NZ196227A - 1,2,5-thiadiazole derivative and ophthalmic compositions - Google Patents
1,2,5-thiadiazole derivative and ophthalmic compositionsInfo
- Publication number
- NZ196227A NZ196227A NZ196227A NZ19622781A NZ196227A NZ 196227 A NZ196227 A NZ 196227A NZ 196227 A NZ196227 A NZ 196227A NZ 19622781 A NZ19622781 A NZ 19622781A NZ 196227 A NZ196227 A NZ 196227A
- Authority
- NZ
- New Zealand
- Prior art keywords
- butylamino
- oxy
- tert
- inserts
- thiadiazol
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 26
- 150000004868 1,2,5-thiadiazoles Chemical class 0.000 title 1
- 230000004048 modification Effects 0.000 claims abstract description 5
- 238000012986 modification Methods 0.000 claims abstract description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 17
- -1 hydroxypropyl Chemical group 0.000 claims description 13
- 230000004410 intraocular pressure Effects 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 208000010412 Glaucoma Diseases 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 238000009472 formulation Methods 0.000 claims description 4
- 230000000699 topical effect Effects 0.000 claims description 4
- 229920002678 cellulose Polymers 0.000 claims description 3
- 239000001913 cellulose Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 238000007906 compression Methods 0.000 claims description 3
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- 239000003755 preservative agent Substances 0.000 claims description 3
- WLRMANUAADYWEA-NWASOUNVSA-N (S)-timolol maleate Chemical compound OC(=O)\C=C/C(O)=O.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1 WLRMANUAADYWEA-NWASOUNVSA-N 0.000 claims description 2
- 239000011521 glass Substances 0.000 claims description 2
- 229960005221 timolol maleate Drugs 0.000 claims description 2
- TWBNMYSKRDRHAT-RCWTXCDDSA-N (S)-timolol hemihydrate Chemical compound O.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1 TWBNMYSKRDRHAT-RCWTXCDDSA-N 0.000 claims 1
- CFYIUBWVKZQDOG-UHFFFAOYSA-N 4-[[2-[[2-[[1-(4-nitroanilino)-1-oxo-3-phenylpropan-2-yl]amino]-2-oxoethyl]amino]-2-oxoethyl]amino]-4-oxobutanoic acid Chemical compound C=1C=C([N+]([O-])=O)C=CC=1NC(=O)C(NC(=O)CNC(=O)CNC(=O)CCC(=O)O)CC1=CC=CC=C1 CFYIUBWVKZQDOG-UHFFFAOYSA-N 0.000 claims 1
- 241000283973 Oryctolagus cuniculus Species 0.000 claims 1
- 230000003385 bacteriostatic effect Effects 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 230000001077 hypotensive effect Effects 0.000 claims 1
- 230000002335 preservative effect Effects 0.000 claims 1
- 230000002035 prolonged effect Effects 0.000 claims 1
- 229960004605 timolol Drugs 0.000 claims 1
- 230000004406 elevated intraocular pressure Effects 0.000 abstract description 6
- 229920000642 polymer Polymers 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
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- 239000010408 film Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 7
- 239000003981 vehicle Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000003513 alkali Substances 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 239000004014 plasticizer Substances 0.000 description 5
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 206010030043 Ocular hypertension Diseases 0.000 description 4
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- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 4
- 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 4
- 229940071676 hydroxypropylcellulose Drugs 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 3
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 3
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- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 229920002125 Sokalan® Polymers 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
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- 239000004615 ingredient Substances 0.000 description 3
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- 229920001223 polyethylene glycol Polymers 0.000 description 3
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- 239000000843 powder Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 229920003169 water-soluble polymer Polymers 0.000 description 3
- 125000004518 1,2,5-thiadiazol-3-yl group Chemical group S1N=C(C=N1)* 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 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
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
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- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
- YGLLICRFEVEWOZ-UHFFFAOYSA-L disodium;3-carboxy-1-[(3-carboxy-2-oxidonaphthalen-1-yl)methyl]naphthalen-2-olate Chemical compound [Na+].[Na+].C1=CC=C2C(CC3=C4C=CC=CC4=CC(=C3O)C([O-])=O)=C(O)C(C([O-])=O)=CC2=C1 YGLLICRFEVEWOZ-UHFFFAOYSA-L 0.000 description 2
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- 238000000465 moulding Methods 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
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- 210000003733 optic disk Anatomy 0.000 description 2
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 2
- 239000000312 peanut oil Substances 0.000 description 2
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- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 238000002360 preparation method Methods 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
- 230000005855 radiation Effects 0.000 description 2
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- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 2
- 229940033663 thimerosal Drugs 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- JCIIKRHCWVHVFF-UHFFFAOYSA-N 1,2,4-thiadiazol-5-amine;hydrochloride Chemical compound Cl.NC1=NC=NS1 JCIIKRHCWVHVFF-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 1
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- 201000004569 Blindness Diseases 0.000 description 1
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- 241000206576 Chondrus Species 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
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- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical class CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
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- 229920000881 Modified starch Polymers 0.000 description 1
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- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- MKRNVBXERAPZOP-UHFFFAOYSA-N Starch acetate Chemical compound O1C(CO)C(OC)C(O)C(O)C1OCC1C(OC2C(C(O)C(OC)C(CO)O2)OC(C)=O)C(O)C(O)C(OC2C(OC(C)C(O)C2O)CO)O1 MKRNVBXERAPZOP-UHFFFAOYSA-N 0.000 description 1
- 235000015125 Sterculia urens Nutrition 0.000 description 1
- 240000001058 Sterculia urens Species 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
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- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
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- 229920000615 alginic acid Polymers 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229910001514 alkali metal chloride Inorganic materials 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229940072107 ascorbate Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960000686 benzalkonium chloride Drugs 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 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
- 230000015572 biosynthetic process Effects 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
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- 125000006309 butyl amino group Chemical group 0.000 description 1
- 239000003489 carbonate dehydratase inhibitor Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229960004926 chlorobutanol Drugs 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 229960001484 edetic acid Drugs 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 235000012438 extruded product Nutrition 0.000 description 1
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- 239000000945 filler Substances 0.000 description 1
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- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
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- 235000011852 gelatine desserts Nutrition 0.000 description 1
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- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 239000001341 hydroxy propyl starch Substances 0.000 description 1
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- 238000001746 injection moulding Methods 0.000 description 1
- 230000000266 injurious effect Effects 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 231100001032 irritation of the eye Toxicity 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 description 1
- 230000008450 motivation Effects 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N p-hydroxybenzoic acid methyl ester Natural products COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
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- 239000001814 pectin Substances 0.000 description 1
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- 229920001277 pectin Polymers 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229940096826 phenylmercuric acetate Drugs 0.000 description 1
- VUXSPDNLYQTOSY-UHFFFAOYSA-N phenylmercuric borate Chemical compound OB(O)O[Hg]C1=CC=CC=C1 VUXSPDNLYQTOSY-UHFFFAOYSA-N 0.000 description 1
- 229960000247 phenylmercuric borate Drugs 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
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- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
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- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
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- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
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- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/10—1,2,5-Thiadiazoles; Hydrogenated 1,2,5-thiadiazoles
-
- 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
-
- 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
- A61P27/06—Antiglaucoma agents or miotics
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Ophthalmology & Optometry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cephalosporin Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12233880A | 1980-02-19 | 1980-02-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ196227A true NZ196227A (en) | 1984-09-28 |
Family
ID=22402132
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ196227A NZ196227A (en) | 1980-02-19 | 1981-02-10 | 1,2,5-thiadiazole derivative and ophthalmic compositions |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP0034542B1 (enExample) |
| JP (1) | JPS56131575A (enExample) |
| AT (1) | ATE15193T1 (enExample) |
| AU (1) | AU540656B2 (enExample) |
| DE (1) | DE3171965D1 (enExample) |
| DK (1) | DK70981A (enExample) |
| ES (1) | ES499570A0 (enExample) |
| GR (1) | GR74105B (enExample) |
| IE (1) | IE50923B1 (enExample) |
| NZ (1) | NZ196227A (enExample) |
| PT (1) | PT72515B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2106852T3 (es) * | 1992-07-08 | 1997-11-16 | Santen Oy | Composicion oftalmica que contiene hemihidrato de timolol. |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3657237A (en) * | 1968-05-22 | 1972-04-18 | Frosst & Co Charles E | Process for making 1 2 5-thiadiazoles in the sinister configuration |
| GB1253709A (en) * | 1968-05-22 | 1971-11-17 | Frosst & Co Charles E | Thiadiazole derivatives |
| US3833727A (en) * | 1972-03-06 | 1974-09-03 | Merck & Co Inc | Hydralazine and beta-adrenergic blocking agent compositions for treating hypertension |
| GB1429420A (en) * | 1974-06-05 | 1976-03-24 | Merck Sharp & Dohme | Thiadiazole derivatives |
| DE2428030A1 (de) * | 1974-06-11 | 1976-01-02 | Merck Sharp & Dohme | Substituierte thiadiazole und verfahren zu ihrer herstellung |
| CH597209A5 (en) * | 1974-06-18 | 1978-03-31 | Merck Sharp & Dohme | 4-(3-Amino-2-acyloxypropoxyl)-1,2,5-thiadiazoles |
| FR2277581A1 (fr) * | 1974-07-09 | 1976-02-06 | Merck Sharp & Dohme | Thiadiazoles substitues et procede pour leur preparation |
-
1981
- 1981-02-10 AU AU67131/81A patent/AU540656B2/en not_active Ceased
- 1981-02-10 NZ NZ196227A patent/NZ196227A/en unknown
- 1981-02-16 GR GR64155A patent/GR74105B/el unknown
- 1981-02-17 IE IE310/81A patent/IE50923B1/en not_active IP Right Cessation
- 1981-02-17 PT PT72515A patent/PT72515B/pt not_active IP Right Cessation
- 1981-02-18 DK DK70981A patent/DK70981A/da not_active Application Discontinuation
- 1981-02-18 AT AT81400251T patent/ATE15193T1/de not_active IP Right Cessation
- 1981-02-18 EP EP81400251A patent/EP0034542B1/en not_active Expired
- 1981-02-18 DE DE8181400251T patent/DE3171965D1/de not_active Expired
- 1981-02-18 ES ES499570A patent/ES499570A0/es active Granted
- 1981-02-19 JP JP2229981A patent/JPS56131575A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| AU6713181A (en) | 1981-08-27 |
| ES8205795A1 (es) | 1982-07-01 |
| EP0034542A2 (en) | 1981-08-26 |
| AU540656B2 (en) | 1984-11-29 |
| EP0034542B1 (en) | 1985-08-28 |
| ES499570A0 (es) | 1982-07-01 |
| EP0034542A3 (en) | 1981-10-21 |
| GR74105B (enExample) | 1984-06-06 |
| PT72515B (en) | 1982-12-20 |
| IE50923B1 (en) | 1986-08-20 |
| JPS56131575A (en) | 1981-10-15 |
| DE3171965D1 (en) | 1985-10-03 |
| DK70981A (da) | 1981-08-20 |
| PT72515A (en) | 1981-03-01 |
| ATE15193T1 (de) | 1985-09-15 |
| IE810310L (en) | 1981-08-19 |
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