AU2006204454B2 - Triazolophthalazines as PDE2-inhibitors - Google Patents
Triazolophthalazines as PDE2-inhibitors Download PDFInfo
- Publication number
- AU2006204454B2 AU2006204454B2 AU2006204454A AU2006204454A AU2006204454B2 AU 2006204454 B2 AU2006204454 B2 AU 2006204454B2 AU 2006204454 A AU2006204454 A AU 2006204454A AU 2006204454 A AU2006204454 A AU 2006204454A AU 2006204454 B2 AU2006204454 B2 AU 2006204454B2
- Authority
- AU
- Australia
- Prior art keywords
- phenyl
- alkyl
- methoxy
- triazolo
- phthalazin
- 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
Links
- 229940121828 Phosphodiesterase 2 inhibitor Drugs 0.000 title abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 286
- -1 1-4C-alkoxycarbonyl Chemical class 0.000 claims description 189
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 90
- 229910052757 nitrogen Inorganic materials 0.000 claims description 85
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 71
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 58
- 150000003839 salts Chemical class 0.000 claims description 54
- 125000004573 morpholin-4-yl group Chemical class N1(CCOCC1)* 0.000 claims description 47
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 45
- RBIIKVXVYVANCQ-CUWPLCDZSA-N (2s,4s,5s)-5-amino-n-(3-amino-2,2-dimethyl-3-oxopropyl)-6-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]-4-hydroxy-2-propan-2-ylhexanamide Chemical compound C1C(C)(C)N(C[C@H](N)[C@@H](O)C[C@@H](C(C)C)C(=O)NCC(C)(C)C(N)=O)CC(=O)N1C1=CC=CC=C1Cl RBIIKVXVYVANCQ-CUWPLCDZSA-N 0.000 claims description 44
- 239000001257 hydrogen Substances 0.000 claims description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 41
- 238000000034 method Methods 0.000 claims description 40
- 229910052736 halogen Inorganic materials 0.000 claims description 39
- 150000002367 halogens Chemical class 0.000 claims description 39
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 37
- 101100177165 Caenorhabditis elegans har-1 gene Proteins 0.000 claims description 36
- 125000004076 pyridyl group Chemical group 0.000 claims description 35
- 125000005842 heteroatom Chemical group 0.000 claims description 25
- 125000001544 thienyl group Chemical group 0.000 claims description 25
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 24
- 239000005864 Sulphur Chemical group 0.000 claims description 24
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 24
- 229910052760 oxygen Inorganic materials 0.000 claims description 24
- 239000001301 oxygen Chemical group 0.000 claims description 24
- 239000008194 pharmaceutical composition Substances 0.000 claims description 24
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 22
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 22
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 21
- 239000000460 chlorine Chemical group 0.000 claims description 21
- 125000002950 monocyclic group Chemical group 0.000 claims description 21
- 125000000623 heterocyclic group Chemical group 0.000 claims description 20
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 20
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- 238000011282 treatment Methods 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 17
- 125000004299 tetrazol-5-yl group Chemical class [H]N1N=NC(*)=N1 0.000 claims description 17
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 16
- ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 208000035475 disorder Diseases 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 15
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 14
- 206010029113 Neovascularisation Diseases 0.000 claims description 14
- SGTXILTYXULEQD-UHFFFAOYSA-N 2H-triazolo[4,5-f]phthalazine Chemical group N1=NC=C2C3=NNN=C3C=CC2=C1 SGTXILTYXULEQD-UHFFFAOYSA-N 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 11
- 125000003277 amino group Chemical group 0.000 claims description 11
- 230000000694 effects Effects 0.000 claims description 11
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 10
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 230000001771 impaired effect Effects 0.000 claims description 10
- 125000000951 phenoxy group Chemical class [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 10
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 10
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 9
- 206010040070 Septic Shock Diseases 0.000 claims description 9
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 9
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- 230000036303 septic shock Effects 0.000 claims description 9
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 8
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- 208000027866 inflammatory disease Diseases 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- BUYUFJZVMVFQLQ-UHFFFAOYSA-N 4-[2-(5,5,8,8-tetramethyl-6,7-dihydroquinoxalin-2-yl)ethynyl]benzoic acid Chemical compound CC1(C=2N=CC(=NC=2C(CC1)(C)C)C#CC1=CC=C(C(=O)O)C=C1)C BUYUFJZVMVFQLQ-UHFFFAOYSA-N 0.000 claims description 6
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 6
- 230000001154 acute effect Effects 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 230000001684 chronic effect Effects 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000004571 thiomorpholin-4-yl group Chemical group N1(CCSCC1)* 0.000 claims description 6
- 206010035664 Pneumonia Diseases 0.000 claims description 5
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
- 206010003246 arthritis Diseases 0.000 claims description 5
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- DMXZEAGYRDSWII-UHFFFAOYSA-N 3-[[3-(4-methoxyphenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]amino]benzonitrile Chemical compound C1=CC(OC)=CC=C1C1=NN=C2N1N=C(NC=1C=C(C=CC=1)C#N)C1=CC=CC=C12 DMXZEAGYRDSWII-UHFFFAOYSA-N 0.000 claims description 4
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 4
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- 125000005805 dimethoxy phenyl group Chemical group 0.000 claims description 4
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- 230000002792 vascular Effects 0.000 claims description 4
- CQXHGLHIADVBQW-UHFFFAOYSA-N 3-(4-methoxyphenyl)-n-[3-(2h-tetrazol-5-yl)phenyl]-[1,2,4]triazolo[3,4-a]phthalazin-6-amine Chemical compound C1=CC(OC)=CC=C1C1=NN=C2N1N=C(NC=1C=C(C=CC=1)C1=NNN=N1)C1=CC=CC=C12 CQXHGLHIADVBQW-UHFFFAOYSA-N 0.000 claims description 3
- NENVQQVAZMKJJY-UHFFFAOYSA-N 3-n-[3-(4-methoxyphenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]benzene-1,3-diamine Chemical compound C1=CC(OC)=CC=C1C1=NN=C2N1N=C(NC=1C=C(N)C=CC=1)C1=CC=CC=C12 NENVQQVAZMKJJY-UHFFFAOYSA-N 0.000 claims description 3
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- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
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- OSGBHVOGBRCXPP-UHFFFAOYSA-N 3-[[3-[(4-methoxyphenyl)methyl]-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]amino]benzonitrile Chemical compound C1=CC(OC)=CC=C1CC1=NN=C2N1N=C(NC=1C=C(C=CC=1)C#N)C1=CC=CC=C12 OSGBHVOGBRCXPP-UHFFFAOYSA-N 0.000 claims description 2
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- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- OFPZTDFQPFJKDG-UHFFFAOYSA-N n-[3-[[3-[(4-methoxyphenyl)methyl]-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]amino]phenyl]methanesulfonamide Chemical compound C1=CC(OC)=CC=C1CC1=NN=C2N1N=C(NC=1C=C(NS(C)(=O)=O)C=CC=1)C1=CC=CC=C12 OFPZTDFQPFJKDG-UHFFFAOYSA-N 0.000 claims description 2
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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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- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Physical Education & Sports Medicine (AREA)
- Pulmonology (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Heart & Thoracic Surgery (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Cardiology (AREA)
- Neurosurgery (AREA)
- Immunology (AREA)
- Neurology (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Pain & Pain Management (AREA)
- Communicable Diseases (AREA)
- Psychology (AREA)
- Ophthalmology & Optometry (AREA)
- Urology & Nephrology (AREA)
- Hospice & Palliative Care (AREA)
- Vascular Medicine (AREA)
- Psychiatry (AREA)
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- Epidemiology (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP05100045.3 | 2005-01-05 | ||
| EP05100045 | 2005-01-05 | ||
| EP05100044 | 2005-01-05 | ||
| EP05100044.6 | 2005-01-05 | ||
| PCT/EP2006/050041 WO2006072615A2 (en) | 2005-01-05 | 2006-01-04 | Triazolophthalazines as pde2-inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2006204454A1 AU2006204454A1 (en) | 2006-07-13 |
| AU2006204454B2 true AU2006204454B2 (en) | 2011-11-10 |
Family
ID=36604687
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2006204454A Ceased AU2006204454B2 (en) | 2005-01-05 | 2006-01-04 | Triazolophthalazines as PDE2-inhibitors |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US8106047B2 (https=) |
| EP (1) | EP1836207B1 (https=) |
| JP (1) | JP5240899B2 (https=) |
| KR (1) | KR20070095986A (https=) |
| CN (1) | CN101103033B (https=) |
| AU (1) | AU2006204454B2 (https=) |
| BR (1) | BRPI0606379A2 (https=) |
| CA (1) | CA2592007C (https=) |
| EA (1) | EA012505B1 (https=) |
| ES (1) | ES2397080T3 (https=) |
| IL (1) | IL183919A (https=) |
| MX (1) | MX2007008137A (https=) |
| NO (1) | NO20073921L (https=) |
| NZ (1) | NZ555661A (https=) |
| WO (1) | WO2006072615A2 (https=) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2005279221C9 (en) * | 2004-09-02 | 2012-08-23 | Takeda Gmbh | Triazolophthalazines |
| EP1874775B1 (en) | 2005-01-05 | 2012-10-10 | Nycomed GmbH | Triazolophthalazines as pde2-inhibitors |
| BRPI0606379A2 (pt) | 2005-01-05 | 2009-06-23 | Nycomed Gmbh | triazolftalazinas |
| PH12012501361A1 (en) | 2009-12-31 | 2012-10-22 | Centro Nac De Investigaciones Oncologicas Cnio | Tricyclic compounds for use as kinase inhibitors |
| US9540379B2 (en) | 2011-01-31 | 2017-01-10 | Boehringer Ingelheim International Gmbh | (1,2,4)triazolo[4,3-A]quinoxaline derivatives as inhibitors of phosphodiesterases |
| SG195085A1 (en) | 2011-06-07 | 2013-12-30 | Pfizer | Pyrazolo[3,4-d]pyrimidine compounds and their use as pde2 inhibitors and/or cyp3a4 inhibitors |
| MX361539B (es) | 2012-04-25 | 2018-12-10 | Takeda Pharmaceuticals Co | Compuesto heterociclico nitrogenado. |
| EP2844660B1 (en) | 2012-05-02 | 2017-11-01 | Southern Research Institute | Triazolopyridazine compounds, use as inhibitors of the kinase lrrk2, and methods for preparation thereof |
| EP2873669A4 (en) * | 2012-07-13 | 2015-11-25 | Takeda Pharmaceutical | HETEROCYCLIC CONNECTION |
| US20140045856A1 (en) | 2012-07-31 | 2014-02-13 | Boehringer Ingelheim International Gmbh | 4-Methyl-2,3,5,9,9b-pentaaza-cyclopenta[a]naphthalenes |
| EP2975031A4 (en) | 2013-03-14 | 2017-04-19 | Takeda Pharmaceutical Company Limited | Heterocyclic compound |
| JP6427491B2 (ja) | 2013-07-03 | 2018-11-21 | 武田薬品工業株式会社 | 複素環化合物 |
| ES2950424T3 (es) | 2013-07-03 | 2023-10-09 | Takeda Pharmaceuticals Co | Compuesto de amida |
| EP3091983B1 (en) | 2014-01-08 | 2019-10-02 | Intra-Cellular Therapies, Inc. | Pharmaceutical compositions comprising a pde-1 inhibitor and a pde-2 inhibitor |
| CN103694244B (zh) * | 2014-01-09 | 2016-03-30 | 郑州大学 | 3,6位取代-1,2,4-三氮唑并[3,4-a]酞嗪类化合物及其制备和用途 |
| DK3134413T3 (da) | 2014-04-23 | 2019-10-14 | Dart Neuroscience Cayman Ltd | Substituerede [1,2,4]triazolo[1,5-a]pyrimidin-7-yl-forbindelser som pde2-inhibitorer |
| US10239882B2 (en) | 2014-11-05 | 2019-03-26 | Dart Neuroscience (Cayman) Ltd. | Substituted 5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-amine compounds as PDE2 inhibitors |
| CN107205993B (zh) | 2014-12-06 | 2021-03-09 | 细胞内治疗公司 | 有机化合物 |
| US10300064B2 (en) | 2014-12-06 | 2019-05-28 | Intra-Cellular Therapies, Inc. | Organic compounds |
| WO2016145614A1 (en) * | 2015-03-17 | 2016-09-22 | Merck Sharp & Dohme Corp. | Triazolyl pyrimidinone compounds as pde2 inhibitors |
| WO2016154081A1 (en) | 2015-03-26 | 2016-09-29 | Merck Sharp & Dohme Corp. | Pyrazolyl pyrimidinone compounds as pde2 inhibitors |
| WO2016179059A1 (en) | 2015-05-05 | 2016-11-10 | Merck Sharp & Dohme Corp. | Heteroaryl-pyrimidinone compounds as pde2 inhibitors |
| WO2016183741A1 (en) | 2015-05-15 | 2016-11-24 | Merck Sharp & Dohme Corp. | Pyrimidinone amide compounds as pde2 inhibitors |
| WO2016191935A1 (en) | 2015-05-29 | 2016-12-08 | Merck Sharp & Dohme Corp. | 6-alkyl dihydropyrazolopyrimidinone compounds as pde2 inhibitors |
| WO2016192083A1 (en) | 2015-06-04 | 2016-12-08 | Merck Sharp & Dohme Corp. | Dihydropyrazolopyrimidinone compounds as pde2 inhibitors |
| US10647727B2 (en) | 2015-06-25 | 2020-05-12 | Merck Sharp & Dohme Corp. | Substituted pyrazolo/imidazolo bicyclic compounds as PDE2 inhibitors |
| WO2017000276A1 (en) | 2015-07-01 | 2017-01-05 | Merck Sharp & Dohme Corp. | Bicyclic heterocyclic compounds as pde2 inhibitors |
| WO2017000277A1 (en) | 2015-07-01 | 2017-01-05 | Merck Sharp & Dohme Corp. | Substituted triazolo bicycliccompounds as pde2 inhibitors |
| EP3156405A1 (en) | 2015-10-13 | 2017-04-19 | Boehringer Ingelheim International GmbH | Spirocyclic ether derivatives of pyrazolo[1,5-a]pyrimidine-3-carboxamide |
| AU2018371216B2 (en) | 2017-11-23 | 2024-09-19 | Oslo University Hospital Hf | Treatment of tachycardia |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006024640A2 (en) * | 2004-09-02 | 2006-03-09 | Altana Pharma Ag | Triazolophthalazines |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI81350C (fi) | 1982-01-18 | 1990-10-10 | Lepetit Spa | Analogfoerfarande foer framstaellning av nya, farmakologiskt aktiva 6-substituerade s-triatsolo/3,4-a/ ftalazinderivat. |
| IT1194310B (it) * | 1983-07-12 | 1988-09-14 | Lepetit Spa | Derivati triazolo (3,4-a) ftalazinici 3,6-disostituiti |
| US5869486A (en) | 1995-02-24 | 1999-02-09 | Ono Pharmaceutical Co., Ltd. | Fused pyrimidines and pyriazines as pharmaceutical compounds |
| ES2194205T3 (es) | 1996-07-25 | 2003-11-16 | Merck Sharp & Dohme | Derivados de triazolo-piridazina sustituidos como ligandos para los receptores gaba. |
| EP0986562B1 (en) | 1997-05-08 | 2002-08-07 | MERCK SHARP & DOHME LTD. | Substituted 1,2,4-triazolo 3,4-a]phthalazine derivatives as gaba alpha 5 ligands |
| US6235741B1 (en) | 1997-05-30 | 2001-05-22 | Merck & Co., Inc. | Angiogenesis inhibitors |
| GB9715977D0 (en) | 1997-07-29 | 1997-10-01 | Merck Sharp & Dohme | Therapeutic agents |
| IT1303272B1 (it) | 1998-10-29 | 2000-11-06 | Zambon Spa | Derivati triciclici inibitori della fosfodiesterasi 4 |
| EP1261609B1 (de) * | 1999-12-24 | 2004-11-03 | Bayer HealthCare AG | Triazolotriazinone und ihre verwendung |
| GB0028583D0 (en) | 2000-11-23 | 2001-01-10 | Merck Sharp & Dohme | Therapeutic compounds |
| WO2002083140A1 (en) | 2001-04-10 | 2002-10-24 | Merck & Co., Inc. | Inhibitors of akt activity |
| NZ539163A (en) | 2002-09-04 | 2007-03-30 | Schering Corp | Pyrazolo[1,5-a]pyrimidine compounds useful as cyclin dependent kinase (CDK) inhibitors |
| US20070179161A1 (en) | 2003-03-31 | 2007-08-02 | Vernalis (Cambridge) Limited. | Pyrazolopyrimidine compounds and their use in medicine |
| BRPI0606379A2 (pt) | 2005-01-05 | 2009-06-23 | Nycomed Gmbh | triazolftalazinas |
| EP1874775B1 (en) * | 2005-01-05 | 2012-10-10 | Nycomed GmbH | Triazolophthalazines as pde2-inhibitors |
-
2006
- 2006-01-04 BR BRPI0606379-9A patent/BRPI0606379A2/pt not_active IP Right Cessation
- 2006-01-04 CN CN2006800017646A patent/CN101103033B/zh not_active Expired - Fee Related
- 2006-01-04 AU AU2006204454A patent/AU2006204454B2/en not_active Ceased
- 2006-01-04 MX MX2007008137A patent/MX2007008137A/es active IP Right Grant
- 2006-01-04 EA EA200701396A patent/EA012505B1/ru not_active IP Right Cessation
- 2006-01-04 EP EP06700240A patent/EP1836207B1/en not_active Expired - Lifetime
- 2006-01-04 NZ NZ555661A patent/NZ555661A/en not_active IP Right Cessation
- 2006-01-04 CA CA2592007A patent/CA2592007C/en not_active Expired - Fee Related
- 2006-01-04 KR KR1020077017407A patent/KR20070095986A/ko not_active Ceased
- 2006-01-04 ES ES06700240T patent/ES2397080T3/es not_active Expired - Lifetime
- 2006-01-04 JP JP2007548843A patent/JP5240899B2/ja not_active Expired - Fee Related
- 2006-01-04 US US11/794,145 patent/US8106047B2/en not_active Expired - Fee Related
- 2006-01-04 WO PCT/EP2006/050041 patent/WO2006072615A2/en not_active Ceased
-
2007
- 2007-06-14 IL IL183919A patent/IL183919A/en not_active IP Right Cessation
- 2007-07-26 NO NO20073921A patent/NO20073921L/no not_active Application Discontinuation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006024640A2 (en) * | 2004-09-02 | 2006-03-09 | Altana Pharma Ag | Triazolophthalazines |
Also Published As
| Publication number | Publication date |
|---|---|
| MX2007008137A (es) | 2007-07-19 |
| NZ555661A (en) | 2010-11-26 |
| IL183919A0 (en) | 2007-10-31 |
| CA2592007A1 (en) | 2006-07-13 |
| US8106047B2 (en) | 2012-01-31 |
| EA012505B1 (ru) | 2009-10-30 |
| WO2006072615A2 (en) | 2006-07-13 |
| NO20073921L (no) | 2007-07-26 |
| JP2008526717A (ja) | 2008-07-24 |
| JP5240899B2 (ja) | 2013-07-17 |
| BRPI0606379A2 (pt) | 2009-06-23 |
| US20080312225A1 (en) | 2008-12-18 |
| EA200701396A1 (ru) | 2007-12-28 |
| EP1836207B1 (en) | 2012-10-10 |
| IL183919A (en) | 2011-06-30 |
| CN101103033A (zh) | 2008-01-09 |
| CN101103033B (zh) | 2010-08-04 |
| EP1836207A2 (en) | 2007-09-26 |
| AU2006204454A1 (en) | 2006-07-13 |
| WO2006072615A3 (en) | 2007-01-04 |
| KR20070095986A (ko) | 2007-10-01 |
| CA2592007C (en) | 2013-12-10 |
| ES2397080T3 (es) | 2013-03-04 |
| HK1116776A1 (en) | 2009-01-02 |
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