MX2010010975A - Amino piridinas/pirimidinas gem-disustituidas y espirociclicas como inhibidores de ciclo celular. - Google Patents

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Publication number

MX2010010975A

MX2010010975A MX2010010975A MX2010010975A MX2010010975A MX 2010010975 A MX2010010975 A MX 2010010975A MX 2010010975 A MX2010010975 A MX 2010010975A MX 2010010975 A MX2010010975 A MX 2010010975A MX 2010010975 A MX2010010975 A MX 2010010975A

Authority

MX

Mexico

Prior art keywords

piperazinyl

spiro

pyrimidin

amine

phenyl

Prior art date

2008-04-07

Links

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• 229940123587 Cell cycle inhibitor Drugs 0.000 title description 2
• 150000003927 aminopyridines Chemical class 0.000 title 1
• 150000003230 pyrimidines Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 239
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims abstract description 68
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 37
• 238000011282 treatment Methods 0.000 claims abstract description 32
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 28
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 22
• 238000000034 method Methods 0.000 claims abstract description 21
• 201000011510 cancer Diseases 0.000 claims abstract description 18
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 16
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
• 229910052739 hydrogen Inorganic materials 0.000 claims description 443
• -1 diastereomers Chemical class 0.000 claims description 369
• 125000003003 spiro group Chemical group 0.000 claims description 91
• 125000002947 alkylene group Chemical group 0.000 claims description 82
• QZHPTGXQGDFGEN-UHFFFAOYSA-N chromene Chemical compound C1=CC=C2C=C[CH]OC2=C1 QZHPTGXQGDFGEN-UHFFFAOYSA-N 0.000 claims description 73
• 125000004432 carbon atom Chemical group C* 0.000 claims description 51
• 229920006395 saturated elastomer Polymers 0.000 claims description 45
• 125000000217 alkyl group Chemical group 0.000 claims description 43
• MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims description 32
• 125000000623 heterocyclic group Chemical group 0.000 claims description 29
• 239000003795 chemical substances by application Substances 0.000 claims description 27
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 24
• 125000003118 aryl group Chemical group 0.000 claims description 22
• 229910052757 nitrogen Inorganic materials 0.000 claims description 22
• 150000003839 salts Chemical class 0.000 claims description 22
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
• 125000003342 alkenyl group Chemical group 0.000 claims description 18
• 125000001072 heteroaryl group Chemical group 0.000 claims description 15
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 14
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 13
• 239000003814 drug Substances 0.000 claims description 12
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
• 229910052799 carbon Inorganic materials 0.000 claims description 11
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
• ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 11
• 125000001188 haloalkyl group Chemical group 0.000 claims description 11
• 229910052736 halogen Inorganic materials 0.000 claims description 11
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 11
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 10
• 125000004193 piperazinyl group Chemical group 0.000 claims description 9
• 125000003386 piperidinyl group Chemical group 0.000 claims description 9
• 239000002671 adjuvant Substances 0.000 claims description 8
• 125000000304 alkynyl group Chemical group 0.000 claims description 8
• 150000001721 carbon Chemical group 0.000 claims description 8
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 8
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
• 239000001257 hydrogen Substances 0.000 claims description 8
• 125000002883 imidazolyl group Chemical group 0.000 claims description 8
• 125000002971 oxazolyl group Chemical group 0.000 claims description 8
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 8
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 8
• 125000000335 thiazolyl group Chemical group 0.000 claims description 8
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
• 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 7
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 7
• 125000004076 pyridyl group Chemical group 0.000 claims description 7
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
• 150000002367 halogens Chemical class 0.000 claims description 6
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
• 239000003085 diluting agent Substances 0.000 claims description 5
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
• 229940100198 alkylating agent Drugs 0.000 claims description 4
• 239000002168 alkylating agent Substances 0.000 claims description 4
• 239000002256 antimetabolite Substances 0.000 claims description 4
• 125000004122 cyclic group Chemical group 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
• 229940125697 hormonal agent Drugs 0.000 claims description 3
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
• 125000004043 oxo group Chemical group O=* 0.000 claims description 3
• 239000012453 solvate Substances 0.000 claims description 3
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 2
• 101100005789 Caenorhabditis elegans cdk-4 gene Proteins 0.000 claims description 2
• 241001024304 Mino Species 0.000 claims description 2
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 2
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 2
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
• 230000003115 biocidal effect Effects 0.000 claims description 2
• 239000000677 immunologic agent Substances 0.000 claims description 2
• 229940124541 immunological agent Drugs 0.000 claims description 2
• ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 2
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 2
• LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 claims description 2
• AUGLRFXMHWXOGR-UHFFFAOYSA-N n-(4-piperazin-1-ylphenyl)spiro[indeno[2,1-d]pyrimidine-9,4'-oxane]-2-amine Chemical compound C1CNCCN1C(C=C1)=CC=C1NC1=NC=C(C=2C(=CC=CC=2)C23CCOCC3)C2=N1 AUGLRFXMHWXOGR-UHFFFAOYSA-N 0.000 claims description 2
• APSVEQFRBIZXFT-UHFFFAOYSA-N n-(5-piperazin-1-ylpyridin-2-yl)spiro[cyclopentane-1,9'-pyrido[4,5]cyclopenta[1,2-d]pyrimidine]-2'-amine Chemical compound C1CCCC21C1=NC(NC=3N=CC(=CC=3)N3CCNCC3)=NC=C1C1=CC=NC=C12 APSVEQFRBIZXFT-UHFFFAOYSA-N 0.000 claims description 2
• WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 2
• PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 2
• 125000006413 ring segment Chemical group 0.000 claims description 2
• VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 2
• 229930192474 thiophene Natural products 0.000 claims description 2
• 150000003852 triazoles Chemical class 0.000 claims description 2
• 125000000547 substituted alkyl group Chemical group 0.000 claims 3
• UZMQNDXJBUGQGR-AREMUKBSSA-N (4r)-2,2-dimethyl-n-(4-piperazin-1-ylphenyl)spiro[oxane-4,5'-pyrido[4,5]pyrano[1,2-d]pyrimidine]-3'-amine Chemical compound C1COC(C)(C)C[C@]21C1=NC(NC=3C=CC(=CC=3)N3CCNCC3)=NC=C1C1=CC=CN=C1O2 UZMQNDXJBUGQGR-AREMUKBSSA-N 0.000 claims 1
• XPAQCWJQFDUFRG-UHFFFAOYSA-N 1'-methyl-n-[4-(4-methylpiperazin-1-yl)phenyl]spiro[indeno[2,1-d]pyrimidine-9,4'-piperidine]-2-amine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=2C(=CC=CC=2)C23CCN(C)CC3)C2=N1 XPAQCWJQFDUFRG-UHFFFAOYSA-N 0.000 claims 1
• MWTYHSLKLDNBBZ-UHFFFAOYSA-N 5-methyl-2-[(5-piperazin-1-ylpyridin-2-yl)amino]spiro[5,6-dihydroquinazoline-8,4'-cyclopentene]-7-one Chemical compound C12=NC(NC=3N=CC(=CC=3)N3CCNCC3)=NC=C2C(C)CC(=O)C21CC=CC2 MWTYHSLKLDNBBZ-UHFFFAOYSA-N 0.000 claims 1
• XOEGISZWMOBKHL-UHFFFAOYSA-N 5-methyl-2-[(5-piperazin-1-ylpyridin-2-yl)amino]spiro[6,7-dihydro-5h-quinazoline-8,1'-cyclopentane]-7-ol Chemical compound C12=NC(NC=3N=CC(=CC=3)N3CCNCC3)=NC=C2C(C)CC(O)C21CCCC2 XOEGISZWMOBKHL-UHFFFAOYSA-N 0.000 claims 1
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