BG107376A - Заместени хиназолинови производни и тяхното използване като инхибитори - Google Patents

Заместени хиназолинови производни и тяхното използване като инхибитори Download PDF

Info

Publication number: BG107376A
Authority: BG; Bulgaria
Prior art keywords: alkyl; compound; mmol; optionally substituted; group
Prior art date: 2000-06-28

Application number

BG107376A

Other languages

Bulgarian (bg)

English (en)

Inventor

Andrew Mortlock

Frederic Jung

Original Assignee

Astrazeneca Ab

Priority date (The priority date 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 date listed.)

2000-06-28

Filing date

2002-12-11

Publication date

2003-09-30

2002-12-11 Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab

2003-09-30 Publication of BG107376A publication Critical patent/BG107376A/bg

Links

239000003112 inhibitor Substances 0.000 title 1
125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 990
238000002360 preparation method Methods 0.000 claims abstract description 392
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 78
239000001257 hydrogen Substances 0.000 claims abstract description 69
108090000461 Aurora Kinase A Proteins 0.000 claims abstract description 41
150000002148 esters Chemical class 0.000 claims abstract description 36
102100032311 Aurora kinase A Human genes 0.000 claims abstract description 33
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 20
150000003839 salts Chemical class 0.000 claims abstract description 20
229910052717 sulfur Inorganic materials 0.000 claims abstract description 16
150000001408 amides Chemical class 0.000 claims abstract description 15
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
229910052760 oxygen Inorganic materials 0.000 claims abstract description 14
239000003814 drug Substances 0.000 claims abstract description 8
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 5
-1 R 54 Chemical compound 0.000 claims description 223
125000000217 alkyl group Chemical group 0.000 claims description 134
229910052757 nitrogen Inorganic materials 0.000 claims description 74
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 68
125000000623 heterocyclic group Chemical group 0.000 claims description 54
125000003545 alkoxy group Chemical group 0.000 claims description 45
150000002431 hydrogen Chemical class 0.000 claims description 36
125000001424 substituent group Chemical group 0.000 claims description 32
125000003118 aryl group Chemical group 0.000 claims description 31
125000005843 halogen group Chemical group 0.000 claims description 27
125000002947 alkylene group Chemical group 0.000 claims description 23
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
229910052799 carbon Inorganic materials 0.000 claims description 21
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 19
125000001183 hydrocarbyl group Chemical group 0.000 claims description 16
238000000034 method Methods 0.000 claims description 16
241001465754 Metazoa Species 0.000 claims description 15
125000000547 substituted alkyl group Chemical group 0.000 claims description 15
125000004093 cyano group Chemical group *C#N 0.000 claims description 14
125000005842 heteroatom Chemical group 0.000 claims description 14
238000001727 in vivo Methods 0.000 claims description 14
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 12
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
125000001589 carboacyl group Chemical group 0.000 claims description 9
229910052736 halogen Inorganic materials 0.000 claims description 9
150000002367 halogens Chemical class 0.000 claims description 9
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
125000003282 alkyl amino group Chemical group 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 8
230000002401 inhibitory effect Effects 0.000 claims description 8
125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
125000004043 oxo group Chemical group O=* 0.000 claims description 8
125000003342 alkenyl group Chemical group 0.000 claims description 7
125000001841 imino group Chemical group [H]N=* 0.000 claims description 7
125000005017 substituted alkenyl group Chemical group 0.000 claims description 7
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 7
JQDFGZKKXBEANU-IMJSIDKUSA-N Ala-Cys Chemical compound C[C@H](N)C(=O)N[C@@H](CS)C(O)=O JQDFGZKKXBEANU-IMJSIDKUSA-N 0.000 claims description 6
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 6
150000001721 carbon Chemical group 0.000 claims description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 5
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 5
239000003795 chemical substances by application Substances 0.000 claims description 5
125000004423 acyloxy group Chemical group 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 4
125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 3
125000005236 alkanoylamino group Chemical group 0.000 claims description 3
125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 3
125000004122 cyclic group Chemical group 0.000 claims description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 claims description 3
101100219283 Amycolatopsis orientalis cyp165C4 gene Proteins 0.000 claims description 2
125000005153 alkyl sulfamoyl group Chemical group 0.000 claims description 2
XPHBRTNHVJSEQD-UHFFFAOYSA-N anidoxime Chemical compound C=1C=CC=CC=1C(CCN(CC)CC)=NOC(=O)NC1=CC=C(OC)C=C1 XPHBRTNHVJSEQD-UHFFFAOYSA-N 0.000 claims description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 2
LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 claims description 2
125000003226 pyrazolyl group Chemical group 0.000 claims description 2
UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical group OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 2
125000003831 tetrazolyl group Chemical group 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims 15
125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 1
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
239000008186 active pharmaceutical agent Substances 0.000 claims 1
230000005764 inhibitory process Effects 0.000 abstract description 5
238000006243 chemical reaction Methods 0.000 description 472
DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 378
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 288
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 122
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 114
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 108
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 98
239000000203 mixture Substances 0.000 description 94
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 88
239000007787 solid Substances 0.000 description 83
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 75
239000000243 solution Substances 0.000 description 70
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 64
239000002904 solvent Substances 0.000 description 60
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 55
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 50
238000004587 chromatography analysis Methods 0.000 description 47
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 43
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 42
239000003480 eluent Substances 0.000 description 42
239000000741 silica gel Substances 0.000 description 42
229910002027 silica gel Inorganic materials 0.000 description 42
YSEMCVGMNUUNRK-UHFFFAOYSA-N 3-chloro-4-fluoroaniline Chemical compound NC1=CC=C(F)C(Cl)=C1 YSEMCVGMNUUNRK-UHFFFAOYSA-N 0.000 description 37
210000004027 cell Anatomy 0.000 description 33
AXNUZKSSQHTNPZ-UHFFFAOYSA-N 3,4-difluoroaniline Chemical compound NC1=CC=C(F)C(F)=C1 AXNUZKSSQHTNPZ-UHFFFAOYSA-N 0.000 description 32
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 31
239000011541 reaction mixture Substances 0.000 description 28
235000019439 ethyl acetate Nutrition 0.000 description 26
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 25
PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 24
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 24
ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 22
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 22
125000002887 hydroxy group Chemical group [H]O* 0.000 description 22
RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 22
238000010992 reflux Methods 0.000 description 21
KQOIBXZRCYFZSO-UHFFFAOYSA-N 3,5-difluoroaniline Chemical compound NC1=CC(F)=CC(F)=C1 KQOIBXZRCYFZSO-UHFFFAOYSA-N 0.000 description 20
OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 20
239000002253 acid Substances 0.000 description 20
238000001914 filtration Methods 0.000 description 20
QZVQQUVWFIZUBQ-UHFFFAOYSA-N 3-fluoroaniline Chemical compound NC1=CC=CC(F)=C1 QZVQQUVWFIZUBQ-UHFFFAOYSA-N 0.000 description 19
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 18
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 18
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
206010028980 Neoplasm Diseases 0.000 description 18
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 description 17
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 16
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
239000004480 active ingredient Substances 0.000 description 16
239000012074 organic phase Substances 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 15
230000022131 cell cycle Effects 0.000 description 15
JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 14
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 14
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 14
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 14
125000000524 functional group Chemical group 0.000 description 14
RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 14
239000002244 precipitate Substances 0.000 description 14
201000010099 disease Diseases 0.000 description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 12
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 12
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
239000000725 suspension Substances 0.000 description 12
QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 11
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
150000001409 amidines Chemical class 0.000 description 11
HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 11
108090000623 proteins and genes Proteins 0.000 description 11
NJXPYZHXZZCTNI-UHFFFAOYSA-N 3-aminobenzonitrile Chemical compound NC1=CC=CC(C#N)=C1 NJXPYZHXZZCTNI-UHFFFAOYSA-N 0.000 description 10
KMHLGVTVACLEJE-UHFFFAOYSA-N 4-fluoro-2-methylaniline Chemical compound CC1=CC(F)=CC=C1N KMHLGVTVACLEJE-UHFFFAOYSA-N 0.000 description 10
NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 10
230000000694 effects Effects 0.000 description 10
VYFOAVADNIHPTR-UHFFFAOYSA-N isatoic anhydride Chemical compound NC1=CC=CC=C1CO VYFOAVADNIHPTR-UHFFFAOYSA-N 0.000 description 10
238000012360 testing method Methods 0.000 description 10
APIMXAGCLCGUGB-UHFFFAOYSA-N 2-(2-azaniumyl-1,3-thiazol-5-yl)acetate Chemical compound NC1=NC=C(CC(O)=O)S1 APIMXAGCLCGUGB-UHFFFAOYSA-N 0.000 description 9
229940058020 2-amino-2-methyl-1-propanol Drugs 0.000 description 9
125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 9
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 9
CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 9
230000015572 biosynthetic process Effects 0.000 description 9
201000011510 cancer Diseases 0.000 description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 9
239000003921 oil Substances 0.000 description 9
235000019198 oils Nutrition 0.000 description 9
229920006395 saturated elastomer Polymers 0.000 description 9
235000017557 sodium bicarbonate Nutrition 0.000 description 9
229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
238000003786 synthesis reaction Methods 0.000 description 9
QZUXMXZNVAJNSE-UHFFFAOYSA-N 2-fluoro-5-methylaniline Chemical compound CC1=CC=C(F)C(N)=C1 QZUXMXZNVAJNSE-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
150000001412 amines Chemical class 0.000 description 8
229910052786 argon Inorganic materials 0.000 description 8
239000000843 powder Substances 0.000 description 8
UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 8
AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 7
ZQEXBVHABAJPHJ-UHFFFAOYSA-N 2-fluoro-4-methylaniline Chemical compound CC1=CC=C(N)C(F)=C1 ZQEXBVHABAJPHJ-UHFFFAOYSA-N 0.000 description 7
108020004414 DNA Proteins 0.000 description 7
102000004190 Enzymes Human genes 0.000 description 7
108090000790 Enzymes Proteins 0.000 description 7
125000000304 alkynyl group Chemical group 0.000 description 7
238000003556 assay Methods 0.000 description 7
230000014509 gene expression Effects 0.000 description 7
238000007429 general method Methods 0.000 description 7
239000002609 medium Substances 0.000 description 7
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
SAQBFOVDJDGAGT-UHFFFAOYSA-N methyl 2-(2-amino-1,3-thiazol-5-yl)acetate Chemical compound COC(=O)CC1=CN=C(N)S1 SAQBFOVDJDGAGT-UHFFFAOYSA-N 0.000 description 7
239000003208 petroleum Substances 0.000 description 7
239000000546 pharmaceutical excipient Substances 0.000 description 7
230000002062 proliferating effect Effects 0.000 description 7
JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 description 7
239000011734 sodium Substances 0.000 description 7
ZWAQJGHGPPDZSF-UHFFFAOYSA-N 1-prop-2-enylpiperazine Chemical compound C=CCN1CCNCC1 ZWAQJGHGPPDZSF-UHFFFAOYSA-N 0.000 description 6
CEPCPXLLFXPZGW-UHFFFAOYSA-N 2,4-difluoroaniline Chemical compound NC1=CC=C(F)C=C1F CEPCPXLLFXPZGW-UHFFFAOYSA-N 0.000 description 6
YNOOQIUSYGWMSS-UHFFFAOYSA-N 2,5-difluoroaniline Chemical compound NC1=CC(F)=CC=C1F YNOOQIUSYGWMSS-UHFFFAOYSA-N 0.000 description 6
LDSQQXKSEFZAPE-UHFFFAOYSA-N 2-piperidin-4-ylethanol Chemical compound OCCC1CCNCC1 LDSQQXKSEFZAPE-UHFFFAOYSA-N 0.000 description 6
LJWAPDSCYTZUJU-UHFFFAOYSA-N 3-fluoro-4-methoxyaniline Chemical compound COC1=CC=C(N)C=C1F LJWAPDSCYTZUJU-UHFFFAOYSA-N 0.000 description 6
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 6
BMFVGAAISNGQNM-UHFFFAOYSA-N isopentylamine Chemical compound CC(C)CCN BMFVGAAISNGQNM-UHFFFAOYSA-N 0.000 description 6
VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 6
XBXHCBLBYQEYTI-UHFFFAOYSA-N piperidin-4-ylmethanol Chemical compound OCC1CCNCC1 XBXHCBLBYQEYTI-UHFFFAOYSA-N 0.000 description 6
102000004169 proteins and genes Human genes 0.000 description 6
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 6
239000012312 sodium hydride Substances 0.000 description 6
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NCJXQSNROJRSSL-UHFFFAOYSA-N tert-butyl n-(1,3-thiazol-2-yl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=NC=CS1 NCJXQSNROJRSSL-UHFFFAOYSA-N 0.000 description 1
SDXIYJKGYGSYTC-UHFFFAOYSA-N tert-butyl n-[4-(phenylcarbamoyl)thiophen-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CSC=C1C(=O)NC1=CC=CC=C1 SDXIYJKGYGSYTC-UHFFFAOYSA-N 0.000 description 1
DJULKKNDMGBJDR-UHFFFAOYSA-N tert-butyl n-[5-[2-(3,4-difluoroanilino)-1-hydroxy-2-oxoethyl]-1,3-thiazol-2-yl]carbamate Chemical compound S1C(NC(=O)OC(C)(C)C)=NC=C1C(O)C(=O)NC1=CC=C(F)C(F)=C1 DJULKKNDMGBJDR-UHFFFAOYSA-N 0.000 description 1
DBZJVUHTECVAPR-UHFFFAOYSA-N tert-butyl n-[5-[2-[(3-fluorophenyl)methylamino]-1-hydroxy-2-oxoethyl]-1,3-thiazol-2-yl]carbamate Chemical compound S1C(NC(=O)OC(C)(C)C)=NC=C1C(O)C(=O)NCC1=CC=CC(F)=C1 DBZJVUHTECVAPR-UHFFFAOYSA-N 0.000 description 1
229930101283 tetracycline Natural products 0.000 description 1
229960002180 tetracycline Drugs 0.000 description 1
235000019364 tetracycline Nutrition 0.000 description 1
150000003522 tetracyclines Chemical class 0.000 description 1
150000003536 tetrazoles Chemical class 0.000 description 1
150000004867 thiadiazoles Chemical class 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
125000005505 thiomorpholino group Chemical group 0.000 description 1
238000013518 transcription Methods 0.000 description 1
230000035897 transcription Effects 0.000 description 1
230000009466 transformation Effects 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
239000012588 trypsin Substances 0.000 description 1
229940121358 tyrosine kinase inhibitor Drugs 0.000 description 1
239000005483 tyrosine kinase inhibitor Substances 0.000 description 1
MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
235000012141 vanillin Nutrition 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
239000011534 wash buffer Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

BG107376A 2000-06-28 2002-12-11 Заместени хиназолинови производни и тяхното използване като инхибитори BG107376A (bg)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP00401842		2000-06-28
PCT/SE2001/001450 WO2002000649A1 (en)	2000-06-28	2001-06-21	Substituted quinazoline derivatives and their use as inhibitors

Publications (1)

Publication Number	Publication Date
BG107376A true BG107376A (bg)	2003-09-30

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Country Status (26)

Country	Link
US (2)	US6919338B2 (pl)
EP (1)	EP1299381B1 (pl)
JP (1)	JP2004501914A (pl)
KR (1)	KR20030014411A (pl)
CN (1)	CN1267431C (pl)
AR (1)	AR030432A1 (pl)
AT (1)	ATE394102T1 (pl)
AU (1)	AU2001266505A1 (pl)
BG (1)	BG107376A (pl)
BR (1)	BR0111754A (pl)
CA (1)	CA2412592A1 (pl)
CZ (1)	CZ20024120A3 (pl)
DE (1)	DE60133897D1 (pl)
EE (1)	EE200200715A (pl)
ES (1)	ES2305081T3 (pl)
HU (1)	HUP0301236A2 (pl)
IL (1)	IL153246A0 (pl)
IS (1)	IS6656A (pl)
MX (1)	MXPA02011974A (pl)
NO (1)	NO20026010D0 (pl)
NZ (1)	NZ522696A (pl)
PL (1)	PL360439A1 (pl)
RU (1)	RU2283311C2 (pl)
SK (1)	SK18102002A3 (pl)
WO (1)	WO2002000649A1 (pl)
ZA (1)	ZA200209412B (pl)

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2001
- 2001-06-21 NZ NZ522696A patent/NZ522696A/en unknown
- 2001-06-21 JP JP2002505773A patent/JP2004501914A/ja active Pending
- 2001-06-21 DE DE60133897T patent/DE60133897D1/de not_active Expired - Fee Related
- 2001-06-21 AT AT01944061T patent/ATE394102T1/de not_active IP Right Cessation
- 2001-06-21 AU AU2001266505A patent/AU2001266505A1/en not_active Abandoned
- 2001-06-21 CN CNB018146201A patent/CN1267431C/zh not_active Expired - Fee Related
- 2001-06-21 SK SK1810-2002A patent/SK18102002A3/sk unknown
- 2001-06-21 CA CA002412592A patent/CA2412592A1/en not_active Abandoned
- 2001-06-21 MX MXPA02011974A patent/MXPA02011974A/es unknown
- 2001-06-21 US US10/311,916 patent/US6919338B2/en not_active Expired - Fee Related
- 2001-06-21 HU HU0301236A patent/HUP0301236A2/hu unknown
- 2001-06-21 PL PL01360439A patent/PL360439A1/pl not_active Application Discontinuation
- 2001-06-21 EP EP01944061A patent/EP1299381B1/en not_active Expired - Lifetime
- 2001-06-21 CZ CZ20024120A patent/CZ20024120A3/cs unknown
- 2001-06-21 EE EEP200200715A patent/EE200200715A/xx unknown
- 2001-06-21 IL IL15324601A patent/IL153246A0/xx unknown
- 2001-06-21 ES ES01944061T patent/ES2305081T3/es not_active Expired - Lifetime
- 2001-06-21 WO PCT/SE2001/001450 patent/WO2002000649A1/en not_active Ceased
- 2001-06-21 BR BR0111754-8A patent/BR0111754A/pt not_active IP Right Cessation
- 2001-06-21 RU RU2003102389/04A patent/RU2283311C2/ru not_active IP Right Cessation
- 2001-06-21 KR KR1020027017913A patent/KR20030014411A/ko not_active Ceased
- 2001-06-28 AR ARP010103092A patent/AR030432A1/es not_active Application Discontinuation
2002
- 2002-11-19 ZA ZA200209412A patent/ZA200209412B/en unknown
- 2002-12-11 BG BG107376A patent/BG107376A/bg unknown
- 2002-12-13 NO NO20026010A patent/NO20026010D0/no unknown
- 2002-12-17 IS IS6656A patent/IS6656A/is unknown
2005
- 2005-03-02 US US11/070,057 patent/US20060046987A1/en not_active Abandoned

Also Published As

Publication number	Publication date
US6919338B2 (en)	2005-07-19
CN1267431C (zh)	2006-08-02
EE200200715A (et)	2004-08-16
NO20026010L (no)	2002-12-13
BR0111754A (pt)	2003-04-29
MXPA02011974A (es)	2004-09-06
JP2004501914A (ja)	2004-01-22
WO2002000649A1 (en)	2002-01-03
HK1053124A1 (en)	2003-10-10
RU2283311C2 (ru)	2006-09-10
IL153246A0 (en)	2003-07-06
AR030432A1 (es)	2003-08-20
ZA200209412B (en)	2004-02-19
CA2412592A1 (en)	2002-01-03
KR20030014411A (ko)	2003-02-17
NO20026010D0 (no)	2002-12-13
EP1299381A1 (en)	2003-04-09
WO2002000649A9 (en)	2007-09-20
ES2305081T3 (es)	2008-11-01
US20030187002A1 (en)	2003-10-02
CZ20024120A3 (cs)	2003-03-12
HUP0301236A2 (hu)	2003-10-28
IS6656A (is)	2002-12-17
ATE394102T1 (de)	2008-05-15
US20060046987A1 (en)	2006-03-02
SK18102002A3 (sk)	2003-07-01
DE60133897D1 (de)	2008-06-19
PL360439A1 (pl)	2004-09-06
NZ522696A (en)	2004-08-27
AU2001266505A1 (en)	2002-01-08
EP1299381B1 (en)	2008-05-07
CN1496364A (zh)	2004-05-12

Publication	Publication Date	Title
RU2283311C2 (ru)	2006-09-10	Замещенные производные хиназолина и их применение в качестве ингибиторов
JP4498741B2 (ja)	2010-07-07	オーロラキナーゼ阻害剤としての置換キナゾリン誘導体
US7709479B1 (en)	2010-05-04	Quinazoline derivatives and their use as pharmaceuticals
US7105669B1 (en)	2006-09-12	Quinazoline derivatives
US7081461B1 (en)	2006-07-25	Quinazoline compounds and pharmaceutical compositions containing them
KR100683512B1 (ko)	2007-02-16	피리미딘 화합물
US20030105129A1 (en)	2003-06-05	Chemical compounds
HK1053124B (en)	2008-08-22	Substituted quinazoline derivatives and their use as inhibitors