AR080267A1 - Compuestos heterociclicos utiles para el control de productos de la glicosilacion avanzada (ages) - Google Patents

Compuestos heterociclicos utiles para el control de productos de la glicosilacion avanzada (ages)

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Publication number
AR080267A1
AR080267A1 ARP100101563A ARP100101563A AR080267A1 AR 080267 A1 AR080267 A1 AR 080267A1 AR P100101563 A ARP100101563 A AR P100101563A AR P100101563 A ARP100101563 A AR P100101563A AR 080267 A1 AR080267 A1 AR 080267A1
Authority
AR
Argentina
Prior art keywords
alkyl
group
aryl
heterocyclyl
perhaloalkyl
Prior art date
Application number
ARP100101563A
Other languages
English (en)
Inventor
Chaitanya Dutt
Vijay Chauthaiwale
Ramesh Chandra Gupta
Manish Patel
Sachin Latad
Jignesh Kotecha
Jaya Abraham
Sanjay Srivastava
Original Assignee
Torrent Pharmaceuticals Ltd
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 Torrent Pharmaceuticals Ltd filed Critical Torrent Pharmaceuticals Ltd
Publication of AR080267A1 publication Critical patent/AR080267A1/es

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • 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
    • A61P17/00—Drugs for dermatological disorders
    • 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
    • A61P25/28—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
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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
    • A61P3/06—Antihyperlipidemics
    • 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
    • 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
    • A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
    • 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
    • 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
    • A61P9/12—Antihypertensives
    • 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
    • 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
    • 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
    • C07D401/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D401/14—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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Hospice & Palliative Care (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Diabetes (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Psychiatry (AREA)
  • Dermatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

Proceso para la preparacion de los mismos, composicion farmacéutica que contiene estos compuestos y a su uso en el tratamiento de enfermedades provocadas por la formacion y acumulacion de AGEs (productos resultantes de la Glicosilacion Avanzada). Los compuestos de la presente, son utiles para el tratamiento de complicaciones relacionadas con el envejecimiento y la diabetes provocadas por la formacion y acumulacion de AGEs, tal como neuropatía, nefropatía, microangiopatía, retinopatía, hipertension, falla cardíaca, aterosclerosis, enfermedad de Alzheimer y desordenes dermatologicos. Reivindicacion 1: N'-(metilsulfonil)-1-[2-oxo-2-(tiofen-2-il)etil]-1,4-dihidropiridina-3-carbohidrazida y sal farmacéuticamente aceptable del mismo. Reivindicacion 2: Un compuesto de la formula (1) y sal farmacéuticamente aceptable del mismo; en donde, la línea punteada en el anillo que contiene nitrogeno representa: (a) dos uniones dobles entre ya sea (i) en C2-3 y C5-6, o (ii) en C2-3 y C4-5, o (iii) en C3-4 y C5-6, o (b) una doble entre ya sea (i) en C2-3 o (ii) en C3-4 o (iii) en C4-5 o (iv) o en C5-6, o (c) ausencia de union doble es decir un sistema de anillo saturado; R1 es -COR3 o anillo heterocíclico de 5 miembros que tiene la formula siguiente: (2); G1 y G2 son independientemente N, NH, NR12, S o O para formar un sistema de anillo heterocíclico, el cual también puede ser ya sea parcialmente o completamente saturado; G3 es -(C1-12) alquileno-P o - (C1-12) alquileno, en donde P es azufre, oxígeno o nitrogeno, y n es 0 o 1; Z es i) -CH2-C(O)-Rx o ii) Ry; Rx es R7, OR7, -N(R7)(R10), -N=C(R7) (R10), -N(R7)N(R7)(R10), -N(R7)N=C(R7)(R10), -CH(R7)C(O)R8 o un compuesto que tiene una de las siguientes formulas: (3); Ry está seleccionado del grupo que consiste de hidrogeno, lineal o ramificado (C1-12) alquilo, (C2-12) alquenilo, (C3-7)cicloalqullo, (C5-7)cicloalquenilo, bicicloalquilo, CH2(CO)R13, CH2 (CO) NHR14, CH2 (CO) NR14R15 y CH2 (CO)OR13; R2 cada vez que aparece es Halogeno, OR7, NO2, alquilo, arilo, heterociclilo, formil, oxo, -NR7R10, -N=C(R7)(R10), -SR7, -SO2NH2, -SO2 alquilo, -SO2 arilo, N=C(R14) (R15), -NR14R15, -OR14, perhaloalquil, -O(CO) R14, -NH(CO)R14, (C2-12) alquenilo, (C3-7)cicloalquilo, (C5-7)cicloalquenilo, bicicloalquilo, bicicloalquenilo, heterocicloalquilo, o aralquilo; m es 0, 1, 2 o 3; R3 es -R4-R5, -N(R7)N(R7)R9 o un compuesto que tiene una de las siguientes formulas: (4); R4 es -N (R7)R6O-, -N (R7)R6N(R7)-, OR6O o -OR6N(R7)-, en donde R6 es alquileno; R5 es hidrogeno, alquilo, arilo, heterociclilo, -COR7, SO2R7, -C(S) NHR7, -C(=NH)NHR7, -COR10, -C(O)NHR7 o (5); en donde R7 es H, alquilo, arilo o heterociclilo; R8 es R7, OR7 o NR7R10; R9 está seleccionado del grupo que consiste de hidrogeno, alquilo, arilo, heterociclilo, C(O)R10, -SO2R10, -C(S)NHR10, -C(N=H)NH(R10) y -C(O)NHR10; R10 está seleccionado del grupo que consiste de H, alquilo, alcoxi, arilo y heterociclilo; R11 está seleccionado del grupo que consiste de hidrogeno, lineal o ramificado (C1-12)alquilo, (C2-12)alquenilo, (C3-7)cicloalquilo, (C5-7)cicloalquenilo, bicicloalquilo, bicicloalquenilo, heterocicloalquilo, arilo, aralquilo, heterociclil y el Compuesto (6), en donde en R11 uno o más heteroátomos cuando están presentes son independientemente O, N, o S y está opcionalmente substituido, en donde los substituyentes están seleccionados de un primer grupo que consiste de halogeno, hidroxi, nitro, ciano, amino, oxo y oxima o de un segundo grupo que consiste de, lineal o ramificado, (C1-8) alquilo, (C3-7) cicloalquilo, alquilcicloalquilo, perhaloalquil, perhalocicloalquilo, arilo, aralquilo, alquilarilo, aralcoxialquilo, perhaloarilo, alquilheterocicloalquilo, heterocicliloalquilo, perhaloheterocicliloalquilo, heterociclilo, perhaloheteroarilo, alcoxialquilo, tioalquilo y tioarilo, en donde los substituyentes de dicho segundo grupo están opcionalmente substituidos por halogeno, hidroxi, nitro, ciano, amino, oxo, perhaloalquil (C1-6) y oxima y están opcionalmente e independientemente unidos por -CO, -(CO)O-, -(CO)NH-, -NH-, -NR14-, -O-, -S-, -(SO)-, -(SO2), -(SO2)NH-, o -NH(CO)-; R12 y R13 son independientemente seleccionados del grupo que consiste de, lineal o ramificado, (C1-8) alquilo, (C3-7) cicloalquilo, alquilcicloalquilo, perhaloalquil, perhalocicloalquilo, arilo, aralquilo, alquilarilo, aralcoxialquilo, perhaloarilo, alquilheterocicloalquilo, heterocicloalquilo, perhaloheterocicloalquilo, heterociclilo, perhaloheterociclilo, -COalkyl, -COarilo, benzoyl, alcoxialquilo, tioalquilo y tioarilo en donde los miembros de dicho grupo están opcionalmente substituidos por R16; R14 y R15 son independientemente seleccionados del grupo que consiste de, lineal o ramificado, (C1-12) alquilo, alcoxiarilo, alcoxialquilo, alcoxicicloalquilo, alcoxiarilo, perhaloalquil, (C2-12) alquenilo, (C3-7) cicloalquilo, perhalocicloalquilo, haloheterocicloalquilo, cianoheterocicloalquilo, perhaloheterocicloalquilo, (C5-7) cicloalquenilo, bicicloalquilo, bicicloalquenilo, heterocicloalquilo, arilo, aralquilo, heterociclilo, perhaloarilo y perhaloheterociclil en donde los substituyentes de dicho grupo están opcionalmente substituidos por R16; R16 es Halogeno, hidroxi, nitro, ciano, amino, oxo, perhaloalquil (C1-6), u oxima; siempre que (i) cuando R1 es -C(O)R3, entonces Z es -CH2-C(O)-Rx; (ii) cuando Z es -CH2-C(O)-Rx y Rx es OR, entonces R7 no es hidrogeno.
ARP100101563A 2009-05-07 2010-05-07 Compuestos heterociclicos utiles para el control de productos de la glicosilacion avanzada (ages) AR080267A1 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IN1207MU2009 2009-05-07

Publications (1)

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AR080267A1 true AR080267A1 (es) 2012-03-28

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ARP100101563A AR080267A1 (es) 2009-05-07 2010-05-07 Compuestos heterociclicos utiles para el control de productos de la glicosilacion avanzada (ages)

Country Status (16)

Country Link
US (1) US20120046317A1 (es)
EP (1) EP2427432A2 (es)
JP (1) JP2012526103A (es)
KR (1) KR20120018185A (es)
CN (1) CN102459175A (es)
AR (1) AR080267A1 (es)
AU (1) AU2010245596A1 (es)
BR (1) BRPI1006611A2 (es)
CA (1) CA2764232A1 (es)
EA (1) EA201171368A1 (es)
IL (1) IL216092A0 (es)
MX (1) MX2011011650A (es)
SG (1) SG175422A1 (es)
TW (1) TW201102380A (es)
WO (1) WO2010128528A2 (es)
ZA (1) ZA201108702B (es)

Families Citing this family (3)

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Publication number Priority date Publication date Assignee Title
CN104744351B (zh) * 2014-09-30 2017-06-06 三峡大学 一种小分子抑制剂及在抑制鸟氨酸脱羧酶(odc)上的应用
MX2017012942A (es) * 2015-04-08 2018-01-30 Torrent Pharmaceuticals Ltd Formulaciones farmaceuticas.
JP2021102589A (ja) * 2019-12-25 2021-07-15 サムライ金沢株式会社 カワラケツメイ属に属する植物の発酵物ならびに前記を含有する化粧料および皮膚外用剤

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Publication number Priority date Publication date Assignee Title
US4758583A (en) 1984-03-19 1988-07-19 The Rockefeller University Method and agents for inhibiting protein aging
GB8714789D0 (en) * 1987-06-24 1987-07-29 Lundbeck & Co As H Heterocyclic compounds
AU678186B2 (en) * 1992-10-23 1997-05-22 Merck Sharp & Dohme Limited Dopamine receptor subtype ligands
PT808163E (pt) 1995-01-18 2003-12-31 Alteon Inc Uso de compostos de tiazolio para prevencao e inversao da formacao de produtos finais com glicosilacao avancada
US5656261A (en) 1995-01-18 1997-08-12 The Picower Institute For Medical Research Preventing and reversing advanced glycosylation endproducts
HUP0301687A2 (hu) 1999-10-06 2003-08-28 Torrent Pharmaceuticals Ltd. Cukorbetegséggel és öregedéssel kapcsolatos érrendszeri szövődmények kezelésére szolgáló piridinium-vegyületek és eljárás az előállításukra
WO2001025208A1 (en) 1999-10-06 2001-04-12 Alangudi Sankaranarayanan Pyridinium derivatives for the management of aging-related and diabetic vascular complications, process for their preparation and therapeutic uses thereof
DK1243581T3 (da) * 2001-03-21 2005-10-31 Torrent Pharmaceuticals Ltd Pyridiniumforbindelser til behandling af AGE-relaterede sygdomme
CN1259316C (zh) 2001-04-05 2006-06-14 托伦脱药品有限公司 用于老龄相关性和糖尿病性血管系统并发症的杂环类化合物
HUP0104831A2 (hu) * 2001-10-19 2003-08-28 Torrent Pharmaceuticals Ltd. Készítmény és eljárás piridíniumszármazékok gyógyászati alkalmazására
KR100437972B1 (ko) * 2001-10-27 2004-07-02 한국과학기술연구원 피롤리디논 유도체, 이의 제조 방법 및 이를 포함하는제약 조성물
MX2009011499A (es) * 2007-04-24 2009-11-09 Solvay Pharm Bv Compuestos heterociclicos con afinidad por los receptores muscarinicos.

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WO2010128528A2 (en) 2010-11-11
MX2011011650A (es) 2012-02-21
US20120046317A1 (en) 2012-02-23
WO2010128528A9 (en) 2011-03-03
CN102459175A (zh) 2012-05-16
CA2764232A1 (en) 2010-11-11
EA201171368A1 (ru) 2012-04-30
IL216092A0 (en) 2012-01-31
EP2427432A2 (en) 2012-03-14
WO2010128528A3 (en) 2010-12-23
AU2010245596A1 (en) 2011-12-22
KR20120018185A (ko) 2012-02-29
JP2012526103A (ja) 2012-10-25
ZA201108702B (en) 2012-09-26
SG175422A1 (en) 2011-11-28
BRPI1006611A2 (pt) 2016-04-19
TW201102380A (en) 2011-01-16

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