AU2007249443B2 - Isothiazolidines useful in the treatment of ocular hypertensive conditions - Google Patents
Isothiazolidines useful in the treatment of ocular hypertensive conditions Download PDFInfo
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- AU2007249443B2 AU2007249443B2 AU2007249443A AU2007249443A AU2007249443B2 AU 2007249443 B2 AU2007249443 B2 AU 2007249443B2 AU 2007249443 A AU2007249443 A AU 2007249443A AU 2007249443 A AU2007249443 A AU 2007249443A AU 2007249443 B2 AU2007249443 B2 AU 2007249443B2
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- Prior art keywords
- compound
- compound according
- carbon atoms
- another embodiment
- phenyl
- Prior art date
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- 206010020772 Hypertension Diseases 0.000 title description 3
- 230000001631 hypertensive effect Effects 0.000 title description 2
- 150000000001 isothiazolidines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 288
- 150000003839 salts Chemical class 0.000 claims abstract description 33
- 239000000203 mixture Substances 0.000 claims abstract description 27
- 239000000651 prodrug Substances 0.000 claims abstract description 20
- 229940002612 prodrug Drugs 0.000 claims abstract description 20
- 239000003814 drug Substances 0.000 claims abstract description 15
- -1 6-hexyl Chemical group 0.000 claims description 86
- 125000004432 carbon atom Chemical group C* 0.000 claims description 43
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 208000010412 Glaucoma Diseases 0.000 claims description 20
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- 241000124008 Mammalia Species 0.000 claims description 13
- 150000002148 esters Chemical class 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 150000001408 amides Chemical class 0.000 claims description 11
- 125000000524 functional group Chemical group 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 10
- 206010030043 Ocular hypertension Diseases 0.000 claims description 9
- 239000004305 biphenyl Substances 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 235000010290 biphenyl Nutrition 0.000 claims description 8
- 125000003107 substituted aryl group Chemical group 0.000 claims description 8
- 150000007524 organic acids Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 101100294102 Caenorhabditis elegans nhr-2 gene Proteins 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 abstract 1
- 235000002639 sodium chloride Nutrition 0.000 description 30
- 239000000243 solution Substances 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 22
- 125000001424 substituent group Chemical group 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 20
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 19
- 125000003118 aryl group Chemical group 0.000 description 18
- 239000000460 chlorine Substances 0.000 description 16
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 14
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropyl acetate Chemical compound CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 238000003818 flash chromatography Methods 0.000 description 11
- 239000000741 silica gel Substances 0.000 description 11
- 229910002027 silica gel Inorganic materials 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- WISDYGSXRXTPNI-UHFFFAOYSA-N 1-phenylmethoxybut-3-en-2-yl acetate Chemical compound CC(=O)OC(C=C)COCC1=CC=CC=C1 WISDYGSXRXTPNI-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 239000012267 brine Substances 0.000 description 10
- 235000019439 ethyl acetate Nutrition 0.000 description 10
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- 238000000746 purification Methods 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 125000004429 atom Chemical group 0.000 description 7
- 125000004122 cyclic group Chemical group 0.000 description 7
- 230000000670 limiting effect Effects 0.000 description 7
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- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 125000000304 alkynyl group Chemical group 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000010502 orange oil Substances 0.000 description 6
- 150000003180 prostaglandins Chemical class 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 235000019502 Orange oil Nutrition 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 150000001768 cations Chemical class 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 239000003755 preservative agent Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 4
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 4
- JNGIREYWMBEJFN-UHFFFAOYSA-N 3-hydroxy-4-phenylmethoxybutane-1-sulfonamide Chemical compound NS(=O)(=O)CCC(O)COCC1=CC=CC=C1 JNGIREYWMBEJFN-UHFFFAOYSA-N 0.000 description 4
- VUTBELPREDJDDH-UHFFFAOYSA-N 4-amino-5-hydroxymethyl-2-methylpyrimidine Chemical compound CC1=NC=C(CO)C(N)=N1 VUTBELPREDJDDH-UHFFFAOYSA-N 0.000 description 4
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
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- 239000000839 emulsion Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- KVUVQIGYQVNEFH-UHFFFAOYSA-N methyl 5-[[2-(4-hexanoylphenyl)-1,1-dioxo-1,2-thiazolidin-3-yl]oxymethyl]thiophene-2-carboxylate Chemical compound C1=CC(C(=O)CCCCC)=CC=C1N1S(=O)(=O)CCC1OCC1=CC=C(C(=O)OC)S1 KVUVQIGYQVNEFH-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- 239000003981 vehicle Substances 0.000 description 4
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 201000002862 Angle-Closure Glaucoma Diseases 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 230000001154 acute effect Effects 0.000 description 3
- 210000002159 anterior chamber Anatomy 0.000 description 3
- 210000001742 aqueous humor Anatomy 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000002738 chelating agent Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 231100000252 nontoxic Toxicity 0.000 description 3
- 230000003000 nontoxic effect Effects 0.000 description 3
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- 239000007858 starting material Substances 0.000 description 3
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 3
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- GDMWWRUTCBSAFE-UHFFFAOYSA-N (1,1-dioxo-1,2-thiazolidin-3-yl)methanol Chemical compound OCC1CCS(=O)(=O)N1 GDMWWRUTCBSAFE-UHFFFAOYSA-N 0.000 description 2
- PXGPLTODNUVGFL-BRIYLRKRSA-N (E,Z)-(1R,2R,3R,5S)-7-(3,5-Dihydroxy-2-((3S)-(3-hydroxy-1-octenyl))cyclopentyl)-5-heptenoic acid Chemical compound CCCCC[C@H](O)C=C[C@H]1[C@H](O)C[C@H](O)[C@@H]1CC=CCCCC(O)=O PXGPLTODNUVGFL-BRIYLRKRSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
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- ZCRRABZFLYWNOM-UHFFFAOYSA-N 3-(phenylmethoxymethyl)-1,2-thiazolidine 1,1-dioxide Chemical compound N1S(=O)(=O)CCC1COCC1=CC=CC=C1 ZCRRABZFLYWNOM-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 208000002177 Cataract Diseases 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
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- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
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- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
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- 229960000281 trometamol Drugs 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 230000004393 visual impairment Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61P27/06—Antiglaucoma agents or miotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
- C07D275/06—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to the ring sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Ophthalmology & Optometry (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US74711506P | 2006-05-12 | 2006-05-12 | |
| US60/747,115 | 2006-05-12 | ||
| US11/745,317 US7557095B2 (en) | 2006-05-12 | 2007-05-07 | Therapeutic compounds |
| US11/745,317 | 2007-05-07 | ||
| PCT/US2007/068518 WO2007134085A2 (en) | 2006-05-12 | 2007-05-09 | Isothiazolidines useful in the treatment of ocular hypertensive conditions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2007249443A1 AU2007249443A1 (en) | 2007-11-22 |
| AU2007249443B2 true AU2007249443B2 (en) | 2012-09-27 |
Family
ID=38606676
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2007249443A Ceased AU2007249443B2 (en) | 2006-05-12 | 2007-05-09 | Isothiazolidines useful in the treatment of ocular hypertensive conditions |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US7557095B2 (enExample) |
| EP (1) | EP2044041A2 (enExample) |
| JP (1) | JP2009536967A (enExample) |
| AU (1) | AU2007249443B2 (enExample) |
| BR (1) | BRPI0711461A2 (enExample) |
| CA (1) | CA2652866A1 (enExample) |
| WO (1) | WO2007134085A2 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7557095B2 (en) * | 2006-05-12 | 2009-07-07 | Allergan, Inc. | Therapeutic compounds |
| US7960379B2 (en) * | 2008-03-14 | 2011-06-14 | Allergan, Inc. | Therapeutic compounds |
| US8314250B2 (en) * | 2009-11-24 | 2012-11-20 | Hoffmann-La Roche Inc. | Sultam derivatives |
| EP2531493B1 (en) | 2010-02-01 | 2015-07-22 | Basf Se | Substituted ketonic isoxazoline compounds and derivatives for combating animal pests |
| JP2013540116A (ja) | 2010-10-01 | 2013-10-31 | ビーエーエスエフ ソシエタス・ヨーロピア | 殺有害生物剤としてのイミン置換−２，４−ジアリール−ピロリン誘導体 |
| AR084486A1 (es) | 2010-10-01 | 2013-05-22 | Basf Se | Compuestos de imina |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995029904A1 (en) * | 1994-04-29 | 1995-11-09 | Allergan | Substituted thiazole sulfonamides as antiglaucoma agents |
| WO1997003973A1 (en) * | 1995-07-21 | 1997-02-06 | Fujisawa Pharmaceutical Co., Ltd. | 4,5-diaryl oxazole derivatives |
| US20020032222A1 (en) * | 2000-07-17 | 2002-03-14 | American Home Products Corporation | Azolidines as beta-3 adrenergic receptor agonists |
| US6476064B1 (en) * | 2001-06-13 | 2002-11-05 | Allergan, Inc. | Cyclopentane heptan(ene) acyl sulfonamide, 2-alkyl or 2-arylalkyl, or 2-heteroarylalkenyl derivatives as therapeutic agents |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5462968A (en) * | 1994-01-19 | 1995-10-31 | Allergan, Inc. | EP2 -receptor agonists as agents for lowering intraocular pressure |
| US5902726A (en) * | 1994-12-23 | 1999-05-11 | Glaxo Wellcome Inc. | Activators of the nuclear orphan receptor peroxisome proliferator-activated receptor gamma |
| US5877211A (en) * | 1997-11-21 | 1999-03-02 | Allergan | EP2 receptor agonists as neuroprotective agents for the eye |
| US6927216B2 (en) * | 2000-10-03 | 2005-08-09 | Bristol-Myers Squibb Pharma Company | Cyclic sulfonyl compounds as inhibitors of metalloproteases |
| EP1439837B1 (en) * | 2001-10-23 | 2008-04-09 | Laboratoires Serono SA | Pyrazolidinone compounds as ligands of the prostaglandin ep2 and/or ep4 receptors |
| ES2337887T3 (es) * | 2001-12-20 | 2010-04-30 | Merck Serono Sa | Derivados de pirrolidina en calidad de moduladores de prostaglandina. |
| NZ535024A (en) * | 2002-03-05 | 2006-10-27 | Ono Pharmaceutical Co | 8-azaprostaglandin derivative compound and agent comprising the compound as active ingredient |
| JP2005104836A (ja) * | 2003-08-08 | 2005-04-21 | Ono Pharmaceut Co Ltd | プロスタグランジン誘導体 |
| US7557095B2 (en) * | 2006-05-12 | 2009-07-07 | Allergan, Inc. | Therapeutic compounds |
| US7960379B2 (en) * | 2008-03-14 | 2011-06-14 | Allergan, Inc. | Therapeutic compounds |
-
2007
- 2007-05-07 US US11/745,317 patent/US7557095B2/en active Active
- 2007-05-09 JP JP2009511159A patent/JP2009536967A/ja active Pending
- 2007-05-09 WO PCT/US2007/068518 patent/WO2007134085A2/en not_active Ceased
- 2007-05-09 AU AU2007249443A patent/AU2007249443B2/en not_active Ceased
- 2007-05-09 BR BRPI0711461-3A patent/BRPI0711461A2/pt not_active IP Right Cessation
- 2007-05-09 EP EP07762032A patent/EP2044041A2/en not_active Withdrawn
- 2007-05-09 CA CA002652866A patent/CA2652866A1/en not_active Abandoned
-
2009
- 2009-06-02 US US12/476,467 patent/US7897629B2/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995029904A1 (en) * | 1994-04-29 | 1995-11-09 | Allergan | Substituted thiazole sulfonamides as antiglaucoma agents |
| WO1997003973A1 (en) * | 1995-07-21 | 1997-02-06 | Fujisawa Pharmaceutical Co., Ltd. | 4,5-diaryl oxazole derivatives |
| US20020032222A1 (en) * | 2000-07-17 | 2002-03-14 | American Home Products Corporation | Azolidines as beta-3 adrenergic receptor agonists |
| US6476064B1 (en) * | 2001-06-13 | 2002-11-05 | Allergan, Inc. | Cyclopentane heptan(ene) acyl sulfonamide, 2-alkyl or 2-arylalkyl, or 2-heteroarylalkenyl derivatives as therapeutic agents |
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0711461A2 (pt) | 2011-11-08 |
| AU2007249443A1 (en) | 2007-11-22 |
| CA2652866A1 (en) | 2007-11-22 |
| US7897629B2 (en) | 2011-03-01 |
| WO2007134085A2 (en) | 2007-11-22 |
| US7557095B2 (en) | 2009-07-07 |
| US20070265321A1 (en) | 2007-11-15 |
| US20090247594A1 (en) | 2009-10-01 |
| JP2009536967A (ja) | 2009-10-22 |
| WO2007134085A3 (en) | 2008-01-10 |
| EP2044041A2 (en) | 2009-04-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |