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
- 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 (OSRAM) | 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 (OSRAM) |
| EP (1) | EP3484904A1 (OSRAM) |
| JP (1) | JP7216634B2 (OSRAM) |
| CN (1) | CN109563119A (OSRAM) |
| CA (1) | CA3025867A1 (OSRAM) |
| WO (1) | WO2018011094A1 (OSRAM) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016120403A1 (en) | 2015-01-30 | 2016-08-04 | Galecto Biotech Ab | Alpha-d-galactoside inhibitors of galectins |
| EP3484903A1 (en) * | 2016-07-12 | 2019-05-22 | Galecto Biotech AB | Alpha-d-galactoside inhibitors of galectins |
| BR112020013647A2 (pt) * | 2018-01-10 | 2020-12-01 | Galecto Biotech Ab | novo inibidor galactosídeo de galectinas |
| WO2020078807A1 (en) * | 2018-10-15 | 2020-04-23 | Galecto Biotech Ab | Prodrug of galactoside inhibitors of galectins |
| WO2020078808A1 (en) * | 2018-10-15 | 2020-04-23 | Galecto Biotech Ab | Galactoside inhibitor of galectins |
| 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 |
| CN113412267B (zh) * | 2018-11-21 | 2025-06-27 | 格莱克特生物技术公司 | 半乳糖凝集素的α-D-半乳糖苷抑制剂 |
| KR20210110645A (ko) * | 2018-12-27 | 2021-09-08 | 글리코미메틱스, 인크. | 갈렉틴-3 억제 c-글리코사이드 |
| 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 |
| US12291547B2 (en) | 2019-06-14 | 2025-05-06 | UNIVERSITé LAVAL | Synthesis of 3-azido-3-deoxy-D-galactopyranose |
| CN114514235A (zh) * | 2019-07-03 | 2022-05-17 | 格莱克特生物技术公司 | 半乳糖凝集素的新型半乳糖苷抑制剂 |
| 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 |
| US12404295B2 (en) | 2019-08-09 | 2025-09-02 | Idorsia Pharmaceuticals Ltd | (Hetero)aryl-methyl-thio-beta-D-galactopyranoside derivatives |
| ES3015725T3 (en) | 2019-08-15 | 2025-05-07 | Idorsia Pharmaceuticals Ltd | 2-hydroxycycloalkane-1-carbamoyl derivatives |
| AU2020338816A1 (en) * | 2019-08-29 | 2022-04-14 | Idorsia Pharmaceuticals Ltd | Alpha-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 |
| CN115244045A (zh) * | 2019-12-24 | 2022-10-25 | 糖模拟物有限公司 | 抑制半乳凝素-3的c-糖苷酮、醚和醇 |
| US20230137160A1 (en) * | 2020-03-31 | 2023-05-04 | Galecto Biotech Ab | Large scale process for preparing 1,2,4, 6-tetra-o-acetyl-3-azido-3-deoxy-d-galactopyranoside |
| UY39189A (es) | 2020-05-06 | 2021-12-31 | Fmc Corp | Fungicidas de tolilo sustituido y sus mezclas |
| EP4225752B1 (en) | 2020-10-06 | 2024-12-11 | Idorsia Pharmaceuticals Ltd | Spiro derivatives of alpha-d-galactopyranosides |
| EP4237419A1 (en) | 2020-11-02 | 2023-09-06 | Idorsia Pharmaceuticals Ltd | Galectin-3 inhibiting 2-hydroxycycloalkane-1 -carbamoyl derivatives |
| IL304923A (en) | 2021-02-09 | 2023-10-01 | Idorsia Pharmaceuticals Ltd | History of hydroxyheterocycloalkane-carbamoyl |
| JP2024517936A (ja) * | 2021-05-14 | 2024-04-23 | グリコミメティクス， インコーポレイテッド | ガレクチン－３阻害性ｃ－グリコシド |
| 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 |
| SE0401300D0 (sv) | 2004-05-21 | 2004-05-21 | Forskarpatent I Syd Ab | Novel Galactoside Inhibitors of Galectins |
| SE0401301D0 (sv) | 2004-05-21 | 2004-05-21 | Forskarpatent I Syd Ab | Novel 3-triazolyl-galactoside inhibitors of galectins |
| US8703720B2 (en) * | 2009-04-28 | 2014-04-22 | Galecto Biotech Ab | 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 |
| EP2914269B1 (en) | 2012-10-31 | 2020-07-29 | Galecto Biotech AB | Galactoside inhibitor of galectin-3 and its use for treating pulmonary fibrosis |
| JP6366598B2 (ja) | 2012-11-15 | 2018-08-01 | タフツ ユニバーシティー | ガレクチンタンパク質阻害剤を用いて被験体の眼の血管新生または繊維症を処置し、調節し、または、予防する方法、組成物、およびキット |
| US9699713B2 (en) * | 2014-02-27 | 2017-07-04 | Qualcomm Incorporated | Enhanced trigger frame based discovery for a neighbor awareness network |
| ES2784873T3 (es) * | 2014-07-09 | 2020-10-01 | Galecto Biotech Ab | Novedoso inhibidor galactósido híbrido de galectinas |
| EP3245216B1 (en) * | 2015-01-16 | 2019-12-11 | Galecto Biotech AB | Novel galactoside inhibitor of galectins |
| WO2016120403A1 (en) | 2015-01-30 | 2016-08-04 | Galecto Biotech Ab | Alpha-d-galactoside inhibitors of galectins |
| US10799522B2 (en) * | 2015-07-27 | 2020-10-13 | Wayne State University | Compositions and methods relating to galectin detection |
| EP3374368B1 (en) * | 2015-11-09 | 2022-06-01 | Galecto Biotech AB | 1,1'-sulfanediyl-di-beta-d-galactopyranosides as inhibitors of galectins |
| EP3484903A1 (en) | 2016-07-12 | 2019-05-22 | 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 EP EP17740711.1A patent/EP3484904A1/en not_active Withdrawn
- 2017-07-09 WO PCT/EP2017/067181 patent/WO2018011094A1/en not_active Ceased
- 2017-07-09 CA CA3025867A patent/CA3025867A1/en active Pending
- 2017-07-09 JP JP2019500851A patent/JP7216634B2/ja active Active
- 2017-07-09 CN CN201780042811.XA patent/CN109563119A/zh active Pending
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