JP2011516607A5 - - Google Patents
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- JP2011516607A5 JP2011516607A5 JP2011505026A JP2011505026A JP2011516607A5 JP 2011516607 A5 JP2011516607 A5 JP 2011516607A5 JP 2011505026 A JP2011505026 A JP 2011505026A JP 2011505026 A JP2011505026 A JP 2011505026A JP 2011516607 A5 JP2011516607 A5 JP 2011516607A5
- Authority
- JP
- Japan
- Prior art keywords
- aryl
- antagonist
- heteroaryl
- lfa
- pharmaceutical formulation
- 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- Withdrawn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 46
- 102100022339 Integrin alpha-L Human genes 0.000 claims description 43
- 108010064548 Lymphocyte Function-Associated Antigen-1 Proteins 0.000 claims description 43
- 125000001072 heteroaryl group Chemical group 0.000 claims description 40
- 125000003118 aryl group Chemical group 0.000 claims description 38
- -1 heteroaliphatic Chemical group 0.000 claims description 32
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 27
- 125000002723 alicyclic group Chemical group 0.000 claims description 26
- 125000001931 aliphatic 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
- 239000008194 pharmaceutical composition Substances 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical group 0.000 claims description 12
- 150000002148 esters Chemical class 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 229940124597 therapeutic agent Drugs 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
- 229940122739 Calcineurin inhibitor Drugs 0.000 claims description 6
- 102100024123 Calcineurin-binding protein cabin-1 Human genes 0.000 claims description 6
- 101710192106 Calcineurin-binding protein cabin-1 Proteins 0.000 claims description 6
- 125000002070 alkenylidene group Chemical group 0.000 claims description 6
- 230000003115 biocidal effect Effects 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
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 claims description 6
- 239000003246 corticosteroid Substances 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 239000002955 immunomodulating agent Substances 0.000 claims description 6
- 229940121354 immunomodulator Drugs 0.000 claims description 6
- 230000002584 immunomodulator Effects 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical group S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 claims description 6
- KBOPZPXVLCULAV-UHFFFAOYSA-M mesalaminate(1-) Chemical group NC1=CC=C(O)C(C([O-])=O)=C1 KBOPZPXVLCULAV-UHFFFAOYSA-M 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 239000004094 surface-active agent Substances 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 230000009885 systemic effect Effects 0.000 claims description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 4
- 239000003242 anti bacterial agent Substances 0.000 claims description 4
- 229920001400 block copolymer Polymers 0.000 claims description 4
- 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
- 239000003961 penetration enhancing agent Substances 0.000 claims description 4
- 229920005862 polyol Polymers 0.000 claims description 4
- 150000003077 polyols Chemical class 0.000 claims description 4
- VOVIALXJUBGFJZ-KWVAZRHASA-N Budesonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O VOVIALXJUBGFJZ-KWVAZRHASA-N 0.000 claims description 3
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical group CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 claims description 3
- 108010036949 Cyclosporine Proteins 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
- UETNIIAIRMUTSM-UHFFFAOYSA-N Jacareubin Natural products CC1(C)OC2=CC3Oc4c(O)c(O)ccc4C(=O)C3C(=C2C=C1)O UETNIIAIRMUTSM-UHFFFAOYSA-N 0.000 claims description 3
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 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
- 210000001744 T-lymphocyte Anatomy 0.000 claims description 3
- QJJXYPPXXYFBGM-LFZNUXCKSA-N Tacrolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1\C=C(/C)[C@@H]1[C@H](C)[C@@H](O)CC(=O)[C@H](CC=C)/C=C(C)/C[C@H](C)C[C@H](OC)[C@H]([C@H](C[C@H]2C)OC)O[C@@]2(O)C(=O)C(=O)N2CCCC[C@H]2C(=O)O1 QJJXYPPXXYFBGM-LFZNUXCKSA-N 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 229960002964 adalimumab Drugs 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
- 239000003963 antioxidant agent Substances 0.000 claims description 3
- 230000003078 antioxidant effect Effects 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- LMEKQMALGUDUQG-UHFFFAOYSA-N azathioprine Chemical compound CN1C=NC([N+]([O-])=O)=C1SC1=NC=NC2=C1NC=N2 LMEKQMALGUDUQG-UHFFFAOYSA-N 0.000 claims description 3
- 229960002170 azathioprine Drugs 0.000 claims description 3
- 229960004436 budesonide Drugs 0.000 claims description 3
- 239000002775 capsule 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
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229960001265 ciclosporin Drugs 0.000 claims description 3
- 229960003405 ciprofloxacin Drugs 0.000 claims description 3
- 230000002860 competitive effect Effects 0.000 claims description 3
- 229930182912 cyclosporin Natural products 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 3
- 229960000598 infliximab Drugs 0.000 claims description 3
- 229960001428 mercaptopurine Drugs 0.000 claims description 3
- KBOPZPXVLCULAV-UHFFFAOYSA-N mesalamine Chemical compound NC1=CC=C(O)C(C(O)=O)=C1 KBOPZPXVLCULAV-UHFFFAOYSA-N 0.000 claims description 3
- 229960004963 mesalazine Drugs 0.000 claims description 3
- 229960000485 methotrexate Drugs 0.000 claims description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 3
- VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 claims description 3
- 229960000282 metronidazole Drugs 0.000 claims description 3
- 239000011859 microparticle Substances 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- 239000002105 nanoparticle Substances 0.000 claims description 3
- KASDHRXLYQOAKZ-ZPSXYTITSA-N pimecrolimus Chemical compound C/C([C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@]2(O)O[C@@H]([C@H](C[C@H]2C)OC)[C@@H](OC)C[C@@H](C)C/C(C)=C/[C@H](C(C[C@H](O)[C@H]1C)=O)CC)=C\[C@@H]1CC[C@@H](Cl)[C@H](OC)C1 KASDHRXLYQOAKZ-ZPSXYTITSA-N 0.000 claims description 3
- 229960005330 pimecrolimus Drugs 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 229960004618 prednisone Drugs 0.000 claims description 3
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 claims description 3
- 125000006239 protecting group Chemical group 0.000 claims description 3
- ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Natural products COCC(O)C(=C/C(C)C(=O)CC(OC(=O)C1CCCCN1C(=O)C(=O)C2(O)OC(CC(OC)C(=CC=CC=CC(C)CC(C)C(=O)C)C)CCC2C)C(C)CC3CCC(O)C(C3)OC)C ZAHRKKWIAAJSAO-UHFFFAOYSA-N 0.000 claims description 3
- QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 claims description 3
- 229960002930 sirolimus Drugs 0.000 claims description 3
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 3
- NCEXYHBECQHGNR-QZQOTICOSA-N sulfasalazine Chemical compound C1=C(O)C(C(=O)O)=CC(\N=N\C=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-QZQOTICOSA-N 0.000 claims description 3
- 229960001940 sulfasalazine Drugs 0.000 claims description 3
- NCEXYHBECQHGNR-UHFFFAOYSA-N sulfasalazine Natural products C1=C(O)C(C(=O)O)=CC(N=NC=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-UHFFFAOYSA-N 0.000 claims description 3
- 239000000829 suppository Substances 0.000 claims description 3
- 239000000725 suspension Substances 0.000 claims description 3
- 239000003826 tablet Substances 0.000 claims description 3
- 229960001967 tacrolimus Drugs 0.000 claims description 3
- QJJXYPPXXYFBGM-SHYZHZOCSA-N tacrolimus Natural products CO[C@H]1C[C@H](CC[C@@H]1O)C=C(C)[C@H]2OC(=O)[C@H]3CCCCN3C(=O)C(=O)[C@@]4(O)O[C@@H]([C@H](C[C@H]4C)OC)[C@@H](C[C@H](C)CC(=C[C@@H](CC=C)C(=O)C[C@H](O)[C@H]2C)C)OC QJJXYPPXXYFBGM-SHYZHZOCSA-N 0.000 claims description 3
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 229920000168 Microcrystalline cellulose Polymers 0.000 claims description 2
- 239000005642 Oleic acid Substances 0.000 claims description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 2
- 229920001213 Polysorbate 20 Polymers 0.000 claims description 2
- 229920002472 Starch Polymers 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 239000012062 aqueous buffer Substances 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 159000000007 calcium salts Chemical class 0.000 claims description 2
- 239000004359 castor oil Substances 0.000 claims description 2
- 235000019438 castor oil Nutrition 0.000 claims description 2
- 229960001927 cetylpyridinium chloride Drugs 0.000 claims description 2
- YMKDRGPMQRFJGP-UHFFFAOYSA-M cetylpyridinium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 YMKDRGPMQRFJGP-UHFFFAOYSA-M 0.000 claims description 2
- 239000002738 chelating agent Substances 0.000 claims description 2
- 239000008139 complexing agent Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 claims description 2
- 235000019441 ethanol Nutrition 0.000 claims description 2
- 150000004665 fatty acids Chemical class 0.000 claims description 2
- 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 2
- 239000003979 granulating agent Substances 0.000 claims description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 229910003002 lithium salt Inorganic materials 0.000 claims description 2
- 159000000002 lithium salts Chemical class 0.000 claims description 2
- 239000000314 lubricant Substances 0.000 claims description 2
- 159000000003 magnesium salts Chemical class 0.000 claims description 2
- 235000019813 microcrystalline cellulose Nutrition 0.000 claims description 2
- 239000008108 microcrystalline cellulose Substances 0.000 claims description 2
- 229940016286 microcrystalline cellulose Drugs 0.000 claims description 2
- 239000003921 oil Substances 0.000 claims description 2
- 229960002969 oleic acid Drugs 0.000 claims description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 2
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 claims description 2
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 claims description 2
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 claims description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims description 2
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 claims description 2
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 claims description 2
- 229920000053 polysorbate 80 Polymers 0.000 claims description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 2
- 159000000000 sodium salts Chemical group 0.000 claims description 2
- 229940083466 soybean lecithin Drugs 0.000 claims description 2
- 239000008107 starch Substances 0.000 claims description 2
- 235000019698 starch Nutrition 0.000 claims description 2
- 230000001954 sterilising effect Effects 0.000 claims description 2
- 150000003462 sulfoxides Chemical group 0.000 claims description 2
- 150000003505 terpenes Chemical class 0.000 claims description 2
- 235000007586 terpenes Nutrition 0.000 claims description 2
- 230000000699 topical effect Effects 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 238000009736 wetting Methods 0.000 claims description 2
- 150000003751 zinc Chemical class 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 6
- 235000005985 organic acids Nutrition 0.000 claims 1
- 238000000034 method Methods 0.000 description 27
- 238000009472 formulation Methods 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- 210000001519 tissue Anatomy 0.000 description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 208000035475 disorder Diseases 0.000 description 3
- 0 CIN(C1*)C(*)(*)Cc2c1cc(*)c(C(NC(*)(*)*)=O)c2* Chemical compound CIN(C1*)C(*)(*)Cc2c1cc(*)c(C(NC(*)(*)*)=O)c2* 0.000 description 2
- 230000002757 inflammatory effect Effects 0.000 description 2
- 206010009900 Colitis ulcerative Diseases 0.000 description 1
- 208000011231 Crohn disease Diseases 0.000 description 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 1
- 201000006704 Ulcerative Colitis Diseases 0.000 description 1
- 239000004037 angiogenesis inhibitor Substances 0.000 description 1
- 230000002424 anti-apoptotic effect Effects 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 210000005095 gastrointestinal system Anatomy 0.000 description 1
- 210000004877 mucosa Anatomy 0.000 description 1
- 206010030983 oral lichen planus Diseases 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4516508P | 2008-04-15 | 2008-04-15 | |
| US61/045,165 | 2008-04-15 | ||
| PCT/US2009/002385 WO2009128932A1 (en) | 2008-04-15 | 2009-04-15 | Delivery of lfa-1 antagonists to the gastrointestinal system |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014080740A Division JP2014133751A (ja) | 2008-04-15 | 2014-04-10 | 胃腸系へのｌｆａ−１アンタゴニストの送達 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011516607A JP2011516607A (ja) | 2011-05-26 |
| JP2011516607A5 true JP2011516607A5 (cg-RX-API-DMAC7.html) | 2012-06-07 |
Family
ID=41164199
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011505026A Withdrawn JP2011516607A (ja) | 2008-04-15 | 2009-04-15 | 胃腸系へのｌｆａ−１アンタゴニストの送達 |
| JP2014080740A Withdrawn JP2014133751A (ja) | 2008-04-15 | 2014-04-10 | 胃腸系へのｌｆａ−１アンタゴニストの送達 |
| JP2016105884A Withdrawn JP2016153432A (ja) | 2008-04-15 | 2016-05-27 | 胃腸系へのｌｆａ−１アンタゴニストの送達 |
| JP2018081289A Pending JP2018127485A (ja) | 2008-04-15 | 2018-04-20 | 胃腸系へのｌｆａ−１アンタゴニストの送達 |
| JP2019190144A Pending JP2020023546A (ja) | 2008-04-15 | 2019-10-17 | 胃腸系へのｌｆａ−１アンタゴニストの送達 |
Family Applications After (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014080740A Withdrawn JP2014133751A (ja) | 2008-04-15 | 2014-04-10 | 胃腸系へのｌｆａ−１アンタゴニストの送達 |
| JP2016105884A Withdrawn JP2016153432A (ja) | 2008-04-15 | 2016-05-27 | 胃腸系へのｌｆａ−１アンタゴニストの送達 |
| JP2018081289A Pending JP2018127485A (ja) | 2008-04-15 | 2018-04-20 | 胃腸系へのｌｆａ−１アンタゴニストの送達 |
| JP2019190144A Pending JP2020023546A (ja) | 2008-04-15 | 2019-10-17 | 胃腸系へのｌｆａ−１アンタゴニストの送達 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20090258069A1 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2276508A4 (cg-RX-API-DMAC7.html) |
| JP (5) | JP2011516607A (cg-RX-API-DMAC7.html) |
| CN (1) | CN102065893A (cg-RX-API-DMAC7.html) |
| WO (1) | WO2009128932A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2383525T3 (es) | 2003-11-05 | 2012-06-21 | Sarcode Bioscience Inc. | Moduladores de la adhesión celular |
| JP5794721B2 (ja) * | 2005-05-17 | 2015-10-14 | サーコード バイオサイエンス インコーポレイテッド | 眼障害の治療のための組成物および方法 |
| ES2630406T3 (es) | 2007-10-19 | 2017-08-21 | Sarcode Bioscience Inc. | Composición y procedimientos para el tratamiento de la retinopatía diabética |
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-
2009
- 2009-04-15 US US12/386,347 patent/US20090258069A1/en not_active Abandoned
- 2009-04-15 EP EP09732599A patent/EP2276508A4/en not_active Ceased
- 2009-04-15 JP JP2011505026A patent/JP2011516607A/ja not_active Withdrawn
- 2009-04-15 CN CN200980121698XA patent/CN102065893A/zh active Pending
- 2009-04-15 WO PCT/US2009/002385 patent/WO2009128932A1/en not_active Ceased
-
2014
- 2014-04-10 JP JP2014080740A patent/JP2014133751A/ja not_active Withdrawn
-
2016
- 2016-05-27 JP JP2016105884A patent/JP2016153432A/ja not_active Withdrawn
-
2018
- 2018-04-20 JP JP2018081289A patent/JP2018127485A/ja active Pending
-
2019
- 2019-10-17 JP JP2019190144A patent/JP2020023546A/ja active Pending
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