BR0011522A - Composto e método de sintetização para a fabricação do composto - Google Patents

Composto e método de sintetização para a fabricação do composto

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Publication number
BR0011522A
BR0011522A BR0011522-3A BR0011522A BR0011522A BR 0011522 A BR0011522 A BR 0011522A BR 0011522 A BR0011522 A BR 0011522A BR 0011522 A BR0011522 A BR 0011522A
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compound
manufacture
synthesis method
produg
interleukin
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BR0011522-3A
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Michael Palladino
Emmanuel A Theodorakis
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Nereus Pharmaceuticals Inc
Univ California
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Publication of BR0011522A publication Critical patent/BR0011522A/pt

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    • 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
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Abstract

"COMPOSTO E MéTODO DE SINTETIZAçãO PARA A FABRICAçãO DO COMPOSTO". A presente, e invenção se refere a novos compostos os quais têm a estrutura química de Formula (II), e seus ésteres pró-droga e sais por adição de ácido, e que são úteis como moduladores de Interleukin-1 e Tumor Necrosis Factor-<sym>, e desta forma são úteis no tratamento de diversas doenças. Na fórmula acima os grupos R são definidos como a seguir: se qualquer R~ 3~-R~ 5~, R~ 7~, R~ 8~, R~ 11~-R~ 13~ não é hidrogênio, R~ 2~ ou R~ 6~ ou R~ 9~ não é metila, ou R~ 10~ não é CH~ 2~, então R~ 1~ é selecionado a partir do grupo consistindo de hidrogênio, um halogênio, COOH, C~ 1~-C~ 12~ ácidos carboxílicos, C~ 1~-C~ 12~ haletos de acila, C~ 1~-C~ 12~ resíduos de acila, C~ 1~-C~ 12~ ésteres, C~ 1~-C~ 12~ amidas secundárias, (C~ 1~-C~ 12~) (C~ 1~-C~ 12~) amidas terciárias, C~ 1~-C~ 12~ álCooiS, (C~ 1~-C~ 12~) (C~ 1~-C~ 12~) éteres, C~ 1~-C~ 12~ alquilas, C~ 1~-C~ 12~ alquilas substituídas, C~ 2~-C~ 12~ alquenilas, C~ 2~-C~ 12~ alquenilas substituídas, e C~ 5~-C~ 12~ arilas. Se todos R~ 3~-R~ 5~, R~ 7~, R~ 8~, R~ 11~-R~ 13~ são hidrogênio, R~ 2~, R~ 6~, e R~ 9~ são cada um metila, e R~ 10~ é CH~ 2~, então R, é selecionado a partir de hidrogênio, um halogênio, C~ 1~-C~ 12~ ácidos carboxílicos, C~ 1~-C~ 12~ haletos de acila, C~ 1~-C~ 12~ resíduos de acila, C~ 2~-C~ 12~ ésteres, C~ 2~-C~ 12~ amidas secundárias, (C~ 1~-C~ 12~) (C~ 1~-C~ 12~) amidas terciárias, C~ 2~-C~ 12~ álcoois, (C~ 1~-C~ 12~) (C~ 1~-C~ 12~) éteres outros além de metila-acetila éter, C~ 2~-C~ 12~ alquilas, C~ 1~-C~ 12~ alquilas substituídas, C~ 2~-C~ 12~ alquenilas, C~ 2~-C~ 12~ alquenilas substituídas, e C~ 2~-C~ 12~ arilas. R~ 2~ e R~ 9~ são cada um separadamente selecionados a partir de hidrogênio, um halogênio, C~ 1~-C~ 12~ alquila, C~ 1~-C~ 12~ alquilas substituídas, C~ 2~-C~ 12~ alquenila, C~ 2~-C~ 12~ alquenila substituída, C~ 2~-C~ 12~ alquinila, C~ 1~-C~ 12~ acila, C~ 1~-C~ 12~ álcool, e C~ 5~-C~ 12~ arila. R~ 3~-R~ 5~, R~ 7~, R~ 8~, e R~ 11~-R~ 13~ são cada um separadamente selecionados a partir de hidrogênio, um halogênio, C~ 1~-C~ 12~ alquila, C~ 1~-C~ 12~ alquilas substituídas, C~ 2~-C~ 12~ alquenila, C~ 2~-C~ 12~ alquenila substituída, C~ 2~-C~ 12~ alquinila, e C~ 5~-C~ 12~ arila. R~ 6~ é selecionado a partir de hidrogênio, um halogênio, C~ 1~-C~ 12~ alquila, C~ 1~-C~ 12~ alquilas substituídas, C~ 2~-C~ 12~ alquenila, C~ 2~-C~ 12~ alquenila substituída, e C~ 2~-C~ 12~ alquinila. R~ 10~ é selecionado a partir de hidrogênio, um halogênio, CH~ 2~, C~ 1~-C~ 6~ alquila, C~ 1~-C~ 6~ alquila substituída, C~ 2~-C~ 6~ alquenila, C~ 2~-C~ 6~ alquenila substituída, C~ 1~-C~ 12~ álcool, e C~ 5~-C~ 12~ arila. Adicionalmente, a presente invenção se refere a novos compostos que têm a estrutura química de Formula (IIA) e seus ésteres pró-droga e sais por adição de ácido são revelados, e que são úteis como moduladores de Interleukin-1 e Tumor Necrosis Factor-<sym>, e desta forma são úteis no tratamento de diversas doenças. Na fórmula acima, os grupos R são definidos como a seguir: se qualquer R~ 3~-R~ 5~, R~ 7~, R~ 8~, R~ 11~-R~ 13~ não é hidrogênio, R~ 2~ ou R~ 6~ não é metila, R~ 10~ não é CH~ 2~, ou se não é verdade que R~ 10~ é CH~ 2~OH e R~ 11~ é OH, então R~ 1~ é selecionado a partir do grupo consistindo de hidrogênio, um halogênio, COOH, C~ 1~-C~ 12~ ácidos carboxílicos, C~ 1~-C~ 12~ haletos de acila, C~ 1~-C~ 12~ resíduos de acila, C~ 1~-C~ 12~ ésteres, C~ 1~-C~ 12~ amidas secundárias, (C~ 1~-C~ 12~) (C~ 1~-C~ 12~) amidas terciárias, C~ 1~-C~ 12~ álcoois, (C~ 1~-C~ 12~) (C~ 1~-C~ 12~) éteres, C~ 1~-C~ 12~ alquilas, C~ 1~-C~ 12~ alquilas substituídas, C~ 2~-C~ 12~ alquenilas, C~ 2~-C~ 12~ alquenilas substituídas. Entretanto, se todos R~ 3~-R~ 5~, R~ 7~, R~ 8~, R~ 11~-R~ 13~ são hidrogênio, R~ 2~ e R~ 6~ são cada um metila, e R~ 10~ é CH~ 2~ ou CH~ 2~OH, então R, é selecionado a partir de hidrogênio, um halogênio, C~ 1~-C~ 12~ ácidos carboxílicos, C~ 1~-C~ 12~ haletos de acila, C~ 1~-C~ 12~ resíduos de acila, C~ 2~-C~ 12~ ésteres, C~ 1~-C~ 12~ amidas secundárias, (C~ 1~-C~ 12~) (C~ 1~-C~ 12~) amidas terciárias, C~ 2~-C~ 12~ álcoois, (C~ 1~,-C~ 12~) (C~ 1~-C~ 12~) éteres, C~ 2~-C~ 12~ alquilas, C~ 2~-C~ 12~ alquilas substituídas, C~ 2~-C~ 12~ alquenila, e C~ 2~-C~ 12~ alquenila substituída. R~ 2~ é selecionado a partir de hidrogênio, um halogênio, C~ 1~-C~ 12~ alquila, C~ 1~-C~ 12~ alquilas substituídas, C~ 2~-C~ 12~ alquenila, C~ 2~-C~ 12~ alquenila substituída, C~ 2~-C~ 12~ alquinila, e C~ 1~-C~ 12~ acila, e C~ 5~-C~ 12~ arila. R~ 3~, R~ 4~, R~ 5~, R~ 7~, R~ 8~, e R~ 11~-R~ 13~ são cada um separadamente selecionados a partir de hidrogênio, um halogênio, C~ 1~-C~ 12~ alquila, C~ 1~-C~ 12~ alquilas substituídas, C~ 2~-C~ 12~ alquenila, C~ 2~-C~ 12~ alquenila substituída, C~ 2~-C~ 12~ alquinila, e C~ 5~-C~ 12~ arila. R~ 6~ é selecionado a partir de hidrogênio, um halogênio, C~ 1~-C~ 12~ alquila, C~ 1~-C~ 12~ alquilas substituídas, C~ 2~-C~ 12~ alquenila, C~ 2~-C~ 12~ alquenila substituída, e C~ 2~-C~ 12~ alquinila. R~ 10~ é selecionado a partir de hidrogenio, um halogênio, CH~ 2~, C~ 1~-C~ 6~ alquila, C~ 1~-C~ 6~ alquila substituída, C~ 2~-C~ 6~ alquenila, C~ 2~-C~ 6~ alquenila substituída, C~ 1~-C~ 12~ álcool, e C~ 5~-C~ 12~ arila. composições farmacêuticas compreendendo uma quantidade terapeuticamente efetiva de ácido acantóico ou dos compostos de Formula (II) e Formula (IIA), e a um suporte farmaceuticamente aceitável, são também revelados, e são úteis as analgésicos antiinflamatórios, no tratamento de desordens imunológicas, como agentes anti-câncer e anti-tumor, e no tratamento de doença cardiovascular, vermelhidão da pele, diabetes, rejeição quando de transplantes, otite do ouvido médio, sinusite, e infecção viral. Adicionalmente, a presente invenção se refere a novos compostos que têm a estrutura química de Formula (IIB) e seus ésteres pró-droga e sais por adição de ácido são revelados, e são úteis como moderadores de Interleukin-1 e Tumor Necrosis Factor-<sym>, e desta forma são úteis no tratamento de diversas doenças. Na fórmula acima, os grupos R incluem o seguinte: R~ 1~ é selecionado a partir do grupo consistindo de hidrogênio, um halogênio, COOH, C~ 1~-C~ 12~ ácidos carboxílicos, C~ 1~-C~ 12~ haletos de acila, C~ 1~-C~ 12~ resíduos de acila, C~ 1~-C~ 12~ ésteres, C~ 1~-C~ 12~ amidas secundárias, (C~ 1~-C~ 12~) (C~ 1~-C~ 12~) amidas terciárias, C~ 1~-C~ 12~ álcoois, (C~ 1~-C~ 12~) (C~ 1~-C~ 12~) éteres, C~ 1~-C~ 12~ alquilas, C~ 1~-C~ 12~ alquilas substituídas, C~ 2~-C~ 12~ alquenilas, C~ 2~-C~ 12~ alquenilas substituídas; R~ 2~ é selecionado a partir de hidrogênio, um halogênio, C~ 1~-C~ 12~ alquila, C~ 1~-C~ 12~ alquilas substituídas, C~ 2~-C~ 12~ alquenila, C~ 2~-C~ 12~ alquenila substituída, C~ 2~-C~ 12~ alquinila, e C~ 1~-C~ 12~ acila, e C~ 5~-C~ 12~ arila. R~ 3~, R~ 4~, R~ 5~, R~ 7~, R~ 8~, e R~ 11~-R~ 13~ são cada um separadamente selecionados a partir de hidrogênio, um halogênio, C~ 1~-C~ 12~ alquila, C~ 1~-C~ 12~ alquilas substituídas, C~ 2~-C~ 12~ alquenila, C~ 2~-C~ 12~ alquenila substituída, C~ 2~-C~ 12~ alquinila, e C~ 5~-C~ 12~ arila. R~ 5~ é selecionado a partir de hidrogênio, um halogênio, C~ 1~-C~ 12~ alquila, C~ 1~-C~ 12~ alquilas substituídas, C~ 2~-C~ 12~ alquenila, C~ 2~-C~ 12~ alquenila substituída, e C~ 2~-C~ 12~ alquinila. R~ 10~ é selecionado a partir de hidrogênio, um halogênio, CH~ 2~, C~ 1~-C~ 6~ alquila, C~ 1~-C~ 6~ alquila substituída, C~ 2~-C~ 6~ alquenila, C~ 2~-C~ 6~ alquenila substituída, C~ 1~-C~ 12~ álcool, e C~ 5~-C~ 12~ arila. Os compostos revelados incluem os ésteres pró-droga dos compostos acima, e os sais por adição de ácido dos mesmos. Composições farmacêuticas compreendendo uma quantidade terapeuticamente efetiva dos novos compostos das fórmulas (II) e (IIA), e seus ésteres pró-drogas, e a um suporte farmaceuticamente aceitável, são também revelados, e são úteis as analgésicos anti-inflamatórios, no tratamento de desordens imunológicas, como agentes anti-câncer e anti-tumor, e no tratamento de doença cardiovascular, vermelhidão da pele, e infecção viral. métodos completamente sintético e semi-sintético de fabricação dos compostos das fórmulas (I) e (II), e seus análogos, e os compostos das fórmulas (II), (IIA) e (IIB) são revelados, como também o são métodos para a utilização destes compostos sintético e semi-sintético no tratamento das condições de doença acima mencionadas.
BR0011522-3A 1999-05-14 2000-05-12 Composto e método de sintetização para a fabricação do composto BR0011522A (pt)

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US13429599P 1999-05-14 1999-05-14
US18685300P 2000-03-03 2000-03-03
PCT/US2000/013202 WO2000073253A1 (en) 1999-05-14 2000-05-12 NOVEL INTERLEUKIN-1 AND TUMOR NECROSIS FACTOR-α MODULATORS, SYNTHESES OF SAID MODULATORS AND METHODS OF USING SAID MODULATORS

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US6365768B1 (en) 2002-04-02
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AU5013300A (en) 2000-12-18
US7342125B2 (en) 2008-03-11
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