JP2011505405A5 - - Google Patents
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- Publication number
- JP2011505405A5 JP2011505405A5 JP2010536418A JP2010536418A JP2011505405A5 JP 2011505405 A5 JP2011505405 A5 JP 2011505405A5 JP 2010536418 A JP2010536418 A JP 2010536418A JP 2010536418 A JP2010536418 A JP 2010536418A JP 2011505405 A5 JP2011505405 A5 JP 2011505405A5
- Authority
- JP
- Japan
- Prior art keywords
- prodrugs
- esters
- mmol
- carboxylic acid
- benzyl
- 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
- 229940002612 prodrug Drugs 0.000 description 9
- 239000000651 prodrug Substances 0.000 description 9
- 229940079593 drug Drugs 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- 125000005907 alkyl ester group Chemical group 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- -1 aliphatic alcohols Chemical class 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical group C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 1
- 206010067484 Adverse reaction Diseases 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- 108090000371 Esterases Proteins 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 230000006838 adverse reaction Effects 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 229940097362 cyclodextrins Drugs 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- CNXMDTWQWLGCPE-UHFFFAOYSA-N ditert-butyl-(2-phenylphenyl)phosphane Chemical group CC(C)(C)P(C(C)(C)C)C1=CC=CC=C1C1=CC=CC=C1 CNXMDTWQWLGCPE-UHFFFAOYSA-N 0.000 description 1
- 239000013583 drug formulation Substances 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 150000003949 imides Chemical group 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Chemical group CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Chemical group C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000035909 sensory irritation Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- CBZYSWJGNTUENK-YADHBBJMSA-N tert-butyl (2r,4s)-4-[[3,5-bis(trifluoromethyl)phenyl]methyl-(5-morpholin-4-ylpyrimidin-2-yl)amino]-2-ethylpyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)[C@H](CC)C[C@@H]1N(C=1N=CC(=CN=1)N1CCOCC1)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 CBZYSWJGNTUENK-YADHBBJMSA-N 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US99189107P | 2007-12-03 | 2007-12-03 | |
| US60/991,891 | 2007-12-03 | ||
| PCT/EP2008/066537 WO2009071509A1 (en) | 2007-12-03 | 2008-12-01 | 1,2-disubstituted-4-benzylamino-pyrrolidine derivatives as cetp inhibitors useful for the treatment of diseases such as hyperli pidemia or arteriosclerosis |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011505405A JP2011505405A (ja) | 2011-02-24 |
| JP2011505405A5 true JP2011505405A5 (https=) | 2012-01-19 |
| JP5421282B2 JP5421282B2 (ja) | 2014-02-19 |
Family
ID=40347796
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010536418A Expired - Fee Related JP5421282B2 (ja) | 2007-12-03 | 2008-12-01 | 高脂血症または動脈硬化症のような疾患の処置に有用なｃｅｔｐ阻害剤としての１，２−二置換−４−ベンジルアミノ−ピロリジン誘導体 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US8759365B2 (https=) |
| EP (2) | EP2404901B1 (https=) |
| JP (1) | JP5421282B2 (https=) |
| KR (1) | KR20100093103A (https=) |
| CN (1) | CN101878199B (https=) |
| AT (1) | ATE528289T1 (https=) |
| AU (1) | AU2008333272B2 (https=) |
| BR (1) | BRPI0820000A2 (https=) |
| CA (1) | CA2707651A1 (https=) |
| EA (1) | EA017939B1 (https=) |
| ES (2) | ES2375527T3 (https=) |
| MX (1) | MX2010006063A (https=) |
| PL (2) | PL2229356T3 (https=) |
| PT (2) | PT2229356E (https=) |
| WO (1) | WO2009071509A1 (https=) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2657258A1 (en) * | 2006-07-20 | 2008-01-24 | Novartis Ag | Amino-piperidine derivatives as cetp inhibitors |
| EP2463282B1 (en) | 2007-11-05 | 2013-08-07 | Novartis AG | 4-Benzylamino-1-carboxyacyl-piperidine derivatives as CETP inhibitors useful for the treatment of diseases such as hyperlipidemia or arteriosclerosis |
| AU2011274903B2 (en) | 2010-07-09 | 2016-09-08 | Daiichi Sankyo Company, Limited | Substituted pyridine compound |
| US8877815B2 (en) | 2010-11-16 | 2014-11-04 | Novartis Ag | Substituted carbamoylcycloalkyl acetic acid derivatives as NEP |
| US8673974B2 (en) | 2010-11-16 | 2014-03-18 | Novartis Ag | Substituted amino bisphenyl pentanoic acid derivatives as NEP inhibitors |
| EP2614065B1 (en) | 2010-12-17 | 2017-04-19 | Nerviano Medical Sciences S.r.l. | Substituted pyrazolo-quinazoline derivatives as kinase inhibitors |
| WO2012101142A1 (en) | 2011-01-26 | 2012-08-02 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Method for assessing a subject's risk of having a cardiovascular disease. |
| ES2683350T3 (es) * | 2011-07-08 | 2018-09-26 | Novartis Ag | Método para tratar la aterosclerosis en sujetos con alto nivel de triglicéridos |
| ES2599757T3 (es) | 2012-01-06 | 2017-02-03 | Daiichi Sankyo Company, Limited | Sales de aducto de ácido de un compuesto de piridina sustituido como inhibidores de la proteína de transferencia de ésteres de colesterilo (PTEC) |
| US20130245259A1 (en) * | 2012-03-16 | 2013-09-19 | Natco Pharma Limited | Process for the preparation of bosentan monohydrate |
| UY35144A (es) | 2012-11-20 | 2014-06-30 | Novartis Ag | Miméticos lineales sintéticos de apelina para el tratamiento de insuficiencia cardiaca |
| CU24330B1 (es) | 2013-02-14 | 2018-03-13 | Novartis Ag | Derivados del ácido 4-((1,1) bifenil-4-il)-3-(3-fosfonopropanamido) butanoico, activos como inhibidores de nep (endopeptidasa neutral) |
| CN105705167A (zh) | 2013-07-25 | 2016-06-22 | 诺华股份有限公司 | 合成的apelin多肽的生物缀合物 |
| MX2016001020A (es) | 2013-07-25 | 2016-08-03 | Novartis Ag | Polipeptidos ciclicos para el tratamiento de insuficiencia cardiaca. |
| CR20170338A (es) | 2015-01-23 | 2017-09-12 | Novartis Ag | Conjugados de ácidos grasos y apelina sintética con mayor vida media |
| UY38072A (es) | 2018-02-07 | 2019-10-01 | Novartis Ag | Compuestos derivados de éster butanoico sustituido con bisfenilo como inhibidores de nep, composiciones y combinaciones de los mismos |
| WO2022216848A1 (en) * | 2021-04-06 | 2022-10-13 | Hemoshear Therapeutics, Inc. | Methods of treating methylmalonic acidemia and propionic acidemia |
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| PT72878B (en) | 1980-04-24 | 1983-03-29 | Merck & Co Inc | Process for preparing mannich-base hydroxamic acid pro-drugs for the improved delivery of non-steroidal anti-inflammatory agents |
| US4889861A (en) | 1982-12-21 | 1989-12-26 | Ciba-Geigy Corp. | Substituted imidazo[1,5-a]pyridine derivatives and other substituted bicyclic derivatives and their use as aromatase inhibitors |
| US4617307A (en) | 1984-06-20 | 1986-10-14 | Ciba-Geigy Corporation | Substituted imidazo[1,5-A]pyridine derivatives as aromatase inhibitors |
| RU2086544C1 (ru) | 1991-06-13 | 1997-08-10 | Хоффманн-Ля Рош АГ | Бензолсульфонамидные производные пиримидина или их соли, фармацевтическая композиция для лечения заболеваний, связанных с активностью эндотелина |
| US5508272A (en) | 1993-06-15 | 1996-04-16 | Bristol-Myers Squibb Company | Compounds containing a fused bicycle ring and processes therefor |
| MY119161A (en) | 1994-04-18 | 2005-04-30 | Novartis Ag | Delta-amino-gamma-hydroxy-omega-aryl-alkanoic acid amides with enzyme especially renin inhibiting activities |
| TW313568B (https=) | 1994-12-20 | 1997-08-21 | Hoffmann La Roche | |
| MXPA04004826A (es) | 1998-09-04 | 2004-08-11 | Millenium Pharmaceuticals Inc | Antagonista del receptor de quimioquinas y metodos para su uso. |
| GT199900147A (es) | 1998-09-17 | 1999-09-06 | 1, 2, 3, 4- tetrahidroquinolinas 2-sustituidas 4-amino sustituidas. | |
| US6140342A (en) | 1998-09-17 | 2000-10-31 | Pfizer Inc. | Oxy substituted 4-carboxyamino-2-methyl-1,2,3,4-tetrahydroquinolines |
| DE69925612T2 (de) | 1998-09-25 | 2006-03-16 | Monsanto Co., Chicago | (r)-chirale halogenierte 1-substituierte amino-(n+1)-alkanolen für die hemmung der aktivität des cholesteryl-ester-transfer-proteins |
| AUPP818099A0 (en) | 1999-01-14 | 1999-02-11 | Fujisawa Pharmaceutical Co., Ltd. | New n-containing heterocyclic compounds |
| US6586433B2 (en) * | 1999-09-23 | 2003-07-01 | Pharmacia Corporation | Substituted N-heteroaryl-N-phenyl aminoalcohol compounds useful for inhibiting cholesteryl ester transfer protein activity |
| AU2001275495B2 (en) | 2000-06-16 | 2006-08-17 | Curis, Inc. | Angiogenesis-modulating compositions and uses |
| GB0021885D0 (en) | 2000-09-06 | 2000-10-18 | Fujisawa Pharmaceutical Co | New use |
| WO2003011837A1 (en) | 2001-08-01 | 2003-02-13 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
| NZ596484A (en) * | 2001-11-21 | 2013-05-31 | Millennium Pharm Inc | Chemokine receptor antagonists and methods of use thereof |
| WO2003047569A1 (en) | 2001-12-03 | 2003-06-12 | Gpc Biotech, Inc. | Compositions and methods for inhibiting prenyltransferases |
| BRPI0314042B8 (pt) | 2002-09-06 | 2021-05-25 | Calando Pharmaceuticals Inc | polímeros à base de ciclodextrina para o fornecimento de agentes terapêuticos ligados a eles por covalência |
| JP4691988B2 (ja) | 2002-10-03 | 2011-06-01 | 小野薬品工業株式会社 | Ｌｐａ受容体拮抗剤 |
| JPWO2004050654A1 (ja) * | 2002-11-29 | 2006-03-30 | 塩野義製薬株式会社 | ピロリジン化合物の合成とその塩 |
| WO2004101529A1 (ja) | 2003-05-19 | 2004-11-25 | Ono Pharmaceutical Co., Ltd. | 含窒素複素環化合物およびその医薬用途 |
| JP2007507481A (ja) | 2003-09-30 | 2007-03-29 | ファイザー・プロダクツ・インク | Ｃｅｔｐ阻害薬及びその代謝産物 |
| GB0325956D0 (en) | 2003-11-06 | 2003-12-10 | Addex Pharmaceuticals Sa | Novel compounds |
| WO2005097805A1 (en) | 2004-03-26 | 2005-10-20 | Eli Lilly And Company | Compounds and methods for treating dyslipidemia |
| UA90269C2 (ru) | 2004-04-02 | 2010-04-26 | Мицубиси Танабе Фарма Корпорейшн | Тетрагидрохинолиновые производные и способ их получения |
| TWI345568B (en) * | 2004-04-02 | 2011-07-21 | Mitsubishi Tanabe Pharma Corp | Tetrahydronaphthyridine derivatives and a process for preparing the same |
| CA2570995A1 (en) | 2004-06-15 | 2006-01-05 | Merck & Co., Inc. | Pyrrolidin-3-yl compounds useful as beta-secretase inhibitors for the treatment of alzheimer's disease |
| US20060063803A1 (en) * | 2004-09-23 | 2006-03-23 | Pfizer Inc | 4-Amino substituted-2-substituted-1,2,3,4-tetrahydroquinoline compounds |
| WO2006069162A1 (en) * | 2004-12-20 | 2006-06-29 | Reddy Us Therapeutics, Inc. | Novel heterocyclic compounds and their pharmaceutical compositions |
| US20060270675A1 (en) * | 2005-03-10 | 2006-11-30 | Groneberg Robert D | Inhibitors of cholesterol ester transfer protein |
| WO2006098394A1 (ja) * | 2005-03-14 | 2006-09-21 | Japan Tobacco Inc. | 脂質吸収抑制方法および脂質吸収抑制剤 |
| MY150958A (en) | 2005-06-16 | 2014-03-31 | Astrazeneca Ab | Compounds for the treatment of multi-drug resistant bacterial infections |
| PE20071025A1 (es) | 2006-01-31 | 2007-10-17 | Mitsubishi Tanabe Pharma Corp | Compuesto amina trisustituido |
| WO2007107843A1 (en) | 2006-03-22 | 2007-09-27 | Pfizer Products Inc. | Methods of treatment with cetp inhibitors |
| TW200808731A (en) * | 2006-03-30 | 2008-02-16 | Tanabe Seiyaku Co | A process for preparing tetrahydroquinoline derivatives |
| CA2657258A1 (en) * | 2006-07-20 | 2008-01-24 | Novartis Ag | Amino-piperidine derivatives as cetp inhibitors |
| JP4846769B2 (ja) | 2007-07-30 | 2011-12-28 | 田辺三菱製薬株式会社 | 医薬組成物 |
| JP4834699B2 (ja) | 2007-07-30 | 2011-12-14 | 田辺三菱製薬株式会社 | 医薬組成物 |
| EP2463282B1 (en) * | 2007-11-05 | 2013-08-07 | Novartis AG | 4-Benzylamino-1-carboxyacyl-piperidine derivatives as CETP inhibitors useful for the treatment of diseases such as hyperlipidemia or arteriosclerosis |
| CA2707989A1 (en) | 2007-12-07 | 2009-06-11 | Novartis Ag | Pyrazole derivatives and use thereof as inhibitors of cyclin dependent kinases |
-
2008
- 2008-12-01 MX MX2010006063A patent/MX2010006063A/es active IP Right Grant
- 2008-12-01 EP EP11184000.5A patent/EP2404901B1/en not_active Not-in-force
- 2008-12-01 CA CA2707651A patent/CA2707651A1/en not_active Abandoned
- 2008-12-01 EP EP08857355A patent/EP2229356B1/en not_active Not-in-force
- 2008-12-01 ES ES08857355T patent/ES2375527T3/es active Active
- 2008-12-01 PL PL08857355T patent/PL2229356T3/pl unknown
- 2008-12-01 US US12/745,105 patent/US8759365B2/en not_active Expired - Fee Related
- 2008-12-01 BR BRPI0820000-9A patent/BRPI0820000A2/pt not_active IP Right Cessation
- 2008-12-01 PL PL11184000T patent/PL2404901T3/pl unknown
- 2008-12-01 CN CN2008801170746A patent/CN101878199B/zh not_active Expired - Fee Related
- 2008-12-01 PT PT08857355T patent/PT2229356E/pt unknown
- 2008-12-01 PT PT111840005T patent/PT2404901E/pt unknown
- 2008-12-01 WO PCT/EP2008/066537 patent/WO2009071509A1/en not_active Ceased
- 2008-12-01 EA EA201000884A patent/EA017939B1/ru not_active IP Right Cessation
- 2008-12-01 AT AT08857355T patent/ATE528289T1/de active
- 2008-12-01 ES ES11184000T patent/ES2425776T3/es active Active
- 2008-12-01 JP JP2010536418A patent/JP5421282B2/ja not_active Expired - Fee Related
- 2008-12-01 AU AU2008333272A patent/AU2008333272B2/en not_active Ceased
- 2008-12-01 KR KR1020107014702A patent/KR20100093103A/ko not_active Withdrawn
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