JP2009538873A5 - - Google Patents
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- JP2009538873A5 JP2009538873A5 JP2009512577A JP2009512577A JP2009538873A5 JP 2009538873 A5 JP2009538873 A5 JP 2009538873A5 JP 2009512577 A JP2009512577 A JP 2009512577A JP 2009512577 A JP2009512577 A JP 2009512577A JP 2009538873 A5 JP2009538873 A5 JP 2009538873A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- phenyl
- oxy
- methyl
- chloro
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 claims description 27
- 201000004792 malaria Diseases 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims 9
- 229920000728 polyester Polymers 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- QGQFNQWZHHSZIC-UHFFFAOYSA-N 5-chloro-2-(hydroxymethyl)-6-methyl-3-[4-[4-(trifluoromethoxy)phenoxy]phenyl]-1H-pyridin-4-one Chemical compound O=C1C(Cl)=C(C)NC(CO)=C1C(C=C1)=CC=C1OC1=CC=C(OC(F)(F)F)C=C1 QGQFNQWZHHSZIC-UHFFFAOYSA-N 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- 206010035500 Plasmodium falciparum infection Diseases 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- VBDWNBIKGCBULL-UHFFFAOYSA-N 3-chloro-2-(hydroxymethyl)-6-methyl-5-[4-[3-(trifluoromethyl)phenoxy]phenyl]-1H-pyridin-4-one Chemical compound N1C(CO)=C(Cl)C(=O)C(C=2C=CC(OC=3C=C(C=CC=3)C(F)(F)F)=CC=2)=C1C VBDWNBIKGCBULL-UHFFFAOYSA-N 0.000 claims 1
- PBBRXPIBBBJNSH-UHFFFAOYSA-N 3-chloro-2-(hydroxymethyl)-6-methyl-5-[4-[4-(trifluoromethoxy)phenoxy]phenyl]-1H-pyridin-4-one Chemical compound N1C(CO)=C(Cl)C(=O)C(C=2C=CC(OC=3C=CC(OC(F)(F)F)=CC=3)=CC=2)=C1C PBBRXPIBBBJNSH-UHFFFAOYSA-N 0.000 claims 1
- YVUMFLJJKXPWIK-UHFFFAOYSA-N 5-chloro-2-(3-hydroxypropyl)-6-methyl-3-[4-[4-(trifluoromethoxy)phenoxy]phenyl]-1H-pyridin-4-one Chemical compound O=C1C(Cl)=C(C)NC(CCCO)=C1C(C=C1)=CC=C1OC1=CC=C(OC(F)(F)F)C=C1 YVUMFLJJKXPWIK-UHFFFAOYSA-N 0.000 claims 1
- OROGEAPBNAKLSB-UHFFFAOYSA-N 5-chloro-2-(methoxyiminomethyl)-6-methyl-3-[4-[4-(trifluoromethoxy)phenoxy]phenyl]-1H-pyridin-4-one Chemical compound N1C(C)=C(Cl)C(=O)C(C=2C=CC(OC=3C=CC(OC(F)(F)F)=CC=3)=CC=2)=C1C=NOC OROGEAPBNAKLSB-UHFFFAOYSA-N 0.000 claims 1
- FPLYZPSLKQLYKK-UHFFFAOYSA-N N1C(C=NO)=C(Cl)C(=O)C(C=2C=CC(OC=3C=CC(OC(F)(F)F)=CC=3)=CC=2)=C1C Chemical compound N1C(C=NO)=C(Cl)C(=O)C(C=2C=CC(OC=3C=CC(OC(F)(F)F)=CC=3)=CC=2)=C1C FPLYZPSLKQLYKK-UHFFFAOYSA-N 0.000 claims 1
- OTKMQZNYPLNRQB-UHFFFAOYSA-N O=C1C(Cl)=C(C)NC(C=NO)=C1C(C=C1)=CC=C1OC1=CC=C(OC(F)(F)F)C=C1 Chemical compound O=C1C(Cl)=C(C)NC(C=NO)=C1C(C=C1)=CC=C1OC1=CC=C(OC(F)(F)F)C=C1 OTKMQZNYPLNRQB-UHFFFAOYSA-N 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 238000002651 drug therapy Methods 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000546 pharmaceutic aid Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000002829 reduced Effects 0.000 claims 1
- 238000007142 ring opening reaction Methods 0.000 claims 1
- GCNTZFIIOFTKIY-UHFFFAOYSA-N 1H-pyridin-4-one Chemical class OC1=CC=NC=C1 GCNTZFIIOFTKIY-UHFFFAOYSA-N 0.000 description 2
- 0 CC1(*)C=CC(Oc(cc2)ccc2C2=C(*)NC(*)=C(*)C2=O)=CC=C1 Chemical compound CC1(*)C=CC(Oc(cc2)ccc2C2=C(*)NC(*)=C(*)C2=O)=CC=C1 0.000 description 2
- 244000045947 parasites Species 0.000 description 2
- 241000223924 Eimeria Species 0.000 description 1
- 241000223960 Plasmodium falciparum Species 0.000 description 1
- 241000233870 Pneumocystis Species 0.000 description 1
Description
Claims (18)
- R1がBr、Cl、F、CF3またはOCF3を表す、請求項1記載の化合物またはその医薬上許容される誘導体。
- R4がBrまたはClを表す、請求項1または請求項2記載の化合物またはその医薬上許容される誘導体。
- R2およびR3の一方がメチルを表し、もう一方が−(CH2)nOHを表し、nが1〜4を表す、前記の請求項のいずれかに記載の化合物またはその医薬上許容される誘導体。
- R3がメチルを表し、R2が−(CH2)nOHを表し、nが1〜4を表す、前記の請求項のいずれかに記載の化合物またはその医薬上許容される誘導体。
- R5がHまたはメチルを表す、前記の請求項のいずれかに記載の化合物またはその医薬上許容される誘導体。
- nが1または3を表す、前記の請求項のいずれかに記載の化合物またはその医薬上許容される誘導体。
- 化合物が、
3−クロロ−6−(ヒドロキシメチル)−2−メチル−5−[4−({4−[(トリフルオロメチル)オキシ]フェニル}オキシ)フェニル]−4(1H)−ピリジノン;
3−クロロ−6−(ヒドロキシメチル)−2−メチル−5−[4−({4−[(トリフルオロメチル)オキシ]フェニル}オキシ)フェニル]−4(1H)−ピリジノン;
3−クロロ−2−(ヒドロキシメチル)−6−メチル−5−[4−({4−[(トリフルオロメチル)オキシ]フェニル}オキシ)フェニル]−4(1H)−ピリジノン;
3−クロロ−2−(ヒドロキシメチル)−6−メチル−5−(4−{[3−(トリフルオロメチル)フェニル]オキシ}フェニル)−4(1H)−ピリジノン;
5−クロロ−6−メチル−4−オキソ−3−[4−({4−[(トリフルオロメチル)オキシ]フェニル}オキシ)フェニル]−1,4−ジヒドロ−2−ピリジンカルバルデヒド オキシム;
5−クロロ−6−メチル−4−オキソ−3−[4−({4−[(トリフルオロメチル)オキシ]フェニル}オキシ)フェニル]−1,4−ジヒドロ−2−ピリジンカルバルデヒド−O−メチルオキシム;
3−クロロ−6−メチル−4−オキソ−5−[4−({4−[(トリフルオロメチル)オキシ]フェニル}オキシ)フェニル]−1,4−ジヒドロ−2−ピリジンカルバルデヒド オキシム;および
3−クロロ−6−(3−ヒドロキシプロピル)−2−メチル−5−[4−({4−[(トリフルオロメチル)オキシ]フェニル}オキシ)フェニル]−4(1H)−ピリジノンからなる群より選択される、請求項1記載の化合物、またはその医薬上許容される誘導体。 - 3−クロロ−6−(ヒドロキシメチル)−2−メチル−5−[4−({4−[(トリフルオロメチル)オキシ]フェニル}オキシ)フェニル]−4(1H)−ピリジノンである化合物。
- 薬物療法に用いるための請求項1〜9のいずれか1項に記載の化合物またはその医薬上許容される誘導体。
- マラリアの治療のための医薬の製造における請求項1〜9のいずれか1項に記載の化合物またはその医薬上許容される誘導体の使用。
- マラリアが、プラスモジウム・ファルシパルム感染によって引き起こされる請求項11記載の使用。
- マラリアに罹患しているヒトまたは動物対象の治療方法であって、該ヒトまたは動物対象に有効量の請求項1〜9のいずれか1項に記載の化合物またはその医薬上許容される誘導体を投与することを含む、方法。
- マラリアが、プラスモジウム・ファルシパルム感染によって引き起こされる請求項13記載の使用。
- 請求項1〜9のいずれか1項に記載の化合物またはその医薬上許容される誘導体ならびに1種または複数の医薬上許容される担体および/または賦形剤を含む医薬組成物。
- 請求項1記載の式Iの化合物の調製方法であって、
(A)R1がハロ、CF3またはOCF3を表す、式IIの化合物をハロゲン供与体と反応させるか;
(B)R1がフルオロ、クロロ、CF3またはOCF3を表す、式XVの化合物をハロゲン供与体と反応させるか;
(C)適当な塩基の存在下において、R1がハロ、CF3またはOCF3を表し、R4がハロを表す、式XXの化合物を、R5がHまたはC1−3アルキルを表す、NH2OR5.HClと反応させるか;
(D)適当な塩基の存在下において、R1がハロ、CF3またはOCF3を表し、R4がハロを表す、式XXIの化合物を、R5がHまたはC1−3アルキルを表す、NH2OR5.HClと反応させるか;
(E)適当な触媒の存在下において、R1がフルオロ、クロロ、CF3またはOCF3を表し、R4がハロを表す、式XXIIの化合物を、水素化反応に付す;
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP06381025A EP1862459A1 (en) | 2006-05-31 | 2006-05-31 | Novel heterocyclic compounds |
EP07380072A EP1967515A1 (en) | 2007-03-08 | 2007-03-08 | Heterocyclic compounds |
PCT/EP2007/055188 WO2007138048A1 (en) | 2006-05-31 | 2007-05-29 | Novel heterocyclic compounds |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2009538873A JP2009538873A (ja) | 2009-11-12 |
JP2009538873A5 true JP2009538873A5 (ja) | 2010-07-15 |
Family
ID=38480438
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2009512577A Pending JP2009538873A (ja) | 2006-05-31 | 2007-05-29 | 新規複素環化合物 |
Country Status (17)
Country | Link |
---|---|
US (2) | US7674808B2 (ja) |
EP (1) | EP2024332A1 (ja) |
JP (1) | JP2009538873A (ja) |
KR (1) | KR20090012342A (ja) |
AR (1) | AR060974A1 (ja) |
AU (1) | AU2007267093A1 (ja) |
BR (1) | BRPI0711783A2 (ja) |
CA (1) | CA2653872A1 (ja) |
CR (1) | CR10492A (ja) |
EA (1) | EA200870545A1 (ja) |
IL (1) | IL195158A0 (ja) |
MA (1) | MA30487B1 (ja) |
MX (1) | MX2008015291A (ja) |
NO (1) | NO20085087L (ja) |
PE (1) | PE20080453A1 (ja) |
TW (1) | TW200817331A (ja) |
WO (1) | WO2007138048A1 (ja) |
Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8877178B2 (en) | 2003-12-19 | 2014-11-04 | The Iams Company | Methods of use of probiotic bifidobacteria for companion animals |
US20050158294A1 (en) | 2003-12-19 | 2005-07-21 | The Procter & Gamble Company | Canine probiotic Bifidobacteria pseudolongum |
AR052472A1 (es) | 2005-05-31 | 2007-03-21 | Iams Company | Lactobacilos probioticos para felinos |
EP1885383B1 (en) | 2005-05-31 | 2016-09-21 | IAMS Europe B.V. | Feline probiotic bifidobacteria |
WO2008093303A2 (en) | 2007-02-01 | 2008-08-07 | The Iams Company | Method for decreasing inflammation and stress in a mammal using glucose antimetaboltes, avocado or avocado extracts |
EP2220043A1 (en) * | 2007-11-30 | 2010-08-25 | Glaxo Group Limited | Crystalline form of an antimalarial compound |
US9771199B2 (en) * | 2008-07-07 | 2017-09-26 | Mars, Incorporated | Probiotic supplement, process for making, and packaging |
US9232813B2 (en) * | 2008-07-07 | 2016-01-12 | The Iams Company | Probiotic supplement, process for making, and packaging |
WO2010081904A1 (en) | 2009-01-19 | 2010-07-22 | Glaxo Group Limited | 4 ( 1h) -pyridinone derivatives and their use as antimalaria agents |
EP2246329A1 (en) | 2009-01-19 | 2010-11-03 | Glaxo Group Limited | 4(1H)-pyridinone derivatives and their use as antimalaria agents |
TW201039834A (en) | 2009-02-20 | 2010-11-16 | Glaxo Group Ltd | Novel heterocyclic compounds |
WO2010142741A1 (en) * | 2009-06-12 | 2010-12-16 | Glaxo Group Limited | Phenylpyridylpyridones for use as antimalarial agents |
US10104903B2 (en) | 2009-07-31 | 2018-10-23 | Mars, Incorporated | Animal food and its appearance |
US10327764B2 (en) * | 2014-09-26 | 2019-06-25 | Ethicon Llc | Method for creating a flexible staple line |
JOP20180072A1 (ar) | 2014-09-11 | 2019-01-30 | Lilly Co Eli | علاج الأعراض المرتبطة بالعلاج بالحرمان من الأندروجين |
WO2016169908A1 (en) * | 2015-04-21 | 2016-10-27 | Glaxosmithkline Intellectual Property Development Limited | Uracil derivatives for the treatment of malaria |
GB201809627D0 (en) * | 2018-06-12 | 2018-07-25 | Biorelevant Com Ltd | Methods for preparing buffer solutions suitable for in vitro drug dissolution testing, drug solubility testing and/or drug profiling |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5403934A (en) * | 1990-03-12 | 1995-04-04 | Burroughs Wellcome Co. | Heterocyclic compounds |
GB9005518D0 (en) | 1990-03-12 | 1990-05-09 | Wellcome Found | Heterocyclic compounds |
GB9100465D0 (en) * | 1991-01-09 | 1991-02-20 | Hider Robert C | Pharmaceutical compositions |
-
2007
- 2007-05-29 KR KR1020087029153A patent/KR20090012342A/ko not_active Application Discontinuation
- 2007-05-29 CA CA002653872A patent/CA2653872A1/en not_active Abandoned
- 2007-05-29 TW TW096119056A patent/TW200817331A/zh unknown
- 2007-05-29 AU AU2007267093A patent/AU2007267093A1/en not_active Abandoned
- 2007-05-29 WO PCT/EP2007/055188 patent/WO2007138048A1/en active Application Filing
- 2007-05-29 MX MX2008015291A patent/MX2008015291A/es unknown
- 2007-05-29 AR ARP070102297A patent/AR060974A1/es not_active Application Discontinuation
- 2007-05-29 US US11/754,382 patent/US7674808B2/en not_active Expired - Fee Related
- 2007-05-29 BR BRPI0711783-3A patent/BRPI0711783A2/pt not_active IP Right Cessation
- 2007-05-29 PE PE2007000667A patent/PE20080453A1/es not_active Application Discontinuation
- 2007-05-29 EA EA200870545A patent/EA200870545A1/ru unknown
- 2007-05-29 JP JP2009512577A patent/JP2009538873A/ja active Pending
- 2007-05-29 EP EP07729610A patent/EP2024332A1/en not_active Withdrawn
- 2007-05-31 US US11/755,849 patent/US7629365B2/en not_active Expired - Fee Related
-
2008
- 2008-11-06 IL IL195158A patent/IL195158A0/en unknown
- 2008-12-01 MA MA31430A patent/MA30487B1/fr unknown
- 2008-12-05 NO NO20085087A patent/NO20085087L/no not_active Application Discontinuation
- 2008-12-10 CR CR10492A patent/CR10492A/es not_active Application Discontinuation
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