JP2007512368A5

JP2007512368A5 -

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Publication number: JP2007512368A5
Authority: JP; Japan
Prior art keywords: substituted; unsubstituted; oxo; chloro; dihydroquinazolin
Prior art date: 2004-11-24
Legal status : Granted

Application number

JP2006541684A

Other languages

English (en)

Japanese (ja)

Other versions

JP4778439B2 (ja

JP2007512368A (ja

Filing date

2004-11-24

Publication date

2011-02-17

2004-11-24 Application filed filed Critical

2004-11-24 Priority claimed from PCT/US2004/039448 external-priority patent/WO2005051922A1/en

2007-05-17 Publication of JP2007512368A publication Critical patent/JP2007512368A/ja

2011-02-17 Publication of JP2007512368A5 publication Critical patent/JP2007512368A5/ja

2011-09-21 Application granted granted Critical

2011-09-21 Publication of JP4778439B2 publication Critical patent/JP4778439B2/ja

2024-11-24 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

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-1 hydroxy, amino Chemical group 0.000 claims description 118
150000001875 compounds Chemical class 0.000 claims description 108
125000000217 alkyl group Chemical group 0.000 claims description 81
125000003118 aryl group Chemical group 0.000 claims description 61
125000000623 heterocyclic group Chemical group 0.000 claims description 56
239000000203 mixture Substances 0.000 claims description 41
229910052739 hydrogen Inorganic materials 0.000 claims description 38
239000001257 hydrogen Substances 0.000 claims description 38
125000001072 heteroaryl group Chemical group 0.000 claims description 36
206010028980 Neoplasm Diseases 0.000 claims description 35
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 29
125000003710 aryl alkyl group Chemical group 0.000 claims description 29
201000011510 cancer Diseases 0.000 claims description 28
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 23
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
125000003342 alkenyl group Chemical group 0.000 claims description 21
229910052757 nitrogen Inorganic materials 0.000 claims description 20
125000003545 alkoxy group Chemical group 0.000 claims description 19
125000000304 alkynyl group Chemical group 0.000 claims description 18
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 18
125000005842 heteroatom Chemical group 0.000 claims description 18
239000003795 chemical substances by application Substances 0.000 claims description 17
150000003839 salts Chemical class 0.000 claims description 16
241001465754 Metazoa Species 0.000 claims description 15
125000001424 substituent group Chemical group 0.000 claims description 14
125000000547 substituted alkyl group Chemical group 0.000 claims description 14
239000003814 drug Substances 0.000 claims description 13
230000000694 effects Effects 0.000 claims description 13
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
150000002367 halogens Chemical class 0.000 claims description 12
125000003282 alkyl amino group Chemical group 0.000 claims description 11
229910052736 halogen Inorganic materials 0.000 claims description 11
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 11
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 10
125000005843 halogen group Chemical group 0.000 claims description 10
150000002431 hydrogen Chemical group 0.000 claims description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
239000005517 L01XE01 - Imatinib Substances 0.000 claims description 9
125000004093 cyano group Chemical group *C#N 0.000 claims description 9
125000000753 cycloalkyl group Chemical group 0.000 claims description 9
KTUFNOKKBVMGRW-UHFFFAOYSA-N imatinib Chemical compound C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 KTUFNOKKBVMGRW-UHFFFAOYSA-N 0.000 claims description 9
230000002401 inhibitory effect Effects 0.000 claims description 9
125000003277 amino group Chemical group 0.000 claims description 7
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
125000004663 dialkyl amino group Chemical group 0.000 claims description 7
229910052760 oxygen Inorganic materials 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
229910052717 sulfur Inorganic materials 0.000 claims description 7
125000005157 alkyl carboxy group Chemical group 0.000 claims description 6
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 6
239000003937 drug carrier Substances 0.000 claims description 6
125000004438 haloalkoxy group Chemical group 0.000 claims description 6
UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 claims description 6
125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 5
125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 5
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 5
125000004414 alkyl thio group Chemical group 0.000 claims description 5
125000004104 aryloxy group Chemical group 0.000 claims description 5
125000002837 carbocyclic group Chemical group 0.000 claims description 5
125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 5
229940080856 gleevec Drugs 0.000 claims description 5
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims description 4
229940123237 Taxane Drugs 0.000 claims description 4
229940122803 Vinca alkaloid Drugs 0.000 claims description 4
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
125000004103 aminoalkyl group Chemical group 0.000 claims description 4
DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims description 4
229960004316 cisplatin Drugs 0.000 claims description 4
229960002949 fluorouracil Drugs 0.000 claims description 4
125000001188 haloalkyl group Chemical group 0.000 claims description 4
229940022353 herceptin Drugs 0.000 claims description 4
229960002411 imatinib Drugs 0.000 claims description 4
229960004768 irinotecan Drugs 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
229960004641 rituximab Drugs 0.000 claims description 4
125000006186 3,5-dimethyl benzyl group Chemical group [H]C1=C(C([H])=C(C([H])=C1C([H])([H])[H])C([H])([H])*)C([H])([H])[H] 0.000 claims description 3
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 3
VVIAGPKUTFNRDU-UHFFFAOYSA-N 6S-folinic acid Natural products C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-UHFFFAOYSA-N 0.000 claims description 3
125000001960 7 membered carbocyclic group Chemical group 0.000 claims description 3
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 3
125000004422 alkyl sulphonamide group Chemical group 0.000 claims description 3
229940045799 anthracyclines and related substance Drugs 0.000 claims description 3
125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 3
229960004562 carboplatin Drugs 0.000 claims description 3
150000003857 carboxamides Chemical class 0.000 claims description 3
125000004112 carboxyamino group Chemical group [H]OC(=O)N([H])[*] 0.000 claims description 3
VVIAGPKUTFNRDU-ABLWVSNPSA-N folinic acid Chemical compound C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-ABLWVSNPSA-N 0.000 claims description 3
235000008191 folinic acid Nutrition 0.000 claims description 3
239000011672 folinic acid Substances 0.000 claims description 3
229960001691 leucovorin Drugs 0.000 claims description 3
125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims description 3
238000006467 substitution reaction Methods 0.000 claims description 3
DKPFODGZWDEEBT-QFIAKTPHSA-N taxane Chemical class C([C@]1(C)CCC[C@@H](C)[C@H]1C1)C[C@H]2[C@H](C)CC[C@@H]1C2(C)C DKPFODGZWDEEBT-QFIAKTPHSA-N 0.000 claims description 3
229950006410 tezacitabine Drugs 0.000 claims description 3
GFFXZLZWLOBBLO-ASKVSEFXSA-N tezacitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(=C/F)/[C@H](O)[C@@H](CO)O1 GFFXZLZWLOBBLO-ASKVSEFXSA-N 0.000 claims description 3
UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 claims description 3
229960000303 topotecan Drugs 0.000 claims description 3
229960000575 trastuzumab Drugs 0.000 claims description 3
YELDUWMYYRJMJD-UHFFFAOYSA-N 2-sulfamoylguanidine Chemical compound NC(N)=NS(N)(=O)=O YELDUWMYYRJMJD-UHFFFAOYSA-N 0.000 claims description 2
125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims description 2
125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims description 2
125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims description 2
125000006500 3-trifluoromethoxy benzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC(F)(F)F)=C1[H])C([H])([H])* 0.000 claims description 2
125000006495 3-trifluoromethyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])*)C(F)(F)F 0.000 claims description 2
125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims description 2
125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
125000004966 cyanoalkyl group Chemical group 0.000 claims description 2
AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
125000004992 haloalkylamino group Chemical group 0.000 claims description 2
125000004446 heteroarylalkyl group Chemical group 0.000 claims description 2
125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 2
125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 2
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
POONXXSQQOXHCC-UHFFFAOYSA-N n-(3-aminopropyl)-n-[1-(3-benzyl-7-chloro-4-oxoquinazolin-2-yl)-2-(dimethylamino)-2-oxoethyl]-4-methylbenzamide Chemical compound N=1C2=CC(Cl)=CC=C2C(=O)N(CC=2C=CC=CC=2)C=1C(C(=O)N(C)C)N(CCCN)C(=O)C1=CC=C(C)C=C1 POONXXSQQOXHCC-UHFFFAOYSA-N 0.000 claims description 2
125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 2
CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims 2
VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 claims 2
229960004397 cyclophosphamide Drugs 0.000 claims 2
WITIKSHMUIOFJB-UHFFFAOYSA-N n-(3-aminopropyl)-n-[1-[7-chloro-3-[(3,5-dimethylphenyl)methyl]-4-oxoquinazolin-2-yl]-2-[ethyl(methyl)amino]-2-oxoethyl]-4-methylbenzamide Chemical compound N=1C2=CC(Cl)=CC=C2C(=O)N(CC=2C=C(C)C=C(C)C=2)C=1C(C(=O)N(C)CC)N(CCCN)C(=O)C1=CC=C(C)C=C1 WITIKSHMUIOFJB-UHFFFAOYSA-N 0.000 claims 2
125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims 1
125000006288 3,5-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(C([H])=C1F)C([H])([H])* 0.000 claims 1
238000001516 cell proliferation assay Methods 0.000 claims 1
LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims 1
AVHOJTLHZDDVOA-UHFFFAOYSA-N n-(3-aminopropyl)-n-[1-(3-benzyl-7-chloro-4-oxoquinazolin-2-yl)-2-(diethylamino)-2-oxoethyl]-4-bromobenzamide Chemical compound N=1C2=CC(Cl)=CC=C2C(=O)N(CC=2C=CC=CC=2)C=1C(C(=O)N(CC)CC)N(CCCN)C(=O)C1=CC=C(Br)C=C1 AVHOJTLHZDDVOA-UHFFFAOYSA-N 0.000 claims 1
VEEJEPDQIUHADP-UHFFFAOYSA-N n-(3-aminopropyl)-n-[1-(3-benzyl-7-chloro-4-oxoquinazolin-2-yl)-2-(diethylamino)-2-oxoethyl]-4-methylbenzamide Chemical compound N=1C2=CC(Cl)=CC=C2C(=O)N(CC=2C=CC=CC=2)C=1C(C(=O)N(CC)CC)N(CCCN)C(=O)C1=CC=C(C)C=C1 VEEJEPDQIUHADP-UHFFFAOYSA-N 0.000 claims 1
XSYDZTXTTOMYBB-UHFFFAOYSA-N n-(3-aminopropyl)-n-[1-(3-benzyl-7-chloro-4-oxoquinazolin-2-yl)-2-(dimethylamino)-2-oxoethyl]-4-bromobenzamide Chemical compound N=1C2=CC(Cl)=CC=C2C(=O)N(CC=2C=CC=CC=2)C=1C(C(=O)N(C)C)N(CCCN)C(=O)C1=CC=C(Br)C=C1 XSYDZTXTTOMYBB-UHFFFAOYSA-N 0.000 claims 1
ZWNDSENQXXDXCW-UHFFFAOYSA-N n-(3-aminopropyl)-n-[1-(3-benzyl-7-chloro-4-oxoquinazolin-2-yl)-2-(dimethylamino)-2-oxoethyl]-4-chlorobenzamide Chemical compound N=1C2=CC(Cl)=CC=C2C(=O)N(CC=2C=CC=CC=2)C=1C(C(=O)N(C)C)N(CCCN)C(=O)C1=CC=C(Cl)C=C1 ZWNDSENQXXDXCW-UHFFFAOYSA-N 0.000 claims 1
MEAPCCYRNOYZDP-UHFFFAOYSA-N n-(3-aminopropyl)-n-[1-(3-benzyl-7-chloro-4-oxoquinazolin-2-yl)-2-[ethyl(methyl)amino]-2-oxoethyl]-4-methylbenzamide Chemical compound N=1C2=CC(Cl)=CC=C2C(=O)N(CC=2C=CC=CC=2)C=1C(C(=O)N(C)CC)N(CCCN)C(=O)C1=CC=C(C)C=C1 MEAPCCYRNOYZDP-UHFFFAOYSA-N 0.000 claims 1
LWYJDXDVXHJUGN-UHFFFAOYSA-N n-(3-aminopropyl)-n-[1-(3-benzyl-7-chloro-4-oxoquinazolin-2-yl)-2-morpholin-4-yl-2-oxoethyl]-4-bromobenzamide Chemical compound C=1C=C(Br)C=CC=1C(=O)N(CCCN)C(C=1N(C(=O)C2=CC=C(Cl)C=C2N=1)CC=1C=CC=CC=1)C(=O)N1CCOCC1 LWYJDXDVXHJUGN-UHFFFAOYSA-N 0.000 claims 1
IFHLXHPKUGAEAO-UHFFFAOYSA-N n-(3-aminopropyl)-n-[1-(3-benzyl-7-chloro-4-oxoquinazolin-2-yl)-2-morpholin-4-yl-2-oxoethyl]-4-chlorobenzamide Chemical compound C=1C=C(Cl)C=CC=1C(=O)N(CCCN)C(C=1N(C(=O)C2=CC=C(Cl)C=C2N=1)CC=1C=CC=CC=1)C(=O)N1CCOCC1 IFHLXHPKUGAEAO-UHFFFAOYSA-N 0.000 claims 1
XKBPBVLWGXMACT-UHFFFAOYSA-N n-(3-aminopropyl)-n-[1-(3-benzyl-7-chloro-4-oxoquinazolin-2-yl)-2-oxo-2-pyrrolidin-1-ylethyl]-4-bromobenzamide Chemical compound C=1C=C(Br)C=CC=1C(=O)N(CCCN)C(C=1N(C(=O)C2=CC=C(Cl)C=C2N=1)CC=1C=CC=CC=1)C(=O)N1CCCC1 XKBPBVLWGXMACT-UHFFFAOYSA-N 0.000 claims 1
RZCWDNXHRSULHO-UHFFFAOYSA-N n-(3-aminopropyl)-n-[1-(3-benzyl-7-chloro-4-oxoquinazolin-2-yl)-2-oxo-2-pyrrolidin-1-ylethyl]-4-chlorobenzamide Chemical compound C=1C=C(Cl)C=CC=1C(=O)N(CCCN)C(C=1N(C(=O)C2=CC=C(Cl)C=C2N=1)CC=1C=CC=CC=1)C(=O)N1CCCC1 RZCWDNXHRSULHO-UHFFFAOYSA-N 0.000 claims 1
LOBHTHORIKJWKT-UHFFFAOYSA-N n-(3-aminopropyl)-n-[1-(3-benzyl-7-chloro-4-oxoquinazolin-2-yl)-2-oxo-2-pyrrolidin-1-ylethyl]-4-methylbenzamide Chemical compound C1=CC(C)=CC=C1C(=O)N(CCCN)C(C=1N(C(=O)C2=CC=C(Cl)C=C2N=1)CC=1C=CC=CC=1)C(=O)N1CCCC1 LOBHTHORIKJWKT-UHFFFAOYSA-N 0.000 claims 1
ACBBOCDJQNMBMX-UHFFFAOYSA-N n-(3-aminopropyl)-n-[1-[7-chloro-3-(naphthalen-2-ylmethyl)-4-oxoquinazolin-2-yl]-2-(dimethylamino)-2-oxoethyl]-4-methylbenzamide Chemical compound N=1C2=CC(Cl)=CC=C2C(=O)N(CC=2C=C3C=CC=CC3=CC=2)C=1C(C(=O)N(C)C)N(CCCN)C(=O)C1=CC=C(C)C=C1 ACBBOCDJQNMBMX-UHFFFAOYSA-N 0.000 claims 1
YAGKZVYRBNAUCT-UHFFFAOYSA-N n-(3-aminopropyl)-n-[1-[7-chloro-3-[(2-chloropyridin-4-yl)methyl]-4-oxoquinazolin-2-yl]-2-(dimethylamino)-2-oxoethyl]-4-methylbenzamide Chemical compound N=1C2=CC(Cl)=CC=C2C(=O)N(CC=2C=C(Cl)N=CC=2)C=1C(C(=O)N(C)C)N(CCCN)C(=O)C1=CC=C(C)C=C1 YAGKZVYRBNAUCT-UHFFFAOYSA-N 0.000 claims 1
WCTPJXDMLTZVGB-UHFFFAOYSA-N n-(3-aminopropyl)-n-[1-[7-chloro-3-[(3-chlorophenyl)methyl]-4-oxoquinazolin-2-yl]-2-(dimethylamino)-2-oxoethyl]-4-methylbenzamide Chemical compound N=1C2=CC(Cl)=CC=C2C(=O)N(CC=2C=C(Cl)C=CC=2)C=1C(C(=O)N(C)C)N(CCCN)C(=O)C1=CC=C(C)C=C1 WCTPJXDMLTZVGB-UHFFFAOYSA-N 0.000 claims 1
KCWAGPKXNHROMB-UHFFFAOYSA-N n-(3-aminopropyl)-n-[1-[7-chloro-3-[(3-cyanophenyl)methyl]-4-oxoquinazolin-2-yl]-2-(dimethylamino)-2-oxoethyl]-4-methylbenzamide Chemical compound N=1C2=CC(Cl)=CC=C2C(=O)N(CC=2C=C(C=CC=2)C#N)C=1C(C(=O)N(C)C)N(CCCN)C(=O)C1=CC=C(C)C=C1 KCWAGPKXNHROMB-UHFFFAOYSA-N 0.000 claims 1
WTHOBWPGVADYCP-UHFFFAOYSA-N n-(3-aminopropyl)-n-[1-[7-chloro-3-[(3-fluorophenyl)methyl]-4-oxoquinazolin-2-yl]-2-(dimethylamino)-2-oxoethyl]-4-methylbenzamide Chemical compound N=1C2=CC(Cl)=CC=C2C(=O)N(CC=2C=C(F)C=CC=2)C=1C(C(=O)N(C)C)N(CCCN)C(=O)C1=CC=C(C)C=C1 WTHOBWPGVADYCP-UHFFFAOYSA-N 0.000 claims 1
FXFKDKAQPMEUHH-UHFFFAOYSA-N n-(3-aminopropyl)-n-[1-[7-chloro-3-[(3-hydroxyphenyl)methyl]-4-oxoquinazolin-2-yl]-2-(dimethylamino)-2-oxoethyl]-4-methylbenzamide Chemical compound N=1C2=CC(Cl)=CC=C2C(=O)N(CC=2C=C(O)C=CC=2)C=1C(C(=O)N(C)C)N(CCCN)C(=O)C1=CC=C(C)C=C1 FXFKDKAQPMEUHH-UHFFFAOYSA-N 0.000 claims 1
YUUZYHHMHDULOO-UHFFFAOYSA-N n-(3-aminopropyl)-n-[1-[7-chloro-3-[(3-methoxyphenyl)methyl]-4-oxoquinazolin-2-yl]-2-(dimethylamino)-2-oxoethyl]-4-methylbenzamide Chemical compound COC1=CC=CC(CN2C(C3=CC=C(Cl)C=C3N=C2C(N(CCCN)C(=O)C=2C=CC(C)=CC=2)C(=O)N(C)C)=O)=C1 YUUZYHHMHDULOO-UHFFFAOYSA-N 0.000 claims 1
KKLQRJWUJNLWKR-UHFFFAOYSA-N n-(3-aminopropyl)-n-[1-[7-chloro-3-[(3-methoxyphenyl)methyl]-4-oxoquinazolin-2-yl]-2-[ethyl(methyl)amino]-2-oxoethyl]-4-methylbenzamide Chemical compound N=1C2=CC(Cl)=CC=C2C(=O)N(CC=2C=C(OC)C=CC=2)C=1C(C(=O)N(C)CC)N(CCCN)C(=O)C1=CC=C(C)C=C1 KKLQRJWUJNLWKR-UHFFFAOYSA-N 0.000 claims 1
LFCFRWGOOZKXAB-UHFFFAOYSA-N n-(3-aminopropyl)-n-[1-[7-chloro-3-[(3-methylphenyl)methyl]-4-oxoquinazolin-2-yl]-2-(dimethylamino)-2-oxoethyl]-4-methylbenzamide Chemical compound N=1C2=CC(Cl)=CC=C2C(=O)N(CC=2C=C(C)C=CC=2)C=1C(C(=O)N(C)C)N(CCCN)C(=O)C1=CC=C(C)C=C1 LFCFRWGOOZKXAB-UHFFFAOYSA-N 0.000 claims 1
BYCJSHLRPLZIRP-UHFFFAOYSA-N n-(3-aminopropyl)-n-[1-[7-chloro-3-[(4-chlorophenyl)methyl]-4-oxoquinazolin-2-yl]-2-(dimethylamino)-2-oxoethyl]-4-methylbenzamide Chemical compound N=1C2=CC(Cl)=CC=C2C(=O)N(CC=2C=CC(Cl)=CC=2)C=1C(C(=O)N(C)C)N(CCCN)C(=O)C1=CC=C(C)C=C1 BYCJSHLRPLZIRP-UHFFFAOYSA-N 0.000 claims 1
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JP2006541684A 2003-11-25 2004-11-24 抗癌剤としてのキナゾリノン化合物 Expired - Fee Related JP4778439B2 (ja)