SK18102002A3 - Substituované chinazolínové deriváty, ich použitie a kompozícia obsahujúca tieto deriváty - Google Patents

Substituované chinazolínové deriváty, ich použitie a kompozícia obsahujúca tieto deriváty Download PDF

Info

Publication number: SK18102002A3
Authority: SK; Slovakia
Prior art keywords: alkyl; group; compound; mmol; alkoxy
Prior art date: 2000-06-28

Application number

SK1810-2002A

Other languages

English (en)

Slovak (sk)

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

2001-06-21

Publication date

2003-07-01

2001-06-21 Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab

2003-07-01 Publication of SK18102002A3 publication Critical patent/SK18102002A3/sk

Links

239000000203 mixture Substances 0.000 title claims description 107
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 1030
238000002360 preparation method Methods 0.000 claims abstract description 392
125000000217 alkyl group Chemical group 0.000 claims abstract description 85
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 55
239000001257 hydrogen Substances 0.000 claims abstract description 55
150000002148 esters Chemical class 0.000 claims abstract description 39
108090000461 Aurora Kinase A Proteins 0.000 claims abstract description 37
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 32
102100032311 Aurora kinase A Human genes 0.000 claims abstract description 29
150000003839 salts Chemical class 0.000 claims abstract description 18
150000001408 amides Chemical class 0.000 claims abstract description 17
229910052717 sulfur Inorganic materials 0.000 claims abstract description 15
229910052760 oxygen Inorganic materials 0.000 claims abstract description 14
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 12
239000003814 drug Substances 0.000 claims abstract description 8
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
-1 C 1-4 -alkyl Chemical group 0.000 claims description 164
229910052757 nitrogen Inorganic materials 0.000 claims description 55
125000000623 heterocyclic group Chemical group 0.000 claims description 37
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 34
125000001424 substituent group Chemical group 0.000 claims description 30
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
229910052736 halogen Inorganic materials 0.000 claims description 24
238000000034 method Methods 0.000 claims description 24
150000002367 halogens Chemical class 0.000 claims description 23
150000002431 hydrogen Chemical class 0.000 claims description 23
125000004432 carbon atom Chemical group C* 0.000 claims description 18
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
125000005842 heteroatom Chemical group 0.000 claims description 14
229920006395 saturated elastomer Polymers 0.000 claims description 14
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
229910052799 carbon Inorganic materials 0.000 claims description 12
238000001727 in vivo Methods 0.000 claims description 12
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
239000001301 oxygen Substances 0.000 claims description 11
239000011593 sulfur Substances 0.000 claims description 11
241001465754 Metazoa Species 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
125000004093 cyano group Chemical group *C#N 0.000 claims description 9
125000004043 oxo group Chemical group O=* 0.000 claims description 8
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
230000002401 inhibitory effect Effects 0.000 claims description 6
125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 5
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 4
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
JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 claims description 3
125000003226 pyrazolyl group Chemical group 0.000 claims description 3
125000003831 tetrazolyl group Chemical class 0.000 claims description 3
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
239000003937 drug carrier Substances 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
UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical group OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 2
238000002560 therapeutic procedure Methods 0.000 claims description 2
AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 claims 1
125000004433 nitrogen atom Chemical group N* 0.000 claims 1
230000005764 inhibitory process Effects 0.000 abstract description 7
238000005160 1H NMR spectroscopy Methods 0.000 description 531
238000006243 chemical reaction Methods 0.000 description 469
DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 315
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 272
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 200
239000007858 starting material Substances 0.000 description 165
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 152
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 124
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 111
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 107
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 98
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 94
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 78
239000007787 solid Substances 0.000 description 78
239000000243 solution Substances 0.000 description 68
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 66
239000002904 solvent Substances 0.000 description 61
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 60
BXPGOVASPWDJAJ-UHFFFAOYSA-N methylsulfinylmethane;2,2,2-trifluoroacetic acid Chemical compound CS(C)=O.OC(=O)C(F)(F)F BXPGOVASPWDJAJ-UHFFFAOYSA-N 0.000 description 57
239000000460 chlorine Substances 0.000 description 52
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 49
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 46
239000003480 eluent Substances 0.000 description 41
238000010898 silica gel chromatography Methods 0.000 description 36
210000004027 cell Anatomy 0.000 description 33
235000019439 ethyl acetate Nutrition 0.000 description 32
239000011541 reaction mixture Substances 0.000 description 32
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 31
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 30
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 29
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 28
235000011121 sodium hydroxide Nutrition 0.000 description 26
125000003118 aryl group Chemical group 0.000 description 24
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 24
125000003545 alkoxy group Chemical group 0.000 description 23
ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 22
RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 22
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 20
239000002244 precipitate Substances 0.000 description 19
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
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 18
PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 17
KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 description 17
206010028980 Neoplasm Diseases 0.000 description 17
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 16
AXNUZKSSQHTNPZ-UHFFFAOYSA-N 3,4-difluoroaniline Chemical compound NC1=CC=C(F)C(F)=C1 AXNUZKSSQHTNPZ-UHFFFAOYSA-N 0.000 description 15
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 15
239000004480 active ingredient Substances 0.000 description 15
239000012074 organic phase Substances 0.000 description 15
YSEMCVGMNUUNRK-UHFFFAOYSA-N 3-chloro-4-fluoroaniline Chemical compound NC1=CC=C(F)C(Cl)=C1 YSEMCVGMNUUNRK-UHFFFAOYSA-N 0.000 description 14
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 14
QZVQQUVWFIZUBQ-UHFFFAOYSA-N 3-fluoroaniline Chemical compound NC1=CC=CC(F)=C1 QZVQQUVWFIZUBQ-UHFFFAOYSA-N 0.000 description 14
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 14
JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 14
OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-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
230000022131 cell cycle Effects 0.000 description 14
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 13
125000000524 functional group Chemical group 0.000 description 13
238000010992 reflux Methods 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 12
238000004587 chromatography analysis Methods 0.000 description 12
201000010099 disease Diseases 0.000 description 12
208000037265 diseases, disorders, signs and symptoms Diseases 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
239000002253 acid Substances 0.000 description 11
150000001409 amidines Chemical class 0.000 description 11
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 11
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
239000003921 oil Substances 0.000 description 11
235000019198 oils Nutrition 0.000 description 11
108090000623 proteins and genes Proteins 0.000 description 11
235000017557 sodium bicarbonate Nutrition 0.000 description 11
229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 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
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
230000015572 biosynthetic process Effects 0.000 description 10
238000009835 boiling Methods 0.000 description 10
230000000694 effects Effects 0.000 description 10
238000001914 filtration Methods 0.000 description 10
125000001183 hydrocarbyl group Chemical group 0.000 description 10
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 10
HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 10
238000003786 synthesis reaction Methods 0.000 description 10
238000012360 testing method Methods 0.000 description 10
FTZQXOJYPFINKJ-UHFFFAOYSA-N 2-fluoroaniline Chemical compound NC1=CC=CC=C1F FTZQXOJYPFINKJ-UHFFFAOYSA-N 0.000 description 9
NJXPYZHXZZCTNI-UHFFFAOYSA-N 3-aminobenzonitrile Chemical compound NC1=CC=CC(C#N)=C1 NJXPYZHXZZCTNI-UHFFFAOYSA-N 0.000 description 9
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
238000003556 assay Methods 0.000 description 9
201000011510 cancer Diseases 0.000 description 9
NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 9
239000000725 suspension Substances 0.000 description 9
AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 8
LJWAPDSCYTZUJU-UHFFFAOYSA-N 3-fluoro-4-methoxyaniline Chemical compound COC1=CC=C(N)C=C1F LJWAPDSCYTZUJU-UHFFFAOYSA-N 0.000 description 8
108020004414 DNA Proteins 0.000 description 8
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 8
125000002947 alkylene group Chemical group 0.000 description 8
150000001412 amines Chemical class 0.000 description 8
NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 8
239000002609 medium Substances 0.000 description 8
239000000843 powder Substances 0.000 description 8
230000002062 proliferating effect Effects 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
CEPCPXLLFXPZGW-UHFFFAOYSA-N 2,4-difluoroaniline Chemical compound NC1=CC=C(F)C=C1F CEPCPXLLFXPZGW-UHFFFAOYSA-N 0.000 description 7
YNOOQIUSYGWMSS-UHFFFAOYSA-N 2,5-difluoroaniline Chemical compound NC1=CC(F)=CC=C1F YNOOQIUSYGWMSS-UHFFFAOYSA-N 0.000 description 7
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 description 7
KQOIBXZRCYFZSO-UHFFFAOYSA-N 3,5-difluoroaniline Chemical compound NC1=CC(F)=CC(F)=C1 KQOIBXZRCYFZSO-UHFFFAOYSA-N 0.000 description 7
XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 7
108091003079 Bovine Serum Albumin Proteins 0.000 description 7
102000004190 Enzymes Human genes 0.000 description 7
108090000790 Enzymes Proteins 0.000 description 7
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 7
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 7
230000014509 gene expression Effects 0.000 description 7
VYFOAVADNIHPTR-UHFFFAOYSA-N isatoic anhydride Chemical compound NC1=CC=CC=C1CO VYFOAVADNIHPTR-UHFFFAOYSA-N 0.000 description 7
VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 7
239000003208 petroleum Substances 0.000 description 7
239000000546 pharmaceutical excipient Substances 0.000 description 7
239000011734 sodium Substances 0.000 description 7
238000003756 stirring Methods 0.000 description 7
229940058020 2-amino-2-methyl-1-propanol Drugs 0.000 description 6
LDSQQXKSEFZAPE-UHFFFAOYSA-N 2-piperidin-4-ylethanol Chemical compound OCCC1CCNCC1 LDSQQXKSEFZAPE-UHFFFAOYSA-N 0.000 description 6
CSFDTBRRIBJILD-UHFFFAOYSA-N 4-chloro-2-fluoroaniline Chemical compound NC1=CC=C(Cl)C=C1F CSFDTBRRIBJILD-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
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
108091000080 Phosphotransferase Proteins 0.000 description 6
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
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KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 6
239000012894 fetal calf serum Substances 0.000 description 6
HVOYZOQVDYHUPF-UHFFFAOYSA-N n,n',n'-trimethylethane-1,2-diamine Chemical compound CNCCN(C)C HVOYZOQVDYHUPF-UHFFFAOYSA-N 0.000 description 6
102000020233 phosphotransferase Human genes 0.000 description 6
239000003755 preservative agent Substances 0.000 description 6
239000000047 product Substances 0.000 description 6
102000004169 proteins and genes Human genes 0.000 description 6
JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 description 6
150000003246 quinazolines Chemical class 0.000 description 6
230000002829 reductive effect Effects 0.000 description 6
239000012312 sodium hydride Substances 0.000 description 6
229910000104 sodium hydride Inorganic materials 0.000 description 6
239000003765 sweetening agent Substances 0.000 description 6
229930192474 thiophene Natural products 0.000 description 6
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 6
DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 6
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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
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- 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
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- 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
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- 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
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- 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
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- 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

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SK1810-2002A 2000-06-28 2001-06-21 Substituované chinazolínové deriváty, ich použitie a kompozícia obsahujúca tieto deriváty SK18102002A3 (sk)

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EP00401842		2000-06-28
PCT/SE2001/001450 WO2002000649A1 (en)	2000-06-28	2001-06-21	Substituted quinazoline derivatives and their use as inhibitors

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US (2)	US6919338B2 (de)
EP (1)	EP1299381B1 (de)
JP (1)	JP2004501914A (de)
KR (1)	KR20030014411A (de)
CN (1)	CN1267431C (de)
AR (1)	AR030432A1 (de)
AT (1)	ATE394102T1 (de)
AU (1)	AU2001266505A1 (de)
BG (1)	BG107376A (de)
BR (1)	BR0111754A (de)
CA (1)	CA2412592A1 (de)
CZ (1)	CZ20024120A3 (de)
DE (1)	DE60133897D1 (de)
EE (1)	EE200200715A (de)
ES (1)	ES2305081T3 (de)
HU (1)	HUP0301236A2 (de)
IL (1)	IL153246A0 (de)
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MX (1)	MXPA02011974A (de)
NO (1)	NO20026010L (de)
NZ (1)	NZ522696A (de)
PL (1)	PL360439A1 (de)
RU (1)	RU2283311C2 (de)
SK (1)	SK18102002A3 (de)
WO (1)	WO2002000649A1 (de)
ZA (1)	ZA200209412B (de)

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2001
- 2001-06-21 PL PL01360439A patent/PL360439A1/xx not_active Application Discontinuation
- 2001-06-21 ES ES01944061T patent/ES2305081T3/es not_active Expired - Lifetime
- 2001-06-21 KR KR1020027017913A patent/KR20030014411A/ko not_active Ceased
- 2001-06-21 EP EP01944061A patent/EP1299381B1/de not_active Expired - Lifetime
- 2001-06-21 RU RU2003102389/04A patent/RU2283311C2/ru not_active IP Right Cessation
- 2001-06-21 MX MXPA02011974A patent/MXPA02011974A/es unknown
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- 2001-06-21 HU HU0301236A patent/HUP0301236A2/hu unknown
- 2001-06-21 DE DE60133897T patent/DE60133897D1/de not_active Expired - Fee Related
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- 2001-06-21 CZ CZ20024120A patent/CZ20024120A3/cs unknown
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- 2001-06-21 AU AU2001266505A patent/AU2001266505A1/en not_active Abandoned
- 2001-06-21 JP JP2002505773A patent/JP2004501914A/ja active Pending
- 2001-06-28 AR ARP010103092A patent/AR030432A1/es not_active Application Discontinuation
2002
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- 2002-12-13 NO NO20026010A patent/NO20026010L/no unknown
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Also Published As

Publication number	Publication date
EE200200715A (et)	2004-08-16
CZ20024120A3 (cs)	2003-03-12
EP1299381A1 (de)	2003-04-09
NO20026010D0 (no)	2002-12-13
HK1053124A1 (en)	2003-10-10
IL153246A0 (en)	2003-07-06
CN1267431C (zh)	2006-08-02
MXPA02011974A (es)	2004-09-06
AR030432A1 (es)	2003-08-20
IS6656A (is)	2002-12-17
BG107376A (bg)	2003-09-30
NZ522696A (en)	2004-08-27
JP2004501914A (ja)	2004-01-22
ATE394102T1 (de)	2008-05-15
US6919338B2 (en)	2005-07-19
ZA200209412B (en)	2004-02-19
NO20026010L (no)	2002-12-13
CN1496364A (zh)	2004-05-12
AU2001266505A1 (en)	2002-01-08
PL360439A1 (en)	2004-09-06
ES2305081T3 (es)	2008-11-01
WO2002000649A9 (en)	2007-09-20
KR20030014411A (ko)	2003-02-17
HUP0301236A2 (hu)	2003-10-28
US20030187002A1 (en)	2003-10-02
EP1299381B1 (de)	2008-05-07
WO2002000649A1 (en)	2002-01-03
RU2283311C2 (ru)	2006-09-10
DE60133897D1 (de)	2008-06-19
CA2412592A1 (en)	2002-01-03
BR0111754A (pt)	2003-04-29
US20060046987A1 (en)	2006-03-02

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