SK7222000A3 - Combination of an aldose reductase inhibitor and a glycogen phosphorylase inhibitor - Google Patents

Combination of an aldose reductase inhibitor and a glycogen phosphorylase inhibitor Download PDF

Info

Publication number: SK7222000A3
Authority: SK; Slovakia
Prior art keywords: chloro; indole; carboxylic acid; amide; benzyl
Prior art date: 1997-11-21

Application number

SK722-2000A

Other languages

English (en)

Slovak (sk)

Inventor

Banavara Lakshman Mylari

Dennis Jay Hoover

Bernard Hulin

Judith Lee Treadway

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.)

1997-11-21

Filing date

1998-11-02

Publication date

2001-09-11

1998-11-02 Application filed by Pfizer Prod Inc filed Critical Pfizer Prod Inc

2001-09-11 Publication of SK7222000A3 publication Critical patent/SK7222000A3/sk

Links

239000003288 aldose reductase inhibitor Substances 0.000 title claims abstract description 52
229940118148 Aldose reductase inhibitor Drugs 0.000 title claims description 41
ROJNYKZWTOHRNU-UHFFFAOYSA-N 2-chloro-4,5-difluoro-n-[[2-methoxy-5-(methylcarbamoylamino)phenyl]carbamoyl]benzamide Chemical compound CNC(=O)NC1=CC=C(OC)C(NC(=O)NC(=O)C=2C(=CC(F)=C(F)C=2)Cl)=C1 ROJNYKZWTOHRNU-UHFFFAOYSA-N 0.000 title claims description 33
MNQZXJOMYWMBOU-UHFFFAOYSA-N glyceraldehyde Chemical compound OCC(O)C=O MNQZXJOMYWMBOU-UHFFFAOYSA-N 0.000 title claims description 16
238000000034 method Methods 0.000 claims abstract description 165
102000007390 Glycogen Phosphorylase Human genes 0.000 claims abstract description 83
108010046163 Glycogen Phosphorylase Proteins 0.000 claims abstract description 83
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims abstract description 74
239000000203 mixture Substances 0.000 claims abstract description 69
238000011282 treatment Methods 0.000 claims abstract description 49
102000004877 Insulin Human genes 0.000 claims abstract description 37
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208000028867 ischemia Diseases 0.000 claims abstract description 25
239000003112 inhibitor Substances 0.000 claims abstract description 14
230000000451 tissue damage Effects 0.000 claims abstract description 10
231100000827 tissue damage Toxicity 0.000 claims abstract description 10
150000001875 compounds Chemical class 0.000 claims description 376
-1 methylcarbamoyl (methyl) -2-phenylethyl Chemical group 0.000 claims description 224
FUQOTYRCMBZFOL-UHFFFAOYSA-N 5-chloro-1H-indole-2-carboxylic acid Chemical compound ClC1=CC=C2NC(C(=O)O)=CC2=C1 FUQOTYRCMBZFOL-UHFFFAOYSA-N 0.000 claims description 86
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 52
210000001519 tissue Anatomy 0.000 claims description 52
239000002253 acid Substances 0.000 claims description 44
150000001408 amides Chemical class 0.000 claims description 33
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125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 31
241000124008 Mammalia Species 0.000 claims description 28
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210000002216 heart Anatomy 0.000 claims description 25
HCUARRIEZVDMPT-UHFFFAOYSA-N Indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 claims description 24
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102000016912 Aldehyde Reductase Human genes 0.000 claims description 8
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125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 5
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HXWKBXMVQHTBPF-UHFFFAOYSA-N 5-chloro-N-(2-oxoethyl)-1H-indole-2-carboxamide Chemical compound O=CCNC(=O)C=1NC2=CC=C(C=C2C1)Cl HXWKBXMVQHTBPF-UHFFFAOYSA-N 0.000 claims 4
JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 claims 3
MYTGFBZJLDLWQG-UHFFFAOYSA-N 5-chloro-1h-indole Chemical compound ClC1=CC=C2NC=CC2=C1 MYTGFBZJLDLWQG-UHFFFAOYSA-N 0.000 claims 3
GZILZCCGDNKAAV-UHFFFAOYSA-N 5-chloro-1h-indole-2-carboxamide Chemical compound ClC1=CC=C2NC(C(=O)N)=CC2=C1 GZILZCCGDNKAAV-UHFFFAOYSA-N 0.000 claims 2
230000001235 sensitizing effect Effects 0.000 claims 2
HEAHLTGDUHXTTO-UHFFFAOYSA-N 1,3-thiazolidine 1,1-dioxide Chemical compound O=S1(=O)CCNC1 HEAHLTGDUHXTTO-UHFFFAOYSA-N 0.000 claims 1
TWKHGKCRNDRGFY-UHFFFAOYSA-N 2-amino-1-(1,1-dioxo-1,3-thiazolidin-3-yl)ethanone Chemical compound NCC(=O)N1CCS(=O)(=O)C1 TWKHGKCRNDRGFY-UHFFFAOYSA-N 0.000 claims 1
KLLOIWZUJAJGPU-IBGZPJMESA-N 5-chloro-n-[(2s)-1-(3-hydroxyazetidin-1-yl)-1-oxo-3-phenylpropan-2-yl]-1h-indole-2-carboxamide Chemical compound C1C(O)CN1C(=O)[C@@H](NC(=O)C=1NC2=CC=C(Cl)C=C2C=1)CC1=CC=CC=C1 KLLOIWZUJAJGPU-IBGZPJMESA-N 0.000 claims 1
DJKMYENTBUQHNM-FQEVSTJZSA-N 5-chloro-n-[(2s)-1-(3-hydroxyiminopyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-yl]-1h-indole-2-carboxamide Chemical compound C1C(=NO)CCN1C(=O)[C@@H](NC(=O)C=1NC2=CC=C(Cl)C=C2C=1)CC1=CC=CC=C1 DJKMYENTBUQHNM-FQEVSTJZSA-N 0.000 claims 1
UXOQYVYSIUSPSZ-UHFFFAOYSA-N ClC=1C=C2C=C(NC2=CC1)C(=O)O.N1C(=CC2=CC=CC=C12)C(=O)O Chemical compound ClC=1C=C2C=C(NC2=CC1)C(=O)O.N1C(=CC2=CC=CC=C12)C(=O)O UXOQYVYSIUSPSZ-UHFFFAOYSA-N 0.000 claims 1
BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 claims 1
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230000002207 retinal effect Effects 0.000 claims 1
208000037816 tissue injury Diseases 0.000 claims 1
229940090865 aldose reductase inhibitors used in diabetes Drugs 0.000 abstract description 11
125000000217 alkyl group Chemical group 0.000 description 180
125000004432 carbon atom Chemical group C* 0.000 description 167
238000006243 chemical reaction Methods 0.000 description 122
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150000001412 amines Chemical class 0.000 description 63
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 63
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CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 36
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125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 34
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239000008213 purified water Substances 0.000 description 1
239000003379 purinergic P1 receptor agonist Substances 0.000 description 1
239000000296 purinergic P1 receptor antagonist Substances 0.000 description 1
150000003212 purines Chemical class 0.000 description 1
238000010791 quenching Methods 0.000 description 1
230000000171 quenching effect Effects 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
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HSSLDCABUXLXKM-UHFFFAOYSA-N resorufin Chemical compound C1=CC(=O)C=C2OC3=CC(O)=CC=C3N=C21 HSSLDCABUXLXKM-UHFFFAOYSA-N 0.000 description 1
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CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000003333 secondary alcohols Chemical class 0.000 description 1
239000012679 serum free medium Substances 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
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CLDWGXZGFUNWKB-UHFFFAOYSA-M silver;benzoate Chemical compound [Ag+].[O-]C(=O)C1=CC=CC=C1 CLDWGXZGFUNWKB-UHFFFAOYSA-M 0.000 description 1
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239000011775 sodium fluoride Substances 0.000 description 1
235000013024 sodium fluoride Nutrition 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000012453 solvate Substances 0.000 description 1
LXANPKRCLVQAOG-NSHDSACASA-N sorbinil Chemical compound C12=CC(F)=CC=C2OCC[C@@]21NC(=O)NC2=O LXANPKRCLVQAOG-NSHDSACASA-N 0.000 description 1
229950004311 sorbinil Drugs 0.000 description 1
125000003003 spiro group Chemical group 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
230000003068 static effect Effects 0.000 description 1
238000007619 statistical method Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
ZSJLQEPLLKMAKR-GKHCUFPYSA-N streptozocin Chemical compound O=NN(C)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O ZSJLQEPLLKMAKR-GKHCUFPYSA-N 0.000 description 1
229960001052 streptozocin Drugs 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
239000000829 suppository Substances 0.000 description 1
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125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000010257 thawing Methods 0.000 description 1
238000009210 therapy by ultrasound Methods 0.000 description 1
230000008719 thickening Effects 0.000 description 1
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OUDSBRTVNLOZBN-UHFFFAOYSA-N tolazamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NN1CCCCCC1 OUDSBRTVNLOZBN-UHFFFAOYSA-N 0.000 description 1
229960002277 tolazamide Drugs 0.000 description 1
229960005371 tolbutamide Drugs 0.000 description 1
LUBHDINQXIHVLS-UHFFFAOYSA-N tolrestat Chemical compound OC(=O)CN(C)C(=S)C1=CC=CC2=C(C(F)(F)F)C(OC)=CC=C21 LUBHDINQXIHVLS-UHFFFAOYSA-N 0.000 description 1
229960003069 tolrestat Drugs 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical group CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
239000006211 transdermal dosage form Substances 0.000 description 1
238000012546 transfer Methods 0.000 description 1
125000005270 trialkylamine group Chemical group 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
GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 description 1
229960001641 troglitazone Drugs 0.000 description 1
229960000281 trometamol Drugs 0.000 description 1
208000035408 type 1 diabetes mellitus 1 Diseases 0.000 description 1
238000002604 ultrasonography Methods 0.000 description 1
229940116269 uric acid Drugs 0.000 description 1
210000002700 urine Anatomy 0.000 description 1
230000006444 vascular growth Effects 0.000 description 1
239000005526 vasoconstrictor agent Substances 0.000 description 1
238000009423 ventilation Methods 0.000 description 1
229950006343 zenarestat Drugs 0.000 description 1
DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- 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
- A61P3/04—Anorexiants; Antiobesity 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
- 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

Landscapes

Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Diabetes (AREA)
Heart & Thoracic Surgery (AREA)
Hematology (AREA)
Epidemiology (AREA)
Cardiology (AREA)
Obesity (AREA)
Endocrinology (AREA)
Urology & Nephrology (AREA)
Emergency Medicine (AREA)
Child & Adolescent Psychology (AREA)
Vascular Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Superheterodyne Receivers (AREA)
Indole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Enzymes And Modification Thereof (AREA)
Noise Elimination (AREA)

SK722-2000A 1997-11-21 1998-11-02 Combination of an aldose reductase inhibitor and a glycogen phosphorylase inhibitor SK7222000A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US6636597P	1997-11-21	1997-11-21
PCT/IB1998/001752 WO1999026659A1 (en)	1997-11-21	1998-11-02	Combination of an aldose reductase inhibitor and a glycogen phosphorylase inhibitor

Publications (1)

Publication Number	Publication Date
SK7222000A3 true SK7222000A3 (en)	2001-09-11

Family

ID=22069038

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK722-2000A SK7222000A3 (en)	1997-11-21	1998-11-02	Combination of an aldose reductase inhibitor and a glycogen phosphorylase inhibitor

Country Status (38)

Country	Link
EP (1)	EP1032424B9 (de)
JP (1)	JP2002504478A (de)
KR (2)	KR20010032304A (de)
CN (1)	CN1279617A (de)
AP (1)	AP911A (de)
AR (1)	AR016423A1 (de)
AT (1)	ATE205403T1 (de)
AU (1)	AU733304B2 (de)
BG (1)	BG104435A (de)
BR (1)	BR9814698A (de)
CA (1)	CA2310069A1 (de)
DE (1)	DE69801680T2 (de)
DK (1)	DK1032424T3 (de)
DZ (1)	DZ2656A1 (de)
EA (1)	EA002365B1 (de)
ES (1)	ES2161548T3 (de)
GR (1)	GR3037071T3 (de)
GT (1)	GT199800166A (de)
HR (1)	HRP20000327A2 (de)
HU (1)	HUP0100272A3 (de)
ID (1)	ID24524A (de)
IL (1)	IL135713A0 (de)
IS (1)	IS5453A (de)
MA (1)	MA26568A1 (de)
NO (1)	NO20002164L (de)
OA (1)	OA11379A (de)
PA (1)	PA8462301A1 (de)
PE (1)	PE135399A1 (de)
PL (1)	PL340643A1 (de)
PT (1)	PT1032424E (de)
SK (1)	SK7222000A3 (de)
TN (1)	TNSN98211A1 (de)
TR (1)	TR200001451T2 (de)
UA (1)	UA57811C2 (de)
UY (1)	UY25258A1 (de)
WO (1)	WO1999026659A1 (de)
YU (1)	YU30700A (de)
ZA (1)	ZA9810636B (de)

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US7825139B2 (en)	2005-05-25	2010-11-02	Forest Laboratories Holdings Limited (BM)	Compounds and methods for selective inhibition of dipeptidyl peptidase-IV
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EP2046753A2 (de)	2006-07-06	2009-04-15	Brystol-Myers Squibb Company	Pyridon/hydroxypyridin-11-beta-hydroxysteroid-dehydrogenase-hemmer vom typ i
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EP2142551B1 (de)	2007-04-17	2015-10-14	Bristol-Myers Squibb Company	KONDENSIERTE HETEROCYCLISCHE Verbindungen als Hemmer der BETA-HYDROXYSTEROID-DEHYDROGENASE -TYP I
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PL2531501T3 (pl)	2010-02-03	2014-05-30	Takeda Pharmaceuticals Co	Inhibitory kinazy 1 regulującej sygnał apoptotyczny
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1998
- 1998-02-11 UA UA2000052869A patent/UA57811C2/uk unknown
- 1998-10-27 GT GT199800166A patent/GT199800166A/es unknown
- 1998-10-28 PA PA19988462301A patent/PA8462301A1/es unknown
- 1998-11-02 TR TR2000/01451T patent/TR200001451T2/xx unknown
- 1998-11-02 AT AT98949193T patent/ATE205403T1/de not_active IP Right Cessation
- 1998-11-02 KR KR1020007005514A patent/KR20010032304A/ko not_active Ceased
- 1998-11-02 DK DK98949193T patent/DK1032424T3/da active
- 1998-11-02 ID IDW20000958A patent/ID24524A/id unknown
- 1998-11-02 CA CA002310069A patent/CA2310069A1/en not_active Abandoned
- 1998-11-02 EP EP98949193A patent/EP1032424B9/de not_active Expired - Lifetime
- 1998-11-02 PL PL98340643A patent/PL340643A1/xx unknown
- 1998-11-02 IL IL13571398A patent/IL135713A0/xx unknown
- 1998-11-02 EA EA200000433A patent/EA002365B1/ru not_active IP Right Cessation
- 1998-11-02 JP JP2000521860A patent/JP2002504478A/ja active Pending
- 1998-11-02 CN CN98811329A patent/CN1279617A/zh active Pending
- 1998-11-02 ES ES98949193T patent/ES2161548T3/es not_active Expired - Lifetime
- 1998-11-02 YU YU30700A patent/YU30700A/sh unknown
- 1998-11-02 HR HR20000327A patent/HRP20000327A2/hr not_active Application Discontinuation
- 1998-11-02 HU HU0100272A patent/HUP0100272A3/hu unknown
- 1998-11-02 DE DE69801680T patent/DE69801680T2/de not_active Expired - Fee Related
- 1998-11-02 PT PT81300054T patent/PT1032424E/pt unknown
- 1998-11-02 AU AU95558/98A patent/AU733304B2/en not_active Ceased
- 1998-11-02 SK SK722-2000A patent/SK7222000A3/sk unknown
- 1998-11-02 WO PCT/IB1998/001752 patent/WO1999026659A1/en not_active Ceased
- 1998-11-02 BR BR9814698-0A patent/BR9814698A/pt not_active IP Right Cessation
- 1998-11-16 PE PE1998001113A patent/PE135399A1/es not_active Application Discontinuation
- 1998-11-18 DZ DZ980266A patent/DZ2656A1/xx active
- 1998-11-18 TN TNTNSN98211A patent/TNSN98211A1/fr unknown
- 1998-11-19 UY UY25258A patent/UY25258A1/es not_active Application Discontinuation
- 1998-11-19 AP APAP/P/1998/001401A patent/AP911A/en active
- 1998-11-19 MA MA25356A patent/MA26568A1/fr unknown
- 1998-11-19 AR ARP980105883A patent/AR016423A1/es not_active Application Discontinuation
- 1998-11-20 ZA ZA9810636A patent/ZA9810636B/xx unknown
1999
- 1999-05-07 KR KR1020007013394A patent/KR100661214B1/ko not_active Expired - Fee Related
2000
- 2000-04-14 IS IS5453A patent/IS5453A/is unknown
- 2000-04-27 NO NO20002164A patent/NO20002164L/no not_active Application Discontinuation
- 2000-05-12 OA OA1200000137A patent/OA11379A/en unknown
- 2000-05-15 BG BG104435A patent/BG104435A/bg unknown
2001
- 2001-10-30 GR GR20010401943T patent/GR3037071T3/el not_active IP Right Cessation

Also Published As

Publication number	Publication date
WO1999026659A1 (en)	1999-06-03
ATE205403T1 (de)	2001-09-15
YU30700A (sh)	2002-12-10
PT1032424E (pt)	2001-12-28
ID24524A (id)	2000-07-20
MA26568A1 (fr)	2004-12-20
BG104435A (bg)	2001-01-31
EP1032424B9 (de)	2004-10-06
HUP0100272A2 (hu)	2001-06-28
EP1032424A1 (de)	2000-09-06
PL340643A1 (en)	2001-02-12
EP1032424B1 (de)	2001-09-12
OA11379A (en)	2004-01-28
NO20002164L (no)	2000-07-19
NO20002164D0 (no)	2000-04-27
AU9555898A (en)	1999-06-15
TNSN98211A1 (fr)	2005-03-15
GR3037071T3 (en)	2002-01-31
PE135399A1 (es)	2000-01-15
IL135713A0 (en)	2001-05-20
KR20010032304A (ko)	2001-04-16
CA2310069A1 (en)	1999-06-03
CN1279617A (zh)	2001-01-10
AU733304B2 (en)	2001-05-10
AP9801401A0 (en)	1998-12-31
HUP0100272A3 (en)	2002-11-28
DE69801680T2 (de)	2002-02-07
KR20010032300A (ko)	2001-04-16
PA8462301A1 (es)	2000-05-24
DZ2656A1 (fr)	2003-03-22
DE69801680D1 (de)	2001-10-18
IS5453A (is)	2000-04-14
AP911A (en)	2000-12-07
AR016423A1 (es)	2001-07-04
ES2161548T3 (es)	2001-12-01
DK1032424T3 (da)	2001-11-19
EA002365B1 (ru)	2002-04-25
KR100661214B1 (ko)	2006-12-26
TR200001451T2 (tr)	2002-06-21
JP2002504478A (ja)	2002-02-12
EA200000433A1 (ru)	2000-12-25
GT199800166A (es)	2000-04-19
HRP20000327A2 (en)	2001-02-28
UY25258A1 (es)	2000-12-29
UA57811C2 (uk)	2003-07-15
ZA9810636B (en)	2000-05-22
BR9814698A (pt)	2000-10-03

Publication	Publication Date	Title
SK7222000A3 (en)	2001-09-11	Combination of an aldose reductase inhibitor and a glycogen phosphorylase inhibitor
US6297269B1 (en)	2001-10-02	Substituted n-(indole-2-carbonyl-) amides and derivatives as glycogen phosphorylase inhibitors
AU717547B2 (en)	2000-03-30	Method of reducing tissue damage associated with non-cardiac ischemia using glycogen phosphorylase inhibitors
JP3314938B2 (ja)	2002-08-19	グリコーゲンホスホリラーゼ抑制剤としての置換されたｎ−（インドール−２−カルボニル）−グリシンアミド類および誘導体
US6277877B1 (en)	2001-08-21	Substituted n-(indole-2-carbonyl)glycinamides and derivates as glycogen phosphorylase inhibitors
US6846820B2 (en)	2005-01-25	Substituted N-(indole-2-carbonyl) -amides and derivatives as glycogen phosphorylase inhibitors
EP1134213A2 (de)	2001-09-19	Verfahren zur Herstellung von substituierten N-(Indol-2-carbonyl)-glycinamiden
CZ20001837A3 (cs)	2001-05-16	Kombinace inhibitoru aldosa reduktasy a inhibitoru glykogen fosforylasy
MXPA00005025A (en)	2001-05-07	Combination of an aldose reductase inhibitor and a glycogen phosphorylase inhibitor