ES2665277T3 - Análogos de purina y su uso como agentes inmunosupresores - Google Patents

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Publication number

ES2665277T3

ES2665277T3 ES15162142.2T ES15162142T ES2665277T3 ES 2665277 T3 ES2665277 T3 ES 2665277T3 ES 15162142 T ES15162142 T ES 15162142T ES 2665277 T3 ES2665277 T3 ES 2665277T3

Authority

ES

Spain

Prior art keywords

amino

piperazin

alkyl

substituted

purin

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.)

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• 125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 title description 67
• 239000003018 immunosuppressive agent Substances 0.000 title description 15
• 229940125721 immunosuppressive agent Drugs 0.000 title description 5
• 229940045686 antimetabolites antineoplastic purine analogs Drugs 0.000 title description 3
• -1 nitro, amino Chemical group 0.000 claims abstract description 377
• 150000001875 compounds Chemical class 0.000 claims abstract description 132
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 83
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 77
• 125000003118 aryl group Chemical group 0.000 claims abstract description 53
• 150000003254 radicals Chemical class 0.000 claims abstract description 49
• 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 45
• 125000002252 acyl group Chemical group 0.000 claims abstract description 28
• 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 28
• 125000001769 aryl amino group Chemical group 0.000 claims abstract description 27
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 27
• 150000002367 halogens Chemical class 0.000 claims abstract description 27
• 125000001424 substituent group Chemical group 0.000 claims abstract description 27
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 26
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 24
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 24
• 125000003396 thiol group Chemical group [H]S* 0.000 claims abstract description 24
• 150000002148 esters Chemical class 0.000 claims abstract description 22
• 125000006310 cycloalkyl amino group Chemical group 0.000 claims abstract description 21
• 150000003839 salts Chemical class 0.000 claims abstract description 21
• 150000001408 amides Chemical class 0.000 claims abstract description 20
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims abstract description 19
• 125000004429 atom Chemical group 0.000 claims abstract description 17
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 17
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 16
• 125000006323 alkenyl amino group Chemical group 0.000 claims abstract description 15
• 125000000304 alkynyl group Chemical group 0.000 claims abstract description 15
• 125000000000 cycloalkoxy group Chemical group 0.000 claims abstract description 15
• AWIJRPNMLHPLNC-UHFFFAOYSA-N methanethioic s-acid Chemical compound SC=O AWIJRPNMLHPLNC-UHFFFAOYSA-N 0.000 claims abstract description 15
• 125000005276 alkyl hydrazino group Chemical group 0.000 claims abstract description 14
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 14
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 14
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 14
• 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims abstract description 14
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 14
• 125000005191 hydroxyalkylamino group Chemical group 0.000 claims abstract description 14
• KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical group N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims abstract description 12
• 125000001931 aliphatic group Chemical group 0.000 claims abstract description 12
• 125000001691 aryl alkyl amino group Chemical group 0.000 claims abstract description 12
• 125000004104 aryloxy group Chemical group 0.000 claims abstract description 12
• 230000006870 function Effects 0.000 claims abstract description 12
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
• 239000001257 hydrogen Substances 0.000 claims abstract description 12
• 229920006395 saturated elastomer Polymers 0.000 claims abstract description 12
• 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims abstract description 12
• 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 11
• 150000001413 amino acids Chemical class 0.000 claims abstract description 11
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 11
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 11
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 11
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 11
• 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 10
• 125000004659 aryl alkyl thio group Chemical group 0.000 claims abstract description 10
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims abstract description 10
• 125000005160 aryl oxy alkyl group Chemical group 0.000 claims abstract description 10
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 10
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 10
• 150000007970 thio esters Chemical class 0.000 claims abstract description 10
• 125000003441 thioacyl group Chemical group 0.000 claims abstract description 10
• 125000003368 amide group Chemical group 0.000 claims abstract description 9
• 150000007942 carboxylates Chemical group 0.000 claims abstract description 9
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 9
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 8
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
• 229910052717 sulfur Chemical group 0.000 claims abstract description 8
• 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims abstract description 8
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 7
• DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims abstract description 7
• 125000005018 aryl alkenyl group Chemical group 0.000 claims abstract description 7
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 7
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 7
• 125000005646 oximino group Chemical group 0.000 claims abstract description 7
• 239000001301 oxygen Chemical group 0.000 claims abstract description 7
• 239000011593 sulfur Chemical group 0.000 claims abstract description 7
• 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims abstract description 6
• 150000005840 aryl radicals Chemical class 0.000 claims abstract description 6
• 125000001841 imino group Chemical group [H]N=* 0.000 claims abstract description 6
• 239000012453 solvate Substances 0.000 claims abstract description 6
• 150000003555 thioacetals Chemical class 0.000 claims abstract description 6
• 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims abstract description 5
• 125000000033 alkoxyamino group Chemical group 0.000 claims abstract description 5
• 150000008064 anhydrides Chemical class 0.000 claims abstract description 5
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 5
• 150000001733 carboxylic acid esters Chemical class 0.000 claims abstract description 5
• 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims abstract description 5
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims abstract description 5
• 125000004442 acylamino group Chemical group 0.000 claims abstract description 4
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 4
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 3
• 125000005257 alkyl acyl group Chemical group 0.000 claims abstract description 3
• 125000005115 alkyl carbamoyl group Chemical group 0.000 claims abstract description 3
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 3
• 125000003435 aroyl group Chemical group 0.000 claims abstract description 3
• 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 claims abstract description 3
• 150000003556 thioamides Chemical class 0.000 claims abstract description 3
• 150000003566 thiocarboxylic acids Chemical class 0.000 claims abstract description 3
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract 2
• 239000003814 drug Substances 0.000 claims description 39
• 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 35
• 239000008194 pharmaceutical composition Substances 0.000 claims description 29
• 210000000056 organ Anatomy 0.000 claims description 28
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 23
• 229940079593 drug Drugs 0.000 claims description 21
• 208000026278 immune system disease Diseases 0.000 claims description 19
• 230000001506 immunosuppresive effect Effects 0.000 claims description 19
• 208000023275 Autoimmune disease Diseases 0.000 claims description 17
• 241000124008 Mammalia Species 0.000 claims description 17
• 241000282414 Homo sapiens Species 0.000 claims description 12
• 230000002265 prevention Effects 0.000 claims description 12
• 229940124589 immunosuppressive drug Drugs 0.000 claims description 11
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 9
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
• 229940124622 immune-modulator drug Drugs 0.000 claims description 6
• 125000005843 halogen group Chemical group 0.000 claims description 5
• 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 claims description 4
• 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 claims description 4
• 125000003277 amino group Chemical group 0.000 claims description 4
• 239000002246 antineoplastic agent Substances 0.000 claims description 4
• 229940041181 antineoplastic drug Drugs 0.000 claims description 4
• 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 claims description 3
• 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 claims description 3
• URNVXIZJMDWEHN-UHFFFAOYSA-N 1-[4-(2-amino-8-tert-butyl-7h-purin-6-yl)piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound N1=C(N)N=C2NC(C(C)(C)C)=NC2=C1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 URNVXIZJMDWEHN-UHFFFAOYSA-N 0.000 claims description 3
• 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 claims description 3
• 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 claims description 3
• 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 claims description 3
• 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 claims description 3
• 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 claims description 3
• 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 claims description 3
• ZNZJDQVICNNAMH-UHFFFAOYSA-N 2-[4-[2-amino-8-(4-fluorophenyl)-7h-purin-6-yl]piperazin-1-yl]-1-pyrrolidin-1-ylethanone Chemical compound C=12N=C(C=3C=CC(F)=CC=3)NC2=NC(N)=NC=1N(CC1)CCN1CC(=O)N1CCCC1 ZNZJDQVICNNAMH-UHFFFAOYSA-N 0.000 claims description 3
• 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 claims description 3
• 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 claims description 3
• KPQKKQDXKWGXKY-UHFFFAOYSA-N [4-[2-amino-8-(4-fluorophenyl)-7h-purin-6-yl]piperazin-1-yl]-(3-methoxyphenyl)methanone Chemical compound COC1=CC=CC(C(=O)N2CCN(CC2)C=2C=3N=C(NC=3N=C(N)N=2)C=2C=CC(F)=CC=2)=C1 KPQKKQDXKWGXKY-UHFFFAOYSA-N 0.000 claims description 3
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 3
• 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 claims 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 claims description 2
• DNZVKNGGVATVPL-UHFFFAOYSA-N 1-[4-[2-amino-8-(4-fluorophenyl)-7h-purin-6-yl]-1,4-diazepan-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=12N=C(C=3C=CC(F)=CC=3)NC2=NC(N)=NC=1N(CC1)CCCN1C(=O)COC1=CC=C(Cl)C=C1 DNZVKNGGVATVPL-UHFFFAOYSA-N 0.000 claims description 2
• 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 claims 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 claims description 2
• 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 claims description 2
• 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 claims description 2
• 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 claims description 2
• 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 claims description 2
• 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 claims description 2
• 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 claims description 2
• 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 claims description 2
• 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 claims description 2
• 125000005116 aryl carbamoyl group Chemical group 0.000 claims description 2
• 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 2
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
• 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 claims 1
• YSEHAQZPUFGSCA-UHFFFAOYSA-N 1-[4-[2-amino-8-(4-fluorophenyl)-7h-purin-6-yl]piperazin-1-yl]-2-thiophen-2-ylethanone Chemical compound C=12N=C(C=3C=CC(F)=CC=3)NC2=NC(N)=NC=1N(CC1)CCN1C(=O)CC1=CC=CS1 YSEHAQZPUFGSCA-UHFFFAOYSA-N 0.000 claims 1
• 125000005907 alkyl ester group Chemical group 0.000 claims 1
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 4
• 125000005251 aryl acyl group Chemical group 0.000 abstract description 3
• 125000001188 haloalkyl group Chemical group 0.000 abstract description 2
• 125000006319 alkynyl amino group Chemical group 0.000 abstract 3
• 125000006852 aliphatic spacer Chemical group 0.000 abstract 2
• 125000000547 substituted alkyl group Chemical group 0.000 abstract 2
• HJMZMZRCABDKKV-UHFFFAOYSA-N carbonocyanidic acid Chemical compound OC(=O)C#N HJMZMZRCABDKKV-UHFFFAOYSA-N 0.000 abstract 1
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
• 230000015572 biosynthetic process Effects 0.000 description 39
• 238000003786 synthesis reaction Methods 0.000 description 35
• 239000000203 mixture Substances 0.000 description 32
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
• 210000004027 cell Anatomy 0.000 description 30
• 238000006243 chemical reaction Methods 0.000 description 28
• 229940083251 peripheral vasodilators purine derivative Drugs 0.000 description 27
• 238000000034 method Methods 0.000 description 24
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
• 210000001744 T-lymphocyte Anatomy 0.000 description 22
• 238000002360 preparation method Methods 0.000 description 22
• 230000000694 effects Effects 0.000 description 19
• 229910001868 water Inorganic materials 0.000 description 19
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
• 230000004913 activation Effects 0.000 description 17
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 16
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 15
• 239000002253 acid Substances 0.000 description 15
• 241001465754 Metazoa Species 0.000 description 14
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