TW201006801A - Imidazole carboxamides - Google Patents
Imidazole carboxamides Download PDFInfo
- Publication number
- TW201006801A TW201006801A TW098123468A TW98123468A TW201006801A TW 201006801 A TW201006801 A TW 201006801A TW 098123468 A TW098123468 A TW 098123468A TW 98123468 A TW98123468 A TW 98123468A TW 201006801 A TW201006801 A TW 201006801A
- Authority
- TW
- Taiwan
- Prior art keywords
- methyl
- compound
- group
- pharmaceutically acceptable
- trifluoromethyl
- Prior art date
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- NMIZONYLXCOHEF-UHFFFAOYSA-N 1h-imidazole-2-carboxamide Chemical class NC(=O)C1=NC=CN1 NMIZONYLXCOHEF-UHFFFAOYSA-N 0.000 title abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 148
- -1 mercapto, methoxy Chemical group 0.000 claims description 102
- 150000003839 salts Chemical class 0.000 claims description 37
- 239000000126 substance Substances 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 238000011282 treatment Methods 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 150000002431 hydrogen Chemical group 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
- 239000011737 fluorine Substances 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 239000007789 gas Substances 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000004981 cycloalkylmethyl group Chemical group 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 208000020401 Depressive disease Diseases 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000005864 Sulphur Substances 0.000 claims description 2
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 35
- 230000008569 process Effects 0.000 abstract description 6
- 238000001819 mass spectrum Methods 0.000 description 194
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 189
- 238000002360 preparation method Methods 0.000 description 91
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- 238000005481 NMR spectroscopy Methods 0.000 description 28
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
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- XKRFYHLGVUSROY-UHFFFAOYSA-N argon Substances [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 23
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 20
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 241000700159 Rattus Species 0.000 description 12
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- 208000019901 Anxiety disease Diseases 0.000 description 11
- 239000002253 acid Substances 0.000 description 11
- 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 11
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 10
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- 230000036506 anxiety Effects 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 8
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- IHMQNZFRFVYNDS-UHFFFAOYSA-N tert-butyl n-amino-n-methylcarbamate Chemical compound CN(N)C(=O)OC(C)(C)C IHMQNZFRFVYNDS-UHFFFAOYSA-N 0.000 description 1
- LPXIOYIHXNPBCQ-UHFFFAOYSA-N tert-butyl n-benzyl-n-methylcarbamate Chemical compound CC(C)(C)OC(=O)N(C)CC1=CC=CC=C1 LPXIOYIHXNPBCQ-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 210000003813 thumb Anatomy 0.000 description 1
- 238000012549 training Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
- C07D233/91—Nitro radicals
- C07D233/92—Nitro radicals attached in position 4 or 5
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
-
- 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
-
- 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
-
- 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
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)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Developing Agents For Electrophotography (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8177408P | 2008-07-18 | 2008-07-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW201006801A true TW201006801A (en) | 2010-02-16 |
Family
ID=41128155
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW098123468A TW201006801A (en) | 2008-07-18 | 2009-07-10 | Imidazole carboxamides |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US7754742B2 (enExample) |
| EP (1) | EP2318375B1 (enExample) |
| JP (1) | JP5379227B2 (enExample) |
| KR (1) | KR101287713B1 (enExample) |
| CN (1) | CN102099344B (enExample) |
| AR (1) | AR074631A1 (enExample) |
| BR (1) | BRPI0915977A2 (enExample) |
| CA (1) | CA2731215C (enExample) |
| CY (1) | CY1113315T1 (enExample) |
| DK (1) | DK2318375T3 (enExample) |
| EA (1) | EA018434B1 (enExample) |
| ES (1) | ES2393243T3 (enExample) |
| HR (1) | HRP20120830T1 (enExample) |
| MX (1) | MX2011000611A (enExample) |
| PL (1) | PL2318375T3 (enExample) |
| PT (1) | PT2318375E (enExample) |
| SI (1) | SI2318375T1 (enExample) |
| TW (1) | TW201006801A (enExample) |
| WO (1) | WO2010009062A1 (enExample) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR059898A1 (es) | 2006-03-15 | 2008-05-07 | Janssen Pharmaceutica Nv | Derivados de 3-ciano-piridona 1,4-disustituida y su uso como moduladores alostericos de los receptores mglur2 |
| TW200900065A (en) | 2007-03-07 | 2009-01-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-pyridinyloxy-phenyl)-pyridin-2-one derivatives |
| TW200845978A (en) | 2007-03-07 | 2008-12-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-tetrahydropyran-phenyl)-pyridin-2-one derivatives |
| BRPI0816970A2 (pt) | 2007-09-14 | 2015-03-24 | Ortho Mcneil Janssen Pharm | 1,3-dissubstituídas-4-fenil-1h-piridin-2-onas |
| EA017648B1 (ru) | 2007-09-14 | 2013-02-28 | Орто-Макнейл-Янссен Фармасьютикалз, Инк. | 1',3'-двузамещенные-4-фенил-3,4,5,6-тетрагидро-2н,1'н-[1,4']бипириди-нил-2'-оны |
| JP5547194B2 (ja) | 2008-09-02 | 2014-07-09 | ジャンセン ファーマシューティカルズ， インコーポレイテッド． | 代謝型グルタミン酸受容体の調節因子としての３−アザビシクロ［３．１．０］ヘキシル誘導体 |
| WO2010043396A1 (en) | 2008-10-16 | 2010-04-22 | Ortho-Mcneil-Janssen Pharmaceuticals, Inc. | Indole and benzomorpholine derivatives as modulators of metabotropic glutamate receptors |
| CN102439015B (zh) | 2009-05-12 | 2015-05-13 | 杨森制药有限公司 | 1,2,4-三唑并[4,3-a]吡啶衍生物和其作为mGluR2受体的正向变构调节剂的用途 |
| MY153913A (en) | 2009-05-12 | 2015-04-15 | Janssen Pharmaceuticals Inc | 7-aryl-1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
| HRP20131122T1 (hr) | 2009-05-12 | 2013-12-20 | Janssen Pharmaceuticals, Inc. | Derivati 1,2,4-triazolo[4,3-a] piridina i njihova uporaba u lijeäśenju ili prevenciji neuroloških i psihijatrijskih poremeä†aja |
| EP2661435B1 (en) | 2010-11-08 | 2015-08-19 | Janssen Pharmaceuticals, Inc. | 1,2,4-TRIAZOLO[4,3-a]PYRIDINE DERIVATIVES AND THEIR USE AS POSITIVE ALLOSTERIC MODULATORS OF MGLUR2 RECEPTORS |
| ES2536433T3 (es) | 2010-11-08 | 2015-05-25 | Janssen Pharmaceuticals, Inc. | Derivados de 1,2,4-triazolo[4,3-a]piridina y su uso como moduladores alostéricos positivos de receptores mGluR2 |
| JP5852664B2 (ja) | 2010-11-08 | 2016-02-03 | ジヤンセン・フアーマシユーチカルズ・インコーポレーテツド | １，２，４−トリアゾロ［４，３−ａ］ピリジン誘導体およびｍＧｌｕＲ２受容体のポジティブアロステリックモジュレーターとしてのそれらの使用 |
| CN103502218B (zh) * | 2011-03-04 | 2016-08-17 | 生命科技公司 | 用于缀合生物分子的化合物和方法 |
| WO2012131539A1 (en) | 2011-03-31 | 2012-10-04 | Pfizer Inc. | Novel bicyclic pyridinones |
| UA110688C2 (uk) | 2012-09-21 | 2016-01-25 | Пфайзер Інк. | Біциклічні піридинони |
| US10154988B2 (en) | 2012-11-14 | 2018-12-18 | The Johns Hopkins University | Methods and compositions for treating schizophrenia |
| JO3368B1 (ar) | 2013-06-04 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 6، 7- ثاني هيدرو بيرازولو [5،1-a] بيرازين- 4 (5 يد)- اون واستخدامها بصفة منظمات تفارغية سلبية لمستقبلات ميجلور 2 |
| JO3367B1 (ar) | 2013-09-06 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 2،1، 4- ثلاثي زولو [3،4-a] بيريدين واستخدامها بصفة منظمات تفارغية موجبة لمستقبلات ميجلور 2 |
| ME03518B (me) | 2014-01-21 | 2020-04-20 | Janssen Pharmaceutica Nv | Kombinacije koje obuhvataju pozitivne alosterične modulatore ili ortosterične agoniste metabotropnog glutamatergičnog receptora podtipa 2 i njihova primjena |
| PL3096790T3 (pl) | 2014-01-21 | 2020-01-31 | Janssen Pharmaceutica, N.V. | Kombinacje zawierające pozytywne modulatory allosteryczne lub agonistów ortosterycznych metabotropowego receptora glutaminergicznego podtypu 2 i ich zastosowanie |
| KR102000382B1 (ko) | 2015-02-03 | 2019-07-15 | 화이자 인코포레이티드 | 신규 시클로프로파벤조푸라닐 피리도피라진디온 |
| US10577332B2 (en) | 2015-04-23 | 2020-03-03 | Hoffmann-La Roche Inc. | Tetrazole derivatives |
| CN104788694B (zh) * | 2015-04-29 | 2018-06-08 | 江苏亚宝绝缘材料股份有限公司 | 一种超低收缩率的聚酰亚胺薄膜 |
| WO2017060202A1 (en) | 2015-10-06 | 2017-04-13 | F. Hoffmann-La Roche Ag | Triazole derivatives |
| EP3411365B1 (en) | 2016-02-02 | 2019-11-20 | H. Hoffnabb-La Roche Ag | Pyrazol-pyridine derivatives as eaat3 inhibitors |
| CN109071451B (zh) | 2016-05-27 | 2022-07-15 | 豪夫迈·罗氏有限公司 | 作为eaat3抑制剂的吡唑化合物 |
| WO2018069362A1 (en) | 2016-10-14 | 2018-04-19 | F. Hoffmann-La Roche Ag | Imidazole compounds as eaat3 inhibitors |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3068213D1 (en) | 1979-09-05 | 1984-07-19 | Glaxo Group Ltd | Phenol derivatives, processes for their preparation and pharmaceutical compositions containing them |
| US4666928A (en) | 1984-08-30 | 1987-05-19 | Merck Frosst Canada, Ind. | Propylphenoxy pyridine carboxylates as leukotriene antagonists |
| DE69210091T2 (de) | 1991-05-31 | 1996-10-02 | Sumitomo Pharma | Leukotrien-B4-Antagonisten |
| AU2001234420A1 (en) | 2000-02-03 | 2001-08-14 | Eli Lilly And Company | Potentiators of glutamate receptors |
| JP2006502143A (ja) * | 2002-08-26 | 2006-01-19 | メルク エンド カムパニー インコーポレーテッド | 向代謝型グルタミン酸受容体のアセトフェノン増強因子 |
| CN1993326A (zh) * | 2004-07-30 | 2007-07-04 | 默克公司 | 代谢型谷氨酸受体的杂环苯乙酮增效剂 |
| CA2574971A1 (en) | 2004-07-30 | 2006-02-09 | Merck & Co., Inc. | Indanone potentiators of metabotropic glutamate receptors |
| TW200613272A (en) | 2004-08-13 | 2006-05-01 | Astrazeneca Ab | Isoindolone compounds and their use as metabotropic glutamate receptor potentiators |
| AU2005299797A1 (en) | 2004-10-25 | 2006-05-04 | Merck & Co., Inc. | Heterocyclic indanone potentiators of metabotropic glutamate receptors |
| ATE543807T1 (de) * | 2004-11-22 | 2012-02-15 | Lilly Co Eli | Verstärker von glutamat-rezeptoren |
| BRPI0517423A (pt) | 2004-12-27 | 2008-10-07 | Astrazeneca Ab | composto, composição farmacêutica, método para o tratamento ou prevenção de distúrbios neurológicos e psiquiátricos associados com disfunção do glutamato em um animal, e, uso em um composto |
| JP5031745B2 (ja) | 2005-08-12 | 2012-09-26 | アストラゼネカ アクチボラグ | 代謝型グルタミン酸受容体増強性イソインドロン |
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2009
- 2009-07-10 TW TW098123468A patent/TW201006801A/zh unknown
- 2009-07-13 AR ARP090102635A patent/AR074631A1/es not_active Application Discontinuation
- 2009-07-14 EA EA201170227A patent/EA018434B1/ru not_active IP Right Cessation
- 2009-07-14 ES ES09790351T patent/ES2393243T3/es active Active
- 2009-07-14 PT PT09790351T patent/PT2318375E/pt unknown
- 2009-07-14 JP JP2011518823A patent/JP5379227B2/ja not_active Expired - Fee Related
- 2009-07-14 KR KR1020117001166A patent/KR101287713B1/ko not_active Expired - Fee Related
- 2009-07-14 BR BRPI0915977A patent/BRPI0915977A2/pt not_active IP Right Cessation
- 2009-07-14 CN CN2009801274345A patent/CN102099344B/zh not_active Expired - Fee Related
- 2009-07-14 PL PL09790351T patent/PL2318375T3/pl unknown
- 2009-07-14 WO PCT/US2009/050440 patent/WO2010009062A1/en not_active Ceased
- 2009-07-14 CA CA2731215A patent/CA2731215C/en not_active Expired - Fee Related
- 2009-07-14 EP EP09790351A patent/EP2318375B1/en active Active
- 2009-07-14 SI SI200930350T patent/SI2318375T1/sl unknown
- 2009-07-14 MX MX2011000611A patent/MX2011000611A/es active IP Right Grant
- 2009-07-14 HR HRP20120830AT patent/HRP20120830T1/hr unknown
- 2009-07-14 US US12/502,252 patent/US7754742B2/en not_active Expired - Fee Related
- 2009-07-14 DK DK09790351.2T patent/DK2318375T3/da active
-
2012
- 2012-11-07 CY CY20121101058T patent/CY1113315T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AR074631A1 (es) | 2011-02-02 |
| HRP20120830T1 (hr) | 2012-11-30 |
| CA2731215C (en) | 2013-08-27 |
| EA018434B1 (ru) | 2013-07-30 |
| EA201170227A1 (ru) | 2011-06-30 |
| CN102099344A (zh) | 2011-06-15 |
| EP2318375B1 (en) | 2012-09-19 |
| CN102099344B (zh) | 2013-10-30 |
| EP2318375A1 (en) | 2011-05-11 |
| DK2318375T3 (da) | 2012-10-08 |
| KR20110022676A (ko) | 2011-03-07 |
| JP5379227B2 (ja) | 2013-12-25 |
| JP2011528658A (ja) | 2011-11-24 |
| MX2011000611A (es) | 2011-03-01 |
| US20100016373A1 (en) | 2010-01-21 |
| CY1113315T1 (el) | 2016-04-13 |
| WO2010009062A1 (en) | 2010-01-21 |
| SI2318375T1 (sl) | 2012-11-30 |
| US7754742B2 (en) | 2010-07-13 |
| KR101287713B1 (ko) | 2013-07-23 |
| CA2731215A1 (en) | 2010-01-21 |
| AU2009271105A1 (en) | 2010-01-21 |
| PT2318375E (pt) | 2012-10-22 |
| PL2318375T3 (pl) | 2013-02-28 |
| BRPI0915977A2 (pt) | 2018-10-30 |
| ES2393243T3 (es) | 2012-12-19 |
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