CA2577251A1 - Pyrimidine derivatives - Google Patents
Pyrimidine derivatives Download PDFInfo
- Publication number
- CA2577251A1 CA2577251A1 CA002577251A CA2577251A CA2577251A1 CA 2577251 A1 CA2577251 A1 CA 2577251A1 CA 002577251 A CA002577251 A CA 002577251A CA 2577251 A CA2577251 A CA 2577251A CA 2577251 A1 CA2577251 A1 CA 2577251A1
- Authority
- CA
- Canada
- Prior art keywords
- ylamino
- methoxy
- pyrimidin
- methyl
- phenylamino
- 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.)
- Abandoned
Links
- 150000003230 pyrimidines Chemical class 0.000 title abstract description 5
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title abstract description 4
- 238000000034 method Methods 0.000 claims abstract description 40
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 13
- 239000003814 drug Substances 0.000 claims abstract description 10
- 238000004519 manufacturing process Methods 0.000 claims abstract description 9
- 230000008569 process Effects 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 117
- 229910052739 hydrogen Inorganic materials 0.000 claims description 69
- 239000001257 hydrogen Substances 0.000 claims description 68
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 43
- 150000003839 salts Chemical class 0.000 claims description 37
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 27
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 27
- 206010028980 Neoplasm Diseases 0.000 claims description 24
- 201000010099 disease Diseases 0.000 claims description 22
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 20
- 125000006413 ring segment Chemical group 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 239000004480 active ingredient Substances 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 230000005764 inhibitory process Effects 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- 150000002367 halogens Chemical group 0.000 claims description 12
- 125000004429 atom Chemical group 0.000 claims description 11
- 150000002431 hydrogen Chemical group 0.000 claims description 11
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 8
- 230000001613 neoplastic effect Effects 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 229940088679 drug related substance Drugs 0.000 claims description 6
- 208000026278 immune system disease Diseases 0.000 claims description 6
- 230000002265 prevention Effects 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 5
- 230000002062 proliferating effect Effects 0.000 claims description 5
- VBOFRRPQWRDUBS-UHFFFAOYSA-N 2-[[5-chloro-2-(2-methoxy-4-morpholin-4-ylanilino)pyrimidin-4-yl]amino]-5-(4-hydroxypiperidin-1-yl)-n-methylbenzamide Chemical compound CNC(=O)C1=CC(N2CCC(O)CC2)=CC=C1NC(C(=CN=1)Cl)=NC=1NC(C(=C1)OC)=CC=C1N1CCOCC1 VBOFRRPQWRDUBS-UHFFFAOYSA-N 0.000 claims description 4
- 239000000969 carrier Substances 0.000 claims description 4
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 4
- QNZSRUNDCIMEQW-HHHXNRCGSA-N (3r)-1-[4-[[5-chloro-4-[(2-methyl-3-oxo-1h-isoindol-4-yl)amino]pyrimidin-2-yl]amino]-3-methoxyphenyl]-3-methylpiperidine-3-carboxamide Chemical compound C=1C=C(NC=2N=C(NC=3C=4C(=O)N(C)CC=4C=CC=3)C(Cl)=CN=2)C(OC)=CC=1N1CCC[C@@](C)(C(N)=O)C1 QNZSRUNDCIMEQW-HHHXNRCGSA-N 0.000 claims description 3
- NIDGJESNBXPTJZ-AREMUKBSSA-N (3r)-1-[4-[[5-chloro-4-[2-(methylcarbamoyl)anilino]pyrimidin-2-yl]amino]-3-methoxyphenyl]-3-methylpiperidine-3-carboxamide Chemical compound CNC(=O)C1=CC=CC=C1NC1=NC(NC=2C(=CC(=CC=2)N2C[C@@](C)(CCC2)C(N)=O)OC)=NC=C1Cl NIDGJESNBXPTJZ-AREMUKBSSA-N 0.000 claims description 3
- ZMRTULLVSRWTIK-UHFFFAOYSA-N 1-[4-[[5-chloro-4-[(2-methyl-3-oxo-1h-isoindol-4-yl)amino]pyrimidin-2-yl]amino]-3-methoxyphenyl]piperidine-3-carboxamide Chemical compound C=1C=C(NC=2N=C(NC=3C=4C(=O)N(C)CC=4C=CC=3)C(Cl)=CN=2)C(OC)=CC=1N1CCCC(C(N)=O)C1 ZMRTULLVSRWTIK-UHFFFAOYSA-N 0.000 claims description 3
- HRLQTDYPYJAQKB-UHFFFAOYSA-N 1-[4-[[5-chloro-4-[(2-methyl-3-oxo-1h-isoindol-4-yl)amino]pyrimidin-2-yl]amino]-3-methoxyphenyl]piperidine-4-carboxamide Chemical compound C=1C=C(NC=2N=C(NC=3C=4C(=O)N(C)CC=4C=CC=3)C(Cl)=CN=2)C(OC)=CC=1N1CCC(C(N)=O)CC1 HRLQTDYPYJAQKB-UHFFFAOYSA-N 0.000 claims description 3
- PCPYKCXGYNSQDW-UHFFFAOYSA-N 2-[[5-bromo-2-(2,4-dimethoxy-5-morpholin-4-ylanilino)pyrimidin-4-yl]amino]-n-propan-2-ylbenzenesulfonamide Chemical compound COC1=CC(OC)=C(N2CCOCC2)C=C1NC(N=1)=NC=C(Br)C=1NC1=CC=CC=C1S(=O)(=O)NC(C)C PCPYKCXGYNSQDW-UHFFFAOYSA-N 0.000 claims description 3
- XZYWSQJGDNNNTA-UHFFFAOYSA-N 2-[[5-bromo-2-(2-methoxy-5-morpholin-4-ylanilino)pyrimidin-4-yl]amino]-n,n-dimethylbenzenesulfonamide Chemical compound COC1=CC=C(N2CCOCC2)C=C1NC(N=1)=NC=C(Br)C=1NC1=CC=CC=C1S(=O)(=O)N(C)C XZYWSQJGDNNNTA-UHFFFAOYSA-N 0.000 claims description 3
- UWGHABCNOXARNC-UHFFFAOYSA-N 2-[[5-bromo-2-[2,4-dimethoxy-5-(2-morpholin-4-ylethoxy)anilino]pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC=C1NC1=NC(NC=2C(=CC(OC)=C(OCCN3CCOCC3)C=2)OC)=NC=C1Br UWGHABCNOXARNC-UHFFFAOYSA-N 0.000 claims description 3
- MEDZUBFZDSXJAC-UHFFFAOYSA-N 2-[[5-bromo-2-[2-methoxy-5-(1-methylpiperidin-4-yl)oxyanilino]pyrimidin-4-yl]amino]-n-propan-2-ylbenzenesulfonamide Chemical compound C1=C(NC=2N=C(NC=3C(=CC=CC=3)S(=O)(=O)NC(C)C)C(Br)=CN=2)C(OC)=CC=C1OC1CCN(C)CC1 MEDZUBFZDSXJAC-UHFFFAOYSA-N 0.000 claims description 3
- ITKGHUPAYWHBIP-UHFFFAOYSA-N 2-[[5-bromo-2-[2-methoxy-5-(1-propan-2-ylpiperidin-4-yl)oxyanilino]pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC=C1NC1=NC(NC=2C(=CC=C(OC3CCN(CC3)C(C)C)C=2)OC)=NC=C1Br ITKGHUPAYWHBIP-UHFFFAOYSA-N 0.000 claims description 3
- YOTZCSJSLZPECF-UHFFFAOYSA-N 2-[[5-bromo-2-[2-methoxy-5-(2-morpholin-4-ylethoxy)anilino]pyrimidin-4-yl]amino]-n,n-dimethylbenzenesulfonamide Chemical compound C1=C(NC=2N=C(NC=3C(=CC=CC=3)S(=O)(=O)N(C)C)C(Br)=CN=2)C(OC)=CC=C1OCCN1CCOCC1 YOTZCSJSLZPECF-UHFFFAOYSA-N 0.000 claims description 3
- NREPZYCCHRXIMV-UHFFFAOYSA-N 2-[[5-bromo-2-[2-methoxy-5-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]amino]-n-propan-2-ylbenzenesulfonamide Chemical compound COC1=CC=C(N2CCN(C)CC2)C=C1NC(N=1)=NC=C(Br)C=1NC1=CC=CC=C1S(=O)(=O)NC(C)C NREPZYCCHRXIMV-UHFFFAOYSA-N 0.000 claims description 3
- WBZMQZPBJXOQBL-UHFFFAOYSA-N 2-[[5-bromo-2-[2-methoxy-5-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]anilino]pyrimidin-4-yl]amino]-n,n-dimethylbenzenesulfonamide Chemical compound COC1=CC=C(N2CCC(CC2)N2CCN(C)CC2)C=C1NC(N=1)=NC=C(Br)C=1NC1=CC=CC=C1S(=O)(=O)N(C)C WBZMQZPBJXOQBL-UHFFFAOYSA-N 0.000 claims description 3
- AGZKTTMKEHBTCY-MRXNPFEDSA-N 2-[[5-bromo-2-[2-methoxy-5-[[(2r)-1-methylpyrrolidin-2-yl]methoxy]anilino]pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC=C1NC1=NC(NC=2C(=CC=C(OC[C@@H]3N(CCC3)C)C=2)OC)=NC=C1Br AGZKTTMKEHBTCY-MRXNPFEDSA-N 0.000 claims description 3
- MTAXVMSPLTYQDA-UHFFFAOYSA-N 2-[[5-bromo-2-[5-(4-hydroxypiperidin-1-yl)-2-methoxyanilino]pyrimidin-4-yl]amino]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC=C1NC1=NC(NC=2C(=CC=C(C=2)N2CCC(O)CC2)OC)=NC=C1Br MTAXVMSPLTYQDA-UHFFFAOYSA-N 0.000 claims description 3
- ZJAYIJSMCXWANH-UHFFFAOYSA-N 2-[[5-chloro-2-(2-methoxy-4-morpholin-4-ylanilino)pyrimidin-4-yl]amino]-n-(2-hydroxyethyl)benzenesulfonamide Chemical compound COC1=CC(N2CCOCC2)=CC=C1NC(N=1)=NC=C(Cl)C=1NC1=CC=CC=C1S(=O)(=O)NCCO ZJAYIJSMCXWANH-UHFFFAOYSA-N 0.000 claims description 3
- GAUIPSIHBYNJAD-UHFFFAOYSA-N 2-[[5-chloro-2-(2-methoxy-4-morpholin-4-ylanilino)pyrimidin-4-yl]amino]-n-(3-hydroxypropyl)benzenesulfonamide Chemical compound COC1=CC(N2CCOCC2)=CC=C1NC(N=1)=NC=C(Cl)C=1NC1=CC=CC=C1S(=O)(=O)NCCCO GAUIPSIHBYNJAD-UHFFFAOYSA-N 0.000 claims description 3
- UIAFSUJLLIGOQU-UHFFFAOYSA-N 2-[[5-chloro-2-(2-methoxy-4-morpholin-4-ylanilino)pyrimidin-4-yl]amino]-n-[2-(dimethylamino)ethyl]benzenesulfonamide Chemical compound COC1=CC(N2CCOCC2)=CC=C1NC(N=1)=NC=C(Cl)C=1NC1=CC=CC=C1S(=O)(=O)NCCN(C)C UIAFSUJLLIGOQU-UHFFFAOYSA-N 0.000 claims description 3
- FJALCYJVUXODQN-UHFFFAOYSA-N 2-[[5-chloro-2-(2-methoxy-4-morpholin-4-ylanilino)pyrimidin-4-yl]amino]-n-ethyl-n-methylbenzenesulfonamide Chemical compound CCN(C)S(=O)(=O)C1=CC=CC=C1NC1=NC(NC=2C(=CC(=CC=2)N2CCOCC2)OC)=NC=C1Cl FJALCYJVUXODQN-UHFFFAOYSA-N 0.000 claims description 3
- OXJMYPXLFFRIBT-UHFFFAOYSA-N 2-[[5-chloro-2-[2-(cyclopropylmethoxy)-4-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]amino]-n-propan-2-ylbenzenesulfonamide Chemical compound CC(C)NS(=O)(=O)C1=CC=CC=C1NC1=NC(NC=2C(=CC(=CC=2)N2CCN(C)CC2)OCC2CC2)=NC=C1Cl OXJMYPXLFFRIBT-UHFFFAOYSA-N 0.000 claims description 3
- LBRVPGIXMBALBV-UHFFFAOYSA-N 2-[[5-chloro-2-[2-ethoxy-4-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]amino]-n-propan-2-ylbenzenesulfonamide Chemical compound CCOC1=CC(N2CCN(C)CC2)=CC=C1NC(N=1)=NC=C(Cl)C=1NC1=CC=CC=C1S(=O)(=O)NC(C)C LBRVPGIXMBALBV-UHFFFAOYSA-N 0.000 claims description 3
- JSWCGIVZNHQNNP-UHFFFAOYSA-N 2-[[5-chloro-2-[2-methoxy-4-(1-methylpiperidin-4-yl)oxyanilino]pyrimidin-4-yl]amino]-n-(2-methylpropyl)benzenesulfonamide Chemical compound C=1C=C(NC=2N=C(NC=3C(=CC=CC=3)S(=O)(=O)NCC(C)C)C(Cl)=CN=2)C(OC)=CC=1OC1CCN(C)CC1 JSWCGIVZNHQNNP-UHFFFAOYSA-N 0.000 claims description 3
- USVFGRLWFJRBAO-UHFFFAOYSA-N 2-[[5-chloro-2-[2-methoxy-4-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]amino]-n-(2-methylpropyl)benzenesulfonamide Chemical compound COC1=CC(N2CCN(C)CC2)=CC=C1NC(N=1)=NC=C(Cl)C=1NC1=CC=CC=C1S(=O)(=O)NCC(C)C USVFGRLWFJRBAO-UHFFFAOYSA-N 0.000 claims description 3
- JABUPWYZDKDXQR-UHFFFAOYSA-N 2-[[5-chloro-2-[2-methoxy-4-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]amino]-n-methyl-n-(2-methylpropyl)benzenesulfonamide Chemical compound COC1=CC(N2CCN(C)CC2)=CC=C1NC(N=1)=NC=C(Cl)C=1NC1=CC=CC=C1S(=O)(=O)N(C)CC(C)C JABUPWYZDKDXQR-UHFFFAOYSA-N 0.000 claims description 3
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- BWJNPIJUMOBXIX-UHFFFAOYSA-N 4-[[5-chloro-4-[2-(2-methylpropylsulfamoyl)anilino]pyrimidin-2-yl]amino]-3-methoxy-n-methylbenzamide Chemical compound COC1=CC(C(=O)NC)=CC=C1NC1=NC=C(Cl)C(NC=2C(=CC=CC=2)S(=O)(=O)NCC(C)C)=N1 BWJNPIJUMOBXIX-UHFFFAOYSA-N 0.000 claims description 3
- JCGLVTFJKQWQLM-UHFFFAOYSA-N 5-chloro-2-n-[4-[4-(4-ethylpiperazin-1-yl)piperidin-1-yl]-2-methoxyphenyl]-4-n-(2-propan-2-ylsulfonylphenyl)pyrimidine-2,4-diamine Chemical compound C1CN(CC)CCN1C1CCN(C=2C=C(OC)C(NC=3N=C(NC=4C(=CC=CC=4)S(=O)(=O)C(C)C)C(Cl)=CN=3)=CC=2)CC1 JCGLVTFJKQWQLM-UHFFFAOYSA-N 0.000 claims description 3
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- CCTCVOLEBOWMOS-UHFFFAOYSA-N 8-[[5-chloro-2-(2-methoxy-4-morpholin-4-ylanilino)pyrimidin-4-yl]amino]-2-ethyl-3,4-dihydroisoquinolin-1-one Chemical compound C=12C(=O)N(CC)CCC2=CC=CC=1NC(C(=CN=1)Cl)=NC=1NC(C(=C1)OC)=CC=C1N1CCOCC1 CCTCVOLEBOWMOS-UHFFFAOYSA-N 0.000 claims description 3
- VRBQCRJAYXBEJP-UHFFFAOYSA-N 8-[[5-chloro-2-[2-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]anilino]pyrimidin-4-yl]amino]-2-methyl-3,4-dihydroisoquinolin-1-one Chemical compound C=1C=C(NC=2N=C(NC=3C=4C(=O)N(C)CCC=4C=CC=3)C(Cl)=CN=2)C(OC)=CC=1N(CC1)CCC1N1CCN(C)CC1 VRBQCRJAYXBEJP-UHFFFAOYSA-N 0.000 claims description 3
- OVNQEFQSYGUPMZ-UHFFFAOYSA-N 8-[[5-chloro-2-[4-(4-hydroxypiperidin-1-yl)-2-methoxyanilino]pyrimidin-4-yl]amino]-2-methyl-3,4-dihydroisoquinolin-1-one Chemical compound C=1C=C(NC=2N=C(NC=3C=4C(=O)N(C)CCC=4C=CC=3)C(Cl)=CN=2)C(OC)=CC=1N1CCC(O)CC1 OVNQEFQSYGUPMZ-UHFFFAOYSA-N 0.000 claims description 3
- AYEVKVJHBPXJNM-LJQANCHMSA-N 8-[[5-chloro-2-[4-[(3r)-3-(dimethylamino)pyrrolidin-1-yl]-2-methoxyanilino]pyrimidin-4-yl]amino]-2-methyl-3,4-dihydroisoquinolin-1-one Chemical compound C=1C=C(NC=2N=C(NC=3C=4C(=O)N(C)CCC=4C=CC=3)C(Cl)=CN=2)C(OC)=CC=1N1CC[C@@H](N(C)C)C1 AYEVKVJHBPXJNM-LJQANCHMSA-N 0.000 claims description 3
- 239000008186 active pharmaceutical agent Substances 0.000 claims description 3
- 201000001441 melanoma Diseases 0.000 claims description 3
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07—ORGANIC CHEMISTRY
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Chemical & Material Sciences (AREA)
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| GBGB0419161.5A GB0419161D0 (en) | 2004-08-27 | 2004-08-27 | Organic compounds |
| GB0419161.5 | 2004-08-27 | ||
| PCT/EP2005/009251 WO2006021454A2 (en) | 2004-08-27 | 2005-08-26 | Pyrimidine derivatives |
Publications (1)
| Publication Number | Publication Date |
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| CA2577251A1 true CA2577251A1 (en) | 2006-03-02 |
Family
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Family Applications (1)
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| CA002577251A Abandoned CA2577251A1 (en) | 2004-08-27 | 2005-08-26 | Pyrimidine derivatives |
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| JP5957003B2 (ja) | 2010-11-10 | 2016-07-27 | セルジーン アヴィロミクス リサーチ, インコーポレイテッド | 変異体選択的egfr阻害剤およびその使用 |
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| ES2880109T3 (es) | 2012-03-15 | 2021-11-23 | Celgene Car Llc | Formas sólidas de un inhibidor de la cinasa del receptor del factor de crecimiento epidérmico |
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| WO2003030909A1 (en) * | 2001-09-25 | 2003-04-17 | Bayer Pharmaceuticals Corporation | 2- and 4-aminopyrimidines n-substtituded by a bicyclic ring for use as kinase inhibitors in the treatment of cancer |
| GB0206215D0 (en) * | 2002-03-15 | 2002-05-01 | Novartis Ag | Organic compounds |
| AU2003231231A1 (en) * | 2002-05-06 | 2003-11-11 | Bayer Pharmaceuticals Corporation | Pyridinyl amino pyrimidine derivatives useful for treating hyper-proliferative disorders |
| GB0305929D0 (en) * | 2003-03-14 | 2003-04-23 | Novartis Ag | Organic compounds |
| RU2395500C2 (ru) * | 2003-08-15 | 2010-07-27 | Новартис Аг | 2,4-пиримидиндиамины, применяемые в лечении неопластических болезней, воспалительных и иммунных расстройств |
| AU2004272288B2 (en) * | 2003-09-18 | 2008-11-13 | Novartis Ag | 2,4-di (phenylamino) pyrimidines useful in the treatment of proliferative disorders |
| GB0419160D0 (en) * | 2004-08-27 | 2004-09-29 | Novartis Ag | Organic compounds |
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- 2007-02-23 MA MA29714A patent/MA28824B1/fr unknown
- 2007-02-26 TN TNP2007000075A patent/TNSN07075A1/en unknown
- 2007-03-27 NO NO20071593A patent/NO20071593L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| TW200621729A (en) | 2006-07-01 |
| ZA200701406B (en) | 2008-08-27 |
| GT200500237A (es) | 2006-03-29 |
| HRP20070076A2 (en) | 2007-07-31 |
| NO20071593L (no) | 2007-05-22 |
| EP1784392A2 (en) | 2007-05-16 |
| ECSP077271A (es) | 2007-03-29 |
| IL181433A0 (en) | 2007-07-04 |
| WO2006021454A2 (en) | 2006-03-02 |
| GB0419161D0 (en) | 2004-09-29 |
| AR054081A1 (es) | 2007-06-06 |
| MX2007002254A (es) | 2007-04-20 |
| US20090131436A1 (en) | 2009-05-21 |
| JP2008510763A (ja) | 2008-04-10 |
| MA28824B1 (fr) | 2007-08-01 |
| AU2005276582B2 (en) | 2009-07-16 |
| BRPI0514681A (pt) | 2008-06-17 |
| TNSN07075A1 (en) | 2008-06-02 |
| PE20060622A1 (es) | 2006-08-14 |
| WO2006021454A3 (en) | 2006-05-04 |
| RU2401260C2 (ru) | 2010-10-10 |
| KR20070054223A (ko) | 2007-05-28 |
| AU2005276582A1 (en) | 2006-03-02 |
| CN101048386A (zh) | 2007-10-03 |
| RU2007110950A (ru) | 2008-10-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |
Effective date: 20130823 |