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AR075599A1 - Amidas derivadas de acidos heterociclicos, medicamentos que las contienen y uso de las mismas para el tratamiento agudo y preventivo de distintos tipos de dolores. - Google Patents

Amidas derivadas de acidos heterociclicos, medicamentos que las contienen y uso de las mismas para el tratamiento agudo y preventivo de distintos tipos de dolores.

Info

Publication number
AR075599A1
AR075599A1 ARP100100537A ARP100100537A AR075599A1 AR 075599 A1 AR075599 A1 AR 075599A1 AR P100100537 A ARP100100537 A AR P100100537A AR P100100537 A ARP100100537 A AR P100100537A AR 075599 A1 AR075599 A1 AR 075599A1
Authority
AR
Argentina
Prior art keywords
alkyl
group
substituted
fluorine atoms
cycloalkyl
Prior art date
Application number
ARP100100537A
Other languages
English (en)
Inventor
Norbert Hauel
Angelo Ceci
Rainer Walter
Henri Doods
Juergen Mack
Ingo Konetzki
Henning Priepke
Annette Schuler-Metz
Dieter Wiedenmayer
Original Assignee
Boehringer Ingelheim Int
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 Boehringer Ingelheim Int filed Critical Boehringer Ingelheim Int
Publication of AR075599A1 publication Critical patent/AR075599A1/es

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/24—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 ring other than a six-membered aromatic ring of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
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    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/273—2-Pyrrolidones 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 other ring carbon atoms
    • C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
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    • 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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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
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    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
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    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
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Abstract

Reivindicacion 1: Compuestos caracterizados porque tienen la formula general 1 en la cual significan n uno de los numeros 0, 1 o 2 y R1 (a) un grupo alquilo C1-6 eventualmente sustituido con un radical R1.1, (b) un grupo alquilo C1-3, en el que cada grupo metileno puede estar sustituido con 1 o 2 átomos de fluor y cada grupo metilo puede estar sustituido con 1, 2 o 3 átomos de fluor, (c) un grupo cicloalquilo C3-6, eventualmente sustituido con un radical R1.2, en el que una unidad -CH2 puede estar reemplazada por un grupo -C(O), (d) un grupo aril-alquileno C0-2, eventualmente sustituido con 1, 2 o 3 radicales R1.3; (e) un radical heteroaril-alquileno C0-2 de cinco miembros, eventualmente sustituido con 1, 2 o 3 radicales R1.4, que al menos contiene un átomo de N, O o S y que eventualmente contiene además uno, dos o tres otros átomos de N y que además puede estar benzocondensado, (f) un radical heteroaril-alquileno C0-2 de seis miembros, eventualmente sustituido con 1 o 2 radicales R1.4, que contiene uno, dos o tres átomos de N y que, adicionalmente, puede estar benzocondensado, (g) un radical heteroarilo de nueve o diez miembros, eventualmente sustituido con 1 o 2 radicales R1.4, que contiene uno, dos o tres átomos de N, (h) un heterociclo de 5 o 6 miembros, eventualmente sustituido con 1 o 2 radicales R1.4, en el que una unidad -CH2 puede estar reemplazada por un grupo -C(O), (i) -O-R1.1.1, (j) -NR1.1.3R1.1.4 o (k) -C(=NR1.5)-CN, R1.1 halogeno, -NO2, -CN, cicloalquilo C3-6, -OR1.1.1, -SR1.1.1, -C(O)R1.1.1, -S(O)2-R1.1.2, -O-S(O)2-R1.1.1, -CO2R1.1.1, -O-C(O)-R1.1.1, -NR1.1.3R1.1.4, -NR1.1.3-C(O)-R1.1.1, -NR1.1.3-C(O)-R1.1.1, -NR1.1.3-CO2-R1.1.1 o -C(O)-NR1.1.3R1.1.4, R1.1.1 (a) H, (b) alquilo C1-4, (c) un grupo alquilo C1-3, en el que cada grupo metileno puede estar sustituido con 1 o 2 átomos de fluor y cada grupo metilo puede estar sustituido con 1, 2 o 3 átomos de fluor, (d) un grupo fenilo, eventualmente sustituido con 1, 2 o 3 radicales R1.1.1.1, (e) cicloalquilo C3-6 o (f) un grupo piridilo, eventualmente sustituido con 1, 2 o 3 radicales R1.1.1.2, R1.1.1.1, de modo independiente entre sí, (a) halogeno, -NO2, -CN, -OH, -O-alquilo C1-4, cicloalquilo C3-6, alquilo C1-4 o (b) un grupo alquilo C1-3, en el que cada grupo metileno puede estar sustituido con 1 o 2 átomos de fluor y cada grupo metilo puede estar sustituido con 1, 2 o 3 átomos de fluor, R1.1.1.2, de modo independiente entre sí, halogeno o alquilo C1-4, R.1.12 (a) alquilo C1-4, (b) un grupo alquilo C1-3, en el que cada grupo metileno puede estar sustituido con 1 o 2 átomos de fluor y cada grupo metilo puede estar sustituido con 1, 2 o 3 átomos de fluor, (c) -O-alquilo C1-4 o (d) un grupo fenilo, eventualmente sustituido con 1, 2 o 3 radicales R1.1.1.1, R1.1.3, R1.1.4, de modo independiente entre sí, (a) H, (b) un grupo alquilo C1-4, eventualmente sustituido con 1, 2 o 3 radicales R1.1.4.1, (c) un grupo fenilo, eventualmente sustituido con 1, 2 o 3 radicales R1.1.1.1, (d) cicloalquilo C3-6 o R1.1.3 y R1.1.4 , junto con el átomo de N al que están unidos, forman un anillo heterocíclico de 5 o 6 miembros que puede contener adicionalmente otro heteroátomo seleccionado de N, O y S, o R1.1.3 y R1.1.4, junto con el átomo de N al que están unidos, forman una imida cíclica, R1.1.4.1, de modo independiente entre sí, halogeno, -NH2, -NH(alquilo C1-4), -N(alquilo C1-4)2 o -SO2-R1.1.2, R1.2 halogeno, -NO2, -CN, OH, -O-CH3 o fenilo, R1.3 (a) halogeno, -NO2, -CN, -OR1.1.1, -SR1.1.1, -CO2R1.1.1, alquilo C1-6 o (b) un grupo alquilo C1-3, en el que cada grupo metileno puede estar sustituido con 1 o 2 átomos de fluor y cada grupo metilo puede estar sustituido con 1, 2 o 3 átomos de fluor, R1.4, de modo independiente entre sí, (a) halogeno, -NO2, -CN, -OR1.1.1, -SR1.1.1, -S(O)-R1.1.2, -S(O)2-R1.1.2, -NR1.1.3R1.1.4, -N(R1.4.1)-C(O)-alquilo C1-4, alquilo C1-6, (b) un grupo alquilo C1-3, en el que cada grupo metileno puede estar sustituido con 1 o 2 átomos de fluor y cada grupo metilo puede estar sustituido con 1, 2 o 3 átomos de fluor, o (c) un grupo oxo, R1.4.1 H o alquilo C1-4, R1.5 -OH u-O-alquilo C1-3-, R2 (a) H, (b) alquilo C1-4, (c) alquil C1-4-C(O)-, R3 y R4, junto con el átomo de carbono al que están unidos, un grupo cicloalquileno C3-6, eventualmente sustituido con un radical R3.1, en el que una unidad -CH2 puede estar reemplazada por un heteroátomo O, N, S o por un grupo CO, SO o SO2, R3.1 H,-OH, R5 (a) H, (b) alquilo C1-4, (c) un grupo alquilo C1-3, en el que cada grupo metileno puede estar sustituido con 1 o 2 átomos de fluor y cada grupo metilo puede estar sustituido con 1, 2 o 3 átomos de fluor, R6, independientemente uno de otro, (a) H, halogeno, -CN, -OH, alquilo C1-6, cicloalquilo C3-7, -O-alquilo C1-4, -O-CF3, -O-cicloalquilo C3-6, -N(alquilo C1-3)2, -C(O)-NH2, -(SO2)NH2, -SO2-alquilo C1-3, o (b) un grupo alquilo C1-3, en el que cada grupo metileno puede estar sustituido con 1 o 2 átomos de fluor y cada grupo metilo puede estar sustituido con 1, 2 o 3 átomos de fluor, R7 (a) H, halogeno, -CN, -OH, (b) alquilo C1-6, (c) alquilo C1-3 u -O-alquilo C1-3, en el que cada grupo metileno puede estar sustituido con 1 o 2 átomos de fluor y cada grupo metilo puede estar sustituido con 1, 2 o 3 átomos de fluor, (d) cicloalquilo C3-7, (e) -O-alquilo C1-6, (f) -O-cicloalquilo C3-7, (g) -NH2, -NH(alquilo C1-3), -N(alquilo C1-3)2, (h) -C(O)-R7.1, (i) -S-alquilo C1-4, -SO2-R7.2, (j) un grupo heteroarilo de cinco miembros, eventualmente sustituido con uno o dos grupos alquilo C1-3, que está seleccionado del grupo compuesto por pirrolilo, oxazolilo, isoxazolilo, oxadiazolilo, tiazolilo, isotiazolilo, tiadiazolilo, imidazolilo, pirazolilo, triazolilo y tetrazolilo o (k) un grupo heteroarilo de seis miembros, eventualmente sustituido con uno o dos grupos alquilo C1-3, que está seleccionado del grupo compuesto por piridilo, pirimidinilo, pirazinilo, piridazinilo y triazinilo, R7.1 -NH2, -NH(alquilo C1-6), -N(aIquilo C1-6)2, N-acetidinilo, N-pirrolidinilo, N-piperidinilo, N-morfolinilo, -OH, -O-alquilo C1-8 u -O-cicloalquilo C3-7, R7.2 -NH2, -NH(alquilo C1-6), -N(alquilo C1-6)2, N-acetidinilo, N-pirrolidinilo, N-piperidinilo o N-morfolinilo y R8 H, halogeno, alquilo C1-4, R9 (a) H, halogeno, -CN, -OH, (b) alquilo C1-6, (c) alquilo C1-3 u -O-alquilo C1-3, en el que cada grupo metileno puede estar sustituido con 1 o 2 átomos de fluor y cada grupo metilo puede estar sustituido con 1, 2 o 3 átomos de fluor, (d) cicloalquilo C3-7, (e) alquinilo C2-4, (f) -O-alquilo C1-6, (g) -O-cicloalquilo C3-7, (h) -NH2, -NH(alquilo C1-3), -N(alquilo C1-3)2, (i) -C(O)-R9.1, (j) -S-alquilo C1-4, -SO-alquilo C1-4, -SO2-alquilo C1-4, R9.1 -NH2, -NH(alquilo C1-6), -N(alquilo C1-6)2, N-acetidinilo, N-pirrolidinilo, N-piperidinilo, N-morfolinilo, -OH, -O-alquilo C1-8 u -O-cicloalquilo C3-7, R10 H, halogeno, alquilo C1-4, R11 (a) H, halogeno, -CN, -OH, (b) alquilo C1-6, (c) alquilo C1-3 u -O-alquilo C1-3, en el que cada grupo metileno puede estar sustituido con 1 o 2 átomos de fluor y cada grupo metilo puede estar sustituido con 1, 2 o 3 átomos de fluor, (d) cicloalquilo C3-7, (e) -O-alquilo C1-6, (f) -O-cicloalquilo C3-7, (g) -NH2, -NH(alquilo C1-3), -N(alquilo C1-3)2, (h) -C(O)-R11.1, (i) -S-alquilo C1-3, -SO2-R11.2, (j) un grupo heteroarilo de cinco miembros, eventualmente sustituido con uno o dos grupos alquilo C13, que está seleccionado del grupo compuesto por pirrolilo, oxazolilo, isoxazolilo, oxadiazolilo, tiazolilo, isotiazolilo, tiadiazolilo, imidazolilo, pirazolilo, triazolilo y tetrazolilo o (k) un grupo heteroarilo de seis miembros, eventualmente sustituido con uno o dos grupos alquilo C1-3, que está seleccionado del grupo compuesto por piridilo, pirimidinilo, pirazinilo, piridazinilo y triazinilo, R11.1 -NH2, -NH(alquilo C1-6), -N(alquilo C1-6)2, N-acetidinilo, N-pirrolidinilo, N-piperidinilo, N-morfolinilo, -OH, -O-alquilo C1-8 u -O-cicloalquilo C3-7, R11.2 -NH2, -NH(alquilo C1-6),-N(alquilo C1-6)2, N-acetidinilo, N-pirrolidinilo, N-piperidinilo o N-morfolinilo y X, independientemente uno de otro, C-R6 o N, sus enantiomeros, sus diastereoisomeros, sus mezclas y sus sales.
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