ES2533434T3 - Inhibidores de la captación de la serotonina - Google Patents

Inhibidores de la captación de la serotonina Download PDF

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Publication number
ES2533434T3
ES2533434T3 ES11773367.5T ES11773367T ES2533434T3 ES 2533434 T3 ES2533434 T3 ES 2533434T3 ES 11773367 T ES11773367 T ES 11773367T ES 2533434 T3 ES2533434 T3 ES 2533434T3
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methanesulfonyl
pyrrolidine
ethyl
formula
optionally substituted
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Eric L. Stangeland
Lori Jean Patterson
Daisuke Roland Saito
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Theravance Biopharma R&D IP LLC
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    • 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
    • C07D207/08—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 hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
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    • A—HUMAN NECESSITIES
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
    • A61P3/14—Drugs for disorders of the metabolism for electrolyte homeostasis for calcium homeostasis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
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    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • 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
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    • 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
    • C07D401/12—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

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Abstract

Un compuesto de fórmula I:**Fórmula** X e Y son -CH-, o X es -CH- e Y es -N-, o X es -N- e Y es -CH-; R1 se selecciona entre -alquilo C1-6 opcionalmente sustituido con 1 a 5 grupos seleccionados entre halo, -NHC(O)CH3 y -C(O)NHCH3; -cicloalquilo C3-6; -alquilen C1-2-OR; -alquilen C1-2-COOR; -alquilen C0-3-fenilo opcionalmente sustituido con -NHC(O)CH3 o -C(O)NHCH3; y -alquilen C0-3-piridilo; donde R se selecciona entre hidrógeno y -alquilo C1-3; R2 se selecciona entre hidrógeno, -alquilo C1-6 y -O-alquilo C1-6; R3 se selecciona entre hidrógeno, halo y ciano; R4 se selecciona entre halo; -alquilo C1-6 opcionalmente sustituido con 1 a 5 átomos de flúor; -O-alquilo C1-6 opcionalmente sustituido con 1 a 5 átomos de flúor; -alquilen C0-1-fenilo; -O-alquilen C0-3-fenilo; -SO2-alquilo C1-6; -C(O)NH2; y -NO2; y n es 1 o 2; o una sal farmacéuticamente aceptable del mismo.

Description

imagen1
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E11773367
19-03-2015
imagen6
donde X, Y, R1, R2, R3, R4 y n son como se han definido para la fórmula I. En un estereoisómero, ambos átomos de carbono identificados por los símbolos * y ** tienen la configuración (R). Esta realización de la invención se muestra en la fórmula a (para n = 1) y la fórmula a’ (para n = 2):
imagen7
En esta realización, los compuestos tienen la configuración (R,R) en los átomos de carbono * y ** o están 10 enriquecidos en una forma estereoisomérica que tenga la configuración (R,R) en estos átomos de carbono.
En otro estereoisómero, ambos átomos de carbono identificados por los símbolos * y ** tienen la configuración (S). Esta realización de la invención se muestra en la fórmula b (para n = 1) y la fórmula b' (para n = 2):
imagen8
En esta realización, los compuestos tienen la configuración (S,S) en los átomos de carbono * y ** o están enriquecidos en una forma estereoisomérica que tiene la configuración (S,S) en estos átomos de carbono.
20 En otro estereoisómero más, el átomo de carbono identificado por el símbolo * tiene la configuración (S) y el átomo de carbono identificado por el símbolo ** tiene la configuración (R). Esta realización de la invención se muestra en la fórmula c (para n = 1) y la fórmula c' (para n = 2):
7
imagen9
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imagen11
E11773367
19-03-2015
-CN Cl -CN -CF3
En una realización particular, n es 1, y X, Y, R1, R2, R3 y R4, son como se han definido para la fórmula I. Esto se puede representar como la fórmula III:
imagen12
Las realizaciones específicas incluyen las fórmulas IIIa, IIIb y IIIc:
imagen13
10 En otra realización particular, n es 2, y X, Y, R1, R2, R3 y R4 son como se han definido en la fórmula I. Esto se puede representar como la fórmula IV:
imagen14
Las realizaciones específicas incluyen las fórmulas IVa, IVb y IVc:
11
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E11773367
19-03-2015
Ej.
R1 R2 R3 R4 Fórmula MS m/z: [M+H]+
Calculado
Encontrado
12
-CH2CH3 H H -CF3 C15H20F3NO3S 352,11 352,0
13
-CH(CH3)2 H H -CF3 C16H22F3NO3S 366,13 366,0
14
-(CH2)2-NHC(O)CH3 H H -CF3 C17H23F3N2O4S 409,13 409,0
15
-(CH2)2-OH H H -CF3 C15H20F3NO4S 368,11 368,0
16
C(O)O-CH3 H H -CF3 C16H20F3NO5S 396,10 396,0
17
fenilo H H -CF3 C19H20F3NO3S 400,11 400,0
18
4-fenilacetamida H H -CF3 C21H23F3N2O4S 457,13 457,0
19
4-piridilo H H -CF3 C18H19F3N2O3S 401,11 401,0
20
-CH3 H -CN -CF3 C15H17F3N2O3S 363,09 363,0
21
-CH3 H -CN -CF3 C15H17F3N2O3S 363,09 363,0
22
-CH3 H -CN -Cl C14H17ClN2O3S 329,07 329,0
23
-CH3 H -CN -Cl C14H17ClN2O3S 329,07 329,0
24
-CH3 H -CN -Cl C14H17ClN2O3S 329,07 329,0
25
-CH3 -OCH3 H -NO2 C14H26N2O6S 345,10 345,0
26
-CH3 -OCH3 H -NO2 C14H20N2O6S 345,10 345,0
27
-CH3 -OCH3 H -NO2 C14H20N2O6S 345,10 345,0
28
-CH3 -CH3 H -Cl C14H20ClNO3S 318,09 318,0
1.
(S)-3-[(R)-2-Metanosulfonil-1-(4-trifluorometilfenoxi)etil]pirrolidina
2.
(R)-3-[(R)-2-Metanosulfonil-1-(4-trifluorometilfenoxi)etil]pirrolidina
3.
(R)-3-[(S)-2-Metanosulfonil-1-(4-trifluorometilfenoxi)etil]pirrolidina
5 4. (S)-3-[(R)-1-(4-Clorofenoxi)-2-metanosulfoniletil]pirrolidina
5.
(S)-3-[(S)-2-Metanosulfonil-1-(4-nitro-fenoxi)etil]pirrolidina
6.
(S)-3-[(R)-2-Metanosulfonil-1-(4-nitro-fenoxi)etil]pirrolidina
7.
(R)-3-[(S)-2-Metanosulfonil-1-(4-nitro-fenoxi)etil]pirrolidina
8.
(R)-3-[(R)-2-Metanosulfonil-1-(4-nitro-fenoxi)etil]pirrolidina
10 9. (S)-3-[(S)-2-Metanosulfonil-1-(4-trifluorometoxifenoxi)etil]pirrolidina
10.
(S)-3-[(R)-2-Metanosulfonil-1-(4-trifluorometoxifenoxi)etil]pirrolidina
11.
(R)-3-[(S)-2-Metanosulfonil-1-(4-trifluorometoxifenoxi)etil]pirrolidina
12.
(S)-3-[(S)-2-Etanosulfonil-1-(4-trifluorometil-fenoxi)etil]pirrolidina
13.
(S)-3-[(S)-2-(Propano-2-sulfonil)-1-(4-trifluorometilfenoxi)etil]pirrolidina 15 14. N-{2-[(S)-2-(S)-Pirrolidin-3-il-2-(4-trifluorometilfenoxi)etanosulfonil]-etil}-acetamida
15.
2-[(S)-2-(S)-Pirrolidin-3-il-2-(4-trifluorometilfenoxi)etanosulfonil]etanol
16.
Metiléster de ácido [(S)-(S)-pirrolidin-3-il-(4-trifluorometilfenoxi)etanosulfonil]acético
17.
(S)-3-[(S)-2-Bencenosulfonil-1-(4-trifluorometilfenoxi)etil]pirrolidina
18.
N-{4-[(S)-2-(S)-Pirrolidin-3-il-2-(4-trifluorometilfenoxi)etanosulfonil]-fenil}-acetamida 20 19. 4-[(S)-2-(S)-Pirrolidin-3-il-2-(4-trifluorometilfenoxi)etanosulfonil]piridina
20.
5-(S)-2-Metanosulfonil-1-(S)-pirrolidin-3-iletoxi)-2-trifluorometilbenzonitrilo
21.
5-(S)-2-Metanosulfonil-1-(R)-pirrolidin-3-iletoxi)-2-trifluorometil-benzonitrilo
22.
2-Cloro-5-((S)-2-metanosulfonil-1-(S)-pirrolidin-3-iletoxi)benzonitrilo
23. 2-Cloro-5-((R)-2-metanosulfonil-1-(S)-pirrolidin-3-iletoxi)benzonitrilo 25 24. 2-Cloro-5-(S)-2-metanosulfonil-1-(R)-pirrolidin-3-iletoxi)benzonitrilo
25.
(S)-3-[(R)-2-Metanosulfonil-1-(2-metoxi-4-nitrofenoxi)etil]pirrolidina
26.
(R)-3-[(S)-2-Metanosulfonil-1-(2-metoxi-4-nitrofenoxi)etil]pirrolidina
27.
(R)-3-[((R)-2-Metanosulfonil-1-(2-metoxi-4-nitrofenoxi)etil]pirrolidina
28.
(S)-3-[(R)-1-(4-Cloro-2-metilfenoxi)-2-metanosulfoniletil]pirrolidina.
30 Preparación 5
t-Butiléster de ácido (R)-3-((S)-1-hidroxi-2-metilsulfaniletil)pirrolidin-1-carboxílico
34
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Claims (1)

  1. imagen1
    imagen2
    imagen3
ES11773367.5T 2010-10-11 2011-10-10 Inhibidores de la captación de la serotonina Active ES2533434T3 (es)

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US39175810P 2010-10-11 2010-10-11
US391758P 2010-10-11
PCT/US2011/055580 WO2012051103A1 (en) 2010-10-11 2011-10-10 Serotonin reuptake inhibitors

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EP (1) EP2627630B1 (es)
JP (1) JP5873877B2 (es)
CN (1) CN103153950B (es)
CA (1) CA2811641A1 (es)
ES (1) ES2533434T3 (es)
WO (1) WO2012051103A1 (es)

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WO2012075239A1 (en) 2010-12-03 2012-06-07 Theravance, Inc. Serotonin reuptake inhibitors
JP2014528416A (ja) 2011-09-30 2014-10-27 セラヴァンス バイオファーマ アール＆ディー アイピー， エルエルシー ３−［２−メタンスルホニル−１−（４−トリフルオロメチル−フェノキシ）エチル］−ピロリジン化合物の結晶形態
TW202408485A (zh) 2022-06-13 2024-03-01 美商埃皮辛特瑞科斯公司 用於減少癌症治療中不良副作用之組合物及方法

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