EA017585B1 - Производные хиназолинамида - Google Patents

Info

Publication number

EA017585B1

EA017585B1 EA201000098A EA201000098A EA017585B1 EA 017585 B1 EA017585 B1 EA 017585B1 EA 201000098 A EA201000098 A EA 201000098A EA 201000098 A EA201000098 A EA 201000098A EA 017585 B1 EA017585 B1 EA 017585B1

Authority

EA

Eurasian Patent Office

Prior art keywords

amino

benzyl

quinazoline

mono

phenyl

Prior art date

2007-07-13

Links

• Espacenet
• Global Dossier
• Discuss

• ABVYZAMNSCVWJA-UHFFFAOYSA-N quinazoline-2-carboxamide Chemical class C1=CC=CC2=NC(C(=O)N)=NC=C21 ABVYZAMNSCVWJA-UHFFFAOYSA-N 0.000 title abstract 2
• -1 benzo1,4-dioxanyl Chemical group 0.000 claims description 598
• 150000001875 compounds Chemical class 0.000 claims description 143
• 150000003839 salts Chemical class 0.000 claims description 65
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
• 125000004432 carbon atom Chemical group C* 0.000 claims description 29
• JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 27
• 125000002757 morpholinyl group Chemical group 0.000 claims description 24
• 125000003386 piperidinyl group Chemical group 0.000 claims description 24
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 24
• 125000004193 piperazinyl group Chemical group 0.000 claims description 21
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 19
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 16
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
• 125000000217 alkyl group Chemical group 0.000 claims description 15
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
• 229910052760 oxygen Inorganic materials 0.000 claims description 15
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
• 125000002541 furyl group Chemical group 0.000 claims description 13
• 125000002883 imidazolyl group Chemical group 0.000 claims description 13
• 125000004076 pyridyl group Chemical group 0.000 claims description 13
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 13
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 13
• 125000001544 thienyl group Chemical group 0.000 claims description 13
• 125000001425 triazolyl group Chemical group 0.000 claims description 13
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 12
• 229910052757 nitrogen Inorganic materials 0.000 claims description 12
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 10
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 10
• 125000003725 azepanyl group Chemical group 0.000 claims description 9
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 9
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
• 229920006395 saturated elastomer Polymers 0.000 claims description 9
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 8
• 239000004305 biphenyl Substances 0.000 claims description 8
• 235000010290 biphenyl Nutrition 0.000 claims description 8
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
• 125000005956 isoquinolyl group Chemical group 0.000 claims description 8
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 8
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 8
• 125000002971 oxazolyl group Chemical group 0.000 claims description 8
• 229910052698 phosphorus Inorganic materials 0.000 claims description 8
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 8
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 8
• 125000005493 quinolyl group Chemical group 0.000 claims description 8
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 8
• 125000000335 thiazolyl group Chemical group 0.000 claims description 8
• 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 7
• 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims description 7
• 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 7
• 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 7
• 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 7
• 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 7
• 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 claims description 7
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 7
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 7
• 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 7
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 7
• 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 6
• 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
• 125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims description 6
• 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 claims description 6
• 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 6
• 125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 claims description 6
• 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
• 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 6
• 125000004611 dihydroisoindolyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims description 6
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
• MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 claims description 5
• 125000003342 alkenyl group Chemical group 0.000 claims description 4
• 125000000304 alkynyl group Chemical group 0.000 claims description 4
• XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 claims description 4
• UFIVXJMKDABCDL-UHFFFAOYSA-N 2-amino-n-propan-2-ylquinazoline-4-carboxamide Chemical compound C1=CC=C2C(C(=O)NC(C)C)=NC(N)=NC2=C1 UFIVXJMKDABCDL-UHFFFAOYSA-N 0.000 claims description 3
• 125000004429 atom Chemical group 0.000 claims description 3
• 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 3
• CPTBLKRLSSEXSD-UHFFFAOYSA-N (2-aminoquinazolin-4-yl)-(3-hydroxypyrrolidin-1-yl)methanone Chemical compound C=12C=CC=CC2=NC(N)=NC=1C(=O)N1CCC(O)C1 CPTBLKRLSSEXSD-UHFFFAOYSA-N 0.000 claims description 2
• RKFLVIXLOXFNNL-UHFFFAOYSA-N 2-amino-4-(cyclopropylmethyl)-n-methylquinazoline-5-carboxamide Chemical compound C=12C(C(=O)NC)=CC=CC2=NC(N)=NC=1CC1CC1 RKFLVIXLOXFNNL-UHFFFAOYSA-N 0.000 claims description 2
• BVRFPDRSKFBRSO-UHFFFAOYSA-N 2-amino-4-butyl-n-methylquinazoline-5-carboxamide Chemical compound C1=CC(C(=O)NC)=C2C(CCCC)=NC(N)=NC2=C1 BVRFPDRSKFBRSO-UHFFFAOYSA-N 0.000 claims description 2
• GLSNSCVRQUSFFK-UHFFFAOYSA-N 2-amino-6-bromo-n,n-diethylquinazoline-4-carboxamide Chemical compound C1=C(Br)C=C2C(C(=O)N(CC)CC)=NC(N)=NC2=C1 GLSNSCVRQUSFFK-UHFFFAOYSA-N 0.000 claims description 2
• VOHJMASLAABYDA-UHFFFAOYSA-N 2-amino-n,n-diethylquinazoline-4-carboxamide Chemical compound C1=CC=C2C(C(=O)N(CC)CC)=NC(N)=NC2=C1 VOHJMASLAABYDA-UHFFFAOYSA-N 0.000 claims description 2
• OPZKQZATBWZGQX-UHFFFAOYSA-N 2-amino-n-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)quinazoline-4-carboxamide Chemical compound C1=CC=CC2=NC(N)=NC(C(=O)NCC=3C=C4OCCOC4=CC=3)=C21 OPZKQZATBWZGQX-UHFFFAOYSA-N 0.000 claims description 2
• RHYDTKGVWVDUSN-UHFFFAOYSA-N 2-amino-n-(2-methoxyethyl)-n-methylquinazoline-4-carboxamide Chemical compound C1=CC=C2C(C(=O)N(C)CCOC)=NC(N)=NC2=C1 RHYDTKGVWVDUSN-UHFFFAOYSA-N 0.000 claims description 2
• JFIFLVRDSHFTKD-UHFFFAOYSA-N 2-amino-n-(furan-2-ylmethyl)-n-methylquinazoline-4-carboxamide Chemical compound N=1C(N)=NC2=CC=CC=C2C=1C(=O)N(C)CC1=CC=CO1 JFIFLVRDSHFTKD-UHFFFAOYSA-N 0.000 claims description 2
• BPYJSXCFKXSSLU-UHFFFAOYSA-N 2-amino-n-but-3-ynylquinazoline-4-carboxamide Chemical compound C1=CC=CC2=NC(N)=NC(C(=O)NCCC#C)=C21 BPYJSXCFKXSSLU-UHFFFAOYSA-N 0.000 claims description 2
• NYZGTHMRHBIOBR-UHFFFAOYSA-N 2-amino-n-ethylquinazoline-4-carboxamide Chemical compound C1=CC=C2C(C(=O)NCC)=NC(N)=NC2=C1 NYZGTHMRHBIOBR-UHFFFAOYSA-N 0.000 claims description 2
• CLGRGSFGZKJTSO-UHFFFAOYSA-N 2-amino-n-methyl-4-(2-methylpropyl)quinazoline-5-carboxamide Chemical compound NC1=NC(CC(C)C)=C2C(C(=O)NC)=CC=CC2=N1 CLGRGSFGZKJTSO-UHFFFAOYSA-N 0.000 claims description 2
• CNHXXKBNKCLGDX-UHFFFAOYSA-N 2-amino-n-methyl-4-propylquinazoline-5-carboxamide Chemical compound C1=CC(C(=O)NC)=C2C(CCC)=NC(N)=NC2=C1 CNHXXKBNKCLGDX-UHFFFAOYSA-N 0.000 claims description 2
• OEIMMMLSRHBECJ-UHFFFAOYSA-N 2-amino-n-methylquinazoline-4-carboxamide Chemical compound C1=CC=C2C(C(=O)NC)=NC(N)=NC2=C1 OEIMMMLSRHBECJ-UHFFFAOYSA-N 0.000 claims description 2
• 244000099147 Ananas comosus Species 0.000 claims description 2
• 235000007119 Ananas comosus Nutrition 0.000 claims description 2
• 241001024304 Mino Species 0.000 claims description 2
• UOKNICPFCTUGJQ-UHFFFAOYSA-N N-(2-aminoethyl)-4-propylquinazoline-2-carboxamide Chemical compound NCCNC(=O)C1=NC2=CC=CC=C2C(=N1)CCC UOKNICPFCTUGJQ-UHFFFAOYSA-N 0.000 claims description 2
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
• PXAOIYKLWOEBDG-UHFFFAOYSA-N 2-amino-n-[2-(dimethylamino)ethyl]-n-methylquinazoline-4-carboxamide Chemical compound C1=CC=C2C(C(=O)N(C)CCN(C)C)=NC(N)=NC2=C1 PXAOIYKLWOEBDG-UHFFFAOYSA-N 0.000 claims 1
• 101100520142 Caenorhabditis elegans pin-2 gene Proteins 0.000 claims 1
• 244000208060 Lawsonia inermis Species 0.000 claims 1
• 101100345589 Mus musculus Mical1 gene Proteins 0.000 claims 1
• 241000933336 Ziziphus rignonii Species 0.000 claims 1
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 40
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• 201000010099 disease Diseases 0.000 abstract description 32
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• 230000033228 biological regulation Effects 0.000 abstract description 5
• 101710113864 Heat shock protein 90 Proteins 0.000 abstract 1
• 102100034051 Heat shock protein HSP 90-alpha Human genes 0.000 abstract 1
• 239000003481 heat shock protein 90 inhibitor Substances 0.000 abstract 1
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 110
• 239000000203 mixture Substances 0.000 description 73
• 238000005481 NMR spectroscopy Methods 0.000 description 63
• 235000002639 sodium chloride Nutrition 0.000 description 51
• 238000000034 method Methods 0.000 description 41
• 239000000243 solution Substances 0.000 description 37
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 35
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
• 238000002360 preparation method Methods 0.000 description 32
• 238000006243 chemical reaction Methods 0.000 description 29
• 108090000623 proteins and genes Proteins 0.000 description 29
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
• 102000004169 proteins and genes Human genes 0.000 description 27
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
• 229940079593 drug Drugs 0.000 description 20
• 206010028980 Neoplasm Diseases 0.000 description 19
• 210000004027 cell Anatomy 0.000 description 19
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
• 239000002253 acid Substances 0.000 description 18
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 18
• 239000002904 solvent Substances 0.000 description 18
• 238000004128 high performance liquid chromatography Methods 0.000 description 17
• 230000014759 maintenance of location Effects 0.000 description 17
• 239000002585 base Substances 0.000 description 16
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
• 239000003826 tablet Substances 0.000 description 13
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
• 239000000843 powder Substances 0.000 description 12
• 229910052796 boron Inorganic materials 0.000 description 11
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
• 150000001412 amines Chemical class 0.000 description 10
• 230000000694 effects Effects 0.000 description 10
• 239000008194 pharmaceutical composition Substances 0.000 description 10
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• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 9
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• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
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• 239000002775 capsule Substances 0.000 description 6
• NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 6
• 210000002472 endoplasmic reticulum Anatomy 0.000 description 6
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• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
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• 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 5
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• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 5
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 5
• 239000002244 precipitate Substances 0.000 description 5
• AYUNIORJHRXIBJ-TXHRRWQRSA-N tanespimycin Chemical compound N1C(=O)\C(C)=C\C=C/[C@H](OC)[C@@H](OC(N)=O)\C(C)=C\[C@H](C)[C@@H](O)[C@@H](OC)C[C@H](C)CC2=C(NCC=C)C(=O)C=C1C2=O AYUNIORJHRXIBJ-TXHRRWQRSA-N 0.000 description 5
• GSVUUDVORUNEGJ-UHFFFAOYSA-N (2-amino-6-iodoquinazolin-4-yl)-(1,3-dihydroisoindol-2-yl)methanone Chemical compound C1=C(I)C=CC2=NC(N)=NC(C(=O)N3CC4=CC=CC=C4C3)=C21 GSVUUDVORUNEGJ-UHFFFAOYSA-N 0.000 description 4
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
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