JP2008528624A - フェニル置換ピロリドン - Google Patents
フェニル置換ピロリドン Download PDFInfo
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- JP2008528624A JP2008528624A JP2007553324A JP2007553324A JP2008528624A JP 2008528624 A JP2008528624 A JP 2008528624A JP 2007553324 A JP2007553324 A JP 2007553324A JP 2007553324 A JP2007553324 A JP 2007553324A JP 2008528624 A JP2008528624 A JP 2008528624A
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- Prior art keywords
- substituted
- compound
- unsubstituted
- hiv
- alkyl
- Prior art date
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims abstract description 22
- 150000004040 pyrrolidinones Chemical class 0.000 title abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 138
- 238000000034 method Methods 0.000 claims abstract description 66
- 208000031886 HIV Infections Diseases 0.000 claims abstract description 40
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- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims abstract description 37
- 230000000903 blocking effect Effects 0.000 claims abstract description 6
- -1 methoxy, vinyl Chemical group 0.000 claims description 85
- 108010092799 RNA-directed DNA polymerase Proteins 0.000 claims description 54
- 102100034343 Integrase Human genes 0.000 claims description 51
- 239000003814 drug Substances 0.000 claims description 37
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 35
- 229910052757 nitrogen Inorganic materials 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
- 229940079593 drug Drugs 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 8
- 230000002265 prevention Effects 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 4
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 2
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- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
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- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 38
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
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- 125000001072 heteroaryl group Chemical group 0.000 description 17
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 17
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- RMCRHTCUBAOZQZ-UHFFFAOYSA-N 4-benzyl-3-[3-(4-chloro-3-phenylmethoxyphenyl)-4-nitrobutanoyl]-1,3-oxazolidin-2-one Chemical compound C=1C=C(Cl)C(OCC=2C=CC=CC=2)=CC=1C(C[N+](=O)[O-])CC(=O)N(C(OC1)=O)C1CC1=CC=CC=C1 RMCRHTCUBAOZQZ-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
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- HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
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- NQDJXKOVJZTUJA-UHFFFAOYSA-N nevirapine Chemical compound C12=NC=CC=C2C(=O)NC=2C(C)=CC=NC=2N1C1CC1 NQDJXKOVJZTUJA-UHFFFAOYSA-N 0.000 description 8
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- TUWKFQNDSCQEDF-LBPRGKRZSA-N 3-chloro-2-[2-chloro-5-[(3r)-5-oxopyrrolidin-3-yl]phenoxy]benzonitrile Chemical compound ClC1=CC=C([C@H]2CC(=O)NC2)C=C1OC1=C(Cl)C=CC=C1C#N TUWKFQNDSCQEDF-LBPRGKRZSA-N 0.000 description 7
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- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Virology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Tropical Medicine & Parasitology (AREA)
- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- Oncology (AREA)
- AIDS & HIV (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US64802705P | 2005-01-28 | 2005-01-28 | |
| PCT/US2006/003217 WO2006081554A2 (en) | 2005-01-28 | 2006-01-30 | Phenyl-substituted pyrrolidones |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008528624A true JP2008528624A (ja) | 2008-07-31 |
| JP2008528624A5 JP2008528624A5 (enExample) | 2009-03-26 |
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| JP2007553324A Pending JP2008528624A (ja) | 2005-01-28 | 2006-01-30 | フェニル置換ピロリドン |
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| EP (1) | EP1841425A4 (enExample) |
| JP (1) | JP2008528624A (enExample) |
| KR (2) | KR100896889B1 (enExample) |
| CN (1) | CN101115481A (enExample) |
| AU (1) | AU2006209245A1 (enExample) |
| BR (1) | BRPI0606123A2 (enExample) |
| CA (1) | CA2594915A1 (enExample) |
| MX (1) | MX2007009137A (enExample) |
| RU (1) | RU2371433C2 (enExample) |
| WO (1) | WO2006081554A2 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2020515583A (ja) * | 2017-03-31 | 2020-05-28 | アエリエ ファーマシューティカルズ インコーポレイテッド | アリールシクロプロピル−アミノ−イソキノリニルアミド化合物 |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2477604A1 (en) | 2002-03-13 | 2003-09-25 | Signum Biosciences, Inc. | Modulation of protein methylation and phosphoprotein phosphate |
| AU2006209241B2 (en) * | 2005-01-28 | 2009-10-22 | Irm Llc | Synthesis of aryl pyrrolidones |
| EP1843734A4 (en) | 2005-02-03 | 2008-09-10 | Signum Biosciences Inc | COMPOSITIONS AND METHOD FOR INTENSIFYING COGNITIVE FUNCTIONS |
| US7923041B2 (en) | 2005-02-03 | 2011-04-12 | Signum Biosciences, Inc. | Compositions and methods for enhancing cognitive function |
| JP5164510B2 (ja) * | 2006-10-06 | 2013-03-21 | 日本曹達株式会社 | 含窒素複素環化合物および有害生物防除剤 |
| US8455513B2 (en) | 2007-01-10 | 2013-06-04 | Aerie Pharmaceuticals, Inc. | 6-aminoisoquinoline compounds |
| CN102014897B (zh) | 2008-04-21 | 2015-08-05 | 西格纳姆生物科学公司 | 化合物、组合物和其制备方法 |
| US8450344B2 (en) | 2008-07-25 | 2013-05-28 | Aerie Pharmaceuticals, Inc. | Beta- and gamma-amino-isoquinoline amide compounds and substituted benzamide compounds |
| CN101747253B (zh) * | 2008-12-02 | 2013-01-16 | 中国人民解放军军事医学科学院毒物药物研究所 | 三取代的手性内酰胺类衍生物及其制备方法和用途 |
| ES2672624T3 (es) | 2009-05-01 | 2018-06-15 | Aerie Pharmaceuticals, Inc. | Inhibidores de mecanismo doble para el tratamiento de enfermedades |
| US9238643B2 (en) | 2010-09-06 | 2016-01-19 | Guangzhou Institutes Of Biomedicine And Health, Chinese Academy Of Sciences | Amide compounds |
| CN101979378B (zh) * | 2010-10-13 | 2012-06-27 | 中国科学院上海有机化学研究所 | 一种手性γ-内酰胺化合物的合成方法 |
| PT3811943T (pt) | 2013-03-15 | 2023-03-15 | Aerie Pharmaceuticals Inc | Composto para uso no tratamento de distúrbios oculares |
| MX2019002396A (es) | 2016-08-31 | 2019-07-08 | Aerie Pharmaceuticals Inc | Composiciones oftalmicas. |
| US11186549B2 (en) | 2017-08-29 | 2021-11-30 | Rutgers, The State University Of New Jersey | Therapeutic indazoles |
| CA3112391A1 (en) | 2018-09-14 | 2020-03-19 | Aerie Pharmaceuticals, Inc. | Aryl cyclopropyl-amino-isoquinolinyl amide compounds |
| AU2019387370A1 (en) | 2018-11-30 | 2021-06-10 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
Citations (1)
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| WO2004037784A2 (en) * | 2002-10-21 | 2004-05-06 | Irm Llc | Pyrrolidones with anti-hiv activity |
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| SU797219A1 (ru) * | 1979-05-08 | 1995-07-25 | Ленинградский государственный педагогический институт им.А.И.Герцена | N-карбамоилметил-4-фенил-2-пирролидон, обладающий гипотензивной активностью |
| TW448172B (en) * | 1996-03-08 | 2001-08-01 | Pharmacia & Upjohn Co Llc | Novel hydroxamic acid derivatives useful for the treatment of diseases related to connective tissue degradation |
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- 2006-01-30 RU RU2007132259/04A patent/RU2371433C2/ru not_active IP Right Cessation
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- 2006-01-30 CA CA002594915A patent/CA2594915A1/en not_active Abandoned
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- 2006-01-30 JP JP2007553324A patent/JP2008528624A/ja active Pending
- 2006-01-30 AU AU2006209245A patent/AU2006209245A1/en not_active Abandoned
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- 2006-01-30 US US11/814,480 patent/US20080287516A1/en not_active Abandoned
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Patent Citations (1)
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| WO2004037784A2 (en) * | 2002-10-21 | 2004-05-06 | Irm Llc | Pyrrolidones with anti-hiv activity |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2020515583A (ja) * | 2017-03-31 | 2020-05-28 | アエリエ ファーマシューティカルズ インコーポレイテッド | アリールシクロプロピル−アミノ−イソキノリニルアミド化合物 |
Also Published As
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| CA2594915A1 (en) | 2006-08-03 |
| WO2006081554A2 (en) | 2006-08-03 |
| KR100896889B1 (ko) | 2009-05-14 |
| KR20070103404A (ko) | 2007-10-23 |
| EP1841425A4 (en) | 2009-02-18 |
| RU2007132259A (ru) | 2009-03-10 |
| MX2007009137A (es) | 2007-09-12 |
| US20080287516A1 (en) | 2008-11-20 |
| RU2371433C2 (ru) | 2009-10-27 |
| WO2006081554A3 (en) | 2006-12-14 |
| KR20090028846A (ko) | 2009-03-19 |
| EP1841425A2 (en) | 2007-10-10 |
| BRPI0606123A2 (pt) | 2009-06-02 |
| AU2006209245A1 (en) | 2006-08-03 |
| CN101115481A (zh) | 2008-01-30 |
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