JP2011518155A5 - - Google Patents
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- JP2011518155A5 JP2011518155A5 JP2011505027A JP2011505027A JP2011518155A5 JP 2011518155 A5 JP2011518155 A5 JP 2011518155A5 JP 2011505027 A JP2011505027 A JP 2011505027A JP 2011505027 A JP2011505027 A JP 2011505027A JP 2011518155 A5 JP2011518155 A5 JP 2011518155A5
- Authority
- JP
- Japan
- Prior art keywords
- pharmaceutical formulation
- antagonist
- item
- lfa
- heteroaryl
- 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.)
- Withdrawn
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- 239000005557 antagonist Substances 0.000 claims description 47
- 102100022339 Integrin alpha-L Human genes 0.000 claims description 44
- 108010064548 Lymphocyte Function-Associated Antigen-1 Proteins 0.000 claims description 44
- 125000001072 heteroaryl group Chemical group 0.000 claims description 39
- 125000003118 aryl group Chemical group 0.000 claims description 37
- 239000000203 mixture Substances 0.000 claims description 32
- 238000009472 formulation Methods 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 27
- -1 heteroaliphatic Chemical group 0.000 claims description 26
- 125000002723 alicyclic group Chemical group 0.000 claims description 25
- 239000008194 pharmaceutical composition Substances 0.000 claims description 25
- 125000001931 aliphatic group Chemical group 0.000 claims description 24
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 24
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 24
- 150000002431 hydrogen Chemical class 0.000 claims description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical group 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 10
- 239000003380 propellant Substances 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000007789 gas Substances 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 239000000443 aerosol Substances 0.000 claims description 8
- 239000004094 surface-active agent Substances 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 7
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical group CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 6
- 125000002070 alkenylidene group Chemical group 0.000 claims description 6
- 239000003963 antioxidant agent Substances 0.000 claims description 6
- 229920001400 block copolymer Polymers 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- BWOVZCWSJFYBRM-UHFFFAOYSA-N carbononitridic isocyanate Chemical group O=C=NC#N BWOVZCWSJFYBRM-UHFFFAOYSA-N 0.000 claims description 6
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 229940124597 therapeutic agent Drugs 0.000 claims description 6
- UJPMYEOUBPIPHQ-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical compound CC(F)(F)F UJPMYEOUBPIPHQ-UHFFFAOYSA-N 0.000 claims description 5
- 230000003078 antioxidant effect Effects 0.000 claims description 5
- 239000006199 nebulizer Substances 0.000 claims description 5
- 229920005862 polyol Polymers 0.000 claims description 5
- 150000003077 polyols Chemical class 0.000 claims description 5
- 230000009885 systemic effect Effects 0.000 claims description 5
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 4
- 239000000194 fatty acid Substances 0.000 claims description 4
- 229930195729 fatty acid Natural products 0.000 claims description 4
- 229940071648 metered dose inhaler Drugs 0.000 claims description 4
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 claims description 4
- 239000003961 penetration enhancing agent Substances 0.000 claims description 4
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 claims description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 3
- YFMFNYKEUDLDTL-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical compound FC(F)(F)C(F)C(F)(F)F YFMFNYKEUDLDTL-UHFFFAOYSA-N 0.000 claims description 3
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 claims description 3
- WXGNWUVNYMJENI-UHFFFAOYSA-N 1,1,2,2-tetrafluoroethane Chemical compound FC(F)C(F)F WXGNWUVNYMJENI-UHFFFAOYSA-N 0.000 claims description 3
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 claims description 3
- WGZYQOSEVSXDNI-UHFFFAOYSA-N 1,1,2-trifluoroethane Chemical compound FCC(F)F WGZYQOSEVSXDNI-UHFFFAOYSA-N 0.000 claims description 3
- FRCHKSNAZZFGCA-UHFFFAOYSA-N 1,1-dichloro-1-fluoroethane Chemical compound CC(F)(Cl)Cl FRCHKSNAZZFGCA-UHFFFAOYSA-N 0.000 claims description 3
- NPNPZTNLOVBDOC-UHFFFAOYSA-N 1,1-difluoroethane Chemical compound CC(F)F NPNPZTNLOVBDOC-UHFFFAOYSA-N 0.000 claims description 3
- DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 claims description 3
- YMRMDGSNYHCUCL-UHFFFAOYSA-N 1,2-dichloro-1,1,2-trifluoroethane Chemical compound FC(Cl)C(F)(F)Cl YMRMDGSNYHCUCL-UHFFFAOYSA-N 0.000 claims description 3
- SKDFWEPBABSFMG-UHFFFAOYSA-N 1,2-dichloro-1,1-difluoroethane Chemical compound FC(F)(Cl)CCl SKDFWEPBABSFMG-UHFFFAOYSA-N 0.000 claims description 3
- RFCAUADVODFSLZ-UHFFFAOYSA-N 1-Chloro-1,1,2,2,2-pentafluoroethane Chemical compound FC(F)(F)C(F)(F)Cl RFCAUADVODFSLZ-UHFFFAOYSA-N 0.000 claims description 3
- JQZFYIGAYWLRCC-UHFFFAOYSA-N 1-chloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)C(F)(F)Cl JQZFYIGAYWLRCC-UHFFFAOYSA-N 0.000 claims description 3
- BHNZEZWIUMJCGF-UHFFFAOYSA-N 1-chloro-1,1-difluoroethane Chemical compound CC(F)(F)Cl BHNZEZWIUMJCGF-UHFFFAOYSA-N 0.000 claims description 3
- BOUGCJDAQLKBQH-UHFFFAOYSA-N 1-chloro-1,2,2,2-tetrafluoroethane Chemical compound FC(Cl)C(F)(F)F BOUGCJDAQLKBQH-UHFFFAOYSA-N 0.000 claims description 3
- FWAQVJAOVDYHAF-UHFFFAOYSA-N 1-chloro-1,2,2-trifluoroethane Chemical compound FC(F)C(F)Cl FWAQVJAOVDYHAF-UHFFFAOYSA-N 0.000 claims description 3
- JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 claims description 3
- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 claims description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 3
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims description 3
- XWCDCDSDNJVCLO-UHFFFAOYSA-N Chlorofluoromethane Chemical compound FCCl XWCDCDSDNJVCLO-UHFFFAOYSA-N 0.000 claims description 3
- 239000004338 Dichlorodifluoromethane Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 102000015271 Intercellular Adhesion Molecule-1 Human genes 0.000 claims description 3
- 108010064593 Intercellular Adhesion Molecule-1 Proteins 0.000 claims description 3
- 229920000168 Microcrystalline cellulose Polymers 0.000 claims description 3
- JTNFLOSMZURXJM-UHFFFAOYSA-N NS(S)(=O)=O Chemical compound NS(S)(=O)=O JTNFLOSMZURXJM-UHFFFAOYSA-N 0.000 claims description 3
- 239000005642 Oleic acid Substances 0.000 claims description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 3
- 229920001213 Polysorbate 20 Polymers 0.000 claims description 3
- 229920002472 Starch Polymers 0.000 claims description 3
- 210000001744 T-lymphocyte Anatomy 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000003275 alpha amino acid group Chemical group 0.000 claims description 3
- 239000004037 angiogenesis inhibitor Substances 0.000 claims description 3
- 239000003242 anti bacterial agent Substances 0.000 claims description 3
- 230000002424 anti-apoptotic effect Effects 0.000 claims description 3
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 3
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 3
- 239000003443 antiviral agent Substances 0.000 claims description 3
- 239000012062 aqueous buffer Substances 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- VCJIGSOOIYBSFA-UHFFFAOYSA-N azido formate Chemical compound [N-]=[N+]=NOC=O VCJIGSOOIYBSFA-UHFFFAOYSA-N 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 3
- 239000001273 butane Substances 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 3
- 239000004359 castor oil Substances 0.000 claims description 3
- 235000019438 castor oil Nutrition 0.000 claims description 3
- 229960001927 cetylpyridinium chloride Drugs 0.000 claims description 3
- YMKDRGPMQRFJGP-UHFFFAOYSA-M cetylpyridinium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 YMKDRGPMQRFJGP-UHFFFAOYSA-M 0.000 claims description 3
- 239000002738 chelating agent Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 235000019406 chloropentafluoroethane Nutrition 0.000 claims description 3
- AFYPFACVUDMOHA-UHFFFAOYSA-N chlorotrifluoromethane Chemical compound FC(F)(F)Cl AFYPFACVUDMOHA-UHFFFAOYSA-N 0.000 claims description 3
- 230000002860 competitive effect Effects 0.000 claims description 3
- 239000008139 complexing agent Substances 0.000 claims description 3
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 3
- 235000019404 dichlorodifluoromethane Nutrition 0.000 claims description 3
- UMNKXPULIDJLSU-UHFFFAOYSA-N dichlorofluoromethane Chemical compound FC(Cl)Cl UMNKXPULIDJLSU-UHFFFAOYSA-N 0.000 claims description 3
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- 239000003085 diluting agent Substances 0.000 claims description 3
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- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical group FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims description 3
- 239000006260 foam Substances 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 3
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- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 3
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- QYSGYZVSCZSLHT-UHFFFAOYSA-N octafluoropropane Chemical compound FC(F)(F)C(F)(F)C(F)(F)F QYSGYZVSCZSLHT-UHFFFAOYSA-N 0.000 claims description 3
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| US8926990B2 (en) | 2009-10-13 | 2015-01-06 | Rutgers, The State University Of New Jersey | Treatment and diagnosis of inflammatory disorders and HIV |
| ES2763703T3 (es) * | 2008-04-15 | 2020-05-29 | Sarcode Bioscience Inc | Antagonistas de LFA-1 tópicos utilizados en el tratamiento localizado de trastornos inmunes |
| JP2011516607A (ja) * | 2008-04-15 | 2011-05-26 | サーコード コーポレイション | 胃腸系へのｌｆａ−１アンタゴニストの送達 |
| WO2011115700A2 (en) * | 2010-03-18 | 2011-09-22 | Precision Dermatology, Inc. | Emollient foams for treatment of seborrheic dermatitis |
| EP2563336A4 (en) * | 2010-03-26 | 2014-07-23 | Prec Dermatology Inc | AEROSOL FOAMS WITH CLINDAMYCIN PHOSPHATE |
| CA2802041A1 (en) * | 2010-06-11 | 2011-12-15 | Precision Dermatology, Inc. | High oil-content emollient aerosol foam compositions |
| RU2612506C2 (ru) * | 2011-03-03 | 2017-03-09 | Импел Ньюрофарма Инк. | Устройство для назальной доставки лекарственных средств |
| ES2846724T3 (es) * | 2012-12-19 | 2021-07-29 | Novartis Ag | Formulaciones de inhibidores de LFA-1 |
| US9757395B2 (en) | 2012-12-20 | 2017-09-12 | Otitopic Inc. | Dry powder inhaler and methods of use |
| US9757529B2 (en) | 2012-12-20 | 2017-09-12 | Otitopic Inc. | Dry powder inhaler and methods of use |
| CN105473133A (zh) | 2013-04-30 | 2016-04-06 | 欧缇托匹克公司 | 干粉制剂及使用方法 |
| EP3104842B1 (en) | 2014-02-14 | 2021-10-06 | Mission Pharmacal Company | Sprayable composition containing zinc oxide and a fluoro-olefin propellant |
| CN105980262B (zh) | 2014-02-14 | 2020-08-04 | 明申医药公司 | 喷雾递送装置 |
| MX375920B (es) * | 2014-02-14 | 2025-03-07 | Mission Pharma Co | Emulsion estabilizada que puede rociarse que contiene particulas de agentes activos. |
| CN103920138A (zh) * | 2014-04-17 | 2014-07-16 | 兆科药业（广州）有限公司 | 一种药物组合物及其制剂与应用 |
| JP6649376B2 (ja) * | 2014-06-20 | 2020-02-19 | ラトガース，ザ ステート ユニバーシティ オブ ニュー ジャージー | 肺の炎症を治療する方法 |
| CN106995439B (zh) * | 2016-01-26 | 2019-09-20 | 镇江圣安医药有限公司 | 氘取代3-(甲磺酰基)-l-苯丙氨酸衍生物及其药物组合物、药物制剂和用途 |
| EP3506907B1 (en) * | 2016-09-01 | 2023-06-07 | Galera Labs, LLC | Combination cancer therapy with a pentaaza macrocyclic ring complex and an ascorbate compound |
| EP3684338A4 (en) | 2017-09-22 | 2021-06-23 | Otitopic Inc. | DRY POWDER COMPOSITIONS WITH MAGNESIUM STEARATE |
| US10786456B2 (en) | 2017-09-22 | 2020-09-29 | Otitopic Inc. | Inhaled aspirin and magnesium to treat inflammation |
| EP3955926A4 (en) * | 2019-04-18 | 2022-11-30 | Azura Ophthalmics Ltd. | COMPOUNDS AND COMPOSITIONS FOR THE TREATMENT OF EYE DISEASES |
| CN111588730A (zh) * | 2020-06-10 | 2020-08-28 | 中山大学中山眼科中心 | FL2-siRNA在制备治疗角膜碱烧伤药物中的应用及角膜碱烧伤药物 |
| IL302174A (en) * | 2020-10-21 | 2023-06-01 | Azura Ophthalmics Ltd | Compounds and methods for the treatment of eye disorders |
| CN119895319A (zh) * | 2022-09-15 | 2025-04-25 | 日油株式会社 | 用于接触镜片的溶液 |
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-
2009
- 2009-04-15 EP EP09733386A patent/EP2265124A4/en not_active Ceased
- 2009-04-15 JP JP2011505027A patent/JP2011518155A/ja not_active Withdrawn
- 2009-04-15 US US12/386,363 patent/US20090257957A1/en not_active Abandoned
- 2009-04-15 CN CN2009801216848A patent/CN102065694A/zh active Pending
- 2009-04-15 WO PCT/US2009/002388 patent/WO2009128933A1/en not_active Ceased
-
2013
- 2013-08-07 US US13/960,915 patent/US20140079784A1/en not_active Abandoned
-
2014
- 2014-04-10 JP JP2014080837A patent/JP2014132033A/ja not_active Withdrawn
-
2016
- 2016-04-01 JP JP2016074257A patent/JP2016128515A/ja active Pending
-
2017
- 2017-05-30 JP JP2017106334A patent/JP2017141310A/ja active Pending
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