JP2012520269A5 - - Google Patents
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- Publication number
- JP2012520269A5 JP2012520269A5 JP2011553476A JP2011553476A JP2012520269A5 JP 2012520269 A5 JP2012520269 A5 JP 2012520269A5 JP 2011553476 A JP2011553476 A JP 2011553476A JP 2011553476 A JP2011553476 A JP 2011553476A JP 2012520269 A5 JP2012520269 A5 JP 2012520269A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- piperazin
- thiazolo
- fluorophenyl
- pyrimidin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- -1 N-protected amino Chemical group 0.000 claims 220
- 125000000217 alkyl group Chemical group 0.000 claims 68
- 125000003118 aryl group Chemical group 0.000 claims 46
- 125000003282 alkyl amino group Chemical group 0.000 claims 36
- 150000001408 amides Chemical class 0.000 claims 28
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 28
- 125000003545 alkoxy group Chemical group 0.000 claims 26
- 125000000623 heterocyclic group Chemical group 0.000 claims 26
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 24
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 22
- 125000001769 aryl amino group Chemical group 0.000 claims 22
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims 21
- 229910052736 halogen Inorganic materials 0.000 claims 21
- 150000008064 anhydrides Chemical class 0.000 claims 20
- 150000004820 halides Chemical class 0.000 claims 20
- 150000002367 halogens Chemical class 0.000 claims 20
- 150000007970 thio esters Chemical class 0.000 claims 19
- 125000005843 halogen group Chemical group 0.000 claims 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 17
- 150000001875 compounds Chemical class 0.000 claims 16
- 150000002148 esters Chemical class 0.000 claims 15
- 125000006323 alkenyl amino group Chemical group 0.000 claims 14
- 125000000304 alkynyl group Chemical group 0.000 claims 14
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 14
- 125000001424 substituent group Chemical group 0.000 claims 14
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 14
- 125000003342 alkenyl group Chemical group 0.000 claims 13
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims 13
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 13
- 125000005191 hydroxyalkylamino group Chemical group 0.000 claims 13
- 125000004414 alkyl thio group Chemical class 0.000 claims 12
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims 12
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims 12
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 12
- 125000004104 aryloxy group Chemical group 0.000 claims 11
- 125000005000 thioaryl group Chemical group 0.000 claims 11
- 125000002252 acyl group Chemical group 0.000 claims 10
- 125000004442 acylamino group Chemical group 0.000 claims 10
- 125000000033 alkoxyamino group Chemical group 0.000 claims 10
- 125000006319 alkynyl amino group Chemical group 0.000 claims 10
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 10
- 125000001072 heteroaryl group Chemical group 0.000 claims 10
- 125000004193 piperazinyl group Chemical group 0.000 claims 10
- 125000005276 alkyl hydrazino group Chemical class 0.000 claims 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims 9
- HJMZMZRCABDKKV-UHFFFAOYSA-N carbonocyanidic acid Chemical compound OC(=O)C#N HJMZMZRCABDKKV-UHFFFAOYSA-N 0.000 claims 9
- 150000003566 thiocarboxylic acids Chemical class 0.000 claims 9
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 8
- 125000003441 thioacyl group Chemical group 0.000 claims 8
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 7
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims 7
- 125000000717 hydrazino group Chemical class [H]N([*])N([H])[H] 0.000 claims 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 6
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 6
- 125000006852 aliphatic spacer Chemical group 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 6
- 150000001733 carboxylic acid esters Chemical class 0.000 claims 6
- 229940124530 sulfonamide Drugs 0.000 claims 6
- 150000003555 thioacetals Chemical class 0.000 claims 6
- PSXDJVGHVKVWDZ-UHFFFAOYSA-N (carbamothioylsulfamoylamino)urea Chemical class NC(=O)NNS(=O)(=O)NC(N)=S PSXDJVGHVKVWDZ-UHFFFAOYSA-N 0.000 claims 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 5
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 5
- 125000004947 alkyl aryl amino group Chemical group 0.000 claims 5
- 125000005018 aryl alkenyl group Chemical group 0.000 claims 5
- 125000004429 atom Chemical group 0.000 claims 5
- 125000000524 functional group Chemical group 0.000 claims 5
- AWIJRPNMLHPLNC-UHFFFAOYSA-N methanethioic s-acid Chemical compound SC=O AWIJRPNMLHPLNC-UHFFFAOYSA-N 0.000 claims 5
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- FVLAYJRLBLHIPV-UHFFFAOYSA-N pyrimidin-5-amine Chemical compound NC1=CN=CN=C1 FVLAYJRLBLHIPV-UHFFFAOYSA-N 0.000 claims 5
- 229920006395 saturated elastomer Polymers 0.000 claims 5
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 5
- 150000003456 sulfonamides Chemical class 0.000 claims 5
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical group N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 4
- 150000001413 amino acids Chemical class 0.000 claims 4
- 150000007942 carboxylates Chemical class 0.000 claims 4
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims 4
- 125000004986 diarylamino group Chemical group 0.000 claims 4
- 125000002757 morpholinyl group Chemical group 0.000 claims 4
- 125000003386 piperidinyl group Chemical group 0.000 claims 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 4
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims 4
- 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 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 3
- 241001024304 Mino Species 0.000 claims 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 3
- 125000004423 acyloxy group Chemical group 0.000 claims 3
- 125000001931 aliphatic group Chemical group 0.000 claims 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 125000005026 carboxyaryl group Chemical group 0.000 claims 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 3
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 208000026278 immune system disease Diseases 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 150000003568 thioethers Chemical class 0.000 claims 3
- UAJFCVURUYZZSL-UHFFFAOYSA-N (carbamoylamino)carbamothioylcarbamic acid Chemical compound N(C(=O)N)NC(NC(=O)O)=S UAJFCVURUYZZSL-UHFFFAOYSA-N 0.000 claims 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 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 2
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 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 2
- CDGFEINVQHEUQV-UHFFFAOYSA-N [1,3]thiazolo[5,4-d]pyrimidine Chemical compound N1=CN=C2SC=NC2=C1 CDGFEINVQHEUQV-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims 2
- 125000005277 alkyl imino group Chemical class 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 150000003556 thioamides Chemical class 0.000 claims 2
- 125000003944 tolyl group Chemical group 0.000 claims 2
- NDYMQOUYJJXCKJ-UHFFFAOYSA-N (4-fluorophenyl)-morpholin-4-ylmethanone Chemical compound C1=CC(F)=CC=C1C(=O)N1CCOCC1 NDYMQOUYJJXCKJ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims 1
- 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 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 claims 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 claims 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 claims 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 claims 1
- NCOVWHUVJSCTNR-UHFFFAOYSA-N 1-[4-(2-amino-6-phenylthieno[2,3-d]pyrimidin-4-yl)piperazin-1-yl]-2-(4-methoxyphenoxy)ethanone Chemical compound C1=CC(OC)=CC=C1OCC(=O)N1CCN(C=2C=3C=C(SC=3N=C(N)N=2)C=2C=CC=CC=2)CC1 NCOVWHUVJSCTNR-UHFFFAOYSA-N 0.000 claims 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 claims 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 claims 1
- ZXDSFURVENMPMT-UHFFFAOYSA-N 1-[4-(2-amino-8-methylsulfanyl-7h-purin-6-yl)piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound N1=C(N)N=C2NC(SC)=NC2=C1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 ZXDSFURVENMPMT-UHFFFAOYSA-N 0.000 claims 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 claims 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 claims 1
- ABKYBCYESRQSQH-UHFFFAOYSA-N 1-[4-(2-amino-8-sulfanylidene-7,9-dihydropurin-6-yl)piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=12NC(=S)NC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 ABKYBCYESRQSQH-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- KDSZIYBABLTQOY-UHFFFAOYSA-N 1-[4-(2-aminothieno[2,3-d]pyrimidin-4-yl)piperazin-1-yl]-2-(4-chlorophenoxy)ethanone Chemical compound C=12C=CSC2=NC(N)=NC=1N(CC1)CCN1C(=O)COC1=CC=C(Cl)C=C1 KDSZIYBABLTQOY-UHFFFAOYSA-N 0.000 claims 1
- 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 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 claims 1
- 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 1
- 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 claims 1
- 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 1
- 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 1
- 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
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- IFXBZCOVKOVHIM-UHFFFAOYSA-N 1-[4-[2-amino-6-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]piperazin-1-yl]-3-phenylpropan-1-one Chemical compound C=12C=C(C=3C=CC(F)=CC=3)SC2=NC(N)=NC=1N(CC1)CCN1C(=O)CCC1=CC=CC=C1 IFXBZCOVKOVHIM-UHFFFAOYSA-N 0.000 claims 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 claims 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 claims 1
- 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 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 claims 1
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- 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 claims 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 claims 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 claims 1
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- 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 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 claims 1
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- 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
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- 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 1
- 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 1
- 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 1
- 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 claims 1
- 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 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 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
- 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 1
- 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 1
- 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 1
- 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 1
- 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 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 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 claims 1
- 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 claims 1
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- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 235000021003 saturated fats Nutrition 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
- RNYWAUFNEDZFSY-CQSZACIVSA-N tert-butyl n-[(3r)-1-[2-amino-6-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]pyrrolidin-3-yl]carbamate Chemical compound C1[C@H](NC(=O)OC(C)(C)C)CCN1C1=NC(N)=NC2=C1C=C(C=1C=CC(F)=CC=1)S2 RNYWAUFNEDZFSY-CQSZACIVSA-N 0.000 claims 1
- 125000004001 thioalkyl group Chemical class 0.000 claims 1
- 238000002054 transplantation Methods 0.000 claims 1
- 235000021081 unsaturated fats Nutrition 0.000 claims 1
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| GB0904353.0 | 2009-03-13 | ||
| GB0904373A GB0904373D0 (en) | 2009-03-13 | 2009-03-13 | Novel thienopyrimidines |
| GB0911022A GB0911022D0 (en) | 2009-06-26 | 2009-06-26 | Novel purines |
| GB0911022.2 | 2009-06-26 | ||
| PCT/EP2010/053318 WO2010103130A2 (en) | 2009-03-13 | 2010-03-15 | Novel bicyclic heterocycles |
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| ES (2) | ES2665277T3 (https=) |
| WO (1) | WO2010103130A2 (https=) |
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| DK2035369T3 (da) | 2006-07-05 | 2014-10-06 | Fibrotech Therapeutics Pty Ltd | Terapeutiske |
| ES2665277T3 (es) * | 2009-03-13 | 2018-04-25 | Katholieke Universiteit Leuven K.U. Leuven R&D | Análogos de purina y su uso como agentes inmunosupresores |
| EP2491030B1 (en) | 2009-10-22 | 2015-07-15 | Fibrotech Therapeutics PTY LTD | Fused ring analogues of anti-fibrotic agents |
| GB201012889D0 (en) | 2010-08-02 | 2010-09-15 | Univ Leuven Kath | Antiviral activity of novel bicyclic heterocycles |
| GB201015411D0 (en) * | 2010-09-15 | 2010-10-27 | Univ Leuven Kath | Anti-cancer activity of novel bicyclic heterocycles |
| GB201114212D0 (en) | 2011-08-18 | 2011-10-05 | Ucb Pharma Sa | Therapeutic agents |
| GB201115665D0 (en) | 2011-09-09 | 2011-10-26 | Univ Leuven Kath | Autoimmune and inflammatory disorder therapy |
| US20130102601A1 (en) | 2011-10-21 | 2013-04-25 | F. Hoffmann-La Roche Ltd | Pyrimidin-4-one derivatives and their use in the treatment, amelioration or prevention of a viral disease |
| GB201119401D0 (en) | 2011-11-10 | 2011-12-21 | Ucb Pharma Sa | Therapeutic agents |
| GB201217704D0 (en) | 2012-10-03 | 2012-11-14 | Ucb Pharma Sa | Therapeutic agents |
| SG11201504291SA (en) * | 2012-12-20 | 2015-07-30 | Ucb Biopharma Sprl | Therapeutically active pyrazolo-pyrimidine derivatives |
| CN103044460B (zh) * | 2013-01-30 | 2015-02-25 | 石家庄学院 | 3,5,7-三苯基-5H-噻唑并[3,2-a]嘧啶类衍生物及应用 |
| MA38455B1 (fr) * | 2013-04-05 | 2018-05-31 | Polichem Sa | Utilisation de pidotimodes pour traiter la maladie inflammatoire de l'intestin |
| BR112016006319A2 (pt) | 2013-09-27 | 2017-08-01 | Nimbus Iris Inc | inibidores de irak e usos dos mesmos |
| TWI648281B (zh) | 2013-10-17 | 2019-01-21 | 日商安斯泰來製藥股份有限公司 | 含硫二環式化合物 |
| CN104892589A (zh) * | 2014-03-07 | 2015-09-09 | 中国科学院上海药物研究所 | 一类杂环化合物、其制备方法和用途 |
| GB201410817D0 (en) | 2014-06-17 | 2014-07-30 | Ucb Biopharma Sprl And Katholieke Universiteit Leuven K U Leuven R & D | Therapeutic agents |
| US9822127B2 (en) * | 2014-07-23 | 2017-11-21 | The Board Of Trustees Of The Leland Stanford Junior University | GAK modulators as antivirals |
| UY36390A (es) | 2014-11-05 | 2016-06-01 | Flexus Biosciences Inc | Compuestos moduladores de la enzima indolamina 2,3-dioxigenasa (ido), sus métodos de síntesis y composiciones farmacéuticas que los contienen |
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| GB201517263D0 (en) | 2015-09-30 | 2015-11-11 | Ucb Biopharma Sprl And Katholieke Universiteit Leuven | Therapeutic agents |
| GB201521767D0 (en) | 2015-12-10 | 2016-01-27 | Ucb Biopharma Sprl And Katholieke Universiteit Leuven K U Leuven R&D | Therapeutic agents |
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| SG11202012616RA (en) | 2018-08-21 | 2021-02-25 | Kyorin Pharmaceutical Co Ltd | Bicyclic heteroaromatic ring derivative |
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-
2010
- 2010-03-15 ES ES15162142.2T patent/ES2665277T3/es active Active
- 2010-03-15 CA CA2754890A patent/CA2754890C/en not_active Expired - Fee Related
- 2010-03-15 WO PCT/EP2010/053318 patent/WO2010103130A2/en not_active Ceased
- 2010-03-15 US US13/255,429 patent/US8901132B2/en not_active Expired - Fee Related
- 2010-03-15 JP JP2011553476A patent/JP5647998B2/ja not_active Expired - Fee Related
- 2010-03-15 EP EP20100711871 patent/EP2405973B1/en active Active
- 2010-03-15 CA CA2987743A patent/CA2987743A1/en not_active Abandoned
- 2010-03-15 ES ES10711871.3T patent/ES2543216T3/es active Active
- 2010-03-15 EP EP15162142.2A patent/EP2923734B1/en not_active Not-in-force
-
2014
- 2014-10-20 US US14/518,480 patent/US9221822B2/en not_active Expired - Fee Related
- 2014-11-10 JP JP2014228403A patent/JP6021880B2/ja not_active Expired - Fee Related
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