CA2770156C - Pyrido[2,3-d]pyrimidinones and their use in the treatment of hyperproliferative diseases - Google Patents
Pyrido[2,3-d]pyrimidinones and their use in the treatment of hyperproliferative diseases Download PDFInfo
- Publication number
- CA2770156C CA2770156C CA2770156A CA2770156A CA2770156C CA 2770156 C CA2770156 C CA 2770156C CA 2770156 A CA2770156 A CA 2770156A CA 2770156 A CA2770156 A CA 2770156A CA 2770156 C CA2770156 C CA 2770156C
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- CA
- Canada
- Prior art keywords
- fluoro
- oxo
- pyrimidin
- phenyl
- tetrahydropyrido
- 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.)
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 29
- 201000010099 disease Diseases 0.000 title claims abstract description 26
- 230000003463 hyperproliferative effect Effects 0.000 title claims abstract description 13
- MHHOMHMNIRXARC-UHFFFAOYSA-N 1h-pyrido[2,3-d]pyrimidin-2-one Chemical class C1=CN=C2NC(=O)N=CC2=C1 MHHOMHMNIRXARC-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 361
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 25
- 201000011510 cancer Diseases 0.000 claims abstract description 15
- 238000002360 preparation method Methods 0.000 claims description 325
- -1 2-oxo-1,2-dihydropyridinyl Chemical group 0.000 claims description 147
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 50
- 150000003839 salts Chemical class 0.000 claims description 49
- 239000012453 solvate Substances 0.000 claims description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
- 229910052731 fluorine Inorganic materials 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 239000004480 active ingredient Substances 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000004434 sulfur atom Chemical group 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
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- 125000006362 methylene amino carbonyl group Chemical group [H]N(C([*:2])=O)C([H])([H])[*:1] 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- XISPDDYROWQPHI-UHFFFAOYSA-N 3,4-dihydro-1h-pyrido[2,3-d]pyrimidin-2-one Chemical group C1=CN=C2NC(=O)NCC2=C1 XISPDDYROWQPHI-UHFFFAOYSA-N 0.000 claims description 2
- 229910006074 SO2NH2 Inorganic materials 0.000 claims description 2
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 2
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- 201000011066 hemangioma Diseases 0.000 claims 3
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- 208000037803 restenosis Diseases 0.000 claims 3
- YOWGCQRWOILZBA-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-[3-fluoro-4-[(2-oxo-3,4-dihydro-1h-pyrido[2,3-d]pyrimidin-5-yl)oxy]phenyl]urea Chemical compound C=1C=C(OC=2C=3CNC(=O)NC=3N=CC=2)C(F)=CC=1NC(=O)NC1=CC=CC(Cl)=C1 YOWGCQRWOILZBA-UHFFFAOYSA-N 0.000 claims 1
- YXHURDDOXJYJCD-UHFFFAOYSA-N 1-[3-fluoro-4-[(2-oxo-3,4-dihydro-1h-pyrido[2,3-d]pyrimidin-5-yl)oxy]phenyl]-3-(4-propan-2-ylphenyl)urea Chemical compound C1=CC(C(C)C)=CC=C1NC(=O)NC(C=C1F)=CC=C1OC1=CC=NC2=C1CNC(=O)N2 YXHURDDOXJYJCD-UHFFFAOYSA-N 0.000 claims 1
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- LEIVNLURDIGCTJ-UHFFFAOYSA-N 2,3-difluoro-n-[2-fluoro-4-[(3-methyl-2-oxo-1,4-dihydropyrido[2,3-d]pyrimidin-5-yl)amino]phenyl]benzamide Chemical compound C1=CN=C2NC(=O)N(C)CC2=C1NC(C=C1F)=CC=C1NC(=O)C1=CC=CC(F)=C1F LEIVNLURDIGCTJ-UHFFFAOYSA-N 0.000 claims 1
- SPNNXEKFUAFBSG-UHFFFAOYSA-N 2,5-dichloro-n-[3-fluoro-4-[(2-oxo-3,4-dihydro-1h-pyrido[2,3-d]pyrimidin-5-yl)oxy]phenyl]pyridine-3-carboxamide Chemical compound C=1C=C(OC=2C=3CNC(=O)NC=3N=CC=2)C(F)=CC=1NC(=O)C1=CC(Cl)=CN=C1Cl SPNNXEKFUAFBSG-UHFFFAOYSA-N 0.000 claims 1
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- NJIDQBULLAICNP-UHFFFAOYSA-N 2-fluoro-n-[3-fluoro-4-[(2-oxo-3,4-dihydro-1h-pyrido[2,3-d]pyrimidin-5-yl)oxy]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C=1C=C(OC=2C=3CNC(=O)NC=3N=CC=2)C(F)=CC=1NC(=O)C1=CC=CC(C(F)(F)F)=C1F NJIDQBULLAICNP-UHFFFAOYSA-N 0.000 claims 1
- XHQBYLDTCYUWQG-UHFFFAOYSA-N 2-fluoro-n-[3-fluoro-4-[(3-methyl-2-oxo-1,4-dihydropyrido[2,3-d]pyrimidin-5-yl)amino]phenyl]benzamide Chemical compound C1=CN=C2NC(=O)N(C)CC2=C1NC(C(=C1)F)=CC=C1NC(=O)C1=CC=CC=C1F XHQBYLDTCYUWQG-UHFFFAOYSA-N 0.000 claims 1
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- FODQLNUOVCCYQE-UHFFFAOYSA-N 3-cyano-n-[3-fluoro-4-[(2-oxo-3,4-dihydro-1h-pyrido[2,3-d]pyrimidin-5-yl)oxy]phenyl]benzamide Chemical compound C=1C=C(OC=2C=3CNC(=O)NC=3N=CC=2)C(F)=CC=1NC(=O)C1=CC=CC(C#N)=C1 FODQLNUOVCCYQE-UHFFFAOYSA-N 0.000 claims 1
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- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 238000012360 testing method Methods 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
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- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical group OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- A—HUMAN NECESSITIES
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- 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
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- A—HUMAN NECESSITIES
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- 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
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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
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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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/14—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Dermatology (AREA)
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- Emergency Medicine (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Rheumatology (AREA)
- Ophthalmology & Optometry (AREA)
- Endocrinology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23187309P | 2009-08-06 | 2009-08-06 | |
| US61/231,873 | 2009-08-06 | ||
| PCT/US2010/043467 WO2011017142A1 (en) | 2009-08-06 | 2010-07-28 | Novel bicyclic urea compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2770156A1 CA2770156A1 (en) | 2011-02-10 |
| CA2770156C true CA2770156C (en) | 2019-02-12 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2770156A Expired - Fee Related CA2770156C (en) | 2009-08-06 | 2010-07-28 | Pyrido[2,3-d]pyrimidinones and their use in the treatment of hyperproliferative diseases |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US8569295B2 (OSRAM) |
| EP (1) | EP2461869B1 (OSRAM) |
| JP (1) | JP5718332B2 (OSRAM) |
| KR (1) | KR20120055608A (OSRAM) |
| CN (1) | CN102573994B (OSRAM) |
| AU (1) | AU2010281368C1 (OSRAM) |
| CA (1) | CA2770156C (OSRAM) |
| EA (1) | EA201200218A1 (OSRAM) |
| ES (1) | ES2433230T3 (OSRAM) |
| IL (1) | IL217651A (OSRAM) |
| MX (1) | MX2012001419A (OSRAM) |
| SG (1) | SG178271A1 (OSRAM) |
| WO (1) | WO2011017142A1 (OSRAM) |
| ZA (1) | ZA201201635B (OSRAM) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
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| KR20110075016A (ko) | 2008-10-14 | 2011-07-05 | 닝 시 | 화합물 및 사용 방법 |
| EP2408300B1 (en) | 2009-03-21 | 2016-05-11 | Sunshine Lake Pharma Co., Ltd. | Amino ester derivatives, salts thereof and methods of use |
| US9290485B2 (en) | 2010-08-04 | 2016-03-22 | Novartis Ag | N-((6-amino-pyridin-3-yl)methyl)-heteroaryl-carboxamides |
| CA2820709C (en) | 2011-02-28 | 2016-02-16 | Sunshine Lake Pharma Co., Ltd. | Substituted quinoline compounds and methods of use |
| AU2012294917A1 (en) * | 2011-08-10 | 2014-03-20 | Merck Patent Gmbh | Pyrido-pyrimidine derivatives |
| GB201201566D0 (en) | 2012-01-30 | 2012-03-14 | Vernalis R&D Ltd | New chemical compounds |
| US8969388B1 (en) | 2012-07-28 | 2015-03-03 | Sunshine Lake Pharma Co., Ltd. | Substituted pyrazolone compounds and methods of use |
| US8975282B2 (en) | 2012-07-28 | 2015-03-10 | Sunshine Lake Pharma Co., Ltd. | Substituted pyrazolone compounds and methods of use |
| EP2890380A2 (en) | 2012-08-29 | 2015-07-08 | Merck Patent GmbH | Ddr2 inhibitors for the treatment of osteoarthritis |
| US9663486B2 (en) | 2013-10-14 | 2017-05-30 | Eisai R&D Management Co., Ltd. | Selectively substituted quinoline compounds |
| EP3626717A1 (en) | 2013-10-14 | 2020-03-25 | Eisai R&D Management Co., Ltd. | Selectively substituted quinoline compounds |
| CN106279147A (zh) * | 2015-05-21 | 2017-01-04 | 中国科学院上海药物研究所 | 一种吡啶并氮杂环化合物及其制备方法和用途 |
| US11096909B2 (en) | 2016-04-06 | 2021-08-24 | University Of Oulu | Compounds for use in the treatment of cancer |
| EA201992584A1 (ru) * | 2017-05-26 | 2020-06-18 | Икнос Сайенсиз Са | Новые ингибиторы map4k1 |
| GB2575490A (en) * | 2018-07-12 | 2020-01-15 | Recordati Ind Chimica E Farmaceutica Spa | P2X3 receptor antagonists |
| CA3109891A1 (en) * | 2018-08-24 | 2020-02-27 | Nanjing Transthera Biosciences Co., Ltd. | Quinoline derivative inhibitor: tam, ntrk, and csf1r kinases |
| AU2020222056A1 (en) * | 2019-02-11 | 2021-10-07 | Phoenix Molecular Designs | Crystalline forms of an RSK inhibitor |
| CN112625026B (zh) * | 2019-09-24 | 2022-09-09 | 药捷安康(南京)科技股份有限公司 | Tam家族激酶抑制剂的喹啉衍生物 |
| AU2021247733A1 (en) | 2020-03-30 | 2022-11-17 | Hutchison Medipharma Limited | Amide compounds and uses thereof |
| CN112225748B (zh) * | 2020-10-20 | 2021-11-30 | 四川大学华西医院 | 一种具有flt3激酶抑制活性的小分子化合物及其应用 |
| WO2022175514A1 (en) | 2021-02-22 | 2022-08-25 | Bayer Aktiengesellschaft | N-(pyridin-2-yl)-acetamides as p2x3 inhibitors |
| KR102726416B1 (ko) * | 2021-12-15 | 2024-11-05 | 한국과학기술연구원 | 엑토뉴클레오티드 피로포스파타아제-포스포디에스터라아제의 저해 활성을 갖는 신규한 피리도피리미딘 유도체 및 이들의 용도 |
| AU2022413540A1 (en) | 2021-12-16 | 2024-07-18 | Kinnate Biopharma Inc. | Inhibitors of met kinase |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2005533039A (ja) * | 2002-05-29 | 2005-11-04 | アムゲン インコーポレイテッド | 細胞増殖関連疾患治療用２−オキソ−１，３，４−トリヒドロキナゾリニル誘導体 |
| DE102004004731A1 (de) * | 2004-01-30 | 2005-08-18 | Merck Patent Gmbh | Harnstoffderivate |
| WO2006094347A1 (en) * | 2005-03-08 | 2006-09-14 | Biota Scientific Management Pty Ltd. | Bicyclic nucleosides and nucleotides as therapeutic agents |
| WO2006127587A1 (en) | 2005-05-20 | 2006-11-30 | Vertex Pharmaceuticals Incorporated | Pyrrolopyridines useful as inhibitors of protein kinase |
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2010
- 2010-07-28 SG SG2012008074A patent/SG178271A1/en unknown
- 2010-07-28 CA CA2770156A patent/CA2770156C/en not_active Expired - Fee Related
- 2010-07-28 AU AU2010281368A patent/AU2010281368C1/en not_active Ceased
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- 2010-07-28 EA EA201200218A patent/EA201200218A1/ru unknown
- 2010-07-28 EP EP10739442.1A patent/EP2461869B1/en not_active Not-in-force
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- 2010-07-28 KR KR1020127005845A patent/KR20120055608A/ko not_active Withdrawn
- 2010-07-28 WO PCT/US2010/043467 patent/WO2011017142A1/en not_active Ceased
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- 2012-03-05 ZA ZA2012/01635A patent/ZA201201635B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EA201200218A1 (ru) | 2012-09-28 |
| US8569295B2 (en) | 2013-10-29 |
| US20120190654A1 (en) | 2012-07-26 |
| JP2013501047A (ja) | 2013-01-10 |
| EP2461869B1 (en) | 2013-08-21 |
| CN102573994B (zh) | 2015-06-24 |
| IL217651A (en) | 2017-08-31 |
| EP2461869A1 (en) | 2012-06-13 |
| AU2010281368C1 (en) | 2016-08-04 |
| KR20120055608A (ko) | 2012-05-31 |
| AU2010281368A1 (en) | 2012-03-22 |
| WO2011017142A1 (en) | 2011-02-10 |
| ES2433230T3 (es) | 2013-12-10 |
| CN102573994A (zh) | 2012-07-11 |
| CA2770156A1 (en) | 2011-02-10 |
| SG178271A1 (en) | 2012-03-29 |
| AU2010281368B2 (en) | 2016-04-14 |
| JP5718332B2 (ja) | 2015-05-13 |
| MX2012001419A (es) | 2012-03-16 |
| ZA201201635B (en) | 2012-11-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20150727 |
|
| MKLA | Lapsed |
Effective date: 20210728 |