MX2008016494A - Tiofenos sustituidos con pirazolalcanamida como potenciadores de acido a-amino-3-hidroxi-5-metil-4-isoxazol-propionico (ampa). - Google Patents
Tiofenos sustituidos con pirazolalcanamida como potenciadores de acido a-amino-3-hidroxi-5-metil-4-isoxazol-propionico (ampa).Info
- Publication number
- MX2008016494A MX2008016494A MX2008016494A MX2008016494A MX2008016494A MX 2008016494 A MX2008016494 A MX 2008016494A MX 2008016494 A MX2008016494 A MX 2008016494A MX 2008016494 A MX2008016494 A MX 2008016494A MX 2008016494 A MX2008016494 A MX 2008016494A
- Authority
- MX
- Mexico
- Prior art keywords
- mmol
- trifluoromethyl
- carbon atoms
- carboxamide
- thiophene
- Prior art date
Links
- 229930192474 thiophene Natural products 0.000 title claims description 5
- UUDAMDVQRQNNHZ-UHFFFAOYSA-N (S)-AMPA Chemical compound CC=1ONC(=O)C=1CC(N)C(O)=O UUDAMDVQRQNNHZ-UHFFFAOYSA-N 0.000 title description 6
- 150000003577 thiophenes Chemical class 0.000 title 1
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 41
- 108090000078 AMPA Receptors Proteins 0.000 claims abstract description 21
- 102000003678 AMPA Receptors Human genes 0.000 claims abstract description 21
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 239000012453 solvate Substances 0.000 claims abstract description 9
- 230000001404 mediated effect Effects 0.000 claims abstract description 8
- 230000009782 synaptic response Effects 0.000 claims abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- 238000002560 therapeutic procedure Methods 0.000 claims abstract description 4
- -1 3-Trifluoromethyl-4,5,6,7-tetrahydro-indazol-1-yl Chemical group 0.000 claims description 138
- 125000004432 carbon atom Chemical group C* 0.000 claims description 71
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 36
- 229910052717 sulfur Inorganic materials 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000002837 carbocyclic group Chemical group 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 4
- WBILXYYUMRUDBZ-UHFFFAOYSA-N 2-[[2-[3-tert-butyl-4-[(dimethylamino)methyl]pyrazol-1-yl]acetyl]amino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide Chemical compound N1=C(C(C)(C)C)C(CN(C)C)=CN1CC(=O)NC1=C(C(N)=O)C(CCCC2)=C2S1 WBILXYYUMRUDBZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
- GCDZDXVTDCMNMN-UHFFFAOYSA-N n-(2-aminoethyl)methanesulfonamide Chemical compound CS(=O)(=O)NCCN GCDZDXVTDCMNMN-UHFFFAOYSA-N 0.000 claims description 3
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 3
- XUAUXHZTEUGYOD-UHFFFAOYSA-N 2-[[2-[4-(1-hydroxyethyl)-3-(trifluoromethyl)pyrazol-1-yl]acetyl]amino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide Chemical compound N1=C(C(F)(F)F)C(C(O)C)=CN1CC(=O)NC1=C(C(N)=O)C(CCCC2)=C2S1 XUAUXHZTEUGYOD-UHFFFAOYSA-N 0.000 claims description 2
- LTUFGCFAPCJOFQ-UHFFFAOYSA-N 2h-pyran-3-carboxamide Chemical compound NC(=O)C1=CC=COC1 LTUFGCFAPCJOFQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 2
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims 1
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 81
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- 238000004007 reversed phase HPLC Methods 0.000 description 30
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- 238000000746 purification Methods 0.000 description 25
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- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 22
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- 239000012267 brine Substances 0.000 description 19
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 18
- 235000019341 magnesium sulphate Nutrition 0.000 description 18
- 239000010410 layer Substances 0.000 description 17
- 238000012799 strong cation exchange Methods 0.000 description 17
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 15
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 15
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 14
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- 238000000034 method Methods 0.000 description 13
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 13
- GLQWRXYOTXRDNH-UHFFFAOYSA-N thiophen-2-amine Chemical class NC1=CC=CS1 GLQWRXYOTXRDNH-UHFFFAOYSA-N 0.000 description 13
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 12
- 229910000027 potassium carbonate Inorganic materials 0.000 description 12
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 11
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 11
- 238000003818 flash chromatography Methods 0.000 description 11
- 230000002829 reductive effect Effects 0.000 description 11
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 10
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 10
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 10
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 10
- 239000003480 eluent Substances 0.000 description 10
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- 239000011593 sulfur Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 229960004132 diethyl ether Drugs 0.000 description 9
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 9
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
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- 238000003756 stirring Methods 0.000 description 9
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- ITHFJIMYHSRWDA-UHFFFAOYSA-N 2-[(2-bromoacetyl)amino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide Chemical compound C1CCCC2=C1SC(NC(=O)CBr)=C2C(=O)N ITHFJIMYHSRWDA-UHFFFAOYSA-N 0.000 description 6
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- 230000000699 topical effect Effects 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4965—Non-condensed pyrazines
- A61K31/497—Non-condensed pyrazines containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
- C07D417/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Vascular Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Psychology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP06116592 | 2006-07-04 | ||
| PCT/EP2007/005851 WO2008003452A1 (en) | 2006-07-04 | 2007-07-02 | Pyrazolealkanamide substituted thiophenes as ampa potentiators |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2008016494A true MX2008016494A (es) | 2009-01-21 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2008016494A MX2008016494A (es) | 2006-07-04 | 2007-07-02 | Tiofenos sustituidos con pirazolalcanamida como potenciadores de acido a-amino-3-hidroxi-5-metil-4-isoxazol-propionico (ampa). |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US7820707B2 (enExample) |
| EP (1) | EP2041124B1 (enExample) |
| JP (1) | JP2009541404A (enExample) |
| KR (1) | KR20090027672A (enExample) |
| CN (1) | CN101484448B (enExample) |
| AR (1) | AR061792A1 (enExample) |
| AU (1) | AU2007271469B2 (enExample) |
| CA (1) | CA2655680A1 (enExample) |
| IL (1) | IL196302A0 (enExample) |
| MX (1) | MX2008016494A (enExample) |
| NZ (1) | NZ573325A (enExample) |
| PE (1) | PE20080378A1 (enExample) |
| TW (1) | TW200817385A (enExample) |
| WO (1) | WO2008003452A1 (enExample) |
| ZA (1) | ZA200810165B (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
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| EP2269990A4 (en) * | 2008-03-25 | 2012-04-18 | Takeda Pharmaceutical | Heterocyclic compound |
| TW201012803A (en) * | 2008-06-06 | 2010-04-01 | Organon Nv | Heterocyclic derivatives |
| WO2011036889A1 (ja) * | 2009-09-25 | 2011-03-31 | 武田薬品工業株式会社 | 複素環化合物 |
| WO2011036885A1 (ja) * | 2009-09-25 | 2011-03-31 | 武田薬品工業株式会社 | 複素環化合物 |
| PT2603494T (pt) | 2010-08-10 | 2017-02-03 | Syngenta Participations Ag | Processo para a preparação de 3-haloalquilopirazóis |
| JO3225B1 (ar) * | 2012-11-27 | 2018-03-08 | Lilly Co Eli | 6-((s)-1-{1-[5-(2-هيدروكسي-إيثوكسي)-بيريدين-2-يل]-1h-بيرازول-3-يل}إيثيل)-3h-1 ، 3-بنزو ثيازول-2- أون باعتباره مضاد مستقبل ampa يعتمد على tarp- جاما 8 |
| EP3030568B1 (en) | 2013-08-08 | 2018-09-19 | Galapagos NV | Thieno[2,3-c]pyrans as cftr modulators |
| CN103772282B (zh) * | 2014-02-26 | 2015-09-23 | 上海毕得医药科技有限公司 | 一种3-叔丁基-1h-吡唑-4-甲醛的制备方法 |
| TW201609719A (zh) * | 2014-05-28 | 2016-03-16 | 美國禮來大藥廠 | 作為ＴＡＲＰ－γ８依賴性ＡＭＰＡ受體拮抗劑之６－經取代－３Ｈ－１，３－苯并噻唑－２－酮化合物 |
| CN107286114B (zh) * | 2016-04-13 | 2020-08-18 | 中国人民解放军军事医学科学院毒物药物研究所 | Ampa受体增效剂的脑靶向前药及其医药用途 |
| GB201702221D0 (en) * | 2017-02-10 | 2017-03-29 | Univ Of Sussex | Compounds |
| GB201803340D0 (en) | 2018-03-01 | 2018-04-18 | Univ Of Sussex | Compounds |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2311131A1 (en) * | 1997-11-21 | 1999-06-03 | Nps Pharmaceuticals, Inc. | Metabotropic glutamate receptor antagonists for treating central nervous system diseases |
| ES2249272T3 (es) * | 1999-06-02 | 2006-04-01 | Nps Pharmaceuticals, Inc. | Antagonistas de receptores de glutamato metabotropicos y su uso para el tratamiento de enfermedades del sistema nervioso central. |
| US6414013B1 (en) * | 2000-06-19 | 2002-07-02 | Pharmacia & Upjohn S.P.A. | Thiophene compounds, process for preparing the same, and pharmaceutical compositions containing the same background of the invention |
| US20040171603A1 (en) | 2001-05-18 | 2004-09-02 | Janos Pato | Novel therapeutic targets for the treatment of mycobacterial infections and compounds useful therefor |
| US7345036B2 (en) * | 2001-06-14 | 2008-03-18 | N.V. Organon | (Pyrido/thieno)—[f]—oxazepine-5-one derivatives |
| US20050085531A1 (en) | 2003-10-03 | 2005-04-21 | Hodge Carl N. | Thiophene-based compounds exhibiting ATP-utilizing enzyme inhibitory activity, and compositions, and uses thereof |
| CA2541458C (en) | 2003-10-08 | 2011-09-20 | Eli Lilly And Company | Pyrrole and pyrazole derivatives as potentiators of glutamate receptors |
| ATE552251T1 (de) | 2004-01-09 | 2012-04-15 | Lilly Co Eli | Thiophen- und furanverbindungen |
| JP2008517061A (ja) | 2004-10-20 | 2008-05-22 | コンパス ファーマシューティカルズ リミティド ライアビリティ カンパニー | 抗腫瘍剤としての化合物及びそれらの使用 |
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2007
- 2007-06-14 TW TW096121620A patent/TW200817385A/zh unknown
- 2007-06-29 US US11/771,198 patent/US7820707B2/en active Active
- 2007-07-02 EP EP07801415.6A patent/EP2041124B1/en active Active
- 2007-07-02 CA CA002655680A patent/CA2655680A1/en not_active Abandoned
- 2007-07-02 WO PCT/EP2007/005851 patent/WO2008003452A1/en not_active Ceased
- 2007-07-02 KR KR1020087031534A patent/KR20090027672A/ko not_active Withdrawn
- 2007-07-02 MX MX2008016494A patent/MX2008016494A/es active IP Right Grant
- 2007-07-02 AR ARP070102955A patent/AR061792A1/es unknown
- 2007-07-02 JP JP2009517024A patent/JP2009541404A/ja not_active Ceased
- 2007-07-02 AU AU2007271469A patent/AU2007271469B2/en not_active Ceased
- 2007-07-02 NZ NZ573325A patent/NZ573325A/en unknown
- 2007-07-02 CN CN2007800248081A patent/CN101484448B/zh not_active Expired - Fee Related
- 2007-07-03 PE PE2007000848A patent/PE20080378A1/es not_active Application Discontinuation
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2008
- 2008-11-28 ZA ZA200810165A patent/ZA200810165B/xx unknown
- 2008-12-31 IL IL196302A patent/IL196302A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| TW200817385A (en) | 2008-04-16 |
| WO2008003452A1 (en) | 2008-01-10 |
| EP2041124B1 (en) | 2013-06-26 |
| EP2041124A1 (en) | 2009-04-01 |
| CA2655680A1 (en) | 2008-01-10 |
| CN101484448B (zh) | 2012-03-14 |
| IL196302A0 (en) | 2009-09-22 |
| AU2007271469B2 (en) | 2012-05-31 |
| NZ573325A (en) | 2011-05-27 |
| KR20090027672A (ko) | 2009-03-17 |
| AU2007271469A1 (en) | 2008-01-10 |
| CN101484448A (zh) | 2009-07-15 |
| JP2009541404A (ja) | 2009-11-26 |
| AR061792A1 (es) | 2008-09-24 |
| ZA200810165B (en) | 2009-09-30 |
| US20080255086A1 (en) | 2008-10-16 |
| PE20080378A1 (es) | 2008-04-25 |
| US7820707B2 (en) | 2010-10-26 |
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