JPH11515024A - ヒドロペルオキシエイコサテトラエン酸誘導体を含む組成物およびドライアイ疾患の治療における使用方法 - Google Patents
ヒドロペルオキシエイコサテトラエン酸誘導体を含む組成物およびドライアイ疾患の治療における使用方法Info
- Publication number
- JPH11515024A JPH11515024A JP9517306A JP51730697A JPH11515024A JP H11515024 A JPH11515024 A JP H11515024A JP 9517306 A JP9517306 A JP 9517306A JP 51730697 A JP51730697 A JP 51730697A JP H11515024 A JPH11515024 A JP H11515024A
- Authority
- JP
- Japan
- Prior art keywords
- hete
- composition
- alkyl
- dry eye
- cycloalkyl
- 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 40
- 208000003556 Dry Eye Syndromes Diseases 0.000 title claims abstract description 29
- 238000000034 method Methods 0.000 title claims abstract description 15
- CWJSCIWGSUCULS-UHFFFAOYSA-N 2-hydroperoxyicosa-2,4,6,8-tetraenoic acid Chemical class CCCCCCCCCCCC=CC=CC=CC=C(OO)C(O)=O CWJSCIWGSUCULS-UHFFFAOYSA-N 0.000 title 1
- 206010013774 Dry eye Diseases 0.000 claims abstract description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 238000011282 treatment Methods 0.000 claims description 12
- 238000009472 formulation Methods 0.000 claims description 9
- JSFATNQSLKRBCI-VAEKSGALSA-N 15(S)-HETE Chemical compound CCCCC[C@H](O)\C=C\C=C/C\C=C/C\C=C/CCCC(O)=O JSFATNQSLKRBCI-VAEKSGALSA-N 0.000 claims description 8
- 230000000699 topical effect Effects 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 238000006467 substitution reaction Methods 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000002091 cationic group Chemical group 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 150000002442 hydroxyeicosatetraenoic acids Chemical class 0.000 description 25
- 102000015728 Mucins Human genes 0.000 description 13
- 108010063954 Mucins Proteins 0.000 description 13
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical class CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 12
- 210000004027 cell Anatomy 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 238000013459 approach Methods 0.000 description 6
- 208000024891 symptom Diseases 0.000 description 6
- 102000003820 Lipoxygenases Human genes 0.000 description 5
- 108090000128 Lipoxygenases Proteins 0.000 description 5
- 229940114079 arachidonic acid Drugs 0.000 description 5
- 235000021342 arachidonic acid Nutrition 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 239000000607 artificial tear Substances 0.000 description 4
- 210000000981 epithelium Anatomy 0.000 description 4
- 230000001050 lubricating effect Effects 0.000 description 4
- 239000003755 preservative agent Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- ZIOZYRSDNLNNNJ-LQWMCKPYSA-N 12(S)-HPETE Chemical compound CCCCC\C=C/C[C@H](OO)\C=C\C=C/C\C=C/CCCC(O)=O ZIOZYRSDNLNNNJ-LQWMCKPYSA-N 0.000 description 3
- -1 12-hydroxy- [S- (E Chemical compound 0.000 description 3
- NNDIXBJHNLFJJP-UHFFFAOYSA-N 20-Hydroxyeicosatetraenoic acid Chemical compound OCCCCCC=CCC=CCC=CCC=CCCCC(O)=O NNDIXBJHNLFJJP-UHFFFAOYSA-N 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 210000004072 lung Anatomy 0.000 description 3
- 229940051875 mucins Drugs 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 230000028327 secretion Effects 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- ZNHVWPKMFKADKW-UHFFFAOYSA-N 12-HETE Chemical compound CCCCCC=CCC(O)C=CC=CCC=CCCCC(O)=O ZNHVWPKMFKADKW-UHFFFAOYSA-N 0.000 description 2
- ZNHVWPKMFKADKW-ZYBDYUKJSA-N 12-HETE Natural products CCCCC\C=C/C[C@@H](O)\C=C\C=C/C\C=C/CCCC(O)=O ZNHVWPKMFKADKW-ZYBDYUKJSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- 102000003886 Glycoproteins Human genes 0.000 description 2
- 108090000288 Glycoproteins Proteins 0.000 description 2
- 206010020751 Hypersensitivity Diseases 0.000 description 2
- 102000003992 Peroxidases Human genes 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 230000007815 allergy Effects 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 210000002919 epithelial cell Anatomy 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- 210000003097 mucus Anatomy 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- ZRVOHYJWSYEIDY-OWVSISMKSA-N (5e,8e,10e,14e)-icosa-5,8,10,14-tetraenoic acid Chemical compound CCCCC\C=C\CC\C=C\C=C\C\C=C\CCCC(O)=O ZRVOHYJWSYEIDY-OWVSISMKSA-N 0.000 description 1
- IJAXPCZCTKDWBJ-VAGPFTOWSA-N (5e,8e,11e,13e)-icosa-5,8,11,13-tetraenoic acid Chemical compound CCCCCC\C=C\C=C\C\C=C\C\C=C\CCCC(O)=O IJAXPCZCTKDWBJ-VAGPFTOWSA-N 0.000 description 1
- JSFATNQSLKRBCI-UHFFFAOYSA-N 15-Hydroxyeicosatetraenoic acid Chemical compound CCCCCC(O)C=CC=CCC=CCC=CCCCC(O)=O JSFATNQSLKRBCI-UHFFFAOYSA-N 0.000 description 1
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
- YAZDSTCFFRZJLW-UHFFFAOYSA-N 2-hydroxyicosa-2,4,6,8-tetraenoic acid Chemical compound CCCCCCCCCCCC=CC=CC=CC=C(O)C(O)=O YAZDSTCFFRZJLW-UHFFFAOYSA-N 0.000 description 1
- KGIJOOYOSFUGPC-CABOLEKPSA-N 5-HETE Natural products CCCCC\C=C/C\C=C/C\C=C/C=C/[C@H](O)CCCC(O)=O KGIJOOYOSFUGPC-CABOLEKPSA-N 0.000 description 1
- JNUUNUQHXIOFDA-XTDASVJISA-N 5-HPETE Chemical compound CCCCC\C=C/C\C=C/C\C=C/C=C/C(OO)CCCC(O)=O JNUUNUQHXIOFDA-XTDASVJISA-N 0.000 description 1
- RDEYORKJEDLLDB-DQVHGTJVSA-N 5-Hydroperoxyeicosatetraenoic acid Chemical compound CCCCCCCCCCC\C=C\C=C\C(\OO)=C\C=C\C(O)=O RDEYORKJEDLLDB-DQVHGTJVSA-N 0.000 description 1
- KGIJOOYOSFUGPC-MSFIICATSA-N 5-Hydroxyeicosatetraenoic acid Chemical compound CCCCCC=CCC=CCC=C\C=C\[C@@H](O)CCCC(O)=O KGIJOOYOSFUGPC-MSFIICATSA-N 0.000 description 1
- 102000011730 Arachidonate 12-Lipoxygenase Human genes 0.000 description 1
- 108010076676 Arachidonate 12-lipoxygenase Proteins 0.000 description 1
- 102000009515 Arachidonate 15-Lipoxygenase Human genes 0.000 description 1
- 108010048907 Arachidonate 15-lipoxygenase Proteins 0.000 description 1
- 102000001381 Arachidonate 5-Lipoxygenase Human genes 0.000 description 1
- 108010093579 Arachidonate 5-lipoxygenase Proteins 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical class [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- 102000002004 Cytochrome P-450 Enzyme System Human genes 0.000 description 1
- 108010015742 Cytochrome P-450 Enzyme System Proteins 0.000 description 1
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 235000003332 Ilex aquifolium Nutrition 0.000 description 1
- 235000002296 Ilex sandwicensis Nutrition 0.000 description 1
- 235000002294 Ilex volkensiana Nutrition 0.000 description 1
- 208000009319 Keratoconjunctivitis Sicca Diseases 0.000 description 1
- 101000844719 Mus musculus Deleted in malignant brain tumors 1 protein Proteins 0.000 description 1
- 101100346764 Mus musculus Mtln gene Proteins 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 206010033799 Paralysis Diseases 0.000 description 1
- 108700020962 Peroxidase Proteins 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960000686 benzalkonium chloride Drugs 0.000 description 1
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 239000007975 buffered saline Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229960004926 chlorobutanol Drugs 0.000 description 1
- 210000000795 conjunctiva Anatomy 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 210000003560 epithelium corneal Anatomy 0.000 description 1
- 229940011871 estrogen Drugs 0.000 description 1
- 239000000262 estrogen Substances 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 210000000744 eyelid Anatomy 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 230000035558 fertility Effects 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 229960002442 glucosamine Drugs 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- 125000001867 hydroperoxy group Chemical group [*]OO[H] 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 239000011859 microparticle Substances 0.000 description 1
- 230000003843 mucus production Effects 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000036407 pain Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 108040007629 peroxidase activity proteins Proteins 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 150000004492 retinoid derivatives Chemical class 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229940037001 sodium edetate Drugs 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 210000004989 spleen cell Anatomy 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 230000004489 tear production Effects 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
- A61K31/202—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids having three or more double bonds, e.g. linolenic
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/04—Artificial tears; Irrigation solutions
Landscapes
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Ophthalmology & Optometry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/551,021 US5696166A (en) | 1995-10-31 | 1995-10-31 | Compositions containing hydroxyeicosatetraenoic acid derivatives and methods of use in treating dry eye disorders |
| US08/551,021 | 1995-10-31 | ||
| PCT/US1996/013441 WO1997016179A1 (en) | 1995-10-31 | 1996-08-19 | Compositions containing hydroperoxyeicosatetraenoic acid derivatives and methods of use in treating dry eye disorders |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH11515024A true JPH11515024A (ja) | 1999-12-21 |
| JPH11515024A5 JPH11515024A5 (https=) | 2004-09-16 |
Family
ID=24199512
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9517306A Abandoned JPH11515024A (ja) | 1995-10-31 | 1996-08-19 | ヒドロペルオキシエイコサテトラエン酸誘導体を含む組成物およびドライアイ疾患の治療における使用方法 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US5696166A (https=) |
| EP (1) | EP0858330B1 (https=) |
| JP (1) | JPH11515024A (https=) |
| AT (1) | ATE198044T1 (https=) |
| AU (1) | AU706373B2 (https=) |
| CA (1) | CA2234367C (https=) |
| DE (1) | DE69611251T2 (https=) |
| DK (1) | DK0858330T3 (https=) |
| ES (1) | ES2152556T3 (https=) |
| GR (1) | GR3035438T3 (https=) |
| PT (1) | PT858330E (https=) |
| WO (1) | WO1997016179A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011500568A (ja) * | 2007-10-12 | 2011-01-06 | リゾルヴィクス・ファーマシューティカルズ・インコーポレイテッド | 眼病治療のための組成物及び方法 |
Families Citing this family (60)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1269484C (zh) * | 1998-09-18 | 2006-08-16 | 艾尔科实验室公司 | 用于治疗青光眼的5－羟色胺激活性激动剂 |
| AU2183900A (en) | 1998-12-24 | 2000-07-31 | Alcon Laboratories, Inc. | Ep4 receptor agonists for treatment of dry eye |
| US6462080B1 (en) | 1998-12-24 | 2002-10-08 | Alcon Manufacturing, Ltd. | Prostaglandin E receptor agonists for treatment of dry eye |
| TWI225398B (en) * | 1999-07-14 | 2004-12-21 | R Tech Ueno Ltd | Composition for treatment of external secretion disorders |
| PL356127A1 (en) | 1999-11-09 | 2004-06-14 | Alcon Inc. | Omega chain modified 15-hydroxyeicosatetraenoic acid derivatives and methods of their use for the treatment of dry eye |
| AU1101301A (en) * | 1999-11-09 | 2001-06-06 | Alcon Universal Limited | 2,2-difluoro 15-hydroxyeicosatetraenoic acid analogs and methods of use |
| US6458854B2 (en) | 1999-11-09 | 2002-10-01 | Alcon Universal Ltd. | Phospholipids of hydroxyeicosatetraenoic acid-like derivatives and methods of use |
| CA2388044A1 (en) * | 1999-11-09 | 2001-05-17 | Alcon, Inc. | Hydroxyeicosatetraenoate salts, compositions and methods of use in treating dry eye disorders |
| EP1228026B1 (en) | 1999-11-09 | 2004-01-02 | Alcon Inc. | 15-hydroxyeicosatetraenoic acid-related compounds and methods of use |
| US6353032B1 (en) | 1999-11-09 | 2002-03-05 | Alcon Universal Ltd. | Phospholipids of hydroxyeicosatetraenoic acid-like derivatives and methods of use |
| CA2386333A1 (en) * | 1999-11-09 | 2001-05-17 | Alcon, Inc. | 3-heteroatom substituted and two carbon homologs 15-hete and methods of use |
| PT1418167E (pt) * | 1999-11-09 | 2005-05-31 | Alcon Inc | Analogos do acido hidroxieicosatetraenoico e metodos para a sua utilizacao no tratamento de doencas do olho seco |
| EP1228030B1 (en) | 1999-11-09 | 2005-06-01 | Alcon Inc. | Benzenoid derivatives of 15-hydroxyeicosatetraenoic acid and methods of their use in treating dry eye disorders |
| MXPA02004702A (es) * | 1999-11-09 | 2004-09-10 | Alcon Inc | Analogos interrumpidos por heteroatomos de acido 15-hidroxieicosatetraenoico y metodos de uso. |
| US6803385B2 (en) | 1999-11-09 | 2004-10-12 | Alcon, Inc. | Hydroxyeicosatetraenoic acid analogs and methods of their use in treating dry eye disorders |
| DK1418167T3 (da) * | 1999-11-09 | 2005-04-25 | Alcon Inc | Hydroxyicosatetraensyreanaloger og fremgangsmåder til deres anvendelse til behandling af öjentörhedslidelser |
| MXPA02004703A (es) | 1999-11-09 | 2004-09-10 | Alcon Inc | Composiciones que contienen derivados de acido hidroxieicostetraenoico y metodos de uso para tratar trastornos de resequedad en los ojos. |
| US6552084B2 (en) | 1999-11-09 | 2003-04-22 | Alcon Universal Ltd. | Hydroxyeicosatetraenoic acid analogs and methods of their use in treating dry eye disorders |
| ES2215752T3 (es) | 1999-11-09 | 2004-10-16 | Alcon, Inc | Lipoxina a4 y analogos para el tratamiento del ojo seco. |
| US6320062B1 (en) | 1999-11-09 | 2001-11-20 | Alcon Universal Ltd. | 15-hydroxyeicosatetraenoic acid analogs with enhanced metabolic stability and methods of their use in treating dry eye disorders |
| US6576663B2 (en) | 1999-12-22 | 2003-06-10 | Alcon, Inc. | 6-Keto prostaglandin F1α and analogs for treating dry eye |
| US6277855B1 (en) * | 2000-04-21 | 2001-08-21 | Inspire Pharmaceuticals, Inc. | Method of treating dry eye disease with nicotinic acetylcholine receptor agonists |
| US20020077358A1 (en) * | 2000-10-23 | 2002-06-20 | Alcon Universal Ltd. | Use of hydroperoxyeicosatetraenoic acid derivatives following refractive surgery |
| DK1330246T3 (da) * | 2000-10-23 | 2005-08-08 | Alcon Inc | Anvendelse af hydroxyicosatetraensyrederivater ved intraokulær kirurgi |
| US8168616B1 (en) | 2000-11-17 | 2012-05-01 | Novartis Ag | Combination comprising a renin inhibitor and an angiotensin receptor inhibitor for hypertension |
| DE60213230T2 (de) | 2001-05-21 | 2006-11-23 | Alcon Inc. | Verwendung von NF-Kappa.B Inhibitoren zur Behandlung von Augentrockenheit |
| US7112588B2 (en) * | 2001-05-21 | 2006-09-26 | Alcon, Inc. | Use of proteasome inhibitors to treat dry eye disorders |
| US6740674B2 (en) | 2001-05-21 | 2004-05-25 | Alcon, Inc. | Use of proteasome inhibitors to treat dry eye disorders |
| US6872382B1 (en) | 2001-05-21 | 2005-03-29 | Alcon, Inc. | Use of selective PDE IV inhibitors to treat dry eye disorders |
| BR0209882A (pt) * | 2001-05-21 | 2004-06-08 | Alcon Inc | Método para o tratamento de distúrbios de olho seco |
| US6645994B1 (en) | 2001-06-01 | 2003-11-11 | Alcon, Inc. | Method of treating dry eye disorders |
| US6750250B1 (en) | 2001-07-12 | 2004-06-15 | Alcon, Inc. | 11,12-oxidoarachidonic acid derivatives and methods of their use in treating dry eye disorders |
| WO2003030892A1 (en) * | 2001-10-11 | 2003-04-17 | Alcon, Inc. | Methods for treating dry eye |
| US20030109508A1 (en) * | 2001-10-11 | 2003-06-12 | Alcon, Inc. | Methods for treating dry eye |
| CA2462272A1 (en) * | 2001-10-11 | 2003-04-17 | Alcon, Inc. | Methods for treating dry eye by a combination of an antiinflammatory steroid and a muc-1 secretagogue |
| WO2003105831A1 (en) * | 2002-06-14 | 2003-12-24 | Alcon, Inc. | Use of hydroxyeicosatetraenoic acid compounds to treat ophthalmic inflammatory disorders |
| WO2003105824A1 (en) * | 2002-06-14 | 2003-12-24 | Alcon, Inc. | Topical use of hydroxyeicosatetraenoic acid compounds to treat psoriasis |
| FR2843026B1 (fr) * | 2002-08-02 | 2006-01-06 | Goemar Lab Sa | Nouveau medicament |
| CA2497977A1 (en) * | 2002-09-20 | 2004-04-01 | Alcon, Inc. | Use of cytokine synthesis inhibitors for the treatment of dry eye disorders |
| AU2003303623A1 (en) * | 2002-12-20 | 2004-07-29 | Alcon, Inc. | Treatment of dry eye by restoring 15-lipoxygenase activity to ocular surface cells |
| WO2004093878A1 (en) | 2003-04-16 | 2004-11-04 | Alcon, Inc. | Use of fused pyridazine derivatives for treating dry eye disorders |
| US8455016B2 (en) | 2004-03-12 | 2013-06-04 | Melbj Holdings, Llc | Treatment for meibomian gland dysfunction or obstruction |
| US20050202097A1 (en) * | 2004-03-12 | 2005-09-15 | Melbj Holdings, Llc, Florida | Lubricant for the ocular surface |
| US7923471B2 (en) * | 2004-05-14 | 2011-04-12 | Alcon, Inc. | Method of treating dry eye disorders and uveitis |
| CN100522147C (zh) * | 2004-05-14 | 2009-08-05 | 爱尔康公司 | 5,6,7-三羟基庚酸及其类似物在制备治疗干眼病和眼色素层炎药物中的应用 |
| US7223737B1 (en) | 2004-08-13 | 2007-05-29 | Alcon, Inc. | Method of treating dry eye disorders using glycosides |
| US20070265353A1 (en) * | 2004-08-27 | 2007-11-15 | Senju Pharmaceutical Co., Ltd. | Eye Drops for the Treatment of Dry Eye |
| WO2006065916A1 (en) * | 2004-12-14 | 2006-06-22 | Alcon, Inc. | Method of treating dry eye disorders using 13(s)-hode and its analogs |
| US7745461B1 (en) | 2006-02-27 | 2010-06-29 | Alcon Research, Ltd. | Method of treating dry eye disorders |
| US8541426B2 (en) * | 2007-07-11 | 2013-09-24 | Pfizer Inc. | Pharmaceutical compositions and methods of treating dry eye disorders |
| US20090048368A1 (en) * | 2007-08-13 | 2009-02-19 | Bash Thomas F | Polyolefin compositions comprising bio-based starch materials |
| AU2014201375B2 (en) * | 2007-10-12 | 2015-11-05 | Resolvyx Pharmaceuticals, Inc. | Omega-3 fatty acids, hydroxy polyunsaturated fatty acids, lipoxin compounds, or oxylipin compounds for the treatment of ophthalmic conditions |
| US20090098136A1 (en) * | 2007-10-15 | 2009-04-16 | Alcon Research, Ltd. | Use of tnf receptor antagonists for treating dry eye |
| TW200927192A (en) * | 2007-11-19 | 2009-07-01 | Alcon Res Ltd | Use of TRPV1 receptor antagonists for treating dry eye and ocular pain |
| US8207226B1 (en) | 2008-06-03 | 2012-06-26 | Alcon Research, Ltd. | Use of FAAH antagonists for treating dry eye and ocular pain |
| GB0907413D0 (en) | 2009-04-29 | 2009-06-10 | Equateq Ltd | Novel methods |
| WO2011057183A1 (en) | 2009-11-06 | 2011-05-12 | Alcon Research, Ltd. | Nutritional supplements for relief of dry eye |
| EP3068757B1 (en) * | 2013-11-15 | 2019-02-27 | DS Biopharma Limited | Lysine salt of 15-hydroxy-8(z),11(z),13(e)-eicosatrienoic acid |
| CN109311976A (zh) | 2016-06-20 | 2019-02-05 | 诺华股份有限公司 | 使用TNFα拮抗剂治疗干眼症的方法 |
| US20210315851A1 (en) | 2020-04-03 | 2021-10-14 | Afimmune Limited | Compositions comprising 15-hepe and methods of treating or preventing hematologic disorders, and/or related diseases |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3991759A (en) * | 1975-10-28 | 1976-11-16 | Alza Corporation | Method and therapeutic system for treating aqueous deficient dry eye |
| US4131651A (en) * | 1977-10-25 | 1978-12-26 | Barnes-Hind Pharmaceuticals, Inc. | Treatment of dry eye |
| US4409205A (en) * | 1979-03-05 | 1983-10-11 | Cooper Laboratories, Inc. | Ophthalmic solution |
| US4370325A (en) * | 1979-03-30 | 1983-01-25 | Dermik Laboratories | Pharmaceutical compositions and method of treatment |
| AU546872B2 (en) * | 1982-06-16 | 1985-09-26 | Unilever Plc | Skin treatment compositions containing a fatty acid or ester |
| GB8319073D0 (en) * | 1983-07-14 | 1983-08-17 | Efamol Ltd | Fatty acid compositions |
| US4883658A (en) * | 1986-04-28 | 1989-11-28 | Holly Frank J | Ophthalmic solution for treatment of dry-eye syndrome |
| US4744980A (en) * | 1986-04-28 | 1988-05-17 | Holly Frank J | Ophthalmic solution for treatment of dry eye syndrome |
| US4818537A (en) * | 1986-10-21 | 1989-04-04 | Liposome Technology, Inc. | Liposome composition for treating dry eye |
| US4966773A (en) * | 1986-11-25 | 1990-10-30 | Alcon Laboratories, Inc. | Topical ophthalmic compositions containing microfine retinoid particles |
| US4914088A (en) * | 1987-04-02 | 1990-04-03 | Thomas Glonek | Dry eye treatment solution and method |
| US4906467A (en) * | 1988-03-24 | 1990-03-06 | New York Medical College | Novel, long-duration treatment for glaucoma |
| US5075104A (en) * | 1989-03-31 | 1991-12-24 | Alcon Laboratories, Inc. | Ophthalmic carboxy vinyl polymer gel for dry eye syndrome |
| US5041434A (en) * | 1991-08-17 | 1991-08-20 | Virginia Lubkin | Drugs for topical application of sex steroids in the treatment of dry eye syndrome, and methods of preparation and application |
| DE69115990T2 (de) * | 1990-05-29 | 1996-05-30 | Ocular Res Of Bonton Inc | Zusammensetzung zur Behandlung von Dry Eye Erkrankungen |
| US5102670A (en) * | 1990-09-14 | 1992-04-07 | Abraham Nader G | Method for treating eye disorders by reducing 12(r)-hydroxyeicosatetraenoic acid and 12(r)-dihydroxyeicosatrienoic acid levels |
| ATE141502T1 (de) * | 1991-01-15 | 1996-09-15 | Alcon Lab Inc | Verwendung von karrageenan in topischen ophthalmologischen zusammensetzungen |
| EP0546728A3 (en) * | 1991-12-13 | 1993-09-08 | Alcon Laboratories Inc | Physiological tear compositions and methods for their preparation |
| US5290572A (en) * | 1992-08-06 | 1994-03-01 | Deo Corporation | Opthalmic composition for treating dry eye |
| US5358706A (en) * | 1992-09-30 | 1994-10-25 | Union Carbide Chemicals & Plastics Technology Corporation | Muco-adhesive polymers |
| US5389383A (en) * | 1993-06-18 | 1995-02-14 | Allergan, Inc. | Method for treating hypoxia-associated ocular complications |
-
1995
- 1995-10-31 US US08/551,021 patent/US5696166A/en not_active Expired - Lifetime
-
1996
- 1996-08-19 ES ES96928944T patent/ES2152556T3/es not_active Expired - Lifetime
- 1996-08-19 JP JP9517306A patent/JPH11515024A/ja not_active Abandoned
- 1996-08-19 CA CA002234367A patent/CA2234367C/en not_active Expired - Fee Related
- 1996-08-19 WO PCT/US1996/013441 patent/WO1997016179A1/en not_active Ceased
- 1996-08-19 AT AT96928944T patent/ATE198044T1/de not_active IP Right Cessation
- 1996-08-19 DE DE69611251T patent/DE69611251T2/de not_active Expired - Fee Related
- 1996-08-19 DK DK96928944T patent/DK0858330T3/da active
- 1996-08-19 PT PT96928944T patent/PT858330E/pt unknown
- 1996-08-19 EP EP96928944A patent/EP0858330B1/en not_active Expired - Lifetime
- 1996-08-19 AU AU68516/96A patent/AU706373B2/en not_active Ceased
-
2001
- 2001-02-20 GR GR20010400269T patent/GR3035438T3/el not_active IP Right Cessation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011500568A (ja) * | 2007-10-12 | 2011-01-06 | リゾルヴィクス・ファーマシューティカルズ・インコーポレイテッド | 眼病治療のための組成物及び方法 |
| JP2014037437A (ja) * | 2007-10-12 | 2014-02-27 | Resolvyx Pharmaceuticals Inc | 眼病治療のための組成物及び方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2234367C (en) | 2002-06-04 |
| DE69611251T2 (de) | 2001-04-05 |
| EP0858330A1 (en) | 1998-08-19 |
| WO1997016179A1 (en) | 1997-05-09 |
| ES2152556T3 (es) | 2001-02-01 |
| ATE198044T1 (de) | 2000-12-15 |
| DK0858330T3 (da) | 2001-01-02 |
| HK1013194A1 (en) | 1999-08-20 |
| PT858330E (pt) | 2001-03-30 |
| EP0858330B1 (en) | 2000-12-13 |
| CA2234367A1 (en) | 1997-05-09 |
| US5696166A (en) | 1997-12-09 |
| AU706373B2 (en) | 1999-06-17 |
| DE69611251D1 (de) | 2001-01-18 |
| AU6851696A (en) | 1997-05-22 |
| GR3035438T3 (en) | 2001-05-31 |
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