JP2009532429A - 新規ビアリールアミン類 - Google Patents
新規ビアリールアミン類 Download PDFInfo
- Publication number
- JP2009532429A JP2009532429A JP2009503560A JP2009503560A JP2009532429A JP 2009532429 A JP2009532429 A JP 2009532429A JP 2009503560 A JP2009503560 A JP 2009503560A JP 2009503560 A JP2009503560 A JP 2009503560A JP 2009532429 A JP2009532429 A JP 2009532429A
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- JP
- Japan
- Prior art keywords
- chloro
- disorders
- mmol
- phenyl
- pyridin
- 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.)
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Classifications
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- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- 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
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Landscapes
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
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Applications Claiming Priority (2)
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| GBGB0606774.8A GB0606774D0 (en) | 2006-04-03 | 2006-04-03 | Organic compounds |
| PCT/EP2007/053155 WO2007113276A1 (en) | 2006-04-03 | 2007-04-02 | Novel bi-aryl amines |
Publications (2)
| Publication Number | Publication Date |
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| JP2009532429A true JP2009532429A (ja) | 2009-09-10 |
| JP2009532429A5 JP2009532429A5 (enExample) | 2010-05-20 |
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| WO (1) | WO2007113276A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2015098991A1 (ja) * | 2013-12-26 | 2015-07-02 | 東レ株式会社 | Ｎ－アルキルアミド誘導体及びその医薬用途 |
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| GB0420722D0 (en) | 2004-09-17 | 2004-10-20 | Addex Pharmaceuticals Sa | Novel allosteric modulators |
| WO2007013830A1 (en) | 2005-07-26 | 2007-02-01 | Portela & Ca. S.A. | Nitrocatechol derivatives as comt inhibitors |
| 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 |
| EP1845097A1 (en) | 2006-04-10 | 2007-10-17 | Portela & Ca., S.A. | Oxadiazole derivatives as COMT inhibitors |
| DK2481410T3 (en) | 2007-01-31 | 2016-10-24 | Bial - Portela & Ca S A | Nitrocatecholderivater as COMT inhibitors administered in a specific dosage regimen |
| TW200845978A (en) | 2007-03-07 | 2008-12-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-tetrahydropyran-phenyl)-pyridin-2-one derivatives |
| TW200900065A (en) | 2007-03-07 | 2009-01-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-pyridinyloxy-phenyl)-pyridin-2-one derivatives |
| TW200922566A (en) | 2007-09-14 | 2009-06-01 | Ortho Mcneil Janssen Pharm | 1,3 disubstituted 4-(aryl-X-phenyl)-1H-pyridin-2-ones |
| 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 |
| CA2704436C (en) | 2007-11-14 | 2016-01-05 | Ortho-Mcneil-Janssen Pharmaceuticals, Inc. | Imidazo[1,2-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
| BRPI0908731A2 (pt) | 2008-03-17 | 2017-05-16 | Bial - Portela & C A S A | formas cristalinas de 5-[3-(2,5-dicloro-4,6-dimetil-1-óxi-piridina-3-il)[1,2,4]oxadiazol-5-il]-3-nitrobenzeno-1,2-diol |
| 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 |
| MY154000A (en) | 2008-09-22 | 2015-04-30 | Cayman Chem Co | Multiheteroaryl compounds as inhibitors of h-pgds and their use for treating prostaglandin d2 mediated diseases |
| CA2739263A1 (en) * | 2008-10-03 | 2010-04-08 | Lexicon Pharmaceuticals, Inc. | Tryptophan hydroxylase inhibitors and methods of their use |
| WO2010043396A1 (en) | 2008-10-16 | 2010-04-22 | Ortho-Mcneil-Janssen Pharmaceuticals, Inc. | Indole and benzomorpholine derivatives as modulators of metabotropic glutamate receptors |
| JP5690277B2 (ja) | 2008-11-28 | 2015-03-25 | 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インドールおよびベンゾオキサジン誘導体 |
| PA8854101A1 (es) | 2008-12-18 | 2010-07-27 | Ortho Mcneil Janssen Pharm | Derivados de imidazol bicíclicos sustituidos como moduladores de gamma secretasa |
| CN102325765B (zh) | 2009-02-06 | 2014-12-24 | 杨森制药公司 | 作为γ-分泌酶调节剂的取代的双环杂环化合物 |
| TWI461425B (zh) | 2009-02-19 | 2014-11-21 | Janssen Pharmaceuticals Inc | 作為伽瑪分泌酶調節劑之新穎經取代的苯并唑、苯并咪唑、唑并吡啶及咪唑并吡啶衍生物類 |
| CN102448444B (zh) | 2009-04-01 | 2016-05-25 | 巴尔-波特拉及康邦亚股份有限公司 | 包括硝基儿茶酚衍生物的药物制剂及其制备方法 |
| EA019702B1 (ru) | 2009-05-07 | 2014-05-30 | Янссен Фармасьютикалз, Инк. | Замещенные производные индазола и азаиндазола в качестве модуляторов гамма-секретазы |
| 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 |
| WO2011006903A1 (en) | 2009-07-15 | 2011-01-20 | Ortho-Mcneil-Janssen Pharmaceuticals, Inc | Substituted triazole and imidazole derivatives as gamma secretase modulators |
| WO2011073298A1 (en) * | 2009-12-18 | 2011-06-23 | Neurosearch A/S | Tetrazole derivatives as nicotinic acetylcholine receptor modulators |
| WO2011073297A1 (en) * | 2009-12-18 | 2011-06-23 | Neurosearch A/S | Tetrazole derivatives as nicotinic acetylcholine receptor moudlators |
| PH12012501381A1 (en) | 2010-01-15 | 2012-10-22 | Janssen Pharmaceuticals Inc | Novel substituted bicyclic triazole derivatives as gamma secretase modulators |
| 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 |
| US20140045900A1 (en) | 2011-02-11 | 2014-02-13 | Bial-Portela & Ca, S.A. | Administration regime for nitrocatechols |
| ES2536442T3 (es) | 2011-03-24 | 2015-05-25 | Janssen Pharmaceuticals, Inc. | Derivados novedosos de triazolil piperazina y triazolil piperidina como moduladores de la gamma secretasa |
| CN103874702B (zh) | 2011-07-15 | 2015-12-09 | 杨森制药公司 | 作为γ分泌酶调节剂的经取代的吲哚衍生物 |
| US9126988B2 (en) | 2011-12-13 | 2015-09-08 | Bial—Portela & Ca, S.A. | Intermediate for preparing a catechol-O-methyltransferase inhibitor |
| CN104583208B (zh) | 2012-05-16 | 2016-09-28 | 杨森制药公司 | 可用于治疗(尤其是)阿尔茨海默病的取代的3,4-二氢-2H-吡啶并[1,2-a]吡嗪-1,6-二酮衍生物 |
| WO2014096212A1 (en) | 2012-12-20 | 2014-06-26 | Janssen Pharmaceutica Nv | NOVEL TRICYCLIC 3,4-DIHYDRO-2H-PYRIDO[1,2-α]PYRAZINE-1,6-DIONE DERIVATIVES AS GAMMA SECRETASE MODULATORS |
| KR102171710B1 (ko) | 2013-01-17 | 2020-10-30 | 얀센 파마슈티카 엔.브이. | 감마 세크레타제 조절 인자로서의 신규 치환 피리도-피페라지논 유도체 |
| 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 |
| US10562897B2 (en) | 2014-01-16 | 2020-02-18 | Janssen Pharmaceutica Nv | Substituted 3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,6-diones as gamma secretase modulators |
| 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 |
| 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 |
| WO2016083863A1 (en) | 2014-11-28 | 2016-06-02 | Bial - Portela & Ca, S.A. | Medicaments for slowing parkinson's disease |
| AU2017233739A1 (en) | 2016-03-15 | 2018-09-20 | Bayer Cropscience Aktiengesellschaft | Substituted sulfonyl amides for controlling animal pests |
| KR101798840B1 (ko) | 2017-05-17 | 2017-11-17 | 주식회사 레고켐 바이오사이언스 | 신규 오토탁신 저해 화합물 및 이를 함유하는 약제학적 조성물 |
| US10961242B2 (en) | 2017-05-17 | 2021-03-30 | Legochem Biosciences, Inc. | Compounds as autotaxin inhibitors and pharmaceutical compositions comprising the same |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60246377A (ja) * | 1984-05-12 | 1985-12-06 | フアイソンズ・ピーエルシー | 新規な複素環化合物を含有する組成物 |
| JP2004510707A (ja) * | 2000-08-08 | 2004-04-08 | オーソ−マクニール・フアーマシユーチカル・インコーポレーテツド | 神経保護性の２−ピリジナミン組成物および関係する方法 |
| WO2005021548A2 (en) * | 2003-08-25 | 2005-03-10 | Adenosine Therapeutics, Llc | Substituted 8-heteroaryl xanthines |
| WO2005113548A1 (en) * | 2004-05-20 | 2005-12-01 | Sugen, Inc. | Thiophene heteroaryl amines |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0164204A1 (en) * | 1984-05-12 | 1985-12-11 | FISONS plc | Novel pharmaceutically useful pyrimidines |
| BR0208010A (pt) * | 2001-03-12 | 2004-12-21 | Avanir Pharmaceuticals | Composto de benzimidazol para modulação de ige e inibição de proliferação celular |
| EP1715867A4 (en) * | 2004-02-12 | 2009-04-15 | Merck & Co Inc | BIPYRIDYLAMIDE AS MODULATORS OF METABOTROPIC GLUTAMATE RECEPTOR-5 |
| WO2008128968A1 (en) * | 2007-04-19 | 2008-10-30 | Novartis Ag | Nicotinic acid derivatives as modulators of metabotropic glutamate receptor-5 |
-
2006
- 2006-04-03 GB GBGB0606774.8A patent/GB0606774D0/en not_active Ceased
-
2007
- 2007-04-02 JP JP2009503560A patent/JP2009532429A/ja active Pending
- 2007-04-02 KR KR1020087026788A patent/KR20090005354A/ko not_active Withdrawn
- 2007-04-02 US US12/296,034 patent/US20090286827A1/en not_active Abandoned
- 2007-04-02 RU RU2008143180/04A patent/RU2008143180A/ru not_active Application Discontinuation
- 2007-04-02 BR BRPI0709936-3A patent/BRPI0709936A2/pt not_active Application Discontinuation
- 2007-04-02 EP EP07727627A patent/EP2004624A1/en not_active Withdrawn
- 2007-04-02 WO PCT/EP2007/053155 patent/WO2007113276A1/en not_active Ceased
- 2007-04-02 MX MX2008012818A patent/MX2008012818A/es not_active Application Discontinuation
- 2007-04-02 AU AU2007233669A patent/AU2007233669A1/en not_active Abandoned
- 2007-04-02 CA CA002646088A patent/CA2646088A1/en not_active Abandoned
- 2007-04-02 CN CNA2007800204897A patent/CN101460478A/zh active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60246377A (ja) * | 1984-05-12 | 1985-12-06 | フアイソンズ・ピーエルシー | 新規な複素環化合物を含有する組成物 |
| JP2004510707A (ja) * | 2000-08-08 | 2004-04-08 | オーソ−マクニール・フアーマシユーチカル・インコーポレーテツド | 神経保護性の２−ピリジナミン組成物および関係する方法 |
| WO2005021548A2 (en) * | 2003-08-25 | 2005-03-10 | Adenosine Therapeutics, Llc | Substituted 8-heteroaryl xanthines |
| WO2005113548A1 (en) * | 2004-05-20 | 2005-12-01 | Sugen, Inc. | Thiophene heteroaryl amines |
Non-Patent Citations (5)
| Title |
|---|
| JPN5009003137; ＤＡＴＡＢＡＳＥ ＣＨＥＭＣＨＡＴＳ， ＲＮ＝３９２７３８-４３-１，３９２６７０-６６-５，３８４８０６-７２-８，３９２６６４-１２-９ * |
| JPN5009003138; ＪＡＹＡＮＴＨ: ＩＮＤＩＡＮ Ｊ． ＣＨＥＭ． Ｖ１１ Ｎ１１, 1973, Ｐ１１１２-１１１４ * |
| JPN5009003139; ＮＡＩＫ Ｈ Ａ: ＩＮＤＩＡＮ ＪＯＵＲＮＡＬ ＯＦ ＣＨＥＭＩＳＴＲＹ Ｖ１５Ｂ Ｎ４, 1977, Ｐ３３８-３４０ * |
| JPN7012003695; ＳＴＮ ＯＮ ＴＨＥ ＷＥＢ， ＦＩＬＥ ＣＡＰＬＵＳ， ＡＣＣＥＳＳＩＯＮ ＮＯ．＝１９８８：２３３０９ * |
| JPN7012003696; ＳＴＮ ＯＮ ＴＨＥ ＷＥＢ， ＦＩＬＥ ＲＥＧＩＳＴＲＹ， ＲＮ＝８７２０１９-１１-９，８６７２９９-２５-０，３９２７３８-４２-０，３９２６７０-６７-６，３９２６７０-５７-４，３９２６７０ * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015098991A1 (ja) * | 2013-12-26 | 2015-07-02 | 東レ株式会社 | Ｎ－アルキルアミド誘導体及びその医薬用途 |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2646088A1 (en) | 2007-10-11 |
| EP2004624A1 (en) | 2008-12-24 |
| AU2007233669A1 (en) | 2007-10-11 |
| RU2008143180A (ru) | 2010-05-10 |
| MX2008012818A (es) | 2008-10-15 |
| KR20090005354A (ko) | 2009-01-13 |
| CN101460478A (zh) | 2009-06-17 |
| US20090286827A1 (en) | 2009-11-19 |
| BRPI0709936A2 (pt) | 2011-08-02 |
| WO2007113276A1 (en) | 2007-10-11 |
| GB0606774D0 (en) | 2006-05-10 |
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