JP2016525573A5 - - Google Patents
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- Publication number
- JP2016525573A5 JP2016525573A5 JP2016531596A JP2016531596A JP2016525573A5 JP 2016525573 A5 JP2016525573 A5 JP 2016525573A5 JP 2016531596 A JP2016531596 A JP 2016531596A JP 2016531596 A JP2016531596 A JP 2016531596A JP 2016525573 A5 JP2016525573 A5 JP 2016525573A5
- Authority
- JP
- Japan
- Prior art keywords
- pharmaceutical formulation
- compound
- formulation according
- dose
- pharmaceutically acceptable
- 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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- 239000008194 pharmaceutical composition Substances 0.000 claims 27
- 150000001875 compounds Chemical class 0.000 claims 20
- 150000003839 salts Chemical class 0.000 claims 12
- 239000012453 solvate Substances 0.000 claims 12
- 238000009472 formulation Methods 0.000 claims 9
- 239000000203 mixture Substances 0.000 claims 9
- 208000019693 Lung disease Diseases 0.000 claims 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims 5
- -1 bronchodilator Substances 0.000 claims 4
- 208000023504 respiratory system disease Diseases 0.000 claims 4
- 206010021143 Hypoxia Diseases 0.000 claims 3
- 206010061218 Inflammation Diseases 0.000 claims 3
- 206010006451 bronchitis Diseases 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 239000003172 expectorant agent Substances 0.000 claims 3
- 230000004054 inflammatory process Effects 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 206010006448 Bronchiolitis Diseases 0.000 claims 2
- 206010006458 Bronchitis chronic Diseases 0.000 claims 2
- 102100036166 C-X-C chemokine receptor type 1 Human genes 0.000 claims 2
- 102000019034 Chemokines Human genes 0.000 claims 2
- 108010012236 Chemokines Proteins 0.000 claims 2
- 201000003883 Cystic fibrosis Diseases 0.000 claims 2
- 208000000059 Dyspnea Diseases 0.000 claims 2
- 206010013975 Dyspnoeas Diseases 0.000 claims 2
- 206010014561 Emphysema Diseases 0.000 claims 2
- GEZJUQFQSVEHKK-UHFFFAOYSA-N FC1=CC=C(C=C1)NC(=O)C1(NC=CC=N1)Cl Chemical compound FC1=CC=C(C=C1)NC(=O)C1(NC=CC=N1)Cl GEZJUQFQSVEHKK-UHFFFAOYSA-N 0.000 claims 2
- 101000947174 Homo sapiens C-X-C chemokine receptor type 1 Proteins 0.000 claims 2
- 206010058490 Hyperoxia Diseases 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 201000009267 bronchiectasis Diseases 0.000 claims 2
- 208000007451 chronic bronchitis Diseases 0.000 claims 2
- 238000011038 discontinuous diafiltration by volume reduction Methods 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 230000000222 hyperoxic effect Effects 0.000 claims 2
- 208000018875 hypoxemia Diseases 0.000 claims 2
- 210000004072 lung Anatomy 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 229940066491 mucolytics Drugs 0.000 claims 2
- JLULRRGANITLAX-UHFFFAOYSA-N n-(4-fluorophenyl)-2-sulfanylidene-1h-pyrimidine-5-carboxamide Chemical compound C1=CC(F)=CC=C1NC(=O)C1=CN=C(S)N=C1 JLULRRGANITLAX-UHFFFAOYSA-N 0.000 claims 2
- 230000002093 peripheral effect Effects 0.000 claims 2
- 230000002685 pulmonary effect Effects 0.000 claims 2
- 208000005069 pulmonary fibrosis Diseases 0.000 claims 2
- 208000002815 pulmonary hypertension Diseases 0.000 claims 2
- 238000001356 surgical procedure Methods 0.000 claims 2
- 238000009423 ventilation Methods 0.000 claims 2
- CJXUOEJTOXQAMB-UHFFFAOYSA-N 2-[2-(bromomethyl)-4-(trifluoromethoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(OC(F)(F)F)C=C1CBr CJXUOEJTOXQAMB-UHFFFAOYSA-N 0.000 claims 1
- DUCXUPKLVVSJKA-UHFFFAOYSA-N 2-chloropyrimidine-5-carboxylic acid Chemical compound OC(=O)C1=CN=C(Cl)N=C1 DUCXUPKLVVSJKA-UHFFFAOYSA-N 0.000 claims 1
- BMIBJCFFZPYJHF-UHFFFAOYSA-N 2-methoxy-5-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Chemical class COC1=NC=C(C)C=C1B1OC(C)(C)C(C)(C)O1 BMIBJCFFZPYJHF-UHFFFAOYSA-N 0.000 claims 1
- ASZZHBXPMOVHCU-UHFFFAOYSA-N 3,9-diazaspiro[5.5]undecane-2,4-dione Chemical compound C1C(=O)NC(=O)CC11CCNCC1 ASZZHBXPMOVHCU-UHFFFAOYSA-N 0.000 claims 1
- LZPWAYBEOJRFAX-UHFFFAOYSA-N 4,4,5,5-tetramethyl-1,3,2$l^{2}-dioxaborolane Chemical compound CC1(C)O[B]OC1(C)C LZPWAYBEOJRFAX-UHFFFAOYSA-N 0.000 claims 1
- KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 claims 1
- 229940124125 5 Lipoxygenase inhibitor Drugs 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 229940122858 Elastase inhibitor Drugs 0.000 claims 1
- 102000018997 Growth Hormone Human genes 0.000 claims 1
- 108010051696 Growth Hormone Proteins 0.000 claims 1
- 239000000867 Lipoxygenase Inhibitor Substances 0.000 claims 1
- 229940124761 MMP inhibitor Drugs 0.000 claims 1
- 108010014865 PLIalpha Proteins 0.000 claims 1
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims 1
- 229940099471 Phosphodiesterase inhibitor Drugs 0.000 claims 1
- 229940123898 Phospholipase A2 inhibitor Drugs 0.000 claims 1
- 229940117896 Phospholipase D inhibitor Drugs 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 206010063837 Reperfusion injury Diseases 0.000 claims 1
- 239000002597 adenosine A2 receptor agonist Substances 0.000 claims 1
- 239000000048 adrenergic agonist Substances 0.000 claims 1
- 239000000443 aerosol Substances 0.000 claims 1
- 230000036428 airway hyperreactivity Effects 0.000 claims 1
- 239000005557 antagonist Substances 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 239000003963 antioxidant agent Substances 0.000 claims 1
- 230000003078 antioxidant effect Effects 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 229940125388 beta agonist Drugs 0.000 claims 1
- 102000014974 beta2-adrenergic receptor activity proteins Human genes 0.000 claims 1
- 108040006828 beta2-adrenergic receptor activity proteins Proteins 0.000 claims 1
- 230000017531 blood circulation Effects 0.000 claims 1
- 210000003123 bronchiole Anatomy 0.000 claims 1
- 229940124630 bronchodilator Drugs 0.000 claims 1
- 206010006475 bronchopulmonary dysplasia Diseases 0.000 claims 1
- 229940127089 cytotoxic agent Drugs 0.000 claims 1
- 239000000850 decongestant Substances 0.000 claims 1
- 239000003136 dopamine receptor stimulating agent Substances 0.000 claims 1
- 239000003602 elastase inhibitor Substances 0.000 claims 1
- 239000000839 emulsion Substances 0.000 claims 1
- 230000003419 expectorant effect Effects 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- 239000003862 glucocorticoid Substances 0.000 claims 1
- 239000000122 growth hormone Substances 0.000 claims 1
- 239000000938 histamine H1 antagonist Substances 0.000 claims 1
- 239000003395 histamine H3 receptor antagonist Substances 0.000 claims 1
- 230000007954 hypoxia Effects 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 230000000302 ischemic effect Effects 0.000 claims 1
- VNYSSYRCGWBHLG-AMOLWHMGSA-N leukotriene B4 Chemical compound CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O VNYSSYRCGWBHLG-AMOLWHMGSA-N 0.000 claims 1
- 239000003199 leukotriene receptor blocking agent Substances 0.000 claims 1
- 230000000510 mucolytic effect Effects 0.000 claims 1
- 239000000234 muscarinic M1 receptor antagonist Substances 0.000 claims 1
- 239000000536 muscarinic M2 receptor agonist Substances 0.000 claims 1
- 239000003681 muscarinic M3 receptor antagonist Substances 0.000 claims 1
- 239000002742 neurokinin 1 receptor antagonist Substances 0.000 claims 1
- 239000002746 neurokinin 2 receptor antagonist Substances 0.000 claims 1
- 239000002740 neurokinin 3 receptor antagonist Substances 0.000 claims 1
- 239000002762 nociceptin receptor agonist Substances 0.000 claims 1
- 230000000414 obstructive effect Effects 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 1
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims 1
- 239000003358 phospholipase A2 inhibitor Substances 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US2013/053376 WO2015016938A1 (en) | 2013-08-02 | 2013-08-02 | 2- [5- [n- (4 -fluorophenyl) carbamoyl] pyrimidin- 2 - ylsulfanylmethyl] -4- (trifluoromet hoxy) phenyl] boronic acid |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019071014A Division JP2019135244A (ja) | 2019-04-03 | 2019-04-03 | ２−［５−［ｎ−（４−フルオロフェニル）カルバモイル］ピリミジン−２−イルスルファニルメチル］−４−（トリフルオロメトキシ）フェニル」ボロン酸 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016525573A JP2016525573A (ja) | 2016-08-25 |
| JP2016525573A5 true JP2016525573A5 (https=) | 2016-10-06 |
| JP6509851B2 JP6509851B2 (ja) | 2019-05-08 |
Family
ID=48998708
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016531596A Active JP6509851B2 (ja) | 2013-08-02 | 2013-08-02 | ２−［５−［ｎ−（４−フルオロフェニル）カルバモイル］ピリミジン−２−イルスルファニルメチル］−４−（トリフルオロメトキシ）フェニル」ボロン酸 |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP3027627B1 (https=) |
| JP (1) | JP6509851B2 (https=) |
| KR (1) | KR102107372B1 (https=) |
| CN (2) | CN110200979A (https=) |
| AU (2) | AU2013395662B2 (https=) |
| CA (1) | CA2920172C (https=) |
| DK (1) | DK3027627T3 (https=) |
| ES (1) | ES2671927T3 (https=) |
| IL (1) | IL243913A0 (https=) |
| MX (1) | MX359556B (https=) |
| NO (1) | NO3027627T3 (https=) |
| WO (1) | WO2015016938A1 (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10046002B2 (en) | 2013-08-02 | 2018-08-14 | Syntrix Biosystems Inc. | Method for treating cancer using chemokine antagonists |
| EP3027627B1 (en) * | 2013-08-02 | 2018-01-31 | Syntrix Biosystems Inc. | 2-[5-[n-(4-fluorophenyl)carbamoyl]pyrimidin-2-ylsulfanylmethyl]-4-(trifluoromethoxy)phenyl]boronic acid |
| US8969365B2 (en) | 2013-08-02 | 2015-03-03 | Syntrix Biosystems, Inc. | Thiopyrimidinecarboxamides as CXCR1/2 modulators |
| JP2019135244A (ja) * | 2019-04-03 | 2019-08-15 | シントリックス・バイオシステムズ・インコーポレイテッドＳｙｎｔｒｉｘ Ｂｉｏｓｙｓｔｅｍｓ， Ｉｎｃ． | ２−［５−［ｎ−（４−フルオロフェニル）カルバモイル］ピリミジン−２−イルスルファニルメチル］−４−（トリフルオロメトキシ）フェニル」ボロン酸 |
| CN117954000A (zh) * | 2023-12-29 | 2024-04-30 | 中山大学附属口腔医院 | 用于筛选对治疗牙周炎及认知障碍的化合物的方法及用途 |
| WO2025193763A1 (en) * | 2024-03-12 | 2025-09-18 | Syntrix Biosystems Inc. | Method for increasing survival in patients with cancer |
| EP4686469A1 (en) * | 2024-07-31 | 2026-02-04 | Dompé farmaceutici SpA | Cxcl8 inhibitors for use in the treatment of diabetes-associated comorbidities |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5411947A (en) | 1989-06-28 | 1995-05-02 | Vestar, Inc. | Method of converting a drug to an orally available form by covalently bonding a lipid to the drug |
| US5475120A (en) | 1990-11-02 | 1995-12-12 | University Of Florida | Method for the isolation and purification of taxol and its natural analogues |
| US5194635A (en) | 1991-03-18 | 1993-03-16 | Virginia Tech Intellectual Properties, Inc. | Rearranged taxol compounds and method of using in testing of in vivo activity |
| US5416225A (en) | 1992-03-30 | 1995-05-16 | Sloan-Kettering Institute For Cancer Research | Total synthesis of taxol |
| US5488116A (en) | 1992-03-30 | 1996-01-30 | Sloan-Kettering Institute For Cancer Research | Total synthesis of taxol and analogues thereof |
| JPH07505887A (ja) | 1992-04-17 | 1995-06-29 | アボツト・ラボラトリーズ | タキソール誘導体 |
| US5440057A (en) | 1993-08-20 | 1995-08-08 | The Scripps Research Institute | Access to taxol analogs |
| US5461169A (en) | 1992-06-23 | 1995-10-24 | The Scripps Research Institute | Total synthesis of taxol and taxol analogs |
| WO1994005282A1 (en) | 1992-09-04 | 1994-03-17 | The Scripps Research Institute | Water soluble taxol derivatives |
| US5478854A (en) | 1992-10-01 | 1995-12-26 | Bristol-Myers Squibb Company | Deoxy taxols |
| US5411984A (en) | 1992-10-16 | 1995-05-02 | Virginia Tech Intellectual Properties, Inc. | Water soluble analogs and prodrugs of taxol |
| WO1994013827A1 (en) | 1992-12-07 | 1994-06-23 | Michigan State University | PROCESS FOR THE ISOLATION AND PURIFICATION OF TAXOL AND TAXANES FROM TAXUS spp |
| US5468769A (en) | 1993-07-15 | 1995-11-21 | Abbott Laboratories | Paclitaxel derivatives |
| FR2707642B1 (fr) | 1993-07-16 | 1995-10-13 | Electricite De France | Dérivés de polyéthers et d'hétérocycles pentacycliques, leurs polymères et leurs applications, notamment à la complexation d'ions métalliques. |
| US5405972A (en) | 1993-07-20 | 1995-04-11 | Florida State University | Synthetic process for the preparation of taxol and other tricyclic and tetracyclic taxanes |
| US5565478A (en) | 1994-03-14 | 1996-10-15 | The United States Of America As Represented By The Department Of Health & Human Services | Combination therapy using signal transduction inhibitors with paclitaxel and other taxane analogs |
| US5508447A (en) | 1994-05-24 | 1996-04-16 | Board Of Regents, The University Of Texas System | Short synthetic route to taxol and taxol derivatives |
| US5489589A (en) | 1994-12-07 | 1996-02-06 | Bristol-Myers Squibb Company | Amino acid derivatives of paclitaxel |
| SE9903544D0 (sv) * | 1999-10-01 | 1999-10-01 | Astra Pharma Prod | Novel compounds |
| US8748623B2 (en) * | 2009-02-17 | 2014-06-10 | Syntrix Biosystems, Inc. | Pyridinecarboxamides as CXCR2 modulators |
| CA2811990C (en) * | 2010-08-23 | 2023-03-21 | Dean Y. Maeda | Aminopyridine- and aminopyrimidinecarboxamides as cxcr2 modulators |
| EP3027627B1 (en) * | 2013-08-02 | 2018-01-31 | Syntrix Biosystems Inc. | 2-[5-[n-(4-fluorophenyl)carbamoyl]pyrimidin-2-ylsulfanylmethyl]-4-(trifluoromethoxy)phenyl]boronic acid |
-
2013
- 2013-08-02 EP EP13750432.0A patent/EP3027627B1/en active Active
- 2013-08-02 KR KR1020167005561A patent/KR102107372B1/ko active Active
- 2013-08-02 JP JP2016531596A patent/JP6509851B2/ja active Active
- 2013-08-02 CA CA2920172A patent/CA2920172C/en active Active
- 2013-08-02 NO NO13750432A patent/NO3027627T3/no unknown
- 2013-08-02 WO PCT/US2013/053376 patent/WO2015016938A1/en not_active Ceased
- 2013-08-02 MX MX2016001490A patent/MX359556B/es active IP Right Grant
- 2013-08-02 CN CN201910299619.XA patent/CN110200979A/zh active Pending
- 2013-08-02 CN CN201380080028.4A patent/CN105683202B/zh active Active
- 2013-08-02 AU AU2013395662A patent/AU2013395662B2/en active Active
- 2013-08-02 ES ES13750432.0T patent/ES2671927T3/es active Active
- 2013-08-02 DK DK13750432.0T patent/DK3027627T3/en active
-
2016
- 2016-02-02 IL IL243913A patent/IL243913A0/en unknown
-
2019
- 2019-06-05 AU AU2019203931A patent/AU2019203931B2/en active Active
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