]2OC(=O)[C@@H](OC(=O)C)[C@@H]21 ZOZKYEHVNDEUCO-XUTVFYLZSA-N 0.000 description 1
• 229950002684 aceglatone Drugs 0.000 description 1
• 239000008351 acetate buffer Substances 0.000 description 1
• VJHCJDRQFCCTHL-UHFFFAOYSA-N acetic acid 2,3,4,5,6-pentahydroxyhexanal Chemical compound CC(O)=O.OCC(O)C(O)C(O)C(O)C=O VJHCJDRQFCCTHL-UHFFFAOYSA-N 0.000 description 1
• DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
• CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 1
• 229930183665 actinomycin Natural products 0.000 description 1
• RJURFGZVJUQBHK-IIXSONLDSA-N actinomycin D Chemical compound C[C@H]1OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@@H]2CCCN2C(=O)[C@@H](C(C)C)NC(=O)[C@H]1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)N[C@@H]4C(=O)N[C@@H](C(N5CCC[C@H]5C(=O)N(C)CC(=O)N(C)[C@@H](C(C)C)C(=O)O[C@@H]4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-IIXSONLDSA-N 0.000 description 1
• 230000003213 activating effect Effects 0.000 description 1
• 239000008186 active pharmaceutical agent Substances 0.000 description 1
• 230000010933 acylation Effects 0.000 description 1
• 238000005917 acylation reaction Methods 0.000 description 1
• 125000005042 acyloxymethyl group Chemical group 0.000 description 1
• 239000000654 additive Substances 0.000 description 1
• 229950004955 adozelesin Drugs 0.000 description 1
• BYRVKDUQDLJUBX-JJCDCTGGSA-N adozelesin Chemical compound C1=CC=C2OC(C(=O)NC=3C=C4C=C(NC4=CC=3)C(=O)N3C[C@H]4C[C@]44C5=C(C(C=C43)=O)NC=C5C)=CC2=C1 BYRVKDUQDLJUBX-JJCDCTGGSA-N 0.000 description 1
• 210000004100 adrenal gland Anatomy 0.000 description 1
• 229940009456 adriamycin Drugs 0.000 description 1
• 239000003463 adsorbent Substances 0.000 description 1
• 230000002411 adverse Effects 0.000 description 1
• 239000000443 aerosol Substances 0.000 description 1
• 125000003158 alcohol group Chemical group 0.000 description 1
• 108700025316 aldesleukin Proteins 0.000 description 1
• 235000010443 alginic acid Nutrition 0.000 description 1
• 239000000783 alginic acid Substances 0.000 description 1
• 229920000615 alginic acid Polymers 0.000 description 1
• 229960001126 alginic acid Drugs 0.000 description 1
• 150000004781 alginic acids Chemical class 0.000 description 1
• 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
• 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
• 125000005206 alkoxycarbonyloxymethyl group Chemical group 0.000 description 1
• 150000003973 alkyl amines Chemical class 0.000 description 1
• 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
• 150000008052 alkyl sulfonates Chemical class 0.000 description 1
• 229940100198 alkylating agent Drugs 0.000 description 1
• 239000002168 alkylating agent Substances 0.000 description 1
• 125000002947 alkylene group Chemical group 0.000 description 1
• SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 description 1
• 229940061720 alpha hydroxy acid Drugs 0.000 description 1
• 150000001280 alpha hydroxy acids Chemical class 0.000 description 1
• HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 description 1
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
• 229960000473 altretamine Drugs 0.000 description 1
• 229910052782 aluminium Inorganic materials 0.000 description 1
• XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
• 229960002749 aminolevulinic acid Drugs 0.000 description 1
• 229960003896 aminopterin Drugs 0.000 description 1
• 229940025084 amphetamine Drugs 0.000 description 1
• 229960001220 amsacrine Drugs 0.000 description 1
• XCPGHVQEEXUHNC-UHFFFAOYSA-N amsacrine Chemical compound COC1=CC(NS(C)(=O)=O)=CC=C1NC1=C(C=CC=C2)C2=NC2=CC=CC=C12 XCPGHVQEEXUHNC-UHFFFAOYSA-N 0.000 description 1
• 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 1
• 201000007538 anal carcinoma Diseases 0.000 description 1
• 229960002932 anastrozole Drugs 0.000 description 1
• BBDAGFIXKZCXAH-CCXZUQQUSA-N ancitabine Chemical compound N=C1C=CN2[C@@H]3O[C@H](CO)[C@@H](O)[C@@H]3OC2=N1 BBDAGFIXKZCXAH-CCXZUQQUSA-N 0.000 description 1
• 229950000242 ancitabine Drugs 0.000 description 1
• 239000003098 androgen Substances 0.000 description 1
• 229940030486 androgens Drugs 0.000 description 1
• 239000004037 angiogenesis inhibitor Substances 0.000 description 1
• SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
• 230000002280 anti-androgenic effect Effects 0.000 description 1
• 229940046836 anti-estrogen Drugs 0.000 description 1
• 230000001833 anti-estrogenic effect Effects 0.000 description 1
• 230000000340 anti-metabolite Effects 0.000 description 1
• 239000000051 antiandrogen Substances 0.000 description 1
• 229940030495 antiandrogen sex hormone and modulator of the genital system Drugs 0.000 description 1
• 238000011319 anticancer therapy Methods 0.000 description 1
• 239000013059 antihormonal agent Substances 0.000 description 1
• 229940100197 antimetabolite Drugs 0.000 description 1
• 239000002256 antimetabolite Substances 0.000 description 1
• 229940045687 antimetabolites folic acid analogs Drugs 0.000 description 1
• 229940045719 antineoplastic alkylating agent nitrosoureas Drugs 0.000 description 1
• 229940041181 antineoplastic drug Drugs 0.000 description 1
• 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 description 1
• 239000000074 antisense oligonucleotide Substances 0.000 description 1
• 238000012230 antisense oligonucleotides Methods 0.000 description 1
• 239000008346 aqueous phase Substances 0.000 description 1
• 150000008209 arabinosides Chemical class 0.000 description 1
• 229940078010 arimidex Drugs 0.000 description 1
• 229940087620 aromasin Drugs 0.000 description 1
• 239000003886 aromatase inhibitor Substances 0.000 description 1
• 229940046844 aromatase inhibitors Drugs 0.000 description 1
• 125000005251 aryl acyl group Chemical group 0.000 description 1
• 229940072107 ascorbate Drugs 0.000 description 1
• 229960005070 ascorbic acid Drugs 0.000 description 1
• 229960001230 asparagine Drugs 0.000 description 1
• 235000009582 asparagine Nutrition 0.000 description 1
• 235000003704 aspartic acid Nutrition 0.000 description 1
• 229940120638 avastin Drugs 0.000 description 1
• 229960002756 azacitidine Drugs 0.000 description 1
• XTKDAFGWCDAMPY-UHFFFAOYSA-N azaperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCN(C=2N=CC=CC=2)CC1 XTKDAFGWCDAMPY-UHFFFAOYSA-N 0.000 description 1
• 229950011321 azaserine Drugs 0.000 description 1
• 125000002393 azetidinyl group Chemical group 0.000 description 1
• 150000001541 aziridines Chemical class 0.000 description 1
• 230000009286 beneficial effect Effects 0.000 description 1
• 229960000686 benzalkonium chloride Drugs 0.000 description 1
• 150000001555 benzenes Chemical class 0.000 description 1
• 229940077388 benzenesulfonate Drugs 0.000 description 1
• SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
• UREZNYTWGJKWBI-UHFFFAOYSA-M benzethonium chloride Chemical compound [Cl-].C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 UREZNYTWGJKWBI-UHFFFAOYSA-M 0.000 description 1
• 229960001950 benzethonium chloride Drugs 0.000 description 1
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
• 125000004601 benzofurazanyl group Chemical group N1=C2C(=NO1)C(=CC=C2)* 0.000 description 1
• 235000010233 benzoic acid Nutrition 0.000 description 1
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
• 235000019445 benzyl alcohol Nutrition 0.000 description 1
• CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
• WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
• 229940000635 beta-alanine Drugs 0.000 description 1
• OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
• 229960000397 bevacizumab Drugs 0.000 description 1
• 150000005347 biaryls Chemical class 0.000 description 1
• 229960000997 bicalutamide Drugs 0.000 description 1
• GPRLTFBKWDERLU-UHFFFAOYSA-N bicyclo[2.2.2]octane Chemical group C1CC2CCC1CC2 GPRLTFBKWDERLU-UHFFFAOYSA-N 0.000 description 1
• GNTFBMAGLFYMMZ-UHFFFAOYSA-N bicyclo[3.2.2]nonane Chemical group C1CC2CCC1CCC2 GNTFBMAGLFYMMZ-UHFFFAOYSA-N 0.000 description 1
• 108091008324 binding proteins Proteins 0.000 description 1
• 230000003115 biocidal effect Effects 0.000 description 1
• 230000004071 biological effect Effects 0.000 description 1
• 238000012925 biological evaluation Methods 0.000 description 1
• 230000033228 biological regulation Effects 0.000 description 1
• 239000012472 biological sample Substances 0.000 description 1
• 239000004305 biphenyl Chemical class 0.000 description 1
• 235000010290 biphenyl Nutrition 0.000 description 1
• HUTDDBSSHVOYJR-UHFFFAOYSA-H bis[(2-oxo-1,3,2$l^{5},4$l^{2}-dioxaphosphaplumbetan-2-yl)oxy]lead Chemical compound [Pb+2].[Pb+2].[Pb+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O HUTDDBSSHVOYJR-UHFFFAOYSA-H 0.000 description 1
• 229950008548 bisantrene Drugs 0.000 description 1
• 150000004663 bisphosphonates Chemical class 0.000 description 1
• 229950006844 bizelesin Drugs 0.000 description 1
• 201000001531 bladder carcinoma Diseases 0.000 description 1
• 201000000053 blastoma Diseases 0.000 description 1
• 230000000740 bleeding effect Effects 0.000 description 1
• OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical class N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 0.000 description 1
• 239000003114 blood coagulation factor Substances 0.000 description 1
• 230000037396 body weight Effects 0.000 description 1
• 229960001467 bortezomib Drugs 0.000 description 1
• RRKTZKIUPZVBMF-UHFFFAOYSA-N brucine Natural products C1=2C=C(OC)C(OC)=CC=2N(C(C2)=O)C3C(C4C5)C2OCC=C4CN2C5C31CC2 RRKTZKIUPZVBMF-UHFFFAOYSA-N 0.000 description 1
• RRKTZKIUPZVBMF-IBTVXLQLSA-N brucine Chemical compound O([C@@H]1[C@H]([C@H]2C3)[C@@H]4N(C(C1)=O)C=1C=C(C(=CC=11)OC)OC)CC=C2CN2[C@@H]3[C@]41CC2 RRKTZKIUPZVBMF-IBTVXLQLSA-N 0.000 description 1
• 229960005520 bryostatin Drugs 0.000 description 1
• MJQUEDHRCUIRLF-TVIXENOKSA-N bryostatin 1 Chemical compound C([C@@H]1CC(/[C@@H]([C@@](C(C)(C)/C=C/2)(O)O1)OC(=O)/C=C/C=C/CCC)=C\C(=O)OC)[C@H]([C@@H](C)O)OC(=O)C[C@H](O)C[C@@H](O1)C[C@H](OC(C)=O)C(C)(C)[C@]1(O)C[C@@H]1C\C(=C\C(=O)OC)C[C@H]\2O1 MJQUEDHRCUIRLF-TVIXENOKSA-N 0.000 description 1
• MUIWQCKLQMOUAT-AKUNNTHJSA-N bryostatin 20 Natural products COC(=O)C=C1C[C@@]2(C)C[C@]3(O)O[C@](C)(C[C@@H](O)CC(=O)O[C@](C)(C[C@@]4(C)O[C@](O)(CC5=CC(=O)O[C@]45C)C(C)(C)C=C[C@@](C)(C1)O2)[C@@H](C)O)C[C@H](OC(=O)C(C)(C)C)C3(C)C MUIWQCKLQMOUAT-AKUNNTHJSA-N 0.000 description 1
• 239000012512 bulk drug substance Substances 0.000 description 1
• 244000309464 bull Species 0.000 description 1
• MBABCNBNDNGODA-LUVUIASKSA-N bullatacin Chemical compound O1[C@@H]([C@@H](O)CCCCCCCCCC)CC[C@@H]1[C@@H]1O[C@@H]([C@H](O)CCCCCCCCCC[C@@H](O)CC=2C(O[C@@H](C)C=2)=O)CC1 MBABCNBNDNGODA-LUVUIASKSA-N 0.000 description 1
• 229960002092 busulfan Drugs 0.000 description 1
• DQXBYHZEEUGOBF-UHFFFAOYSA-N but-3-enoic acid;ethene Chemical compound C=C.OC(=O)CC=C DQXBYHZEEUGOBF-UHFFFAOYSA-N 0.000 description 1
• KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
• LRHPLDYGYMQRHN-UHFFFAOYSA-N butyl alcohol Substances CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 239000006227 byproduct Substances 0.000 description 1
• 108700002839 cactinomycin Proteins 0.000 description 1
• 229950009908 cactinomycin Drugs 0.000 description 1
• 239000011575 calcium Substances 0.000 description 1
• 229910052791 calcium Inorganic materials 0.000 description 1
• VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
• 229910000019 calcium carbonate Inorganic materials 0.000 description 1
• 239000001506 calcium phosphate Substances 0.000 description 1
• 229910000389 calcium phosphate Inorganic materials 0.000 description 1
• 235000011010 calcium phosphates Nutrition 0.000 description 1
• 229950009823 calusterone Drugs 0.000 description 1
• IVFYLRMMHVYGJH-PVPPCFLZSA-N calusterone Chemical compound C1C[C@]2(C)[C@](O)(C)CC[C@H]2[C@@H]2[C@@H](C)CC3=CC(=O)CC[C@]3(C)[C@H]21 IVFYLRMMHVYGJH-PVPPCFLZSA-N 0.000 description 1
• VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical compound C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 description 1
• 229940127093 camptothecin Drugs 0.000 description 1
• 239000003560 cancer drug Substances 0.000 description 1
• 230000005907 cancer growth Effects 0.000 description 1
• 229960004117 capecitabine Drugs 0.000 description 1
• 150000001721 carbon Chemical group 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
• YAYRGNWWLMLWJE-UHFFFAOYSA-L carboplatin Chemical compound O=C1O[Pt](N)(N)OC(=O)C11CCC1 YAYRGNWWLMLWJE-UHFFFAOYSA-L 0.000 description 1
• 229960004562 carboplatin Drugs 0.000 description 1
• 229960002115 carboquone Drugs 0.000 description 1
• 239000001768 carboxy methyl cellulose Substances 0.000 description 1
• UHBYWPGGCSDKFX-UHFFFAOYSA-N carboxyglutamic acid Chemical compound OC(=O)C(N)CC(C(O)=O)C(O)=O UHBYWPGGCSDKFX-UHFFFAOYSA-N 0.000 description 1
• 150000007942 carboxylates Chemical class 0.000 description 1
• 125000002843 carboxylic acid group Chemical group 0.000 description 1
• 150000001735 carboxylic acids Chemical class 0.000 description 1
• XREUEWVEMYWFFA-CSKJXFQVSA-N carminomycin Chemical compound C1[C@H](N)[C@H](O)[C@H](C)O[C@H]1O[C@@H]1C2=C(O)C(C(=O)C3=C(O)C=CC=C3C3=O)=C3C(O)=C2C[C@@](O)(C(C)=O)C1 XREUEWVEMYWFFA-CSKJXFQVSA-N 0.000 description 1
• 229930188550 carminomycin Natural products 0.000 description 1
• XREUEWVEMYWFFA-UHFFFAOYSA-N carminomycin I Natural products C1C(N)C(O)C(C)OC1OC1C2=C(O)C(C(=O)C3=C(O)C=CC=C3C3=O)=C3C(O)=C2CC(O)(C(C)=O)C1 XREUEWVEMYWFFA-UHFFFAOYSA-N 0.000 description 1
• 229960003261 carmofur Drugs 0.000 description 1
• 229960005243 carmustine Drugs 0.000 description 1
• 239000012876 carrier material Substances 0.000 description 1
• 229950001725 carubicin Drugs 0.000 description 1
• BBZDXMBRAFTCAA-AREMUKBSSA-N carzelesin Chemical compound C1=2NC=C(C)C=2C([C@H](CCl)CN2C(=O)C=3NC4=CC=C(C=C4C=3)NC(=O)C3=CC4=CC=C(C=C4O3)N(CC)CC)=C2C=C1OC(=O)NC1=CC=CC=C1 BBZDXMBRAFTCAA-AREMUKBSSA-N 0.000 description 1
• 229950007509 carzelesin Drugs 0.000 description 1
• 108010047060 carzinophilin Proteins 0.000 description 1
• 239000006143 cell culture medium Substances 0.000 description 1
• 230000006037 cell lysis Effects 0.000 description 1
• 230000004663 cell proliferation Effects 0.000 description 1
• 230000003833 cell viability Effects 0.000 description 1
• 230000005754 cellular signaling Effects 0.000 description 1
• 206010008118 cerebral infarction Diseases 0.000 description 1
• 201000010881 cervical cancer Diseases 0.000 description 1
• 229940082500 cetostearyl alcohol Drugs 0.000 description 1
• 230000008859 change Effects 0.000 description 1
• 238000001311 chemical methods and process Methods 0.000 description 1
• 239000007795 chemical reaction product Substances 0.000 description 1
• 230000000973 chemotherapeutic effect Effects 0.000 description 1
• 238000002512 chemotherapy Methods 0.000 description 1
• 238000004296 chiral HPLC Methods 0.000 description 1
• 229960004630 chlorambucil Drugs 0.000 description 1
• JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 description 1
• 229910052801 chlorine Inorganic materials 0.000 description 1
• 239000000460 chlorine Chemical group 0.000 description 1
• 229950008249 chlornaphazine Drugs 0.000 description 1
• 229960001480 chlorozotocin Drugs 0.000 description 1
• 235000013985 cinnamic acid Nutrition 0.000 description 1
• 229930016911 cinnamic acid Natural products 0.000 description 1
• 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
• 238000002983 circular dichroism Methods 0.000 description 1
• 229960004316 cisplatin Drugs 0.000 description 1
• DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 1
• 229940001468 citrate Drugs 0.000 description 1
• 229960002173 citrulline Drugs 0.000 description 1
• 235000013477 citrulline Nutrition 0.000 description 1
• ACSIXWWBWUQEHA-UHFFFAOYSA-N clodronic acid Chemical compound OP(O)(=O)C(Cl)(Cl)P(O)(O)=O ACSIXWWBWUQEHA-UHFFFAOYSA-N 0.000 description 1
• 229960002286 clodronic acid Drugs 0.000 description 1
• 238000005354 coacervation Methods 0.000 description 1
• 229940110456 cocoa butter Drugs 0.000 description 1
• 235000019868 cocoa butter Nutrition 0.000 description 1
• 208000029742 colonic neoplasm Diseases 0.000 description 1
• 230000000295 complement effect Effects 0.000 description 1
• 238000010668 complexation reaction Methods 0.000 description 1
• 239000007891 compressed tablet Substances 0.000 description 1
• 208000010247 contact dermatitis Diseases 0.000 description 1
• 238000013270 controlled release Methods 0.000 description 1
• 238000007796 conventional method Methods 0.000 description 1
• 239000012084 conversion product Substances 0.000 description 1
• 229910052802 copper Inorganic materials 0.000 description 1
• 239000010949 copper Substances 0.000 description 1
• 239000006184 cosolvent Substances 0.000 description 1
• 229960005168 croscarmellose Drugs 0.000 description 1
• 239000001767 crosslinked sodium carboxy methyl cellulose Substances 0.000 description 1
• 150000003983 crown ethers Chemical class 0.000 description 1
• PSNOPSMXOBPNNV-VVCTWANISA-N cryptophycin 1 Chemical compound C1=C(Cl)C(OC)=CC=C1C[C@@H]1C(=O)NC[C@@H](C)C(=O)O[C@@H](CC(C)C)C(=O)O[C@H]([C@H](C)[C@@H]2[C@H](O2)C=2C=CC=CC=2)C/C=C/C(=O)N1 PSNOPSMXOBPNNV-VVCTWANISA-N 0.000 description 1
• 108010089438 cryptophycin 1 Proteins 0.000 description 1
• 108010090203 cryptophycin 8 Proteins 0.000 description 1
• PSNOPSMXOBPNNV-UHFFFAOYSA-N cryptophycin-327 Natural products C1=C(Cl)C(OC)=CC=C1CC1C(=O)NCC(C)C(=O)OC(CC(C)C)C(=O)OC(C(C)C2C(O2)C=2C=CC=CC=2)CC=CC(=O)N1 PSNOPSMXOBPNNV-UHFFFAOYSA-N 0.000 description 1
• 238000002425 crystallisation Methods 0.000 description 1
• 230000008025 crystallization Effects 0.000 description 1
• 238000012258 culturing Methods 0.000 description 1
• 125000004122 cyclic group Chemical group 0.000 description 1
• 108010011222 cyclo(Arg-Pro) Proteins 0.000 description 1
• 125000000753 cycloalkyl group Chemical group 0.000 description 1
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 1
• HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 229960004397 cyclophosphamide Drugs 0.000 description 1
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
• 229960000684 cytarabine Drugs 0.000 description 1
• 229940104302 cytosine Drugs 0.000 description 1
• 239000000824 cytostatic agent Substances 0.000 description 1
• 239000002254 cytotoxic agent Substances 0.000 description 1
• 231100000599 cytotoxic agent Toxicity 0.000 description 1
• 230000003013 cytotoxicity Effects 0.000 description 1
• 231100000135 cytotoxicity Toxicity 0.000 description 1
• KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 1
• 229960003901 dacarbazine Drugs 0.000 description 1
• 229960000640 dactinomycin Drugs 0.000 description 1
• 229960000975 daunorubicin Drugs 0.000 description 1
• 230000001934 delay Effects 0.000 description 1
• YSMODUONRAFBET-UHFFFAOYSA-N delta-DL-hydroxylysine Natural products NCC(O)CCC(N)C(O)=O YSMODUONRAFBET-UHFFFAOYSA-N 0.000 description 1
• 229960005052 demecolcine Drugs 0.000 description 1
• 230000001419 dependent effect Effects 0.000 description 1
• 238000010511 deprotection reaction Methods 0.000 description 1
• 238000001212 derivatisation Methods 0.000 description 1
• 231100000223 dermal penetration Toxicity 0.000 description 1
• 238000001514 detection method Methods 0.000 description 1
• 229950003913 detorubicin Drugs 0.000 description 1
• 229910052805 deuterium Inorganic materials 0.000 description 1
• 238000011161 development Methods 0.000 description 1
• 229950006137 dexfosfoserine Drugs 0.000 description 1
• 235000019425 dextrin Nutrition 0.000 description 1
• 125000004663 dialkyl amino group Chemical group 0.000 description 1
• 125000002576 diazepinyl group Chemical group N1N=C(C=CC=C1)* 0.000 description 1
• WVYXNIXAMZOZFK-UHFFFAOYSA-N diaziquone Chemical compound O=C1C(NC(=O)OCC)=C(N2CC2)C(=O)C(NC(=O)OCC)=C1N1CC1 WVYXNIXAMZOZFK-UHFFFAOYSA-N 0.000 description 1
• 229950002389 diaziquone Drugs 0.000 description 1
• 229960004132 diethyl ether Drugs 0.000 description 1
• 125000005057 dihydrothienyl group Chemical group S1C(CC=C1)* 0.000 description 1
• 238000007865 diluting Methods 0.000 description 1
• IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
• XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
• PSHRANCNVXNITH-UHFFFAOYSA-N dimethylamino acetate Chemical compound CN(C)OC(C)=O PSHRANCNVXNITH-UHFFFAOYSA-N 0.000 description 1
• IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
• 108700003601 dimethylglycine Proteins 0.000 description 1
• 125000000532 dioxanyl group Chemical group 0.000 description 1
• MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 1
• 150000002016 disaccharides Chemical class 0.000 description 1
• 208000037765 diseases and disorders Diseases 0.000 description 1
• 239000006185 dispersion Substances 0.000 description 1
• 238000004090 dissolution Methods 0.000 description 1
• 125000005883 dithianyl group Chemical group 0.000 description 1
• 125000005411 dithiolanyl group Chemical group S1SC(CC1)* 0.000 description 1
• VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 description 1
• PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 description 1
• 239000003534 dna topoisomerase inhibitor Substances 0.000 description 1
• 229960003668 docetaxel Drugs 0.000 description 1
• AMRJKAQTDDKMCE-UHFFFAOYSA-N dolastatin Chemical compound CC(C)C(N(C)C)C(=O)NC(C(C)C)C(=O)N(C)C(C(C)C)C(OC)CC(=O)N1CCCC1C(OC)C(C)C(=O)NC(C=1SC=CN=1)CC1=CC=CC=C1 AMRJKAQTDDKMCE-UHFFFAOYSA-N 0.000 description 1
• 229930188854 dolastatin Natural products 0.000 description 1
• ZWAOHEXOSAUJHY-ZIYNGMLESA-N doxifluridine Chemical compound O[C@@H]1[C@H](O)[C@@H](C)O[C@H]1N1C(=O)NC(=O)C(F)=C1 ZWAOHEXOSAUJHY-ZIYNGMLESA-N 0.000 description 1
• 229950005454 doxifluridine Drugs 0.000 description 1
• 229960004679 doxorubicin Drugs 0.000 description 1
• 229950004203 droloxifene Drugs 0.000 description 1
• NOTIQUSPUUHHEH-UXOVVSIBSA-N dromostanolone propionate Chemical compound C([C@@H]1CC2)C(=O)[C@H](C)C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](OC(=O)CC)[C@@]2(C)CC1 NOTIQUSPUUHHEH-UXOVVSIBSA-N 0.000 description 1
• 229950004683 drostanolone propionate Drugs 0.000 description 1
• 238000009510 drug design Methods 0.000 description 1
• 230000036267 drug metabolism Effects 0.000 description 1
• 229960005501 duocarmycin Drugs 0.000 description 1
• VQNATVDKACXKTF-XELLLNAOSA-N duocarmycin Chemical compound COC1=C(OC)C(OC)=C2NC(C(=O)N3C4=CC(=O)C5=C([C@@]64C[C@@H]6C3)C=C(N5)C(=O)OC)=CC2=C1 VQNATVDKACXKTF-XELLLNAOSA-N 0.000 description 1
• 229930184221 duocarmycin Natural products 0.000 description 1
• AFMYMMXSQGUCBK-AKMKHHNQSA-N dynemicin a Chemical compound C1#C\C=C/C#C[C@@H]2NC(C=3C(=O)C4=C(O)C=CC(O)=C4C(=O)C=3C(O)=C3)=C3[C@@]34O[C@]32[C@@H](C)C(C(O)=O)=C(OC)[C@H]41 AFMYMMXSQGUCBK-AKMKHHNQSA-N 0.000 description 1
• FSIRXIHZBIXHKT-MHTVFEQDSA-N edatrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CC(CC)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FSIRXIHZBIXHKT-MHTVFEQDSA-N 0.000 description 1
• 229950006700 edatrexate Drugs 0.000 description 1
• 230000002526 effect on cardiovascular system Effects 0.000 description 1
• VLCYCQAOQCDTCN-UHFFFAOYSA-N eflornithine Chemical compound NCCCC(N)(C(F)F)C(O)=O VLCYCQAOQCDTCN-UHFFFAOYSA-N 0.000 description 1
• 229960002759 eflornithine Drugs 0.000 description 1
• 229920001971 elastomer Polymers 0.000 description 1
• 238000001962 electrophoresis Methods 0.000 description 1
• XOPYFXBZMVTEJF-PDACKIITSA-N eleutherobin Chemical compound C(/[C@H]1[C@H](C(=CC[C@@H]1C(C)C)C)C[C@@H]([C@@]1(C)O[C@@]2(C=C1)OC)OC(=O)\C=C\C=1N=CN(C)C=1)=C2\CO[C@@H]1OC[C@@H](O)[C@@H](O)[C@@H]1OC(C)=O XOPYFXBZMVTEJF-PDACKIITSA-N 0.000 description 1
• XOPYFXBZMVTEJF-UHFFFAOYSA-N eleutherobin Natural products C1=CC2(OC)OC1(C)C(OC(=O)C=CC=1N=CN(C)C=1)CC(C(=CCC1C(C)C)C)C1C=C2COC1OCC(O)C(O)C1OC(C)=O XOPYFXBZMVTEJF-UHFFFAOYSA-N 0.000 description 1
• 229950000549 elliptinium acetate Drugs 0.000 description 1
• 229940120655 eloxatin Drugs 0.000 description 1
• 201000008184 embryoma Diseases 0.000 description 1
• 230000001804 emulsifying effect Effects 0.000 description 1
• 239000008387 emulsifying waxe Substances 0.000 description 1
• 201000003914 endometrial carcinoma Diseases 0.000 description 1
• 239000003623 enhancer Substances 0.000 description 1
• JOZGNYDSEBIJDH-UHFFFAOYSA-N eniluracil Chemical compound O=C1NC=C(C#C)C(=O)N1 JOZGNYDSEBIJDH-UHFFFAOYSA-N 0.000 description 1
• 229950010213 eniluracil Drugs 0.000 description 1
• 229950011487 enocitabine Drugs 0.000 description 1
• 229940088598 enzyme Drugs 0.000 description 1
• 229960002179 ephedrine Drugs 0.000 description 1
• 229960001904 epirubicin Drugs 0.000 description 1
• 229950002973 epitiostanol Drugs 0.000 description 1
• 229930013356 epothilone Natural products 0.000 description 1
• 150000003883 epothilone derivatives Chemical class 0.000 description 1
• 229960001433 erlotinib Drugs 0.000 description 1
• YSMODUONRAFBET-UHNVWZDZSA-N erythro-5-hydroxy-L-lysine Chemical compound NC[C@H](O)CC[C@H](N)C(O)=O YSMODUONRAFBET-UHNVWZDZSA-N 0.000 description 1
• ITSGNOIFAJAQHJ-BMFNZSJVSA-N esorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)C[C@H](C)O1 ITSGNOIFAJAQHJ-BMFNZSJVSA-N 0.000 description 1
• 229950002017 esorubicin Drugs 0.000 description 1
• LJQQFQHBKUKHIS-WJHRIEJJSA-N esperamicin Chemical compound O1CC(NC(C)C)C(OC)CC1OC1C(O)C(NOC2OC(C)C(SC)C(O)C2)C(C)OC1OC1C(\C2=C/CSSSC)=C(NC(=O)OC)C(=O)C(OC3OC(C)C(O)C(OC(=O)C=4C(=CC(OC)=C(OC)C=4)NC(=O)C(=C)OC)C3)C2(O)C#C\C=C/C#C1 LJQQFQHBKUKHIS-WJHRIEJJSA-N 0.000 description 1
• FRPJXPJMRWBBIH-RBRWEJTLSA-N estramustine Chemical compound ClCCN(CCCl)C(=O)OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 FRPJXPJMRWBBIH-RBRWEJTLSA-N 0.000 description 1
• 229960001842 estramustine Drugs 0.000 description 1
• 229940011871 estrogen Drugs 0.000 description 1
• 239000000262 estrogen Substances 0.000 description 1
• 239000000328 estrogen antagonist Substances 0.000 description 1
• 229940052303 ethers for general anesthesia Drugs 0.000 description 1
• QSRLNKCNOLVZIR-KRWDZBQOSA-N ethyl (2s)-2-[[2-[4-[bis(2-chloroethyl)amino]phenyl]acetyl]amino]-4-methylsulfanylbutanoate Chemical compound CCOC(=O)[C@H](CCSC)NC(=O)CC1=CC=C(N(CCCl)CCCl)C=C1 QSRLNKCNOLVZIR-KRWDZBQOSA-N 0.000 description 1
• 238000003810 ethyl acetate extraction Methods 0.000 description 1
• 239000005038 ethylene vinyl acetate Substances 0.000 description 1
• 125000005469 ethylenyl group Chemical group 0.000 description 1
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
• 229960005237 etoglucid Drugs 0.000 description 1
• VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 description 1
• 230000007717 exclusion Effects 0.000 description 1
• 230000029142 excretion Effects 0.000 description 1
• 229960000255 exemestane Drugs 0.000 description 1
• 239000003889 eye drop Substances 0.000 description 1
• 229940012356 eye drops Drugs 0.000 description 1
• 229950011548 fadrozole Drugs 0.000 description 1
• 229940043168 fareston Drugs 0.000 description 1
• 229940087861 faslodex Drugs 0.000 description 1
• ODKNJVUHOIMIIZ-RRKCRQDMSA-N floxuridine Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(F)=C1 ODKNJVUHOIMIIZ-RRKCRQDMSA-N 0.000 description 1
• 229960000961 floxuridine Drugs 0.000 description 1
• XRECTZIEBJDKEO-UHFFFAOYSA-N flucytosine Chemical compound NC1=NC(=O)NC=C1F XRECTZIEBJDKEO-UHFFFAOYSA-N 0.000 description 1
• 229960004413 flucytosine Drugs 0.000 description 1
• 229960000390 fludarabine Drugs 0.000 description 1
• GIUYCYHIANZCFB-FJFJXFQQSA-N fludarabine phosphate Chemical compound C1=NC=2C(N)=NC(F)=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O GIUYCYHIANZCFB-FJFJXFQQSA-N 0.000 description 1
• 239000011737 fluorine Chemical group 0.000 description 1
• 229960002074 flutamide Drugs 0.000 description 1
• MKXKFYHWDHIYRV-UHFFFAOYSA-N flutamide Chemical compound CC(C)C(=O)NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 MKXKFYHWDHIYRV-UHFFFAOYSA-N 0.000 description 1
• 239000006260 foam Substances 0.000 description 1
• 239000011888 foil Substances 0.000 description 1
• 235000019152 folic acid Nutrition 0.000 description 1
• 239000011724 folic acid Substances 0.000 description 1
• 229960000304 folic acid Drugs 0.000 description 1
• 150000002224 folic acids Chemical class 0.000 description 1
• VVIAGPKUTFNRDU-ABLWVSNPSA-N folinic acid Chemical compound C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-ABLWVSNPSA-N 0.000 description 1
• 235000008191 folinic acid Nutrition 0.000 description 1
• 239000011672 folinic acid Substances 0.000 description 1
• 229960004783 fotemustine Drugs 0.000 description 1
• YAKWPXVTIGTRJH-UHFFFAOYSA-N fotemustine Chemical compound CCOP(=O)(OCC)C(C)NC(=O)N(CCCl)N=O YAKWPXVTIGTRJH-UHFFFAOYSA-N 0.000 description 1
• 239000012458 free base Substances 0.000 description 1
• 229940050411 fumarate Drugs 0.000 description 1
• 239000001530 fumaric acid Substances 0.000 description 1
• 230000006870 function Effects 0.000 description 1
• CYEFKCRAAGLNHW-UHFFFAOYSA-N furan-3-ylboronic acid Chemical compound OB(O)C=1C=COC=1 CYEFKCRAAGLNHW-UHFFFAOYSA-N 0.000 description 1
• 150000002240 furans Chemical class 0.000 description 1
• 125000003838 furazanyl group Chemical group 0.000 description 1
• 125000004612 furopyridinyl group Chemical group O1C(=CC2=C1C=CC=N2)* 0.000 description 1
• 229940044658 gallium nitrate Drugs 0.000 description 1
• 229960003692 gamma aminobutyric acid Drugs 0.000 description 1
• 210000001035 gastrointestinal tract Anatomy 0.000 description 1
• 229960002584 gefitinib Drugs 0.000 description 1
• 239000000499 gel Substances 0.000 description 1
• 239000007903 gelatin capsule Substances 0.000 description 1
• SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 description 1
• 229960005277 gemcitabine Drugs 0.000 description 1
• 229940020967 gemzar Drugs 0.000 description 1
• 238000001415 gene therapy Methods 0.000 description 1
• 235000021474 generally recognized As safe (food) Nutrition 0.000 description 1
• 235000021473 generally recognized as safe (food ingredients) Nutrition 0.000 description 1
• 229940080856 gleevec Drugs 0.000 description 1
• 229940050410 gluconate Drugs 0.000 description 1
• 239000008103 glucose Substances 0.000 description 1
• 229940097042 glucuronate Drugs 0.000 description 1
• 229940097043 glucuronic acid Drugs 0.000 description 1
• 235000013922 glutamic acid Nutrition 0.000 description 1
• 239000004220 glutamic acid Substances 0.000 description 1
• ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
• 229940074045 glyceryl distearate Drugs 0.000 description 1
• 229930182470 glycoside Natural products 0.000 description 1
• 125000003147 glycosyl group Chemical group 0.000 description 1
• 229960002913 goserelin Drugs 0.000 description 1
• 230000012010 growth Effects 0.000 description 1
• 239000003102 growth factor Substances 0.000 description 1
• 229940093915 gynecological organic acid Drugs 0.000 description 1
• 150000004820 halides Chemical class 0.000 description 1
• 239000007902 hard capsule Substances 0.000 description 1
• 201000010536 head and neck cancer Diseases 0.000 description 1
• 208000014829 head and neck neoplasm Diseases 0.000 description 1
• 150000002373 hemiacetals Chemical group 0.000 description 1
• 230000002440 hepatic effect Effects 0.000 description 1
• 210000003494 hepatocyte Anatomy 0.000 description 1
• 150000002391 heterocyclic compounds Chemical class 0.000 description 1
• 239000008241 heterogeneous mixture Substances 0.000 description 1
• UUVWYPNAQBNQJQ-UHFFFAOYSA-N hexamethylmelamine Chemical compound CN(C)C1=NC(N(C)C)=NC(N(C)C)=N1 UUVWYPNAQBNQJQ-UHFFFAOYSA-N 0.000 description 1
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
• 230000003054 hormonal effect Effects 0.000 description 1
• 239000000017 hydrogel Substances 0.000 description 1
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
• 230000003301 hydrolyzing effect Effects 0.000 description 1
• 239000008309 hydrophilic cream Substances 0.000 description 1
• 229920001477 hydrophilic polymer Polymers 0.000 description 1
• 230000002209 hydrophobic effect Effects 0.000 description 1
• 229920001600 hydrophobic polymer Polymers 0.000 description 1
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
• QJHBJHUKURJDLG-UHFFFAOYSA-N hydroxy-L-lysine Natural products NCCCCC(NO)C(O)=O QJHBJHUKURJDLG-UHFFFAOYSA-N 0.000 description 1
• 229960001330 hydroxycarbamide Drugs 0.000 description 1
• 229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
• 229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
• 229960002591 hydroxyproline Drugs 0.000 description 1
• 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
• 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
• 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
• 230000007954 hypoxia Effects 0.000 description 1
• 229940015872 ibandronate Drugs 0.000 description 1
• 229960000908 idarubicin Drugs 0.000 description 1
• 238000003384 imaging method Methods 0.000 description 1
• 229960003685 imatinib mesylate Drugs 0.000 description 1
• 125000002632 imidazolidinyl group Chemical group 0.000 description 1
• MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical group C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
• 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 description 1
• 230000036039 immunity Effects 0.000 description 1
• 102000018358 immunoglobulin Human genes 0.000 description 1
• 229940072221 immunoglobulins Drugs 0.000 description 1
• 230000001506 immunosuppresive effect Effects 0.000 description 1
• DBIGHPPNXATHOF-UHFFFAOYSA-N improsulfan Chemical compound CS(=O)(=O)OCCCNCCCOS(C)(=O)=O DBIGHPPNXATHOF-UHFFFAOYSA-N 0.000 description 1
• 229950008097 improsulfan Drugs 0.000 description 1
• 238000000099 in vitro assay Methods 0.000 description 1
• 125000003392 indanyl group Chemical class C1(CCC2=CC=CC=C12)* 0.000 description 1
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
• 125000003454 indenyl group Chemical class C1(C=CC2=CC=CC=C12)* 0.000 description 1
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Chemical group CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Chemical group C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
• 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
• 125000001041 indolyl group Chemical group 0.000 description 1
• 230000006698 induction Effects 0.000 description 1
• 230000006882 induction of apoptosis Effects 0.000 description 1
• 230000008595 infiltration Effects 0.000 description 1
• 238000001764 infiltration Methods 0.000 description 1
• 230000005764 inhibitory process Effects 0.000 description 1
• 229940102223 injectable solution Drugs 0.000 description 1
• 229940102213 injectable suspension Drugs 0.000 description 1
• 208000014674 injury Diseases 0.000 description 1
• 150000007529 inorganic bases Chemical class 0.000 description 1
• CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical group O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 description 1
• CDAISMWEOUEBRE-UHFFFAOYSA-N inositol Chemical group OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
• 239000002198 insoluble material Substances 0.000 description 1
• 230000002452 interceptive effect Effects 0.000 description 1
• 238000001361 intraarterial administration Methods 0.000 description 1
• 230000031146 intracellular signal transduction Effects 0.000 description 1
• 238000007918 intramuscular administration Methods 0.000 description 1
• 238000007912 intraperitoneal administration Methods 0.000 description 1
• 238000007913 intrathecal administration Methods 0.000 description 1
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
• 238000005342 ion exchange Methods 0.000 description 1
• 239000012500 ion exchange media Substances 0.000 description 1
• 229940084651 iressa Drugs 0.000 description 1
• UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 description 1
• 229910052742 iron Inorganic materials 0.000 description 1
• AWJUIBRHMBBTKR-UHFFFAOYSA-N iso-quinoline Natural products C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 1
• 229940047889 isobutyramide Drugs 0.000 description 1
• GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical group C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 1
• TWBYWOBDOCUKOW-UHFFFAOYSA-M isonicotinate Chemical compound [O-]C(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-M 0.000 description 1
• QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
• ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical group C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
• 125000001786 isothiazolyl group Chemical group 0.000 description 1
• 239000008101 lactose Substances 0.000 description 1
• 229960004891 lapatinib Drugs 0.000 description 1
• 210000002429 large intestine Anatomy 0.000 description 1
• 235000010445 lecithin Nutrition 0.000 description 1
• 239000000787 lecithin Substances 0.000 description 1
• 229940067606 lecithin Drugs 0.000 description 1
• 229940115286 lentinan Drugs 0.000 description 1
• 229960001691 leucovorin Drugs 0.000 description 1
• RGLRXNKKBLIBQS-XNHQSDQCSA-N leuprolide acetate Chemical compound CC(O)=O.CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H]1NC(=O)CC1)CC1=CC=C(O)C=C1 RGLRXNKKBLIBQS-XNHQSDQCSA-N 0.000 description 1
• 210000000088 lip Anatomy 0.000 description 1
• 230000004576 lipid-binding Effects 0.000 description 1
• 238000004811 liquid chromatography Methods 0.000 description 1
• 229910052744 lithium Inorganic materials 0.000 description 1
• 201000007270 liver cancer Diseases 0.000 description 1
• 201000002250 liver carcinoma Diseases 0.000 description 1
• 229960002247 lomustine Drugs 0.000 description 1
• DHMTURDWPRKSOA-RUZDIDTESA-N lonafarnib Chemical compound C1CN(C(=O)N)CCC1CC(=O)N1CCC([C@@H]2C3=C(Br)C=C(Cl)C=C3CCC3=CC(Br)=CN=C32)CC1 DHMTURDWPRKSOA-RUZDIDTESA-N 0.000 description 1
• YROQEQPFUCPDCP-UHFFFAOYSA-N losoxantrone Chemical compound OCCNCCN1N=C2C3=CC=CC(O)=C3C(=O)C3=C2C1=CC=C3NCCNCCO YROQEQPFUCPDCP-UHFFFAOYSA-N 0.000 description 1
• 229950008745 losoxantrone Drugs 0.000 description 1
• 238000003819 low-pressure liquid chromatography Methods 0.000 description 1
• 201000005202 lung cancer Diseases 0.000 description 1
• 208000020816 lung neoplasm Diseases 0.000 description 1
• 229940087857 lupron Drugs 0.000 description 1
• RVFGKBWWUQOIOU-NDEPHWFRSA-N lurtotecan Chemical compound O=C([C@]1(O)CC)OCC(C(N2CC3=4)=O)=C1C=C2C3=NC1=CC=2OCCOC=2C=C1C=4CN1CCN(C)CC1 RVFGKBWWUQOIOU-NDEPHWFRSA-N 0.000 description 1
• 229950002654 lurtotecan Drugs 0.000 description 1
• 239000008176 lyophilized powder Substances 0.000 description 1
• 239000011777 magnesium Substances 0.000 description 1
• 229910052749 magnesium Inorganic materials 0.000 description 1
• 235000019359 magnesium stearate Nutrition 0.000 description 1
• 239000011976 maleic acid Substances 0.000 description 1
• 230000036212 malign transformation Effects 0.000 description 1
• 230000036210 malignancy Effects 0.000 description 1
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 1
• WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
• MQXVYODZCMMZEM-ZYUZMQFOSA-N mannomustine Chemical compound ClCCNC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CNCCCl MQXVYODZCMMZEM-ZYUZMQFOSA-N 0.000 description 1
• 229950008612 mannomustine Drugs 0.000 description 1
• WKPWGQKGSOKKOO-RSFHAFMBSA-N maytansine Chemical compound CO[C@@H]([C@@]1(O)C[C@](OC(=O)N1)([C@H]([C@@H]1O[C@@]1(C)[C@@H](OC(=O)[C@H](C)N(C)C(C)=O)CC(=O)N1C)C)[H])\C=C\C=C(C)\CC2=CC(OC)=C(Cl)C1=C2 WKPWGQKGSOKKOO-RSFHAFMBSA-N 0.000 description 1
• 229960004961 mechlorethamine Drugs 0.000 description 1
• HAWPXGHAZFHHAD-UHFFFAOYSA-N mechlorethamine Chemical compound ClCCN(C)CCCl HAWPXGHAZFHHAD-UHFFFAOYSA-N 0.000 description 1
• 229960004296 megestrol acetate Drugs 0.000 description 1
• RQZAXGRLVPAYTJ-GQFGMJRRSA-N megestrol acetate Chemical compound C1=C(C)C2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 RQZAXGRLVPAYTJ-GQFGMJRRSA-N 0.000 description 1
• SGDBTWWWUNNDEQ-LBPRGKRZSA-N melphalan Chemical compound OC(=O)[C@@H](N)CC1=CC=C(N(CCCl)CCCl)C=C1 SGDBTWWWUNNDEQ-LBPRGKRZSA-N 0.000 description 1
• 229960001924 melphalan Drugs 0.000 description 1
• 238000002844 melting Methods 0.000 description 1
• 230000008018 melting Effects 0.000 description 1
• 229950009246 mepitiostane Drugs 0.000 description 1
• 230000009401 metastasis Effects 0.000 description 1
• TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical compound Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 description 1
• 229940098779 methanesulfonic acid Drugs 0.000 description 1
• 229930182817 methionine Natural products 0.000 description 1
• VJRAUFKOOPNFIQ-TVEKBUMESA-N methyl (1r,2r,4s)-4-[(2r,4s,5s,6s)-5-[(2s,4s,5s,6s)-5-[(2s,4s,5s,6s)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-4-(dimethylamino)-6-methyloxan-2-yl]oxy-2-ethyl-2,5,7,10-tetrahydroxy-6,11-dioxo-3,4-dihydro-1h-tetracene-1-carboxylat Chemical compound O([C@H]1[C@@H](O)C[C@@H](O[C@H]1C)O[C@H]1[C@H](C[C@@H](O[C@H]1C)O[C@H]1C[C@]([C@@H](C2=CC=3C(=O)C4=C(O)C=CC(O)=C4C(=O)C=3C(O)=C21)C(=O)OC)(O)CC)N(C)C)[C@H]1C[C@H](O)[C@H](O)[C@H](C)O1 VJRAUFKOOPNFIQ-TVEKBUMESA-N 0.000 description 1
• QRMNENFZDDYDEF-GOSISDBHSA-N methyl (8s)-8-(bromomethyl)-2-methyl-4-(4-methylpiperazine-1-carbonyl)oxy-6-(5,6,7-trimethoxy-1h-indole-2-carbonyl)-7,8-dihydro-3h-pyrrolo[3,2-e]indole-1-carboxylate Chemical compound C1([C@H](CBr)CN(C1=C1)C(=O)C=2NC3=C(OC)C(OC)=C(OC)C=C3C=2)=C2C(C(=O)OC)=C(C)NC2=C1OC(=O)N1CCN(C)CC1 QRMNENFZDDYDEF-GOSISDBHSA-N 0.000 description 1
• TWEQNZZOOFKOER-UHFFFAOYSA-N methyl 3-aminothiophene-2-carboxylate Chemical compound COC(=O)C=1SC=CC=1N TWEQNZZOOFKOER-UHFFFAOYSA-N 0.000 description 1
• 229920000609 methyl cellulose Polymers 0.000 description 1
• 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
• 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
• WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
• 235000010981 methylcellulose Nutrition 0.000 description 1
• 239000001923 methylcellulose Substances 0.000 description 1
• 229960002900 methylcellulose Drugs 0.000 description 1
• HRHKSTOGXBBQCB-VFWICMBZSA-N methylmitomycin Chemical compound O=C1C(N)=C(C)C(=O)C2=C1[C@@H](COC(N)=O)[C@@]1(OC)[C@H]3N(C)[C@H]3CN12 HRHKSTOGXBBQCB-VFWICMBZSA-N 0.000 description 1
• 229960002216 methylparaben Drugs 0.000 description 1
• HPNSFSBZBAHARI-UHFFFAOYSA-N micophenolic acid Natural products OC1=C(CC=C(C)CCC(O)=O)C(OC)=C(C)C2=C1C(=O)OC2 HPNSFSBZBAHARI-UHFFFAOYSA-N 0.000 description 1
• 239000004530 micro-emulsion Substances 0.000 description 1
• 239000002480 mineral oil Substances 0.000 description 1
• 235000010446 mineral oil Nutrition 0.000 description 1
• 150000007522 mineralic acids Chemical class 0.000 description 1
• 229960005485 mitobronitol Drugs 0.000 description 1
• 229960003539 mitoguazone Drugs 0.000 description 1
• MXWHMTNPTTVWDM-NXOFHUPFSA-N mitoguazone Chemical compound NC(N)=N\N=C(/C)\C=N\N=C(N)N MXWHMTNPTTVWDM-NXOFHUPFSA-N 0.000 description 1
• VFKZTMPDYBFSTM-GUCUJZIJSA-N mitolactol Chemical compound BrC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CBr VFKZTMPDYBFSTM-GUCUJZIJSA-N 0.000 description 1
• 229950010913 mitolactol Drugs 0.000 description 1
• 229960004857 mitomycin Drugs 0.000 description 1
• 229960000350 mitotane Drugs 0.000 description 1
• 239000007932 molded tablet Substances 0.000 description 1
• 230000009456 molecular mechanism Effects 0.000 description 1
• 239000002808 molecular sieve Substances 0.000 description 1
• 125000001620 monocyclic carbocycle group Chemical group 0.000 description 1
• 150000002772 monosaccharides Chemical class 0.000 description 1
• 230000004899 motility Effects 0.000 description 1
• 238000000465 moulding Methods 0.000 description 1
• 239000002324 mouth wash Substances 0.000 description 1
• 230000035772 mutation Effects 0.000 description 1
• 229960000951 mycophenolic acid Drugs 0.000 description 1
• HPNSFSBZBAHARI-RUDMXATFSA-N mycophenolic acid Chemical compound OC1=C(C\C=C(/C)CCC(O)=O)C(OC)=C(C)C2=C1C(=O)OC2 HPNSFSBZBAHARI-RUDMXATFSA-N 0.000 description 1
• 208000010125 myocardial infarction Diseases 0.000 description 1
• 229940043348 myristyl alcohol Drugs 0.000 description 1
• NPZALOYDCLWIJS-UHFFFAOYSA-N n,1-dimethyl-n-[(4-morpholin-4-yl-2-pyrimidin-5-ylthieno[2,3-d]pyrimidin-6-yl)methyl]piperidin-4-amine Chemical compound C1CN(C)CCC1N(C)CC(SC1=N2)=CC1=C(N1CCOCC1)N=C2C1=CN=CN=C1 NPZALOYDCLWIJS-UHFFFAOYSA-N 0.000 description 1
• LOTFUQVQKAVQHB-UHFFFAOYSA-N n,1-dimethyl-n-[(7-methyl-4-morpholin-4-yl-2-pyridin-3-ylthieno[3,2-d]pyrimidin-6-yl)methyl]piperidin-4-amine Chemical compound C1CN(C)CCC1N(C)CC(=C(C1=N2)C)SC1=C(N1CCOCC1)N=C2C1=CC=CN=C1 LOTFUQVQKAVQHB-UHFFFAOYSA-N 0.000 description 1
• QTJFRYLYLQKBJA-UHFFFAOYSA-N n,2-dimethyl-2-piperazin-1-ylpropanamide Chemical compound CNC(=O)C(C)(C)N1CCNCC1 QTJFRYLYLQKBJA-UHFFFAOYSA-N 0.000 description 1
• HLKAXMBNTHBWKS-UHFFFAOYSA-N n,n-diethylpiperidine-4-carboxamide Chemical compound CCN(CC)C(=O)C1CCNCC1 HLKAXMBNTHBWKS-UHFFFAOYSA-N 0.000 description 1
• RMPRVJCNMPFBCX-UHFFFAOYSA-N n,n-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine Chemical compound C1=NC(N(C)C)=NC=C1B1OC(C)(C)C(C)(C)O1 RMPRVJCNMPFBCX-UHFFFAOYSA-N 0.000 description 1
• UPNMYWICFZVSLL-UHFFFAOYSA-N n,n-dimethyl-5-[6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1=NC(N(C)C)=NC=C1C1=NC(N2CCOCC2)=C(C=C(CN2CCN(CC2)S(C)(=O)=O)S2)C2=N1 UPNMYWICFZVSLL-UHFFFAOYSA-N 0.000 description 1
• 229940078490 n,n-dimethylglycine Drugs 0.000 description 1
• NQZDGTYTTVHKPE-UHFFFAOYSA-N n,n-dimethylpiperazine-1-sulfonamide Chemical compound CN(C)S(=O)(=O)N1CCNCC1 NQZDGTYTTVHKPE-UHFFFAOYSA-N 0.000 description 1
• QJAOEUZOXCTOSB-UHFFFAOYSA-N n-[(2-chloro-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl)methyl]-n,1-dimethylpiperidin-4-amine Chemical compound C1CN(C)CCC1N(C)CC(=C(C1=NC(Cl)=N2)C)SC1=C2N1CCOCC1 QJAOEUZOXCTOSB-UHFFFAOYSA-N 0.000 description 1
• NJSMWLQOCQIOPE-OCHFTUDZSA-N n-[(e)-[10-[(e)-(4,5-dihydro-1h-imidazol-2-ylhydrazinylidene)methyl]anthracen-9-yl]methylideneamino]-4,5-dihydro-1h-imidazol-2-amine Chemical compound N1CCN=C1N\N=C\C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1\C=N\NC1=NCCN1 NJSMWLQOCQIOPE-OCHFTUDZSA-N 0.000 description 1
• LBWFXVZLPYTWQI-IPOVEDGCSA-N n-[2-(diethylamino)ethyl]-5-[(z)-(5-fluoro-2-oxo-1h-indol-3-ylidene)methyl]-2,4-dimethyl-1h-pyrrole-3-carboxamide;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.CCN(CC)CCNC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C LBWFXVZLPYTWQI-IPOVEDGCSA-N 0.000 description 1
• MMIHZJBEXXLLGH-UHFFFAOYSA-N n-[5-[4-morpholin-4-yl-6-[[4-[2-(oxan-2-yloxy)acetyl]piperazin-1-yl]methyl]thieno[3,2-d]pyrimidin-2-yl]pyridin-2-yl]acetamide Chemical compound C1=NC(NC(=O)C)=CC=C1C1=NC(N2CCOCC2)=C(SC(CN2CCN(CC2)C(=O)COC2OCCCC2)=C2)C2=N1 MMIHZJBEXXLLGH-UHFFFAOYSA-N 0.000 description 1
• VFBILHPIHUPBPZ-UHFFFAOYSA-N n-[[2-[4-(difluoromethoxy)-3-propan-2-yloxyphenyl]-1,3-oxazol-4-yl]methyl]-2-ethoxybenzamide Chemical compound CCOC1=CC=CC=C1C(=O)NCC1=COC(C=2C=C(OC(C)C)C(OC(F)F)=CC=2)=N1 VFBILHPIHUPBPZ-UHFFFAOYSA-N 0.000 description 1
• 239000002088 nanocapsule Substances 0.000 description 1
• 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
• 229930014626 natural product Natural products 0.000 description 1
• 229940086322 navelbine Drugs 0.000 description 1
• 230000007135 neurotoxicity Effects 0.000 description 1
• 231100000228 neurotoxicity Toxicity 0.000 description 1
• 229940080607 nexavar Drugs 0.000 description 1
• 229960002653 nilutamide Drugs 0.000 description 1
• XWXYUMMDTVBTOU-UHFFFAOYSA-N nilutamide Chemical compound O=C1C(C)(C)NC(=O)N1C1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 XWXYUMMDTVBTOU-UHFFFAOYSA-N 0.000 description 1
• 229960001420 nimustine Drugs 0.000 description 1
• VFEDRRNHLBGPNN-UHFFFAOYSA-N nimustine Chemical compound CC1=NC=C(CNC(=O)N(CCCl)N=O)C(N)=N1 VFEDRRNHLBGPNN-UHFFFAOYSA-N 0.000 description 1
• 229910017604 nitric acid Inorganic materials 0.000 description 1
• KGTDRFCXGRULNK-JYOBTZKQSA-N nogalamycin Chemical compound CO[C@@H]1[C@@](OC)(C)[C@@H](OC)[C@H](C)O[C@H]1O[C@@H]1C2=C(O)C(C(=O)C3=C(O)C=C4[C@@]5(C)O[C@H]([C@H]([C@@H]([C@H]5O)N(C)C)O)OC4=C3C3=O)=C3C=C2[C@@H](C(=O)OC)[C@@](C)(O)C1 KGTDRFCXGRULNK-JYOBTZKQSA-N 0.000 description 1
• 229950009266 nogalamycin Drugs 0.000 description 1
• 229940085033 nolvadex Drugs 0.000 description 1
• 239000002736 nonionic surfactant Substances 0.000 description 1
• UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical group C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
• 239000002777 nucleoside Substances 0.000 description 1
• GYCKQBWUSACYIF-UHFFFAOYSA-N o-hydroxybenzoic acid ethyl ester Natural products CCOC(=O)C1=CC=CC=C1O GYCKQBWUSACYIF-UHFFFAOYSA-N 0.000 description 1
• GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 1
• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
• OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
• CQYBNXGHMBNGCG-RNJXMRFFSA-N octahydroindole-2-carboxylic acid Chemical compound C1CCC[C@H]2N[C@H](C(=O)O)C[C@@H]21 CQYBNXGHMBNGCG-RNJXMRFFSA-N 0.000 description 1
• 239000012053 oil suspension Substances 0.000 description 1
• 239000002674 ointment Substances 0.000 description 1
• 229940049964 oleate Drugs 0.000 description 1
• CZDBNBLGZNWKMC-MWQNXGTOSA-N olivomycin Chemical class O([C@@H]1C[C@@H](O[C@H](C)[C@@H]1O)OC=1C=C2C=C3C[C@H]([C@@H](C(=O)C3=C(O)C2=C(O)C=1)O[C@H]1O[C@@H](C)[C@H](O)[C@@H](OC2O[C@@H](C)[C@H](O)[C@@H](O)C2)C1)[C@H](OC)C(=O)[C@@H](O)[C@@H](C)O)[C@H]1C[C@H](O)[C@H](OC)[C@H](C)O1 CZDBNBLGZNWKMC-MWQNXGTOSA-N 0.000 description 1
• 229950011093 onapristone Drugs 0.000 description 1
• 238000011275 oncology therapy Methods 0.000 description 1
• 102000027450 oncoproteins Human genes 0.000 description 1
• 108091008819 oncoproteins Proteins 0.000 description 1
• 235000005985 organic acids Nutrition 0.000 description 1
• 150000007530 organic bases Chemical class 0.000 description 1
• 239000003960 organic solvent Substances 0.000 description 1
• 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
• 229960003104 ornithine Drugs 0.000 description 1
• 125000001715 oxadiazolyl group Chemical group 0.000 description 1
• 229940116315 oxalic acid Drugs 0.000 description 1
• 235000006408 oxalic acid Nutrition 0.000 description 1
• DWAFYCQODLXJNR-BNTLRKBRSA-L oxaliplatin Chemical compound O1C(=O)C(=O)O[Pt]11N[C@@H]2CCCC[C@H]2N1 DWAFYCQODLXJNR-BNTLRKBRSA-L 0.000 description 1
• 229960001756 oxaliplatin Drugs 0.000 description 1
• 125000003551 oxepanyl group Chemical group 0.000 description 1
• 125000003566 oxetanyl group Chemical group 0.000 description 1
• LXCFILQKKLGQFO-UHFFFAOYSA-N p-hydroxybenzoic acid methyl ester Natural products COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
• 229910052763 palladium Inorganic materials 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
• VREZDOWOLGNDPW-UHFFFAOYSA-N pancratistatine Natural products C1=C2C3C(O)C(O)C(O)C(O)C3NC(=O)C2=C(O)C2=C1OCO2 VREZDOWOLGNDPW-UHFFFAOYSA-N 0.000 description 1
• 201000002528 pancreatic cancer Diseases 0.000 description 1
• 208000008443 pancreatic carcinoma Diseases 0.000 description 1
• 229940014662 pantothenate Drugs 0.000 description 1
• 235000019161 pantothenic acid Nutrition 0.000 description 1
• 239000011713 pantothenic acid Substances 0.000 description 1
• FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
• 201000010198 papillary carcinoma Diseases 0.000 description 1
• 238000007911 parenteral administration Methods 0.000 description 1
• 239000006072 paste Substances 0.000 description 1
• 235000010603 pastilles Nutrition 0.000 description 1
• 230000037361 pathway Effects 0.000 description 1
• 230000035515 penetration Effects 0.000 description 1
• 229960001639 penicillamine Drugs 0.000 description 1
• 208000030940 penile carcinoma Diseases 0.000 description 1
• 201000008174 penis carcinoma Diseases 0.000 description 1
• 229960002340 pentostatin Drugs 0.000 description 1
• FPVKHBSQESCIEP-JQCXWYLXSA-N pentostatin Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(N=CNC[C@H]2O)=C2N=C1 FPVKHBSQESCIEP-JQCXWYLXSA-N 0.000 description 1
• QIMGFXOHTOXMQP-GFAGFCTOSA-N peplomycin Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCCN[C@@H](C)C=1C=CC=CC=1)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1NC=NC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C QIMGFXOHTOXMQP-GFAGFCTOSA-N 0.000 description 1
• 229950003180 peplomycin Drugs 0.000 description 1
• 239000002304 perfume Substances 0.000 description 1
• 230000002093 peripheral effect Effects 0.000 description 1
• 201000002628 peritoneum cancer Diseases 0.000 description 1
• 230000035699 permeability Effects 0.000 description 1
• 239000000825 pharmaceutical preparation Substances 0.000 description 1
• 229940127557 pharmaceutical product Drugs 0.000 description 1
• 230000003285 pharmacodynamic effect Effects 0.000 description 1
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
• WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 1
• USRGIUJOYOXOQJ-GBXIJSLDSA-N phosphothreonine Chemical compound OP(=O)(O)O[C@H](C)[C@H](N)C(O)=O USRGIUJOYOXOQJ-GBXIJSLDSA-N 0.000 description 1
• DCWXELXMIBXGTH-UHFFFAOYSA-N phosphotyrosine Chemical compound OC(=O)C(N)CC1=CC=C(OP(O)(O)=O)C=C1 DCWXELXMIBXGTH-UHFFFAOYSA-N 0.000 description 1
• 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
• 230000000704 physical effect Effects 0.000 description 1
• 230000004962 physiological condition Effects 0.000 description 1
• NJBFOOCLYDNZJN-UHFFFAOYSA-N pipobroman Chemical compound BrCCC(=O)N1CCN(C(=O)CCBr)CC1 NJBFOOCLYDNZJN-UHFFFAOYSA-N 0.000 description 1
• 229960000952 pipobroman Drugs 0.000 description 1
• NUKCGLDCWQXYOQ-UHFFFAOYSA-N piposulfan Chemical compound CS(=O)(=O)OCCC(=O)N1CCN(C(=O)CCOS(C)(=O)=O)CC1 NUKCGLDCWQXYOQ-UHFFFAOYSA-N 0.000 description 1
• 229950001100 piposulfan Drugs 0.000 description 1
• 229960001221 pirarubicin Drugs 0.000 description 1
• 150000003057 platinum Chemical class 0.000 description 1
• 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
• 229920000747 poly(lactic acid) Polymers 0.000 description 1
• 229920000728 polyester Polymers 0.000 description 1
• 229920002338 polyhydroxyethylmethacrylate Polymers 0.000 description 1
• 229920000642 polymer Polymers 0.000 description 1
• 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
• 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
• 229920001282 polysaccharide Polymers 0.000 description 1
• 239000005017 polysaccharide Substances 0.000 description 1
• 150000004804 polysaccharides Chemical class 0.000 description 1
• 229920000136 polysorbate Polymers 0.000 description 1
• 229920000053 polysorbate 80 Polymers 0.000 description 1
• 229920002451 polyvinyl alcohol Polymers 0.000 description 1
• 229950004406 porfiromycin Drugs 0.000 description 1
• 238000002600 positron emission tomography Methods 0.000 description 1
• 229910052700 potassium Inorganic materials 0.000 description 1
• 239000011591 potassium Substances 0.000 description 1
• SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 1
• 235000015320 potassium carbonate Nutrition 0.000 description 1
• 235000011181 potassium carbonates Nutrition 0.000 description 1
• 229940069328 povidone Drugs 0.000 description 1
• 229960004694 prednimustine Drugs 0.000 description 1
• 230000002335 preservative effect Effects 0.000 description 1
• 230000002265 prevention Effects 0.000 description 1
• CPTBDICYNRMXFX-UHFFFAOYSA-N procarbazine Chemical compound CNNCC1=CC=C(C(=O)NC(C)C)C=C1 CPTBDICYNRMXFX-UHFFFAOYSA-N 0.000 description 1
• 229960000624 procarbazine Drugs 0.000 description 1
• 238000012545 processing Methods 0.000 description 1
• 229940087463 proleukin Drugs 0.000 description 1
• 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
• 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
• 235000013772 propylene glycol Nutrition 0.000 description 1
• 229960003415 propylparaben Drugs 0.000 description 1
• 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
• 239000003909 protein kinase inhibitor Substances 0.000 description 1
• 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
• WOLQREOUPKZMEX-UHFFFAOYSA-N pteroyltriglutamic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC(O)=O)C(O)=O)C(O)=O)C(O)=O)C=C1 WOLQREOUPKZMEX-UHFFFAOYSA-N 0.000 description 1
• 150000003212 purines Chemical class 0.000 description 1
• 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
• 229950010131 puromycin Drugs 0.000 description 1
• DMEUDSHBHKHLPD-UHFFFAOYSA-N pyrazin-2-amine Chemical compound NC1=CN=C=C[N]1 DMEUDSHBHKHLPD-UHFFFAOYSA-N 0.000 description 1
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
• DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical group C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
• 125000002755 pyrazolinyl group Chemical group 0.000 description 1
• 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
• 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
• 125000004941 pyridazin-5-yl group Chemical group N1=NC=CC(=C1)* 0.000 description 1
• PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
• QLULGIRFKAWHOJ-UHFFFAOYSA-N pyridin-4-ylboronic acid Chemical compound OB(O)C1=CC=NC=C1 QLULGIRFKAWHOJ-UHFFFAOYSA-N 0.000 description 1
• VFGHOEGFPHLMIK-UHFFFAOYSA-N pyridine-2-carbonitrile Chemical compound N#CC1=C=CC=C[N]1 VFGHOEGFPHLMIK-UHFFFAOYSA-N 0.000 description 1
• WIRTYVGMQVIVDM-UHFFFAOYSA-N pyridine-3-carbonitrile Chemical compound N#CC1=C=NC=C[CH]1 WIRTYVGMQVIVDM-UHFFFAOYSA-N 0.000 description 1
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
• HZFPPBMKGYINDF-UHFFFAOYSA-N pyrimidin-5-ylboronic acid Chemical compound OB(O)C1=CN=CN=C1 HZFPPBMKGYINDF-UHFFFAOYSA-N 0.000 description 1
• VPIDYWHXQFUKNG-UHFFFAOYSA-N pyrimidine thieno[3,2-d]pyrimidine Chemical compound N1=CN=CC=C1.N1=CN=CC2=C1C=CS2 VPIDYWHXQFUKNG-UHFFFAOYSA-N 0.000 description 1
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
• 229940107700 pyruvic acid Drugs 0.000 description 1
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
• 229960000948 quinine Drugs 0.000 description 1
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
• UOWVMDUEMSNCAV-WYENRQIDSA-N rachelmycin Chemical compound C1([C@]23C[C@@H]2CN1C(=O)C=1NC=2C(OC)=C(O)C4=C(C=2C=1)CCN4C(=O)C1=CC=2C=4CCN(C=4C(O)=C(C=2N1)OC)C(N)=O)=CC(=O)C1=C3C(C)=CN1 UOWVMDUEMSNCAV-WYENRQIDSA-N 0.000 description 1
• 238000001959 radiotherapy Methods 0.000 description 1
• 229940099538 rapamune Drugs 0.000 description 1
• BMKDZUISNHGIBY-UHFFFAOYSA-N razoxane Chemical compound C1C(=O)NC(=O)CN1C(C)CN1CC(=O)NC(=O)C1 BMKDZUISNHGIBY-UHFFFAOYSA-N 0.000 description 1
• 229960000460 razoxane Drugs 0.000 description 1
• 230000009257 reactivity Effects 0.000 description 1
• 102000005962 receptors Human genes 0.000 description 1
• 108020003175 receptors Proteins 0.000 description 1
• 238000003259 recombinant expression Methods 0.000 description 1
• 206010038038 rectal cancer Diseases 0.000 description 1
• 210000000664 rectum Anatomy 0.000 description 1
• 201000001275 rectum cancer Diseases 0.000 description 1
• 230000022983 regulation of cell cycle Effects 0.000 description 1
• 201000010174 renal carcinoma Diseases 0.000 description 1
• 238000011160 research Methods 0.000 description 1
• 230000004044 response Effects 0.000 description 1
• 229930002330 retinoic acid Natural products 0.000 description 1
• 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
• 206010039073 rheumatoid arthritis Diseases 0.000 description 1
• OWPCHSCAPHNHAV-LMONGJCWSA-N rhizoxin Chemical compound C/C([C@H](OC)[C@@H](C)[C@@H]1C[C@H](O)[C@]2(C)O[C@@H]2/C=C/[C@@H](C)[C@]2([H])OC(=O)C[C@@](C2)(C[C@@H]2O[C@H]2C(=O)O1)[H])=C\C=C\C(\C)=C\C1=COC(C)=N1 OWPCHSCAPHNHAV-LMONGJCWSA-N 0.000 description 1
• 229910052703 rhodium Inorganic materials 0.000 description 1
• 108091092562 ribozyme Proteins 0.000 description 1
• 229950004892 rodorubicin Drugs 0.000 description 1
• MBABCNBNDNGODA-WPZDJQSSSA-N rolliniastatin 1 Natural products O1[C@@H]([C@@H](O)CCCCCCCCCC)CC[C@H]1[C@H]1O[C@@H]([C@H](O)CCCCCCCCCC[C@@H](O)CC=2C(O[C@@H](C)C=2)=O)CC1 MBABCNBNDNGODA-WPZDJQSSSA-N 0.000 description 1
• IMUQLZLGWJSVMV-UOBFQKKOSA-N roridin A Natural products CC(O)C1OCCC(C)C(O)C(=O)OCC2CC(=CC3OC4CC(OC(=O)C=C/C=C/1)C(C)(C23)C45CO5)C IMUQLZLGWJSVMV-UOBFQKKOSA-N 0.000 description 1
• VHXNKPBCCMUMSW-FQEVSTJZSA-N rubitecan Chemical compound C1=CC([N+]([O-])=O)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VHXNKPBCCMUMSW-FQEVSTJZSA-N 0.000 description 1
• CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
• 229940081974 saccharin Drugs 0.000 description 1
• 235000019204 saccharin Nutrition 0.000 description 1
• 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
• 229960004889 salicylic acid Drugs 0.000 description 1
• 201000003804 salivary gland carcinoma Diseases 0.000 description 1
• 229930182947 sarcodictyin Natural products 0.000 description 1
• 229940043230 sarcosine Drugs 0.000 description 1
• 239000012047 saturated solution Substances 0.000 description 1
• HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical class O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
• XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
• 238000011452 sequencing regimen Methods 0.000 description 1
• 238000007493 shaping process Methods 0.000 description 1
• 230000019491 signal transduction Effects 0.000 description 1
• 229910001923 silver oxide Inorganic materials 0.000 description 1
• XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
• 229950001403 sizofiran Drugs 0.000 description 1
• 208000000587 small cell lung carcinoma Diseases 0.000 description 1
• 210000000813 small intestine Anatomy 0.000 description 1
• 239000001632 sodium acetate Substances 0.000 description 1
• 235000017281 sodium acetate Nutrition 0.000 description 1
• 235000010413 sodium alginate Nutrition 0.000 description 1
• 239000000661 sodium alginate Substances 0.000 description 1
• 229940005550 sodium alginate Drugs 0.000 description 1
• URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
• 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
• 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
• 239000011780 sodium chloride Substances 0.000 description 1
• 239000012312 sodium hydride Substances 0.000 description 1
• 229910000104 sodium hydride Inorganic materials 0.000 description 1
• 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
• 239000001488 sodium phosphate Substances 0.000 description 1
• 229910000162 sodium phosphate Inorganic materials 0.000 description 1
• 239000007901 soft capsule Substances 0.000 description 1
• 239000008247 solid mixture Substances 0.000 description 1
• 239000007790 solid phase Substances 0.000 description 1
• 239000011877 solvent mixture Substances 0.000 description 1
• 229960003787 sorafenib Drugs 0.000 description 1
• 238000001179 sorption measurement Methods 0.000 description 1
• 241000894007 species Species 0.000 description 1
• 230000003595 spectral effect Effects 0.000 description 1
• 125000003003 spiro group Chemical group 0.000 description 1
• 229950006315 spirogermanium Drugs 0.000 description 1
• ICXJVZHDZFXYQC-UHFFFAOYSA-N spongistatin 1 Natural products OC1C(O2)(O)CC(O)C(C)C2CCCC=CC(O2)CC(O)CC2(O2)CC(OC)CC2CC(=O)C(C)C(OC(C)=O)C(C)C(=C)CC(O2)CC(C)(O)CC2(O2)CC(OC(C)=O)CC2CC(=O)OC2C(O)C(CC(=C)CC(O)C=CC(Cl)=C)OC1C2C ICXJVZHDZFXYQC-UHFFFAOYSA-N 0.000 description 1
• 239000007921 spray Substances 0.000 description 1
• 235000019698 starch Nutrition 0.000 description 1
• 239000008107 starch Substances 0.000 description 1
• DFVFTMTWCUHJBL-BQBZGAKWSA-N statine Chemical compound CC(C)C[C@H](N)[C@@H](O)CC(O)=O DFVFTMTWCUHJBL-BQBZGAKWSA-N 0.000 description 1
• SFVFIFLLYFPGHH-UHFFFAOYSA-M stearalkonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 SFVFIFLLYFPGHH-UHFFFAOYSA-M 0.000 description 1
• 239000008117 stearic acid Substances 0.000 description 1
• 238000011146 sterile filtration Methods 0.000 description 1
• 230000001954 sterilising effect Effects 0.000 description 1
• 238000004659 sterilization and disinfection Methods 0.000 description 1
• 229960001052 streptozocin Drugs 0.000 description 1
• ZSJLQEPLLKMAKR-GKHCUFPYSA-N streptozocin Chemical compound O=NN(C)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O ZSJLQEPLLKMAKR-GKHCUFPYSA-N 0.000 description 1
• 238000007920 subcutaneous administration Methods 0.000 description 1
• 238000006467 substitution reaction Methods 0.000 description 1
• 235000000346 sugar Nutrition 0.000 description 1
• 150000005846 sugar alcohols Polymers 0.000 description 1
• 150000008163 sugars Chemical class 0.000 description 1
• 150000003871 sulfonates Chemical class 0.000 description 1
• 150000003460 sulfonic acids Chemical class 0.000 description 1
• 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
• 239000013589 supplement Substances 0.000 description 1
• 239000000829 suppository Substances 0.000 description 1
• 230000002459 sustained effect Effects 0.000 description 1
• 238000013268 sustained release Methods 0.000 description 1
• 239000012730 sustained-release form Substances 0.000 description 1
• 229940034785 sutent Drugs 0.000 description 1
• 239000006188 syrup Substances 0.000 description 1
• 235000020357 syrup Nutrition 0.000 description 1
• 239000000454 talc Substances 0.000 description 1
• 235000012222 talc Nutrition 0.000 description 1
• 229910052623 talc Inorganic materials 0.000 description 1
• 229960001603 tamoxifen Drugs 0.000 description 1
• 229960003454 tamoxifen citrate Drugs 0.000 description 1
• 229940120982 tarceva Drugs 0.000 description 1
• 229940095064 tartrate Drugs 0.000 description 1
• RCINICONZNJXQF-XAZOAEDWSA-N taxol® Chemical compound O([C@@H]1[C@@]2(CC(C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3(C21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-XAZOAEDWSA-N 0.000 description 1
• 229940063683 taxotere Drugs 0.000 description 1
• NRUKOCRGYNPUPR-QBPJDGROSA-N teniposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@@H](OC[C@H]4O3)C=3SC=CC=3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 NRUKOCRGYNPUPR-QBPJDGROSA-N 0.000 description 1
• 229960001278 teniposide Drugs 0.000 description 1
• FMLPQHJYUZTHQS-QMMMGPOBSA-N tert-butyl (3s)-3-methylpiperazine-1-carboxylate Chemical compound C[C@H]1CN(C(=O)OC(C)(C)C)CCN1 FMLPQHJYUZTHQS-QMMMGPOBSA-N 0.000 description 1
• BVTUDVNBQYLPMZ-UHFFFAOYSA-N tert-butyl 4-(dimethylcarbamoyl)piperazine-1-carboxylate Chemical compound CN(C)C(=O)N1CCN(C(=O)OC(C)(C)C)CC1 BVTUDVNBQYLPMZ-UHFFFAOYSA-N 0.000 description 1
• VRVUOIHXJJWKIY-UHFFFAOYSA-N tert-butyl 4-(dimethylcarbamoyl)piperidine-1-carboxylate Chemical compound CN(C)C(=O)C1CCN(C(=O)OC(C)(C)C)CC1 VRVUOIHXJJWKIY-UHFFFAOYSA-N 0.000 description 1
• CBJGTHZUHVNXFG-UHFFFAOYSA-N tert-butyl 4-[2-(dimethylamino)-2-oxoethyl]piperazine-1-carboxylate Chemical compound CN(C)C(=O)CN1CCN(C(=O)OC(C)(C)C)CC1 CBJGTHZUHVNXFG-UHFFFAOYSA-N 0.000 description 1
• KCQLRNNVATXXOV-UHFFFAOYSA-N tert-butyl 4-[2-methoxyethyl(methyl)amino]piperidine-1-carboxylate Chemical compound COCCN(C)C1CCN(C(=O)OC(C)(C)C)CC1 KCQLRNNVATXXOV-UHFFFAOYSA-N 0.000 description 1
• HDIQYMCOHWFMMJ-UHFFFAOYSA-N tert-butyl 4-[2-methoxyethyl(methyl)carbamoyl]piperazine-1-carboxylate Chemical compound COCCN(C)C(=O)N1CCN(C(=O)OC(C)(C)C)CC1 HDIQYMCOHWFMMJ-UHFFFAOYSA-N 0.000 description 1
• VLFPROXJLUGLSB-UHFFFAOYSA-N tert-butyl 4-[2-methyl-1-(methylamino)-1-oxopropan-2-yl]piperazine-1-carboxylate Chemical compound CNC(=O)C(C)(C)N1CCN(C(=O)OC(C)(C)C)CC1 VLFPROXJLUGLSB-UHFFFAOYSA-N 0.000 description 1
• IHDXIBWOARFYTR-UHFFFAOYSA-N tert-butyl 4-[[2-(2-aminopyrimidin-5-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1CC1=CC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 IHDXIBWOARFYTR-UHFFFAOYSA-N 0.000 description 1
• KEVJRVHXORTWTR-UHFFFAOYSA-N tert-butyl 4-methylsulfonylpiperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(S(C)(=O)=O)CC1 KEVJRVHXORTWTR-UHFFFAOYSA-N 0.000 description 1
• DHTIMDYRZSTIDL-UHFFFAOYSA-N tert-butyl n-[5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-6-methylpyridin-2-yl]carbamate Chemical compound CC1=NC(NC(=O)OC(C)(C)C)=CC=C1B1OCC(C)(C)CO1 DHTIMDYRZSTIDL-UHFFFAOYSA-N 0.000 description 1
• 150000003512 tertiary amines Chemical class 0.000 description 1
• 238000012360 testing method Methods 0.000 description 1
• BPEWUONYVDABNZ-DZBHQSCQSA-N testolactone Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)(OC(=O)CC4)[C@@H]4[C@@H]3CCC2=C1 BPEWUONYVDABNZ-DZBHQSCQSA-N 0.000 description 1
• 229960005353 testolactone Drugs 0.000 description 1
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
• 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
• 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
• 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
• OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
• 125000005308 thiazepinyl group Chemical group S1N=C(C=CC=C1)* 0.000 description 1
• 239000002562 thickening agent Substances 0.000 description 1
• 125000001583 thiepanyl group Chemical group 0.000 description 1
• 125000002053 thietanyl group Chemical group 0.000 description 1
• 238000004809 thin layer chromatography Methods 0.000 description 1
• DKGYESBFCGKOJC-UHFFFAOYSA-N thiophen-3-amine Chemical compound NC=1C=CSC=1 DKGYESBFCGKOJC-UHFFFAOYSA-N 0.000 description 1
• 150000003577 thiophenes Chemical class 0.000 description 1
• RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
• 201000002510 thyroid cancer Diseases 0.000 description 1
• 208000030901 thyroid gland follicular carcinoma Diseases 0.000 description 1
• YFTWHEBLORWGNI-UHFFFAOYSA-N tiamiprine Chemical compound CN1C=NC([N+]([O-])=O)=C1SC1=NC(N)=NC2=C1NC=N2 YFTWHEBLORWGNI-UHFFFAOYSA-N 0.000 description 1
• 229950011457 tiamiprine Drugs 0.000 description 1
• 210000001519 tissue Anatomy 0.000 description 1
• 238000003354 tissue distribution assay Methods 0.000 description 1
• 238000004448 titration Methods 0.000 description 1
• 210000002105 tongue Anatomy 0.000 description 1
• 229940100611 topical cream Drugs 0.000 description 1
• 230000000699 topical effect Effects 0.000 description 1
• 229940100615 topical ointment Drugs 0.000 description 1
• 239000012049 topical pharmaceutical composition Substances 0.000 description 1
• 229940044693 topoisomerase inhibitor Drugs 0.000 description 1
• UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 description 1
• 229960000303 topotecan Drugs 0.000 description 1
• 231100000331 toxic Toxicity 0.000 description 1
• 230000002588 toxic effect Effects 0.000 description 1
• 230000001988 toxicity Effects 0.000 description 1
• 231100000419 toxicity Toxicity 0.000 description 1
• 235000010487 tragacanth Nutrition 0.000 description 1
• 239000000196 tragacanth Substances 0.000 description 1
• 229940116362 tragacanth Drugs 0.000 description 1
• 230000005945 translocation Effects 0.000 description 1
• 230000008736 traumatic injury Effects 0.000 description 1
• IUCJMVBFZDHPDX-UHFFFAOYSA-N tretamine Chemical compound C1CN1C1=NC(N2CC2)=NC(N2CC2)=N1 IUCJMVBFZDHPDX-UHFFFAOYSA-N 0.000 description 1
• 229950001353 tretamine Drugs 0.000 description 1
• 229960001727 tretinoin Drugs 0.000 description 1
• 125000004306 triazinyl group Chemical group 0.000 description 1
• PXSOHRWMIRDKMP-UHFFFAOYSA-N triaziquone Chemical compound O=C1C(N2CC2)=C(N2CC2)C(=O)C=C1N1CC1 PXSOHRWMIRDKMP-UHFFFAOYSA-N 0.000 description 1
• 229960004560 triaziquone Drugs 0.000 description 1
• GOWNSHUNTJWVOM-UHFFFAOYSA-N tributyl(1,3-thiazol-5-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CN=CS1 GOWNSHUNTJWVOM-UHFFFAOYSA-N 0.000 description 1
• 229930013292 trichothecene Natural products 0.000 description 1
• 150000003327 trichothecene derivatives Chemical class 0.000 description 1
• KVJXBPDAXMEYOA-CXANFOAXSA-N trilostane Chemical compound OC1=C(C#N)C[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CC[C@@]32O[C@@H]31 KVJXBPDAXMEYOA-CXANFOAXSA-N 0.000 description 1
• 229960001670 trilostane Drugs 0.000 description 1
• NOYPYLRCIDNJJB-UHFFFAOYSA-N trimetrexate Chemical compound COC1=C(OC)C(OC)=CC(NCC=2C(=C3C(N)=NC(N)=NC3=CC=2)C)=C1 NOYPYLRCIDNJJB-UHFFFAOYSA-N 0.000 description 1
• 229960001099 trimetrexate Drugs 0.000 description 1
• 229950000212 trioxifene Drugs 0.000 description 1
• RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
• 229960000875 trofosfamide Drugs 0.000 description 1
• UMKFEPPTGMDVMI-UHFFFAOYSA-N trofosfamide Chemical compound ClCCN(CCCl)P1(=O)OCCCN1CCCl UMKFEPPTGMDVMI-UHFFFAOYSA-N 0.000 description 1
• 229950010147 troxacitabine Drugs 0.000 description 1
• RXRGZNYSEHTMHC-BQBZGAKWSA-N troxacitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1O[C@@H](CO)OC1 RXRGZNYSEHTMHC-BQBZGAKWSA-N 0.000 description 1
• HDZZVAMISRMYHH-LITAXDCLSA-N tubercidin Chemical compound C1=CC=2C(N)=NC=NC=2N1[C@@H]1O[C@@H](CO)[C@H](O)[C@H]1O HDZZVAMISRMYHH-LITAXDCLSA-N 0.000 description 1
• 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 description 1
• 229940094060 tykerb Drugs 0.000 description 1
• 208000027930 type IV hypersensitivity disease Diseases 0.000 description 1
• 229950009811 ubenimex Drugs 0.000 description 1
• 208000010576 undifferentiated carcinoma Diseases 0.000 description 1
• 229960001055 uracil mustard Drugs 0.000 description 1
• 201000005112 urinary bladder cancer Diseases 0.000 description 1
• 208000010570 urinary bladder carcinoma Diseases 0.000 description 1
• 210000002700 urine Anatomy 0.000 description 1
• 206010046766 uterine cancer Diseases 0.000 description 1
• 208000012991 uterine carcinoma Diseases 0.000 description 1
• 229950000578 vatalanib Drugs 0.000 description 1
• YCOYDOIWSSHVCK-UHFFFAOYSA-N vatalanib Chemical compound C1=CC(Cl)=CC=C1NC(C1=CC=CC=C11)=NN=C1CC1=CC=NC=C1 YCOYDOIWSSHVCK-UHFFFAOYSA-N 0.000 description 1
• 229940099039 velcade Drugs 0.000 description 1
• 230000035899 viability Effects 0.000 description 1
• 229960003048 vinblastine Drugs 0.000 description 1
• JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
• OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
• 229960004528 vincristine Drugs 0.000 description 1
• OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
• UGGWPQSBPIFKDZ-KOTLKJBCSA-N vindesine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(N)=O)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1N=C1[C]2C=CC=C1 UGGWPQSBPIFKDZ-KOTLKJBCSA-N 0.000 description 1
• 229960004355 vindesine Drugs 0.000 description 1
• GBABOYUKABKIAF-IELIFDKJSA-N vinorelbine Chemical compound C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC GBABOYUKABKIAF-IELIFDKJSA-N 0.000 description 1
• 229960002066 vinorelbine Drugs 0.000 description 1
• CILBMBUYJCWATM-PYGJLNRPSA-N vinorelbine ditartrate Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.OC(=O)[C@H](O)[C@@H](O)C(O)=O.C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC CILBMBUYJCWATM-PYGJLNRPSA-N 0.000 description 1
• 229920002554 vinyl polymer Polymers 0.000 description 1
• 229960001771 vorozole Drugs 0.000 description 1
• XLMPPFTZALNBFS-INIZCTEOSA-N vorozole Chemical compound C1([C@@H](C2=CC=C3N=NN(C3=C2)C)N2N=CN=C2)=CC=C(Cl)C=C1 XLMPPFTZALNBFS-INIZCTEOSA-N 0.000 description 1
• 201000005102 vulva cancer Diseases 0.000 description 1
• 239000003643 water by type Substances 0.000 description 1
• 238000003809 water extraction Methods 0.000 description 1
• 229940053867 xeloda Drugs 0.000 description 1
• 229910052725 zinc Inorganic materials 0.000 description 1
• 239000011701 zinc Substances 0.000 description 1
• 229950009268 zinostatin Drugs 0.000 description 1
• FBTUMDXHSRTGRV-ALTNURHMSA-N zorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(\C)=N\NC(=O)C=1C=CC=CC=1)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 FBTUMDXHSRTGRV-ALTNURHMSA-N 0.000 description 1
• 229960000641 zorubicin Drugs 0.000 description 1