JP5002460B2 - タンパク質キナーゼインヒビターとして有用なラクタム化合物 - Google Patents

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Publication number

JP5002460B2

JP5002460B2 JP2007534851A JP2007534851A JP5002460B2 JP 5002460 B2 JP5002460 B2 JP 5002460B2 JP 2007534851 A JP2007534851 A JP 2007534851A JP 2007534851 A JP2007534851 A JP 2007534851A JP 5002460 B2 JP5002460 B2 JP 5002460B2

Authority

JP

Japan

Prior art keywords

pyrimido

dihydro

amino

benzazepin

oxo

Prior art date

2004-10-04

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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• -1 Lactam compounds Chemical class 0.000 title claims description 780
• 239000003909 protein kinase inhibitor Substances 0.000 title description 11
• 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 title description 7
• 150000001875 compounds Chemical class 0.000 claims description 187
• 125000003118 aryl group Chemical group 0.000 claims description 76
• 125000001072 heteroaryl group Chemical group 0.000 claims description 71
• 125000000623 heterocyclic group Chemical group 0.000 claims description 64
• 229910052757 nitrogen Inorganic materials 0.000 claims description 58
• 206010028980 Neoplasm Diseases 0.000 claims description 54
• 229910052739 hydrogen Inorganic materials 0.000 claims description 54
• 125000003342 alkenyl group Chemical group 0.000 claims description 52
• 239000001257 hydrogen Substances 0.000 claims description 52
• 125000000304 alkynyl group Chemical group 0.000 claims description 50
• 150000003839 salts Chemical class 0.000 claims description 45
• 125000000217 alkyl group Chemical group 0.000 claims description 44
• 125000002947 alkylene group Chemical group 0.000 claims description 42
• 229910052799 carbon Inorganic materials 0.000 claims description 42
• 125000001424 substituent group Chemical group 0.000 claims description 41
• 239000003814 drug Substances 0.000 claims description 31
• 229910052760 oxygen Inorganic materials 0.000 claims description 29
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 28
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 28
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 27
• 201000011510 cancer Diseases 0.000 claims description 27
• 229910052717 sulfur Inorganic materials 0.000 claims description 27
• 125000005842 heteroatom Chemical group 0.000 claims description 26
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
• 125000003107 substituted aryl group Chemical group 0.000 claims description 25
• 101150050673 CHK1 gene Proteins 0.000 claims description 24
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• 125000006413 ring segment Chemical group 0.000 claims description 23
• 239000005441 aurora Substances 0.000 claims description 22
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
• 125000001475 halogen functional group Chemical group 0.000 claims description 21
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 20
• 239000008194 pharmaceutical composition Substances 0.000 claims description 19
• 125000004432 carbon atom Chemical group C* 0.000 claims description 18
• 150000002431 hydrogen Chemical class 0.000 claims description 18
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 13
• 108091000080 Phosphotransferase Proteins 0.000 claims description 13
• 125000006574 non-aromatic ring group Chemical group 0.000 claims description 13
• 102000020233 phosphotransferase Human genes 0.000 claims description 13
• 125000005843 halogen group Chemical group 0.000 claims description 12
• 239000002246 antineoplastic agent Substances 0.000 claims description 11
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
• 229940127089 cytotoxic agent Drugs 0.000 claims description 8
• 125000005605 benzo group Chemical group 0.000 claims description 7
• 125000000532 dioxanyl group Chemical group 0.000 claims description 7
• WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 5
• 230000002401 inhibitory effect Effects 0.000 claims description 5
• 238000001959 radiotherapy Methods 0.000 claims description 5
• 229910052731 fluorine Inorganic materials 0.000 claims description 3
• 125000000732 arylene group Chemical group 0.000 claims description 2
• 238000009833 condensation Methods 0.000 claims description 2
• 230000005494 condensation Effects 0.000 claims description 2
• 125000005549 heteroarylene group Chemical group 0.000 claims description 2
• 125000006165 cyclic alkyl group Chemical group 0.000 claims 36
• 125000004991 fluoroalkenyl group Chemical group 0.000 claims 12
• JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims 1
• DEFLNOSTNCSZRB-IDTAVKCVSA-N 9-[(2r,3r,4r,5r)-3,4-dimethoxy-5-(methoxymethyl)oxolan-2-yl]-n-methoxypurin-6-amine Chemical compound CO[C@@H]1[C@H](OC)[C@@H](COC)O[C@H]1N1C2=NC=NC(NOC)=C2N=C1 DEFLNOSTNCSZRB-IDTAVKCVSA-N 0.000 claims 1
• 239000002254 cytotoxic agent Substances 0.000 claims 1
• 231100000599 cytotoxic agent Toxicity 0.000 claims 1
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 561
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 278
• 238000000034 method Methods 0.000 description 213
• QAYPFHIZJSDUSF-UHFFFAOYSA-N azepin-3-one Chemical compound O=C1C=CC=CN=C1 QAYPFHIZJSDUSF-UHFFFAOYSA-N 0.000 description 119
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 74
• 125000001931 aliphatic group Chemical group 0.000 description 70
• 210000004027 cell Anatomy 0.000 description 70
• 239000000203 mixture Substances 0.000 description 67
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 66
• 239000000243 solution Substances 0.000 description 63
• NAMXZEZCNUIYCF-UHFFFAOYSA-N 8-chloro-4-(dimethylaminomethylidene)-1h-1-benzazepine-2,5-dione Chemical compound O=C1C(=CN(C)C)CC(=O)NC2=CC(Cl)=CC=C21 NAMXZEZCNUIYCF-UHFFFAOYSA-N 0.000 description 60
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 49
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 47
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
• 238000006243 chemical reaction Methods 0.000 description 40
• 239000011541 reaction mixture Substances 0.000 description 40
• OCUSYBHPZIFMRI-UHFFFAOYSA-N 1-benzazepin-6-one Chemical compound N1=CC=CC=C2C(=O)C=CC=C21 OCUSYBHPZIFMRI-UHFFFAOYSA-N 0.000 description 36
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 36
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 35
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 33
• ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 32
• 102000001253 Protein Kinase Human genes 0.000 description 31
• 108060006633 protein kinase Proteins 0.000 description 31
• 239000003112 inhibitor Substances 0.000 description 29
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 26
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 22
• 239000007787 solid Substances 0.000 description 22
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 21
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 20
• 238000000746 purification Methods 0.000 description 20
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 19
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 19
• 150000001412 amines Chemical class 0.000 description 19
• 238000004587 chromatography analysis Methods 0.000 description 19
• 230000005764 inhibitory process Effects 0.000 description 19
• SYEIAEYQBUCQFE-UHFFFAOYSA-N 2-(3,4-dimethoxyanilino)-9-iodo-5,7-dihydropyrimido[5,4-d][1]benzazepin-6-one Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC=C(CC(=O)NC=2C3=CC=C(I)C=2)C3=N1 SYEIAEYQBUCQFE-UHFFFAOYSA-N 0.000 description 18
• 125000002723 alicyclic group Chemical group 0.000 description 18
• 230000015572 biosynthetic process Effects 0.000 description 18
• 229960004198 guanidine Drugs 0.000 description 18
• 239000000725 suspension Substances 0.000 description 18
• CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 17
• SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 17
• 238000003786 synthesis reaction Methods 0.000 description 17
• 238000003556 assay Methods 0.000 description 16
• KJESCGNRQKHPDB-UHFFFAOYSA-N 2-(3,4-dimethoxyanilino)-6-oxo-5,7-dihydropyrimido[5,4-d][1]benzazepine-10-carboxylic acid Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC=C(CC(=O)NC=2C3=CC(=CC=2)C(O)=O)C3=N1 KJESCGNRQKHPDB-UHFFFAOYSA-N 0.000 description 15
• PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical compound NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 description 15
• 208000035475 disorder Diseases 0.000 description 15
• 239000011347 resin Substances 0.000 description 15
• 229920005989 resin Polymers 0.000 description 15
• 238000011282 treatment Methods 0.000 description 15
• 150000001408 amides Chemical class 0.000 description 14
• 239000003153 chemical reaction reagent Substances 0.000 description 14
• 229940079593 drug Drugs 0.000 description 14
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
• 238000012360 testing method Methods 0.000 description 14
• 150000001721 carbon Chemical group 0.000 description 13
• 230000001404 mediated effect Effects 0.000 description 13
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
• 230000014509 gene expression Effects 0.000 description 12
• 239000011780 sodium chloride Substances 0.000 description 12
• 229940124597 therapeutic agent Drugs 0.000 description 12
• ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Natural products CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
• RKRGZCAHMPOYJC-UHFFFAOYSA-N 2-(3,4-dimethoxyanilino)-6-oxo-5,7-dihydropyrimido[5,4-d][1]benzazepine-9-carboxylic acid Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC=C(CC(=O)NC=2C3=CC=C(C=2)C(O)=O)C3=N1 RKRGZCAHMPOYJC-UHFFFAOYSA-N 0.000 description 11
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
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• 239000005711 Benzoic acid Substances 0.000 description 11
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• 239000000706 filtrate Substances 0.000 description 11
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 11
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 11
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
• 239000002244 precipitate Substances 0.000 description 11
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 11
• 230000002829 reductive effect Effects 0.000 description 11
• 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 10
• BUYMLVMIVKWJSQ-UHFFFAOYSA-N 8-chloro-3,4-dihydro-1h-1-benzazepine-2,5-dione Chemical compound N1C(=O)CCC(=O)C=2C1=CC(Cl)=CC=2 BUYMLVMIVKWJSQ-UHFFFAOYSA-N 0.000 description 10
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical class NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
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• XXIDAACLUQTSAZ-UHFFFAOYSA-N 4-(dimethylaminomethylidene)-8-methyl-1h-1-benzazepine-2,5-dione Chemical compound O=C1C(=CN(C)C)CC(=O)NC2=CC(C)=CC=C21 XXIDAACLUQTSAZ-UHFFFAOYSA-N 0.000 description 6
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