CZ295145B6 - Derivát chinazolinu - Google Patents

Derivát chinazolinu Download PDF

Info

Publication number: CZ295145B6
Authority: CZ; Czechia
Prior art keywords: hydrocarbyl; carbon atoms; group; methoxyethoxy; halogen
Prior art date: 1995-03-30

Application number

CZ19972067A

Other languages

Czech (cs)

English (en)

Inventor

Rodney Caughren Schnur

Lee Daniel Arnold

Original Assignee

Osi Pharmaceuticals, Inc.

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.)

1995-03-30

Filing date

1996-03-29

Publication date

2005-06-15

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=23636708&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CZ295145(B6) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1996-03-29 Application filed by Osi Pharmaceuticals, Inc. filed Critical Osi Pharmaceuticals, Inc.

2005-06-15 Publication of CZ295145B6 publication Critical patent/CZ295145B6/cs

Links

125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 title abstract 3
-1 4-(substituted phenylamino)quinazoline compounds Chemical class 0.000 claims abstract description 49
229910052736 halogen Inorganic materials 0.000 claims abstract description 19
150000003839 salts Chemical class 0.000 claims abstract description 14
125000005843 halogen group Chemical group 0.000 claims abstract description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 31
125000001183 hydrocarbyl group Chemical group 0.000 claims description 28
150000002367 halogens Chemical group 0.000 claims description 17
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
150000003246 quinazolines Chemical class 0.000 claims description 13
229910052717 sulfur Inorganic materials 0.000 claims description 12
ZPJLDMNVDPGZIU-UHFFFAOYSA-N 4-chloro-6,7-bis(2-methoxyethoxy)quinazoline Chemical compound C1=NC(Cl)=C2C=C(OCCOC)C(OCCOC)=CC2=N1 ZPJLDMNVDPGZIU-UHFFFAOYSA-N 0.000 claims description 10
229910052760 oxygen Inorganic materials 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 8
125000004434 sulfur atom Chemical group 0.000 claims description 8
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 6
125000004122 cyclic group Chemical group 0.000 claims description 6
125000005842 heteroatom Chemical group 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 5
PMQWTUWLIGJTQD-UHFFFAOYSA-N 6,7-bis(2-methoxyethoxy)-1h-quinazolin-4-one Chemical compound N1C=NC(=O)C2=C1C=C(OCCOC)C(OCCOC)=C2 PMQWTUWLIGJTQD-UHFFFAOYSA-N 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
239000011593 sulfur Chemical group 0.000 claims description 4
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
125000002252 acyl group Chemical group 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 3
125000001841 imino group Chemical group [H]N=* 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 3
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
229930195734 saturated hydrocarbon Natural products 0.000 claims description 3
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 3
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 2
238000011282 treatment Methods 0.000 abstract description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 6
201000010099 disease Diseases 0.000 abstract description 2
230000003463 hyperproliferative effect Effects 0.000 abstract description 2
238000002360 preparation method Methods 0.000 abstract description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
150000001875 compounds Chemical class 0.000 description 20
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
239000000203 mixture Substances 0.000 description 15
206010028980 Neoplasm Diseases 0.000 description 11
239000007787 solid Substances 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 9
108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
239000000243 solution Substances 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
102000001301 EGF receptor Human genes 0.000 description 6
108060006698 EGF receptor Proteins 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
201000011510 cancer Diseases 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
239000000047 product Substances 0.000 description 6
229910052938 sodium sulfate Inorganic materials 0.000 description 6
235000011152 sodium sulphate Nutrition 0.000 description 6
239000002904 solvent Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
150000002431 hydrogen Chemical class 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
230000001594 aberrant effect Effects 0.000 description 4
239000012267 brine Substances 0.000 description 4
208000035475 disorder Diseases 0.000 description 4
KBPUBCVJHFXPOC-UHFFFAOYSA-N ethyl 3,4-dihydroxybenzoate Chemical compound CCOC(=O)C1=CC=C(O)C(O)=C1 KBPUBCVJHFXPOC-UHFFFAOYSA-N 0.000 description 4
238000001914 filtration Methods 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
RORJMEOQKVOQBC-UHFFFAOYSA-N 4-chloro-6-(2-chloroethoxy)-7-(2-methoxyethoxy)quinazoline Chemical compound C1=NC(Cl)=C2C=C(OCCCl)C(OCCOC)=CC2=N1 RORJMEOQKVOQBC-UHFFFAOYSA-N 0.000 description 3
HFGVHQGBDDTDIJ-UHFFFAOYSA-N 4-chloro-7-(2-chloroethoxy)-6-(2-methoxyethoxy)quinazoline Chemical compound N1=CN=C2C=C(OCCCl)C(OCCOC)=CC2=C1Cl HFGVHQGBDDTDIJ-UHFFFAOYSA-N 0.000 description 3
XSLSFNALFKUARJ-UHFFFAOYSA-N 6,7-bis(2-methoxyethoxy)-1h-quinazolin-2-one Chemical compound C1=NC(=O)NC2=C1C=C(OCCOC)C(OCCOC)=C2 XSLSFNALFKUARJ-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
210000004027 cell Anatomy 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
238000000034 method Methods 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
108090000623 proteins and genes Proteins 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 2
WXAZLCUYDRYLFC-UHFFFAOYSA-N 4-chloro-6,7-bis(2-chloroethoxy)quinazoline Chemical compound C1=NC(Cl)=C2C=C(OCCCl)C(OCCCl)=CC2=N1 WXAZLCUYDRYLFC-UHFFFAOYSA-N 0.000 description 2
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
239000005695 Ammonium acetate Substances 0.000 description 2
201000009030 Carcinoma Diseases 0.000 description 2
230000006820 DNA synthesis Effects 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
108700020796 Oncogene Proteins 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
108091000080 Phosphotransferase Proteins 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
102100033237 Pro-epidermal growth factor Human genes 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
230000004913 activation Effects 0.000 description 2
235000019257 ammonium acetate Nutrition 0.000 description 2
229940043376 ammonium acetate Drugs 0.000 description 2
VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 2
230000001093 anti-cancer Effects 0.000 description 2
239000002246 antineoplastic agent Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
210000000481 breast Anatomy 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
239000003480 eluent Substances 0.000 description 2
VGFZRAVMWXHEJB-UHFFFAOYSA-N ethyl 3,4-bis(2-methoxyethoxy)benzoate Chemical compound CCOC(=O)C1=CC=C(OCCOC)C(OCCOC)=C1 VGFZRAVMWXHEJB-UHFFFAOYSA-N 0.000 description 2
239000000284 extract Substances 0.000 description 2
239000012458 free base Substances 0.000 description 2
230000014509 gene expression Effects 0.000 description 2
230000012010 growth Effects 0.000 description 2
206010020718 hyperplasia Diseases 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
208000032839 leukemia Diseases 0.000 description 2
210000004072 lung Anatomy 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
102000020233 phosphotransferase Human genes 0.000 description 2
210000002307 prostate Anatomy 0.000 description 2
102000004169 proteins and genes Human genes 0.000 description 2
102000027426 receptor tyrosine kinases Human genes 0.000 description 2
108091008598 receptor tyrosine kinases Proteins 0.000 description 2
230000011664 signaling Effects 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
238000003756 stirring Methods 0.000 description 2
DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
231100000331 toxic Toxicity 0.000 description 2
230000002588 toxic effect Effects 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
210000004881 tumor cell Anatomy 0.000 description 2
229940121358 tyrosine kinase inhibitor Drugs 0.000 description 2
239000005483 tyrosine kinase inhibitor Substances 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
FQQRNBROXUGYPQ-UHFFFAOYSA-N 2-(2-methoxyethoxy)quinazoline Chemical compound C1=CC=CC2=NC(OCCOC)=NC=C21 FQQRNBROXUGYPQ-UHFFFAOYSA-N 0.000 description 1
SLAMLWHELXOEJZ-UHFFFAOYSA-M 2-nitrobenzoate Chemical compound [O-]C(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-M 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
NNKQLUVBPJEUOR-UHFFFAOYSA-N 3-ethynylaniline Chemical compound NC1=CC=CC(C#C)=C1 NNKQLUVBPJEUOR-UHFFFAOYSA-N 0.000 description 1
UAKIOQBEKUXJNJ-UHFFFAOYSA-N 4-(2-methoxyethoxy)-1H-quinazolin-2-one Chemical compound COCCOC1=NC(NC2=CC=CC=C12)=O UAKIOQBEKUXJNJ-UHFFFAOYSA-N 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
UASVPQOWYLTXIE-UHFFFAOYSA-N 5-ethynyl-2-methylaniline Chemical compound CC1=CC=C(C#C)C=C1N UASVPQOWYLTXIE-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
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208000026310 Breast neoplasm Diseases 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
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206010017993 Gastrointestinal neoplasms Diseases 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
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102100029981 Receptor tyrosine-protein kinase erbB-4 Human genes 0.000 description 1
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208000005718 Stomach Neoplasms Diseases 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000009471 action Effects 0.000 description 1
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YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
230000002411 adverse Effects 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
150000001345 alkine derivatives Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
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230000002491 angiogenic effect Effects 0.000 description 1
230000001028 anti-proliverative effect Effects 0.000 description 1
238000013459 approach Methods 0.000 description 1
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239000007864 aqueous solution Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
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125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
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SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
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Classifications

- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/94—Nitrogen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents

Landscapes

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

CZ19972067A 1995-03-30 1996-03-29 Derivát chinazolinu CZ295145B6 (cs)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US41330095A	1995-03-30	1995-03-30
PCT/IB1995/000436 WO1996030347A1 (en)	1995-03-30	1995-06-06	Quinazoline derivatives

Publications (1)

Publication Number	Publication Date
CZ295145B6 true CZ295145B6 (cs)	2005-06-15

Family

ID=23636708

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CZ19972067A CZ295145B6 (cs)	1995-03-30	1996-03-29	Derivát chinazolinu
CZ1996931A CZ294967B6 (cs)	1995-03-30	1996-03-29	4-(Substituovaný fenylamino)chinazolinové deriváty, způsob jejich výroby a použití a farmaceutické prostředky na jejich bázi

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CZ1996931A CZ294967B6 (cs)	1995-03-30	1996-03-29	4-(Substituovaný fenylamino)chinazolinové deriváty, způsob jejich výroby a použití a farmaceutické prostředky na jejich bázi

Country Status (43)

Country	Link
EP (5)	EP1110953B1 (2)
JP (1)	JP3088018B2 (2)
KR (1)	KR100232335B1 (2)
CN (1)	CN1066142C (2)
AP (1)	AP735A (2)
AR (1)	AR002723A1 (2)
AT (2)	ATE446955T1 (2)
AU (2)	AU703638B2 (2)
BR (1)	BR9601200B1 (2)
CA (1)	CA2216796C (2)
CO (1)	CO4410333A1 (2)
CZ (2)	CZ295145B6 (2)
DE (3)	DE69522717T2 (2)
DK (1)	DK0817775T3 (2)
EG (1)	EG24229A (2)
ES (2)	ES2161290T3 (2)
FI (1)	FI120646B (2)
FR (1)	FR06C0010I2 (2)
GR (1)	GR3037070T3 (2)
HR (1)	HRP960147B1 (2)
HU (2)	HU229120B1 (2)
IL (7)	IL189037A (2)
LU (1)	LU91209I2 (2)
MA (1)	MA23831A1 (2)
MX (1)	MX9707453A (2)
MY (1)	MY117896A (2)
NL (1)	NL300214I2 (2)
NO (2)	NO308740B1 (2)
NZ (1)	NZ286263A (2)
OA (1)	OA10277A (2)
PE (1)	PE43897A1 (2)
PL (1)	PL186843B1 (2)
PT (1)	PT817775E (2)
RU (2)	RU2694252C2 (2)
SA (1)	SA96160707B1 (2)
SG (1)	SG43262A1 (2)
SI (1)	SI9600102A (2)
SK (2)	SK283762B6 (2)
TR (1)	TR199600265A1 (2)
TW (1)	TW454000B (2)
UA (1)	UA44254C2 (2)
WO (1)	WO1996030347A1 (2)
ZA (1)	ZA962522B (2)

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Publication number	Publication date
ATE446955T1 (de)	2009-11-15
EP2163546A1 (en)	2010-03-17
FR06C0010I1 (2)	2006-05-19
IL129994A0 (en)	2000-02-29
EP1110953A1 (en)	2001-06-27
BR9601200A (pt)	1998-01-06
PE43897A1 (es)	1997-10-10
NZ286263A (en)	1997-11-24
DE69536015D1 (de)	2009-12-10
KR100232335B1 (ko)	1999-12-01
EP0817775A1 (en)	1998-01-14
HU229120B1 (en)	2013-08-28
IL129996A0 (en)	2000-02-29
RU2174977C2 (ru)	2001-10-20
ES2161290T3 (es)	2001-12-01
SK283762B6 (sk)	2004-01-08
FI120646B (fi)	2010-01-15
AU703638B2 (en)	1999-03-25
NO2006004I2 (no)	2011-07-25
HK1038740A1 (en)	2002-03-28
SG43262A1 (en)	1997-10-17
DK0817775T3 (da)	2001-11-19
EP3103799A1 (en)	2016-12-14
HUS1400001I1 (hu)	2016-02-29
AU3585499A (en)	1999-08-19
NO961299D0 (no)	1996-03-29
LU91209I2 (fr)	2006-10-05
MY117896A (en)	2004-08-30
HRP960147B1 (en)	2002-04-30
CZ294967B6 (cs)	2005-04-13
KR960034184A (ko)	1996-10-22
SK283763B6 (sk)	2004-01-08
OA10277A (en)	1997-10-07
HUP9600834A3 (en)	1997-08-28
IL189037A0 (en)	2008-06-05
EP2295415A1 (en)	2011-03-16
CN1137037A (zh)	1996-12-04
JPH10506633A (ja)	1998-06-30
RU2694252C2 (ru)	2019-07-10
CO4410333A1 (es)	1997-01-09
NO308740B1 (no)	2000-10-23
PL186843B1 (pl)	2004-03-31
GR3037070T3 (en)	2002-01-31
HRP960147A2 (en)	1997-08-31
SI9600102A (en)	1997-02-28
DE69522717T2 (de)	2002-02-14
CA2216796C (en)	2003-09-02
EP3103799B1 (en)	2018-06-06
NL300214I2 (nl)	2006-07-03
IL189037A (en)	2011-03-31
AP9600788A0 (en)	1996-04-30
HUP9600834A1 (en)	1997-05-28
SA96160707B1 (ar)	2006-03-25
CZ93196A3 (en)	1997-02-12
RU2694252C3 (ru)	2019-08-20
MX9707453A (es)	1997-12-31
SK38796A3 (en)	1997-08-06
TW454000B (en)	2001-09-11
DE122005000053I1 (de)	2006-03-16
AR002723A1 (es)	1998-04-29
NO961299L (no)	1996-10-01
EP1110953B1 (en)	2009-10-28
PL313541A1 (en)	1996-10-14
FI973832A0 (fi)	1997-09-29
BR9601200B1 (pt)	2010-12-14
AU5040696A (en)	1996-10-10
JP3088018B2 (ja)	2000-09-18
NL300214I1 (nl)	2006-03-01
DE69522717D1 (de)	2001-10-18
AP735A (en)	1999-02-25
IL129995A (en)	2005-11-20
EG24229A (2)	2008-11-10
EP2163546B1 (en)	2016-06-01
IL129994A (en)	2008-04-13
WO1996030347A1 (en)	1996-10-03
ES2332984T3 (es)	2010-02-16
CA2216796A1 (en)	1996-10-03
ZA962522B (en)	1997-09-29
CN1066142C (zh)	2001-05-23
FI973832L (fi)	1997-09-29
NO2006004I1 (no)	2006-03-20
IL117598A (en)	2005-11-20
IL129995A0 (en)	2000-02-29
EP0817775B1 (en)	2001-09-12
DE122005000053I2 (de)	2008-01-17
FR06C0010I2 (2)	2006-12-29
PT817775E (pt)	2002-01-30
TR199600265A1 (tr)	1997-03-21
ATE205483T1 (de)	2001-09-15
UA44254C2 (uk)	2002-02-15
MA23831A1 (fr)	1996-10-01
HU9600834D0 (en)	1996-05-28
IL117598A0 (en)	1996-07-23

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2016-04-06	MK4A	Patent expired	Effective date: 20160329

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