HRP990259A2 - Polymorf of zopolrestat monohydrate - Google Patents
Polymorf of zopolrestat monohydrate Download PDFInfo
- Publication number
- HRP990259A2 HRP990259A2 HR990259A HRP990259A HRP990259A2 HR P990259 A2 HRP990259 A2 HR P990259A2 HR 990259 A HR990259 A HR 990259A HR P990259 A HRP990259 A HR P990259A HR P990259 A2 HRP990259 A2 HR P990259A2
- Authority
- HR
- Croatia
- Prior art keywords
- dihydro
- oxo
- trifluoromethyl
- benzothiazolyl
- mammal
- Prior art date
Links
- 229950005346 zopolrestat Drugs 0.000 title description 57
- -1 zopolrestat monohydrate Chemical class 0.000 title description 40
- 238000000034 method Methods 0.000 claims description 71
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 55
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 39
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 38
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 29
- 241000124008 Mammalia Species 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 18
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- CHRHIMURNMPPRB-UHFFFAOYSA-M sodium;2-[4-oxo-3-[[5-(trifluoromethyl)-1,3-benzothiazol-2-yl]methyl]phthalazin-1-yl]acetate Chemical compound [Na+].O=C1C2=CC=CC=C2C(CC(=O)[O-])=NN1CC1=NC2=CC(C(F)(F)F)=CC=C2S1 CHRHIMURNMPPRB-UHFFFAOYSA-M 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 206010012601 diabetes mellitus Diseases 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 239000003021 water soluble solvent Substances 0.000 claims description 11
- 239000008280 blood Substances 0.000 claims description 10
- 210000004369 blood Anatomy 0.000 claims description 10
- 238000001914 filtration Methods 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 239000002798 polar solvent Substances 0.000 claims description 9
- 239000003085 diluting agent Substances 0.000 claims description 8
- 239000003937 drug carrier Substances 0.000 claims description 8
- 238000001035 drying Methods 0.000 claims description 8
- 102000016912 Aldehyde Reductase Human genes 0.000 claims description 7
- 108010053754 Aldehyde reductase Proteins 0.000 claims description 7
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 claims description 6
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 claims description 6
- 150000007522 mineralic acids Chemical class 0.000 claims description 6
- 150000004682 monohydrates Chemical class 0.000 claims description 6
- 229940116269 uric acid Drugs 0.000 claims description 6
- 208000032781 Diabetic cardiomyopathy Diseases 0.000 claims description 5
- 238000002441 X-ray diffraction Methods 0.000 claims description 5
- 230000002401 inhibitory effect Effects 0.000 claims description 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 210000001519 tissue Anatomy 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 4
- 150000002632 lipids Chemical class 0.000 claims description 4
- 230000002265 prevention Effects 0.000 claims description 4
- 206010002383 Angina Pectoris Diseases 0.000 claims description 3
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims description 3
- 230000003683 cardiac damage Effects 0.000 claims description 3
- 230000006378 damage Effects 0.000 claims description 3
- 208000033679 diabetic kidney disease Diseases 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- 210000005003 heart tissue Anatomy 0.000 claims description 3
- 238000001953 recrystallisation Methods 0.000 claims description 3
- 230000000451 tissue damage Effects 0.000 claims description 3
- 231100000827 tissue damage Toxicity 0.000 claims description 3
- 210000004556 brain Anatomy 0.000 claims description 2
- 230000000747 cardiac effect Effects 0.000 claims description 2
- 125000004494 ethyl ester group Chemical group 0.000 claims description 2
- 230000000968 intestinal effect Effects 0.000 claims description 2
- 210000000936 intestine Anatomy 0.000 claims description 2
- 208000028867 ischemia Diseases 0.000 claims description 2
- 230000000302 ischemic effect Effects 0.000 claims description 2
- 210000003734 kidney Anatomy 0.000 claims description 2
- 210000004185 liver Anatomy 0.000 claims description 2
- 210000004072 lung Anatomy 0.000 claims description 2
- 208000031225 myocardial ischemia Diseases 0.000 claims description 2
- 210000004165 myocardium Anatomy 0.000 claims description 2
- 210000000496 pancreas Anatomy 0.000 claims description 2
- 230000002207 retinal effect Effects 0.000 claims description 2
- 210000002027 skeletal muscle Anatomy 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims 8
- 229940079593 drug Drugs 0.000 claims 3
- 230000005764 inhibitory process Effects 0.000 claims 1
- 210000000952 spleen Anatomy 0.000 claims 1
- 239000000243 solution Substances 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
- BCSVCWVQNOXFGL-UHFFFAOYSA-N 3,4-dihydro-4-oxo-3-((5-trifluoromethyl-2-benzothiazolyl)methyl)-1-phthalazine acetic acid Chemical compound O=C1C2=CC=CC=C2C(CC(=O)O)=NN1CC1=NC2=CC(C(F)(F)F)=CC=C2S1 BCSVCWVQNOXFGL-UHFFFAOYSA-N 0.000 description 14
- 239000002002 slurry Substances 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 206010007749 Cataract diabetic Diseases 0.000 description 3
- 208000032131 Diabetic Neuropathies Diseases 0.000 description 3
- 206010012689 Diabetic retinopathy Diseases 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 201000007025 diabetic cataract Diseases 0.000 description 3
- 230000007823 neuropathy Effects 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229940118148 Aldose reductase inhibitor Drugs 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 208000002249 Diabetes Complications Diseases 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 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 1
- 239000004705 High-molecular-weight polyethylene Substances 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 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
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 244000000231 Sesamum indicum Species 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- FIAGYDIJZOWVAB-UHFFFAOYSA-N [2-sulfanyl-5-(trifluoromethyl)phenyl]azanium;chloride Chemical compound Cl.NC1=CC(C(F)(F)F)=CC=C1S FIAGYDIJZOWVAB-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003288 aldose reductase inhibitor Substances 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000009499 grossing Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 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
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Hematology (AREA)
- Vascular Medicine (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Steroid Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9747498P | 1998-08-21 | 1998-08-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP990259A2 true HRP990259A2 (en) | 2000-06-30 |
Family
ID=22263562
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR990259A HRP990259A2 (en) | 1998-08-21 | 1999-08-20 | Polymorf of zopolrestat monohydrate |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US6159976A (ko) |
| EP (1) | EP0982306A3 (ko) |
| JP (1) | JP2000072769A (ko) |
| KR (1) | KR20000017411A (ko) |
| CN (1) | CN1245804A (ko) |
| AP (1) | AP9901662A0 (ko) |
| AU (1) | AU4453299A (ko) |
| BG (1) | BG103674A (ko) |
| BR (1) | BR9903873A (ko) |
| CA (1) | CA2280590A1 (ko) |
| EA (1) | EA199900675A3 (ko) |
| EE (1) | EE9900385A (ko) |
| GT (1) | GT199900137A (ko) |
| HR (1) | HRP990259A2 (ko) |
| HU (1) | HUP9902783A3 (ko) |
| ID (1) | ID23307A (ko) |
| IL (1) | IL131419A0 (ko) |
| IS (1) | IS5155A (ko) |
| MA (1) | MA26678A1 (ko) |
| NO (1) | NO994027L (ko) |
| NZ (1) | NZ337363A (ko) |
| OA (1) | OA11150A (ko) |
| PA (1) | PA8480601A1 (ko) |
| PE (1) | PE20000993A1 (ko) |
| PL (1) | PL335016A1 (ko) |
| SG (1) | SG83147A1 (ko) |
| TN (1) | TNSN99159A1 (ko) |
| TR (1) | TR199901996A2 (ko) |
| UY (1) | UY25668A1 (ko) |
| YU (1) | YU39899A (ko) |
| ZA (1) | ZA995297B (ko) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5934206B2 (ja) | 2010-07-16 | 2016-06-15 | ザ・トラスティーズ・オブ・コロンビア・ユニバーシティ・イン・ザ・シティ・オブ・ニューヨーク | アルドース還元酵素阻害剤および同使用方法 |
| US8916563B2 (en) | 2010-07-16 | 2014-12-23 | The Trustees Of Columbia University In The City Of New York | Aldose reductase inhibitors and uses thereof |
| US20140228319A1 (en) * | 2013-02-13 | 2014-08-14 | Banavara L. Mylari | Water soluble salts of aldose reductase inhibitors for treatment of diabetic complications |
| ES2836500T3 (es) | 2016-06-21 | 2021-06-25 | Univ Columbia | Inhibidores de aldosa reductasa y métodos de uso de los mismos |
| US11590131B2 (en) | 2017-07-28 | 2023-02-28 | Applied Therapeutics, Inc. | Compositions and methods for treating galactosemia |
| SG11202110590PA (en) | 2019-04-01 | 2021-10-28 | Applied Therapeutics Inc | Inhibitors of aldose reductase |
| WO2021202523A1 (en) | 2020-03-31 | 2021-10-07 | Applied Therapeutics, Inc. | Aldose reductase inhibitors for the treatment of acute respiratory distress syndrome, acute lung inflammation/injury, cardiac injury and anti-viral therapy |
| CN115996725A (zh) | 2020-05-01 | 2023-04-21 | 应用治疗公司 | 用于治疗山梨糖醇脱氢酶缺乏症的醛糖还原酶抑制剂 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4939140A (en) * | 1985-11-07 | 1990-07-03 | Pfizer Inc. | Heterocyclic oxophthalazinyl acetic acids |
| US4748280A (en) * | 1985-11-07 | 1988-05-31 | Pfizer Inc. | Certain chlorination process for preparing 2-chloro-1,1,1-(C1 -C6) |
| JPH0676391B2 (ja) * | 1987-06-09 | 1994-09-28 | フアイザー・インコーポレイテツド | ベンゾチアゾール等の複素環側鎖を有するオキソフタラジニル酢酸類の製造方法 |
| US4868301A (en) * | 1987-06-09 | 1989-09-19 | Pfizer Inc. | Processes and intermediates for the preparation of oxophthalazinyl acetic acids having benzothiazole or other heterocyclic side chains |
| US4904782A (en) * | 1988-02-29 | 1990-02-27 | Pfizer Inc. | Process for the production of phthalazineacetic acid ester derivatives and a novel intermediate |
| US4954629A (en) * | 1989-05-11 | 1990-09-04 | Pfizer Inc. | Process and intermediates for the preparation of oxophthalazinyl acetic acids and analogs thereof |
| WO1992003432A1 (en) * | 1990-08-28 | 1992-03-05 | Pfizer Inc. | 3-(5-trifluoromethylbenzothiazol-2-ylmethyl)-4-oxo-3h-phythalazin-1-ylacetic acid monohydrate |
| US5391551A (en) * | 1993-05-10 | 1995-02-21 | Pfizer Inc. | Method of lowering blood lipid levels |
| US6127367A (en) * | 1996-02-29 | 2000-10-03 | Pfizer, Inc. | Method of reducing tissue damage associated with non-cardiac ischemia |
-
1999
- 1999-08-06 EP EP99306252A patent/EP0982306A3/en not_active Withdrawn
- 1999-08-13 US US09/374,729 patent/US6159976A/en not_active Expired - Fee Related
- 1999-08-16 IL IL13141999A patent/IL131419A0/xx unknown
- 1999-08-17 IS IS5155A patent/IS5155A/is unknown
- 1999-08-17 AU AU44532/99A patent/AU4453299A/en not_active Abandoned
- 1999-08-18 TN TNTNSN99159A patent/TNSN99159A1/fr unknown
- 1999-08-18 MA MA25738A patent/MA26678A1/fr unknown
- 1999-08-19 UY UY25668A patent/UY25668A1/es not_active Application Discontinuation
- 1999-08-19 HU HU9902783A patent/HUP9902783A3/hu unknown
- 1999-08-19 OA OA9900185A patent/OA11150A/en unknown
- 1999-08-19 GT GT199900137A patent/GT199900137A/es unknown
- 1999-08-19 ZA ZA9905297A patent/ZA995297B/xx unknown
- 1999-08-19 CA CA002280590A patent/CA2280590A1/en not_active Abandoned
- 1999-08-19 EE EEP199900385A patent/EE9900385A/xx unknown
- 1999-08-19 YU YU39899A patent/YU39899A/sh unknown
- 1999-08-19 SG SG9904131A patent/SG83147A1/en unknown
- 1999-08-19 AP APAP/P/1999/001662A patent/AP9901662A0/en unknown
- 1999-08-20 EA EA199900675A patent/EA199900675A3/ru unknown
- 1999-08-20 PE PE1999000844A patent/PE20000993A1/es not_active Application Discontinuation
- 1999-08-20 BR BR9903873-0A patent/BR9903873A/pt not_active Application Discontinuation
- 1999-08-20 HR HR990259A patent/HRP990259A2/hr not_active Application Discontinuation
- 1999-08-20 KR KR1019990034527A patent/KR20000017411A/ko not_active Application Discontinuation
- 1999-08-20 TR TR1999/01996A patent/TR199901996A2/xx unknown
- 1999-08-20 NZ NZ337363A patent/NZ337363A/xx unknown
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- 1999-08-23 CN CN99118068A patent/CN1245804A/zh active Pending
- 1999-08-23 JP JP11235855A patent/JP2000072769A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| HUP9902783A2 (hu) | 2000-12-28 |
| CA2280590A1 (en) | 2000-02-21 |
| PA8480601A1 (es) | 2000-09-29 |
| EP0982306A3 (en) | 2000-07-05 |
| BR9903873A (pt) | 2000-09-19 |
| AU4453299A (en) | 2000-03-09 |
| EA199900675A2 (ru) | 2000-02-28 |
| TNSN99159A1 (fr) | 2005-11-10 |
| OA11150A (en) | 2003-04-16 |
| EA199900675A3 (ru) | 2000-06-26 |
| TR199901996A2 (xx) | 2000-03-21 |
| AP9901662A0 (en) | 1999-09-30 |
| KR20000017411A (ko) | 2000-03-25 |
| YU39899A (sh) | 2002-12-10 |
| PE20000993A1 (es) | 2000-10-04 |
| IL131419A0 (en) | 2001-01-28 |
| ZA995297B (en) | 2001-02-19 |
| NO994027D0 (no) | 1999-08-20 |
| NO994027L (no) | 2000-02-22 |
| PL335016A1 (en) | 2000-02-28 |
| EE9900385A (et) | 2000-04-17 |
| UY25668A1 (es) | 2001-08-27 |
| MA26678A1 (fr) | 2004-12-20 |
| US6159976A (en) | 2000-12-12 |
| NZ337363A (en) | 2001-01-26 |
| CN1245804A (zh) | 2000-03-01 |
| GT199900137A (es) | 2001-02-09 |
| ID23307A (id) | 2000-04-05 |
| JP2000072769A (ja) | 2000-03-07 |
| BG103674A (en) | 2000-03-31 |
| IS5155A (is) | 2000-02-22 |
| HUP9902783A3 (en) | 2001-01-29 |
| SG83147A1 (en) | 2001-09-18 |
| EP0982306A2 (en) | 2000-03-01 |
| HU9902783D0 (en) | 1999-10-28 |
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