JP2019522007A5 - - Google Patents
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- JP2019522007A5 JP2019522007A5 JP2019500851A JP2019500851A JP2019522007A5 JP 2019522007 A5 JP2019522007 A5 JP 2019522007A5 JP 2019500851 A JP2019500851 A JP 2019500851A JP 2019500851 A JP2019500851 A JP 2019500851A JP 2019522007 A5 JP2019522007 A5 JP 2019522007A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- optionally
- alkyl
- deoxy
- triazole
- 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.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims description 58
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 27
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 26
- -1 D-galactopyranose compound Chemical class 0.000 claims description 25
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 150000002367 halogens Chemical class 0.000 claims description 21
- 125000002496 methyl group Chemical class [H]C([H])([H])* 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 20
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 229910052740 iodine Inorganic materials 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000005349 heteroarylcycloalkyl group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims description 3
- 229960003082 Galactose Drugs 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 150000003214 pyranose derivatives Chemical group 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000011780 sodium chloride Substances 0.000 claims description 3
- 239000012453 solvate Substances 0.000 claims description 3
- WQZGKKKJIJFFOK-PHYPRBDBSA-N α-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 claims description 3
- 125000004361 3,4,5-trifluorophenyl group Chemical group [H]C1=C(F)C(F)=C(F)C([H])=C1* 0.000 claims 5
- 206010016654 Fibrosis Diseases 0.000 claims 4
- 230000033115 angiogenesis Effects 0.000 claims 4
- 230000004761 fibrosis Effects 0.000 claims 4
- 201000011510 cancer Diseases 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 2
- 208000008466 Metabolic Disease Diseases 0.000 claims 2
- 230000027455 binding Effects 0.000 claims 2
- 206010059837 Adhesion Diseases 0.000 claims 1
- 206010003210 Arteriosclerosis Diseases 0.000 claims 1
- 208000006673 Asthma Diseases 0.000 claims 1
- 206010003816 Autoimmune disease Diseases 0.000 claims 1
- 206010007554 Cardiac failure Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 206010011401 Crohn's disease Diseases 0.000 claims 1
- 206010012601 Diabetes mellitus Diseases 0.000 claims 1
- 208000009745 Eye Disease Diseases 0.000 claims 1
- 102000000802 Galectin 3 Human genes 0.000 claims 1
- 108010001517 Galectin 3 Proteins 0.000 claims 1
- 206010019280 Heart failure Diseases 0.000 claims 1
- 208000006454 Hepatitis Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 208000006897 Interstitial Lung Disease Diseases 0.000 claims 1
- 208000002260 Keloid Diseases 0.000 claims 1
- 210000001117 Keloid Anatomy 0.000 claims 1
- 206010023330 Keloid scar Diseases 0.000 claims 1
- 206010024324 Leukaemias Diseases 0.000 claims 1
- 210000004185 Liver Anatomy 0.000 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- ZMXRBTNYSARFEU-DABHTEOTSA-N OC[C@H]1O[C@H](SC2=CC(Br)=C(N=C2)C#N)[C@H](O)[C@H]([C@H]1O)N1C=C(N=N1)C1=CC(F)=C(Cl)C(F)=C1 Chemical compound OC[C@H]1O[C@H](SC2=CC(Br)=C(N=C2)C#N)[C@H](O)[C@H]([C@H]1O)N1C=C(N=N1)C1=CC(F)=C(Cl)C(F)=C1 ZMXRBTNYSARFEU-DABHTEOTSA-N 0.000 claims 1
- FXAVWGPNWZCDHN-RBUQIHAASA-N OC[C@H]1O[C@H](SC2=CC(Br)=CN=C2C#N)[C@H](O)[C@H]([C@H]1O)N1C=C(N=N1)C1=CC(F)=C(Cl)C(F)=C1 Chemical compound OC[C@H]1O[C@H](SC2=CC(Br)=CN=C2C#N)[C@H](O)[C@H]([C@H]1O)N1C=C(N=N1)C1=CC(F)=C(Cl)C(F)=C1 FXAVWGPNWZCDHN-RBUQIHAASA-N 0.000 claims 1
- ZIZMKGYAKCDXAV-DABHTEOTSA-N OC[C@H]1O[C@H](SC2=CC(Cl)=C(N=C2)C#N)[C@H](O)[C@H]([C@H]1O)N1C=C(N=N1)C1=CC(F)=C(Cl)C(F)=C1 Chemical compound OC[C@H]1O[C@H](SC2=CC(Cl)=C(N=C2)C#N)[C@H](O)[C@H]([C@H]1O)N1C=C(N=N1)C1=CC(F)=C(Cl)C(F)=C1 ZIZMKGYAKCDXAV-DABHTEOTSA-N 0.000 claims 1
- YGCUIZJEHKOBCY-ICBNADEASA-N OC[C@H]1O[C@H](SC2=CC(Cl)=CN=C2)[C@H](O)[C@H]([C@H]1O)N1C=C(N=N1)C1=CC(F)=C(Cl)C=C1 Chemical compound OC[C@H]1O[C@H](SC2=CC(Cl)=CN=C2)[C@H](O)[C@H]([C@H]1O)N1C=C(N=N1)C1=CC(F)=C(Cl)C=C1 YGCUIZJEHKOBCY-ICBNADEASA-N 0.000 claims 1
- SWKFRXPLZKGBMW-RBUQIHAASA-N OC[C@H]1O[C@H](SC2=CC(Cl)=CN=C2C#N)[C@H](O)[C@H]([C@H]1O)N1C=C(N=N1)C1=CC(F)=C(Cl)C(F)=C1 Chemical compound OC[C@H]1O[C@H](SC2=CC(Cl)=CN=C2C#N)[C@H](O)[C@H]([C@H]1O)N1C=C(N=N1)C1=CC(F)=C(Cl)C(F)=C1 SWKFRXPLZKGBMW-RBUQIHAASA-N 0.000 claims 1
- QHXFOIHAIAOUHI-CAEUUNHDSA-N OC[C@H]1O[C@H](SC2=CC(Cl)=NC=C2)[C@H](O)[C@H]([C@H]1O)N1C=C(N=N1)C1=CC(F)=C(F)C(F)=C1 Chemical compound OC[C@H]1O[C@H](SC2=CC(Cl)=NC=C2)[C@H](O)[C@H]([C@H]1O)N1C=C(N=N1)C1=CC(F)=C(F)C(F)=C1 QHXFOIHAIAOUHI-CAEUUNHDSA-N 0.000 claims 1
- PQSOKCUAMAYMEO-CAEUUNHDSA-N OC[C@H]1O[C@H](SC2=NC=CC(Cl)=C2)[C@H](O)[C@H]([C@H]1O)N1C=C(N=N1)C1=CC(F)=C(F)C(F)=C1 Chemical compound OC[C@H]1O[C@H](SC2=NC=CC(Cl)=C2)[C@H](O)[C@H]([C@H]1O)N1C=C(N=N1)C1=CC(F)=C(F)C(F)=C1 PQSOKCUAMAYMEO-CAEUUNHDSA-N 0.000 claims 1
- 206010025310 Other lymphomas Diseases 0.000 claims 1
- 208000005069 Pulmonary Fibrosis Diseases 0.000 claims 1
- 206010039073 Rheumatoid arthritis Diseases 0.000 claims 1
- 206010039491 Sarcoma Diseases 0.000 claims 1
- 206010040070 Septic shock Diseases 0.000 claims 1
- 210000003491 Skin Anatomy 0.000 claims 1
- 206010042971 T-cell lymphoma Diseases 0.000 claims 1
- 230000002159 abnormal effect Effects 0.000 claims 1
- 230000000996 additive Effects 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000001476 alcoholic Effects 0.000 claims 1
- 201000001320 atherosclerosis Diseases 0.000 claims 1
- 201000009596 autoimmune hypersensitivity disease Diseases 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 201000000159 corneal neovascularization Diseases 0.000 claims 1
- 201000010870 diseases of metabolism Diseases 0.000 claims 1
- 238000005755 formation reaction Methods 0.000 claims 1
- 201000010238 heart disease Diseases 0.000 claims 1
- 231100000283 hepatitis Toxicity 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 239000003446 ligand Substances 0.000 claims 1
- 201000009673 liver disease Diseases 0.000 claims 1
- 230000000938 luteal Effects 0.000 claims 1
- 200000000023 metastatic cancer Diseases 0.000 claims 1
- 230000001575 pathological Effects 0.000 claims 1
- 201000004681 psoriasis Diseases 0.000 claims 1
- 201000002793 renal fibrosis Diseases 0.000 claims 1
- 231100000241 scar Toxicity 0.000 claims 1
- 230000036573 scar formation Effects 0.000 claims 1
- 230000036303 septic shock Effects 0.000 claims 1
- 201000002661 spondylitis Diseases 0.000 claims 1
- 201000010874 syndrome Diseases 0.000 claims 1
- 230000001256 tonic Effects 0.000 claims 1
- 201000006704 ulcerative colitis Diseases 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP16179070.4 | 2016-07-12 | ||
| EP16179070 | 2016-07-12 | ||
| PCT/EP2017/067181 WO2018011094A1 (en) | 2016-07-12 | 2017-07-09 | Alpha-d-galactoside inhibitors of galectins |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019522007A JP2019522007A (ja) | 2019-08-08 |
| JP2019522007A5 true JP2019522007A5 (US07846941-20101207-C00217.png) | 2021-11-04 |
| JP7216634B2 JP7216634B2 (ja) | 2023-02-01 |
Family
ID=56411455
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019500851A Active JP7216634B2 (ja) | 2016-07-12 | 2017-07-09 | ガレクチンのα－Ｄ－ガラクトシド阻害剤 |
Country Status (6)
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6904906B2 (ja) | 2015-01-30 | 2021-07-21 | ガレクト・バイオテック・エイビイ | ガレクチンの新規なガラクトシド阻害剤 |
| US10988502B2 (en) * | 2016-07-12 | 2021-04-27 | Galecto Biotech Ab | Alpha-D-galactoside inhibitors of galectins |
| EA202091684A1 (ru) * | 2018-01-10 | 2020-12-04 | Галекто Биотек Аб | Новый галактозидный ингибитор галектинов |
| CA3114055A1 (en) * | 2018-10-15 | 2020-04-23 | Galecto Biotech Ab | Prodrug of galactoside inhibitors of galectins |
| CN113366007A (zh) * | 2018-10-15 | 2021-09-07 | 格莱克特生物技术公司 | 半乳糖凝集素的半乳糖苷抑制剂 |
| TWI832917B (zh) | 2018-11-06 | 2024-02-21 | 美商富曼西公司 | 經取代之甲苯基殺真菌劑 |
| JP7486484B2 (ja) | 2018-11-21 | 2024-05-17 | ガレクト バイオテック エービー | ガレクチンのα－Ｄ－ガラクトシド阻害剤 |
| BR112021012482A2 (pt) * | 2018-12-27 | 2021-09-08 | Glycomimetics, Inc. | C-glicosídeos inibidores de galectina-3 |
| CN113727988A (zh) | 2019-03-26 | 2021-11-30 | 百时美施贵宝公司 | 半乳糖凝集素-3的小分子抑制剂 |
| JP2022538634A (ja) * | 2019-07-03 | 2022-09-05 | ガレクト バイオテック エービー | ガレクチンの新規なガラクトシド阻害剤 |
| WO2021028323A1 (en) * | 2019-08-09 | 2021-02-18 | Idorsia Pharmaceuticals Ltd | (2-acetamidyl)thio-beta-d-galactopyranoside derivatives |
| CN110743017B (zh) * | 2019-10-22 | 2021-03-09 | 北京大学 | 一种靶向半乳糖凝集素-1的放射性药物及其制备方法 |
| WO2021086816A1 (en) * | 2019-10-29 | 2021-05-06 | Glycomimetics, Inc. | Galectin-3 inhibiting c-glycosides |
| EP3838909A1 (en) * | 2019-12-16 | 2021-06-23 | Galecto Biotech AB | Large scale process for the preparation of 5-bromopyridin-3-yl-3-deoxy-3-[4-(3,4,5-trifluorophenyl)-1h-1,2,3-triazol-1-yl]- 1-thio-alpha-d-galactopyranoside |
| WO2021198160A1 (en) * | 2020-03-31 | 2021-10-07 | Galecto Biotech Ab | Large scale process for preparing 1,2,4, 6-tetra-0-acetyl-3-azid0-3-de0xy-d-galact0pyran0side |
| UY39189A (es) | 2020-05-06 | 2021-12-31 | Fmc Corp | Fungicidas de tolilo sustituido y sus mezclas |
| EP4337657A1 (en) * | 2021-05-14 | 2024-03-20 | GlycoMimetics, Inc. | Galectin-3 inhibiting c-glycosides |
| WO2022250976A1 (en) * | 2021-05-28 | 2022-12-01 | Glycomimetics, Inc. | Galectin-3 inhibiting c-glycoside oximes |
| CN115611700B (zh) * | 2022-10-11 | 2024-06-14 | 辽宁东大光明化工科技有限责任公司 | 一种1-溴-2,5-二氯-3-氟苯的制备方法 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060148712A1 (en) * | 2000-03-13 | 2006-07-06 | Fu-Tong Liu | Monocyte chemoattractant activity of galectin-3 |
| SE0401301D0 (sv) * | 2004-05-21 | 2004-05-21 | Forskarpatent I Syd Ab | Novel 3-triazolyl-galactoside inhibitors of galectins |
| SE0401300D0 (sv) | 2004-05-21 | 2004-05-21 | Forskarpatent I Syd Ab | Novel Galactoside Inhibitors of Galectins |
| WO2010126435A1 (en) | 2009-04-28 | 2010-11-04 | Forskarpatent I Syd Ab | Novel galactoside inhibitors of galectins |
| US9243021B2 (en) * | 2012-10-31 | 2016-01-26 | Galecto Biotech Ab | Galactoside inhibitor of galectins |
| EP2620443A1 (en) * | 2012-01-25 | 2013-07-31 | Galecto Biotech AB | Novel galactoside inhibitors of galectins |
| JP6055928B2 (ja) | 2012-10-10 | 2016-12-27 | ガレクティン・セラピューティクス・インコーポレイテッドＧａｌｅｃｔｉｎ Ｔｈｅｒａｐｅｕｔｉｃｓ， Ｉｎｃ． | 糖尿病性腎症および関連障害の処置のためのガラクトース分枝炭水化物化合物 |
| IN2015DN02573A (US07846941-20101207-C00217.png) | 2012-10-31 | 2015-09-11 | Galecto Biotech Ab | |
| CA2926480A1 (en) * | 2012-11-15 | 2014-05-22 | Tufts University | Methods, compositions and kits for treating, modulating, or preventing ocular angiogenesis or fibrosis in a subject using a galectin protein inhibitor |
| US9699713B2 (en) * | 2014-02-27 | 2017-07-04 | Qualcomm Incorporated | Enhanced trigger frame based discovery for a neighbor awareness network |
| JP6735680B2 (ja) * | 2014-07-09 | 2020-08-05 | ガレクト バイオテック エービー | ガレクチンの新規ハイブリッドガラクトシド阻害剤 |
| WO2016113335A1 (en) * | 2015-01-16 | 2016-07-21 | Galecto Biotech Ab | Novel galactoside inhibitor of galectins |
| JP6904906B2 (ja) * | 2015-01-30 | 2021-07-21 | ガレクト・バイオテック・エイビイ | ガレクチンの新規なガラクトシド阻害剤 |
| WO2017019770A1 (en) * | 2015-07-27 | 2017-02-02 | Wayne State University | Compositions and methods relating to galectin detection |
| WO2017080973A1 (en) * | 2015-11-09 | 2017-05-18 | Galecto Biotech Ab | 1,1 '-sulfanediyl-di-beta-d-galactopyranosides as inhibitors of galectins |
| US10988502B2 (en) * | 2016-07-12 | 2021-04-27 | Galecto Biotech Ab | Alpha-D-galactoside inhibitors of galectins |
-
2017
- 2017-07-09 US US16/313,628 patent/US10889610B2/en active Active
- 2017-07-09 CN CN201780042811.XA patent/CN109563119A/zh active Pending
- 2017-07-09 EP EP17740711.1A patent/EP3484904A1/en not_active Withdrawn
- 2017-07-09 CA CA3025867A patent/CA3025867A1/en active Pending
- 2017-07-09 WO PCT/EP2017/067181 patent/WO2018011094A1/en unknown
- 2017-07-09 JP JP2019500851A patent/JP7216634B2/ja active Active
