WO2007028789A1 - Dérivés de quinazoline en tant qu'agents antiviraux - Google Patents

Dérivés de quinazoline en tant qu'agents antiviraux Download PDF

Info

Publication number
WO2007028789A1
WO2007028789A1 PCT/EP2006/066002 EP2006066002W WO2007028789A1 WO 2007028789 A1 WO2007028789 A1 WO 2007028789A1 EP 2006066002 W EP2006066002 W EP 2006066002W WO 2007028789 A1 WO2007028789 A1 WO 2007028789A1
Authority
WO
WIPO (PCT)
Prior art keywords
chlorophenyl
amino
optionally substituted
hydroxy
hydrogen
Prior art date
Application number
PCT/EP2006/066002
Other languages
English (en)
Inventor
Monica Donghi
Marco Ferrara
Uwe Koch
Frank Narjes
Jesus Maria Ontoria Ontoria
Vincenzo Summa
Original Assignee
Istituto Di Ricerche Di Biologia Molecolare P. Angeletti Spa
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from GB0518231A external-priority patent/GB0518231D0/en
Priority claimed from GB0601068A external-priority patent/GB0601068D0/en
Priority claimed from GB0604037A external-priority patent/GB0604037D0/en
Application filed by Istituto Di Ricerche Di Biologia Molecolare P. Angeletti Spa filed Critical Istituto Di Ricerche Di Biologia Molecolare P. Angeletti Spa
Publication of WO2007028789A1 publication Critical patent/WO2007028789A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
    • C07D239/96—Two oxygen atoms
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—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
    • C07D401/02—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
    • C07D401/12—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 linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D471/02—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 in which the condensed system contains two hetero rings
    • C07D471/06—Peri-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/06—Peri-condensed systems

Definitions

  • R 5 , R 6 and R 7 are independently selected from hydrogen, (CH 2 ) 0 _ 3 Het, (CH 2 ) 0 _ 3 aryl and (CH 2 )o_ 3 heteroaryl;
  • R 1 is (CH 2 ) 0 . 3 aryl, more preferably (CH 2 ) 0 . 3 phenyl, most preferably phenyl or benzyl, especially phenyl, optionally substituted by one or two groups independently selected from halo, hydroxy, Ci- ⁇ alkyl, CO 2 R 5 or CONR 5 R 6 where R 5 and R 6 are as hereinbefore defined, preferably halo, hydroxy, CO 2 H or CONHMe, more preferably, fluorine, chlorine, CO 2 H or CONHMe.
  • R 1 is substituted, it is preferably mono- or di-substituted.
  • Suitable NR c R d groups include:
  • R >4 substituent is attached to the 6- or 7- position of the bicyclic moiety:
  • R 4 substituent is attached to the 7-position of the bicyclic moiety.
  • R 4 is hydrogen, C ⁇ alkyl and Ci- ⁇ alkoxy groups are optionally substituted by hydroxy or 1 to 5 halogen atoms, and where R c and R d are as hereinbefore defined. More preferably, R 4 is hydroxy, halo or NR c R d where R c and R d are as hereinbefore defined. Most preferably, R 4 is chlorine, fluorine or NR c R d where R c and R d are as hereinbefore defined. Especially, R 4 is chlorine or NR c R d where R c and R d are as hereinbefore defined.
  • R c and R d are independently selected from hydrogen, methyl, ethyl, i-propyl, cyclohexyl, benzyl and piperidinyl, optionally substituted by hydroxy, methyl, CO 2 H, benzyl and (CH 2 )pyridyl.
  • Q 1 is hydrogen, hydroxy or halo. More preferably, Q 1 is hydroxy, fluorine or chlorine. Most preferably, Q 1 is chlorine.
  • Q 1 is at the 3 -position of the phenyl ring.
  • the salts may be formed by conventional means, such as by reacting the free base form of the product with one or more equivalents of the appropriate acid in a solvent or medium in which the salt is insoluble, or in a solvent such as water which is removed in vacuo or by freeze drying or by exchanging the anions of an existing salt for another anion on a suitable ion exchange resin.
  • the present invention includes within its scope prodrugs of the compounds of formula (I) above.
  • Step 2 7-chloro-3-(3-chlorophenyl)-l-methylquinazolme-2,4(lH.,3H)-dione
  • a solution (0.26 M) 7-chloro-3-(3-chlorophenyl)quinazoline-2,4(lH,3H)-dione (from Step 1) in DMF was treated with DBU (1.2 eq.) and MeI (1.2 eq.). The reaction mixture was stirred at RT for 1 h. After dilution with water, the resulting precipitate was filtered off affording the title compound (71%) as white solid.
  • Step 3 5-fluoro-l,2,3,4-tetrahvdroquinoline-8-carboxylic acid A solution (0.25 M) of 5-fluoroquinoline-8-carboxylic acid (from Step 2) in acetic acid was treated with PtO 2 (0.3 eq.) and stirred under hydrogen at atmospheric pressure for 3 h.
  • Step 1 methyl 3-chloro-5-nitrobenzoate A solution (0.96 M) OfNaNO 2 (7.0 eq.) in water was added to a solution (0.09 M) of 3-amino-5-nitrobenzoic acid in HCl (cone.) at 0 0 C. The reaction mixture was left to warm up to RT over a period of 30 min and then was added to a solution (1.37 M) of CuCl (10.0 eq.) in water. The reaction mixture was stirred at RT for 3 h and then heated to 70 0 C for 30 min. After addition Of Et 2 O and water, the organic phase was separated and the aqueous phase extracted with Et 2 O.
  • Step 5 l-benzyl-4- ⁇ r2-(3-carboxy-5-chlorophenyl)-l,3-dioxo-2,3,6,7-tetrahvdro-lH5H-pyridor3,2,l-

Abstract

La présente invention a pour objet des dérivés de quinazoline de formule (I) : où A, B, R1, R2, R3 et R4 sont tels que définis dans l'invention, ainsi que des sels de qualité pharmaceutique desdits dérivés, pour le traitement prophylactique ou thérapeutique d'une infection par le virus de l'hépatite C.
PCT/EP2006/066002 2005-09-07 2006-09-05 Dérivés de quinazoline en tant qu'agents antiviraux WO2007028789A1 (fr)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
GB0518231A GB0518231D0 (en) 2005-09-07 2005-09-07 Therapeutic agents
GB0518231.6 2005-09-07
GB0601068A GB0601068D0 (en) 2006-01-19 2006-01-19 Therapeutic Agents
GB0601068.0 2006-01-19
GB0604037A GB0604037D0 (en) 2006-03-01 2006-03-01 therapeutic agents
GB0604037.2 2006-03-01

Publications (1)

Publication Number Publication Date
WO2007028789A1 true WO2007028789A1 (fr) 2007-03-15

Family

ID=37220452

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2006/066002 WO2007028789A1 (fr) 2005-09-07 2006-09-05 Dérivés de quinazoline en tant qu'agents antiviraux

Country Status (1)

Country Link
WO (1) WO2007028789A1 (fr)

Cited By (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008133155A1 (fr) 2007-04-19 2008-11-06 Astellas Pharma Inc. Composé hétérocyclique bicyclique
WO2009076747A1 (fr) 2007-12-19 2009-06-25 Boehringer Ingelheim International Gmbh Inhibiteurs de polymérase virale
DE102008022221A1 (de) 2008-05-06 2009-11-12 Universität des Saarlandes Inhibitoren der humanen Aldosteronsynthase CYP11B2
WO2010080874A1 (fr) 2009-01-07 2010-07-15 Scynexis, Inc. Dérivé de cyclosporine convenant au traitement de l'infection par vhc et vih
US7767660B2 (en) 2006-12-20 2010-08-03 Istituto Di Richerche Di Biologia Molecolare P. Angeletti Spa Antiviral indoles
US7781422B2 (en) 2006-12-20 2010-08-24 Istituto Di Ricerche Di Biologia Molecolare P. Angeletti Spa Antiviral indoles
US7879797B2 (en) 2005-05-02 2011-02-01 Merck Sharp & Dohme Corp. HCV NS3 protease inhibitors
US7973040B2 (en) 2008-07-22 2011-07-05 Merck Sharp & Dohme Corp. Macrocyclic quinoxaline compounds as HCV NS3 protease inhibitors
US7989438B2 (en) 2007-07-17 2011-08-02 Istituto Di Ricerche Di Biologia Molecolare P. Angeletti Spa Therapeutic compounds
US8101595B2 (en) 2006-12-20 2012-01-24 Istituto di Ricerche di Biologia Molecolare P. Angletti SpA Antiviral indoles
US8138164B2 (en) 2006-10-24 2012-03-20 Merck Sharp & Dohme Corp. HCV NS3 protease inhibitors
US8178520B2 (en) 2006-05-15 2012-05-15 Istituto Di Ricerche Di Biologia Molecolare P. Angeletti Spa Macrocyclic compounds as antiviral agents
EP2494991A1 (fr) 2007-05-04 2012-09-05 Vertex Pharmaceuticals Incorporated Polythérapie pour le traitement de l'infection par VHC
US8278322B2 (en) 2005-08-01 2012-10-02 Merck Sharp & Dohme Corp. HCV NS3 protease inhibitors
US8309540B2 (en) 2006-10-24 2012-11-13 Merck Sharp & Dohme Corp. HCV NS3 protease inhibitors
US8314062B2 (en) 2006-06-23 2012-11-20 Instituto Di Ricerche Di Biologia Molecolare P. Angeletti S.P.A. Macrocyclic compounds as antiviral agents
US8377873B2 (en) 2006-10-24 2013-02-19 Merck Sharp & Dohme Corp. HCV NS3 protease inhibitors
US8377874B2 (en) 2006-10-27 2013-02-19 Merck Sharp & Dohme Corp. HCV NS3 protease inhibitors
CN102993105A (zh) * 2012-12-19 2013-03-27 西南大学 1-甲基-2,4-喹唑啉二酮衍生物及其制备方法和应用
US8461107B2 (en) 2008-04-28 2013-06-11 Merck Sharp & Dohme Corp. HCV NS3 protease inhibitors
US8541404B2 (en) 2009-11-09 2013-09-24 Elexopharm Gmbh Inhibitors of the human aldosterone synthase CYP11B2
US8828930B2 (en) 2009-07-30 2014-09-09 Merck Sharp & Dohme Corp. Hepatitis C virus NS3 protease inhibitors
US8927569B2 (en) 2007-07-19 2015-01-06 Merck Sharp & Dohme Corp. Macrocyclic compounds as antiviral agents
US9738661B2 (en) 2006-10-27 2017-08-22 Merck Sharp & Dohme Corp. HCV NS3 protease inhibitors
WO2017149469A1 (fr) 2016-03-03 2017-09-08 Emcure Pharmaceuticals Limited Composés hétérocycliques utiles en tant que modulateurs de l'ido et/ou de la tdo
WO2019141808A1 (fr) 2018-01-19 2019-07-25 Idorsia Pharmaceuticals Ltd Modulateurs du récepteur c5a
US10513515B2 (en) 2017-08-25 2019-12-24 Biotheryx, Inc. Ether compounds and uses thereof
US11236103B2 (en) 2018-07-27 2022-02-01 Biotheryx, Inc. Bifunctional compounds
CN114539148A (zh) * 2022-01-25 2022-05-27 北京英飞智药科技有限公司 一种环状n-羟基酰亚胺类化合物及其用途
CN115197225A (zh) * 2021-09-03 2022-10-18 贵州大学 一种五元杂环并喹唑啉酮类化合物及其制备方法
CN115490643A (zh) * 2022-11-21 2022-12-20 南京合创药业有限公司 一种一锅法合成3-二氯苯基-6-氟-2,4(1h,3h)-喹唑啉二酮的方法
US11897930B2 (en) 2020-04-28 2024-02-13 Anwita Biosciences, Inc. Interleukin-2 polypeptides and fusion proteins thereof, and their pharmaceutical compositions and therapeutic applications

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006027628A2 (fr) * 2004-09-07 2006-03-16 Istituto Di Ricerche Di Biologia Molecolare P. Angeletti Spa Derives de naphtalimide en tant qu'agents antiviraux
EP1700850A1 (fr) * 2003-12-22 2006-09-13 Ajinomoto Co., Inc. Nouveau derive phenylalanine

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1700850A1 (fr) * 2003-12-22 2006-09-13 Ajinomoto Co., Inc. Nouveau derive phenylalanine
WO2006027628A2 (fr) * 2004-09-07 2006-03-16 Istituto Di Ricerche Di Biologia Molecolare P. Angeletti Spa Derives de naphtalimide en tant qu'agents antiviraux

Cited By (36)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7879797B2 (en) 2005-05-02 2011-02-01 Merck Sharp & Dohme Corp. HCV NS3 protease inhibitors
US8278322B2 (en) 2005-08-01 2012-10-02 Merck Sharp & Dohme Corp. HCV NS3 protease inhibitors
US8178520B2 (en) 2006-05-15 2012-05-15 Istituto Di Ricerche Di Biologia Molecolare P. Angeletti Spa Macrocyclic compounds as antiviral agents
US8314062B2 (en) 2006-06-23 2012-11-20 Instituto Di Ricerche Di Biologia Molecolare P. Angeletti S.P.A. Macrocyclic compounds as antiviral agents
US8138164B2 (en) 2006-10-24 2012-03-20 Merck Sharp & Dohme Corp. HCV NS3 protease inhibitors
US8377873B2 (en) 2006-10-24 2013-02-19 Merck Sharp & Dohme Corp. HCV NS3 protease inhibitors
US8309540B2 (en) 2006-10-24 2012-11-13 Merck Sharp & Dohme Corp. HCV NS3 protease inhibitors
US8377874B2 (en) 2006-10-27 2013-02-19 Merck Sharp & Dohme Corp. HCV NS3 protease inhibitors
US9738661B2 (en) 2006-10-27 2017-08-22 Merck Sharp & Dohme Corp. HCV NS3 protease inhibitors
US7767660B2 (en) 2006-12-20 2010-08-03 Istituto Di Richerche Di Biologia Molecolare P. Angeletti Spa Antiviral indoles
US8101595B2 (en) 2006-12-20 2012-01-24 Istituto di Ricerche di Biologia Molecolare P. Angletti SpA Antiviral indoles
US7781422B2 (en) 2006-12-20 2010-08-24 Istituto Di Ricerche Di Biologia Molecolare P. Angeletti Spa Antiviral indoles
WO2008133155A1 (fr) 2007-04-19 2008-11-06 Astellas Pharma Inc. Composé hétérocyclique bicyclique
EP2494991A1 (fr) 2007-05-04 2012-09-05 Vertex Pharmaceuticals Incorporated Polythérapie pour le traitement de l'infection par VHC
US7989438B2 (en) 2007-07-17 2011-08-02 Istituto Di Ricerche Di Biologia Molecolare P. Angeletti Spa Therapeutic compounds
US8927569B2 (en) 2007-07-19 2015-01-06 Merck Sharp & Dohme Corp. Macrocyclic compounds as antiviral agents
WO2009076747A1 (fr) 2007-12-19 2009-06-25 Boehringer Ingelheim International Gmbh Inhibiteurs de polymérase virale
US8461107B2 (en) 2008-04-28 2013-06-11 Merck Sharp & Dohme Corp. HCV NS3 protease inhibitors
DE102008022221A1 (de) 2008-05-06 2009-11-12 Universität des Saarlandes Inhibitoren der humanen Aldosteronsynthase CYP11B2
US8080654B2 (en) 2008-07-22 2011-12-20 Insituto di Ricerche di Biologia Molecolare P. Angeletti SpA Macrocyclic quinoxaline compounds as HCV NS3 protease inhibitors
US7973040B2 (en) 2008-07-22 2011-07-05 Merck Sharp & Dohme Corp. Macrocyclic quinoxaline compounds as HCV NS3 protease inhibitors
WO2010080874A1 (fr) 2009-01-07 2010-07-15 Scynexis, Inc. Dérivé de cyclosporine convenant au traitement de l'infection par vhc et vih
US8828930B2 (en) 2009-07-30 2014-09-09 Merck Sharp & Dohme Corp. Hepatitis C virus NS3 protease inhibitors
US8541404B2 (en) 2009-11-09 2013-09-24 Elexopharm Gmbh Inhibitors of the human aldosterone synthase CYP11B2
CN102993105A (zh) * 2012-12-19 2013-03-27 西南大学 1-甲基-2,4-喹唑啉二酮衍生物及其制备方法和应用
CN102993105B (zh) * 2012-12-19 2014-06-11 西南大学 1-甲基-2,4-喹唑啉二酮衍生物及其制备方法和应用
WO2017149469A1 (fr) 2016-03-03 2017-09-08 Emcure Pharmaceuticals Limited Composés hétérocycliques utiles en tant que modulateurs de l'ido et/ou de la tdo
US10513515B2 (en) 2017-08-25 2019-12-24 Biotheryx, Inc. Ether compounds and uses thereof
US10927104B2 (en) 2017-08-25 2021-02-23 Biotheryx, Inc. Ether compounds and uses thereof
WO2019141808A1 (fr) 2018-01-19 2019-07-25 Idorsia Pharmaceuticals Ltd Modulateurs du récepteur c5a
US11236103B2 (en) 2018-07-27 2022-02-01 Biotheryx, Inc. Bifunctional compounds
US11897930B2 (en) 2020-04-28 2024-02-13 Anwita Biosciences, Inc. Interleukin-2 polypeptides and fusion proteins thereof, and their pharmaceutical compositions and therapeutic applications
CN115197225A (zh) * 2021-09-03 2022-10-18 贵州大学 一种五元杂环并喹唑啉酮类化合物及其制备方法
CN115197225B (zh) * 2021-09-03 2023-04-11 贵州大学 一种五元杂环并喹唑啉酮类化合物及其制备方法
CN114539148A (zh) * 2022-01-25 2022-05-27 北京英飞智药科技有限公司 一种环状n-羟基酰亚胺类化合物及其用途
CN115490643A (zh) * 2022-11-21 2022-12-20 南京合创药业有限公司 一种一锅法合成3-二氯苯基-6-氟-2,4(1h,3h)-喹唑啉二酮的方法

Similar Documents

Publication Publication Date Title
WO2007028789A1 (fr) Dérivés de quinazoline en tant qu'agents antiviraux
CN112368272B (zh) Shp2抑制剂及其用途
US10717711B2 (en) Amino quinazolines as kinase inhibitors
EP2464647B1 (fr) Azaindoles en tant qe modulateurs du recepteur btk et leur utilisation
ES2389907T3 (es) Compuesto de amida heterocíclica y uso del mismo como un inhibidor de MMP-13
ES2274526T3 (es) Pirido(2,3-d)pirimidinas para inhibir la proliferacion celular mediada por tirosinaquinasa.
JP2010511727A5 (fr)
AU2006273692B8 (en) 1,4-Dihydropyridine-fused heterocycles, process for preparing the same, use and compositions containing them
EP2185556A1 (fr) Analogues de l'imidazopyridine et leur utilisation en tant qu'agonistes du système de messagerie cellulaire wnt-bêta-caténine
AU2006232105A1 (en) Purine and imidazopyridine derivatives for immunosuppression
WO2006027628A2 (fr) Derives de naphtalimide en tant qu'agents antiviraux
BRPI0622030A2 (pt) Derivados de purina 7-substituída, para imunossupressão
JP2010511727A (ja) アデノシン受容体アンタゴニストとしての置換ピリミジン
WO2007117494A1 (fr) Désazapurines utiles comme inhibiteurs des kinases janus
SK13532001A3 (sk) Aminopiridíny ako inhibítory sorbitoldehydrogenázy
CA2557541A1 (fr) Derives de pyrimidine
AU2007211399A1 (en) Tricyclic N-heteroaryl-carboxamide derivatives containing a benzimidazole unit, method for preparing same and their therapeutic use
CA2646023A1 (fr) Piperazinyl-oxoalkyl-tetrahydroisoquinoleines et analogues apparentes
AU2011366498A1 (en) Derivatives of N- [(1H-pyrazol-1-yl) aryl] - 1H - indole or 1H - indazole - 3 - carboxamide, their preparation and their use as P2Y12 antagonists
AU2011206475A1 (en) 5-oxo-5, 8-dihydropyrido [2, 3-d] pyrimidine derivatives as CaMKII kinase inhibitors for treating cardiovascular diseases
WO2014026467A1 (fr) Composés de pyrimidine substitués bicycliques
ES2208063A1 (es) Nuevos derivados de la 4-(pirrolopirimidin-6-il)bencenosulfonamida.
Linz et al. Design, synthesis and dopamine D4 receptor binding activities of new N-heteroaromatic 5/6-ring Mannich bases
AU2009329426A1 (en) Derivatives of 6-cycloamino-2-thienyl-3-(pyridin-4-yl)imidazo[1,2-b]-pyridazine and 6-cycloamino-2-furanyl-3-(pyridin-4-yl)imidazo1,2-b]-pyridazine, preparation and therapeutic application thereof
WO2009154870A1 (fr) Inhibiteurs de l'intégrase vih

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application
NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 06778415

Country of ref document: EP

Kind code of ref document: A1