JP2011516558A5 - - Google Patents
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- Publication number
- JP2011516558A5 JP2011516558A5 JP2011504114A JP2011504114A JP2011516558A5 JP 2011516558 A5 JP2011516558 A5 JP 2011516558A5 JP 2011504114 A JP2011504114 A JP 2011504114A JP 2011504114 A JP2011504114 A JP 2011504114A JP 2011516558 A5 JP2011516558 A5 JP 2011516558A5
- Authority
- JP
- Japan
- Prior art keywords
- piperazinyl
- pyrimidine
- spiro
- alkylene
- amine
- 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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- 150000001875 compounds Chemical class 0.000 claims 35
- 125000002947 alkylene group Chemical group 0.000 claims 29
- 125000000217 alkyl group Chemical group 0.000 claims 16
- 125000000623 heterocyclic group Chemical group 0.000 claims 9
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims 7
- 229910052757 nitrogen Inorganic materials 0.000 claims 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 7
- 125000003342 alkenyl group Chemical group 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- -1 diastereomers Chemical class 0.000 claims 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims 5
- 150000001721 carbon Chemical group 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 5
- 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 5
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 5
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 5
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 5
- 125000002883 imidazolyl group Chemical group 0.000 claims 5
- 125000002971 oxazolyl group Chemical group 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000004193 piperazinyl group Chemical group 0.000 claims 5
- 125000003386 piperidinyl group Chemical group 0.000 claims 5
- 125000003373 pyrazinyl group Chemical group 0.000 claims 5
- 125000002098 pyridazinyl group Chemical group 0.000 claims 5
- 125000004076 pyridyl group Chemical group 0.000 claims 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims 5
- 125000000335 thiazolyl group Chemical group 0.000 claims 5
- 206010028980 Neoplasm Diseases 0.000 claims 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 4
- 239000003795 chemical substances by application Substances 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 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 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000003003 spiro group Chemical group 0.000 claims 2
- 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
- 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 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
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- XSGYMNQFEOGOMJ-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)anilino]spiro[6h-pyrrolo[3,4-d]pyrimidine-7,1'-cyclohexane]-5-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(=O)NC23CCCCC3)C2=N1 XSGYMNQFEOGOMJ-UHFFFAOYSA-N 0.000 claims 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 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
- YWHKOEZHEOTZPZ-UHFFFAOYSA-N 5-methyl-2-[(5-piperazin-1-ylpyridin-2-yl)amino]spiro[6,7-dihydro-5h-quinazoline-8,4'-cyclopentene]-7-ol Chemical compound C12=NC(NC=3N=CC(=CC=3)N3CCNCC3)=NC=C2C(C)CC(O)C21CC=CC2 YWHKOEZHEOTZPZ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- MNRNLELEHAIVAG-UHFFFAOYSA-N 9,9-diethyl-n-(5-piperazin-1-ylpyridin-2-yl)pyrido[4,5]cyclopenta[1,2-d]pyrimidin-2-amine Chemical compound N1=C2C(CC)(CC)C3=CN=CC=C3C2=CN=C1NC(N=C1)=CC=C1N1CCNCC1 MNRNLELEHAIVAG-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 101100005789 Caenorhabditis elegans cdk-4 gene Proteins 0.000 claims 1
- 102000014150 Interferons Human genes 0.000 claims 1
- 108010050904 Interferons Proteins 0.000 claims 1
- 206010027476 Metastases Diseases 0.000 claims 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 239000002168 alkylating agent Substances 0.000 claims 1
- 229940100198 alkylating agent Drugs 0.000 claims 1
- 230000000340 anti-metabolite Effects 0.000 claims 1
- 239000002256 antimetabolite Substances 0.000 claims 1
- 229940100197 antimetabolite Drugs 0.000 claims 1
- 230000003115 biocidal effect Effects 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 239000005556 hormone Substances 0.000 claims 1
- 229940088597 hormone Drugs 0.000 claims 1
- 229940124452 immunizing agent Drugs 0.000 claims 1
- 229940079322 interferon Drugs 0.000 claims 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 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 1
- 230000009401 metastasis Effects 0.000 claims 1
- RVUSMBDDJZRKSD-UHFFFAOYSA-N n-(2-piperazin-1-ylpyrimidin-5-yl)spiro[chromeno[3,4-d]pyrimidine-5,4'-oxane]-3-amine Chemical class C1CNCCN1C(N=C1)=NC=C1NC1=NC=C(C=2C(=CC=CC=2)OC23CCOCC3)C2=N1 RVUSMBDDJZRKSD-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- HFUXZQLGBZXVKA-UHFFFAOYSA-N n-(4-piperazin-1-ylphenyl)spiro[chromeno[3,4-d]pyrimidine-5,4'-oxane]-3-amine Chemical compound C1CNCCN1C(C=C1)=CC=C1NC1=NC=C(C=2C(=CC=CC=2)OC23CCOCC3)C2=N1 HFUXZQLGBZXVKA-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
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-
2009
- 2009-04-06 US US12/936,725 patent/US8389533B2/en active Active
- 2009-04-06 EP EP09730921A patent/EP2278973B1/en active Active
- 2009-04-06 MX MX2010010975A patent/MX2010010975A/es active IP Right Grant
- 2009-04-06 AT AT09730921T patent/ATE531372T1/de active
- 2009-04-06 WO PCT/US2009/039678 patent/WO2009126584A1/en not_active Ceased
- 2009-04-06 AU AU2009233951A patent/AU2009233951B2/en not_active Ceased
- 2009-04-06 CA CA2719538A patent/CA2719538C/en not_active Expired - Fee Related
- 2009-04-06 JP JP2011504114A patent/JP5530422B2/ja not_active Expired - Fee Related
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