CA2663178C - Dibenzofuran derivatives as inhibitors of pde-4 and pde-10 - Google Patents
Dibenzofuran derivatives as inhibitors of pde-4 and pde-10 Download PDFInfo
- Publication number
- CA2663178C CA2663178C CA2663178A CA2663178A CA2663178C CA 2663178 C CA2663178 C CA 2663178C CA 2663178 A CA2663178 A CA 2663178A CA 2663178 A CA2663178 A CA 2663178A CA 2663178 C CA2663178 C CA 2663178C
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- Canada
- Prior art keywords
- methoxydibenzo
- furan
- cyano
- compound
- formula
- Prior art date
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- 239000003112 inhibitor Substances 0.000 title claims abstract description 21
- 101100296719 Caenorhabditis elegans pde-4 gene Proteins 0.000 title 1
- 150000004826 dibenzofurans Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 144
- 150000003839 salts Chemical class 0.000 claims abstract description 24
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims abstract description 17
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 claims abstract description 16
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- 150000001204 N-oxides Chemical class 0.000 claims abstract description 10
- 210000003169 central nervous system Anatomy 0.000 claims abstract description 10
- 239000012453 solvate Substances 0.000 claims abstract description 10
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- 206010069698 Langerhans' cell histiocytosis Diseases 0.000 claims abstract description 6
- 201000004681 Psoriasis Diseases 0.000 claims abstract description 6
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims abstract description 6
- 206010039085 Rhinitis allergic Diseases 0.000 claims abstract description 6
- 206010040070 Septic Shock Diseases 0.000 claims abstract description 6
- 208000002205 allergic conjunctivitis Diseases 0.000 claims abstract description 6
- 201000010105 allergic rhinitis Diseases 0.000 claims abstract description 6
- 208000024998 atopic conjunctivitis Diseases 0.000 claims abstract description 6
- 208000003401 eosinophilic granuloma Diseases 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims abstract description 6
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- 208000011580 syndromic disease Diseases 0.000 claims abstract description 4
- -1 cyano, carboxy Chemical group 0.000 claims description 80
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- 125000000217 alkyl group Chemical group 0.000 claims description 36
- 229920006395 saturated elastomer Polymers 0.000 claims description 35
- 239000001257 hydrogen Substances 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 125000005842 heteroatom Chemical group 0.000 claims description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 17
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 17
- 125000004122 cyclic group Chemical group 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 17
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
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- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
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- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
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- LVFLQDXYFYWNSJ-UHFFFAOYSA-N 1-(4-methoxydibenzofuran-1-yl)-4-methoxyiminocyclohexane-1-carbonitrile Chemical compound C1CC(=NOC)CCC1(C#N)C1=CC=C(OC)C2=C1C1=CC=CC=C1O2 LVFLQDXYFYWNSJ-UHFFFAOYSA-N 0.000 claims 1
- DEOOIBVIBRHOOO-UHFFFAOYSA-N 1-(4-methoxydibenzofuran-1-yl)-4-oxocyclohexane-1-carbonitrile Chemical compound O1C2=CC=CC=C2C2=C1C(OC)=CC=C2C1(C#N)CCC(=O)CC1 DEOOIBVIBRHOOO-UHFFFAOYSA-N 0.000 claims 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims 1
- KEOIXQQDQABMPL-UHFFFAOYSA-N 2-[6-cyano-6-(4-methoxydibenzofuran-1-yl)-4-oxo-7,8-dihydro-5h-quinazolin-3-yl]acetic acid Chemical compound N1=CN(CC(O)=O)C(=O)C(C2)=C1CCC2(C#N)C1=CC=C(OC)C2=C1C1=CC=CC=C1O2 KEOIXQQDQABMPL-UHFFFAOYSA-N 0.000 claims 1
- FDJDWXHNIUYDQQ-UHFFFAOYSA-N 2-[[6-cyano-6-(4-methoxydibenzofuran-1-yl)-7,8-dihydro-5h-quinazolin-2-yl]amino]acetic acid Chemical compound C1CC2=NC(NCC(O)=O)=NC=C2CC1(C#N)C1=CC=C(OC)C2=C1C1=CC=CC=C1O2 FDJDWXHNIUYDQQ-UHFFFAOYSA-N 0.000 claims 1
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- VXLSJDHGLZNWCZ-UHFFFAOYSA-N 2-amino-6-(4-methoxydibenzofuran-1-yl)-7,8-dihydro-5h-quinazoline-6-carbonitrile Chemical compound C1CC2=NC(N)=NC=C2CC1(C#N)C1=CC=C(OC)C2=C1C1=CC=CC=C1O2 VXLSJDHGLZNWCZ-UHFFFAOYSA-N 0.000 claims 1
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- 229940075420 xanthine Drugs 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
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- C07—ORGANIC CHEMISTRY
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- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- 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
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- A—HUMAN NECESSITIES
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- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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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
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- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Pulmonology (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Rheumatology (AREA)
- Immunology (AREA)
- Urology & Nephrology (AREA)
- Dermatology (AREA)
- Hematology (AREA)
- Vascular Medicine (AREA)
- Obesity (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Psychology (AREA)
- Otolaryngology (AREA)
- Ophthalmology & Optometry (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN1647CH2006 | 2006-09-11 | ||
| IN1647/CHE/2006 | 2006-09-11 | ||
| PCT/IB2007/002596 WO2008032171A1 (en) | 2006-09-11 | 2007-09-10 | Dibenzofuran derivatives as inhibitors of pde-4 and pde-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2663178A1 CA2663178A1 (en) | 2008-03-20 |
| CA2663178C true CA2663178C (en) | 2016-01-12 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2663178A Expired - Fee Related CA2663178C (en) | 2006-09-11 | 2007-09-10 | Dibenzofuran derivatives as inhibitors of pde-4 and pde-10 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US8263648B2 (enExample) |
| EP (1) | EP2074106B1 (enExample) |
| JP (1) | JP2010502689A (enExample) |
| CN (1) | CN101573348A (enExample) |
| AU (1) | AU2007297221B2 (enExample) |
| BR (1) | BRPI0716804A2 (enExample) |
| CA (1) | CA2663178C (enExample) |
| IL (1) | IL197507A (enExample) |
| MX (1) | MX2009002657A (enExample) |
| NZ (1) | NZ575389A (enExample) |
| RU (1) | RU2009113585A (enExample) |
| SG (1) | SG174810A1 (enExample) |
| WO (1) | WO2008032171A1 (enExample) |
| ZA (1) | ZA200901714B (enExample) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009115874A2 (en) * | 2008-03-17 | 2009-09-24 | Matrix Laboratories Ltd. | Novel heterocyclic compounds, pharmaceutical compositions containing them and processes for their preparation |
| JP5487214B2 (ja) | 2008-12-19 | 2014-05-07 | ブリストル−マイヤーズ スクイブ カンパニー | キナーゼ阻害剤として有用なカルバゾールカルボキシアミド化合物 |
| WO2010084402A2 (en) * | 2009-01-22 | 2010-07-29 | Orchid Research Laboratories Ltd. | Heterocyclic compounds as phosphodiesterase inhibitors |
| WO2011132051A2 (en) * | 2010-04-19 | 2011-10-27 | Glenmark Pharmaceuticals S.A. | Tricycle compounds as phosphodiesterase-10 inhibitors |
| SG192839A1 (en) | 2011-02-18 | 2013-09-30 | Allergan Inc | Substituted 6,7-dialkoxy-3-isoquinolinol derivatives as inhibitors of phosphodiesterase 10 (pde10a) |
| WO2014071044A1 (en) | 2012-11-01 | 2014-05-08 | Allergan, Inc. | Substituted 6,7-dialkoxy-3-isoquinoline derivatives as inhibitors of phosphodiesterase 10 (pde10a) |
| UY35625A (es) | 2013-06-25 | 2014-12-31 | Bristol Myers Squibb Company Una Corporación Del Estado De Delaware | Compuestos de tetrahidrocarbazol y carbazol carboxamida sustituidos como inhibidores de quinasa |
| CA2916504A1 (en) | 2013-06-25 | 2014-12-31 | Bristol-Myers Squibb Company | Carbazole carboxamide compounds useful as kinase inhibitors |
| US10039764B2 (en) | 2013-07-12 | 2018-08-07 | University Of South Alabama | Treatment and diagnosis of cancer and precancerous conditions using PDE10A inhibitors and methods to measure PDE10A expression |
| US9200016B2 (en) | 2013-12-05 | 2015-12-01 | Allergan, Inc. | Substituted 6, 7-dialkoxy-3-isoquinoline derivatives as inhibitors of phosphodiesterase 10 (PDE 10A) |
| KR102280686B1 (ko) | 2014-02-11 | 2021-07-22 | 삼성전자주식회사 | 카바졸계 화합물 및 이를 포함한 유기 발광 소자 |
| US9876181B2 (en) | 2014-08-13 | 2018-01-23 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
| EP3461821B1 (en) | 2014-10-24 | 2020-05-13 | Bristol-Myers Squibb Company | Indole carboxamide compounds useful as kinase inhibitors |
| BR112017007545A2 (pt) | 2014-10-24 | 2017-12-19 | Bristol Myers Squibb Co | derivados de carbazol |
| SG11201703186RA (en) | 2014-10-24 | 2017-05-30 | Bristol Myers Squibb Co | Tricyclic atropisomer compounds |
| ES2928164T3 (es) | 2015-10-19 | 2022-11-15 | Incyte Corp | Compuestos heterocíclicos como inmunomoduladores |
| HUE060680T2 (hu) | 2015-11-19 | 2023-04-28 | Incyte Corp | Heterociklusos vegyületek mint immunmodulátorok |
| DK3394033T3 (da) | 2015-12-22 | 2021-01-04 | Incyte Corp | Heterocykliske forbindelser som immunmodulatorer |
| MA44860A (fr) | 2016-05-06 | 2019-03-13 | Incyte Holdings Corp | Composés hétérocycliques utilisés comme immunomodulateurs |
| WO2017205464A1 (en) | 2016-05-26 | 2017-11-30 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| SG11201811414TA (en) | 2016-06-20 | 2019-01-30 | Incyte Corp | Heterocyclic compounds as immunomodulators |
| ES2930092T3 (es) | 2016-07-14 | 2022-12-07 | Incyte Corp | Compuestos heterocíclicos como inmunomoduladores |
| EP3504198B1 (en) | 2016-08-29 | 2023-01-25 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| EP3558989B1 (en) | 2016-12-22 | 2021-04-14 | Incyte Corporation | Triazolo[1,5-a]pyridine derivatives as immunomodulators |
| US20180179179A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| MA47123A (fr) | 2016-12-22 | 2021-03-17 | Incyte Corp | Dérivés de benzooxazole en tant qu'mmunomodulateurs |
| CA3047991A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Bicyclic heteroaromatic compounds as immunomodulators |
| CN108084128B (zh) * | 2017-12-28 | 2020-01-03 | 福建中医药大学 | 一种二苯并呋喃衍生物及其制备方法和用途 |
| US10669271B2 (en) | 2018-03-30 | 2020-06-02 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| CN110407741B (zh) | 2018-04-26 | 2023-03-21 | 启元生物(杭州)有限公司 | 一种抗炎化合物及其制备和应用 |
| LT3790877T (lt) | 2018-05-11 | 2023-05-10 | Incyte Corporation | Tetrahidro-imidazo[4,5-c]piridino dariniai kaip pd-l1 imunomoduliatoriai |
| TW202115059A (zh) | 2019-08-09 | 2021-04-16 | 美商英塞特公司 | Ｐｄ—１／ｐｄ—ｌ１抑制劑之鹽 |
| EP4037773A1 (en) | 2019-09-30 | 2022-08-10 | Incyte Corporation | Pyrido[3,2-d]pyrimidine compounds as immunomodulators |
| PE20230407A1 (es) | 2019-11-11 | 2023-03-07 | Incyte Corp | Sales y formas cristalinas de un inhibidor de pd-1/pd-l1 |
| GB202002926D0 (en) * | 2020-02-28 | 2020-04-15 | Benevolentai Tech Limited | Compositions and uses thereof |
| WO2022099071A1 (en) | 2020-11-06 | 2022-05-12 | Incyte Corporation | Process for making a pd-1/pd-l1 inhibitor and salts and crystalline forms thereof |
| WO2022099075A1 (en) | 2020-11-06 | 2022-05-12 | Incyte Corporation | Crystalline form of a pd-1/pd-l1 inhibitor |
| US11780836B2 (en) | 2020-11-06 | 2023-10-10 | Incyte Corporation | Process of preparing a PD-1/PD-L1 inhibitor |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MXPA05004432A (es) * | 2002-10-23 | 2005-11-23 | Glenmark Pharmaceuticals Ltd | Compuestos triciclicos novedosos utiles para el tratamiento de desordenes inflamatorios y alergicos, procedimiento para su preparacion y composiciones farmaceuticas que lo contienen. |
| ATE427308T1 (de) * | 2003-04-11 | 2009-04-15 | Glenmark Pharmaceuticals Sa | Neue heterozyklische verbindungen, die sich fur die behandlung von entzundlichen und allergischen erkrankungen eignen: verfahren zu deren herstellung und pharmazeutische zusammensetzungen,die diese enthalten |
| WO2004111044A1 (en) * | 2003-06-17 | 2004-12-23 | Glenmark Pharmaceuticals Ltd. | Tricyclic compounds useful for the treatment of inflammatory and allergic disorders:process for their preparation |
| WO2006011024A2 (en) * | 2004-07-19 | 2006-02-02 | Glenmark Pharmaceuticals Ltd. | New tricyclic compounds useful for the treatment of inflammatory and allergic disorders: process for their preparation and pharmaceutical compositions containing them |
| WO2006051390A1 (en) * | 2004-11-10 | 2006-05-18 | Glenmark Pharmaceuticals S.A. | Heterocyclic compounds useful for the treatment of inflammatory and allergic disorders, pharmaceutical compositions containing them, and methods of preparing them |
| JP5122974B2 (ja) * | 2004-12-17 | 2013-01-16 | グレンマーク・ファーマシューティカルズ・エスエー | 炎症性障害およびアレルギー障害の治療に有用な新規な複素環式化合物 |
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- 2007-09-10 RU RU2009113585/04A patent/RU2009113585A/ru not_active Application Discontinuation
- 2007-09-10 JP JP2009527220A patent/JP2010502689A/ja active Pending
- 2007-09-10 MX MX2009002657A patent/MX2009002657A/es active IP Right Grant
- 2007-09-10 BR BRPI0716804-7A2A patent/BRPI0716804A2/pt not_active IP Right Cessation
- 2007-09-10 NZ NZ575389A patent/NZ575389A/en not_active IP Right Cessation
- 2007-09-10 WO PCT/IB2007/002596 patent/WO2008032171A1/en not_active Ceased
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- 2007-09-10 EP EP07825083.4A patent/EP2074106B1/en not_active Not-in-force
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Also Published As
| Publication number | Publication date |
|---|---|
| AU2007297221A1 (en) | 2008-03-20 |
| WO2008032171A1 (en) | 2008-03-20 |
| SG174810A1 (en) | 2011-10-28 |
| JP2010502689A (ja) | 2010-01-28 |
| IL197507A (en) | 2014-05-28 |
| EP2074106B1 (en) | 2013-04-17 |
| IL197507A0 (en) | 2009-12-24 |
| RU2009113585A (ru) | 2010-10-20 |
| US8263648B2 (en) | 2012-09-11 |
| CA2663178A1 (en) | 2008-03-20 |
| US20090281131A1 (en) | 2009-11-12 |
| NZ575389A (en) | 2012-03-30 |
| AU2007297221B2 (en) | 2012-11-08 |
| ZA200901714B (en) | 2010-02-24 |
| CN101573348A (zh) | 2009-11-04 |
| MX2009002657A (es) | 2009-08-18 |
| BRPI0716804A2 (pt) | 2013-11-05 |
| EP2074106A1 (en) | 2009-07-01 |
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Legal Events
| Date | Code | Title | Description |
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| EEER | Examination request |
Effective date: 20130628 |
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| MKLA | Lapsed |
Effective date: 20170911 |