JP2011521978A - 新規化合物、それを含む医薬組成物、およびこれらの使用方法 - Google Patents
新規化合物、それを含む医薬組成物、およびこれらの使用方法 Download PDFInfo
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- JP2011521978A JP2011521978A JP2011511901A JP2011511901A JP2011521978A JP 2011521978 A JP2011521978 A JP 2011521978A JP 2011511901 A JP2011511901 A JP 2011511901A JP 2011511901 A JP2011511901 A JP 2011511901A JP 2011521978 A JP2011521978 A JP 2011521978A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 165
- 238000000034 method Methods 0.000 title claims description 70
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 50
- 125000003118 aryl group Chemical group 0.000 claims abstract description 50
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 42
- 125000001424 substituent group Chemical group 0.000 claims abstract description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 34
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 32
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 24
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 23
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 22
- 125000004429 atom Chemical group 0.000 claims abstract description 20
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 19
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 17
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 16
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 8
- 108010039731 Fatty Acid Synthases Proteins 0.000 claims description 52
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 36
- 125000005843 halogen group Chemical group 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 22
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 20
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 20
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 230000000694 effects Effects 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 9
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 9
- 241001465754 Metazoa Species 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 230000000813 microbial effect Effects 0.000 claims description 5
- 206010028980 Neoplasm Diseases 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 229940124531 pharmaceutical excipient Drugs 0.000 claims description 4
- 230000004580 weight loss Effects 0.000 claims description 4
- 201000011510 cancer Diseases 0.000 claims description 3
- 230000012010 growth Effects 0.000 claims description 3
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims 8
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 102000015303 Fatty Acid Synthases Human genes 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 230000001939 inductive effect Effects 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 description 60
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 55
- 102100022089 Acyl-[acyl-carrier-protein] hydrolase Human genes 0.000 description 51
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 49
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 36
- 239000000460 chlorine Substances 0.000 description 31
- 239000007787 solid Substances 0.000 description 31
- 239000000203 mixture Substances 0.000 description 28
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 26
- 210000004027 cell Anatomy 0.000 description 26
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- 239000003112 inhibitor Substances 0.000 description 21
- 102000004190 Enzymes Human genes 0.000 description 20
- 108090000790 Enzymes Proteins 0.000 description 20
- 235000019439 ethyl acetate Nutrition 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 229920006395 saturated elastomer Polymers 0.000 description 18
- 239000000047 product Substances 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 239000012043 crude product Substances 0.000 description 14
- 230000004136 fatty acid synthesis Effects 0.000 description 14
- 230000005764 inhibitory process Effects 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- 238000012360 testing method Methods 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- ACFIXJIJDZMPPO-NNYOXOHSSA-N NADPH Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](OP(O)(O)=O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 ACFIXJIJDZMPPO-NNYOXOHSSA-N 0.000 description 12
- 235000014113 dietary fatty acids Nutrition 0.000 description 12
- 239000000194 fatty acid Substances 0.000 description 12
- 229930195729 fatty acid Natural products 0.000 description 12
- 238000003818 flash chromatography Methods 0.000 description 12
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 11
- 230000003647 oxidation Effects 0.000 description 11
- 238000007254 oxidation reaction Methods 0.000 description 11
- 239000000843 powder Substances 0.000 description 11
- LTYOQGRJFJAKNA-KKIMTKSISA-N Malonyl CoA Natural products S(C(=O)CC(=O)O)CCNC(=O)CCNC(=O)[C@@H](O)C(CO[P@](=O)(O[P@](=O)(OC[C@H]1[C@@H](OP(=O)(O)O)[C@@H](O)[C@@H](n2c3ncnc(N)c3nc2)O1)O)O)(C)C LTYOQGRJFJAKNA-KKIMTKSISA-N 0.000 description 10
- GVEZIHKRYBHEFX-NQQPLRFYSA-N cerulenin Chemical compound C\C=C\C\C=C\CCC(=O)[C@H]1O[C@H]1C(N)=O GVEZIHKRYBHEFX-NQQPLRFYSA-N 0.000 description 10
- 150000004665 fatty acids Chemical class 0.000 description 10
- LTYOQGRJFJAKNA-DVVLENMVSA-N malonyl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CC(O)=O)O[C@H]1N1C2=NC=NC(N)=C2N=C1 LTYOQGRJFJAKNA-DVVLENMVSA-N 0.000 description 10
- 229940079593 drug Drugs 0.000 description 9
- 239000003814 drug Substances 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 238000012417 linear regression Methods 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000003981 vehicle Substances 0.000 description 9
- 208000008589 Obesity Diseases 0.000 description 8
- 239000012267 brine Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 235000020824 obesity Nutrition 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 230000002255 enzymatic effect Effects 0.000 description 7
- 238000011534 incubation Methods 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
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- 235000019198 oils Nutrition 0.000 description 7
- 230000037361 pathway Effects 0.000 description 7
- 0 *CC(Nc(cc1)c(C(F)(F)F)cc1Cl)=O Chemical compound *CC(Nc(cc1)c(C(F)(F)F)cc1Cl)=O 0.000 description 6
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 6
- PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical compound CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 description 6
- 101150064015 FAS gene Proteins 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 238000003556 assay Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
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- 239000002552 dosage form Substances 0.000 description 6
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 6
- GVEZIHKRYBHEFX-MNOVXSKESA-N 13C-Cerulenin Natural products CC=CCC=CCCC(=O)[C@H]1O[C@@H]1C(N)=O GVEZIHKRYBHEFX-MNOVXSKESA-N 0.000 description 5
- 206010006187 Breast cancer Diseases 0.000 description 5
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- GVEZIHKRYBHEFX-UHFFFAOYSA-N caerulein A Natural products CC=CCC=CCCC(=O)C1OC1C(N)=O GVEZIHKRYBHEFX-UHFFFAOYSA-N 0.000 description 5
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- -1 thiolate anion Chemical class 0.000 description 5
- FJJYHTVHBVXEEQ-UHFFFAOYSA-N 2,2-dimethylpropanal Chemical compound CC(C)(C)C=O FJJYHTVHBVXEEQ-UHFFFAOYSA-N 0.000 description 4
- YSTUPBOIUOUMHG-UHFFFAOYSA-N 2-bromo-n-(4-chlorophenyl)acetamide Chemical compound ClC1=CC=C(NC(=O)CBr)C=C1 YSTUPBOIUOUMHG-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
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- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 4
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- 101000573542 Penicillium citrinum Compactin nonaketide synthase, enoyl reductase component Proteins 0.000 description 2
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
- C07D333/30—Hetero atoms other than halogen
- C07D333/32—Oxygen atoms
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom 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
- C07D307/60—Two oxygen atoms, e.g. succinic anhydride
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Child & Adolescent Psychology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12904408P | 2008-06-02 | 2008-06-02 | |
| US61/129,044 | 2008-06-02 | ||
| US19312708P | 2008-10-30 | 2008-10-30 | |
| US61/193,127 | 2008-10-30 | ||
| PCT/US2009/045945 WO2009149066A1 (en) | 2008-06-02 | 2009-06-02 | Novel compounds, pharmaceutical compositions containing same, and methods of use for same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011521978A true JP2011521978A (ja) | 2011-07-28 |
| JP2011521978A5 JP2011521978A5 (enExample) | 2012-07-12 |
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| JP2011511901A Pending JP2011521978A (ja) | 2008-06-02 | 2009-06-02 | 新規化合物、それを含む医薬組成物、およびこれらの使用方法 |
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| Country | Link |
|---|---|
| US (1) | US20110288052A1 (enExample) |
| EP (1) | EP2285215A4 (enExample) |
| JP (1) | JP2011521978A (enExample) |
| CN (1) | CN102111998A (enExample) |
| CA (1) | CA2725749A1 (enExample) |
| WO (1) | WO2009149066A1 (enExample) |
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| WO2010118324A2 (en) | 2009-04-09 | 2010-10-14 | Nuclea Biotechnologies, LLC | Antibodies against fatty acid synthase |
| EP2655706A4 (en) * | 2010-11-24 | 2014-10-15 | Gabrielle Ronnett | METHODS OF SCREENING COMPOUNDS THAT ARE CYTOTOXIC FOR TUMOR CELLS AND METHODS OF TREATING TUMOR CELLS USING SUCH COMPOUND |
| US9695133B2 (en) | 2012-07-13 | 2017-07-04 | The Trustees Of Columbia University In The City Of New York | Quinazolinone-based oncogenic-RAS-selective lethal compounds and their use |
| US11202795B2 (en) | 2014-11-20 | 2021-12-21 | Vib Vzw | Means and methods for treatment of early-onset Parkinson's disease |
| CN107847765B (zh) | 2015-06-18 | 2021-05-04 | 89生物有限公司 | 1,4-取代的哌啶衍生物 |
| EP3310773B1 (en) | 2015-06-18 | 2020-12-02 | 89Bio Ltd. | Substituted 4-benzyl and 4-benzoyl piperidine derivatives |
| CN114773241A (zh) * | 2022-04-20 | 2022-07-22 | 益丰新材料股份有限公司 | 一种巯基羧酸酯的连续化合成方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2005533835A (ja) * | 2002-07-09 | 2005-11-10 | ファスゲン，エルエルシー． | 新規の化合物、それを含有する医薬組成物、およびその使用方法 |
| WO2008057585A1 (en) * | 2006-11-08 | 2008-05-15 | Fasgen Llc | Novel compounds, pharmaceutical compositions containing same, and methods of use for same |
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| US4062786A (en) * | 1976-09-24 | 1977-12-13 | Exxon Research And Engineering Company | Lactone oxazolines as oleaginous additives |
| US5981575A (en) * | 1996-11-15 | 1999-11-09 | Johns Hopkins University, The | Inhibition of fatty acid synthase as a means to reduce adipocyte mass |
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2009
- 2009-06-02 EP EP09759226A patent/EP2285215A4/en not_active Withdrawn
- 2009-06-02 US US12/995,663 patent/US20110288052A1/en not_active Abandoned
- 2009-06-02 CN CN2009801292841A patent/CN102111998A/zh active Pending
- 2009-06-02 WO PCT/US2009/045945 patent/WO2009149066A1/en not_active Ceased
- 2009-06-02 JP JP2011511901A patent/JP2011521978A/ja active Pending
- 2009-06-02 CA CA2725749A patent/CA2725749A1/en not_active Abandoned
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005533835A (ja) * | 2002-07-09 | 2005-11-10 | ファスゲン，エルエルシー． | 新規の化合物、それを含有する医薬組成物、およびその使用方法 |
| WO2008057585A1 (en) * | 2006-11-08 | 2008-05-15 | Fasgen Llc | Novel compounds, pharmaceutical compositions containing same, and methods of use for same |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2725749A1 (en) | 2009-12-10 |
| EP2285215A1 (en) | 2011-02-23 |
| CN102111998A (zh) | 2011-06-29 |
| WO2009149066A1 (en) | 2009-12-10 |
| US20110288052A1 (en) | 2011-11-24 |
| EP2285215A4 (en) | 2012-04-04 |
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