AU2007297221B2 - 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
- AU2007297221B2 AU2007297221B2 AU2007297221A AU2007297221A AU2007297221B2 AU 2007297221 B2 AU2007297221 B2 AU 2007297221B2 AU 2007297221 A AU2007297221 A AU 2007297221A AU 2007297221 A AU2007297221 A AU 2007297221A AU 2007297221 B2 AU2007297221 B2 AU 2007297221B2
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- Australia
- Prior art keywords
- methoxydibenzo
- furan
- cyano
- alkyl
- compound
- 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.)
- Ceased
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- 239000003112 inhibitor Substances 0.000 title claims abstract description 22
- 101100296719 Caenorhabditis elegans pde-4 gene Proteins 0.000 title 1
- 150000004826 dibenzofurans Chemical class 0.000 title 1
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 claims abstract description 17
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 claims abstract description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 154
- -1 cyano, carboxy Chemical group 0.000 claims description 80
- 238000006243 chemical reaction Methods 0.000 claims description 69
- 229920006395 saturated elastomer Polymers 0.000 claims description 41
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 239000001257 hydrogen Substances 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 23
- 125000005842 heteroatom Chemical group 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 20
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 19
- 150000002431 hydrogen Chemical class 0.000 claims description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 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
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- 208000006673 asthma Diseases 0.000 claims description 15
- 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
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 11
- 125000003107 substituted aryl group Chemical group 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 150000001204 N-oxides Chemical class 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000003367 polycyclic group Chemical group 0.000 claims description 9
- 239000012453 solvate Substances 0.000 claims description 9
- 125000002723 alicyclic group Chemical group 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
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- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000002950 monocyclic group Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 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 description 5
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
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- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 5
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 5
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
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- 125000001424 substituent group Chemical group 0.000 claims description 5
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- 125000002619 bicyclic group Chemical group 0.000 claims description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
- 230000004968 inflammatory condition Effects 0.000 claims description 4
- HIGCNPFUSCKGDA-UHFFFAOYSA-N methyl 5-cyano-5-(4-methoxydibenzofuran-1-yl)-2-oxocyclohexane-1-carboxylate Chemical compound C1CC(=O)C(C(=O)OC)CC1(C#N)C1=CC=C(OC)C2=C1C1=CC=CC=C1O2 HIGCNPFUSCKGDA-UHFFFAOYSA-N 0.000 claims description 4
- 230000009467 reduction Effects 0.000 claims description 4
- 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 description 3
- JAARYBGJMQKFRG-UHFFFAOYSA-N 5-(4-methoxydibenzofuran-1-yl)-1,4,6,7-tetrahydroindazole-5-carbonitrile Chemical compound C1CC2=NNC=C2CC1(C#N)C1=CC=C(OC)C2=C1C1=CC=CC=C1O2 JAARYBGJMQKFRG-UHFFFAOYSA-N 0.000 claims description 3
- WNPVRTAIVIPCLC-UHFFFAOYSA-N 6-(4-methoxydibenzofuran-1-yl)-2-methyl-4-oxo-1,5,7,8-tetrahydroquinazoline-6-carbonitrile Chemical compound N1=C(C)NC(=O)C(C2)=C1CCC2(C#N)C1=CC=C(OC)C2=C1C1=CC=CC=C1O2 WNPVRTAIVIPCLC-UHFFFAOYSA-N 0.000 claims description 3
- VSFHCICWCLDERG-UHFFFAOYSA-N 6-(4-methoxydibenzofuran-1-yl)-7,8-dihydro-5h-quinazoline-6-carbonitrile Chemical compound C1CC2=NC=NC=C2CC1(C#N)C1=CC=C(OC)C2=C1C1=CC=CC=C1O2 VSFHCICWCLDERG-UHFFFAOYSA-N 0.000 claims description 3
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- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000003368 amide group Chemical group 0.000 claims description 3
- 201000008937 atopic dermatitis Diseases 0.000 claims description 3
- 206010006451 bronchitis Diseases 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 208000007451 chronic bronchitis Diseases 0.000 claims description 3
- 208000037976 chronic inflammation Diseases 0.000 claims description 3
- 230000006020 chronic inflammation Effects 0.000 claims description 3
- 238000007333 cyanation reaction Methods 0.000 claims description 3
- GRTGGSXWHGKRSB-UHFFFAOYSA-N dichloromethyl methyl ether Chemical compound COC(Cl)Cl GRTGGSXWHGKRSB-UHFFFAOYSA-N 0.000 claims description 3
- WZUXAFMNSHCLIL-UHFFFAOYSA-N n-[4-cyano-4-(4-methoxydibenzofuran-1-yl)cyclohexyl]methanesulfonamide Chemical compound C1=2C3=CC=CC=C3OC=2C(OC)=CC=C1C1(C#N)CCC(NS(C)(=O)=O)CC1 WZUXAFMNSHCLIL-UHFFFAOYSA-N 0.000 claims description 3
- 201000008383 nephritis Diseases 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 201000008482 osteoarthritis Diseases 0.000 claims description 3
- 230000036303 septic shock Effects 0.000 claims description 3
- 208000011580 syndromic disease Diseases 0.000 claims description 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
- 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 description 2
- NMBMYZIIGIVTTK-UHFFFAOYSA-N 2-amino-6-(4-methoxydibenzofuran-1-yl)-4-oxo-1,5,7,8-tetrahydroquinazoline-6-carbonitrile Chemical compound N1=C(N)NC(=O)C(C2)=C1CCC2(C#N)C1=CC=C(OC)C2=C1C1=CC=CC=C1O2 NMBMYZIIGIVTTK-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- MSYGAHOHLUJIKV-UHFFFAOYSA-N 3,5-dimethyl-1-(3-nitrophenyl)-1h-pyrazole-4-carboxylic acid ethyl ester Chemical compound CC1=C(C(=O)OCC)C(C)=NN1C1=CC=CC([N+]([O-])=O)=C1 MSYGAHOHLUJIKV-UHFFFAOYSA-N 0.000 claims description 2
- SZBXZDLWKDKXRL-UHFFFAOYSA-N 4-cyano-4-(4-methoxydibenzofuran-1-yl)cyclohexane-1-carboxylic acid Chemical compound C1=2C3=CC=CC=C3OC=2C(OC)=CC=C1C1(C#N)CCC(C(O)=O)CC1 SZBXZDLWKDKXRL-UHFFFAOYSA-N 0.000 claims description 2
- QIZKODSPPKGICU-UHFFFAOYSA-N 5-(4-ethoxydibenzofuran-1-yl)-6,7-dihydro-4h-2,1-benzoxazole-5-carbonitrile Chemical compound C1CC2=NOC=C2CC1(C#N)C1=CC=C(OCC)C2=C1C1=CC=CC=C1O2 QIZKODSPPKGICU-UHFFFAOYSA-N 0.000 claims description 2
- YOIULBPZMKZVOO-UHFFFAOYSA-N 5-(4-methoxydibenzofuran-1-yl)-2-phenyl-6,7-dihydro-4h-indazole-5-carbonitrile Chemical compound C1=2C3=CC=CC=C3OC=2C(OC)=CC=C1C(CC1=C2)(C#N)CCC1=NN2C1=CC=CC=C1 YOIULBPZMKZVOO-UHFFFAOYSA-N 0.000 claims description 2
- MIWJDIQCBMZBPS-UHFFFAOYSA-N 5-(4-methoxydibenzofuran-1-yl)-3-oxo-3a,4,6,7-tetrahydro-2h-indazole-5-carbonitrile Chemical compound C1CC2=NNC(=O)C2CC1(C#N)C1=CC=C(OC)C2=C1C1=CC=CC=C1O2 MIWJDIQCBMZBPS-UHFFFAOYSA-N 0.000 claims description 2
- KYAZWEZZTAVVAH-UHFFFAOYSA-N 6-(4-methoxydibenzofuran-1-yl)-3-methyl-4-oxo-7,8-dihydro-5h-quinazoline-6-carbonitrile Chemical compound N1=CN(C)C(=O)C(C2)=C1CCC2(C#N)C1=CC=C(OC)C2=C1C1=CC=CC=C1O2 KYAZWEZZTAVVAH-UHFFFAOYSA-N 0.000 claims description 2
- LTLBUSHXQYASQU-UHFFFAOYSA-N 6-(4-methoxydibenzofuran-1-yl)-4-oxo-1,5,7,8-tetrahydroquinazoline-6-carbonitrile Chemical compound N1=CNC(=O)C(C2)=C1CCC2(C#N)C1=CC=C(OC)C2=C1C1=CC=CC=C1O2 LTLBUSHXQYASQU-UHFFFAOYSA-N 0.000 claims description 2
- KACYDLOZYXBEMS-UHFFFAOYSA-N 6-cyano-6-(4-methoxydibenzofuran-1-yl)-2-methyl-7,8-dihydro-5h-quinoline-3-carboxylic acid Chemical compound C1CC2=NC(C)=C(C(O)=O)C=C2CC1(C#N)C1=CC=C(OC)C2=C1C1=CC=CC=C1O2 KACYDLOZYXBEMS-UHFFFAOYSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
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- IEMGWBMVQLVHEY-UHFFFAOYSA-N ethyl 2-(3-amino-6,7-dihydro-5h-cyclopenta[b]pyridin-7-yl)acetate Chemical compound NC1=CN=C2C(CC(=O)OCC)CCC2=C1 IEMGWBMVQLVHEY-UHFFFAOYSA-N 0.000 claims description 2
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- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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)
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- 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 |
|---|---|
| AU2007297221A1 AU2007297221A1 (en) | 2008-03-20 |
| AU2007297221B2 true AU2007297221B2 (en) | 2012-11-08 |
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| Application Number | Title | Priority Date | Filing Date |
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| AU2007297221A Ceased AU2007297221B2 (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 (OSRAM) |
| EP (1) | EP2074106B1 (OSRAM) |
| JP (1) | JP2010502689A (OSRAM) |
| CN (1) | CN101573348A (OSRAM) |
| AU (1) | AU2007297221B2 (OSRAM) |
| BR (1) | BRPI0716804A2 (OSRAM) |
| CA (1) | CA2663178C (OSRAM) |
| IL (1) | IL197507A (OSRAM) |
| MX (1) | MX2009002657A (OSRAM) |
| NZ (1) | NZ575389A (OSRAM) |
| RU (1) | RU2009113585A (OSRAM) |
| SG (1) | SG174810A1 (OSRAM) |
| WO (1) | WO2008032171A1 (OSRAM) |
| ZA (1) | ZA200901714B (OSRAM) |
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| 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 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| 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 |
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| 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 |
| 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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| Publication number | Priority date | Publication date | Assignee | Title |
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| 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 |
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| 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 |
| CA2663178C (en) | 2016-01-12 |
| 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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