ZA200300991B - Bicyclic heterocycles, medicaments containing these compounds, their use, and methods for the production thereof. - Google Patents
Bicyclic heterocycles, medicaments containing these compounds, their use, and methods for the production thereof. Download PDFInfo
- Publication number
- ZA200300991B ZA200300991B ZA200300991A ZA200300991A ZA200300991B ZA 200300991 B ZA200300991 B ZA 200300991B ZA 200300991 A ZA200300991 A ZA 200300991A ZA 200300991 A ZA200300991 A ZA 200300991A ZA 200300991 B ZA200300991 B ZA 200300991B
- Authority
- ZA
- South Africa
- Prior art keywords
- amino
- oxo
- quinazoline
- morpholin
- chloro
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 32
- 125000002618 bicyclic heterocycle group Chemical group 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title claims 3
- 239000003814 drug Substances 0.000 title 1
- -1 methoxy, cyclobutyloxy Chemical group 0.000 claims description 164
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 78
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 21
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
- RWAHVEYSYXHNAL-UHFFFAOYSA-N 4-[2-[4-(3-chloro-4-fluoroanilino)-6-cyclopentyloxyquinazolin-7-yl]oxyethyl]-6,6-dimethylmorpholin-2-one Chemical compound C1C(=O)OC(C)(C)CN1CCOC1=CC2=NC=NC(NC=3C=C(Cl)C(F)=CC=3)=C2C=C1OC1CCCC1 RWAHVEYSYXHNAL-UHFFFAOYSA-N 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- RJPCPYPTZYKLJM-UHFFFAOYSA-N 4-[2-[4-(3-bromoanilino)-7-methoxyquinazolin-6-yl]oxyethyl-methylamino]oxolan-2-one Chemical compound C=12C=C(OCCN(C)C3CC(=O)OC3)C(OC)=CC2=NC=NC=1NC1=CC=CC(Br)=C1 RJPCPYPTZYKLJM-UHFFFAOYSA-N 0.000 claims description 7
- BAUCTDMQPYLVQN-UHFFFAOYSA-N 4-[2-[4-(3-bromoanilino)-7-methoxyquinazolin-6-yl]oxyethyl]-3-methylmorpholin-2-one Chemical compound C=12C=C(OCCN3C(C(=O)OCC3)C)C(OC)=CC2=NC=NC=1NC1=CC=CC(Br)=C1 BAUCTDMQPYLVQN-UHFFFAOYSA-N 0.000 claims description 7
- JSLMOUXQBQDGLP-UHFFFAOYSA-N 4-[2-[4-(3-bromoanilino)-7-methoxyquinazolin-6-yl]oxyethyl]-6,6-dimethylmorpholin-2-one Chemical compound C=12C=C(OCCN3CC(C)(C)OC(=O)C3)C(OC)=CC2=NC=NC=1NC1=CC=CC(Br)=C1 JSLMOUXQBQDGLP-UHFFFAOYSA-N 0.000 claims description 7
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 7
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 7
- DJVWLKJVZDSJMO-UHFFFAOYSA-N ethyl 2-[2-[4-(3-chloro-4-fluoroanilino)-6-cyclopentyloxyquinazolin-7-yl]oxyethyl-(2-hydroxy-2-methylpropyl)amino]acetate Chemical compound C=12C=C(OC3CCCC3)C(OCCN(CC(=O)OCC)CC(C)(C)O)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 DJVWLKJVZDSJMO-UHFFFAOYSA-N 0.000 claims description 6
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 6
- GVMFBYFHOKWOFP-UHFFFAOYSA-N 4-[2-[4-(3-bromoanilino)-7-methoxyquinazolin-6-yl]oxyethyl]-5,5-dimethylmorpholin-2-one Chemical compound C=12C=C(OCCN3C(COC(=O)C3)(C)C)C(OC)=CC2=NC=NC=1NC1=CC=CC(Br)=C1 GVMFBYFHOKWOFP-UHFFFAOYSA-N 0.000 claims description 5
- ZCWYAZUJPZABLJ-UHFFFAOYSA-N 4-[2-[4-(3-chloro-4-fluoroanilino)-6-methoxyquinazolin-7-yl]oxyethyl]-6,6-dimethylmorpholin-2-one Chemical compound N1=CN=C2C=C(OCCN3CC(C)(C)OC(=O)C3)C(OC)=CC2=C1NC1=CC=C(F)C(Cl)=C1 ZCWYAZUJPZABLJ-UHFFFAOYSA-N 0.000 claims description 5
- GYVRDMNWJPTXML-UHFFFAOYSA-N 4-[2-[4-(3-chloro-4-fluoroanilino)-7-(cyclopropylmethoxy)quinazolin-6-yl]oxyethyl]-6,6-dimethylmorpholin-2-one Chemical compound C1C(=O)OC(C)(C)CN1CCOC(C(=CC1=NC=N2)OCC3CC3)=CC1=C2NC1=CC=C(F)C(Cl)=C1 GYVRDMNWJPTXML-UHFFFAOYSA-N 0.000 claims description 5
- OFWKTIYGKIJXOE-UHFFFAOYSA-N 4-[2-[4-(3-chloro-4-fluoroanilino)-7-cyclobutyloxyquinazolin-6-yl]oxyethyl]-6,6-dimethylmorpholin-2-one Chemical compound C1C(=O)OC(C)(C)CN1CCOC(C(=CC1=NC=N2)OC3CCC3)=CC1=C2NC1=CC=C(F)C(Cl)=C1 OFWKTIYGKIJXOE-UHFFFAOYSA-N 0.000 claims description 5
- VBCDIYXYEHUGQT-UHFFFAOYSA-N 4-[2-[4-(3-chloro-4-fluoroanilino)-7-methoxyquinazolin-6-yl]oxyethyl-methylamino]oxolan-2-one Chemical compound C=12C=C(OCCN(C)C3CC(=O)OC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 VBCDIYXYEHUGQT-UHFFFAOYSA-N 0.000 claims description 5
- DFENXCTZLWKHRS-UHFFFAOYSA-N 4-[3-[4-(3-chloro-4-fluoroanilino)-6-cyclopentyloxyquinazolin-7-yl]oxypropyl]-6,6-dimethylmorpholin-2-one Chemical compound C1C(=O)OC(C)(C)CN1CCCOC1=CC2=NC=NC(NC=3C=C(Cl)C(F)=CC=3)=C2C=C1OC1CCCC1 DFENXCTZLWKHRS-UHFFFAOYSA-N 0.000 claims description 5
- PENJTVNVWKGZKD-UHFFFAOYSA-N 4-[3-[4-(3-chloro-4-fluoroanilino)-7-methoxyquinazolin-6-yl]oxypropyl]-6,6-dimethylmorpholin-2-one Chemical compound C=12C=C(OCCCN3CC(C)(C)OC(=O)C3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 PENJTVNVWKGZKD-UHFFFAOYSA-N 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- WSRABTAALVGLSH-UHFFFAOYSA-N 4-[2-[4-(3-chloro-4-fluoroanilino)-6-(cyclopentylmethoxy)quinazolin-7-yl]oxyethyl-methylamino]oxolan-2-one Chemical compound C1OC(=O)CC1N(C)CCOC(C(=CC1=2)OCC3CCCC3)=CC1=NC=NC=2NC1=CC=C(F)C(Cl)=C1 WSRABTAALVGLSH-UHFFFAOYSA-N 0.000 claims description 4
- DAIBLUSVAFXMJJ-UHFFFAOYSA-N 4-[2-[4-(3-chloro-4-fluoroanilino)-7-methoxyquinazolin-6-yl]oxyethyl]-6,6-dimethylmorpholin-2-one Chemical compound C=12C=C(OCCN3CC(C)(C)OC(=O)C3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 DAIBLUSVAFXMJJ-UHFFFAOYSA-N 0.000 claims description 4
- BNQKFXMIUFAING-UHFFFAOYSA-N 4-[3-[4-(3-chloro-4-fluoroanilino)-6-methoxyquinazolin-7-yl]oxypropyl]-6,6-dimethylmorpholin-2-one Chemical compound N1=CN=C2C=C(OCCCN3CC(C)(C)OC(=O)C3)C(OC)=CC2=C1NC1=CC=C(F)C(Cl)=C1 BNQKFXMIUFAING-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- NZBVKCLSEPVJHF-UHFFFAOYSA-N 4-[2-[4-(3-chloro-4-fluoroanilino)-6-(cyclopropylmethoxy)quinazolin-7-yl]oxyethyl]-6,6-dimethylmorpholin-2-one Chemical compound C1C(=O)OC(C)(C)CN1CCOC1=CC2=NC=NC(NC=3C=C(Cl)C(F)=CC=3)=C2C=C1OCC1CC1 NZBVKCLSEPVJHF-UHFFFAOYSA-N 0.000 claims description 3
- CCEJFLUXVPEPKO-UHFFFAOYSA-N 4-[2-[4-(3-chloro-4-fluoroanilino)-6-cyclobutyloxyquinazolin-7-yl]oxyethyl]-6,6-dimethylmorpholin-2-one Chemical compound C1C(=O)OC(C)(C)CN1CCOC1=CC2=NC=NC(NC=3C=C(Cl)C(F)=CC=3)=C2C=C1OC1CCC1 CCEJFLUXVPEPKO-UHFFFAOYSA-N 0.000 claims description 3
- TYTIBVDKISSGSI-UHFFFAOYSA-N 4-[2-[4-(3-chloro-4-fluoroanilino)-6-methoxyquinazolin-7-yl]oxyethyl-methylamino]oxolan-2-one Chemical compound N1=CN=C2C=C(OCCN(C)C3CC(=O)OC3)C(OC)=CC2=C1NC1=CC=C(F)C(Cl)=C1 TYTIBVDKISSGSI-UHFFFAOYSA-N 0.000 claims description 3
- LIKMFAJDPFCRSP-UHFFFAOYSA-N 4-[2-[4-(3-chloro-4-fluoroanilino)-7-cyclopentyloxyquinazolin-6-yl]oxyethyl]-6,6-dimethylmorpholin-2-one Chemical compound C1C(=O)OC(C)(C)CN1CCOC(C(=CC1=NC=N2)OC3CCCC3)=CC1=C2NC1=CC=C(F)C(Cl)=C1 LIKMFAJDPFCRSP-UHFFFAOYSA-N 0.000 claims description 3
- MJWGUQUVMQNFPO-UHFFFAOYSA-N 4-[3-[4-(3-chloro-4-fluoroanilino)-6-(cyclopentylmethoxy)quinazolin-7-yl]oxypropyl]-6,6-dimethylmorpholin-2-one Chemical compound C1C(=O)OC(C)(C)CN1CCCOC1=CC2=NC=NC(NC=3C=C(Cl)C(F)=CC=3)=C2C=C1OCC1CCCC1 MJWGUQUVMQNFPO-UHFFFAOYSA-N 0.000 claims description 3
- NWNSEKIWSUBXNV-UHFFFAOYSA-N 4-[3-[4-(3-chloro-4-fluoroanilino)-7-(cyclopentylmethoxy)quinazolin-6-yl]oxypropyl]-6,6-dimethylmorpholin-2-one Chemical compound C1C(=O)OC(C)(C)CN1CCCOC(C(=CC1=NC=N2)OCC3CCCC3)=CC1=C2NC1=CC=C(F)C(Cl)=C1 NWNSEKIWSUBXNV-UHFFFAOYSA-N 0.000 claims description 3
- JCRXOOXQHWVXCX-OAQYLSRUSA-N 4-[3-[6-cyclopentyloxy-4-[[(1r)-1-phenylethyl]amino]quinazolin-7-yl]oxypropyl]-6,6-dimethylmorpholin-2-one Chemical compound N([C@H](C)C=1C=CC=CC=1)C(C1=CC=2OC3CCCC3)=NC=NC1=CC=2OCCCN1CC(=O)OC(C)(C)C1 JCRXOOXQHWVXCX-OAQYLSRUSA-N 0.000 claims description 3
- MQNVZWJAFPETRQ-UHFFFAOYSA-N 4-[2-[4-(3-chloro-4-fluoroanilino)-7-(cyclopentylmethoxy)quinazolin-6-yl]oxyethyl-methylamino]oxolan-2-one Chemical compound C1OC(=O)CC1N(C)CCOC(C(=CC1=NC=N2)OCC3CCCC3)=CC1=C2NC1=CC=C(F)C(Cl)=C1 MQNVZWJAFPETRQ-UHFFFAOYSA-N 0.000 claims description 2
- KAZLMIBQIIGVMX-UHFFFAOYSA-N 4-[2-[4-(3-chloro-4-fluoroanilino)-7-cyclopentyloxyquinazolin-6-yl]oxyethyl-methylamino]oxolan-2-one Chemical compound C1OC(=O)CC1N(C)CCOC(C(=CC1=NC=N2)OC3CCCC3)=CC1=C2NC1=CC=C(F)C(Cl)=C1 KAZLMIBQIIGVMX-UHFFFAOYSA-N 0.000 claims description 2
- AROYRXOYFGHXLP-UHFFFAOYSA-N 4-[3-[4-(3-chloro-4-fluoroanilino)-7-cyclopentyloxyquinazolin-6-yl]oxypropyl]-6,6-dimethylmorpholin-2-one Chemical compound C1C(=O)OC(C)(C)CN1CCCOC(C(=CC1=NC=N2)OC3CCCC3)=CC1=C2NC1=CC=C(F)C(Cl)=C1 AROYRXOYFGHXLP-UHFFFAOYSA-N 0.000 claims description 2
- MSWAPRHYKIDXQU-OAQYLSRUSA-N 4-[3-[7-cyclopentyloxy-4-[[(1r)-1-phenylethyl]amino]quinazolin-6-yl]oxypropyl]-6,6-dimethylmorpholin-2-one Chemical compound N([C@H](C)C=1C=CC=CC=1)C(C1=CC=2OCCCN3CC(C)(C)OC(=O)C3)=NC=NC1=CC=2OC1CCCC1 MSWAPRHYKIDXQU-OAQYLSRUSA-N 0.000 claims description 2
- IISUFHXUQWEMSR-UHFFFAOYSA-N ethyl 2-[2-[4-(3-bromoanilino)-7-methoxyquinazolin-6-yl]oxyethyl-(2-hydroxy-2-methylpropyl)amino]acetate Chemical compound N1=CN=C2C=C(OC)C(OCCN(CC(=O)OCC)CC(C)(C)O)=CC2=C1NC1=CC=CC(Br)=C1 IISUFHXUQWEMSR-UHFFFAOYSA-N 0.000 claims description 2
- 210000004072 lung Anatomy 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- VHKZTIYWIQXOBG-CQSZACIVSA-N (6r)-4-[2-[4-(3-bromoanilino)-7-methoxyquinazolin-6-yl]oxyethyl]-6-methylmorpholin-2-one Chemical compound C=12C=C(OCCN3CC(=O)O[C@H](C)C3)C(OC)=CC2=NC=NC=1NC1=CC=CC(Br)=C1 VHKZTIYWIQXOBG-CQSZACIVSA-N 0.000 claims 1
- HBQDVCAYRXMBGM-ZWKOTPCHSA-N (6s)-4-[3-[7-methoxy-4-[[(1r)-1-phenylethyl]amino]quinazolin-6-yl]oxypropyl]-6-methylmorpholin-2-one Chemical compound C1([C@@H](C)NC=2N=CN=C3C=C(C(=CC3=2)OCCCN2CC(=O)O[C@@H](C)C2)OC)=CC=CC=C1 HBQDVCAYRXMBGM-ZWKOTPCHSA-N 0.000 claims 1
- QTQNMKOQYNBYDT-UHFFFAOYSA-N 4-[2-[4-(3-chloro-4-fluoroanilino)-6-(cyclopentylmethoxy)quinazolin-7-yl]oxyethyl]-6,6-dimethylmorpholin-2-one Chemical compound C1C(=O)OC(C)(C)CN1CCOC1=CC2=NC=NC(NC=3C=C(Cl)C(F)=CC=3)=C2C=C1OCC1CCCC1 QTQNMKOQYNBYDT-UHFFFAOYSA-N 0.000 claims 1
- KLUXUPFXUSDNOO-UHFFFAOYSA-N 4-[2-[4-(3-chloro-4-fluoroanilino)-6-cyclopentyloxyquinazolin-7-yl]oxyethyl-methylamino]oxolan-2-one Chemical compound C1OC(=O)CC1N(C)CCOC(C(=CC1=2)OC3CCCC3)=CC1=NC=NC=2NC1=CC=C(F)C(Cl)=C1 KLUXUPFXUSDNOO-UHFFFAOYSA-N 0.000 claims 1
- BTWIMCNTLBHGKQ-UHFFFAOYSA-N 7-cyclopentyloxyquinazoline Chemical compound C1CCCC1OC1=CC=C(C=NC=N2)C2=C1 BTWIMCNTLBHGKQ-UHFFFAOYSA-N 0.000 claims 1
- 210000000013 bile duct Anatomy 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 210000000232 gallbladder Anatomy 0.000 claims 1
- 210000001035 gastrointestinal tract Anatomy 0.000 claims 1
- 210000003734 kidney Anatomy 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 9
- ORNNDXINECIJIS-UHFFFAOYSA-N 3-methylmorpholin-2-one Chemical compound CC1NCCOC1=O ORNNDXINECIJIS-UHFFFAOYSA-N 0.000 description 1
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 1
- KXTJAPWHGXHDSX-UHFFFAOYSA-N 5,5-dimethylmorpholin-2-one Chemical compound CC1(C)COC(=O)CN1 KXTJAPWHGXHDSX-UHFFFAOYSA-N 0.000 description 1
- BLJROXUIKLDLBD-UHFFFAOYSA-N COC1C(C(C(OC1)(OC1COCC1)OCC1CCCC1)(OCC1CCC1)OCC1CC1)(OC1CCCC1)OC1CCC1 Chemical compound COC1C(C(C(OC1)(OC1COCC1)OCC1CCCC1)(OCC1CCC1)OCC1CC1)(OC1CCCC1)OC1CCC1 BLJROXUIKLDLBD-UHFFFAOYSA-N 0.000 description 1
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 1
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 230000001173 tumoral effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A—HUMAN NECESSITIES
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A—HUMAN NECESSITIES
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- A61P11/08—Bronchodilators
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- 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
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- 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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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Oncology (AREA)
- Immunology (AREA)
- Dermatology (AREA)
- Gastroenterology & Hepatology (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10042058A DE10042058A1 (de) | 2000-08-26 | 2000-08-26 | Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200300991B true ZA200300991B (en) | 2004-04-16 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200300991A ZA200300991B (en) | 2000-08-26 | 2003-02-05 | Bicyclic heterocycles, medicaments containing these compounds, their use, and methods for the production thereof. |
Country Status (30)
| Country | Link |
|---|---|
| EP (1) | EP1315705A1 (cs) |
| JP (1) | JP4834282B2 (cs) |
| KR (1) | KR100862873B1 (cs) |
| CN (1) | CN100404517C (cs) |
| AR (1) | AR033562A1 (cs) |
| AU (2) | AU8769401A (cs) |
| BG (1) | BG107559A (cs) |
| BR (1) | BR0113519A (cs) |
| CA (1) | CA2417897C (cs) |
| CZ (1) | CZ302567B6 (cs) |
| DE (1) | DE10042058A1 (cs) |
| EA (1) | EA005679B1 (cs) |
| EC (1) | ECSP034464A (cs) |
| EE (1) | EE05269B1 (cs) |
| HR (1) | HRP20030138A2 (cs) |
| HU (1) | HUP0300819A3 (cs) |
| IL (2) | IL154602A0 (cs) |
| ME (1) | MEP58708A (cs) |
| MX (1) | MXPA03001483A (cs) |
| MY (1) | MY126132A (cs) |
| NO (1) | NO324866B1 (cs) |
| NZ (1) | NZ524668A (cs) |
| PL (1) | PL360248A1 (cs) |
| RS (1) | RS52279B (cs) |
| SK (1) | SK287747B6 (cs) |
| TW (1) | TWI294422B (cs) |
| UA (1) | UA73004C2 (cs) |
| UY (1) | UY26903A1 (cs) |
| WO (1) | WO2002018351A1 (cs) |
| ZA (1) | ZA200300991B (cs) |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT1731511E (pt) | 1999-06-21 | 2015-11-13 | Boehringer Ingelheim Pharma | Heterociclos bicíclicos, medicamentos contendo estes compostos, a sua utilização e processos para a sua preparação |
| DE10042059A1 (de) * | 2000-08-26 | 2002-03-07 | Boehringer Ingelheim Pharma | Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
| US7019012B2 (en) | 2000-12-20 | 2006-03-28 | Boehringer Ingelheim International Pharma Gmbh & Co. Kg | Quinazoline derivatives and pharmaceutical compositions containing them |
| TW200813014A (en) * | 2002-03-28 | 2008-03-16 | Astrazeneca Ab | Quinazoline derivatives |
| DE10214412A1 (de) * | 2002-03-30 | 2003-10-09 | Boehringer Ingelheim Pharma | Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
| US6924285B2 (en) | 2002-03-30 | 2005-08-02 | Boehringer Ingelheim Pharma Gmbh & Co. | Bicyclic heterocyclic compounds, pharmaceutical compositions containing these compounds, their use and process for preparing them |
| IL164167A0 (en) * | 2002-03-30 | 2005-12-18 | Boehringer Ingelheim Pharma | 4-(N-phenylamino)-quinazolines/ quinolines as tyrosine kinase inhibitors |
| JP4703183B2 (ja) | 2002-07-15 | 2011-06-15 | シンフォニー エボルーション， インク． | 受容体型キナーゼモジュレーターおよびその使用方法 |
| DE10326186A1 (de) | 2003-06-06 | 2004-12-23 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
| DE10334226A1 (de) * | 2003-07-28 | 2005-02-17 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Verwendung von Tyrosinkinase-Inhibitoren zur Behandlung inflammatorischer Prozesse |
| GB0317665D0 (en) | 2003-07-29 | 2003-09-03 | Astrazeneca Ab | Qinazoline derivatives |
| JP4795952B2 (ja) | 2003-09-16 | 2011-10-19 | アストラゼネカ アクチボラグ | チロシンキナーゼ阻害剤としてのキナゾリン誘導体 |
| DK1667992T3 (da) | 2003-09-19 | 2007-04-30 | Astrazeneca Ab | Quinazolinderivater |
| EP2213661B1 (en) | 2003-09-26 | 2011-07-20 | Exelixis Inc. | c-Met Modulators and Methods of Use |
| DE10345875A1 (de) * | 2003-09-30 | 2005-04-21 | Boehringer Ingelheim Pharma | Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, deren Vewendung und Verfahren zu ihrer Herstellung |
| US7456189B2 (en) | 2003-09-30 | 2008-11-25 | Boehringer Ingelheim International Gmbh | Bicyclic heterocycles, medicaments containing these compounds, their use and processes for their preparation |
| DE10350717A1 (de) * | 2003-10-30 | 2005-06-02 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Verwendung von Tyrosinkinase-Inhibitoren zur Behandlung inflammatorischer Prozesse |
| US20060035893A1 (en) | 2004-08-07 | 2006-02-16 | Boehringer Ingelheim International Gmbh | Pharmaceutical compositions for treatment of respiratory and gastrointestinal disorders |
| PE20060777A1 (es) | 2004-12-24 | 2006-10-06 | Boehringer Ingelheim Int | Derivados de indolinona para el tratamiento o la prevencion de enfermedades fibroticas |
| ATE521603T1 (de) | 2005-02-26 | 2011-09-15 | Astrazeneca Ab | Chinazolinderivate als tyrosinkinaseinhibitoren |
| KR100673775B1 (ko) * | 2005-04-08 | 2007-01-24 | 엘지전자 주식회사 | 냉장고용 홈바 |
| US20100234371A1 (en) * | 2005-08-22 | 2010-09-16 | Frank Himmelsbach | Bicyclic heterocycles, pharmaceutical compositions containing these compounds, the use thereof and processes for the preparation thereof |
| US8404697B2 (en) | 2005-11-11 | 2013-03-26 | Boehringer Ingelheim International Gmbh | Quinazoline derivatives for the treatment of cancer diseases |
| US20090306105A1 (en) * | 2006-03-09 | 2009-12-10 | Boehringer Ingelheim International Gmbh | Bicyclic heterocycles, medicaments containing these compounds, their use and process for preparing them |
| MX2009002710A (es) | 2006-09-18 | 2009-03-25 | Boehringer Ingelheim Int | Metodos para tratar canceres que portan mutaciones de egfr. |
| EP1921070A1 (de) | 2006-11-10 | 2008-05-14 | Boehringer Ingelheim Pharma GmbH & Co. KG | Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstelllung |
| EP2118075A1 (de) | 2007-02-06 | 2009-11-18 | Boehringer Ingelheim International GmbH | Bicyclische heterocyclen, diese verbindungen enthaltende arzneimittel, deren verwendung und verfahren zu ihrer herstellung |
| EA019709B1 (ru) | 2008-02-07 | 2014-05-30 | Бёрингер Ингельхайм Интернациональ Гмбх | Спирогетероциклы и их применение в качестве лекарственных средств |
| ES2444128T3 (es) | 2008-05-13 | 2014-02-24 | Astrazeneca Ab | Nueva SAL-554 |
| US8648191B2 (en) | 2008-08-08 | 2014-02-11 | Boehringer Ingelheim International Gmbh | Cyclohexyloxy substituted heterocycles, pharmaceutical compositions containing these compounds and processes for preparing them |
| AR075025A1 (es) | 2009-01-16 | 2011-03-02 | Bristol Myers Squibb Co | Sales de malato de n-(4-((6,7-bis(metiloxi) quinolin-4-il) oxi)fenil)-n'-(4-fluorofenil) ciclopropan-1,1-dicarboxamida y formas cristalinas de las mismas |
| JP5963672B2 (ja) | 2009-07-06 | 2016-08-03 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｂｉｂｗ２９９２、その塩及びこの活性成分を含む固体医薬製剤の乾燥方法 |
| UA108618C2 (uk) | 2009-08-07 | 2015-05-25 | Застосування c-met-модуляторів в комбінації з темозоломідом та/або променевою терапією для лікування раку | |
| KR101317809B1 (ko) | 2011-06-07 | 2013-10-16 | 한미약품 주식회사 | 암세포의 성장을 억제하는 아마이드 유도체 및 비금속염 활택제를 포함하는 약학 조성물 |
| KR20140096571A (ko) | 2013-01-28 | 2014-08-06 | 한미약품 주식회사 | 1-(4-(4-(3,4-디클로로-2-플루오로페닐아미노)-7-메톡시퀴나졸린-6-일옥시)피페리딘-1-일)프로프-2-엔-1-온의 제조방법 |
| HUE034568T2 (en) | 2013-03-06 | 2018-02-28 | Astrazeneca Ab | Quinazoline inhibitors of activating mutant forms of epidermal growth factor receptor |
| US9242965B2 (en) | 2013-12-31 | 2016-01-26 | Boehringer Ingelheim International Gmbh | Process for the manufacture of (E)-4-N,N-dialkylamino crotonic acid in HX salt form and use thereof for synthesis of EGFR tyrosine kinase inhibitors |
| AP2016009521A0 (en) * | 2014-04-04 | 2016-10-31 | Lundbeck & Co As H | Halogenated quinazolin-thf-amines as pde1 inhibitors |
| US20170176028A1 (en) | 2015-12-18 | 2017-06-22 | Lg Electronics Inc. | Air conditioner |
| MA46852A (fr) | 2016-11-17 | 2019-09-25 | Univ Texas | Composés à activité antitumorale contre des cellules cancéreuses porteuses de mutations egfr ou her2 exon 20 |
| CN112321814B (zh) * | 2020-12-30 | 2021-03-23 | 广州初曲科技有限公司 | 一种吉非替尼艾地苯醌轭合物的制备及用途 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9508538D0 (en) * | 1995-04-27 | 1995-06-14 | Zeneca Ltd | Quinazoline derivatives |
| GB9624482D0 (en) * | 1995-12-18 | 1997-01-15 | Zeneca Phaema S A | Chemical compounds |
| IL125686A (en) * | 1996-02-13 | 2002-11-10 | Zeneca Ltd | Quinazoline derivatives, processes for their preparation, pharmaceutical preparations containing them and their use in the manufacture of a drug with an anti-angiogenic effect and / or an effect of reducing vascular permeability |
| GB9603095D0 (en) * | 1996-02-14 | 1996-04-10 | Zeneca Ltd | Quinazoline derivatives |
| IL125954A (en) * | 1996-03-05 | 2003-06-24 | Zeneca Ltd | Quinazoline derivatives, processes for their preparation, pharmaceutical compositions containing them and use thereof in the manufacture of medicaments having an antiangiogenic and/or vascular permeability reducing effect |
| NZ332119A (en) * | 1996-04-12 | 2001-08-31 | Warner Lambert Co | Quinazoline compounds which are irreversible inhibitors of tyrosine kinases |
| GB9718972D0 (en) * | 1996-09-25 | 1997-11-12 | Zeneca Ltd | Chemical compounds |
| DE19911509A1 (de) * | 1999-03-15 | 2000-09-21 | Boehringer Ingelheim Pharma | Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
-
2000
- 2000-08-26 DE DE10042058A patent/DE10042058A1/de not_active Ceased
-
2001
- 2001-08-18 KR KR1020037002744A patent/KR100862873B1/ko not_active Expired - Fee Related
- 2001-08-18 EA EA200300219A patent/EA005679B1/ru not_active IP Right Cessation
- 2001-08-18 SK SK231-2003A patent/SK287747B6/sk not_active IP Right Cessation
- 2001-08-18 EP EP01967285A patent/EP1315705A1/de not_active Ceased
- 2001-08-18 CZ CZ20030870A patent/CZ302567B6/cs not_active IP Right Cessation
- 2001-08-18 JP JP2002523469A patent/JP4834282B2/ja not_active Expired - Fee Related
- 2001-08-18 AU AU8769401A patent/AU8769401A/xx active Pending
- 2001-08-18 AU AU2001287694A patent/AU2001287694B2/en not_active Ceased
- 2001-08-18 IL IL15460201A patent/IL154602A0/xx unknown
- 2001-08-18 UA UA2003032533A patent/UA73004C2/uk unknown
- 2001-08-18 NZ NZ524668A patent/NZ524668A/en not_active IP Right Cessation
- 2001-08-18 RS YU14003A patent/RS52279B/en unknown
- 2001-08-18 CA CA002417897A patent/CA2417897C/en not_active Expired - Fee Related
- 2001-08-18 MX MXPA03001483A patent/MXPA03001483A/es active IP Right Grant
- 2001-08-18 CN CNB01814635XA patent/CN100404517C/zh not_active Expired - Fee Related
- 2001-08-18 HR HR20030138A patent/HRP20030138A2/hr not_active Application Discontinuation
- 2001-08-18 EE EEP200300077A patent/EE05269B1/xx not_active IP Right Cessation
- 2001-08-18 HU HU0300819A patent/HUP0300819A3/hu unknown
- 2001-08-18 ME MEP-587/08A patent/MEP58708A/xx unknown
- 2001-08-18 WO PCT/EP2001/009532 patent/WO2002018351A1/de active Application Filing
- 2001-08-18 BR BR0113519-8A patent/BR0113519A/pt not_active Application Discontinuation
- 2001-08-18 PL PL36024801A patent/PL360248A1/xx not_active Application Discontinuation
- 2001-08-23 UY UY26903A patent/UY26903A1/es not_active Application Discontinuation
- 2001-08-24 MY MYPI20013985A patent/MY126132A/en unknown
- 2001-08-24 TW TW090120905A patent/TWI294422B/zh not_active IP Right Cessation
- 2001-08-24 AR ARP010104041A patent/AR033562A1/es unknown
-
2003
- 2003-02-03 EC EC2003004464A patent/ECSP034464A/es unknown
- 2003-02-05 ZA ZA200300991A patent/ZA200300991B/en unknown
- 2003-02-14 BG BG107559A patent/BG107559A/bg unknown
- 2003-02-24 IL IL154602A patent/IL154602A/en not_active IP Right Cessation
- 2003-02-25 NO NO20030870A patent/NO324866B1/no not_active IP Right Cessation
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