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- Withdrawn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 |
| EP3632444A3 (en) * | 2008-04-15 | 2020-08-26 | SARcode Bioscience Inc. | Topical lfa-1 antagonists for use in localized treatment of immune related disorders |
| EP2276508A4 (en) * | 2008-04-15 | 2011-12-28 | Sarcode Bioscience Inc | ADMINISTRATION OF LFA-1 ANTAGONISTS TO THE GASTROINTESTINAL SYSTEM |
| WO2011115700A2 (en) * | 2010-03-18 | 2011-09-22 | Precision Dermatology, Inc. | Emollient foams for treatment of seborrheic dermatitis |
| US8592380B2 (en) * | 2010-03-26 | 2013-11-26 | Precision Dermatology, Inc. | Aerosol foams comprising clindamycin phosphate |
| ES2918299T3 (es) * | 2010-06-11 | 2022-07-15 | Prec Dermatology Inc | Composiciones de espuma a base de aerosol emoliente con alto contenido de aceite |
| EP2680913B1 (en) | 2011-03-03 | 2020-05-06 | Impel NeuroPharma Inc. | Nasal drug delivery device |
| EP3827823A1 (en) * | 2012-12-19 | 2021-06-02 | Novartis AG | Lfa-1 inhibitor formulations |
| US9757529B2 (en) | 2012-12-20 | 2017-09-12 | Otitopic Inc. | Dry powder inhaler and methods of use |
| US9757395B2 (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 |
| US9381156B2 (en) | 2014-02-14 | 2016-07-05 | Mission Pharmacal Company | Stabilized, sprayable emulsion containing active agent particles |
| CA2936409C (en) | 2014-02-14 | 2023-03-14 | Mission Pharmacal Company | Spray delivery device |
| EP3104842B1 (en) | 2014-02-14 | 2021-10-06 | Mission Pharmacal Company | Sprayable composition containing zinc oxide and a fluoro-olefin propellant |
| 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 |
| JP7166634B2 (ja) * | 2016-09-01 | 2022-11-08 | ガレラ・ラブス・リミテッド・ライアビリティ・カンパニー | ペンタアザ大環状環複合体およびアスコルビン酸化合物による組み合わせ癌療法 |
| US10786456B2 (en) | 2017-09-22 | 2020-09-29 | Otitopic Inc. | Inhaled aspirin and magnesium to treat inflammation |
| CA3076353A1 (en) | 2017-09-22 | 2019-03-28 | Otitopic Inc. | Dry powder compositions with magnesium stearate |
| WO2020212755A1 (en) * | 2019-04-18 | 2020-10-22 | Azura Ophthalmics Ltd. | Compounds and methods for the treatment of ocular disorders |
| 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 |
| CN116635032A (zh) * | 2020-10-21 | 2023-08-22 | 阿祖拉眼科有限公司 | 用于治疗眼部病症的化合物和方法 |
| EP4589369A4 (en) * | 2022-09-15 | 2026-08-12 | Nof Corp | CONTACT LENS SOLUTION |
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| US4992445A (en) * | 1987-06-12 | 1991-02-12 | American Cyanamid Co. | Transdermal delivery of pharmaceuticals |
| DE3802996A1 (de) * | 1988-02-02 | 1989-08-10 | Cassella Ag | Verwendung von 2-oxo-pyrrolidin-1-acetamid zur bestimmung der glomerulaeren filtrationsrate beim menschen |
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| EP3632444A3 (en) * | 2008-04-15 | 2020-08-26 | SARcode Bioscience Inc. | Topical lfa-1 antagonists for use in localized treatment of immune related disorders |
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-
2009
- 2009-04-15 CN CN2009801216848A patent/CN102065694A/zh active Pending
- 2009-04-15 US US12/386,363 patent/US20090257957A1/en not_active Abandoned
- 2009-04-15 EP EP09733386A patent/EP2265124A4/en not_active Ceased
- 2009-04-15 WO PCT/US2009/002388 patent/WO2009128933A1/en not_active Ceased
- 2009-04-15 JP JP2011505027A patent/JP2011518155A/ja not_active Withdrawn
-
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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