ES2427726T3 - Nuevos difeniléteres heterocíclicos - Google Patents
Nuevos difeniléteres heterocíclicos Download PDFInfo
- Publication number
- ES2427726T3 ES2427726T3 ES07750819T ES07750819T ES2427726T3 ES 2427726 T3 ES2427726 T3 ES 2427726T3 ES 07750819 T ES07750819 T ES 07750819T ES 07750819 T ES07750819 T ES 07750819T ES 2427726 T3 ES2427726 T3 ES 2427726T3
- Authority
- ES
- Spain
- Prior art keywords
- phenoxy
- thiazolidin
- phenyl
- acetic acid
- ylmethyl
- 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.)
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- -1 heterocyclic diphenyl ethers Chemical class 0.000 title claims abstract description 32
- 150000001875 compounds Chemical class 0.000 claims abstract description 91
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 47
- 239000001257 hydrogen Substances 0.000 claims abstract description 47
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 36
- 150000003839 salts Chemical class 0.000 claims abstract description 29
- 239000012453 solvate Substances 0.000 claims abstract description 23
- 125000003118 aryl group Chemical group 0.000 claims abstract description 22
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 20
- 150000004677 hydrates Chemical class 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 13
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 13
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 12
- 150000002367 halogens Chemical class 0.000 claims abstract description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 11
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 10
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 4
- 229940124530 sulfonamide Drugs 0.000 claims abstract description 4
- 150000003456 sulfonamides Chemical class 0.000 claims abstract description 4
- 150000001735 carboxylic acids Chemical class 0.000 claims abstract description 3
- 238000011282 treatment Methods 0.000 claims description 37
- 239000000203 mixture Substances 0.000 claims description 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 21
- 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 claims description 20
- 206010012601 diabetes mellitus Diseases 0.000 claims description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
- 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 description 19
- 239000008103 glucose Substances 0.000 claims description 19
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 17
- 230000004054 inflammatory process Effects 0.000 claims description 16
- 206010061218 Inflammation Diseases 0.000 claims description 15
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- VBCIBLUDWOQXTK-UHFFFAOYSA-N 2-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 VBCIBLUDWOQXTK-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
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- 208000023275 Autoimmune disease Diseases 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
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- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 5
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- 229910052708 sodium Inorganic materials 0.000 claims description 5
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- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
- 239000011575 calcium Substances 0.000 claims description 4
- 239000011591 potassium Substances 0.000 claims description 4
- 150000003626 triacylglycerols Chemical class 0.000 claims description 4
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 4
- MEJBANGHCJDFPZ-UHFFFAOYSA-N 2-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy]phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=O)S1 MEJBANGHCJDFPZ-UHFFFAOYSA-N 0.000 claims description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 3
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims description 3
- 229910052791 calcium Inorganic materials 0.000 claims description 3
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 3
- 239000000194 fatty acid Substances 0.000 claims description 3
- 229930195729 fatty acid Natural products 0.000 claims description 3
- 150000004665 fatty acids Chemical class 0.000 claims description 3
- 159000000003 magnesium salts Chemical class 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- ONXSZFPCOKFCNR-UHFFFAOYSA-N 2-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]-2-fluorophenoxy]phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1OC(C(=C1)F)=CC=C1CC1C(=O)NC(=O)S1 ONXSZFPCOKFCNR-UHFFFAOYSA-N 0.000 claims description 2
- PAIZTWWKQQRGAM-UHFFFAOYSA-N 2-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]-2-methoxyphenoxy]phenyl]acetic acid Chemical compound C=1C=C(OC=2C=CC(CC(O)=O)=CC=2)C(OC)=CC=1CC1SC(=O)NC1=O PAIZTWWKQQRGAM-UHFFFAOYSA-N 0.000 claims description 2
- RKCQQCKSCYBFGA-UHFFFAOYSA-N 2-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]-3-fluorophenoxy]phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1OC(C=C1F)=CC=C1CC1C(=O)NC(=O)S1 RKCQQCKSCYBFGA-UHFFFAOYSA-N 0.000 claims description 2
- IAVXQVOUTHYEQQ-UHFFFAOYSA-N 2-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]-n-methylanilino]phenyl]acetic acid Chemical compound C=1C=C(CC(O)=O)C=CC=1N(C)C(C=C1)=CC=C1CC1SC(=O)NC1=O IAVXQVOUTHYEQQ-UHFFFAOYSA-N 0.000 claims description 2
- OWEQNHZUOXAAMY-UHFFFAOYSA-N 2-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]-2-fluorophenyl]acetic acid Chemical compound C1=C(F)C(CC(=O)O)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 OWEQNHZUOXAAMY-UHFFFAOYSA-N 0.000 claims description 2
- JVLKBYPXCUMJPX-UHFFFAOYSA-N 2-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]phenyl]-n,n-dimethylacetamide Chemical compound C1=CC(CC(=O)N(C)C)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 JVLKBYPXCUMJPX-UHFFFAOYSA-N 0.000 claims description 2
- GVUYKUAZFPFMEM-UHFFFAOYSA-N 2-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]phenyl]butanoic acid Chemical compound C1=CC(C(C(O)=O)CC)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 GVUYKUAZFPFMEM-UHFFFAOYSA-N 0.000 claims description 2
- RBBWFSJZNPXNBH-UHFFFAOYSA-N 2-[4-[4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]-2-(trifluoromethyl)phenoxy]phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1OC(C(=C1)C(F)(F)F)=CC=C1C=C1C(=O)NC(=O)S1 RBBWFSJZNPXNBH-UHFFFAOYSA-N 0.000 claims description 2
- VEGNXICEXUPIFA-UHFFFAOYSA-N 2-[4-[4-[(2-oxo-1,3-dihydroindol-3-yl)methyl]-2-(trifluoromethyl)phenoxy]phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1OC(C(=C1)C(F)(F)F)=CC=C1CC1C2=CC=CC=C2NC1=O VEGNXICEXUPIFA-UHFFFAOYSA-N 0.000 claims description 2
- LZGPALLAOQVAGB-UHFFFAOYSA-N 2-[4-[4-[(4-oxo-2-sulfanylidene-1,3-thiazolidin-5-ylidene)methyl]phenoxy]phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1OC(C=C1)=CC=C1C=C1C(=O)NC(=S)S1 LZGPALLAOQVAGB-UHFFFAOYSA-N 0.000 claims description 2
- ZYKLVVRPCTYYEF-UHFFFAOYSA-N 2-[4-[4-[[3-(carboxymethyl)-4-oxo-2-sulfanylidene-1,3-thiazolidin-5-yl]methyl]-3-fluorophenoxy]phenyl]acetic acid Chemical compound O=C1N(CC(=O)O)C(=S)SC1CC(C(=C1)F)=CC=C1OC1=CC=C(CC(O)=O)C=C1 ZYKLVVRPCTYYEF-UHFFFAOYSA-N 0.000 claims description 2
- SXKCGCRZLNSIAF-UHFFFAOYSA-N 2-[4-[4-[[3-(carboxymethyl)-4-oxo-2-sulfanylidene-1,3-thiazolidin-5-yl]methyl]phenoxy]phenyl]acetic acid Chemical compound O=C1N(CC(=O)O)C(=S)SC1CC(C=C1)=CC=C1OC1=CC=C(CC(O)=O)C=C1 SXKCGCRZLNSIAF-UHFFFAOYSA-N 0.000 claims description 2
- UKIFBTLFPXEAME-UHFFFAOYSA-N 2-[6-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]pyridin-3-yl]acetic acid Chemical compound N1=CC(CC(=O)O)=CC=C1OC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 UKIFBTLFPXEAME-UHFFFAOYSA-N 0.000 claims description 2
- RTZUONIACREHOA-UHFFFAOYSA-N 2-[6-[4-[(2-oxo-1,3-dihydroindol-3-yl)methyl]-2-(trifluoromethyl)phenoxy]pyridin-3-yl]acetic acid Chemical compound N1=CC(CC(=O)O)=CC=C1OC(C(=C1)C(F)(F)F)=CC=C1CC1C2=CC=CC=C2NC1=O RTZUONIACREHOA-UHFFFAOYSA-N 0.000 claims description 2
- XRAQRDBRFHRLBY-UHFFFAOYSA-N 2-[6-[4-[[3-(carboxymethyl)-4-oxo-2-sulfanylidene-1,3-thiazolidin-5-yl]methyl]phenoxy]pyridin-3-yl]acetic acid Chemical compound O=C1N(CC(=O)O)C(=S)SC1CC(C=C1)=CC=C1OC1=CC=C(CC(O)=O)C=N1 XRAQRDBRFHRLBY-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D277/34—Oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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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
- 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
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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
- 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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- A—HUMAN NECESSITIES
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- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D277/36—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
- C07D401/12—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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
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- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Immunology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Transplantation (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
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|---|---|---|---|
| US11/359,657 US7781464B2 (en) | 2003-01-17 | 2006-02-21 | Heterocyclic diphenyl ethers |
| US359657 | 2006-02-21 | ||
| PCT/US2007/004007 WO2007097992A2 (en) | 2006-02-21 | 2007-02-15 | Novel heterocyclic diphenyl ethers |
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| ES2427726T3 true ES2427726T3 (es) | 2013-10-31 |
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| ES07750819T Active ES2427726T3 (es) | 2006-02-21 | 2007-02-15 | Nuevos difeniléteres heterocíclicos |
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|---|---|
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| EP (1) | EP2004185B1 (enExample) |
| JP (1) | JP5414280B2 (enExample) |
| CA (1) | CA2642650C (enExample) |
| ES (1) | ES2427726T3 (enExample) |
| PL (1) | PL2004185T3 (enExample) |
| TW (1) | TWI394748B (enExample) |
| WO (1) | WO2007097992A2 (enExample) |
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| US7087576B2 (en) * | 2003-10-07 | 2006-08-08 | Bexel Pharmaceuticals, Inc. | Dipeptide phenyl ethers |
| US20090203744A1 (en) * | 2005-07-29 | 2009-08-13 | Pande Y Surendrakumar Satyanarayan | Novel pyridine derivatives |
| JP2010520306A (ja) * | 2007-03-07 | 2010-06-10 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | エストロゲン関連受容体−αモジュレーターとしての置換フェノキシチアゾリジンジオン |
| WO2009025170A1 (ja) * | 2007-08-23 | 2009-02-26 | Konica Minolta Opto, Inc. | 長尺の位相差フィルム、長尺の楕円偏光フィルム、楕円偏光板、及び画像表示装置 |
| ATE536347T1 (de) | 2008-05-20 | 2011-12-15 | Merck Sharp & Dohme | Effiziente herstellung heterologer proteine unter verwendung von mannosyltransferaseinhibitoren |
| US20140187594A1 (en) * | 2010-07-28 | 2014-07-03 | Orchid Chemicals And Pharmaceuticals Ltd | Diphenyl ether compounds for the treatment of liver, lung disorders, diabetic complications and cardiovascular diseases |
| WO2012153775A1 (ja) | 2011-05-10 | 2012-11-15 | 国立大学法人神戸大学 | Ras機能阻害作用を有するチオキソチアゾリジン誘導体 |
| US12151372B2 (en) | 2019-02-27 | 2024-11-26 | Berkshire Grey Operating Company, Inc. | Systems and methods for hose routing in programmable motion systems |
| WO2020219480A1 (en) | 2019-04-25 | 2020-10-29 | Berkshire Grey, Inc. | Systems and methods for maintaining vacuum hose life in hose routing systems in programmable motion systems |
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| US20020049240A1 (en) | 1994-12-19 | 2002-04-25 | Beecham Group P.1.C. | Novel compounds |
| US5166137A (en) | 1991-03-27 | 1992-11-24 | Nobipols Forskningsstiftelse | Guluronic acid polymers and use of same for inhibition of cytokine production |
| US5441971A (en) | 1991-04-11 | 1995-08-15 | The Upjohn Company | Thiazolidinedione derivatives, production and use thereof |
| TW268952B (enExample) | 1993-02-26 | 1996-01-21 | Takeda Pharm Industry Co Ltd | |
| US6251928B1 (en) * | 1994-03-16 | 2001-06-26 | Eli Lilly And Company | Treatment of alzheimer's disease employing inhibitors of cathepsin D |
| US5527546A (en) | 1994-08-10 | 1996-06-18 | Bayer Corporation | Human interleukin 6 inhibitor |
| ATE271128T1 (de) | 1995-05-11 | 2004-07-15 | Applied Research Systems | Inhibitoren der il-6 aktivitaet |
| TW577875B (en) | 1997-01-31 | 2004-03-01 | Shionogi & Co | Pyrrolidine derivatives with inhibitory activity for phospholipase A2 |
| CA2289102A1 (en) * | 1997-05-07 | 1998-11-12 | Sugen, Inc. | 2-indolinone derivatives as modulators of protein kinase activity |
| EP1048659A4 (en) * | 1997-11-12 | 2002-11-20 | Inst Med Molecular Design Inc | Retinoid receptor Antagonist |
| US7105552B2 (en) * | 1998-05-08 | 2006-09-12 | Theracos, Inc. | Heterocyclic analogs of diphenylethylene compounds |
| US6331633B1 (en) | 1998-05-08 | 2001-12-18 | Calyx Therapeutics Inc. | Heterocyclic analogs of diphenylethylene compounds |
| US6699896B1 (en) | 1998-05-12 | 2004-03-02 | Wyeth | Oxazole-aryl-carboxylic acids useful in the treatment of insulin resistance and hyperglycemia |
| EP1082323A2 (en) | 1998-06-05 | 2001-03-14 | AstraZeneca UK Limited | Oxazolidinone derivatives, process for their preparation and pharmaceutical compositions containing them |
| WO2000000194A1 (en) | 1998-06-27 | 2000-01-06 | Photogenesis, Inc. | Ophthalmic uses of ppargamma agonists and ppargamma antagonists |
| EP1108713A4 (en) | 1998-08-27 | 2006-04-05 | Ono Pharmaceutical Co | CARBOXYLENE DERIVATIVES AND MEDICAMENTS CONTAINING THEM AS AN ACTIVE COMPONENT |
| US7407978B2 (en) * | 1999-04-06 | 2008-08-05 | Theracos, Inc. | Heterocyclic analogs of diphenylethylene compounds |
| HUP0200996A3 (en) | 1999-04-07 | 2003-01-28 | Sankyo Company Ltd Chuo Ku | Amine derivatives, pharmaceutical compositions containing them and their use |
| HRP20010795A2 (en) | 1999-04-28 | 2003-02-28 | Aventis Pharma Gmbh | Di-aryl acid derivatives as ppar receptor ligands |
| TWI284533B (en) | 1999-05-24 | 2007-08-01 | Sankyo Co | Pharmaceutical composition for treating hyperglycemia, impaired glucose tolerance, diabetes complications and for improving insulin resistant |
| ID29875A (id) | 1999-07-01 | 2001-10-18 | Geron Corp Cs | Penghambat-penghambat telomerase dan metode penggunaannya |
| JP2001072592A (ja) * | 1999-07-01 | 2001-03-21 | Kyowa Hakko Kogyo Co Ltd | テロメラーゼ阻害剤 |
| SE514748C2 (sv) * | 1999-08-03 | 2001-04-09 | Sahlin Gjutteknik Ab | Spolsten |
| US6730687B1 (en) | 1999-08-23 | 2004-05-04 | Kyorin Pharmaceutical Co., Ltd. | Substituted benzylthiazolidine-2, 4-dione derivatives |
| CN1384825A (zh) | 1999-08-31 | 2002-12-11 | 马克西亚药品公司 | 亚苄基－噻唑烷二酮及其类似物以及它们在治疗糖尿病中的应用 |
| JP2001199888A (ja) | 2000-01-24 | 2001-07-24 | Fujimoto Brothers:Kk | 糖尿病治療剤 |
| JP2001308814A (ja) | 2000-04-19 | 2001-11-02 | Hitachi Ltd | フレーム構成自動識別通信装置 |
| DE60115132T2 (de) | 2000-04-21 | 2006-07-06 | Pfizer Products Inc., Groton | Thyroid-Rezeptorliganden |
| US6620830B2 (en) | 2000-04-21 | 2003-09-16 | Pfizer, Inc. | Thyroid receptor ligands |
| US6680387B2 (en) | 2000-04-24 | 2004-01-20 | Aryx Therapeutics | Materials and methods for the treatment of diabetes, hyperlipidemia, hypercholesterolemia, and atherosclerosis |
| ATE363278T1 (de) | 2001-09-14 | 2007-06-15 | Novo Nordisk As | Neue liganden für die hisb10 zn2+ stellen des insulin-hexamers in der r-konformation |
| US7521465B2 (en) | 2003-01-17 | 2009-04-21 | Bexel Pharmaceuticals, Inc. | Diphenyl ether derivatives |
| US6794401B2 (en) | 2003-01-17 | 2004-09-21 | Bexel Pharmaceuticals, Inc. | Amino acid phenoxy ethers |
| JP2007523842A (ja) | 2003-03-11 | 2007-08-23 | ノボ ノルディスク アクティーゼルスカブ | 酸安定化されたインスリンを含有する薬学的製剤 |
| US7087576B2 (en) | 2003-10-07 | 2006-08-08 | Bexel Pharmaceuticals, Inc. | Dipeptide phenyl ethers |
| JP2008533122A (ja) * | 2005-03-18 | 2008-08-21 | オーキッド ケミカルズ アンド ファーマシューティカルズ リミテッド | 新規なチロシン誘導体 |
-
2006
- 2006-02-21 US US11/359,657 patent/US7781464B2/en not_active Expired - Fee Related
-
2007
- 2007-02-15 ES ES07750819T patent/ES2427726T3/es active Active
- 2007-02-15 EP EP07750819.0A patent/EP2004185B1/en not_active Not-in-force
- 2007-02-15 WO PCT/US2007/004007 patent/WO2007097992A2/en not_active Ceased
- 2007-02-15 PL PL07750819T patent/PL2004185T3/pl unknown
- 2007-02-15 CA CA2642650A patent/CA2642650C/en not_active Expired - Fee Related
- 2007-02-15 JP JP2008556356A patent/JP5414280B2/ja not_active Expired - Fee Related
- 2007-02-26 TW TW096106502A patent/TWI394748B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CA2642650C (en) | 2015-04-14 |
| JP5414280B2 (ja) | 2014-02-12 |
| US7781464B2 (en) | 2010-08-24 |
| WO2007097992A2 (en) | 2007-08-30 |
| EP2004185A4 (en) | 2012-02-29 |
| WO2007097992A3 (en) | 2008-11-06 |
| CA2642650A1 (en) | 2007-08-30 |
| EP2004185A2 (en) | 2008-12-24 |
| TW200812989A (en) | 2008-03-16 |
| EP2004185B1 (en) | 2013-06-26 |
| US20060247285A1 (en) | 2006-11-02 |
| PL2004185T3 (pl) | 2013-11-29 |
| TWI394748B (zh) | 2013-05-01 |
| JP2009528997A (ja) | 2009-08-13 |
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