SK9182002A3 - Novel derivatives of 3-imino-1,2-dithioles, method for producing them and pharmaceutical compositions containing the same - Google Patents

Novel derivatives of 3-imino-1,2-dithioles, method for producing them and pharmaceutical compositions containing the same Download PDF

Info

Publication number: SK9182002A3
Authority: SK; Slovakia
Prior art keywords: formula; compound; pyridyl; group; het
Prior art date: 1999-12-22

Application number

SK918-2002A

Other languages

English (en)

Slovak (sk)

Inventor

Muriel Duflos

Jean-Michel Robert

Marie-Renee Nourrisson

Baut Guillaume Le

Daniel-Henri Caignard

Jean-Guy Bizot-Espiard

Pierre Renard

Original Assignee

Servier Dept Brevets Fontanes

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.)

1999-12-22

Filing date

2000-12-21

Publication date

2002-11-06

2000-12-21 Application filed by Servier Dept Brevets Fontanes filed Critical Servier Dept Brevets Fontanes

2002-11-06 Publication of SK9182002A3 publication Critical patent/SK9182002A3/sk

Links

239000008194 pharmaceutical composition Substances 0.000 title claims description 8
238000004519 manufacturing process Methods 0.000 title claims 3
RWIUQKWSQMMBQD-UHFFFAOYSA-N dithiol-3-imine Chemical class N=C1C=CSS1 RWIUQKWSQMMBQD-UHFFFAOYSA-N 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 49
239000002253 acid Substances 0.000 claims abstract description 12
150000003839 salts Chemical class 0.000 claims abstract description 11
239000003814 drug Substances 0.000 claims abstract 2
238000002360 preparation method Methods 0.000 claims description 17
238000000034 method Methods 0.000 claims description 10
-1 4,6-dimethyl-2-pyridyl Chemical group 0.000 claims description 7
201000004681 Psoriasis Diseases 0.000 claims description 7
125000001072 heteroaryl group Chemical group 0.000 claims description 7
MPPYZMRXIFDUOU-UHFFFAOYSA-N n-(4,6-dimethylpyridin-2-yl)-5-pyridin-3-yldithiol-3-imine Chemical compound CC1=CC(C)=NC(N=C2SSC(=C2)C=2C=NC=CC=2)=C1 MPPYZMRXIFDUOU-UHFFFAOYSA-N 0.000 claims description 7
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
125000004076 pyridyl group Chemical group 0.000 claims description 5
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 claims description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 4
231100000252 nontoxic Toxicity 0.000 claims description 4
230000003000 nontoxic effect Effects 0.000 claims description 4
230000003287 optical effect Effects 0.000 claims description 4
238000000746 purification Methods 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 3
230000015572 biosynthetic process Effects 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
238000003786 synthesis reaction Methods 0.000 claims description 3
125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
229940124599 anti-inflammatory drug Drugs 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
125000002619 bicyclic group Chemical group 0.000 claims description 2
239000003153 chemical reaction reagent Substances 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000005842 heteroatom Chemical group 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
229910052717 sulfur Chemical group 0.000 claims description 2
239000011593 sulfur Chemical group 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
239000004480 active ingredient Substances 0.000 claims 1
239000000969 carrier Substances 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
125000001841 imino group Chemical group [H]N=* 0.000 description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
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230000000694 effects Effects 0.000 description 4
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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PHEDXBVPIONUQT-RGYGYFBISA-N phorbol 13-acetate 12-myristate Chemical compound C([C@]1(O)C(=O)C(C)=C[C@H]1[C@@]1(O)[C@H](C)[C@H]2OC(=O)CCCCCCCCCCCCC)C(CO)=C[C@H]1[C@H]1[C@]2(OC(C)=O)C1(C)C PHEDXBVPIONUQT-RGYGYFBISA-N 0.000 description 3
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
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NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
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BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
239000002644 phorbol ester Substances 0.000 description 2
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 2
210000003491 skin Anatomy 0.000 description 2
230000009885 systemic effect Effects 0.000 description 2
230000000699 topical effect Effects 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
MIHADVKEHAFNPG-UHFFFAOYSA-N 2-Amino-5-nitrothiazole Chemical compound NC1=NC=C([N+]([O-])=O)S1 MIHADVKEHAFNPG-UHFFFAOYSA-N 0.000 description 1
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
LLJRXVHJOJRCSM-UHFFFAOYSA-N 3-pyridin-4-yl-1H-indole Chemical group C=1NC2=CC=CC=C2C=1C1=CC=NC=C1 LLJRXVHJOJRCSM-UHFFFAOYSA-N 0.000 description 1
BRBUBVKGJRPRRD-UHFFFAOYSA-N 4,6-dimethylpyridin-2-amine Chemical compound CC1=CC(C)=NC(N)=C1 BRBUBVKGJRPRRD-UHFFFAOYSA-N 0.000 description 1
SNWZXTZIZWBIDQ-UHFFFAOYSA-N 4-methoxy-6-methylpyrimidin-2-amine Chemical compound COC1=CC(C)=NC(N)=N1 SNWZXTZIZWBIDQ-UHFFFAOYSA-N 0.000 description 1
RWWDMPKLJVARBW-UHFFFAOYSA-N 5-(5-methylthiophen-2-yl)-n-(5-nitro-1,3-thiazol-2-yl)dithiol-3-imine Chemical compound S1C(C)=CC=C1C(SS1)=CC1=NC1=NC=C([N+]([O-])=O)S1 RWWDMPKLJVARBW-UHFFFAOYSA-N 0.000 description 1
MAXBVGJEFDMHNV-UHFFFAOYSA-N 5-chloropyridin-2-amine Chemical compound NC1=CC=C(Cl)C=N1 MAXBVGJEFDMHNV-UHFFFAOYSA-N 0.000 description 1
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PHEDXBVPIONUQT-UHFFFAOYSA-N Cocarcinogen A1 Natural products CCCCCCCCCCCCCC(=O)OC1C(C)C2(O)C3C=C(C)C(=O)C3(O)CC(CO)=CC2C2C1(OC(C)=O)C2(C)C PHEDXBVPIONUQT-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
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KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
229930003316 Vitamin D Natural products 0.000 description 1
QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 description 1
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JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
229940030999 antipsoriatics Drugs 0.000 description 1
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239000011668 ascorbic acid Substances 0.000 description 1
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SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
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125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
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125000005956 isoquinolyl group Chemical group 0.000 description 1
125000001786 isothiazolyl group Chemical group 0.000 description 1
125000000842 isoxazolyl group Chemical group 0.000 description 1
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
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NEPZGUGQLAOODR-UHFFFAOYSA-N methyl 5-methylthiophene-2-carboxylate Chemical compound COC(=O)C1=CC=C(C)S1 NEPZGUGQLAOODR-UHFFFAOYSA-N 0.000 description 1
TWIIRMSFZNYMQE-UHFFFAOYSA-N methyl pyrazine-2-carboxylate Chemical compound COC(=O)C1=CN=CC=N1 TWIIRMSFZNYMQE-UHFFFAOYSA-N 0.000 description 1
OLXYLDUSSBULGU-UHFFFAOYSA-N methyl pyridine-4-carboxylate Chemical compound COC(=O)C1=CC=NC=C1 OLXYLDUSSBULGU-UHFFFAOYSA-N 0.000 description 1
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Classifications

- 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
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
- 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
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- 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]
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Rheumatology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pain & Pain Management (AREA)
Dermatology (AREA)
Immunology (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Pyridine Compounds (AREA)

SK918-2002A 1999-12-22 2000-12-21 Novel derivatives of 3-imino-1,2-dithioles, method for producing them and pharmaceutical compositions containing the same SK9182002A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9916194A FR2802926B1 (fr)	1999-12-22	1999-12-22	Nouveaux derives de 3-imino-1,2-dithioles, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
PCT/FR2000/003632 WO2001046180A2 (fr)	1999-12-22	2000-12-21	Nouveaux derives de 3-imino-1,2-dithioles, leur procede de preparation et les compositions pharmaceutiques qui les contiennent

Publications (1)

Publication Number	Publication Date
SK9182002A3 true SK9182002A3 (en)	2002-11-06

Family

ID=9553587

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK918-2002A SK9182002A3 (en)	1999-12-22	2000-12-21	Novel derivatives of 3-imino-1,2-dithioles, method for producing them and pharmaceutical compositions containing the same

Country Status (24)

Country	Link
US (1)	US6686378B2 (de)
EP (1)	EP1240162B1 (de)
JP (1)	JP2003518113A (de)
KR (1)	KR20020062370A (de)
CN (1)	CN1413208A (de)
AT (1)	ATE240322T1 (de)
AU (1)	AU774563B2 (de)
BR (1)	BR0016568A (de)
CA (1)	CA2394139A1 (de)
CZ (1)	CZ20022159A3 (de)
DE (1)	DE60002759T2 (de)
DK (1)	DK1240162T3 (de)
EA (1)	EA004291B1 (de)
ES (1)	ES2199190T3 (de)
FR (1)	FR2802926B1 (de)
HU (1)	HUP0203643A2 (de)
MX (1)	MXPA02006075A (de)
NO (1)	NO20023023D0 (de)
NZ (1)	NZ519144A (de)
PL (1)	PL355763A1 (de)
PT (1)	PT1240162E (de)
SK (1)	SK9182002A3 (de)
WO (1)	WO2001046180A2 (de)
ZA (1)	ZA200203964B (de)

1999
- 1999-12-22 FR FR9916194A patent/FR2802926B1/fr not_active Expired - Fee Related
2000
- 2000-12-21 EP EP00990091A patent/EP1240162B1/de not_active Expired - Lifetime
- 2000-12-21 HU HU0203643A patent/HUP0203643A2/hu unknown
- 2000-12-21 ES ES00990091T patent/ES2199190T3/es not_active Expired - Lifetime
- 2000-12-21 WO PCT/FR2000/003632 patent/WO2001046180A2/fr not_active Ceased
- 2000-12-21 AU AU26890/01A patent/AU774563B2/en not_active Ceased
- 2000-12-21 MX MXPA02006075A patent/MXPA02006075A/es not_active Application Discontinuation
- 2000-12-21 AT AT00990091T patent/ATE240322T1/de not_active IP Right Cessation
- 2000-12-21 US US10/168,875 patent/US6686378B2/en not_active Expired - Fee Related
- 2000-12-21 KR KR1020027008061A patent/KR20020062370A/ko not_active Ceased
- 2000-12-21 CN CN00817648A patent/CN1413208A/zh active Pending
- 2000-12-21 PL PL00355763A patent/PL355763A1/xx not_active Application Discontinuation
- 2000-12-21 SK SK918-2002A patent/SK9182002A3/sk unknown
- 2000-12-21 BR BR0016568-9A patent/BR0016568A/pt not_active IP Right Cessation
- 2000-12-21 NZ NZ519144A patent/NZ519144A/en unknown
- 2000-12-21 DK DK00990091T patent/DK1240162T3/da active
- 2000-12-21 JP JP2001547090A patent/JP2003518113A/ja active Pending
- 2000-12-21 PT PT00990091T patent/PT1240162E/pt unknown
- 2000-12-21 DE DE60002759T patent/DE60002759T2/de not_active Expired - Fee Related
- 2000-12-21 CA CA002394139A patent/CA2394139A1/fr not_active Abandoned
- 2000-12-21 EA EA200200636A patent/EA004291B1/ru not_active IP Right Cessation
- 2000-12-21 CZ CZ20022159A patent/CZ20022159A3/cs unknown
2002
- 2002-05-17 ZA ZA200203964A patent/ZA200203964B/en unknown
- 2002-06-21 NO NO20023023A patent/NO20023023D0/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
FR2802926A1 (fr)	2001-06-29
KR20020062370A (ko)	2002-07-25
EP1240162A2 (de)	2002-09-18
BR0016568A (pt)	2002-10-01
PT1240162E (pt)	2003-08-29
US6686378B2 (en)	2004-02-03
NO20023023L (no)	2002-06-21
EA004291B1 (ru)	2004-02-26
HUP0203643A2 (hu)	2003-03-28
CN1413208A (zh)	2003-04-23
WO2001046180A8 (fr)	2001-07-26
AU2689001A (en)	2001-07-03
FR2802926B1 (fr)	2002-02-01
MXPA02006075A (es)	2002-12-05
WO2001046180A3 (fr)	2002-05-16
ATE240322T1 (de)	2003-05-15
PL355763A1 (en)	2004-05-17
EA200200636A1 (ru)	2002-12-26
NZ519144A (en)	2003-10-31
US20030013742A1 (en)	2003-01-16
DE60002759T2 (de)	2004-04-29
DK1240162T3 (da)	2003-08-11
WO2001046180A2 (fr)	2001-06-28
JP2003518113A (ja)	2003-06-03
EP1240162B1 (de)	2003-05-14
NO20023023D0 (no)	2002-06-21
CZ20022159A3 (cs)	2002-09-11
CA2394139A1 (fr)	2001-06-28
ZA200203964B (en)	2003-05-19
DE60002759D1 (de)	2003-06-18
AU774563B2 (en)	2004-07-01
ES2199190T3 (es)	2004-02-16

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