AR045368A1 - DERIVATIVES OF CYCLOPROPYL AS ANTAGONISTS OF THE NK3 RECEIVER - Google Patents

DERIVATIVES OF CYCLOPROPYL AS ANTAGONISTS OF THE NK3 RECEIVER

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AR045368A1
AR045368A1 ARP040102914A ARP040102914A AR045368A1 AR 045368 A1 AR045368 A1 AR 045368A1 AR P040102914 A ARP040102914 A AR P040102914A AR P040102914 A ARP040102914 A AR P040102914A AR 045368 A1 AR045368 A1 AR 045368A1
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alkyl
cycloalkyl
ilo
independently selected
amino
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Lundbeck & Co As H
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    • C—CHEMISTRY; METALLURGY
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    • 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
    • C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/10—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
    • C07D211/14—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
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    • 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
    • C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/30—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
    • C07D211/32—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen atoms
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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
    • C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/34—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon 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
    • 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
    • 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
    • C07D211/52—Oxygen atoms attached in position 4 having an aryl radical as the second substituent in position 4
    • 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
    • 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
    • C07D211/58—Nitrogen atoms attached in position 4
    • 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
    • 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
    • C07D211/64—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 an aryl radical as the second substituent in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/155—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—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
    • C07D401/02—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
    • C07D401/06—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 carbon chain containing only aliphatic carbon atoms
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/10—Spiro-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

La presente se relaciona con derivados de ciclopropilo y sal de los mismos. Estos compuestos son antagonistas del receptor NK3 y, por lo tanto, pueden ser de utilidad para el tratamiento de enfermedades en las que está implicado el receptor NK3, por ejemplo los trastornos psicóticos. Reivindicación 1: Un compuesto de la fórmula (1) o una sal del mismo, tal como una sal farmacéuticamente aceptable donde: R1-R5 son independientemente seleccionados del grupo formado por H, halógeno, ciano, nitro, alqu(en/in)ilo-C1-6, cicloalqu(en)ilo-C3-8, cicloalqu(en)il-C3-8-alqu(en/in)ilo-C1-6, amino, alqu(en/in)ilo-C1-6-amino, di(alqu(en/in)il-C1-6)amino, alqu(en/in)il-C1-6carbonilo, aminocarbonilo, alqu(en/in)il-C1-6aminocarbonilo, di(alqu(en/in)il-C1-6-aminocarbonilo,, hidroxi, alqu(en/in)iloxi C1-6, alqu(en/in)il-C1-6tio, halo-alqu(en/in)ilo-C1-6, halo-alqu(en/in)il-c1-6sulfonilo, halo-alqu(en/in)il-C1-6sulfanilo y alqu(en/in)il-C1-6sulfonilo; R6 es seleccionado entre H, halo-alqu(en/in)ilo-C1-6, alqu(en/in)ilo-C1-6, cicloalqu(en)ilo-C3-8 y cicloalqu(en)il-C3-8-alqu(en/in)ilo-C1-6; R7 es arilo o un heteroarilo, o bien R7 es un grupo aril-CR8R9-, donde R8 y R9 son independientemente seleccionados entre H, alqu(en/in)ilo-C1-6, cicloalqu(en)ilo-C3-8 y cicloalqu(en)il-C3-8-alqu(en/in)ilo-C1-6; n representa 0, 1 o 2; Q es seleccionado entre (i9-(vii), donde la flecha indica el punto de unión, donde R10 es un arilo; donde R11 es seleccionado entre arilo o un bencilo, halo-alqu(en/in)il-C1-6sulfonilo, alqu(en/in)il-c1-6sulfonilo, arilsulfonilo, arilacilo, alqu(en/in)il-C1-6carbonilo, aminocarbonilo, alqu(en/in)il-C1-6amionocarbonilo y di-alqu(en/in)il-C1-6aminocarbonilo; donde R12 es un arilo; donde R13 es H, hidroxi, ciano o amino, o uno de los siguientes grupos -NH-alqu(en/in)ilo-C1-6; -N(alqu(en/in)ilo-C1-6)2;-NR14COR15, donde R14 es H o alqu(en/in)ilo-C1-6 y R15 es alqu(en/in)ilo-C1-6 o cicloalqu(en)ilo-C3-8; -NR16COCONR17R18, donde R16 es H o alqu(en/in)ilo-C1-6 y R17 y r18 son independientemente seleccionados entre H y alqu(en/in)ilo-C1-6 y cicloalquilo-C3-8, o bien R17 y R18, junto con el N al cual están unidos, forman un piperidilo, piperazinilo o morfolinilo, donde dichos piperidilo, piperazinilo y morfolinilo están optativamente sustituidos con un alqu(en/in)ilo-C1-6, -NR19CONR20R21, donde R19 es H o alqu(en/in)-C1-6 y R20 y R21 son independientemente seleccionados entre H y alqu(en/in)-C1-6 o cicloalquilo-C3-8; o bien R20 y R21, junto con el N al cual están unidos, forman un piperidilo, piperazinilo o morfolinilo, donde dichos piperidilo, piperazinilo y morfolinilo están optativamente sustituidos con un alqu(en/in)ilo-C1-6; -NR22SO2R23, donde R22 es H o alqu(en/in)-C1-6 o cicloalquilo C3-8 y R23 es amino, alqu(en/in)ilo-C1-6 o cicloalquilo-C3-8; -COR24, donde R24 de alqu(en/in)ilo-C1-6 o cicloalquilo-C3-8; -CONR25R26, donde R25 y R26 son seleccionados independientemente entre H, alqu(en/in)ilo-C1-6 y cicloalquilo-C3-8, o bien R25 y R26 junto con el N al cual están unidos, forman un piperidilo, piperazinilo o morfolinilo, donde dichos piperidilo, piperazinilo y morfolinilo están optativamente sustituidos con un alquilo C1-6; -NHCOOR42, donde R42 es alqu(en/in)ilo-C1-6 o cicloalqu(en)ilo C3-8; donde X, Y y Z son seleccionados independientemente entre un enlace, O, NR27; CR28R29 y S(O)m, donde m es 0, 1 o 2; donde R27 es seleccionado entre H, alqu(en/in)ilo-C1-6, cicloalquilo-C3-8, cicloalquil-C3-8-alquilo C1-6, trifluormetilo, acilo, tioacilo y trifluormetilsulfonilo, o bien R27 es un grupo R30SO2-, R30OCO- o R30SCO-, donde R30 es alqu(en/in)ilo-C1-6, cicloalquilo-C3-8 o cicloalquil-C3-8-alquilo-C1-6, o R27 es un grupo R341R32NCO- o R31R32NCS-, en el cual R31 y R32 son independientemente seleccionados entre H, alqu(en/in)ilo-C1-6, cicloalquilo-C3-8, cicloalquil-C3-8-alquilo C1-6 y arilo, o donde R31 y R32, junto con el átomo de N al cual están ligados, forman un grupo pirrolidinilo, piperidinilo o perhidroazepinilo; donde R28 y R29 son independientemente seleccionados entre H, F, alqu(en/in)ilo-C1-6, cicloalquilo-C3-8 y cicloalquil-C3-8-alquilo C1-6; donde R33-R36 son independientemente seleccionados entre H, halógeno, ciano, nitro, alqu(en/in)ilo-C1-6, cicloalquilo-C3-8, cicloalquil-C3-8-alquilo, amino, alquilamino C1-6, di(alquil C1-6)amino, alquilcarbonilo C1-6,. Aminocarbonilo, alquilaminocarbonilo C1-6, di-(alquil C1-6)aminocarbonilo, alcoxi C1-6, alquiltio C1-6, hidroxi, trifluormetilo, trifluormetilsulfonilo y alquilsulfonilo C1-6, donde R37-R38 son ambos H o bien están fusionados entre sí en una cadena de etileno CH2-CH2-formando un aza-biciclo[3.2.1]octan-ilo; donde R39 -R41 son independientemente seleccionados del grupo formado por H y halógeno; siempre que no más de uno de X, Y y Z pueda ser un enlace, y con la condición de que dos grupos adyacentes X, Y o Z no pueden ser seleccionados al mismo tiempo entre O y S.This is related to cyclopropyl derivatives and salt thereof. These compounds are antagonists of the NK3 receptor and, therefore, may be useful for the treatment of diseases in which the NK3 receptor is involved, for example psychotic disorders. Claim 1: A compound of the formula (1) or a salt thereof, such as a pharmaceutically acceptable salt wherein: R1-R5 are independently selected from the group consisting of H, halogen, cyano, nitro, alkyl (en / in) yl -C1-6, cycloalkyl (en) ilo-C3-8, cycloalkyl (en) yl-C3-8-alkyl (en / in) ilo-C1-6, amino, alkyl (en / in) ilo-C1-6 -amino, di (alky (in / in) il-C1-6) amino, alky (en / in) yl-C1-6carbonyl, aminocarbonyl, alkyne (in / in) yl-C1-6aminocarbonyl, di (alky (en / in) il-C1-6-aminocarbonyl ,, hydroxy, alkyl (en / in) C1-6 yloxy, alkyl (en / in) il-C1-6thio, halo-alkyl (en / in) ilo-C1-6 , halo-alkyl (en / in) yl-C1-6sulfonyl, halo-alkyl (en / in) yl-C1-6sulfanyl and alkyl (en / in) yl-C1-6sulfonyl; R6 is selected from H, halo-alkyl (en / in) ilo-C1-6, alky (en / in) ilo-C1-6, cycloalk (en) ilo-C3-8 and cycloalkyl (en) il-C3-8-alky (en / in) ilo -C1-6; R7 is aryl or a heteroaryl, or R7 is an aryl-CR8R9- group, where R8 and R9 are independently selected from H, alkyl (en / in) ilo-C1-6, cycloalkyl (en) yl -C3-8 and cycloalkyl (en) il-C3-8-alkyl (en / in) yl-C1-6; n represents 0, 1 or 2; Q is selected from (i9- (vii), where the arrow indicates the point of attachment, where R10 is an aryl; where R11 is selected from aryl or a benzyl, halo-alkyl (en / in) il-C1-6sulfonyl, alky (en / in) yl-c1-6sulfonyl, arylsulfonyl, arylacyl, alkynes (in / in) yl-C1-6carbonyl, aminocarbonyl, alkynes (in / in) yl-C1-6amionocarbonyl and di-alkynes (in / in) il-C1-6 aminocarbonyl; where R12 is an aryl; where R13 is H, hydroxy, cyano or amino, or one of the following groups -NH-alkyl (en / in) yl-C1-6; -N (alkyl (en / in) ilo-C1-6) 2; -NR14COR15, where R14 is H or alkyl (en / in) ilo-C1-6 and R15 is alkyl (en / in) ilo-C1-6 or cycloalkyl (en) ilo -C3-8; -NR16COCONR17R18, where R16 is H or alkyl (in / in) ilo-C1-6 and R17 and r18 are independently selected from H and alkyl (in / in) ilo-C1-6 and cycloalkyl-C3- 8, or R17 and R18, together with the N to which they are attached, form a piperidyl, piperazinyl or morpholinyl, wherein said piperidyl, piperazinyl and morpholinyl are optionally substituted with an (en / in) ilo-C1-6 alkyl, - NR19CONR20R21, gift of R19 is H or alkyl (in / in) -C1-6 and R20 and R21 are independently selected from H and alkyl (in / in) -C1-6 or cycloalkyl-C3-8; or R20 and R21, together with the N to which they are attached, form a piperidyl, piperazinyl or morpholinyl, wherein said piperidyl, piperazinyl and morpholinyl are optionally substituted with a (en / in) yl-C1-6 alkyl; -NR22SO2R23, where R22 is H or alkyl (en / in) -C1-6 or C3-8 cycloalkyl and R23 is amino, alkyl (en / in) ilo-C1-6 or cycloalkyl-C3-8; -COR24, where R24 of alkyl (en / in) yl-C1-6 or cycloalkyl-C3-8; -CONR25R26, where R25 and R26 are independently selected from H, alkyl (in / in) ilo-C1-6 and cycloalkyl-C3-8, or R25 and R26 together with the N to which they are attached, form a piperidyl, piperazinyl or morpholinyl, wherein said piperidyl, piperazinyl and morpholinyl are optionally substituted with a C1-6 alkyl; -NHCOOR42, where R42 is alkyl (en / in) ilo-C1-6 or cycloalkyl (en) ilo C3-8; where X, Y and Z are independently selected from a link, O, NR27; CR28R29 and S (O) m, where m is 0, 1 or 2; where R27 is selected from H, alkyl (en / in) yl-C1-6, cycloalkyl-C3-8, cycloalkyl-C3-8-C1-6 alkyl, trifluoromethyl, acyl, thioacyl and trifluoromethylsulfonyl, or R27 is a group R30SO2-, R30OCO- or R30SCO-, where R30 is alkyl (en / in) ilo-C1-6, cycloalkyl-C3-8 or cycloalkyl-C3-8-alkyl-C1-6, or R27 is a group R341R32NCO- or R31R32NCS-, in which R31 and R32 are independently selected from H, alkyl (en / in) C1-6 yl, C3-8 cycloalkyl, C3-8 cycloalkyl- C1-6 alkyl and aryl, or where R31 and R32, together with the N atom to which they are attached, form a pyrrolidinyl, piperidinyl or perhydroazepinyl group; where R28 and R29 are independently selected from H, F, alkyl (en / in) C1-6 yl, C3-8 cycloalkyl and C1-8 cycloalkyl-C1-6 alkyl; where R33-R36 are independently selected from H, halogen, cyano, nitro, alkyl (en / in) C1-6 yl, C3-8 cycloalkyl, C3-8 cycloalkyl, amino, C1-6 alkylamino, di (C1-6 alkyl) amino, C1-6 alkylcarbonyl ,. Aminocarbonyl, C 1-6 alkylaminocarbonyl, di- (C 1-6 alkyl) aminocarbonyl, C 1-6 alkoxy, C 1-6 alkylthio, hydroxy, trifluoromethyl, trifluoromethylsulfonyl and C 1-6 alkylsulfonyl, where R37-R38 are both H or are fused between yes in an ethylene chain CH2-CH2-forming an aza-bicyclo [3.2.1] octan-yl; where R39 -R41 are independently selected from the group consisting of H and halogen; provided that no more than one of X, Y and Z can be a link, and with the proviso that two adjacent groups X, Y or Z cannot be selected at the same time between O and S.

ARP040102914A 2003-08-15 2004-08-13 DERIVATIVES OF CYCLOPROPYL AS ANTAGONISTS OF THE NK3 RECEIVER AR045368A1 (en)

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US8324250B2 (en) * 2009-03-19 2012-12-04 Hoffmann-La Roche Inc. Piperidine derivatives as NK3 receptor antagonists
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FR2719311B1 (en) * 1994-03-18 1998-06-26 Sanofi Sa Compounds that are selective antagonists of the human NK3 receptor and their use as drugs and diagnostic tools.
US5434158A (en) * 1994-04-26 1995-07-18 Merck & Co., Inc. Spiro-substituted azacycles as neurokinin-3 antagonists
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