AR045950A1 - COMPOUNDS DERIVED FROM PIPERAZINE, PHARMACEUTICAL COMPOSITIONS THAT CONTAIN THEM AND THEIR USE IN THE MANUFACTURE OF MEDICINES. - Google Patents

COMPOUNDS DERIVED FROM PIPERAZINE, PHARMACEUTICAL COMPOSITIONS THAT CONTAIN THEM AND THEIR USE IN THE MANUFACTURE OF MEDICINES.

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Publication number
AR045950A1
AR045950A1 ARP040103493A ARP040103493A AR045950A1 AR 045950 A1 AR045950 A1 AR 045950A1 AR P040103493 A ARP040103493 A AR P040103493A AR P040103493 A ARP040103493 A AR P040103493A AR 045950 A1 AR045950 A1 AR 045950A1
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AR
Argentina
Prior art keywords
alkyl
alk
atom
absent
groups
Prior art date
Application number
ARP040103493A
Other languages
Spanish (es)
Original Assignee
Speedel Experimenta Ag
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
Application filed by Speedel Experimenta Ag filed Critical Speedel Experimenta Ag
Publication of AR045950A1 publication Critical patent/AR045950A1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/12—Drugs for disorders of the urinary system of the kidneys
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Abstract

La presente se refiere a compuestos derivados de piperazina, composiciones farmacéuticas que los contienen y su uso en la fabricación de medicamentos. Los compuestos son apropiados en especial como inhibidores de la renina y también para ser usados en composiciones farmacéuticas y medicamentos para el tratamiento o prevención de la hipertensión, insuficiencia cardíaca, glaucoma, infarto de miocardio, insuficiencia renal y restenosis. Reivindicación 1: Compuestos de fórmula (1) o (2) en donde: R1 es arilo o heterociclilo; R2 es fenilo, naftilo, acenaftilo, ciclohexilo, piridilo, pirimidinilo, pirazinilo, oxopiridinilo, diazinilo, triazolilo, tienilo, oxazolilo, oxadiazolilo, tiazolilo, pirrolilo, furilo, tetrazolilo o imidazolilo, radicales que pueden estar sustituidos con 1-3 grupos halógeno, hidroxi, ciano, trifluorometilo, alquilo C1-6, haloalquilo C1-6, hidroxialquilo C1-6,. alcoxi C1-6-alquilo C1-6, cianoalquilo C1-6, carboxialquilo C1-6, alcanoiloxi 1-6-alquilo C1-6, alcoxicarboniloxi C1-6-alquilo C1-6, alcoxicarbonilo C1-6 o grupos alcoxi C1-6 o un grupo alquilendioxi C1-6 y/o con un radical L1-T1-L2-T2-L3-T3-L4-T4-L5-U; L1, L2, L3, L4 y L5 son, se modo independiente entre sí, un enlace, alquileno C1-8, alquenileno C2-8 o alquinileno C2-8 o están ausentes; T1, T2, T3 y T4 son, de modo independiente entre sí, (a) un enlace o están ausentes, o uno de los grupos (b) -CH(O)-, (c) -CH(OR6)-, (d) -CH(NR5R6)-, (e) -CO-, (f) -CR7R8-, (g) -O- o -NR6-, (h) - S(O)0-2-, (i) -SO2NR6-, (j) -NR6SO2-, (k) -CONR6-, (l)-NR6CO-, (m) -O-CO-, (n) -CO-O-, (o) -O-CO-O-, (p) -O-CO-NR6-, (q) -N(R6)-CO-N(R6)-, (r) -N(R6)-CO-O-, (s) pirrolidinileno, piperidinileno o piperazinileno, y (t) -C(R11)(R12)-, en donde los enlaces que parten de (b)-(t) llevan a un átomo de C saturado o aromático del grupo adyacente, en caso de que el enlace parte de un heteroátomo, y en donde no más de dos grupos (b)-(f), tres grupos (g)-(h) y un grupo (i)-(t) están ausentes; R3 es H, alquilo C1-6, alquenilo C1-6, alcoxi C1-6, hidroxialquilo C1-6, alcoxi C1-6-alquilo C1-6, bencilo, oxo o un grupo R4-Z1-X1-, en donde R4 es (a) H-, (b) alquilo C1-6-, (c) alquenilo C1-6, (d) hidroxialquilo C1-6, (e) polihidroxialquilo C1-6, (f) alquil C1-6-O-alquilo C1-6-, (g) arilo, (h) heterociclilo, (i) arilalquilo, (j) heterociclilalquilo, (k) ariloxialquilo, (l) heterocicliloxialquilo, (m) (R5,R6)N-(CH2)1-3-, (n) (R5,R6)N-, (o) alquil C1-6-S(O)0-2-, (p) aril-S(O)0-2, (q) heterociclil- S(O)0-2-, (r) HO-SO3- o sus sales, (s) H2N-C(NH)-NH-, y (t) NC-, y los enlaces que parten de (n)-(t) llevan a un átomo de C del grupo adyacente y este átomo de C está saturado, en caso de que el enlace parta de un heteroátomo; Z1 es (a) un enlace, está ausente, o es uno de los grupos, (b) alquileno C1-6, (c) alquenileno C1-6-, (d)-O-, -N(R11)-, -S(O)0-2-, (e) -CO-, (f) -O-CO-, (g) -O-CO-O-, (h) -O-CO-N(R11)-, (i) -N(R11)-CO-O-, (j) -CO-N(R11)-, (k) -N(R11)-CO-, (l) -N(R11)-CO-N-(R11)-, y (m) - CH(OR9)- y los compuestos que parten de (d) y (f)-(m) llevan a un átomo de C del grupo adyacente y este átomo de C está saturado, en caso de que el enlace parta de un heteroátomo; X1 es un enlace, está ausente o es -(CH2)1-3-; R5 y R6 son H, alquilo C1-6, alquenilo C1-6, arilalquilo C1-6 o acilo o, junto con el átomo de N al que están unidos, son un anillo heterocíclico de 5 o 6 miembros que puede contener un átomo de N, O o S adicional o un grupo -SO- o -SO2-, en donde el átomo de N adicional puede estar opcionalmente sustituido con radicales alquilo C1-6; R7 y R8 son junto con el átomo de C al que están unidos, un anillo de 3-7 miembros que puede contener uno o dos átomos de -O- o -S- o grupos -SO- o -SO2-; R9 es H, alquilo C1-6, cicloalquilo C3-8, alcoxi C1-6-alquilo C1-6, acilo o arilalquilo; R10 es carboxialquilo, alcoxicarbonilalquilo, alquilo o H, R11 es H o alquilo C1-6 R12 es H o alquilo C1-6; U es H, alquilo C1-6, cicloalquilo, ciano, cicloalquilo opcionalmente sustituido, arilo o heterociclilo; Q es etileno o está ausente (fórmula 1) o es etileno o metileno (fórmula 2); X es un enlace o un grupo >CH-R11, >CR9R11, >CHOR9, >CO o >C=NOR10; Z está ausente o es alquileno C1-6, alquenileno C1-6, hidroxialquilideno C1-6, -CH-R11-CO-NR9-, -O-, -S-, -NR9, -O-Alk-, -S-Alk-, -NR9-Alk-, -Alk-O-, -Alk-S- o -Alk-NR9-, en donde Alk es alquileno C1-6; y en donde (a) en caso de que Z sea -O- o -S-, X es -CR9R11- y R2 contiene un sustituyente L1-T1-L2- T2-L3-T3-L4-T4-L5-U o R3 es un sustituyente distinto de H tal como se definió con anterioridad; (b) en caso de que Z sea -O-Alk-, -S-Alk- o -NR9-Alk-, X es -CR9R11-; y (c) en caso de que X sea un enlace, Z es alquenileno C1-6, -Alk-O-, -Alk-S- o - Alk-NR9-; y sus sales de utilidad farmacéutica.This refers to piperazine-derived compounds, pharmaceutical compositions containing them and their use in the manufacture of medicaments. The compounds are especially suitable as renin inhibitors and also for use in pharmaceutical compositions and medicaments for the treatment or prevention of hypertension, heart failure, glaucoma, myocardial infarction, renal failure and restenosis. Claim 1: Compounds of formula (1) or (2) wherein: R 1 is aryl or heterocyclyl; R2 is phenyl, naphthyl, acenaphthyl, cyclohexyl, pyridyl, pyrimidinyl, pyrazinyl, oxopyridinyl, diazinyl, triazolyl, thienyl, oxazolyl, oxadiazolyl, thiazolyl, pyrrolyl, furyl, tetrazolyl or imidazolyl radicals which may be substituted with 1-3 halogen groups hydroxy, cyano, trifluoromethyl, C1-6 alkyl, C1-6 haloalkyl, C1-6 hydroxyalkyl ,. C 1-6 alkoxy-C 1-6 alkyl, C 1-6 cyanoalkyl, C 1-6 carboxyalkyl, C 1-6 alkanoyloxy, C 1-6 alkoxycarbonyloxy-C 1-6 alkyl, C 1-6 alkoxycarbonyl or C 1-6 alkoxy groups or a C1-6 alkylenedioxy group and / or with a radical L1-T1-L2-T2-L3-T3-L4-T4-L5-U; L1, L2, L3, L4 and L5 are, independently of each other, a bond, C1-8 alkylene, C2-8 alkenylene or C2-8 alkynylene or are absent; T1, T2, T3 and T4 are, independently of each other, (a) a link or are absent, or one of the groups (b) -CH (O) -, (c) -CH (OR6) -, ( d) -CH (NR5R6) -, (e) -CO-, (f) -CR7R8-, (g) -O- or -NR6-, (h) - S (O) 0-2-, (i) -SO2NR6-, (j) -NR6SO2-, (k) -CONR6-, (l) -NR6CO-, (m) -O-CO-, (n) -CO-O-, (o) -O-CO -O-, (p) -O-CO-NR6-, (q) -N (R6) -CO-N (R6) -, (r) -N (R6) -CO-O-, (s) pyrrolidinylene , piperidinylene or piperazinylene, and (t) -C (R11) (R12) -, where the bonds that start from (b) - (t) lead to a saturated or aromatic C atom of the adjacent group, in case the link starts from a heteroatom, and where no more than two groups (b) - (f), three groups (g) - (h) and one group (i) - (t) are absent; R3 is H, C1-6 alkyl, C1-6 alkenyl, C1-6 alkoxy, C1-6 hydroxyalkyl, C1-6 alkoxy-C1-6 alkyl, benzyl, oxo or a group R4-Z1-X1-, wherein R4 is (a) H-, (b) C1-6- alkyl, (c) C1-6 alkenyl, (d) C1-6 hydroxyalkyl, (e) C1-6 polyhydroxyalkyl, (f) C1-6-O-alkyl C1-6- alkyl, (g) aryl, (h) heterocyclyl, (i) arylalkyl, (j) heterocyclylalkyl, (k) aryloxyalkyl, (l) heterocyclyloxyalkyl, (m) (R5, R6) N- (CH2) 1 -3-, (n) (R5, R6) N-, (o) C1-6-S-alkyl (O) 0-2-, (p) aryl-S (O) 0-2, (q) heterocyclyl- S (O) 0-2-, (r) HO-SO3- or its salts, (s) H2N-C (NH) -NH-, and (t) NC-, and the bonds starting from (n) - (t) lead to a C atom of the adjacent group and this C atom is saturated, in case the bond starts from a heteroatom; Z1 is (a) a bond, is absent, or is one of the groups, (b) C1-6 alkylene, (c) C1-6 alkenylene, (d) -O-, -N (R11) -, - S (O) 0-2-, (e) -CO-, (f) -O-CO-, (g) -O-CO-O-, (h) -O-CO-N (R11) -, (i) -N (R11) -CO-O-, (j) -CO-N (R11) -, (k) -N (R11) -CO-, (l) -N (R11) -CO-N - (R11) -, and (m) - CH (OR9) - and the compounds that start from (d) and (f) - (m) lead to a C atom of the adjacent group and this C atom is saturated, in case the link starts from a heteroatom; X1 is a link, is absent or is - (CH2) 1-3-; R5 and R6 are H, C1-6 alkyl, C1-6 alkenyl, C1-6 arylalkyl or acyl or, together with the N atom to which they are attached, they are a 5- or 6-membered heterocyclic ring that may contain an atom of Additional N, O or S or a group -SO- or -SO2-, wherein the additional N atom may be optionally substituted with C1-6 alkyl radicals; R7 and R8 are together with the C atom to which they are attached, a 3-7 membered ring that may contain one or two atoms of -O- or -S- or groups -SO- or -SO2-; R9 is H, C1-6 alkyl, C3-8 cycloalkyl, C1-6 alkoxy-C1-6 alkyl, acyl or arylalkyl; R10 is carboxyalkyl, alkoxycarbonylalkyl, alkyl or H, R11 is H or C1-6 alkyl R12 is H or C1-6 alkyl; U is H, C1-6 alkyl, cycloalkyl, cyano, optionally substituted cycloalkyl, aryl or heterocyclyl; Q is ethylene or is absent (formula 1) or is ethylene or methylene (formula 2); X is a link or group> CH-R11,> CR9R11,> CHOR9,> CO or> C = NOR10; Z is absent or is C1-6 alkylene, C1-6 alkenylene, C1-6 hydroxyalkylidene, -CH-R11-CO-NR9-, -O-, -S-, -NR9, -O-Alk-, -S- Alk-, -NR9-Alk-, -Alk-O-, -Alk-S- or -Alk-NR9-, where Alk is C1-6 alkylene; and where (a) in case Z is -O- or -S-, X is -CR9R11- and R2 contains a substituent L1-T1-L2-T2-L3-T3-L4-T4-L5-U or R3 is a substituent other than H as defined above; (b) in case Z is -O-Alk-, -S-Alk- or -NR9-Alk-, X is -CR9R11-; and (c) in case X is a bond, Z is C1-6 alkenylene, -Alk-O-, -Alk-S- or - Alk-NR9-; and its salts of pharmaceutical utility.

ARP040103493A 2003-10-09 2004-09-27 COMPOUNDS DERIVED FROM PIPERAZINE, PHARMACEUTICAL COMPOSITIONS THAT CONTAIN THEM AND THEIR USE IN THE MANUFACTURE OF MEDICINES. AR045950A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH17252003 2003-10-09

Publications (1)

Publication Number Publication Date
AR045950A1 true AR045950A1 (en) 2005-11-16

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ID=34438156

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ARP040103493A AR045950A1 (en) 2003-10-09 2004-09-27 COMPOUNDS DERIVED FROM PIPERAZINE, PHARMACEUTICAL COMPOSITIONS THAT CONTAIN THEM AND THEIR USE IN THE MANUFACTURE OF MEDICINES.

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AR (1) AR045950A1 (en)
TW (1) TW200528449A (en)
WO (1) WO2005037803A1 (en)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1707206A1 (en) * 2005-03-31 2006-10-04 Speedel Experimenta AG Piperazine derivates for the inhibition of beta-secretase, cathepsin D, plasmepsin ll and HIV protease and for the treatment of malaria, Alzeheimer and AIDS
GB0511063D0 (en) * 2005-05-31 2005-07-06 Novartis Ag Organic compounds
WO2007034445A2 (en) * 2005-09-26 2007-03-29 Actelion Pharmaceuticals Ltd Novel piperazine derivatives as renin inhibitors for cardiovascular events and renal insufficiency
WO2007049224A1 (en) * 2005-10-25 2007-05-03 Actelion Pharmaceuticals Ltd Novel hexahydro- or octahydro-cyclopenta[c]pyrrole derivatives
WO2008074450A2 (en) * 2006-12-20 2008-06-26 Nicox S.A. Non-peptidic renin inhibitors nitroderivatives
JP5092111B2 (en) * 2007-02-05 2012-12-05 トーアエイヨー株式会社 Butoxyaniline derivatives
JPWO2009022731A1 (en) * 2007-08-10 2010-11-18 日本ケミファ株式会社 P2X4 receptor antagonist
TW200932241A (en) 2007-12-05 2009-08-01 Speedel Experimenta Ag Organic compounds
UY33535A (en) * 2010-08-13 2011-12-01 Biolab Sanus Farmaceutuca Limitada DERIVATIVES OF 6,7-DIHIDRO-3H-OXAZOLO [3,4] PIRAZIN-5,8-DIONA
AU2013219799C1 (en) 2012-02-15 2017-12-07 The United States Of America, As Represented By The Secretary, Department Of Health And Human Services Methods of treating and preventing diseases and disorders of the central nervous system
AR099523A1 (en) * 2014-02-24 2016-07-27 Biolab Sanus Farmacêutica Ltda COMPOUNDS DERIVED FROM 6,7-DIHIDRO-3H-OXAZOLO [3,4-A] PIRAZINA-5,8-DIONA

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE59610509D1 (en) * 1995-09-07 2003-07-10 Hoffmann La Roche NEW 4- (OXYALKOXYPHENYL) -3-OXY-PIPERIDINE FOR TREATING HEART AND KIDNEY INSUFFICIENCY
US6376672B1 (en) * 1999-04-27 2002-04-23 Hoffmann-La Roche Inc. Naphthalenylmethoxypiperidines as renin inhibitors
US6197959B1 (en) * 1999-04-27 2001-03-06 Hoffmann-La Roche Inc. Piperidine derivatives
GB0119797D0 (en) * 2001-08-14 2001-10-03 Glaxo Group Ltd Chemical compounds
US20040214832A1 (en) * 2003-04-10 2004-10-28 Cuiman Cai Piperazine derivative renin inhibitors

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WO2005037803A1 (en) 2005-04-28

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