TWI373471B - 2-amino-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-ones - Google Patents

Info

Publication number

TWI373471B

TWI373471B TW095136162A TW95136162A TWI373471B TW I373471 B TWI373471 B TW I373471B TW 095136162 A TW095136162 A TW 095136162A TW 95136162 A TW95136162 A TW 95136162A TW I373471 B TWI373471 B TW I373471B

Authority

TW

Taiwan

Prior art keywords

group

phenyl

substituted

doc

unsubstituted

Prior art date

2005-09-30

Links

• Espacenet
• Global Dossier
• Discuss

• CZOQBGHFZWUWPV-UHFFFAOYSA-N 2-amino-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical class O=C1NCCC2=NC(N)=NC=C21 CZOQBGHFZWUWPV-UHFFFAOYSA-N 0.000 title description 3
• -1 morpholinylpropyl groups Chemical group 0.000 claims description 606
• 150000001875 compounds Chemical class 0.000 claims description 245
• 125000000217 alkyl group Chemical group 0.000 claims description 106
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 96
• 229910052739 hydrogen Inorganic materials 0.000 claims description 82
• 239000001257 hydrogen Substances 0.000 claims description 82
• 239000002585 base Substances 0.000 claims description 80
• 125000003118 aryl group Chemical group 0.000 claims description 70
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 67
• 125000001072 heteroaryl group Chemical group 0.000 claims description 60
• 206010028980 Neoplasm Diseases 0.000 claims description 49
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 49
• 125000000623 heterocyclic group Chemical group 0.000 claims description 48
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 44
• 239000000203 mixture Substances 0.000 claims description 44
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 41
• 238000000034 method Methods 0.000 claims description 41
• 150000003839 salts Chemical class 0.000 claims description 40
• 125000003545 alkoxy group Chemical group 0.000 claims description 39
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 38
• 102100034051 Heat shock protein HSP 90-alpha Human genes 0.000 claims description 32
• 125000003277 amino group Chemical group 0.000 claims description 32
• 201000011510 cancer Diseases 0.000 claims description 31
• 101710113864 Heat shock protein 90 Proteins 0.000 claims description 29
• 150000001412 amines Chemical class 0.000 claims description 29
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 27
• 239000007789 gas Substances 0.000 claims description 26
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 25
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 25
• 238000011282 treatment Methods 0.000 claims description 25
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 21
• 125000005843 halogen group Chemical group 0.000 claims description 20
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 20
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 19
• 229910052757 nitrogen Inorganic materials 0.000 claims description 19
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
• 239000003814 drug Substances 0.000 claims description 15
• 239000002253 acid Substances 0.000 claims description 14
• 125000003342 alkenyl group Chemical group 0.000 claims description 14
• 125000000304 alkynyl group Chemical group 0.000 claims description 14
• 239000003795 chemical substances by application Substances 0.000 claims description 14
• 230000000694 effects Effects 0.000 claims description 14
• 125000004076 pyridyl group Chemical group 0.000 claims description 13
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 13
• 241001465754 Metazoa Species 0.000 claims description 12
• 238000002360 preparation method Methods 0.000 claims description 12
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 12
• 125000003107 substituted aryl group Chemical group 0.000 claims description 12
• 125000001544 thienyl group Chemical group 0.000 claims description 12
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 12
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 11
• 229910052736 halogen Inorganic materials 0.000 claims description 11
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 11
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 11
• 125000000335 thiazolyl group Chemical group 0.000 claims description 11
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 10
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
• 125000002883 imidazolyl group Chemical group 0.000 claims description 9
• 125000002971 oxazolyl group Chemical group 0.000 claims description 9
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 9
• 150000003573 thiols Chemical class 0.000 claims description 9
• 229940079593 drug Drugs 0.000 claims description 8
• 239000011737 fluorine Substances 0.000 claims description 8
• 229910052731 fluorine Inorganic materials 0.000 claims description 8
• 150000002367 halogens Chemical class 0.000 claims description 8
• WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 8
• 125000001425 triazolyl group Chemical group 0.000 claims description 8
• 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 claims description 7
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
• MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 claims description 7
• 125000001153 fluoro group Chemical group F* 0.000 claims description 7
• 125000002541 furyl group Chemical group 0.000 claims description 7
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 7
• 125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 6
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 6
• 239000005517 L01XE01 - Imatinib Substances 0.000 claims description 6
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 6
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
• KTUFNOKKBVMGRW-UHFFFAOYSA-N imatinib Chemical compound 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 KTUFNOKKBVMGRW-UHFFFAOYSA-N 0.000 claims description 6
• 150000002923 oximes Chemical class 0.000 claims description 6
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 5
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 5
• 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 5
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 5
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 5
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
• 150000001345 alkine derivatives Chemical class 0.000 claims description 5
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
• 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 5
• 125000004212 difluorophenyl group Chemical group 0.000 claims description 5
• 239000012458 free base Substances 0.000 claims description 5
• 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 claims description 5
• 125000005956 isoquinolyl group Chemical group 0.000 claims description 5
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 5
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
• 125000005493 quinolyl group Chemical group 0.000 claims description 5
• 230000001225 therapeutic effect Effects 0.000 claims description 5
• 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 4
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 4
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 125000005805 dimethoxy phenyl group Chemical group 0.000 claims description 4
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 4
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
• 229960004641 rituximab Drugs 0.000 claims description 4
• RRXSYZFVDIRTFB-UHFFFAOYSA-N C[CH]C1=CC=C(OC)C=C1 Chemical group C[CH]C1=CC=C(OC)C=C1 RRXSYZFVDIRTFB-UHFFFAOYSA-N 0.000 claims description 3
• 150000002429 hydrazines Chemical class 0.000 claims description 3
• 229960002411 imatinib Drugs 0.000 claims description 3
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 3
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
• 239000007921 spray Substances 0.000 claims description 3
• GOYDNIKZWGIXJT-UHFFFAOYSA-N 1,2-difluorobenzene Chemical compound FC1=CC=CC=C1F GOYDNIKZWGIXJT-UHFFFAOYSA-N 0.000 claims description 2
• CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims description 2
• 102100034535 Histone H3.1 Human genes 0.000 claims description 2
• 101001067844 Homo sapiens Histone H3.1 Proteins 0.000 claims description 2
• 239000005551 L01XE03 - Erlotinib Substances 0.000 claims description 2
• 239000002147 L01XE04 - Sunitinib Substances 0.000 claims description 2
• 229940123237 Taxane Drugs 0.000 claims description 2
• 229930013930 alkaloid Natural products 0.000 claims description 2
• 150000001356 alkyl thiols Chemical class 0.000 claims description 2
• 229940045799 anthracyclines and related substance Drugs 0.000 claims description 2
• VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 claims description 2
• 229960004562 carboplatin Drugs 0.000 claims description 2
• DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims description 2
• 229960004316 cisplatin Drugs 0.000 claims description 2
• 229960004397 cyclophosphamide Drugs 0.000 claims 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 claims description 2
• 229960001433 erlotinib Drugs 0.000 claims description 2
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
• 230000001105 regulatory effect Effects 0.000 claims description 2
• WINHZLLDWRZWRT-ATVHPVEESA-N sunitinib Chemical compound CCN(CC)CCNC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C WINHZLLDWRZWRT-ATVHPVEESA-N 0.000 claims description 2
• 229960001796 sunitinib Drugs 0.000 claims description 2
• 238000012360 testing method Methods 0.000 claims description 2
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
• 150000002431 hydrogen Chemical group 0.000 claims 10
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims 4
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 3
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
• 229910052786 argon Inorganic materials 0.000 claims 2
• WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims 2
• 241000894007 species Species 0.000 claims 2
• VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims 2
• HYFLWBNQFMXCPA-UHFFFAOYSA-N 1-ethyl-2-methylbenzene Chemical compound CCC1=CC=CC=C1C HYFLWBNQFMXCPA-UHFFFAOYSA-N 0.000 claims 1
• BESOQRFWCAJXLE-UHFFFAOYSA-N 2,3-bis(bromomethyl)-1,4-dimethoxybenzene Chemical compound COC1=CC=C(OC)C(CBr)=C1CBr BESOQRFWCAJXLE-UHFFFAOYSA-N 0.000 claims 1
• YTYIMDRWPTUAHP-UHFFFAOYSA-N 6-Chloroindole Chemical compound ClC1=CC=C2C=CNC2=C1 YTYIMDRWPTUAHP-UHFFFAOYSA-N 0.000 claims 1
• 102100037651 AP-2 complex subunit sigma Human genes 0.000 claims 1
• 229920003026 Acene Polymers 0.000 claims 1
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 1
• 241001674044 Blattodea Species 0.000 claims 1
• 101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 claims 1
• 206010011224 Cough Diseases 0.000 claims 1
• 241001071795 Gentiana Species 0.000 claims 1
• 101000806914 Homo sapiens AP-2 complex subunit sigma Proteins 0.000 claims 1
• 206010020850 Hyperthyroidism Diseases 0.000 claims 1
• BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims 1
• 125000005036 alkoxyphenyl group Chemical group 0.000 claims 1
• AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical group [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 claims 1
• 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
• 229910052747 lanthanoid Inorganic materials 0.000 claims 1
• 150000002602 lanthanoids Chemical class 0.000 claims 1
• 125000003431 oxalo group Chemical group 0.000 claims 1
• DPZNOMCNRMUKPS-UHFFFAOYSA-N resorcinol dimethyl ether Natural products COC1=CC=CC(OC)=C1 DPZNOMCNRMUKPS-UHFFFAOYSA-N 0.000 claims 1
• 229910052709 silver Inorganic materials 0.000 claims 1
• 239000004332 silver Substances 0.000 claims 1
• 239000002689 soil Substances 0.000 claims 1
• DKPFODGZWDEEBT-QFIAKTPHSA-N taxane Chemical class C([C@]1(C)CCC[C@@H](C)[C@H]1C1)C[C@H]2[C@H](C)CC[C@@H]1C2(C)C DKPFODGZWDEEBT-QFIAKTPHSA-N 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 74
• BDTRIDKONHOQQN-UHFFFAOYSA-N 4h-pyrimidin-5-one Chemical class O=C1CN=CN=C1 BDTRIDKONHOQQN-UHFFFAOYSA-N 0.000 description 61
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 59
• 235000019439 ethyl acetate Nutrition 0.000 description 36
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
• 239000011541 reaction mixture Substances 0.000 description 30
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 26
• 238000006243 chemical reaction Methods 0.000 description 24
• 229910052799 carbon Inorganic materials 0.000 description 22
• 210000004027 cell Anatomy 0.000 description 22
• 125000001424 substituent group Chemical group 0.000 description 22
• 125000003710 aryl alkyl group Chemical group 0.000 description 21
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 20
• 125000004432 carbon atom Chemical group C* 0.000 description 20
• 108090000623 proteins and genes Proteins 0.000 description 20
• 102000004169 proteins and genes Human genes 0.000 description 20
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 19
• 229940002612 prodrug Drugs 0.000 description 19
• 239000000651 prodrug Substances 0.000 description 19
• 239000000243 solution Substances 0.000 description 19
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
• 201000010099 disease Diseases 0.000 description 18
• 239000003481 heat shock protein 90 inhibitor Substances 0.000 description 15
• 150000002576 ketones Chemical class 0.000 description 15
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 14
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
• 150000001721 carbon Chemical group 0.000 description 13
• 239000002904 solvent Substances 0.000 description 13
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
• 230000005764 inhibitory process Effects 0.000 description 11
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 11
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
• 238000004128 high performance liquid chromatography Methods 0.000 description 10
• 239000007787 solid Substances 0.000 description 10
• 230000003612 virological effect Effects 0.000 description 10
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 9
• 125000003282 alkyl amino group Chemical group 0.000 description 9
• 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
• 230000002062 proliferating effect Effects 0.000 description 9
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 8
• 208000024172 Cardiovascular disease Diseases 0.000 description 8
• 239000002246 antineoplastic agent Substances 0.000 description 8
• 230000006907 apoptotic process Effects 0.000 description 8
• 230000002526 effect on cardiovascular system Effects 0.000 description 8
• 125000005842 heteroatom Chemical group 0.000 description 8
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
• 239000000543 intermediate Substances 0.000 description 8
• 239000010410 layer Substances 0.000 description 8
• 230000001404 mediated effect Effects 0.000 description 8
• 125000004433 nitrogen atom Chemical group N* 0.000 description 8
• ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 7
• 206010006187 Breast cancer Diseases 0.000 description 7
• 208000026310 Breast neoplasm Diseases 0.000 description 7
• 125000006519 CCH3 Chemical group 0.000 description 7
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
• 230000001363 autoimmune Effects 0.000 description 7
• 208000015114 central nervous system disease Diseases 0.000 description 7
• 125000004446 heteroarylalkyl group Chemical group 0.000 description 7
• 229910052717 sulfur Inorganic materials 0.000 description 7
• 239000000725 suspension Substances 0.000 description 7
• 206010012812 Diffuse cutaneous mastocytosis Diseases 0.000 description 6
• 206010036790 Productive cough Diseases 0.000 description 6
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
• MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 6
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
• 230000004663 cell proliferation Effects 0.000 description 6
• 208000035475 disorder Diseases 0.000 description 6
• 230000012010 growth Effects 0.000 description 6
• 125000001188 haloalkyl group Chemical group 0.000 description 6
• 230000002401 inhibitory effect Effects 0.000 description 6
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 6
• 229940043355 kinase inhibitor Drugs 0.000 description 6
• 239000002502 liposome Substances 0.000 description 6
• 125000001715 oxadiazolyl group Chemical group 0.000 description 6
• 229910052760 oxygen Inorganic materials 0.000 description 6
• 239000001301 oxygen Substances 0.000 description 6
• 239000003757 phosphotransferase inhibitor Substances 0.000 description 6
• 238000010992 reflux Methods 0.000 description 6
• 210000003802 sputum Anatomy 0.000 description 6
• 208000024794 sputum Diseases 0.000 description 6
• 239000000126 substance Substances 0.000 description 6
• 239000011593 sulfur Substances 0.000 description 6
• 229940124597 therapeutic agent Drugs 0.000 description 6
• 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 description 5
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 5
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 5
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
• 238000005481 NMR spectroscopy Methods 0.000 description 5
• 206010060862 Prostate cancer Diseases 0.000 description 5
• 208000000236 Prostatic Neoplasms Diseases 0.000 description 5
• 208000005718 Stomach Neoplasms Diseases 0.000 description 5
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 5
• 208000035362 autoimmune disorder of the nervous system Diseases 0.000 description 5
• 239000003937 drug carrier Substances 0.000 description 5
• 125000000524 functional group Chemical group 0.000 description 5
• 125000004438 haloalkoxy group Chemical group 0.000 description 5
• 229940088597 hormone Drugs 0.000 description 5
• 239000005556 hormone Substances 0.000 description 5
• 239000003112 inhibitor Substances 0.000 description 5
• 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 5
• 201000001441 melanoma Diseases 0.000 description 5
• 231100000252 nontoxic Toxicity 0.000 description 5
• 230000003000 nontoxic effect Effects 0.000 description 5
• 239000003921 oil Substances 0.000 description 5
• 239000000546 pharmaceutical excipient Substances 0.000 description 5
• 239000000843 powder Substances 0.000 description 5
• 238000000159 protein binding assay Methods 0.000 description 5
• 238000006467 substitution reaction Methods 0.000 description 5
• 238000004809 thin layer chromatography Methods 0.000 description 5
• 239000000052 vinegar Substances 0.000 description 5
• 235000021419 vinegar Nutrition 0.000 description 5
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
• 102000001301 EGF receptor Human genes 0.000 description 4
• 108060006698 EGF receptor Proteins 0.000 description 4
• 108010002616 Interleukin-5 Proteins 0.000 description 4
• 108010006519 Molecular Chaperones Proteins 0.000 description 4
• 102000005431 Molecular Chaperones Human genes 0.000 description 4
• 208000034578 Multiple myelomas Diseases 0.000 description 4
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
• 206010033128 Ovarian cancer Diseases 0.000 description 4
• 206010061535 Ovarian neoplasm Diseases 0.000 description 4
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
• 108091000080 Phosphotransferase Proteins 0.000 description 4
• 206010035226 Plasma cell myeloma Diseases 0.000 description 4
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
• 238000006069 Suzuki reaction reaction Methods 0.000 description 4
• 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 4
• 208000024770 Thyroid neoplasm Diseases 0.000 description 4
• 102400000336 Thyrotropin-releasing hormone Human genes 0.000 description 4
• 238000003556 assay Methods 0.000 description 4
• 230000015572 biosynthetic process Effects 0.000 description 4
• 208000029742 colonic neoplasm Diseases 0.000 description 4
• 238000001816 cooling Methods 0.000 description 4
• 239000002552 dosage form Substances 0.000 description 4
• 150000002148 esters Chemical class 0.000 description 4
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
• 206010017758 gastric cancer Diseases 0.000 description 4
• 238000010438 heat treatment Methods 0.000 description 4
• 230000007062 hydrolysis Effects 0.000 description 4
• 238000006460 hydrolysis reaction Methods 0.000 description 4
• 201000007270 liver cancer Diseases 0.000 description 4
• 208000014018 liver neoplasm Diseases 0.000 description 4
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
• 238000004949 mass spectrometry Methods 0.000 description 4
• 125000002950 monocyclic group Chemical group 0.000 description 4
• 125000004043 oxo group Chemical group O=* 0.000 description 4
• 102000020233 phosphotransferase Human genes 0.000 description 4
• 239000000047 product Substances 0.000 description 4
• 238000000746 purification Methods 0.000 description 4
• 238000004007 reversed phase HPLC Methods 0.000 description 4
• 230000002441 reversible effect Effects 0.000 description 4
• 201000011549 stomach cancer Diseases 0.000 description 4
• 229910021653 sulphate ion Inorganic materials 0.000 description 4
• PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 3
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 3
• CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 3
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
• 206010005003 Bladder cancer Diseases 0.000 description 3
• 208000003174 Brain Neoplasms Diseases 0.000 description 3
• 206010008342 Cervix carcinoma Diseases 0.000 description 3
• 208000010833 Chronic myeloid leukaemia Diseases 0.000 description 3
• 206010048832 Colon adenoma Diseases 0.000 description 3
• 206010009944 Colon cancer Diseases 0.000 description 3
• 208000000461 Esophageal Neoplasms Diseases 0.000 description 3
• 101001016865 Homo sapiens Heat shock protein HSP 90-alpha Proteins 0.000 description 3
• 206010023825 Laryngeal cancer Diseases 0.000 description 3
• 206010025323 Lymphomas Diseases 0.000 description 3
• 208000003445 Mouth Neoplasms Diseases 0.000 description 3
• 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 description 3
• 206010030155 Oesophageal carcinoma Diseases 0.000 description 3
• 206010061902 Pancreatic neoplasm Diseases 0.000 description 3
• 208000009565 Pharyngeal Neoplasms Diseases 0.000 description 3
• 206010034811 Pharyngeal cancer Diseases 0.000 description 3
• 108091008611 Protein Kinase B Proteins 0.000 description 3
• 208000015634 Rectal Neoplasms Diseases 0.000 description 3
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 3
• 208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 3
• 125000004183 alkoxy alkyl group Chemical group 0.000 description 3
• 238000004458 analytical method Methods 0.000 description 3
• 229940046836 anti-estrogen Drugs 0.000 description 3
• 230000001833 anti-estrogenic effect Effects 0.000 description 3
• 125000004104 aryloxy group Chemical group 0.000 description 3
• 125000004429 atom Chemical group 0.000 description 3
• 239000011203 carbon fibre reinforced carbon Substances 0.000 description 3
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
• 230000025084 cell cycle arrest Effects 0.000 description 3
• 230000010261 cell growth Effects 0.000 description 3
• 230000001413 cellular effect Effects 0.000 description 3
• 201000010881 cervical cancer Diseases 0.000 description 3
• 208000006990 cholangiocarcinoma Diseases 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
• 239000012043 crude product Substances 0.000 description 3
• 239000013078 crystal Substances 0.000 description 3
• 230000001419 dependent effect Effects 0.000 description 3
• 239000000839 emulsion Substances 0.000 description 3
• 201000004101 esophageal cancer Diseases 0.000 description 3
• 239000000328 estrogen antagonist Substances 0.000 description 3
• 239000000706 filtrate Substances 0.000 description 3
• 229940080856 gleevec Drugs 0.000 description 3
• 208000014829 head and neck neoplasm Diseases 0.000 description 3
• 150000002430 hydrocarbons Chemical group 0.000 description 3
• 238000000338 in vitro Methods 0.000 description 3
• 239000003701 inert diluent Substances 0.000 description 3
• 201000007450 intrahepatic cholangiocarcinoma Diseases 0.000 description 3
• 229960004768 irinotecan Drugs 0.000 description 3
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 3
• 206010023841 laryngeal neoplasm Diseases 0.000 description 3
• 230000000670 limiting effect Effects 0.000 description 3
• 208000012987 lip and oral cavity carcinoma Diseases 0.000 description 3
• 208000020816 lung neoplasm Diseases 0.000 description 3
• 210000004698 lymphocyte Anatomy 0.000 description 3
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 3
• 239000000463 material Substances 0.000 description 3
• 239000011159 matrix material Substances 0.000 description 3
• 208000025113 myeloid leukemia Diseases 0.000 description 3
• 229940127084 other anti-cancer agent Drugs 0.000 description 3
• 201000002528 pancreatic cancer Diseases 0.000 description 3
• 208000008443 pancreatic carcinoma Diseases 0.000 description 3
• 230000037361 pathway Effects 0.000 description 3
• 239000012071 phase Substances 0.000 description 3
• 150000003904 phospholipids Chemical class 0.000 description 3
• 239000006187 pill Substances 0.000 description 3
• 150000003254 radicals Chemical class 0.000 description 3
• 102000005962 receptors Human genes 0.000 description 3
• 108020003175 receptors Proteins 0.000 description 3
• 206010038038 rectal cancer Diseases 0.000 description 3
• 201000001275 rectum cancer Diseases 0.000 description 3
• 238000007363 ring formation reaction Methods 0.000 description 3
• 238000000926 separation method Methods 0.000 description 3
• 230000035939 shock Effects 0.000 description 3
• 201000002314 small intestine cancer Diseases 0.000 description 3
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
• 238000003756 stirring Methods 0.000 description 3
• 125000005017 substituted alkenyl group Chemical group 0.000 description 3
• 125000004426 substituted alkynyl group Chemical group 0.000 description 3
• 238000003786 synthesis reaction Methods 0.000 description 3
• 125000001113 thiadiazolyl group Chemical group 0.000 description 3
• 201000002510 thyroid cancer Diseases 0.000 description 3
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
• 210000004881 tumor cell Anatomy 0.000 description 3
• 201000005112 urinary bladder cancer Diseases 0.000 description 3
• FDKXTQMXEQVLRF-ZHACJKMWSA-N (E)-dacarbazine Chemical compound CN(C)\N=N\c1[nH]cnc1C(N)=O FDKXTQMXEQVLRF-ZHACJKMWSA-N 0.000 description 2
• UKSNPQPAROIFBP-NDHCZCPUSA-N (z)-2-amino-n-[(2s,3s,4r,5r)-5-[6-(dimethylamino)purin-9-yl]-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-enamide Chemical compound C1=C(O)C(OC)=CC=C1\C=C(/N)C(=O)N[C@H]1[C@@H](O)[C@H](N2C3=NC=NC(=C3N=C2)N(C)C)O[C@@H]1CO UKSNPQPAROIFBP-NDHCZCPUSA-N 0.000 description 2
• VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 2
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
• AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
• FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
• IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 description 2
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
• ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 description 2
• WEVYNIUIFUYDGI-UHFFFAOYSA-N 3-[6-[4-(trifluoromethoxy)anilino]-4-pyrimidinyl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2N=CN=C(NC=3C=CC(OC(F)(F)F)=CC=3)C=2)=C1 WEVYNIUIFUYDGI-UHFFFAOYSA-N 0.000 description 2
• 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 2
• 208000031261 Acute myeloid leukaemia Diseases 0.000 description 2
• 208000023345 Autoimmune Diseases of the Nervous System Diseases 0.000 description 2
• 208000023275 Autoimmune disease Diseases 0.000 description 2
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 2
• 101710163595 Chaperone protein DnaK Proteins 0.000 description 2
• 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
• 229920000858 Cyclodextrin Polymers 0.000 description 2
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
• 206010014733 Endometrial cancer Diseases 0.000 description 2
• 206010014759 Endometrial neoplasm Diseases 0.000 description 2
• ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 2
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
• GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 2
• JRZJKWGQFNTSRN-UHFFFAOYSA-N Geldanamycin Natural products C1C(C)CC(OC)C(O)C(C)C=C(C)C(OC(N)=O)C(OC)CCC=C(C)C(=O)NC2=CC(=O)C(OC)=C1C2=O JRZJKWGQFNTSRN-UHFFFAOYSA-N 0.000 description 2
• 101710178376 Heat shock 70 kDa protein Proteins 0.000 description 2
• 101710152018 Heat shock cognate 70 kDa protein Proteins 0.000 description 2
• 108010004889 Heat-Shock Proteins Proteins 0.000 description 2
• 102000002812 Heat-Shock Proteins Human genes 0.000 description 2
• 241000700721 Hepatitis B virus Species 0.000 description 2
• 241000700588 Human alphaherpesvirus 1 Species 0.000 description 2
• 206010058467 Lung neoplasm malignant Diseases 0.000 description 2
• TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
• LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
• 208000033776 Myeloid Acute Leukemia Diseases 0.000 description 2
• 208000012902 Nervous system disease Diseases 0.000 description 2
• 208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 2
• 108091008606 PDGF receptors Proteins 0.000 description 2
• 206010061336 Pelvic neoplasm Diseases 0.000 description 2
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
• 102000011653 Platelet-Derived Growth Factor Receptors Human genes 0.000 description 2
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
• 206010039424 Salivary hypersecretion Diseases 0.000 description 2
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
• PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
• 108091008605 VEGF receptors Proteins 0.000 description 2
• 102000009484 Vascular Endothelial Growth Factor Receptors Human genes 0.000 description 2
• 238000010521 absorption reaction Methods 0.000 description 2
• DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
• 230000004913 activation Effects 0.000 description 2
• 230000001154 acute effect Effects 0.000 description 2
• 239000002671 adjuvant Substances 0.000 description 2
• 150000001335 aliphatic alkanes Chemical group 0.000 description 2
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
• 150000001342 alkaline earth metals Chemical class 0.000 description 2
• 150000003973 alkyl amines Chemical class 0.000 description 2
• 125000004448 alkyl carbonyl group Chemical group 0.000 description 2
• 125000004414 alkyl thio group Chemical group 0.000 description 2
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
• 125000004103 aminoalkyl group Chemical group 0.000 description 2
• 230000033115 angiogenesis Effects 0.000 description 2
• 230000000692 anti-sense effect Effects 0.000 description 2
• 229940041181 antineoplastic drug Drugs 0.000 description 2
• 125000005099 aryl alkyl carbonyl group Chemical group 0.000 description 2
• 125000001769 aryl amino group Chemical group 0.000 description 2
• 125000005129 aryl carbonyl group Chemical group 0.000 description 2
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
• 210000004369 blood Anatomy 0.000 description 2
• 239000008280 blood Substances 0.000 description 2
• 230000037396 body weight Effects 0.000 description 2
• 239000012267 brine Substances 0.000 description 2
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
• 229910052794 bromium Inorganic materials 0.000 description 2
• 125000001246 bromo group Chemical group Br* 0.000 description 2
• 239000000872 buffer Substances 0.000 description 2
• 239000002775 capsule Substances 0.000 description 2
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
• 208000015606 cardiovascular system disease Diseases 0.000 description 2
• 230000024245 cell differentiation Effects 0.000 description 2
• 210000003169 central nervous system Anatomy 0.000 description 2
• 239000000460 chlorine Substances 0.000 description 2
• 238000004587 chromatography analysis Methods 0.000 description 2
• 229910052802 copper Inorganic materials 0.000 description 2
• 239000010949 copper Substances 0.000 description 2
• OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
• 125000004122 cyclic group Chemical group 0.000 description 2
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 2
• 230000006378 damage Effects 0.000 description 2
• 238000010511 deprotection reaction Methods 0.000 description 2
• 238000011161 development Methods 0.000 description 2
• 230000018109 developmental process Effects 0.000 description 2
• 125000004663 dialkyl amino group Chemical group 0.000 description 2
• 238000010494 dissociation reaction Methods 0.000 description 2
• 150000002081 enamines Chemical class 0.000 description 2
• 125000004185 ester group Chemical group 0.000 description 2
• PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 2
• 238000003818 flash chromatography Methods 0.000 description 2
• 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 2
• 125000001207 fluorophenyl group Chemical group 0.000 description 2
• 229960002949 fluorouracil Drugs 0.000 description 2
• 238000009472 formulation Methods 0.000 description 2
• 201000011243 gastrointestinal stromal tumor Diseases 0.000 description 2
• QTQAWLPCGQOSGP-GBTDJJJQSA-N geldanamycin Chemical compound N1C(=O)\C(C)=C/C=C\[C@@H](OC)[C@H](OC(N)=O)\C(C)=C/[C@@H](C)[C@@H](O)[C@H](OC)C[C@@H](C)CC2=C(OC)C(=O)C=C1C2=O QTQAWLPCGQOSGP-GBTDJJJQSA-N 0.000 description 2
• 230000002068 genetic effect Effects 0.000 description 2
• 208000005017 glioblastoma Diseases 0.000 description 2
• 150000004820 halides Chemical class 0.000 description 2
• 201000005787 hematologic cancer Diseases 0.000 description 2
• 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 description 2
• 229940022353 herceptin Drugs 0.000 description 2
• 125000005223 heteroarylcarbonyl group Chemical group 0.000 description 2
• 125000000592 heterocycloalkyl group Chemical group 0.000 description 2
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
• 125000001841 imino group Chemical group [H]N=* 0.000 description 2
• 238000001727 in vivo Methods 0.000 description 2
• 238000011065 in-situ storage Methods 0.000 description 2
• 238000002347 injection Methods 0.000 description 2
• 239000007924 injection Substances 0.000 description 2
• 238000002955 isolation Methods 0.000 description 2
• 208000032839 leukemia Diseases 0.000 description 2
• 150000002632 lipids Chemical class 0.000 description 2
• 201000005202 lung cancer Diseases 0.000 description 2
• 235000019359 magnesium stearate Nutrition 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
• 208000000516 mast-cell leukemia Diseases 0.000 description 2
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
• UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
• 229920000609 methyl cellulose Polymers 0.000 description 2
• 239000001923 methylcellulose Substances 0.000 description 2
• 235000010981 methylcellulose Nutrition 0.000 description 2
• 150000007522 mineralic acids Chemical class 0.000 description 2
• BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
• 125000002757 morpholinyl group Chemical group 0.000 description 2
• 230000035772 mutation Effects 0.000 description 2
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
• 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 2
• 239000000346 nonvolatile oil Substances 0.000 description 2
• 150000007524 organic acids Chemical class 0.000 description 2
• 239000012044 organic layer Substances 0.000 description 2
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 2
• 125000004430 oxygen atom Chemical group O* 0.000 description 2
• 239000008194 pharmaceutical composition Substances 0.000 description 2
• 230000026731 phosphorylation Effects 0.000 description 2
• 238000006366 phosphorylation reaction Methods 0.000 description 2
• 238000002953 preparative HPLC Methods 0.000 description 2
• 230000008569 process Effects 0.000 description 2
• PLZDHJUUEGCXJH-UHFFFAOYSA-N pyrido[4,3-d]pyrimidine Chemical compound C1=NC=C2C=NC=CC2=N1 PLZDHJUUEGCXJH-UHFFFAOYSA-N 0.000 description 2
• 238000006268 reductive amination reaction Methods 0.000 description 2
• 230000010076 replication Effects 0.000 description 2
• 230000004044 response Effects 0.000 description 2
• 125000006413 ring segment Chemical group 0.000 description 2
• 208000026451 salivation Diseases 0.000 description 2
• 229920006395 saturated elastomer Polymers 0.000 description 2
• 230000019491 signal transduction Effects 0.000 description 2
• 239000000741 silica gel Substances 0.000 description 2
• 229910002027 silica gel Inorganic materials 0.000 description 2
• 239000011734 sodium Substances 0.000 description 2
• 229910052708 sodium Inorganic materials 0.000 description 2
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
• 229910000029 sodium carbonate Inorganic materials 0.000 description 2
• 239000007909 solid dosage form Substances 0.000 description 2
• PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
• 235000021286 stilbenes Nutrition 0.000 description 2
• KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
• 125000004434 sulfur atom Chemical group 0.000 description 2
• 239000000375 suspending agent Substances 0.000 description 2
• 230000002459 sustained effect Effects 0.000 description 2
• 229960001603 tamoxifen Drugs 0.000 description 2
• WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 2
• 238000012546 transfer Methods 0.000 description 2
• 229960000575 trastuzumab Drugs 0.000 description 2
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 2
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
• 229940124676 vascular endothelial growth factor receptor Drugs 0.000 description 2
• 239000003981 vehicle Substances 0.000 description 2
• 238000005406 washing Methods 0.000 description 2
• 239000003643 water by type Substances 0.000 description 2
• BMKDZUISNHGIBY-ZETCQYMHSA-N (+)-dexrazoxane Chemical compound C([C@H](C)N1CC(=O)NC(=O)C1)N1CC(=O)NC(=O)C1 BMKDZUISNHGIBY-ZETCQYMHSA-N 0.000 description 1
• LSPHULWDVZXLIL-UHFFFAOYSA-N (+/-)-Camphoric acid Chemical compound CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 description 1
• JTDGKQNNPKXKII-ZETCQYMHSA-N (1s)-1-(4-methoxyphenyl)ethanamine Chemical compound COC1=CC=C([C@H](C)N)C=C1 JTDGKQNNPKXKII-ZETCQYMHSA-N 0.000 description 1
• XMAYWYJOQHXEEK-OZXSUGGESA-N (2R,4S)-ketoconazole Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OC[C@@H]1O[C@@](CN2C=NC=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 XMAYWYJOQHXEEK-OZXSUGGESA-N 0.000 description 1
• OWKFMMGDGVSSCH-CQSZACIVSA-N (7r)-2-amino-7-[2-(2,4-dimethoxypyrimidin-5-yl)-4-fluorophenyl]-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound COC1=NC(OC)=NC=C1C1=CC(F)=CC=C1[C@@H]1NC(=O)C2=CN=C(N)N=C2C1 OWKFMMGDGVSSCH-CQSZACIVSA-N 0.000 description 1
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
• WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-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
• 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
• FBZVZUSVGKOWHG-UHFFFAOYSA-N 1,1-dimethoxy-n,n-dimethylethanamine Chemical compound COC(C)(OC)N(C)C FBZVZUSVGKOWHG-UHFFFAOYSA-N 0.000 description 1
• KVGZZAHHUNAVKZ-UHFFFAOYSA-N 1,4-Dioxin Chemical compound O1C=COC=C1 KVGZZAHHUNAVKZ-UHFFFAOYSA-N 0.000 description 1
• VUQPJRPDRDVQMN-UHFFFAOYSA-N 1-chlorooctadecane Chemical class CCCCCCCCCCCCCCCCCCCl VUQPJRPDRDVQMN-UHFFFAOYSA-N 0.000 description 1
• KVGOXGQSTGQXDD-UHFFFAOYSA-N 1-decane-sulfonic-acid Chemical compound CCCCCCCCCCS(O)(=O)=O KVGOXGQSTGQXDD-UHFFFAOYSA-N 0.000 description 1
• BTQZKHUEUDPRST-UHFFFAOYSA-N 1-fluoro-3-methylbenzene Chemical compound CC1=CC=CC(F)=C1 BTQZKHUEUDPRST-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
• ABEXEQSGABRUHS-UHFFFAOYSA-N 16-methylheptadecyl 16-methylheptadecanoate Chemical compound CC(C)CCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCC(C)C ABEXEQSGABRUHS-UHFFFAOYSA-N 0.000 description 1
• 238000005160 1H NMR spectroscopy Methods 0.000 description 1
• UHOPWFKONJYLCF-UHFFFAOYSA-N 2-(2-sulfanylethyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCS)C(=O)C2=C1 UHOPWFKONJYLCF-UHFFFAOYSA-N 0.000 description 1
• JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
• OPZDXMCOWFPQPE-UHFFFAOYSA-N 2-bromo-4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C(Br)=C1 OPZDXMCOWFPQPE-UHFFFAOYSA-N 0.000 description 1
• GELVZYOEQVJIRR-UHFFFAOYSA-N 2-chloropyrazine Chemical compound ClC1=CN=CC=N1 GELVZYOEQVJIRR-UHFFFAOYSA-N 0.000 description 1
• DSWNYIKPLMHHFE-UHFFFAOYSA-N 2-ethynylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C#C)=C1 DSWNYIKPLMHHFE-UHFFFAOYSA-N 0.000 description 1
• MTAODLNXWYIKSO-UHFFFAOYSA-N 2-fluoropyridine Chemical compound FC1=CC=CC=N1 MTAODLNXWYIKSO-UHFFFAOYSA-N 0.000 description 1
• HQQMJHTXWNNGIT-UHFFFAOYSA-N 2-methoxy-6-pyridin-2-ylpyridin-3-amine Chemical group C1=C(N)C(OC)=NC(C=2N=CC=CC=2)=C1 HQQMJHTXWNNGIT-UHFFFAOYSA-N 0.000 description 1
• 229940080296 2-naphthalenesulfonate Drugs 0.000 description 1
• WMPPDTMATNBGJN-UHFFFAOYSA-N 2-phenylethylbromide Chemical compound BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-UHFFFAOYSA-N 0.000 description 1
• NTWSIHDXQCZTIB-UHFFFAOYSA-N 2-pyrazin-2-yloxyethanamine Chemical compound NCCOC1=CN=CC=N1 NTWSIHDXQCZTIB-UHFFFAOYSA-N 0.000 description 1
• PCXCZMYBFGWKKH-UHFFFAOYSA-N 2-pyrrolidin-1-ylpyrimidine Chemical compound C1CCCN1C1=NC=CC=N1 PCXCZMYBFGWKKH-UHFFFAOYSA-N 0.000 description 1
• LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
• VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 1
• REQGRJQLONTTLF-UHFFFAOYSA-N 3,6-dimethyl-1h-indole Chemical compound CC1=CC=C2C(C)=CNC2=C1 REQGRJQLONTTLF-UHFFFAOYSA-N 0.000 description 1
• IZTZWJGUGIPLAE-UHFFFAOYSA-N 3-(chloromethoxy)-3-oxopropanoic acid Chemical compound ClCOC(CC(=O)O)=O IZTZWJGUGIPLAE-UHFFFAOYSA-N 0.000 description 1
• UDVWSTBKKYWADN-UHFFFAOYSA-N 4-ethoxypyrimidine Chemical compound CCOC1=CC=NC=N1 UDVWSTBKKYWADN-UHFFFAOYSA-N 0.000 description 1
• PENVYHXKYYCYML-UHFFFAOYSA-N 4-methoxypyrimidine Chemical compound COC1=CC=NC=N1 PENVYHXKYYCYML-UHFFFAOYSA-N 0.000 description 1
• OILJIEKQCVHNMM-UHFFFAOYSA-N 4-tert-butylmorpholine Chemical group CC(C)(C)N1CCOCC1 OILJIEKQCVHNMM-UHFFFAOYSA-N 0.000 description 1
• CPCHRGFQWZMVNX-UHFFFAOYSA-N 5-(trifluoromethyl)pyrimidine Chemical compound FC(F)(F)C1=CN=CN=C1 CPCHRGFQWZMVNX-UHFFFAOYSA-N 0.000 description 1
• XNNJRXKCQCFXLP-UHFFFAOYSA-N 5-chloro-4-methoxypyrimidine Chemical compound COC1=NC=NC=C1Cl XNNJRXKCQCFXLP-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
• FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
• 102100038222 60 kDa heat shock protein, mitochondrial Human genes 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
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• XASOHFCUIQARJT-UHFFFAOYSA-N 8-methoxy-6-[7-(2-morpholin-4-ylethoxy)imidazo[1,2-a]pyridin-3-yl]-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one Chemical compound C(N1C(=O)C2=C(OC)C=C(C=3N4C(=NC=3)C=C(C=C4)OCCN3CCOCC3)C=C2CC1)C(F)(F)F XASOHFCUIQARJT-UHFFFAOYSA-N 0.000 description 1
• QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
• 102100033793 ALK tyrosine kinase receptor Human genes 0.000 description 1
• 101710168331 ALK tyrosine kinase receptor Proteins 0.000 description 1
• 108091006112 ATPases Proteins 0.000 description 1
• OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical group CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 description 1
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
• NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
• 102000057290 Adenosine Triphosphatases Human genes 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
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
• 102100032187 Androgen receptor Human genes 0.000 description 1
• DTDADHMBRZKXSC-GKASHWOUSA-N Aricine Chemical compound C1=C(OC)C=C2C(CCN3C[C@H]4[C@H](C)OC=C([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 DTDADHMBRZKXSC-GKASHWOUSA-N 0.000 description 1
• 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 1
• 102000036365 BRCA1 Human genes 0.000 description 1
• 108700020463 BRCA1 Proteins 0.000 description 1
• 102100021663 Baculoviral IAP repeat-containing protein 5 Human genes 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
• 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
• ZTHQBROSBNNGPU-UHFFFAOYSA-N Butyl hydrogen sulfate Chemical compound CCCCOS(O)(=O)=O ZTHQBROSBNNGPU-UHFFFAOYSA-N 0.000 description 1
• FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
• CBXPRFSDKGUDHI-UHFFFAOYSA-N CCCCCCCCCCOC(C)=O.CCP(CC)CC Chemical compound CCCCCCCCCCOC(C)=O.CCP(CC)CC CBXPRFSDKGUDHI-UHFFFAOYSA-N 0.000 description 1
• JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 1
• PKMUHQIDVVOXHQ-HXUWFJFHSA-N C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O Chemical compound C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O PKMUHQIDVVOXHQ-HXUWFJFHSA-N 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
• 208000005623 Carcinogenesis Diseases 0.000 description 1
• 201000009030 Carcinoma Diseases 0.000 description 1
• 206010007572 Cardiac hypertrophy Diseases 0.000 description 1
• 208000006029 Cardiomegaly Diseases 0.000 description 1
• 102000053642 Catalytic RNA Human genes 0.000 description 1
• 108090000994 Catalytic RNA Proteins 0.000 description 1
• 229940123587 Cell cycle inhibitor Drugs 0.000 description 1
• 108010058432 Chaperonin 60 Proteins 0.000 description 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 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
• KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
• 238000003512 Claisen condensation reaction Methods 0.000 description 1
• 239000005749 Copper compound Substances 0.000 description 1
• VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 1
• 244000241257 Cucumis melo Species 0.000 description 1
• 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 1
• 108010025464 Cyclin-Dependent Kinase 4 Proteins 0.000 description 1
• 108010025468 Cyclin-Dependent Kinase 6 Proteins 0.000 description 1
• 102100036252 Cyclin-dependent kinase 4 Human genes 0.000 description 1
• 102100026804 Cyclin-dependent kinase 6 Human genes 0.000 description 1
• 108090000695 Cytokines Proteins 0.000 description 1
• 102000004127 Cytokines Human genes 0.000 description 1
• 229940123780 DNA topoisomerase I inhibitor Drugs 0.000 description 1
• MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
• 238000006228 Dieckmann condensation reaction Methods 0.000 description 1
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
• 206010059866 Drug resistance Diseases 0.000 description 1
• 241000196324 Embryophyta Species 0.000 description 1
• 102000004190 Enzymes Human genes 0.000 description 1
• 108090000790 Enzymes Proteins 0.000 description 1
• 239000004593 Epoxy Substances 0.000 description 1
• 102100038595 Estrogen receptor Human genes 0.000 description 1
• JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
• PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
• 102000007665 Extracellular Signal-Regulated MAP Kinases Human genes 0.000 description 1
• 108010007457 Extracellular Signal-Regulated MAP Kinases Proteins 0.000 description 1
• 239000001116 FEMA 4028 Substances 0.000 description 1
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
• 206010061968 Gastric neoplasm Diseases 0.000 description 1
• 206010051066 Gastrointestinal stromal tumour Diseases 0.000 description 1
• 208000034951 Genetic Translocation Diseases 0.000 description 1
• XYZZKVRWGOWVGO-UHFFFAOYSA-N Glycerol-phosphate Chemical compound OP(O)(O)=O.OCC(O)CO XYZZKVRWGOWVGO-UHFFFAOYSA-N 0.000 description 1
• 239000007995 HEPES buffer Substances 0.000 description 1
• 241001343354 Halenia corniculata Species 0.000 description 1
• 208000005176 Hepatitis C Diseases 0.000 description 1
• HVDUEHWSHQORJW-UHFFFAOYSA-N Hetereophyllin Natural products CCN1CC2(C)CCC(O)C34C5CC6CCC(O)(C(CC23)C14)C5C(=O)O6 HVDUEHWSHQORJW-UHFFFAOYSA-N 0.000 description 1
• CBYLXVCMCVXUQQ-UHFFFAOYSA-N Heterophyllin Chemical group CC(C)=CCC1=C2OC(C)(C)C=CC2=C(O)C(C(C=2CC=C(C)C)=O)=C1OC=2C1=CC(O)=C(O)C=C1O CBYLXVCMCVXUQQ-UHFFFAOYSA-N 0.000 description 1
• 208000017604 Hodgkin disease Diseases 0.000 description 1
• 208000021519 Hodgkin lymphoma Diseases 0.000 description 1
• 208000010747 Hodgkins lymphoma Diseases 0.000 description 1
• 101001012157 Homo sapiens Receptor tyrosine-protein kinase erbB-2 Proteins 0.000 description 1
• 101001059454 Homo sapiens Serine/threonine-protein kinase MARK2 Proteins 0.000 description 1
• 101150065069 Hsp90b1 gene Proteins 0.000 description 1
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
• 241000257303 Hymenoptera Species 0.000 description 1
• 206010020751 Hypersensitivity Diseases 0.000 description 1
• 206010021143 Hypoxia Diseases 0.000 description 1
• 235000003332 Ilex aquifolium Nutrition 0.000 description 1
• 235000002296 Ilex sandwicensis Nutrition 0.000 description 1
• 235000002294 Ilex volkensiana Nutrition 0.000 description 1
• 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 1
• 206010061218 Inflammation Diseases 0.000 description 1
• 102000014150 Interferons Human genes 0.000 description 1
• 108010050904 Interferons Proteins 0.000 description 1
• 108010002350 Interleukin-2 Proteins 0.000 description 1
• 108010063738 Interleukins Proteins 0.000 description 1
• 102000015696 Interleukins Human genes 0.000 description 1
• 241000764238 Isis Species 0.000 description 1
• OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical group N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 1
• 208000008839 Kidney Neoplasms Diseases 0.000 description 1
• 239000005909 Kieselgur Substances 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
• 239000005411 L01XE02 - Gefitinib Substances 0.000 description 1
• 239000005511 L01XE05 - Sorafenib Substances 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
• 208000028018 Lymphocytic leukaemia Diseases 0.000 description 1
• 108091054455 MAP kinase family Proteins 0.000 description 1
• 102000043136 MAP kinase family Human genes 0.000 description 1
• ZRVUJXDFFKFLMG-UHFFFAOYSA-N Meloxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=NC=C(C)S1 ZRVUJXDFFKFLMG-UHFFFAOYSA-N 0.000 description 1
• 206010027476 Metastases Diseases 0.000 description 1
• WKSXRWSOSLGSTN-UHFFFAOYSA-N Methoxypyrazine Chemical compound COC1=CN=CC=N1 WKSXRWSOSLGSTN-UHFFFAOYSA-N 0.000 description 1
• 241001529936 Murinae Species 0.000 description 1
• 101100335081 Mus musculus Flt3 gene Proteins 0.000 description 1
• 101100447665 Mus musculus Gas2 gene Proteins 0.000 description 1
• 108010021466 Mutant Proteins Proteins 0.000 description 1
• 102000008300 Mutant Proteins Human genes 0.000 description 1
• 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 1
• KYFSAJXDPRWKJG-UHFFFAOYSA-N NN(CCCCCCCCCC)N Chemical compound NN(CCCCCCCCCC)N KYFSAJXDPRWKJG-UHFFFAOYSA-N 0.000 description 1
• UCWOUUCJIKTHDY-UHFFFAOYSA-N NN.CCCC Chemical compound NN.CCCC UCWOUUCJIKTHDY-UHFFFAOYSA-N 0.000 description 1
• KTDZCOWXCWUPEO-UHFFFAOYSA-N NS-398 Chemical compound CS(=O)(=O)NC1=CC=C([N+]([O-])=O)C=C1OC1CCCCC1 KTDZCOWXCWUPEO-UHFFFAOYSA-N 0.000 description 1
• PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical class OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
• JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
• 239000006057 Non-nutritive feed additive Substances 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
• 108010058765 Oncogene Protein pp60(v-src) Proteins 0.000 description 1
• 229910019142 PO4 Inorganic materials 0.000 description 1
• 229930012538 Paclitaxel Natural products 0.000 description 1
• 229920002230 Pectic acid Polymers 0.000 description 1
• 239000004698 Polyethylene Substances 0.000 description 1
• 239000002202 Polyethylene glycol Substances 0.000 description 1
• 102000029797 Prion Human genes 0.000 description 1
• 108091000054 Prion Proteins 0.000 description 1
• OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
• 101710166307 Protein lines Proteins 0.000 description 1
• 102100030086 Receptor tyrosine-protein kinase erbB-2 Human genes 0.000 description 1
• 206010038389 Renal cancer Diseases 0.000 description 1
• KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
• 102100028904 Serine/threonine-protein kinase MARK2 Human genes 0.000 description 1
• 229920002472 Starch Polymers 0.000 description 1
• 229910000831 Steel Inorganic materials 0.000 description 1
• 229930182558 Sterol Natural products 0.000 description 1
• 108010090804 Streptavidin Proteins 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
• 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 1
• 229930006000 Sucrose Natural products 0.000 description 1
• 108010002687 Survivin Proteins 0.000 description 1
• 208000024313 Testicular Neoplasms Diseases 0.000 description 1
• ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
• 239000000365 Topoisomerase I Inhibitor Substances 0.000 description 1
• 102000040945 Transcription factor Human genes 0.000 description 1
• 108091023040 Transcription factor Proteins 0.000 description 1
• 102100023935 Transmembrane glycoprotein NMB Human genes 0.000 description 1
• 108090000848 Ubiquitin Proteins 0.000 description 1
• 102000044159 Ubiquitin Human genes 0.000 description 1
• 229940122803 Vinca alkaloid Drugs 0.000 description 1
• 241000700605 Viruses Species 0.000 description 1
• 102100023038 WD and tetratricopeptide repeats protein 1 Human genes 0.000 description 1
• DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
• ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 1
• SAHIZENKTPRYSN-UHFFFAOYSA-N [2-[3-(phenoxymethyl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound O(C1=CC=CC=C1)CC=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 SAHIZENKTPRYSN-UHFFFAOYSA-N 0.000 description 1
• ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 1
• 230000002159 abnormal effect Effects 0.000 description 1
• 238000009825 accumulation Methods 0.000 description 1
• DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
• SPEUIVXLLWOEMJ-UHFFFAOYSA-N acetaldehyde dimethyl acetal Natural products COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 1
• 150000001241 acetals Chemical class 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• 230000009471 action Effects 0.000 description 1
• 239000004480 active ingredient Substances 0.000 description 1
• WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
• 230000001919 adrenal effect Effects 0.000 description 1
• 230000002776 aggregation Effects 0.000 description 1
• 238000004220 aggregation Methods 0.000 description 1
• 229940072056 alginate Drugs 0.000 description 1
• 235000010443 alginic acid Nutrition 0.000 description 1
• 229920000615 alginic acid Polymers 0.000 description 1
• 229910052783 alkali metal Inorganic materials 0.000 description 1
• 150000001340 alkali metals Chemical class 0.000 description 1
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 1
• 125000005277 alkyl imino group Chemical group 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
• 230000007815 allergy Effects 0.000 description 1
• AEMOLEFTQBMNLQ-BKBMJHBISA-N alpha-D-galacturonic acid Chemical compound O[C@H]1O[C@H](C(O)=O)[C@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-BKBMJHBISA-N 0.000 description 1
• 230000004075 alteration Effects 0.000 description 1
• 229940037003 alum Drugs 0.000 description 1
• AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
• 229940024606 amino acid Drugs 0.000 description 1
• 125000000539 amino acid group Chemical group 0.000 description 1
• BIVUUOPIAYRCAP-UHFFFAOYSA-N aminoazanium;chloride Chemical compound Cl.NN BIVUUOPIAYRCAP-UHFFFAOYSA-N 0.000 description 1
• 150000005005 aminopyrimidines Chemical class 0.000 description 1
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
• 108010080146 androgen receptors Proteins 0.000 description 1
• MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 1
• 125000005577 anthracene group Chemical group 0.000 description 1
• 150000001454 anthracenes Chemical class 0.000 description 1
• 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
• 230000002280 anti-androgenic effect Effects 0.000 description 1
• 230000001093 anti-cancer Effects 0.000 description 1
• 230000000340 anti-metabolite Effects 0.000 description 1
• 230000000259 anti-tumor effect 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
• 229940100197 antimetabolite Drugs 0.000 description 1
• 239000002256 antimetabolite Substances 0.000 description 1
• 239000003972 antineoplastic antibiotic Substances 0.000 description 1
• 239000012736 aqueous medium Substances 0.000 description 1
• 239000007864 aqueous solution Substances 0.000 description 1
• 125000005125 aryl alkyl amino carbonyl group Chemical group 0.000 description 1
• 125000001691 aryl alkyl amino group Chemical group 0.000 description 1
• 125000005264 aryl amine group Chemical group 0.000 description 1
• 125000005100 aryl amino carbonyl group Chemical group 0.000 description 1
• 150000001543 aryl boronic acids Chemical class 0.000 description 1
• 125000004658 aryl carbonyl amino group Chemical group 0.000 description 1
• 125000005199 aryl carbonyloxy group Chemical group 0.000 description 1
• 125000005160 aryl oxy alkyl group Chemical group 0.000 description 1
• 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
• 229940009098 aspartate Drugs 0.000 description 1
• 239000012298 atmosphere Substances 0.000 description 1
• 230000005784 autoimmunity Effects 0.000 description 1
• HKVFISRIUUGTIB-UHFFFAOYSA-O azanium;cerium;nitrate Chemical compound [NH4+].[Ce].[O-][N+]([O-])=O HKVFISRIUUGTIB-UHFFFAOYSA-O 0.000 description 1
• 230000001580 bacterial effect Effects 0.000 description 1
• 102000004441 bcr-abl Fusion Proteins Human genes 0.000 description 1
• 108010056708 bcr-abl Fusion Proteins Proteins 0.000 description 1
• 235000013405 beer Nutrition 0.000 description 1
• 230000008901 benefit Effects 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
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
• 229940050390 benzoate Drugs 0.000 description 1
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
• AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
• WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 1
• 229960004853 betadex Drugs 0.000 description 1
• 229960000997 bicalutamide Drugs 0.000 description 1
• 239000012148 binding buffer Substances 0.000 description 1
• 230000003115 biocidal effect Effects 0.000 description 1
• 229910052797 bismuth Inorganic materials 0.000 description 1
• JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
• 230000000903 blocking effect Effects 0.000 description 1
• 238000009835 boiling Methods 0.000 description 1
• 210000001185 bone marrow Anatomy 0.000 description 1
• KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
• 239000004327 boric acid Substances 0.000 description 1
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
• 229940098773 bovine serum albumin Drugs 0.000 description 1
• 150000001649 bromium compounds Chemical class 0.000 description 1
• 230000005587 bubbling Effects 0.000 description 1
• 239000006172 buffering agent Substances 0.000 description 1
• 244000309464 bull Species 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
• 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
• 239000006227 byproduct Substances 0.000 description 1
• KVUAALJSMIVURS-ZEDZUCNESA-L calcium folinate Chemical compound [Ca+2].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 KVUAALJSMIVURS-ZEDZUCNESA-L 0.000 description 1
• FATUQANACHZLRT-KMRXSBRUSA-L calcium glucoheptonate Chemical compound [Ca+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O FATUQANACHZLRT-KMRXSBRUSA-L 0.000 description 1
• 159000000007 calcium salts Chemical class 0.000 description 1
• MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
• 229940088954 camptosar Drugs 0.000 description 1
• 230000036952 cancer formation Effects 0.000 description 1
• 230000005907 cancer growth Effects 0.000 description 1
• 208000035269 cancer or benign tumor Diseases 0.000 description 1
• 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
• 150000007942 carboxylates Chemical class 0.000 description 1
• 125000002843 carboxylic acid group Chemical group 0.000 description 1
• 231100000504 carcinogenesis Toxicity 0.000 description 1
• 230000003293 cardioprotective effect Effects 0.000 description 1
• 239000000969 carrier Substances 0.000 description 1
• 239000012876 carrier material Substances 0.000 description 1
• 230000015556 catabolic process Effects 0.000 description 1
• 230000003197 catalytic effect Effects 0.000 description 1
• 125000002091 cationic group Chemical group 0.000 description 1
• RZEKVGVHFLEQIL-UHFFFAOYSA-N celecoxib Chemical compound C1=CC(C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 RZEKVGVHFLEQIL-UHFFFAOYSA-N 0.000 description 1
• 229960000590 celecoxib Drugs 0.000 description 1
• 230000020411 cell activation Effects 0.000 description 1
• 230000022131 cell cycle Effects 0.000 description 1
• 230000030833 cell death Effects 0.000 description 1
• 230000004637 cellular stress Effects 0.000 description 1
• 239000001913 cellulose Substances 0.000 description 1
• 229920002678 cellulose Polymers 0.000 description 1
• 235000010980 cellulose Nutrition 0.000 description 1
• XMPZTFVPEKAKFH-UHFFFAOYSA-P ceric ammonium nitrate Chemical compound [NH4+].[NH4+].[Ce+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O XMPZTFVPEKAKFH-UHFFFAOYSA-P 0.000 description 1
• 230000000739 chaotic effect Effects 0.000 description 1
• 238000012512 characterization method Methods 0.000 description 1
• 150000001793 charged compounds Chemical class 0.000 description 1
• 239000003153 chemical reaction reagent Substances 0.000 description 1
• 230000000973 chemotherapeutic effect Effects 0.000 description 1
• 229940044683 chemotherapy drug Drugs 0.000 description 1
• 229910052801 chlorine Inorganic materials 0.000 description 1
• 125000001309 chloro group Chemical group Cl* 0.000 description 1
• 229960001231 choline Drugs 0.000 description 1
• OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
• 229940114081 cinnamate Drugs 0.000 description 1
• 235000013985 cinnamic acid Nutrition 0.000 description 1
• 229930016911 cinnamic acid Natural products 0.000 description 1
• 229940001468 citrate Drugs 0.000 description 1
• 229940110456 cocoa butter Drugs 0.000 description 1
• 235000019868 cocoa butter Nutrition 0.000 description 1
• 210000001072 colon Anatomy 0.000 description 1
• 238000004040 coloring Methods 0.000 description 1
• 230000002860 competitive effect Effects 0.000 description 1
• 229940126179 compound 72 Drugs 0.000 description 1
• 239000012141 concentrate Substances 0.000 description 1
• 235000008504 concentrate Nutrition 0.000 description 1
• 230000021615 conjugation Effects 0.000 description 1
• 150000001880 copper compounds Chemical class 0.000 description 1
• 239000003246 corticosteroid Substances 0.000 description 1
• 229960001334 corticosteroids Drugs 0.000 description 1
• 239000010779 crude oil Substances 0.000 description 1
• 238000012866 crystallographic experiment Methods 0.000 description 1
• 150000001923 cyclic compounds Chemical class 0.000 description 1
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 229940097362 cyclodextrins Drugs 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
• 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
• NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 1
• BALGDZWGNCXXES-UHFFFAOYSA-N cyclopentane;propanoic acid Chemical compound CCC(O)=O.C1CCCC1 BALGDZWGNCXXES-UHFFFAOYSA-N 0.000 description 1
• XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
• 229960003901 dacarbazine Drugs 0.000 description 1
• 238000006114 decarboxylation reaction Methods 0.000 description 1
• 238000006731 degradation reaction Methods 0.000 description 1
• UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 1
• 229960003957 dexamethasone Drugs 0.000 description 1
• 229960000605 dexrazoxane Drugs 0.000 description 1
• 239000008121 dextrose Substances 0.000 description 1
• 238000010586 diagram Methods 0.000 description 1
• 150000001983 dialkylethers Chemical class 0.000 description 1
• 125000005266 diarylamine group Chemical group 0.000 description 1
• 230000037213 diet Effects 0.000 description 1
• 235000005911 diet Nutrition 0.000 description 1
• 235000014113 dietary fatty acids Nutrition 0.000 description 1
• ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
• DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
• 239000003085 diluting agent Substances 0.000 description 1
• VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
• 150000002016 disaccharides Chemical class 0.000 description 1
• VDQVEACBQKUUSU-UHFFFAOYSA-M disodium;sulfanide Chemical compound [Na+].[Na+].[SH-] VDQVEACBQKUUSU-UHFFFAOYSA-M 0.000 description 1
• 239000002270 dispersing agent Substances 0.000 description 1
• 230000005593 dissociations Effects 0.000 description 1
• 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
• 229940043264 dodecyl sulfate Drugs 0.000 description 1
• 239000000890 drug combination Substances 0.000 description 1
• 238000012377 drug delivery Methods 0.000 description 1
• 238000009510 drug design Methods 0.000 description 1
• 238000001035 drying Methods 0.000 description 1
• 230000002500 effect on skin Effects 0.000 description 1
• 238000000921 elemental analysis Methods 0.000 description 1
• 238000010828 elution Methods 0.000 description 1
• 239000003995 emulsifying agent Substances 0.000 description 1
• 230000001804 emulsifying effect Effects 0.000 description 1
• 239000003623 enhancer Substances 0.000 description 1
• 239000002702 enteric coating Substances 0.000 description 1
• 238000009505 enteric coating Methods 0.000 description 1
• 229960003276 erythromycin Drugs 0.000 description 1
• 229940011871 estrogen Drugs 0.000 description 1
• 239000000262 estrogen Substances 0.000 description 1
• 108010038795 estrogen receptors Proteins 0.000 description 1
• CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
• KVJUYUKNCVBWOX-UHFFFAOYSA-N ethanol;pyrrolidine Chemical compound CCO.C1CCNC1 KVJUYUKNCVBWOX-UHFFFAOYSA-N 0.000 description 1
• 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
• OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 1
• 229960005420 etoposide Drugs 0.000 description 1
• 238000001704 evaporation Methods 0.000 description 1
• 230000008020 evaporation Effects 0.000 description 1
• 230000029142 excretion Effects 0.000 description 1
• 235000019197 fats Nutrition 0.000 description 1
• 239000000194 fatty acid Substances 0.000 description 1
• 229930195729 fatty acid Natural products 0.000 description 1
• 150000004665 fatty acids Chemical class 0.000 description 1
• 210000002950 fibroblast Anatomy 0.000 description 1
• 238000011049 filling Methods 0.000 description 1
• 238000001914 filtration Methods 0.000 description 1
• DBEPLOCGEIEOCV-WSBQPABSSA-N finasteride Chemical compound N([C@@H]1CC2)C(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)NC(C)(C)C)[C@@]2(C)CC1 DBEPLOCGEIEOCV-WSBQPABSSA-N 0.000 description 1
• 229960004039 finasteride Drugs 0.000 description 1
• 239000000796 flavoring agent Substances 0.000 description 1
• 229960000390 fludarabine Drugs 0.000 description 1
• 229960005304 fludarabine phosphate Drugs 0.000 description 1
• 238000002875 fluorescence polarization Methods 0.000 description 1
• NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical group FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 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
• 235000008191 folinic acid Nutrition 0.000 description 1
• 239000011672 folinic acid Substances 0.000 description 1
• 238000005755 formation reaction Methods 0.000 description 1
• 230000002538 fungal effect Effects 0.000 description 1
• 238000004817 gas chromatography Methods 0.000 description 1
• 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
• 230000002496 gastric effect Effects 0.000 description 1
• 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 1
• 229960002584 gefitinib Drugs 0.000 description 1
• 239000010437 gem Substances 0.000 description 1
• 229910001751 gemstone Inorganic materials 0.000 description 1
• 229960003297 gemtuzumab ozogamicin Drugs 0.000 description 1
• 230000014509 gene expression Effects 0.000 description 1
• 238000001415 gene therapy Methods 0.000 description 1
• 239000008187 granular material Substances 0.000 description 1
• 239000003102 growth factor Substances 0.000 description 1
• 230000009036 growth inhibition Effects 0.000 description 1
• 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 1
• 230000003394 haemopoietic effect Effects 0.000 description 1
• 230000036541 health Effects 0.000 description 1
• 230000008642 heat stress Effects 0.000 description 1
• 230000002440 hepatic effect Effects 0.000 description 1
• 208000006454 hepatitis Diseases 0.000 description 1
• 231100000283 hepatitis Toxicity 0.000 description 1
• MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical class CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
• 125000004475 heteroaralkyl group Chemical group 0.000 description 1
• 125000005343 heterocyclic alkyl group Chemical group 0.000 description 1
• FVMMOSQBOWPRQW-UHFFFAOYSA-N heterophylline Natural products CC(=O)OC1C2(C)C(OC(=O)C=3C=CC=CC=3)CC(C(O3)(C)C)C(OC(=O)C=4C=NC=CC=4)C32C(C)CC1OC(=O)C1=CC=CN=C1 FVMMOSQBOWPRQW-UHFFFAOYSA-N 0.000 description 1
• IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
• FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
• 208000018819 hormone-resistant breast carcinoma Diseases 0.000 description 1
• 150000004678 hydrides Chemical group 0.000 description 1
• ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
• 206010020718 hyperplasia Diseases 0.000 description 1
• 238000005417 image-selected in vivo spectroscopy Methods 0.000 description 1
• 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 1
• 150000002466 imines Chemical class 0.000 description 1
• 208000026278 immune system disease Diseases 0.000 description 1
• 239000000367 immunologic factor Substances 0.000 description 1
• 239000002955 immunomodulating agent Substances 0.000 description 1
• 230000001771 impaired effect Effects 0.000 description 1
• 230000002779 inactivation Effects 0.000 description 1
• 230000001939 inductive effect Effects 0.000 description 1
• 230000004054 inflammatory process Effects 0.000 description 1
• 238000001802 infusion Methods 0.000 description 1
• 229940102223 injectable solution Drugs 0.000 description 1
• 229940102213 injectable suspension Drugs 0.000 description 1
• 230000002608 insulinlike Effects 0.000 description 1
• 238000012739 integrated shape imaging system Methods 0.000 description 1
• 230000003993 interaction Effects 0.000 description 1
• 229940079322 interferon Drugs 0.000 description 1
• 239000007927 intramuscular injection Substances 0.000 description 1
• 238000010255 intramuscular injection Methods 0.000 description 1
• 238000010253 intravenous injection Methods 0.000 description 1
• 230000009545 invasion Effects 0.000 description 1
• 150000004694 iodide salts Chemical class 0.000 description 1
• 229910052740 iodine Inorganic materials 0.000 description 1
• 239000011630 iodine Substances 0.000 description 1
• 125000002346 iodo group Chemical group I* 0.000 description 1
• 239000003456 ion exchange resin Substances 0.000 description 1
• 229920003303 ion-exchange polymer Polymers 0.000 description 1
• 150000002500 ions Chemical class 0.000 description 1
• 230000001788 irregular Effects 0.000 description 1
• 230000007794 irritation Effects 0.000 description 1
• 230000000302 ischemic effect Effects 0.000 description 1
• SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
• AWJUIBRHMBBTKR-UHFFFAOYSA-N iso-quinoline Natural products C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 1
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
• QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
• 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 description 1
• 229960004125 ketoconazole Drugs 0.000 description 1
• 210000003734 kidney Anatomy 0.000 description 1
• 201000010982 kidney cancer Diseases 0.000 description 1
• 210000000244 kidney pelvis Anatomy 0.000 description 1
• 210000003127 knee Anatomy 0.000 description 1
• 239000008101 lactose Substances 0.000 description 1
• 239000000787 lecithin Substances 0.000 description 1
• 235000010445 lecithin Nutrition 0.000 description 1
• 229940067606 lecithin Drugs 0.000 description 1
• 229960001691 leucovorin Drugs 0.000 description 1
• 229920005610 lignin Polymers 0.000 description 1
• 239000007788 liquid Substances 0.000 description 1
• 238000004811 liquid chromatography Methods 0.000 description 1
• 239000004973 liquid crystal related substance Substances 0.000 description 1
• 239000008297 liquid dosage form Substances 0.000 description 1
• 239000007791 liquid phase Substances 0.000 description 1
• 229910003002 lithium salt Inorganic materials 0.000 description 1
• 159000000002 lithium salts Chemical class 0.000 description 1
• 238000011068 loading method Methods 0.000 description 1
• 230000007774 longterm Effects 0.000 description 1
• 239000007937 lozenge Substances 0.000 description 1
• 239000000314 lubricant Substances 0.000 description 1
• 210000004072 lung Anatomy 0.000 description 1
• 208000037841 lung tumor Diseases 0.000 description 1
• 230000000527 lymphocytic effect Effects 0.000 description 1
• 208000003747 lymphoid leukemia Diseases 0.000 description 1
• 229910001629 magnesium chloride Inorganic materials 0.000 description 1
• 159000000003 magnesium salts Chemical class 0.000 description 1
• 238000012423 maintenance Methods 0.000 description 1
• 239000011976 maleic acid Substances 0.000 description 1
• 230000003211 malignant effect Effects 0.000 description 1
• 208000026037 malignant tumor of neck Diseases 0.000 description 1
• 210000004962 mammalian cell Anatomy 0.000 description 1
• 238000004519 manufacturing process Methods 0.000 description 1
• 238000005259 measurement Methods 0.000 description 1
• 230000007246 mechanism Effects 0.000 description 1
• 239000002609 medium Substances 0.000 description 1
• 229960001929 meloxicam Drugs 0.000 description 1
• 239000000155 melt Substances 0.000 description 1
• 238000002844 melting Methods 0.000 description 1
• 230000008018 melting Effects 0.000 description 1
• 108020004999 messenger RNA Proteins 0.000 description 1
• 239000002207 metabolite Substances 0.000 description 1
• 229910052751 metal Inorganic materials 0.000 description 1
• 239000002184 metal Substances 0.000 description 1
• 230000009401 metastasis Effects 0.000 description 1
• 229940098779 methanesulfonic acid Drugs 0.000 description 1
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 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
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
• CHJJGSNFBQVOTG-UHFFFAOYSA-N methylguanidine Chemical compound CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
• 230000000116 mitigating effect Effects 0.000 description 1
• 239000002829 mitogen activated protein kinase inhibitor Substances 0.000 description 1
• 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 1
• 229960001156 mitoxantrone Drugs 0.000 description 1
• 238000002156 mixing Methods 0.000 description 1
• 239000002808 molecular sieve Substances 0.000 description 1
• VYGYNVZNSSTDLJ-HKCOAVLJSA-N monorden Natural products CC1CC2OC2C=C/C=C/C(=O)CC3C(C(=CC(=C3Cl)O)O)C(=O)O1 VYGYNVZNSSTDLJ-HKCOAVLJSA-N 0.000 description 1
• 150000002772 monosaccharides Chemical class 0.000 description 1
• 229960005181 morphine Drugs 0.000 description 1
• 239000012452 mother liquor Substances 0.000 description 1
• 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• MTKJRUNLKOGMRG-UHFFFAOYSA-N n,n-dimethylmethanamine;ethanamine Chemical compound CCN.CN(C)C MTKJRUNLKOGMRG-UHFFFAOYSA-N 0.000 description 1
• CNLIZIJWOMRBLD-UHFFFAOYSA-N n,n-dimethylpyridin-1-ium-1-amine Chemical compound CN(C)[N+]1=CC=CC=C1 CNLIZIJWOMRBLD-UHFFFAOYSA-N 0.000 description 1
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• KVBGVZZKJNLNJU-UHFFFAOYSA-M naphthalene-2-sulfonate Chemical compound C1=CC=CC2=CC(S(=O)(=O)[O-])=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-M 0.000 description 1
• 125000001624 naphthyl group Chemical group 0.000 description 1
• 208000025189 neoplasm of testis Diseases 0.000 description 1
• 230000000324 neuroprotective effect Effects 0.000 description 1
• SFDJOSRHYKHMOK-UHFFFAOYSA-N nitramide Chemical compound N[N+]([O-])=O SFDJOSRHYKHMOK-UHFFFAOYSA-N 0.000 description 1
• 150000002825 nitriles Chemical class 0.000 description 1
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
• 239000012299 nitrogen atmosphere Substances 0.000 description 1
• 231100000344 non-irritating Toxicity 0.000 description 1
• 235000012149 noodles Nutrition 0.000 description 1
• DYSIROANKWMSGC-KWFINLGMSA-N npaf Chemical compound C([C@H](NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@H](C)N)CC(C)C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)C1=CC=CC=C1 DYSIROANKWMSGC-KWFINLGMSA-N 0.000 description 1
• 239000002773 nucleotide Substances 0.000 description 1
• 125000003729 nucleotide group Chemical group 0.000 description 1
• 235000015097 nutrients Nutrition 0.000 description 1
• 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
• 230000004650 oncogenic pathway Effects 0.000 description 1
• 230000006712 oncogenic signaling pathway Effects 0.000 description 1
• 230000006548 oncogenic transformation Effects 0.000 description 1
• 238000011275 oncology therapy Methods 0.000 description 1
• 235000005985 organic acids Nutrition 0.000 description 1
• 150000002894 organic compounds Chemical class 0.000 description 1
• 230000002018 overexpression Effects 0.000 description 1
• 235000006408 oxalic acid Nutrition 0.000 description 1
• 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 description 1
• 125000000160 oxazolidinyl group Chemical group 0.000 description 1
• 125000003544 oxime group Chemical group 0.000 description 1
• 239000005022 packaging material Substances 0.000 description 1
• 229960001592 paclitaxel Drugs 0.000 description 1
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
• 239000002304 perfume Substances 0.000 description 1
• 239000012466 permeate Substances 0.000 description 1
• JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
• 230000002085 persistent effect Effects 0.000 description 1
• 239000008177 pharmaceutical agent Substances 0.000 description 1
• 239000000825 pharmaceutical preparation Substances 0.000 description 1
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
• 239000010452 phosphate Substances 0.000 description 1
• 229940075930 picrate Drugs 0.000 description 1
• OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
• 229950010765 pivalate Drugs 0.000 description 1
• IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
• 239000004033 plastic Substances 0.000 description 1
• 229920003023 plastic Polymers 0.000 description 1
• 150000003058 platinum compounds Chemical class 0.000 description 1
• 125000003367 polycyclic group Chemical group 0.000 description 1
• 229920000573 polyethylene Polymers 0.000 description 1
• 229920001223 polyethylene glycol Polymers 0.000 description 1
• 108091033319 polynucleotide Proteins 0.000 description 1
• 102000040430 polynucleotide Human genes 0.000 description 1
• 239000002157 polynucleotide Substances 0.000 description 1
• 229920001184 polypeptide Polymers 0.000 description 1
• 229920001296 polysiloxane Polymers 0.000 description 1
• 238000010837 poor prognosis Methods 0.000 description 1
• 159000000001 potassium salts Chemical class 0.000 description 1
• 239000002243 precursor Substances 0.000 description 1
• 239000003755 preservative agent Substances 0.000 description 1
• 230000002265 prevention Effects 0.000 description 1
• 102000004196 processed proteins & peptides Human genes 0.000 description 1
• 108090000765 processed proteins & peptides Proteins 0.000 description 1
• KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
• DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
• 125000006239 protecting group Chemical group 0.000 description 1
• 230000004845 protein aggregation Effects 0.000 description 1
• 238000009163 protein therapy Methods 0.000 description 1
• 125000004941 pyridazin-5-yl group Chemical group N1=NC=CC(=C1)* 0.000 description 1
• JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
• 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
• 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 description 1
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
• 150000004060 quinone imines Chemical class 0.000 description 1
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
• 230000005855 radiation Effects 0.000 description 1
• AECPBJMOGBFQDN-YMYQVXQQSA-N radicicol Chemical compound C1CCCC(=O)C[C@H]2[C@H](Cl)C(=O)CC(=O)[C@H]2C(=O)O[C@H](C)C[C@H]2O[C@@H]21 AECPBJMOGBFQDN-YMYQVXQQSA-N 0.000 description 1
• 229930192524 radicicol Natural products 0.000 description 1
• 102000009929 raf Kinases Human genes 0.000 description 1
• 108010077182 raf Kinases Proteins 0.000 description 1
• 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 1
• 229960004622 raloxifene Drugs 0.000 description 1
• 210000000664 rectum Anatomy 0.000 description 1
• 230000002829 reductive effect Effects 0.000 description 1
• 208000037803 restenosis Diseases 0.000 description 1
• 229930002330 retinoic acid Natural products 0.000 description 1
• 108091092562 ribozyme Proteins 0.000 description 1
• 229910052707 ruthenium Inorganic materials 0.000 description 1
• 210000003296 saliva Anatomy 0.000 description 1
• 229930195734 saturated hydrocarbon Natural products 0.000 description 1
• 150000003335 secondary amines Chemical class 0.000 description 1
• 230000035945 sensitivity Effects 0.000 description 1
• 230000001568 sexual effect Effects 0.000 description 1
• 108091006024 signal transducing proteins Proteins 0.000 description 1
• 102000034285 signal transducing proteins Human genes 0.000 description 1
• 230000011664 signaling Effects 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
• 239000012279 sodium borohydride Substances 0.000 description 1
• 229910000033 sodium borohydride Inorganic materials 0.000 description 1
• 159000000000 sodium salts Chemical class 0.000 description 1
• 229910052938 sodium sulfate Inorganic materials 0.000 description 1
• 229910052979 sodium sulfide Inorganic materials 0.000 description 1
• 235000011152 sodium sulphate Nutrition 0.000 description 1
• 229960003787 sorafenib Drugs 0.000 description 1
• 230000003595 spectral effect Effects 0.000 description 1
• 238000005507 spraying Methods 0.000 description 1
• 239000003381 stabilizer Substances 0.000 description 1
• 239000008107 starch Substances 0.000 description 1
• 235000019698 starch Nutrition 0.000 description 1
• 239000007858 starting material Substances 0.000 description 1
• 239000010959 steel Substances 0.000 description 1
• 235000003702 sterols Nutrition 0.000 description 1
• 239000007929 subcutaneous injection Substances 0.000 description 1
• 238000010254 subcutaneous injection Methods 0.000 description 1
• 125000005415 substituted alkoxy group Chemical group 0.000 description 1
• 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
• 229960002317 succinimide Drugs 0.000 description 1
• 239000005720 sucrose Substances 0.000 description 1
• PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
• 229940124530 sulfonamide Drugs 0.000 description 1
• 150000003456 sulfonamides Chemical class 0.000 description 1
• 150000003457 sulfones Chemical class 0.000 description 1
• 125000003375 sulfoxide group Chemical group 0.000 description 1
• 239000000829 suppository Substances 0.000 description 1
• 238000002198 surface plasmon resonance spectroscopy Methods 0.000 description 1
• 239000003765 sweetening agent Substances 0.000 description 1
• 208000024891 symptom Diseases 0.000 description 1
• 238000010189 synthetic method Methods 0.000 description 1
• 239000006188 syrup Substances 0.000 description 1
• 235000020357 syrup Nutrition 0.000 description 1
• 239000003826 tablet Substances 0.000 description 1
• 239000000454 talc Substances 0.000 description 1
• 229910052623 talc Inorganic materials 0.000 description 1
• AYUNIORJHRXIBJ-TXHRRWQRSA-N tanespimycin Chemical compound N1C(=O)\C(C)=C\C=C/[C@H](OC)[C@@H](OC(N)=O)\C(C)=C\[C@H](C)[C@@H](O)[C@@H](OC)C[C@H](C)CC2=C(NCC=C)C(=O)C=C1C2=O AYUNIORJHRXIBJ-TXHRRWQRSA-N 0.000 description 1
• 235000018553 tannin Nutrition 0.000 description 1
• 229920001864 tannin Polymers 0.000 description 1
• 239000001648 tannin Substances 0.000 description 1
• 229940095064 tartrate Drugs 0.000 description 1
• 238000003419 tautomerization reaction Methods 0.000 description 1
• 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 1
• 229940063683 taxotere Drugs 0.000 description 1
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 201000003120 testicular cancer Diseases 0.000 description 1
• CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
• QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
• 229950006410 tezacitabine Drugs 0.000 description 1
• GFFXZLZWLOBBLO-ASKVSEFXSA-N tezacitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(=C/F)/[C@H](O)[C@@H](CO)O1 GFFXZLZWLOBBLO-ASKVSEFXSA-N 0.000 description 1
• 230000004797 therapeutic response Effects 0.000 description 1
• RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical compound SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 description 1
• 208000013076 thyroid tumor Diseases 0.000 description 1
• 210000001519 tissue Anatomy 0.000 description 1
• 239000010936 titanium Substances 0.000 description 1
• JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical compound [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 description 1
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
• 125000003944 tolyl group Chemical group 0.000 description 1
• 230000000699 topical effect Effects 0.000 description 1
• 229960000303 topotecan 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
• 231100000331 toxic Toxicity 0.000 description 1
• 230000002588 toxic effect Effects 0.000 description 1
• 231100000419 toxicity Toxicity 0.000 description 1
• 230000001988 toxicity Effects 0.000 description 1
• 239000003053 toxin Substances 0.000 description 1
• 231100000765 toxin Toxicity 0.000 description 1
• 108700012359 toxins Proteins 0.000 description 1
• 108091007466 transmembrane glycoproteins Proteins 0.000 description 1
• 230000004614 tumor growth Effects 0.000 description 1
• 239000005483 tyrosine kinase inhibitor Substances 0.000 description 1
• 229940121358 tyrosine kinase inhibitor Drugs 0.000 description 1
• ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
• XBEADGFTLHRJRB-UHFFFAOYSA-N undecylbenzene Chemical compound CCCCCCCCCCCC1=CC=CC=C1 XBEADGFTLHRJRB-UHFFFAOYSA-N 0.000 description 1
• 230000003827 upregulation Effects 0.000 description 1
• 229960005486 vaccine Drugs 0.000 description 1
• 229910052720 vanadium Inorganic materials 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
• 229950000578 vatalanib Drugs 0.000 description 1
• 239000011534 wash buffer Substances 0.000 description 1
• 239000000080 wetting agent Substances 0.000 description 1
• 229910052727 yttrium Inorganic materials 0.000 description 1