JPWO2020069043A5 - - Google Patents
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- Publication number
- JPWO2020069043A5 JPWO2020069043A5 JP2021540398A JP2021540398A JPWO2020069043A5 JP WO2020069043 A5 JPWO2020069043 A5 JP WO2020069043A5 JP 2021540398 A JP2021540398 A JP 2021540398A JP 2021540398 A JP2021540398 A JP 2021540398A JP WO2020069043 A5 JPWO2020069043 A5 JP WO2020069043A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- substituted
- independently
- formula
- phenyl
- 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.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims description 93
- -1 dimethylene, trimethylene Chemical group 0.000 claims description 49
- 229910052799 carbon Inorganic materials 0.000 claims description 48
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 42
- 125000005843 halogen group Chemical group 0.000 claims description 37
- 125000003118 aryl group Chemical group 0.000 claims description 29
- 229910052736 halogen Inorganic materials 0.000 claims description 28
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 21
- 150000003839 salts Chemical group 0.000 claims description 21
- 229940121836 Phosphodiesterase 1 inhibitor Drugs 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 12
- 210000002540 macrophage Anatomy 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 206010061218 Inflammation Diseases 0.000 claims description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
- 230000004054 inflammatory process Effects 0.000 claims description 11
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- 239000000651 prodrug Chemical group 0.000 claims description 9
- 229940002612 prodrug Drugs 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 241000725303 Human immunodeficiency virus Species 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 8
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims description 8
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims description 8
- 125000004512 1,2,3-thiadiazol-4-yl group Chemical group S1N=NC(=C1)* 0.000 claims description 6
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 108090000695 Cytokines Proteins 0.000 claims description 6
- 102000004127 Cytokines Human genes 0.000 claims description 6
- 241000725619 Dengue virus Species 0.000 claims description 6
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 6
- 241000187917 Mycobacterium ulcerans Species 0.000 claims description 5
- 241001135989 Porcine reproductive and respiratory syndrome virus Species 0.000 claims description 5
- 241000223997 Toxoplasma gondii Species 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 241000701386 African swine fever virus Species 0.000 claims description 4
- 201000001320 Atherosclerosis Diseases 0.000 claims description 4
- 208000035143 Bacterial infection Diseases 0.000 claims description 4
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 4
- 241000710777 Classical swine fever virus Species 0.000 claims description 4
- 241000710198 Foot-and-mouth disease virus Species 0.000 claims description 4
- 208000005176 Hepatitis C Diseases 0.000 claims description 4
- 206010019799 Hepatitis viral Diseases 0.000 claims description 4
- 241000713772 Human immunodeficiency virus 1 Species 0.000 claims description 4
- 241000712431 Influenza A virus Species 0.000 claims description 4
- 206010022489 Insulin Resistance Diseases 0.000 claims description 4
- 241000186779 Listeria monocytogenes Species 0.000 claims description 4
- 241000187479 Mycobacterium tuberculosis Species 0.000 claims description 4
- 208000008589 Obesity Diseases 0.000 claims description 4
- 208000030852 Parasitic disease Diseases 0.000 claims description 4
- 206010035664 Pneumonia Diseases 0.000 claims description 4
- 241001673669 Porcine circovirus 2 Species 0.000 claims description 4
- 241000725643 Respiratory syncytial virus Species 0.000 claims description 4
- 241000315672 SARS coronavirus Species 0.000 claims description 4
- 241000293871 Salmonella enterica subsp. enterica serovar Typhi Species 0.000 claims description 4
- 241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 claims description 4
- 206010040047 Sepsis Diseases 0.000 claims description 4
- 241000701093 Suid alphaherpesvirus 1 Species 0.000 claims description 4
- 241000244158 Taenia crassiceps Species 0.000 claims description 4
- 208000036142 Viral infection Diseases 0.000 claims description 4
- 241000710886 West Nile virus Species 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 4
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 208000005252 hepatitis A Diseases 0.000 claims description 4
- 208000002672 hepatitis B Diseases 0.000 claims description 4
- 230000001404 mediated effect Effects 0.000 claims description 4
- 235000020824 obesity Nutrition 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 230000000770 proinflammatory effect Effects 0.000 claims description 4
- 208000005069 pulmonary fibrosis Diseases 0.000 claims description 4
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 4
- 201000001862 viral hepatitis Diseases 0.000 claims description 4
- 230000009385 viral infection Effects 0.000 claims description 4
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 3
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 3
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 101150052909 CCL2 gene Proteins 0.000 claims description 3
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 3
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 3
- 108090001005 Interleukin-6 Proteins 0.000 claims description 3
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims description 3
- 108060008682 Tumor Necrosis Factor Proteins 0.000 claims description 3
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 230000004913 activation Effects 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000004419 alkynylene group Chemical group 0.000 claims description 3
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims description 3
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 3
- 125000001769 aryl amino group Chemical group 0.000 claims description 3
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 3
- 125000000732 arylene group Chemical group 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 201000008937 atopic dermatitis Diseases 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000002720 diazolyl group Chemical group 0.000 claims description 3
- 208000035475 disorder Diseases 0.000 claims description 3
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 3
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 3
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 3
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 3
- 125000005549 heteroarylene group Chemical group 0.000 claims description 3
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
- 125000002757 morpholinyl group Chemical group 0.000 claims description 3
- 208000022155 mycobacterium avium complex disease Diseases 0.000 claims description 3
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- 125000005551 pyridylene group Chemical group 0.000 claims description 3
- HJORMJIFDVBMOB-UHFFFAOYSA-N rolipram Chemical compound COC1=CC=C(C2CC(=O)NC2)C=C1OC1CCCC1 HJORMJIFDVBMOB-UHFFFAOYSA-N 0.000 claims description 3
- 229950005741 rolipram Drugs 0.000 claims description 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
- 125000001425 triazolyl group Chemical group 0.000 claims description 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 2
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 2
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims 8
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 4
- 206010003827 Autoimmune hepatitis Diseases 0.000 claims 2
- 241000222697 Leishmania infantum Species 0.000 claims 2
- 241000186367 Mycobacterium avium Species 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- 230000029663 wound healing Effects 0.000 claims 2
- 241000222722 Leishmania <genus> Species 0.000 claims 1
- 241000242678 Schistosoma Species 0.000 claims 1
- 241000242680 Schistosoma mansoni Species 0.000 claims 1
- 241000700605 Viruses Species 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 229940124530 sulfonamide Drugs 0.000 claims 1
- 150000003456 sulfonamides Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 description 18
- 208000006448 Buruli Ulcer Diseases 0.000 description 2
- 241000711573 Coronaviridae Species 0.000 description 2
- 201000003883 Cystic fibrosis Diseases 0.000 description 2
- 208000011623 Obstructive Lung disease Diseases 0.000 description 2
- 102100031950 Polyunsaturated fatty acid lipoxygenase ALOX15 Human genes 0.000 description 2
- 101710164073 Polyunsaturated fatty acid lipoxygenase ALOX15 Proteins 0.000 description 2
- 230000000747 cardiac effect Effects 0.000 description 2
- 206010012601 diabetes mellitus Diseases 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 239000002207 metabolite Substances 0.000 description 2
- 208000004296 neuralgia Diseases 0.000 description 2
- 208000021722 neuropathic pain Diseases 0.000 description 2
- 230000037361 pathway Effects 0.000 description 2
- 206010034674 peritonitis Diseases 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- 208000011580 syndromic disease Diseases 0.000 description 2
- 201000008827 tuberculosis Diseases 0.000 description 2
- ZNHVWPKMFKADKW-UHFFFAOYSA-N 12-HETE Chemical compound CCCCCC=CCC(O)C=CC=CCC=CCCCC(O)=O ZNHVWPKMFKADKW-UHFFFAOYSA-N 0.000 description 1
- ZNHVWPKMFKADKW-ZYBDYUKJSA-N 12-HETE Natural products CCCCC\C=C/C[C@@H](O)\C=C\C=C/C\C=C/CCCC(O)=O ZNHVWPKMFKADKW-ZYBDYUKJSA-N 0.000 description 1
- JSFATNQSLKRBCI-VAEKSGALSA-N 15-HETE Natural products CCCCC[C@H](O)\C=C\C=C/C\C=C/C\C=C/CCCC(O)=O JSFATNQSLKRBCI-VAEKSGALSA-N 0.000 description 1
- JSFATNQSLKRBCI-UHFFFAOYSA-N 15-Hydroxyeicosatetraenoic acid Chemical compound CCCCCC(O)C=CC=CCC=CCC=CCCCC(O)=O JSFATNQSLKRBCI-UHFFFAOYSA-N 0.000 description 1
- 101000620009 Homo sapiens Polyunsaturated fatty acid 5-lipoxygenase Proteins 0.000 description 1
- 102100022364 Polyunsaturated fatty acid 5-lipoxygenase Human genes 0.000 description 1
- 239000000090 biomarker Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 1
- 229960002986 dinoprostone Drugs 0.000 description 1
- VNYSSYRCGWBHLG-AMOLWHMGSA-N leukotriene B4 Chemical compound CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O VNYSSYRCGWBHLG-AMOLWHMGSA-N 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 230000004647 pro-inflammatory pathway Effects 0.000 description 1
- XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 1
- 230000007115 recruitment Effects 0.000 description 1
- XNRNNGPBEPRNAR-JQBLCGNGSA-N thromboxane B2 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1OC(O)C[C@H](O)[C@@H]1C\C=C/CCCC(O)=O XNRNNGPBEPRNAR-JQBLCGNGSA-N 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2024082290A JP2024109735A (ja) | 2018-09-25 | 2024-05-21 | 新規使用 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201862736324P | 2018-09-25 | 2018-09-25 | |
| US62/736,324 | 2018-09-25 | ||
| PCT/US2019/053032 WO2020069043A1 (en) | 2018-09-25 | 2019-09-25 | Novel uses |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2024082290A Division JP2024109735A (ja) | 2018-09-25 | 2024-05-21 | 新規使用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2022502501A JP2022502501A (ja) | 2022-01-11 |
| JPWO2020069043A5 true JPWO2020069043A5 (https=) | 2022-10-04 |
| JP2022502501A5 JP2022502501A5 (https=) | 2022-10-04 |
Family
ID=69953335
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021540398A Pending JP2022502501A (ja) | 2018-09-25 | 2019-09-25 | 新規使用 |
| JP2024082290A Pending JP2024109735A (ja) | 2018-09-25 | 2024-05-21 | 新規使用 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2024082290A Pending JP2024109735A (ja) | 2018-09-25 | 2024-05-21 | 新規使用 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US20210338679A1 (https=) |
| EP (1) | EP3856191A4 (https=) |
| JP (2) | JP2022502501A (https=) |
| WO (1) | WO2020069043A1 (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US12396992B2 (en) | 2019-01-07 | 2025-08-26 | Intra-Cellular Therapies, Inc. | Organic compounds |
| AU2020343329C1 (en) | 2019-09-03 | 2026-02-12 | Intra-Cellular Therapies, Inc. | Methods of treatment |
| WO2021127517A1 (en) * | 2019-12-18 | 2021-06-24 | Intra-Cellular Therapies, Inc. | Novel uses |
| US12364695B2 (en) | 2020-06-02 | 2025-07-22 | Intra-Cellular Therapies, Inc. | Methods of treating inflammatory disease |
| WO2025212780A1 (en) * | 2024-04-02 | 2025-10-09 | Intra-Cellular Therapies, Inc. | Organic compounds |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8273750B2 (en) | 2005-06-06 | 2012-09-25 | Takeda Pharmaceutical Company Limited | Organic compounds |
| JP5453086B2 (ja) | 2006-06-06 | 2014-03-26 | イントラ−セルラー・セラピーズ・インコーポレイテッド | 有機化合物 |
| ES2588238T3 (es) | 2007-12-06 | 2016-10-31 | Intra-Cellular Therapies, Inc. | Derivados de pirazolopirimidin-4,6-diona y su uso como producto farmacéutico |
| AU2008335811B2 (en) | 2007-12-06 | 2012-05-17 | Intra-Cellular Therapies, Inc. | Organic compounds |
| JP5989993B2 (ja) | 2008-12-06 | 2016-09-07 | イントラ−セルラー・セラピーズ・インコーポレイテッドＩｎｔｒａ−Ｃｅｌｌｕｌａｒ Ｔｈｅｒａｐｉｅｓ， Ｉｎｃ． | 有機化合物 |
| WO2010065147A1 (en) | 2008-12-06 | 2010-06-10 | Intra-Cellular Therapies, Inc. | Organic compounds |
| AU2009322904A1 (en) | 2008-12-06 | 2010-06-10 | Intra-Cellular Therapies, Inc. | Organic compounds |
| KR20110098732A (ko) | 2008-12-06 | 2011-09-01 | 인트라-셀룰라 써래피스, 인코퍼레이티드. | 유기 화합물 |
| CN102231953A (zh) | 2008-12-06 | 2011-11-02 | 细胞内治疗公司 | 有机化合物 |
| EP2560676B8 (en) | 2010-04-22 | 2016-10-12 | Intra-Cellular Therapies, Inc. | Organic compounds |
| TW201206937A (en) | 2010-05-31 | 2012-02-16 | Intra Cellular Therapies Inc | Organic compounds |
| WO2011153135A1 (en) | 2010-05-31 | 2011-12-08 | Intra-Cellular Therapies, Inc. | Organic compounds |
| US9434730B2 (en) | 2010-05-31 | 2016-09-06 | Intra-Cellular Therapies, Inc. | PDE1 inhibitor compounds |
| US9763948B2 (en) | 2010-05-31 | 2017-09-19 | Intra-Cellular Therapies, Inc. | PDE1 inhibitory compounds and methods |
| US10695431B2 (en) * | 2010-10-29 | 2020-06-30 | Infirst Healthcare Limited | Solid solution compositions and use in cardiovascular disease |
| US9308213B2 (en) * | 2010-10-29 | 2016-04-12 | Infirst Healthcare Limited | Solid solution compositions and use in chronic inflammation |
| WO2013138118A1 (en) * | 2012-03-14 | 2013-09-19 | The Regents Of The University Of California | Treatment of inflammatory disorders in non-human mammals |
| CA2906640C (en) | 2013-03-15 | 2021-07-20 | Intra-Cellular Therapies, Inc. | Substituted imidazo-[1,2-a]pyrazolo[4.3-e]pyrimidin-4[5h]-one compounds and pharmaceutical compositions and use therof as pde1 inhibitors |
| WO2018049417A1 (en) | 2016-09-12 | 2018-03-15 | Intra-Cellular Therapies, Inc. | Novel uses |
-
2019
- 2019-09-25 JP JP2021540398A patent/JP2022502501A/ja active Pending
- 2019-09-25 WO PCT/US2019/053032 patent/WO2020069043A1/en not_active Ceased
- 2019-09-25 EP EP19864482.5A patent/EP3856191A4/en active Pending
- 2019-09-25 US US17/279,518 patent/US20210338679A1/en active Pending
-
2024
- 2024-05-21 JP JP2024082290A patent/JP2024109735A/ja active Pending
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