BRPI0401031A - Compostos de isoquinolina, processo para sua preparação e composições farmacêuticas contendo os mesmos - Google Patents

Compostos de isoquinolina, processo para sua preparação e composições farmacêuticas contendo os mesmos

Info

Publication number
BRPI0401031A
BRPI0401031A BR0401031-0A BRPI0401031A BRPI0401031A BR PI0401031 A BRPI0401031 A BR PI0401031A BR PI0401031 A BRPI0401031 A BR PI0401031A BR PI0401031 A BRPI0401031 A BR PI0401031A
Authority
BR
Brazil
Prior art keywords
preparation
pharmaceutical compositions
compositions containing
isoquinoline compounds
group
Prior art date
Application number
BR0401031-0A
Other languages
English (en)
Inventor
Sophie Poissonnier-Durieux
Valerie Wallez
Anne Gasnereau
Said Yous
Daniel Lesieur
Philippe Delagrange
Pierre Renard
Caroline Bennejean
Jean Albert Boutin
Valerie Audinot
Original Assignee
Servier Lab
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 Servier Lab filed Critical Servier Lab
Publication of BRPI0401031A publication Critical patent/BRPI0401031A/pt

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
    • C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
    • C07D217/16—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals substituted by oxygen atoms
    • A—HUMAN NECESSITIES
    • A45—HAND OR TRAVELLING ARTICLES
    • A45F—TRAVELLING OR CAMP EQUIPMENT: SACKS OR PACKS CARRIED ON THE BODY
    • A45F5/00—Holders or carriers for hand articles; Holders or carriers for use while travelling or camping
    • 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
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/18—Feminine contraceptives
    • 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
    • A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
    • 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
    • A61P25/06—Antimigraine agents
    • 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
    • A61P25/08—Antiepileptics; Anticonvulsants
    • 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
    • A61P25/20—Hypnotics; Sedatives
    • 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
    • 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
    • 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
    • A61P3/02—Nutrients, e.g. vitamins, minerals
    • 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
    • A61P3/04—Anorexiants; Antiobesity agents
    • 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
    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • 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
    • 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
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
    • F16B—DEVICES FOR FASTENING OR SECURING CONSTRUCTIONAL ELEMENTS OR MACHINE PARTS TOGETHER, e.g. NAILS, BOLTS, CIRCLIPS, CLAMPS, CLIPS OR WEDGES; JOINTS OR JOINTING
    • F16B45/00—Hooks; Eyes
    • F16B45/02—Hooks with pivoting or elastically bending closing member
    • A—HUMAN NECESSITIES
    • A45—HAND OR TRAVELLING ARTICLES
    • A45F—TRAVELLING OR CAMP EQUIPMENT: SACKS OR PACKS CARRIED ON THE BODY
    • A45F5/00—Holders or carriers for hand articles; Holders or carriers for use while travelling or camping
    • A45F2005/006—Holders or carriers for hand articles; Holders or carriers for use while travelling or camping comprising a suspension strap or lanyard
    • A—HUMAN NECESSITIES
    • A45—HAND OR TRAVELLING ARTICLES
    • A45F—TRAVELLING OR CAMP EQUIPMENT: SACKS OR PACKS CARRIED ON THE BODY
    • A45F2200/00—Details not otherwise provided for in A45F
    • A45F2200/05—Holder or carrier for specific articles
    • A45F2200/0516—Portable handheld communication devices, e.g. mobile phone, pager, beeper, PDA, smart phone

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Diabetes (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Pain & Pain Management (AREA)
  • Endocrinology (AREA)
  • Immunology (AREA)
  • Psychiatry (AREA)
  • Psychology (AREA)
  • Reproductive Health (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • General Engineering & Computer Science (AREA)
  • Child & Adolescent Psychology (AREA)
  • Hospice & Palliative Care (AREA)
  • Emergency Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Nutrition Science (AREA)
  • Anesthesiology (AREA)
  • Rheumatology (AREA)
  • Mechanical Engineering (AREA)
  • Gynecology & Obstetrics (AREA)
  • Vascular Medicine (AREA)

Abstract

"COMPOSTOS DE ISOQUINOLINA, PROCESSO PARA SUA PREPARAçãO E COMPOSIçõES FARMACêUTICAS CONTENDO OS MESMOS". Composto da fórmula (i): onde: n é 1, 2 ou 3, A representa um grupo ou um grupo X representa N ou NR^ 1, R^ 2^ representa um grupo alcóxi, cicloalquilóxi ou cicloalquilalquilóxi.
BR0401031-0A 2003-04-09 2004-04-07 Compostos de isoquinolina, processo para sua preparação e composições farmacêuticas contendo os mesmos BRPI0401031A (pt)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR0304381A FR2853649B1 (fr) 2003-04-09 2003-04-09 Nouveaux derives d'isoquinoleine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent

Publications (1)

Publication Number Publication Date
BRPI0401031A true BRPI0401031A (pt) 2005-01-18

Family

ID=32865399

Family Applications (1)

Application Number Title Priority Date Filing Date
BR0401031-0A BRPI0401031A (pt) 2003-04-09 2004-04-07 Compostos de isoquinolina, processo para sua preparação e composições farmacêuticas contendo os mesmos

Country Status (31)

Country Link
US (2) US7214689B2 (pt)
EP (1) EP1466604B1 (pt)
JP (1) JP4195869B2 (pt)
KR (1) KR100673702B1 (pt)
CN (1) CN100497313C (pt)
AR (1) AR043997A1 (pt)
AT (1) ATE377421T1 (pt)
AU (1) AU2004201595B2 (pt)
BR (1) BRPI0401031A (pt)
CA (1) CA2462939C (pt)
CY (1) CY1107158T1 (pt)
DE (1) DE602004009849T2 (pt)
DK (1) DK1466604T3 (pt)
EA (1) EA007714B1 (pt)
EG (1) EG24369A (pt)
ES (1) ES2295794T3 (pt)
FR (1) FR2853649B1 (pt)
GE (1) GEP20053636B (pt)
HK (1) HK1067121A1 (pt)
HR (1) HRP20070549T3 (pt)
MA (1) MA27070A1 (pt)
MX (1) MXPA04003200A (pt)
MY (1) MY136928A (pt)
NO (1) NO327107B1 (pt)
NZ (1) NZ532221A (pt)
PL (1) PL1466604T3 (pt)
PT (1) PT1466604E (pt)
SG (1) SG145542A1 (pt)
SI (1) SI1466604T1 (pt)
UA (1) UA81610C2 (pt)
ZA (1) ZA200402657B (pt)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2881138B1 (fr) * 2005-01-27 2007-03-02 Servier Lab Nouveaux derives d'oximes heterocycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
EP1731507A1 (en) 2005-04-26 2006-12-13 Institut National des Sciences Appliquees de Rouen (INSA) New heterocyclic compounds, their preparation and their use as medicaments, in particular as anti-alzheimer agents
CN100386319C (zh) * 2005-12-05 2008-05-07 中国人民解放军第二军医大学 具有抗生育和抗真菌活性的四氢异喹啉类化合物或其盐类
US8389544B2 (en) * 2007-01-17 2013-03-05 The Hong Kong University Of Science And Technology Isoquinolone compounds as subtype-selective agonists for melatonin receptors MT1 and MT2
WO2009118765A2 (en) * 2008-03-28 2009-10-01 Panacea Biotec Limited Novel monoamine re-uptake inhibitor
ES2580702B1 (es) 2015-02-25 2017-06-08 Palobiofarma, S.L. Derivados de 2-aminopiridina como antagonistas del receptor A2b de adenosina y ligandos del receptor MT3 de melatonina
CN116249691A (zh) * 2020-07-28 2023-06-09 上海翰森生物医药科技有限公司 双环类衍生物调节剂、其制备方法和应用

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HU189764B (en) * 1983-10-25 1986-07-28 Richter Gedeon Vegyeszeti Gyar Rt,Hu Process for preparing 1-(bis (substituted methyl)-methyl)-isoquinoline-derivatives
US4584379A (en) * 1985-01-22 1986-04-22 Merrell Dow Pharmaceuticals Inc. Isoquinoline thromboxane synthetase inhibitors
DE3640641A1 (de) * 1986-11-28 1988-07-14 Thomae Gmbh Dr K Neue heteroaromatische aminderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung
DE3718570A1 (de) * 1987-06-03 1988-12-15 Boehringer Ingelheim Kg Benzo- und thieno-3,4-dihydro-1- pyridinylessigsaeurederivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
FR2658818B1 (fr) * 1990-02-27 1993-12-31 Adir Cie Nouveaux derives a structure naphtalenique, leur procede de preparation et les compositions pharmaceutiques qui les contiennent.
AU688833B2 (en) * 1993-12-21 1998-03-19 Boehringer Ingelheim International Gmbh Anellated dihydropyridines and their use in the production of pharmaceutical preparations
FR2729147A1 (fr) * 1995-01-11 1996-07-12 Adir Nouveaux composes (hetero) cycliques alkyles, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
US5708005A (en) * 1995-06-27 1998-01-13 Takeda Chemical Industries, Ltd. Quinolines, their production and use
FR2778662B1 (fr) * 1998-05-12 2000-06-16 Adir Nouveaux composes cycliques substitues, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
FR2801885B1 (fr) * 1999-12-06 2002-01-11 Adir Nouveaux derives (dihydro)benzoxaziniques et (dihydro) benzothiaziniques substitues, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
ES2172376B1 (es) * 2000-01-28 2003-11-16 Servier Lab Nuevos derivados de isoquinoleinas, su procedimiento de preparacion y las composiciones farmaceuticas que los contienen.

Also Published As

Publication number Publication date
HK1067121A1 (en) 2005-04-01
EP1466604A1 (fr) 2004-10-13
US7214689B2 (en) 2007-05-08
AR043997A1 (es) 2005-08-17
EA007714B1 (ru) 2006-12-29
DK1466604T3 (da) 2008-03-03
GEP20053636B (en) 2005-10-10
EG24369A (en) 2009-03-15
EP1466604B1 (fr) 2007-11-07
DE602004009849T2 (de) 2008-09-04
JP4195869B2 (ja) 2008-12-17
CA2462939A1 (fr) 2004-10-09
HRP20070549T3 (en) 2008-07-31
CY1107158T1 (el) 2012-10-24
CN100497313C (zh) 2009-06-10
DE602004009849D1 (de) 2007-12-20
CN1535957A (zh) 2004-10-13
ATE377421T1 (de) 2007-11-15
ZA200402657B (en) 2004-10-14
AU2004201595B2 (en) 2010-01-21
FR2853649B1 (fr) 2006-07-14
SG145542A1 (en) 2008-09-29
PL1466604T3 (pl) 2008-03-31
KR100673702B1 (ko) 2007-01-24
SI1466604T1 (sl) 2008-02-29
EA200400409A1 (ru) 2004-10-28
NO327107B1 (no) 2009-04-20
JP2004307492A (ja) 2004-11-04
MA27070A1 (fr) 2004-12-20
UA81610C2 (ru) 2008-01-25
PT1466604E (pt) 2007-12-21
MXPA04003200A (es) 2004-10-14
NO20041313L (no) 2004-10-11
MY136928A (en) 2008-11-28
AU2004201595A1 (en) 2004-10-28
NZ532221A (en) 2005-07-29
US20070191328A1 (en) 2007-08-16
ES2295794T3 (es) 2008-04-16
US20040204449A1 (en) 2004-10-14
CA2462939C (fr) 2010-04-27
FR2853649A1 (fr) 2004-10-15
KR20040087964A (ko) 2004-10-15

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Legal Events

Date Code Title Description
B06F Objections, documents and/or translations needed after an examination request according [chapter 6.6 patent gazette]
B15K Others concerning applications: alteration of classification

Free format text: PARA INT.CL: C07D 217/12, A61K 31/47, A61P 15/00

Ipc: C07D 217/12 (2011.01), A61K 31/47 (2011.01)

B08L Patent application lapsed because of non payment of annual fee [chapter 8.12 patent gazette]

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