HRP20010542A2 - Substituted bicyclic derivatives useful as anticancer agents - Google Patents
Substituted bicyclic derivatives useful as anticancer agents Download PDFInfo
- Publication number
- HRP20010542A2 HRP20010542A2 HR20010542A HRP20010542A HRP20010542A2 HR P20010542 A2 HRP20010542 A2 HR P20010542A2 HR 20010542 A HR20010542 A HR 20010542A HR P20010542 A HRP20010542 A HR P20010542A HR P20010542 A2 HRP20010542 A2 HR P20010542A2
- Authority
- HR
- Croatia
- Prior art keywords
- quinazolin
- cr1r2
- phenoxy
- methyl
- ylethynyl
- Prior art date
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- 125000002619 bicyclic group Chemical group 0.000 title claims description 7
- 239000002246 antineoplastic agent Substances 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 158
- -1 -NR1R2 Chemical group 0.000 claims description 75
- 238000000034 method Methods 0.000 claims description 73
- 150000003839 salts Chemical class 0.000 claims description 42
- 206010028980 Neoplasm Diseases 0.000 claims description 35
- 125000000623 heterocyclic group Chemical group 0.000 claims description 32
- 125000001424 substituent group Chemical group 0.000 claims description 32
- 238000006243 chemical reaction Methods 0.000 claims description 29
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 25
- 230000002159 abnormal effect Effects 0.000 claims description 25
- 230000010261 cell growth Effects 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 239000012453 solvate Substances 0.000 claims description 16
- 241000124008 Mammalia Species 0.000 claims description 15
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 14
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- 125000005843 halogen group Chemical group 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 239000003112 inhibitor Substances 0.000 claims description 11
- 230000008569 process Effects 0.000 claims description 11
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 11
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 9
- 125000001041 indolyl group Chemical group 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000004076 pyridyl group Chemical group 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
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- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims description 5
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- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 4
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- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
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- 239000002168 alkylating agent Substances 0.000 claims description 4
- 229940100198 alkylating agent Drugs 0.000 claims description 4
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- 230000003388 anti-hormonal effect Effects 0.000 claims description 4
- 239000000051 antiandrogen Substances 0.000 claims description 4
- 229940030495 antiandrogen sex hormone and modulator of the genital system Drugs 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
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- 125000003342 alkenyl group Chemical group 0.000 claims description 3
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- 208000026045 malignant tumor of parathyroid gland Diseases 0.000 claims description 3
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 3
- NAKADWFMXIXRIU-UHFFFAOYSA-N n-[2-methyl-4-[4-(3-methyl-4-phenoxyanilino)quinazolin-6-yl]but-3-yn-2-yl]acetamide Chemical compound C12=CC(C#CC(C)(C)NC(=O)C)=CC=C2N=CN=C1NC(C=C1C)=CC=C1OC1=CC=CC=C1 NAKADWFMXIXRIU-UHFFFAOYSA-N 0.000 claims description 3
- FCCVFKMRFKBOGT-UHFFFAOYSA-N n-[4-[4-(3-chloro-4-phenoxyanilino)quinazolin-6-yl]but-3-yn-2-yl]acetamide Chemical compound C12=CC(C#CC(NC(C)=O)C)=CC=C2N=CN=C1NC(C=C1Cl)=CC=C1OC1=CC=CC=C1 FCCVFKMRFKBOGT-UHFFFAOYSA-N 0.000 claims description 3
- YNIOCFVFVVQJQQ-UHFFFAOYSA-N n-[4-[4-(3-methyl-4-phenoxyanilino)quinazolin-6-yl]but-3-yn-2-yl]acetamide Chemical compound C12=CC(C#CC(NC(C)=O)C)=CC=C2N=CN=C1NC(C=C1C)=CC=C1OC1=CC=CC=C1 YNIOCFVFVVQJQQ-UHFFFAOYSA-N 0.000 claims description 3
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
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- LCSKDSPTQOLVAF-QFIPXVFZSA-N (3s)-3-[2-[4-(3-methoxy-4-phenoxyanilino)quinazolin-6-yl]ethynyl]-n-methylpiperidine-1-carboxamide Chemical compound C1N(C(=O)NC)CCC[C@H]1C#CC1=CC=C(N=CN=C2NC=3C=C(OC)C(OC=4C=CC=CC=4)=CC=3)C2=C1 LCSKDSPTQOLVAF-QFIPXVFZSA-N 0.000 claims description 2
- RCKFOMMDLQFOKY-QHCPKHFHSA-N (3s)-n-methyl-3-[2-[4-(3-methyl-4-phenoxyanilino)quinazolin-6-yl]ethynyl]piperidine-1-carboxamide Chemical compound C1N(C(=O)NC)CCC[C@H]1C#CC1=CC=C(N=CN=C2NC=3C=C(C)C(OC=4C=CC=CC=4)=CC=3)C2=C1 RCKFOMMDLQFOKY-QHCPKHFHSA-N 0.000 claims description 2
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- KGPYXNKNYVFNEW-UHFFFAOYSA-N 1-[3-[4-(3-methyl-4-phenoxyanilino)quinazolin-6-yl]prop-2-ynyl]piperidin-4-ol Chemical compound C=1C=C(OC=2C=CC=CC=2)C(C)=CC=1NC(C1=C2)=NC=NC1=CC=C2C#CCN1CCC(O)CC1 KGPYXNKNYVFNEW-UHFFFAOYSA-N 0.000 claims description 2
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- NVTUOMHARHYTMI-UHFFFAOYSA-N 2-methyl-4-[4-(3-methyl-4-phenoxyanilino)quinazolin-6-yl]but-3-yn-2-ol Chemical compound CC1=CC(NC=2C3=CC(=CC=C3N=CN=2)C#CC(C)(C)O)=CC=C1OC1=CC=CC=C1 NVTUOMHARHYTMI-UHFFFAOYSA-N 0.000 claims description 2
- VFKIMJALKPOEOX-UHFFFAOYSA-N 3-[2-[4-(3-bromo-4-phenoxyanilino)quinazolin-6-yl]ethynyl]piperidin-3-ol Chemical compound C=1C=C2N=CN=C(NC=3C=C(Br)C(OC=4C=CC=CC=4)=CC=3)C2=CC=1C#CC1(O)CCCNC1 VFKIMJALKPOEOX-UHFFFAOYSA-N 0.000 claims description 2
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- CKPXQVILGNKODG-UHFFFAOYSA-N 3-[2-[4-(3-methyl-4-phenoxyanilino)quinazolin-6-yl]ethynyl]-8-azabicyclo[3.2.1]octan-3-ol Chemical compound CC1=CC(NC=2C3=CC(=CC=C3N=CN=2)C#CC2(O)CC3CCC(N3)C2)=CC=C1OC1=CC=CC=C1 CKPXQVILGNKODG-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/94—Nitrogen atoms
-
- 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
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
-
- 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
- C07D403/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D403/06—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 carbon chain containing only aliphatic carbon atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
Applications Claiming Priority (2)
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US11734699P | 1999-01-27 | 1999-01-27 | |
PCT/IB1999/001934 WO2000044728A1 (en) | 1999-01-27 | 1999-12-06 | Substituted bicyclic derivatives useful as anticancer agents |
Publications (1)
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HRP20010542A2 true HRP20010542A2 (en) | 2002-08-31 |
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HR20010542A HRP20010542A2 (en) | 1999-01-27 | 2001-07-18 | Substituted bicyclic derivatives useful as anticancer agents |
Country Status (45)
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- 1999-12-08 DZ DZ990263A patent/DZ2963A1/xx active
- 1999-12-08 TN TNTNSN99236A patent/TNSN99236A1/fr unknown
- 1999-12-08 MA MA25863A patent/MA26712A1/fr unknown
- 1999-12-13 CO CO99077826A patent/CO5080774A1/es unknown
- 1999-12-15 PE PE1999001256A patent/PE20001363A1/es not_active Application Discontinuation
- 1999-12-15 AR ARP990106428A patent/AR023346A1/es not_active Application Discontinuation
- 1999-12-17 PA PA19998487601A patent/PA8487601A1/es unknown
- 1999-12-22 SV SV1999000252A patent/SV1999000252A/es unknown
- 1999-12-29 UY UY25887A patent/UY25887A1/es unknown
- 1999-12-30 UY UY25889A patent/UY25889A1/es unknown
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2000
- 2000-01-20 US US09/488,350 patent/US6284764B1/en not_active Expired - Fee Related
- 2000-01-26 GT GT200000005A patent/GT200000005A/es unknown
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2001
- 2001-04-12 US US09/834,259 patent/US6541481B2/en not_active Expired - Fee Related
- 2001-05-22 IS IS5949A patent/IS5949A/is unknown
- 2001-06-27 CR CR6404A patent/CR6404A/es not_active Application Discontinuation
- 2001-07-17 ZA ZA200105867A patent/ZA200105867B/en unknown
- 2001-07-18 HR HR20010542A patent/HRP20010542A2/hr not_active Application Discontinuation
- 2001-07-26 NO NO20013671A patent/NO322297B1/no unknown
- 2001-08-24 BG BG105842A patent/BG105842A/bg unknown
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2002
- 2002-07-24 HK HK02105471.5A patent/HK1043795B/zh not_active IP Right Cessation
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2003
- 2003-01-21 US US10/349,475 patent/US20030186995A1/en not_active Abandoned
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2004
- 2004-07-23 JP JP2004216138A patent/JP2005002125A/ja active Pending
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