JP2021105029A5 - - Google Patents
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- Publication number
- JP2021105029A5 JP2021105029A5 JP2021062805A JP2021062805A JP2021105029A5 JP 2021105029 A5 JP2021105029 A5 JP 2021105029A5 JP 2021062805 A JP2021062805 A JP 2021062805A JP 2021062805 A JP2021062805 A JP 2021062805A JP 2021105029 A5 JP2021105029 A5 JP 2021105029A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- galactopyranoside
- fluorophenyl
- triazole
- bis
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims description 53
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 44
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 24
- 230000008569 process Effects 0.000 claims description 22
- 239000000843 powder Substances 0.000 claims description 21
- 239000003960 organic solvent Substances 0.000 claims description 13
- 238000001035 drying Methods 0.000 claims description 10
- BLUGYPPOFIHFJS-UUFHNPECSA-N (2s)-n-[(2s)-1-[[(3r,4s,5s)-3-methoxy-1-[(2s)-2-[(1r,2r)-1-methoxy-2-methyl-3-oxo-3-[[(1s)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]amino]propyl]pyrrolidin-1-yl]-5-methyl-1-oxoheptan-4-yl]-methylamino]-3-methyl-1-oxobutan-2-yl]-3-methyl-2-(methylamino)butanamid Chemical compound CN[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N(C)[C@@H]([C@@H](C)CC)[C@H](OC)CC(=O)N1CCC[C@H]1[C@H](OC)[C@@H](C)C(=O)N[C@H](C=1SC=CN=1)CC1=CC=CC=C1 BLUGYPPOFIHFJS-UUFHNPECSA-N 0.000 claims description 8
- 208000007934 ACTH-independent macronodular adrenal hyperplasia Diseases 0.000 claims description 8
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- 239000010419 fine particle Substances 0.000 claims description 2
- 229940112141 dry powder inhaler Drugs 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 210000004072 lung Anatomy 0.000 description 18
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 229940079593 drug Drugs 0.000 description 13
- 239000008194 pharmaceutical composition Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000002002 slurry Substances 0.000 description 12
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
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- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
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- 239000008101 lactose Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
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- WNANQHRGHUEEFC-UHFFFAOYSA-N 4-(3-fluorophenyl)-2h-triazole Chemical compound FC1=CC=CC(C=2N=NNC=2)=C1 WNANQHRGHUEEFC-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 2
- 102100032341 PCNA-interacting partner Human genes 0.000 description 2
- 102000046299 Transforming Growth Factor beta1 Human genes 0.000 description 2
- 101800002279 Transforming growth factor beta-1 Proteins 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
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- 230000008859 change Effects 0.000 description 2
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- 238000002425 crystallisation Methods 0.000 description 2
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- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- WQZGKKKJIJFFOK-SVZMEOIVSA-N (+)-Galactose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-SVZMEOIVSA-N 0.000 description 1
- 206010067484 Adverse reaction Diseases 0.000 description 1
- LERNTVKEWCAPOY-VOGVJGKGSA-N C[N+]1(C)[C@H]2C[C@H](C[C@@H]1[C@H]1O[C@@H]21)OC(=O)C(O)(c1cccs1)c1cccs1 Chemical compound C[N+]1(C)[C@H]2C[C@H](C[C@@H]1[C@H]1O[C@@H]21)OC(=O)C(O)(c1cccs1)c1cccs1 LERNTVKEWCAPOY-VOGVJGKGSA-N 0.000 description 1
- 208000017667 Chronic Disease Diseases 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- 102000004127 Cytokines Human genes 0.000 description 1
- 108090000695 Cytokines Proteins 0.000 description 1
- 206010061818 Disease progression Diseases 0.000 description 1
- 206010016654 Fibrosis Diseases 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- GWRFIZPBOYQSQC-YFOZLWGASA-N OC[C@H](C(C1[n]2nnc(-c3cccc(F)c3)c2)O)OC(CS[C@@H](C(C2[n]3nnc(-c4cc(F)ccc4)c3)O)OC(CO)[C@@H]2O)[C@@H]1O Chemical compound OC[C@H](C(C1[n]2nnc(-c3cccc(F)c3)c2)O)OC(CS[C@@H](C(C2[n]3nnc(-c4cc(F)ccc4)c3)O)OC(CO)[C@@H]2O)[C@@H]1O GWRFIZPBOYQSQC-YFOZLWGASA-N 0.000 description 1
- 101710196737 PCNA-interacting partner Proteins 0.000 description 1
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 1
- 208000004756 Respiratory Insufficiency Diseases 0.000 description 1
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- 230000002159 abnormal effect Effects 0.000 description 1
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- 239000004480 active ingredient Substances 0.000 description 1
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- GJPICJJJRGTNOD-UHFFFAOYSA-N bosentan Chemical compound COC1=CC=CC=C1OC(C(=NC(=N1)C=2N=CC=CN=2)OCCO)=C1NS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 GJPICJJJRGTNOD-UHFFFAOYSA-N 0.000 description 1
- 229960003065 bosentan Drugs 0.000 description 1
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- 239000003205 fragrance Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
- 231100000021 irritant Toxicity 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000011866 long-term treatment Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 231100000516 lung damage Toxicity 0.000 description 1
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- 238000012986 modification Methods 0.000 description 1
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- 210000000651 myofibroblast Anatomy 0.000 description 1
- JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
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- 229960000257 tiotropium bromide Drugs 0.000 description 1
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- 229940099456 transforming growth factor beta 1 Drugs 0.000 description 1
- PAJMKGZZBBTTOY-ZFORQUDYSA-N treprostinil Chemical compound C1=CC=C(OCC(O)=O)C2=C1C[C@@H]1[C@@H](CC[C@@H](O)CCCCC)[C@H](O)C[C@@H]1C2 PAJMKGZZBBTTOY-ZFORQUDYSA-N 0.000 description 1
- 229940014025 tyvaso Drugs 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2021142305A JP7254130B2 (ja) | 2015-12-18 | 2021-09-01 | 結晶多形および医薬組成物 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP15201223.3 | 2015-12-18 | ||
| EP15201223 | 2015-12-18 | ||
| JP2018528313A JP6863984B2 (ja) | 2015-12-18 | 2016-12-16 | 結晶多形とプロセス |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018528313A Division JP6863984B2 (ja) | 2015-12-18 | 2016-12-16 | 結晶多形とプロセス |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021142305A Division JP7254130B2 (ja) | 2015-12-18 | 2021-09-01 | 結晶多形および医薬組成物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2021105029A JP2021105029A (ja) | 2021-07-26 |
| JP2021105029A5 true JP2021105029A5 (https=) | 2021-10-14 |
Family
ID=54979474
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018528313A Expired - Fee Related JP6863984B2 (ja) | 2015-12-18 | 2016-12-16 | 結晶多形とプロセス |
| JP2021062805A Pending JP2021105029A (ja) | 2015-12-18 | 2021-04-01 | 結晶多形とプロセス |
| JP2021142305A Active JP7254130B2 (ja) | 2015-12-18 | 2021-09-01 | 結晶多形および医薬組成物 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018528313A Expired - Fee Related JP6863984B2 (ja) | 2015-12-18 | 2016-12-16 | 結晶多形とプロセス |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021142305A Active JP7254130B2 (ja) | 2015-12-18 | 2021-09-01 | 結晶多形および医薬組成物 |
Country Status (7)
| Country | Link |
|---|---|
| US (3) | US10369136B2 (https=) |
| EP (2) | EP3896075A1 (https=) |
| JP (3) | JP6863984B2 (https=) |
| CN (1) | CN108602847A (https=) |
| CA (1) | CA3004632A1 (https=) |
| ES (1) | ES2925864T3 (https=) |
| WO (1) | WO2017103109A1 (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9243021B2 (en) * | 2012-10-31 | 2016-01-26 | Galecto Biotech Ab | Galactoside inhibitor of galectins |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9027234D0 (en) | 1990-12-15 | 1991-02-06 | Harris Pharma Ltd | An inhalation device |
| DE69230613T2 (de) | 1991-07-02 | 2000-12-28 | Inhale Inc | Verfahren und vorrichtung zum abgeben von medikamenten in aerosolform |
| EP0938907B1 (en) | 1996-01-03 | 2001-12-05 | Glaxo Group Limited | Inhalation device |
| US6962151B1 (en) | 1999-11-05 | 2005-11-08 | Pari GmbH Spezialisten für effektive Inhalation | Inhalation nebulizer |
| US6482847B2 (en) * | 2000-10-03 | 2002-11-19 | Hoffmann-La Roche Inc. | Amorphous form of cell cycle inhibitor having improved solubility and bioavailability |
| DE10102846B4 (de) | 2001-01-23 | 2012-04-12 | Pari Pharma Gmbh | Aerosolgenerator |
| ATE269735T1 (de) | 2001-10-18 | 2004-07-15 | Pari Gmbh | Inhalationstherapievorrichtung |
| DE60235883D1 (de) | 2002-08-02 | 2010-05-20 | Pari Pharma Gmbh | Vorrichtung zur Erzeugung von Flüssigkeitströpfchen |
| DE10250625A1 (de) | 2002-10-30 | 2004-05-19 | Pari GmbH Spezialisten für effektive Inhalation | Inhalationstherapievorrichtung |
| DE10257381B4 (de) | 2002-12-09 | 2006-09-14 | Pari GmbH Spezialisten für effektive Inhalation | Inhalationstherapievorrichtung |
| PT104350A (pt) * | 2009-01-23 | 2010-07-23 | Hovione Farmaci Ncia S A | Processo de isolamento de tigeciclina |
| DE102009026636B4 (de) | 2009-06-02 | 2011-04-14 | Pari Pharma Gmbh | Verfahren zum Verschweißen einer Membran mit einem Träger bei der Herstellung eines Membranverneblers |
| US9243021B2 (en) | 2012-10-31 | 2016-01-26 | Galecto Biotech Ab | Galactoside inhibitor of galectins |
| CN104755088A (zh) * | 2012-10-31 | 2015-07-01 | 格莱克特生物技术公司 | 半乳凝集素-3的半乳糖苷抑制剂及其用于治疗肺纤维化的应用 |
| EP2919802A4 (en) * | 2012-11-15 | 2016-09-14 | Univ Tufts | METHOD, COMPOSITIONS AND KITS FOR TREATING, MODULATING OR PREVENTING ANGIOGENESIS OR FIBROSIS IN A PATIENT USING A GALECTINE PROTEIN HEMMER |
| WO2015155207A1 (en) * | 2014-04-08 | 2015-10-15 | Galecto Biotech Ab | Galactoside inhibitors for the treatment of alpha-synucleinopthies |
-
2016
- 2016-12-16 EP EP21175042.7A patent/EP3896075A1/en not_active Withdrawn
- 2016-12-16 EP EP16809870.5A patent/EP3390423B1/en active Active
- 2016-12-16 CN CN201680071057.8A patent/CN108602847A/zh active Pending
- 2016-12-16 ES ES16809870T patent/ES2925864T3/es active Active
- 2016-12-16 US US16/062,206 patent/US10369136B2/en active Active
- 2016-12-16 WO PCT/EP2016/081432 patent/WO2017103109A1/en not_active Ceased
- 2016-12-16 CA CA3004632A patent/CA3004632A1/en active Pending
- 2016-12-16 JP JP2018528313A patent/JP6863984B2/ja not_active Expired - Fee Related
-
2018
- 2018-11-28 US US16/202,487 patent/US10307403B2/en active Active
-
2019
- 2019-05-13 US US16/410,110 patent/US10799482B2/en active Active
-
2021
- 2021-04-01 JP JP2021062805A patent/JP2021105029A/ja active Pending
- 2021-09-01 JP JP2021142305A patent/JP7254130B2/ja active Active
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