SK9122003A3 - Tetrahydropyridine derivatives, their preparation and their use as cell proliferation inhibitors - Google Patents

Tetrahydropyridine derivatives, their preparation and their use as cell proliferation inhibitors Download PDF

Info

Publication number: SK9122003A3
Authority: SK; Slovakia
Prior art keywords: dihydro; isoquinolin; group; formula; compound
Prior art date: 2000-12-23

Application number

SK912-2003A

Other languages

English (en)

Slovak (sk)

Inventor

Guy Georges

Adelbert Grossmann

Olaf Mundigl

Der Saal Wolfgang Von

Tim Sattelkau

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.)

2000-12-23

Filing date

2001-12-21

Publication date

2004-02-03

2001-12-21 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

2004-02-03 Publication of SK9122003A3 publication Critical patent/SK9122003A3/sk

Links

230000004663 cell proliferation Effects 0.000 title claims description 7
238000002360 preparation method Methods 0.000 title claims description 7
239000003112 inhibitor Substances 0.000 title claims description 5
VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical class C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 title description 16
150000001875 compounds Chemical class 0.000 claims abstract description 51
238000000034 method Methods 0.000 claims abstract description 19
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 4
230000008569 process Effects 0.000 claims abstract description 4
-1 amino- Chemical class 0.000 claims description 41
125000000217 alkyl group Chemical group 0.000 claims description 19
125000001424 substituent group Chemical group 0.000 claims description 17
150000003839 salts Chemical class 0.000 claims description 14
239000000203 mixture Substances 0.000 claims description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 8
102000003964 Histone deacetylase Human genes 0.000 claims description 8
108090000353 Histone deacetylase Proteins 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
125000006239 protecting group Chemical group 0.000 claims description 8
125000003282 alkyl amino group Chemical group 0.000 claims description 7
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 6
239000000460 chlorine Substances 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
230000002401 inhibitory effect Effects 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
125000005236 alkanoylamino group Chemical group 0.000 claims description 5
125000005530 alkylenedioxy group Chemical group 0.000 claims 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 claims description 4
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UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
239000003814 drug Substances 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
125000001041 indolyl group Chemical group 0.000 claims description 4
RGUVUPQQFXCJFC-UHFFFAOYSA-N n-hydroxyoctanamide Chemical compound CCCCCCCC(=O)NO RGUVUPQQFXCJFC-UHFFFAOYSA-N 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
125000004434 sulfur atom Chemical group 0.000 claims description 4
NIDFZDATJZQXTB-UHFFFAOYSA-N 8-(3,4-dihydro-1h-isoquinolin-2-yl)-n-hydroxyoctanamide Chemical compound C1=CC=C2CN(CCCCCCCC(=O)NO)CCC2=C1 NIDFZDATJZQXTB-UHFFFAOYSA-N 0.000 claims description 3
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125000002009 alkene group Chemical group 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
238000007327 hydrogenolysis reaction Methods 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
WSOCEYYLZHIVEI-UHFFFAOYSA-N 8-(6,7-diethoxy-3,4-dihydro-1h-isoquinolin-2-yl)-n-hydroxyoctanamide Chemical compound C1CN(CCCCCCCC(=O)NO)CC2=C1C=C(OCC)C(OCC)=C2 WSOCEYYLZHIVEI-UHFFFAOYSA-N 0.000 claims description 2
CNUTXVMVZXKCPJ-UHFFFAOYSA-N 8-(6,7-dimethoxy-1-phenyl-3,4-dihydro-1h-isoquinolin-2-yl)-n-hydroxyoctanamide Chemical compound C1=2C=C(OC)C(OC)=CC=2CCN(CCCCCCCC(=O)NO)C1C1=CC=CC=C1 CNUTXVMVZXKCPJ-UHFFFAOYSA-N 0.000 claims description 2
GWBJXKKKWGIYMG-UHFFFAOYSA-N 8-(6,7-dimethoxy-1-propan-2-yl-3,4-dihydro-1h-isoquinolin-2-yl)-n-hydroxyoctanamide Chemical compound C1CN(CCCCCCCC(=O)NO)C(C(C)C)C2=C1C=C(OC)C(OC)=C2 GWBJXKKKWGIYMG-UHFFFAOYSA-N 0.000 claims description 2
MIIOZNKTWSSHFH-UHFFFAOYSA-N 8-(6,7-dimethoxy-3-methyl-3,4-dihydro-1h-isoquinolin-2-yl)-n-hydroxyoctanamide Chemical compound C1C(C)N(CCCCCCCC(=O)NO)CC2=C1C=C(OC)C(OC)=C2 MIIOZNKTWSSHFH-UHFFFAOYSA-N 0.000 claims description 2
239000004480 active ingredient Substances 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
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RZIWVBYJMFCTQG-UHFFFAOYSA-N 8-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)-n-hydroxyoctanamide Chemical compound C1CN(CCCCCCCC(=O)NO)CC2=C1C=C(OC)C(OC)=C2 RZIWVBYJMFCTQG-UHFFFAOYSA-N 0.000 claims 1
125000002947 alkylene group Chemical group 0.000 claims 1
125000005237 alkyleneamino group Chemical group 0.000 claims 1
230000000694 effects Effects 0.000 abstract description 5
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230000035755 proliferation Effects 0.000 abstract 1
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239000002585 base Substances 0.000 description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
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DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
241000124008 Mammalia Species 0.000 description 6
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
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UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical group C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 4
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235000013024 sodium fluoride Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
201000000498 stomach carcinoma Diseases 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
229960001603 tamoxifen Drugs 0.000 description 1
RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
ZXLDQJLIBNPEFJ-UHFFFAOYSA-N tetrahydro-beta-carboline Natural products C1CNC(C)C2=C1C1=CC=C(OC)C=C1N2 ZXLDQJLIBNPEFJ-UHFFFAOYSA-N 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
229940044693 topoisomerase inhibitor Drugs 0.000 description 1
230000002103 transcriptional effect Effects 0.000 description 1
230000009466 transformation Effects 0.000 description 1
229960000575 trastuzumab Drugs 0.000 description 1
210000003932 urinary bladder Anatomy 0.000 description 1
229960003048 vinblastine Drugs 0.000 description 1
JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- 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
- 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
- A61P35/02—Antineoplastic agents specific for leukemia
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Hematology (AREA)
Oncology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Other In-Based Heterocyclic Compounds (AREA)

SK912-2003A 2000-12-23 2001-12-21 Tetrahydropyridine derivatives, their preparation and their use as cell proliferation inhibitors SK9122003A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP00128487		2000-12-23
PCT/EP2001/015390 WO2002051842A1 (en)	2000-12-23	2001-12-21	Tetrahydropyridine derivatives, their preparation and their use as cell proliferation inhibitors

Publications (1)

Publication Number	Publication Date
SK9122003A3 true SK9122003A3 (en)	2004-02-03

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ID=8170814

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK912-2003A SK9122003A3 (en)	2000-12-23	2001-12-21	Tetrahydropyridine derivatives, their preparation and their use as cell proliferation inhibitors

Country Status (27)

Country	Link
US (1)	US6800638B2 (cs)
EP (1)	EP1353921B1 (cs)
JP (1)	JP2004516325A (cs)
KR (1)	KR100836545B1 (cs)
CN (1)	CN1213046C (cs)
AR (1)	AR035513A1 (cs)
AT (1)	ATE323700T1 (cs)
AU (1)	AU2002226397B2 (cs)
BG (1)	BG107935A (cs)
BR (1)	BR0116402A (cs)
CA (1)	CA2431471A1 (cs)
CZ (1)	CZ20031940A3 (cs)
DE (1)	DE60118975T2 (cs)
EC (1)	ECSP034664A (cs)
ES (1)	ES2261519T3 (cs)
HU (1)	HUP0400554A2 (cs)
IL (1)	IL156131A0 (cs)
MA (1)	MA26976A1 (cs)
MX (1)	MXPA03005713A (cs)
NO (1)	NO20032830L (cs)
NZ (1)	NZ526189A (cs)
PL (1)	PL365531A1 (cs)
RU (1)	RU2276140C2 (cs)
SK (1)	SK9122003A3 (cs)
WO (1)	WO2002051842A1 (cs)
YU (1)	YU48803A (cs)
ZA (1)	ZA200304264B (cs)

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CN1905881A (zh) *	2003-11-26	2007-01-31	阿托恩药品公司	二胺和亚氨二醋酸异羟肟酸衍生物
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JP2008524246A (ja)	2004-12-16	2008-07-10	タケダサンディエゴインコーポレイテッド	ヒストンデアセチラーゼ阻害剤
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WO2006122319A2 (en)	2005-05-11	2006-11-16	Takeda San Diego, Inc.	Histone deacetylase inhibitors
ZA200800901B (en)	2005-07-14	2010-05-26	Takeda San Diego Inc	Histone deacetylase inhibitors
EP2258359A3 (en)	2005-08-26	2011-04-06	Braincells, Inc.	Neurogenesis by muscarinic receptor modulation with sabcomelin
JP2009506069A (ja)	2005-08-26	2009-02-12	ブレインセルス，インコーポレイティド	ムスカリン性受容体調節による神経発生
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WO2007053596A1 (en)	2005-10-31	2007-05-10	Braincells, Inc.	Gaba receptor mediated modulation of neurogenesis
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US20100216734A1 (en)	2006-03-08	2010-08-26	Braincells, Inc.	Modulation of neurogenesis by nootropic agents
WO2007134077A2 (en)	2006-05-09	2007-11-22	Braincells, Inc.	5 ht receptor mediated neurogenesis
WO2007134136A2 (en)	2006-05-09	2007-11-22	Braincells, Inc.	Neurogenesis by modulating angiotensin
EP2068872A1 (en)	2006-09-08	2009-06-17	Braincells, Inc.	Combinations containing a 4-acylaminopyridine derivative
US20100184806A1 (en)	2006-09-19	2010-07-22	Braincells, Inc.	Modulation of neurogenesis by ppar agents
TWI425945B (zh) *	2007-05-28	2014-02-11	Seldar Pharma Inc	四氫異喹啉－１－酮衍生物或其鹽
WO2010099217A1 (en)	2009-02-25	2010-09-02	Braincells, Inc.	Modulation of neurogenesis using d-cycloserine combinations
US8431538B2 (en) *	2009-07-22	2013-04-30	The Board Of Trustees Of The University Of Illinois	HDAC inhibitors and therapeutic methods of using same
CN102153549B (zh) *	2010-12-14	2012-11-14	华东理工大学	γ咔啉化合物、制备方法和用途
HUE041881T2 (hu)	2013-04-29	2019-06-28	Chong Kun Dang Pharmaceutical Corp	Új vegyületek mint szelektív hiszton dezacetiláz inhibitorok és az ezeket tartalmazó gyógyszerkészítmények
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2001
- 2001-12-06 AR ARP010105675A patent/AR035513A1/es not_active Application Discontinuation
- 2001-12-21 HU HU0400554A patent/HUP0400554A2/hu unknown
- 2001-12-21 CZ CZ20031940A patent/CZ20031940A3/cs unknown
- 2001-12-21 AU AU2002226397A patent/AU2002226397B2/en not_active Ceased
- 2001-12-21 CA CA002431471A patent/CA2431471A1/en not_active Abandoned
- 2001-12-21 PL PL01365531A patent/PL365531A1/xx not_active Application Discontinuation
- 2001-12-21 DE DE60118975T patent/DE60118975T2/de not_active Expired - Fee Related
- 2001-12-21 NZ NZ526189A patent/NZ526189A/en unknown
- 2001-12-21 EP EP01995721A patent/EP1353921B1/en not_active Expired - Lifetime
- 2001-12-21 ES ES01995721T patent/ES2261519T3/es not_active Expired - Lifetime
- 2001-12-21 BR BR0116402-3A patent/BR0116402A/pt not_active IP Right Cessation
- 2001-12-21 IL IL15613101A patent/IL156131A0/xx unknown
- 2001-12-21 RU RU2003122190/04A patent/RU2276140C2/ru active
- 2001-12-21 CN CNB018212050A patent/CN1213046C/zh not_active Expired - Fee Related
- 2001-12-21 MX MXPA03005713A patent/MXPA03005713A/es active IP Right Grant
- 2001-12-21 SK SK912-2003A patent/SK9122003A3/sk unknown
- 2001-12-21 AT AT01995721T patent/ATE323700T1/de not_active IP Right Cessation
- 2001-12-21 KR KR1020037008028A patent/KR100836545B1/ko not_active Expired - Fee Related
- 2001-12-21 JP JP2002552937A patent/JP2004516325A/ja not_active Ceased
- 2001-12-21 YU YU48803A patent/YU48803A/sh unknown
- 2001-12-21 US US10/451,757 patent/US6800638B2/en not_active Expired - Fee Related
- 2001-12-21 WO PCT/EP2001/015390 patent/WO2002051842A1/en not_active Ceased
2003
- 2003-05-30 ZA ZA200304264A patent/ZA200304264B/en unknown
- 2003-06-20 NO NO20032830A patent/NO20032830L/no not_active Application Discontinuation
- 2003-06-20 MA MA27207A patent/MA26976A1/fr unknown
- 2003-06-22 EC EC2003004664A patent/ECSP034664A/es unknown
- 2003-06-23 BG BG107935A patent/BG107935A/bg unknown

Also Published As

Publication number	Publication date
ES2261519T3 (es)	2006-11-16
US6800638B2 (en)	2004-10-05
JP2004516325A (ja)	2004-06-03
IL156131A0 (en)	2003-12-23
AR035513A1 (es)	2004-06-02
AU2002226397B2 (en)	2006-10-05
CA2431471A1 (en)	2002-07-04
ATE323700T1 (de)	2006-05-15
CN1483033A (zh)	2004-03-17
KR20030063424A (ko)	2003-07-28
CN1213046C (zh)	2005-08-03
EP1353921B1 (en)	2006-04-19
ZA200304264B (en)	2004-08-30
DE60118975T2 (de)	2006-12-21
NO20032830D0 (no)	2003-06-20
RU2276140C2 (ru)	2006-05-10
YU48803A (sh)	2006-05-25
PL365531A1 (en)	2005-01-10
HUP0400554A2 (hu)	2004-06-28
WO2002051842A1 (en)	2002-07-04
NO20032830L (no)	2003-08-04
MXPA03005713A (es)	2003-10-06
BR0116402A (pt)	2003-11-11
KR100836545B1 (ko)	2008-06-10
NZ526189A (en)	2004-10-29
BG107935A (bg)	2004-08-31
CZ20031940A3 (cs)	2003-10-15
RU2003122190A (ru)	2005-02-27
MA26976A1 (fr)	2004-12-20
US20040053960A1 (en)	2004-03-18
EP1353921A1 (en)	2003-10-22
ECSP034664A (es)	2003-07-25
DE60118975D1 (de)	2006-05-24

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