JP5530422B2 - 細胞周期阻害薬としてのｇｅｍ−二置換およびスピロ環式アミノピリジン／ピリミジン - Google Patents

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Publication number

JP5530422B2

JP5530422B2 JP2011504114A JP2011504114A JP5530422B2 JP 5530422 B2 JP5530422 B2 JP 5530422B2 JP 2011504114 A JP2011504114 A JP 2011504114A JP 2011504114 A JP2011504114 A JP 2011504114A JP 5530422 B2 JP5530422 B2 JP 5530422B2

Authority

JP

Japan

Prior art keywords

pyrimidine

piperazinyl

amine

spiro

alkylene

Prior art date

2008-04-07

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

Expired - Fee Related

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• 229940123587 Cell cycle inhibitor Drugs 0.000 title 1
• 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 224
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 30
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 20
• 201000011510 cancer Diseases 0.000 claims abstract description 19
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 16
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 15
• 238000011282 treatment Methods 0.000 claims abstract description 12
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims abstract description 11
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 8
• 230000001404 mediated effect Effects 0.000 claims abstract description 4
• -1 diastereomers Chemical class 0.000 claims description 119
• 125000000217 alkyl group Chemical group 0.000 claims description 62
• 125000002947 alkylene group Chemical group 0.000 claims description 58
• 125000004432 carbon atom Chemical group C* 0.000 claims description 49
• 229910052739 hydrogen Inorganic materials 0.000 claims description 42
• 229920006395 saturated elastomer Polymers 0.000 claims description 41
• 125000000623 heterocyclic group Chemical group 0.000 claims description 35
• 125000003118 aryl group Chemical group 0.000 claims description 30
• 239000003814 drug Substances 0.000 claims description 24
• 229910052757 nitrogen Inorganic materials 0.000 claims description 23
• 239000003795 chemical substances by application Substances 0.000 claims description 21
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
• 150000003839 salts Chemical class 0.000 claims description 21
• 125000003342 alkenyl group Chemical group 0.000 claims description 20
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 19
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
• 125000001072 heteroaryl group Chemical group 0.000 claims description 18
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 14
• 125000001188 haloalkyl group Chemical group 0.000 claims description 14
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
• 125000005843 halogen group Chemical group 0.000 claims description 13
• 229910052799 carbon Inorganic materials 0.000 claims description 12
• ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 12
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 12
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
• 125000000304 alkynyl group Chemical group 0.000 claims description 11
• 150000001412 amines Chemical class 0.000 claims description 11
• 150000001721 carbon Chemical group 0.000 claims description 11
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 10
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
• 125000004193 piperazinyl group Chemical group 0.000 claims description 9
• 125000003386 piperidinyl group Chemical group 0.000 claims description 9
• 125000003003 spiro group Chemical group 0.000 claims description 9
• 239000002671 adjuvant Substances 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
• 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 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
• 125000002883 imidazolyl group Chemical group 0.000 claims description 8
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 8
• 125000000714 pyrimidinyl 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
• 239000001257 hydrogen Substances 0.000 claims description 7
• 125000002971 oxazolyl group Chemical group 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
• IBRCIRUFQOJXNZ-UHFFFAOYSA-N 2-(4-piperazin-1-ylanilino)spiro[6h-pyrrolo[3,4-d]pyrimidine-7,1'-cycloheptane]-5-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCNCC3)=NC=C2C(=O)NC21CCCCCC2 IBRCIRUFQOJXNZ-UHFFFAOYSA-N 0.000 claims description 6
• UWVZXQFYSXOSHR-UHFFFAOYSA-N n-(4-piperazin-1-ylphenyl)spiro[oxane-4,6'-pyrido[4,5]pyrano[1,2-d]pyrimidine]-8'-amine Chemical compound C1CNCCN1C(C=C1)=CC=C1NC1=NC=C(C=2C(=CC=CN=2)OC23CCOCC3)C2=N1 UWVZXQFYSXOSHR-UHFFFAOYSA-N 0.000 claims description 6
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
• 125000004122 cyclic group Chemical group 0.000 claims description 5
• 239000003085 diluting agent Substances 0.000 claims description 5
• JWOHGGWZVXDGKE-UHFFFAOYSA-N n-[6-[4-(dimethylamino)piperidin-1-yl]pyridin-3-yl]-6,6-dimethylspiro[cyclohexene-3,9'-pyrido[4,5]cyclopenta[1,2-d]pyrimidine]-2'-amine Chemical compound C1CC(N(C)C)CCN1C(N=C1)=CC=C1NC1=NC=C(C=2C(=CN=CC=2)C23C=CC(C)(C)CC3)C2=N1 JWOHGGWZVXDGKE-UHFFFAOYSA-N 0.000 claims description 5
• 238000002360 preparation method Methods 0.000 claims description 5
• CNSRBQCJNXYMLH-UHFFFAOYSA-N 1,1-dimethyl-n-(5-piperazin-1-ylpyridin-2-yl)spiro[cyclohexane-4,5'-pyrido[4,5]pyrano[1,2-d]pyrimidine]-3'-amine Chemical compound C1CC(C)(C)CCC21C1=NC(NC=3N=CC(=CC=3)N3CCNCC3)=NC=C1C1=CC=CN=C1O2 CNSRBQCJNXYMLH-UHFFFAOYSA-N 0.000 claims description 4
• 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
• 230000000340 anti-metabolite Effects 0.000 claims description 4
• 229940100197 antimetabolite Drugs 0.000 claims description 4
• 239000002256 antimetabolite Substances 0.000 claims description 4
• VACDZZNBZFTEDK-UHFFFAOYSA-N n-(4-piperazin-1-ylphenyl)spiro[chromeno[3,4-d]pyrimidine-5,1'-cyclohexane]-3-amine Chemical compound C1CCCCC21C1=NC(NC=3C=CC(=CC=3)N3CCNCC3)=NC=C1C1=CC=CC=C1O2 VACDZZNBZFTEDK-UHFFFAOYSA-N 0.000 claims description 4
• 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 description 3
• UZMQNDXJBUGQGR-SANMLTNESA-N (4s)-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-SANMLTNESA-N 0.000 claims description 3
• JSQWLDVGNRBXGT-UHFFFAOYSA-N 6,6-dimethyl-n-(5-piperazin-1-ylpyridin-2-yl)spiro[cyclohexene-3,9'-pyrido[4,5]cyclopenta[1,2-d]pyrimidine]-2'-amine Chemical compound C1=CC(C)(C)CCC21C1=NC(NC=3N=CC(=CC=3)N3CCNCC3)=NC=C1C1=CC=NC=C12 JSQWLDVGNRBXGT-UHFFFAOYSA-N 0.000 claims description 3
• VOYMJQMEQSHQNF-UHFFFAOYSA-N C12=NC(N)=NC=C2C2=CC=CN=C2OC1(CC1)CCC21OCCO2 Chemical compound C12=NC(N)=NC=C2C2=CC=CN=C2OC1(CC1)CCC21OCCO2 VOYMJQMEQSHQNF-UHFFFAOYSA-N 0.000 claims description 3
• UEWYRELXNLHLNX-KNBSFFNGSA-N C1[C@@H](C)N[C@@H](C)CN1C1=NC=CC=C1C1C2(C3=NC(N)=NC=C3C3=CC=NC=C32)C=CCC1 Chemical compound C1[C@@H](C)N[C@@H](C)CN1C1=NC=CC=C1C1C2(C3=NC(N)=NC=C3C3=CC=NC=C32)C=CCC1 UEWYRELXNLHLNX-KNBSFFNGSA-N 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
• 239000003981 vehicle Substances 0.000 claims description 3
• 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 description 2
• VKQXFISZNCIIPG-UHFFFAOYSA-N 1,1-dimethyl-n-(6-piperazin-1-ylpyridin-3-yl)spiro[cyclohexane-4,5'-pyrido[4,5]pyrano[1,2-d]pyrimidine]-3'-amine Chemical compound C1CC(C)(C)CCC21C1=NC(NC=3C=NC(=CC=3)N3CCNCC3)=NC=C1C1=CC=CN=C1O2 VKQXFISZNCIIPG-UHFFFAOYSA-N 0.000 claims description 2
• UZMQNDXJBUGQGR-UHFFFAOYSA-N 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)CC21C1=NC(NC=3C=CC(=CC=3)N3CCNCC3)=NC=C1C1=CC=CN=C1O2 UZMQNDXJBUGQGR-UHFFFAOYSA-N 0.000 claims description 2
• RAUKUSHQQZGEEB-UHFFFAOYSA-N 2-(4-piperazin-1-ylanilino)spiro[6h-pyrrolo[3,4-d]pyrimidine-7,1'-cyclohexane]-5-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCNCC3)=NC=C2C(=O)NC21CCCCC2 RAUKUSHQQZGEEB-UHFFFAOYSA-N 0.000 claims description 2
• YIWVUGXZQFJCKX-UHFFFAOYSA-N 2-(4-piperazin-1-ylanilino)spiro[6h-pyrrolo[3,4-d]pyrimidine-7,1'-cyclopentane]-5-one Chemical compound C12=NC(NC=3C=CC(=CC=3)N3CCNCC3)=NC=C2C(=O)NC21CCCC2 YIWVUGXZQFJCKX-UHFFFAOYSA-N 0.000 claims description 2
• MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims description 2
• VVXCEQMAKYLXNK-UHFFFAOYSA-N 3'-[(5-piperazin-1-ylpyridin-2-yl)amino]spiro[cyclohexane-4,5'-pyrido[4,5]pyrano[1,2-d]pyrimidine]-1-ol Chemical compound C1CC(O)CCC21C1=NC(NC=3N=CC(=CC=3)N3CCNCC3)=NC=C1C1=CC=CN=C1O2 VVXCEQMAKYLXNK-UHFFFAOYSA-N 0.000 claims description 2
• UKRNUFJCRZLYBC-UHFFFAOYSA-N 3-[(5-piperazin-1-ylpyridin-2-yl)amino]spiro[chromeno[3,4-d]pyrimidine-5,1'-cyclohexane]-7-carbonitrile Chemical compound N#CC1=CC=CC(C2=CN=C(NC=3N=CC(=CC=3)N3CCNCC3)N=C22)=C1OC12CCCCC1 UKRNUFJCRZLYBC-UHFFFAOYSA-N 0.000 claims description 2
• SBOMELLQHJRNSW-UHFFFAOYSA-N 4,4-difluoro-n-(5-piperazin-1-ylpyridin-2-yl)spiro[cyclohexane-1,5'-pyrido[4,5]pyrano[1,2-d]pyrimidine]-3'-amine Chemical compound C1CC(F)(F)CCC21C1=NC(NC=3N=CC(=CC=3)N3CCNCC3)=NC=C1C1=CC=CN=C1O2 SBOMELLQHJRNSW-UHFFFAOYSA-N 0.000 claims description 2
• SWIJTIWQYNFTBM-UHFFFAOYSA-N 5'-methyl-2'-[(5-piperazin-1-ylpyridin-2-yl)amino]spiro[cyclopentane-1,8'-quinazoline]-7'-one Chemical compound C12=NC(NC=3N=CC(=CC=3)N3CCNCC3)=NC=C2C(C)=CC(=O)C21CCCC2 SWIJTIWQYNFTBM-UHFFFAOYSA-N 0.000 claims description 2
• BCMALGYLQMMZKE-UHFFFAOYSA-N 6,6-dimethyl-n-(4-piperazin-1-ylphenyl)spiro[cyclohexene-3,9'-pyrido[4,5]cyclopenta[1,2-d]pyrimidine]-2'-amine Chemical compound C1=CC(C)(C)CCC21C1=NC(NC=3C=CC(=CC=3)N3CCNCC3)=NC=C1C1=CC=NC=C12 BCMALGYLQMMZKE-UHFFFAOYSA-N 0.000 claims description 2
• PXZHKPVIQILAKW-UHFFFAOYSA-N 6,6-dimethyl-n-[6-(4-methylpiperazin-1-yl)pyridin-3-yl]spiro[cyclohexene-3,9'-pyrido[4,5]cyclopenta[1,2-d]pyrimidine]-2'-amine Chemical compound C1CN(C)CCN1C(N=C1)=CC=C1NC1=NC=C(C=2C(=CN=CC=2)C23C=CC(C)(C)CC3)C2=N1 PXZHKPVIQILAKW-UHFFFAOYSA-N 0.000 claims description 2
• VXENGFFESGAOFS-UHFFFAOYSA-N 7,7-dimethyl-n-(4-piperazin-1-ylphenyl)-5,6-dihydrocyclopenta[d]pyrimidin-2-amine Chemical compound N1=C2C(C)(C)CCC2=CN=C1NC(C=C1)=CC=C1N1CCNCC1 VXENGFFESGAOFS-UHFFFAOYSA-N 0.000 claims description 2
• VIGKNLNXPXDLFR-UHFFFAOYSA-N 7-fluoro-n-(4-piperazin-1-ylphenyl)spiro[chromeno[3,4-d]pyrimidine-5,1'-cyclohexane]-3-amine Chemical compound FC1=CC=CC(C2=CN=C(NC=3C=CC(=CC=3)N3CCNCC3)N=C22)=C1OC12CCCCC1 VIGKNLNXPXDLFR-UHFFFAOYSA-N 0.000 claims description 2
• XTSLKLUDVUHHNZ-UHFFFAOYSA-N 7-fluoro-n-(4-piperazin-1-ylphenyl)spiro[chromeno[3,4-d]pyrimidine-5,4'-oxane]-3-amine Chemical compound FC1=CC=CC(C2=CN=C(NC=3C=CC(=CC=3)N3CCNCC3)N=C22)=C1OC12CCOCC1 XTSLKLUDVUHHNZ-UHFFFAOYSA-N 0.000 claims description 2
• NEDQOLGOHNRKTJ-UHFFFAOYSA-N 7-fluoro-n-(5-piperazin-1-ylpyridin-2-yl)spiro[chromeno[3,4-d]pyrimidine-5,1'-cyclohexane]-3-amine Chemical compound FC1=CC=CC(C2=CN=C(NC=3N=CC(=CC=3)N3CCNCC3)N=C22)=C1OC12CCCCC1 NEDQOLGOHNRKTJ-UHFFFAOYSA-N 0.000 claims description 2
• PXUISTCKLMIIBO-UHFFFAOYSA-N 7-methylsulfonyl-n-(5-piperazin-1-ylpyridin-2-yl)spiro[chromeno[3,4-d]pyrimidine-5,1'-cyclohexane]-3-amine Chemical compound CS(=O)(=O)C1=CC=CC(C2=CN=C(NC=3N=CC(=CC=3)N3CCNCC3)N=C22)=C1OC12CCCCC1 PXUISTCKLMIIBO-UHFFFAOYSA-N 0.000 claims description 2
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 2
• 102000014150 Interferons Human genes 0.000 claims description 2
• 108010050904 Interferons Proteins 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
• WWUAGYOXKOQRIU-UHFFFAOYSA-N [3-[4-(4-methylpiperazin-1-yl)anilino]spiro[chromeno[3,4-d]pyrimidine-5,4'-piperidine]-1'-yl]-phenylmethanone Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=2C(=CC=CC=2)OC23CCN(CC3)C(=O)C=3C=CC=CC=3)C2=N1 WWUAGYOXKOQRIU-UHFFFAOYSA-N 0.000 claims description 2
• 229940100198 alkylating agent Drugs 0.000 claims description 2
• 239000002168 alkylating agent Substances 0.000 claims description 2
• 230000003115 biocidal effect Effects 0.000 claims description 2
• 229940088597 hormone Drugs 0.000 claims description 2
• 239000005556 hormone Substances 0.000 claims description 2
• 229940124452 immunizing agent Drugs 0.000 claims description 2
• 229940079322 interferon 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
• ASADGIQCNZJGEI-UHFFFAOYSA-N n-(4-morpholin-4-ylphenyl)spiro[indeno[2,1-d]pyrimidine-9,4'-piperidine]-2-amine Chemical compound C1CNCCC21C1=NC(NC=3C=CC(=CC=3)N3CCOCC3)=NC=C1C1=CC=CC=C12 ASADGIQCNZJGEI-UHFFFAOYSA-N 0.000 claims description 2
• GPNCHAIPUWFBTF-UHFFFAOYSA-N n-(4-piperazin-1-ylphenyl)spiro[chromeno[3,4-d]pyrimidine-5,1'-cyclobutane]-3-amine Chemical compound C1CCC21C1=NC(NC=3C=CC(=CC=3)N3CCNCC3)=NC=C1C1=CC=CC=C1O2 GPNCHAIPUWFBTF-UHFFFAOYSA-N 0.000 claims description 2
• ALUSCKNZIZOCPD-UHFFFAOYSA-N n-(4-piperazin-1-ylphenyl)spiro[chromeno[3,4-d]pyrimidine-5,1'-cyclopentane]-3-amine Chemical compound C1CCCC21C1=NC(NC=3C=CC(=CC=3)N3CCNCC3)=NC=C1C1=CC=CC=C1O2 ALUSCKNZIZOCPD-UHFFFAOYSA-N 0.000 claims description 2
• NDWBITNDLJOFGE-UHFFFAOYSA-N n-(4-piperazin-1-ylphenyl)spiro[cyclohexane-1,5'-pyrido[4,5]pyrano[1,2-d]pyrimidine]-3'-amine Chemical compound C1CCCCC21C1=NC(NC=3C=CC(=CC=3)N3CCNCC3)=NC=C1C1=CC=CN=C1O2 NDWBITNDLJOFGE-UHFFFAOYSA-N 0.000 claims description 2
• PODFSHPTZVABJF-UHFFFAOYSA-N n-(4-piperazin-1-ylphenyl)spiro[cyclohexane-1,9'-indeno[2,1-d]pyrimidine]-2'-amine Chemical compound C1CCCCC21C1=NC(NC=3C=CC(=CC=3)N3CCNCC3)=NC=C1C1=CC=CC=C12 PODFSHPTZVABJF-UHFFFAOYSA-N 0.000 claims description 2
• SPCHTHPFSHHDSL-UHFFFAOYSA-N n-(4-piperazin-1-ylphenyl)spiro[indeno[2,1-d]pyrimidine-9,4'-piperidine]-2-amine Chemical compound C1CNCCN1C(C=C1)=CC=C1NC1=NC=C(C=2C(=CC=CC=2)C23CCNCC3)C2=N1 SPCHTHPFSHHDSL-UHFFFAOYSA-N 0.000 claims description 2
• PSQHUJNAOWDFNJ-UHFFFAOYSA-N n-(4-piperazin-1-ylphenyl)spiro[oxane-4,5'-pyrido[4,5]pyrano[1,2-d]pyrimidine]-3'-amine Chemical compound C1CNCCN1C(C=C1)=CC=C1NC1=NC=C(C=2C(=NC=CC=2)OC23CCOCC3)C2=N1 PSQHUJNAOWDFNJ-UHFFFAOYSA-N 0.000 claims description 2
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