CA2526663C - Indole derivatives with apoptosis-inducing effect - Google Patents

Indole derivatives with apoptosis-inducing effect Download PDF

Info

Publication number: CA2526663C
Authority: CA; Canada
Prior art keywords: tautomer; stereoisomer; indole derivative; substituted; physiologically tolerated
Prior art date: 2003-06-05
Legal status (The legal status 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 status listed.): Expired - Fee Related

Application number

CA2526663A

Other languages

English (en)

French (fr)

Other versions

CA2526663A1 (en

Inventor

Matthias Gerlach

Tilmann Schuster

Peter Emig

Peter Schmidt

Silke Bassner

Eckhard Guenther

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Aeterna Zentaris GmbH

Original Assignee

Zentaris AG

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.)

2003-06-05

Filing date

2004-05-25

Publication date

2011-07-19

2003-06-06 Priority claimed from EP03012868A external-priority patent/EP1484329A1/de

2004-05-15 Priority claimed from EP04011598A external-priority patent/EP1595878A1/de

2004-05-25 Application filed by Zentaris AG filed Critical Zentaris AG

2004-12-16 Publication of CA2526663A1 publication Critical patent/CA2526663A1/en

2011-07-19 Application granted granted Critical

2011-07-19 Publication of CA2526663C publication Critical patent/CA2526663C/en

2024-05-25 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

150000002475 indoles Chemical class 0.000 title claims abstract description 28
229940054051 antipsychotic indole derivative Drugs 0.000 title abstract description 10
230000006907 apoptotic process Effects 0.000 title description 8
230000001939 inductive effect Effects 0.000 title description 2
239000003814 drug Substances 0.000 claims abstract description 13
201000009030 Carcinoma Diseases 0.000 claims abstract description 5
150000001875 compounds Chemical class 0.000 claims description 81
-1 6-quinolyl Chemical group 0.000 claims description 35
239000000126 substance Substances 0.000 claims description 34
150000003839 salts Chemical class 0.000 claims description 24
206010028980 Neoplasm Diseases 0.000 claims description 19
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 17
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
229910052739 hydrogen Inorganic materials 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 11
229910052757 nitrogen Inorganic materials 0.000 claims description 9
WPPLMWPBWRANIX-UHFFFAOYSA-N 2-[1-[(4-chlorophenyl)methyl]indol-3-yl]-2-oxo-n-pyrido[2,3-b]pyrazin-7-ylacetamide Chemical compound C1=CC(Cl)=CC=C1CN1C2=CC=CC=C2C(C(=O)C(=O)NC=2C=C3N=CC=NC3=NC=2)=C1 WPPLMWPBWRANIX-UHFFFAOYSA-N 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
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125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 4
206010059866 Drug resistance Diseases 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
239000011593 sulfur Substances 0.000 claims description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 claims description 3
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 3
150000001408 amides Chemical class 0.000 claims description 3
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
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OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 8
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MQLACMBJVPINKE-UHFFFAOYSA-N 10-[(3-hydroxy-4-methoxyphenyl)methylidene]anthracen-9-one Chemical compound C1=C(O)C(OC)=CC=C1C=C1C2=CC=CC=C2C(=O)C2=CC=CC=C21 MQLACMBJVPINKE-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
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125000004435 hydrogen atom Chemical class [H]* 0.000 description 6
PUUYOBLKPDNCBV-UHFFFAOYSA-N 2-[1-[(4-chlorophenyl)methyl]indol-3-yl]-n-(2-methylquinolin-6-yl)-2-oxoacetamide Chemical compound C1=CC2=NC(C)=CC=C2C=C1NC(=O)C(=O)C(C1=CC=CC=C11)=CN1CC1=CC=C(Cl)C=C1 PUUYOBLKPDNCBV-UHFFFAOYSA-N 0.000 description 5
ULMUUHCTNJJUIP-UHFFFAOYSA-N 2-[1-[(4-chlorophenyl)methyl]indol-3-yl]-n-isoquinolin-5-yl-2-oxoacetamide Chemical compound C1=CC(Cl)=CC=C1CN1C2=CC=CC=C2C(C(=O)C(=O)NC=2C3=CC=NC=C3C=CC=2)=C1 ULMUUHCTNJJUIP-UHFFFAOYSA-N 0.000 description 5
WZSTWPSBLYYIPI-UHFFFAOYSA-N 2-[1-[(4-chlorophenyl)methyl]indol-3-yl]-n-quinolin-6-yl-2-sulfanylideneacetamide Chemical compound C1=CC(Cl)=CC=C1CN1C2=CC=CC=C2C(C(=S)C(=O)NC=2C=C3C=CC=NC3=CC=2)=C1 WZSTWPSBLYYIPI-UHFFFAOYSA-N 0.000 description 5
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 5
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230000022131 cell cycle Effects 0.000 description 5
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125000000623 heterocyclic group Chemical group 0.000 description 5
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150000002690 malonic acid derivatives Chemical class 0.000 description 1
229960002510 mandelic acid Drugs 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
230000010534 mechanism of action Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
230000009401 metastasis Effects 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
206010063344 microscopic polyangiitis Diseases 0.000 description 1
210000004688 microtubule Anatomy 0.000 description 1
230000000394 mitotic effect Effects 0.000 description 1
230000036457 multidrug resistance Effects 0.000 description 1
230000000926 neurological effect Effects 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
208000013371 ovarian adenocarcinoma Diseases 0.000 description 1
201000006588 ovary adenocarcinoma Diseases 0.000 description 1
150000003891 oxalate salts Chemical class 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000013641 positive control Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
235000018102 proteins Nutrition 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
229940107700 pyruvic acid Drugs 0.000 description 1
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000013558 reference substance Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000010076 replication Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
239000011369 resultant mixture Substances 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
230000003381 solubilizing effect Effects 0.000 description 1
201000011549 stomach cancer Diseases 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
AGGIJOLULBJGTQ-UHFFFAOYSA-N sulfoacetic acid Chemical compound OC(=O)CS(O)(=O)=O AGGIJOLULBJGTQ-UHFFFAOYSA-N 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
150000003536 tetrazoles Chemical class 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
125000005490 tosylate group Chemical group 0.000 description 1
150000008648 triflates Chemical class 0.000 description 1
231100000588 tumorigenic Toxicity 0.000 description 1
230000000381 tumorigenic effect Effects 0.000 description 1
229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
238000009736 wetting Methods 0.000 description 1

Classifications

- 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
- C07D401/12—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 chain containing hetero atoms as chain links
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

CA2526663A 2003-06-05 2004-05-25 Indole derivatives with apoptosis-inducing effect Expired - Fee Related CA2526663C (en)

Applications Claiming Priority (7)

Application Number	Priority Date	Filing Date	Title
US47627703P	2003-06-05	2003-06-05
US60/476,277		2003-06-05
EP03012868A EP1484329A1 (de)	2003-06-06	2003-06-06	Indolderivate mit Apoptose induzierender Wirkung
EP03012868.0		2003-06-06
EP04011598A EP1595878A1 (de)	2004-05-15	2004-05-15	Indolderivate mit Apoptose induzierender Wirkung
EP04011598.2		2004-05-15
PCT/EP2004/005593 WO2004108702A1 (de)	2003-06-05	2004-05-25	Indolderivate mit apoptose induzierender wirkung

Publications (2)

Publication Number	Publication Date
CA2526663A1 CA2526663A1 (en)	2004-12-16
CA2526663C true CA2526663C (en)	2011-07-19

Family

ID=43661564

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA2526663A Expired - Fee Related CA2526663C (en)	2003-06-05	2004-05-25	Indole derivatives with apoptosis-inducing effect

Country Status (12)

Country	Link
EP (1)	EP1641777A1 (pt)
JP (1)	JP4878285B2 (pt)
KR (1)	KR101132599B1 (pt)
CN (1)	CN1816543B (pt)
AU (1)	AU2004245198B2 (pt)
BR (1)	BRPI0410998A (pt)
CA (1)	CA2526663C (pt)
MX (1)	MXPA05013121A (pt)
NZ (1)	NZ543853A (pt)
RS (1)	RS20050901A (pt)
RU (1)	RU2327696C2 (pt)
WO (1)	WO2004108702A1 (pt)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2007054556A1 (de) *	2005-11-11	2007-05-18	Æterna Zentaris Gmbh	Neue pyridopyrazine und deren verwendung als modulatoren von kinasen
EP1790342A1 (de)	2005-11-11	2007-05-30	Zentaris GmbH	Pyridopyrazin-Derivate und deren Verwendung als Modulatoren der Signaltransduktionswege
US8217042B2 (en)	2005-11-11	2012-07-10	Zentaris Gmbh	Pyridopyrazines and their use as modulators of kinases
JP5460054B2 (ja) *	2005-11-23	2014-04-02	ザボードオブリージェンツオブザユニバーシティーオブテキサスシステム	腫瘍形成性ｒａｓ特異的細胞障害性化合物およびその使用法
SG176477A1 (en) *	2006-08-07	2011-12-29	Ironwood Pharmaceuticals Inc	Indole compounds
CA2670778A1 (en) *	2006-11-28	2008-06-05	Ziopharm Oncology, Inc.	Use of indolyl-3-glyoxylic acid derivatives including indibulin, alone or in combination with further agents for treating cancer
DK2349259T3 (en) *	2008-10-16	2016-02-29	Array Biopharma Inc	MITOSE INHIBITORS TO INCREASE APOPTOSE IN THERAPY
WO2012017325A2 (en) *	2010-07-19	2012-02-09	Procaps Sa	Apparatus and process for encapsulating microparticles with liquid in soft gel capsules

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9216009D0 (en) *	1992-07-28	1992-09-09	Almirall Lab	New indol derivatives
DE19814838C2 (de) *	1998-04-02	2001-01-18	Asta Medica Ag	Indolyl-3-glyoxylsäure-Derivate mit Antitumorwirkung
TWI269654B (en) *	1999-09-28	2007-01-01	Baxter Healthcare Sa	N-substituted indole-3-glyoxylamide compounds having anti-tumor action
DE19962300A1 (de) *	1999-12-23	2001-06-28	Asta Medica Ag	Substituierte N-Benzyl-Indol-3-yl-glyoxylsäure-Derivate mit Antitumorwirkung
IT1318641B1 (it) *	2000-07-25	2003-08-27	Novuspharma Spa	Ammidi di acidi 2-(1h-indol-3-il)-2-oxo-acetici ad attivita'antitumorale.
DE10037310A1 (de) *	2000-07-28	2002-02-07	Asta Medica Ag	Neue Indolderivate und deren Verwendung als Arzneimittel
CA2460347A1 (en) *	2001-09-13	2003-03-20	Synta Pharmaceuticals Corp.	3-glyoxlylamideindoles for treating cancer

2004
- 2004-05-25 EP EP04734662A patent/EP1641777A1/de not_active Withdrawn
- 2004-05-25 CA CA2526663A patent/CA2526663C/en not_active Expired - Fee Related
- 2004-05-25 WO PCT/EP2004/005593 patent/WO2004108702A1/de not_active Ceased
- 2004-05-25 KR KR1020057023347A patent/KR101132599B1/ko not_active Expired - Fee Related
- 2004-05-25 JP JP2006508197A patent/JP4878285B2/ja not_active Expired - Fee Related
- 2004-05-25 BR BRPI0410998-8A patent/BRPI0410998A/pt not_active IP Right Cessation
- 2004-05-25 AU AU2004245198A patent/AU2004245198B2/en not_active Ceased
- 2004-05-25 RU RU2006100022/04A patent/RU2327696C2/ru not_active IP Right Cessation
- 2004-05-25 NZ NZ543853A patent/NZ543853A/en not_active IP Right Cessation
- 2004-05-25 MX MXPA05013121A patent/MXPA05013121A/es active IP Right Grant
- 2004-05-25 RS YUP-2005/0901A patent/RS20050901A/sr unknown
- 2004-05-25 CN CN2004800192716A patent/CN1816543B/zh not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CN1816543A (zh)	2006-08-09
JP2007523850A (ja)	2007-08-23
BRPI0410998A (pt)	2006-07-04
RU2327696C2 (ru)	2008-06-27
CA2526663A1 (en)	2004-12-16
AU2004245198A1 (en)	2004-12-16
NZ543853A (en)	2009-09-25
EP1641777A1 (de)	2006-04-05
KR101132599B1 (ko)	2012-06-21
RS20050901A (sr)	2007-12-31
JP4878285B2 (ja)	2012-02-15
CN1816543B (zh)	2011-01-19
WO2004108702A1 (de)	2004-12-16
KR20060034230A (ko)	2006-04-21
MXPA05013121A (es)	2006-03-17
AU2004245198B2 (en)	2009-04-23
RU2006100022A (ru)	2006-05-27

Legal Events

Date	Code	Title	Description
2008-06-13	EEER	Examination request
2014-07-08	MKLA	Lapsed	Effective date: 20140527

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