OA11150A - Polymorph of zopolrestat monohydrate - Google Patents

Polymorph of zopolrestat monohydrate Download PDF

Info

Publication number: OA11150A
Authority: OA; OAPI
Prior art keywords: solution; dihydro; oxo; benzothiazolyl; methyl
Prior art date: 1998-08-21

Application number

OA9900185A

Other languages

English (en)

Inventor

John Francis Lambert

Timothy Norris

Original Assignee

Pfizer Prod Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1998-08-21

Filing date

1999-08-19

Publication date

2003-04-16

1999-08-19 Application filed by Pfizer Prod Inc filed Critical Pfizer Prod Inc

2003-04-16 Publication of OA11150A publication Critical patent/OA11150A/en

Links

-1 zopolrestat monohydrate Chemical class 0.000 title claims abstract description 31
229950005346 zopolrestat Drugs 0.000 title abstract description 47
238000000034 method Methods 0.000 claims abstract description 48
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 claims abstract description 17
239000000203 mixture Substances 0.000 claims abstract description 12
239000008280 blood Substances 0.000 claims abstract description 9
210000004369 blood Anatomy 0.000 claims abstract description 9
LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 claims abstract description 5
150000002632 lipids Chemical class 0.000 claims abstract description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 48
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 35
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 35
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 28
150000001875 compounds Chemical class 0.000 claims description 19
241000124008 Mammalia Species 0.000 claims description 17
229940093499 ethyl acetate Drugs 0.000 claims description 16
235000019439 ethyl acetate Nutrition 0.000 claims description 16
238000004519 manufacturing process Methods 0.000 claims description 16
239000003021 water soluble solvent Substances 0.000 claims description 13
239000011734 sodium Substances 0.000 claims description 10
229910052708 sodium Inorganic materials 0.000 claims description 10
239000002798 polar solvent Substances 0.000 claims description 9
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 9
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 claims description 8
239000003085 diluting agent Substances 0.000 claims description 8
238000001035 drying Methods 0.000 claims description 8
239000008194 pharmaceutical composition Substances 0.000 claims description 8
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 7
102000016912 Aldehyde Reductase Human genes 0.000 claims description 5
108010053754 Aldehyde reductase Proteins 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
150000007522 mineralic acids Chemical class 0.000 claims description 5
150000004682 monohydrates Chemical class 0.000 claims description 5
239000007787 solid Substances 0.000 claims description 5
238000010438 heat treatment Methods 0.000 claims description 4
230000002401 inhibitory effect Effects 0.000 claims description 4
ANGLUYKTDCFFSI-UHFFFAOYSA-N 2-[4-oxo-3-[[5-(trifluoromethyl)-1,3-benzothiazol-2-yl]methyl]phthalazin-1-yl]acetic acid;hydrate Chemical compound O.O=C1C2=CC=CC=C2C(CC(=O)O)=NN1CC1=NC2=CC(C(F)(F)F)=CC=C2S1 ANGLUYKTDCFFSI-UHFFFAOYSA-N 0.000 claims description 3
TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 claims description 3
230000000694 effects Effects 0.000 claims description 3
229940116269 uric acid Drugs 0.000 claims description 3
206010002383 Angina Pectoris Diseases 0.000 claims description 2
208000007342 Diabetic Nephropathies Diseases 0.000 claims description 2
208000032781 Diabetic cardiomyopathy Diseases 0.000 claims description 2
208000033679 diabetic kidney disease Diseases 0.000 claims description 2
238000000634 powder X-ray diffraction Methods 0.000 claims description 2
230000000451 tissue damage Effects 0.000 claims description 2
231100000827 tissue damage Toxicity 0.000 claims description 2
SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 1
150000001323 aldoses Chemical class 0.000 claims 1
230000003683 cardiac damage Effects 0.000 claims 1
210000005003 heart tissue Anatomy 0.000 claims 1
206010007749 Cataract diabetic Diseases 0.000 abstract description 2
201000007025 diabetic cataract Diseases 0.000 abstract description 2
208000002249 Diabetes Complications Diseases 0.000 abstract 1
208000032131 Diabetic Neuropathies Diseases 0.000 abstract 1
206010012655 Diabetic complications Diseases 0.000 abstract 1
206010012689 Diabetic retinopathy Diseases 0.000 abstract 1
239000000243 solution Substances 0.000 description 31
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
239000002002 slurry Substances 0.000 description 11
238000001914 filtration Methods 0.000 description 8
239000002904 solvent Substances 0.000 description 8
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
239000013078 crystal Substances 0.000 description 6
239000002253 acid Substances 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
239000000047 product Substances 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
238000002441 X-ray diffraction Methods 0.000 description 4
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
230000006378 damage Effects 0.000 description 3
201000001119 neuropathy Diseases 0.000 description 3
230000007823 neuropathy Effects 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
208000033808 peripheral neuropathy Diseases 0.000 description 3
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
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
208000017442 Retinal disease Diseases 0.000 description 2
206010038923 Retinopathy Diseases 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
150000007942 carboxylates Chemical class 0.000 description 2
239000000969 carrier Substances 0.000 description 2
206010012601 diabetes mellitus Diseases 0.000 description 2
239000000945 filler Substances 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
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
239000000126 substance Substances 0.000 description 2
239000003826 tablet Substances 0.000 description 2
MVTRQRSNYWDWMY-UHFFFAOYSA-N 2-amino-4-(trifluoromethyl)benzenethiol Chemical compound NC1=CC(C(F)(F)F)=CC=C1S MVTRQRSNYWDWMY-UHFFFAOYSA-N 0.000 description 1
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
208000002177 Cataract Diseases 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
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
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
244000000231 Sesamum indicum Species 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
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
239000007900 aqueous suspension Substances 0.000 description 1
101150099875 atpE gene Proteins 0.000 description 1
101150018639 atpFH gene Proteins 0.000 description 1
101150048329 atpH gene Proteins 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
210000004556 brain Anatomy 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
230000000747 cardiac effect Effects 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000004040 coloring Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
239000000975 dye Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
210000001035 gastrointestinal tract Anatomy 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
239000000543 intermediate Substances 0.000 description 1
230000000968 intestinal effect Effects 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
208000028867 ischemia Diseases 0.000 description 1
229960004592 isopropanol Drugs 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
239000008101 lactose Substances 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
208000031225 myocardial ischemia Diseases 0.000 description 1
210000004165 myocardium Anatomy 0.000 description 1
238000010979 pH adjustment Methods 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000002207 retinal effect Effects 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
210000002027 skeletal muscle Anatomy 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000007858 starting material 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
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)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Diabetes (AREA)
Heart & Thoracic Surgery (AREA)
Urology & Nephrology (AREA)
Hematology (AREA)
Obesity (AREA)
Cardiology (AREA)
Vascular Medicine (AREA)
Endocrinology (AREA)
Emergency Medicine (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)

OA9900185A 1998-08-21 1999-08-19 Polymorph of zopolrestat monohydrate OA11150A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US9747498P	1998-08-21	1998-08-21

Publications (1)

Publication Number	Publication Date
OA11150A true OA11150A (en)	2003-04-16

Family

ID=22263562

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA9900185A OA11150A (en)	1998-08-21	1999-08-19	Polymorph of zopolrestat monohydrate

Country Status (31)

Country	Link
US (1)	US6159976A (is)
EP (1)	EP0982306A3 (is)
JP (1)	JP2000072769A (is)
KR (1)	KR20000017411A (is)
CN (1)	CN1245804A (is)
AP (1)	AP9901662A0 (is)
AU (1)	AU4453299A (is)
BG (1)	BG103674A (is)
BR (1)	BR9903873A (is)
CA (1)	CA2280590A1 (is)
EA (1)	EA199900675A3 (is)
EE (1)	EE9900385A (is)
GT (1)	GT199900137A (is)
HR (1)	HRP990259A2 (is)
HU (1)	HUP9902783A3 (is)
ID (1)	ID23307A (is)
IL (1)	IL131419A0 (is)
IS (1)	IS5155A (is)
MA (1)	MA26678A1 (is)
NO (1)	NO994027L (is)
NZ (1)	NZ337363A (is)
OA (1)	OA11150A (is)
PA (1)	PA8480601A1 (is)
PE (1)	PE20000993A1 (is)
PL (1)	PL335016A1 (is)
SG (1)	SG83147A1 (is)
TN (1)	TNSN99159A1 (is)
TR (1)	TR199901996A2 (is)
UY (1)	UY25668A1 (is)
YU (1)	YU39899A (is)
ZA (1)	ZA995297B (is)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US12653825B2 (en)	2010-07-16	2026-06-16	The Trustees Of Columbia University In The City Of New York	Aldose reductase inhibitors and uses thereof
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
HUE031506T2 (en)	2010-07-16	2017-07-28	Univ Columbia	Aldose reductase inhibitors and their use
US20140228319A1 (en) *	2013-02-13	2014-08-14	Banavara L. Mylari	Water soluble salts of aldose reductase inhibitors for treatment of diabetic complications
ES2966094T3 (es)	2016-06-21	2024-04-18	Univ Columbia	Compuestos 4-oxo-3,4-dihidrotieno[3,4-d]piridazina como inhibidores de la aldosa reductasa y métodos de uso de los mismos
IL272246B2 (en)	2017-07-28	2026-01-01	Applied Therapeutics Inc	History of 2-(4-oxo/thioketone/azo-3-((substituted)benzo[d]thiazol-2-yl)methyl)- 3,4-dihydrothieno[3,4-d]pyridazin-1-yl)acetic acid for use as an aldose reductase inhibitor for the treatment of galactosemia or prevention of galactosemia-related complications
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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 AU AU44532/99A patent/AU4453299A/en not_active Abandoned
- 1999-08-17 IS IS5155A patent/IS5155A/is unknown
- 1999-08-18 MA MA25738A patent/MA26678A1/fr unknown
- 1999-08-18 TN TNTNSN99159A patent/TNSN99159A1/fr unknown
- 1999-08-19 HU HU9902783A patent/HUP9902783A3/hu unknown
- 1999-08-19 EE EEP199900385A patent/EE9900385A/xx unknown
- 1999-08-19 GT GT199900137A patent/GT199900137A/es unknown
- 1999-08-19 OA OA9900185A patent/OA11150A/en unknown
- 1999-08-19 UY UY25668A patent/UY25668A1/es not_active Application Discontinuation
- 1999-08-19 ZA ZA9905297A patent/ZA995297B/xx unknown
- 1999-08-19 CA CA002280590A patent/CA2280590A1/en not_active Abandoned
- 1999-08-19 YU YU39899A patent/YU39899A/sh unknown
- 1999-08-19 AP APAP/P/1999/001662A patent/AP9901662A0/en unknown
- 1999-08-19 SG SG9904131A patent/SG83147A1/en unknown
- 1999-08-20 PE PE1999000844A patent/PE20000993A1/es not_active Application Discontinuation
- 1999-08-20 PA PA19998480601A patent/PA8480601A1/es unknown
- 1999-08-20 BG BG103674A patent/BG103674A/xx unknown
- 1999-08-20 NO NO994027A patent/NO994027L/no not_active Application Discontinuation
- 1999-08-20 NZ NZ337363A patent/NZ337363A/xx unknown
- 1999-08-20 TR TR1999/01996A patent/TR199901996A2/xx unknown
- 1999-08-20 EA EA199900675A patent/EA199900675A3/ru unknown
- 1999-08-20 HR HR990259A patent/HRP990259A2/hr not_active Application Discontinuation
- 1999-08-20 PL PL99335016A patent/PL335016A1/xx not_active Application Discontinuation
- 1999-08-20 BR BR9903873-0A patent/BR9903873A/pt not_active Application Discontinuation
- 1999-08-20 KR KR1019990034527A patent/KR20000017411A/ko not_active Ceased
- 1999-08-20 ID IDP990796A patent/ID23307A/id unknown
- 1999-08-23 JP JP11235855A patent/JP2000072769A/ja active Pending
- 1999-08-23 CN CN99118068A patent/CN1245804A/zh active Pending

Also Published As

Publication number	Publication date
EA199900675A2 (ru)	2000-02-28
YU39899A (sh)	2002-12-10
PE20000993A1 (es)	2000-10-04
BG103674A (en)	2000-03-31
GT199900137A (es)	2001-02-09
IS5155A (is)	2000-02-22
EP0982306A3 (en)	2000-07-05
HUP9902783A3 (en)	2001-01-29
NO994027L (no)	2000-02-22
PA8480601A1 (es)	2000-09-29
TR199901996A2 (xx)	2000-03-21
HRP990259A2 (en)	2000-06-30
CN1245804A (zh)	2000-03-01
HUP9902783A2 (hu)	2000-12-28
PL335016A1 (en)	2000-02-28
HU9902783D0 (en)	1999-10-28
AU4453299A (en)	2000-03-09
US6159976A (en)	2000-12-12
EP0982306A2 (en)	2000-03-01
CA2280590A1 (en)	2000-02-21
EE9900385A (et)	2000-04-17
SG83147A1 (en)	2001-09-18
EA199900675A3 (ru)	2000-06-26
BR9903873A (pt)	2000-09-19
NZ337363A (en)	2001-01-26
JP2000072769A (ja)	2000-03-07
ZA995297B (en)	2001-02-19
ID23307A (id)	2000-04-05
NO994027D0 (no)	1999-08-20
AP9901662A0 (en)	1999-09-30
TNSN99159A1 (fr)	2005-11-10
KR20000017411A (ko)	2000-03-25
IL131419A0 (en)	2001-01-28
UY25668A1 (es)	2001-08-27
MA26678A1 (fr)	2004-12-20

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JPH0141629B2 (is)	1989-09-06
US6159976A (en)	2000-12-12	Polymorph of zopolrestat monohydrate
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EP2594570B1 (en)	2015-02-25	Crystal of thienopyrimidine derivative
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JPH0573754B2 (is)	1993-10-15
JP3195455B2 (ja)	2001-08-06	キノリン−３−酢酸誘導体、その製造法と用途
MXPA99007842A (en)	2000-06-05	Polymopher of monopidrate of zopolres
CZ9902918A3 (cs)	2001-01-17	Polymorfy monohydrátu zopolrestatu, farmaceutické kompozice na jejich bázi a způsob jejich výroby
HK1025967A (en)	2000-12-01	Polymorph of zopolrestat monohydrate
KR840001286B1 (ko)	1984-09-07	2-이미다졸린 유도체류의 제조방법
HK40044237A (en)	2021-09-30	4-oxo-3,4-dihydrothieno[3,4-d]pyridazine compounds as aldose reductase inhibitors and methods of use thereof
JPH04128285A (ja)	1992-04-28	キサンチン誘導体
JPH03148262A (ja)	1991-06-25	イミダゾール誘導体およびその製造法ならびにこれを含有する抗潰瘍剤
JP2001089372A (ja)	2001-04-03	癌の予防剤及び治療剤
JPH08231510A (ja)	1996-09-10	新規光学活性アミノピリジン誘導体結晶、その製法および用途