JP2008540520A - Glyrのモジュレータ又はアゴニストである安息香酸誘導体 - Google Patents
Glyrのモジュレータ又はアゴニストである安息香酸誘導体 Download PDFInfo
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- JP2008540520A JP2008540520A JP2008511081A JP2008511081A JP2008540520A JP 2008540520 A JP2008540520 A JP 2008540520A JP 2008511081 A JP2008511081 A JP 2008511081A JP 2008511081 A JP2008511081 A JP 2008511081A JP 2008540520 A JP2008540520 A JP 2008540520A
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- hydroxy
- butyl
- tert
- methyl
- acid
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- GWNVDXQDILPJIG-NXOLIXFESA-N leukotriene C4 Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@H]([C@@H](O)CCCC(O)=O)SC[C@@H](C(=O)NCC(O)=O)NC(=O)CC[C@H](N)C(O)=O GWNVDXQDILPJIG-NXOLIXFESA-N 0.000 description 1
- YEESKJGWJFYOOK-IJHYULJSSA-N leukotriene D4 Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@H]([C@@H](O)CCCC(O)=O)SC[C@H](N)C(=O)NCC(O)=O YEESKJGWJFYOOK-IJHYULJSSA-N 0.000 description 1
- OTZRAYGBFWZKMX-JUDRUQEKSA-N leukotriene E4 Chemical compound CCCCCC=CCC=C\C=C\C=C\[C@@H](SC[C@H](N)C(O)=O)[C@@H](O)CCCC(O)=O OTZRAYGBFWZKMX-JUDRUQEKSA-N 0.000 description 1
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- OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 1
- MZOBRYTXZZFSOJ-UHFFFAOYSA-N methyl 3,5-dibromo-2,6-dihydroxybenzoate Chemical compound COC(=O)C1=C(O)C(Br)=CC(Br)=C1O MZOBRYTXZZFSOJ-UHFFFAOYSA-N 0.000 description 1
- SVSGXLZYOXVPCG-UHFFFAOYSA-N methyl 3,5-dibromo-2-methoxybenzoate Chemical compound COC(=O)C1=CC(Br)=CC(Br)=C1OC SVSGXLZYOXVPCG-UHFFFAOYSA-N 0.000 description 1
- BZCXYBIOKLTGJW-UHFFFAOYSA-N methyl 3-bromo-5-iodo-2-methoxybenzoate;methyl 5-(3-tert-butyl-5-methylphenyl)-2-methoxy-3-pyridin-3-ylbenzoate Chemical compound COC(=O)C1=CC(I)=CC(Br)=C1OC.COC=1C(C(=O)OC)=CC(C=2C=C(C=C(C)C=2)C(C)(C)C)=CC=1C1=CC=CN=C1 BZCXYBIOKLTGJW-UHFFFAOYSA-N 0.000 description 1
- KOODOQULOCHXBN-UHFFFAOYSA-N methyl 3-tert-butyl-2,6-dihydroxybenzoate Chemical compound COC(=O)C1=C(O)C=CC(C(C)(C)C)=C1O KOODOQULOCHXBN-UHFFFAOYSA-N 0.000 description 1
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- DSXHUIJDHYMYSE-UHFFFAOYSA-N methyl 3-tert-butyl-2-methoxy-5-(2-methoxybenzoyl)-6-methylbenzoate Chemical compound CC(C)(C)C1=C(OC)C(C(=O)OC)=C(C)C(C(=O)C=2C(=CC=CC=2)OC)=C1 DSXHUIJDHYMYSE-UHFFFAOYSA-N 0.000 description 1
- OGLNIAWCUDLETF-UHFFFAOYSA-N methyl 3-tert-butyl-2-methoxy-6-methyl-5-(3-nitrobenzoyl)benzoate Chemical compound CC(C)(C)C1=C(OC)C(C(=O)OC)=C(C)C(C(=O)C=2C=C(C=CC=2)[N+]([O-])=O)=C1 OGLNIAWCUDLETF-UHFFFAOYSA-N 0.000 description 1
- KBFAQNLWEHEPFQ-UHFFFAOYSA-N methyl 3-tert-butyl-2-methoxy-6-methyl-5-(3-propan-2-ylbenzoyl)benzoate Chemical compound CC(C)(C)C1=C(OC)C(C(=O)OC)=C(C)C(C(=O)C=2C=C(C=CC=2)C(C)C)=C1 KBFAQNLWEHEPFQ-UHFFFAOYSA-N 0.000 description 1
- MTKNXSZOWACDDZ-UHFFFAOYSA-N methyl 3-tert-butyl-2-methoxy-6-methyl-5-(4-methylbenzoyl)benzoate Chemical compound CC(C)(C)C1=C(OC)C(C(=O)OC)=C(C)C(C(=O)C=2C=CC(C)=CC=2)=C1 MTKNXSZOWACDDZ-UHFFFAOYSA-N 0.000 description 1
- MWOOMSFTLUNGOB-UHFFFAOYSA-N methyl 3-tert-butyl-2-methoxy-6-methyl-5-(4-morpholin-4-ylphenyl)benzoate Chemical compound CC(C)(C)C1=C(OC)C(C(=O)OC)=C(C)C(C=2C=CC(=CC=2)N2CCOCC2)=C1 MWOOMSFTLUNGOB-UHFFFAOYSA-N 0.000 description 1
- ANUKSBNZBUWCEY-UHFFFAOYSA-N methyl 3-tert-butyl-2-methoxy-6-methyl-5-[2-(trifluoromethyl)benzoyl]benzoate Chemical compound CC(C)(C)C1=C(OC)C(C(=O)OC)=C(C)C(C(=O)C=2C(=CC=CC=2)C(F)(F)F)=C1 ANUKSBNZBUWCEY-UHFFFAOYSA-N 0.000 description 1
- IHZAKBSXDRIIJT-UHFFFAOYSA-N methyl 3-tert-butyl-2-methoxy-6-methyl-5-[3-(trifluoromethoxy)benzoyl]benzoate Chemical compound CC(C)(C)C1=C(OC)C(C(=O)OC)=C(C)C(C(=O)C=2C=C(OC(F)(F)F)C=CC=2)=C1 IHZAKBSXDRIIJT-UHFFFAOYSA-N 0.000 description 1
- QJGXPJAPEPOGLS-UHFFFAOYSA-N methyl 3-tert-butyl-2-methoxy-6-methyl-5-[4-(trifluoromethyl)benzoyl]benzoate Chemical compound CC(C)(C)C1=C(OC)C(C(=O)OC)=C(C)C(C(=O)C=2C=CC(=CC=2)C(F)(F)F)=C1 QJGXPJAPEPOGLS-UHFFFAOYSA-N 0.000 description 1
- PQKLJKJNNNSZFU-UHFFFAOYSA-N methyl 3-tert-butyl-2-methoxy-6-methyl-5-quinolin-3-ylbenzoate Chemical compound CC(C)(C)C1=C(OC)C(C(=O)OC)=C(C)C(C=2C=C3C=CC=CC3=NC=2)=C1 PQKLJKJNNNSZFU-UHFFFAOYSA-N 0.000 description 1
- GNZYEWUVACBPOB-UHFFFAOYSA-N methyl 3-tert-butyl-2-methoxy-6-methyl-5-quinolin-6-ylbenzoate Chemical compound CC(C)(C)C1=C(OC)C(C(=O)OC)=C(C)C(C=2C=C3C=CC=NC3=CC=2)=C1 GNZYEWUVACBPOB-UHFFFAOYSA-N 0.000 description 1
- ZMBGTFVGBGUVPI-UHFFFAOYSA-N methyl 3-tert-butyl-2-methoxy-6-methyl-5-quinolin-8-ylbenzoate Chemical compound CC(C)(C)C1=C(OC)C(C(=O)OC)=C(C)C(C=2C3=NC=CC=C3C=CC=2)=C1 ZMBGTFVGBGUVPI-UHFFFAOYSA-N 0.000 description 1
- ZXOAOCFOMGHMJG-UHFFFAOYSA-N methyl 3-tert-butyl-5-(2,4-dichlorobenzoyl)-2-methoxy-6-methylbenzoate Chemical compound CC(C)(C)C1=C(OC)C(C(=O)OC)=C(C)C(C(=O)C=2C(=CC(Cl)=CC=2)Cl)=C1 ZXOAOCFOMGHMJG-UHFFFAOYSA-N 0.000 description 1
- WKLZIFNOJMQEHY-UHFFFAOYSA-N methyl 3-tert-butyl-5-(3,4-dichlorobenzoyl)-2-methoxy-6-methylbenzoate Chemical compound CC(C)(C)C1=C(OC)C(C(=O)OC)=C(C)C(C(=O)C=2C=C(Cl)C(Cl)=CC=2)=C1 WKLZIFNOJMQEHY-UHFFFAOYSA-N 0.000 description 1
- PRTNLZOCVVYUSN-UHFFFAOYSA-N methyl 3-tert-butyl-5-(3,4-dichlorophenyl)-2-methoxy-6-methylbenzoate Chemical compound CC(C)(C)C1=C(OC)C(C(=O)OC)=C(C)C(C=2C=C(Cl)C(Cl)=CC=2)=C1 PRTNLZOCVVYUSN-UHFFFAOYSA-N 0.000 description 1
- UYGPKMSWIAWKSU-UHFFFAOYSA-N methyl 3-tert-butyl-5-(4-chlorobenzoyl)-2,6-dihydroxybenzoate Chemical compound CC(C)(C)C1=C(O)C(C(=O)OC)=C(O)C(C(=O)C=2C=CC(Cl)=CC=2)=C1 UYGPKMSWIAWKSU-UHFFFAOYSA-N 0.000 description 1
- XCZRAAAUBUGEJU-UHFFFAOYSA-N methyl 3-tert-butyl-5-[n'-(4-chlorobenzoyl)oxycarbamimidoyl]-2-methoxy-6-methylbenzoate Chemical compound CC(C)(C)C1=C(OC)C(C(=O)OC)=C(C)C(C(N)=NOC(=O)C=2C=CC(Cl)=CC=2)=C1 XCZRAAAUBUGEJU-UHFFFAOYSA-N 0.000 description 1
- DJLKLKHIPLKLRW-UHFFFAOYSA-N methyl 3-tert-butyl-5-isoquinolin-4-yl-2-methoxy-6-methylbenzoate Chemical compound CC(C)(C)C1=C(OC)C(C(=O)OC)=C(C)C(C=2C3=CC=CC=C3C=NC=2)=C1 DJLKLKHIPLKLRW-UHFFFAOYSA-N 0.000 description 1
- XUDLXLIYBCZTQJ-UHFFFAOYSA-N methyl 5-(1-benzothiophen-2-yl)-3-tert-butyl-2-methoxy-6-methylbenzoate Chemical compound CC(C)(C)C1=C(OC)C(C(=O)OC)=C(C)C(C=2SC3=CC=CC=C3C=2)=C1 XUDLXLIYBCZTQJ-UHFFFAOYSA-N 0.000 description 1
- BIESPOWEIOTTND-UHFFFAOYSA-N methyl 5-chloro-2-methoxy-3-phenylbenzoate Chemical compound COC(=O)C1=CC(Cl)=CC(C=2C=CC=CC=2)=C1OC BIESPOWEIOTTND-UHFFFAOYSA-N 0.000 description 1
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- HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-UHFFFAOYSA-N 0.000 description 1
- KPTRDYONBVUWPD-UHFFFAOYSA-N naphthalen-2-ylboronic acid Chemical compound C1=CC=CC2=CC(B(O)O)=CC=C21 KPTRDYONBVUWPD-UHFFFAOYSA-N 0.000 description 1
- SEXOVMIIVBKGGM-UHFFFAOYSA-N naphthalene-1-thiol Chemical compound C1=CC=C2C(S)=CC=CC2=C1 SEXOVMIIVBKGGM-UHFFFAOYSA-N 0.000 description 1
- 230000008764 nerve damage Effects 0.000 description 1
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- ZBRJXVVKPBZPAN-UHFFFAOYSA-L nickel(2+);triphenylphosphane;dichloride Chemical compound [Cl-].[Cl-].[Ni+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 ZBRJXVVKPBZPAN-UHFFFAOYSA-L 0.000 description 1
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- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
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- 239000011148 porous material Substances 0.000 description 1
- CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 1
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- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
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- 238000011321 prophylaxis Methods 0.000 description 1
- BHMBVRSPMRCCGG-OUTUXVNYSA-N prostaglandin D2 Chemical compound CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)[C@@H](O)CC1=O BHMBVRSPMRCCGG-OUTUXVNYSA-N 0.000 description 1
- BHMBVRSPMRCCGG-UHFFFAOYSA-N prostaglandine D2 Natural products CCCCCC(O)C=CC1C(CC=CCCCC(O)=O)C(O)CC1=O BHMBVRSPMRCCGG-UHFFFAOYSA-N 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
- ABMYEXAYWZJVOV-UHFFFAOYSA-N pyridin-3-ylboronic acid Chemical compound OB(O)C1=CC=CN=C1 ABMYEXAYWZJVOV-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
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- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- YGDICLRMNDWZAK-UHFFFAOYSA-N quinolin-3-ylboronic acid Chemical compound C1=CC=CC2=CC(B(O)O)=CN=C21 YGDICLRMNDWZAK-UHFFFAOYSA-N 0.000 description 1
- NWIJBOCPTGHGIK-UHFFFAOYSA-N quinolin-5-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=CC2=N1 NWIJBOCPTGHGIK-UHFFFAOYSA-N 0.000 description 1
- JLOLSBLXNMVKGY-UHFFFAOYSA-N quinolin-6-ylboronic acid Chemical compound N1=CC=CC2=CC(B(O)O)=CC=C21 JLOLSBLXNMVKGY-UHFFFAOYSA-N 0.000 description 1
- KXJJSKYICDAICD-UHFFFAOYSA-N quinolin-8-ylboronic acid Chemical compound C1=CN=C2C(B(O)O)=CC=CC2=C1 KXJJSKYICDAICD-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
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- 230000006798 recombination Effects 0.000 description 1
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- 230000002441 reversible effect Effects 0.000 description 1
- 229950000975 salicylanilide Drugs 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
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- 238000000638 solvent extraction Methods 0.000 description 1
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- 238000001228 spectrum Methods 0.000 description 1
- 210000000278 spinal cord Anatomy 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
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- 125000003107 substituted aryl group Chemical group 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
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- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 125000005505 thiomorpholino group Chemical group 0.000 description 1
- DSNBHJFQCNUKMA-SCKDECHMSA-N thromboxane A2 Chemical compound OC(=O)CCC\C=C/C[C@@H]1[C@@H](/C=C/[C@@H](O)CCCCC)O[C@@H]2O[C@H]1C2 DSNBHJFQCNUKMA-SCKDECHMSA-N 0.000 description 1
- 150000003595 thromboxanes Chemical class 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- XFHPRJKZBJUJOO-UHFFFAOYSA-N trifluoromethyl 3-phenylbenzoate Chemical compound FC(F)(F)OC(=O)C=1C=C(C=CC=1)C1=CC=CC=C1 XFHPRJKZBJUJOO-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 230000008728 vascular permeability Effects 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 229960001600 xylazine Drugs 0.000 description 1
- BPICBUSOMSTKRF-UHFFFAOYSA-N xylazine Chemical compound CC1=CC=CC(C)=C1NC1=NCCCS1 BPICBUSOMSTKRF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/04—Monocyclic monocarboxylic acids
-
- 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
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0501058 | 2005-05-09 | ||
| PCT/SE2006/000547 WO2006121390A2 (en) | 2005-05-09 | 2006-05-08 | Benzoic acid derivatives that are modulators or agonists of glyr |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008540520A true JP2008540520A (ja) | 2008-11-20 |
| JP2008540520A5 JP2008540520A5 (enExample) | 2009-06-25 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| JP2008511081A Pending JP2008540520A (ja) | 2005-05-09 | 2006-05-08 | Glyrのモジュレータ又はアゴニストである安息香酸誘導体 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US20090192190A1 (enExample) |
| EP (1) | EP1890993A4 (enExample) |
| JP (1) | JP2008540520A (enExample) |
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| BR (1) | BRPI0610240A2 (enExample) |
| CA (1) | CA2607938A1 (enExample) |
| IL (1) | IL186852A0 (enExample) |
| MX (1) | MX2007013879A (enExample) |
| NO (1) | NO20076297L (enExample) |
| TW (1) | TW200718684A (enExample) |
| WO (1) | WO2006121390A2 (enExample) |
| ZA (1) | ZA200709488B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012111730A (ja) * | 2010-11-26 | 2012-06-14 | Kowa Co | 二環性アリール環又は二環性へテロアリール環を有するピラジン誘導体 |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2068871B1 (en) | 2006-09-25 | 2013-12-25 | PTC Therapeutics, Inc. | Hydroxylated 1,2,4-oxadiazole benzoic acid compounds, compositions thereof and the use for nonsense suppression |
| JP2010100552A (ja) * | 2008-10-22 | 2010-05-06 | Tosoh Corp | 1,3,5−トリアジン化合物の製造方法 |
| WO2010114896A1 (en) | 2009-03-31 | 2010-10-07 | Arqule, Inc. | Substituted indolo-pyridinone compounds |
| CN103142569B (zh) * | 2013-02-27 | 2016-01-20 | 南京医科大学 | 2,6-二异丙基苯甲酸及其衍生物作为神经保护剂的应用 |
| ES2886641T3 (es) | 2014-08-11 | 2021-12-20 | Angion Biomedica Corp | Inhibidores de citocromo P450 y sus usos |
| US10287282B2 (en) | 2014-12-31 | 2019-05-14 | Angion Biomedica Corp. | Methods and agents for treating disease |
| CN109942427B (zh) * | 2019-04-17 | 2022-02-18 | 云南农业大学 | 一种单萜酚类衍生物及其合成方法和在农药中的应用 |
| CN114540844B (zh) * | 2022-02-24 | 2024-02-20 | 青岛科技大学 | 一种电催化下苯并噻吩衍生物的制备方法 |
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| DE2431360A1 (de) * | 1974-06-29 | 1976-01-15 | Castaigne Sa | O-thymotinsaeurederivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittelzubereitungen |
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- 2006-05-08 AU AU2006244709A patent/AU2006244709A1/en not_active Abandoned
- 2006-05-08 WO PCT/SE2006/000547 patent/WO2006121390A2/en not_active Ceased
- 2006-05-08 US US11/912,552 patent/US20090192190A1/en not_active Abandoned
- 2006-05-08 MX MX2007013879A patent/MX2007013879A/es not_active Application Discontinuation
- 2006-05-08 CA CA002607938A patent/CA2607938A1/en not_active Abandoned
- 2006-05-08 CN CNA2006800250551A patent/CN101218201A/zh active Pending
- 2006-05-08 EP EP06733399A patent/EP1890993A4/en not_active Withdrawn
- 2006-05-08 KR KR1020077025919A patent/KR20080015788A/ko not_active Withdrawn
- 2006-05-08 BR BRPI0610240-9A patent/BRPI0610240A2/pt not_active IP Right Cessation
- 2006-05-08 JP JP2008511081A patent/JP2008540520A/ja active Pending
- 2006-05-09 TW TW095116314A patent/TW200718684A/zh unknown
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2007
- 2007-10-22 IL IL186852A patent/IL186852A0/en unknown
- 2007-11-02 ZA ZA200709488A patent/ZA200709488B/xx unknown
- 2007-12-06 NO NO20076297A patent/NO20076297L/no not_active Application Discontinuation
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| US4005218A (en) * | 1975-03-18 | 1977-01-25 | Janssen Pharmaceutica N.V. | Antiparasitic salicylanilide derivatives |
| JPS5287244A (en) * | 1976-01-05 | 1977-07-20 | Yoshitomi Pharmaceut Ind Ltd | Anti-arteriosclerotic agents |
| US4301159A (en) * | 1980-06-20 | 1981-11-17 | Shionogi & Co., Ltd. | N-(Diethylaminoethyl)-2-alkoxy-benzamide derivatives |
| WO2004041256A2 (en) * | 2002-11-08 | 2004-05-21 | Novo Nordisk A/S | Safe chemical uncouplers for the treatment of obesity |
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| JP2012111730A (ja) * | 2010-11-26 | 2012-06-14 | Kowa Co | 二環性アリール環又は二環性へテロアリール環を有するピラジン誘導体 |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2607938A1 (en) | 2006-11-16 |
| EP1890993A2 (en) | 2008-02-27 |
| KR20080015788A (ko) | 2008-02-20 |
| TW200718684A (en) | 2007-05-16 |
| WO2006121390A2 (en) | 2006-11-16 |
| ZA200709488B (en) | 2008-11-26 |
| AR056339A1 (es) | 2007-10-03 |
| NO20076297L (no) | 2007-12-06 |
| MX2007013879A (es) | 2008-01-24 |
| WO2006121390A3 (en) | 2007-01-11 |
| IL186852A0 (en) | 2008-02-09 |
| AU2006244709A1 (en) | 2006-11-16 |
| BRPI0610240A2 (pt) | 2012-09-25 |
| US20090192190A1 (en) | 2009-07-30 |
| CN101218201A (zh) | 2008-07-09 |
| WO2006121390A8 (en) | 2007-11-15 |
| EP1890993A4 (en) | 2010-09-08 |
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