SK285405B6 - Bicyklické heteroaromatické zlúčeniny, spôsob ichprípravy, farmaceutický prostriedok s ich obsahoma ich použitie - Google Patents
Bicyklické heteroaromatické zlúčeniny, spôsob ichprípravy, farmaceutický prostriedok s ich obsahoma ich použitie Download PDFInfo
- Publication number
- SK285405B6 SK285405B6 SK1050-2000A SK10502000A SK285405B6 SK 285405 B6 SK285405 B6 SK 285405B6 SK 10502000 A SK10502000 A SK 10502000A SK 285405 B6 SK285405 B6 SK 285405B6
- Authority
- SK
- Slovakia
- Prior art keywords
- methyl
- ethyl
- amino
- fluorobenzyloxy
- quinazolinamine
- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 19
- -1 Bicyclic heteroaromatic compounds Chemical class 0.000 title claims description 138
- 238000004519 manufacturing process Methods 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 118
- 238000011282 treatment Methods 0.000 claims abstract description 27
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 17
- 238000002360 preparation method Methods 0.000 claims abstract description 15
- 101710100968 Receptor tyrosine-protein kinase erbB-2 Proteins 0.000 claims abstract description 13
- 102100030086 Receptor tyrosine-protein kinase erbB-2 Human genes 0.000 claims abstract description 13
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 12
- 201000011510 cancer Diseases 0.000 claims abstract description 11
- 239000003814 drug Substances 0.000 claims abstract description 10
- 230000001404 mediated effect Effects 0.000 claims abstract description 7
- 150000003839 salts Chemical class 0.000 claims description 39
- 239000012453 solvate Substances 0.000 claims description 27
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 239000004480 active ingredient Substances 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 208000035475 disorder Diseases 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 10
- 108060006698 EGF receptor Proteins 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 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
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 201000004681 Psoriasis Diseases 0.000 claims description 6
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 5
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 5
- 125000000335 thiazolyl group Chemical group 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- BCFGMOOMADDAQU-UHFFFAOYSA-N lapatinib Chemical compound O1C(CNCCS(=O)(=O)C)=CC=C1C1=CC=C(N=CN=C2NC=3C=C(Cl)C(OCC=4C=C(F)C=CC=4)=CC=3)C2=C1 BCFGMOOMADDAQU-UHFFFAOYSA-N 0.000 claims description 3
- MNHCZHFLNIOWQH-UHFFFAOYSA-N n-[3-fluoro-4-[(3-fluorophenyl)methoxy]phenyl]-6-[5-[(2-methylsulfonylethylamino)methyl]furan-2-yl]quinazolin-4-amine Chemical compound O1C(CNCCS(=O)(=O)C)=CC=C1C1=CC=C(N=CN=C2NC=3C=C(F)C(OCC=4C=C(F)C=CC=4)=CC=3)C2=C1 MNHCZHFLNIOWQH-UHFFFAOYSA-N 0.000 claims description 3
- QEHYWVNDAWPVRJ-UHFFFAOYSA-N n-[4-[(3-fluorophenyl)methoxy]phenyl]-6-[2-[(2-methylsulfonylethylamino)methyl]-1,3-thiazol-4-yl]quinazolin-4-amine Chemical compound S1C(CNCCS(=O)(=O)C)=NC(C=2C=C3C(NC=4C=CC(OCC=5C=C(F)C=CC=5)=CC=4)=NC=NC3=CC=2)=C1 QEHYWVNDAWPVRJ-UHFFFAOYSA-N 0.000 claims description 3
- RZEMPBRXCDBLDH-UHFFFAOYSA-N n-[4-[(3-fluorophenyl)methoxy]phenyl]-6-[5-[(2-methylsulfonylethylamino)methyl]furan-2-yl]quinazolin-4-amine Chemical compound O1C(CNCCS(=O)(=O)C)=CC=C1C1=CC=C(N=CN=C2NC=3C=CC(OCC=4C=C(F)C=CC=4)=CC=3)C2=C1 RZEMPBRXCDBLDH-UHFFFAOYSA-N 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 206010006187 Breast cancer Diseases 0.000 claims description 2
- 208000026310 Breast neoplasm Diseases 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- ZADGIWJEHDJLCZ-UHFFFAOYSA-N n-(3-bromo-4-phenylmethoxyphenyl)-7-fluoro-6-[5-[(2-methylsulfonylethylamino)methyl]furan-2-yl]quinazolin-4-amine Chemical compound O1C(CNCCS(=O)(=O)C)=CC=C1C(C(=CC1=NC=N2)F)=CC1=C2NC(C=C1Br)=CC=C1OCC1=CC=CC=C1 ZADGIWJEHDJLCZ-UHFFFAOYSA-N 0.000 claims description 2
- NKLDCSQPJCETMA-UHFFFAOYSA-N n-(3-bromo-4-phenylmethoxyphenyl)-7-methoxy-6-[5-[(2-methylsulfonylethylamino)methyl]furan-2-yl]quinazolin-4-amine Chemical compound C=12C=C(C=3OC(CNCCS(C)(=O)=O)=CC=3)C(OC)=CC2=NC=NC=1NC(C=C1Br)=CC=C1OCC1=CC=CC=C1 NKLDCSQPJCETMA-UHFFFAOYSA-N 0.000 claims description 2
- AXVKGZLOECWENV-UHFFFAOYSA-N n-(3-chloro-4-phenylmethoxyphenyl)-6-[2-[(2-methylsulfonylethylamino)methyl]-1,3-thiazol-4-yl]quinazolin-4-amine Chemical compound S1C(CNCCS(=O)(=O)C)=NC(C=2C=C3C(NC=4C=C(Cl)C(OCC=5C=CC=CC=5)=CC=4)=NC=NC3=CC=2)=C1 AXVKGZLOECWENV-UHFFFAOYSA-N 0.000 claims description 2
- NOJHSHOVOCTOHJ-UHFFFAOYSA-N n-(3-chloro-4-phenylmethoxyphenyl)-7-fluoro-6-[5-[(2-methylsulfonylethylamino)methyl]furan-2-yl]quinazolin-4-amine Chemical compound O1C(CNCCS(=O)(=O)C)=CC=C1C(C(=CC1=NC=N2)F)=CC1=C2NC(C=C1Cl)=CC=C1OCC1=CC=CC=C1 NOJHSHOVOCTOHJ-UHFFFAOYSA-N 0.000 claims description 2
- UTGTXIQFRUQSMS-UHFFFAOYSA-N n-(3-chloro-4-phenylmethoxyphenyl)-7-methoxy-6-[2-[(2-methylsulfonylethylamino)methyl]-1,3-thiazol-4-yl]quinazolin-4-amine Chemical compound C=12C=C(C=3N=C(CNCCS(C)(=O)=O)SC=3)C(OC)=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=C1 UTGTXIQFRUQSMS-UHFFFAOYSA-N 0.000 claims description 2
- GITHWNVRQPKFEJ-UHFFFAOYSA-N n-(3-fluoro-4-phenylmethoxyphenyl)-6-[5-[(2-methylsulfonylethylamino)methyl]furan-2-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound O1C(CNCCS(=O)(=O)C)=CC=C1C(N=CC1=NC=N2)=CC1=C2NC(C=C1F)=CC=C1OCC1=CC=CC=C1 GITHWNVRQPKFEJ-UHFFFAOYSA-N 0.000 claims description 2
- GFRIWQBALIBSCZ-UHFFFAOYSA-N n-(3-fluoro-4-phenylmethoxyphenyl)-7-methoxy-6-[5-[(2-methylsulfonylethylamino)methyl]furan-2-yl]quinazolin-4-amine Chemical compound C=12C=C(C=3OC(CNCCS(C)(=O)=O)=CC=3)C(OC)=CC2=NC=NC=1NC(C=C1F)=CC=C1OCC1=CC=CC=C1 GFRIWQBALIBSCZ-UHFFFAOYSA-N 0.000 claims description 2
- FVRXRENVHJBKFO-UHFFFAOYSA-N n-[3-bromo-4-[(3-fluorophenyl)methoxy]phenyl]-7-fluoro-6-[5-[(2-methylsulfonylethylamino)methyl]furan-2-yl]quinazolin-4-amine Chemical compound O1C(CNCCS(=O)(=O)C)=CC=C1C(C(=CC1=NC=N2)F)=CC1=C2NC(C=C1Br)=CC=C1OCC1=CC=CC(F)=C1 FVRXRENVHJBKFO-UHFFFAOYSA-N 0.000 claims description 2
- QLHIYBDUQPWZAA-UHFFFAOYSA-N n-[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]-7-fluoro-6-[5-[(2-methylsulfonylethylamino)methyl]furan-2-yl]quinazolin-4-amine Chemical compound O1C(CNCCS(=O)(=O)C)=CC=C1C(C(=CC1=NC=N2)F)=CC1=C2NC(C=C1Cl)=CC=C1OCC1=CC=CC(F)=C1 QLHIYBDUQPWZAA-UHFFFAOYSA-N 0.000 claims description 2
- WIDSGQVCKXSTPB-UHFFFAOYSA-N n-[3-fluoro-4-[(3-fluorophenyl)methoxy]phenyl]-6-[2-[(2-methylsulfonylethylamino)methyl]-1,3-thiazol-4-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound S1C(CNCCS(=O)(=O)C)=NC(C=2N=CC3=NC=NC(NC=4C=C(F)C(OCC=5C=C(F)C=CC=5)=CC=4)=C3C=2)=C1 WIDSGQVCKXSTPB-UHFFFAOYSA-N 0.000 claims description 2
- YAPPGADRBQSUIE-UHFFFAOYSA-N n-[4-[(3-fluorophenyl)methoxy]-3-methoxyphenyl]-6-[2-[(2-methylsulfonylethylamino)methyl]-1,3-thiazol-4-yl]quinazolin-4-amine Chemical compound C=1C=C(OCC=2C=C(F)C=CC=2)C(OC)=CC=1NC(C1=C2)=NC=NC1=CC=C2C1=CSC(CNCCS(C)(=O)=O)=N1 YAPPGADRBQSUIE-UHFFFAOYSA-N 0.000 claims description 2
- ZUPCLUORSUOTAD-UHFFFAOYSA-N 4-[2-[(3-fluorophenyl)methoxy]phenyl]-6-[4-[(2-methylsulfonylethylamino)methyl]furan-2-yl]-1h-pyrido[3,4-d]pyrimidin-4-amine Chemical compound CS(=O)(=O)CCNCC1=COC(C=2N=CC3=C(C(N=CN3)(N)C=3C(=CC=CC=3)OCC=3C=C(F)C=CC=3)C=2)=C1 ZUPCLUORSUOTAD-UHFFFAOYSA-N 0.000 claims 1
- CMPYWDJZUOBIIO-UHFFFAOYSA-N 7-fluoro-n-(3-fluoro-4-phenylmethoxyphenyl)-6-[5-[(2-methylsulfonylethylamino)methyl]furan-2-yl]quinazolin-4-amine Chemical compound O1C(CNCCS(=O)(=O)C)=CC=C1C(C(=CC1=NC=N2)F)=CC1=C2NC(C=C1F)=CC=C1OCC1=CC=CC=C1 CMPYWDJZUOBIIO-UHFFFAOYSA-N 0.000 claims 1
- YOHWLAPRGKJAEL-UHFFFAOYSA-N 7-fluoro-n-[3-fluoro-4-[(3-fluorophenyl)methoxy]phenyl]-6-[5-[(2-methylsulfonylethylamino)methyl]furan-2-yl]quinazolin-4-amine Chemical compound O1C(CNCCS(=O)(=O)C)=CC=C1C(C(=CC1=NC=N2)F)=CC1=C2NC(C=C1F)=CC=C1OCC1=CC=CC(F)=C1 YOHWLAPRGKJAEL-UHFFFAOYSA-N 0.000 claims 1
- 206010005003 Bladder cancer Diseases 0.000 claims 1
- HMWAXNWFVBPMKK-UHFFFAOYSA-N CCNCC1=NC(=CS1)C2=NC=C3C(=C2)C(=NC=N3)NC4=CC(=C(C=C4)OCC5=CC(=CC=C5)F)Cl Chemical compound CCNCC1=NC(=CS1)C2=NC=C3C(=C2)C(=NC=N3)NC4=CC(=C(C=C4)OCC5=CC(=CC=C5)F)Cl HMWAXNWFVBPMKK-UHFFFAOYSA-N 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- MNNXRVSQOABRRP-UHFFFAOYSA-N N-[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]-6-[2-[(2-methylsulfonylethylamino)methyl]-4-thiazolyl]-4-quinazolinamine Chemical compound S1C(CNCCS(=O)(=O)C)=NC(C=2C=C3C(NC=4C=C(Cl)C(OCC=5C=C(F)C=CC=5)=CC=4)=NC=NC3=CC=2)=C1 MNNXRVSQOABRRP-UHFFFAOYSA-N 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
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- HQHSVSSDBPWQBD-UHFFFAOYSA-N n-(3-bromo-4-phenylmethoxyphenyl)-6-[2-[(2-methylsulfonylethylamino)methyl]-1,3-thiazol-4-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound S1C(CNCCS(=O)(=O)C)=NC(C=2N=CC3=NC=NC(NC=4C=C(Br)C(OCC=5C=CC=CC=5)=CC=4)=C3C=2)=C1 HQHSVSSDBPWQBD-UHFFFAOYSA-N 0.000 claims 1
- LPHALCCJJMLFMZ-UHFFFAOYSA-N n-(3-chloro-4-phenylmethoxyphenyl)-6-[2-[(2-methylsulfonylethylamino)methyl]-1,3-thiazol-4-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound S1C(CNCCS(=O)(=O)C)=NC(C=2N=CC3=NC=NC(NC=4C=C(Cl)C(OCC=5C=CC=CC=5)=CC=4)=C3C=2)=C1 LPHALCCJJMLFMZ-UHFFFAOYSA-N 0.000 claims 1
- WVPMKVVGRCIEBV-UHFFFAOYSA-N n-(3-chloro-4-phenylmethoxyphenyl)-6-[5-[(2-methylsulfonylethylamino)methyl]furan-3-yl]quinazolin-4-amine Chemical compound O1C(CNCCS(=O)(=O)C)=CC(C=2C=C3C(NC=4C=C(Cl)C(OCC=5C=CC=CC=5)=CC=4)=NC=NC3=CC=2)=C1 WVPMKVVGRCIEBV-UHFFFAOYSA-N 0.000 claims 1
- INOHEVIDYKGWNH-UHFFFAOYSA-N n-(3-chloro-4-phenylmethoxyphenyl)-7-methoxy-6-[5-[(2-methylsulfonylethylamino)methyl]furan-2-yl]quinazolin-4-amine Chemical compound C=12C=C(C=3OC(CNCCS(C)(=O)=O)=CC=3)C(OC)=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=C1 INOHEVIDYKGWNH-UHFFFAOYSA-N 0.000 claims 1
- RPBYFFUZCIDSBL-UHFFFAOYSA-N n-(3-fluoro-4-phenylmethoxyphenyl)-6-[2-[(2-methylsulfonylethylamino)methyl]-1,3-thiazol-4-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound S1C(CNCCS(=O)(=O)C)=NC(C=2N=CC3=NC=NC(NC=4C=C(F)C(OCC=5C=CC=CC=5)=CC=4)=C3C=2)=C1 RPBYFFUZCIDSBL-UHFFFAOYSA-N 0.000 claims 1
- IVNDWQOKRSEWBH-UHFFFAOYSA-N n-[3-bromo-4-[(3-fluorophenyl)methoxy]phenyl]-6-[2-[(2-methylsulfonylethylamino)methyl]-1,3-thiazol-4-yl]quinazolin-4-amine Chemical compound S1C(CNCCS(=O)(=O)C)=NC(C=2C=C3C(NC=4C=C(Br)C(OCC=5C=C(F)C=CC=5)=CC=4)=NC=NC3=CC=2)=C1 IVNDWQOKRSEWBH-UHFFFAOYSA-N 0.000 claims 1
- OKOQGGNYPJNMTO-UHFFFAOYSA-N n-[3-bromo-4-[(3-fluorophenyl)methoxy]phenyl]-6-[5-[(2-methylsulfonylethylamino)methyl]furan-2-yl]quinazolin-4-amine Chemical compound O1C(CNCCS(=O)(=O)C)=CC=C1C1=CC=C(N=CN=C2NC=3C=C(Br)C(OCC=4C=C(F)C=CC=4)=CC=3)C2=C1 OKOQGGNYPJNMTO-UHFFFAOYSA-N 0.000 claims 1
- UODLBPXYHJNREK-UHFFFAOYSA-N n-[3-bromo-4-[(3-fluorophenyl)methoxy]phenyl]-7-methoxy-6-[5-[(2-methylsulfonylethylamino)methyl]furan-2-yl]quinazolin-4-amine Chemical compound C=12C=C(C=3OC(CNCCS(C)(=O)=O)=CC=3)C(OC)=CC2=NC=NC=1NC(C=C1Br)=CC=C1OCC1=CC=CC(F)=C1 UODLBPXYHJNREK-UHFFFAOYSA-N 0.000 claims 1
- QKXNWCXDCUQVGR-UHFFFAOYSA-N n-[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]-6-[5-[(2-methylsulfonylethylamino)methyl]furan-2-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound O1C(CNCCS(=O)(=O)C)=CC=C1C(N=CC1=NC=N2)=CC1=C2NC(C=C1Cl)=CC=C1OCC1=CC=CC(F)=C1 QKXNWCXDCUQVGR-UHFFFAOYSA-N 0.000 claims 1
- HNCNTMHPAYQWSL-UHFFFAOYSA-N n-[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]-7-fluoro-6-[2-[(2-methylsulfonylethylamino)methyl]-1,3-thiazol-4-yl]quinazolin-4-amine Chemical compound S1C(CNCCS(=O)(=O)C)=NC(C=2C(=CC3=NC=NC(NC=4C=C(Cl)C(OCC=5C=C(F)C=CC=5)=CC=4)=C3C=2)F)=C1 HNCNTMHPAYQWSL-UHFFFAOYSA-N 0.000 claims 1
- LNFFTZLZPLIOIX-UHFFFAOYSA-N n-[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]-7-methoxy-6-[5-[(2-methylsulfonylethylamino)methyl]furan-2-yl]quinazolin-4-amine Chemical compound C=12C=C(C=3OC(CNCCS(C)(=O)=O)=CC=3)C(OC)=CC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC(F)=C1 LNFFTZLZPLIOIX-UHFFFAOYSA-N 0.000 claims 1
- KOUKAMXSEWAFHF-UHFFFAOYSA-N n-[3-fluoro-4-[(3-fluorophenyl)methoxy]phenyl]-6-[5-[(2-methylsulfonylethylamino)methyl]furan-2-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound O1C(CNCCS(=O)(=O)C)=CC=C1C(N=CC1=NC=N2)=CC1=C2NC(C=C1F)=CC=C1OCC1=CC=CC(F)=C1 KOUKAMXSEWAFHF-UHFFFAOYSA-N 0.000 claims 1
- CJGPKVRBUPRPTR-UHFFFAOYSA-N n-[4-[(3-fluorophenyl)methoxy]-3-methoxyphenyl]-6-[5-[(2-methylsulfonylethylamino)methyl]furan-2-yl]quinazolin-4-amine Chemical compound C=1C=C(OCC=2C=C(F)C=CC=2)C(OC)=CC=1NC(C1=C2)=NC=NC1=CC=C2C1=CC=C(CNCCS(C)(=O)=O)O1 CJGPKVRBUPRPTR-UHFFFAOYSA-N 0.000 claims 1
- CAORRJWMBDQDQW-UHFFFAOYSA-N n-[4-[(3-fluorophenyl)methoxy]phenyl]-6-[2-[(2-methylsulfonylethylamino)methyl]-1,3-thiazol-5-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound S1C(CNCCS(=O)(=O)C)=NC=C1C(N=CC1=NC=N2)=CC1=C2NC(C=C1)=CC=C1OCC1=CC=CC(F)=C1 CAORRJWMBDQDQW-UHFFFAOYSA-N 0.000 claims 1
- IZSWEZTZKROPAX-UHFFFAOYSA-N n-[4-[(3-fluorophenyl)methoxy]phenyl]-6-[2-[(2-methylsulfonylethylamino)methyl]-1,3-thiazol-5-yl]quinazolin-4-amine Chemical compound S1C(CNCCS(=O)(=O)C)=NC=C1C1=CC=C(N=CN=C2NC=3C=CC(OCC=4C=C(F)C=CC=4)=CC=3)C2=C1 IZSWEZTZKROPAX-UHFFFAOYSA-N 0.000 claims 1
- FLWJDTAEWRNVFU-UHFFFAOYSA-N n-[4-[(3-fluorophenyl)methoxy]phenyl]-6-[4-[(2-methylsulfonylethylamino)methyl]-1,3-thiazol-2-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound CS(=O)(=O)CCNCC1=CSC(C=2N=CC3=NC=NC(NC=4C=CC(OCC=5C=C(F)C=CC=5)=CC=4)=C3C=2)=N1 FLWJDTAEWRNVFU-UHFFFAOYSA-N 0.000 claims 1
- MJIYTTGQKXMTKS-UHFFFAOYSA-N n-[4-[(3-fluorophenyl)methoxy]phenyl]-6-[4-[(2-methylsulfonylethylamino)methyl]-1,3-thiazol-2-yl]quinazolin-4-amine Chemical compound CS(=O)(=O)CCNCC1=CSC(C=2C=C3C(NC=4C=CC(OCC=5C=C(F)C=CC=5)=CC=4)=NC=NC3=CC=2)=N1 MJIYTTGQKXMTKS-UHFFFAOYSA-N 0.000 claims 1
- BOKWTLKKZRQINZ-UHFFFAOYSA-N n-[4-[(3-fluorophenyl)methoxy]phenyl]-6-[5-[(2-methylsulfonylethylamino)methyl]-1,3-thiazol-2-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound S1C(CNCCS(=O)(=O)C)=CN=C1C(N=CC1=NC=N2)=CC1=C2NC(C=C1)=CC=C1OCC1=CC=CC(F)=C1 BOKWTLKKZRQINZ-UHFFFAOYSA-N 0.000 claims 1
- 208000000649 small cell carcinoma Diseases 0.000 claims 1
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- 238000002560 therapeutic procedure Methods 0.000 claims 1
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- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 abstract description 16
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 abstract description 16
- 230000000694 effects Effects 0.000 abstract description 7
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- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9800569.7A GB9800569D0 (en) | 1998-01-12 | 1998-01-12 | Heterocyclic compounds |
| PCT/EP1999/000048 WO1999035146A1 (en) | 1998-01-12 | 1999-01-08 | Bicyclic heteroaromatic compounds as protein tyrosine kinase inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK10502000A3 SK10502000A3 (sk) | 2001-08-06 |
| SK285405B6 true SK285405B6 (sk) | 2007-01-04 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1050-2000A SK285405B6 (sk) | 1998-01-12 | 1999-01-08 | Bicyklické heteroaromatické zlúčeniny, spôsob ichprípravy, farmaceutický prostriedok s ich obsahoma ich použitie |
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Owner name: LEO OSPREY LTD, GB Free format text: FORMER OWNER: GLAXOSMITHKLINE LLC; US Spc suppl protection certif: DO 73; 5005-2008 Effective date: 20160525 Owner name: NOVARTIS AG, CH Free format text: FORMER OWNER: LEO OSPREY LTD, GB Spc suppl protection certif: DO 73; 5005-2008 Effective date: 20160525 |
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| SPCM | Change of validity term of an spc as amended by art. 17 (2) of ec reg. no. 1610/96 and art. 18 of ec reg. no. 469/2009 |
Free format text: PRODUCT NAME: LAPATINIB; FIRST REGISTRATION NO/DATE: EU/1/07/440/001, EU/1/07/440/002, 20080610, Spc suppl protection certif: 73 5005-2008 Filing date: 20081008 Extension date: 20230612 |
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| MK4A | Patent expired |
Expiry date: 20190108 |