NZ546477A - 4-Alkylamino-2-(heterocyclic)quinazolines and their use in cancer therapy - Google Patents
4-Alkylamino-2-(heterocyclic)quinazolines and their use in cancer therapyInfo
- Publication number
- NZ546477A NZ546477A NZ546477A NZ54647706A NZ546477A NZ 546477 A NZ546477 A NZ 546477A NZ 546477 A NZ546477 A NZ 546477A NZ 54647706 A NZ54647706 A NZ 54647706A NZ 546477 A NZ546477 A NZ 546477A
- Authority
- NZ
- New Zealand
- Prior art keywords
- benzofuran
- dimethyl
- propanediamine
- quinazolinyl
- dihydrochloride
- Prior art date
Links
- 238000011275 oncology therapy Methods 0.000 title claims description 6
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 80
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 31
- 238000000034 method Methods 0.000 claims abstract description 27
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 90
- 239000000203 mixture Substances 0.000 claims description 87
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 62
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 56
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 56
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 55
- -1 amino, hydroxyl Chemical group 0.000 claims description 53
- 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 claims description 51
- 210000004027 cell Anatomy 0.000 claims description 49
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 48
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 32
- PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical class NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 claims description 31
- 229910052760 oxygen Inorganic materials 0.000 claims description 31
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 28
- 239000001301 oxygen Substances 0.000 claims description 28
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 26
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 26
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 24
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
- 229940002612 prodrug Drugs 0.000 claims description 17
- 239000000651 prodrug Substances 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 201000011510 cancer Diseases 0.000 claims description 14
- BIDXGEXQRVWXMY-UHFFFAOYSA-N 1-azaniumylpropylazanium;dichloride Chemical compound Cl.Cl.CCC(N)N BIDXGEXQRVWXMY-UHFFFAOYSA-N 0.000 claims description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 10
- 235000001014 amino acid Nutrition 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 229910019142 PO4 Inorganic materials 0.000 claims description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 9
- 239000010452 phosphate Substances 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 239000002246 antineoplastic agent Substances 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
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- PDVPJSCNFLKENT-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-4-oxo-1h-quinazoline-6-carboxamide Chemical compound C1=CC=C2OC(C3=NC4=CC=C(C=C4C(=O)N3)C(=O)N)=CC2=C1 PDVPJSCNFLKENT-UHFFFAOYSA-N 0.000 claims description 3
- VXYABLYQCMPUIA-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-4-oxo-1h-quinazoline-8-carboxamide Chemical compound C1=CC=C2OC(C3=NC4=C(C(N3)=O)C=CC=C4C(=O)N)=CC2=C1 VXYABLYQCMPUIA-UHFFFAOYSA-N 0.000 claims description 3
- ISSCYMWJYBQJML-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-5-chloro-1h-quinazolin-4-one Chemical compound C1=CC=C2OC(C3=NC=4C=CC=C(C=4C(=O)N3)Cl)=CC2=C1 ISSCYMWJYBQJML-UHFFFAOYSA-N 0.000 claims description 3
- BRRCSZLDAXAOBO-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-6,8-dichloro-1h-quinazolin-4-one Chemical compound C1=CC=C2OC(C3=NC4=C(Cl)C=C(C=C4C(=O)N3)Cl)=CC2=C1 BRRCSZLDAXAOBO-UHFFFAOYSA-N 0.000 claims description 3
- GNOMBDCSOYAOEV-UHFFFAOYSA-N 2-(1-benzofuran-2-yl)-8-methoxy-1h-quinazolin-4-one Chemical compound C1=CC=C2OC(C3=NC4=C(C(N3)=O)C=CC=C4OC)=CC2=C1 GNOMBDCSOYAOEV-UHFFFAOYSA-N 0.000 claims description 3
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- KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 claims description 2
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- HCLLOQLXKCCWLJ-UHFFFAOYSA-N methyl 2-amino-6-methylbenzoate Chemical compound COC(=O)C1=C(C)C=CC=C1N HCLLOQLXKCCWLJ-UHFFFAOYSA-N 0.000 description 1
- NFPMHGVGDWXWRJ-UHFFFAOYSA-N methyl 2-amino-6-nitrobenzoate Chemical compound COC(=O)C1=C(N)C=CC=C1[N+]([O-])=O NFPMHGVGDWXWRJ-UHFFFAOYSA-N 0.000 description 1
- NZZDEODTCXHCRS-UHFFFAOYSA-N methyl 2-aminopyridine-3-carboxylate Chemical compound COC(=O)C1=CC=CN=C1N NZZDEODTCXHCRS-UHFFFAOYSA-N 0.000 description 1
- WHMQTPBEFHEYJI-UHFFFAOYSA-N methyl 3-aminonaphthalene-2-carboxylate Chemical compound C1=CC=C2C=C(N)C(C(=O)OC)=CC2=C1 WHMQTPBEFHEYJI-UHFFFAOYSA-N 0.000 description 1
- YQKTYFNLRUWQFV-UHFFFAOYSA-N methyl 3-aminopyridine-2-carboxylate Chemical compound COC(=O)C1=NC=CC=C1N YQKTYFNLRUWQFV-UHFFFAOYSA-N 0.000 description 1
- 239000013081 microcrystal Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- KPTRDYONBVUWPD-UHFFFAOYSA-N naphthalen-2-ylboronic acid Chemical compound C1=CC=CC2=CC(B(O)O)=CC=C21 KPTRDYONBVUWPD-UHFFFAOYSA-N 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- 230000017095 negative regulation of cell growth Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000011580 nude mouse model Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 201000008968 osteosarcoma Diseases 0.000 description 1
- 230000002611 ovarian Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- PRWVAPJXQCMOFT-UHFFFAOYSA-M potassium;azane;hydroxide Chemical compound N.[OH-].[K+] PRWVAPJXQCMOFT-UHFFFAOYSA-M 0.000 description 1
- VLYFRFHWUBBLRR-UHFFFAOYSA-L potassium;sodium;carbonate Chemical compound [Na+].[K+].[O-]C([O-])=O VLYFRFHWUBBLRR-UHFFFAOYSA-L 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- XJMOSONTPMZWPB-UHFFFAOYSA-M propidium iodide Chemical compound [I-].[I-].C12=CC(N)=CC=C2C2=CC=C(N)C=C2[N+](CCC[N+](C)(CC)CC)=C1C1=CC=CC=C1 XJMOSONTPMZWPB-UHFFFAOYSA-M 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- CZAAKPFIWJXPQT-UHFFFAOYSA-N quinazolin-2-amine Chemical class C1=CC=CC2=NC(N)=NC=C21 CZAAKPFIWJXPQT-UHFFFAOYSA-N 0.000 description 1
- ABVYZAMNSCVWJA-UHFFFAOYSA-N quinazoline-2-carboxamide Chemical compound C1=CC=CC2=NC(C(=O)N)=NC=C21 ABVYZAMNSCVWJA-UHFFFAOYSA-N 0.000 description 1
- YGDICLRMNDWZAK-UHFFFAOYSA-N quinolin-3-ylboronic acid Chemical compound C1=CC=CC2=CC(B(O)O)=CN=C21 YGDICLRMNDWZAK-UHFFFAOYSA-N 0.000 description 1
- 101150013400 rag1 gene Proteins 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 230000028617 response to DNA damage stimulus Effects 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 229940082569 selenite Drugs 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000008354 sodium chloride injection Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005556 structure-activity relationship Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- 230000004580 weight loss 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
- C07D405/04—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 directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- 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
- C07D405/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/5005—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells
- G01N33/5008—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells for testing or evaluating the effect of chemical or biological compounds, e.g. drugs, cosmetics
- G01N33/5011—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells for testing or evaluating the effect of chemical or biological compounds, e.g. drugs, cosmetics for testing antineoplastic activity
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Immunology (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Cell Biology (AREA)
- Food Science & Technology (AREA)
- Biotechnology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- Toxicology (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Quinoline Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NZ546477A NZ546477A (en) | 2006-04-07 | 2006-04-07 | 4-Alkylamino-2-(heterocyclic)quinazolines and their use in cancer therapy |
| PCT/NZ2007/000077 WO2007117161A1 (en) | 2006-04-07 | 2007-04-04 | Substituted ring fused azines and their use in cancer therapy |
| EP07747705A EP2004637A4 (en) | 2006-04-07 | 2007-04-04 | SUBSTITUTED RING-CONDENSED AZINES AND THEIR USE IN CANCER THERAPY |
| AU2007235751A AU2007235751A1 (en) | 2006-04-07 | 2007-04-04 | Substituted ring fused azines and their use in cancer therapy |
| CNA2007800204647A CN101460490A (zh) | 2006-04-07 | 2007-04-04 | 取代的环稠合吖嗪类及其在癌症疗法中的应用 |
| CA002648323A CA2648323A1 (en) | 2006-04-07 | 2007-04-04 | Substituted ring fused azines and their use in cancer therapy |
| JP2009504144A JP2009533338A (ja) | 2006-04-07 | 2007-04-04 | 置換環縮合アジンおよび癌治療におけるそれらの使用 |
| US12/296,377 US20090318479A1 (en) | 2006-04-07 | 2007-04-04 | Substituted ring fused azines and their use in cancer therapy |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NZ546477A NZ546477A (en) | 2006-04-07 | 2006-04-07 | 4-Alkylamino-2-(heterocyclic)quinazolines and their use in cancer therapy |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ546477A true NZ546477A (en) | 2009-04-30 |
Family
ID=38581368
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ546477A NZ546477A (en) | 2006-04-07 | 2006-04-07 | 4-Alkylamino-2-(heterocyclic)quinazolines and their use in cancer therapy |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20090318479A1 (enExample) |
| EP (1) | EP2004637A4 (enExample) |
| JP (1) | JP2009533338A (enExample) |
| CN (1) | CN101460490A (enExample) |
| AU (1) | AU2007235751A1 (enExample) |
| CA (1) | CA2648323A1 (enExample) |
| NZ (1) | NZ546477A (enExample) |
| WO (1) | WO2007117161A1 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012046207A1 (en) * | 2010-10-08 | 2012-04-12 | Paraco Technology Limited | Anti-parasitic substituted ring fused azine compounds |
| US8710064B2 (en) * | 2011-10-20 | 2014-04-29 | China Medical University | 2-aryl-4-quinazolinones and their pharmaceutical compositions |
| KR20150016406A (ko) | 2012-06-07 | 2015-02-11 | 에프. 호프만-라 로슈 아게 | 탄키라제의 피라졸로피리미돈 및 피라졸로피리돈 억제제 |
| WO2013182580A1 (en) | 2012-06-07 | 2013-12-12 | F. Hoffmann-La Roche Ag | Pyrrolopyrimidone and pyrrolopyridone inhibitors of tankyrase |
| WO2014143609A1 (en) | 2013-03-11 | 2014-09-18 | Bristol-Myers Squibb Company | Isoquinolines as potassium ion channel inhibitors |
| CN105916506B (zh) | 2013-11-20 | 2020-01-07 | 圣诺康生命科学公司 | 作为tam家族激酶抑制剂的喹唑啉衍生物 |
| MX2017005346A (es) * | 2014-10-29 | 2017-08-02 | Dong A St Co Ltd | Nuevos compuestos de piridopirimidinona para modular la actividad catalitica de histona lisina desmetilasas (kdm). |
| US20170057955A1 (en) * | 2015-08-26 | 2017-03-02 | Dong-A Socio Holdings Co., Ltd. | Pyridopyrimidinone Compounds for Modulating the Catalytic Activity of Histone Lysine Demethylases (KDMs) |
| CN107721982B (zh) * | 2017-10-16 | 2019-12-03 | 中山大学 | 一种抗肥胖症化合物及其制备方法和应用 |
| CN110483394A (zh) * | 2019-09-02 | 2019-11-22 | 广东工业大学 | 一种化合物的应用 |
| CN113072543B (zh) * | 2020-01-03 | 2022-07-22 | 南方医科大学 | 一种2-芳杂环基喹唑啉酮类化合物及其制备方法和用途 |
| WO2021155426A1 (en) * | 2020-02-04 | 2021-08-12 | TroBio Therapeutics Pty Ltd | Quinazoline compounds and the use thereof in the treatment of cancer |
| WO2022061224A1 (en) | 2020-09-21 | 2022-03-24 | Landos Biopharma, Inc. | Nlrx1 ligands |
| CN114044769B (zh) * | 2021-11-25 | 2023-12-12 | 中山大学 | 一种β-吲哚喹唑啉酮衍生物及其制备方法和应用 |
| CN117247374A (zh) * | 2022-06-10 | 2023-12-19 | 成都先导药物开发股份有限公司 | 一种bcl-xl抑制剂及其制药用途 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3897432A (en) * | 1971-04-21 | 1975-07-29 | Merck & Co Inc | Substituted benzimidazole derivatives |
| HUP0201215A2 (en) * | 1998-12-02 | 2002-08-28 | Pfizer Prod Inc | Methods and compositions for restoring conformational stability of a protein of the p53 family |
| EP1088818B1 (en) * | 1999-10-01 | 2004-11-03 | F. Hoffmann-La Roche Ag | Quinolin-4-yl derivatives |
| CN1186324C (zh) * | 2000-04-27 | 2005-01-26 | 山之内制药株式会社 | 稠合杂芳基衍生物 |
| WO2002062767A1 (en) * | 2001-02-07 | 2002-08-15 | Sumitomo Pharmaceuticals Company, Limited | Novel quinazoline derivatives |
-
2006
- 2006-04-07 NZ NZ546477A patent/NZ546477A/en not_active IP Right Cessation
-
2007
- 2007-04-04 WO PCT/NZ2007/000077 patent/WO2007117161A1/en not_active Ceased
- 2007-04-04 EP EP07747705A patent/EP2004637A4/en not_active Withdrawn
- 2007-04-04 CA CA002648323A patent/CA2648323A1/en not_active Abandoned
- 2007-04-04 AU AU2007235751A patent/AU2007235751A1/en not_active Abandoned
- 2007-04-04 CN CNA2007800204647A patent/CN101460490A/zh active Pending
- 2007-04-04 JP JP2009504144A patent/JP2009533338A/ja active Pending
- 2007-04-04 US US12/296,377 patent/US20090318479A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| CN101460490A (zh) | 2009-06-17 |
| CA2648323A1 (en) | 2007-10-18 |
| US20090318479A1 (en) | 2009-12-24 |
| AU2007235751A1 (en) | 2007-10-18 |
| JP2009533338A (ja) | 2009-09-17 |
| EP2004637A1 (en) | 2008-12-24 |
| EP2004637A4 (en) | 2010-11-03 |
| WO2007117161A1 (en) | 2007-10-18 |
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| PSEA | Patent sealed | ||
| RENW | Renewal (renewal fees accepted) | ||
| LAPS | Patent lapsed |