JP2019533714A5 - - Google Patents
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- JP2019533714A5 JP2019533714A5 JP2019524943A JP2019524943A JP2019533714A5 JP 2019533714 A5 JP2019533714 A5 JP 2019533714A5 JP 2019524943 A JP2019524943 A JP 2019524943A JP 2019524943 A JP2019524943 A JP 2019524943A JP 2019533714 A5 JP2019533714 A5 JP 2019533714A5
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- JP
- Japan
- Prior art keywords
- alkyl
- halogen
- cycloalkyl
- case
- independently
- 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.)
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- 229910052736 halogen Inorganic materials 0.000 claims description 1665
- 150000002367 halogens Chemical class 0.000 claims description 1660
- 125000000217 alkyl group Chemical group 0.000 claims description 1401
- 229910052739 hydrogen Inorganic materials 0.000 claims description 593
- 125000000623 heterocyclic group Chemical group 0.000 claims description 384
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 318
- 229910052799 carbon Inorganic materials 0.000 claims description 268
- 150000003839 salts Chemical class 0.000 claims description 248
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 214
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 214
- 229910052757 nitrogen Inorganic materials 0.000 claims description 213
- 229910052760 oxygen Inorganic materials 0.000 claims description 213
- 239000001301 oxygen Substances 0.000 claims description 213
- 239000001257 hydrogen Substances 0.000 claims description 211
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 211
- 125000001072 heteroaryl group Chemical group 0.000 claims description 196
- 125000003118 aryl group Chemical group 0.000 claims description 70
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 57
- -1 azetidine-1-yl Chemical group 0.000 claims description 38
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 38
- 229940123469 Fatty acid synthase inhibitor Drugs 0.000 claims description 33
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims description 27
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 15
- 208000010706 fatty liver disease Diseases 0.000 claims description 7
- 206010016654 Fibrosis Diseases 0.000 claims description 6
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 5
- 230000004761 fibrosis Effects 0.000 claims description 4
- 208000001145 Metabolic Syndrome Diseases 0.000 claims description 2
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 2
- 230000007882 cirrhosis Effects 0.000 claims description 2
- 201000007270 liver cancer Diseases 0.000 claims description 2
- 208000014018 liver neoplasm Diseases 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 54
- 125000005842 heteroatom Chemical group 0.000 claims 14
- 125000006661 (C4-C6) heterocyclic group Chemical group 0.000 claims 13
- 102000015303 Fatty Acid Synthases Human genes 0.000 claims 13
- 108010039731 Fatty Acid Synthases Proteins 0.000 claims 13
- 239000003112 inhibitor Substances 0.000 claims 13
- 201000010099 disease Diseases 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- 208000011580 syndromic disease Diseases 0.000 claims 4
- 210000002443 helper t lymphocyte Anatomy 0.000 claims 3
- 208000024891 symptom Diseases 0.000 claims 3
- 208000002874 Acne Vulgaris Diseases 0.000 claims 2
- 206010016207 Familial Mediterranean fever Diseases 0.000 claims 2
- 208000032672 Histiocytosis haematophagic Diseases 0.000 claims 2
- 206010072010 Hyper IgD syndrome Diseases 0.000 claims 2
- 208000018208 Hyperimmunoglobulinemia D with periodic fever Diseases 0.000 claims 2
- 208000004987 Macrophage activation syndrome Diseases 0.000 claims 2
- 206010000496 acne Diseases 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 210000004185 liver Anatomy 0.000 claims 2
- 206010072221 mevalonate kinase deficiency Diseases 0.000 claims 2
- 230000000306 recurrent effect Effects 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- LOGFVTREOLYCPF-KXNHARMFSA-N (2s,3r)-2-[[(2r)-1-[(2s)-2,6-diaminohexanoyl]pyrrolidine-2-carbonyl]amino]-3-hydroxybutanoic acid Chemical compound C[C@@H](O)[C@@H](C(O)=O)NC(=O)[C@H]1CCCN1C(=O)[C@@H](N)CCCCN LOGFVTREOLYCPF-KXNHARMFSA-N 0.000 claims 1
- 206010000748 Acute febrile neutrophilic dermatosis Diseases 0.000 claims 1
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims 1
- 206010053555 Arthritis bacterial Diseases 0.000 claims 1
- 208000009766 Blau syndrome Diseases 0.000 claims 1
- 208000020084 Bone disease Diseases 0.000 claims 1
- 208000005623 Carcinogenesis Diseases 0.000 claims 1
- 206010008685 Chondritis Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 241001475178 Dira Species 0.000 claims 1
- 206010014476 Elevated cholesterol Diseases 0.000 claims 1
- 102000004190 Enzymes Human genes 0.000 claims 1
- 108090000790 Enzymes Proteins 0.000 claims 1
- 208000004930 Fatty Liver Diseases 0.000 claims 1
- 201000005569 Gout Diseases 0.000 claims 1
- 206010019708 Hepatic steatosis Diseases 0.000 claims 1
- 208000035150 Hypercholesterolemia Diseases 0.000 claims 1
- 206010061216 Infarction Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 102000003777 Interleukin-1 beta Human genes 0.000 claims 1
- 108090000193 Interleukin-1 beta Proteins 0.000 claims 1
- 102100026018 Interleukin-1 receptor antagonist protein Human genes 0.000 claims 1
- 101710144554 Interleukin-1 receptor antagonist protein Proteins 0.000 claims 1
- 208000004852 Lung Injury Diseases 0.000 claims 1
- 102100022691 NACHT, LRR and PYD domains-containing protein 3 Human genes 0.000 claims 1
- 101710126825 NACHT, LRR and PYD domains-containing protein 3 Proteins 0.000 claims 1
- 201000007100 Pharyngitis Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 208000006311 Pyoderma Diseases 0.000 claims 1
- 206010037660 Pyrexia Diseases 0.000 claims 1
- 241000876474 Sapho Species 0.000 claims 1
- 201000010848 Schnitzler Syndrome Diseases 0.000 claims 1
- 208000004346 Smoldering Multiple Myeloma Diseases 0.000 claims 1
- 208000010265 Sweet syndrome Diseases 0.000 claims 1
- 206010052779 Transplant rejections Diseases 0.000 claims 1
- 206010069363 Traumatic lung injury Diseases 0.000 claims 1
- 108060008683 Tumor Necrosis Factor Receptor Proteins 0.000 claims 1
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 claims 1
- 206010069351 acute lung injury Diseases 0.000 claims 1
- 208000002399 aphthous stomatitis Diseases 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 210000004369 blood Anatomy 0.000 claims 1
- 239000008280 blood Substances 0.000 claims 1
- 230000036952 cancer formation Effects 0.000 claims 1
- 231100000504 carcinogenesis Toxicity 0.000 claims 1
- 210000004027 cell Anatomy 0.000 claims 1
- 230000007812 deficiency Effects 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 230000014509 gene expression Effects 0.000 claims 1
- 230000002440 hepatic effect Effects 0.000 claims 1
- 208000006454 hepatitis Diseases 0.000 claims 1
- 201000008298 histiocytosis Diseases 0.000 claims 1
- 230000007574 infarction Effects 0.000 claims 1
- 230000000366 juvenile effect Effects 0.000 claims 1
- 208000018191 liver inflammation Diseases 0.000 claims 1
- 231100000515 lung injury Toxicity 0.000 claims 1
- 201000003265 lymphadenitis Diseases 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 230000002956 necrotizing effect Effects 0.000 claims 1
- 230000011164 ossification Effects 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 230000000737 periodic effect Effects 0.000 claims 1
- 208000025487 periodic fever syndrome Diseases 0.000 claims 1
- 208000005069 pulmonary fibrosis Diseases 0.000 claims 1
- 210000003289 regulatory T cell Anatomy 0.000 claims 1
- 206010048628 rheumatoid vasculitis Diseases 0.000 claims 1
- 208000010721 smoldering plasma cell myeloma Diseases 0.000 claims 1
- LXMSZDCAJNLERA-ZHYRCANASA-N spironolactone Chemical compound C([C@@H]1[C@]2(C)CC[C@@H]3[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)SC(=O)C)C[C@@]21CCC(=O)O1 LXMSZDCAJNLERA-ZHYRCANASA-N 0.000 claims 1
- 231100000240 steatosis hepatitis Toxicity 0.000 claims 1
- 208000026082 sterile multifocal osteomyelitis with periostitis and pustulosis Diseases 0.000 claims 1
- 201000004595 synovitis Diseases 0.000 claims 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims 1
- 102000003298 tumor necrosis factor receptor Human genes 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
- 230000029936 alkylation Effects 0.000 description 24
- 238000005804 alkylation reaction Methods 0.000 description 24
- 238000000034 method Methods 0.000 description 21
- PKWIYNIDEDLDCJ-UHFFFAOYSA-N guanazole Chemical compound NC1=NNC(N)=N1 PKWIYNIDEDLDCJ-UHFFFAOYSA-N 0.000 description 12
- 125000005843 halogen group Chemical group 0.000 description 5
- 239000003814 drug Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2023000165A JP2023033259A (ja) | 2016-11-11 | 2023-01-04 | 脂質合成の複素環式モジュレーター |
| JP2024229040A JP2025036565A (ja) | 2016-11-11 | 2024-12-25 | 脂質合成の複素環式モジュレーター |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15/349,960 | 2016-11-11 | ||
| US15/349,960 US20170119786A1 (en) | 2011-03-08 | 2016-11-11 | Heterocyclic modulators of lipid synthesis |
| US201762574497P | 2017-10-19 | 2017-10-19 | |
| US62/574,497 | 2017-10-19 | ||
| PCT/US2017/061330 WO2018089904A1 (en) | 2016-11-11 | 2017-11-13 | Heterocyclic modulators of lipid synthesis |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2023000165A Division JP2023033259A (ja) | 2016-11-11 | 2023-01-04 | 脂質合成の複素環式モジュレーター |
| JP2024229040A Division JP2025036565A (ja) | 2016-11-11 | 2024-12-25 | 脂質合成の複素環式モジュレーター |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019533714A JP2019533714A (ja) | 2019-11-21 |
| JP2019533714A5 true JP2019533714A5 (OSRAM) | 2020-12-10 |
| JP7668509B2 JP7668509B2 (ja) | 2025-04-25 |
Family
ID=60473676
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019524943A Active JP7668509B2 (ja) | 2016-11-11 | 2017-11-13 | 脂質合成の複素環式モジュレーター |
| JP2023000165A Pending JP2023033259A (ja) | 2016-11-11 | 2023-01-04 | 脂質合成の複素環式モジュレーター |
| JP2024229040A Pending JP2025036565A (ja) | 2016-11-11 | 2024-12-25 | 脂質合成の複素環式モジュレーター |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2023000165A Pending JP2023033259A (ja) | 2016-11-11 | 2023-01-04 | 脂質合成の複素環式モジュレーター |
| JP2024229040A Pending JP2025036565A (ja) | 2016-11-11 | 2024-12-25 | 脂質合成の複素環式モジュレーター |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US11034690B2 (OSRAM) |
| EP (1) | EP3538088A1 (OSRAM) |
| JP (3) | JP7668509B2 (OSRAM) |
| KR (3) | KR20250169632A (OSRAM) |
| CN (2) | CN110177551B (OSRAM) |
| AU (2) | AU2017356214B2 (OSRAM) |
| CA (1) | CA3043308A1 (OSRAM) |
| IL (1) | IL266505B2 (OSRAM) |
| NZ (1) | NZ754372A (OSRAM) |
| WO (1) | WO2018089904A1 (OSRAM) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20170119786A1 (en) | 2011-03-08 | 2017-05-04 | 3-V Biosciences, Inc. | Heterocyclic modulators of lipid synthesis |
| TWI767148B (zh) | 2018-10-10 | 2022-06-11 | 美商弗瑪治療公司 | 抑制脂肪酸合成酶(fasn) |
| CN110078613B (zh) * | 2019-05-31 | 2022-04-22 | 杭州科耀医药科技有限公司 | 一种2-卤-5-碘苯甲酸的合成方法 |
| TW202128664A (zh) | 2019-10-09 | 2021-08-01 | 德商拜耳廠股份有限公司 | 作為除害劑之新穎雜芳基三唑化合物 |
| CN114469945A (zh) * | 2020-10-28 | 2022-05-13 | 歌礼生物科技（杭州）有限公司 | 脂肪酸合酶抑制剂的用途和药物组合物 |
| US20250166821A1 (en) * | 2021-11-11 | 2025-05-22 | Sagimet Biosciences Inc. | Methods for prediction of treatment response in non-alcoholic fatty liver disease |
| CN114436979B (zh) * | 2022-02-22 | 2024-03-26 | 成都化润药业有限公司 | 一种合成1,2,4-三氮唑-3-羧酸甲酯的方法 |
| JPWO2024172156A1 (OSRAM) * | 2023-02-16 | 2024-08-22 | ||
| CN119080742A (zh) * | 2023-06-05 | 2024-12-06 | 甘莱制药有限公司 | 脂质合成的杂环调节剂的工业化制备 |
| WO2025086054A1 (zh) * | 2023-10-23 | 2025-05-01 | 歌礼生物科技（杭州）有限公司 | 一种包含苯甲腈衍生物的药物组合物 |
| CN119868349A (zh) * | 2023-10-23 | 2025-04-25 | 歌礼生物科技（杭州）有限公司 | 一种包含苯甲腈衍生物的药物组合物 |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6939874B2 (en) | 2001-08-22 | 2005-09-06 | Amgen Inc. | Substituted pyrimidinyl derivatives and methods of use |
| WO2007052843A1 (ja) | 2005-11-04 | 2007-05-10 | Takeda Pharmaceutical Company Limited | 複素環アミド化合物およびその用途 |
| RU2396269C2 (ru) | 2005-12-01 | 2010-08-10 | Ф.Хоффманн-Ля Рош Аг | Производные гетероарилзамещенного пиперидина в качестве ингибиторов печеночной карнитин пальмитоилтрансферазы (l-cpt1) |
| JP2010502731A (ja) | 2006-09-05 | 2010-01-28 | バイパー サイエンシズ，インコーポレイティド | Ｐａｒｐ阻害剤による脂肪酸合成の阻害、及びその治療方法 |
| WO2008059214A1 (en) * | 2006-11-13 | 2008-05-22 | Astrazeneca Ab | Bisamlde derivatives and use thereof as fatty acid synthase inhibitors |
| WO2008075077A1 (en) | 2006-12-21 | 2008-06-26 | Astrazeneca Ab | Piperidine derivatives for the treatment of obesity |
| TW200833663A (en) | 2006-12-21 | 2008-08-16 | Astrazeneca Ab | Therapeutic agents |
| TW200831092A (en) | 2006-12-21 | 2008-08-01 | Astrazeneca Ab | Therapeutic agents |
| EP2485678A4 (en) | 2009-10-07 | 2013-04-03 | Univ Cornell | Coferons and methods of making and using them |
| AU2011218830B2 (en) * | 2010-02-25 | 2014-07-24 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| US20170119786A1 (en) | 2011-03-08 | 2017-05-04 | 3-V Biosciences, Inc. | Heterocyclic modulators of lipid synthesis |
| US9624173B2 (en) * | 2011-03-08 | 2017-04-18 | 3-V Biosciences, Inc. | Heterocyclic modulators of lipid synthesis |
| TWI522348B (zh) | 2011-03-08 | 2016-02-21 | ３ Ｖ生物科技公司 | 脂質合成之雜環調節劑 |
| EP2683244B1 (en) * | 2011-03-08 | 2017-02-01 | 3-V Biosciences, Inc. | Heterocyclic modulators of lipid synthesis |
| EP2870150B1 (en) | 2012-07-03 | 2019-06-19 | 3-V Biosciences, Inc. | Heterocyclic modulators of lipid synthesis |
| CA2884355C (en) * | 2012-09-07 | 2022-05-17 | Janssen Pharmaceutica Nv | Imidazolin-5-one derivative useful as fasn inhobitors for the treatment of cancer |
| EP3077387B1 (en) * | 2013-12-03 | 2017-12-20 | Janssen Pharmaceutica NV | Benzamide derivative useful as fasn inhibitors for the treatment of cancer |
| JP6617106B2 (ja) * | 2013-12-17 | 2019-12-04 | ヤンセン ファーマシューティカ エヌ．ベー． | 癌の治療用のｆａｓｎ阻害剤として有用なイミダゾリン−５−オン誘導体 |
| CA2934251C (en) * | 2013-12-20 | 2024-01-02 | 3-V Biosciences, Inc. | A combination of heterocyclic modulators of lipid synthesis and chemotherapeutic drugs in treatment of cancer |
| RU2766087C2 (ru) | 2014-01-07 | 2022-02-07 | Сагимет Байосайенсиз Инк. | Гетероциклические модуляторы синтеза липидов для применения против рака и вирусных инфекций |
| RS57384B1 (sr) * | 2014-03-17 | 2018-09-28 | Pfizer | Inhibitori diacilglicerol aciltransferaze 2 za upotrebu u tretmanu metaboličkih i srodnih poremećaja |
| KR102504168B1 (ko) * | 2014-08-15 | 2023-02-27 | 새지메트 바이오사이언시스, 인코포레이티드 | 약물 내성 암의 치료에서 사용하기 위한 지방산 신타제 억제제 |
| ES2910049T3 (es) * | 2015-03-19 | 2022-05-11 | Sagimet Biosciences Inc | Moduladores heterocíclicos de la síntesis de lípidos |
-
2017
- 2017-11-13 US US16/348,138 patent/US11034690B2/en active Active
- 2017-11-13 JP JP2019524943A patent/JP7668509B2/ja active Active
- 2017-11-13 AU AU2017356214A patent/AU2017356214B2/en active Active
- 2017-11-13 KR KR1020257039033A patent/KR20250169632A/ko active Pending
- 2017-11-13 KR KR1020197016754A patent/KR102644934B1/ko active Active
- 2017-11-13 NZ NZ754372A patent/NZ754372A/en unknown
- 2017-11-13 CA CA3043308A patent/CA3043308A1/en active Pending
- 2017-11-13 EP EP17804772.6A patent/EP3538088A1/en active Pending
- 2017-11-13 CN CN201780083446.7A patent/CN110177551B/zh active Active
- 2017-11-13 KR KR1020247007294A patent/KR102890891B1/ko active Active
- 2017-11-13 CN CN202310077929.3A patent/CN116139138A/zh active Pending
- 2017-11-13 WO PCT/US2017/061330 patent/WO2018089904A1/en not_active Ceased
-
2019
- 2019-05-07 IL IL266505A patent/IL266505B2/en unknown
-
2023
- 2023-01-04 JP JP2023000165A patent/JP2023033259A/ja active Pending
-
2024
- 2024-02-19 AU AU2024201067A patent/AU2024201067A1/en active Pending
- 2024-12-25 JP JP2024229040A patent/JP2025036565A/ja active Pending
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