JP2019522007A5 - - Google Patents
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- Publication number
- 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
Links
- 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
- 125000001072 heteroaryl group Chemical group 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
- 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
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-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
- GZCGUPFRVQAUEE-UHFFFAOYSA-N alpha-D-galactose Natural products OCC(O)C(O)C(O)C(O)C=O GZCGUPFRVQAUEE-UHFFFAOYSA-N 0.000 claims description 3
- WQZGKKKJIJFFOK-UHFFFAOYSA-N alpha-D-glucopyranose Natural products OCC1OC(O)C(O)C(O)C1O WQZGKKKJIJFFOK-UHFFFAOYSA-N 0.000 claims description 3
- 229960003082 galactose Drugs 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
- 239000012453 solvate Substances 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 3
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 230000033115 angiogenesis Effects 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 230000004761 fibrosis Effects 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
- 208000035475 disorder Diseases 0.000 claims 2
- 208000030159 metabolic disease Diseases 0.000 claims 2
- QHXFOIHAIAOUHI-CAEUUNHDSA-N (2R,3R,4S,5R,6R)-2-(2-chloropyridin-4-yl)sulfanyl-6-(hydroxymethyl)-4-[4-(3,4,5-trifluorophenyl)triazol-1-yl]oxane-3,5-diol 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 (2R,3R,4S,5R,6R)-2-(4-chloropyridin-2-yl)sulfanyl-6-(hydroxymethyl)-4-[4-(3,4,5-trifluorophenyl)triazol-1-yl]oxane-3,5-diol 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
- YGCUIZJEHKOBCY-ICBNADEASA-N (2R,3R,4S,5R,6R)-4-[4-(4-chloro-3-fluorophenyl)triazol-1-yl]-2-(5-chloropyridin-3-yl)sulfanyl-6-(hydroxymethyl)oxane-3,5-diol 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
- ZMXRBTNYSARFEU-DABHTEOTSA-N 3-bromo-5-[(2R,3R,4S,5R,6R)-4-[4-(4-chloro-3,5-difluorophenyl)triazol-1-yl]-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanylpyridine-2-carbonitrile 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
- ZIZMKGYAKCDXAV-DABHTEOTSA-N 3-chloro-5-[(2R,3R,4S,5R,6R)-4-[4-(4-chloro-3,5-difluorophenyl)triazol-1-yl]-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanylpyridine-2-carbonitrile 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
- FXAVWGPNWZCDHN-RBUQIHAASA-N 5-bromo-3-[(2R,3R,4S,5R,6R)-4-[4-(4-chloro-3,5-difluorophenyl)triazol-1-yl]-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanylpyridine-2-carbonitrile 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
- SWKFRXPLZKGBMW-RBUQIHAASA-N 5-chloro-3-[(2R,3R,4S,5R,6R)-4-[4-(4-chloro-3,5-difluorophenyl)triazol-1-yl]-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanylpyridine-2-carbonitrile 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
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 208000011231 Crohn 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 failures Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 208000029523 Interstitial Lung disease Diseases 0.000 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 208000034038 Pathologic Neovascularization Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 206010039491 Sarcoma Diseases 0.000 claims 1
- 206010040070 Septic Shock Diseases 0.000 claims 1
- 201000002661 Spondylitis Diseases 0.000 claims 1
- 206010042971 T-cell lymphoma Diseases 0.000 claims 1
- 208000027585 T-cell non-Hodgkin lymphoma Diseases 0.000 claims 1
- 208000031737 Tissue Adhesions Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 230000002159 abnormal effect Effects 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 208000019425 cirrhosis of liver Diseases 0.000 claims 1
- 201000000159 corneal neovascularization Diseases 0.000 claims 1
- 230000007850 degeneration Effects 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000016097 disease of metabolism Diseases 0.000 claims 1
- 208000030533 eye disease Diseases 0.000 claims 1
- 208000019622 heart disease Diseases 0.000 claims 1
- 208000006454 hepatitis Diseases 0.000 claims 1
- 231100000283 hepatitis Toxicity 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 208000011379 keloid formation Diseases 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 239000003446 ligand Substances 0.000 claims 1
- 208000019423 liver disease Diseases 0.000 claims 1
- 230000000938 luteal effect Effects 0.000 claims 1
- 208000037819 metastatic cancer Diseases 0.000 claims 1
- 208000011575 metastatic malignant neoplasm Diseases 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 208000005069 pulmonary fibrosis Diseases 0.000 claims 1
- 201000002793 renal fibrosis Diseases 0.000 claims 1
- 206010039073 rheumatoid arthritis 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
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 230000009885 systemic effect Effects 0.000 claims 1
- 230000001256 tonic effect Effects 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 (enExample) | 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)
| Country | Link |
|---|---|
| US (1) | US10889610B2 (enExample) |
| EP (1) | EP3484904A1 (enExample) |
| JP (1) | JP7216634B2 (enExample) |
| CN (1) | CN109563119A (enExample) |
| CA (1) | CA3025867A1 (enExample) |
| WO (1) | WO2018011094A1 (enExample) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3828191A3 (en) | 2015-01-30 | 2021-08-18 | Galecto Biotech AB | Novel galactoside inhibitor of galectins |
| EP3484903A1 (en) * | 2016-07-12 | 2019-05-22 | Galecto Biotech AB | Alpha-d-galactoside inhibitors of galectins |
| MX2020007391A (es) * | 2018-01-10 | 2020-09-03 | Galecto Biotech Ab | Nuevo galactosido inhibidor de galectinas. |
| CA3114055A1 (en) * | 2018-10-15 | 2020-04-23 | Galecto Biotech Ab | Prodrug of galactoside inhibitors of galectins |
| EP3867260A1 (en) * | 2018-10-15 | 2021-08-25 | Galecto Biotech AB | Galactoside inhibitor of galectins |
| TWI846654B (zh) | 2018-11-06 | 2024-06-21 | 美商富曼西公司 | 經取代之甲苯基殺真菌劑 |
| US11447517B2 (en) | 2018-11-21 | 2022-09-20 | Galecto Biotech Ab | Galactoside inhibitor of galectins |
| EP3902797A1 (en) * | 2018-12-27 | 2021-11-03 | GlycoMimetics, Inc. | Galectin-3 inhibiting c-glycosides |
| US12275719B2 (en) | 2019-03-26 | 2025-04-15 | Bristol-Myers Squibb Company | Small molecule inhibitors of galectin-3 |
| US12291547B2 (en) | 2019-06-14 | 2025-05-06 | UNIVERSITé LAVAL | Synthesis of 3-azido-3-deoxy-D-galactopyranose |
| WO2021001538A1 (en) * | 2019-07-03 | 2021-01-07 | Galecto Biotech Ab | Novel galactoside inhibitor of galectins |
| WO2021028336A1 (en) | 2019-08-09 | 2021-02-18 | Idorsia Pharmaceuticals Ltd | (hetero)aryl-methyl-thio-beta-d-galactopyranoside derivatives |
| JP7612663B2 (ja) * | 2019-08-09 | 2025-01-14 | イドルシア・ファーマシューティカルズ・リミテッド | （２－アセタミジル）チオ－ベータ－ｄ－ガラクトピラノシド誘導体 |
| CA3147454A1 (en) | 2019-08-15 | 2021-02-18 | Martin Bolli | 2-hydroxycycloalkane-1-carbamoyl derivatives |
| RS65294B1 (sr) | 2019-08-29 | 2024-04-30 | Idorsia Pharmaceuticals Ltd | Derivati alfa-d-galaktopiranozida |
| 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 |
| US20230091472A1 (en) * | 2019-12-24 | 2023-03-23 | Glycomimetics, Inc. | Galectin-3 inhibiting c-glycoside ketones, ethers, and alcohols |
| JP2023519952A (ja) * | 2020-03-31 | 2023-05-15 | ガレクト バイオテック エービー | １，２，４，６－テトラ－ｏ－アセチル－３－アジド－３－デオキシ－ｄ－ガラクトピラノシドを調製するための大規模方法 |
| UY39189A (es) | 2020-05-06 | 2021-12-31 | Fmc Corp | Fungicidas de tolilo sustituido y sus mezclas |
| WO2022073969A1 (en) | 2020-10-06 | 2022-04-14 | Idorsia Pharmaceuticals Ltd | Spiro derivatives of alpha-d-galactopyranosides |
| US12291520B2 (en) | 2020-11-02 | 2025-05-06 | Idorsia Pharmaceuticals Ltd | Galectin-3 inhibiting 2-hydroxycycloalkane-1-carbamoyl derivatives |
| US12304902B2 (en) | 2021-02-09 | 2025-05-20 | Idorsia Pharmaceuticals Ltd | Hydroxyheterocycloalkane-carbamoyl derivatives |
| EP4337657A1 (en) * | 2021-05-14 | 2024-03-20 | GlycoMimetics, Inc. | Galectin-3 inhibiting c-glycosides |
| US20240287121A1 (en) * | 2021-05-28 | 2024-08-29 | 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 |
| ES2698101T3 (es) | 2012-10-10 | 2019-01-31 | Galectin Therapeutics Inc | Compuestos de carbohidrato con restos de galactosa para el tratamiento de la nefropatía diabética y trastornos asociados |
| ES2817888T3 (es) * | 2012-10-31 | 2021-04-08 | Galecto Biotech Ab | Inhibidor de galactósido de galectina-3 y su uso para tratar fibrosis pulmonar |
| WO2014078655A1 (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 |
| EP3415522A1 (en) * | 2014-07-09 | 2018-12-19 | Galecto Biotech AB | Novel hybrid galactoside inhibitor of galectins |
| US10464964B2 (en) * | 2015-01-16 | 2019-11-05 | Galecto Biotech Ab | Galactoside inhibitor of galectins |
| EP3828191A3 (en) * | 2015-01-30 | 2021-08-18 | Galecto Biotech AB | Novel galactoside inhibitor of galectins |
| US10799522B2 (en) * | 2015-07-27 | 2020-10-13 | Wayne State University | Compositions and methods relating to galectin detection |
| CA3000924A1 (en) * | 2015-11-09 | 2017-05-18 | Galecto Biotech Ab | Novel galactoside inhibitors of galectins |
| EP3484903A1 (en) | 2016-07-12 | 2019-05-22 | Galecto Biotech AB | Alpha-d-galactoside inhibitors of galectins |
-
2017
- 2017-07-09 WO PCT/EP2017/067181 patent/WO2018011094A1/en not_active Ceased
- 2017-07-09 EP EP17740711.1A patent/EP3484904A1/en not_active Withdrawn
- 2017-07-09 JP JP2019500851A patent/JP7216634B2/ja active Active
- 2017-07-09 CN CN201780042811.XA patent/CN109563119A/zh active Pending
- 2017-07-09 US US16/313,628 patent/US10889610B2/en active Active
- 2017-07-09 CA CA3025867A patent/CA3025867A1/en active Pending
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