BR9909253A - Derivados de 2-ariletil-(piperidin-4-ilmetil) amina como antagonistas de receptor muscarìnico - Google Patents

Derivados de 2-ariletil-(piperidin-4-ilmetil) amina como antagonistas de receptor muscarìnico

Info

Publication number
BR9909253A
BR9909253A BR9909253-0A BR9909253A BR9909253A BR 9909253 A BR9909253 A BR 9909253A BR 9909253 A BR9909253 A BR 9909253A BR 9909253 A BR9909253 A BR 9909253A
Authority
BR
Brazil
Prior art keywords
receptor antagonists
muscarinic receptor
piperidin
amine derivatives
arylethyl
Prior art date
Application number
BR9909253-0A
Other languages
English (en)
Inventor
Joan Marie Caroon
Robin Douglas Clark
Michael Patrick Dillon
Ralph New Ii Harris
Sharathchandra Surendra Hegde
Clara Jeou Jen Lin
Hans Maag
David Bruce Repke
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 BR9909253A publication Critical patent/BR9909253A/pt

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    • 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
    • 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
    • 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
    • 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
    • A61P1/06—Anti-spasmodics, e.g. drugs for colics, esophagic dyskinesia
    • 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
    • A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
    • 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
    • A61P1/12—Antidiarrhoeals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • 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
    • 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
    • A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
    • 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
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • 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
    • A61P25/28—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
    • A61P27/08—Mydriatics or cycloplegics
    • 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
    • A61P9/06—Antiarrhythmics
    • 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
    • C07D211/08—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
    • C07D211/26—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 nitrogen atoms
    • 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
    • C07D405/02—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 two hetero rings
    • C07D405/06—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 two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D405/02—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 two hetero rings
    • C07D405/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

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

Abstract

Patente de Invenção: <B>"DERIVADOS DE 2-ARILETIL-(PIPERIDIN-4-ILMETIL) AMINA COMO ANTAGONISTAS DE RECEPTOR MUSCARìNICO"<D>. A invenção refere-se a compostos de antagonistas de receptor muscarínico da fórmula (I) e a seus sais farmaceuticamente aceitáveis, a isómeros individuais ou a uma mistura racêmica ou não racêmica; a composições farmacêuticas contendo eles, e a métodos para o seu uso como agentes terapêuticos.
BR9909253-0A 1998-02-27 1999-02-19 Derivados de 2-ariletil-(piperidin-4-ilmetil) amina como antagonistas de receptor muscarìnico BR9909253A (pt)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US7611398P 1998-02-27 1998-02-27
US10909798P 1998-11-19 1998-11-19
PCT/EP1999/001102 WO1999043657A1 (en) 1998-02-27 1999-02-19 2-arylethyl-(piperidin-4-ylmethyl)amine derivatives as muscarinic receptor antagonists

Publications (1)

Publication Number Publication Date
BR9909253A true BR9909253A (pt) 2000-11-28

Family

ID=26757679

Family Applications (1)

Application Number Title Priority Date Filing Date
BR9909253-0A BR9909253A (pt) 1998-02-27 1999-02-19 Derivados de 2-ariletil-(piperidin-4-ilmetil) amina como antagonistas de receptor muscarìnico

Country Status (26)

Country Link
US (1) US6319920B1 (pt)
EP (1) EP1058680B1 (pt)
JP (1) JP3523198B2 (pt)
KR (1) KR100384906B1 (pt)
CN (1) CN1143848C (pt)
AR (1) AR015523A1 (pt)
AT (1) ATE400554T1 (pt)
AU (1) AU753255B2 (pt)
BR (1) BR9909253A (pt)
CA (1) CA2321198C (pt)
CO (1) CO4990939A1 (pt)
DE (1) DE69939053D1 (pt)
ES (1) ES2310032T3 (pt)
HR (1) HRP20000544A2 (pt)
HU (1) HUP0100760A3 (pt)
IL (1) IL137936A0 (pt)
MA (1) MA26610A1 (pt)
MY (1) MY133445A (pt)
NO (1) NO317106B1 (pt)
NZ (1) NZ506317A (pt)
PE (1) PE20000325A1 (pt)
PL (1) PL194037B1 (pt)
RU (1) RU2220138C2 (pt)
TR (1) TR200002481T2 (pt)
WO (1) WO1999043657A1 (pt)
YU (1) YU53100A (pt)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU7687998A (en) * 1997-05-19 1998-12-11 Sugen, Inc. Heteroarylcarboxamide compounds active against protein tyrosine kinase related disorders
HUP0302015A2 (hu) 2000-05-25 2003-10-28 F. Hoffmann-La Roche Ag. Helyettesített 1-aminoalkil-laktámok és felhasználásuk muszkarin receptor antagonistaként
EP1289965B1 (en) * 2000-05-25 2005-10-26 F. Hoffmann-La Roche Ag Substituted 1-aminoalkyl-lactams and their use as muscarinic receptor antagonists
EP1453806B1 (en) 2001-12-03 2007-12-19 F. Hoffmann-La Roche Ag Aminotetralin derivatives as muscarinic receptor antagonist
PL370765A1 (en) * 2001-12-03 2005-05-30 F.Hoffmann-La Roche Ag 4-piperidinyl alkylamine derivatives as muscarinic receptor antagonists
CA2487899A1 (en) * 2002-06-07 2003-12-18 Yamanouchi Pharmaceutical Co., Ltd. Overactive bladder treating drug
NZ537584A (en) 2002-07-08 2006-07-28 Ranbaxy Lab Ltd 3,6-disubstituted azabicyclo [3.1.0]hexane derivatives useful as muscarinic receptor antagonists
TW200800953A (en) * 2002-10-30 2008-01-01 Theravance Inc Intermediates for preparing substituted 4-amino-1-(pyridylmethyl) piperidine
CN100364990C (zh) * 2002-10-30 2008-01-30 施万制药 取代的4-氨基-1-(吡啶甲基)哌啶和相关化合物
EP1424079A1 (en) * 2002-11-27 2004-06-02 Boehringer Ingelheim International GmbH Combination of a beta-3-receptor agonist and of a reuptake inhibitor of serotonin and/or norepinephrine
DE60315258T2 (de) * 2002-12-20 2008-05-08 Dynogen Pharmaceuticals Inc., Waltham Behandlung von nicht-schmerzhaften blasenstörungen mit modulatoren der alpha-2-delta-untereinheit des calciumkanals
EP1492519B1 (en) * 2003-03-21 2006-11-15 Dynogen Pharmaceuticals, Inc. Methods for treating lower urinary tract disorders using antimuscarinics and alpha-2-delta subunit calcium channel modulators
WO2004089898A1 (en) 2003-04-09 2004-10-21 Ranbaxy Laboratories Limited Substituted azabicyclo hexane derivatives as muscarinic receptor antagonists
BRPI0409302A (pt) 2003-04-11 2006-04-11 Ranbaxy Lab Ltd derivados azabiciclo como antagonistas de recetores muscarìnicos, método para sua preparação e composição farmacêutica contendo os mesmos
JP2007524641A (ja) * 2003-07-11 2007-08-30 セラヴァンス， インコーポレーテッド 置換４−アミノ−１−ベンジルピペリジン化合物
FR2861073B1 (fr) * 2003-10-17 2006-01-06 Sanofi Synthelabo Derives de n-[heteroaryl(piperidin-2-yl)methyl]benzamide, leur preparation et leur application en therapeutique
US7214439B2 (en) * 2003-12-19 2007-05-08 Millennium Cell, Inc. Triborohydride salts as hydrogen storage materials and preparation thereof
WO2008133900A1 (en) 2007-04-24 2008-11-06 Theravance, Inc. Quaternary ammonium compounds useful as muscarinic receptor antagonists
DE102007020492A1 (de) * 2007-04-30 2008-11-06 Grünenthal GmbH Substituierte Sulfonamid-Derivate
EP3170807B1 (en) * 2015-11-23 2019-12-11 Frau Pharma S.r.l. New method for synthesis of fenfluramine
SI25272A (sl) 2016-09-23 2018-03-30 Univerza V Ljubljani Disubstituirani azetidini, pirolidini, piperidini in azepani kot zaviralci monoamin oksidaze B za zdravljenje nevrodegenerativnih bolezni
CN112824378A (zh) * 2019-11-20 2021-05-21 珠海润都制药股份有限公司 一种盐酸坦索罗辛的制备方法

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Publication number Priority date Publication date Assignee Title
EP0361791B1 (en) 1988-09-26 1995-11-08 Smithkline Beecham Farmaceutici S.p.A. Azacyclic derivatives useful as medicaments
SU1829346A1 (ru) * 1991-04-01 1996-01-10 Институт Тонкой Органической Химии Им.А.Л.Мнджояна ДИГИДРОХЛОРИДЫ N-[β-(1,2,5-ТРИМЕТИЛ-4-АРИЛПИПЕРИДИН-4-ИЛ)ЭТИЛ]-N-АЛКИЛ-N-(3,4-ДИМЕТОКСИБЕНЗИЛ)АМИНОВ, ЯВЛЯЮЩИЕСЯ ИНГИБИТОРАМИ КАЛЬЦИЙ-КАЛЬМОДУЛИНЗАВИСИМЫХ ПРОЦЕССОВ
MY110227A (en) 1991-08-12 1998-03-31 Ciba Geigy Ag 1-acylpiperindine compounds.
FR2681320B1 (fr) 1991-09-12 1994-01-14 Synthelabo Derives de n-(4,7dimethoxyindan-2-yl)-1-(phenylcarbonyl)-n-propyl-piperidine-4-methanamine, leur preparation et leur application en therapeutique.
FR2681325B1 (fr) 1991-09-16 1993-12-17 Fabre Medicament Pierre Derives de l'aminomethyl-4 piperidine, leur preparation et leur application en therapeutique.
ATE256110T1 (de) 1995-09-15 2003-12-15 Neurosearch As Piperindinverbindungen als calcium-kanal-blocker
DE69615214T2 (de) * 1995-10-13 2002-06-27 Banyu Pharmaceutical Co., Ltd. Substituierte heteroaromatische derivate

Also Published As

Publication number Publication date
KR100384906B1 (ko) 2003-05-23
CA2321198C (en) 2009-11-17
CA2321198A1 (en) 1999-09-02
DE69939053D1 (de) 2008-08-21
IL137936A0 (en) 2001-10-31
RU2220138C2 (ru) 2003-12-27
JP3523198B2 (ja) 2004-04-26
KR20010041321A (ko) 2001-05-15
HUP0100760A2 (hu) 2001-08-28
HRP20000544A2 (en) 2001-02-28
HUP0100760A3 (en) 2002-12-28
AU753255B2 (en) 2002-10-10
MY133445A (en) 2007-11-30
HK1036623A1 (en) 2002-01-11
ATE400554T1 (de) 2008-07-15
CN1295563A (zh) 2001-05-16
EP1058680A1 (en) 2000-12-13
MA26610A1 (fr) 2004-12-20
NO20004261L (no) 2000-08-25
CN1143848C (zh) 2004-03-31
CO4990939A1 (es) 2000-12-26
EP1058680B1 (en) 2008-07-09
PL194037B1 (pl) 2007-04-30
YU53100A (sh) 2003-04-30
ES2310032T3 (es) 2008-12-16
WO1999043657A1 (en) 1999-09-02
AR015523A1 (es) 2001-05-02
US6319920B1 (en) 2001-11-20
NO317106B1 (no) 2004-08-09
AU2835399A (en) 1999-09-15
PE20000325A1 (es) 2000-05-08
JP2002504543A (ja) 2002-02-12
NO20004261D0 (no) 2000-08-25
NZ506317A (en) 2003-08-29
PL342692A1 (en) 2001-07-02
TR200002481T2 (tr) 2000-11-21

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Legal Events

Date Code Title Description
B07A Application suspended after technical examination (opinion) [chapter 7.1 patent gazette]
B15K Others concerning applications: alteration of classification

Free format text: ALTERADA DE INT.CL: C07D 211/06, C07D 405/15, C07D 413/12, C07D 411/14, C07D 401/12, C07D 405/12, C07D 411/12, C07D 413/14, A61K 31/455, A61K 31/496, A61K 31/5375 A61P 11/00, A61P 9/00, A61P 27/08

Ipc: C07D 211/06 (2008.04), C07D 405/14 (2008.04), C07D

B09B Patent application refused [chapter 9.2 patent gazette]

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