DE60217930T2 - Pyridazinon Aldose Reductase Inhibitoren - Google Patents
Pyridazinon Aldose Reductase Inhibitoren Download PDFInfo
- Publication number
- DE60217930T2 DE60217930T2 DE60217930T DE60217930T DE60217930T2 DE 60217930 T2 DE60217930 T2 DE 60217930T2 DE 60217930 T DE60217930 T DE 60217930T DE 60217930 T DE60217930 T DE 60217930T DE 60217930 T2 DE60217930 T2 DE 60217930T2
- Authority
- DE
- Germany
- Prior art keywords
- compound
- inhibitor
- sulfonyl
- alkyl
- pyridazin
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Fee Related
Links
- 239000003288 aldose reductase inhibitor Substances 0.000 title description 11
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 title description 8
- 229940090865 aldose reductase inhibitors used in diabetes Drugs 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 303
- -1 pyrazinopyrazinyl Chemical group 0.000 claims description 186
- 229940002612 prodrug Drugs 0.000 claims description 96
- 239000000651 prodrug Substances 0.000 claims description 96
- 150000003839 salts Chemical class 0.000 claims description 62
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims description 50
- 239000003112 inhibitor Substances 0.000 claims description 44
- 125000001424 substituent group Chemical group 0.000 claims description 42
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 28
- OGNSCSPNOLGXSM-UHFFFAOYSA-N (+/-)-DABA Natural products NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 claims description 25
- 229960003692 gamma aminobutyric acid Drugs 0.000 claims description 25
- 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 claims description 25
- 239000012896 selective serotonin reuptake inhibitor Substances 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 102100030980 Sodium/hydrogen exchanger 1 Human genes 0.000 claims description 22
- 108010093115 growth factor-activatable Na-H exchanger NHE-1 Proteins 0.000 claims description 22
- 239000008194 pharmaceutical composition Substances 0.000 claims description 22
- 239000003379 purinergic P1 receptor agonist Substances 0.000 claims description 22
- 229940123659 Sorbitol dehydrogenase inhibitor Drugs 0.000 claims description 21
- 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 claims description 20
- 102000005862 Angiotensin II Human genes 0.000 claims description 20
- 101800000733 Angiotensin-2 Proteins 0.000 claims description 20
- CZGUSIXMZVURDU-JZXHSEFVSA-N Ile(5)-angiotensin II Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C([O-])=O)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@@H]([NH3+])CC([O-])=O)C(C)C)C1=CC=C(O)C=C1 CZGUSIXMZVURDU-JZXHSEFVSA-N 0.000 claims description 20
- 229950006323 angiotensin ii Drugs 0.000 claims description 20
- 125000002883 imidazolyl group Chemical group 0.000 claims description 20
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 19
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 19
- 125000002971 oxazolyl group Chemical group 0.000 claims description 19
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 125000000335 thiazolyl group Chemical group 0.000 claims description 18
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 claims description 17
- UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 102000004270 Peptidyl-Dipeptidase A Human genes 0.000 claims description 17
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 16
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 125000004076 pyridyl group Chemical group 0.000 claims description 16
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- 125000000168 pyrrolyl group Chemical group 0.000 claims description 15
- 125000001544 thienyl group Chemical group 0.000 claims description 15
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 14
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- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 14
- 125000002541 furyl group Chemical group 0.000 claims description 14
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- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 14
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 14
- 125000005493 quinolyl group Chemical group 0.000 claims description 14
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 14
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 14
- 125000001425 triazolyl group Chemical group 0.000 claims description 14
- 102400001190 Vastatin Human genes 0.000 claims description 13
- 101800000422 Vastatin Proteins 0.000 claims description 13
- 239000000556 agonist Substances 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 13
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 13
- 125000001153 fluoro group Chemical group F* 0.000 claims description 12
- 125000005554 pyridyloxy group Chemical group 0.000 claims description 12
- 208000002249 Diabetes Complications Diseases 0.000 claims description 11
- 230000003178 anti-diabetic effect Effects 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 239000003937 drug carrier Substances 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 125000001624 naphthyl group Chemical group 0.000 claims description 11
- 239000003085 diluting agent Substances 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
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- 239000002590 phosphodiesterase V inhibitor Substances 0.000 claims description 10
- 102100029077 3-hydroxy-3-methylglutaryl-coenzyme A reductase Human genes 0.000 claims description 9
- 101710158485 3-hydroxy-3-methylglutaryl-coenzyme A reductase Proteins 0.000 claims description 9
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims description 9
- 229940079593 drug Drugs 0.000 claims description 9
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 8
- 239000003477 4 aminobutyric acid receptor stimulating agent Substances 0.000 claims description 8
- 239000005541 ACE inhibitor Substances 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 7
- 125000004647 alkyl sulfenyl group Chemical group 0.000 claims description 7
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 7
- 239000002552 dosage form Substances 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- NKOHRVBBQISBSB-UHFFFAOYSA-N 5-[(4-hydroxyphenyl)methyl]-1,3-thiazolidine-2,4-dione Chemical compound C1=CC(O)=CC=C1CC1C(=O)NC(=O)S1 NKOHRVBBQISBSB-UHFFFAOYSA-N 0.000 claims description 6
- 239000002333 angiotensin II receptor antagonist Substances 0.000 claims description 6
- 229940125708 antidiabetic agent Drugs 0.000 claims description 6
- 239000002464 receptor antagonist Substances 0.000 claims description 6
- 229940044551 receptor antagonist Drugs 0.000 claims description 6
- 239000003981 vehicle Substances 0.000 claims description 6
- 229940123934 Reductase inhibitor Drugs 0.000 claims description 5
- 125000006365 alkylene oxy carbonyl group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 230000001225 therapeutic effect Effects 0.000 claims description 5
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 4
- 101710129690 Angiotensin-converting enzyme inhibitor Proteins 0.000 claims description 4
- 101710086378 Bradykinin-potentiating and C-type natriuretic peptides Proteins 0.000 claims description 4
- 229940126317 angiotensin II receptor antagonist Drugs 0.000 claims description 4
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 3
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
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- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 2
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- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000006085 pyrrolopyridyl group Chemical group 0.000 claims description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
- 125000004588 thienopyridyl group Chemical group S1C(=CC2=C1C=CC=N2)* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- DDZGQYREBDXECY-UHFFFAOYSA-N 1h-pyrazolo[3,4-b]pyrazine Chemical compound C1=CN=C2C=NNC2=N1 DDZGQYREBDXECY-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
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- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/12—Antidiuretics, e.g. drugs for diabetes insipidus
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
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- General Chemical & Material Sciences (AREA)
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- Pharmacology & Pharmacy (AREA)
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- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28005101P | 2001-03-30 | 2001-03-30 | |
| US280051P | 2001-03-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60217930D1 DE60217930D1 (de) | 2007-03-15 |
| DE60217930T2 true DE60217930T2 (de) | 2007-10-18 |
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| DE60202452T Expired - Fee Related DE60202452C5 (de) | 2001-03-30 | 2002-01-31 | Pyridazinonaldose reductase inhibitoren |
| DE60216823T Expired - Fee Related DE60216823T2 (de) | 2001-03-30 | 2002-01-31 | Zwischenprodukten für die Herstellung von Pyridazinon Aldose Reductase Inhibitoren. |
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| DE60202452T Expired - Fee Related DE60202452C5 (de) | 2001-03-30 | 2002-01-31 | Pyridazinonaldose reductase inhibitoren |
| DE60216823T Expired - Fee Related DE60216823T2 (de) | 2001-03-30 | 2002-01-31 | Zwischenprodukten für die Herstellung von Pyridazinon Aldose Reductase Inhibitoren. |
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| CN101663262B (zh) | 2006-12-01 | 2014-03-26 | 百时美施贵宝公司 | 用于治疗动脉粥样硬化和心血管疾病的作为cetp抑制剂的n-(3-苄基)-2,2-(二苯基)-丙-1胺衍生物 |
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| 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 |
| US9296692B2 (en) * | 2011-09-15 | 2016-03-29 | Taipei Medical University | Use of indolyl and indolinyl hydroxamates for treating heart failure of neuronal injury |
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| CN103739547B (zh) * | 2014-01-03 | 2015-09-02 | 沈阳药科大学 | 2-[6-甲氧基-3-(2,3-二氯苯基)甲基-4-氧代-1,4-二氢-1(4h)-喹啉基]乙酸的合成方法 |
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| AU2016248080A1 (en) * | 2015-04-14 | 2017-11-02 | Board Of Regents Of The University Of Texas System | Compositions and methods of modulating short-chain dehydrogenase activity |
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| JP2020514323A (ja) | 2017-02-06 | 2020-05-21 | ケース ウエスタン リザーブ ユニバーシティ | 短鎖デヒドロゲナーゼ活性を調節する組成物と方法 |
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| KR102921276B1 (ko) | 2018-11-21 | 2026-02-03 | 케이스 웨스턴 리저브 유니버시티 | 단쇄 데히드로게나아제 활성을 조절하는 조성물 및 방법 |
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| FR2822827B1 (fr) * | 2001-03-28 | 2003-05-16 | Sanofi Synthelabo | Nouveaux derives de n-(arylsulfonyl) beta-aminoacides comportant un groupe aminomethyle substitue, leur procede de preparation et les compositions pharmaceutiques en contenant |
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