OA12760A - Metabolites of (3-ÄÄ4-tert-butyl-benzyl)-(pyridine-3-sulfonyl)-aminoÜ-methylÜ-phenoxy)-acetic acid. - Google Patents
Metabolites of (3-ÄÄ4-tert-butyl-benzyl)-(pyridine-3-sulfonyl)-aminoÜ-methylÜ-phenoxy)-acetic acid. Download PDFInfo
- Publication number
- OA12760A OA12760A OA1200400198A OA1200400198A OA12760A OA 12760 A OA12760 A OA 12760A OA 1200400198 A OA1200400198 A OA 1200400198A OA 1200400198 A OA1200400198 A OA 1200400198A OA 12760 A OA12760 A OA 12760A
- Authority
- OA
- OAPI
- Prior art keywords
- methyl
- pyridine
- sulfonyl
- benzyl
- amino
- Prior art date
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title claims abstract description 130
- 239000002207 metabolite Substances 0.000 title abstract description 8
- 150000001875 compounds Chemical class 0.000 claims description 170
- -1 hydroxy-phenoxy Chemical group 0.000 claims description 36
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 21
- 210000000941 bile Anatomy 0.000 claims description 19
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- 208000001132 Osteoporosis Diseases 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 13
- 229930182480 glucuronide Natural products 0.000 claims description 11
- 230000035876 healing Effects 0.000 claims description 11
- XKQNMAZMTKTTIA-UHFFFAOYSA-N 2-[3-[[[4-(1-hydroxy-2-methylpropan-2-yl)phenyl]methyl-pyridin-3-ylsulfonylamino]methyl]phenoxy]acetic acid Chemical compound C1=CC(C(C)(CO)C)=CC=C1CN(S(=O)(=O)C=1C=NC=CC=1)CC1=CC=CC(OCC(O)=O)=C1 XKQNMAZMTKTTIA-UHFFFAOYSA-N 0.000 claims description 8
- 230000002550 fecal effect Effects 0.000 claims description 8
- HJFXNHIJZXNYSB-UHFFFAOYSA-N n-[[4-(1-hydroxy-2-methylpropan-2-yl)phenyl]methyl]pyridine-3-sulfonamide Chemical compound C1=CC(C(C)(CO)C)=CC=C1CNS(=O)(=O)C1=CC=CN=C1 HJFXNHIJZXNYSB-UHFFFAOYSA-N 0.000 claims description 8
- RHSCSNLXWMXZJZ-UHFFFAOYSA-N 2-[4-(aminomethyl)phenyl]-2-methylpropan-1-ol Chemical compound CC(C)(CO)C1=CC=C(CN)C=C1 RHSCSNLXWMXZJZ-UHFFFAOYSA-N 0.000 claims description 7
- 208000010392 Bone Fractures Diseases 0.000 claims description 7
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- PAQVSTUVBKFCSE-UHFFFAOYSA-N 2-[3-[[(4-prop-1-en-2-ylphenyl)methyl-pyridin-3-ylsulfonylamino]methyl]phenoxy]acetic acid Chemical compound C1=CC(C(=C)C)=CC=C1CN(S(=O)(=O)C=1C=NC=CC=1)CC1=CC=CC(OCC(O)=O)=C1 PAQVSTUVBKFCSE-UHFFFAOYSA-N 0.000 claims description 6
- 210000002381 plasma Anatomy 0.000 claims description 6
- 229940095574 propionic acid Drugs 0.000 claims description 6
- PUZBOEISUBJHKQ-UHFFFAOYSA-N 2-[3-[[[4-(1,2-dihydroxypropan-2-yl)phenyl]methyl-pyridin-3-ylsulfonylamino]methyl]phenoxy]acetic acid Chemical compound C1=CC(C(O)(CO)C)=CC=C1CN(S(=O)(=O)C=1C=NC=CC=1)CC1=CC=CC(OCC(O)=O)=C1 PUZBOEISUBJHKQ-UHFFFAOYSA-N 0.000 claims description 5
- JOJLHDZTZBZWSZ-UHFFFAOYSA-N 2-[4-[[[3-(carboxymethoxy)phenyl]methyl-pyridin-3-ylsulfonylamino]methyl]phenyl]-2-methylpropanoic acid Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1CN(S(=O)(=O)C=1C=NC=CC=1)CC1=CC=CC(OCC(O)=O)=C1 JOJLHDZTZBZWSZ-UHFFFAOYSA-N 0.000 claims description 5
- PNCHTNBMWFKGKF-UHFFFAOYSA-N 2-[5-[[(4-tert-butylphenyl)methyl-pyridin-3-ylsulfonylamino]methyl]-2-hydroxyphenoxy]acetic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1CN(S(=O)(=O)C=1C=NC=CC=1)CC1=CC=C(O)C(OCC(O)=O)=C1 PNCHTNBMWFKGKF-UHFFFAOYSA-N 0.000 claims description 5
- SKMRHCOWINZBQG-UHFFFAOYSA-N 2-methyl-2-[4-[(pyridin-3-ylsulfonylamino)methyl]phenyl]propanoic acid Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1CNS(=O)(=O)C1=CC=CN=C1 SKMRHCOWINZBQG-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- QCKBNFRFJGPPNF-UHFFFAOYSA-N 2-[3-[[[4-(2-hydroxypropan-2-yl)phenyl]methyl-pyridin-3-ylsulfonylamino]methyl]phenoxy]acetic acid Chemical compound C1=CC(C(C)(O)C)=CC=C1CN(S(=O)(=O)C=1C=NC=CC=1)CC1=CC=CC(OCC(O)=O)=C1 QCKBNFRFJGPPNF-UHFFFAOYSA-N 0.000 claims description 3
- JEUHKODDXNRYIK-UHFFFAOYSA-N 2-[3-[[[4-(2-methyl-1-oxopropan-2-yl)phenyl]methyl-pyridin-3-ylsulfonylamino]methyl]phenoxy]acetic acid Chemical compound C1=CC(C(C)(C=O)C)=CC=C1CN(S(=O)(=O)C=1C=NC=CC=1)CC1=CC=CC(OCC(O)=O)=C1 JEUHKODDXNRYIK-UHFFFAOYSA-N 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
- 125000003352 4-tert-butyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims 1
- 150000002500 ions Chemical class 0.000 description 146
- 229960000583 acetic acid Drugs 0.000 description 103
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 50
- 238000001360 collision-induced dissociation Methods 0.000 description 45
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 44
- 239000000047 product Substances 0.000 description 43
- 238000001228 spectrum Methods 0.000 description 40
- 238000004128 high performance liquid chromatography Methods 0.000 description 39
- 239000000243 solution Substances 0.000 description 36
- 150000001793 charged compounds Chemical class 0.000 description 34
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
- 125000000217 alkyl group Chemical group 0.000 description 33
- 241000700159 Rattus Species 0.000 description 28
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 23
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- 229940002612 prodrug Drugs 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000005557 antagonist Substances 0.000 description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- 239000002775 capsule Substances 0.000 description 16
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 16
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- SXERGJJQSKIUIC-UHFFFAOYSA-N 2-Phenoxypropionic acid Chemical group OC(=O)C(C)OC1=CC=CC=C1 SXERGJJQSKIUIC-UHFFFAOYSA-N 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
- 210000004027 cell Anatomy 0.000 description 15
- 239000003826 tablet Substances 0.000 description 15
- 210000001853 liver microsome Anatomy 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- 238000004587 chromatography analysis Methods 0.000 description 13
- 230000000694 effects Effects 0.000 description 13
- 238000011534 incubation Methods 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 239000007864 aqueous solution Substances 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 10
- 238000013467 fragmentation Methods 0.000 description 10
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- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 10
- 239000012528 membrane Substances 0.000 description 10
- 230000011164 ossification Effects 0.000 description 10
- 238000007254 oxidation reaction Methods 0.000 description 10
- 125000006488 t-butyl benzyl group Chemical group 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 9
- 239000003085 diluting agent Substances 0.000 description 9
- 210000003608 fece Anatomy 0.000 description 9
- 230000003647 oxidation Effects 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 102000005962 receptors Human genes 0.000 description 9
- 108020003175 receptors Proteins 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 235000019253 formic acid Nutrition 0.000 description 8
- 229940013688 formic acid Drugs 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- 235000012054 meals Nutrition 0.000 description 8
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- 239000001301 oxygen Substances 0.000 description 8
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- 239000000523 sample Substances 0.000 description 8
- 239000011775 sodium fluoride Substances 0.000 description 8
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- 238000011282 treatment Methods 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 7
- 150000001204 N-oxides Chemical class 0.000 description 7
- 125000004423 acyloxy group Chemical group 0.000 description 7
- 125000004429 atom Chemical group 0.000 description 7
- 125000004093 cyano group Chemical class *C#N 0.000 description 7
- 229960002986 dinoprostone Drugs 0.000 description 7
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- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical group OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 7
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- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 6
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- IAJILQKETJEXLJ-QTBDOELSSA-N aldehydo-D-glucuronic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-QTBDOELSSA-N 0.000 description 4
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- XFCLJVABOIYOMF-QPLCGJKRSA-N toremifene Chemical group C1=CC(OCCN(C)C)=CC=C1C(\C=1C=CC=CC=1)=C(\CCCl)C1=CC=CC=C1 XFCLJVABOIYOMF-QPLCGJKRSA-N 0.000 description 1
- 229960005026 toremifene Drugs 0.000 description 1
- 238000001890 transfection Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 239000013598 vector Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000005550 wet granulation Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- XRASPMIURGNCCH-UHFFFAOYSA-N zoledronic acid Chemical compound OP(=O)(O)C(P(O)(O)=O)(O)CN1C=CN=C1 XRASPMIURGNCCH-UHFFFAOYSA-N 0.000 description 1
- 229960004276 zoledronic acid Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4406—Non condensed pyridines; Hydrogenated derivatives thereof only substituted in position 3, e.g. zimeldine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
- C07D213/71—Sulfur atoms to which a second hetero atom is attached
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Epidemiology (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US35374802P | 2002-01-31 | 2002-01-31 |
Publications (1)
Publication Number | Publication Date |
---|---|
OA12760A true OA12760A (en) | 2006-07-04 |
Family
ID=27663249
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
OA1200400198A OA12760A (en) | 2002-01-31 | 2003-01-20 | Metabolites of (3-ÄÄ4-tert-butyl-benzyl)-(pyridine-3-sulfonyl)-aminoÜ-methylÜ-phenoxy)-acetic acid. |
Country Status (29)
Country | Link |
---|---|
US (1) | US6852863B2 (fr) |
EP (1) | EP1470109A1 (fr) |
JP (1) | JP2005521668A (fr) |
KR (1) | KR20040077884A (fr) |
CN (1) | CN1625549A (fr) |
AP (1) | AP2004003094A0 (fr) |
AR (1) | AR038332A1 (fr) |
BR (1) | BR0307339A (fr) |
CA (1) | CA2473984A1 (fr) |
EA (1) | EA200400724A1 (fr) |
EC (1) | ECSP045215A (fr) |
GB (1) | GB2400100B (fr) |
HN (1) | HN2003000051A (fr) |
HR (1) | HRP20040683A2 (fr) |
HU (1) | HUP0500012A2 (fr) |
IL (1) | IL162167A0 (fr) |
IS (1) | IS7281A (fr) |
MA (1) | MA27169A1 (fr) |
MX (1) | MXPA04004960A (fr) |
NO (1) | NO20043569D0 (fr) |
OA (1) | OA12760A (fr) |
PA (1) | PA8564601A1 (fr) |
PE (1) | PE20030978A1 (fr) |
PL (1) | PL371982A1 (fr) |
TN (1) | TNSN04138A1 (fr) |
TW (1) | TW200302080A (fr) |
UY (1) | UY27632A1 (fr) |
WO (1) | WO2003064391A1 (fr) |
ZA (1) | ZA200404067B (fr) |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
UA67754C2 (uk) * | 1997-10-10 | 2004-07-15 | Пфайзер, Інк. | Агоністи простагландину, фармацевтична композиція на їх основі (варіанти), спосіб нарощення та збереження кісткової маси у хребетних та спосіб лікування (варіанти) |
TWI332937B (en) * | 2005-04-20 | 2010-11-11 | Lg Chemical Ltd | Additive for non-aqueous electrolyte and secondary battery using the same |
EP2059507B1 (fr) * | 2006-07-28 | 2013-03-20 | Pfizer Products Inc. | Agoniste de ep2 |
JP2010523476A (ja) | 2007-03-08 | 2010-07-15 | ザ ボード オブ トラスティーズ オブ ザ リーランド スタンフォード ジュニア ユニバーシティ | ミトコンドリアアルデヒドデヒドロゲナーゼ−2モジュレーター及びその使用方法 |
EP2002834A1 (fr) * | 2007-06-13 | 2008-12-17 | Bayer Schering Pharma Aktiengesellschaft | Aryle/hétarylamides en tant que modulateurs du récepteur EP2 |
CA2718393C (fr) * | 2008-03-12 | 2015-06-16 | Ube Industries, Ltd. | Compose d'acide pyridylaminoacetique |
EP2149551A1 (fr) | 2008-07-30 | 2010-02-03 | Bayer Schering Pharma AG | Dérivés de N-(indol-3-ylalkyl)-(hétéro)arylamide en tant que modulateurs du récepteur EP2 |
EP2149552A1 (fr) | 2008-07-30 | 2010-02-03 | Bayer Schering Pharma AG | Dérivés de benzamide 5,6 substitués en tant que modulateurs du récepteur EP2 |
EP2149554A1 (fr) | 2008-07-30 | 2010-02-03 | Bayer Schering Pharma Aktiengesellschaft | Indolylamides en tant que modulateurs du récepteur EP2 |
JP2012502048A (ja) * | 2008-09-08 | 2012-01-26 | ボード オブ トラスティーズ オブ ザ レランド スタンフォード ジュニア ユニバーシティ | アルデヒドデヒドロゲナーゼ活性のモジュレーターおよびその使用方法 |
JP2012506856A (ja) | 2008-10-28 | 2012-03-22 | ボード オブ トラスティーズ オブ ザ レランド スタンフォード ジュニア ユニバーシティ | アルデヒドデヒドロゲナーゼのモジュレーターおよびその使用方法 |
HUE026742T2 (en) | 2009-03-30 | 2016-07-28 | Ube Industries | A pharmaceutical composition for the treatment or prevention of glaucoma |
DE102009049662A1 (de) | 2009-10-13 | 2011-04-14 | Bayer Schering Pharma Aktiengesellschaft | 2,5-Disubstituierte 2H-Indazole als EP2-Rezeptor-Antagonisten |
US10457659B2 (en) | 2011-04-29 | 2019-10-29 | The Board Of Trustees Of The Leland Stanford Junior University | Compositions and methods for increasing proliferation of adult salivary stem cells |
TW201326154A (zh) | 2011-11-28 | 2013-07-01 | 拜耳知識產權公司 | 作為ep2受體拮抗劑之新穎2h-吲唑 |
CN105358531B (zh) | 2013-03-14 | 2017-11-14 | 利兰-斯坦福大学初级学院的董事会 | 线粒体醛脱氢酶‑2调节剂和其使用方法 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
UA67754C2 (uk) | 1997-10-10 | 2004-07-15 | Пфайзер, Інк. | Агоністи простагландину, фармацевтична композиція на їх основі (варіанти), спосіб нарощення та збереження кісткової маси у хребетних та спосіб лікування (варіанти) |
-
2003
- 2003-01-20 GB GB0413967A patent/GB2400100B/en not_active Expired - Fee Related
- 2003-01-20 MX MXPA04004960A patent/MXPA04004960A/es unknown
- 2003-01-20 EA EA200400724A patent/EA200400724A1/ru unknown
- 2003-01-20 WO PCT/IB2003/000121 patent/WO2003064391A1/fr active Application Filing
- 2003-01-20 BR BR0307339-4A patent/BR0307339A/pt not_active IP Right Cessation
- 2003-01-20 KR KR10-2004-7011618A patent/KR20040077884A/ko not_active Application Discontinuation
- 2003-01-20 JP JP2003564014A patent/JP2005521668A/ja active Pending
- 2003-01-20 OA OA1200400198A patent/OA12760A/en unknown
- 2003-01-20 CA CA002473984A patent/CA2473984A1/fr not_active Abandoned
- 2003-01-20 CN CNA038029952A patent/CN1625549A/zh active Pending
- 2003-01-20 AP APAP/P/2004/003094A patent/AP2004003094A0/en unknown
- 2003-01-20 EP EP03700072A patent/EP1470109A1/fr not_active Withdrawn
- 2003-01-20 IL IL16216703A patent/IL162167A0/xx unknown
- 2003-01-20 HU HU0500012A patent/HUP0500012A2/hu unknown
- 2003-01-20 PL PL03371982A patent/PL371982A1/xx not_active Application Discontinuation
- 2003-01-24 TW TW092101619A patent/TW200302080A/zh unknown
- 2003-01-28 PE PE2003000086A patent/PE20030978A1/es not_active Application Discontinuation
- 2003-01-28 HN HN2003000051A patent/HN2003000051A/es unknown
- 2003-01-29 US US10/353,671 patent/US6852863B2/en not_active Expired - Fee Related
- 2003-01-29 AR ARP030100254A patent/AR038332A1/es unknown
- 2003-01-30 PA PA20038564601A patent/PA8564601A1/es unknown
- 2003-01-30 UY UY27632A patent/UY27632A1/es not_active Application Discontinuation
-
2004
- 2004-05-21 IS IS7281A patent/IS7281A/is unknown
- 2004-05-25 ZA ZA200404067A patent/ZA200404067B/en unknown
- 2004-07-21 MA MA27796A patent/MA27169A1/fr unknown
- 2004-07-23 HR HR20040683A patent/HRP20040683A2/hr not_active Application Discontinuation
- 2004-07-27 TN TNP2004000138A patent/TNSN04138A1/fr unknown
- 2004-07-30 EC EC2004005215A patent/ECSP045215A/es unknown
- 2004-08-26 NO NO20043569A patent/NO20043569D0/no not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
IS7281A (is) | 2004-05-21 |
NO20043569L (no) | 2004-08-26 |
GB0413967D0 (en) | 2004-07-28 |
UY27632A1 (es) | 2003-08-29 |
PL371982A1 (en) | 2005-07-11 |
AP2004003094A0 (en) | 2004-09-30 |
TNSN04138A1 (fr) | 2007-03-12 |
CN1625549A (zh) | 2005-06-08 |
GB2400100A (en) | 2004-10-06 |
GB2400100B (en) | 2006-04-12 |
TW200302080A (en) | 2003-08-01 |
KR20040077884A (ko) | 2004-09-07 |
WO2003064391A1 (fr) | 2003-08-07 |
ZA200404067B (en) | 2005-08-29 |
HN2003000051A (es) | 2003-09-24 |
MA27169A1 (fr) | 2005-01-03 |
HUP0500012A2 (hu) | 2005-04-28 |
ECSP045215A (es) | 2004-09-28 |
JP2005521668A (ja) | 2005-07-21 |
MXPA04004960A (es) | 2005-04-08 |
NO20043569D0 (no) | 2004-08-26 |
EP1470109A1 (fr) | 2004-10-27 |
IL162167A0 (en) | 2005-11-20 |
AR038332A1 (es) | 2005-01-12 |
BR0307339A (pt) | 2004-12-07 |
PA8564601A1 (es) | 2003-09-05 |
CA2473984A1 (fr) | 2003-08-07 |
US20030216445A1 (en) | 2003-11-20 |
HRP20040683A2 (en) | 2004-10-31 |
EA200400724A1 (ru) | 2004-12-30 |
US6852863B2 (en) | 2005-02-08 |
PE20030978A1 (es) | 2003-11-19 |
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