CA2861390A1 - Tricyclic sulfonamide compounds and methods of making and using same - Google Patents
Tricyclic sulfonamide compounds and methods of making and using same Download PDFInfo
- Publication number
- CA2861390A1 CA2861390A1 CA2861390A CA2861390A CA2861390A1 CA 2861390 A1 CA2861390 A1 CA 2861390A1 CA 2861390 A CA2861390 A CA 2861390A CA 2861390 A CA2861390 A CA 2861390A CA 2861390 A1 CA2861390 A1 CA 2861390A1
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- CA
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- Prior art keywords
- 6alkyl
- group
- substituted
- optionally
- hydrogen
- 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.)
- Abandoned
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- -1 sulfonamide compounds Chemical class 0.000 title claims abstract description 84
- 238000000034 method Methods 0.000 title claims abstract description 70
- 229940124530 sulfonamide Drugs 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 186
- 208000008589 Obesity Diseases 0.000 claims abstract description 25
- 235000020824 obesity Nutrition 0.000 claims abstract description 24
- 239000000203 mixture Substances 0.000 claims description 105
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 58
- 125000001424 substituent group Chemical group 0.000 claims description 58
- 229910052739 hydrogen Inorganic materials 0.000 claims description 57
- 239000001257 hydrogen Substances 0.000 claims description 57
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 53
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 52
- 125000000623 heterocyclic group Chemical group 0.000 claims description 43
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 40
- 235000019000 fluorine Nutrition 0.000 claims description 39
- 229910052757 nitrogen Inorganic materials 0.000 claims description 38
- 229910052731 fluorine Inorganic materials 0.000 claims description 34
- 239000011737 fluorine Substances 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 30
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 29
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 25
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 24
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 23
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 150000002367 halogens Chemical class 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- 125000001153 fluoro group Chemical group F* 0.000 claims description 20
- 125000004043 oxo group Chemical group O=* 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 150000002148 esters Chemical class 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 17
- 125000005842 heteroatom Chemical group 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 229940002612 prodrug Drugs 0.000 claims description 11
- 239000000651 prodrug Substances 0.000 claims description 11
- 230000004580 weight loss Effects 0.000 claims description 11
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 9
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
- 125000002837 carbocyclic group Chemical group 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 230000005764 inhibitory process Effects 0.000 claims description 6
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 5
- 241000282326 Felis catus Species 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 238000007920 subcutaneous administration Methods 0.000 claims description 3
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 2
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 2
- 102000002933 Thioredoxin Human genes 0.000 claims description 2
- 230000033115 angiogenesis Effects 0.000 claims description 2
- 230000003579 anti-obesity Effects 0.000 claims description 2
- 230000001939 inductive effect Effects 0.000 claims description 2
- 230000003834 intracellular effect Effects 0.000 claims description 2
- 238000001990 intravenous administration Methods 0.000 claims description 2
- 210000000056 organ Anatomy 0.000 claims description 2
- 230000000638 stimulation Effects 0.000 claims description 2
- 108060008226 thioredoxin Proteins 0.000 claims description 2
- 229940094937 thioredoxin Drugs 0.000 claims description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 20
- 150000002431 hydrogen Chemical class 0.000 claims 18
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 8
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 6
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 6
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 2
- UIFKHHKRQMKRGQ-WAYWQWQTSA-N 8-[[2-[(z)-3-(diethylamino)prop-1-enyl]-4-fluorophenyl]sulfonylamino]-5h-chromeno[3,4-c]pyridazine-7-carboxylic acid Chemical compound CCN(CC)C\C=C/C1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C2C3=CC=NN=C3COC2=C1C(O)=O UIFKHHKRQMKRGQ-WAYWQWQTSA-N 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 17
- 230000000694 effects Effects 0.000 abstract description 13
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 12
- 101000979001 Homo sapiens Methionine aminopeptidase 2 Proteins 0.000 abstract description 2
- 102100023174 Methionine aminopeptidase 2 Human genes 0.000 abstract 1
- 239000002904 solvent Substances 0.000 description 72
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
- 239000000543 intermediate Substances 0.000 description 52
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 50
- 206010033307 Overweight Diseases 0.000 description 42
- 238000011282 treatment Methods 0.000 description 41
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 37
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 34
- 239000003795 chemical substances by application Substances 0.000 description 32
- 235000002639 sodium chloride Nutrition 0.000 description 29
- 239000007787 solid Substances 0.000 description 29
- 239000002585 base Substances 0.000 description 28
- 235000019441 ethanol Nutrition 0.000 description 28
- 239000000243 solution Substances 0.000 description 28
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 26
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 238000010992 reflux Methods 0.000 description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 22
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 21
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
- 239000002253 acid Substances 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 239000003826 tablet Substances 0.000 description 18
- 239000002775 capsule Substances 0.000 description 17
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 16
- 125000000217 alkyl group Chemical group 0.000 description 16
- 125000004432 carbon atom Chemical group C* 0.000 description 16
- 229910052763 palladium Inorganic materials 0.000 description 16
- 238000005160 1H NMR spectroscopy Methods 0.000 description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000003054 catalyst Substances 0.000 description 15
- 238000004587 chromatography analysis Methods 0.000 description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
- 150000001412 amines Chemical class 0.000 description 14
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 14
- 239000000706 filtrate Substances 0.000 description 14
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- 241001465754 Metazoa Species 0.000 description 13
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 12
- 239000003153 chemical reaction reagent Substances 0.000 description 12
- 239000003937 drug carrier Substances 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 239000001301 oxygen Substances 0.000 description 12
- 239000000377 silicon dioxide Substances 0.000 description 12
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
- 229910000027 potassium carbonate Inorganic materials 0.000 description 11
- 238000006722 reduction reaction Methods 0.000 description 11
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 11
- 101150041968 CDC13 gene Proteins 0.000 description 10
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- 210000000577 adipose tissue Anatomy 0.000 description 10
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 10
- 125000006239 protecting group Chemical group 0.000 description 10
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 201000010099 disease Diseases 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
- 125000003277 amino group Chemical group 0.000 description 8
- 230000003647 oxidation Effects 0.000 description 8
- 238000007254 oxidation reaction Methods 0.000 description 8
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].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.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 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
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- 238000003786 synthesis reaction Methods 0.000 description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 8
- 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 7
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
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- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 7
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- NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical compound NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 description 6
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/052—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being six-membered
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261587828P | 2012-01-18 | 2012-01-18 | |
| US61/587,828 | 2012-01-18 | ||
| PCT/US2013/021919 WO2013109739A1 (en) | 2012-01-18 | 2013-01-17 | Tricyclic sulfonamide compounds and methods of making and using same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2861390A1 true CA2861390A1 (en) | 2013-07-25 |
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| JP6169716B2 (ja) | 2012-11-05 | 2017-07-26 | ザフゲン，インコーポレイテッド | 肝疾患を治療する方法 |
| BR112015010223A2 (pt) | 2012-11-05 | 2017-07-11 | Zafgen Inc | compostos tricíclicos para o uso no tratamento e/ou controle de obesidade |
| BR112015010225A2 (pt) | 2012-11-05 | 2017-07-11 | Zafgen Inc | compostos tricíclicos e seus métodos de produção e utilização |
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| JP7335893B2 (ja) | 2017-12-22 | 2023-08-30 | ラヴェンナ ファーマシューティカルズ，インコーポレイテッド | ホスファチジルイノシトールリン酸キナーゼ阻害剤としてのクロメノピリジン誘導体 |
| TW202112784A (zh) | 2019-06-17 | 2021-04-01 | 美商佩特拉製藥公司 | 作為磷脂酸肌醇磷酸激酶抑制劑之𠳭唏并嘧啶衍生物 |
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-
2013
- 2013-01-17 CA CA2861390A patent/CA2861390A1/en not_active Abandoned
- 2013-01-17 AU AU2013209723A patent/AU2013209723B2/en not_active Ceased
- 2013-01-17 KR KR1020147022926A patent/KR20140112565A/ko not_active Withdrawn
- 2013-01-17 EP EP13702684.5A patent/EP2804866B1/en active Active
- 2013-01-17 JP JP2014553405A patent/JP6035347B2/ja not_active Expired - Fee Related
- 2013-01-17 US US14/372,893 patent/US9359369B2/en not_active Expired - Fee Related
- 2013-01-17 BR BR112014017673A patent/BR112014017673A8/pt not_active IP Right Cessation
- 2013-01-17 MX MX2014008706A patent/MX2014008706A/es unknown
- 2013-01-17 WO PCT/US2013/021919 patent/WO2013109739A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| WO2013109739A1 (en) | 2013-07-25 |
| CN104203954A (zh) | 2014-12-10 |
| BR112014017673A8 (pt) | 2017-07-11 |
| EP2804866A1 (en) | 2014-11-26 |
| BR112014017673A2 (cg-RX-API-DMAC7.html) | 2017-06-20 |
| MX2014008706A (es) | 2015-03-05 |
| KR20140112565A (ko) | 2014-09-23 |
| JP2015504091A (ja) | 2015-02-05 |
| EP2804866B1 (en) | 2016-11-16 |
| AU2013209723B2 (en) | 2016-11-24 |
| US20140378462A1 (en) | 2014-12-25 |
| JP6035347B2 (ja) | 2016-11-30 |
| AU2013209723A1 (en) | 2014-08-07 |
| US9359369B2 (en) | 2016-06-07 |
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