CA2452372A1 - Composition for topical administration comprising an interleukin-2 inhibitor and an antimicrobial agent - Google Patents
Composition for topical administration comprising an interleukin-2 inhibitor and an antimicrobial agent Download PDFInfo
- Publication number
- CA2452372A1 CA2452372A1 CA002452372A CA2452372A CA2452372A1 CA 2452372 A1 CA2452372 A1 CA 2452372A1 CA 002452372 A CA002452372 A CA 002452372A CA 2452372 A CA2452372 A CA 2452372A CA 2452372 A1 CA2452372 A1 CA 2452372A1
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- Canada
- Prior art keywords
- hydrogen atom
- hydroxy
- alkyl
- antimicrobial agent
- group
- 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.)
- Abandoned
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 49
- 239000004599 antimicrobial Substances 0.000 title claims abstract description 48
- 108010045851 interleukin 2 inhibitor Proteins 0.000 title claims abstract description 37
- 238000011200 topical administration Methods 0.000 title claims abstract description 18
- 206010061218 Inflammation Diseases 0.000 claims abstract description 41
- 150000001875 compounds Chemical class 0.000 claims abstract description 39
- 230000004054 inflammatory process Effects 0.000 claims abstract description 38
- 238000011282 treatment Methods 0.000 claims abstract description 38
- 208000015181 infectious disease Diseases 0.000 claims abstract description 32
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- 239000004480 active ingredient Substances 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 52
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 43
- 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 33
- 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 32
- GSDSWSVVBLHKDQ-UHFFFAOYSA-N 9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid Chemical compound FC1=CC(C(C(C(O)=O)=C2)=O)=C3N2C(C)COC3=C1N1CCN(C)CC1 GSDSWSVVBLHKDQ-UHFFFAOYSA-N 0.000 claims description 30
- 229960001699 ofloxacin Drugs 0.000 claims description 30
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 239000003120 macrolide antibiotic agent Substances 0.000 claims description 16
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical group C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 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 10
- 229930182912 cyclosporin Natural products 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound 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 6
- 229930105110 Cyclosporin A Natural products 0.000 claims description 6
- 108010036949 Cyclosporine Proteins 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 229960001265 ciclosporin Drugs 0.000 claims description 6
- WUWFMDMBOJLQIV-UHFFFAOYSA-N 7-(3-aminopyrrolidin-1-yl)-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid Chemical compound C1C(N)CCN1C(C(=C1)F)=NC2=C1C(=O)C(C(O)=O)=CN2C1=CC=C(F)C=C1F WUWFMDMBOJLQIV-UHFFFAOYSA-N 0.000 claims description 5
- SPFYMRJSYKOXGV-UHFFFAOYSA-N Baytril Chemical compound C1CN(CC)CCN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 SPFYMRJSYKOXGV-UHFFFAOYSA-N 0.000 claims description 5
- GSDSWSVVBLHKDQ-JTQLQIEISA-N Levofloxacin Chemical compound C([C@@H](N1C2=C(C(C(C(O)=O)=C1)=O)C=C1F)C)OC2=C1N1CCN(C)CC1 GSDSWSVVBLHKDQ-JTQLQIEISA-N 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 229960003405 ciprofloxacin Drugs 0.000 claims description 5
- IDYZIJYBMGIQMJ-UHFFFAOYSA-N enoxacin Chemical compound N1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 IDYZIJYBMGIQMJ-UHFFFAOYSA-N 0.000 claims description 5
- 229960002549 enoxacin Drugs 0.000 claims description 5
- 229960000740 enrofloxacin Drugs 0.000 claims description 5
- XBJBPGROQZJDOJ-UHFFFAOYSA-N fleroxacin Chemical compound C1CN(C)CCN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(CCF)C2=C1F XBJBPGROQZJDOJ-UHFFFAOYSA-N 0.000 claims description 5
- 229960003306 fleroxacin Drugs 0.000 claims description 5
- 229960003376 levofloxacin Drugs 0.000 claims description 5
- ZEKZLJVOYLTDKK-UHFFFAOYSA-N lomefloxacin Chemical compound FC1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNC(C)C1 ZEKZLJVOYLTDKK-UHFFFAOYSA-N 0.000 claims description 5
- 229960002422 lomefloxacin Drugs 0.000 claims description 5
- MHWLWQUZZRMNGJ-UHFFFAOYSA-N nalidixic acid Chemical group C1=C(C)N=C2N(CC)C=C(C(O)=O)C(=O)C2=C1 MHWLWQUZZRMNGJ-UHFFFAOYSA-N 0.000 claims description 5
- 229960000210 nalidixic acid Drugs 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- OGJPXUAPXNRGGI-UHFFFAOYSA-N norfloxacin Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 OGJPXUAPXNRGGI-UHFFFAOYSA-N 0.000 claims description 5
- 229960001180 norfloxacin Drugs 0.000 claims description 5
- JOHZPMXAZQZXHR-UHFFFAOYSA-N pipemidic acid Chemical compound N1=C2N(CC)C=C(C(O)=O)C(=O)C2=CN=C1N1CCNCC1 JOHZPMXAZQZXHR-UHFFFAOYSA-N 0.000 claims description 5
- 229960001732 pipemidic acid Drugs 0.000 claims description 5
- RCIMBBZXSXFZBV-UHFFFAOYSA-N piromidic acid Chemical compound N1=C2N(CC)C=C(C(O)=O)C(=O)C2=CN=C1N1CCCC1 RCIMBBZXSXFZBV-UHFFFAOYSA-N 0.000 claims description 5
- 229960004444 piromidic acid Drugs 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 229960004954 sparfloxacin Drugs 0.000 claims description 5
- DZZWHBIBMUVIIW-DTORHVGOSA-N sparfloxacin Chemical compound C1[C@@H](C)N[C@@H](C)CN1C1=C(F)C(N)=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F DZZWHBIBMUVIIW-DTORHVGOSA-N 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- 229950008187 tosufloxacin Drugs 0.000 claims description 5
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 4
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 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 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- -1 3,4-dioxocyclohexyl Chemical group 0.000 description 74
- 229960001967 tacrolimus Drugs 0.000 description 23
- 108010002350 Interleukin-2 Proteins 0.000 description 15
- 102000000588 Interleukin-2 Human genes 0.000 description 15
- 230000000694 effects Effects 0.000 description 13
- 239000000126 substance Substances 0.000 description 12
- 229960002930 sirolimus Drugs 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Chemical class 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 description 10
- 238000009472 formulation Methods 0.000 description 9
- 239000003112 inhibitor Substances 0.000 description 8
- 230000002401 inhibitory effect Effects 0.000 description 8
- 230000001580 bacterial effect Effects 0.000 description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
- 239000002674 ointment Substances 0.000 description 7
- QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical class 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 description 7
- 239000003795 chemical substances by application Substances 0.000 description 6
- 210000004087 cornea Anatomy 0.000 description 6
- 230000003247 decreasing effect Effects 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- 238000011081 inoculation Methods 0.000 description 6
- 230000000699 topical effect Effects 0.000 description 6
- 108010036941 Cyclosporins Proteins 0.000 description 5
- 230000002411 adverse Effects 0.000 description 5
- 239000003889 eye drop Substances 0.000 description 5
- 229940012356 eye drops Drugs 0.000 description 5
- 206010023332 keratitis Diseases 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 208000035473 Communicable disease Diseases 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 238000010162 Tukey test Methods 0.000 description 4
- 125000005115 alkyl carbamoyl group Chemical group 0.000 description 4
- 125000005103 alkyl silyl group Chemical group 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 230000000495 immunoinflammatory effect Effects 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 239000012453 solvate Substances 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- ZDQSOHOQTUFQEM-PKUCKEGBSA-N ascomycin Chemical class 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](O)[C@H](OC)C1 ZDQSOHOQTUFQEM-PKUCKEGBSA-N 0.000 description 3
- 201000008937 atopic dermatitis Diseases 0.000 description 3
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- 230000004073 interleukin-2 production Effects 0.000 description 3
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- QGMRQYFBGABWDR-UHFFFAOYSA-M Pentobarbital sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)[N-]C1=O QGMRQYFBGABWDR-UHFFFAOYSA-M 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 2
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- Health & Medical Sciences (AREA)
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- Veterinary Medicine (AREA)
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- Public Health (AREA)
- Chemical & Material Sciences (AREA)
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| US30314801P | 2001-07-06 | 2001-07-06 | |
| US60/303,148 | 2001-07-06 | ||
| PCT/JP2002/006670 WO2003004098A1 (en) | 2001-07-06 | 2002-07-02 | Composition for topical administration comprising an interleukin-2 inhibitor and an antimicrobial agent |
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| CA2452372A1 true CA2452372A1 (en) | 2003-01-16 |
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| US20050239813A1 (en) * | 2002-08-09 | 2005-10-27 | Sucampo Pharmaceuticals Inc. | Pharmaceutical compositions comprising fk506 derivatives and their use for the treatment of allergic diseases |
| US7354574B2 (en) | 2002-11-07 | 2008-04-08 | Advanced Ocular Systems Limited | Treatment of ocular disease |
| GB0307862D0 (en) * | 2003-04-04 | 2003-05-14 | Novartis Ag | Pharmaceutical composition |
| US7083802B2 (en) | 2003-07-31 | 2006-08-01 | Advanced Ocular Systems Limited | Treatment of ocular disease |
| US20050059583A1 (en) | 2003-09-15 | 2005-03-17 | Allergan, Inc. | Methods of providing therapeutic effects using cyclosporin components |
| WO2005027906A1 (en) * | 2003-09-18 | 2005-03-31 | Macusight, Inc. | Transscleral delivery |
| US7083803B2 (en) | 2003-09-19 | 2006-08-01 | Advanced Ocular Systems Limited | Ocular solutions |
| US7087237B2 (en) | 2003-09-19 | 2006-08-08 | Advanced Ocular Systems Limited | Ocular solutions |
| KR101140039B1 (ko) * | 2004-01-26 | 2012-05-02 | (주)아모레퍼시픽 | 진세노사이드 ｆ1 또는 화합물 ｋ를 함유하는 피부외용제조성물 |
| US7135455B2 (en) * | 2004-11-15 | 2006-11-14 | Allergan, Inc | Methods for the therapeutic use of cyclosporine components |
| US7151085B2 (en) * | 2004-11-15 | 2006-12-19 | Allergan, Inc. | Therapeutic methods using cyclosporine components |
| GB2438544A (en) * | 2005-02-09 | 2007-11-28 | Cooper Internat Corp | Liquid formulations for treatment of diseases or conditions |
| US8663639B2 (en) * | 2005-02-09 | 2014-03-04 | Santen Pharmaceutical Co., Ltd. | Formulations for treating ocular diseases and conditions |
| CA2635797C (en) | 2006-02-09 | 2015-03-31 | Macusight, Inc. | Stable formulations, and methods of their preparation and use |
| CN101443004B (zh) | 2006-03-23 | 2013-03-06 | 参天制药株式会社 | 用于与血管通透性有关的疾病或病症的制剂 |
| SI2944306T1 (sl) | 2006-06-16 | 2021-04-30 | Regeneron Pharmaceuticals, Inc. | Formulacije antagonista VEGF, primerne za intravitrealno dajanje |
| US20080265343A1 (en) * | 2007-04-26 | 2008-10-30 | International Business Machines Corporation | Field effect transistor with inverted t shaped gate electrode and methods for fabrication thereof |
| MX2010003364A (es) | 2007-10-08 | 2010-07-06 | Lux Biosciences Inc | Composiciones oftalmicas que comprenden inhibidores de calcineurina o inhibidores de mtor. |
| US10206813B2 (en) | 2009-05-18 | 2019-02-19 | Dose Medical Corporation | Implants with controlled drug delivery features and methods of using same |
| US12478503B2 (en) | 2009-05-18 | 2025-11-25 | Glaukos Corporation | Implants with controlled drug delivery features and methods of using same |
| US9017725B2 (en) * | 2009-06-09 | 2015-04-28 | Aurinia Pharmaceuticals Inc. | Topical drug delivery systems for ophthalmic use |
| SI2665486T1 (sl) | 2011-01-18 | 2020-07-31 | Bioniz, Llc | Sestavki za moduliranje aktivnosti gama-C-citokina |
| WO2015089217A2 (en) | 2013-12-10 | 2015-06-18 | Bionz, Llc | Methods of developing selective peptide antagonists |
| WO2014159679A1 (en) | 2013-03-12 | 2014-10-02 | The United States Of America, As Represented By The Secretary, Department Of Health & Human Services | Methods for using lubiprostone to absorb fluid from the subretinal space |
| WO2014167327A1 (en) * | 2013-04-09 | 2014-10-16 | Cresset Biomolecular Discovery Ltd | The treatment of inflammatory disorders |
| WO2017062685A1 (en) | 2015-10-09 | 2017-04-13 | Bioniz, Llc | Modulating gamma - c -cytokine activity |
| CN114712497B (zh) | 2015-12-03 | 2024-03-22 | 雷杰纳荣制药公司 | 抗vegf剂在制备用于治疗新生血管性年龄相关性黄斑变性患者的药物中的用途 |
| US20190224275A1 (en) | 2017-05-12 | 2019-07-25 | Aurinia Pharmaceuticals Inc. | Protocol for treatment of lupus nephritis |
| US11519020B2 (en) | 2018-05-25 | 2022-12-06 | Regeneron Pharmaceuticals, Inc. | Methods of associating genetic variants with a clinical outcome in patients suffering from age-related macular degeneration treated with anti-VEGF |
| WO2020227019A1 (en) | 2019-05-03 | 2020-11-12 | Bioniz, Llc | Modulating the effects of gamma-c-cytokine signaling for the treatment of alopecia and alopecia associated disorders |
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| US4117118A (en) | 1976-04-09 | 1978-09-26 | Sandoz Ltd. | Organic compounds |
| FI65914C (fi) | 1978-03-07 | 1984-08-10 | Sandoz Ag | Foerfarande foer framstaellning av farmaceutiska kompositionerinnehaollande cyklosporin a |
| US4215199A (en) | 1978-06-05 | 1980-07-29 | Sandoz Ltd. | Antibiotic production |
| SE448386B (sv) | 1978-10-18 | 1987-02-16 | Sandoz Ag | Nya cyklosporinderivat, forfarande for framstellning av dem samt farmaceutisk komposition innehallande dem |
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| US5143918A (en) * | 1990-10-11 | 1992-09-01 | Merck & Co., Inc. | Halomacrolides and derivatives having immunosuppressive activity |
| US5348966A (en) * | 1990-10-24 | 1994-09-20 | Fujisawa Pharmaceutical Co., Ltd. | Method for treating pyoderma and Sezary's syndrome using FK 506 and related compounds |
| ATE198708T1 (de) | 1991-04-26 | 2001-02-15 | Fujisawa Pharmaceutical Co | Verwendung von makrolid-verbindungen gegen augenerkrankungen |
| IT1253711B (it) * | 1991-12-17 | 1995-08-23 | Alfa Wassermann Spa | Formulazioni farmaceutiche vaginali contenenti rifaximin e loro uso nel trattamento delle infezioni vaginali |
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| US5340572A (en) * | 1993-02-08 | 1994-08-23 | Insite Vision Incorporated | Alkaline ophthalmic suspensions |
| JPH06345646A (ja) * | 1993-06-08 | 1994-12-20 | Fujisawa Pharmaceut Co Ltd | ローション剤 |
| US5489435A (en) * | 1993-07-06 | 1996-02-06 | Ratcliff; Perry A. | Composition for treatment of abnormal conditions of the epithelium of bodily orifices |
| CA2194049A1 (en) * | 1994-06-28 | 1996-01-11 | Georgi Stankov | Novel clinical uses of polyene macrolides |
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| US5929086A (en) * | 1996-05-10 | 1999-07-27 | Pharmacia & Upjohn Company | Topical administration of antimicrobial agents for the treatment of systemic bacterial diseases |
| US6248776B1 (en) | 1997-08-26 | 2001-06-19 | Bioavailability Systems, L.L.C. | Anti-first-pass effect compounds |
| US5912255A (en) * | 1998-02-27 | 1999-06-15 | Bussell; Letantia | Topical fluoroquinolone antibiotics combined with benzoyl peroxide |
| US6312715B1 (en) | 1998-05-01 | 2001-11-06 | 3M Innovative Properties Company | Adhesive microsphere drug delivery composition |
| AUPP437698A0 (en) * | 1998-06-30 | 1998-07-23 | Baumgart, Karl | Methods for treatment of coronary, carotid and other vascular disease |
| US6864232B1 (en) * | 1998-12-24 | 2005-03-08 | Sucampo Ag | Agent for treating visual cell function disorder |
| US6294192B1 (en) | 1999-02-26 | 2001-09-25 | Lipocine, Inc. | Triglyceride-free compositions and methods for improved delivery of hydrophobic therapeutic agents |
| US6174859B1 (en) * | 1999-04-06 | 2001-01-16 | J & D Sciences, Inc. | Method of treatment |
| US7063857B1 (en) * | 1999-04-30 | 2006-06-20 | Sucampo Ag | Use of macrolide compounds for the treatment of dry eye |
| CA2372448A1 (en) | 1999-04-30 | 2000-11-09 | Sucampo Ag | Use of macrolide compounds for the treatment of dry eye |
| PL201130B1 (pl) * | 1999-09-24 | 2009-03-31 | Alcon Inc | Kompozycje zawiesinowe zawierające ciprofloksacynę i deksametazon do podawania miejscowego do oczu, uszu lub nosa |
| AR033151A1 (es) | 2001-04-12 | 2003-12-03 | Sucampo Pharmaceuticals Inc | Agente para el tratamiento oftalmico topico de las enfermedades inflamatorias oculares |
| WO2003004098A1 (en) | 2001-07-06 | 2003-01-16 | Sucampo Ag | Composition for topical administration comprising an interleukin-2 inhibitor and an antimicrobial agent |
| US20030114416A1 (en) * | 2001-08-14 | 2003-06-19 | Pharmacia Corporation | Method and compositions for the treatment and prevention of pain and inflammation with a cyclooxygenase-2 selective inhibitor and chondroitin sulfate |
| WO2003043650A1 (en) * | 2001-11-21 | 2003-05-30 | Sucampo Ag | Use of fk506 and analogues for treating allergic diseases |
| CA2492387A1 (en) * | 2002-07-17 | 2004-01-22 | Warner-Lambert Company Llc | Combination of an allosteric carboxylic of matrix metalloproteinase-13 with a selective inhibitor of cyclooxygenase-2 that is not celecoxib or valdecoxib |
| US20050239813A1 (en) * | 2002-08-09 | 2005-10-27 | Sucampo Pharmaceuticals Inc. | Pharmaceutical compositions comprising fk506 derivatives and their use for the treatment of allergic diseases |
| US20040198763A1 (en) * | 2003-01-16 | 2004-10-07 | Sucampo Ag | Method of treating dry eye with a macrolide compound |
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2002
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- 2002-07-02 CA CA002452372A patent/CA2452372A1/en not_active Abandoned
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Also Published As
| Publication number | Publication date |
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| US20030044452A1 (en) | 2003-03-06 |
| CN1259049C (zh) | 2006-06-14 |
| KR20040019034A (ko) | 2004-03-04 |
| CN1524003A (zh) | 2004-08-25 |
| EP1406700A1 (en) | 2004-04-14 |
| US7033604B2 (en) | 2006-04-25 |
| WO2003004098A1 (en) | 2003-01-16 |
| JP2005502621A (ja) | 2005-01-27 |
| US20060034892A1 (en) | 2006-02-16 |
| NZ530845A (en) | 2006-03-31 |
| AR036127A1 (es) | 2004-08-11 |
| WO2003004098A8 (en) | 2003-02-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |