PE20121438A1 - Derivados de imidazopiridina o imidazopirimidina como inhibidores de fosfodiesterasa 10a - Google Patents

Derivados de imidazopiridina o imidazopirimidina como inhibidores de fosfodiesterasa 10a

Info

Publication number
PE20121438A1
PE20121438A1 PE2012000365A PE2012000365A PE20121438A1 PE 20121438 A1 PE20121438 A1 PE 20121438A1 PE 2012000365 A PE2012000365 A PE 2012000365A PE 2012000365 A PE2012000365 A PE 2012000365A PE 20121438 A1 PE20121438 A1 PE 20121438A1
Authority
PE
Peru
Prior art keywords
lower alkyl
alcoxy
fluoroalkyl
imidazo
pyridin
Prior art date
Application number
PE2012000365A
Other languages
English (en)
Inventor
Daniela Alberati
Sanchez Ruben Alvarez
Konrad Bleicher
Alexander Flohr
Katrin Groebke Zbinden
Matthias Koerner
Bernd Kuhn
Jens-Uwe Peters
Markus Rudolph
Original Assignee
Hoffmann La Roche
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 Hoffmann La Roche filed Critical Hoffmann La Roche
Publication of PE20121438A1 publication Critical patent/PE20121438A1/es

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    • C—CHEMISTRY; METALLURGY
    • 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
    • C07D471/04—Ortho-condensed systems
    • 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
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/50—Pyridazines; Hydrogenated pyridazines
    • A61K31/5025—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with heterocyclic ring systems
    • 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
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
    • 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
    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • A61K31/553—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having at least one nitrogen and one oxygen as ring hetero atoms, e.g. loxapine, staurosporine
    • 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
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/22—Anxiolytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • 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
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Epidemiology (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Psychiatry (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Psychology (AREA)
  • Urology & Nephrology (AREA)
  • Emergency Medicine (AREA)
  • Obesity (AREA)
  • Hospice & Palliative Care (AREA)
  • Oncology (AREA)
  • Endocrinology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Addiction (AREA)
  • Pain & Pain Management (AREA)
  • Cardiology (AREA)
  • Vascular Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

SE REFIERE A UN COMPUESTO DERIVADO DE IMIDAZOPIRIDINA DE FORMULA (I) DONDE: A ES N O C(R6); R1 ES H, ALQUILO INFERIOR O FLUOROALQUILO INFERIOR; R2 ES HALOGENO, C(O)NR7R8 O C(O)OR9; R3 ES H, ALQUILO INFERIOR, ALCOXI INFERIOR, FLUORO-ALCOXI INFERIOR, ENTRE OTROS; R4 ES H, ALQUILO INFERIOR, FLUOROALQUILO INFERIOR, ALCOXI INFERIOR, ENTRE OTROS; R5 ES ARILO O HETEROARILO OPCIONALMENTE SUSTITUIDO POR 1 A 3 SUSTITUYENTES SELECCIONADOS ENTRE ALQUILO INFERIOR, ALCOXI INFERIOR, ENTRE OTROS; R6 ES H, HALOGENO, CN, CICLOALQUILO, ENTRE OTROS; R7 Y R8 SON INDEPENDIENTEMENTE H, ALQUILO INFERIOR, CICLOALQUILO, FLUOROALQUILO INFERIOR, ENTRE OTROS; R9 ES H, ALQUILO INFERIOR O FLUOROALQUILO INFERIOR; SON COMPUESTOS PREFERIDOS: (2-FENIL-IMIDAZO[1,2-a]PIRIDIN-7-IL)-AMIDA DEL ACIDO 4-CLORO-2-METIL-2H-PIRAZOL-3-CARBOXILICO; 4-DIMETILAMIDA 3-[(2-FENIL-IMIDAZO[1,2-a]PIRIDIN-7-IL)-AMIDA] DEL ACIDO 2-METIL-2H-PIRAZOL-3,4-DICARBOXILICO; (2-FENIL-IMIDAZO[1,2-a]PIRIDIN-7-IL)-AMIDA DEL ACIDO 2-METIL-4-(MORFOLINA-4-CARBONIL)-2H-PIRAZOL-3-CARBOXILICO, ENTRE OTROS. SE REFIERE TAMBIEN A UNA COMPOSICION. DICHO COMPUESTO ES UN INHIBIDOR DE LA ENZIMA PDE10A, SIENDO UTIL EN EL TRATAMIENTO DE LA ESQUIZOFRENIA, ENFERMEDAD DE PARKINSON, ESCLEROSIS MULTIPLE, APOPLEJIA
PE2012000365A 2009-09-24 2010-09-21 Derivados de imidazopiridina o imidazopirimidina como inhibidores de fosfodiesterasa 10a PE20121438A1 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP09171253 2009-09-24

Publications (1)

Publication Number Publication Date
PE20121438A1 true PE20121438A1 (es) 2012-10-26

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ID=43416552

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US (2) US8017604B2 (es)
EP (1) EP2480546B1 (es)
JP (1) JP5629322B2 (es)
KR (1) KR101426624B1 (es)
CN (1) CN102548991B (es)
AR (1) AR078437A1 (es)
BR (1) BR112012006531A2 (es)
CA (1) CA2770087C (es)
CL (1) CL2012000708A1 (es)
CY (1) CY1116120T1 (es)
DK (1) DK2480546T3 (es)
ES (1) ES2530884T3 (es)
HR (1) HRP20150345T1 (es)
IL (1) IL218032A (es)
MX (1) MX2012003469A (es)
PE (1) PE20121438A1 (es)
PH (1) PH12012500355A1 (es)
PL (1) PL2480546T3 (es)
PT (1) PT2480546E (es)
RU (1) RU2502737C2 (es)
SI (1) SI2480546T1 (es)
TW (1) TWI402268B (es)
WO (1) WO2011036127A1 (es)

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US8470820B2 (en) * 2010-01-22 2013-06-25 Hoffman-La Roche Inc. Nitrogen-containing heteroaryl derivatives
WO2012105594A1 (ja) * 2011-02-01 2012-08-09 協和発酵キリン株式会社 縮環複素環誘導体
MX2013009575A (es) 2011-02-18 2014-10-14 Exonhit Therapeutics Sa Derivados de 6, 7-dialcoxi-3-isoquinolinol sustituidos como inhibidores de fosfodiesterasa 10 (pdei0a).
US8975276B2 (en) 2011-06-29 2015-03-10 Bristol-Myers Squibb Company Inhibitors of PDE10
EP2574607A1 (en) * 2011-09-06 2013-04-03 F. Hoffmann-La Roche AG PDE10 modulators
CA2846758C (en) * 2011-09-19 2017-09-12 F. Hoffmann-La Roche Ag Triazolopyridine compounds as pde10a inhibitors
WO2014071044A1 (en) 2012-11-01 2014-05-08 Allergan, Inc. Substituted 6,7-dialkoxy-3-isoquinoline derivatives as inhibitors of phosphodiesterase 10 (pde10a)
BR112015017674A2 (pt) * 2013-01-31 2017-07-11 Hoffmann La Roche compostos rádio marcados
HUE043059T2 (hu) 2013-02-27 2019-07-29 Mochida Pharm Co Ltd Új pirazolszármazék
JP6212628B2 (ja) 2013-04-29 2017-10-11 エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ ２−フェニル又は２−ヘタリールイミダゾール［１，２−ａ］ピリジン誘導体
JP2016520047A (ja) * 2013-04-30 2016-07-11 エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ ピラゾールアミドのＰｄ触媒カップリング
US10039764B2 (en) 2013-07-12 2018-08-07 University Of South Alabama Treatment and diagnosis of cancer and precancerous conditions using PDE10A inhibitors and methods to measure PDE10A expression
WO2015044095A1 (en) * 2013-09-26 2015-04-02 F. Hoffmann-La Roche Ag Imidazo[1,2-a]pyridin-7-amines as imaging tools
US9200016B2 (en) 2013-12-05 2015-12-01 Allergan, Inc. Substituted 6, 7-dialkoxy-3-isoquinoline derivatives as inhibitors of phosphodiesterase 10 (PDE 10A)
EP3872080B1 (en) 2016-09-02 2023-08-16 Cyclerion Therapeutics, Inc. Fused bicyclic sgc stimulators
CN113698406A (zh) * 2021-08-30 2021-11-26 成都药明康德新药开发有限公司 6-甲基吡唑并[1,5-a]嘧啶-3-胺的合成方法
AR134414A1 (es) * 2023-11-21 2026-01-14 Novartis Ag Imidazoarenos sustituidos y métodos para su uso

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Also Published As

Publication number Publication date
PH12012500355A1 (en) 2019-11-29
IL218032A (en) 2014-06-30
DK2480546T3 (en) 2015-02-02
BR112012006531A2 (pt) 2016-11-22
EP2480546B1 (en) 2014-12-31
CL2012000708A1 (es) 2012-09-07
CA2770087C (en) 2014-09-09
TW201116530A (en) 2011-05-16
SI2480546T1 (sl) 2015-03-31
CN102548991B (zh) 2015-03-25
RU2502737C2 (ru) 2013-12-27
CN102548991A (zh) 2012-07-04
TWI402268B (zh) 2013-07-21
CA2770087A1 (en) 2011-03-31
JP2013505911A (ja) 2013-02-21
KR20120068943A (ko) 2012-06-27
US8263584B2 (en) 2012-09-11
AR078437A1 (es) 2011-11-09
WO2011036127A1 (en) 2011-03-31
AU2010299927A1 (en) 2012-03-15
RU2012113128A (ru) 2013-11-10
US20110294779A1 (en) 2011-12-01
ES2530884T3 (es) 2015-03-06
PL2480546T3 (pl) 2015-05-29
IL218032A0 (en) 2012-04-30
CY1116120T1 (el) 2017-02-08
PT2480546E (pt) 2015-02-09
JP5629322B2 (ja) 2014-11-19
US8017604B2 (en) 2011-09-13
MX2012003469A (es) 2012-04-19
EP2480546A1 (en) 2012-08-01
KR101426624B1 (ko) 2014-08-05
HRP20150345T1 (hr) 2015-05-08
US20110071128A1 (en) 2011-03-24

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