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AR035430A1 - Indanil aminas aciladas, un metodo para su sintesis, composiciones farmaceuticas que las comprenden y el uso de las mismas para la fabricacion de un medicamento - Google Patents

Indanil aminas aciladas, un metodo para su sintesis, composiciones farmaceuticas que las comprenden y el uso de las mismas para la fabricacion de un medicamento

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Publication number
AR035430A1
AR035430A1 ARP020100439A ARP020100439A AR035430A1 AR 035430 A1 AR035430 A1 AR 035430A1 AR P020100439 A ARP020100439 A AR P020100439A AR P020100439 A ARP020100439 A AR P020100439A AR 035430 A1 AR035430 A1 AR 035430A1
Authority
AR
Argentina
Prior art keywords
alkyl
group
phenyl
substituents
heteroaryl
Prior art date
Application number
ARP020100439A
Other languages
English (en)
Original Assignee
Aventis Pharma Gmbh
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 Aventis Pharma Gmbh filed Critical Aventis Pharma Gmbh
Publication of AR035430A1 publication Critical patent/AR035430A1/es

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    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
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    • C07C233/67—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/74—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a ring other than a six-membered aromatic ring
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    • C07C233/76—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen atoms
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    • C07C237/38—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having the nitrogen atom of the carboxamide group bound to a carbon atom of a ring other than a six-membered aromatic ring
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    • C07C237/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
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Abstract

Una indanil amina acilada que comprende la fórmula general (1) en cualquiera de sus formas estereoisómeras, o una de sus mezclas en cualquier proporción, o una de sus sales farmacéuticamente aceptables, en la que: R1 y R4 se seleccionan, independientemente uno de otro, del grupo formado por: H, alquilo C1-10, alquenilo C2-10 y alquinilo C2-10 no sustituidos y al menos monosustituidos, cuyos sustituyentes se seleccionan del grupo formado por F, OH, alcoxi C1-8, alquil C1-8 mercapto, CN, COOR6, CONR7R8 y fenilo y heteroarilo no sustituidos y al menos monosustituidos, cuyos sustituyentes se seleccionan del grupo formado por halógenos, pseudohalógenos, alquilo C1-3, alcoxi C1-3 y CF3; fenilo y heteroarilo no sustituidos y al menos monosustituidos, cuyos sustituyentes se seleccionan del grupo formado por halógenos, pseudohalógenos, alquilo C1-3, alcoxi C1-3 y CF3; R9CO, CONR10R11, COOR12, CF3, halógenos, pseudohalógenos, NR13R14, OR15, S(O)mR16, SO2NR17R18 y NO2; R2 y R3 se seleccionan, independientemente uno de otro, a partir del grupo formado por: H, halógenos, pseudohalógenos, alquilo C1-10 no sustituido y al menos monosustituido, cuyos sustituyentes se seleccionan del grupo formado por OH, fenilo y heteroarilo, OH, alcoxi C1-10, fenoxi, S(O)mR19, CF3, CN, NO2, alquil C1-10 amino, di-alquil C1-10 amino, alquil C1-6-CONH-, fenil-CONH- y fenil-SO2-O- no sustituidos y al menos monosustituidos, cuyos sustituyentes se seleccionan del grupo formado por halógenos, pseudohalógenos, CH3 y metoxi, alquil C1-6 SO2-O-, alquil C1-6 CO no sustituido y al menos monosustituido, cuyos sustituyentes se seleccionan del grupo formado por F, di-alquil C1-3 amino, pirrolidinilo y piperidinilo, y fenil-CO, cuya parte fenilo puede estar sustituida por uno o más sustituyentes del grupo formado por alquilo C1-3, halógenos y metoxi; A se selecciona del grupo formado por CH2, CHOH y CH-(alquilo C1-3); B se selecciona del grupo formado por CH2 y CH-(alquilo C1-3); R5 es un grupo Ar o un grupo Hetar, ambos de los cuales pueden ser no sustituidos o llevar uno o más sustituyentes seleccionados del grupo formado por halógenos, pseudohalógenos, NH2, alquilo C1-10, alquenilo C2-10, alquinilo C2-10, alcoxi C1-10, alquil C1-10 amino y di-alquil C1-10 amino no sustituidos y al menos monosustituidos, cuyos sustituyentes se seleccionan del grupo formado por F, OH, alcoxi C1-8, ariloxi, alquil C1-8 mercapto, NH2, alquil C1-8 amino y di-alquil C1-8 amino, alcanodiilo C3-5, fenilo, heteroarilo, alquilo C1-4 sustituido con arilo o heteroarilo, CF3, NO2, OH, fenoxi, bencil-oxi, alquil C1-10COO, S(O)mR20, SH, fenilamino, bencilamino, alquil C1-10-CONH, alquil C1-10-CON-alquilo C1-4, fenil-CONH-, fenil-CON-alquilo C1-4, heteroaril-CONH-, heteroaril-CON-alquilo C1-4-, alquil C1-10-CO, fenil-CO, heteroaril-CO, CF3-CO, -OCH2O-, -OCF2O-, -OCH2CH2O-; -CH2CH2O-; COOR21, CONR22R23, CONH(NH2), SO2NR24R25, R26SO2NH-, R27SO2N-alquilo C1-6, y heterociclos de 5 a 7 miembros mononucleares, alifáticos, saturados y al menos monoinsaturados, que contienen 1 a 3 heteroátomos seleccionados del grupo formado por N, O y S, heterociclos que pueden estar sustituidos con uno o más sustituyentes seleccionados del grupo formado por halógenos, alquilo C1-3, alcoxi C1-3, OH, oxo y CF3, donde dichos heterociclos pueden estar opcionalmente condensados con dicho grupo Ar o dicho grupo Hetar, donde todos los grupos arilo, heteroarilo, fenilo, que contienen arilo, que contienen heteroarilo y que contienen fenilo, que están presentes opcionalmente en dichos sustituyentes de dicho grupo Ar o dicho grupo Hetar, pueden estar sustituidos con uno o más sustituyentes seleccionados del grupo formado por halógenos, pseudohalógenos, alquilo C1-3, OH, alcoxi C1-3 y CF3; R6 se selecciona del grupo formado por: H, alquilo C1-10, que puede estar sustituido con uno o más sustituyentes seleccionados del grupo formado por F, alcoxi C1-8 y di-alquil C1-8 amino, aril-alquilo C1-4 y heteroaril-alquilo C1-4, que pueden estar sustituidos con uno o más sustituyentes seleccionados del grupo formado por halógenos, alcoxi C1-4 y di-alquil C1-6 amino; R7 se selecciona del grupo formado por: H, alquilo C1-10 que puede estar sustituido con uno o más sustituyentes seleccionados del grupo formado por F, alcoxi C1-8 y di-alquil C1-8 amino y fenilo; fenilo; indanilo y heteroarilo; y donde cada uno de los grupos aromáticos mencionado anteriormente puede ser no sustituido o llevar uno o más sustituyentes del grupo formado por halógenos, pseudohalógenos, alquilo C1-3, alcoxi C1-3 y CF3; R8 es H o alquilo C1-10; R9 se selecciona del grupo formado por: alquilo C1-10 que puede ser no sustituido o llevar uno o más sustituyentes del grupo formado por: F, alcoxi C1-4, di-alquil C1-3 amino, y fenilo y heteroarilo no sustituidos y al menos monosustituidos, cuyos sustituyentes se seleccionan del grupo formado por alquilo C1-3, alcoxi C1-3, halógenos, pseudohalógenos y CF3; R10, independientemente, tiene el mismo significado que R7; R11, independientemente, tiene el mismo significado que R8; R12, independientemente, tiene el mismo significado que R6; R13 se selecciona del grupo formado por: H, alquilo C1-6, fenilo, bencilo, heteroarilo, alquil C1-6-CO, fenil-CO y heteroaril-CO no sustituidos y sustituidos, cuyos sustituyentes se seleccionan del grupo formado por halógenos, pseudohalógenos, alquilo C1-3, alcoxi C1-3 y CF3 y donde puede estar presentes uno o más de estos sustituyentes; R14, independientemente, tiene el mismo significado que R13; R15 se selecciona del grupo formado por: h, alquilo C1-10, alcoxi C1-3-alquilo C1-3 y bencilo, fenilo y heteroarilo sustituidos y no sustituidos, cuyos sustituyentes se seleccionan del grupo formado por halógenos, pseudohalógenos, alquilo C1-3, alcoxi C1-3 y CF3, y donde pueden estar presentes uno o más de estos sustituyentes; R16 se selecciona del grupo formado por: alquilo C1-10 que puede estar sustituido con uno o más sustituyentes seleccionados del grupo formado por F, OH, alcoxi C1-8, ariloxi, alquil C1-8 mercapto, alquil C1-8 amino y di-alquil C1-8 amino, CF3 y fenilo y heteroarilo sustituido y no sustituido, cuyos sustituyentes se seleccionan del grupo formado por halógenos, pseudohalógenos, alquilo C1-3, alcoxi C1-3 y CF3, y donde puede estar presentes uno o más de estos sustituyentes; R17, independientemente, tiene el mismo significado que R7; R18, independientemente, tiene el mismo significado que R8; R19, independientemente, tiene el mismo significado que R16; R20, independientemente, tiene el mismo significado que R16; R21, independientemente, tiene el mismo significado que R6; R22, independientemente, tiene el mismo significado que R7; R23, independientemente, tiene el mismo significado que R8¸ R24, independientemente, tiene el mismo significado que R7; R25, independientemente, tiene el mismo significado que R8; R26, independientemente, tiene el mismo significado que R16; R27, independientemente, tiene el mismo significado que R16; heteroarilo es un heterociclo mono- o bicíclico, aromático de 5 a 10 miembros, que contiene uno o más heteroátomos seleccionados del grupo formado por N, O y S; el grupo Hetar es un heterociclo mono- o bicíclico, aromático, de 5 a 10 miembros, que contiene uno o más heteroátomos seleccionados del grupo formado por N, O y S, arilo es fenilo, naft-1-ilo o naft-2-ilo; el grupo Ar es fenilo, naft-1-ilo o naft-2-ilo; m es 0, 1 o 2; con la condiciones de que, en caso de que R1, R2, R3 y R4 sean todos H, R5 no es fenilo no sustituido, piridilo no sustituido, fenilo monosustituido con halógeno, 5-cloro-2-etoxifenilo, 5-cloro-2-metoxifenilo, 5-bromo-2-metoxifenilo, o quinoxalin-2-ilo; en caso de que R5 sea fenilo, A no es CHOH, R1 no es metoxi o metilo; R2 no es metilo o B no es CH-CH3; y en caso de que R2 sea NO2, R5 no es 3-clorofenilo. Un método para su síntesis, composiciones farmacéuticas que las comprenden y el uso de dichos compuestos indanil aminas aciladas para la fabricación de medicamentos para el tratamiento de enfermedades cardiovasculares, angina de pecho estable e inestable, cardiopatía coronaria, angina de Prinzmetal, síndrome agudo de las coronarias, insuficiencia cardíaca, infarto de miocardio, ataque de apoplejía, trombosis, enfermedad oclusiva de las arterias periféricas, disfunción endotelial, arteriosclerosis, restenosis, danos endotelial después de PTCA, hipertensión esencial, hipertensión pulmonar, hipertensión secundaria, hipertensión renovascular, glomerulonefritis crónica, disfunción eréctil, arritmia ventricular, diabetes, complicaciones de la diabetes, nefropatía, retinopatía, angiogénesis, asma bronquial, insuficiencia renal crónica, cirrosis hepática, osteoporosis, o funcionamiento limitado de la memoria o capacidad de aprendizaje limitada, o disminución del riesgo cardiovascular de las mujeres menopáusicas o después de ingerir contraceptivos.
ARP020100439A 2001-02-13 2002-02-11 Indanil aminas aciladas, un metodo para su sintesis, composiciones farmaceuticas que las comprenden y el uso de las mismas para la fabricacion de un medicamento AR035430A1 (es)

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