JP2004504400A5 - - Google Patents
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- Publication number
- JP2004504400A5 JP2004504400A5 JP2002514138A JP2002514138A JP2004504400A5 JP 2004504400 A5 JP2004504400 A5 JP 2004504400A5 JP 2002514138 A JP2002514138 A JP 2002514138A JP 2002514138 A JP2002514138 A JP 2002514138A JP 2004504400 A5 JP2004504400 A5 JP 2004504400A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- compound
- formula
- bis
- trifluoromethyl
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims 23
- -1 2-hydroxy-ethoxy Chemical group 0.000 claims 7
- 238000000034 method Methods 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 102000002002 Neurokinin-1 Receptors Human genes 0.000 claims 3
- 108010040718 Neurokinin-1 Receptors Proteins 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 239000002464 receptor antagonist Substances 0.000 claims 3
- 229940044551 receptor antagonist Drugs 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- ADTNSTHKMIPKIJ-UHFFFAOYSA-N 1-[3,5-bis(trifluoromethyl)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 ADTNSTHKMIPKIJ-UHFFFAOYSA-N 0.000 claims 1
- OGIQAENFMMDNMW-UHFFFAOYSA-N 2-(2-methylphenyl)pyridine-3-carboxamide Chemical compound CC1=CC=CC=C1C1=NC=CC=C1C(N)=O OGIQAENFMMDNMW-UHFFFAOYSA-N 0.000 claims 1
- OERDCPDEJUGQEH-UHFFFAOYSA-N 2-[3,5-bis(trifluoromethyl)phenyl]-N,2-dimethyl-N-[6-(methylamino)-4-(2-methylphenyl)pyridin-3-yl]propanamide Chemical compound CC(C)(C(N(C)C(C(C1=C(C)C=CC=C1)=C1)=CN=C1NC)=O)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 OERDCPDEJUGQEH-UHFFFAOYSA-N 0.000 claims 1
- IPDWLEJECDILKJ-UHFFFAOYSA-N 2-[3,5-bis(trifluoromethyl)phenyl]-n-[6-(2,3-dihydro-1,4-oxazin-4-yl)-4-(2-methylphenyl)pyridin-3-yl]-n,2-dimethylpropanamide Chemical compound C=1N=C(N2C=COCC2)C=C(C=2C(=CC=CC=2)C)C=1N(C)C(=O)C(C)(C)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 IPDWLEJECDILKJ-UHFFFAOYSA-N 0.000 claims 1
- NIHBNLUMJKDSTD-UHFFFAOYSA-N 2-[3,5-bis(trifluoromethyl)phenyl]-n-[6-(2-hydroxyethylamino)-4-(2-methylphenyl)pyridin-3-yl]-n,2-dimethylpropanamide Chemical compound C=1N=C(NCCO)C=C(C=2C(=CC=CC=2)C)C=1N(C)C(=O)C(C)(C)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 NIHBNLUMJKDSTD-UHFFFAOYSA-N 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 229940047889 isobutyramide Drugs 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- FSDMACCWCGENQO-UHFFFAOYSA-N n-[6-[acetyl(methyl)amino]-4-(2-methylphenyl)pyridin-3-yl]-2-[3,5-bis(trifluoromethyl)phenyl]-n,2-dimethylpropanamide Chemical compound C1=NC(N(C(C)=O)C)=CC(C=2C(=CC=CC=2)C)=C1N(C)C(=O)C(C)(C)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 FSDMACCWCGENQO-UHFFFAOYSA-N 0.000 claims 1
- JGFYMRNGUGQDSG-UHFFFAOYSA-N n-[6-acetamido-4-(2-methylphenyl)pyridin-3-yl]-2-[3,5-bis(trifluoromethyl)phenyl]-n,2-dimethylpropanamide Chemical compound C=1N=C(NC(C)=O)C=C(C=2C(=CC=CC=2)C)C=1N(C)C(=O)C(C)(C)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 JGFYMRNGUGQDSG-UHFFFAOYSA-N 0.000 claims 1
- UJIYLHIYNCDQKJ-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-6-(2-hydroxyethylamino)-n-methyl-4-(2-methylphenyl)pyridine-3-carboxamide Chemical compound C=1N=C(NCCO)C=C(C=2C(=CC=CC=2)C)C=1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 UJIYLHIYNCDQKJ-UHFFFAOYSA-N 0.000 claims 1
- QZCGOXXOGYPNLN-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-6-(4-hydroxypiperidin-1-yl)-n-methyl-4-(2-methylphenyl)pyridine-3-carboxamide Chemical compound C=1N=C(N2CCC(O)CC2)C=C(C=2C(=CC=CC=2)C)C=1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 QZCGOXXOGYPNLN-UHFFFAOYSA-N 0.000 claims 1
- GPPHCXLGQAMULD-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-n-methyl-4-(2-methylphenyl)-6-(1,2,4-triazol-1-yl)pyridine-3-carboxamide Chemical compound C=1N=C(N2N=CN=C2)C=C(C=2C(=CC=CC=2)C)C=1C(=O)N(C)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 GPPHCXLGQAMULD-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP00115846 | 2000-07-24 | ||
| PCT/EP2001/008432 WO2002008232A1 (en) | 2000-07-24 | 2001-07-20 | 4-phenyl-pyridine derivatives as neurokinin-1 receptor antagonists |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004504400A JP2004504400A (ja) | 2004-02-12 |
| JP2004504400A5 true JP2004504400A5 (enExample) | 2005-02-24 |
| JP4118673B2 JP4118673B2 (ja) | 2008-07-16 |
Family
ID=8169331
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002514138A Expired - Lifetime JP4118673B2 (ja) | 2000-07-24 | 2001-07-20 | ニューロキニン１受容体アンタゴニストとしての４−フェニル−ピリジン誘導体 |
Country Status (37)
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1103545B1 (en) * | 1999-11-29 | 2003-11-05 | F. Hoffmann-La Roche Ag | 2-(3,5-Bis-trifluoromethyl-phenyl)-N-methyl-N-(6-morpholin-4-yl-4-o-tolyl-pyridin-3-yl)-isobutyramide |
| EA007720B1 (ru) | 2002-04-26 | 2006-12-29 | Эли Лилли Энд Компани | Производные триазола в качестве антагонистов рецептора тахикинина |
| ES2307925T3 (es) | 2002-04-26 | 2008-12-01 | Eli Lilly And Company | Antagonistas de los receptores de la taquiquinina. |
| EP1556039A2 (en) * | 2002-10-11 | 2005-07-27 | Bristol-Myers Squibb Company | Process for the preparation of tri-nitrogen containing heteroaryl-diamine derivatives useful as pharmaceutical agents and methods of producing pharmaceutical agents |
| EP1638944A1 (en) * | 2003-06-12 | 2006-03-29 | Eli Lilly And Company | Tachykinin receptor antagonists |
| JP4490421B2 (ja) * | 2003-07-03 | 2010-06-23 | エフ．ホフマン−ラ ロシュ アーゲー | 統合失調症を処置するデュアルｎｋ１／ｎｋ３アンタゴニスト |
| TWI280239B (en) * | 2003-07-15 | 2007-05-01 | Hoffmann La Roche | Process for preparation of pyridine derivatives |
| DE602005026669D1 (de) | 2004-07-06 | 2011-04-14 | Hoffmann La Roche | Herstellungsverfahren für carboxamid-pyridin-derivate als zwischenprodukte bei der synthese von nk-1-rezeptor-antagonisten |
| US20060030600A1 (en) * | 2004-08-06 | 2006-02-09 | Patrick Schnider | Dual NK1/NK3 receptor antagonists for the treatment of schizophrenia |
| US20080045610A1 (en) * | 2004-09-23 | 2008-02-21 | Alexander Michalow | Methods for regulating neurotransmitter systems by inducing counteradaptations |
| JP2008514612A (ja) * | 2004-09-23 | 2008-05-08 | ミシャロウ、アレクサンダー | 対抗適応を誘発することにより神経伝達物質系を調節する方法 |
| UA90708C2 (ru) | 2005-02-25 | 2010-05-25 | Ф. Хоффманн-Ля Рош Аг | Таблетки с улучшенной дисперсностью лекарственного вещества |
| US8067662B2 (en) | 2009-04-01 | 2011-11-29 | Aalnex, Inc. | Systems and methods for wound protection and exudate management |
| US7816577B2 (en) | 2006-02-13 | 2010-10-19 | Aalnex, Inc. | Wound shield |
| ATE438632T1 (de) | 2006-05-31 | 2009-08-15 | Hoffmann La Roche | Aryl-4-ethinylisoxazolderivate |
| WO2008090117A1 (en) | 2007-01-24 | 2008-07-31 | Glaxo Group Limited | Pharmaceutical compositions comprising 3, 5-diamin0-6- (2, 3-dichl0phenyl) -l, 2, 4-triazine or r (-) -2, 4-diamino-5- (2, 3-dichlorophenyl) -6-fluoromethyl pyrimidine and an nk1 |
| GB0808747D0 (en) | 2008-05-14 | 2008-06-18 | Glaxo Wellcome Mfg Pte Ltd | Novel compounds |
| US8426450B1 (en) * | 2011-11-29 | 2013-04-23 | Helsinn Healthcare Sa | Substituted 4-phenyl pyridines having anti-emetic effect |
| US10100030B2 (en) | 2013-11-08 | 2018-10-16 | Kissei Pharmaceutical Co., Ltd. | Carboxymethyl piperidine derivative |
| TWI649307B (zh) | 2014-05-07 | 2019-02-01 | 日商橘生藥品工業股份有限公司 | Cyclohexylpyridine derivative |
| US10538491B2 (en) | 2015-03-16 | 2020-01-21 | Vanderbilt University | 4,5-substituted picolinamide and picolinonitrile metabotropic glutamate receptor 2 negative allosteric modulators |
| US11324832B2 (en) * | 2015-12-22 | 2022-05-10 | Endosome Therapeutics, Inc. | Tripartite modulators of endosomal G protein-coupled receptors |
| RU2020131446A (ru) | 2018-02-26 | 2022-03-28 | Оспедале Сан Раффаэле С.Р.Л. | Антагонисты nk-1 для применения в лечении глазной боли |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL111960A (en) | 1993-12-17 | 1999-12-22 | Merck & Co Inc | Morpholines and thiomorpholines their preparation and pharmaceutical compositions containing them |
| HU221139B1 (en) | 1993-12-29 | 2002-08-28 | Merck Sharp & Dohme | Tachykinin antagonist substituted morpholine derivatives, preparation and use thereof |
| IL112778A0 (en) | 1994-03-04 | 1995-05-26 | Merck & Co Inc | Substituted heterocycles, their preparation and pharmaceutical compositions containing them |
| US5972938A (en) | 1997-12-01 | 1999-10-26 | Merck & Co., Inc. | Method for treating or preventing psychoimmunological disorders |
| JPH11322748A (ja) * | 1998-03-19 | 1999-11-24 | Takeda Chem Ind Ltd | 複素環化合物、その製造法および用途 |
| EP1061926A2 (en) | 1998-03-19 | 2000-12-27 | Takeda Chemical Industries, Ltd. | Heterocyclic compounds, their production and use as tachykinin receptor antagonists |
| ES2359235T3 (es) * | 1999-02-24 | 2011-05-19 | F. Hoffmann-La Roche Ag | Derivados de 4-fenilpiridina y su empleo como antagonistas del receptor nk-1. |
| IL144717A0 (en) * | 1999-02-24 | 2002-06-30 | Hoffmann La Roche | Phenyl-and pyridinyl derivatives |
| CA2364662C (en) * | 1999-02-24 | 2009-10-20 | F. Hoffmann-La Roche Ag | 3-phenylpyridine derivatives and their use as nk-1 receptor antagonists |
| US6291465B1 (en) * | 1999-03-09 | 2001-09-18 | Hoffmann-La Roche Inc. | Biphenyl derivatives |
| US6303790B1 (en) * | 1999-11-29 | 2001-10-16 | Hoffman-La Roche Inc. | Process for the preparation of pyridine derivatives |
| EP1103545B1 (en) * | 1999-11-29 | 2003-11-05 | F. Hoffmann-La Roche Ag | 2-(3,5-Bis-trifluoromethyl-phenyl)-N-methyl-N-(6-morpholin-4-yl-4-o-tolyl-pyridin-3-yl)-isobutyramide |
| ME01311B (me) * | 2000-07-14 | 2013-12-20 | Hoffmann La Roche | N-oksidi kao proljekovi 4-fenil-piridinskih derivata koji su antagonisti nki receptora |
-
2001
- 2001-07-06 TW TW090116615A patent/TWI287003B/zh not_active IP Right Cessation
- 2001-07-09 US US09/901,311 patent/US6576762B2/en not_active Expired - Lifetime
- 2001-07-17 JO JO2001117A patent/JO2321B1/en active
- 2001-07-18 PE PE2001000730A patent/PE20020258A1/es not_active Application Discontinuation
- 2001-07-19 PA PA20018522801A patent/PA8522801A1/es unknown
- 2001-07-20 NZ NZ523452A patent/NZ523452A/en unknown
- 2001-07-20 DE DE60118569T patent/DE60118569T2/de not_active Expired - Lifetime
- 2001-07-20 KR KR10-2003-7001022A patent/KR100527214B1/ko not_active Expired - Lifetime
- 2001-07-20 MX MXPA03000367A patent/MXPA03000367A/es active IP Right Grant
- 2001-07-20 AT AT01960529T patent/ATE322496T1/de active
- 2001-07-20 DK DK01960529T patent/DK1305319T3/da active
- 2001-07-20 HU HU0301272A patent/HU229231B1/hu unknown
- 2001-07-20 YU YU2803A patent/YU2803A/sh unknown
- 2001-07-20 PT PT01960529T patent/PT1305319E/pt unknown
- 2001-07-20 PL PL01366173A patent/PL366173A1/xx not_active Application Discontinuation
- 2001-07-20 CZ CZ2003528A patent/CZ2003528A3/cs unknown
- 2001-07-20 HR HR20030031A patent/HRP20030031A2/xx not_active Application Discontinuation
- 2001-07-20 BR BR0112695-4A patent/BR0112695A/pt not_active IP Right Cessation
- 2001-07-20 CA CA2416874A patent/CA2416874C/en not_active Expired - Lifetime
- 2001-07-20 MY MYPI20013445A patent/MY129224A/en unknown
- 2001-07-20 SI SI200130532T patent/SI1305319T1/sl unknown
- 2001-07-20 AU AU8200501A patent/AU8200501A/xx active Pending
- 2001-07-20 WO PCT/EP2001/008432 patent/WO2002008232A1/en not_active Ceased
- 2001-07-20 RU RU2003104794/04A patent/RU2276139C2/ru not_active IP Right Cessation
- 2001-07-20 AU AU2001282005A patent/AU2001282005B2/en not_active Expired
- 2001-07-20 IL IL15383701A patent/IL153837A0/xx active IP Right Grant
- 2001-07-20 CN CNB018132863A patent/CN1192032C/zh not_active Expired - Lifetime
- 2001-07-20 ES ES01960529T patent/ES2260265T3/es not_active Expired - Lifetime
- 2001-07-20 JP JP2002514138A patent/JP4118673B2/ja not_active Expired - Lifetime
- 2001-07-20 EP EP01960529A patent/EP1305319B1/en not_active Expired - Lifetime
- 2001-07-23 GT GT200100148A patent/GT200100148A/es unknown
- 2001-07-23 AR ARP010103499A patent/AR029875A1/es not_active Application Discontinuation
- 2001-07-23 UY UY26851A patent/UY26851A1/es not_active Application Discontinuation
-
2002
- 2002-10-29 US US10/282,357 patent/US6624176B2/en not_active Expired - Lifetime
-
2003
- 2003-01-07 IL IL153837A patent/IL153837A/en unknown
- 2003-01-08 ZA ZA200300219A patent/ZA200300219B/en unknown
- 2003-01-22 MA MA27006A patent/MA26933A1/fr unknown
- 2003-01-23 EC EC2003004446A patent/ECSP034446A/es unknown
- 2003-01-23 NO NO20030353A patent/NO20030353D0/no not_active Application Discontinuation
-
2006
- 2006-07-04 CY CY20061100918T patent/CY1106113T1/el unknown