JP5647998B2 - 免疫抑制剤としてのチアゾロピリミジン調節因子 - Google Patents

Info

Publication number

JP5647998B2

JP5647998B2 JP2011553476A JP2011553476A JP5647998B2 JP 5647998 B2 JP5647998 B2 JP 5647998B2 JP 2011553476 A JP2011553476 A JP 2011553476A JP 2011553476 A JP2011553476 A JP 2011553476A JP 5647998 B2 JP5647998 B2 JP 5647998B2

Authority

JP

Japan

Prior art keywords

amino

thiazolo

piperazin

pyrimidin

fluorophenyl

Prior art date

2009-03-13

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Fee Related

Links

• Espacenet
• Global Dossier
• Discuss

• 239000003018 immunosuppressive agent Substances 0.000 title description 15
• 150000008634 thiazolopyrimidines Chemical class 0.000 title description 3
• 229960003444 immunosuppressant agent Drugs 0.000 title description 2
• -1 Hydroxylamino Chemical group 0.000 claims description 740
• 150000001875 compounds Chemical class 0.000 claims description 181
• 125000000217 alkyl group Chemical group 0.000 claims description 153
• 125000003118 aryl group Chemical group 0.000 claims description 112
• 125000003282 alkyl amino group Chemical group 0.000 claims description 88
• 238000000034 method Methods 0.000 claims description 77
• 150000001408 amides Chemical class 0.000 claims description 69
• 125000001424 substituent group Chemical group 0.000 claims description 66
• CDGFEINVQHEUQV-UHFFFAOYSA-N [1,3]thiazolo[5,4-d]pyrimidine Chemical group N1=CN=C2SC=NC2=C1 CDGFEINVQHEUQV-UHFFFAOYSA-N 0.000 claims description 60
• 125000001769 aryl amino group Chemical group 0.000 claims description 60
• 229910052736 halogen Inorganic materials 0.000 claims description 58
• 150000002367 halogens Chemical class 0.000 claims description 57
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 55
• 239000003814 drug Substances 0.000 claims description 54
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 53
• 125000003545 alkoxy group Chemical group 0.000 claims description 49
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 49
• 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 45
• 208000026278 immune system disease Diseases 0.000 claims description 43
• 239000008194 pharmaceutical composition Substances 0.000 claims description 36
• 210000000056 organ Anatomy 0.000 claims description 35
• 125000006323 alkenyl amino group Chemical group 0.000 claims description 33
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 33
• 125000003342 alkenyl group Chemical group 0.000 claims description 32
• 125000000304 alkynyl group Chemical group 0.000 claims description 30
• 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 30
• 125000004432 carbon atom Chemical group C* 0.000 claims description 29
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 29
• 238000002054 transplantation Methods 0.000 claims description 29
• 125000002252 acyl group Chemical group 0.000 claims description 28
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 28
• 125000005191 hydroxyalkylamino group Chemical group 0.000 claims description 28
• 125000006319 alkynyl amino group Chemical group 0.000 claims description 27
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 27
• 125000005843 halogen group Chemical group 0.000 claims description 27
• 125000004193 piperazinyl group Chemical group 0.000 claims description 27
• 150000003839 salts Chemical class 0.000 claims description 27
• 241000124008 Mammalia Species 0.000 claims description 26
• 241001465754 Metazoa Species 0.000 claims description 25
• 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 25
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 25
• 229940079593 drug Drugs 0.000 claims description 25
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 24
• 125000004442 acylamino group Chemical group 0.000 claims description 24
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 24
• 125000004104 aryloxy group Chemical group 0.000 claims description 24
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 24
• 208000023275 Autoimmune disease Diseases 0.000 claims description 23
• 230000001506 immunosuppresive effect Effects 0.000 claims description 22
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 21
• 125000000033 alkoxyamino group Chemical group 0.000 claims description 21
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
• 125000005276 alkyl hydrazino group Chemical group 0.000 claims description 19
• 125000001072 heteroaryl group Chemical group 0.000 claims description 19
• 125000005000 thioaryl group Chemical group 0.000 claims description 19
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 18
• 150000003566 thiocarboxylic acids Chemical class 0.000 claims description 18
• 239000000654 additive Substances 0.000 claims description 17
• 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 17
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
• 229920006395 saturated elastomer Polymers 0.000 claims description 17
• 125000004947 alkyl aryl amino group Chemical group 0.000 claims description 16
• AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims description 16
• 229940124530 sulfonamide Drugs 0.000 claims description 16
• 125000003441 thioacyl group Chemical group 0.000 claims description 16
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 15
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 14
• 125000001931 aliphatic group Chemical group 0.000 claims description 14
• 125000005018 aryl alkenyl group Chemical group 0.000 claims description 14
• 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 14
• 150000003456 sulfonamides Chemical class 0.000 claims description 14
• 125000006852 aliphatic spacer Chemical group 0.000 claims description 13
• 125000004429 atom Chemical group 0.000 claims description 13
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
• 125000000524 functional group Chemical group 0.000 claims description 13
• 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims description 12
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
• BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 claims description 11
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 11
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 10
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 9
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 9
• 150000007942 carboxylates Chemical class 0.000 claims description 9
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 9
• 239000012453 solvate Substances 0.000 claims description 9
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 8
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 8
• 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 8
• 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
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
• 125000004986 diarylamino group Chemical group 0.000 claims description 7
• 229940124622 immune-modulator drug Drugs 0.000 claims description 7
• 229940124589 immunosuppressive drug Drugs 0.000 claims description 7
• 125000002757 morpholinyl group Chemical group 0.000 claims description 7
• 125000003386 piperidinyl group Chemical group 0.000 claims description 7
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
• 150000003568 thioethers Chemical class 0.000 claims description 7
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 6
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
• 125000005026 carboxyaryl group Chemical group 0.000 claims description 6
• 230000001613 neoplastic effect Effects 0.000 claims description 6
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 6
• XXNYVMZIPHCWCM-UHFFFAOYSA-N 1-[4-[5-amino-2-(4-fluorophenyl)-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-bromophenoxy)ethanone Chemical compound C=12N=C(C=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Br)C=C1 XXNYVMZIPHCWCM-UHFFFAOYSA-N 0.000 claims description 5
• TYCJFZIWSCJVJW-UHFFFAOYSA-N 2-(4-chlorophenoxy)-1-piperazin-1-ylethanone Chemical compound C1=CC(Cl)=CC=C1OCC(=O)N1CCNCC1 TYCJFZIWSCJVJW-UHFFFAOYSA-N 0.000 claims description 5
• TWTYIRXSDNFQPI-UHFFFAOYSA-N 1-[4-[5-amino-2-[2-(4-fluorophenyl)ethyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(2,4-dichlorophenoxy)ethanone Chemical compound C=12N=C(CCC=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1Cl TWTYIRXSDNFQPI-UHFFFAOYSA-N 0.000 claims description 4
• LNVYSVHERQQLJV-UHFFFAOYSA-N 1-[4-[5-amino-2-[2-(4-fluorophenyl)ethyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(3-methylphenoxy)ethanone Chemical compound CC1=CC=CC(OCC(=O)N2CCN(CC2)C=2C=3N=C(CCC=4C=CC(F)=CC=4)SC=3N=C(N)N=2)=C1 LNVYSVHERQQLJV-UHFFFAOYSA-N 0.000 claims description 4
• YAXXQUZQCLSGFL-UHFFFAOYSA-N 1-[4-[5-amino-2-[2-(4-fluorophenyl)ethyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=12N=C(CCC=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 YAXXQUZQCLSGFL-UHFFFAOYSA-N 0.000 claims description 4
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
• SHDNTOJIAPVOQC-UHFFFAOYSA-N 7-(4-benzylpiperazin-1-yl)-2-(4-fluorophenyl)-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound C=12N=C(C=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1CC1=CC=CC=C1 SHDNTOJIAPVOQC-UHFFFAOYSA-N 0.000 claims description 4
• RWVALRMOWBIJHB-SFHVURJKSA-N 1-[(3s)-3-[[5-amino-2-[2-(4-fluorophenyl)ethyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]amino]pyrrolidin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C([C@@H](C1)NC=2N=C(N=C3SC(CCC=4C=CC(F)=CC=4)=NC3=2)N)CN1C(=O)COC1=CC=C(Cl)C=C1 RWVALRMOWBIJHB-SFHVURJKSA-N 0.000 claims description 3
• AGYGNJCHCJDIFU-UHFFFAOYSA-N 1-[4-(5-amino-2-methylsulfanyl-[1,3]thiazolo[5,4-d]pyrimidin-7-yl)piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound N1=C(N)N=C2SC(SC)=NC2=C1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 AGYGNJCHCJDIFU-UHFFFAOYSA-N 0.000 claims description 3
• PBAJDSDQGTWEPG-UHFFFAOYSA-N 1-[4-(5-amino-2-pyridin-3-yl-[1,3]thiazolo[5,4-d]pyrimidin-7-yl)piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=12N=C(C=3C=NC=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 PBAJDSDQGTWEPG-UHFFFAOYSA-N 0.000 claims description 3
• BGTAIFYUYWWVFH-UHFFFAOYSA-N 1-[4-[5-amino-2-(2-phenylethyl)-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=12N=C(CCC=3C=CC=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 BGTAIFYUYWWVFH-UHFFFAOYSA-N 0.000 claims description 3
• IGRDTEUVLUVFRF-UHFFFAOYSA-N 1-[4-[5-amino-2-(2-thiophen-2-ylethyl)-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-chlorophenyl)ethanone Chemical compound C=12N=C(CCC=3SC=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)CC1=CC=C(Cl)C=C1 IGRDTEUVLUVFRF-UHFFFAOYSA-N 0.000 claims description 3
• ZIBXOJHPXLDWBG-UHFFFAOYSA-N 1-[4-[5-amino-2-(3,4-dichlorophenyl)-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=12N=C(C=3C=C(Cl)C(Cl)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 ZIBXOJHPXLDWBG-UHFFFAOYSA-N 0.000 claims description 3
• XDOSZWBFJKIRSQ-UHFFFAOYSA-N 1-[4-[5-amino-2-(3-methoxyphenyl)-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound COC1=CC=CC(C=2SC3=NC(N)=NC(=C3N=2)N2CCN(CC2)C(=O)COC=2C=CC(Cl)=CC=2)=C1 XDOSZWBFJKIRSQ-UHFFFAOYSA-N 0.000 claims description 3
• JGRCFYSJXXAVJW-UHFFFAOYSA-N 1-[4-[5-amino-2-(4-chlorophenyl)-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=12N=C(C=3C=CC(Cl)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 JGRCFYSJXXAVJW-UHFFFAOYSA-N 0.000 claims description 3
• CESDYLQQGLEKAW-UHFFFAOYSA-N 1-[4-[5-amino-2-(4-fluoroanilino)-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=12N=C(NC=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 CESDYLQQGLEKAW-UHFFFAOYSA-N 0.000 claims description 3
• BXKFJPOPOHKAFN-UHFFFAOYSA-N 1-[4-[5-amino-2-(4-fluorophenyl)-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(3-nitrophenoxy)ethanone Chemical compound C=12N=C(C=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=CC([N+]([O-])=O)=C1 BXKFJPOPOHKAFN-UHFFFAOYSA-N 0.000 claims description 3
• KURFWIPHTYUQTR-UHFFFAOYSA-N 1-[4-[5-amino-2-(4-fluorophenyl)-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=12N=C(C=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 KURFWIPHTYUQTR-UHFFFAOYSA-N 0.000 claims description 3
• AFPOCDSWTQIMCH-UHFFFAOYSA-N 1-[4-[5-amino-2-[(4-fluorophenyl)methyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=12N=C(CC=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 AFPOCDSWTQIMCH-UHFFFAOYSA-N 0.000 claims description 3
• SCMNQHAJDPTKGO-UHFFFAOYSA-N 1-[4-[5-amino-2-[1-(4-fluorophenyl)propyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=1C=C(F)C=CC=1C(CC)C(SC1=NC(N)=N2)=NC1=C2N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 SCMNQHAJDPTKGO-UHFFFAOYSA-N 0.000 claims description 3
• AGOUPLUOZKXDIW-UHFFFAOYSA-N 1-[4-[5-amino-2-[2-(4-fluorophenyl)ethyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-bromophenoxy)ethanone Chemical compound C=12N=C(CCC=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Br)C=C1 AGOUPLUOZKXDIW-UHFFFAOYSA-N 0.000 claims description 3
• KQADOWXCIFMNDP-UHFFFAOYSA-N 1-[4-[5-amino-2-[2-(4-fluorophenyl)ethyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-chlorophenyl)ethanone Chemical compound C=12N=C(CCC=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)CC1=CC=C(Cl)C=C1 KQADOWXCIFMNDP-UHFFFAOYSA-N 0.000 claims description 3
• IHVXEJVBRMYPGX-UHFFFAOYSA-N 1-[4-[5-amino-2-[2-(4-fluorophenyl)ethyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-fluorophenoxy)ethanone Chemical compound C=12N=C(CCC=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(F)C=C1 IHVXEJVBRMYPGX-UHFFFAOYSA-N 0.000 claims description 3
• DBFCIRAYUIGTEY-UHFFFAOYSA-N 1-[4-[5-amino-2-[2-(4-fluorophenyl)ethyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-methoxyphenoxy)ethanone Chemical compound C1=CC(OC)=CC=C1OCC(=O)N1CCN(C=2C=3N=C(CCC=4C=CC(F)=CC=4)SC=3N=C(N)N=2)CC1 DBFCIRAYUIGTEY-UHFFFAOYSA-N 0.000 claims description 3
• HGKRGWQHCHIQFA-UHFFFAOYSA-N 1-[4-[5-amino-2-[2-(4-fluorophenyl)ethyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-phenoxyethanone Chemical compound C=12N=C(CCC=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=CC=C1 HGKRGWQHCHIQFA-UHFFFAOYSA-N 0.000 claims description 3
• GLXJSZVRBSONQF-UHFFFAOYSA-N 1-[4-[5-amino-2-[2-(4-fluorophenyl)ethyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-3-(4-fluorophenoxy)propan-1-one Chemical compound C=12N=C(CCC=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)CCOC1=CC=C(F)C=C1 GLXJSZVRBSONQF-UHFFFAOYSA-N 0.000 claims description 3
• IYYQYHPOEBKOQE-UHFFFAOYSA-N 1-[4-[5-amino-2-[2-(4-fluorophenyl)ethyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-3-phenylpropan-1-one Chemical compound C=12N=C(CCC=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)CCC1=CC=CC=C1 IYYQYHPOEBKOQE-UHFFFAOYSA-N 0.000 claims description 3
• UGAWSUBVALMCTC-UHFFFAOYSA-N 1-[4-[5-amino-2-[cyclopentyl-(4-fluorophenyl)methyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=12N=C(C(C3CCCC3)C=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 UGAWSUBVALMCTC-UHFFFAOYSA-N 0.000 claims description 3
• LISKJKUMLVQGKE-UHFFFAOYSA-N 1-morpholin-4-yl-2-piperazin-1-ylethanone Chemical compound C1COCCN1C(=O)CN1CCNCC1 LISKJKUMLVQGKE-UHFFFAOYSA-N 0.000 claims description 3
• DGHLAFBJSWAJIZ-UHFFFAOYSA-N 2-(4-chlorophenoxy)-1-[4-[2-(4-fluorophenyl)-5-methyl-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]ethanone Chemical compound C=12N=C(C=3C=CC(F)=CC=3)SC2=NC(C)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 DGHLAFBJSWAJIZ-UHFFFAOYSA-N 0.000 claims description 3
• RFUYQLOLZSUJLA-UHFFFAOYSA-N 2-(4-fluorophenyl)-7-(2-methoxyethoxy)-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound N=1C=2C(OCCOC)=NC(N)=NC=2SC=1C1=CC=C(F)C=C1 RFUYQLOLZSUJLA-UHFFFAOYSA-N 0.000 claims description 3
• VMNXWHGGIWMLBQ-UHFFFAOYSA-N 2-(4-fluorophenyl)-7-(4-pentylpiperazin-1-yl)-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound C1CN(CCCCC)CCN1C1=NC(N)=NC2=C1N=C(C=1C=CC(F)=CC=1)S2 VMNXWHGGIWMLBQ-UHFFFAOYSA-N 0.000 claims description 3
• KEJIHXKRBKXUJJ-UHFFFAOYSA-N 2-(4-fluorophenyl)-7-[4-(1,3-thiazol-2-yl)piperazin-1-yl]-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound C=12N=C(C=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C1=NC=CS1 KEJIHXKRBKXUJJ-UHFFFAOYSA-N 0.000 claims description 3
• RSTBWUBZEGOJOB-UHFFFAOYSA-N 2-(4-fluorophenyl)-7-[4-(3-methylphenyl)piperazin-1-yl]-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound CC1=CC=CC(N2CCN(CC2)C=2C=3N=C(SC=3N=C(N)N=2)C=2C=CC(F)=CC=2)=C1 RSTBWUBZEGOJOB-UHFFFAOYSA-N 0.000 claims description 3
• RATQQHHPXFJWAE-UHFFFAOYSA-N 2-[(4-fluorophenyl)methyl]-7-morpholin-4-yl-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound C=12N=C(CC=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N1CCOCC1 RATQQHHPXFJWAE-UHFFFAOYSA-N 0.000 claims description 3
• ORLAOQKPDJUERV-UHFFFAOYSA-N 2-[2-(4-fluorophenyl)ethyl]-7-[4-(2-phenoxyethyl)piperazin-1-yl]-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound C=12N=C(CCC=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1CCOC1=CC=CC=C1 ORLAOQKPDJUERV-UHFFFAOYSA-N 0.000 claims description 3
• AYUCYQYSRFCJNO-UHFFFAOYSA-N 2-[2-(4-fluorophenyl)ethyl]-7-piperazin-1-yl-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound C=12N=C(CCC=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N1CCNCC1 AYUCYQYSRFCJNO-UHFFFAOYSA-N 0.000 claims description 3
• LYMJTSXMIUWZSW-UHFFFAOYSA-N 4-[5-amino-2-[2-(4-fluorophenyl)ethyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]-n-(3-methylphenyl)piperazine-1-carboxamide Chemical compound CC1=CC=CC(NC(=O)N2CCN(CC2)C=2C=3N=C(CCC=4C=CC(F)=CC=4)SC=3N=C(N)N=2)=C1 LYMJTSXMIUWZSW-UHFFFAOYSA-N 0.000 claims description 3
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 3
• WEWKDLATYYFPLJ-UHFFFAOYSA-N 7-(4-benzylsulfonylpiperazin-1-yl)-2-[2-(4-fluorophenyl)ethyl]-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound C=12N=C(CCC=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1S(=O)(=O)CC1=CC=CC=C1 WEWKDLATYYFPLJ-UHFFFAOYSA-N 0.000 claims description 3
• YHSAVZQAAIOMFG-UHFFFAOYSA-N 7-[4-(benzenesulfonyl)piperazin-1-yl]-2-(4-fluorophenyl)-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound C=12N=C(C=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1S(=O)(=O)C1=CC=CC=C1 YHSAVZQAAIOMFG-UHFFFAOYSA-N 0.000 claims description 3
• KPDJDLDLQWMEEF-UHFFFAOYSA-N 7-ethoxy-2-(4-fluorophenyl)-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound N=1C=2C(OCC)=NC(N)=NC=2SC=1C1=CC=C(F)C=C1 KPDJDLDLQWMEEF-UHFFFAOYSA-N 0.000 claims description 3
• IOTQXHBOLWBDNO-UHFFFAOYSA-N [1-[5-amino-2-[2-(4-fluorophenyl)ethyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperidin-4-yl]-phenylmethanone Chemical compound C=12N=C(CCC=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N(CC1)CCC1C(=O)C1=CC=CC=C1 IOTQXHBOLWBDNO-UHFFFAOYSA-N 0.000 claims description 3
• XYOPNYPNRJVRKR-UHFFFAOYSA-N [4-[5-amino-2-(2-thiophen-2-ylethyl)-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-(4-chlorophenyl)methanone Chemical compound C=12N=C(CCC=3SC=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)C1=CC=C(Cl)C=C1 XYOPNYPNRJVRKR-UHFFFAOYSA-N 0.000 claims description 3
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
• WBNIMWDRBIBUEK-UHFFFAOYSA-N benzyl 4-[5-amino-2-(4-fluorophenyl)-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazine-1-carboxylate Chemical compound C=12N=C(C=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)OCC1=CC=CC=C1 WBNIMWDRBIBUEK-UHFFFAOYSA-N 0.000 claims description 3
• WNJOQYYEHQVKSI-HNNXBMFYSA-N tert-butyl (3s)-3-[[5-amino-2-[2-(4-fluorophenyl)ethyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]amino]pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC[C@@H]1NC1=NC(N)=NC2=C1N=C(CCC=1C=CC(F)=CC=1)S2 WNJOQYYEHQVKSI-HNNXBMFYSA-N 0.000 claims description 3
• JFLCLRXZVNJXLY-UHFFFAOYSA-N (4-methylphenyl) 4-(5-amino-2-pyridin-3-yl-[1,3]thiazolo[5,4-d]pyrimidin-7-yl)piperazine-1-carboxylate Chemical compound C1=CC(C)=CC=C1OC(=O)N1CCN(C=2C=3N=C(SC=3N=C(N)N=2)C=2C=NC=CC=2)CC1 JFLCLRXZVNJXLY-UHFFFAOYSA-N 0.000 claims description 2
• ONRXBNJZNNNJKH-UHFFFAOYSA-N 1-[4-(5-amino-2-cyclohexyl-[1,3]thiazolo[5,4-d]pyrimidin-7-yl)piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=12N=C(C3CCCCC3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 ONRXBNJZNNNJKH-UHFFFAOYSA-N 0.000 claims description 2
• MDJGNAZNHPVYES-UHFFFAOYSA-N 1-[4-(5-amino-2-cyclopropyl-[1,3]thiazolo[5,4-d]pyrimidin-7-yl)piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=12N=C(C3CC3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 MDJGNAZNHPVYES-UHFFFAOYSA-N 0.000 claims description 2
• FFYIDMIDTRSYCM-UHFFFAOYSA-N 1-[4-(5-amino-2-pentyl-[1,3]thiazolo[5,4-d]pyrimidin-7-yl)piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound N1=C(N)N=C2SC(CCCCC)=NC2=C1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 FFYIDMIDTRSYCM-UHFFFAOYSA-N 0.000 claims description 2
• NIILYBAXFOQFJE-UHFFFAOYSA-N 1-[4-(5-amino-2-pentyl-[1,3]thiazolo[5,4-d]pyrimidin-7-yl)piperazin-1-yl]-2-(4-methoxyphenoxy)ethanone Chemical compound N1=C(N)N=C2SC(CCCCC)=NC2=C1N(CC1)CCN1C(=O)COC1=CC=C(OC)C=C1 NIILYBAXFOQFJE-UHFFFAOYSA-N 0.000 claims description 2
• UGFOVUJJPRYQAK-UHFFFAOYSA-N 1-[4-(5-amino-2-phenyl-[1,3]thiazolo[5,4-d]pyrimidin-7-yl)piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=12N=C(C=3C=CC=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 UGFOVUJJPRYQAK-UHFFFAOYSA-N 0.000 claims description 2
• YDRDFSKLJIKUTM-UHFFFAOYSA-N 1-[4-(5-amino-2-pyridin-3-yl-[1,3]thiazolo[5,4-d]pyrimidin-7-yl)piperazin-1-yl]-2-(3-methylphenoxy)ethanone Chemical compound CC1=CC=CC(OCC(=O)N2CCN(CC2)C=2C=3N=C(SC=3N=C(N)N=2)C=2C=NC=CC=2)=C1 YDRDFSKLJIKUTM-UHFFFAOYSA-N 0.000 claims description 2
• FEACADSWWIGHLO-UHFFFAOYSA-N 1-[4-(5-amino-2-pyridin-3-yl-[1,3]thiazolo[5,4-d]pyrimidin-7-yl)piperazin-1-yl]-2-(4-chlorophenoxy)-2-methylpropan-1-one Chemical compound C1CN(C=2C=3N=C(SC=3N=C(N)N=2)C=2C=NC=CC=2)CCN1C(=O)C(C)(C)OC1=CC=C(Cl)C=C1 FEACADSWWIGHLO-UHFFFAOYSA-N 0.000 claims description 2
• LQDJVNXWAUMXGY-UHFFFAOYSA-N 1-[4-(5-amino-2-pyridin-3-yl-[1,3]thiazolo[5,4-d]pyrimidin-7-yl)piperazin-1-yl]-2-(4-fluorophenoxy)ethanone Chemical compound C=12N=C(C=3C=NC=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(F)C=C1 LQDJVNXWAUMXGY-UHFFFAOYSA-N 0.000 claims description 2
• CXCCIUUTRKWCEH-UHFFFAOYSA-N 1-[4-(5-amino-2-pyridin-3-yl-[1,3]thiazolo[5,4-d]pyrimidin-7-yl)piperazin-1-yl]-2-(4-methoxyphenoxy)ethanone Chemical compound C1=CC(OC)=CC=C1OCC(=O)N1CCN(C=2C=3N=C(SC=3N=C(N)N=2)C=2C=NC=CC=2)CC1 CXCCIUUTRKWCEH-UHFFFAOYSA-N 0.000 claims description 2
• YQEORQRIVXMANJ-UHFFFAOYSA-N 1-[4-(5-amino-2-pyridin-3-yl-[1,3]thiazolo[5,4-d]pyrimidin-7-yl)piperazin-1-yl]-2-[4-(trifluoromethoxy)phenoxy]ethanone Chemical compound C=12N=C(C=3C=NC=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(OC(F)(F)F)C=C1 YQEORQRIVXMANJ-UHFFFAOYSA-N 0.000 claims description 2
• MHNBQNCHUDWNAY-UHFFFAOYSA-N 1-[4-(5-amino-2-pyridin-4-yl-[1,3]thiazolo[5,4-d]pyrimidin-7-yl)piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=12N=C(C=3C=CN=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 MHNBQNCHUDWNAY-UHFFFAOYSA-N 0.000 claims description 2
• BOIQTHTYOPRRMI-UHFFFAOYSA-N 1-[4-[2-(4-fluorophenyl)-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-methoxyphenoxy)ethanone Chemical compound C1=CC(OC)=CC=C1OCC(=O)N1CCN(C=2C=3N=C(SC=3N=CN=2)C=2C=CC(F)=CC=2)CC1 BOIQTHTYOPRRMI-UHFFFAOYSA-N 0.000 claims description 2
• AVFMULBAPJSXEE-UHFFFAOYSA-N 1-[4-[2-[2-(4-fluorophenyl)ethyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-methoxyphenoxy)ethanone Chemical compound C1=CC(OC)=CC=C1OCC(=O)N1CCN(C=2C=3N=C(CCC=4C=CC(F)=CC=4)SC=3N=CN=2)CC1 AVFMULBAPJSXEE-UHFFFAOYSA-N 0.000 claims description 2
• KRYFVVOWHBKCIW-UHFFFAOYSA-N 1-[4-[5-amino-2-(4-fluorophenyl)-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(2,4-dichlorophenoxy)ethanone Chemical compound C=12N=C(C=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1Cl KRYFVVOWHBKCIW-UHFFFAOYSA-N 0.000 claims description 2
• YQVHACJRDOVTDZ-UHFFFAOYSA-N 1-[4-[5-amino-2-(4-fluorophenyl)-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(3-chlorophenoxy)ethanone Chemical compound C=12N=C(C=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=CC(Cl)=C1 YQVHACJRDOVTDZ-UHFFFAOYSA-N 0.000 claims description 2
• HSDPBPVPFVKIKS-UHFFFAOYSA-N 1-[4-[5-amino-2-(4-fluorophenyl)-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(3-methylphenoxy)ethanone Chemical compound CC1=CC=CC(OCC(=O)N2CCN(CC2)C=2C=3N=C(SC=3N=C(N)N=2)C=2C=CC(F)=CC=2)=C1 HSDPBPVPFVKIKS-UHFFFAOYSA-N 0.000 claims description 2
• HZNMPBDKNXTQDG-UHFFFAOYSA-N 1-[4-[5-amino-2-(4-fluorophenyl)-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-chloro-2-methylphenoxy)ethanone Chemical compound CC1=CC(Cl)=CC=C1OCC(=O)N1CCN(C=2C=3N=C(SC=3N=C(N)N=2)C=2C=CC(F)=CC=2)CC1 HZNMPBDKNXTQDG-UHFFFAOYSA-N 0.000 claims description 2
• ZFJMLJXZMDIEJI-UHFFFAOYSA-N 1-[4-[5-amino-2-(4-fluorophenyl)-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-chlorophenoxy)-2-methylpropan-1-one Chemical compound C1CN(C=2C=3N=C(SC=3N=C(N)N=2)C=2C=CC(F)=CC=2)CCN1C(=O)C(C)(C)OC1=CC=C(Cl)C=C1 ZFJMLJXZMDIEJI-UHFFFAOYSA-N 0.000 claims description 2
• WLDHICAHBAKWEB-UHFFFAOYSA-N 1-[4-[5-amino-2-(4-fluorophenyl)-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-methoxyphenoxy)ethanone Chemical compound C1=CC(OC)=CC=C1OCC(=O)N1CCN(C=2C=3N=C(SC=3N=C(N)N=2)C=2C=CC(F)=CC=2)CC1 WLDHICAHBAKWEB-UHFFFAOYSA-N 0.000 claims description 2
• GGNKZXNKCNEDBD-UHFFFAOYSA-N 1-[4-[5-amino-2-(4-fluorophenyl)-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-phenoxyethanone Chemical compound C=12N=C(C=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=CC=C1 GGNKZXNKCNEDBD-UHFFFAOYSA-N 0.000 claims description 2
• UUEJVCMVMAWPRX-UHFFFAOYSA-N 1-[4-[5-amino-2-(4-fluorophenyl)-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-3-(4-fluorophenyl)propan-1-one Chemical compound C=12N=C(C=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)CCC1=CC=C(F)C=C1 UUEJVCMVMAWPRX-UHFFFAOYSA-N 0.000 claims description 2
• LHGQBVDWIADCEH-UHFFFAOYSA-N 1-[4-[5-amino-2-(4-methylphenyl)-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C1=CC(C)=CC=C1C1=NC2=C(N3CCN(CC3)C(=O)COC=3C=CC(Cl)=CC=3)N=C(N)N=C2S1 LHGQBVDWIADCEH-UHFFFAOYSA-N 0.000 claims description 2
• GKGKGSPCILMFDY-UHFFFAOYSA-N 1-[4-[5-amino-2-(4-methylphenyl)-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-methoxyphenoxy)ethanone Chemical compound C1=CC(OC)=CC=C1OCC(=O)N1CCN(C=2C=3N=C(SC=3N=C(N)N=2)C=2C=CC(C)=CC=2)CC1 GKGKGSPCILMFDY-UHFFFAOYSA-N 0.000 claims description 2
• VFPNLHBPLKGLIW-UHFFFAOYSA-N 1-[4-[5-amino-2-(furan-2-yl)-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(3-methylphenoxy)ethanone Chemical compound CC1=CC=CC(OCC(=O)N2CCN(CC2)C=2C=3N=C(SC=3N=C(N)N=2)C=2OC=CC=2)=C1 VFPNLHBPLKGLIW-UHFFFAOYSA-N 0.000 claims description 2
• CSYZHVMTSLUGND-UHFFFAOYSA-N 1-[4-[5-amino-2-(furan-2-yl)-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-fluorophenoxy)ethanone Chemical compound C=12N=C(C=3OC=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(F)C=C1 CSYZHVMTSLUGND-UHFFFAOYSA-N 0.000 claims description 2
• CUULOWVQNUHTQE-UHFFFAOYSA-N 1-[4-[5-amino-2-[(4-chlorophenyl)methyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=12N=C(CC=3C=CC(Cl)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 CUULOWVQNUHTQE-UHFFFAOYSA-N 0.000 claims description 2
• OKFXMLCTWHZGIU-UHFFFAOYSA-N 1-[4-[5-amino-2-[(4-fluorophenyl)methyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-bromophenoxy)ethanone Chemical compound C=12N=C(CC=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Br)C=C1 OKFXMLCTWHZGIU-UHFFFAOYSA-N 0.000 claims description 2
• ROQZGBPPTPAGNF-UHFFFAOYSA-N 1-[4-[5-amino-2-[1-(4-chlorophenyl)cyclopropyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=12N=C(C3(CC3)C=3C=CC(Cl)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 ROQZGBPPTPAGNF-UHFFFAOYSA-N 0.000 claims description 2
• AJCILFMEZBIBSQ-UHFFFAOYSA-N 1-[4-[5-amino-2-[1-(4-chlorophenyl)ethyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=1C=C(Cl)C=CC=1C(C)C(SC1=NC(N)=N2)=NC1=C2N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 AJCILFMEZBIBSQ-UHFFFAOYSA-N 0.000 claims description 2
• KPWUVBHJGDYOGE-UHFFFAOYSA-N 1-[4-[5-amino-2-[1-(4-fluorophenyl)-2-phenylethyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=12N=C(C(CC=3C=CC=CC=3)C=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 KPWUVBHJGDYOGE-UHFFFAOYSA-N 0.000 claims description 2
• YJWDQXWACDUIPM-UHFFFAOYSA-N 1-[4-[5-amino-2-[1-(4-fluorophenyl)ethyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=1C=C(F)C=CC=1C(C)C(SC1=NC(N)=N2)=NC1=C2N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 YJWDQXWACDUIPM-UHFFFAOYSA-N 0.000 claims description 2
• LPLQRAXZUOONCH-UHFFFAOYSA-N 1-[4-[5-amino-2-[2-(3,4-dimethoxyphenyl)ethyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-bromophenoxy)ethanone Chemical compound C1=C(OC)C(OC)=CC=C1CCC1=NC2=C(N3CCN(CC3)C(=O)COC=3C=CC(Br)=CC=3)N=C(N)N=C2S1 LPLQRAXZUOONCH-UHFFFAOYSA-N 0.000 claims description 2
• XNKXOXZSNZKEOM-UHFFFAOYSA-N 1-[4-[5-amino-2-[2-(3,4-dimethoxyphenyl)ethyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-methoxyphenoxy)ethanone Chemical compound C1=CC(OC)=CC=C1OCC(=O)N1CCN(C=2C=3N=C(CCC=4C=C(OC)C(OC)=CC=4)SC=3N=C(N)N=2)CC1 XNKXOXZSNZKEOM-UHFFFAOYSA-N 0.000 claims description 2
• FPVUEEFJDLFBQK-UHFFFAOYSA-N 1-[4-[5-amino-2-[2-(3-methoxyphenyl)ethyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-bromophenoxy)ethanone Chemical compound COC1=CC=CC(CCC=2SC3=NC(N)=NC(=C3N=2)N2CCN(CC2)C(=O)COC=2C=CC(Br)=CC=2)=C1 FPVUEEFJDLFBQK-UHFFFAOYSA-N 0.000 claims description 2
• FVWGNQFBISULMT-UHFFFAOYSA-N 1-[4-[5-amino-2-[2-(3-methoxyphenyl)ethyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound COC1=CC=CC(CCC=2SC3=NC(N)=NC(=C3N=2)N2CCN(CC2)C(=O)COC=2C=CC(Cl)=CC=2)=C1 FVWGNQFBISULMT-UHFFFAOYSA-N 0.000 claims description 2
• MXCVAZWMSRFAPM-UHFFFAOYSA-N 1-[4-[5-amino-2-[2-(3-methoxyphenyl)ethyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-methoxyphenoxy)ethanone Chemical compound C1=CC(OC)=CC=C1OCC(=O)N1CCN(C=2C=3N=C(CCC=4C=C(OC)C=CC=4)SC=3N=C(N)N=2)CC1 MXCVAZWMSRFAPM-UHFFFAOYSA-N 0.000 claims description 2
• GBYZEOPIDMJAJT-UHFFFAOYSA-N 1-[4-[5-amino-2-[2-(4-bromophenyl)ethyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=12N=C(CCC=3C=CC(Br)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 GBYZEOPIDMJAJT-UHFFFAOYSA-N 0.000 claims description 2
• CGMGZFAXLOIMHO-UHFFFAOYSA-N 1-[4-[5-amino-2-[2-(4-bromophenyl)ethyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-methoxyphenoxy)ethanone Chemical compound C1=CC(OC)=CC=C1OCC(=O)N1CCN(C=2C=3N=C(CCC=4C=CC(Br)=CC=4)SC=3N=C(N)N=2)CC1 CGMGZFAXLOIMHO-UHFFFAOYSA-N 0.000 claims description 2
• JJAZUDGUCBHPLM-UHFFFAOYSA-N 1-[4-[5-amino-2-[2-(4-fluorophenoxy)ethyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=12N=C(CCOC=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 JJAZUDGUCBHPLM-UHFFFAOYSA-N 0.000 claims description 2
• LAPVDJYQYXEPJA-UHFFFAOYSA-N 1-[4-[5-amino-2-[2-(4-fluorophenyl)ethyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]-1,4-diazepan-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=12N=C(CCC=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N(CC1)CCCN1C(=O)COC1=CC=C(Cl)C=C1 LAPVDJYQYXEPJA-UHFFFAOYSA-N 0.000 claims description 2
• LRSJEAFJBZAIKH-UHFFFAOYSA-N 1-[4-[5-amino-2-[2-(4-fluorophenyl)ethyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(3-chlorophenoxy)ethanone Chemical compound C=12N=C(CCC=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=CC(Cl)=C1 LRSJEAFJBZAIKH-UHFFFAOYSA-N 0.000 claims description 2
• BZASDOUCFUIFGM-UHFFFAOYSA-N 1-[4-[5-amino-2-[2-(4-fluorophenyl)ethyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(3-nitrophenoxy)ethanone Chemical compound C=12N=C(CCC=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=CC([N+]([O-])=O)=C1 BZASDOUCFUIFGM-UHFFFAOYSA-N 0.000 claims description 2
• UBODTBYRYKMWOV-UHFFFAOYSA-N 1-[4-[5-amino-2-[2-(4-fluorophenyl)ethyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-hydroxyphenoxy)ethanone Chemical compound C=12N=C(CCC=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(O)C=C1 UBODTBYRYKMWOV-UHFFFAOYSA-N 0.000 claims description 2
• HISDHUMFQUKFPM-UHFFFAOYSA-N 1-[4-[5-amino-2-[2-(4-fluorophenyl)ethyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-[4-(trifluoromethoxy)phenoxy]ethanone Chemical compound C=12N=C(CCC=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(OC(F)(F)F)C=C1 HISDHUMFQUKFPM-UHFFFAOYSA-N 0.000 claims description 2
• JXSHRKAJNUZSPG-UHFFFAOYSA-N 1-[4-[5-amino-2-[2-(4-fluorophenyl)ethyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-3-(4-bromophenyl)propan-1-one Chemical compound C=12N=C(CCC=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)CCC1=CC=C(Br)C=C1 JXSHRKAJNUZSPG-UHFFFAOYSA-N 0.000 claims description 2
• WFWXCWYFLZYHOJ-UHFFFAOYSA-N 1-[4-[5-amino-2-[2-(4-methylphenyl)ethyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-bromophenoxy)ethanone Chemical compound C1=CC(C)=CC=C1CCC1=NC2=C(N3CCN(CC3)C(=O)COC=3C=CC(Br)=CC=3)N=C(N)N=C2S1 WFWXCWYFLZYHOJ-UHFFFAOYSA-N 0.000 claims description 2
• OTZCMVAMJKQGLU-UHFFFAOYSA-N 1-[4-[5-amino-2-[2-(4-methylphenyl)ethyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-methoxyphenoxy)ethanone Chemical compound C1=CC(OC)=CC=C1OCC(=O)N1CCN(C=2C=3N=C(CCC=4C=CC(C)=CC=4)SC=3N=C(N)N=2)CC1 OTZCMVAMJKQGLU-UHFFFAOYSA-N 0.000 claims description 2
• ZMWVFMSNLOCTRT-UHFFFAOYSA-N 1-[4-[5-amino-2-[3-(4-fluorophenyl)propyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=12N=C(CCCC=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 ZMWVFMSNLOCTRT-UHFFFAOYSA-N 0.000 claims description 2
• ZZWNCBAMZREDMI-UHFFFAOYSA-N 1-[4-[5-amino-2-[3-(4-fluorophenyl)propyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-methoxyphenoxy)ethanone Chemical compound C1=CC(OC)=CC=C1OCC(=O)N1CCN(C=2C=3N=C(CCCC=4C=CC(F)=CC=4)SC=3N=C(N)N=2)CC1 ZZWNCBAMZREDMI-UHFFFAOYSA-N 0.000 claims description 2
• NOCYVOZNFYXYHJ-UHFFFAOYSA-N 1-[4-[5-amino-2-[4-(4-fluorophenyl)butyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=12N=C(CCCCC=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 NOCYVOZNFYXYHJ-UHFFFAOYSA-N 0.000 claims description 2
• OOQIYNAFAJTXPY-UHFFFAOYSA-N 1-[4-[5-amino-2-[4-(4-fluorophenyl)butyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-methoxyphenoxy)ethanone Chemical compound C1=CC(OC)=CC=C1OCC(=O)N1CCN(C=2C=3N=C(CCCCC=4C=CC(F)=CC=4)SC=3N=C(N)N=2)CC1 OOQIYNAFAJTXPY-UHFFFAOYSA-N 0.000 claims description 2
• URGUCKDVRFXOOU-UHFFFAOYSA-N 1-piperazin-1-yl-2-[4-(trifluoromethoxy)phenoxy]ethanone Chemical compound C1=CC(OC(F)(F)F)=CC=C1OCC(=O)N1CCNCC1 URGUCKDVRFXOOU-UHFFFAOYSA-N 0.000 claims description 2
• VDFSNWBNLMGIEC-UHFFFAOYSA-N 2-(3-methylphenoxy)-1-piperazin-1-ylethanone Chemical compound CC1=CC=CC(OCC(=O)N2CCNCC2)=C1 VDFSNWBNLMGIEC-UHFFFAOYSA-N 0.000 claims description 2
• VSTIACPBLPUUQL-UHFFFAOYSA-N 2-(4-acetylphenoxy)-1-[4-[5-amino-2-[2-(4-fluorophenyl)ethyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1OCC(=O)N1CCN(C=2C=3N=C(CCC=4C=CC(F)=CC=4)SC=3N=C(N)N=2)CC1 VSTIACPBLPUUQL-UHFFFAOYSA-N 0.000 claims description 2
• PSAWQBIAETZLGD-UHFFFAOYSA-N 2-(4-acetylphenoxy)-1-piperazin-1-ylethanone Chemical compound C1=CC(C(=O)C)=CC=C1OCC(=O)N1CCNCC1 PSAWQBIAETZLGD-UHFFFAOYSA-N 0.000 claims description 2
• DTXZJPBYINJULD-UHFFFAOYSA-N 2-(4-bromophenoxy)-1-piperazin-1-ylethanone Chemical compound C1=CC(Br)=CC=C1OCC(=O)N1CCNCC1 DTXZJPBYINJULD-UHFFFAOYSA-N 0.000 claims description 2
• AYLVKZNYQVSDLY-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)-1-piperazin-1-ylethanone Chemical compound CC1=CC(Cl)=CC=C1OCC(=O)N1CCNCC1 AYLVKZNYQVSDLY-UHFFFAOYSA-N 0.000 claims description 2
• RIOIXQWQYCVOHU-UHFFFAOYSA-N 2-(4-chlorophenoxy)-1-[4-[2-(4-fluorophenyl)-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]ethanone Chemical compound C1=CC(F)=CC=C1C1=NC2=C(N3CCN(CC3)C(=O)COC=3C=CC(Cl)=CC=3)N=CN=C2S1 RIOIXQWQYCVOHU-UHFFFAOYSA-N 0.000 claims description 2
• PBUWPDLSZWMUBF-UHFFFAOYSA-N 2-(4-chlorophenoxy)-1-[4-[2-[2-(4-fluorophenyl)ethyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]ethanone Chemical compound C1=CC(F)=CC=C1CCC1=NC2=C(N3CCN(CC3)C(=O)COC=3C=CC(Cl)=CC=3)N=CN=C2S1 PBUWPDLSZWMUBF-UHFFFAOYSA-N 0.000 claims description 2
• XEISABBVEFAHAO-UHFFFAOYSA-N 2-(4-chlorophenoxy)-2-methyl-1-piperazin-1-ylpropan-1-one Chemical compound C1CNCCN1C(=O)C(C)(C)OC1=CC=C(Cl)C=C1 XEISABBVEFAHAO-UHFFFAOYSA-N 0.000 claims description 2
• UDBHBSDKADXKIT-UHFFFAOYSA-N 2-(4-fluorophenoxy)-1-piperazin-1-ylethanone Chemical compound C1=CC(F)=CC=C1OCC(=O)N1CCNCC1 UDBHBSDKADXKIT-UHFFFAOYSA-N 0.000 claims description 2
• QJFJCCRSKJPSMC-UHFFFAOYSA-N 2-(4-fluorophenyl)-7-morpholin-4-yl-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound C=12N=C(C=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N1CCOCC1 QJFJCCRSKJPSMC-UHFFFAOYSA-N 0.000 claims description 2
• NQELVURVHKIMJG-UHFFFAOYSA-N 2-(4-fluorophenyl)-7-piperazin-1-yl-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound C=12N=C(C=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N1CCNCC1 NQELVURVHKIMJG-UHFFFAOYSA-N 0.000 claims description 2
• UFAYWPNRXCCSJH-UHFFFAOYSA-N 2-(4-hydroxyphenoxy)-1-piperazin-1-ylethanone Chemical compound C1=CC(O)=CC=C1OCC(=O)N1CCNCC1 UFAYWPNRXCCSJH-UHFFFAOYSA-N 0.000 claims description 2
• GPRWAVJHNOECBQ-UHFFFAOYSA-N 2-(4-methoxyphenoxy)-1-piperazin-1-ylethanone Chemical compound C1=CC(OC)=CC=C1OCC(=O)N1CCNCC1 GPRWAVJHNOECBQ-UHFFFAOYSA-N 0.000 claims description 2
• PKALSDULVHJCMK-UHFFFAOYSA-N 2-[(4-fluorophenyl)methyl]-7-piperazin-1-yl-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound C=12N=C(CC=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N1CCNCC1 PKALSDULVHJCMK-UHFFFAOYSA-N 0.000 claims description 2
• ZORBHCDIZNKKRN-UHFFFAOYSA-N 2-[2-(4-methylphenyl)ethyl]-7-piperazin-1-yl-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound C1=CC(C)=CC=C1CCC1=NC2=C(N3CCNCC3)N=C(N)N=C2S1 ZORBHCDIZNKKRN-UHFFFAOYSA-N 0.000 claims description 2
• NSBAUMIEYZOCFH-UHFFFAOYSA-N 2-[4-[5-amino-2-(4-fluorophenyl)-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-1-morpholin-4-ylethanone Chemical compound C=12N=C(C=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1CC(=O)N1CCOCC1 NSBAUMIEYZOCFH-UHFFFAOYSA-N 0.000 claims description 2
• JIUBKRFMEIWBJQ-UHFFFAOYSA-N 2-[4-[5-amino-2-[2-(4-fluorophenyl)ethyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-n-methyl-n-phenylacetamide Chemical compound C=1C=CC=CC=1N(C)C(=O)CN(CC1)CCN1C(C=1N=2)=NC(N)=NC=1SC=2CCC1=CC=C(F)C=C1 JIUBKRFMEIWBJQ-UHFFFAOYSA-N 0.000 claims description 2
• IPFLHLWPVQVKAL-UHFFFAOYSA-N 2-cyclopropyl-7-methoxy-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound N=1C=2C(OC)=NC(N)=NC=2SC=1C1CC1 IPFLHLWPVQVKAL-UHFFFAOYSA-N 0.000 claims description 2
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
• DVYUZHWQRJJQII-UHFFFAOYSA-N 3-(4-bromophenyl)-1-piperazin-1-ylpropan-1-one Chemical compound C1=CC(Br)=CC=C1CCC(=O)N1CCNCC1 DVYUZHWQRJJQII-UHFFFAOYSA-N 0.000 claims description 2
• CHEFSLQUMQCXFW-UHFFFAOYSA-N 3-(4-fluorophenyl)-1-piperazin-1-ylpropan-1-one Chemical compound C1=CC(F)=CC=C1CCC(=O)N1CCNCC1 CHEFSLQUMQCXFW-UHFFFAOYSA-N 0.000 claims description 2
• BGMMWAVADSFHFV-UHFFFAOYSA-N 4-(5-amino-2-pyridin-3-yl-[1,3]thiazolo[5,4-d]pyrimidin-7-yl)-n-(4-chlorophenyl)piperazine-1-carboxamide Chemical compound C=12N=C(C=3C=NC=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)NC1=CC=C(Cl)C=C1 BGMMWAVADSFHFV-UHFFFAOYSA-N 0.000 claims description 2
• BGYPAUDZVQJLJK-UHFFFAOYSA-N 4-(5-amino-2-pyridin-3-yl-[1,3]thiazolo[5,4-d]pyrimidin-7-yl)-n-(4-cyanophenyl)piperazine-1-carboxamide Chemical compound C=12N=C(C=3C=NC=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)NC1=CC=C(C#N)C=C1 BGYPAUDZVQJLJK-UHFFFAOYSA-N 0.000 claims description 2
• CSUNQMPVPSYRGH-UHFFFAOYSA-N 4-(5-amino-2-pyridin-3-yl-[1,3]thiazolo[5,4-d]pyrimidin-7-yl)-n-[(4-methoxyphenyl)methyl]piperazine-1-carboxamide Chemical compound C1=CC(OC)=CC=C1CNC(=O)N1CCN(C=2C=3N=C(SC=3N=C(N)N=2)C=2C=NC=CC=2)CC1 CSUNQMPVPSYRGH-UHFFFAOYSA-N 0.000 claims description 2
• QBGFMDIGQMQAAY-UHFFFAOYSA-N 4-(5-amino-2-pyridin-3-yl-[1,3]thiazolo[5,4-d]pyrimidin-7-yl)-n-cyclohexylpiperazine-1-carboxamide Chemical compound C=12N=C(C=3C=NC=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)NC1CCCCC1 QBGFMDIGQMQAAY-UHFFFAOYSA-N 0.000 claims description 2
• JKUUKGFWIJBOIZ-UHFFFAOYSA-N 4-[5-amino-2-(2-thiophen-2-ylethyl)-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]-n-(3-methylphenyl)piperazine-1-carboxamide Chemical compound CC1=CC=CC(NC(=O)N2CCN(CC2)C=2C=3N=C(CCC=4SC=CC=4)SC=3N=C(N)N=2)=C1 JKUUKGFWIJBOIZ-UHFFFAOYSA-N 0.000 claims description 2
• 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 2
• SGSJTIHRAWXBGQ-UHFFFAOYSA-N 7-ethoxy-2-[(4-fluorophenyl)methyl]-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound N=1C=2C(OCC)=NC(N)=NC=2SC=1CC1=CC=C(F)C=C1 SGSJTIHRAWXBGQ-UHFFFAOYSA-N 0.000 claims description 2
• KCVVYWILFYFBKX-UHFFFAOYSA-N [4-[5-amino-2-[2-(4-fluorophenyl)ethyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-(4-chlorophenyl)methanone Chemical compound C=12N=C(CCC=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)C1=CC=C(Cl)C=C1 KCVVYWILFYFBKX-UHFFFAOYSA-N 0.000 claims description 2
• 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
• KNHZEKUNXNECCN-UHFFFAOYSA-N n-(2-methoxyphenyl)piperazine-1-carboxamide Chemical compound COC1=CC=CC=C1NC(=O)N1CCNCC1 KNHZEKUNXNECCN-UHFFFAOYSA-N 0.000 claims description 2
• XVGDSVSDVPYBSF-GOSISDBHSA-N n-[(3r)-1-[5-amino-2-[2-(4-fluorophenyl)ethyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]pyrrolidin-3-yl]-2-(4-chlorophenoxy)acetamide Chemical compound N([C@@H]1CCN(C1)C=1N=C(N=C2SC(CCC=3C=CC(F)=CC=3)=NC2=1)N)C(=O)COC1=CC=C(Cl)C=C1 XVGDSVSDVPYBSF-GOSISDBHSA-N 0.000 claims description 2
• JFJXOYMTJHHYAU-GOSISDBHSA-N n-[(3r)-1-[5-amino-2-[2-(4-fluorophenyl)ethyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]pyrrolidin-3-yl]-4-chlorobenzamide Chemical compound N([C@@H]1CCN(C1)C=1N=C(N=C2SC(CCC=3C=CC(F)=CC=3)=NC2=1)N)C(=O)C1=CC=C(Cl)C=C1 JFJXOYMTJHHYAU-GOSISDBHSA-N 0.000 claims description 2
• FHZVQMXIOZIBQO-UHFFFAOYSA-N 1-[4-[5-amino-2-(4-chlorophenyl)-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-methoxyphenoxy)ethanone Chemical compound C1=CC(OC)=CC=C1OCC(=O)N1CCN(C=2C=3N=C(SC=3N=C(N)N=2)C=2C=CC(Cl)=CC=2)CC1 FHZVQMXIOZIBQO-UHFFFAOYSA-N 0.000 claims 2
• KSWWWUGSAGJHDW-UHFFFAOYSA-N 1-[4-(5-amino-2-phenyl-[1,3]thiazolo[5,4-d]pyrimidin-7-yl)piperazin-1-yl]-2-(4-methoxyphenoxy)ethanone Chemical compound C1=CC(OC)=CC=C1OCC(=O)N1CCN(C=2C=3N=C(SC=3N=C(N)N=2)C=2C=CC=CC=2)CC1 KSWWWUGSAGJHDW-UHFFFAOYSA-N 0.000 claims 1
• CNLMRCWINTWWLY-UHFFFAOYSA-N 1-[4-(5-amino-2-pyridin-2-yl-[1,3]thiazolo[5,4-d]pyrimidin-7-yl)piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=12N=C(C=3N=CC=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 CNLMRCWINTWWLY-UHFFFAOYSA-N 0.000 claims 1
• YXOFGHDHCNKHOQ-UHFFFAOYSA-N 1-[4-[5-amino-2-(1-phenylcyclopropyl)-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=12N=C(C3(CC3)C=3C=CC=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 YXOFGHDHCNKHOQ-UHFFFAOYSA-N 0.000 claims 1
• ZIBGHZGPFOOSMD-UHFFFAOYSA-N 1-[4-[5-amino-2-(2-thiophen-2-ylethyl)-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=12N=C(CCC=3SC=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 ZIBGHZGPFOOSMD-UHFFFAOYSA-N 0.000 claims 1
• IVSKUPHKMKWFGI-UHFFFAOYSA-N 1-[4-[5-amino-2-(4-fluorophenyl)-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-fluorophenoxy)ethanone Chemical compound C=12N=C(C=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(F)C=C1 IVSKUPHKMKWFGI-UHFFFAOYSA-N 0.000 claims 1
• BDGATOOPYPZCLY-UHFFFAOYSA-N 1-[4-[5-amino-2-[(4-fluorophenyl)methyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-methoxyphenoxy)ethanone Chemical compound C1=CC(OC)=CC=C1OCC(=O)N1CCN(C=2C=3N=C(CC=4C=CC(F)=CC=4)SC=3N=C(N)N=2)CC1 BDGATOOPYPZCLY-UHFFFAOYSA-N 0.000 claims 1
• FIUURXKVYLZCIK-UHFFFAOYSA-N 1-[4-[5-amino-2-[2-(4-methylphenyl)ethyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C1=CC(C)=CC=C1CCC1=NC2=C(N3CCN(CC3)C(=O)COC=3C=CC(Cl)=CC=3)N=C(N)N=C2S1 FIUURXKVYLZCIK-UHFFFAOYSA-N 0.000 claims 1
• YEGXJZKXGWYYGG-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)-1-piperazin-1-ylethanone Chemical compound ClC1=CC(Cl)=CC=C1OCC(=O)N1CCNCC1 YEGXJZKXGWYYGG-UHFFFAOYSA-N 0.000 claims 1
• LMCJAXCSJHSFRC-UHFFFAOYSA-N 2-(3-chlorophenoxy)-1-piperazin-1-ylethanone Chemical compound ClC1=CC=CC(OCC(=O)N2CCNCC2)=C1 LMCJAXCSJHSFRC-UHFFFAOYSA-N 0.000 claims 1
• SSBDHFUDPFLFSS-UHFFFAOYSA-N 2-(4-chlorophenyl)-7-piperazin-1-yl-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound C=12N=C(C=3C=CC(Cl)=CC=3)SC2=NC(N)=NC=1N1CCNCC1 SSBDHFUDPFLFSS-UHFFFAOYSA-N 0.000 claims 1
• PRTRKRZZJKJTKM-UHFFFAOYSA-N 2-(4-fluorophenyl)-7-piperazin-1-yl-[1,3]thiazolo[5,4-d]pyrimidine Chemical compound C1=CC(F)=CC=C1C1=NC2=C(N3CCNCC3)N=CN=C2S1 PRTRKRZZJKJTKM-UHFFFAOYSA-N 0.000 claims 1
• DOGDGOGCRKKMIA-UHFFFAOYSA-N 2-(4-methylphenyl)-7-piperazin-1-yl-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound C1=CC(C)=CC=C1C1=NC2=C(N3CCNCC3)N=C(N)N=C2S1 DOGDGOGCRKKMIA-UHFFFAOYSA-N 0.000 claims 1
• LQRWOIAZEUKNOQ-UHFFFAOYSA-N 2-[2-(3,4-dimethoxyphenyl)ethyl]-7-piperazin-1-yl-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound C1=C(OC)C(OC)=CC=C1CCC1=NC2=C(N3CCNCC3)N=C(N)N=C2S1 LQRWOIAZEUKNOQ-UHFFFAOYSA-N 0.000 claims 1
• POHCZCHJNMZJBE-UHFFFAOYSA-N 2-[2-(3-methoxyphenyl)ethyl]-7-piperazin-1-yl-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound COC1=CC=CC(CCC=2SC3=NC(N)=NC(=C3N=2)N2CCNCC2)=C1 POHCZCHJNMZJBE-UHFFFAOYSA-N 0.000 claims 1
• TWWRDCDKFACSOM-UHFFFAOYSA-N 2-[2-(4-bromophenyl)ethyl]-7-piperazin-1-yl-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound C=12N=C(CCC=3C=CC(Br)=CC=3)SC2=NC(N)=NC=1N1CCNCC1 TWWRDCDKFACSOM-UHFFFAOYSA-N 0.000 claims 1
• OXLMODKFMCOXNV-UHFFFAOYSA-N 2-[2-(4-fluorophenyl)ethyl]-7-piperazin-1-yl-[1,3]thiazolo[5,4-d]pyrimidine Chemical compound C1=CC(F)=CC=C1CCC1=NC2=C(N3CCNCC3)N=CN=C2S1 OXLMODKFMCOXNV-UHFFFAOYSA-N 0.000 claims 1
• SMPGSDDXVCKAJW-UHFFFAOYSA-N 2-[3-(4-fluorophenyl)propyl]-7-piperazin-1-yl-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound C=12N=C(CCCC=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N1CCNCC1 SMPGSDDXVCKAJW-UHFFFAOYSA-N 0.000 claims 1
• IDFZTNSSSIAQRV-UHFFFAOYSA-N 2-[4-(4-fluorophenyl)butyl]-7-piperazin-1-yl-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound C=12N=C(CCCCC=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N1CCNCC1 IDFZTNSSSIAQRV-UHFFFAOYSA-N 0.000 claims 1
• PVMRKUCFNMEUQK-UHFFFAOYSA-N 2-[4-[5-amino-2-[2-(4-fluorophenyl)ethyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-n-(2-phenylethyl)acetamide Chemical compound C=12N=C(CCC=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1CC(=O)NCCC1=CC=CC=C1 PVMRKUCFNMEUQK-UHFFFAOYSA-N 0.000 claims 1
• RDPMCUVVUNXNNU-UHFFFAOYSA-N 2-pentyl-7-piperazin-1-yl-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound N1=C(N)N=C2SC(CCCCC)=NC2=C1N1CCNCC1 RDPMCUVVUNXNNU-UHFFFAOYSA-N 0.000 claims 1
• YMAZHUVQDZKBHV-UHFFFAOYSA-N 4-(5-amino-2-pyridin-3-yl-[1,3]thiazolo[5,4-d]pyrimidin-7-yl)-n-hexylpiperazine-1-carboxamide Chemical compound C1CN(C(=O)NCCCCCC)CCN1C1=NC(N)=NC2=C1N=C(C=1C=NC=CC=1)S2 YMAZHUVQDZKBHV-UHFFFAOYSA-N 0.000 claims 1
• RHWUBFTZEIZGSI-UHFFFAOYSA-N 4-(5-amino-2-pyridin-3-yl-[1,3]thiazolo[5,4-d]pyrimidin-7-yl)-n-phenylpiperazine-1-carboxamide Chemical compound C=12N=C(C=3C=NC=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)NC1=CC=CC=C1 RHWUBFTZEIZGSI-UHFFFAOYSA-N 0.000 claims 1
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
• VCFYKQVLQBUZSX-UHFFFAOYSA-N 7-piperazin-1-yl-2-(2-thiophen-2-ylethyl)-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound C=12N=C(CCC=3SC=CC=3)SC2=NC(N)=NC=1N1CCNCC1 VCFYKQVLQBUZSX-UHFFFAOYSA-N 0.000 claims 1
• FAPHFXKXUWZLLJ-UHFFFAOYSA-N 7-piperazin-1-yl-2-pyridin-2-yl-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound C=12N=C(C=3N=CC=CC=3)SC2=NC(N)=NC=1N1CCNCC1 FAPHFXKXUWZLLJ-UHFFFAOYSA-N 0.000 claims 1
• HHCFYILHMVJKAW-UHFFFAOYSA-N 7-piperazin-1-yl-2-pyridin-3-yl-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound C=12N=C(C=3C=NC=CC=3)SC2=NC(N)=NC=1N1CCNCC1 HHCFYILHMVJKAW-UHFFFAOYSA-N 0.000 claims 1
• GISKMZJKXVZYRY-UHFFFAOYSA-N 7-piperazin-1-yl-2-pyridin-4-yl-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound C=12N=C(C=3C=CN=CC=3)SC2=NC(N)=NC=1N1CCNCC1 GISKMZJKXVZYRY-UHFFFAOYSA-N 0.000 claims 1
• XPLLVMOMMKUTJI-UHFFFAOYSA-N benzyl 3-[[5-amino-2-[2-(4-fluorophenyl)ethyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]amino]piperidine-1-carboxylate Chemical compound C=12N=C(CCC=3C=CC(F)=CC=3)SC2=NC(N)=NC=1NC(C1)CCCN1C(=O)OCC1=CC=CC=C1 XPLLVMOMMKUTJI-UHFFFAOYSA-N 0.000 claims 1
• HLFMAANNMCCSMF-UHFFFAOYSA-N n-(2,4-difluorophenyl)piperazine-1-carboxamide Chemical compound FC1=CC(F)=CC=C1NC(=O)N1CCNCC1 HLFMAANNMCCSMF-UHFFFAOYSA-N 0.000 claims 1
• HRFZUFHAHQHMAY-UHFFFAOYSA-N n-(4-bromophenyl)piperazine-1-carboxamide Chemical compound C1=CC(Br)=CC=C1NC(=O)N1CCNCC1 HRFZUFHAHQHMAY-UHFFFAOYSA-N 0.000 claims 1
• 230000015572 biosynthetic process Effects 0.000 description 111
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 105
• 238000003786 synthesis reaction Methods 0.000 description 104
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 78
• 125000000623 heterocyclic group Chemical group 0.000 description 64
• 125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 description 64
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 63
• DDWBRNXDKNIQDY-UHFFFAOYSA-N thieno[2,3-d]pyrimidine Chemical class N1=CN=C2SC=CC2=C1 DDWBRNXDKNIQDY-UHFFFAOYSA-N 0.000 description 54
• 239000007787 solid Substances 0.000 description 53
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 50
• BRIOKNPDCPJCOD-UHFFFAOYSA-N [1,3]oxazolo[5,4-d]pyrimidine Chemical class N1=CN=C2OC=NC2=C1 BRIOKNPDCPJCOD-UHFFFAOYSA-N 0.000 description 49
• 238000006243 chemical reaction Methods 0.000 description 48
• 239000000460 chlorine Substances 0.000 description 46
• 150000004820 halides Chemical class 0.000 description 46
• 150000008064 anhydrides Chemical class 0.000 description 42
• 239000000203 mixture Substances 0.000 description 42
• 238000011282 treatment Methods 0.000 description 41
• 150000007970 thio esters Chemical class 0.000 description 40
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
• 150000002148 esters Chemical class 0.000 description 39
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 36
• 239000011541 reaction mixture Substances 0.000 description 36
• 125000004149 thio group Chemical group *S* 0.000 description 36
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 35
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
• 239000000243 solution Substances 0.000 description 34
• 238000003818 flash chromatography Methods 0.000 description 33
• 239000002904 solvent Substances 0.000 description 33
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 32
• 239000011734 sodium Substances 0.000 description 32
• 239000000377 silicon dioxide Substances 0.000 description 31
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
• 210000004027 cell Anatomy 0.000 description 28
• 229940083251 peripheral vasodilators purine derivative Drugs 0.000 description 28
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 27
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
• 239000002253 acid Substances 0.000 description 24
• 239000003153 chemical reaction reagent Substances 0.000 description 24
• 125000004414 alkyl thio group Chemical class 0.000 description 23
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 22
• 125000000753 cycloalkyl group Chemical group 0.000 description 22
• 235000019439 ethyl acetate Nutrition 0.000 description 22
• 210000001744 T-lymphocyte Anatomy 0.000 description 20
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 20
• 238000002360 preparation method Methods 0.000 description 20
• 239000002585 base Substances 0.000 description 19
• 239000012038 nucleophile Substances 0.000 description 19
• 230000002829 reductive effect Effects 0.000 description 19
• HJMZMZRCABDKKV-UHFFFAOYSA-N carbonocyanidic acid Chemical compound OC(=O)C#N HJMZMZRCABDKKV-UHFFFAOYSA-N 0.000 description 18
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 18
• KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 17
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 17
• 230000004913 activation Effects 0.000 description 17
• 238000003556 assay Methods 0.000 description 17
• 230000000694 effects Effects 0.000 description 17
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 16
• 230000008878 coupling Effects 0.000 description 16
• 238000010168 coupling process Methods 0.000 description 16
• 238000005859 coupling reaction Methods 0.000 description 16
• 229910052739 hydrogen Inorganic materials 0.000 description 16
• 239000001257 hydrogen Substances 0.000 description 16
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical group C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 15
• 229910052799 carbon Inorganic materials 0.000 description 15
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 14
• 238000007792 addition Methods 0.000 description 14
• 238000009472 formulation Methods 0.000 description 14
• 210000004698 lymphocyte Anatomy 0.000 description 14
• 150000003230 pyrimidines Chemical class 0.000 description 14
• 239000000741 silica gel Substances 0.000 description 14
• 229910002027 silica gel Inorganic materials 0.000 description 14
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical group OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 13
• DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 13
• 150000001241 acetals Chemical class 0.000 description 13
• 235000001014 amino acid Nutrition 0.000 description 13
• 150000001413 amino acids Chemical class 0.000 description 13
• 239000012267 brine Substances 0.000 description 13
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 13
• 229910052757 nitrogen Inorganic materials 0.000 description 13
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
• 150000001733 carboxylic acid esters Chemical class 0.000 description 12
• 125000005842 heteroatom Chemical group 0.000 description 12
• 238000004519 manufacturing process Methods 0.000 description 12
• 238000010534 nucleophilic substitution reaction Methods 0.000 description 12
• 229910052760 oxygen Inorganic materials 0.000 description 12
• 150000003555 thioacetals Chemical class 0.000 description 12
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
• PSXDJVGHVKVWDZ-UHFFFAOYSA-N (carbamothioylsulfamoylamino)urea Chemical class NC(=O)NNS(=O)(=O)NC(N)=S PSXDJVGHVKVWDZ-UHFFFAOYSA-N 0.000 description 11
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 11
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 11
• 238000004587 chromatography analysis Methods 0.000 description 11
• 229940083542 sodium Drugs 0.000 description 11
• 229910052708 sodium Inorganic materials 0.000 description 11
• 230000002195 synergetic effect Effects 0.000 description 11
• 125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 description 11
• FPIRBHDGWMWJEP-UHFFFAOYSA-N 1-hydroxy-7-azabenzotriazole Chemical compound C1=CN=C2N(O)N=NC2=C1 FPIRBHDGWMWJEP-UHFFFAOYSA-N 0.000 description 10
• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 10
• OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 10
• 125000003277 amino group Chemical group 0.000 description 10
• RROBIDXNTUAHFW-UHFFFAOYSA-N benzotriazol-1-yloxy-tris(dimethylamino)phosphanium Chemical compound C1=CC=C2N(O[P+](N(C)C)(N(C)C)N(C)C)N=NC2=C1 RROBIDXNTUAHFW-UHFFFAOYSA-N 0.000 description 10
• 238000001816 cooling Methods 0.000 description 10
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 10
• 150000002430 hydrocarbons Chemical group 0.000 description 10
• AWIJRPNMLHPLNC-UHFFFAOYSA-N methanethioic s-acid Chemical compound SC=O AWIJRPNMLHPLNC-UHFFFAOYSA-N 0.000 description 10
• CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical group S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 10
• 229910052717 sulfur Inorganic materials 0.000 description 10
• 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 10
• 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 9
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
• PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 description 9
• 108010036949 Cyclosporine Proteins 0.000 description 9
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
• 239000004480 active ingredient Substances 0.000 description 9
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 9
• 239000003795 chemical substances by application Substances 0.000 description 9
• 229960001265 ciclosporin Drugs 0.000 description 9
• 229940125721 immunosuppressive agent Drugs 0.000 description 9
• 239000003112 inhibitor Substances 0.000 description 9
• 150000003951 lactams Chemical group 0.000 description 9
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
• 239000001301 oxygen Substances 0.000 description 9
• 239000002244 precipitate Substances 0.000 description 9
• 229940002612 prodrug Drugs 0.000 description 9
• 239000000651 prodrug Substances 0.000 description 9
• 206010062016 Immunosuppression Diseases 0.000 description 8
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
• 125000002877 alkyl aryl group Chemical group 0.000 description 8
• 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 8
• 239000007800 oxidant agent Substances 0.000 description 8
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
• 238000007363 ring formation reaction Methods 0.000 description 8
• 238000012360 testing method Methods 0.000 description 8
• 238000006177 thiolation reaction Methods 0.000 description 8
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 7
• 239000004215 Carbon black (E152) Substances 0.000 description 7
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 7
• 102000004190 Enzymes Human genes 0.000 description 7
• 108090000790 Enzymes Proteins 0.000 description 7
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
• 230000002378 acidificating effect Effects 0.000 description 7
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 7
• 150000001350 alkyl halides Chemical class 0.000 description 7
• 238000005804 alkylation reaction Methods 0.000 description 7
• AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 7
• 230000026030 halogenation Effects 0.000 description 7
• 238000005658 halogenation reaction Methods 0.000 description 7
• 229930195733 hydrocarbon Natural products 0.000 description 7
• 238000001727 in vivo Methods 0.000 description 7
• CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 7
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 7
• 239000012299 nitrogen atmosphere Substances 0.000 description 7
• 125000004433 nitrogen atom Chemical group N* 0.000 description 7
• 238000010651 palladium-catalyzed cross coupling reaction Methods 0.000 description 7
• 239000000047 product Substances 0.000 description 7
• 125000000714 pyrimidinyl group Chemical group 0.000 description 7
• QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 description 7
• 239000007858 starting material Substances 0.000 description 7
• 150000003457 sulfones Chemical group 0.000 description 7
• 239000004094 surface-active agent Substances 0.000 description 7
• 239000003039 volatile agent Substances 0.000 description 7
• 239000008096 xylene Substances 0.000 description 7
• BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 6
• ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 6
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
• 108010002350 Interleukin-2 Proteins 0.000 description 6
• 102000000588 Interleukin-2 Human genes 0.000 description 6
• 125000004423 acyloxy group Chemical group 0.000 description 6
• 150000001543 aryl boronic acids Chemical class 0.000 description 6
• 230000001363 autoimmune Effects 0.000 description 6
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
• 238000009835 boiling Methods 0.000 description 6
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
• 229910052794 bromium Inorganic materials 0.000 description 6
• 150000001721 carbon Chemical group 0.000 description 6
• 230000000139 costimulatory effect Effects 0.000 description 6
• 229930182912 cyclosporin Natural products 0.000 description 6
• 201000010099 disease Diseases 0.000 description 6
• 239000003937 drug carrier Substances 0.000 description 6
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
• 230000002519 immonomodulatory effect Effects 0.000 description 6
• 238000000338 in vitro Methods 0.000 description 6
• 239000000543 intermediate Substances 0.000 description 6
• 210000002540 macrophage Anatomy 0.000 description 6
• 230000001404 mediated effect Effects 0.000 description 6
• 125000002950 monocyclic group Chemical group 0.000 description 6
• BXGTVNLGPMZLAZ-UHFFFAOYSA-N n'-ethylmethanediimine;hydrochloride Chemical compound Cl.CCN=C=N BXGTVNLGPMZLAZ-UHFFFAOYSA-N 0.000 description 6
• 239000012044 organic layer Substances 0.000 description 6
• 238000007254 oxidation reaction Methods 0.000 description 6
• 230000002265 prevention Effects 0.000 description 6
• FVLAYJRLBLHIPV-UHFFFAOYSA-N pyrimidin-5-amine Chemical compound NC1=CN=CN=C1 FVLAYJRLBLHIPV-UHFFFAOYSA-N 0.000 description 6
• ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Natural products COCC(O)C(=C/C(C)C(=O)CC(OC(=O)C1CCCCN1C(=O)C(=O)C2(O)OC(CC(OC)C(=CC=CC=CC(C)CC(C)C(=O)C)C)CCC2C)C(C)CC3CCC(O)C(C3)OC)C ZAHRKKWIAAJSAO-UHFFFAOYSA-N 0.000 description 6
• 229960002930 sirolimus Drugs 0.000 description 6
• 239000000126 substance Substances 0.000 description 6
• 239000011593 sulfur Chemical group 0.000 description 6
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
• 101150026303 HEX1 gene Proteins 0.000 description 5
• PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
• 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 5
• 150000007513 acids Chemical class 0.000 description 5
• 230000010933 acylation Effects 0.000 description 5
• 238000005917 acylation reaction Methods 0.000 description 5
• 150000001299 aldehydes Chemical class 0.000 description 5
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 5
• 230000029936 alkylation Effects 0.000 description 5
• 239000000427 antigen Substances 0.000 description 5
• 229910052801 chlorine Inorganic materials 0.000 description 5
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 5
• 238000001212 derivatisation Methods 0.000 description 5
• 235000014113 dietary fatty acids Nutrition 0.000 description 5
• 239000000194 fatty acid Substances 0.000 description 5
• 229930195729 fatty acid Natural products 0.000 description 5
• 150000004665 fatty acids Chemical class 0.000 description 5
• NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 5
• 239000002955 immunomodulating agent Substances 0.000 description 5
• 210000004185 liver Anatomy 0.000 description 5
• 125000000018 nitroso group Chemical group N(=O)* 0.000 description 5
• 239000002736 nonionic surfactant Substances 0.000 description 5
• 231100000252 nontoxic Toxicity 0.000 description 5
• 230000003000 nontoxic effect Effects 0.000 description 5
• 125000004043 oxo group Chemical group O=* 0.000 description 5
• 125000003367 polycyclic group Chemical group 0.000 description 5
• 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 5
• 210000001519 tissue Anatomy 0.000 description 5
• UAJFCVURUYZZSL-UHFFFAOYSA-N (carbamoylamino)carbamothioylcarbamic acid Chemical compound N(C(=O)N)NC(NC(=O)O)=S UAJFCVURUYZZSL-UHFFFAOYSA-N 0.000 description 4
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
• HWSJQFCTYLBBOF-UHFFFAOYSA-N 2,5-diamino-4-hydroxy-1h-pyrimidin-6-one Chemical compound NC1=NC(O)=C(N)C(O)=N1 HWSJQFCTYLBBOF-UHFFFAOYSA-N 0.000 description 4
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 4
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
• 101000914514 Homo sapiens T-cell-specific surface glycoprotein CD28 Proteins 0.000 description 4
• 241001024304 Mino Species 0.000 description 4
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical group CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
• 206010039897 Sedation Diseases 0.000 description 4
• 102100027213 T-cell-specific surface glycoprotein CD28 Human genes 0.000 description 4
• 206010052779 Transplant rejections Diseases 0.000 description 4
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
• 238000004458 analytical method Methods 0.000 description 4
• 230000001028 anti-proliverative effect Effects 0.000 description 4
• 108091007433 antigens Proteins 0.000 description 4
• 102000036639 antigens Human genes 0.000 description 4
• 239000011575 calcium Substances 0.000 description 4
• 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 4
• 210000004443 dendritic cell Anatomy 0.000 description 4
• GLFVNTDRBTZJIY-UHFFFAOYSA-N diethyl 2-aminopropanedioate;hydron;chloride Chemical compound Cl.CCOC(=O)C(N)C(=O)OCC GLFVNTDRBTZJIY-UHFFFAOYSA-N 0.000 description 4
• 208000035475 disorder Diseases 0.000 description 4
• 150000002431 hydrogen Chemical class 0.000 description 4
• 125000002632 imidazolidinyl group Chemical group 0.000 description 4
• 230000028993 immune response Effects 0.000 description 4
• 208000027866 inflammatory disease Diseases 0.000 description 4
• 238000002347 injection Methods 0.000 description 4
• 239000007924 injection Substances 0.000 description 4
• 230000003993 interaction Effects 0.000 description 4
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
• 239000000546 pharmaceutical excipient Substances 0.000 description 4
• 239000002798 polar solvent Substances 0.000 description 4
• 229910000027 potassium carbonate Inorganic materials 0.000 description 4
• 229930195734 saturated hydrocarbon Natural products 0.000 description 4
• 230000036280 sedation Effects 0.000 description 4
• 238000010561 standard procedure Methods 0.000 description 4
• 150000003462 sulfoxides Chemical class 0.000 description 4
• HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 4
• 230000001225 therapeutic effect Effects 0.000 description 4
• 150000003556 thioamides Chemical class 0.000 description 4
• UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
• WYWHKKSPHMUBEB-UHFFFAOYSA-N tioguanine Chemical compound N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 description 4
• 230000001988 toxicity Effects 0.000 description 4
• 231100000419 toxicity Toxicity 0.000 description 4
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
• BUTTVUBNXIIXRH-UHFFFAOYSA-N 1-(cyclopropylmethyl)pyrazole-4-carbaldehyde Chemical compound C1=C(C=O)C=NN1CC1CC1 BUTTVUBNXIIXRH-UHFFFAOYSA-N 0.000 description 3
• FJIYBSRUHOAVDM-UHFFFAOYSA-N 2-(4-fluorophenyl)-7-methylsulfanyl-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound N=1C=2C(SC)=NC(N)=NC=2SC=1C1=CC=C(F)C=C1 FJIYBSRUHOAVDM-UHFFFAOYSA-N 0.000 description 3
• 238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 description 3
• 101150013553 CD40 gene Proteins 0.000 description 3
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
• 229930105110 Cyclosporin A Natural products 0.000 description 3
• 102000004127 Cytokines Human genes 0.000 description 3
• 108090000695 Cytokines Proteins 0.000 description 3
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
• 238000007341 Heck reaction Methods 0.000 description 3
• 241000282412 Homo Species 0.000 description 3
• 108010074328 Interferon-gamma Proteins 0.000 description 3
• 102000013462 Interleukin-12 Human genes 0.000 description 3
• 108010065805 Interleukin-12 Proteins 0.000 description 3
• 238000005577 Kumada cross-coupling reaction Methods 0.000 description 3
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
• OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 3
• 241000699670 Mus sp. Species 0.000 description 3
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 3
• 238000006411 Negishi coupling reaction Methods 0.000 description 3
• 206010028980 Neoplasm Diseases 0.000 description 3
• 229910019142 PO4 Inorganic materials 0.000 description 3
• 208000002193 Pain Diseases 0.000 description 3
• 239000002202 Polyethylene glycol Substances 0.000 description 3
• 201000004681 Psoriasis Diseases 0.000 description 3
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
• 241000283984 Rodentia Species 0.000 description 3
• 238000006069 Suzuki reaction reaction Methods 0.000 description 3
• 102100040245 Tumor necrosis factor receptor superfamily member 5 Human genes 0.000 description 3
• 230000009471 action Effects 0.000 description 3
• 230000000996 additive effect Effects 0.000 description 3
• 229910052783 alkali metal Inorganic materials 0.000 description 3
• 150000001340 alkali metals Chemical class 0.000 description 3
• 150000001336 alkenes Chemical group 0.000 description 3
• 150000001345 alkine derivatives Chemical group 0.000 description 3
• 125000005257 alkyl acyl group Chemical group 0.000 description 3
• 125000005277 alkyl imino group Chemical class 0.000 description 3
• 150000001412 amines Chemical class 0.000 description 3
• 229910021529 ammonia Inorganic materials 0.000 description 3
• 150000003863 ammonium salts Chemical class 0.000 description 3
• 150000004982 aromatic amines Chemical class 0.000 description 3
• 150000001502 aryl halides Chemical class 0.000 description 3
• 229960002170 azathioprine Drugs 0.000 description 3
• LMEKQMALGUDUQG-UHFFFAOYSA-N azathioprine Chemical compound CN1C=NC([N+]([O-])=O)=C1SC1=NC=NC2=C1NC=N2 LMEKQMALGUDUQG-UHFFFAOYSA-N 0.000 description 3
• 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 3
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
• 230000004071 biological effect Effects 0.000 description 3
• 230000037396 body weight Effects 0.000 description 3
• 201000011510 cancer Diseases 0.000 description 3
• 239000003246 corticosteroid Substances 0.000 description 3
• 229960001334 corticosteroids Drugs 0.000 description 3
• MHDFJESNGMDHQD-UHFFFAOYSA-N dimethyl 2-aminopropanedioate Chemical compound COC(=O)C(N)C(=O)OC MHDFJESNGMDHQD-UHFFFAOYSA-N 0.000 description 3
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
• LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
• 239000003349 gelling agent Substances 0.000 description 3
• 210000002216 heart Anatomy 0.000 description 3
• 238000010438 heat treatment Methods 0.000 description 3
• 229940121354 immunomodulator Drugs 0.000 description 3
• 230000002584 immunomodulator Effects 0.000 description 3
• 230000005764 inhibitory process Effects 0.000 description 3
• 239000012948 isocyanate Chemical group 0.000 description 3
• DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 3
• BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 3
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
• 238000007799 mixed lymphocyte reaction assay Methods 0.000 description 3
• 201000006417 multiple sclerosis Diseases 0.000 description 3
• MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
• 230000003647 oxidation Effects 0.000 description 3
• 230000036407 pain Effects 0.000 description 3
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
• 235000021317 phosphate Nutrition 0.000 description 3
• RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 3
• 229920001223 polyethylene glycol Polymers 0.000 description 3
• 229920001451 polypropylene glycol Polymers 0.000 description 3
• 239000000843 powder Substances 0.000 description 3
• 230000002062 proliferating effect Effects 0.000 description 3
• 230000035755 proliferation Effects 0.000 description 3
• 238000006467 substitution reaction Methods 0.000 description 3
• 150000003460 sulfonic acids Chemical class 0.000 description 3
• 238000011287 therapeutic dose Methods 0.000 description 3
• NIYGIWBXQHELDN-UHFFFAOYSA-N thieno[2,3-d]pyrimidine-2-carboxylic acid Chemical compound OC(=O)C1=NC=C2C=CSC2=N1 NIYGIWBXQHELDN-UHFFFAOYSA-N 0.000 description 3
• 150000003571 thiolactams Chemical group 0.000 description 3
• RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical group SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
• 231100000331 toxic Toxicity 0.000 description 3
• 230000002588 toxic effect Effects 0.000 description 3
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
• 238000013389 whole blood assay Methods 0.000 description 3
• 238000002689 xenotransplantation Methods 0.000 description 3
• JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 2
• MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 description 2
• 125000006701 (C1-C7) alkyl group Chemical group 0.000 description 2
• 125000006717 (C3-C10) cycloalkenyl group Chemical group 0.000 description 2
• GVDORJZDLXJLLC-UHFFFAOYSA-N 1-[4-(2-amino-8-cyclopentylsulfanyl-7h-purin-6-yl)piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=12N=C(SC3CCCC3)NC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 GVDORJZDLXJLLC-UHFFFAOYSA-N 0.000 description 2
• ZDGQRAWDQIUTKI-UHFFFAOYSA-N 1-[4-(2-amino-9-methyl-8-methylsulfanylpurin-6-yl)piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound N1=C(N)N=C2N(C)C(SC)=NC2=C1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 ZDGQRAWDQIUTKI-UHFFFAOYSA-N 0.000 description 2
• OHEFJYWOYMPUHR-UHFFFAOYSA-N 1-[4-(5-amino-2-pentyl-[1,3]oxazolo[5,4-d]pyrimidin-7-yl)piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound N1=C(N)N=C2OC(CCCCC)=NC2=C1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 OHEFJYWOYMPUHR-UHFFFAOYSA-N 0.000 description 2
• IFCLDWSGEICRTE-UHFFFAOYSA-N 1-[4-[2-amino-6-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=12C=C(C=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 IFCLDWSGEICRTE-UHFFFAOYSA-N 0.000 description 2
• FDWOKRZSLGPTBG-UHFFFAOYSA-N 1-[4-[2-amino-8-(3-chlorophenyl)-7h-purin-6-yl]piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=12N=C(C=3C=C(Cl)C=CC=3)NC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 FDWOKRZSLGPTBG-UHFFFAOYSA-N 0.000 description 2
• ANIZKKQNDMMBMZ-UHFFFAOYSA-N 1-[4-[2-amino-8-(4-fluorophenyl)-7h-purin-6-yl]piperazin-1-yl]-3-phenylpropan-1-one Chemical compound C=12N=C(C=3C=CC(F)=CC=3)NC2=NC(N)=NC=1N(CC1)CCN1C(=O)CCC1=CC=CC=C1 ANIZKKQNDMMBMZ-UHFFFAOYSA-N 0.000 description 2
• MPYXGDVWYORQLA-UHFFFAOYSA-N 1-[4-[2-amino-8-[4-(trifluoromethoxy)phenyl]-7h-purin-6-yl]piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=12N=C(C=3C=CC(OC(F)(F)F)=CC=3)NC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 MPYXGDVWYORQLA-UHFFFAOYSA-N 0.000 description 2
• MQRPBANEXOSDGN-UHFFFAOYSA-N 1-[4-[5-amino-2-(4-fluorophenyl)-[1,3]oxazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(3-nitrophenoxy)ethanone Chemical compound C=12N=C(C=3C=CC(F)=CC=3)OC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=CC([N+]([O-])=O)=C1 MQRPBANEXOSDGN-UHFFFAOYSA-N 0.000 description 2
• XMDQAICFEBPNJK-UHFFFAOYSA-N 1-[4-[5-amino-2-(4-fluorophenyl)-[1,3]oxazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=12N=C(C=3C=CC(F)=CC=3)OC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 XMDQAICFEBPNJK-UHFFFAOYSA-N 0.000 description 2
• WKNLBNROOFYBDI-UHFFFAOYSA-N 1-[4-[5-amino-2-[2-(4-fluorophenyl)ethyl]-[1,3]oxazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=12N=C(CCC=3C=CC(F)=CC=3)OC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 WKNLBNROOFYBDI-UHFFFAOYSA-N 0.000 description 2
• PAOZUHUVVUJRDT-UHFFFAOYSA-N 1-[4-[5-amino-2-[2-(4-fluorophenyl)ethyl]-[1,3]oxazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-chlorophenyl)ethanone Chemical compound C=12N=C(CCC=3C=CC(F)=CC=3)OC2=NC(N)=NC=1N(CC1)CCN1C(=O)CC1=CC=C(Cl)C=C1 PAOZUHUVVUJRDT-UHFFFAOYSA-N 0.000 description 2
• CPPGZWWUPFWALU-UHFFFAOYSA-N 1-isocyanato-3-methylbenzene Chemical compound CC1=CC=CC(N=C=O)=C1 CPPGZWWUPFWALU-UHFFFAOYSA-N 0.000 description 2
• ZJFSQVPWMJRWFD-UHFFFAOYSA-N 2-(4-chlorophenoxy)-1-[4-[2-(4-fluorophenyl)-5-methyl-[1,3]oxazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]ethanone Chemical compound C=12N=C(C=3C=CC(F)=CC=3)OC2=NC(C)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 ZJFSQVPWMJRWFD-UHFFFAOYSA-N 0.000 description 2
• ISJYYLKISXNLLZ-UHFFFAOYSA-N 2-(4-chlorophenoxy)-1-[4-[2-(4-fluorophenyl)-[1,3]oxazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]ethanone Chemical compound C1=CC(F)=CC=C1C1=NC2=C(N3CCN(CC3)C(=O)COC=3C=CC(Cl)=CC=3)N=CN=C2O1 ISJYYLKISXNLLZ-UHFFFAOYSA-N 0.000 description 2
• QWEIUROUCNABOD-UHFFFAOYSA-N 2-(4-chlorophenoxy)-1-[4-[2-[(4-fluorophenyl)methyl]-5-methyl-[1,3]oxazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]ethanone Chemical compound C=12N=C(CC=3C=CC(F)=CC=3)OC2=NC(C)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 QWEIUROUCNABOD-UHFFFAOYSA-N 0.000 description 2
• FRSCHISFKLZDNE-UHFFFAOYSA-N 2-(4-chlorophenoxy)-1-[4-[6-(4-fluorophenyl)-2-methylthieno[2,3-d]pyrimidin-4-yl]piperazin-1-yl]ethanone Chemical compound C=12C=C(C=3C=CC(F)=CC=3)SC2=NC(C)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 FRSCHISFKLZDNE-UHFFFAOYSA-N 0.000 description 2
• ZIZHOHVSCJKUQF-UHFFFAOYSA-N 2-(4-chlorophenoxy)-1-[4-[6-(4-fluorophenyl)-2-phenylthieno[2,3-d]pyrimidin-4-yl]piperazin-1-yl]ethanone Chemical compound C1=CC(F)=CC=C1C1=CC2=C(N3CCN(CC3)C(=O)COC=3C=CC(Cl)=CC=3)N=C(C=3C=CC=CC=3)N=C2S1 ZIZHOHVSCJKUQF-UHFFFAOYSA-N 0.000 description 2
• VRBVHQUSAOKVDH-UHFFFAOYSA-N 2-(4-chlorophenoxy)acetyl chloride Chemical compound ClC(=O)COC1=CC=C(Cl)C=C1 VRBVHQUSAOKVDH-UHFFFAOYSA-N 0.000 description 2
• LAVOFWAAXWYLJR-UHFFFAOYSA-N 2-(4-fluorophenyl)-5,7-bis(methylsulfanyl)-[1,3]thiazolo[5,4-d]pyrimidine Chemical compound S1C2=NC(SC)=NC(SC)=C2N=C1C1=CC=C(F)C=C1 LAVOFWAAXWYLJR-UHFFFAOYSA-N 0.000 description 2
• FNYNAXQIHPQOSG-UHFFFAOYSA-N 2-[(4-fluorophenyl)methyl]-7-methylsulfanyl-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound N=1C=2C(SC)=NC(N)=NC=2SC=1CC1=CC=C(F)C=C1 FNYNAXQIHPQOSG-UHFFFAOYSA-N 0.000 description 2
• DKIAOICEHLLJNU-UHFFFAOYSA-N 2-[1-(4-fluorophenyl)-2-phenylethyl]-7-methylsulfanyl-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound N=1C=2C(SC)=NC(N)=NC=2SC=1C(C=1C=CC(F)=CC=1)CC1=CC=CC=C1 DKIAOICEHLLJNU-UHFFFAOYSA-N 0.000 description 2
• MKVSYRRPGYYUJD-UHFFFAOYSA-N 2-[2-(4-fluorophenoxy)ethyl]-7-methylsulfanyl-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound N=1C=2C(SC)=NC(N)=NC=2SC=1CCOC1=CC=C(F)C=C1 MKVSYRRPGYYUJD-UHFFFAOYSA-N 0.000 description 2
• HUSPMFNPRHBKFE-UHFFFAOYSA-N 2-[2-(4-fluorophenyl)ethyl]-7-[4-(1,3-thiazol-2-yl)piperazin-1-yl]-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound C=12N=C(CCC=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C1=NC=CS1 HUSPMFNPRHBKFE-UHFFFAOYSA-N 0.000 description 2
• XXOMNMWCPWSPLS-UHFFFAOYSA-N 2-[2-(4-fluorophenyl)ethyl]-7-methylsulfanyl-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound N=1C=2C(SC)=NC(N)=NC=2SC=1CCC1=CC=C(F)C=C1 XXOMNMWCPWSPLS-UHFFFAOYSA-N 0.000 description 2
• IWARXXBAUZGEAF-UHFFFAOYSA-N 2-[2-(4-fluorophenyl)ethyl]-7-methylsulfonyl-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound N=1C=2C(S(=O)(=O)C)=NC(N)=NC=2SC=1CCC1=CC=C(F)C=C1 IWARXXBAUZGEAF-UHFFFAOYSA-N 0.000 description 2
• DJNIIAQCDNXCCX-UHFFFAOYSA-N 2-[4-[4-[2-(4-chlorophenoxy)acetyl]piperazin-1-yl]-6-(4-fluorophenyl)thieno[2,3-d]pyrimidin-2-yl]acetamide Chemical compound C=12C=C(C=3C=CC(F)=CC=3)SC2=NC(CC(=O)N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 DJNIIAQCDNXCCX-UHFFFAOYSA-N 0.000 description 2
• YPCGDGWLGZUUST-UHFFFAOYSA-N 2-butyl-n-(3-chloro-4-fluorophenyl)-6-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-amine Chemical compound C=12C=C(C=3C=CC(F)=CC=3)SC2=NC(CCCC)=NC=1NC1=CC=C(F)C(Cl)=C1 YPCGDGWLGZUUST-UHFFFAOYSA-N 0.000 description 2
• BMIBJCFFZPYJHF-UHFFFAOYSA-N 2-methoxy-5-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Chemical compound COC1=NC=C(C)C=C1B1OC(C)(C)C(C)(C)O1 BMIBJCFFZPYJHF-UHFFFAOYSA-N 0.000 description 2
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
• QCEDXODAYRWQRH-UHFFFAOYSA-N 3-(4-fluorophenoxy)propanoic acid Chemical compound OC(=O)CCOC1=CC=C(F)C=C1 QCEDXODAYRWQRH-UHFFFAOYSA-N 0.000 description 2
• DUFGYCAXVIUXIP-UHFFFAOYSA-N 4,6-dihydroxypyrimidine Chemical class OC1=CC(O)=NC=N1 DUFGYCAXVIUXIP-UHFFFAOYSA-N 0.000 description 2
• UMSFRPADYZSSFV-UHFFFAOYSA-N 4-(2-amino-6-phenylthieno[2,3-d]pyrimidin-4-yl)-n-(4-chlorophenyl)piperazine-1-carboxamide Chemical compound C=12C=C(C=3C=CC=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)NC1=CC=C(Cl)C=C1 UMSFRPADYZSSFV-UHFFFAOYSA-N 0.000 description 2
• HBPMNASYNVTFOC-UHFFFAOYSA-N 4-[4-[2-(4-chlorophenoxy)acetyl]piperazin-1-yl]-6-(4-fluorophenyl)-n-(2-methoxyethyl)thieno[2,3-d]pyrimidine-2-carboxamide Chemical compound C=12C=C(C=3C=CC(F)=CC=3)SC2=NC(C(=O)NCCOC)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 HBPMNASYNVTFOC-UHFFFAOYSA-N 0.000 description 2
• PWRBPXKVDUZDKI-UHFFFAOYSA-N 4-[5-amino-2-[2-(4-fluorophenyl)ethyl]-[1,3]oxazolo[5,4-d]pyrimidin-7-yl]-n-(3-methylphenyl)piperazine-1-carboxamide Chemical compound CC1=CC=CC(NC(=O)N2CCN(CC2)C=2C=3N=C(CCC=4C=CC(F)=CC=4)OC=3N=C(N)N=2)=C1 PWRBPXKVDUZDKI-UHFFFAOYSA-N 0.000 description 2
• WUBBRNOQWQTFEX-UHFFFAOYSA-M 4-aminosalicylate(1-) Chemical compound NC1=CC=C(C([O-])=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-M 0.000 description 2
• CEGRCQZYSINSRI-UHFFFAOYSA-N 5,7-bis(benzylsulfanyl)-2-(4-fluorophenyl)-[1,3]thiazolo[5,4-d]pyrimidine Chemical compound C1=CC(F)=CC=C1C(SC1=NC(SCC=2C=CC=CC=2)=N2)=NC1=C2SCC1=CC=CC=C1 CEGRCQZYSINSRI-UHFFFAOYSA-N 0.000 description 2
• YPQWPFBLOQNPBE-UHFFFAOYSA-N 5,7-bis(butylsulfanyl)-2-(4-fluorophenyl)-[1,3]thiazolo[5,4-d]pyrimidine Chemical compound S1C2=NC(SCCCC)=NC(SCCCC)=C2N=C1C1=CC=C(F)C=C1 YPQWPFBLOQNPBE-UHFFFAOYSA-N 0.000 description 2
• HESVXKZDSUGWQM-UHFFFAOYSA-N 7-benzylsulfanyl-2-(4-fluorophenyl)-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound C=12N=C(C=3C=CC(F)=CC=3)SC2=NC(N)=NC=1SCC1=CC=CC=C1 HESVXKZDSUGWQM-UHFFFAOYSA-N 0.000 description 2
• JUKPTTSTHGFSGD-UHFFFAOYSA-N 7-chloro-2-(4-fluorophenyl)-5-methyl-[1,3]thiazolo[5,4-d]pyrimidine Chemical compound S1C2=NC(C)=NC(Cl)=C2N=C1C1=CC=C(F)C=C1 JUKPTTSTHGFSGD-UHFFFAOYSA-N 0.000 description 2
• FAYGVDHTAUGZLD-UHFFFAOYSA-N 7-ethoxy-2-(4-fluorophenyl)-5-methylsulfanyl-[1,3]thiazolo[5,4-d]pyrimidine Chemical compound N=1C=2C(OCC)=NC(SC)=NC=2SC=1C1=CC=C(F)C=C1 FAYGVDHTAUGZLD-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
• 231100000039 Ames test Toxicity 0.000 description 2
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
• 208000008439 Biliary Liver Cirrhosis Diseases 0.000 description 2
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
• 102000004631 Calcineurin Human genes 0.000 description 2
• 108010042955 Calcineurin Proteins 0.000 description 2
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
• 241000282472 Canis lupus familiaris Species 0.000 description 2
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
• 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
• 208000011231 Crohn disease Diseases 0.000 description 2
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
• KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
• HKVAMNSJSFKALM-GKUWKFKPSA-N Everolimus Chemical compound C1C[C@@H](OCCO)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 HKVAMNSJSFKALM-GKUWKFKPSA-N 0.000 description 2
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
• ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
• 108010010803 Gelatin Proteins 0.000 description 2
• ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
• 206010019842 Hepatomegaly Diseases 0.000 description 2
• 101001012157 Homo sapiens Receptor tyrosine-protein kinase erbB-2 Proteins 0.000 description 2
• 206010020751 Hypersensitivity Diseases 0.000 description 2
• 206010020772 Hypertension Diseases 0.000 description 2
• 208000022559 Inflammatory bowel disease Diseases 0.000 description 2
• 102000008070 Interferon-gamma Human genes 0.000 description 2
• 102000000589 Interleukin-1 Human genes 0.000 description 2
• 108010002352 Interleukin-1 Proteins 0.000 description 2
• 102000003812 Interleukin-15 Human genes 0.000 description 2
• 108090000172 Interleukin-15 Proteins 0.000 description 2
• 108090001005 Interleukin-6 Proteins 0.000 description 2
• 102000004889 Interleukin-6 Human genes 0.000 description 2
• FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 description 2
• JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 2
• 101150058160 Lyn gene Proteins 0.000 description 2
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
• 108091000080 Phosphotransferase Proteins 0.000 description 2
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
• 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
• ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 2
• 102100030086 Receptor tyrosine-protein kinase erbB-2 Human genes 0.000 description 2
• 102000001332 SRC Human genes 0.000 description 2
• 108060006706 SRC Proteins 0.000 description 2
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
• 229920002125 Sokalan® Polymers 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
• 230000006044 T cell activation Effects 0.000 description 2
• 239000012317 TBTU Substances 0.000 description 2
• QJJXYPPXXYFBGM-LFZNUXCKSA-N Tacrolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1\C=C(/C)[C@@H]1[C@H](C)[C@@H](O)CC(=O)[C@H](CC=C)/C=C(C)/C[C@H](C)C[C@H](OC)[C@H]([C@H](C[C@H]2C)OC)O[C@@]2(O)C(=O)C(=O)N2CCCC[C@H]2C(=O)O1 QJJXYPPXXYFBGM-LFZNUXCKSA-N 0.000 description 2
• FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
• GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
• 102000008236 Toll-Like Receptor 7 Human genes 0.000 description 2
• 108010060825 Toll-Like Receptor 7 Proteins 0.000 description 2
• 108060008682 Tumor Necrosis Factor Proteins 0.000 description 2
• 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 2
• 206010046851 Uveitis Diseases 0.000 description 2
• 102000005789 Vascular Endothelial Growth Factors Human genes 0.000 description 2
• 108010019530 Vascular Endothelial Growth Factors Proteins 0.000 description 2
• RTFCJMYSXJQTOP-UHFFFAOYSA-N [4-[5-amino-2-[2-(4-fluorophenyl)ethyl]-[1,3]oxazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-(4-chlorophenyl)methanone Chemical compound C=12N=C(CCC=3C=CC(F)=CC=3)OC2=NC(N)=NC=1N(CC1)CCN1C(=O)C1=CC=C(Cl)C=C1 RTFCJMYSXJQTOP-UHFFFAOYSA-N 0.000 description 2
• 239000012190 activator Substances 0.000 description 2
• 230000001154 acute effect Effects 0.000 description 2
• 239000000443 aerosol Substances 0.000 description 2
• 239000003513 alkali Substances 0.000 description 2
• 150000004703 alkoxides Chemical class 0.000 description 2
• 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 2
• 125000002947 alkylene group Chemical group 0.000 description 2
• 125000003368 amide group Chemical group 0.000 description 2
• 238000010171 animal model Methods 0.000 description 2
• 239000003945 anionic surfactant Substances 0.000 description 2
• 239000007864 aqueous solution Substances 0.000 description 2
• 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
• 206010003246 arthritis Diseases 0.000 description 2
• 125000005251 aryl acyl group Chemical group 0.000 description 2
• 150000001500 aryl chlorides Chemical class 0.000 description 2
• 208000006673 asthma Diseases 0.000 description 2
• 239000005441 aurora Substances 0.000 description 2
• 210000003719 b-lymphocyte Anatomy 0.000 description 2
• 229940050390 benzoate Drugs 0.000 description 2
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 2
• 210000001185 bone marrow Anatomy 0.000 description 2
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
• 229910052791 calcium Inorganic materials 0.000 description 2
• 159000000007 calcium salts Chemical class 0.000 description 2
• 235000013877 carbamide Nutrition 0.000 description 2
• 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 2
• 239000001768 carboxy methyl cellulose Substances 0.000 description 2
• 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
• 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
• 239000000969 carrier Substances 0.000 description 2
• 239000004359 castor oil Substances 0.000 description 2
• 235000019438 castor oil Nutrition 0.000 description 2
• 239000003093 cationic surfactant Substances 0.000 description 2
• 239000001913 cellulose Substances 0.000 description 2
• 229920002678 cellulose Polymers 0.000 description 2
• 239000012320 chlorinating reagent Substances 0.000 description 2
• 150000001805 chlorine compounds Chemical class 0.000 description 2
• FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical group ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 2
• 125000001309 chloro group Chemical group Cl* 0.000 description 2
• OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
• 239000008139 complexing agent Substances 0.000 description 2
• 238000013270 controlled release Methods 0.000 description 2
• 239000007819 coupling partner Substances 0.000 description 2
• 125000000392 cycloalkenyl group Chemical group 0.000 description 2
• 230000034994 death Effects 0.000 description 2
• 229960003957 dexamethasone Drugs 0.000 description 2
• 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 2
• 206010012601 diabetes mellitus Diseases 0.000 description 2
• TZFQICFHDMXLIX-UHFFFAOYSA-N diethyl 2-(hexanoylamino)propanedioate Chemical compound CCCCCC(=O)NC(C(=O)OCC)C(=O)OCC TZFQICFHDMXLIX-UHFFFAOYSA-N 0.000 description 2
• 230000004069 differentiation Effects 0.000 description 2
• BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 2
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
• 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 2
• 238000001647 drug administration Methods 0.000 description 2
• 239000003995 emulsifying agent Substances 0.000 description 2
• 102000052116 epidermal growth factor receptor activity proteins Human genes 0.000 description 2
• 108700015053 epidermal growth factor receptor activity proteins Proteins 0.000 description 2
• BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 2
• 150000002170 ethers Chemical class 0.000 description 2
• MKJQYFVTEPGXIE-UHFFFAOYSA-N ethyl 2-aminothiophene-3-carboxylate Chemical compound CCOC(=O)C=1C=CSC=1N MKJQYFVTEPGXIE-UHFFFAOYSA-N 0.000 description 2
• VRUIWWATCNYPKW-UHFFFAOYSA-N ethyl 4-[(3-methylphenyl)carbamoyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1C(=O)NC1=CC=CC(C)=C1 VRUIWWATCNYPKW-UHFFFAOYSA-N 0.000 description 2
• 150000002191 fatty alcohols Chemical class 0.000 description 2
• 238000001914 filtration Methods 0.000 description 2
• 239000011737 fluorine Substances 0.000 description 2
• 229910052731 fluorine Inorganic materials 0.000 description 2
• 125000001207 fluorophenyl group Chemical group 0.000 description 2
• 230000006870 function Effects 0.000 description 2
• 239000000499 gel Substances 0.000 description 2
• 239000008273 gelatin Substances 0.000 description 2
• 229920000159 gelatin Polymers 0.000 description 2
• 235000019322 gelatine Nutrition 0.000 description 2
• 235000011852 gelatine desserts Nutrition 0.000 description 2
• ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
• 150000004795 grignard reagents Chemical class 0.000 description 2
• JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 2
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
• 125000002883 imidazolyl group Chemical group 0.000 description 2
• 230000005847 immunogenicity Effects 0.000 description 2
• PCKPVGOLPKLUHR-UHFFFAOYSA-N indoxyl Chemical group C1=CC=C2C(O)=CNC2=C1 PCKPVGOLPKLUHR-UHFFFAOYSA-N 0.000 description 2
• 230000006698 induction Effects 0.000 description 2
• 230000002401 inhibitory effect Effects 0.000 description 2
• NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
• 230000008611 intercellular interaction Effects 0.000 description 2
• 229960003130 interferon gamma Drugs 0.000 description 2
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
• 150000002513 isocyanates Chemical group 0.000 description 2
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
• 210000003734 kidney Anatomy 0.000 description 2
• 208000032839 leukemia Diseases 0.000 description 2
• 239000003446 ligand Substances 0.000 description 2
• 239000007788 liquid Substances 0.000 description 2
• 239000000395 magnesium oxide Substances 0.000 description 2
• CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
• AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 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
• 239000012528 membrane Substances 0.000 description 2
• GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 description 2
• 229960000485 methotrexate Drugs 0.000 description 2
• DGGJQLCAYQCPDD-UHFFFAOYSA-N methyl 2-aminothiophene-3-carboxylate Chemical compound COC(=O)C=1C=CSC=1N DGGJQLCAYQCPDD-UHFFFAOYSA-N 0.000 description 2
• 239000004005 microsphere Substances 0.000 description 2
• 206010028417 myasthenia gravis Diseases 0.000 description 2
• YOHYSYJDKVYCJI-UHFFFAOYSA-N n-[3-[[6-[3-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]phenyl]cyclopropanecarboxamide Chemical compound FC(F)(F)C1=CC=CC(NC=2N=CN=C(NC=3C=C(NC(=O)C4CC4)C=CC=3)C=2)=C1 YOHYSYJDKVYCJI-UHFFFAOYSA-N 0.000 description 2
• 229910052759 nickel Inorganic materials 0.000 description 2
• 150000002825 nitriles Chemical class 0.000 description 2
• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
• 125000005429 oxyalkyl group Chemical group 0.000 description 2
• 125000004430 oxygen atom Chemical group O* 0.000 description 2
• 229910052763 palladium Inorganic materials 0.000 description 2
• 125000000913 palmityl 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])C([H])([H])C([H])([H])[H] 0.000 description 2
• 210000000496 pancreas Anatomy 0.000 description 2
• 238000005897 peptide coupling reaction Methods 0.000 description 2
• 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 2
• 239000010452 phosphate Substances 0.000 description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
• 150000003904 phospholipids Chemical class 0.000 description 2
• XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 2
• 102000020233 phosphotransferase Human genes 0.000 description 2
• 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 2
• 239000010695 polyglycol Substances 0.000 description 2
• 229920000151 polyglycol Polymers 0.000 description 2
• 229920000642 polymer Polymers 0.000 description 2
• 239000002243 precursor Substances 0.000 description 2
• 229960005205 prednisolone Drugs 0.000 description 2
• OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 2
• 230000008569 process Effects 0.000 description 2
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
• 125000006239 protecting group Chemical group 0.000 description 2
• 108090000623 proteins and genes Proteins 0.000 description 2
• 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
• UYLWKSJTHLRFBX-UHFFFAOYSA-N purin-6-one Chemical class O=C1N=CN=C2N=CN=C12 UYLWKSJTHLRFBX-UHFFFAOYSA-N 0.000 description 2
• 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 2
• 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
• 230000009257 reactivity Effects 0.000 description 2
• 238000011160 research Methods 0.000 description 2
• 230000004044 response Effects 0.000 description 2
• 206010039073 rheumatoid arthritis Diseases 0.000 description 2
• YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 2
• 150000003335 secondary amines Chemical class 0.000 description 2
• 230000028327 secretion Effects 0.000 description 2
• 210000002966 serum Anatomy 0.000 description 2
• 235000012239 silicon dioxide Nutrition 0.000 description 2
• 239000000344 soap Substances 0.000 description 2
• QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
• 239000012265 solid product Substances 0.000 description 2
• 235000010199 sorbic acid Nutrition 0.000 description 2
• 239000004334 sorbic acid Substances 0.000 description 2
• 229940075582 sorbic acid Drugs 0.000 description 2
• 241000894007 species Species 0.000 description 2
• ATHGHQPFGPMSJY-UHFFFAOYSA-N spermidine Chemical compound NCCCCNCCCN ATHGHQPFGPMSJY-UHFFFAOYSA-N 0.000 description 2
• 239000007921 spray Substances 0.000 description 2
• 210000002784 stomach Anatomy 0.000 description 2
• KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
• KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
• 150000003871 sulfonates Chemical class 0.000 description 2
• 125000004434 sulfur atom Chemical group 0.000 description 2
• 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
• 238000013268 sustained release Methods 0.000 description 2
• 239000012730 sustained-release form Substances 0.000 description 2
• 239000011885 synergistic combination Substances 0.000 description 2
• 229960001967 tacrolimus Drugs 0.000 description 2
• QJJXYPPXXYFBGM-SHYZHZOCSA-N tacrolimus Natural products CO[C@H]1C[C@H](CC[C@@H]1O)C=C(C)[C@H]2OC(=O)[C@H]3CCCCN3C(=O)C(=O)[C@@]4(O)O[C@@H]([C@H](C[C@H]4C)OC)[C@@H](C[C@H](C)CC(=C[C@@H](CC=C)C(=O)C[C@H](O)[C@H]2C)C)OC QJJXYPPXXYFBGM-SHYZHZOCSA-N 0.000 description 2
• 229940095064 tartrate Drugs 0.000 description 2
• SXZGWXDUNIURRN-UHFFFAOYSA-N tert-butyl 4-[2-(4-chlorophenoxy)acetyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C(=O)COC1=CC=C(Cl)C=C1 SXZGWXDUNIURRN-UHFFFAOYSA-N 0.000 description 2
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
• ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 2
• 125000000335 thiazolyl group Chemical group 0.000 description 2
• 239000002562 thickening agent Substances 0.000 description 2
• RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical compound C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 description 2
• 125000001544 thienyl group Chemical group 0.000 description 2
• 125000004568 thiomorpholinyl group Chemical group 0.000 description 2
• 125000001425 triazolyl group Chemical group 0.000 description 2
• CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 2
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
• 208000035408 type 1 diabetes mellitus 1 Diseases 0.000 description 2
• QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical class O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
• VUAFHZCUKUDDBC-SCSAIBSYSA-N (2s)-2-[(2-methyl-2-sulfanylpropanoyl)amino]-3-sulfanylpropanoic acid Chemical compound CC(C)(S)C(=O)N[C@H](CS)C(O)=O VUAFHZCUKUDDBC-SCSAIBSYSA-N 0.000 description 1
• ASWBNKHCZGQVJV-UHFFFAOYSA-N (3-hexadecanoyloxy-2-hydroxypropyl) 2-(trimethylazaniumyl)ethyl phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(O)COP([O-])(=O)OCC[N+](C)(C)C ASWBNKHCZGQVJV-UHFFFAOYSA-N 0.000 description 1
• VEEGZPWAAPPXRB-BJMVGYQFSA-N (3e)-3-(1h-imidazol-5-ylmethylidene)-1h-indol-2-one Chemical compound O=C1NC2=CC=CC=C2\C1=C/C1=CN=CN1 VEEGZPWAAPPXRB-BJMVGYQFSA-N 0.000 description 1
• KEUPLGRNURQXAR-UHFFFAOYSA-N (4-chlorophenyl) acetate Chemical compound CC(=O)OC1=CC=C(Cl)C=C1 KEUPLGRNURQXAR-UHFFFAOYSA-N 0.000 description 1
• 125000006586 (C3-C10) cycloalkylene group Chemical group 0.000 description 1
• GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 1
• WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
• WHTVZRBIWZFKQO-AWEZNQCLSA-N (S)-chloroquine Chemical compound ClC1=CC=C2C(N[C@@H](C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-AWEZNQCLSA-N 0.000 description 1
• MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 1
• NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 description 1
• KILNVBDSWZSGLL-KXQOOQHDSA-N 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC KILNVBDSWZSGLL-KXQOOQHDSA-N 0.000 description 1
• TZCPCKNHXULUIY-RGULYWFUSA-N 1,2-distearoyl-sn-glycero-3-phosphoserine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCCCC TZCPCKNHXULUIY-RGULYWFUSA-N 0.000 description 1
• YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
• SRGYIOWEOTVTRE-UHFFFAOYSA-N 1,3-oxazinane-2,6-dione Chemical compound O=C1CCNC(=O)O1 SRGYIOWEOTVTRE-UHFFFAOYSA-N 0.000 description 1
• JIWHIRLNKIUYSM-UHFFFAOYSA-N 1-(3-methylphenyl)piperazine Chemical compound CC1=CC=CC(N2CCNCC2)=C1 JIWHIRLNKIUYSM-UHFFFAOYSA-N 0.000 description 1
• NCXUNZWLEYGQAH-UHFFFAOYSA-N 1-(dimethylamino)propan-2-ol Chemical compound CC(O)CN(C)C NCXUNZWLEYGQAH-UHFFFAOYSA-N 0.000 description 1
• GONNHMAPYIHDPT-UHFFFAOYSA-N 1-[4-(2-amino-6-phenylthieno[2,3-d]pyrimidin-4-yl)-1,4-diazepan-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=12C=C(C=3C=CC=CC=3)SC2=NC(N)=NC=1N(CC1)CCCN1C(=O)COC1=CC=C(Cl)C=C1 GONNHMAPYIHDPT-UHFFFAOYSA-N 0.000 description 1
• JPGLGKQUTDLUOC-UHFFFAOYSA-N 1-[4-(2-amino-6-phenylthieno[2,3-d]pyrimidin-4-yl)piperazin-1-yl]-2-(4-bromophenoxy)ethanone Chemical compound C=12C=C(C=3C=CC=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Br)C=C1 JPGLGKQUTDLUOC-UHFFFAOYSA-N 0.000 description 1
• XXJOHQDWDMUUGE-UHFFFAOYSA-N 1-[4-(2-amino-6-phenylthieno[2,3-d]pyrimidin-4-yl)piperazin-1-yl]-2-(4-chlorophenoxy)-2-methylpropan-1-one Chemical compound C1CN(C=2C=3C=C(SC=3N=C(N)N=2)C=2C=CC=CC=2)CCN1C(=O)C(C)(C)OC1=CC=C(Cl)C=C1 XXJOHQDWDMUUGE-UHFFFAOYSA-N 0.000 description 1
• IATXSWLYBQMJTH-UHFFFAOYSA-N 1-[4-(2-amino-6-phenylthieno[2,3-d]pyrimidin-4-yl)piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=12C=C(C=3C=CC=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 IATXSWLYBQMJTH-UHFFFAOYSA-N 0.000 description 1
• IOUKLJNBQDYRIB-UHFFFAOYSA-N 1-[4-(2-amino-8-benzylsulfanyl-7h-purin-6-yl)piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=12N=C(SCC=3C=CC=CC=3)NC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 IOUKLJNBQDYRIB-UHFFFAOYSA-N 0.000 description 1
• ZWRPCTMWPFCZDK-UHFFFAOYSA-N 1-[4-(2-amino-8-benzylsulfanyl-7h-purin-6-yl)piperazin-1-yl]-2-(4-chlorophenoxy)ethanone;1-[4-(2-amino-8-propylsulfanyl-7h-purin-6-yl)piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=12NC(SCCC)=NC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1.C=12NC(SCC=3C=CC=CC=3)=NC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 ZWRPCTMWPFCZDK-UHFFFAOYSA-N 0.000 description 1
• YLBSGBSYQLDSSL-UHFFFAOYSA-N 1-[4-(2-amino-8-cyclopropyl-7h-purin-6-yl)piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=12N=C(C3CC3)NC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 YLBSGBSYQLDSSL-UHFFFAOYSA-N 0.000 description 1
• ZGTJRVRNJHZDLH-UHFFFAOYSA-N 1-[4-(2-amino-8-methyl-7h-purin-6-yl)piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound N1=C(N)N=C2NC(C)=NC2=C1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 ZGTJRVRNJHZDLH-UHFFFAOYSA-N 0.000 description 1
• HYVRVCOMRAOJDK-UHFFFAOYSA-N 1-[4-(2-amino-8-propyl-7h-purin-6-yl)piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound N1=C(N)N=C2NC(CCC)=NC2=C1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 HYVRVCOMRAOJDK-UHFFFAOYSA-N 0.000 description 1
• LESAQKWQUCDXPW-UHFFFAOYSA-N 1-[4-(2-amino-8-propylsulfanyl-7h-purin-6-yl)piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound N1=C(N)N=C2NC(SCCC)=NC2=C1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 LESAQKWQUCDXPW-UHFFFAOYSA-N 0.000 description 1
• DOEBSTUCINVUTO-UHFFFAOYSA-N 1-[4-(5-amino-2-cyclopropyl-[1,3]oxazolo[5,4-d]pyrimidin-7-yl)piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=12N=C(C3CC3)OC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 DOEBSTUCINVUTO-UHFFFAOYSA-N 0.000 description 1
• WAVVXNVGFPXSCD-UHFFFAOYSA-N 1-[4-[2-amino-8-(2-phenylethylsulfanyl)-7h-purin-6-yl]piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=12N=C(SCCC=3C=CC=CC=3)NC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 WAVVXNVGFPXSCD-UHFFFAOYSA-N 0.000 description 1
• WDRHYMDLFWFQFE-UHFFFAOYSA-N 1-[4-[2-amino-8-(3,4-dimethoxyphenyl)-7h-purin-6-yl]piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C1=C(OC)C(OC)=CC=C1C1=NC2=C(N3CCN(CC3)C(=O)COC=3C=CC(Cl)=CC=3)N=C(N)N=C2N1 WDRHYMDLFWFQFE-UHFFFAOYSA-N 0.000 description 1
• IOEBTBZVJQTXQV-UHFFFAOYSA-N 1-[4-[2-amino-8-(4-bromophenyl)-7h-purin-6-yl]piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=12N=C(C=3C=CC(Br)=CC=3)NC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 IOEBTBZVJQTXQV-UHFFFAOYSA-N 0.000 description 1
• QUQMEEYGORZRTH-UHFFFAOYSA-N 1-[4-[2-amino-8-(4-chlorophenyl)-7h-purin-6-yl]piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=12N=C(C=3C=CC(Cl)=CC=3)NC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 QUQMEEYGORZRTH-UHFFFAOYSA-N 0.000 description 1
• GKLIAQTVQNVXGM-UHFFFAOYSA-N 1-[4-[2-amino-8-(4-fluorophenyl)-7h-purin-6-yl]piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=12N=C(C=3C=CC(F)=CC=3)NC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 GKLIAQTVQNVXGM-UHFFFAOYSA-N 0.000 description 1
• VQWCESHIRHWTOD-UHFFFAOYSA-N 1-[4-[2-amino-8-(4-fluorophenyl)-7h-purin-6-yl]piperazin-1-yl]-2-phenoxyethanone Chemical compound C=12N=C(C=3C=CC(F)=CC=3)NC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=CC=C1 VQWCESHIRHWTOD-UHFFFAOYSA-N 0.000 description 1
• SJEYVDWEQVJKAL-UHFFFAOYSA-N 1-[4-[2-amino-8-(4-fluorophenyl)-7h-purin-6-yl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C1=NC(N)=NC2=C1N=C(C=1C=CC(F)=CC=1)N2 SJEYVDWEQVJKAL-UHFFFAOYSA-N 0.000 description 1
• KSASEXVJPIPSDF-UHFFFAOYSA-N 1-[4-[2-amino-8-(4-fluorophenyl)-9-methylpurin-6-yl]piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound N1=C(N)N=C2N(C)C(C=3C=CC(F)=CC=3)=NC2=C1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 KSASEXVJPIPSDF-UHFFFAOYSA-N 0.000 description 1
• ANFGFYABVFGTFG-UHFFFAOYSA-N 1-[4-[2-amino-8-(4-methylphenyl)-7h-purin-6-yl]piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C1=CC(C)=CC=C1C1=NC2=C(N3CCN(CC3)C(=O)COC=3C=CC(Cl)=CC=3)N=C(N)N=C2N1 ANFGFYABVFGTFG-UHFFFAOYSA-N 0.000 description 1
• OZJWOWGFJNFARS-UHFFFAOYSA-N 1-[4-[2-amino-8-[4-(trifluoromethyl)phenyl]-7h-purin-6-yl]piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=12N=C(C=3C=CC(=CC=3)C(F)(F)F)NC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 OZJWOWGFJNFARS-UHFFFAOYSA-N 0.000 description 1
• LHXCVBNRLGZMEN-UHFFFAOYSA-N 1-[4-[2-amino-9-benzyl-8-(4-fluorophenyl)purin-6-yl]piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=12N=C(C=3C=CC(F)=CC=3)N(CC=3C=CC=CC=3)C2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 LHXCVBNRLGZMEN-UHFFFAOYSA-N 0.000 description 1
• RWHWHFCCKXUYNL-UHFFFAOYSA-N 1-[4-[2-butyl-6-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=12C=C(C=3C=CC(F)=CC=3)SC2=NC(CCCC)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 RWHWHFCCKXUYNL-UHFFFAOYSA-N 0.000 description 1
• LKGWCVVCRQXACR-UHFFFAOYSA-N 1-[4-[5-amino-2-(4-fluorophenyl)-[1,3]oxazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C1=NC(N)=NC2=C1N=C(C=1C=CC(F)=CC=1)O2 LKGWCVVCRQXACR-UHFFFAOYSA-N 0.000 description 1
• CRCCYIGTBSZZRH-UHFFFAOYSA-N 1-[4-[5-amino-2-(methoxymethyl)-[1,3]oxazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound N1=C(N)N=C2OC(COC)=NC2=C1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 CRCCYIGTBSZZRH-UHFFFAOYSA-N 0.000 description 1
• XHQBIYCRFVVHFD-UHFFFAOYSA-N 1-benzothiophen-3-ol Chemical group C1=CC=C2C(O)=CSC2=C1 XHQBIYCRFVVHFD-UHFFFAOYSA-N 0.000 description 1
• IQXXEPZFOOTTBA-UHFFFAOYSA-N 1-benzylpiperazine Chemical compound C=1C=CC=CC=1CN1CCNCC1 IQXXEPZFOOTTBA-UHFFFAOYSA-N 0.000 description 1
• MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
• 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
• 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
• CCZMQYGSXWZFKI-UHFFFAOYSA-N 1-chloro-4-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=C(OP(Cl)(Cl)=O)C=C1 CCZMQYGSXWZFKI-UHFFFAOYSA-N 0.000 description 1
• LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical class CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 description 1
• QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 description 1
• WLXGQMVCYPUOLM-UHFFFAOYSA-N 1-hydroxyethanesulfonic acid Chemical compound CC(O)S(O)(=O)=O WLXGQMVCYPUOLM-UHFFFAOYSA-N 0.000 description 1
• 125000001088 1-naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 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
• MJWWNBHUIIRNDZ-UHFFFAOYSA-N 1-pentylpiperazine Chemical compound CCCCCN1CCNCC1 MJWWNBHUIIRNDZ-UHFFFAOYSA-N 0.000 description 1
• 125000006017 1-propenyl group Chemical group 0.000 description 1
• 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
• SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 1
• WVXRAFOPTSTNLL-NKWVEPMBSA-N 2',3'-dideoxyadenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@H]1CC[C@@H](CO)O1 WVXRAFOPTSTNLL-NKWVEPMBSA-N 0.000 description 1
• OHZAHWOAMVVGEL-UHFFFAOYSA-N 2,2'-bithiophene Chemical group C1=CSC(C=2SC=CC=2)=C1 OHZAHWOAMVVGEL-UHFFFAOYSA-N 0.000 description 1
• YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
• QZEDXQFZACVDJE-UHFFFAOYSA-N 2,3-dibutylnaphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(O)(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 QZEDXQFZACVDJE-UHFFFAOYSA-N 0.000 description 1
• 125000005808 2,4,6-trimethoxyphenyl group Chemical group [H][#6]-1=[#6](-[#8]C([H])([H])[H])-[#6](-*)=[#6](-[#8]C([H])([H])[H])-[#6]([H])=[#6]-1-[#8]C([H])([H])[H] 0.000 description 1
• 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 1
• HXKWSTRRCHTUEC-UHFFFAOYSA-N 2,4-Dichlorophenoxyaceticacid Chemical compound OC(=O)C(Cl)OC1=CC=C(Cl)C=C1 HXKWSTRRCHTUEC-UHFFFAOYSA-N 0.000 description 1
• CHHHXKFHOYLYRE-UHFFFAOYSA-M 2,4-Hexadienoic acid, potassium salt (1:1), (2E,4E)- Chemical compound [K+].CC=CC=CC([O-])=O CHHHXKFHOYLYRE-UHFFFAOYSA-M 0.000 description 1
• IIVYOQGIZSPVFZ-UHFFFAOYSA-N 2,5-diamino-4-hydroxy-1h-pyrimidin-6-one;hydrochloride Chemical compound Cl.NC1=NC(O)=C(N)C(=O)N1 IIVYOQGIZSPVFZ-UHFFFAOYSA-N 0.000 description 1
• UBAQQGNYBQOJRN-UHFFFAOYSA-N 2,5-diamino-6h-[1,3]thiazolo[5,4-d]pyrimidin-7-one Chemical compound S1C(N)=NC2=C1N=C(N)NC2=O UBAQQGNYBQOJRN-UHFFFAOYSA-N 0.000 description 1
• SOUUDGAWOJKDRN-UHFFFAOYSA-N 2,6-diamino-1h-pyrimidine-4-thione Chemical compound NC1=CC(=S)N=C(N)N1 SOUUDGAWOJKDRN-UHFFFAOYSA-N 0.000 description 1
• WYDKPTZGVLTYPG-UHFFFAOYSA-N 2,8-diamino-3,7-dihydropurin-6-one Chemical compound N1C(N)=NC(=O)C2=C1N=C(N)N2 WYDKPTZGVLTYPG-UHFFFAOYSA-N 0.000 description 1
• UGEBOCSGBZAQTQ-UHFFFAOYSA-N 2-(3-methoxyphenyl)-7-methylsulfanyl-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound COC1=CC=CC(C=2SC3=NC(N)=NC(SC)=C3N=2)=C1 UGEBOCSGBZAQTQ-UHFFFAOYSA-N 0.000 description 1
• VZECTCSEONQIPP-UHFFFAOYSA-N 2-(3-methylphenoxy)acetic acid Chemical compound CC1=CC=CC(OCC(O)=O)=C1 VZECTCSEONQIPP-UHFFFAOYSA-N 0.000 description 1
• SZEBGAQWWSUOHT-UHFFFAOYSA-N 2-(4-bromophenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1 SZEBGAQWWSUOHT-UHFFFAOYSA-N 0.000 description 1
• KEJUVESGYKXKRJ-UHFFFAOYSA-N 2-(4-chlorophenoxy)-1-[4-(2-cyclohexyl-[1,3]oxazolo[5,4-d]pyrimidin-7-yl)piperazin-1-yl]ethanone Chemical compound C1(CCCCC1)C=1OC=2N=CN=C(C=2N=1)N1CCN(CC1)C(COC1=CC=C(C=C1)Cl)=O KEJUVESGYKXKRJ-UHFFFAOYSA-N 0.000 description 1
• DNNJZQXVILQBDM-UHFFFAOYSA-N 2-(4-chlorophenoxy)-1-[4-[2-[(4-fluorophenyl)methyl]-[1,3]oxazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]ethanone Chemical compound C1=CC(F)=CC=C1CC1=NC2=C(N3CCN(CC3)C(=O)COC=3C=CC(Cl)=CC=3)N=CN=C2O1 DNNJZQXVILQBDM-UHFFFAOYSA-N 0.000 description 1
• HESMLHIIUNOASP-UHFFFAOYSA-N 2-(4-chlorophenoxy)-1-[4-[6-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]piperazin-1-yl]ethanone Chemical compound C1=CC(F)=CC=C1C1=CC2=C(N3CCN(CC3)C(=O)COC=3C=CC(Cl)=CC=3)N=CN=C2S1 HESMLHIIUNOASP-UHFFFAOYSA-N 0.000 description 1
• IXFAWIBSYOAYSU-UHFFFAOYSA-N 2-(4-chlorophenyl)-7-methylsulfanyl-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound N=1C=2C(SC)=NC(N)=NC=2SC=1C1=CC=C(Cl)C=C1 IXFAWIBSYOAYSU-UHFFFAOYSA-N 0.000 description 1
• UMQUIRYNOVNYPA-UHFFFAOYSA-N 2-(4-chlorophenyl)acetyl chloride Chemical compound ClC(=O)CC1=CC=C(Cl)C=C1 UMQUIRYNOVNYPA-UHFFFAOYSA-N 0.000 description 1
• ZBIULCVFFJJYTN-UHFFFAOYSA-N 2-(4-fluorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(F)C=C1 ZBIULCVFFJJYTN-UHFFFAOYSA-N 0.000 description 1
• ZRMQGVACZIFSLZ-UHFFFAOYSA-N 2-(4-fluorophenyl)-4h-[1,3]thiazolo[5,4-d]pyrimidine-5,7-dithione Chemical compound C1=CC(F)=CC=C1C1=NC2=C(S)N=C(S)N=C2S1 ZRMQGVACZIFSLZ-UHFFFAOYSA-N 0.000 description 1
• OYECRNGLIYYTBL-UHFFFAOYSA-N 2-(4-fluorophenyl)-5-methyl-6h-[1,3]thiazolo[5,4-d]pyrimidin-7-one Chemical compound N=1C=2C(=O)NC(C)=NC=2SC=1C1=CC=C(F)C=C1 OYECRNGLIYYTBL-UHFFFAOYSA-N 0.000 description 1
• SVXVEIBAXPIVFB-UHFFFAOYSA-N 2-(4-fluorophenyl)-5-methyl-6h-[1,3]thiazolo[5,4-d]pyrimidine-7-thione Chemical compound S1C2=NC(C)=NC(S)=C2N=C1C1=CC=C(F)C=C1 SVXVEIBAXPIVFB-UHFFFAOYSA-N 0.000 description 1
• RDIHTEMYAICGMD-UHFFFAOYSA-N 2-(4-fluorophenyl)-5-methyl-7-methylsulfanyl-[1,3]thiazolo[5,4-d]pyrimidine Chemical compound N=1C=2C(SC)=NC(C)=NC=2SC=1C1=CC=C(F)C=C1 RDIHTEMYAICGMD-UHFFFAOYSA-N 0.000 description 1
• NOJHUDGKTBYFRU-UHFFFAOYSA-N 2-(4-fluorophenyl)-7-[4-(2-methylpropyl)piperazin-1-yl]-[1,3]oxazolo[5,4-d]pyrimidin-5-amine Chemical compound C1CN(CC(C)C)CCN1C1=NC(N)=NC2=C1N=C(C=1C=CC(F)=CC=1)O2 NOJHUDGKTBYFRU-UHFFFAOYSA-N 0.000 description 1
• FJBRVQYRRWGYHD-UHFFFAOYSA-N 2-(4-fluorophenyl)-7-methylsulfonyl-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound N=1C=2C(S(=O)(=O)C)=NC(N)=NC=2SC=1C1=CC=C(F)C=C1 FJBRVQYRRWGYHD-UHFFFAOYSA-N 0.000 description 1
• IXSCGBODJGIJNN-UHFFFAOYSA-N 2-(4-fluorophenyl)propanoic acid Chemical compound OC(=O)C(C)C1=CC=C(F)C=C1 IXSCGBODJGIJNN-UHFFFAOYSA-N 0.000 description 1
• BHFSBJHPPFJCOS-UHFFFAOYSA-N 2-(4-methoxyphenoxy)acetic acid Chemical compound COC1=CC=C(OCC(O)=O)C=C1 BHFSBJHPPFJCOS-UHFFFAOYSA-N 0.000 description 1
• URGLRVDCCMBOEK-UHFFFAOYSA-N 2-(4-methylphenyl)-7-piperazin-1-yl-[1,3]thiazolo[5,4-d]pyrimidin-5-amine;2-pentyl-7-piperazin-1-yl-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound N1=C(N)N=C2SC(CCCCC)=NC2=C1N1CCNCC1.C1=CC(C)=CC=C1C1=NC2=C(N3CCNCC3)N=C(N)N=C2S1 URGLRVDCCMBOEK-UHFFFAOYSA-N 0.000 description 1
• XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
• IPUMKAQQCSJGFB-UHFFFAOYSA-N 2-[(4-chlorophenyl)methyl]-7-methylsulfanyl-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound N=1C=2C(SC)=NC(N)=NC=2SC=1CC1=CC=C(Cl)C=C1 IPUMKAQQCSJGFB-UHFFFAOYSA-N 0.000 description 1
• UCFIHBXKQJVCIC-UHFFFAOYSA-N 2-[(4-fluorophenyl)methyl]-7-methylsulfonyl-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound N=1C=2C(S(=O)(=O)C)=NC(N)=NC=2SC=1CC1=CC=C(F)C=C1 UCFIHBXKQJVCIC-UHFFFAOYSA-N 0.000 description 1
• HPLHHNBCEGVWNC-UHFFFAOYSA-N 2-[(4-fluorophenyl)methyl]-7-piperazin-1-yl-[1,3]thiazolo[5,4-d]pyrimidin-5-amine;2-(4-fluorophenyl)-7-piperazin-1-yl-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound C=12N=C(C=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N1CCNCC1.C=12N=C(CC=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N1CCNCC1 HPLHHNBCEGVWNC-UHFFFAOYSA-N 0.000 description 1
• HBBYRODSROHRMX-UHFFFAOYSA-N 2-[1-(4-fluorophenyl)-2-phenylethyl]-7-methylsulfonyl-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound N=1C=2C(S(=O)(=O)C)=NC(N)=NC=2SC=1C(C=1C=CC(F)=CC=1)CC1=CC=CC=C1 HBBYRODSROHRMX-UHFFFAOYSA-N 0.000 description 1
• HKQSTYGBFSURJP-UHFFFAOYSA-N 2-[1-(4-fluorophenyl)ethyl]-7-methylsulfanyl-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound N=1C=2C(SC)=NC(N)=NC=2SC=1C(C)C1=CC=C(F)C=C1 HKQSTYGBFSURJP-UHFFFAOYSA-N 0.000 description 1
• QLIUUNOYGYNZMY-UHFFFAOYSA-N 2-[1-(4-fluorophenyl)ethyl]-7-methylsulfonyl-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound N=1C2=C(S(C)(=O)=O)N=C(N)N=C2SC=1C(C)C1=CC=C(F)C=C1 QLIUUNOYGYNZMY-UHFFFAOYSA-N 0.000 description 1
• JDSQBDGCMUXRBM-UHFFFAOYSA-N 2-[2-(2-butoxypropoxy)propoxy]propan-1-ol Chemical group CCCCOC(C)COC(C)COC(C)CO JDSQBDGCMUXRBM-UHFFFAOYSA-N 0.000 description 1
• RVYUPHXLYVTPBM-UHFFFAOYSA-N 2-[2-(4-fluorophenoxy)ethyl]-7-methylsulfonyl-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound N=1C=2C(S(=O)(=O)C)=NC(N)=NC=2SC=1CCOC1=CC=C(F)C=C1 RVYUPHXLYVTPBM-UHFFFAOYSA-N 0.000 description 1
• QATFSUVESUNVFL-UHFFFAOYSA-N 2-[2-(4-fluorophenyl)ethyl]-7-[4-(2-phenoxyethyl)piperazin-1-yl]-[1,3]oxazolo[5,4-d]pyrimidin-5-amine Chemical compound C=12N=C(CCC=3C=CC(F)=CC=3)OC2=NC(N)=NC=1N(CC1)CCN1CCOC1=CC=CC=C1 QATFSUVESUNVFL-UHFFFAOYSA-N 0.000 description 1
• AWFGQOQKQHOGAT-UHFFFAOYSA-L 2-[3,5-bis(3-heptyl-4-methyl-1,3-thiazol-3-ium-2-yl)penta-2,4-dienylidene]-3-heptyl-4-methyl-1,3-thiazole;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCN1C(C)=CS\C1=C\C=C(/C1=[N+](C(C)=CS1)CCCCCCC)\C=C\C1=[N+](CCCCCCC)C(C)=CS1 AWFGQOQKQHOGAT-UHFFFAOYSA-L 0.000 description 1
• ZFNILYIEESEHPH-UHFFFAOYSA-N 2-[4-(2-amino-6-phenylthieno[2,3-d]pyrimidin-4-yl)piperazin-1-yl]-n-methyl-n-phenylacetamide Chemical compound C=1C=CC=CC=1N(C)C(=O)CN(CC1)CCN1C(C=1C=2)=NC(N)=NC=1SC=2C1=CC=CC=C1 ZFNILYIEESEHPH-UHFFFAOYSA-N 0.000 description 1
• IULOBWFWYDMECP-UHFFFAOYSA-N 2-[4-[2-[(4-chlorophenyl)sulfonylamino]ethyl]phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1CCNS(=O)(=O)C1=CC=C(Cl)C=C1 IULOBWFWYDMECP-UHFFFAOYSA-N 0.000 description 1
• ZLHOYOKEKGKMSG-UHFFFAOYSA-N 2-[4-[2-amino-8-(4-fluorophenyl)-7h-purin-6-yl]piperazin-1-yl]-1-morpholin-4-ylethanone Chemical compound C=12N=C(C=3C=CC(F)=CC=3)NC2=NC(N)=NC=1N(CC1)CCN1CC(=O)N1CCOCC1 ZLHOYOKEKGKMSG-UHFFFAOYSA-N 0.000 description 1
• FMSUYVDCMWCMNR-UHFFFAOYSA-N 2-[4-[2-amino-8-(4-fluorophenyl)-7h-purin-6-yl]piperazin-1-yl]-1-morpholin-4-ylethanone;2-[4-[2-amino-8-(4-fluorophenyl)-7h-purin-6-yl]piperazin-1-yl]-1-pyrrolidin-1-ylethanone Chemical compound C=12NC(C=3C=CC(F)=CC=3)=NC2=NC(N)=NC=1N(CC1)CCN1CC(=O)N1CCCC1.C=12NC(C=3C=CC(F)=CC=3)=NC2=NC(N)=NC=1N(CC1)CCN1CC(=O)N1CCOCC1 FMSUYVDCMWCMNR-UHFFFAOYSA-N 0.000 description 1
• JSQVSRNGBHAUTR-UHFFFAOYSA-N 2-[4-[2-amino-8-(4-fluorophenyl)-7h-purin-6-yl]piperazin-1-yl]-n-methyl-n-phenylacetamide Chemical compound C=1C=CC=CC=1N(C)C(=O)CN(CC1)CCN1C(C=1N=2)=NC(N)=NC=1NC=2C1=CC=C(F)C=C1 JSQVSRNGBHAUTR-UHFFFAOYSA-N 0.000 description 1
• YRJZOTQVRYZBLK-UHFFFAOYSA-N 2-[4-[5-amino-2-[2-(4-fluorophenyl)ethyl]-[1,3]oxazolo[5,4-d]pyrimidin-7-yl]piperazin-1-yl]-n-methyl-n-phenylacetamide Chemical compound C=1C=CC=CC=1N(C)C(=O)CN(CC1)CCN1C(C=1N=2)=NC(N)=NC=1OC=2CCC1=CC=C(F)C=C1 YRJZOTQVRYZBLK-UHFFFAOYSA-N 0.000 description 1
• SWHMMZXZNMEPBP-UHFFFAOYSA-N 2-[5-(2-phenylethylamino)furan-2-yl]-[1,3]oxazolo[5,4-d]pyrimidin-7-amine Chemical compound N=1C=2C(N)=NC=NC=2OC=1C(O1)=CC=C1NCCC1=CC=CC=C1 SWHMMZXZNMEPBP-UHFFFAOYSA-N 0.000 description 1
• CFWRDBDJAOHXSH-SECBINFHSA-N 2-azaniumylethyl [(2r)-2,3-diacetyloxypropyl] phosphate Chemical compound CC(=O)OC[C@@H](OC(C)=O)COP(O)(=O)OCCN CFWRDBDJAOHXSH-SECBINFHSA-N 0.000 description 1
• 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
• 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
• DYWAPFDKPAHSED-UHFFFAOYSA-N 2-cycloheptyloxepane Chemical group C1CCCCCC1C1OCCCCC1 DYWAPFDKPAHSED-UHFFFAOYSA-N 0.000 description 1
• XXNDHVZLNBSADF-UHFFFAOYSA-N 2-cyclohexyl-7-methylsulfanyl-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound N=1C=2C(SC)=NC(N)=NC=2SC=1C1CCCCC1 XXNDHVZLNBSADF-UHFFFAOYSA-N 0.000 description 1
• KBGTUVBEKLMLLL-UHFFFAOYSA-N 2-cyclopropyl-7-methylsulfanyl-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound N=1C=2C(SC)=NC(N)=NC=2SC=1C1CC1 KBGTUVBEKLMLLL-UHFFFAOYSA-N 0.000 description 1
• WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical class CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
• 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
• 125000006040 2-hexenyl group Chemical group 0.000 description 1
• JJKWHOSQTYYFAE-UHFFFAOYSA-N 2-methoxyacetyl chloride Chemical compound COCC(Cl)=O JJKWHOSQTYYFAE-UHFFFAOYSA-N 0.000 description 1
• ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 1
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
• XXUNIGZDNWWYED-UHFFFAOYSA-N 2-methylbenzamide Chemical compound CC1=CC=CC=C1C(N)=O XXUNIGZDNWWYED-UHFFFAOYSA-N 0.000 description 1
• 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
• 125000005916 2-methylpentyl group Chemical group 0.000 description 1
• AUXBHVTXXUIPHQ-UHFFFAOYSA-N 2-methylsulfanyl-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound N1=C(N)N=C2SC(SC)=NC2=C1 AUXBHVTXXUIPHQ-UHFFFAOYSA-N 0.000 description 1
• DZZZOZKLXYSJMW-UHFFFAOYSA-N 2-methylsulfonyl-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound N1=C(N)N=C2SC(S(=O)(=O)C)=NC2=C1 DZZZOZKLXYSJMW-UHFFFAOYSA-N 0.000 description 1
• 125000001216 2-naphthoyl group Chemical group C1=C(C=CC2=CC=CC=C12)C(=O)* 0.000 description 1
• 125000006024 2-pentenyl group Chemical group 0.000 description 1
• XZCPXUCNSORUCQ-UHFFFAOYSA-N 2-phenoxy-1-piperazin-1-ylethanone Chemical compound C1CNCCN1C(=O)COC1=CC=CC=C1 XZCPXUCNSORUCQ-UHFFFAOYSA-N 0.000 description 1
• PKUPAJQAJXVUEK-UHFFFAOYSA-N 2-phenoxyacetyl chloride Chemical compound ClC(=O)COC1=CC=CC=C1 PKUPAJQAJXVUEK-UHFFFAOYSA-N 0.000 description 1
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
• LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
• VTXNOVCTHUBABW-UHFFFAOYSA-N 3,4-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C(Cl)=C1 VTXNOVCTHUBABW-UHFFFAOYSA-N 0.000 description 1
• 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 description 1
• 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 description 1
• MSYGAHOHLUJIKV-UHFFFAOYSA-N 3,5-dimethyl-1-(3-nitrophenyl)-1h-pyrazole-4-carboxylic acid ethyl ester Chemical compound CC1=C(C(=O)OCC)C(C)=NN1C1=CC=CC([N+]([O-])=O)=C1 MSYGAHOHLUJIKV-UHFFFAOYSA-N 0.000 description 1
• ALKYHXVLJMQRLQ-UHFFFAOYSA-M 3-carboxynaphthalen-2-olate Chemical compound C1=CC=C2C=C(C([O-])=O)C(O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-M 0.000 description 1
• 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 description 1
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
• 125000006041 3-hexenyl group Chemical group 0.000 description 1
• RUQIUASLAXJZIE-UHFFFAOYSA-N 3-methoxybenzoyl chloride Chemical compound COC1=CC=CC(C(Cl)=O)=C1 RUQIUASLAXJZIE-UHFFFAOYSA-N 0.000 description 1
• FAXDZWQIWUSWJH-UHFFFAOYSA-N 3-methoxypropan-1-amine Chemical compound COCCCN FAXDZWQIWUSWJH-UHFFFAOYSA-N 0.000 description 1
• 125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 description 1
• 125000005917 3-methylpentyl group Chemical group 0.000 description 1
• MFEILWXBDBCWKF-UHFFFAOYSA-N 3-phenylpropanoyl chloride Chemical compound ClC(=O)CCC1=CC=CC=C1 MFEILWXBDBCWKF-UHFFFAOYSA-N 0.000 description 1
• PPAULTVPKLVLII-UHFFFAOYSA-N 4,5-diaminopyrimidine Chemical compound NC1=CN=CN=C1N PPAULTVPKLVLII-UHFFFAOYSA-N 0.000 description 1
• IJYHFOIORVYBLB-UHFFFAOYSA-N 4-(2-amino-6-phenylthieno[2,3-d]pyrimidin-4-yl)-n-(3-methylphenyl)piperazine-1-carboxamide Chemical compound CC1=CC=CC(NC(=O)N2CCN(CC2)C=2C=3C=C(SC=3N=C(N)N=2)C=2C=CC=CC=2)=C1 IJYHFOIORVYBLB-UHFFFAOYSA-N 0.000 description 1
• VXTYGWVEFJNJFT-UHFFFAOYSA-N 4-(6-phenylthieno[2,3-d]pyrimidin-2-yl)piperazin-2-amine Chemical compound C1CNC(N)CN1C1=NC=C(C=C(S2)C=3C=CC=CC=3)C2=N1 VXTYGWVEFJNJFT-UHFFFAOYSA-N 0.000 description 1
• XWNDUWVHUAYRRB-UHFFFAOYSA-N 4-[2-amino-8-(4-fluorophenyl)-7h-purin-6-yl]-n-(3-methylphenyl)-1,4-diazepane-1-carboxamide Chemical compound CC1=CC=CC(NC(=O)N2CCN(CCC2)C=2C=3N=C(NC=3N=C(N)N=2)C=2C=CC(F)=CC=2)=C1 XWNDUWVHUAYRRB-UHFFFAOYSA-N 0.000 description 1
• HOFXMOCSYGWGPY-UHFFFAOYSA-N 4-[4-(2-phenoxyethyl)piperazin-1-yl]-6-phenylthieno[2,3-d]pyrimidin-2-amine Chemical compound C=12C=C(C=3C=CC=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1CCOC1=CC=CC=C1 HOFXMOCSYGWGPY-UHFFFAOYSA-N 0.000 description 1
• PZWOOCJOKIKIDT-UHFFFAOYSA-N 4-[4-[2-(4-chlorophenoxy)acetyl]piperazin-1-yl]-6-(4-fluorophenyl)thieno[2,3-d]pyrimidine-2-carboxamide Chemical compound C=12C=C(C=3C=CC(F)=CC=3)SC2=NC(C(=O)N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 PZWOOCJOKIKIDT-UHFFFAOYSA-N 0.000 description 1
• FPESSAJSCCWLRY-UHFFFAOYSA-N 4-[4-[2-(4-chlorophenoxy)acetyl]piperazin-1-yl]-6-(4-fluorophenyl)thieno[2,3-d]pyrimidine-2-carboxylic acid Chemical compound C=12C=C(C=3C=CC(F)=CC=3)SC2=NC(C(=O)O)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 FPESSAJSCCWLRY-UHFFFAOYSA-N 0.000 description 1
• HZBZCSWVUXVFSC-UHFFFAOYSA-N 4-[6-(4-fluorophenyl)thieno[2,3-d]pyrimidin-2-yl]piperazin-2-amine Chemical compound C1CNC(N)CN1C1=NC=C(C=C(S2)C=3C=CC(F)=CC=3)C2=N1 HZBZCSWVUXVFSC-UHFFFAOYSA-N 0.000 description 1
• WRFYIYOXJWKONR-UHFFFAOYSA-N 4-bromo-2-methoxyaniline Chemical compound COC1=CC(Br)=CC=C1N WRFYIYOXJWKONR-UHFFFAOYSA-N 0.000 description 1
• 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
• LHGMCUVJFRBVBH-UHFFFAOYSA-N 4-chloropyrimidin-5-amine Chemical compound NC1=CN=CN=C1Cl LHGMCUVJFRBVBH-UHFFFAOYSA-N 0.000 description 1
• NZCRUBBNZGVREM-UHFFFAOYSA-N 4-chlorothieno[2,3-d]pyrimidine Chemical class ClC1=NC=NC2=C1C=CS2 NZCRUBBNZGVREM-UHFFFAOYSA-N 0.000 description 1
• QRJBCQJWZPXKOS-UHFFFAOYSA-N 4-ethoxy-6-(4-fluorophenyl)thieno[2,3-d]pyrimidin-2-amine Chemical compound C=1C=2C(OCC)=NC(N)=NC=2SC=1C1=CC=C(F)C=C1 QRJBCQJWZPXKOS-UHFFFAOYSA-N 0.000 description 1
• WNWVKZTYMQWFHE-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound [CH2]CN1CCOCC1 WNWVKZTYMQWFHE-UHFFFAOYSA-N 0.000 description 1
• UJVUCXPJUNPWPR-UHFFFAOYSA-N 4-fluoro-N-(6-hydroxy-4-oxo-2-sulfanylidene-1H-pyrimidin-5-yl)benzamide thiourea Chemical compound NC(=S)N.OC1=NC(=NC(=C1NC(C1=CC=C(C=C1)F)=O)O)S UJVUCXPJUNPWPR-UHFFFAOYSA-N 0.000 description 1
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
• 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 1
• UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 1
• KBIWNQVZKHSHTI-UHFFFAOYSA-N 4-n,4-n-dimethylbenzene-1,4-diamine;oxalic acid Chemical compound OC(=O)C(O)=O.CN(C)C1=CC=C(N)C=C1 KBIWNQVZKHSHTI-UHFFFAOYSA-N 0.000 description 1
• IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
• PILFPZMUDJMYMY-UHFFFAOYSA-N 4-thieno[2,3-d]pyrimidin-2-ylpiperazin-2-amine Chemical class C1CNC(N)CN1C1=NC=C(C=CS2)C2=N1 PILFPZMUDJMYMY-UHFFFAOYSA-N 0.000 description 1
• NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
• MYPZDIIFCMVUOZ-UHFFFAOYSA-N 5-amino-2-(4-fluorophenyl)-6h-[1,3]thiazolo[5,4-d]pyrimidine-7-thione Chemical compound S1C2=NC(N)=NC(S)=C2N=C1C1=CC=C(F)C=C1 MYPZDIIFCMVUOZ-UHFFFAOYSA-N 0.000 description 1
• PIKTYDBZFQILGB-UHFFFAOYSA-N 5-amino-2-[(4-fluorophenyl)methyl]-6h-[1,3]thiazolo[5,4-d]pyrimidine-7-thione Chemical compound S1C2=NC(N)=NC(S)=C2N=C1CC1=CC=C(F)C=C1 PIKTYDBZFQILGB-UHFFFAOYSA-N 0.000 description 1
• CNFKHRLFOBAPKJ-UHFFFAOYSA-N 5-amino-2-[2-(4-fluorophenoxy)ethyl]-6h-[1,3]thiazolo[5,4-d]pyrimidine-7-thione Chemical compound S1C2=NC(N)=NC(S)=C2N=C1CCOC1=CC=C(F)C=C1 CNFKHRLFOBAPKJ-UHFFFAOYSA-N 0.000 description 1
• QCLAELJXWLOJAW-UHFFFAOYSA-N 5-amino-2-[2-(4-fluorophenyl)ethyl]-6h-[1,3]thiazolo[5,4-d]pyrimidine-7-thione Chemical compound S1C2=NC(N)=NC(S)=C2N=C1CCC1=CC=C(F)C=C1 QCLAELJXWLOJAW-UHFFFAOYSA-N 0.000 description 1
• YWKOMSVMLIYEKS-UHFFFAOYSA-N 5-bromothieno[2,3-d]pyrimidine Chemical compound C1=NC=C2C(Br)=CSC2=N1 YWKOMSVMLIYEKS-UHFFFAOYSA-N 0.000 description 1
• IZSHZLKNFQAAKX-UHFFFAOYSA-N 5-cyclopenta-2,4-dien-1-ylcyclopenta-1,3-diene Chemical group C1=CC=CC1C1C=CC=C1 IZSHZLKNFQAAKX-UHFFFAOYSA-N 0.000 description 1
• YZFUAIWTNMWSEP-UHFFFAOYSA-N 5-nitrosopyrimidine Chemical class O=NC1=CN=CN=C1 YZFUAIWTNMWSEP-UHFFFAOYSA-N 0.000 description 1
• KQMPBNYANZUHJC-UHFFFAOYSA-N 6-(1,4-diazepan-1-yl)-8-(4-fluorophenyl)-7h-purin-2-amine Chemical compound C=12N=C(C=3C=CC(F)=CC=3)NC2=NC(N)=NC=1N1CCCNCC1 KQMPBNYANZUHJC-UHFFFAOYSA-N 0.000 description 1
• YMMWIKRJZHFROV-UHFFFAOYSA-N 6-(1h-1,2,4-triazol-5-yl)-7h-purine Chemical class N1C=NC(C=2C=3NC=NC=3N=CN=2)=N1 YMMWIKRJZHFROV-UHFFFAOYSA-N 0.000 description 1
• WFCDDGCDORMVSX-UHFFFAOYSA-N 6-(4-benzylsulfonylpiperazin-1-yl)-8-(4-fluorophenyl)-7h-purin-2-amine Chemical compound C=12N=C(C=3C=CC(F)=CC=3)NC2=NC(N)=NC=1N(CC1)CCN1S(=O)(=O)CC1=CC=CC=C1 WFCDDGCDORMVSX-UHFFFAOYSA-N 0.000 description 1
• WGXOXPSFNAVBMN-UHFFFAOYSA-N 6-(4-fluorophenyl)-4-morpholin-4-ylthieno[2,3-d]pyrimidin-2-amine Chemical compound C=12C=C(C=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N1CCOCC1 WGXOXPSFNAVBMN-UHFFFAOYSA-N 0.000 description 1
• ZKBQDFAWXLTYKS-UHFFFAOYSA-N 6-Chloro-1H-purine Chemical class ClC1=NC=NC2=C1NC=N2 ZKBQDFAWXLTYKS-UHFFFAOYSA-N 0.000 description 1
• YFYYRKDBDBILSD-UHFFFAOYSA-N 6-amino-2-sulfanylidene-1h-pyrimidin-4-one Chemical compound NC1=CC(=O)NC(=S)N1 YFYYRKDBDBILSD-UHFFFAOYSA-N 0.000 description 1
• CCQQNRDRMMVUQI-UHFFFAOYSA-N 6-bromothieno[2,3-d]pyrimidine Chemical compound N1=CN=C2SC(Br)=CC2=C1 CCQQNRDRMMVUQI-UHFFFAOYSA-N 0.000 description 1
• QJIUMVUZDYPQRT-UHFFFAOYSA-N 6-chloro-2,4-pyrimidinediamine Chemical compound NC1=CC(Cl)=NC(N)=N1 QJIUMVUZDYPQRT-UHFFFAOYSA-N 0.000 description 1
• IUIYEHXOIMMQJY-NGXOUOCZSA-N 60135-22-0 Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)C(OC)OC)[C@@]2(C)C[C@@H]1O IUIYEHXOIMMQJY-NGXOUOCZSA-N 0.000 description 1
• 125000003341 7 membered heterocyclic group Chemical group 0.000 description 1
• HRVOQQBVTAAZEZ-UHFFFAOYSA-N 7-ethoxy-2-(4-fluorophenyl)-5-methylsulfonyl-[1,3]thiazolo[5,4-d]pyrimidine Chemical compound N=1C=2C(OCC)=NC(S(C)(=O)=O)=NC=2SC=1C1=CC=C(F)C=C1 HRVOQQBVTAAZEZ-UHFFFAOYSA-N 0.000 description 1
• PDTXWPHNZWMTOW-UHFFFAOYSA-N 7-methylsulfanyl-2-(2-phenylethyl)-[1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound N=1C=2C(SC)=NC(N)=NC=2SC=1CCC1=CC=CC=C1 PDTXWPHNZWMTOW-UHFFFAOYSA-N 0.000 description 1
• LLYNBBMSVVHPDH-UHFFFAOYSA-N 8-(4-fluorophenyl)-6-(4-pyridin-4-ylpiperazin-1-yl)-7h-purin-2-amine Chemical compound C=12N=C(C=3C=CC(F)=CC=3)NC2=NC(N)=NC=1N(CC1)CCN1C1=CC=NC=C1 LLYNBBMSVVHPDH-UHFFFAOYSA-N 0.000 description 1
• WZUPOVBJDVBHBF-UHFFFAOYSA-N 8-(4-fluorophenyl)-6-[4-(1,3-thiazol-2-yl)piperazin-1-yl]-7h-purin-2-amine Chemical compound C=12N=C(C=3C=CC(F)=CC=3)NC2=NC(N)=NC=1N(CC1)CCN1C1=NC=CS1 WZUPOVBJDVBHBF-UHFFFAOYSA-N 0.000 description 1
• UIUXHYDISLPXPU-UHFFFAOYSA-N 8-(4-fluorophenyl)-6-[4-(4-fluorophenyl)piperazin-1-yl]-7h-purin-2-amine Chemical compound C=12N=C(C=3C=CC(F)=CC=3)NC2=NC(N)=NC=1N(CC1)CCN1C1=CC=C(F)C=C1 UIUXHYDISLPXPU-UHFFFAOYSA-N 0.000 description 1
• CMRRBCRDZQRYSA-UHFFFAOYSA-N 8-(4-fluorophenyl)-6-[4-[(4-fluorophenyl)methyl]piperazin-1-yl]-7h-purin-2-amine Chemical compound C=12N=C(C=3C=CC(F)=CC=3)NC2=NC(N)=NC=1N(CC1)CCN1CC1=CC=C(F)C=C1 CMRRBCRDZQRYSA-UHFFFAOYSA-N 0.000 description 1
• IAHMVZVRRIVXRK-UHFFFAOYSA-N 8-(4-fluorophenyl)-6-piperazin-1-yl-7h-purin-2-amine Chemical compound C=12N=C(C=3C=CC(F)=CC=3)NC2=NC(N)=NC=1N1CCNCC1 IAHMVZVRRIVXRK-UHFFFAOYSA-N 0.000 description 1
• RTAPDZBZLSXHQQ-UHFFFAOYSA-N 8-methyl-3,7-dihydropurine-2,6-dione Chemical class N1C(=O)NC(=O)C2=C1N=C(C)N2 RTAPDZBZLSXHQQ-UHFFFAOYSA-N 0.000 description 1
• QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
• LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 1
• 208000021959 Abnormal metabolism Diseases 0.000 description 1
• 244000215068 Acacia senegal Species 0.000 description 1
• OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound 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
• 208000026872 Addison Disease Diseases 0.000 description 1
• 102000009346 Adenosine receptors Human genes 0.000 description 1
• 108050000203 Adenosine receptors Proteins 0.000 description 1
• 229910002012 Aerosil® Inorganic materials 0.000 description 1
• 238000010953 Ames test Methods 0.000 description 1
• 206010002556 Ankylosing Spondylitis Diseases 0.000 description 1
• 208000032467 Aplastic anaemia Diseases 0.000 description 1
• 206010003658 Atrial Fibrillation Diseases 0.000 description 1
• 206010003827 Autoimmune hepatitis Diseases 0.000 description 1
• 210000002237 B-cell of pancreatic islet Anatomy 0.000 description 1
• 208000023328 Basedow disease Diseases 0.000 description 1
• VGGGPCQERPFHOB-MCIONIFRSA-N Bestatin Chemical compound CC(C)C[C@H](C(O)=O)NC(=O)[C@@H](O)[C@H](N)CC1=CC=CC=C1 VGGGPCQERPFHOB-MCIONIFRSA-N 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
• 206010004659 Biliary cirrhosis Diseases 0.000 description 1
• 208000033222 Biliary cirrhosis primary Diseases 0.000 description 1
• 206010065553 Bone marrow failure Diseases 0.000 description 1
• 101710143185 Calcium-dependent protein kinase 1 Proteins 0.000 description 1
• 102000000584 Calmodulin Human genes 0.000 description 1
• 108010041952 Calmodulin Proteins 0.000 description 1
• 206010062746 Carditis Diseases 0.000 description 1
• 239000005973 Carvone Substances 0.000 description 1
• 102000011727 Caspases Human genes 0.000 description 1
• 108010076667 Caspases Proteins 0.000 description 1
• 241000700198 Cavia Species 0.000 description 1
• 102000000844 Cell Surface Receptors Human genes 0.000 description 1
• 108010001857 Cell Surface Receptors Proteins 0.000 description 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
• FDGUQENKSIXSNW-UHFFFAOYSA-N Cl.C(C)(=N)N.OC1=NC(=NC(=C1NC(C1=CC=C(C=C1)F)=O)O)C Chemical compound Cl.C(C)(=N)N.OC1=NC(=NC(=C1NC(C1=CC=C(C=C1)F)=O)O)C FDGUQENKSIXSNW-UHFFFAOYSA-N 0.000 description 1
• CTRIRFNVEMKMSG-UHFFFAOYSA-N Cl.NC(=N)N.NC1=NC(=C(C(=N1)O)NC(C1=CC=C(C=C1)F)=O)O Chemical compound Cl.NC(=N)N.NC1=NC(=C(C(=N1)O)NC(C1=CC=C(C=C1)F)=O)O CTRIRFNVEMKMSG-UHFFFAOYSA-N 0.000 description 1
• QVTOXYVNSQMBSD-UHFFFAOYSA-N ClC1=CC=C(OCC(=O)N2CCN(CC2)C2=NC=C3N=C(NC3=N2)C2=CC(=C(C=C2)OC)OC)C=C1 Chemical compound ClC1=CC=C(OCC(=O)N2CCN(CC2)C2=NC=C3N=C(NC3=N2)C2=CC(=C(C=C2)OC)OC)C=C1 QVTOXYVNSQMBSD-UHFFFAOYSA-N 0.000 description 1
• 206010011224 Cough Diseases 0.000 description 1
• 241000699800 Cricetinae Species 0.000 description 1
• 229920000858 Cyclodextrin Polymers 0.000 description 1
• CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 1
• 206010011831 Cytomegalovirus infection Diseases 0.000 description 1
• RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
• 206010012438 Dermatitis atopic Diseases 0.000 description 1
• 208000002249 Diabetes Complications Diseases 0.000 description 1
• 238000009007 Diagnostic Kit Methods 0.000 description 1
• SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
• 208000000059 Dyspnea Diseases 0.000 description 1
• 206010013975 Dyspnoeas Diseases 0.000 description 1
• 102100025137 Early activation antigen CD69 Human genes 0.000 description 1
• 241000196324 Embryophyta Species 0.000 description 1
• 208000017701 Endocrine disease Diseases 0.000 description 1
• 108010008165 Etanercept Proteins 0.000 description 1
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
• 239000005977 Ethylene Substances 0.000 description 1
• IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
• PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
• MXLFYXAMMNFMHY-UHFFFAOYSA-N FC1=CC=C(C=C1)C(C)C=1SC=2N=C(N=C(C2N1)S(=O)(=O)C)N.C(C)=O Chemical compound FC1=CC=C(C=C1)C(C)C=1SC=2N=C(N=C(C2N1)S(=O)(=O)C)N.C(C)=O MXLFYXAMMNFMHY-UHFFFAOYSA-N 0.000 description 1
• QUPIREHYGDZZJI-UHFFFAOYSA-N FC1=CC=C(C=C1)C=1SC=2N=C(N=C(C2N1)N1CCNCC1)N.FC1=CC=C(C=C1)C=1SC=2N=C(N=C(C2N1)SC)C Chemical compound FC1=CC=C(C=C1)C=1SC=2N=C(N=C(C2N1)N1CCNCC1)N.FC1=CC=C(C=C1)C=1SC=2N=C(N=C(C2N1)SC)C QUPIREHYGDZZJI-UHFFFAOYSA-N 0.000 description 1
• KSLWIKPTICOFLA-UHFFFAOYSA-N FC1=CC=C(C=C1)C=1SC=2N=C(N=C(C2N1)N1CCNCC1)N.NC=1N=C(C2=C(N1)SC(=N2)C2=CC=C(C=C2)F)N2CCN(CC2)C(COC2=CC=C(C=C2)Cl)=O Chemical compound FC1=CC=C(C=C1)C=1SC=2N=C(N=C(C2N1)N1CCNCC1)N.NC=1N=C(C2=C(N1)SC(=N2)C2=CC=C(C=C2)F)N2CCN(CC2)C(COC2=CC=C(C=C2)Cl)=O KSLWIKPTICOFLA-UHFFFAOYSA-N 0.000 description 1
• BNUSJPBXLDGQNH-UHFFFAOYSA-N FC1=CC=C(CCC=2SC=3N=C(N=C(C3N2)S(=O)(=O)C)N)C=C1.NC=1N=C(C2=C(N1)SC(=N2)CCC2=CC=C(C=C2)F)N2CCN(CC2)C(COC2=CC=C(C=C2)OC)=O Chemical compound FC1=CC=C(CCC=2SC=3N=C(N=C(C3N2)S(=O)(=O)C)N)C=C1.NC=1N=C(C2=C(N1)SC(=N2)CCC2=CC=C(C=C2)F)N2CCN(CC2)C(COC2=CC=C(C=C2)OC)=O BNUSJPBXLDGQNH-UHFFFAOYSA-N 0.000 description 1
• 238000006937 Gewald synthesis reaction Methods 0.000 description 1
• 206010018364 Glomerulonephritis Diseases 0.000 description 1
• JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 description 1
• ZWZWYGMENQVNFU-UHFFFAOYSA-N Glycerophosphorylserin Natural products OC(=O)C(N)COP(O)(=O)OCC(O)CO ZWZWYGMENQVNFU-UHFFFAOYSA-N 0.000 description 1
• AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 1
• 208000024869 Goodpasture syndrome Diseases 0.000 description 1
• 208000015023 Graves' disease Diseases 0.000 description 1
• 239000007818 Grignard reagent Substances 0.000 description 1
• 102000009465 Growth Factor Receptors Human genes 0.000 description 1
• 108010009202 Growth Factor Receptors Proteins 0.000 description 1
• 229920002907 Guar gum Polymers 0.000 description 1
• 229920000084 Gum arabic Polymers 0.000 description 1
• 102000006354 HLA-DR Antigens Human genes 0.000 description 1
• 108010058597 HLA-DR Antigens Proteins 0.000 description 1
• IVDFJHOHABJVEH-UHFFFAOYSA-N HOCMe2CMe2OH Natural products CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 1
• 208000002250 Hematologic Neoplasms Diseases 0.000 description 1
• 206010019851 Hepatotoxicity Diseases 0.000 description 1
• 208000029433 Herpesviridae infectious disease Diseases 0.000 description 1
• 206010020112 Hirsutism Diseases 0.000 description 1
• 101000934374 Homo sapiens Early activation antigen CD69 Proteins 0.000 description 1
• 101000628949 Homo sapiens Mitogen-activated protein kinase 10 Proteins 0.000 description 1
• 101000777277 Homo sapiens Serine/threonine-protein kinase Chk2 Proteins 0.000 description 1
• 101000914484 Homo sapiens T-lymphocyte activation antigen CD80 Proteins 0.000 description 1
• 101000835093 Homo sapiens Transferrin receptor protein 1 Proteins 0.000 description 1
• 101000679851 Homo sapiens Tumor necrosis factor receptor superfamily member 4 Proteins 0.000 description 1
• 101000934996 Homo sapiens Tyrosine-protein kinase JAK3 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 group ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
• 108060006678 I-kappa-B kinase Proteins 0.000 description 1
• 206010021245 Idiopathic thrombocytopenic purpura Diseases 0.000 description 1
• 206010061218 Inflammation Diseases 0.000 description 1
• 102100021854 Inhibitor of nuclear factor kappa-B kinase subunit beta Human genes 0.000 description 1
• UGQMRVRMYYASKQ-KQYNXXCUSA-N Inosine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC=NC(O)=C2N=C1 UGQMRVRMYYASKQ-KQYNXXCUSA-N 0.000 description 1
• 229930010555 Inosine Natural products 0.000 description 1
• 102000004877 Insulin Human genes 0.000 description 1
• 108090001061 Insulin Proteins 0.000 description 1
• 102100037850 Interferon gamma Human genes 0.000 description 1
• 108090000467 Interferon-beta Proteins 0.000 description 1
• 102000003996 Interferon-beta Human genes 0.000 description 1
• 102000051628 Interleukin-1 receptor antagonist Human genes 0.000 description 1
• 108700021006 Interleukin-1 receptor antagonist Proteins 0.000 description 1
• 102000010789 Interleukin-2 Receptors Human genes 0.000 description 1
• 108010038453 Interleukin-2 Receptors Proteins 0.000 description 1
• 108090000978 Interleukin-4 Proteins 0.000 description 1
• 108090001007 Interleukin-8 Proteins 0.000 description 1
• 102000004890 Interleukin-8 Human genes 0.000 description 1
• 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
• 108010024121 Janus Kinases Proteins 0.000 description 1
• 102000015617 Janus Kinases Human genes 0.000 description 1
• 239000005909 Kieselgur Substances 0.000 description 1
• QAQJMLQRFWZOBN-LAUBAEHRSA-N L-ascorbyl-6-palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O QAQJMLQRFWZOBN-LAUBAEHRSA-N 0.000 description 1
• 239000011786 L-ascorbyl-6-palmitate Substances 0.000 description 1
• WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
• 229920001491 Lentinan Polymers 0.000 description 1
• HLFSDGLLUJUHTE-SNVBAGLBSA-N Levamisole Chemical compound C1([C@H]2CN3CCSC3=N2)=CC=CC=C1 HLFSDGLLUJUHTE-SNVBAGLBSA-N 0.000 description 1
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
• 206010067125 Liver injury Diseases 0.000 description 1
• 102000043131 MHC class II family Human genes 0.000 description 1
• 108091054438 MHC class II family Proteins 0.000 description 1
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
• 108700018351 Major Histocompatibility Complex Proteins 0.000 description 1
• PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical group O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
• FQISKWAFAHGMGT-SGJOWKDISA-M Methylprednisolone sodium succinate Chemical compound [Na+].C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)[C@@](O)(C(=O)COC(=O)CCC([O-])=O)CC[C@H]21 FQISKWAFAHGMGT-SGJOWKDISA-M 0.000 description 1
• 102100026931 Mitogen-activated protein kinase 10 Human genes 0.000 description 1
• HZQDCMWJEBCWBR-UUOKFMHZSA-N Mizoribine Chemical compound OC1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 HZQDCMWJEBCWBR-UUOKFMHZSA-N 0.000 description 1
• 208000009525 Myocarditis Diseases 0.000 description 1
• CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
• MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
• YBPODVKBQSHOHF-UHFFFAOYSA-N N1(CCNCC1)C(=O)NC1=C(C=C(C=C1)F)F.N1(CCNCC1)C(=O)NC1=CC=C(C=C1)Br Chemical compound N1(CCNCC1)C(=O)NC1=C(C=C(C=C1)F)F.N1(CCNCC1)C(=O)NC1=CC=C(C=C1)Br YBPODVKBQSHOHF-UHFFFAOYSA-N 0.000 description 1
• PHBNZQQBOBVRCE-UHFFFAOYSA-N N1=CN=CC=C1.N1=COC2=C1C=NC=N2 Chemical compound N1=CN=CC=C1.N1=COC2=C1C=NC=N2 PHBNZQQBOBVRCE-UHFFFAOYSA-N 0.000 description 1
• QFFJHMAOVNIHRE-UHFFFAOYSA-N N1=CN=CC=C1.[S-2].[Na+].[Na+] Chemical class N1=CN=CC=C1.[S-2].[Na+].[Na+] QFFJHMAOVNIHRE-UHFFFAOYSA-N 0.000 description 1
• QLYCLHXRKWXYIL-UHFFFAOYSA-N NC1=NC(=C2N=C(NC2=N1)SC)N1C(CNCC1)C(COC1=CC=C(C=C1)Cl)=O Chemical compound NC1=NC(=C2N=C(NC2=N1)SC)N1C(CNCC1)C(COC1=CC=C(C=C1)Cl)=O QLYCLHXRKWXYIL-UHFFFAOYSA-N 0.000 description 1
• 229910002651 NO3 Inorganic materials 0.000 description 1
• 206010029155 Nephropathy toxic Diseases 0.000 description 1
• 206010029350 Neurotoxicity Diseases 0.000 description 1
• NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
• OVIQUYVVZZMTBI-UHFFFAOYSA-N O1CCOCC1.ClC1=CC=C(OCC(=O)N2CCN(CC2)C=2C3=C(N=C(N2)C)SC(=N3)C3=CC=C(C=C3)F)C=C1 Chemical compound O1CCOCC1.ClC1=CC=C(OCC(=O)N2CCN(CC2)C=2C3=C(N=C(N2)C)SC(=N3)C3=CC=C(C=C3)F)C=C1 OVIQUYVVZZMTBI-UHFFFAOYSA-N 0.000 description 1
• APQVPXMCZGURJR-UHFFFAOYSA-N O=C(COC1=CC=CC=C1)N(CC1)CCN1C1=NC(C=NC=N2)=C2S1 Chemical compound O=C(COC1=CC=CC=C1)N(CC1)CCN1C1=NC(C=NC=N2)=C2S1 APQVPXMCZGURJR-UHFFFAOYSA-N 0.000 description 1
• 208000021384 Obsessive-Compulsive disease Diseases 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
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
• 108091007960 PI3Ks Proteins 0.000 description 1
• 102000038030 PI3Ks Human genes 0.000 description 1
• 208000018737 Parkinson disease Diseases 0.000 description 1
• 241000721454 Pemphigus Species 0.000 description 1
• BYPFEZZEUUWMEJ-UHFFFAOYSA-N Pentoxifylline Chemical compound O=C1N(CCCCC(=O)C)C(=O)N(C)C2=C1N(C)C=N2 BYPFEZZEUUWMEJ-UHFFFAOYSA-N 0.000 description 1
• 208000031845 Pernicious anaemia Diseases 0.000 description 1
• 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 description 1
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
• 206010035664 Pneumonia Diseases 0.000 description 1
• 239000004698 Polyethylene Substances 0.000 description 1
• 239000004743 Polypropylene Substances 0.000 description 1
• 229920001214 Polysorbate 60 Polymers 0.000 description 1
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
• 102000004257 Potassium Channel Human genes 0.000 description 1
• 208000012654 Primary biliary cholangitis Diseases 0.000 description 1
• 101710101148 Probable 6-oxopurine nucleoside phosphorylase Proteins 0.000 description 1
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
• GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
• 102000007327 Protamines Human genes 0.000 description 1
• 108010007568 Protamines Proteins 0.000 description 1
• 208000003251 Pruritus Diseases 0.000 description 1
• 201000001263 Psoriatic Arthritis Diseases 0.000 description 1
• 208000036824 Psoriatic arthropathy Diseases 0.000 description 1
• 208000028017 Psychotic disease Diseases 0.000 description 1
• 102000030764 Purine-nucleoside phosphorylase Human genes 0.000 description 1
• LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 description 1
• 239000007868 Raney catalyst Substances 0.000 description 1
• 229910000564 Raney nickel Inorganic materials 0.000 description 1
• 241001115903 Raphus cucullatus Species 0.000 description 1
• 241000700159 Rattus Species 0.000 description 1
• HWVXKQIPAIDRSJ-UHFFFAOYSA-N S1C(=CC=C1)CCC=1SC=2N=CN=C(C2N1)N1CCN(CC1)C(NC=1C=C(C=CC1)C)=O Chemical compound S1C(=CC=C1)CCC=1SC=2N=CN=C(C2N1)N1CCN(CC1)C(NC=1C=C(C=CC1)C)=O HWVXKQIPAIDRSJ-UHFFFAOYSA-N 0.000 description 1
• 239000002262 Schiff base Substances 0.000 description 1
• 150000004753 Schiff bases Chemical class 0.000 description 1
• 206010039710 Scleroderma Diseases 0.000 description 1
• BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
• 102100031075 Serine/threonine-protein kinase Chk2 Human genes 0.000 description 1
• 208000021386 Sjogren Syndrome Diseases 0.000 description 1
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
• DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
• IOEJYZSZYUROLN-UHFFFAOYSA-M Sodium diethyldithiocarbamate Chemical compound [Na+].CCN(CC)C([S-])=S IOEJYZSZYUROLN-UHFFFAOYSA-M 0.000 description 1
• DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
• 238000003477 Sonogashira cross-coupling reaction Methods 0.000 description 1
• 239000004147 Sorbitan trioleate Substances 0.000 description 1
• PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 1
• 235000021355 Stearic acid Nutrition 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
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
• ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
• 208000018359 Systemic autoimmune disease Diseases 0.000 description 1
• 230000006052 T cell proliferation Effects 0.000 description 1
• 108091008874 T cell receptors Proteins 0.000 description 1
• 102000016266 T-Cell Antigen Receptors Human genes 0.000 description 1
• 102100027222 T-lymphocyte activation antigen CD80 Human genes 0.000 description 1
• 102000003566 TRPV1 Human genes 0.000 description 1
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
• 208000031981 Thrombocytopenic Idiopathic Purpura Diseases 0.000 description 1
• 101800001703 Thymopentin Proteins 0.000 description 1
• 102400000160 Thymopentin Human genes 0.000 description 1
• 206010044221 Toxic encephalopathy Diseases 0.000 description 1
• 229920001615 Tragacanth Polymers 0.000 description 1
• 102000040945 Transcription factor Human genes 0.000 description 1
• 108091023040 Transcription factor Proteins 0.000 description 1
• 102100026144 Transferrin receptor protein 1 Human genes 0.000 description 1
• 102100029613 Transient receptor potential cation channel subfamily V member 1 Human genes 0.000 description 1
• 108050004388 Transient receptor potential cation channel subfamily V member 1 Proteins 0.000 description 1
• 239000007983 Tris buffer Substances 0.000 description 1
• 101150016206 Trpv1 gene Proteins 0.000 description 1
• 102100022153 Tumor necrosis factor receptor superfamily member 4 Human genes 0.000 description 1
• 102000011017 Type 4 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 description 1
• 108010037584 Type 4 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 description 1
• 108091005906 Type I transmembrane proteins Proteins 0.000 description 1
• 108091005956 Type II transmembrane proteins Proteins 0.000 description 1
• 102100025387 Tyrosine-protein kinase JAK3 Human genes 0.000 description 1
• 208000025865 Ulcer Diseases 0.000 description 1
• 206010047115 Vasculitis Diseases 0.000 description 1
• 208000036142 Viral infection Diseases 0.000 description 1
• MXUDBSJPEFSOGN-UHFFFAOYSA-N [1,3]thiazolo[5,4-d]pyrimidin-5-amine Chemical compound NC1=NC=C2N=CSC2=N1 MXUDBSJPEFSOGN-UHFFFAOYSA-N 0.000 description 1
• WCBKNACDYVCBLV-UHFFFAOYSA-N [1-[2-amino-6-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]piperidin-4-yl]-phenylmethanone Chemical compound C=12C=C(C=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N(CC1)CCC1C(=O)C1=CC=CC=C1 WCBKNACDYVCBLV-UHFFFAOYSA-N 0.000 description 1
• CVWNWFURXOCMRH-UHFFFAOYSA-N [2-[2-amino-6-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]piperazin-1-yl]-cyclohexylmethanone Chemical compound C=12C=C(C=3C=CC(F)=CC=3)SC2=NC(N)=NC=1C1CNCCN1C(=O)C1CCCCC1 CVWNWFURXOCMRH-UHFFFAOYSA-N 0.000 description 1
• SSWNCVHPWOKMEB-UHFFFAOYSA-N [2-[2-amino-6-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]piperazin-1-yl]-pyridin-4-ylmethanone Chemical compound C=12C=C(C=3C=CC(F)=CC=3)SC2=NC(N)=NC=1C1CNCCN1C(=O)C1=CC=NC=C1 SSWNCVHPWOKMEB-UHFFFAOYSA-N 0.000 description 1
• CMLPPNNEVNLWJY-UHFFFAOYSA-N [4-(2-amino-6-phenylthieno[2,3-d]pyrimidin-4-yl)-1,4-diazepan-1-yl]-(4-chlorophenyl)methanone Chemical compound C=12C=C(C=3C=CC=CC=3)SC2=NC(N)=NC=1N(CC1)CCCN1C(=O)C1=CC=C(Cl)C=C1 CMLPPNNEVNLWJY-UHFFFAOYSA-N 0.000 description 1
• BSQJEEFPASHMIJ-UHFFFAOYSA-N [4-[2-amino-6-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]piperazin-1-yl]-cyclohexylmethanone 4-(4-benzylsulfonylpiperazin-1-yl)-6-(4-fluorophenyl)thieno[2,3-d]pyrimidin-2-amine Chemical compound C=12C=C(C=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)C1CCCCC1.C=12C=C(C=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1S(=O)(=O)CC1=CC=CC=C1 BSQJEEFPASHMIJ-UHFFFAOYSA-N 0.000 description 1
• FCRYKXXNLBDWDD-UHFFFAOYSA-N [4-[2-amino-8-(4-fluorophenyl)-7h-purin-6-yl]piperazin-1-yl]-(4-chlorophenyl)methanone Chemical compound C=12N=C(C=3C=CC(F)=CC=3)NC2=NC(N)=NC=1N(CC1)CCN1C(=O)C1=CC=C(Cl)C=C1 FCRYKXXNLBDWDD-UHFFFAOYSA-N 0.000 description 1
• SEUIDDVFWVCCCJ-UHFFFAOYSA-N [4-[2-amino-8-(4-fluorophenyl)-7h-purin-6-yl]piperazin-1-yl]-naphthalen-1-ylmethanone Chemical compound N1C2=NC(N)=NC(N3CCN(CC3)C(=O)C=3C4=CC=CC=C4C=CC=3)=C2N=C1C1=CC=C(F)C=C1 SEUIDDVFWVCCCJ-UHFFFAOYSA-N 0.000 description 1
• KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 description 1
• CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 1
• MCGSCOLBFJQGHM-SCZZXKLOSA-N abacavir Chemical compound C=12N=CN([C@H]3C=C[C@@H](CO)C3)C2=NC(N)=NC=1NC1CC1 MCGSCOLBFJQGHM-SCZZXKLOSA-N 0.000 description 1
• 229960004748 abacavir Drugs 0.000 description 1
• 239000006096 absorbing agent Substances 0.000 description 1
• 235000010489 acacia gum Nutrition 0.000 description 1
• 239000000205 acacia gum Substances 0.000 description 1
• WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
• 239000012346 acetyl chloride Substances 0.000 description 1
• 229960004150 aciclovir Drugs 0.000 description 1
• 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
• 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
• 230000003213 activating effect Effects 0.000 description 1
• 239000013543 active substance Substances 0.000 description 1
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
• 239000003121 adenosine kinase inhibitor Substances 0.000 description 1
• 239000000853 adhesive Substances 0.000 description 1
• 230000001070 adhesive effect Effects 0.000 description 1
• 230000002411 adverse Effects 0.000 description 1
• 150000001298 alcohols Chemical class 0.000 description 1
• 150000001342 alkaline earth metals Chemical class 0.000 description 1
• 125000004171 alkoxy aryl group Chemical group 0.000 description 1
• 150000003973 alkyl amines Chemical class 0.000 description 1
• 125000005115 alkyl carbamoyl group Chemical group 0.000 description 1
• 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
• 208000030961 allergic reaction Diseases 0.000 description 1
• 230000000961 alloantigen Effects 0.000 description 1
• 229910052782 aluminium Inorganic materials 0.000 description 1
• XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
• 239000003708 ampul Substances 0.000 description 1
• 230000036592 analgesia Effects 0.000 description 1
• 230000000202 analgesic effect Effects 0.000 description 1
• 230000033115 angiogenesis Effects 0.000 description 1
• 239000004037 angiogenesis inhibitor Substances 0.000 description 1
• 229940121369 angiogenesis inhibitor Drugs 0.000 description 1
• 230000003042 antagnostic effect Effects 0.000 description 1
• 230000008485 antagonism Effects 0.000 description 1
• 239000005557 antagonist Substances 0.000 description 1
• 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
• 239000003242 anti bacterial agent Substances 0.000 description 1
• 239000002259 anti human immunodeficiency virus agent Substances 0.000 description 1
• 230000000844 anti-bacterial effect Effects 0.000 description 1
• 230000003110 anti-inflammatory effect Effects 0.000 description 1
• 230000000259 anti-tumor effect Effects 0.000 description 1
• 230000000840 anti-viral effect Effects 0.000 description 1
• 239000003429 antifungal agent Substances 0.000 description 1
• 229940121375 antifungal agent Drugs 0.000 description 1
• 230000030741 antigen processing and presentation Effects 0.000 description 1
• 210000000612 antigen-presenting cell Anatomy 0.000 description 1
• 230000000890 antigenic effect Effects 0.000 description 1
• 239000002246 antineoplastic agent Substances 0.000 description 1
• 239000003963 antioxidant agent Substances 0.000 description 1
• 239000003443 antiviral agent Substances 0.000 description 1
• 230000006907 apoptotic process Effects 0.000 description 1
• 239000012062 aqueous buffer Substances 0.000 description 1
• 239000008346 aqueous phase Substances 0.000 description 1
• 235000009697 arginine Nutrition 0.000 description 1
• 150000001484 arginines Chemical class 0.000 description 1
• 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
• 125000003435 aroyl group Chemical group 0.000 description 1
• 206010003119 arrhythmia Diseases 0.000 description 1
• 125000005116 aryl carbamoyl group Chemical group 0.000 description 1
• 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
• 125000005110 aryl thio group Chemical group 0.000 description 1
• 235000010385 ascorbyl palmitate Nutrition 0.000 description 1
• 239000000305 astragalus gummifer gum Substances 0.000 description 1
• 201000008937 atopic dermatitis Diseases 0.000 description 1
• 201000003710 autoimmune thrombocytopenic purpura Diseases 0.000 description 1
• 230000005784 autoimmunity Effects 0.000 description 1
• 125000005602 azabenzimidazolyl group Chemical group 0.000 description 1
• 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 description 1
• 125000002393 azetidinyl group Chemical group 0.000 description 1
• 125000004069 aziridinyl group Chemical group 0.000 description 1
• 239000000987 azo dye Substances 0.000 description 1
• 238000007630 basic procedure Methods 0.000 description 1
• 230000008901 benefit Effects 0.000 description 1
• 239000000440 bentonite Substances 0.000 description 1
• 229910000278 bentonite Inorganic materials 0.000 description 1
• SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 1
• 229940077388 benzenesulfonate Drugs 0.000 description 1
• SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
• CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
• 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 description 1
• 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
• 229940049706 benzodiazepine Drugs 0.000 description 1
• 125000004602 benzodiazinyl group Chemical group N1=NC(=CC2=C1C=CC=C2)* 0.000 description 1
• 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
• 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
• 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
• 125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 description 1
• PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
• HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
• 238000012925 biological evaluation Methods 0.000 description 1
• 235000010290 biphenyl Nutrition 0.000 description 1
• 239000004305 biphenyl Substances 0.000 description 1
• 210000004369 blood Anatomy 0.000 description 1
• 239000008280 blood Substances 0.000 description 1
• 210000004204 blood vessel Anatomy 0.000 description 1
• 210000000988 bone and bone Anatomy 0.000 description 1
• 210000002798 bone marrow cell Anatomy 0.000 description 1
• 210000004556 brain Anatomy 0.000 description 1
• 125000001246 bromo group Chemical group Br* 0.000 description 1
• RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
• 229960004272 bucillamine Drugs 0.000 description 1
• 239000000872 buffer Substances 0.000 description 1
• 239000004067 bulking agent Substances 0.000 description 1
• 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
• 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 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
• 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
• 239000004202 carbamide Substances 0.000 description 1
• 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
• 125000004623 carbolinyl group Chemical group 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
• KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
• 150000003857 carboxamides Chemical class 0.000 description 1
• 150000001735 carboxylic acids Chemical class 0.000 description 1
• 230000000747 cardiac effect Effects 0.000 description 1
• 230000002612 cardiopulmonary effect Effects 0.000 description 1
• 239000012876 carrier material Substances 0.000 description 1
• 239000003054 catalyst Substances 0.000 description 1
• 125000002091 cationic group Chemical group 0.000 description 1
• 230000032823 cell division Effects 0.000 description 1
• 230000001413 cellular effect Effects 0.000 description 1
• 229920002301 cellulose acetate Polymers 0.000 description 1
• 229940082500 cetostearyl alcohol Drugs 0.000 description 1
• 239000013626 chemical specie Substances 0.000 description 1
• 229960004926 chlorobutanol Drugs 0.000 description 1
• VDANGULDQQJODZ-UHFFFAOYSA-N chloroprocaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1Cl VDANGULDQQJODZ-UHFFFAOYSA-N 0.000 description 1
• 229960002023 chloroprocaine Drugs 0.000 description 1
• 229960003677 chloroquine Drugs 0.000 description 1
• WHTVZRBIWZFKQO-UHFFFAOYSA-N chloroquine Natural products ClC1=CC=C2C(NC(C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-UHFFFAOYSA-N 0.000 description 1
• OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
• 229960001231 choline Drugs 0.000 description 1
• 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 description 1
• 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 description 1
• 230000001684 chronic effect Effects 0.000 description 1
• 208000025302 chronic primary adrenal insufficiency Diseases 0.000 description 1
• 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
• 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
• 229940001468 citrate Drugs 0.000 description 1
• 238000003501 co-culture Methods 0.000 description 1
• 239000011248 coating agent Substances 0.000 description 1
• 239000003240 coconut oil Substances 0.000 description 1
• 235000019864 coconut oil Nutrition 0.000 description 1
• 206010009887 colitis Diseases 0.000 description 1
• 238000004440 column chromatography Methods 0.000 description 1
• 239000012141 concentrate Substances 0.000 description 1
• 239000007859 condensation product Substances 0.000 description 1
• OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
• 210000004087 cornea Anatomy 0.000 description 1
• 238000012937 correction Methods 0.000 description 1
• 239000002537 cosmetic Substances 0.000 description 1
• 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 description 1
• 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 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
• 125000002188 cycloheptatrienyl group Chemical group C1(=CC=CC=CC1)* 0.000 description 1
• 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 1
• RVOJTCZRIKWHDX-UHFFFAOYSA-N cyclohexanecarbonyl chloride Chemical compound ClC(=O)C1CCCCC1 RVOJTCZRIKWHDX-UHFFFAOYSA-N 0.000 description 1
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
• NKLCHDQGUHMCGL-UHFFFAOYSA-N cyclohexylidenemethanone Chemical group O=C=C1CCCCC1 NKLCHDQGUHMCGL-UHFFFAOYSA-N 0.000 description 1
• 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 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
• 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
• 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
• 229960004397 cyclophosphamide Drugs 0.000 description 1
• ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 1
• 125000000298 cyclopropenyl group Chemical group [H]C1=C([H])C1([H])* 0.000 description 1
• 230000000445 cytocidal effect Effects 0.000 description 1
• 210000001151 cytotoxic T lymphocyte Anatomy 0.000 description 1
• 229950008150 daltroban Drugs 0.000 description 1
• 230000006378 damage Effects 0.000 description 1
• 230000002950 deficient Effects 0.000 description 1
• 230000001419 dependent effect Effects 0.000 description 1
• 239000003599 detergent Substances 0.000 description 1
• 238000011161 development Methods 0.000 description 1
• GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
• 125000002576 diazepinyl group Chemical group N1N=C(C=CC=C1)* 0.000 description 1
• 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
• 125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 description 1
• 150000001991 dicarboxylic acids Chemical class 0.000 description 1
• 125000003963 dichloro group Chemical group Cl* 0.000 description 1
• 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
• ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
• 229940043237 diethanolamine Drugs 0.000 description 1
• LQDJGPTUSMDFBA-UHFFFAOYSA-N diethyl 2-[(4-fluorobenzoyl)amino]propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)NC(=O)C1=CC=C(F)C=C1 LQDJGPTUSMDFBA-UHFFFAOYSA-N 0.000 description 1
• UQIFUBUFYITEAI-UHFFFAOYSA-N diethyl 2-[[2-(4-fluorophenyl)acetyl]amino]propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)NC(=O)CC1=CC=C(F)C=C1 UQIFUBUFYITEAI-UHFFFAOYSA-N 0.000 description 1
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical group OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
• 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 description 1
• 125000004655 dihydropyridinyl group Chemical group N1(CC=CC=C1)* 0.000 description 1
• 125000005057 dihydrothienyl group Chemical group S1C(CC=C1)* 0.000 description 1
• 229950009815 dimepranol Drugs 0.000 description 1
• CYPOXSVGVPUXKE-UHFFFAOYSA-N dimethyl 2-[3-(4-fluorophenoxy)propanoylamino]propanedioate Chemical compound COC(=O)C(C(=O)OC)NC(=O)CCOC1=CC=C(F)C=C1 CYPOXSVGVPUXKE-UHFFFAOYSA-N 0.000 description 1
• SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
• 150000002009 diols Chemical class 0.000 description 1
• 239000001177 diphosphate Substances 0.000 description 1
• 235000011180 diphosphates Nutrition 0.000 description 1
• ZGSPNIOCEDOHGS-UHFFFAOYSA-L disodium [3-[2,3-di(octadeca-9,12-dienoyloxy)propoxy-oxidophosphoryl]oxy-2-hydroxypropyl] 2,3-di(octadeca-9,12-dienoyloxy)propyl phosphate Chemical compound [Na+].[Na+].CCCCCC=CCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCC=CCCCCC)COP([O-])(=O)OCC(O)COP([O-])(=O)OCC(OC(=O)CCCCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC ZGSPNIOCEDOHGS-UHFFFAOYSA-L 0.000 description 1
• 239000002270 dispersing agent Substances 0.000 description 1
• 239000006185 dispersion Substances 0.000 description 1
• 238000004090 dissolution Methods 0.000 description 1
• 125000005883 dithianyl group Chemical group 0.000 description 1
• 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
• 239000000890 drug combination Substances 0.000 description 1
• 238000012377 drug delivery Methods 0.000 description 1
• 238000007876 drug discovery Methods 0.000 description 1
• 229940009662 edetate Drugs 0.000 description 1
• 229960001484 edetic acid Drugs 0.000 description 1
• 230000001804 emulsifying effect Effects 0.000 description 1
• 239000000839 emulsion Substances 0.000 description 1
• ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
• 239000003623 enhancer Substances 0.000 description 1
• 230000002708 enhancing effect Effects 0.000 description 1
• 229960000403 etanercept Drugs 0.000 description 1
• AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 description 1
• CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
• 235000019441 ethanol Nutrition 0.000 description 1
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
• NJMDQJMSRKJURW-UHFFFAOYSA-N ethyl 2-[4-[4-[2-(4-chlorophenoxy)acetyl]piperazin-1-yl]-6-(4-fluorophenyl)thieno[2,3-d]pyrimidin-2-yl]acetate Chemical compound C=12C=C(C=3C=CC(F)=CC=3)SC2=NC(CC(=O)OCC)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 NJMDQJMSRKJURW-UHFFFAOYSA-N 0.000 description 1
• ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
• UWQHZCTYYIVMQR-UHFFFAOYSA-N ethyl 4-[4-[2-(4-chlorophenoxy)acetyl]piperazin-1-yl]-6-(4-fluorophenyl)thieno[2,3-d]pyrimidine-2-carboxylate Chemical compound C=12C=C(C=3C=CC(F)=CC=3)SC2=NC(C(=O)OCC)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 UWQHZCTYYIVMQR-UHFFFAOYSA-N 0.000 description 1
• RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
• 125000004494 ethyl ester group Chemical group 0.000 description 1
• RQRTZWLAEIQXNZ-UHFFFAOYSA-N ethyl n-(2-amino-4-hydroxy-6-oxo-1h-pyrimidin-5-yl)carbamate Chemical compound CCOC(=O)NC1=C(O)N=C(N)N=C1O RQRTZWLAEIQXNZ-UHFFFAOYSA-N 0.000 description 1
• LNOQURRKNJKKBU-UHFFFAOYSA-N ethyl piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCNCC1 LNOQURRKNJKKBU-UHFFFAOYSA-N 0.000 description 1
• 239000005038 ethylene vinyl acetate Substances 0.000 description 1
• 229940012017 ethylenediamine Drugs 0.000 description 1
• 238000011156 evaluation Methods 0.000 description 1
• 230000003631 expected effect Effects 0.000 description 1
• 210000001508 eye Anatomy 0.000 description 1
• 210000000887 face Anatomy 0.000 description 1
• 150000002194 fatty esters Chemical class 0.000 description 1
• 239000000945 filler Substances 0.000 description 1
• 239000012467 final product Substances 0.000 description 1
• 239000000796 flavoring agent Substances 0.000 description 1
• AAXVEMMRQDVLJB-BULBTXNYSA-N fludrocortisone Chemical compound O=C1CC[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 AAXVEMMRQDVLJB-BULBTXNYSA-N 0.000 description 1
• 229960002011 fludrocortisone Drugs 0.000 description 1
• 229950002998 flumoxonide Drugs 0.000 description 1
• 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
• 235000013355 food flavoring agent Nutrition 0.000 description 1
• 229940050411 fumarate Drugs 0.000 description 1
• 125000002541 furyl group Chemical group 0.000 description 1
• 229960002963 ganciclovir Drugs 0.000 description 1
• 239000007789 gas Substances 0.000 description 1
• 210000001035 gastrointestinal tract Anatomy 0.000 description 1
• 239000003862 glucocorticoid Substances 0.000 description 1
• 229940050410 gluconate Drugs 0.000 description 1
• 229930195712 glutamate Natural products 0.000 description 1
• 150000002334 glycols Chemical class 0.000 description 1
• 239000008187 granular material Substances 0.000 description 1
• 229960004198 guanidine Drugs 0.000 description 1
• 229960000789 guanidine hydrochloride Drugs 0.000 description 1
• PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 1
• 239000000665 guar gum Substances 0.000 description 1
• 235000010417 guar gum Nutrition 0.000 description 1
• 229960002154 guar gum Drugs 0.000 description 1
• IDINUJSAMVOPCM-UHFFFAOYSA-N gusperimus Chemical compound NCCCNCCCCNC(=O)C(O)NC(=O)CCCCCCN=C(N)N IDINUJSAMVOPCM-UHFFFAOYSA-N 0.000 description 1
• 229960002706 gusperimus Drugs 0.000 description 1
• 210000004209 hair Anatomy 0.000 description 1
• 210000002837 heart atrium Anatomy 0.000 description 1
• 210000003709 heart valve Anatomy 0.000 description 1
• 239000003481 heat shock protein 90 inhibitor Substances 0.000 description 1
• 210000002443 helper t lymphocyte Anatomy 0.000 description 1
• 208000007475 hemolytic anemia Diseases 0.000 description 1
• 230000002949 hemolytic effect Effects 0.000 description 1
• 231100000234 hepatic damage Toxicity 0.000 description 1
• 210000003494 hepatocyte Anatomy 0.000 description 1
• 231100000304 hepatotoxicity Toxicity 0.000 description 1
• 230000007686 hepatotoxicity Effects 0.000 description 1
• UBHWBODXJBSFLH-UHFFFAOYSA-N hexadecan-1-ol;octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO.CCCCCCCCCCCCCCCCCCO UBHWBODXJBSFLH-UHFFFAOYSA-N 0.000 description 1
• YWGHUJQYGPDNKT-UHFFFAOYSA-N hexanoyl chloride Chemical compound CCCCCC(Cl)=O YWGHUJQYGPDNKT-UHFFFAOYSA-N 0.000 description 1
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 238000004128 high performance liquid chromatography Methods 0.000 description 1
• 210000003630 histaminocyte Anatomy 0.000 description 1
• 229960000890 hydrocortisone Drugs 0.000 description 1
• 239000000017 hydrogel Substances 0.000 description 1
• MSYBLBLAMDYKKZ-UHFFFAOYSA-N hydron;pyridine-3-carbonyl chloride;chloride Chemical compound Cl.ClC(=O)C1=CC=CN=C1 MSYBLBLAMDYKKZ-UHFFFAOYSA-N 0.000 description 1
• XXSMGPRMXLTPCZ-UHFFFAOYSA-N hydroxychloroquine Chemical compound ClC1=CC=C2C(NC(C)CCCN(CCO)CC)=CC=NC2=C1 XXSMGPRMXLTPCZ-UHFFFAOYSA-N 0.000 description 1
• 229960004171 hydroxychloroquine Drugs 0.000 description 1
• 229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
• 229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
• 230000003463 hyperproliferative effect Effects 0.000 description 1
• 239000005457 ice water Substances 0.000 description 1
• DOUYETYNHWVLEO-UHFFFAOYSA-N imiquimod Chemical compound C1=CC=CC2=C3N(CC(C)C)C=NC3=C(N)N=C21 DOUYETYNHWVLEO-UHFFFAOYSA-N 0.000 description 1
• 229960002751 imiquimod Drugs 0.000 description 1
• 230000003053 immunization Effects 0.000 description 1
• 238000002649 immunization Methods 0.000 description 1
• 230000001965 increasing effect Effects 0.000 description 1
• 125000003427 indacenyl group Chemical group 0.000 description 1
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
• 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
• 125000001041 indolyl group Chemical group 0.000 description 1
• 239000000411 inducer Substances 0.000 description 1
• 208000015181 infectious disease Diseases 0.000 description 1
• 208000000509 infertility Diseases 0.000 description 1
• 230000036512 infertility Effects 0.000 description 1
• 231100000535 infertility Toxicity 0.000 description 1
• 230000008595 infiltration Effects 0.000 description 1
• 238000001764 infiltration Methods 0.000 description 1
• 208000021646 inflammation of heart layer Diseases 0.000 description 1
• 230000002757 inflammatory effect Effects 0.000 description 1
• 230000004054 inflammatory process Effects 0.000 description 1
• 229960000598 infliximab Drugs 0.000 description 1
• 239000004615 ingredient Substances 0.000 description 1
• 210000005007 innate immune system Anatomy 0.000 description 1
• 150000007529 inorganic bases Chemical class 0.000 description 1
• 239000001023 inorganic pigment Substances 0.000 description 1
• 229910001867 inorganic solvent Inorganic materials 0.000 description 1
• 239000003049 inorganic solvent Substances 0.000 description 1
• 229960003786 inosine Drugs 0.000 description 1
• 229940125396 insulin Drugs 0.000 description 1
• 229960001388 interferon-beta Drugs 0.000 description 1
• 210000000936 intestine Anatomy 0.000 description 1
• 238000010253 intravenous injection Methods 0.000 description 1
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
• 238000005040 ion trap Methods 0.000 description 1
• RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
• 230000007794 irritation Effects 0.000 description 1
• 125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 1
• QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
• JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
• 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
• 125000005956 isoquinolyl group Chemical group 0.000 description 1
• 125000001786 isothiazolyl group Chemical group 0.000 description 1
• 150000002540 isothiocyanates Chemical class 0.000 description 1
• 239000007951 isotonicity adjuster Substances 0.000 description 1
• NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
• 150000002576 ketones Chemical class 0.000 description 1
• 229940043355 kinase inhibitor Drugs 0.000 description 1
• 229940054136 kineret Drugs 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
• 229960000681 leflunomide Drugs 0.000 description 1
• VHOGYURTWQBHIL-UHFFFAOYSA-N leflunomide Chemical compound O1N=CC(C(=O)NC=2C=CC(=CC=2)C(F)(F)F)=C1C VHOGYURTWQBHIL-UHFFFAOYSA-N 0.000 description 1
• 229940115286 lentinan Drugs 0.000 description 1
• 210000000265 leukocyte Anatomy 0.000 description 1
• 229960001614 levamisole Drugs 0.000 description 1
• 230000000670 limiting effect Effects 0.000 description 1
• 239000002502 liposome Substances 0.000 description 1
• 229910052744 lithium Inorganic materials 0.000 description 1
• 230000008818 liver damage Effects 0.000 description 1
• 230000007774 longterm Effects 0.000 description 1
• 231100000053 low toxicity Toxicity 0.000 description 1
• 210000004072 lung Anatomy 0.000 description 1
• 206010025135 lupus erythematosus Diseases 0.000 description 1
• 235000018977 lysine Nutrition 0.000 description 1
• 150000002669 lysines Chemical class 0.000 description 1
• 125000004401 m-toluyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C(*)=O 0.000 description 1
• 239000011777 magnesium Substances 0.000 description 1
• 229910052749 magnesium Inorganic materials 0.000 description 1
• 201000004792 malaria Diseases 0.000 description 1
• 229940049920 malate Drugs 0.000 description 1
• 239000001630 malic acid Substances 0.000 description 1
• 235000011090 malic acid Nutrition 0.000 description 1
• 150000002690 malonic acid derivatives Chemical class 0.000 description 1
• 230000000873 masking effect Effects 0.000 description 1
• 238000001819 mass spectrum Methods 0.000 description 1
• 239000000463 material Substances 0.000 description 1
• 230000035800 maturation Effects 0.000 description 1
• 238000005259 measurement Methods 0.000 description 1
• 230000007246 mechanism Effects 0.000 description 1
• 238000002844 melting Methods 0.000 description 1
• 230000008018 melting Effects 0.000 description 1
• 229960001428 mercaptopurine Drugs 0.000 description 1
• 230000006371 metabolic abnormality Effects 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
• 229910000000 metal hydroxide Inorganic materials 0.000 description 1
• 150000004692 metal hydroxides Chemical class 0.000 description 1
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
• 229920000609 methyl cellulose Polymers 0.000 description 1
• 150000004702 methyl esters Chemical class 0.000 description 1
• JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
• 230000011987 methylation Effects 0.000 description 1
• 238000007069 methylation reaction Methods 0.000 description 1
• 239000001923 methylcellulose Substances 0.000 description 1
• 229960004584 methylprednisolone Drugs 0.000 description 1
• 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
• HPNSFSBZBAHARI-UHFFFAOYSA-N micophenolic acid Natural products OC1=C(CC=C(C)CCC(O)=O)C(OC)=C(C)C2=C1C(=O)OC2 HPNSFSBZBAHARI-UHFFFAOYSA-N 0.000 description 1
• 239000004530 micro-emulsion Substances 0.000 description 1
• 230000000813 microbial effect Effects 0.000 description 1
• 239000003094 microcapsule Substances 0.000 description 1
• 244000309715 mini pig Species 0.000 description 1
• 230000011278 mitosis Effects 0.000 description 1
• 229950000844 mizoribine Drugs 0.000 description 1
• 229950007856 mofetil Drugs 0.000 description 1
• 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
• 150000002763 monocarboxylic acids Chemical class 0.000 description 1
• 210000005087 mononuclear cell Anatomy 0.000 description 1
• 229910052901 montmorillonite Inorganic materials 0.000 description 1
• 210000003205 muscle Anatomy 0.000 description 1
• 231100000150 mutagenicity / genotoxicity testing Toxicity 0.000 description 1
• HPNSFSBZBAHARI-RUDMXATFSA-N mycophenolic acid Chemical compound OC1=C(C\C=C(/C)CCC(O)=O)C(OC)=C(C)C2=C1C(=O)OC2 HPNSFSBZBAHARI-RUDMXATFSA-N 0.000 description 1
• 229960000951 mycophenolic acid Drugs 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
• QGAKGZQFOBVYGW-UHFFFAOYSA-N n-(2-amino-4-hydroxy-6-oxo-1h-pyrimidin-5-yl)-2-(4-chlorophenyl)acetamide Chemical compound OC1=NC(N)=NC(O)=C1NC(=O)CC1=CC=C(Cl)C=C1 QGAKGZQFOBVYGW-UHFFFAOYSA-N 0.000 description 1
• HWRKKHWRPUURLQ-UHFFFAOYSA-N n-(2-amino-4-hydroxy-6-oxo-1h-pyrimidin-5-yl)-2-methoxyacetamide Chemical compound COCC(=O)NC1=C(O)N=C(N)N=C1O HWRKKHWRPUURLQ-UHFFFAOYSA-N 0.000 description 1
• HBAZTXPXIYWDJB-UHFFFAOYSA-N n-(2-amino-4-hydroxy-6-oxo-1h-pyrimidin-5-yl)-3,4-dichlorobenzamide Chemical compound OC1=NC(N)=NC(O)=C1NC(=O)C1=CC=C(Cl)C(Cl)=C1 HBAZTXPXIYWDJB-UHFFFAOYSA-N 0.000 description 1
• ZZRBFZOYSRTIAN-UHFFFAOYSA-N n-(2-amino-4-hydroxy-6-oxo-1h-pyrimidin-5-yl)-3-(4-fluorophenoxy)propanamide Chemical compound OC1=NC(N)=NC(O)=C1NC(=O)CCOC1=CC=C(F)C=C1 ZZRBFZOYSRTIAN-UHFFFAOYSA-N 0.000 description 1
• NOAFAXBXYKLLTJ-UHFFFAOYSA-N n-(2-amino-4-hydroxy-6-oxo-1h-pyrimidin-5-yl)-3-methoxybenzamide Chemical compound COC1=CC=CC(C(=O)NC=2C(=NC(N)=NC=2O)O)=C1 NOAFAXBXYKLLTJ-UHFFFAOYSA-N 0.000 description 1
• LKGKWHBHCMQTQV-UHFFFAOYSA-N n-(2-amino-4-hydroxy-6-oxo-1h-pyrimidin-5-yl)hexanamide Chemical compound CCCCCC(=O)NC1=C(O)N=C(N)N=C1O LKGKWHBHCMQTQV-UHFFFAOYSA-N 0.000 description 1
• BSYZDWWOBZSPTI-UHFFFAOYSA-N n-(2-phenylethyl)-2-[4-([1,3]thiazolo[5,4-d]pyrimidin-2-yl)piperazin-1-yl]acetamide Chemical compound C1CN(C=2SC3=NC=NC=C3N=2)CCN1CC(=O)NCCC1=CC=CC=C1 BSYZDWWOBZSPTI-UHFFFAOYSA-N 0.000 description 1
• JNRLWYFGYIOHLO-UHFFFAOYSA-N n-(3-chloro-4-fluorophenyl)-2-(4-fluorophenyl)-[1,3]oxazolo[5,4-d]pyrimidin-7-amine Chemical compound C1=CC(F)=CC=C1C(OC1=NC=N2)=NC1=C2NC1=CC=C(F)C(Cl)=C1 JNRLWYFGYIOHLO-UHFFFAOYSA-N 0.000 description 1
• BUPDLPLGFRDHSJ-UHFFFAOYSA-N n-(4-fluorophenyl)formamide Chemical compound FC1=CC=C(NC=O)C=C1 BUPDLPLGFRDHSJ-UHFFFAOYSA-N 0.000 description 1
• MQLRGWUBLRQSOU-QGZVFWFLSA-N n-[(3r)-1-(2-amino-6-phenylthieno[2,3-d]pyrimidin-4-yl)pyrrolidin-3-yl]-2-(4-chlorophenoxy)acetamide Chemical compound N([C@@H]1CCN(C1)C=1N=C(N=C2SC(=CC2=1)C=1C=CC=CC=1)N)C(=O)COC1=CC=C(Cl)C=C1 MQLRGWUBLRQSOU-QGZVFWFLSA-N 0.000 description 1
• UMZNPYAAVCVJAB-QGZVFWFLSA-N n-[(3r)-1-(2-amino-6-phenylthieno[2,3-d]pyrimidin-4-yl)pyrrolidin-3-yl]-4-chlorobenzamide Chemical compound N([C@@H]1CCN(C1)C=1N=C(N=C2SC(=CC2=1)C=1C=CC=CC=1)N)C(=O)C1=CC=C(Cl)C=C1 UMZNPYAAVCVJAB-QGZVFWFLSA-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
• 125000003136 n-heptyl 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])* 0.000 description 1
• 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 239000002088 nanocapsule Substances 0.000 description 1
• 239000002105 nanoparticle Substances 0.000 description 1
• PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
• 125000004626 naphthothienyl group Chemical group C1(=CSC2=C1C1=CC=CC=C1C=C2)* 0.000 description 1
• 125000001624 naphthyl group Chemical group 0.000 description 1
• 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
• 229920001206 natural gum Polymers 0.000 description 1
• 230000007694 nephrotoxicity Effects 0.000 description 1
• 231100000417 nephrotoxicity Toxicity 0.000 description 1
• 230000000926 neurological effect Effects 0.000 description 1
• 230000007135 neurotoxicity Effects 0.000 description 1
• 231100000228 neurotoxicity Toxicity 0.000 description 1
• 229960003966 nicotinamide Drugs 0.000 description 1
• 239000011570 nicotinamide Substances 0.000 description 1
• 150000002832 nitroso derivatives Chemical class 0.000 description 1
• 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
• 239000002777 nucleoside Substances 0.000 description 1
• 125000003835 nucleoside group Chemical group 0.000 description 1
• 125000005441 o-toluyl group Chemical group [H]C1=C([H])C(C(*)=O)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
• OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
• UYDLBVPAAFVANX-UHFFFAOYSA-N octylphenoxy polyethoxyethanol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(OCCOCCOCCOCCO)C=C1 UYDLBVPAAFVANX-UHFFFAOYSA-N 0.000 description 1
• 239000002674 ointment Substances 0.000 description 1
• ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
• 235000021313 oleic acid Nutrition 0.000 description 1
• 125000001117 oleyl 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])=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])[H] 0.000 description 1
• 231100000590 oncogenic Toxicity 0.000 description 1
• 230000002246 oncogenic effect Effects 0.000 description 1
• 238000010915 one-step procedure Methods 0.000 description 1
• 230000003287 optical effect Effects 0.000 description 1
• 150000007530 organic bases Chemical class 0.000 description 1
• 150000002894 organic compounds Chemical class 0.000 description 1
• 239000012860 organic pigment Substances 0.000 description 1
• 239000003960 organic solvent Substances 0.000 description 1
• 150000002905 orthoesters Chemical class 0.000 description 1
• 125000000160 oxazolidinyl group Chemical group 0.000 description 1
• 125000005968 oxazolinyl group Chemical group 0.000 description 1
• 125000002971 oxazolyl group Chemical group 0.000 description 1
• 125000003566 oxetanyl group Chemical group 0.000 description 1
• 238000007243 oxidative cyclization reaction Methods 0.000 description 1
• 230000001590 oxidative effect Effects 0.000 description 1
• 125000000466 oxiranyl group Chemical group 0.000 description 1
• TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
• 125000000352 p-cymenyl group Chemical group C1(=C(C=C(C=C1)C)*)C(C)C 0.000 description 1
• 125000005440 p-toluyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C(*)=O)C([H])([H])[H] 0.000 description 1
• 229940014662 pantothenate Drugs 0.000 description 1
• 235000019161 pantothenic acid Nutrition 0.000 description 1
• 239000011713 pantothenic acid Substances 0.000 description 1
• 239000002245 particle Substances 0.000 description 1
• 230000007170 pathology Effects 0.000 description 1
• 239000008188 pellet Substances 0.000 description 1
• 235000019371 penicillin G benzathine Nutrition 0.000 description 1
• 210000003899 penis Anatomy 0.000 description 1
• WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
• 229960001476 pentoxifylline Drugs 0.000 description 1
• 125000005327 perimidinyl group Chemical group N1C(=NC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
• 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
• 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
• 229960003742 phenol Drugs 0.000 description 1
• 125000005954 phenoxathiinyl group Chemical group 0.000 description 1
• 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
• 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
• 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
• 125000004344 phenylpropyl group Chemical group 0.000 description 1
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
• 150000008104 phosphatidylethanolamines Chemical class 0.000 description 1
• UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical group [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
• 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
• 150000003014 phosphoric acid esters Chemical class 0.000 description 1
• 229910052698 phosphorus Inorganic materials 0.000 description 1
• 239000011574 phosphorus Substances 0.000 description 1
• 239000003757 phosphotransferase inhibitor Substances 0.000 description 1
• 125000005633 phthalidyl group Chemical group 0.000 description 1
• 125000001388 picenyl group Chemical group C1(=CC=CC2=CC=C3C4=CC=C5C=CC=CC5=C4C=CC3=C21)* 0.000 description 1
• IVXQBCUBSIPQGU-UHFFFAOYSA-N piperazine-1-carboxamide Chemical compound NC(=O)N1CCNCC1 IVXQBCUBSIPQGU-UHFFFAOYSA-N 0.000 description 1
• 239000000902 placebo Substances 0.000 description 1
• 229940068196 placebo Drugs 0.000 description 1
• 239000003880 polar aprotic solvent Substances 0.000 description 1
• 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
• 229920000747 poly(lactic acid) Polymers 0.000 description 1
• 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
• 239000004584 polyacrylic acid Substances 0.000 description 1
• 229920000768 polyamine Chemical group 0.000 description 1
• 229920000728 polyester Polymers 0.000 description 1
• 229920000573 polyethylene Polymers 0.000 description 1
• 239000004626 polylactic acid Substances 0.000 description 1
• 239000002861 polymer material Substances 0.000 description 1
• 239000004926 polymethyl methacrylate Substances 0.000 description 1
• 208000005987 polymyositis Diseases 0.000 description 1
• 229920005862 polyol Chemical group 0.000 description 1
• 150000003077 polyols Chemical group 0.000 description 1
• 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
• 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
• 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
• 230000034190 positive regulation of NF-kappaB transcription factor activity Effects 0.000 description 1
• 239000011591 potassium Substances 0.000 description 1
• 229910052700 potassium Inorganic materials 0.000 description 1
• XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
• 108020001213 potassium channel Proteins 0.000 description 1
• 235000010241 potassium sorbate Nutrition 0.000 description 1
• 239000004302 potassium sorbate Substances 0.000 description 1
• 229940069338 potassium sorbate Drugs 0.000 description 1
• 230000003389 potentiating effect Effects 0.000 description 1
• 229960004618 prednisone Drugs 0.000 description 1
• XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
• 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 239000003755 preservative agent Substances 0.000 description 1
• MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
• 229960004919 procaine Drugs 0.000 description 1
• XYWJNTOURDMTPI-UHFFFAOYSA-N procodazole Chemical compound C1=CC=C2NC(CCC(=O)O)=NC2=C1 XYWJNTOURDMTPI-UHFFFAOYSA-N 0.000 description 1
• 229950000989 procodazole Drugs 0.000 description 1
• XEABSBMNTNXEJM-UHFFFAOYSA-N propagermanium Chemical compound OC(=O)CC[Ge](=O)O[Ge](=O)CCC(O)=O XEABSBMNTNXEJM-UHFFFAOYSA-N 0.000 description 1
• 229950002828 propagermanium Drugs 0.000 description 1
• ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
• 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
• 235000010388 propyl gallate Nutrition 0.000 description 1
• 239000000473 propyl gallate Substances 0.000 description 1
• 229940075579 propyl gallate Drugs 0.000 description 1
• 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
• 229950008679 protamine sulfate Drugs 0.000 description 1
• 239000011253 protective coating Substances 0.000 description 1
• 235000018102 proteins Nutrition 0.000 description 1
• 102000004169 proteins and genes Human genes 0.000 description 1
• 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
• 238000000746 purification Methods 0.000 description 1
• 239000002212 purine nucleoside Substances 0.000 description 1
• 125000003373 pyrazinyl group Chemical group 0.000 description 1
• 125000003226 pyrazolyl group Chemical group 0.000 description 1
• 125000001725 pyrenyl group Chemical group 0.000 description 1
• 125000002098 pyridazinyl group Chemical group 0.000 description 1
• CMMSUVYMWKBPQK-UHFFFAOYSA-N pyrido[3,2-d]pyrimidine-2,4-diamine Chemical class N1=CC=CC2=NC(N)=NC(N)=C21 CMMSUVYMWKBPQK-UHFFFAOYSA-N 0.000 description 1
• 125000004076 pyridyl group Chemical group 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
• 125000001422 pyrrolinyl group Chemical group 0.000 description 1
• 125000000168 pyrrolyl group Chemical group 0.000 description 1
• 238000011002 quantification Methods 0.000 description 1
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
• 125000005493 quinolyl group Chemical group 0.000 description 1
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
• 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
• 150000003254 radicals Chemical class 0.000 description 1
• 230000035484 reaction time Effects 0.000 description 1
• 102000005962 receptors Human genes 0.000 description 1
• 108020003175 receptors Proteins 0.000 description 1
• 238000006476 reductive cyclization reaction Methods 0.000 description 1
• 238000010992 reflux Methods 0.000 description 1
• 230000002441 reversible effect Effects 0.000 description 1
• 238000006798 ring closing metathesis reaction Methods 0.000 description 1
• 239000003419 rna directed dna polymerase inhibitor Substances 0.000 description 1
• XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 1
• 229960001860 salicylate Drugs 0.000 description 1
• 235000021003 saturated fats Nutrition 0.000 description 1
• 150000004671 saturated fatty acids Chemical class 0.000 description 1
• 235000003441 saturated fatty acids Nutrition 0.000 description 1
• HOZOZZFCZRXYEK-HNHWXVNLSA-M scopolamine butylbromide Chemical compound [Br-].C1([C@@H](CO)C(=O)OC2C[C@@H]3[N+]([C@H](C2)[C@@H]2[C@H]3O2)(C)CCCC)=CC=CC=C1 HOZOZZFCZRXYEK-HNHWXVNLSA-M 0.000 description 1
• 210000005212 secondary lymphoid organ Anatomy 0.000 description 1
• 230000001624 sedative effect Effects 0.000 description 1
• 229910052711 selenium Inorganic materials 0.000 description 1
• 239000011669 selenium Substances 0.000 description 1
• JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical group O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 1
• 239000003352 sequestering agent Substances 0.000 description 1
• 150000004760 silicates Chemical class 0.000 description 1
• 125000005624 silicic acid group Chemical class 0.000 description 1
• 210000003491 skin Anatomy 0.000 description 1
• WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
• 235000010234 sodium benzoate Nutrition 0.000 description 1
• 239000004299 sodium benzoate Substances 0.000 description 1
• 229960003885 sodium benzoate Drugs 0.000 description 1
• 239000011780 sodium chloride Substances 0.000 description 1
• HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
• JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
• 239000012312 sodium hydride Substances 0.000 description 1
• 229910000104 sodium hydride Inorganic materials 0.000 description 1
• 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
• 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
• 229940001584 sodium metabisulfite Drugs 0.000 description 1
• 235000010262 sodium metabisulphite Nutrition 0.000 description 1
• 235000010288 sodium nitrite Nutrition 0.000 description 1
• 159000000000 sodium salts Chemical class 0.000 description 1
• JJICLMJFIKGAAU-UHFFFAOYSA-M sodium;2-amino-9-(1,3-dihydroxypropan-2-yloxymethyl)purin-6-olate Chemical compound [Na+].NC1=NC([O-])=C2N=CN(COC(CO)CO)C2=N1 JJICLMJFIKGAAU-UHFFFAOYSA-M 0.000 description 1
• RMLUKZWYIKEASN-UHFFFAOYSA-M sodium;2-amino-9-(2-hydroxyethoxymethyl)purin-6-olate Chemical compound [Na+].O=C1[N-]C(N)=NC2=C1N=CN2COCCO RMLUKZWYIKEASN-UHFFFAOYSA-M 0.000 description 1
• WBQTXTBONIWRGK-UHFFFAOYSA-N sodium;propan-2-olate Chemical compound [Na+].CC(C)[O-] WBQTXTBONIWRGK-UHFFFAOYSA-N 0.000 description 1
• 235000019337 sorbitan trioleate Nutrition 0.000 description 1
• 229960000391 sorbitan trioleate Drugs 0.000 description 1
• 229940063673 spermidine Drugs 0.000 description 1
• 230000002269 spontaneous effect Effects 0.000 description 1
• 238000011272 standard treatment Methods 0.000 description 1
• 239000008117 stearic acid Substances 0.000 description 1
• 230000004936 stimulating effect Effects 0.000 description 1
• 230000000638 stimulation Effects 0.000 description 1
• 238000003860 storage Methods 0.000 description 1
• 125000005504 styryl group Chemical group 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
• 229960005137 succinic acid Drugs 0.000 description 1
• 229960002317 succinimide Drugs 0.000 description 1
• 239000005720 sucrose Substances 0.000 description 1
• 235000000346 sugar Nutrition 0.000 description 1
• 150000008163 sugars Chemical class 0.000 description 1
• 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
• BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
• 125000003375 sulfoxide group Chemical group 0.000 description 1
• YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
• 230000001629 suppression Effects 0.000 description 1
• 230000020382 suppression by virus of host antigen processing and presentation of peptide antigen via MHC class I Effects 0.000 description 1
• 239000000725 suspension Substances 0.000 description 1
• 230000002459 sustained effect Effects 0.000 description 1
• 208000011580 syndromic disease Diseases 0.000 description 1
• 229920001059 synthetic polymer Polymers 0.000 description 1
• 229940065721 systemic for obstructive airway disease xanthines Drugs 0.000 description 1
• 229940037128 systemic glucocorticoids Drugs 0.000 description 1
• 201000000596 systemic lupus erythematosus Diseases 0.000 description 1
• 239000003760 tallow Substances 0.000 description 1
• 231100000378 teratogenic Toxicity 0.000 description 1
• 230000003390 teratogenic effect Effects 0.000 description 1
• UTNUDOFZCWSZMS-YFHOEESVSA-N teriflunomide Chemical compound C\C(O)=C(/C#N)C(=O)NC1=CC=C(C(F)(F)F)C=C1 UTNUDOFZCWSZMS-YFHOEESVSA-N 0.000 description 1
• 150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
• 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
• 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 description 1
• 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
• 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
• 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
• CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
• OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
• 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
• 125000003831 tetrazolyl group Chemical group 0.000 description 1
• 229960000278 theophylline Drugs 0.000 description 1
• 229940124597 therapeutic agent Drugs 0.000 description 1
• 125000004525 thiadiazinyl group Chemical group S1NN=C(C=C1)* 0.000 description 1
• 125000001113 thiadiazolyl group Chemical group 0.000 description 1
• 125000006407 thiazinanyl group Chemical group 0.000 description 1
• 125000001984 thiazolidinyl group Chemical group 0.000 description 1
• 125000002769 thiazolinyl group Chemical group 0.000 description 1
• MQRQMKYOQVNZPZ-UHFFFAOYSA-N thieno[2,3-d]pyrimidine-2-carboxamide Chemical compound NC(=O)C1=NC=C2C=CSC2=N1 MQRQMKYOQVNZPZ-UHFFFAOYSA-N 0.000 description 1
• 125000004001 thioalkyl group Chemical class 0.000 description 1
• 125000004862 thiobutyl group Chemical group 0.000 description 1
• 125000005300 thiocarboxy group Chemical group C(=S)(O)* 0.000 description 1
• 125000000101 thioether group Chemical group 0.000 description 1
• 125000004014 thioethyl group Chemical group [H]SC([H])([H])C([H])([H])* 0.000 description 1
• 125000004035 thiopropyl group Chemical group [H]SC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000005503 thioxanyl group Chemical group 0.000 description 1
• PSWFFKRAVBDQEG-YGQNSOCVSA-N thymopentin Chemical compound NC(N)=NCCC[C@H](N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(O)=O)CC1=CC=C(O)C=C1 PSWFFKRAVBDQEG-YGQNSOCVSA-N 0.000 description 1
• 229960004517 thymopentin Drugs 0.000 description 1
• 206010043778 thyroiditis Diseases 0.000 description 1
• 229960003087 tioguanine Drugs 0.000 description 1
• KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
• 239000004408 titanium dioxide Substances 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
• 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
• 125000005425 toluyl group Chemical group 0.000 description 1
• 125000003944 tolyl group Chemical group 0.000 description 1
• 238000013518 transcription Methods 0.000 description 1
• 230000035897 transcription Effects 0.000 description 1
• 238000013271 transdermal drug delivery Methods 0.000 description 1
• 230000009466 transformation Effects 0.000 description 1
• 230000032258 transport Effects 0.000 description 1
• 238000011269 treatment regimen Methods 0.000 description 1
• 229960005294 triamcinolone Drugs 0.000 description 1
• GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 description 1
• 125000004306 triazinyl group Chemical group 0.000 description 1
• 150000003628 tricarboxylic acids Chemical class 0.000 description 1
• GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
• 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
• LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
• 230000004614 tumor growth Effects 0.000 description 1
• 230000007306 turnover Effects 0.000 description 1
• 229950009811 ubenimex Drugs 0.000 description 1
• 235000021081 unsaturated fats Nutrition 0.000 description 1
• 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
• 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
• 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
• 230000003827 upregulation Effects 0.000 description 1
• 150000003672 ureas Chemical class 0.000 description 1
• 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
• FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
• 235000012141 vanillin Nutrition 0.000 description 1
• 230000002792 vascular Effects 0.000 description 1
• 210000003462 vein Anatomy 0.000 description 1
• 230000035899 viability Effects 0.000 description 1
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
• 229920002554 vinyl polymer Polymers 0.000 description 1
• 230000009385 viral infection Effects 0.000 description 1
• 238000009736 wetting Methods 0.000 description 1
• 239000000080 wetting agent Substances 0.000 description 1
• 239000000230 xanthan gum Substances 0.000 description 1
• 229920001285 xanthan gum Polymers 0.000 description 1
• 235000010493 xanthan gum Nutrition 0.000 description 1
• 229940082509 xanthan gum Drugs 0.000 description 1
• 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
• 239000003064 xanthine oxidase inhibitor Substances 0.000 description 1
• 150000003752 zinc compounds Chemical class 0.000 description 1
• UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical class [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1