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AR066999A2 - Piperidinas sustituidas, preparados farmaceuticos y uso como inhibidores de renina - Google Patents

Piperidinas sustituidas, preparados farmaceuticos y uso como inhibidores de renina

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Publication number
AR066999A2
AR066999A2 ARP080102063A ARP080102063A AR066999A2 AR 066999 A2 AR066999 A2 AR 066999A2 AR P080102063 A ARP080102063 A AR P080102063A AR P080102063 A ARP080102063 A AR P080102063A AR 066999 A2 AR066999 A2 AR 066999A2
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AR
Argentina
Prior art keywords
alkyl
alkoxy
oxo
hydroxy
alq
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ARP080102063A
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English (en)
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Speedel Experimenta Ag
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Publication of AR066999A2 publication Critical patent/AR066999A2/es

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
    • C07D211/40—Oxygen atoms
    • C07D211/42—Oxygen atoms attached in position 3 or 5
    • 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
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/06—Antiglaucoma agents or miotics
    • 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
    • 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
    • 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
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Urology & Nephrology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Vascular Medicine (AREA)
  • Hospice & Palliative Care (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

Piperidina sustituida de la formula (1) en la cual (A) R1 es oxazolilo, indolilo, pirrolilo, pirazolilo, triazinilo, 2-oxo-dihidro-benzo-[d][1,3]oxazinilo, 4-oxo-dihidro-imidazolilo, 5-oxo-4H-[1,2,4]triazinilo, 3-oxo-4H-benzo[1,4]tiazinilo, tetrahidro-quinoxalinilo, 1,1,3-trioxo-dihidro-2H-1lambda*6*-benzo[1,4]tiazinilo, 1-oxo-piridilo, dihidro-2H-benzo[1,4]oxazinilo, 2-oxo-tetrahidro-benzo[e][1,4]diazepinilo, 2-oxo-dihidro-benzo[e][1,4]diazepinilo, 1H-pirrolizinilo, ftalazinilo, 1-oxo-3H-isobenzofuranilo, 4-oxo-3H-tieno[2,3-d]-pirimidinilo, 3-oxo-4H-benzo[1,4]oxazinilo, [1,5]naftiridilo, dihidro-2H-benzo[1,4]tiazinilo, 1,1-dioxo-dihidro-2H-benzo[1,4]tiazinilo, 2-oxo-1H-pirido[2,3-b]-[1,4]oxazinilo, dihidro-1H-pirido[2,3-b][1,4]oxazinilo, 1H-pirrolo[2,3-b]piridilo, benzooxazoliIo, 2-oxo-benzooxazolilo, 2-oxo-1,3-dihidro-indolilo, 2,3-dihidroindolilo, indazolilo, benzofuranilo, dihidrobenzofuranilo. Tetrahidropiranilo, 2-oxo-piperidinilo o 2-oxo-azepanilo sustituidos o no sustituidos; o (B) R1 es arilo, que está sustituido con al menos un sustituyente seleccionado de alcoxi C1-6-alcoxi C1-6-alquilo C1-6, cicloalquil C3-8-alquilo C1-6, alcoxi C1-6-carbonilo, alquilcarbonilamino C0-6, alquilcarbonilamino C0-6-alquilo-C1-6, alquilcarbonilamino C0-6-alcoxi C1-6, N-alquil C1-6-alquilcarbonilamino C0-6-alquilo C1-6, N-alquil C1-6-alquilcarbonilamino C0-6-alcoxi C1-6,cicloalquilcarbonilamino C3-8-alquilo C1-6, cicloalquilcarbonilamino C3-8-alcoxi C1-6, alcoxi C1-6-alquilo C1-6, hidroxi-alquilo C1-6, hidroxi-alcoxi-C1-6-alquilo C1-6, hidroxi-alcoxi C 1-6-alcoxi C1-6, alcoxicarbonilamino C1-6-alquilo C1-6, alcoxicarbonilamino C1-6-alcoxi C1-6, alquilaminocarbonilamino C1-6-alquilo C1-6, alquilcarbonilamino C1-6-alcoxi C1-6, alquilaminocarbonil C1-6-alquilo C1-6, alquilaminocarbonil C1-6-alcoxi C1-6, alquilaminocarbonil C1-6-alcoxi C1-6-alquilo C1-6, di-alquilaminocarbonil C1-6-alquilo C1-6, di-alquilaminocarbonil C1-6-alcoxi C1-6, alquilcarboniloxi C1-6-alquiIo C1-6, alcoxicarboniloxi C1-6-alquilo C1-6, alquilcarboniloxi C1-6-alcoxi C1-6, ciano-alquilo C1-6, ciano-alcoxi C1-6, alcoxicarbonil C1-6-alquilo C1-6, alcoxicarbonil C1-6-alcoxi C1-6,. Alquilsulfonilamino C1-6-alquilo C1-6, alquilsulfonilamino C1-6-alcoxi C1-6, N-alquil C1-6-alquilsulfonilamino C1-6-alquilo C1-6, N-alquil C1-6-alquilsulfonilamino C1-6-alcoxi C1-6, aminoalquilo C1-6, aminoalcoxi C1-6, alquilamino C1-6-alquilo C1-6, alquilamino C1-6-alcoxi C1-6, di-alquilamino C1-6-alquilo C1-6, di-alquilamino C1-6-alcoxi C1-6, alquilsulfonil C1-6-alquilo C1-6, alquilsulfonil C1-6-alcoxi C1-6, carboxialquilo C1-6, carboxialcoxi C1-6, carboxialcoxi C1-6-alquilo C1-6, alcoxi C1-6-alquil C1-6-carbonilo, acil-alcoxi C1-6-alquilo C1-6, N-alquil C1-6-alcoxi C1-6-carbonilamino, N-hidroxi-alquilaminocarbonil C1-6-alquilo C1-6, N-hidroxi-alquilaminocarbonil C1-6-alcoxi C1-6, N-hidroxi-aminocarbonilalquilo C1-6, N-hidroxi-aminocarbonilalcoxi C1-6, alcoxi C1-6-aminocarbonilalquilo C1-6, alcoxi C1-6-aminocarbonilalcoxi C1-6, N-alcoxi C1-6-alquilaminocarbonil C1-6-alquilo C1-6, N-alcoxi C1-6-alquilaminocarbonil C1-6-alcoxi C1-6, N-acil-alcoxi-C1-6-alquilamino C1-6, alcoxi C1-6-alquil C1-6-carbamoílo, N-alquil C1-6-alcoxi C1-6-alquil C1-6-carbamoílo, alcoxi C1-6-alquil C1-6-carbonilo, alcoxi C1-6-alquil C1-6-carbonilamino, N-alquil C1-6-alcoxi C1-6-alquil C1-6-carbonilamino, carbamoilalquilo C1-6, carbamoilalcoxi C1-6, alquil C1-6-carbamoílo, di-alquil C1-6-carbamoílo, alquil C1-6-sulfonilo, alquil C1-6-amidinilo, acetamidinil-alquilo C1-6. O-metiloximil-alquilo C1-6 y O,N-dimetilhidroxilamino-alquilo C1-6 o (C) R1 es arilo o heterociclilo, que está sustituido con al menos un sustituyente seleccionado de [1,2,4]-triazol-1-il-alquilo, [1,2,4j-triazol-1-il-alcoxi, [1,2,4]-triazol-4-il-alquilo, [1,2,4]-triazol-4-il-alcoxi, [1,2,4]-oxadiazol-5-il-alquilo, [1,2,4]-oxadiazol-5-il-alcoxi, 3-metil-[1,2,4]-oxadiazol-5-il- alquilo, 3-metil-[1,2,4]-oxadiazol-5-il-alcoxi, 5-metil-[1,2,4]-oxadiazol-3-il-alquilo, 5-metil-[1,2,4]-oxadiazol-3-il-alcoxi, tetrazol-1-il-alquilo, tetrazol-1-il-alcoxi, tetrazol-2-il-alquilo, tetrazol-2-il-alcoxi, tetrazol-5-il-alquilo, tetrazol-5-iI-alcoxi, 5-metil-tetrazol-1-il-alquilo, 5-metil-tetrazol-1-il-alcoxi, tiazol-4-il-alquilo, tiazol-4-il-alcoxi, oxazol-4-il-alquilo, oxazol-4-il-alcoxi, 2-oxo-pirrolidinil-alquilo, 2-oxo-pirrolidinil-alcoxi, imidazolil-alquilo, imidazolil-alcoxi, 2-metil-imidazolil-alquilo, 2-metil-imidazolil-alcoxi, dioxolanilo, dioxanilo, ditiolanilo, ditianilo, pirrolidinilo, piperidinilo, piperazinilo, pirrolilo, 4-metilpiperazinilo, morfolinilo. tiomorfolinilo. 2-hidroximetilpirrolidinilo, 3-hidroxipirrolidinilo, 3,4-dihidroxipirrolidinilo, 3-acetamidametilpirrolidinilo, 3-alcoxi C1-6-alquil C1-6-pirrolidinilo, 4-hidroxi piperidinilo, 4-oxopiperidinilo, 3,5-dimetilmorfolinilo, 4,4-dioxotiomorfolinilo, 4-oxotiomorfolinilo, 2,6-dimetilmorfolinilo, 2-oxo-imidazolidinilo, 2-oxo-oxazolidinilo, 2-oxo-pirrolidinilo, 2-oxo-[1,3]oxazinilo, 2-oxo-tetrahidro-pirimidinilo, 2-oxo-oxazolidinil-alquilo C1-6, 2-oxo-oxazolidinil-alcoxi C1-6, 1-alcoxi C1-6-alquil C1-6-imidazol-2-ilo, 1-alcoxi-C1-6-alquil C1-6-tetrazol C1-6-5-ilo, 5-alcoxi C1-6-alquil C1-6-tetrazol-1-ilo y 2-aIcoxi C1-6-alquil C1-6-4-oxo-imidazol-1-ilo; o (D) R1 es arilo o heterociclilo, cuando n es 0 y X es -O-CH-R11-CO-NR9-, o cuando n y m son 0 y X es -O-CH-R11- y R2 es fenilo sustituido con alcoxibenciloxi C1-6-alcoxi C1-6; o (E) R1 es arilo o heterociclilo, cuando n es 1 y Z es -aIq-NR9-, en la cual alq significa alquilen C1-6 o (F) R1es arilo o heterociclilo, cuando R2 significa tetrazolilo o imidazolilo, que pueden estar sustituidos con 1-3 grupos halogeno, hidroxi, ciano, trifluorometilo, alquilo C1-6. halo-alquilo C1-6, hidroxi-alquilo C1-6, alcoxi C1-6-alquilo C1-6, ciano-alquilo C1-6, carboxialquilo C1-6, alcanoiloxi C1-6-alquilo C1-6, alcoxicarboniloxi C1-6-alquilo C1-6, alcoxicarbonilo o alcoxi C1-6, o un grupo alquilendioxi y/o con un radical L1-T1-L2-T2-L3-T3-L4-T4-L5-U; R2 sustituye fenilo con 1-3 grupos halogeno, hidroxi, ciano, trifluorometilo, alquilo C1-6, halo-alquilo C1-6, hidroxi-alquilo C1-6, alcoxi C1-6-alquilo C1-6, ciano-alquilo C1-6, carboxialquilo C1-6, alcanoiloxi C1-6-alquilo C1-6, alcoxicarboniloxi C1-6-alquilo C1-6, alcoxicarbonilo o 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 significan independientemente entre sí una union, alquileno C1-8, alquenileno C2-8 o alquinileno C2-8 o están ausentes; T1, T2, T3 y T4 significan independientemente entre sí: (a) una union o están ausentes, o uno de los grupos (b) -CH(OH)-, (c) -CH(OR6)-, (d) -CH(NR5R6)-, (e) -CO-, (f) -CR7R8-, (g) -O- o -NR6- ,(h) -S(O)0-2, (l) -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, (t) -C(R11)(R12)-, donde las uniones que parten de (b)-(t) llevan a un átomo de carbono aromático o saturado del grupo adyacente, cuando la union parte de un heteroátomo, y donde no existen más de dos grupos (b)-(f), tres grupos (g)-(h) y un grupo (i)-(t); R3 es hidroxi, alcoxi C1-6 o alqueniloxi C1-6; R4 es hidrogeno; R5 y R6 significan hidrogeno, alquilo C1-6, alquenilo C2-6, arilalquilo C1-6 o acilo, o conjuntamente con el átomo de nitrogeno al que están unidos, significan un anillo heterocíclico de 5 o 6 miembros, que pueden contener un átomo de N, O o S adicional o un grupo -SO- o -SO2-, donde el átomo de N adicional puede, eventualmente, estar sustituido con radicales alquilo C1-6; R7 y R8 conjuntamente con el átomo de C al que están unidos, representan un anillo de 3-7 miembros, que pueden contener uno o dos átomos de -O- o -S- o grupos -SO- o -SO2-; R9 es hidrogeno, alquilo C1-6, alcoxi C1-6-alquilo C1-6, acilo o arilalquilo; R10 es carboxialquilo, alcoxicarbonilalquilo, alquilo o hidrogeno; R11 es hidrogeno o alquilo C1-6; R12 es hidrogeno o alquilo C1-6; U significa hidrogeno, alquilo C1-6, cicloalquilo C3-8, ciano, eventualmente cicloalquilo C3-8 sustituido, arilo o heterociclilo; Q está ausente; X representa una union, oxígeno o azufre, donde la union que parte de un átomo de oxígeno o azufre, lleva a un átomo de C saturado del grupo Z o a R1, o un grupo >CH-R11, >CHOR9, -O-CO-, >CO, >C=NOR10, -O-CHR11- u -O-CHR11-CO-NR9-; W significa oxígeno o azufre; Z es alquileno C1-6, alquenileno C2-6, hidroxi-alquilideno C1-6. -O-, -S-. -O-alq-, -S-alq-, -alq-O-, -alq-S- o -alq-NR9-, donde alq significa alquileno C1-6; y donde (a) si Z significa -O- o -S-, X es -CH-R11-, y, o R2 contiene un sustituyente L1-T1-L2-T2-L3-T3-L4-T4-L5-U o R4 es un sustituyente como el definido arriba, distinto de hidrogeno; (b) si Z significa -O-alq-, o -S-alq-, X es -CH-R11-; y (c) si X representa una union, Z significa alquenileno C2-6, -alq-O- o -alq-S-, n es el numero 0 o 1; m es el numero 0; y sales aceptables para uso farmacéutico. Composiciones farmacéuticas que contienen dichos compuestos y usos como inhibidores de renina.
ARP080102063A 2003-10-01 2008-05-15 Piperidinas sustituidas, preparados farmaceuticos y uso como inhibidores de renina AR066999A2 (es)

Applications Claiming Priority (2)

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CH16692003 2003-10-01
CH3432004 2004-02-27

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ARP080102063A AR066999A2 (es) 2003-10-01 2008-05-15 Piperidinas sustituidas, preparados farmaceuticos y uso como inhibidores de renina

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US (2) US7790715B2 (es)
EP (2) EP1961752A3 (es)
AR (2) AR046269A1 (es)
TW (2) TW200513461A (es)
WO (1) WO2005061457A1 (es)

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