CA2531140C - 2-imino-4-(thio) oxo-5-polycyclovinylazolines for use as pi3 kinase inhibitors - Google Patents
2-imino-4-(thio) oxo-5-polycyclovinylazolines for use as pi3 kinase inhibitors Download PDFInfo
- Publication number
- CA2531140C CA2531140C CA2531140A CA2531140A CA2531140C CA 2531140 C CA2531140 C CA 2531140C CA 2531140 A CA2531140 A CA 2531140A CA 2531140 A CA2531140 A CA 2531140A CA 2531140 C CA2531140 C CA 2531140C
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- Canada
- Prior art keywords
- alkyl
- ylmethylene
- thiazolidin
- benzo
- oxo
- Prior art date
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- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 102000027426 receptor tyrosine kinases Human genes 0.000 description 1
- 108091008598 receptor tyrosine kinases Proteins 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000008521 reorganization Effects 0.000 description 1
- 230000019254 respiratory burst Effects 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 235000002020 sage Nutrition 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000003345 scintillation counting Methods 0.000 description 1
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 230000019100 sperm motility Effects 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003461 sulfonyl halides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical group ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000015523 tannic acid Nutrition 0.000 description 1
- 229940033123 tannic acid Drugs 0.000 description 1
- 229920002258 tannic acid Polymers 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 150000003555 thioacetals Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical class CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 102000027257 transmembrane receptors Human genes 0.000 description 1
- 108091008578 transmembrane receptors Proteins 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- 235000011178 triphosphate Nutrition 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
- IHIXIJGXTJIKRB-UHFFFAOYSA-N trisodium vanadate Chemical compound [Na+].[Na+].[Na+].[O-][V]([O-])([O-])=O IHIXIJGXTJIKRB-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 230000028973 vesicle-mediated transport Effects 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- 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
-
- 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]
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
-
- 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
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- 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
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Transplantation (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Biomedical Technology (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03102313.8 | 2003-07-28 | ||
| EP03102313 | 2003-07-28 | ||
| PCT/EP2004/051625 WO2005011686A1 (en) | 2003-07-28 | 2004-07-27 | 2-imino-4-(thio) oxo-5-poly cyclovinylazolines for use as p13 kinase ihibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2531140A1 CA2531140A1 (en) | 2005-02-10 |
| CA2531140C true CA2531140C (en) | 2013-06-18 |
Family
ID=34112474
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2531140A Expired - Fee Related CA2531140C (en) | 2003-07-28 | 2004-07-27 | 2-imino-4-(thio) oxo-5-polycyclovinylazolines for use as pi3 kinase inhibitors |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8106214B2 (https=) |
| EP (1) | EP1648452B1 (https=) |
| JP (1) | JP4908210B2 (https=) |
| CA (1) | CA2531140C (https=) |
| DE (1) | DE602004022170D1 (https=) |
| ES (1) | ES2328146T3 (https=) |
| IL (1) | IL173195A (https=) |
| NO (1) | NO332434B1 (https=) |
| WO (1) | WO2005011686A1 (https=) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007523957A (ja) * | 2004-02-25 | 2007-08-23 | スミスクライン・ビーチャム・コーポレイション | 新規化学化合物 |
| EP1765817A1 (en) | 2004-07-01 | 2007-03-28 | F.Hoffmann-La Roche Ag | Thiazolinone unsubstituted quinolines |
| CA2576765C (en) * | 2004-09-03 | 2013-05-28 | Applied Research Systems Ars Holding N.V. | Pyridine methylene azolidinones and use thereof phosphoinositide inhibitors |
| US7253285B2 (en) * | 2004-09-17 | 2007-08-07 | Hoffmann-La Roche Inc. | Thiazolinone 4-monosubstituted quinolines |
| US7241893B2 (en) | 2004-09-17 | 2007-07-10 | Hoffman-La Roche Inc. | Thiazolinone 2-substituted quinolines |
| RU2405782C2 (ru) * | 2004-10-14 | 2010-12-10 | Ф.Хоффманн-Ля Рош Аг | Хиназолинилметилентиазолиноны в качестве cdk-1 ингибиторов |
| US7304074B2 (en) * | 2005-04-05 | 2007-12-04 | Hoffmann-La Roche Inc. | Substituted 1,5-naphthyridine azolinones |
| PE20070083A1 (es) * | 2005-06-08 | 2007-01-27 | Smithkline Beecham Corp | (5z)-5-(6-quinoxalinilmetilideno)-2-[(2,6-diclorofenil)amino]-1,3-tiazol-4(5h)-ona |
| JP2009507072A (ja) * | 2005-09-07 | 2009-02-19 | ラボラトワール セローノ ソシエテ アノニム | 子宮内膜症の処置のためのｐｉ３ｋ阻害剤 |
| US20080306057A1 (en) * | 2005-10-11 | 2008-12-11 | Laboratories Serono Sa | P13K Inhibitors for the Treatment of Endometriosis |
| WO2007076875A2 (en) * | 2006-01-06 | 2007-07-12 | Aarhus Universitet | Compounds acting on the serotonin transporter |
| WO2007113005A2 (en) * | 2006-04-03 | 2007-10-11 | European Molecular Biology Laboratory (Embl) | 2-substituted 3-aminosulfonyl-thiophene derivatives as aurora kinase inhibitors |
| TW200815429A (en) * | 2006-04-11 | 2008-04-01 | Smithkline Beecham Corp | Thiazolidinedione derivatives as PI3 kinase inhibitors |
| US20100286041A1 (en) * | 2007-03-22 | 2010-11-11 | Smithkline Beecham Corporation | (5z)-5-(6-quinoxalinylmethylidene)-2-[(2,6-dichlorophenyl)amino]-1,3-thiazol-4(5h)-one |
| US20080255115A1 (en) * | 2007-04-11 | 2008-10-16 | Michael Gerard Darcy | Thiazolidinedione derivatives as pi3 kinase inhibitors |
| PE20090288A1 (es) * | 2007-05-10 | 2009-04-03 | Smithkline Beecham Corp | Derivados de quinoxalina como inhibidores de la pi3 quinasa |
| PE20090717A1 (es) * | 2007-05-18 | 2009-07-18 | Smithkline Beecham Corp | Derivados de quinolina como inhibidores de la pi3 quinasa |
| FR2919608B1 (fr) * | 2007-08-01 | 2012-10-05 | Univ Rennes | Derives d'imidazolones,procede de preparation et applications biologiques |
| TW200942544A (en) | 2008-03-03 | 2009-10-16 | Takeda Pharmaceutical | Combination drug |
| WO2010146059A2 (en) | 2009-06-16 | 2010-12-23 | F. Hoffmann-La Roche Ag | Biomarkers for igf-1r inhibitor therapy |
| CN103108873A (zh) * | 2010-07-16 | 2013-05-15 | 皮拉马尔企业有限公司 | 作为激酶抑制剂的取代的咪唑并喹啉衍生物 |
| CN102584809B (zh) * | 2011-01-14 | 2014-12-24 | 湘北威尔曼制药股份有限公司 | 胺基噻唑烷酮化合物及其制备方法与在制备抗肿瘤药物中的应用 |
| CN104520303B (zh) | 2012-07-30 | 2017-04-12 | 国立大学法人京都大学 | 关于精神神经疾病或恶性肿瘤的化合物及医药组合物 |
| US10310802B2 (en) * | 2014-03-26 | 2019-06-04 | Unanimous A. I., Inc. | System and method for moderating real-time closed-loop collaborative decisions on mobile devices |
| CN106588909B (zh) * | 2017-01-06 | 2019-08-27 | 广东工业大学 | 一种喹啉类衍生物的制备及其在抗炎中的应用 |
| CR20200553A (es) | 2018-04-18 | 2021-04-08 | Constellation Pharmaceuticals Inc | Moduladores de enzimas modificadoras de metilo, composiciones y usos de estos |
| CN120097995A (zh) | 2018-05-21 | 2025-06-06 | 星座制药公司 | 甲基修饰酶的调节剂、其组合物和用途 |
| WO2021016414A1 (en) | 2019-07-24 | 2021-01-28 | Constellation Pharmaceuticals, Inc. | Crystalline forms of 7-chloro-2-(4-(3-methoxyazetidin-1-yl)cyclohexyl)-2,4-dimethyl-n-((6-methyl-4-(methylthio)-2-oxo-1,2-dihydropyridin-3-yl)methyl)benzo[d][1,3]dioxole-5-carboxamide |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JPH052200A (ja) | 1990-09-28 | 1993-01-08 | Toshiba Corp | 有機非線形光学材料 |
| JP3871354B2 (ja) * | 1994-07-29 | 2007-01-24 | 株式会社フジモト・コーポレーション | 新規な２−（ｎ−シアノイミノ）チアゾリジン−４−オン誘導体 |
| CN1681811B (zh) | 2002-07-10 | 2010-05-26 | 默克雪兰诺有限公司 | 唑烷酮-乙烯基稠合的-苯衍生物 |
| MXPA05005406A (es) * | 2002-11-22 | 2005-08-03 | Smithkline Beecham Corp | Compuestos quimicos novedosos. |
| CA2576765C (en) | 2004-09-03 | 2013-05-28 | Applied Research Systems Ars Holding N.V. | Pyridine methylene azolidinones and use thereof phosphoinositide inhibitors |
-
2004
- 2004-07-27 DE DE602004022170T patent/DE602004022170D1/de not_active Expired - Lifetime
- 2004-07-27 WO PCT/EP2004/051625 patent/WO2005011686A1/en not_active Ceased
- 2004-07-27 CA CA2531140A patent/CA2531140C/en not_active Expired - Fee Related
- 2004-07-27 ES ES04766335T patent/ES2328146T3/es not_active Expired - Lifetime
- 2004-07-27 US US10/565,976 patent/US8106214B2/en not_active Expired - Fee Related
- 2004-07-27 JP JP2006521581A patent/JP4908210B2/ja not_active Expired - Fee Related
- 2004-07-27 EP EP04766335A patent/EP1648452B1/en not_active Expired - Lifetime
-
2006
- 2006-01-17 IL IL173195A patent/IL173195A/en not_active IP Right Cessation
- 2006-02-03 NO NO20060573A patent/NO332434B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JP2007500171A (ja) | 2007-01-11 |
| IL173195A (en) | 2013-04-30 |
| NO20060573L (no) | 2006-02-03 |
| CA2531140A1 (en) | 2005-02-10 |
| EP1648452B1 (en) | 2009-07-22 |
| ES2328146T3 (es) | 2009-11-10 |
| EP1648452A1 (en) | 2006-04-26 |
| IL173195A0 (en) | 2006-06-11 |
| US20070021447A1 (en) | 2007-01-25 |
| DE602004022170D1 (de) | 2009-09-03 |
| JP4908210B2 (ja) | 2012-04-04 |
| AU2004260836A1 (en) | 2005-02-10 |
| WO2005011686A1 (en) | 2005-02-10 |
| US8106214B2 (en) | 2012-01-31 |
| NO332434B1 (no) | 2012-09-17 |
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| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20160727 |