AR061458A1 - Derivados de aril y heteroaril-etil-acilguanidina, su preparacion y su aplicacion en terapeutica - Google Patents

Derivados de aril y heteroaril-etil-acilguanidina, su preparacion y su aplicacion en terapeutica

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Publication number
AR061458A1
AR061458A1 ARP070102606A ARP070102606A AR061458A1 AR 061458 A1 AR061458 A1 AR 061458A1 AR P070102606 A ARP070102606 A AR P070102606A AR P070102606 A ARP070102606 A AR P070102606A AR 061458 A1 AR061458 A1 AR 061458A1
Authority
AR
Argentina
Prior art keywords
alkyl
group
groups
alk
cycloalkyl
Prior art date
Application number
ARP070102606A
Other languages
English (en)
Inventor
Henning Steinhagen
Berangere Thiers
Jozsef Zsolt Bocskei
Gary Mccort
Hans Matter
Original Assignee
Sanofi Aventis
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 Sanofi Aventis filed Critical Sanofi Aventis
Publication of AR061458A1 publication Critical patent/AR061458A1/es

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/20—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
    • C07C279/22—Y being a hydrogen or a carbon atom, e.g. benzoylguanidines
    • 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
    • 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
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
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    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/08—Vasodilators for multiple indications
    • A—HUMAN NECESSITIES
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    • 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
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—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
    • C07D207/04—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 no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—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 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
    • C07D207/14—Nitrogen atoms not forming part of a nitro radical
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
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    • 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
    • C07D211/44—Oxygen atoms attached in position 4
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    • 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
    • C07D211/56—Nitrogen atoms
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    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
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    • C07D211/68—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 one double bond between ring members or between a ring member and a non-ring member
    • C07D211/72—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 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, directly attached to ring carbon atoms
    • C07D211/74—Oxygen atoms
    • C07D211/76—Oxygen atoms attached in position 2 or 6
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    • 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
    • C07D211/80—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 two double bonds between ring members or between ring members and non-ring members
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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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
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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
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    • 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
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    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
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    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
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    • C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
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    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
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    • C07D313/06—Seven-membered rings condensed with carbocyclic rings or ring systems
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    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/60—Radicals substituted by 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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    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
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    • 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

Abstract

Procedimientos para su preparacion, su uso en terapéutica y preparaciones farmacéuticas que lo comprenden. Reivindicacion 1: Un compuesto correspondiente a la formula general (1): en la que: - A representa un anillo seleccionado entre un grupo fenilo, un grupo heteroarilo o un grupo cicloalquilo (C4-8), - Q representa un átomo de oxígeno o un enlace -CH2- , -X, Y y Z representan átomos de carbono o nitrogeno, entendiéndose que bien X, Y, Z representan átomos de carbono, uno de X, Y y Z representa un átomo de nitrogeno (produciendo un anillo piridinilo), X y Z, o Y y Z, representan átomos de nitrogeno (produciendo anillos pirazinilo o piridazinilo, respectivamente), R1 y R2, idénticos o diferentes, se seleccionan entre los siguientes átomos y grupos: hidrogeno, halogeno, hidroxilo, ciano, oxo, -CF3, alquilo C1-6), Alk, alcoxi (C1-6), alquil (C1- 6)-O-alquilo (C1-6), -O-alquil (C1-6)-O-alquilo (C1-6), cicloalquilo (C3-8), -O-cicloalquilo (C3-8), -(CH2)m-SO2-alquilo (C1- 6) con m igual a 0, 1 o 2, bencilo, pirazolilo, -CH2-triazolilo opcionalmente sustituido con uno a tres grupos alquilo (C1- 6) y -L-R12, donde L representa un enlace o un ligamento -CH2- y/o -CO- y/o -SO2-, y R12 representa un grupo cicloalquilo (C3- 8) o un grupo de formula del grupo (2) en la que: - n = 0 o 1, -R13 representa uno a tres grupos, idénticos o diferentes, seleccionados entre átomos de hidrogeno y halogeno e hidroxilo, alquilo (C1-4), grupos oxo y fenilo, - R14 representa un átomo de hidrogeno o se selecciona entre los grupos -NR18R19, -NR18-Alk-R20 y -R21, donde R18, R19, R20, R21 y Alk son tal como se define a continuacion, o R13 y R14 juntos forman, con el mismo átomo de carbono al que están unidos, un grupo cicloalquilo (C3-8), que está por lo tanto presente en la posicion espiro en el anillo de formula (c), - R14' representa un grupo -CO-alquilo (C1-6), - R15 se selecciona entre los grupos -NR18R19, -Alk, -R20, -Alk-R20, -Alk-R21, -CO-Alk, -CO-R20, -CO-R21, -Alk- CO-NR18R19, cicloalquilo (C3-8) y -CO-cicloalquilo (C3-8), donde R18, R19, R20, R21 y Alk son como se define a continuacion, - R16 representa un átomo de hidrogeno o un grupo Alk, donde Alk es tal como se define a continuacion, - R17 representa un grupo -Alk, -Alk-R20 o -Alk-R21, donde Alk, R20 y R21 son tal como se define a continuacion, grupos -CO-alquilo (C1-6), -CO-cicloalquilo (C3-8), -CO-heterocicloalquilo, - R18 y R19, idénticos o diferentes, representan un átomo de hidrogeno o un grupo alquilo (C1-6), - R20 representa un grupo fenilo o heteroarilo (como un grupo piridinilo, pirazolilo, pirimidinilo o bencimidazolilo), que está opcionalmente sustituido con uno o más átomos de halogeno o grupos alquilo (C1-6), hidroxilo o alcoxi (C1-4), - R21 representa un grupo heterocicloalquilo opcionalmente sustituido con uno o más átomos de halogeno o grupos alquilo (C1-6), hidroxilo o alcoxi (C1-4), y - Alk representa un grupo alquilo (C1-6) que es lineal o ramificado y que está opcionalmente sustituido con uno a tres grupos, idénticos o diferentes, seleccionados entre los átomos de halogeno y los grupos hidroxilo, fenilo, alcoxi (C1-4) y -NR18R19, donde R18 y R19 son tal como se definio anteriormente, - R3 representa un grupo alquilo (C1-10) lineal que está opcionalmente sustituido con uno a tres grupos, idénticos o diferentes, seleccionado entre átomos de halogeno y grupos alcoxi (C1-4), - R4 representa un átomo de hidrogeno o halogeno o un grupo hidroxilo, ciano, alquilo (C1-6) o alcoxi (C1-6), - R5 y R6 representan, independientemente uno del otro, un átomo de hidrogeno o halogeno o un grupo alquilo (C1-5), o R5 y R6 juntos forman, con el átomo de carbono al que están unidos, un grupo cicloalquilo (C3-6), - R7 y R8 representan, independientemente uno del otro, un átomo de hidrogeno o un grupo alquilo (C1-5), o R7 y R8 juntos forman, con el átomo de carbonmo al que están unidos, un grupo cicloalquilo (C3-6), - R9 y R10 representan, independientemente uno del otro, un átomo de hidrogeno o un grupo hidroxilo, -CO-alquilo (C1-6) o -COO-alquilo (C1- 6), o R9 y R10 juntos forman una cadena alquileno (C2-3) lineal, formando así un anillo de 5 o 6 miembros con los átomos de nitrogeno a los que están unidos, estando dicha cadena de alquileno opcionalmente sustituida con uno a tres grupos seleccionados entre: grupos alquilo (C1-4), cicloalquilo (C3-6) en la posicion espiro, grupos oxo, hidroxilo y amino, -R11 representa un átomo de hidrogeno o un grupo alquilo (C1-8) o cicloalquilo (C3-6), que está opcionalmente sustituido con uno a tres grupos seleccionados entre: átomos de halogeno, grupos hidroxilo, ciano, alcoxi (C1-6), -NR18R19, -COOR18, -CO-NR18R19 o piridinilo, donde R18 y R19 son tal como se definio anteriormente; en la forma de una base libre o de una sal de adicion con un ácido o base, como también en la forma de un hidrato o de un solvato.
ARP070102606A 2006-06-15 2007-06-14 Derivados de aril y heteroaril-etil-acilguanidina, su preparacion y su aplicacion en terapeutica AR061458A1 (es)

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