AR031550A1 - Derivados del acido alfa-sulfonil hidroxamico, metodos para su preparacion, y para la preparacion de compuestos intermediarios, composiciones farmaceuticas, y, el uso de dichos derivados para la manufactura de un medicamento - Google Patents

Derivados del acido alfa-sulfonil hidroxamico, metodos para su preparacion, y para la preparacion de compuestos intermediarios, composiciones farmaceuticas, y, el uso de dichos derivados para la manufactura de un medicamento

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Publication number
AR031550A1
AR031550A1 ARP010100352A ARP010100352A AR031550A1 AR 031550 A1 AR031550 A1 AR 031550A1 AR P010100352 A ARP010100352 A AR P010100352A AR P010100352 A ARP010100352 A AR P010100352A AR 031550 A1 AR031550 A1 AR 031550A1
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Argentina
Prior art keywords
alkyl
cycloalkyl
aryl
membered
hydrogen
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ARP010100352A
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English (en)
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Wyeth Corp
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    • 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
    • C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
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    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A61P35/04—Antineoplastic agents specific for metastasis
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A—HUMAN NECESSITIES
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    • A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
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    • 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
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    • A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
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    • 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
    • C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
    • C07D211/66—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4 having a hetero atom as the second substituent in position 4

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Abstract

Derivados del ácido alfa-sulfonil hidroxámico de Formula (2), en donde: X es hidrogeno o alquilo C1-6; Y es hidrogeno, alquilo C1-6, arilo C6-10, heteroarilo de 5-10 miembros que tiene 1-3 heteroátomos, cicloalquilo C3-6, cicloheteroalquilo de 5-10 miembros, estando todos opcionalmente sustituidos; R3 es alquilo C1-18, alquenilo C2-18, alquinilo C2-18, cicloalquilo C3-6, cicloheteroalquilo de 5-10 miembros, arilo C6-10, heteroarilo de 5-6 miembros que tiene 1-3 heteroátomos seleccionados entre N, NR4, O y S, estando todos opcionalmente sustituidos; R4 es hidrogeno, arilo, aralquilo, heteroarilo, heteroaralquilo, alquilo C1-6, cicloalquilo C3-6, C(O)nR5, -CONR5R6 o SO2R5; R5 y R6 son cada uno independientemente hidrogeno, arilo, heteroarilo de 4-8 miembros, cicloalquilo C3-6, cicloheteroalquilo de 5-10 miembros, alquilo C1-18, alquenilo C2-18; o R5 y R6 tomados junto con el átomo de nitrogeno al cual están unidos pueden formar un anillo cicloheteroalquilo de 5-10 miembros; y n es 1 o 2; o sales farmacéuticas del mismo; método de preparacion de derivados de ácido alfa-sulfonil hidroxámico de la formula (1), en donde: X es hidrogeno, alquilo C1-6, bencilo, hidroxietilo, t-butildimetilsililo, trimetilsililo o tetrahidropiranilo; Y es hidrogeno, alquilo C1-6, arilo C6-10, heteroarilo de 5-10 miembros, cicloalquilo C3-6, cicloheteroalquilo de 5-10 miembros, pudiendo estar todos opcionalmente sustituidos; R1 y R2 son cada uno, independientemente, hidrogeno, arilo C6-10, heteroarilo de 5-10 miembros, cicloalquilo C3-6, cicloheteroalquilo de 5-10 miembros, alquilo C1-18, alquenilo C2-18, alquinilo C2-18; o R1 y R2 tomados junto con el átomo de carbono al cual están unidos forman un anillo cicloalquilo C3-8, o un anillo cicloheteroalquilo de 5-10 miembros, todos opcionalmente sustituidos; R3 es alquilo C1-18, alquenilo C2-18, alquinilo C2-18, cicloalquilo C3-6, cicloheteroalquilo de 5-10 miembros, arilo C6-10, heteroarilo de 5-6 miembros, todos opcionalmente sustituidos; R4 es hidrogeno, arilo, aralquilo, heteroarilo, heteroaralquilo, alquilo C1-6, cicloalquilo C3-6, -C(O)nR5, -CONR5R6 o SO2R5; R5 y R6 son cada uno independientemente hidrogeno, arilo, heteroarilo de 4-8 miembros, cicloalquilo C3-6, cicloheteroalquilo de 5-10 miembros, alquilo C1-18, alquenilo C2-18; o R5 y R6 tomados junto con el átomo de nitrogeno al cual están unidos pueden formar un anillo cicloheteroalquilo de 5-10 miembros; y n es 1 o 2; o sales farmacéuticas de los mismos, que comprende los pasos de: a) hacer reaccionar un fluoruro de sulfonilo de la formula (3): R3'SO2F, en donde R3' es como se define anteriormente en la presente para R3, con la condicion de que R3' no contiene un grupo que puede formar un anion bajo condiciones básicas; con un compuesto carbonilo de formula (4) en donde Z es H, OH, YNOX, o OR5, y X, Y, R1, R2, R5 y R6 son como se definen anteriormente; en presencia de un hidruro metálico o base amida en un solvente orgánico de éter, a temperaturas desde aproximadamente -78 degree C a aproximadamente temperatura ambiente, para producir un compuesto alfa-sulfonil carbonilo de formula (5), en donde Z, R1, R2 y R3' son como se definen anteriormente en la presente; y b) convertir el compuesto de formula (5) en un derivado de ácido hidroxámico; método para la preparacion de compuestos de formula (5), composiciones farmacéuticas y el uso de dichos derivados para la manufactura de un medicamento destinado como inhibidores de la enzima conversora de TNF-alfa (TACE) y metaloproteinasa de matriz (MMP), inhibidores de fosfodiesterasa, inhibidores de renina, antitromboticos e inhibidores de 5-lipoxigenasa, son preparador por los nuevos métodos de la presente.
ARP010100352A 2000-01-27 2001-01-26 Derivados del acido alfa-sulfonil hidroxamico, metodos para su preparacion, y para la preparacion de compuestos intermediarios, composiciones farmaceuticas, y, el uso de dichos derivados para la manufactura de un medicamento AR031550A1 (es)

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US49297500A 2000-01-27 2000-01-27

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EP (1) EP1252143A1 (es)
JP (1) JP2003520852A (es)
CN (1) CN1400968A (es)
AR (1) AR031550A1 (es)
AU (1) AU2001233034A1 (es)
BR (1) BR0107862A (es)
CA (1) CA2398561A1 (es)
MX (1) MXPA02007291A (es)
WO (1) WO2001055112A1 (es)

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EP1147085B1 (en) * 1999-01-27 2005-11-16 Wyeth Holdings Corporation Alkynyl containing hydroxamic acid derivatives, their preparation and their use as matrix metalloproteinase (mmp) inhibitors / tnf-alpha converting enzyme (tace) inhibitors
US6583299B1 (en) * 1999-05-20 2003-06-24 G.D. Searle & Co. α-amino-β-sulfonyl hydroxamic acid compounds

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EP1252143A1 (en) 2002-10-30
BR0107862A (pt) 2002-11-05
CN1400968A (zh) 2003-03-05
WO2001055112A1 (en) 2001-08-02

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