ES2663124T3 - Compuestos tricíclicos de piperidina - Google Patents

Compuestos tricíclicos de piperidina Download PDF

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ES2663124T3
ES2663124T3 ES14799473T ES14799473T ES2663124T3 ES 2663124 T3 ES2663124 T3 ES 2663124T3 ES 14799473 T ES14799473 T ES 14799473T ES 14799473 T ES14799473 T ES 14799473T ES 2663124 T3 ES2663124 T3 ES 2663124T3
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alkyl
ring
alkoxy
heteroaryl
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Daniel Bur
Corinna Grisostomi
Oliver Nayler
Lubos Remen
Magali VERCAUTEREN
Richard Welford
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Actelion Pharmaceuticals Ltd
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    • C07—ORGANIC CHEMISTRY
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    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains three hetero rings
    • C07D513/14—Ortho-condensed systems
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    • 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
    • A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/4365—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system having sulfur as a ring hetero atom, e.g. ticlopidine
    • 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
    • A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/437—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
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    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • A—HUMAN NECESSITIES
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    • A61P19/00—Drugs for skeletal disorders
    • A—HUMAN NECESSITIES
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    • A61P19/00—Drugs for skeletal disorders
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
    • A—HUMAN NECESSITIES
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    • A—HUMAN NECESSITIES
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    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
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    • 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
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    • A61P35/00—Antineoplastic agents
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    • A61P37/00—Drugs for immunological or allergic disorders
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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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    • A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
    • 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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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
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  • Urology & Nephrology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Un compuesto de Fórmula (I)**Fórmula** Donde X representa CH, o N; R representa hidrógeno, alquilo(C1 - 4 ), c icloalquilo(C3 - 6 ), o trifluoroalqui lo (C1 - 3 ); R1 a y R 1 b representan independientemente hid rógeno, metilo, etilo ; o R1 a y R 1 b j u n t o con el átomo de carbono al cual están unidos para formar un anillo c ic lopropilo; R2 representa a r i lo o heteroarilo, e n donde d icho arilo o heteroarilo e stá independientemente sin sustituir, o sustituido una, dos o tre s veces, d o n d e los sustitu ye ntes se se leccionan independientemente entre: - alquilo(C 1 - 4 ); - alcoxi(C 1 - 4 ); - c ic loalquilo(C 3 - 6 ), que contiene opcionalmente uno o dos áto m o s de oxígeno en el anillo ; - f luoroalqu ilo(C1 - 3 ); - f lu o r o alco xi(C 1 - 3) ; - halógeno; - c iano; - - (CH 2 )n - N R 21 R2 2 , donde n representa el número entero 0 o 1; y - R2 1 y R2 2 representan independientemente hid rógeno o alqui lo (C1 - 3 ); o - R2 1 y R 2 2 j u n to c on el á to mo d e nitrógeno al c u a l e st á n unidos para formar u n anillo saturado d e 4 a 7 m iembros, en d o n d e d i c h o a n i l l o c o n t iene opcionalmente u n átomo de oxígeno en el anillo , y en d o n d e d icho anillo está o p c ionalmente sustitu id o con uno o dos sustituyentes flú o r ; - c arboxi; - -C O-NR2 3 R 2 4 , donde R2 3 y R2 4 representan independientemente hid rógeno o alquilo(C 1 - 4 ); - -C O- alcoxi(C 1 - 4 ); - -N R25 - CO- R2 6 , e n donde R2 5 representa h idrógeno o alquilo(C 1 - 4 ); y R2 6 representa alquilo(C1 - 4 ) o un grupo -NR27R2 8 donde R2 7 y R2 8 representan independientemente hidrógeno o alq u i lo (C 1 - 4 ); - hidroxi- alquilo(C 1 - 4 ) ; - alcoxi(C 1 - 3 )- alquilo(C 1 - 4 ); - hidroxi- alcoxi(C 2 - 4 ); - alcoxi(C1 - 3 )-alcoxi(C2 - 4 ); - fenilo; - heteroarilo de 5 miembros; o - 3 -metoxi- o xe ta n -3 - ilo ; R3 representa ar i lo o heteroarilo , en donde dicho arilo o heteroarilo e stá independientemente sin sustituir, o sustituido una, dos, tre s o cuatro veces, e n donde lo s sustitu ye ntes se se leccionan independientemente entre: - -N R4- SO 2 -Y- R 5, d onde - R4 representa hidrógeno o alquilo(C1 - 3 ); Y representa un enlace directo; y R5 representa alquilo(C 1 - 4 ), o cicloalquilo(C 3 - 6 ); o - R4 representa h id ró g en o o alquilo(C 1 - 3 ); Y representa - N RY- donde R Y representa hidrógeno o alq u i lo (C 1 - 3 ); y R 5 representa alquilo(C 1 - 4 ); o - R4 y R5 j u n t o c o n el n it ró g en o y e l g ru p o -S O 2- Y- al cual están unidos para fo rmar un a nillo de 5 , 6, o 7 miembros, donde Y representa un enlace directo o -NRY- donde RY representa alquilo(C 1 - 3 ); - -C O-NR6 R7 , d o n d e R6 y R 7 representa in dependientemente hidrógeno, alquilo(C 1 - 4 ) , o c ic loalquilo(C 3 - 6 ); o R6 representa hidrógeno y R7 representa hidroxi, metoxi, o cia n o ; - -S O 2- R8 d o n d e R8 representa alquilo(C 1 - 5 ), - alquilen(C 2 - 4 )- C O- alcoxi(C 1 - 3 ), o - NR8 1R8 2 , en donde R 81 y R8 2 representan independientemente hidrógeno o alquilo(C 1 - 4) ; - alquilo(C1 - 4 ); - alcoxi(C 1 - 4 ); - f lu o r o alqu ilo(C 1 - 3 ); - f lu o r o alco xi(C 1 - 3) ; - c ic loalquilo(C 3 - 6 ) opcionalmente sustituido una vez con dimetilamino; - halógeno; - c iano; - alcoxi(C 1 - 3 )- alquilo(C 1 - 4 ); - alcoxi(C 1 - 3 )- alcoxi(C 2 - 4 ); - -C O- alcoxi(C 1 - 4 ) ; - heteroarilo de 5 miembros; - - (CH 2 )m - N R9 R1 0 ; d onde m representa el número entero 0 o 1 ; y - R9 y R 1 0 representan independientemente h id r ó g eno, alquilo(C 1 - 4 ), fluoro alquilo(C 2 - 3) , hidroxi- alquilo(C 2 - 4 ), o alcoxi(C 1 - 4)- alquilo(C 2 - 4 ); o - R9 y R 1 0 j u n t o con el nitrógeno al cual están unidos para fo rmar un anillo monocíclico de 4 a 7 miembros saturado o un sistema de anillos puenteado o fusionados b ic íc l ic os de 7 u 8 miembros saturado; donde independientemente dicho anillo o sistema d e a n illo s c o n t iene opcionalmente u n átomo de oxíg e n o e n e l anillo o u n g rupo -NR 11 - en d o n d e R1 1 representa alquilo(C 1 - 4 ); y en donde d ic h o anillo o sistema d e anillo s e s independiente y opcionalmente sustituido con: - uno o dos sustitu yen te s flúor; o - uno o dos sustitu yen te s metilo; o - un sustitu yen te o xo u n i d o a u n á t o mo d e c a r b o n o d e l anillo e n posic ió n alfa a un átomo de nitrógeno en el anillo; e n donde e n e l c aso partic u lar e n d o n d e R3 representa heteroarilo e l c u a l es p i r id in ilo, d ic ho pirid in ilo puede estar presente ad ic io nalmente en forma del respectivo N -ó xi d o ; o su sal farmacéuticamente aceptable.
ES14799473T 2013-11-19 2014-11-18 Compuestos tricíclicos de piperidina Active ES2663124T3 (es)

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IB2013060237 2013-11-19
PCT/EP2014/074885 WO2015075023A1 (en) 2013-11-19 2014-11-18 Tricyclic piperidine compounds

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EP (1) EP3071578B1 (es)
JP (1) JP6466937B2 (es)
KR (1) KR102390234B1 (es)
CN (1) CN105745214B (es)
AR (1) AR098436A1 (es)
AU (1) AU2014352008B2 (es)
CA (1) CA2926600A1 (es)
EA (1) EA029391B1 (es)
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WO (1) WO2015075023A1 (es)

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UA119247C2 (uk) 2013-09-06 2019-05-27 РОЙВЕНТ САЙЕНСИЗ ҐмбГ Спіроциклічні сполуки як інгібітори триптофангідроксилази
TW201609721A (zh) 2013-11-19 2016-03-16 艾克泰聯製藥有限公司 三環咪唑化合物
US9611201B2 (en) 2015-03-05 2017-04-04 Karos Pharmaceuticals, Inc. Processes for preparing (R)-1-(5-chloro-[1,1′-biphenyl]-2-yl)-2,2,2-trifluoroethanol and 1-(5-chloro-[1,1′-biphenyl]-2-yl)-2,2,2-trifluoroethanone
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US9765092B2 (en) 2017-09-19
TW201605868A (zh) 2016-02-16
MX2016006509A (es) 2016-08-04
WO2015075023A1 (en) 2015-05-28
CN105745214B (zh) 2019-02-19
CN105745214A (zh) 2016-07-06
TWI658043B (zh) 2019-05-01
MX368635B (es) 2019-10-09
KR102390234B1 (ko) 2022-04-22
US20160272655A1 (en) 2016-09-22
AU2014352008B2 (en) 2018-08-16
EA201600394A1 (ru) 2016-10-31
EP3071578A1 (en) 2016-09-28
EA029391B1 (ru) 2018-03-30
KR20160077216A (ko) 2016-07-01
JP2016537376A (ja) 2016-12-01
JP6466937B2 (ja) 2019-02-06
PL3071578T3 (pl) 2018-07-31
CA2926600A1 (en) 2015-05-28
AR098436A1 (es) 2016-05-26
EP3071578B1 (en) 2018-01-10

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