MD2336F2 - Crystalline hydrate of 6-hydroxy-3-(4-[2-(piperidine-1-yl)ethoxy]phenoxy)-2-(4-methoxyphenyl)benzo[b]thiophene hydrochloride, process for obtaining, pharmaceutical composition containing thereof and application for inhibition of the pathologic states and activation choline acetyltransferase - Google Patents

Crystalline hydrate of 6-hydroxy-3-(4-[2-(piperidine-1-yl)ethoxy]phenoxy)-2-(4-methoxyphenyl)benzo[b]thiophene hydrochloride, process for obtaining, pharmaceutical composition containing thereof and application for inhibition of the pathologic states and activation choline acetyltransferase

Info

Publication number
MD2336F2
MD2336F2 MDA20000162A MD20000162A MD2336F2 MD 2336 F2 MD2336 F2 MD 2336F2 MD A20000162 A MDA20000162 A MD A20000162A MD 20000162 A MD20000162 A MD 20000162A MD 2336 F2 MD2336 F2 MD 2336F2
Authority
MD
Moldova
Prior art keywords
benzo
methoxyphenyl
piperidine
phenoxy
ethoxy
Prior art date
Application number
MDA20000162A
Other languages
Romanian (ro)
Other versions
MD2336G2 (en
MD20000162A (en
Inventor
Julie Kay Bush
Preston Charles Conrad
Merlyn Gerard Flom
Wayne Douglas Luke
Original Assignee
Lilly Co Eli
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 Lilly Co Eli filed Critical Lilly Co Eli
Publication of MD20000162A publication Critical patent/MD20000162A/en
Publication of MD2336F2 publication Critical patent/MD2336F2/en
Publication of MD2336G2 publication Critical patent/MD2336G2/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
    • C07D333/64—Oxygen atoms
    • 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
    • C07D409/12—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 chain containing hetero atoms as chain links
    • 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
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/4535—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a heterocyclic ring having sulfur as a ring hetero atom, e.g. pizotifen
    • 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
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
    • A61K31/567—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in position 17 alpha, e.g. mestranol, norethandrolone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
    • A61K38/08—Peptides having 5 to 11 amino acids
    • A61K38/09—Luteinising hormone-releasing hormone [LHRH], i.e. Gonadotropin-releasing hormone [GnRH]; Related peptides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • 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
    • 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
    • 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
    • A61P3/06—Antihyperlipidemics
    • 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
    • A61P35/04—Antineoplastic agents specific for metastasis
    • 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
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
    • A61P5/30—Oestrogens
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
    • A61P5/32—Antioestrogens
    • 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

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Epidemiology (AREA)
  • Diabetes (AREA)
  • Endocrinology (AREA)
  • Biomedical Technology (AREA)
  • Rheumatology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Reproductive Health (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Psychiatry (AREA)
  • Urology & Nephrology (AREA)
  • Hospice & Palliative Care (AREA)
  • Oncology (AREA)
  • Vascular Medicine (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Immunology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

The invention relates to the pharmaceutical technology, in particular to a new crystalline form of 6-hydroxy-3-(4-[2-(piperidine-1-yl)ethoxy]phenoxy)-2-(4-methoxyphenyl)benzo [b]thiophene hydrochloride, to a process for obtaining thereof and to a composition containing it. The crystalline hydrate of 6-hydroxy-3-(4-[2-(piperidine-1-yl)ethoxy]phenoxy)-2-(4-methoxyphenyl)benzo[b]thiophene hydrochloride (arzophene), F-1, represents a compound with a high degree of crystallinity. The pharmaceutical composition on base thereof contains one or more carriers, diluents or substituents and, if appropriate, estrogen, progestin, an aromatase inhibitor, a hormone analogue, releasing the luteinizing hormone (LHRH) and an acetylcholine esterase inhibitor. The process for obtaining of said compound provides for the crystallization of 6-hydroxy-3-(4-[2-(piperidine-1-yl)ethoxy]phenoxy)-2-(4-methoxyphenyl) benzo [b]thiophene hydrochloride from tetrahydrofuran.The claimed compound may be used for inhibition of pathological states associated with estrogen deficiency, such as uterine fibrosis, endometriosis, proliferation of aortal, smooth muscular cells in aorta, restenosis, estrogen-dependent cancer (including the mammary cancer and the uterine cancer), prostate cancer, prostate benign hyperplasia, osteoporosis, cardiovascular affections, hyperlipoidemia, disorders of the CNS and the Alzheimer's disease, prevention of the mammary cancer and activation of the choline acetyl transferase.Claims: 16
MDA20000162A 1999-07-29 2000-07-28 Crystalline hydrate of 6-hydroxy-3-(4-[2-(piperidine-1-yl)ethoxy]phenoxy)-2-(4-methoxyphenyl)benzo[b]thiophene hydrochloride, process for obtaining, pharmaceutical composition comprising it and use for inhibition of pathological states and activation of choline acetyltransferase MD2336G2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US14628699P 1999-07-29 1999-07-29
US14757099P 1999-08-06 1999-08-06
US14977399P 1999-08-19 1999-08-19

Publications (3)

Publication Number Publication Date
MD20000162A MD20000162A (en) 2001-04-30
MD2336F2 true MD2336F2 (en) 2003-12-31
MD2336G2 MD2336G2 (en) 2004-06-30

Family

ID=27386379

Family Applications (1)

Application Number Title Priority Date Filing Date
MDA20000162A MD2336G2 (en) 1999-07-29 2000-07-28 Crystalline hydrate of 6-hydroxy-3-(4-[2-(piperidine-1-yl)ethoxy]phenoxy)-2-(4-methoxyphenyl)benzo[b]thiophene hydrochloride, process for obtaining, pharmaceutical composition comprising it and use for inhibition of pathological states and activation of choline acetyltransferase

Country Status (45)

Country Link
EP (1) EP1204656A2 (en)
JP (1) JP2001064277A (en)
KR (1) KR100697177B1 (en)
CN (1) CN1138770C (en)
AR (1) AR031073A1 (en)
AT (1) AT502318A1 (en)
AU (1) AU6335600A (en)
BE (1) BE1013411A3 (en)
BR (1) BR0003209A (en)
CA (1) CA2314682A1 (en)
CO (1) CO5180570A1 (en)
CZ (1) CZ299311B6 (en)
DE (1) DE10036854A1 (en)
DK (1) DK200001151A (en)
DZ (1) DZ3060A1 (en)
FI (1) FI20001722A (en)
FR (1) FR2796944B1 (en)
GB (1) GB2352717A (en)
GR (1) GR1004084B (en)
HK (1) HK1035370A1 (en)
HR (1) HRP20000503B1 (en)
HU (1) HUP0003001A2 (en)
ID (1) ID27078A (en)
IL (1) IL137553A (en)
IT (1) IT1318660B1 (en)
LT (1) LT4790B (en)
LU (1) LU90617B1 (en)
LV (1) LV12623B (en)
MD (1) MD2336G2 (en)
MX (1) MXPA00007461A (en)
MY (1) MY128764A (en)
NL (1) NL1015821C2 (en)
NO (1) NO20003879L (en)
PE (1) PE20010385A1 (en)
PL (1) PL341749A1 (en)
PT (1) PT102502A (en)
RO (1) RO121851B1 (en)
SE (1) SE0002792L (en)
SG (1) SG91296A1 (en)
SI (1) SI20426A (en)
SV (1) SV2002000132A (en)
TR (1) TR200002206A2 (en)
TW (1) TWI276437B (en)
UA (1) UA72885C2 (en)
WO (1) WO2001009116A2 (en)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE60005693T2 (en) * 1999-07-29 2004-07-29 Eli Lilly And Co., Indianapolis A CRYSTALLINE FORM OF 6-HYDROXY-3- (4- [2- (PIPERIDIN-1-YL) ETHOXY] PHENOXY) -2- (4-METHOXYPHENYL) BENZO [B] THIOPHENE HYDROCHLORIDE
WO2001085147A2 (en) * 2000-05-08 2001-11-15 Eli Lilly And Company STABILIZED FORMULATIONS OF 6-HYDROXY-3-(4-[2-(PIPERIDIN-1-YL) ETHOXY]PHENOXY)-2-(4-METHOXYPHENYL) BENZO[b]THIOPHENE AND SALTS THEREOF
EP1757291A3 (en) * 2000-05-08 2009-07-15 Eli Lilly & Company Stabilized formulations of 6-hydroxy-3-(4-[2-(piperidin-1-YL)ethoxy]phenoxy)-2-(4-methoxyphenyl)benzo[b]thiophene and salts thereof
US7122203B2 (en) 2000-05-08 2006-10-17 Eli Lilly And Company Stabilized formulations of 6-hydroxy-3-(-4-[2-(piperidin-1-yl) ethoxy]phenoxy)-2-(4-methoxyphenyl) benzo[b]thiophene and salts thereof
EP1157996A1 (en) * 2000-05-23 2001-11-28 JENAPHARM GmbH New solid forms of mesoprogestin 11beta-(4E-(hydroxyiminomethyl)-phenyl)-17alpha-methoxymethyl-17beta-methoxy-estra-4,9-dien-3-on
KR20030037690A (en) * 2000-10-20 2003-05-14 일라이 릴리 앤드 캄파니 A NOVEL CRYSTALLINE FORM OF 6-HYDROXY-3-(4-[2-(PIPERIDIN-1-YL)ETHOXY]PHENOXY)-2-(4-METHOXYPHENYL)BENZO[b] THIOPHENE HYDROCHLORIDE
US6921827B2 (en) 2000-11-27 2005-07-26 Eli Lilly And Company Process for preparing 3-aryl-benzo{b} thiophenes
CA2393720C (en) * 2002-07-12 2010-09-14 Eli Lilly And Company Crystalline 2,5-dione-3-(1-methyl-1h-indol-3-yl)-4-[1-(pyridin-2-ylmethyl)piperidin-4-yl]-1h-indol-3-yl]-1h-pyrrole mono-hydrochloride
ES2349798T3 (en) * 2004-07-22 2011-01-11 Eli Lilly And Company CRYSTAL VARIABLE HYDRATION OF SALT HEMISUCCINATE FROM (S) -6- (4- (2 - ((3- (9H-CARBAZOL-4-ILOXI) -2-HYDROXIPROPIL) AMINO) -2-METHYLPROPIL) PHENOXY) -3- PYRIDINOCARBOXAMIDE.

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL182493B1 (en) * 1995-02-28 2002-01-31 Lilly Co Eli Novel derivatives of bezothiophene, method of obtaining them, novel intermediate compounds and pharmaceutical agent
US5510357A (en) 1995-02-28 1996-04-23 Eli Lilly And Company Benzothiophene compounds as anti-estrogenic agents
ZA9710262B (en) * 1996-11-19 1999-05-13 Lilly Co Eli Process for the synthesis of benzothiophenes
ZA982877B (en) * 1997-04-09 1999-10-04 Lilly Co Eli Treatment of central nervous system disorders with selective estrogen receptor modulators.

Also Published As

Publication number Publication date
ITMI20001759A0 (en) 2000-07-28
MY128764A (en) 2007-02-28
HU0003001D0 (en) 2000-10-28
LV12623B (en) 2001-07-20
PE20010385A1 (en) 2001-04-06
HUP0003001A2 (en) 2002-04-29
GR20000100265A (en) 2001-03-30
AT502318A1 (en) 2007-02-15
SG91296A1 (en) 2002-09-17
IE20000605A1 (en) 2001-04-04
NL1015821C2 (en) 2002-01-03
CO5180570A1 (en) 2002-07-30
MD2336G2 (en) 2004-06-30
PL341749A1 (en) 2001-02-12
EP1204656A2 (en) 2002-05-15
NO20003879L (en) 2001-01-30
MXPA00007461A (en) 2004-07-16
LV12623A (en) 2001-03-20
BE1013411A3 (en) 2001-12-04
RO121851B1 (en) 2008-06-30
FI20001722A0 (en) 2000-07-28
AR031073A1 (en) 2003-09-10
FI20001722A (en) 2001-01-30
NL1015821A1 (en) 2001-01-30
LT4790B (en) 2001-05-25
IL137553A (en) 2005-09-25
IL137553A0 (en) 2001-07-24
GB0018641D0 (en) 2000-09-13
GR1004084B (en) 2002-12-11
MD20000162A (en) 2001-04-30
DK200001151A (en) 2001-01-30
GB2352717A (en) 2001-02-07
SE0002792D0 (en) 2000-07-28
LU90617B1 (en) 2001-06-15
UA72885C2 (en) 2005-05-16
HRP20000503B1 (en) 2008-04-30
FR2796944A1 (en) 2001-02-02
DE10036854A1 (en) 2001-03-01
HK1035370A1 (en) 2001-11-23
KR20010049916A (en) 2001-06-15
WO2001009116A2 (en) 2001-02-08
DZ3060A1 (en) 2004-05-22
BR0003209A (en) 2001-03-20
CN1138770C (en) 2004-02-18
CA2314682A1 (en) 2001-01-29
FR2796944B1 (en) 2003-01-31
AU6335600A (en) 2001-02-19
SE0002792L (en) 2001-01-30
WO2001009116A3 (en) 2001-05-17
LT2000076A (en) 2001-02-26
TR200002206A2 (en) 2001-03-21
KR100697177B1 (en) 2007-03-21
SV2002000132A (en) 2002-06-07
ID27078A (en) 2001-02-22
CZ20002716A3 (en) 2001-05-16
SI20426A (en) 2001-06-30
TWI276437B (en) 2007-03-21
CN1288007A (en) 2001-03-21
IT1318660B1 (en) 2003-08-27
ITMI20001759A1 (en) 2002-01-28
PT102502A (en) 2001-01-31
CZ299311B6 (en) 2008-06-18
NO20003879D0 (en) 2000-07-28
JP2001064277A (en) 2001-03-13
HRP20000503A2 (en) 2001-06-30

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KA4A Patent for invention lapsed due to non-payment of fees (with right of restoration)
MM4A Patent for invention definitely lapsed due to non-payment of fees