NO800059L - Preparat for behandling av glaukom. - Google Patents
Preparat for behandling av glaukom.Info
- Publication number
- NO800059L NO800059L NO800059A NO800059A NO800059L NO 800059 L NO800059 L NO 800059L NO 800059 A NO800059 A NO 800059A NO 800059 A NO800059 A NO 800059A NO 800059 L NO800059 L NO 800059L
- Authority
- NO
- Norway
- Prior art keywords
- hydroxy
- stated
- glaucoma
- propoxy
- preparation
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 49
- 150000001875 compounds Chemical class 0.000 claims description 42
- 208000010412 Glaucoma Diseases 0.000 claims description 38
- -1 hydroxy, ureido Chemical group 0.000 claims description 19
- FVXYRXMYPXVHNY-UHFFFAOYSA-N 3-propoxy-3,4-dihydro-1H-quinolin-2-one Chemical compound C(CC)OC1C(NC2=CC=CC=C2C1)=O FVXYRXMYPXVHNY-UHFFFAOYSA-N 0.000 claims description 18
- 125000006309 butyl amino group Chemical group 0.000 claims description 18
- 239000002997 ophthalmic solution Substances 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000005606 carbostyryl group Chemical group 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 229940054534 ophthalmic solution Drugs 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 5
- 230000004410 intraocular pressure Effects 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 235000002639 sodium chloride Nutrition 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000000546 pharmaceutical excipient Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000003885 eye ointment Substances 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 206010030348 Open-Angle Glaucoma Diseases 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 230000001603 reducing effect Effects 0.000 description 3
- 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
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- 230000005856 abnormality Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000001768 carboxy methyl cellulose 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
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- MUCZHBLJLSDCSD-UHFFFAOYSA-N diisopropyl fluorophosphate Chemical compound CC(C)OP(F)(=O)OC(C)C MUCZHBLJLSDCSD-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 229960005051 fluostigmine Drugs 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QCHFTSOMWOSFHM-WPRPVWTQSA-N (+)-Pilocarpine Chemical compound C1OC(=O)[C@@H](CC)[C@H]1CC1=CN=CN1C QCHFTSOMWOSFHM-WPRPVWTQSA-N 0.000 description 1
- FFJCNSLCJOQHKM-CLFAGFIQSA-N (z)-1-[(z)-octadec-9-enoxy]octadec-9-ene Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCCCCCCC\C=C/CCCCCCCC FFJCNSLCJOQHKM-CLFAGFIQSA-N 0.000 description 1
- MUHFRORXWCGZGE-KTKRTIGZSA-N 2-hydroxyethyl (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCO MUHFRORXWCGZGE-KTKRTIGZSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- YNZNESKPSHZISM-UHFFFAOYSA-N 3-propoxy-1h-quinolin-2-one Chemical compound C1=CC=C2NC(=O)C(OCCC)=CC2=C1 YNZNESKPSHZISM-UHFFFAOYSA-N 0.000 description 1
- HBNKDRKDIGEFQB-UHFFFAOYSA-N 3-propoxy-3,4-dihydro-1H-quinolin-2-one hydrochloride Chemical compound Cl.CCCOC1Cc2ccccc2NC1=O HBNKDRKDIGEFQB-UHFFFAOYSA-N 0.000 description 1
- BQVFQQWEPXJUMY-UHFFFAOYSA-N 5-[3-(tert-butylamino)-2-hydroxypropoxy]-1-prop-2-enyl-3,4-dihydroquinolin-2-one;hydrochloride Chemical compound Cl.C=CCN1C(=O)CCC2=C1C=CC=C2OCC(O)CNC(C)(C)C BQVFQQWEPXJUMY-UHFFFAOYSA-N 0.000 description 1
- GMXOQDKFOUEEEK-UHFFFAOYSA-N 5-[3-[(2-hydroxycyclohexyl)amino]propoxy]-1h-quinolin-2-one Chemical compound OC1CCCCC1NCCCOC1=CC=CC2=C1C=CC(=O)N2 GMXOQDKFOUEEEK-UHFFFAOYSA-N 0.000 description 1
- KPVIJNKXBAQQIU-UHFFFAOYSA-N 5-[3-[(2-hydroxycyclohexyl)amino]propoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound OC1CCCCC1NCCCOC1=CC=CC2=C1CCC(=O)N2 KPVIJNKXBAQQIU-UHFFFAOYSA-N 0.000 description 1
- NYYFHSKWAIZWCI-UHFFFAOYSA-N 5-[3-[(2-hydroxycyclooctyl)amino]propoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound OC1CCCCCCC1NCCCOC1=CC=CC2=C1CCC(=O)N2 NYYFHSKWAIZWCI-UHFFFAOYSA-N 0.000 description 1
- LODHLGQSQVDRCY-UHFFFAOYSA-N 8-[2-hydroxy-3-(propan-2-ylamino)propoxy]-3,4-dihydro-1h-quinolin-2-one;hydrochloride Chemical compound Cl.C1CC(=O)NC2=C1C=CC=C2OCC(O)CNC(C)C LODHLGQSQVDRCY-UHFFFAOYSA-N 0.000 description 1
- DHMGHZYTYDLGRC-UHFFFAOYSA-N 8-but-2-enoxy-5-[3-[(2-hydroxycyclohexyl)amino]propoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound C1=2CCC(=O)NC=2C(OCC=CC)=CC=C1OCCCNC1CCCCC1O DHMGHZYTYDLGRC-UHFFFAOYSA-N 0.000 description 1
- GDLIUXSSLYAOSA-UHFFFAOYSA-N 8-hydroxy-5-[3-[(2-hydroxycyclohexyl)amino]propoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound OC1CCCCC1NCCCOC1=CC=C(O)C2=C1CCC(=O)N2 GDLIUXSSLYAOSA-UHFFFAOYSA-N 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 208000002177 Cataract Diseases 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 206010010741 Conjunctivitis Diseases 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- PIJVFDBKTWXHHD-UHFFFAOYSA-N Physostigmine Natural products C12=CC(OC(=O)NC)=CC=C2N(C)C2C1(C)CCN2C PIJVFDBKTWXHHD-UHFFFAOYSA-N 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- QCHFTSOMWOSFHM-UHFFFAOYSA-N SJ000285536 Natural products C1OC(=O)C(CC)C1CC1=CN=CN1C QCHFTSOMWOSFHM-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- VKMSBFYZHGDBAG-UHFFFAOYSA-N [5-[3-[(2-hydroxycyclohexyl)amino]propoxy]-2-oxo-3,4-dihydro-1h-quinolin-8-yl]urea Chemical compound C1=2CCC(=O)NC=2C(NC(=O)N)=CC=C1OCCCNC1CCCCC1O VKMSBFYZHGDBAG-UHFFFAOYSA-N 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 1
- 238000011047 acute toxicity test Methods 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 125000005336 allyloxy group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 230000006793 arrhythmia Effects 0.000 description 1
- 206010003119 arrhythmia 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
- UREZNYTWGJKWBI-UHFFFAOYSA-M benzethonium chloride Chemical compound [Cl-].C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 UREZNYTWGJKWBI-UHFFFAOYSA-M 0.000 description 1
- 229960001950 benzethonium chloride Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
- 229910021538 borax Inorganic materials 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 235000010338 boric acid Nutrition 0.000 description 1
- AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical compound [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 229960001927 cetylpyridinium chloride Drugs 0.000 description 1
- YMKDRGPMQRFJGP-UHFFFAOYSA-M cetylpyridinium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 YMKDRGPMQRFJGP-UHFFFAOYSA-M 0.000 description 1
- 229960004926 chlorobutanol Drugs 0.000 description 1
- 239000000544 cholinesterase inhibitor Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- RWZVPVOZTJJMNU-UHFFFAOYSA-N demarcarium Chemical compound C=1C=CC([N+](C)(C)C)=CC=1OC(=O)N(C)CCCCCCCCCCN(C)C(=O)OC1=CC=CC([N+](C)(C)C)=C1 RWZVPVOZTJJMNU-UHFFFAOYSA-N 0.000 description 1
- 229960004656 demecarium Drugs 0.000 description 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
- 229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
- 235000019797 dipotassium phosphate Nutrition 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- LNGNZSMIUVQZOX-UHFFFAOYSA-L disodium;dioxido(sulfanylidene)-$l^{4}-sulfane Chemical compound [Na+].[Na+].[O-]S([O-])=S LNGNZSMIUVQZOX-UHFFFAOYSA-L 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000005290 ethynyloxy group Chemical group C(#C)O* 0.000 description 1
- 210000000744 eyelid Anatomy 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- FVIZARNDLVOMSU-UHFFFAOYSA-N ginsenoside K Natural products C1CC(C2(CCC3C(C)(C)C(O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC1OC(CO)C(O)C(O)C1O FVIZARNDLVOMSU-UHFFFAOYSA-N 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 229960002362 neostigmine Drugs 0.000 description 1
- LULNWZDBKTWDGK-UHFFFAOYSA-M neostigmine bromide Chemical compound [Br-].CN(C)C(=O)OC1=CC=CC([N+](C)(C)C)=C1 LULNWZDBKTWDGK-UHFFFAOYSA-M 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- PIJVFDBKTWXHHD-HIFRSBDPSA-N physostigmine Chemical compound C12=CC(OC(=O)NC)=CC=C2N(C)[C@@H]2[C@@]1(C)CCN2C PIJVFDBKTWXHHD-HIFRSBDPSA-N 0.000 description 1
- 229960001697 physostigmine Drugs 0.000 description 1
- 229960001416 pilocarpine Drugs 0.000 description 1
- 229920000056 polyoxyethylene ether Polymers 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- HELHAJAZNSDZJO-OLXYHTOASA-L sodium L-tartrate Chemical compound [Na+].[Na+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O HELHAJAZNSDZJO-OLXYHTOASA-L 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000011083 sodium citrates Nutrition 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000001433 sodium tartrate Substances 0.000 description 1
- 229960002167 sodium tartrate Drugs 0.000 description 1
- 235000011004 sodium tartrates Nutrition 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000003826 tablet Substances 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
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000004382 visual function Effects 0.000 description 1
- 239000003871 white petrolatum Substances 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP54010108A JPS5951927B2 (ja) | 1979-01-30 | 1979-01-30 | 緑内障治療剤 |
JP54070361A JPS5951928B2 (ja) | 1979-06-04 | 1979-06-04 | 緑内障治療剤 |
Publications (1)
Publication Number | Publication Date |
---|---|
NO800059L true NO800059L (no) | 1980-07-31 |
Family
ID=26345304
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO800059A NO800059L (no) | 1979-01-30 | 1980-01-11 | Preparat for behandling av glaukom. |
Country Status (15)
Country | Link |
---|---|
US (1) | US4309432A (da) |
AT (1) | AT371340B (da) |
AU (1) | AU518814B2 (da) |
CA (1) | CA1139669A (da) |
CH (1) | CH646057A5 (da) |
DE (1) | DE3001011C2 (da) |
DK (1) | DK11580A (da) |
ES (1) | ES8100268A1 (da) |
FI (1) | FI800089A (da) |
FR (1) | FR2447721A1 (da) |
GB (1) | GB2042338B (da) |
IT (1) | IT1141662B (da) |
NL (1) | NL191575C (da) |
NO (1) | NO800059L (da) |
SE (1) | SE451069B (da) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0056420A1 (en) * | 1981-01-15 | 1982-07-28 | Schering Corporation | Ophthalmic gel |
FR2539413A1 (fr) * | 1983-01-17 | 1984-07-20 | Pos Lab | Carbostyriloximinopropanolamines utiles comme medicaments et procede pour leur preparation |
US4792561A (en) * | 1986-05-29 | 1988-12-20 | Syntex (U.S.A.) Inc. | Carbostyril derivatives as combined thromboxane synthetase and cyclic-AMP phosphodiesterase inhibitors |
US4921862A (en) * | 1986-05-29 | 1990-05-01 | Syntex (U.S.A.) Inc. | Carbostyril derivatives as combined thromboxane synthetase and cyclic-amp phosphodiesterase inhibitors |
US5198448A (en) * | 1988-08-10 | 1993-03-30 | Otsuka Pharmaceutical Company, Limited | Cardiotonics |
EP0355583B1 (en) * | 1988-08-10 | 1995-01-25 | Otsuka Pharmaceutical Co., Ltd. | Cardiotonics |
DE69019774T2 (de) * | 1989-03-28 | 1995-11-09 | Nisshin Flour Milling Co | Isochinolin-Derivate zur Behandlung des Glaukoms oder der okulären Hypertonie. |
FR2676740B1 (fr) * | 1991-05-23 | 1993-11-05 | Roussel Uclaf | Nouveaux derives sterouides du pregna-4,9(11),17(20)-trie-3-one, leur preparation, leur application a la preparation de composes sterouides de type pregna-4,9(11),16-triene-3,20-dione et nouveaux intermediaires. |
US5629345A (en) * | 1993-07-23 | 1997-05-13 | Vide Pharmaceuticals | Methods and compositions for ATP-sensitive K+ channel inhibition for lowering intraocular pressure |
US5965620A (en) * | 1993-07-23 | 1999-10-12 | Vide Pharmaceuticals | Methods and compositions for ATP-sensitive K+ channel inhibition for lowering intraocular pressure |
US5776482A (en) * | 1996-03-29 | 1998-07-07 | University Of Iowa Research Foundation | Tetrahydroquinoline analogues for use in glaucoma treatment |
MY116782A (en) | 1997-12-22 | 2004-03-31 | Otsuka Pharma Co Ltd | Water-soluble eye drop |
BRPI0719396A2 (pt) * | 2006-12-06 | 2014-02-18 | United States Borax Inc | Composição de ração animal, uso de boro suplementar e vitamina c suplementar e método não terapêutico para aumentar a eficiência de absorção de fósforo em um animal, diminuir a quantidade de fósforo excretada por um animal, ou reduzir a poluição de fósforo ambiental em uma fazenda de criação |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS517672B2 (da) * | 1972-04-13 | 1976-03-10 | ||
US3910924A (en) * | 1972-04-13 | 1975-10-07 | Otsuka Pharma Co Ltd | 3,4-Dihydrocarbostyril derivatives and a process for preparing the same |
AR207554A1 (es) * | 1972-12-02 | 1976-10-15 | Otsuka Pharma Co Ltd | Procedimiento para producir derivados de 3-alquil-5-((3,4-dihidro-5-carbostiril)oximetil)-oxazolidinona-(2) |
JPS5239035B2 (da) * | 1972-12-14 | 1977-10-03 | ||
US3975391A (en) * | 1973-12-26 | 1976-08-17 | Otsuka Pharmaceutical Company Limited | 5-[1-Hydroxy-2-(substituted-amino)]ethyl-8-hydroxy-3,4-dihydrocarbostyril derivatives |
US3953546A (en) * | 1973-07-31 | 1976-04-27 | Sumitomo Chemical Company, Limited | Thio(dithio)phosphorates |
JPS5082218A (da) * | 1973-11-10 | 1975-07-03 | ||
US3994901A (en) * | 1974-06-13 | 1976-11-30 | Otsuka Pharmaceutical Company Limited | 5-[1-Hydroxy-2-(substituted-amino)]alkyl-8-hydroxy-3,4-dihydrocarbostyril derivatives |
US4081447A (en) * | 1975-04-09 | 1978-03-28 | Abbott Laboratories | 5-[2-Hydroxy-3-(3,4-dimethoxy phenethylamino)]-propoxy-3,4-dihydro carbostyril and pharmaceutically acceptable salts thereof |
CH619453A5 (da) * | 1976-03-17 | 1980-09-30 | Otsuka Pharma Co Ltd | |
US4210753A (en) * | 1976-03-17 | 1980-07-01 | Otsuka Pharmaceutical Co., Ltd. | Carbostyril compounds |
GB1574665A (en) * | 1976-05-08 | 1980-09-10 | Otsuka Pharma Co Ltd | 3,4-dihydrocarbostyril derivatives and process for preparing the same |
JPS552631A (en) * | 1978-06-19 | 1980-01-10 | Otsuka Pharmaceut Co Ltd | 3,4-dihydrocarbostyril derivative |
JPS5513241A (en) * | 1978-07-14 | 1980-01-30 | Otsuka Pharmaceut Co Ltd | Remedy for glaucoma |
-
1979
- 1979-12-28 AU AU54265/79A patent/AU518814B2/en not_active Expired
-
1980
- 1980-01-02 US US06/109,057 patent/US4309432A/en not_active Expired - Lifetime
- 1980-01-07 GB GB8000411A patent/GB2042338B/en not_active Expired
- 1980-01-09 IT IT05106/80A patent/IT1141662B/it active Protection Beyond IP Right Term
- 1980-01-10 DK DK11580A patent/DK11580A/da not_active Application Discontinuation
- 1980-01-11 FI FI800089A patent/FI800089A/fi not_active Application Discontinuation
- 1980-01-11 SE SE8000245A patent/SE451069B/sv not_active IP Right Cessation
- 1980-01-11 CA CA000343491A patent/CA1139669A/en not_active Expired
- 1980-01-11 FR FR8000552A patent/FR2447721A1/fr active Granted
- 1980-01-11 CH CH22080A patent/CH646057A5/de not_active IP Right Cessation
- 1980-01-11 ES ES487642A patent/ES8100268A1/es not_active Expired
- 1980-01-11 NO NO800059A patent/NO800059L/no unknown
- 1980-01-11 AT AT0014480A patent/AT371340B/de not_active IP Right Cessation
- 1980-01-12 DE DE3001011A patent/DE3001011C2/de not_active Expired
- 1980-01-14 NL NL8000211A patent/NL191575C/xx not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
FR2447721A1 (fr) | 1980-08-29 |
DE3001011A1 (de) | 1980-08-28 |
CA1139669A (en) | 1983-01-18 |
GB2042338B (en) | 1983-11-30 |
SE451069B (sv) | 1987-08-31 |
DK11580A (da) | 1980-07-31 |
IT8005106A0 (it) | 1980-01-09 |
FI800089A (fi) | 1980-07-31 |
NL8000211A (nl) | 1980-08-01 |
NL191575C (nl) | 1995-10-03 |
AU518814B2 (en) | 1981-10-22 |
ES487642A0 (es) | 1980-11-01 |
ES8100268A1 (es) | 1980-11-01 |
NL191575B (nl) | 1995-06-01 |
DE3001011C2 (de) | 1986-02-06 |
ATA14480A (de) | 1982-11-15 |
SE8000245L (sv) | 1980-07-31 |
IT1141662B (it) | 1986-10-08 |
GB2042338A (en) | 1980-09-24 |
AT371340B (de) | 1983-06-27 |
FR2447721B1 (da) | 1983-03-11 |
CH646057A5 (de) | 1984-11-15 |
AU5426579A (en) | 1980-08-07 |
US4309432A (en) | 1982-01-05 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US5061714A (en) | Isoquinoline composition for the treatment of glaucoma or ocular hypertension | |
NO800059L (no) | Preparat for behandling av glaukom. | |
CA2029657C (en) | Compositions and their use in lowering intraocular pressure | |
US5134124A (en) | Use of a statin derivative in the treatment of eye complaints | |
AU616748B2 (en) | Ophthalmic solution for intraocular pressure adjustment | |
EP0114333B1 (en) | Pharmaceutical composition | |
US5827862A (en) | Agent for prophylaxis or treatment of cataract | |
US4382953A (en) | Ophthalmic solution for intraocular pressure reduction | |
EP0509752B1 (en) | Ophthalmic compositions comprising combinations of a carbonic anhydrase inhibitor and a beta-adrenergic antagonist | |
EP0140789B1 (en) | Use of peripherally selective dopamine antagonists for the preparation of a medicament for the topical treatment of ocular hypertension | |
EP1225890B1 (en) | Rivastigmine for the treatment of ocular disorders | |
US5041450A (en) | Treatment of ocular inflammation | |
KR980008226A (ko) | 시각기능장애의 예방 및 치료제 | |
US4322425A (en) | Compositions for treating glaucoma | |
SE451070B (sv) | Anvendning av ett karbostyrilderivat for framstellning av ett lekemedel for behandling av glaukom | |
JP3066561B2 (ja) | 近視予防・治療剤 | |
US4826812A (en) | Antiglaucoma agent | |
US5252583A (en) | Isoquinoline derivatives for the treatment of glaucoma or ocular hypertension | |
JPS6232171B2 (da) | ||
JPS5951927B2 (ja) | 緑内障治療剤 | |
EP0277814A2 (en) | Anti-glaucoma use of trifluoromethanesulfonamide | |
EP0555717A1 (en) | Pharmaceutical compositions in the form of solutions containing nedocromil | |
JPS5951928B2 (ja) | 緑内障治療剤 | |
IE904261A1 (en) | Use of a statin derivative in the treatment of eye¹complaints | |
JPH04134029A (ja) | 緑内障治療剤 |