JP4778439B2 - 抗癌剤としてのキナゾリノン化合物 - Google Patents

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Publication number

JP4778439B2

JP4778439B2 JP2006541684A JP2006541684A JP4778439B2 JP 4778439 B2 JP4778439 B2 JP 4778439B2 JP 2006541684 A JP2006541684 A JP 2006541684A JP 2006541684 A JP2006541684 A JP 2006541684A JP 4778439 B2 JP4778439 B2 JP 4778439B2

Authority

JP

Japan

Prior art keywords

substituted

unsubstituted

oxo

chloro

dihydroquinazolin

Prior art date

2003-11-25

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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• AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical class C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 title abstract description 13
• 239000002246 antineoplastic agent Substances 0.000 title description 9
• 150000003839 salts Chemical class 0.000 claims abstract description 17
• -1 hydroxy, amino Chemical group 0.000 claims description 113
• 150000001875 compounds Chemical class 0.000 claims description 101
• 125000000217 alkyl group Chemical group 0.000 claims description 80
• 125000003118 aryl group Chemical group 0.000 claims description 61
• 125000000623 heterocyclic group Chemical group 0.000 claims description 55
• 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
• 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
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 24
• 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
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 19
• 125000000304 alkynyl group Chemical group 0.000 claims description 18
• 125000005842 heteroatom Chemical group 0.000 claims description 18
• 125000001424 substituent group Chemical group 0.000 claims description 15
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 14
• 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
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
• 125000000753 cycloalkyl group Chemical group 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
• 125000004438 haloalkoxy group Chemical group 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
• 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
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
• 125000004414 alkyl thio group Chemical group 0.000 claims description 4
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 4
• 125000001188 haloalkyl group Chemical group 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
• 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
• 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 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
• 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims description 3
• 238000006467 substitution reaction Methods 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
• 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
• 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
• 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
• 150000000660 7-membered heterocyclic compounds Chemical class 0.000 claims 1
• 125000004967 formylalkyl group Chemical group 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
• QHSREIXXUCQSJB-UHFFFAOYSA-N n-(3-aminopropyl)-n-[1-[7-chloro-3-[(6-chloropyridin-2-yl)methyl]-4-oxoquinazolin-2-yl]-2-(dimethylamino)-2-oxoethyl]-4-methylbenzamide Chemical compound N=1C2=CC(Cl)=CC=C2C(=O)N(CC=2N=C(Cl)C=CC=2)C=1C(C(=O)N(C)C)N(CCCN)C(=O)C1=CC=C(C)C=C1 QHSREIXXUCQSJB-UHFFFAOYSA-N 0.000 claims 1
• TYOPSQBNGUCXIT-UHFFFAOYSA-N n-(3-aminopropyl)-n-[1-[7-chloro-4-oxo-3-[(3-phenylphenyl)methyl]quinazolin-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=2C=CC=CC=2)C=1C(C(=O)N(C)C)N(CCCN)C(=O)C1=CC=C(C)C=C1 TYOPSQBNGUCXIT-UHFFFAOYSA-N 0.000 claims 1
• MMUBVVLHJMVNNI-UHFFFAOYSA-N n-(3-aminopropyl)-n-[1-[7-chloro-4-oxo-3-[[3-(trifluoromethoxy)phenyl]methyl]quinazolin-2-yl]-2-(dimethylamino)-2-oxoethyl]-4-methylbenzamide Chemical compound N=1C2=CC(Cl)=CC=C2C(=O)N(CC=2C=C(OC(F)(F)F)C=CC=2)C=1C(C(=O)N(C)C)N(CCCN)C(=O)C1=CC=C(C)C=C1 MMUBVVLHJMVNNI-UHFFFAOYSA-N 0.000 claims 1
• MSOLDLXOAIVCRD-UHFFFAOYSA-N n-(3-aminopropyl)-n-[1-[7-chloro-4-oxo-3-[[3-(trifluoromethyl)phenyl]methyl]quinazolin-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(F)(F)F)C=1C(C(=O)N(C)C)N(CCCN)C(=O)C1=CC=C(C)C=C1 MSOLDLXOAIVCRD-UHFFFAOYSA-N 0.000 claims 1
• SZIUNCQWNWCERK-UHFFFAOYSA-N n-(3-aminopropyl)-n-[1-[7-chloro-4-oxo-3-[[4-(trifluoromethoxy)phenyl]methyl]quinazolin-2-yl]-2-(dimethylamino)-2-oxoethyl]-4-methylbenzamide Chemical compound N=1C2=CC(Cl)=CC=C2C(=O)N(CC=2C=CC(OC(F)(F)F)=CC=2)C=1C(C(=O)N(C)C)N(CCCN)C(=O)C1=CC=C(C)C=C1 SZIUNCQWNWCERK-UHFFFAOYSA-N 0.000 claims 1
• 239000000203 mixture Substances 0.000 abstract description 32
• 238000000034 method Methods 0.000 abstract description 28
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 22
• 230000002062 proliferating effect Effects 0.000 abstract description 17
• 238000011282 treatment Methods 0.000 abstract description 16
• 239000003814 drug Substances 0.000 abstract description 14
• 229940002612 prodrug Drugs 0.000 abstract description 14
• 239000000651 prodrug Substances 0.000 abstract description 14
• 201000010099 disease Diseases 0.000 abstract description 10
• 239000003937 drug carrier Substances 0.000 abstract description 6
• 229940124597 therapeutic agent Drugs 0.000 abstract description 5
• 238000011321 prophylaxis Methods 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 56
• 206010028980 Neoplasm Diseases 0.000 description 28
• 229910052799 carbon Inorganic materials 0.000 description 25
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 23
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
• 201000011510 cancer Diseases 0.000 description 20
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 19
• 210000004027 cell Anatomy 0.000 description 19
• 235000019439 ethyl acetate Nutrition 0.000 description 19
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 17
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 15
• 239000000243 solution Substances 0.000 description 15
• 239000002904 solvent Substances 0.000 description 15
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
• 125000004432 carbon atom Chemical group C* 0.000 description 14
• 239000003112 inhibitor Substances 0.000 description 14
• 239000007787 solid Substances 0.000 description 14
• 239000003795 chemical substances by application Substances 0.000 description 13
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