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
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- compound
- substituted
- group
- unsubstituted
- Prior art date
Links
- 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
- 150000003857 carboxamides Chemical class 0.000 claims description 9
- 125000000524 functional group Chemical group 0.000 claims description 9
- 108010007622 LDL Lipoproteins Proteins 0.000 claims description 8
- 102000007330 LDL Lipoproteins Human genes 0.000 claims description 8
- 150000003536 tetrazoles Chemical class 0.000 claims description 8
- 150000003626 triacylglycerols Chemical class 0.000 claims description 8
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 7
- 210000004369 blood Anatomy 0.000 claims description 7
- 239000008280 blood Substances 0.000 claims description 7
- 102000005962 receptors Human genes 0.000 claims description 7
- 108020003175 receptors Proteins 0.000 claims description 7
- 208000008589 Obesity Diseases 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 6
- 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
- 108010010234 HDL Lipoproteins Proteins 0.000 claims 6
- 239000008103 glucose Substances 0.000 claims 6
- 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
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- 238000004965 Hartree-Fock calculation Methods 0.000 claims 1
- 102000004895 Lipoproteins Human genes 0.000 claims 1
- 108090001030 Lipoproteins Proteins 0.000 claims 1
- 238000002441 X-ray diffraction Methods 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 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
- 108091023040 Transcription factor Proteins 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 208000010643 digestive system disease Diseases 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 229940125753 fibrate Drugs 0.000 description 1
- 208000018685 gastrointestinal system disease Diseases 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 231100000304 hepatotoxicity Toxicity 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 230000007056 liver toxicity Effects 0.000 description 1
- 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
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 208000024891 symptom Diseases 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
- 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
-
- 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
-
- 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
-
- 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
-
- 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
-
- 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
-
- 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
-
- 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
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 (es) |
EP (1) | EP1335908B1 (es) |
JP (1) | JP4243101B2 (es) |
KR (1) | KR100839705B1 (es) |
CN (1) | CN1479728A (es) |
AR (1) | AR031305A1 (es) |
AT (1) | ATE386026T1 (es) |
AU (3) | AU2859202A (es) |
BR (1) | BR0114986A (es) |
CA (1) | CA2421154A1 (es) |
CY (1) | CY1107388T1 (es) |
CZ (1) | CZ20031283A3 (es) |
DE (1) | DE60132799T2 (es) |
DK (1) | DK1335908T3 (es) |
EA (1) | EA006920B1 (es) |
EC (1) | ECSP034595A (es) |
ES (1) | ES2300378T3 (es) |
HK (1) | HK1058790A1 (es) |
HR (1) | HRP20030365A2 (es) |
HU (1) | HUP0301655A2 (es) |
IL (2) | IL154840A0 (es) |
MX (1) | MXPA03004141A (es) |
MY (1) | MY157884A (es) |
NO (1) | NO20032059L (es) |
NZ (1) | NZ524569A (es) |
PE (1) | PE20020693A1 (es) |
PL (1) | PL362692A1 (es) |
PT (1) | PT1335908E (es) |
SI (1) | SI1335908T1 (es) |
SK (1) | SK5412003A3 (es) |
SV (1) | SV2003000727A (es) |
TW (1) | TW200716572A (es) |
UA (1) | UA82048C2 (es) |
WO (1) | WO2002038553A2 (es) |
ZA (1) | ZA200302517B (es) |
Families Citing this family (37)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2003043997A1 (en) * | 2001-11-15 | 2003-05-30 | Eli Lilly And Company | Peroxisome proliferator activated receptor alpha agonists |
GB0314079D0 (en) * | 2003-06-18 | 2003-07-23 | Astrazeneca Ab | Therapeutic agents |
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 |
KR100803481B1 (ko) * | 2004-07-27 | 2008-02-14 | 에프. 호프만-라 로슈 아게 | 비-뉴클레오사이드 역전사효소 억제제로서의벤질트라이아졸론 화합물 |
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 |
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 |
CN101189231B (zh) * | 2005-03-23 | 2011-05-18 | 杏林制药株式会社 | 环状氨基苯基链烷酸衍生物 |
JP2008534456A (ja) * | 2005-03-24 | 2008-08-28 | エフ.ホフマン−ラ ロシュ アーゲー | ヘテロ環式逆転写酵素インヒビターとしての1,2,4−トリアゾール−5−オン化合物 |
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 |
US20100099725A1 (en) * | 2007-02-23 | 2010-04-22 | Lance Allen Pfeifer | Peroxisome proliferator activated receptor modulators |
JP2010522706A (ja) | 2007-03-29 | 2010-07-08 | エフ.ホフマン−ラ ロシュ アーゲー | 非ヌクレオシド逆転写酵素阻害剤 |
US8323360B2 (en) * | 2008-06-30 | 2012-12-04 | 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 |
US8497382B2 (en) | 2008-12-01 | 2013-07-30 | 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 |
US20130156720A1 (en) | 2010-08-27 | 2013-06-20 | 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 |
PE20160880A1 (es) * | 2013-09-06 | 2016-09-22 | Inception 2 Inc | Compuestos de triazolona y usos de los mismos |
RU177130U1 (ru) * | 2017-11-29 | 2018-02-09 | Владимир Алексеевич Коннов | Плита изоляционная облицовочная |
WO2021205803A1 (ja) | 2020-04-10 | 2021-10-14 | パナソニックIpマネジメント株式会社 | 熱電変換素子、熱電変換モジュール、接合材、及び熱電変換素子を製造する方法 |
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 |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2090283A1 (en) * | 1992-02-28 | 1993-08-29 | Nobuyuki Hamanaka | Phenoxyacetic acid derivatives |
US5641796A (en) * | 1994-11-01 | 1997-06-24 | Eli Lilly And Company | Oral hypoglycemic agents |
DE19517505A1 (de) * | 1995-05-12 | 1996-11-14 | Bayer Ag | Sulfonylamino(thio)carbonyltriazolin(thi)one mit Aryloxy- oder Arylthio-Substituenten |
CA2229617A1 (en) * | 1995-10-20 | 1997-05-01 | Dr. Karl Thomae Gmbh | 5-membered heterocycles, medicaments containing these compounds, their use and processes for their preparation |
JP3193706B2 (ja) | 1997-10-17 | 2001-07-30 | 山之内製薬株式会社 | アミド誘導体又はその塩 |
AU1120599A (en) * | 1998-04-23 | 1999-03-08 | Dr. Reddy's Research Foundation | New heterocyclic compounds and their use in medicine, process for their reparation and pharmaceutical compositions containing them |
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 |
US6573287B2 (en) | 2001-04-12 | 2003-06-03 | Bristo-Myers Squibb Company | 2,1-oxazoline and 1,2-pyrazoline-based inhibitors of dipeptidyl peptidase IV and method |
USPP14578P2 (en) * | 2002-09-23 | 2004-03-09 | Plant Sciences, Inc. | Artichoke plant named ‘PS-MSC0003’ |
-
2001
- 2001-09-11 UA UA2003054187A patent/UA82048C2/uk unknown
- 2001-11-07 AR ARP010105214A patent/AR031305A1/es unknown
- 2001-11-08 MY MYPI20015155A patent/MY157884A/en unknown
- 2001-11-08 PE PE2001001108A patent/PE20020693A1/es not_active Application Discontinuation
- 2001-11-08 TW TW095138799A patent/TW200716572A/zh unknown
- 2001-11-09 CN CNA018185878A patent/CN1479728A/zh active Pending
- 2001-11-09 BR BR0114986-5A patent/BR0114986A/pt not_active IP Right Cessation
- 2001-11-09 PT PT01989704T patent/PT1335908E/pt 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 DK DK01989704T patent/DK1335908T3/da active
- 2001-11-09 SK SK541-2003A patent/SK5412003A3/sk not_active Application Discontinuation
- 2001-11-09 NZ NZ524569A patent/NZ524569A/en unknown
- 2001-11-09 CA CA002421154A patent/CA2421154A1/en not_active Abandoned
- 2001-11-09 MX MXPA03004141A patent/MXPA03004141A/es active IP Right Grant
- 2001-11-09 ES ES01989704T patent/ES2300378T3/es not_active Expired - Lifetime
- 2001-11-09 HU HU0301655A patent/HUP0301655A2/hu unknown
- 2001-11-09 SI SI200130828T patent/SI1335908T1/sl unknown
- 2001-11-09 PL PL01362692A patent/PL362692A1/xx unknown
- 2001-11-09 JP JP2002541088A patent/JP4243101B2/ja not_active Expired - Fee Related
- 2001-11-09 AU AU2859202A patent/AU2859202A/xx active Pending
- 2001-11-09 AU AU2002228592A patent/AU2002228592B8/en not_active Ceased
- 2001-11-09 WO PCT/US2001/042928 patent/WO2002038553A2/en active IP Right Grant
- 2001-11-09 KR KR1020037006301A patent/KR100839705B1/ko not_active IP Right Cessation
- 2001-11-09 EP EP01989704A patent/EP1335908B1/en not_active Expired - Lifetime
- 2001-11-09 CZ CZ20031283A patent/CZ20031283A3/cs unknown
- 2001-11-09 IL IL15484001A patent/IL154840A0/xx unknown
- 2001-11-09 AT AT01989704T patent/ATE386026T1/de not_active IP Right Cessation
- 2001-11-09 US US10/415,673 patent/US7304062B2/en not_active Expired - Fee Related
- 2001-11-09 SV SV2001000727A patent/SV2003000727A/es not_active Application Discontinuation
-
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 HR HR20030365A patent/HRP20030365A2/hr not_active Application Discontinuation
- 2003-05-08 NO NO20032059A patent/NO20032059L/no unknown
- 2003-05-08 EC EC2003004595A patent/ECSP034595A/es unknown
-
2004
- 2004-01-15 HK HK04100338A patent/HK1058790A1/xx not_active IP Right Cessation
-
2006
- 2006-06-29 AU AU2006202811A patent/AU2006202811A1/en not_active Abandoned
-
2007
- 2007-07-26 US US11/828,446 patent/US20090062358A1/en not_active Abandoned
-
2008
- 2008-04-10 CY CY20081100391T patent/CY1107388T1/el unknown
- 2008-06-27 US US12/215,466 patent/US7868225B2/en not_active Expired - Lifetime
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
ZA200302517B (en) | Peroxisome proliferator activated receptor alpha agonists. | |
EP1915994B1 (en) | Cyclic amine derivatives in combination with ppar regulators | |
JP2004520292A5 (es) | ||
JP2004529174A5 (es) | ||
CA2513092A1 (en) | Compounds for the treatment of metabolic disorders | |
CA2603385A1 (en) | Desferrithiocin polyether analogues and uses thereof for treating metal overload, oxidative stress, and neoplastic and preneoplastic conditions | |
CA2460313A1 (en) | Bisphenylsulfanyl and sulphonate compounds and use thereof for elevating hdl cholesterol levels | |
JP2007502806A5 (es) | ||
JP2004534824A5 (es) | ||
CA2626402A1 (en) | Potassium channel inhibitors | |
JP2005526696A5 (es) | ||
AU2004275808A1 (en) | Substituted oxadiazolidinediones ALS PAI-1 inhibitors | |
KR960041168A (ko) | 베타-아드레날린 효능성 작용물질 | |
KR930701411A (ko) | 치환된 히스티딘 | |
CA3037146A1 (en) | Method of reducing thyroid-associated side effects | |
KR20120099378A (ko) | 염증 또는 에너지 대사/생산 관련 질환의 치료 또는 예방을 위한 ppar 델타 리간드의 용도 | |
JP2005532331A5 (es) | ||
JP2004506721A5 (es) | ||
ZA200300570B (en) | Oxazolyl-arylpropionic acid derivatives and their use as PPAR agonists. | |
JP2004521150A5 (es) | ||
JP2814600B2 (ja) | 排尿障害治療剤 | |
JP4246997B2 (ja) | 糖尿病由来虚血性心疾患の治療及び/または予防剤 | |
JP2007519633A5 (es) | ||
ZA200209152B (en) | Heterocyclic compounds. | |
JP2004520267A5 (es) |