CZ20022929A3 - 5-Alkylpyrido[2,3-d]pyrimidinové inhibitory tyrosinových kinas - Google Patents

5-Alkylpyrido[2,3-d]pyrimidinové inhibitory tyrosinových kinas Download PDF

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Publication number: CZ20022929A3
Authority: CZ; Czechia
Prior art keywords: compound; methyl; pyrido; pyrimidin; cyclopentyl
Prior art date: 2000-03-06

Application number

CZ20022929A

Other languages

Czech (cs)

English (en)

Inventor

Richard John Booth

Ellen Myra Dobrusin

Peter Laurence Toogood

Scott Norman Vanderwel

Original Assignee

Warner-Lambert Company

Priority date (The priority date 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 date listed.)

2000-03-06

Filing date

2001-01-29

Publication date

2003-02-12

2001-01-29 Application filed by Warner-Lambert Company filed Critical Warner-Lambert Company

2003-02-12 Publication of CZ20022929A3 publication Critical patent/CZ20022929A3/cs

Links

102000004022 Protein-Tyrosine Kinases Human genes 0.000 title claims description 5
108090000412 Protein-Tyrosine Kinases Proteins 0.000 title claims description 5
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title claims description 5
239000003112 inhibitor Substances 0.000 title description 7
150000001875 compounds Chemical class 0.000 claims description 422
-1 (CH2) nAr Chemical group 0.000 claims description 246
125000000217 alkyl group Chemical group 0.000 claims description 97
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 61
229910052757 nitrogen Inorganic materials 0.000 claims description 54
229910052736 halogen Inorganic materials 0.000 claims description 50
125000003545 alkoxy group Chemical group 0.000 claims description 49
125000002837 carbocyclic group Chemical group 0.000 claims description 44
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 43
229910052760 oxygen Inorganic materials 0.000 claims description 42
229910052717 sulfur Inorganic materials 0.000 claims description 42
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 39
125000003118 aryl group Chemical group 0.000 claims description 37
239000001301 oxygen Substances 0.000 claims description 37
239000011593 sulfur Substances 0.000 claims description 35
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 34
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 34
229910052739 hydrogen Inorganic materials 0.000 claims description 34
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 34
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 34
239000001257 hydrogen Substances 0.000 claims description 33
150000002367 halogens Chemical class 0.000 claims description 30
125000005842 heteroatom Chemical group 0.000 claims description 29
125000005843 halogen group Chemical group 0.000 claims description 28
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 26
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 25
125000004663 dialkyl amino group Chemical group 0.000 claims description 25
125000001072 heteroaryl group Chemical group 0.000 claims description 22
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 20
238000000034 method Methods 0.000 claims description 19
125000004433 nitrogen atom Chemical group N* 0.000 claims description 19
150000003839 salts Chemical class 0.000 claims description 19
206010028980 Neoplasm Diseases 0.000 claims description 18
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 18
125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 17
125000004103 aminoalkyl group Chemical group 0.000 claims description 17
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 17
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 16
150000002825 nitriles Chemical class 0.000 claims description 16
125000003342 alkenyl group Chemical group 0.000 claims description 15
125000000304 alkynyl group Chemical group 0.000 claims description 15
150000001408 amides Chemical class 0.000 claims description 15
201000011510 cancer Diseases 0.000 claims description 15
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 15
LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 claims description 14
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
150000002148 esters Chemical class 0.000 claims description 13
WDHAAJIGSXNPFO-UHFFFAOYSA-N 8h-pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=CN=C2NC(=O)C=CC2=C1 WDHAAJIGSXNPFO-UHFFFAOYSA-N 0.000 claims description 12
201000010099 disease Diseases 0.000 claims description 12
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 11
125000001188 haloalkyl group Chemical group 0.000 claims description 11
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
229910052721 tungsten Inorganic materials 0.000 claims description 11
229960001171 acetohydroxamic acid Drugs 0.000 claims description 10
239000000651 prodrug Substances 0.000 claims description 10
229940002612 prodrug Drugs 0.000 claims description 10
102000003903 Cyclin-dependent kinases Human genes 0.000 claims description 9
108090000266 Cyclin-dependent kinases Proteins 0.000 claims description 9
125000003277 amino group Chemical group 0.000 claims description 9
125000000753 cycloalkyl group Chemical group 0.000 claims description 9
FQTDEBGLGLWEQA-UHFFFAOYSA-N 2-(9h-carbazol-3-ylamino)-8-cyclopentyl-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=C4C5=CC=CC=C5NC4=CC=3)=NC=C2C(C)=CC(=O)N1C1CCCC1 FQTDEBGLGLWEQA-UHFFFAOYSA-N 0.000 claims description 8
RMNWLVFFWRBNQK-UHFFFAOYSA-N 8-cyclopentyl-5-methyl-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCCCC3)=NC=C2C(C)=CC(=O)N1C1CCCC1 RMNWLVFFWRBNQK-UHFFFAOYSA-N 0.000 claims description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 8
125000003710 aryl alkyl group Chemical group 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
230000002062 proliferating effect Effects 0.000 claims description 8
VEMYILRVAQWCCT-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-8-cyclopentyl-6-fluoro-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(C)=C(F)C(=O)N2C3CCCC3)C2=N1 VEMYILRVAQWCCT-UHFFFAOYSA-N 0.000 claims description 7
DIDKOYSHJAGQQS-UHFFFAOYSA-N 8-cyclohexyl-5-methyl-2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCNCC3)=NC=C2C(C)=CC(=O)N1C1CCCCC1 DIDKOYSHJAGQQS-UHFFFAOYSA-N 0.000 claims description 7
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
230000004663 cell proliferation Effects 0.000 claims description 7
239000012634 fragment Substances 0.000 claims description 7
230000002401 inhibitory effect Effects 0.000 claims description 7
KSGVUGHSMXGDIY-UHFFFAOYSA-N 2-(2-acetyl-1-benzofuran-5-yl)-4-amino-8-cyclopentyl-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound CC(=O)c1cc2cc(ccc2o1)-c1nc(N)c2c(C)cc(=O)n(C3CCCC3)c2n1 KSGVUGHSMXGDIY-UHFFFAOYSA-N 0.000 claims description 6
ATLXXIXQFJFKSW-UHFFFAOYSA-N 2-amino-8h-pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(=O)NC2=NC(N)=NC=C21 ATLXXIXQFJFKSW-UHFFFAOYSA-N 0.000 claims description 6
SGOQBRBDGUKJRR-UHFFFAOYSA-N 4-amino-2-(1-benzofuran-5-yl)-8-cyclopentyl-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(C=3C=C4C=COC4=CC=3)=NC(N)=C2C(C)=CC(=O)N1C1CCCC1 SGOQBRBDGUKJRR-UHFFFAOYSA-N 0.000 claims description 6
VYQVLIJXHSKRIZ-UHFFFAOYSA-N 4-amino-8-cyclopentyl-2-(2,3-dimethyl-1H-indol-5-yl)-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound Cc1[nH]c2ccc(cc2c1C)-c1nc(N)c2c(C)cc(=O)n(C3CCCC3)c2n1 VYQVLIJXHSKRIZ-UHFFFAOYSA-N 0.000 claims description 6
125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 6
TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 claims description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
108091000080 Phosphotransferase Proteins 0.000 claims description 6
RRUDCFGSUDOHDG-UHFFFAOYSA-N acetohydroxamic acid Chemical compound CC(O)=NO RRUDCFGSUDOHDG-UHFFFAOYSA-N 0.000 claims description 6
150000001299 aldehydes Chemical class 0.000 claims description 6
150000001450 anions Chemical class 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 6
229910002091 carbon monoxide Inorganic materials 0.000 claims description 6
125000004181 carboxyalkyl group Chemical group 0.000 claims description 6
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 6
125000002560 nitrile group Chemical group 0.000 claims description 6
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
102000020233 phosphotransferase Human genes 0.000 claims description 6
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 6
208000037803 restenosis Diseases 0.000 claims description 6
AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 claims description 5
OQSUTVNZWPPSCU-UHFFFAOYSA-N 8-cyclopentyl-2-(4-piperazin-1-ylanilino)-5-propylpyrido[2,3-d]pyrimidin-7-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=NC(NC=3C=CC(=CC=3)N3CCNCC3)=NC=C2C(CCC)=CC(=O)N1C1CCCC1 OQSUTVNZWPPSCU-UHFFFAOYSA-N 0.000 claims description 5
LDWPCANEKZCUQT-UHFFFAOYSA-N 8-cyclopentyl-2-[4-(1,4-diazepan-1-yl)anilino]-5-methylpyrido[2,3-d]pyrimidin-7-one;hydrochloride Chemical compound Cl.C12=NC(NC=3C=CC(=CC=3)N3CCNCCC3)=NC=C2C(C)=CC(=O)N1C1CCCC1 LDWPCANEKZCUQT-UHFFFAOYSA-N 0.000 claims description 5
201000001320 Atherosclerosis Diseases 0.000 claims description 5
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
229940125904 compound 1 Drugs 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 5
239000003102 growth factor Substances 0.000 claims description 5
125000004446 heteroarylalkyl group Chemical group 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 5
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 5
125000005936 piperidyl group Chemical group 0.000 claims description 5
230000035755 proliferation Effects 0.000 claims description 5
210000004509 vascular smooth muscle cell Anatomy 0.000 claims description 5
GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 claims description 4
QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 claims description 4
YFYMPZSVMCVYOO-UHFFFAOYSA-N 2-(1-benzothiophen-5-ylamino)-8-cyclopentyl-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=C4C=CSC4=CC=3)=NC=C2C(C)=CC(=O)N1C1CCCC1 YFYMPZSVMCVYOO-UHFFFAOYSA-N 0.000 claims description 4
QCNGGERJGDWDQD-UHFFFAOYSA-N 2-(3-chloro-4-morpholin-4-ylanilino)-8-cyclopentyl-6-fluoro-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=C(Cl)C(N4CCOCC4)=CC=3)=NC=C2C(C)=C(F)C(=O)N1C1CCCC1 QCNGGERJGDWDQD-UHFFFAOYSA-N 0.000 claims description 4
KMNIJKOGOHNBGK-UHFFFAOYSA-N 2-[4-(3-aminopyrrolidin-1-yl)-3-fluoroanilino]-6-bromo-8-cyclopentyl-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=C(F)C(N4CC(N)CC4)=CC=3)=NC=C2C(C)=C(Br)C(=O)N1C1CCCC1 KMNIJKOGOHNBGK-UHFFFAOYSA-N 0.000 claims description 4
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
MABISOYNQBKDCJ-UHFFFAOYSA-N 4-[(8-cyclopentyl-5-methyl-7-oxopyrido[2,3-d]pyrimidin-2-yl)amino]benzoic acid Chemical compound C12=NC(NC=3C=CC(=CC=3)C(O)=O)=NC=C2C(C)=CC(=O)N1C1CCCC1 MABISOYNQBKDCJ-UHFFFAOYSA-N 0.000 claims description 4
MWEYAYDODYSNDX-UHFFFAOYSA-N 5-methyl-2-[4-(4-propanoylpiperazin-1-yl)anilino]-8-propan-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(C(=O)CC)CCN1C(C=C1)=CC=C1NC1=NC=C(C(C)=CC(=O)N2C(C)C)C2=N1 MWEYAYDODYSNDX-UHFFFAOYSA-N 0.000 claims description 4
RTDWYVYQMRWDTK-UHFFFAOYSA-N 6-bromo-8-cyclopentyl-5-methyl-2-[4-[4-[3-(2h-tetrazol-5-yl)propyl]piperidin-1-yl]anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCC(CCCC4=NNN=N4)CC3)=NC=C2C(C)=C(Br)C(=O)N1C1CCCC1 RTDWYVYQMRWDTK-UHFFFAOYSA-N 0.000 claims description 4
MQMVVICIZXNENP-UHFFFAOYSA-N 8-cyclopentyl-2-(1h-indol-5-ylamino)-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=C4C=CNC4=CC=3)=NC=C2C(C)=CC(=O)N1C1CCCC1 MQMVVICIZXNENP-UHFFFAOYSA-N 0.000 claims description 4
APNAVIIJIKHXNQ-UHFFFAOYSA-N 8-cyclopentyl-2-[(2,3-dimethyl-1h-indol-5-yl)amino]-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1=C2C(C)=C(C)NC2=CC=C1NC(N=C12)=NC=C1C(C)=CC(=O)N2C1CCCC1 APNAVIIJIKHXNQ-UHFFFAOYSA-N 0.000 claims description 4
NBQXGCYGWSWENM-HDICACEKSA-N 8-cyclopentyl-2-[4-[(3r,5s)-3,5-dimethylpiperazin-1-yl]anilino]-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(C=C1)=CC=C1NC1=NC=C(C(C)=CC(=O)N2C3CCCC3)C2=N1 NBQXGCYGWSWENM-HDICACEKSA-N 0.000 claims description 4
FXFIUDXEHWHQFN-UHFFFAOYSA-N 8-cyclopentyl-5-ethyl-2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCNCC3)=NC=C2C(CC)=CC(=O)N1C1CCCC1 FXFIUDXEHWHQFN-UHFFFAOYSA-N 0.000 claims description 4
DUHLLNLEDJUKLD-UHFFFAOYSA-N 8-cyclopentyl-5-methyl-2-[4-(1h-1,2,4-triazol-5-ylsulfanylmethyl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(CSC=4NN=CN=4)=CC=3)=NC=C2C(C)=CC(=O)N1C1CCCC1 DUHLLNLEDJUKLD-UHFFFAOYSA-N 0.000 claims description 4
IKBCIJGXYMBUJT-UHFFFAOYSA-N 8-cyclopentyl-5-methyl-2-[4-[4-(1h-1,2,4-triazol-5-ylsulfonyl)piperidin-1-yl]anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCC(CC3)S(=O)(=O)C=3NN=CN=3)=NC=C2C(C)=CC(=O)N1C1CCCC1 IKBCIJGXYMBUJT-UHFFFAOYSA-N 0.000 claims description 4
VAOIKEAHXLZAEU-UHFFFAOYSA-N 8-cyclopentyl-6-fluoro-2-(4-hydroxy-3,5-dimethylanilino)-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound CC1=C(O)C(C)=CC(NC=2N=C3N(C4CCCC4)C(=O)C(F)=C(C)C3=CN=2)=C1 VAOIKEAHXLZAEU-UHFFFAOYSA-N 0.000 claims description 4
YJJIFJQRRDUAEQ-UHFFFAOYSA-N 8-cyclopentyl-6-fluoro-5-methyl-2-[4-[4-[3-[(5-oxo-1,2-dihydro-1,2,4-triazol-3-yl)sulfonyl]propyl]piperidin-1-yl]anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCC(CCCS(=O)(=O)C=4NNC(=O)N=4)CC3)=NC=C2C(C)=C(F)C(=O)N1C1CCCC1 YJJIFJQRRDUAEQ-UHFFFAOYSA-N 0.000 claims description 4
XUPHGISRHZLRHR-UHFFFAOYSA-N 8-cyclopentyl-6-iodo-5-methyl-2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCNCC3)=NC=C2C(C)=C(I)C(=O)N1C1CCCC1 XUPHGISRHZLRHR-UHFFFAOYSA-N 0.000 claims description 4
229940125797 compound 12 Drugs 0.000 claims description 4
229940127573 compound 38 Drugs 0.000 claims description 4
PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 claims description 4
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 4
ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 claims description 3
SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 claims description 3
WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 claims description 3
DVKBNNLGHOZFCH-UHFFFAOYSA-N 2-anilino-8-cyclopentyl-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC=CC=3)=NC=C2C(C)=CC(=O)N1C1CCCC1 DVKBNNLGHOZFCH-UHFFFAOYSA-N 0.000 claims description 3
WZUQEQVVKZPNLV-UHFFFAOYSA-N 3-[4-[(8-cyclopentyl-5-methyl-7-oxopyrido[2,3-d]pyrimidin-2-yl)amino]phenyl]-n,n-diethylpropanamide Chemical compound C1=CC(CCC(=O)N(CC)CC)=CC=C1NC1=NC=C(C(C)=CC(=O)N2C3CCCC3)C2=N1 WZUQEQVVKZPNLV-UHFFFAOYSA-N 0.000 claims description 3
WYFCZWSWFGJODV-MIANJLSGSA-N 4-[[(1s)-2-[(e)-3-[3-chloro-2-fluoro-6-(tetrazol-1-yl)phenyl]prop-2-enoyl]-5-(4-methyl-2-oxopiperazin-1-yl)-3,4-dihydro-1h-isoquinoline-1-carbonyl]amino]benzoic acid Chemical compound O=C1CN(C)CCN1C1=CC=CC2=C1CCN(C(=O)\C=C\C=1C(=CC=C(Cl)C=1F)N1N=NN=C1)[C@@H]2C(=O)NC1=CC=C(C(O)=O)C=C1 WYFCZWSWFGJODV-MIANJLSGSA-N 0.000 claims description 3
GTMYJLACTBZULS-UHFFFAOYSA-N 5-ethyl-2-(4-piperazin-1-ylanilino)-8-propan-2-ylpyrido[2,3-d]pyrimidin-7-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N=1C=C2C(CC)=CC(=O)N(C(C)C)C2=NC=1NC(C=C1)=CC=C1N1CCNCC1 GTMYJLACTBZULS-UHFFFAOYSA-N 0.000 claims description 3
YGNUMNPBRNRSBA-UHFFFAOYSA-N 5-methyl-8-pentan-3-yl-2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C(C)=CC(=O)N(C(CC)CC)C2=NC=1NC(C=C1)=CC=C1N1CCNCC1 YGNUMNPBRNRSBA-UHFFFAOYSA-N 0.000 claims description 3
UAQURTWIOVINMP-UHFFFAOYSA-N 6-bromo-8-cyclopentyl-2-[4-(3,3-dimethylpiperazin-1-yl)anilino]-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CC(C)(C)NCC3)=NC=C2C(C)=C(Br)C(=O)N1C1CCCC1 UAQURTWIOVINMP-UHFFFAOYSA-N 0.000 claims description 3
MSXZBEHSDIOJQX-UHFFFAOYSA-N 6-chloro-8-cyclopentyl-5-methyl-2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCNCC3)=NC=C2C(C)=C(Cl)C(=O)N1C1CCCC1 MSXZBEHSDIOJQX-UHFFFAOYSA-N 0.000 claims description 3
RACNDJAQNJWRIL-UHFFFAOYSA-N 8-cyclohexyl-6-fluoro-5-methyl-2-[4-[4-(3-morpholin-4-ylpropyl)piperidin-1-yl]anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCC(CCCN4CCOCC4)CC3)=NC=C2C(C)=C(F)C(=O)N1C1CCCCC1 RACNDJAQNJWRIL-UHFFFAOYSA-N 0.000 claims description 3
UAQYOQLPVWALBE-UHFFFAOYSA-N 8-cyclopentyl-2-(3,4-dichloroanilino)-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=C(Cl)C(Cl)=CC=3)=NC=C2C(C)=CC(=O)N1C1CCCC1 UAQYOQLPVWALBE-UHFFFAOYSA-N 0.000 claims description 3
SVAQWRWKZMHRHE-UHFFFAOYSA-N 8-cyclopentyl-2-(4-hydroxy-3,5-dimethylanilino)-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound CC1=C(O)C(C)=CC(NC=2N=C3N(C4CCCC4)C(=O)C=C(C)C3=CN=2)=C1 SVAQWRWKZMHRHE-UHFFFAOYSA-N 0.000 claims description 3
IZCQBCIFVPXHCQ-UHFFFAOYSA-N 8-cyclopentyl-2-(4-piperazin-1-ylanilino)-5-(trifluoromethyl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCNCC3)=NC=C2C(C(F)(F)F)=CC(=O)N1C1CCCC1 IZCQBCIFVPXHCQ-UHFFFAOYSA-N 0.000 claims description 3
UCRGEQPRUAWQGL-UHFFFAOYSA-N 8-cyclopentyl-2-[4-(1,4-diazepan-1-yl)anilino]-6-fluoro-5-methylpyrido[2,3-d]pyrimidin-7-one;hydrochloride Chemical compound Cl.C12=NC(NC=3C=CC(=CC=3)N3CCNCCC3)=NC=C2C(C)=C(F)C(=O)N1C1CCCC1 UCRGEQPRUAWQGL-UHFFFAOYSA-N 0.000 claims description 3
KOHCENFNOCYUTH-UHFFFAOYSA-N 8-cyclopentyl-2-[4-(2-hydroxyethyl)anilino]-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(CCO)=CC=3)=NC=C2C(C)=CC(=O)N1C1CCCC1 KOHCENFNOCYUTH-UHFFFAOYSA-N 0.000 claims description 3
KQCSRBKMYHPKNE-UHFFFAOYSA-N 8-cyclopentyl-2-[4-(3,3-dimethylpiperazin-1-yl)anilino]-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CC(C)(C)NCC3)=NC=C2C(C)=CC(=O)N1C1CCCC1 KQCSRBKMYHPKNE-UHFFFAOYSA-N 0.000 claims description 3
FSADLTOIDQVCAJ-UHFFFAOYSA-N 8-cyclopentyl-2-[4-(3-hydroxypyrrolidin-1-yl)anilino]-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CC(O)CC3)=NC=C2C(C)=CC(=O)N1C1CCCC1 FSADLTOIDQVCAJ-UHFFFAOYSA-N 0.000 claims description 3
MWSKJJGXWZYMIK-UHFFFAOYSA-N 8-cyclopentyl-2-[4-(diethoxyphosphorylmethyl)anilino]-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(CP(=O)(OCC)OCC)=CC=C1NC1=NC=C(C(C)=CC(=O)N2C3CCCC3)C2=N1 MWSKJJGXWZYMIK-UHFFFAOYSA-N 0.000 claims description 3
LRSMFTYPNCRAQC-UHFFFAOYSA-N 8-cyclopentyl-5-methyl-2-(4-morpholin-4-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCOCC3)=NC=C2C(C)=CC(=O)N1C1CCCC1 LRSMFTYPNCRAQC-UHFFFAOYSA-N 0.000 claims description 3
WRFAJWXPENQXQB-UHFFFAOYSA-N 8-cyclopentyl-5-methyl-2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=NC(NC=3C=CC(=CC=3)N3CCNCC3)=NC=C2C(C)=CC(=O)N1C1CCCC1 WRFAJWXPENQXQB-UHFFFAOYSA-N 0.000 claims description 3
WBQACJQSIIUNKB-UHFFFAOYSA-N 8-cyclopentyl-6-fluoro-2-[4-(2-hydroxyethyl)anilino]-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(CCO)=CC=3)=NC=C2C(C)=C(F)C(=O)N1C1CCCC1 WBQACJQSIIUNKB-UHFFFAOYSA-N 0.000 claims description 3
JAZAOFQFCQAIQC-UHFFFAOYSA-N 8-cyclopentyl-6-fluoro-5-methyl-2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCNCC3)=NC=C2C(C)=C(F)C(=O)N1C1CCCC1 JAZAOFQFCQAIQC-UHFFFAOYSA-N 0.000 claims description 3
MRDFVTIHCKTWJD-UHFFFAOYSA-N C1(CCCC1)N1C(C=C(C2=C1N=C(N=C2)NC1=CC=C(C=C1)N1CCN(CC1)C(C)=O)CC)=O Chemical compound C1(CCCC1)N1C(C=C(C2=C1N=C(N=C2)NC1=CC=C(C=C1)N1CCN(CC1)C(C)=O)CC)=O MRDFVTIHCKTWJD-UHFFFAOYSA-N 0.000 claims description 3
ZGYUAHGVIXLJOA-UHFFFAOYSA-N CC1CN(CC(C)N1)c1ccc(Nc2ncc3c(cc(=O)n(C4CCCC4)c3n2)C(F)(F)F)cc1 Chemical compound CC1CN(CC(C)N1)c1ccc(Nc2ncc3c(cc(=O)n(C4CCCC4)c3n2)C(F)(F)F)cc1 ZGYUAHGVIXLJOA-UHFFFAOYSA-N 0.000 claims description 3
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
241000124008 Mammalia Species 0.000 claims description 3
201000004681 Psoriasis Diseases 0.000 claims description 3
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 3
AKLKDIAFSUQHLC-UHFFFAOYSA-N [4-[(8-cyclopentyl-5-methyl-7-oxopyrido[2,3-d]pyrimidin-2-yl)amino]phenyl]methylphosphonic acid Chemical compound C12=NC(NC=3C=CC(CP(O)(O)=O)=CC=3)=NC=C2C(C)=CC(=O)N1C1CCCC1 AKLKDIAFSUQHLC-UHFFFAOYSA-N 0.000 claims description 3
229940126208 compound 22 Drugs 0.000 claims description 3
239000003814 drug Substances 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
125000004001 thioalkyl group Chemical group 0.000 claims description 3
ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 claims description 2
UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 claims description 2
GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 claims description 2
GCTFTMWXZFLTRR-GFCCVEGCSA-N (2r)-2-amino-n-[3-(difluoromethoxy)-4-(1,3-oxazol-5-yl)phenyl]-4-methylpentanamide Chemical compound FC(F)OC1=CC(NC(=O)[C@H](N)CC(C)C)=CC=C1C1=CN=CO1 GCTFTMWXZFLTRR-GFCCVEGCSA-N 0.000 claims description 2
IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 claims description 2
YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 claims description 2
STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 claims description 2
FNHHVPPSBFQMEL-KQHDFZBMSA-N (3S)-5-N-[(1S,5R)-3-hydroxy-6-bicyclo[3.1.0]hexanyl]-7-N,3-dimethyl-3-phenyl-2H-1-benzofuran-5,7-dicarboxamide Chemical compound CNC(=O)c1cc(cc2c1OC[C@@]2(C)c1ccccc1)C(=O)NC1[C@H]2CC(O)C[C@@H]12 FNHHVPPSBFQMEL-KQHDFZBMSA-N 0.000 claims description 2
IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 claims description 2
OOKAZRDERJMRCJ-KOUAFAAESA-N (3r)-7-[(1s,2s,4ar,6s,8s)-2,6-dimethyl-8-[(2s)-2-methylbutanoyl]oxy-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-hydroxy-5-oxoheptanoic acid Chemical compound C1=C[C@H](C)[C@H](CCC(=O)C[C@@H](O)CC(O)=O)C2[C@@H](OC(=O)[C@@H](C)CC)C[C@@H](C)C[C@@H]21 OOKAZRDERJMRCJ-KOUAFAAESA-N 0.000 claims description 2
HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 claims description 2
MPDDTAJMJCESGV-CTUHWIOQSA-M (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[(1r)-1-phenylethyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate Chemical compound C1([C@@H](C)N(C)C(=O)C2=NN(C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C2C(C)C)C=2C=CC(F)=CC=2)=CC=CC=C1 MPDDTAJMJCESGV-CTUHWIOQSA-M 0.000 claims description 2
YQOLEILXOBUDMU-KRWDZBQOSA-N (4R)-5-[(6-bromo-3-methyl-2-pyrrolidin-1-ylquinoline-4-carbonyl)amino]-4-(2-chlorophenyl)pentanoic acid Chemical compound CC1=C(C2=C(C=CC(=C2)Br)N=C1N3CCCC3)C(=O)NC[C@H](CCC(=O)O)C4=CC=CC=C4Cl YQOLEILXOBUDMU-KRWDZBQOSA-N 0.000 claims description 2
OIIOPWHTJZYKIL-PMACEKPBSA-N (5S)-5-[[[5-[2-chloro-3-[2-chloro-3-[6-methoxy-5-[[[(2S)-5-oxopyrrolidin-2-yl]methylamino]methyl]pyrazin-2-yl]phenyl]phenyl]-3-methoxypyrazin-2-yl]methylamino]methyl]pyrrolidin-2-one Chemical compound C1(=C(N=C(C2=C(C(C3=CC=CC(=C3Cl)C3=NC(OC)=C(N=C3)CNC[C@H]3NC(=O)CC3)=CC=C2)Cl)C=N1)OC)CNC[C@H]1NC(=O)CC1 OIIOPWHTJZYKIL-PMACEKPBSA-N 0.000 claims description 2
DEVSOMFAQLZNKR-RJRFIUFISA-N (z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-n'-pyrazin-2-ylprop-2-enehydrazide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C2=NN(\C=C/C(=O)NNC=3N=CC=NC=3)C=N2)=C1 DEVSOMFAQLZNKR-RJRFIUFISA-N 0.000 claims description 2
KKHFRAFPESRGGD-UHFFFAOYSA-N 1,3-dimethyl-7-[3-(n-methylanilino)propyl]purine-2,6-dione Chemical compound C1=NC=2N(C)C(=O)N(C)C(=O)C=2N1CCCN(C)C1=CC=CC=C1 KKHFRAFPESRGGD-UHFFFAOYSA-N 0.000 claims description 2
KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 claims description 2
WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 claims description 2
ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 claims description 2
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
WGFNXGPBPIJYLI-UHFFFAOYSA-N 2,6-difluoro-3-[(3-fluorophenyl)sulfonylamino]-n-(3-methoxy-1h-pyrazolo[3,4-b]pyridin-5-yl)benzamide Chemical compound C1=C2C(OC)=NNC2=NC=C1NC(=O)C(C=1F)=C(F)C=CC=1NS(=O)(=O)C1=CC=CC(F)=C1 WGFNXGPBPIJYLI-UHFFFAOYSA-N 0.000 claims description 2
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VCUXVXLUOHDHKK-UHFFFAOYSA-N 2-(2-aminopyrimidin-4-yl)-4-(2-chloro-4-methoxyphenyl)-1,3-thiazole-5-carboxamide Chemical compound ClC1=CC(OC)=CC=C1C1=C(C(N)=O)SC(C=2N=C(N)N=CC=2)=N1 VCUXVXLUOHDHKK-UHFFFAOYSA-N 0.000 claims description 2
QEBYEVQKHRUYPE-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-[(1-methylpyrazol-3-yl)methyl]-4-[[methyl(pyridin-3-ylmethyl)amino]methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CN(C)N=C1CN1C(=O)C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C1CN(C)CC1=CC=CN=C1 QEBYEVQKHRUYPE-UHFFFAOYSA-N 0.000 claims description 2
BJPYBSQNPHNFMK-UHFFFAOYSA-N 2-(3-chloro-4-morpholin-4-ylanilino)-5-methyl-8-propan-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C(C)=CC(=O)N(C(C)C)C2=NC=1NC(C=C1Cl)=CC=C1N1CCOCC1 BJPYBSQNPHNFMK-UHFFFAOYSA-N 0.000 claims description 2
FSEAJWDJTQNCKC-UHFFFAOYSA-N 2-(3-chloro-4-morpholin-4-ylanilino)-8-cyclohexyl-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=C(Cl)C(N4CCOCC4)=CC=3)=NC=C2C(C)=CC(=O)N1C1CCCCC1 FSEAJWDJTQNCKC-UHFFFAOYSA-N 0.000 claims description 2
HOUMJZRXFKUZMJ-UHFFFAOYSA-N 2-(3-chloro-4-morpholin-4-ylanilino)-8-cyclopentyl-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=C(Cl)C(N4CCOCC4)=CC=3)=NC=C2C(C)=CC(=O)N1C1CCCC1 HOUMJZRXFKUZMJ-UHFFFAOYSA-N 0.000 claims description 2
RWOIIXDVHZVDFU-UHFFFAOYSA-N 2-(3-chloro-4-piperazin-1-ylanilino)-5-methyl-8-propan-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C(C)=CC(=O)N(C(C)C)C2=NC=1NC(C=C1Cl)=CC=C1N1CCNCC1 RWOIIXDVHZVDFU-UHFFFAOYSA-N 0.000 claims description 2
MUYJNLKPTCJLRX-UHFFFAOYSA-N 2-(3-chloro-4-piperazin-1-ylanilino)-8-cyclohexyl-6-fluoro-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=C(Cl)C(N4CCNCC4)=CC=3)=NC=C2C(C)=C(F)C(=O)N1C1CCCCC1 MUYJNLKPTCJLRX-UHFFFAOYSA-N 0.000 claims description 2
HBKSAUJHTFQTMK-UHFFFAOYSA-N 2-(3-chloro-4-piperazin-1-ylanilino)-8-cyclopentyl-6-fluoro-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=C(Cl)C(N4CCNCC4)=CC=3)=NC=C2C(C)=C(F)C(=O)N1C1CCCC1 HBKSAUJHTFQTMK-UHFFFAOYSA-N 0.000 claims description 2
LBOFTEHAAWGLCB-UHFFFAOYSA-N 2-[(2-acetyl-1-benzofuran-5-yl)amino]-8-cyclopentyl-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C=1C=C2OC(C(=O)C)=CC2=CC=1NC(N=C12)=NC=C1C(C)=CC(=O)N2C1CCCC1 LBOFTEHAAWGLCB-UHFFFAOYSA-N 0.000 claims description 2
YGPKKACYBUOPFP-UHFFFAOYSA-N 2-[4-(3-aminopyrrolidin-1-yl)-3-chloroanilino]-8-cyclopentyl-5-methylpyrido[2,3-d]pyrimidin-7-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=NC(NC=3C=C(Cl)C(N4CC(N)CC4)=CC=3)=NC=C2C(C)=CC(=O)N1C1CCCC1 YGPKKACYBUOPFP-UHFFFAOYSA-N 0.000 claims description 2
ZMHQYNZUFRWYBH-UHFFFAOYSA-N 2-[4-(3-aminopyrrolidin-1-yl)-3-chloroanilino]-8-cyclopentyl-6-fluoro-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=C(Cl)C(N4CC(N)CC4)=CC=3)=NC=C2C(C)=C(F)C(=O)N1C1CCCC1 ZMHQYNZUFRWYBH-UHFFFAOYSA-N 0.000 claims description 2
ZRHATDJOALGBMT-UHFFFAOYSA-N 2-[4-(3-aminopyrrolidin-1-yl)-3-fluoroanilino]-8-cyclopentyl-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=C(F)C(N4CC(N)CC4)=CC=3)=NC=C2C(C)=CC(=O)N1C1CCCC1 ZRHATDJOALGBMT-UHFFFAOYSA-N 0.000 claims description 2
HKPXHAZGINRUQI-UHFFFAOYSA-N 2-[4-(3-aminopyrrolidin-1-yl)anilino]-5-methyl-8-propan-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C(C)=CC(=O)N(C(C)C)C2=NC=1NC(C=C1)=CC=C1N1CCC(N)C1 HKPXHAZGINRUQI-UHFFFAOYSA-N 0.000 claims description 2
NWFSVKZROQXYRI-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-8-cyclopentyl-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(C)=CC(=O)N2C3CCCC3)C2=N1 NWFSVKZROQXYRI-UHFFFAOYSA-N 0.000 claims description 2
VBEOXLHLWZSPHW-UHFFFAOYSA-N 2-[4-[4-[3-(3-aminopyrrolidin-1-yl)propyl]piperidin-1-yl]anilino]-6-bromo-8-cyclopentyl-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCC(CCCN4CC(N)CC4)CC3)=NC=C2C(C)=C(Br)C(=O)N1C1CCCC1 VBEOXLHLWZSPHW-UHFFFAOYSA-N 0.000 claims description 2
PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 claims description 2
FMKGJQHNYMWDFJ-CVEARBPZSA-N 2-[[4-(2,2-difluoropropoxy)pyrimidin-5-yl]methylamino]-4-[[(1R,4S)-4-hydroxy-3,3-dimethylcyclohexyl]amino]pyrimidine-5-carbonitrile Chemical compound FC(COC1=NC=NC=C1CNC1=NC=C(C(=N1)N[C@H]1CC([C@H](CC1)O)(C)C)C#N)(C)F FMKGJQHNYMWDFJ-CVEARBPZSA-N 0.000 claims description 2
PAYROHWFGZADBR-UHFFFAOYSA-N 2-[[4-amino-5-(5-iodo-4-methoxy-2-propan-2-ylphenoxy)pyrimidin-2-yl]amino]propane-1,3-diol Chemical compound C1=C(I)C(OC)=CC(C(C)C)=C1OC1=CN=C(NC(CO)CO)N=C1N PAYROHWFGZADBR-UHFFFAOYSA-N 0.000 claims description 2
VVCMGAUPZIKYTH-VGHSCWAPSA-N 2-acetyloxybenzoic acid;[(2s,3r)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] propanoate;1,3,7-trimethylpurine-2,6-dione Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O.CN1C(=O)N(C)C(=O)C2=C1N=CN2C.C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 VVCMGAUPZIKYTH-VGHSCWAPSA-N 0.000 claims description 2
YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 claims description 2
TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 claims description 2
LFOIDLOIBZFWDO-UHFFFAOYSA-N 2-methoxy-6-[6-methoxy-4-[(3-phenylmethoxyphenyl)methoxy]-1-benzofuran-2-yl]imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=C2SC(OC)=NN2C=C1C(OC1=CC(OC)=C2)=CC1=C2OCC(C=1)=CC=CC=1OCC1=CC=CC=C1 LFOIDLOIBZFWDO-UHFFFAOYSA-N 0.000 claims description 2
DFRAKBCRUYUFNT-UHFFFAOYSA-N 3,8-dicyclohexyl-2,4,7,9-tetrahydro-[1,3]oxazino[5,6-h][1,3]benzoxazine Chemical compound C1CCCCC1N1CC(C=CC2=C3OCN(C2)C2CCCCC2)=C3OC1 DFRAKBCRUYUFNT-UHFFFAOYSA-N 0.000 claims description 2
QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 claims description 2
WFOVEDJTASPCIR-UHFFFAOYSA-N 3-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)methylamino]-n-[[2-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1CNC(C=1)=CC=CC=1C(=O)NCC1=CC=CC=C1C(F)(F)F WFOVEDJTASPCIR-UHFFFAOYSA-N 0.000 claims description 2
125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
GSDQYSSLIKJJOG-UHFFFAOYSA-N 4-chloro-2-(3-chloroanilino)benzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1NC1=CC=CC(Cl)=C1 GSDQYSSLIKJJOG-UHFFFAOYSA-N 0.000 claims description 2
VKLKXFOZNHEBSW-UHFFFAOYSA-N 5-[[3-[(4-morpholin-4-ylbenzoyl)amino]phenyl]methoxy]pyridine-3-carboxamide Chemical compound O1CCN(CC1)C1=CC=C(C(=O)NC=2C=C(COC=3C=NC=C(C(=O)N)C=3)C=CC=2)C=C1 VKLKXFOZNHEBSW-UHFFFAOYSA-N 0.000 claims description 2
XFJBGINZIMNZBW-CRAIPNDOSA-N 5-chloro-2-[4-[(1r,2s)-2-[2-(5-methylsulfonylpyridin-2-yl)oxyethyl]cyclopropyl]piperidin-1-yl]pyrimidine Chemical compound N1=CC(S(=O)(=O)C)=CC=C1OCC[C@H]1[C@@H](C2CCN(CC2)C=2N=CC(Cl)=CN=2)C1 XFJBGINZIMNZBW-CRAIPNDOSA-N 0.000 claims description 2
IJRKLHTZAIFUTB-UHFFFAOYSA-N 5-nitro-2-(2-phenylethylamino)benzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC=C1NCCC1=CC=CC=C1 IJRKLHTZAIFUTB-UHFFFAOYSA-N 0.000 claims description 2
RSIWALKZYXPAGW-NSHDSACASA-N 6-(3-fluorophenyl)-3-methyl-7-[(1s)-1-(7h-purin-6-ylamino)ethyl]-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C=1([C@@H](NC=2C=3N=CNC=3N=CN=2)C)N=C2SC=C(C)N2C(=O)C=1C1=CC=CC(F)=C1 RSIWALKZYXPAGW-NSHDSACASA-N 0.000 claims description 2
GCMUGFPWXCJFKF-UHFFFAOYSA-N 6-bromo-2-(3-chloro-4-morpholin-4-ylanilino)-8-cyclopentyl-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=C(Cl)C(N4CCOCC4)=CC=3)=NC=C2C(C)=C(Br)C(=O)N1C1CCCC1 GCMUGFPWXCJFKF-UHFFFAOYSA-N 0.000 claims description 2
BASOEDFAVJLEPY-UHFFFAOYSA-N 6-bromo-2-(3-chloro-4-piperazin-1-ylanilino)-8-cyclopentyl-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=C(Cl)C(N4CCNCC4)=CC=3)=NC=C2C(C)=C(Br)C(=O)N1C1CCCC1 BASOEDFAVJLEPY-UHFFFAOYSA-N 0.000 claims description 2
GDUANFXPOZTYKS-UHFFFAOYSA-N 6-bromo-8-[(2,6-difluoro-4-methoxybenzoyl)amino]-4-oxochromene-2-carboxylic acid Chemical compound FC1=CC(OC)=CC(F)=C1C(=O)NC1=CC(Br)=CC2=C1OC(C(O)=O)=CC2=O GDUANFXPOZTYKS-UHFFFAOYSA-N 0.000 claims description 2
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JHKFPBYWRHLHJH-UHFFFAOYSA-N 6-bromo-8-cyclopentyl-2-[3-fluoro-4-[4-(3-morpholin-4-ylpropyl)piperidin-1-yl]anilino]-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=C(F)C(N4CCC(CCCN5CCOCC5)CC4)=CC=3)=NC=C2C(C)=C(Br)C(=O)N1C1CCCC1 JHKFPBYWRHLHJH-UHFFFAOYSA-N 0.000 claims description 2
WGHAHMLSCBKLAY-UHFFFAOYSA-N 6-bromo-8-cyclopentyl-5-methyl-2-[4-[4-(3-morpholin-4-ylpropyl)piperidin-1-yl]anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCC(CCCN4CCOCC4)CC3)=NC=C2C(C)=C(Br)C(=O)N1C1CCCC1 WGHAHMLSCBKLAY-UHFFFAOYSA-N 0.000 claims description 2
NJIAKNWTIVDSDA-FQEVSTJZSA-N 7-[4-(1-methylsulfonylpiperidin-4-yl)phenyl]-n-[[(2s)-morpholin-2-yl]methyl]pyrido[3,4-b]pyrazin-5-amine Chemical compound C1CN(S(=O)(=O)C)CCC1C1=CC=C(C=2N=C(NC[C@H]3OCCNC3)C3=NC=CN=C3C=2)C=C1 NJIAKNWTIVDSDA-FQEVSTJZSA-N 0.000 claims description 2
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PLGJGWGEGIDLLL-UHFFFAOYSA-N 8-cyclopentyl-2-(4-fluoroanilino)-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(F)=CC=3)=NC=C2C(C)=CC(=O)N1C1CCCC1 PLGJGWGEGIDLLL-UHFFFAOYSA-N 0.000 claims description 2
HVLGMASKQOZOKV-UHFFFAOYSA-N 8-cyclopentyl-2-[4-[4-(3-hydroxypropyl)piperidin-1-yl]anilino]-5-methylpyrido[2,3-d]pyrimidin-7-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=NC(NC=3C=CC(=CC=3)N3CCC(CCCO)CC3)=NC=C2C(C)=CC(=O)N1C1CCCC1 HVLGMASKQOZOKV-UHFFFAOYSA-N 0.000 claims description 2
LRDLFKVCAQLFQM-UHFFFAOYSA-N 8-cyclopentyl-5-methyl-2-(4-piperazin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCNCC3)=NC=C2C(C)=CC(=O)N1C1CCCC1 LRDLFKVCAQLFQM-UHFFFAOYSA-N 0.000 claims description 2
WGXBYOLLZVPZLI-UHFFFAOYSA-N 8-cyclopentyl-6-fluoro-2-(3-fluoro-4-piperazin-1-ylanilino)-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=C(F)C(N4CCNCC4)=CC=3)=NC=C2C(C)=C(F)C(=O)N1C1CCCC1 WGXBYOLLZVPZLI-UHFFFAOYSA-N 0.000 claims description 2
JQYGWHKPVMQBNB-UHFFFAOYSA-N 8-cyclopentyl-6-fluoro-2-[3-fluoro-4-[4-(3-morpholin-4-ylpropyl)piperidin-1-yl]anilino]-5-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NC=3C=C(F)C(N4CCC(CCCN5CCOCC5)CC4)=CC=3)=NC=C2C(C)=C(F)C(=O)N1C1CCCC1 JQYGWHKPVMQBNB-UHFFFAOYSA-N 0.000 claims description 2
XASOHFCUIQARJT-UHFFFAOYSA-N 8-methoxy-6-[7-(2-morpholin-4-ylethoxy)imidazo[1,2-a]pyridin-3-yl]-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one Chemical compound C(N1C(=O)C2=C(OC)C=C(C=3N4C(=NC=3)C=C(C=C4)OCCN3CCOCC3)C=C2CC1)C(F)(F)F XASOHFCUIQARJT-UHFFFAOYSA-N 0.000 claims description 2
IRBAWVGZNJIROV-SFHVURJKSA-N 9-(2-cyclopropylethynyl)-2-[[(2s)-1,4-dioxan-2-yl]methoxy]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C#CC4CC4)C=C3CCN2C(=O)N=C1OC[C@@H]1COCCO1 IRBAWVGZNJIROV-SFHVURJKSA-N 0.000 claims description 2
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125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000003333 secondary alcohols Chemical class 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
210000000813 small intestine Anatomy 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
CMZUMMUJMWNLFH-UHFFFAOYSA-N sodium metavanadate Chemical compound [Na+].[O-][V](=O)=O CMZUMMUJMWNLFH-UHFFFAOYSA-N 0.000 description 1
KSAVQLQVUXSOCR-UHFFFAOYSA-N sodium;2-[dodecanoyl(methyl)amino]acetic acid Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC(O)=O KSAVQLQVUXSOCR-UHFFFAOYSA-N 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
239000012453 solvate Substances 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
238000012289 standard assay Methods 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
125000005415 substituted alkoxy group Chemical group 0.000 description 1
125000004426 substituted alkynyl group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
239000007916 tablet composition Substances 0.000 description 1
239000007885 tablet disintegrant Substances 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
210000001550 testis Anatomy 0.000 description 1
CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000005307 thiatriazolyl group Chemical group S1N=NN=C1* 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
210000001685 thyroid gland Anatomy 0.000 description 1
210000001519 tissue Anatomy 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
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
125000004665 trialkylsilyl group Chemical group 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
125000006000 trichloroethyl group Chemical group 0.000 description 1
GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
229940121358 tyrosine kinase inhibitor Drugs 0.000 description 1
239000005483 tyrosine kinase inhibitor Substances 0.000 description 1
208000010576 undifferentiated carcinoma Diseases 0.000 description 1
125000005289 uranyl group Chemical group 0.000 description 1
210000003932 urinary bladder Anatomy 0.000 description 1
230000002485 urinary effect Effects 0.000 description 1
229940070710 valerate Drugs 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 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
239000011345 viscous material Substances 0.000 description 1
229910000166 zirconium phosphate Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

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Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Dermatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

CZ20022929A 2000-03-06 2001-01-29 5-Alkylpyrido[2,3-d]pyrimidinové inhibitory tyrosinových kinas CZ20022929A3 (cs)

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Application Number	Priority Date	Filing Date	Title
US18712400P	2000-03-06	2000-03-06

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Publication Number	Publication Date
CZ20022929A3 true CZ20022929A3 (cs)	2003-02-12

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CZ20022929A CZ20022929A3 (cs)	2000-03-06	2001-01-29	5-Alkylpyrido[2,3-d]pyrimidinové inhibitory tyrosinových kinas

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Country	Link
EP (1)	EP1268476A1 (et)
JP (1)	JP2003528101A (et)
KR (1)	KR20020075805A (et)
CN (1)	CN1422268A (et)
AP (1)	AP2002002643A0 (et)
AR (1)	AR034119A1 (et)
AU (1)	AU2001233028A1 (et)
BG (1)	BG107161A (et)
BR (1)	BR0109056A (et)
CA (1)	CA2401368A1 (et)
CO (1)	CO5280200A1 (et)
CR (1)	CR6736A (et)
CZ (1)	CZ20022929A3 (et)
DZ (1)	DZ3308A1 (et)
EA (1)	EA200200802A1 (et)
EE (1)	EE200200506A (et)
GT (1)	GT200100037A (et)
HN (1)	HN2001000040A (et)
HR (1)	HRP20020798A2 (et)
HU (1)	HUP0300136A2 (et)
IL (1)	IL151480A0 (et)
IS (1)	IS6524A (et)
MA (1)	MA26881A1 (et)
MX (1)	MXPA02008535A (et)
NO (1)	NO20024235L (et)
NZ (1)	NZ520962A (et)
OA (1)	OA12227A (et)
PA (1)	PA8513201A1 (et)
PE (1)	PE20011177A1 (et)
PL (1)	PL358271A1 (et)
SK (1)	SK12472002A3 (et)
SV (1)	SV2001000338A (et)
TN (1)	TNSN01036A1 (et)
WO (1)	WO2001070741A1 (et)
YU (1)	YU66502A (et)
ZA (1)	ZA200207110B (et)

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Publication number	Publication date
TNSN01036A1 (en)	2005-11-10
CO5280200A1 (es)	2003-05-30
KR20020075805A (ko)	2002-10-05
BG107161A (en)	2003-06-30
ZA200207110B (en)	2003-12-04
AU2001233028A1 (en)	2001-10-03
DZ3308A1 (fr)	2001-09-27
YU66502A (sh)	2005-09-19
IS6524A (is)	2002-08-23
PE20011177A1 (es)	2001-11-23
CA2401368A1 (en)	2001-09-27
NO20024235D0 (no)	2002-09-05
PL358271A1 (en)	2004-08-09
SK12472002A3 (sk)	2003-04-01
MXPA02008535A (es)	2002-12-13
NZ520962A (en)	2003-09-26
IL151480A0 (en)	2003-04-10
SV2001000338A (es)	2001-11-30
BR0109056A (pt)	2003-06-03
AR034119A1 (es)	2004-02-04
PA8513201A1 (es)	2003-06-30
HUP0300136A2 (en)	2003-05-28
GT200100037A (es)	2002-03-04
NO20024235L (no)	2002-11-05
MA26881A1 (fr)	2004-12-20
CR6736A (es)	2004-03-10
EA200200802A1 (ru)	2003-02-27
AP2002002643A0 (en)	2002-12-31
WO2001070741A1 (en)	2001-09-27
JP2003528101A (ja)	2003-09-24
OA12227A (en)	2004-03-18
HN2001000040A (es)	2001-09-06
CN1422268A (zh)	2003-06-04
HRP20020798A2 (en)	2004-02-29
EP1268476A1 (en)	2003-01-02
EE200200506A (et)	2004-02-16

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