ZA200302517B - Peroxisome proliferator activated receptor alpha agonists. - Google Patents
Peroxisome proliferator activated receptor alpha agonists. Download PDFInfo
- Publication number
- ZA200302517B ZA200302517B ZA200302517A ZA200302517A ZA200302517B ZA 200302517 B ZA200302517 B ZA 200302517B ZA 200302517 A ZA200302517 A ZA 200302517A ZA 200302517 A ZA200302517 A ZA 200302517A ZA 200302517 B ZA200302517 B ZA 200302517B
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- South Africa
- Prior art keywords
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- compound
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- 229940127520 Peroxisome Proliferator-activated Receptor alpha Agonists Drugs 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 133
- 125000000217 alkyl group Chemical group 0.000 claims description 105
- 229910052739 hydrogen Inorganic materials 0.000 claims description 44
- 239000001257 hydrogen Substances 0.000 claims description 42
- 150000003839 salts Chemical class 0.000 claims description 39
- 239000012453 solvate Substances 0.000 claims description 39
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 37
- 125000003545 alkoxy group Chemical group 0.000 claims description 29
- 125000001475 halogen functional group Chemical group 0.000 claims description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
- 229910052717 sulfur Inorganic materials 0.000 claims description 20
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 19
- -1 and (iv) R4 is H Chemical group 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 19
- 229940124530 sulfonamide Drugs 0.000 claims description 15
- 150000003456 sulfonamides Chemical class 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 229920006395 saturated elastomer Polymers 0.000 claims description 13
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 claims description 12
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims description 12
- 125000005466 alkylenyl group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000005647 linker group Chemical group 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 150000004677 hydrates Chemical class 0.000 claims description 11
- 208000011580 syndromic disease Diseases 0.000 claims description 10
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- 125000005002 aryl methyl group Chemical group 0.000 claims description 6
- 206010012601 diabetes mellitus Diseases 0.000 claims description 6
- 235000020824 obesity Nutrition 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 3
- 238000000034 method Methods 0.000 claims 55
- 241000124008 Mammalia Species 0.000 claims 53
- 239000000203 mixture Substances 0.000 claims 44
- 239000000126 substance Substances 0.000 claims 42
- 150000002431 hydrogen Chemical class 0.000 claims 24
- 125000002947 alkylene group Chemical group 0.000 claims 14
- 238000004519 manufacturing process Methods 0.000 claims 12
- 210000002966 serum Anatomy 0.000 claims 9
- 125000005001 aminoaryl group Chemical group 0.000 claims 7
- 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 claims 6
- 102000015779 HDL Lipoproteins Human genes 0.000 claims 6
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- 125000001188 haloalkyl group Chemical group 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 239000002253 acid Substances 0.000 claims 3
- 125000005596 alkyl carboxamido group Chemical group 0.000 claims 3
- 239000010949 copper Substances 0.000 claims 3
- 125000005000 thioaryl group Chemical group 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 2
- 125000004104 aryloxy group Chemical group 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims 2
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 235000019260 propionic acid Nutrition 0.000 claims 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 238000002560 therapeutic procedure Methods 0.000 claims 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
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- 238000004965 Hartree-Fock calculation Methods 0.000 claims 1
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- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
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- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims 1
- 230000005855 radiation Effects 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 claims 1
- 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 description 6
- 229940123464 Thiazolidinedione Drugs 0.000 description 5
- 150000001467 thiazolidinediones Chemical class 0.000 description 5
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
- 102000004877 Insulin Human genes 0.000 description 3
- 108090001061 Insulin Proteins 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229940125396 insulin Drugs 0.000 description 3
- 206010022489 Insulin Resistance Diseases 0.000 description 2
- 235000012000 cholesterol Nutrition 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 230000004584 weight gain Effects 0.000 description 2
- 235000019786 weight gain Nutrition 0.000 description 2
- 206010014486 Elevated triglycerides Diseases 0.000 description 1
- 208000018522 Gastrointestinal disease Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 206010021000 Hypoglycaemic coma Diseases 0.000 description 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 1
- 108010028554 LDL Cholesterol Proteins 0.000 description 1
- 238000008214 LDL Cholesterol Methods 0.000 description 1
- 102000007399 Nuclear hormone receptor Human genes 0.000 description 1
- 108020005497 Nuclear hormone receptor Proteins 0.000 description 1
- 229940126033 PPAR agonist Drugs 0.000 description 1
- 102000000536 PPAR gamma Human genes 0.000 description 1
- 108010016731 PPAR gamma Proteins 0.000 description 1
- 102000040945 Transcription factor Human genes 0.000 description 1
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- 230000014509 gene expression Effects 0.000 description 1
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- 239000003446 ligand Substances 0.000 description 1
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- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- 150000004667 medium chain fatty acids Chemical class 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002307 peroxisome proliferator activated receptor agonist Substances 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
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- 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
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- GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/06—Compounds containing any of the groups, e.g. semicarbazides
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
- C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
- C07C257/22—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having nitrogen atoms of amidino groups further bound to nitrogen atoms, e.g. hydrazidines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/02—Compounds containing any of the groups, e.g. carbazates
- C07C281/04—Compounds containing any of the groups, e.g. carbazates the other nitrogen atom being further doubly-bound to a carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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 ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms
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- 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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms
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- 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
- C07D405/06—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 carbon chain containing only aliphatic carbon atoms
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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
- C07D409/06—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 carbon chain containing only aliphatic carbon atoms
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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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Plant Substances (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Breeding Of Plants And Reproduction By Means Of Culturing (AREA)
- Cultivation Of Plants (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US24731700P | 2000-11-10 | 2000-11-10 |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200302517B true ZA200302517B (en) | 2004-06-30 |
Family
ID=22934453
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200302517A ZA200302517B (en) | 2000-11-10 | 2003-03-31 | Peroxisome proliferator activated receptor alpha agonists. |
Country Status (35)
Country | Link |
---|---|
US (3) | US7304062B2 (ru) |
EP (1) | EP1335908B1 (ru) |
JP (1) | JP4243101B2 (ru) |
KR (1) | KR100839705B1 (ru) |
CN (1) | CN1479728A (ru) |
AR (1) | AR031305A1 (ru) |
AT (1) | ATE386026T1 (ru) |
AU (3) | AU2002228592B8 (ru) |
BR (1) | BR0114986A (ru) |
CA (1) | CA2421154A1 (ru) |
CY (1) | CY1107388T1 (ru) |
CZ (1) | CZ20031283A3 (ru) |
DE (1) | DE60132799T2 (ru) |
DK (1) | DK1335908T3 (ru) |
EA (1) | EA006920B1 (ru) |
EC (1) | ECSP034595A (ru) |
ES (1) | ES2300378T3 (ru) |
HK (1) | HK1058790A1 (ru) |
HR (1) | HRP20030365A2 (ru) |
HU (1) | HUP0301655A2 (ru) |
IL (2) | IL154840A0 (ru) |
MX (1) | MXPA03004141A (ru) |
MY (1) | MY157884A (ru) |
NO (1) | NO20032059L (ru) |
NZ (1) | NZ524569A (ru) |
PE (1) | PE20020693A1 (ru) |
PL (1) | PL362692A1 (ru) |
PT (1) | PT1335908E (ru) |
SI (1) | SI1335908T1 (ru) |
SK (1) | SK5412003A3 (ru) |
SV (1) | SV2003000727A (ru) |
TW (1) | TW200716572A (ru) |
UA (1) | UA82048C2 (ru) |
WO (1) | WO2002038553A2 (ru) |
ZA (1) | ZA200302517B (ru) |
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CN1662487A (zh) | 2002-06-19 | 2005-08-31 | 伊莱利利公司 | 酰胺连接基过氧化物酶体增殖物激活受体调节剂 |
TW200505441A (en) | 2003-03-24 | 2005-02-16 | Hoffmann La Roche | Non-nucleoside reverse transcriptase inhibitorsⅠ |
FR2866339B1 (fr) * | 2004-02-18 | 2006-05-05 | Pf Medicament | Derives de 1,2,4-triazines, leur preparation et leur application en therapeutique humaine |
US7262318B2 (en) * | 2004-03-10 | 2007-08-28 | Pfizer, Inc. | Substituted heteroaryl- and phenylsulfamoyl compounds |
US20050288340A1 (en) * | 2004-06-29 | 2005-12-29 | Pfizer Inc | Substituted heteroaryl- and phenylsulfamoyl compounds |
US8293778B2 (en) | 2004-07-27 | 2012-10-23 | Roche Palo Alto Llc | Heterocyclic antiviral compounds |
RU2394028C2 (ru) | 2004-07-27 | 2010-07-10 | Ф.Хоффманн-Ля Рош Аг | Производные бензилтриазолона в качестве ненуклеозидных ингибиторов обратной транскриптазы |
KR100803481B1 (ko) * | 2004-07-27 | 2008-02-14 | 에프. 호프만-라 로슈 아게 | 비-뉴클레오사이드 역전사효소 억제제로서의벤질트라이아졸론 화합물 |
BRPI0515015A (pt) * | 2004-08-11 | 2008-07-01 | Kyorin Seiyaku Kk | derivado cìclico de ácido aminobenzóico; medicamento; agonista ppar(alpha); agonista duplo ppar(alpha), y; agonista duplo ppar(alpha), (delta); modulador ppar; agente lipìdeo; agente profilático ou terapêutico compreendendo pelo menos um dos derivados cìclicos de ácido aminobenzóico ou sal do mesmo farmacêuticamente aceitável |
WO2006068199A1 (ja) * | 2004-12-22 | 2006-06-29 | Mochida Pharmaceutical Co., Ltd. | 代謝的に安定な3-オキシ-1,2,4-トリアゾール誘導体 |
PE20061041A1 (es) * | 2005-01-28 | 2006-10-12 | Lilly Co Eli | Formulaciones y regimen de dosificacion para moduladores alfa de ppar |
FR2882750B1 (fr) | 2005-03-03 | 2007-05-11 | Pierre Fabre Medicament Sa | Derives de 1,2,4-triazines, leur preparation et leur application en therapeutique humaine |
US20090036489A1 (en) * | 2005-03-22 | 2009-02-05 | Masahiro Nomura | Novel Cyclic Aminophenylalkanoic Acid Derivative |
CA2600759A1 (en) * | 2005-03-24 | 2006-09-28 | F. Hoffmann-La Roche Ag | 1,2,4-triazole-5-one compounds as heterocyclic reverse transcriptase inhibitors |
WO2007126043A1 (ja) * | 2006-04-27 | 2007-11-08 | Mitsubishi Tanabe Pharma Corporation | チアゾール環を含むカルボン酸誘導体の医薬用途 |
WO2008103574A2 (en) * | 2007-02-23 | 2008-08-28 | Eli Lilly And Company | Peroxisome proliferator activated receptor modulators |
AU2008233929A1 (en) | 2007-03-29 | 2008-10-09 | F. Hoffmann-La Roche Ag | Non-nucleoside reverse transcriptase inhibitors |
WO2010002712A2 (en) * | 2008-06-30 | 2010-01-07 | 3M Innovative Properties Company | Method of crystallization |
CN101643451B (zh) * | 2008-08-07 | 2013-03-06 | 浙江海正药业股份有限公司 | 过氧化物酶增殖物激活受体亚型δ类激动剂化合物及其制备方法 |
AU2009323367B2 (en) | 2008-12-01 | 2013-05-23 | Mitsubishi Tanabe Pharma Corporation | Carboxylic acid derivative containing thiazole ring and pharmaceutical use thereof |
US8575430B2 (en) * | 2010-03-02 | 2013-11-05 | Nunhems, B.V. | Hybrid artichoke variety NUN 4006 AR |
US20110167512A1 (en) * | 2009-03-02 | 2011-07-07 | Nunhems B.V. | Hybrid artichoke variety nun 4006 ar |
DE102010001064A1 (de) * | 2009-03-18 | 2010-09-23 | Bayer Schering Pharma Aktiengesellschaft | Substituierte 2-Acetamido-5-Aryl-1,2,4-triazolone und deren Verwendung |
US20100245582A1 (en) * | 2009-03-25 | 2010-09-30 | Syclipse Technologies, Inc. | System and method of remote surveillance and applications therefor |
WO2012027331A1 (en) | 2010-08-27 | 2012-03-01 | Ironwood Pharmaceuticals, Inc. | Compositions and methods for treating or preventing metabolic syndrome and related diseases and disorders |
US8648233B2 (en) * | 2010-09-20 | 2014-02-11 | Nunhems B.V. | Hybrid artichoke variety NUN 4021 AR |
US8669420B2 (en) | 2012-02-29 | 2014-03-11 | Nunhems B.V. | Hybrid artichoke variety NUN 4060 AR |
WO2013134562A1 (en) | 2012-03-09 | 2013-09-12 | Inception 2, Inc. | Triazolone compounds and uses thereof |
WO2014099503A1 (en) | 2012-12-20 | 2014-06-26 | Inception 2, Inc. | Triazolone compounds and uses thereof |
CN105579440A (zh) * | 2013-09-06 | 2016-05-11 | 因森普深2公司 | 三唑酮化合物及其应用 |
RU177130U1 (ru) * | 2017-11-29 | 2018-02-09 | Владимир Алексеевич Коннов | Плита изоляционная облицовочная |
CN115398657A (zh) | 2020-04-10 | 2022-11-25 | 松下知识产权经营株式会社 | 热电转换元件、热电转换组件、接合材料和热电转换元件的制造方法 |
CN112774869B (zh) * | 2020-12-25 | 2022-09-16 | 厦门紫金矿冶技术有限公司 | 黄铁矿抑制剂及其制备和在铜铅锌多金属硫化矿中的应用 |
CN114853686B (zh) * | 2021-08-23 | 2023-06-20 | 中国药科大学 | 三氮唑酮类化合物及其医药用途 |
CN115894379A (zh) * | 2022-01-20 | 2023-04-04 | 中国药科大学 | 海因类化合物及其医药用途 |
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CA2090283A1 (en) * | 1992-02-28 | 1993-08-29 | Nobuyuki Hamanaka | Phenoxyacetic acid derivatives |
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DE19517505A1 (de) * | 1995-05-12 | 1996-11-14 | Bayer Ag | Sulfonylamino(thio)carbonyltriazolin(thi)one mit Aryloxy- oder Arylthio-Substituenten |
EP0858457A1 (de) * | 1995-10-20 | 1998-08-19 | Dr. Karl Thomae GmbH | 5-gliedrige heterocyclen, diese verbindungen enthaltende arzneimittel und deren verwendung sowie verfahren zu ihrer herstellung |
DK1028111T3 (da) * | 1997-10-17 | 2004-09-20 | Yamanouchi Pharma Co Ltd | Amidderivater eller salte heraf |
DE69828445D1 (de) * | 1998-04-23 | 2005-02-03 | Reddys Lab Ltd Dr | Heterozyklische verbindungen,und deren verwendung in arzneimittel,verfahren zu deren herstellung und diese enthaltende pharmazeutische zusammenstellungen |
GB9914977D0 (en) | 1999-06-25 | 1999-08-25 | Glaxo Group Ltd | Chemical compounds |
PE20011010A1 (es) | 1999-12-02 | 2001-10-18 | Glaxo Group Ltd | Oxazoles y tiazoles sustituidos como agonista del receptor activado por el proliferador de peroxisomas humano |
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USPP14578P2 (en) * | 2002-09-23 | 2004-03-09 | Plant Sciences, Inc. | Artichoke plant named ‘PS-MSC0003’ |
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2001
- 2001-09-11 UA UA2003054187A patent/UA82048C2/ru unknown
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- 2001-11-08 PE PE2001001108A patent/PE20020693A1/es not_active Application Discontinuation
- 2001-11-08 TW TW095138799A patent/TW200716572A/zh unknown
- 2001-11-09 EA EA200300558A patent/EA006920B1/ru not_active IP Right Cessation
- 2001-11-09 DE DE60132799T patent/DE60132799T2/de not_active Expired - Fee Related
- 2001-11-09 CN CNA018185878A patent/CN1479728A/zh active Pending
- 2001-11-09 US US10/415,673 patent/US7304062B2/en not_active Expired - Fee Related
- 2001-11-09 SK SK541-2003A patent/SK5412003A3/sk not_active Application Discontinuation
- 2001-11-09 ES ES01989704T patent/ES2300378T3/es not_active Expired - Lifetime
- 2001-11-09 SV SV2001000727A patent/SV2003000727A/es not_active Application Discontinuation
- 2001-11-09 HU HU0301655A patent/HUP0301655A2/hu unknown
- 2001-11-09 PT PT01989704T patent/PT1335908E/pt unknown
- 2001-11-09 EP EP01989704A patent/EP1335908B1/en not_active Expired - Lifetime
- 2001-11-09 NZ NZ524569A patent/NZ524569A/en unknown
- 2001-11-09 CA CA002421154A patent/CA2421154A1/en not_active Abandoned
- 2001-11-09 JP JP2002541088A patent/JP4243101B2/ja not_active Expired - Fee Related
- 2001-11-09 KR KR1020037006301A patent/KR100839705B1/ko not_active IP Right Cessation
- 2001-11-09 AU AU2002228592A patent/AU2002228592B8/en not_active Ceased
- 2001-11-09 IL IL15484001A patent/IL154840A0/xx unknown
- 2001-11-09 DK DK01989704T patent/DK1335908T3/da active
- 2001-11-09 CZ CZ20031283A patent/CZ20031283A3/cs unknown
- 2001-11-09 SI SI200130828T patent/SI1335908T1/sl unknown
- 2001-11-09 BR BR0114986-5A patent/BR0114986A/pt not_active IP Right Cessation
- 2001-11-09 WO PCT/US2001/042928 patent/WO2002038553A2/en active IP Right Grant
- 2001-11-09 PL PL01362692A patent/PL362692A1/xx unknown
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- 2001-11-09 AU AU2859202A patent/AU2859202A/xx active Pending
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2003
- 2003-03-10 IL IL154840A patent/IL154840A/en active IP Right Grant
- 2003-03-31 ZA ZA200302517A patent/ZA200302517B/en unknown
- 2003-05-08 NO NO20032059A patent/NO20032059L/no unknown
- 2003-05-08 EC EC2003004595A patent/ECSP034595A/es unknown
- 2003-05-08 HR HR20030365A patent/HRP20030365A2/hr not_active Application Discontinuation
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2004
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2006
- 2006-06-29 AU AU2006202811A patent/AU2006202811A1/en not_active Abandoned
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2007
- 2007-07-26 US US11/828,446 patent/US20090062358A1/en not_active Abandoned
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2008
- 2008-04-10 CY CY20081100391T patent/CY1107388T1/el unknown
- 2008-06-27 US US12/215,466 patent/US7868225B2/en not_active Expired - Lifetime
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