CA2426775A1 - Thienopyrimidine-based inhibitors of the src family - Google Patents
Thienopyrimidine-based inhibitors of the src family Download PDFInfo
- Publication number
- CA2426775A1 CA2426775A1 CA002426775A CA2426775A CA2426775A1 CA 2426775 A1 CA2426775 A1 CA 2426775A1 CA 002426775 A CA002426775 A CA 002426775A CA 2426775 A CA2426775 A CA 2426775A CA 2426775 A1 CA2426775 A1 CA 2426775A1
- Authority
- CA
- Canada
- Prior art keywords
- hydrazone
- pyrimidin
- methylthieno
- aromatic ring
- phenyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
Links
- RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical compound C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 title abstract description 58
- 239000003112 inhibitor Substances 0.000 title description 42
- 150000001875 compounds Chemical class 0.000 claims abstract description 140
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 72
- 201000010099 disease Diseases 0.000 claims abstract description 67
- 238000011282 treatment Methods 0.000 claims abstract description 55
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims abstract description 42
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims abstract description 42
- 208000026935 allergic disease Diseases 0.000 claims abstract description 22
- 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 19
- 230000000172 allergic effect Effects 0.000 claims abstract description 17
- 208000014951 hematologic disease Diseases 0.000 claims abstract description 17
- 208000012902 Nervous system disease Diseases 0.000 claims abstract description 16
- 208000026278 immune system disease Diseases 0.000 claims abstract description 16
- 208000036142 Viral infection Diseases 0.000 claims abstract description 15
- 230000003463 hyperproliferative effect Effects 0.000 claims abstract description 15
- 230000009385 viral infection Effects 0.000 claims abstract description 15
- 208000025966 Neurological disease Diseases 0.000 claims abstract description 14
- 208000001132 Osteoporosis Diseases 0.000 claims abstract description 13
- 150000007857 hydrazones Chemical class 0.000 claims description 430
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 165
- GOUHYARYYWKXHS-UHFFFAOYSA-N 4-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-N 0.000 claims description 160
- JVTZFYYHCGSXJV-UHFFFAOYSA-N isovanillin Chemical compound COC1=CC=C(C=O)C=C1O JVTZFYYHCGSXJV-UHFFFAOYSA-N 0.000 claims description 140
- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 claims description 114
- 229910052739 hydrogen Inorganic materials 0.000 claims description 111
- 239000001257 hydrogen Substances 0.000 claims description 109
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 100
- 125000000217 alkyl group Chemical group 0.000 claims description 93
- 238000000034 method Methods 0.000 claims description 89
- 125000003118 aryl group Chemical group 0.000 claims description 80
- 210000004027 cell Anatomy 0.000 claims description 77
- -1 4-OCH3-phenyl Chemical group 0.000 claims description 70
- CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 claims description 67
- 206010028980 Neoplasm Diseases 0.000 claims description 65
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 62
- 229910052736 halogen Inorganic materials 0.000 claims description 56
- 150000002367 halogens Chemical group 0.000 claims description 56
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 50
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 44
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 25
- 201000011510 cancer Diseases 0.000 claims description 23
- 238000010992 reflux Methods 0.000 claims description 22
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 16
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 16
- 210000001519 tissue Anatomy 0.000 claims description 14
- 230000002401 inhibitory effect Effects 0.000 claims description 12
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 9
- AAKJQPDSJSZPEX-UHFFFAOYSA-N 7-methyl-n-(pyridin-3-ylmethylideneamino)thieno[3,2-d]pyrimidin-4-amine Chemical compound N1=CN=C2C(C)=CSC2=C1NN=CC1=CC=CN=C1 AAKJQPDSJSZPEX-UHFFFAOYSA-N 0.000 claims description 9
- 241000700605 Viruses Species 0.000 claims description 9
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 8
- 239000003937 drug carrier Substances 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 208000035143 Bacterial infection Diseases 0.000 claims description 7
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 7
- 230000012010 growth Effects 0.000 claims description 7
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 7
- UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 claims description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 6
- 230000014509 gene expression Effects 0.000 claims description 6
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- 101001004391 Drosophila melanogaster Protein jim lovell Proteins 0.000 claims description 5
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- 108010019530 Vascular Endothelial Growth Factors Proteins 0.000 claims description 5
- 210000000601 blood cell Anatomy 0.000 claims description 5
- 238000007912 intraperitoneal administration Methods 0.000 claims description 5
- BYYVBPIKZCTQLO-UHFFFAOYSA-N n-(pyridin-3-ylmethylideneamino)-6-thiophen-3-ylthieno[3,2-d]pyrimidin-4-amine Chemical compound N=1C=NC=2C=C(C3=CSC=C3)SC=2C=1NN=CC1=CC=CN=C1 BYYVBPIKZCTQLO-UHFFFAOYSA-N 0.000 claims description 5
- 238000007920 subcutaneous administration Methods 0.000 claims description 5
- ADZUEEUKBYCSEY-UHFFFAOYSA-N 1h-indole-5-carbaldehyde Chemical compound O=CC1=CC=C2NC=CC2=C1 ADZUEEUKBYCSEY-UHFFFAOYSA-N 0.000 claims description 4
- WEGYGNROSJDEIW-UHFFFAOYSA-N 3-Acetylpyridine Chemical compound CC(=O)C1=CC=CN=C1 WEGYGNROSJDEIW-UHFFFAOYSA-N 0.000 claims description 4
- UHDNUPHSDMOGCR-UHFFFAOYSA-N 3-Formylbenzoic acid Chemical compound OC(=O)C1=CC=CC(C=O)=C1 UHDNUPHSDMOGCR-UHFFFAOYSA-N 0.000 claims description 4
- WMPDAIZRQDCGFH-UHFFFAOYSA-N 3-methoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1 WMPDAIZRQDCGFH-UHFFFAOYSA-N 0.000 claims description 4
- DCIPCSQXMBFWDJ-UHFFFAOYSA-N 7-bromo-n-(pyridin-3-ylmethylideneamino)thieno[3,2-d]pyrimidin-4-amine Chemical compound N1=CN=C2C(Br)=CSC2=C1NN=CC1=CC=CN=C1 DCIPCSQXMBFWDJ-UHFFFAOYSA-N 0.000 claims description 4
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 4
- 206010002198 Anaphylactic reaction Diseases 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 4
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 4
- 102000038012 SFKs Human genes 0.000 claims description 4
- 108091008118 SFKs Proteins 0.000 claims description 4
- 150000001299 aldehydes Chemical class 0.000 claims description 4
- 230000036783 anaphylactic response Effects 0.000 claims description 4
- 208000003455 anaphylaxis Diseases 0.000 claims description 4
- 210000004556 brain Anatomy 0.000 claims description 4
- 206010015037 epilepsy Diseases 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- CBOQJANXLMLOSS-UHFFFAOYSA-N ethyl vanillin Chemical compound CCOC1=CC(C=O)=CC=C1O CBOQJANXLMLOSS-UHFFFAOYSA-N 0.000 claims description 4
- 238000007918 intramuscular administration Methods 0.000 claims description 4
- 238000007911 parenteral administration Methods 0.000 claims description 4
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 claims description 4
- HGZJJKZPPMFIBU-UHFFFAOYSA-N 3-formylbenzonitrile Chemical compound O=CC1=CC=CC(C#N)=C1 HGZJJKZPPMFIBU-UHFFFAOYSA-N 0.000 claims description 3
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 210000001185 bone marrow Anatomy 0.000 claims description 3
- 210000000481 breast Anatomy 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- JMYVMOUINOAAPA-UHFFFAOYSA-N cyclopropanecarbaldehyde Chemical compound O=CC1CC1 JMYVMOUINOAAPA-UHFFFAOYSA-N 0.000 claims description 3
- 230000004069 differentiation Effects 0.000 claims description 3
- 230000035755 proliferation Effects 0.000 claims description 3
- 210000002307 prostate Anatomy 0.000 claims description 3
- 230000010076 replication Effects 0.000 claims description 3
- ZGTFNNUASMWGTM-UHFFFAOYSA-N 1,3-thiazole-2-carbaldehyde Chemical compound O=CC1=NC=CS1 ZGTFNNUASMWGTM-UHFFFAOYSA-N 0.000 claims description 2
- UEBFLTZXUXZPJO-UHFFFAOYSA-N 1-methylimidazole-2-carbaldehyde Chemical compound CN1C=CN=C1C=O UEBFLTZXUXZPJO-UHFFFAOYSA-N 0.000 claims description 2
- 125000006017 1-propenyl group Chemical group 0.000 claims description 2
- ZQEXIXXJFSQPNA-UHFFFAOYSA-N 1h-imidazole-5-carbaldehyde Chemical compound O=CC1=CNC=N1 ZQEXIXXJFSQPNA-UHFFFAOYSA-N 0.000 claims description 2
- ZPKFAUMSOQNWKC-UHFFFAOYSA-N 2-chloro-4-[[(7-methylthieno[3,2-d]pyrimidin-4-yl)hydrazinylidene]methyl]phenol Chemical compound Cc1csc2c(NN=Cc3ccc(O)c(Cl)c3)ncnc12 ZPKFAUMSOQNWKC-UHFFFAOYSA-N 0.000 claims description 2
- IBMUHJIDXFMZPI-UHFFFAOYSA-N 2-chlorobenzaldehyde Chemical compound ClC1=CC=CC=C1C=O.ClC1=CC=CC=C1C=O IBMUHJIDXFMZPI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
- NTBXLLOVTLCQGG-UHFFFAOYSA-N 2-ethoxy-4-[[(7-methylthieno[3,2-d]pyrimidin-4-yl)hydrazinylidene]methyl]phenol Chemical compound CCOc1cc(C=NNc2ncnc3c(C)csc23)ccc1O NTBXLLOVTLCQGG-UHFFFAOYSA-N 0.000 claims description 2
- RVOCDIXIRGHFTC-UHFFFAOYSA-N 2-methoxy-4-[[(7-methylthieno[3,2-d]pyrimidin-4-yl)hydrazinylidene]methyl]phenol Chemical compound COc1cc(C=NNc2ncnc3c(C)csc23)ccc1O RVOCDIXIRGHFTC-UHFFFAOYSA-N 0.000 claims description 2
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- LOPRJHOLWKJBAP-UHFFFAOYSA-N 3-[[(7-methylthieno[3,2-d]pyrimidin-4-yl)hydrazinylidene]methyl]phenol Chemical compound N1=CN=C2C(C)=CSC2=C1NN=CC1=CC=CC(O)=C1 LOPRJHOLWKJBAP-UHFFFAOYSA-N 0.000 claims description 2
- SUISZCALMBHJQX-UHFFFAOYSA-N 3-bromobenzaldehyde Chemical compound BrC1=CC=CC(C=O)=C1 SUISZCALMBHJQX-UHFFFAOYSA-N 0.000 claims description 2
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 2
- VGSOCYWCRMXQAB-UHFFFAOYSA-N 3-chloro-4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1Cl VGSOCYWCRMXQAB-UHFFFAOYSA-N 0.000 claims description 2
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- QZMGMXBYJZVAJN-UHFFFAOYSA-N 3-ethoxybenzaldehyde Chemical compound CCOC1=CC=CC(C=O)=C1 QZMGMXBYJZVAJN-UHFFFAOYSA-N 0.000 claims description 2
- PIKNVEVCWAAOMJ-UHFFFAOYSA-N 3-fluorobenzaldehyde Chemical compound FC1=CC=CC(C=O)=C1 PIKNVEVCWAAOMJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
- AZVSIHIBYRHSLB-UHFFFAOYSA-N 3-furaldehyde Chemical compound O=CC=1C=COC=1 AZVSIHIBYRHSLB-UHFFFAOYSA-N 0.000 claims description 2
- BSQKBHXYEKVKMN-UHFFFAOYSA-N 3-methylthiophene-2-carbaldehyde Chemical compound CC=1C=CSC=1C=O BSQKBHXYEKVKMN-UHFFFAOYSA-N 0.000 claims description 2
- GFFJBSXKNZDYOJ-UHFFFAOYSA-N 3-propoxybenzaldehyde Chemical compound CCCOC1=CC=CC(C=O)=C1 GFFJBSXKNZDYOJ-UHFFFAOYSA-N 0.000 claims description 2
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 claims description 2
- NTKUBRYZSDFVJT-UHFFFAOYSA-N 4-[[(7-methylthieno[3,2-d]pyrimidin-4-yl)hydrazinylidene]methyl]-2-nitrophenol Chemical compound Cc1csc2c(NN=Cc3ccc(O)c(c3)[N+]([O-])=O)ncnc12 NTKUBRYZSDFVJT-UHFFFAOYSA-N 0.000 claims description 2
- BAKXJKBQQFNGEM-UHFFFAOYSA-N 4-[[(7-methylthieno[3,2-d]pyrimidin-4-yl)hydrazinylidene]methyl]benzene-1,2-diol Chemical compound Cc1csc2c(NN=Cc3ccc(O)c(O)c3)ncnc12 BAKXJKBQQFNGEM-UHFFFAOYSA-N 0.000 claims description 2
- ZMAQUBYUBYLLAP-UHFFFAOYSA-N 4-[[(7-methylthieno[3,2-d]pyrimidin-4-yl)hydrazinylidene]methyl]benzonitrile Chemical compound N1=CN=C2C(C)=CSC2=C1NN=CC1=CC=C(C#N)C=C1 ZMAQUBYUBYLLAP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
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- AVPJUEOAFHTBQK-UHFFFAOYSA-N 6-phenyl-n-(pyridin-3-ylmethylideneamino)thieno[3,2-d]pyrimidin-4-amine Chemical compound N=1C=NC=2C=C(C=3C=CC=CC=3)SC=2C=1NN=CC1=CC=CN=C1 AVPJUEOAFHTBQK-UHFFFAOYSA-N 0.000 claims description 2
- AXRYWHGOVYOUOF-UHFFFAOYSA-N 7-methyl-4-[2-(thiophen-2-ylmethylidene)hydrazinyl]thieno[3,2-d]pyrimidine-6-carboxylic acid Chemical compound N1=CN=C2C(C)=C(C(O)=O)SC2=C1NN=CC1=CC=CS1 AXRYWHGOVYOUOF-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- 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
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
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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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
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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
- A61P37/08—Antiallergic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- Neurosurgery (AREA)
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- Physical Education & Sports Medicine (AREA)
- Immunology (AREA)
- Neurology (AREA)
- Oncology (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Communicable Diseases (AREA)
- Epidemiology (AREA)
- Psychiatry (AREA)
- Virology (AREA)
- Pulmonology (AREA)
- Hospice & Palliative Care (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/694,145 | 2000-10-23 | ||
| US09/694,145 US6503914B1 (en) | 2000-10-23 | 2000-10-23 | Thienopyrimidine-based inhibitors of the Src family |
| PCT/US2001/050198 WO2002057271A2 (en) | 2000-10-23 | 2001-10-23 | Thienopyrimidine-based inhibitors of the src family |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2426775A1 true CA2426775A1 (en) | 2002-07-25 |
Family
ID=24787577
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002426775A Abandoned CA2426775A1 (en) | 2000-10-23 | 2001-10-23 | Thienopyrimidine-based inhibitors of the src family |
Country Status (8)
| Country | Link |
|---|---|
| US (3) | US6503914B1 (enExample) |
| EP (1) | EP1409491A2 (enExample) |
| JP (1) | JP2004517898A (enExample) |
| KR (1) | KR20030040554A (enExample) |
| AU (1) | AU2002246817B2 (enExample) |
| CA (1) | CA2426775A1 (enExample) |
| MX (1) | MXPA03003580A (enExample) |
| WO (1) | WO2002057271A2 (enExample) |
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| WO2003064428A1 (en) * | 2002-01-29 | 2003-08-07 | H. Lundbeck A/S | Furano- and thienopyrimidines as neurokinase inhibitors |
| US7071190B2 (en) * | 2002-02-15 | 2006-07-04 | Rigel Pharmaceuticals, Inc. | Inhibitors to tubulin polymerization |
| GB0226434D0 (en) * | 2002-11-13 | 2002-12-18 | Astrazeneca Ab | Combination product |
| US7365103B2 (en) * | 2002-12-12 | 2008-04-29 | Board Of Regents, The University Of Texas System | Compositions for dark-field polymerization and method of using the same for imprint lithography processes |
| US20040112862A1 (en) * | 2002-12-12 | 2004-06-17 | Molecular Imprints, Inc. | Planarization composition and method of patterning a substrate using the same |
| US20040168613A1 (en) * | 2003-02-27 | 2004-09-02 | Molecular Imprints, Inc. | Composition and method to form a release layer |
| US7122079B2 (en) | 2004-02-27 | 2006-10-17 | Molecular Imprints, Inc. | Composition for an etching mask comprising a silicon-containing material |
| US7396475B2 (en) | 2003-04-25 | 2008-07-08 | Molecular Imprints, Inc. | Method of forming stepped structures employing imprint lithography |
| US7157036B2 (en) | 2003-06-17 | 2007-01-02 | Molecular Imprints, Inc | Method to reduce adhesion between a conformable region and a pattern of a mold |
| US7307118B2 (en) * | 2004-11-24 | 2007-12-11 | Molecular Imprints, Inc. | Composition to reduce adhesion between a conformable region and a mold |
| US20060108710A1 (en) * | 2004-11-24 | 2006-05-25 | Molecular Imprints, Inc. | Method to reduce adhesion between a conformable region and a mold |
| US20050160934A1 (en) * | 2004-01-23 | 2005-07-28 | Molecular Imprints, Inc. | Materials and methods for imprint lithography |
| GB0314943D0 (en) * | 2003-06-25 | 2003-07-30 | Proteome Sciences Plc | Screening methods |
| CA2532084A1 (en) * | 2003-07-11 | 2005-02-03 | Oregon Health And Science University | Methods of treatment and diagnosis using modulators of virus-induced cellular gene sequences |
| US20060014165A1 (en) * | 2003-07-14 | 2006-01-19 | Decode Genetics Ehf. | Methods of diagnosis and treatment for asthma and other respiratory diseases based on haplotype association |
| EP1645263B2 (en) * | 2003-07-15 | 2019-04-24 | Kao Corporation | Oral cavity composition |
| US20050084804A1 (en) * | 2003-10-16 | 2005-04-21 | Molecular Imprints, Inc. | Low surface energy templates |
| US7122482B2 (en) * | 2003-10-27 | 2006-10-17 | Molecular Imprints, Inc. | Methods for fabricating patterned features utilizing imprint lithography |
| CA2546360A1 (en) * | 2003-11-19 | 2005-06-09 | Signal Pharmaceuticals, Llc | Methods of treating diseases and disorders by targeting multiple kinases |
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| JP6978003B2 (ja) * | 2015-12-03 | 2021-12-08 | チョーチアン チアンフェン−イエン バイオテクノロジー カンパニー リミテッド | 複素環式化合物およびその使用 |
| EP3383401B1 (en) | 2015-12-03 | 2020-05-20 | Zheijiang Jianfreng-Yien Biotechnology Co., Ltd. | Thieno-pyrimidine derivatives and uses thereof |
| US10722484B2 (en) | 2016-03-09 | 2020-07-28 | K-Gen, Inc. | Methods of cancer treatment |
| US12390467B2 (en) * | 2018-04-13 | 2025-08-19 | The University Of Toledo | Necroptosis inducers or autophagy inhibitors or a combination thereof |
| US20240116856A1 (en) * | 2020-11-05 | 2024-04-11 | Young Biopharma, Llc | Novel capsaicin analogs and uses thereof |
| WO2025140721A1 (zh) * | 2023-12-28 | 2025-07-03 | 粤港澳大湾区精准医学研究院(广州) | 腙类化合物、其药物组合物及其应用 |
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| US5593997A (en) * | 1995-05-23 | 1997-01-14 | Pfizer Inc. | 4-aminopyrazolo(3-,4-D)pyrimidine and 4-aminopyrazolo-(3,4-D)pyridine tyrosine kinase inhibitors |
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| AR004010A1 (es) | 1995-10-11 | 1998-09-30 | Glaxo Group Ltd | Compuestos heterociclicos |
| CA2233307A1 (en) * | 1996-02-07 | 1997-08-14 | Terence J. Moran | Thiophenopyrimidines |
| HUP0100287A3 (en) | 1997-11-11 | 2003-04-28 | Pfizer Prod Inc | Thienopyrimidine and thienopyridine derivatives useful as anticancer agents |
| AU5654399A (en) | 1998-09-22 | 2000-04-10 | Ishihara Sangyo Kaisha Ltd. | Medical composition containing nitroetheneamine derivative or salt thereof as active constituent |
| US5948911A (en) * | 1998-11-20 | 1999-09-07 | Cell Pathways, Inc. | Method for inhibiting neoplastic cells and related conditions by exposure to thienopyrimidine derivatives |
| KR20020029419A (ko) | 1999-07-07 | 2002-04-18 | 다비드 에 질레스 | 퀴나졸린 유도체 |
| US6313168B1 (en) * | 1999-12-15 | 2001-11-06 | Allergan Sales, Inc. | Use of retinoid receptor antagonists in the treatment of cartilage and bone pathologies |
| US6276782B1 (en) | 2000-01-11 | 2001-08-21 | Eastman Kodak Company | Assisted drop-on-demand inkjet printer |
| WO2001066099A2 (en) | 2000-03-06 | 2001-09-13 | Astrazeneca Ab | Use of quinazoline derivatives as angiogenesis inhibitors |
| US20060004002A1 (en) * | 2004-07-02 | 2006-01-05 | Thomas Thrash | Small molecule thienopyrimidine-based protein tyrosine kinase inhibitors |
-
2000
- 2000-10-23 US US09/694,145 patent/US6503914B1/en not_active Ceased
-
2001
- 2001-10-23 KR KR10-2003-7005566A patent/KR20030040554A/ko not_active Abandoned
- 2001-10-23 JP JP2002557948A patent/JP2004517898A/ja active Pending
- 2001-10-23 MX MXPA03003580A patent/MXPA03003580A/es not_active Application Discontinuation
- 2001-10-23 AU AU2002246817A patent/AU2002246817B2/en not_active Ceased
- 2001-10-23 EP EP01994425A patent/EP1409491A2/en not_active Withdrawn
- 2001-10-23 WO PCT/US2001/050198 patent/WO2002057271A2/en not_active Ceased
- 2001-10-23 US US10/399,816 patent/US7285556B2/en not_active Expired - Fee Related
- 2001-10-23 CA CA002426775A patent/CA2426775A1/en not_active Abandoned
-
2004
- 2004-06-28 US US10/878,140 patent/USRE39267E1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP1409491A2 (en) | 2004-04-21 |
| MXPA03003580A (es) | 2005-04-08 |
| USRE39267E1 (en) | 2006-09-05 |
| JP2004517898A (ja) | 2004-06-17 |
| WO2002057271A3 (en) | 2003-01-30 |
| WO2002057271A2 (en) | 2002-07-25 |
| US20040077663A1 (en) | 2004-04-22 |
| AU2002246817B2 (en) | 2007-07-26 |
| KR20030040554A (ko) | 2003-05-22 |
| US7285556B2 (en) | 2007-10-23 |
| US6503914B1 (en) | 2003-01-07 |
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| Date | Code | Title | Description |
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| EEER | Examination request | ||
| FZDE | Discontinued |