SK1742001A3 - Crystalline forms of osanetant - Google Patents

Crystalline forms of osanetant Download PDF

Info

Publication number: SK1742001A3
Authority: SK; Slovakia
Prior art keywords: osanetant; mixture; crystalline form; cooled; ethanol
Prior art date: 1998-08-05

Application number

SK174-2001A

Other languages

English (en)

Slovak (sk)

Inventor

Alain Alcade

Gilles Anne-Archard

Patrick Grosclaude

Olivier Monnier

Jerome Roche

Original Assignee

Sanofi Synthelabo

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.)

1998-08-05

Filing date

1999-08-03

Publication date

2001-11-06

1999-08-03 Application filed by Sanofi Synthelabo filed Critical Sanofi Synthelabo

2001-11-06 Publication of SK1742001A3 publication Critical patent/SK1742001A3/sk

Links

DZOJBGLFWINFBF-UMSFTDKQSA-N osanetant Chemical compound C([C@](C1)(CCCN2CCC(CC2)(N(C(C)=O)C)C=2C=CC=CC=2)C=2C=C(Cl)C(Cl)=CC=2)CCN1C(=O)C1=CC=CC=C1 DZOJBGLFWINFBF-UMSFTDKQSA-N 0.000 title claims abstract description 180
229950009875 osanetant Drugs 0.000 title claims abstract description 174
238000000034 method Methods 0.000 claims abstract description 49
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims abstract description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 119
239000000203 mixture Substances 0.000 claims description 78
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 49
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 40
239000013078 crystal Substances 0.000 claims description 32
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 29
238000002425 crystallisation Methods 0.000 claims description 26
230000008025 crystallization Effects 0.000 claims description 26
238000001816 cooling Methods 0.000 claims description 25
238000002844 melting Methods 0.000 claims description 18
230000008018 melting Effects 0.000 claims description 18
239000004480 active ingredient Substances 0.000 claims description 16
239000002904 solvent Substances 0.000 claims description 16
238000010992 reflux Methods 0.000 claims description 15
239000008194 pharmaceutical composition Substances 0.000 claims description 8
239000000725 suspension Substances 0.000 claims description 8
239000012535 impurity Substances 0.000 claims description 6
230000003472 neutralizing effect Effects 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 5
150000001875 compounds Chemical class 0.000 claims description 4
239000000843 powder Substances 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
238000003756 stirring Methods 0.000 description 17
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
229940077388 benzenesulfonate Drugs 0.000 description 12
238000010438 heat treatment Methods 0.000 description 12
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 11
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 10
239000000047 product Substances 0.000 description 10
239000002585 base Substances 0.000 description 8
238000000634 powder X-ray diffraction Methods 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
238000004458 analytical method Methods 0.000 description 5
239000012453 solvate Substances 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
238000010533 azeotropic distillation Methods 0.000 description 4
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 4
229940092714 benzenesulfonic acid Drugs 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 3
201000010099 disease Diseases 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000007903 gelatin capsule Substances 0.000 description 3
238000006386 neutralization reaction Methods 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
102000002003 Neurokinin-3 Receptors Human genes 0.000 description 2
108010040716 Neurokinin-3 Receptors Proteins 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000012297 crystallization seed Substances 0.000 description 2
238000004821 distillation Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000004128 high performance liquid chromatography Methods 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
230000003071 parasitic effect Effects 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
239000002464 receptor antagonist Substances 0.000 description 2
229940044551 receptor antagonist Drugs 0.000 description 2
-1 {3- [1-benzoyl-3- (3,4-dichlorophenyl) piperidin-3-yl] prop-1-yl} -4- phenylpiperidin-4-yl Chemical group 0.000 description 2
JZHYLWLHFLKJDG-UHFFFAOYSA-N 3-[1-benzoyl-3-(3,4-dichlorophenyl)piperidin-3-yl]propyl methanesulfonate Chemical compound C1C(CCCOS(=O)(=O)C)(C=2C=C(Cl)C(Cl)=CC=2)CCCN1C(=O)C1=CC=CC=C1 JZHYLWLHFLKJDG-UHFFFAOYSA-N 0.000 description 1
241000220479 Acacia Species 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
229920000858 Cyclodextrin Polymers 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 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
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
238000002441 X-ray diffraction Methods 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
230000000954 anitussive effect Effects 0.000 description 1
229940125715 antihistaminic agent Drugs 0.000 description 1
239000000739 antihistaminic agent Substances 0.000 description 1
239000003434 antitussive agent Substances 0.000 description 1
229940124584 antitussives Drugs 0.000 description 1
238000013475 authorization Methods 0.000 description 1
230000037396 body weight Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229940124630 bronchodilator Drugs 0.000 description 1
239000000168 bronchodilator agent Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
229940097362 cyclodextrins Drugs 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
238000010586 diagram Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
229910052738 indium Inorganic materials 0.000 description 1
APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000003094 microcapsule Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
VZUGBLTVBZJZOE-KRWDZBQOSA-N n-[3-[(4s)-2-amino-1,4-dimethyl-6-oxo-5h-pyrimidin-4-yl]phenyl]-5-chloropyrimidine-2-carboxamide Chemical compound N1=C(N)N(C)C(=O)C[C@@]1(C)C1=CC=CC(NC(=O)C=2N=CC(Cl)=CN=2)=C1 VZUGBLTVBZJZOE-KRWDZBQOSA-N 0.000 description 1
SRKPQUARWXXLDO-UHFFFAOYSA-N n-methyl-n-(4-phenylpiperidin-4-yl)acetamide Chemical compound C=1C=CC=CC=1C1(N(C(C)=O)C)CCNCC1 SRKPQUARWXXLDO-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
238000004237 preparative chromatography Methods 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
238000010926 purge Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
229940077386 sodium benzenesulfonate Drugs 0.000 description 1
MZSDGDXXBZSFTG-UHFFFAOYSA-M sodium;benzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=CC=C1 MZSDGDXXBZSFTG-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
238000001757 thermogravimetry curve Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
- 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

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

SK174-2001A 1998-08-05 1999-08-03 Crystalline forms of osanetant SK1742001A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9810107A FR2782082B3 (fr)	1998-08-05	1998-08-05	Formes cristallines de (r)-(+)-n-[[3-[1-benzoyl-3-(3,4- dichlorophenyl)piperidin-3-yl]prop-1-yl]-4-phenylpiperidin-4 -yl]-n-methylacetamide (osanetant) et procede pour la preparation dudit compose
PCT/FR1999/001914 WO2000007987A1 (fr)	1998-08-05	1999-08-03	Formes cristallines du osanetant

Publications (1)

Publication Number	Publication Date
SK1742001A3 true SK1742001A3 (en)	2001-11-06

Family

ID=9529458

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK174-2001A SK1742001A3 (en)	1998-08-05	1999-08-03	Crystalline forms of osanetant

Country Status (31)

Country	Link
US (1)	US7041679B2 (de)
EP (1)	EP1102747B1 (de)
JP (1)	JP3807938B2 (de)
KR (1)	KR100571944B1 (de)
CN (1)	CN1114592C (de)
AR (1)	AR019953A1 (de)
AT (1)	ATE243197T1 (de)
AU (1)	AU748177B2 (de)
BR (1)	BR9913357A (de)
CA (1)	CA2339007A1 (de)
CO (1)	CO5070576A1 (de)
DE (1)	DE69908951T2 (de)
DK (1)	DK1102747T3 (de)
DZ (1)	DZ3074A1 (de)
EA (1)	EA003205B1 (de)
EE (1)	EE04274B1 (de)
ES (1)	ES2200535T3 (de)
FR (1)	FR2782082B3 (de)
HU (1)	HUP0103134A3 (de)
IS (1)	IS5821A (de)
MY (1)	MY121447A (de)
NO (1)	NO320645B1 (de)
NZ (1)	NZ509561A (de)
PL (1)	PL345999A1 (de)
PT (1)	PT1102747E (de)
SK (1)	SK1742001A3 (de)
TR (1)	TR200100261T2 (de)
TW (1)	TW527354B (de)
UA (1)	UA72890C2 (de)
WO (1)	WO2000007987A1 (de)
YU (1)	YU8601A (de)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SE0100902D0 (sv)	2001-03-15	2001-03-15	Astrazeneca Ab	Compounds
SE0202539D0 (sv)	2002-08-27	2002-08-27	Astrazeneca Ab	Compounds
US7648992B2 (en) *	2004-07-05	2010-01-19	Astrazeneca Ab	Hydantoin derivatives for the treatment of obstructive airway diseases
SE0401762D0 (sv) *	2004-07-05	2004-07-05	Astrazeneca Ab	Novel compounds
SE0403085D0 (sv) *	2004-12-17	2004-12-17	Astrazeneca Ab	Novel componds
SE0403086D0 (sv) *	2004-12-17	2004-12-17	Astrazeneca Ab	Compounds
TW200800954A (en) *	2006-03-16	2008-01-01	Astrazeneca Ab	Novel crystal modifications
TW200831488A (en) *	2006-11-29	2008-08-01	Astrazeneca Ab	Novel compounds
US20240336565A1 (en) *	2021-07-02	2024-10-10	Acer Therapeutics, Inc.	Solid forms of osanetant

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2719311B1 (fr)	1994-03-18	1998-06-26	Sanofi Sa	Composés antagonistes sélectifs du récepteur NK3 humain et leur utilisation comme médicaments et outils de diagnostic.
JPH1053576A (ja) *	1996-06-07	1998-02-24	Eisai Co Ltd	塩酸ドネペジルの多形結晶およびその製造法
EP0915849A2 (de) *	1996-08-05	1999-05-19	Smithkline Beecham S.p.A.	Verfahren zur herstellung von 3,3-disubstituierten piperidinen
US6040316A (en) *	1996-09-16	2000-03-21	Warner-Lambert Company	3-alkyl-3-phenyl-piperidines
FR2757543B1 (fr) *	1996-12-23	1999-04-02	Sanofi Sa	Procede pour la cristallisation d'un derive de tetrahydropyridine et formes cristallines ainsi obtenues

1998
- 1998-08-05 FR FR9810107A patent/FR2782082B3/fr not_active Expired - Lifetime
1999
- 1999-07-25 DZ DZ990156A patent/DZ3074A1/xx active
- 1999-07-28 AR ARP990103741A patent/AR019953A1/es unknown
- 1999-08-03 SK SK174-2001A patent/SK1742001A3/sk unknown
- 1999-08-03 NZ NZ509561A patent/NZ509561A/xx unknown
- 1999-08-03 WO PCT/FR1999/001914 patent/WO2000007987A1/fr not_active Ceased
- 1999-08-03 EP EP99936672A patent/EP1102747B1/de not_active Expired - Lifetime
- 1999-08-03 AT AT99936672T patent/ATE243197T1/de not_active IP Right Cessation
- 1999-08-03 DK DK99936672T patent/DK1102747T3/da active
- 1999-08-03 BR BR9913357-1A patent/BR9913357A/pt not_active IP Right Cessation
- 1999-08-03 HU HU0103134A patent/HUP0103134A3/hu unknown
- 1999-08-03 DE DE69908951T patent/DE69908951T2/de not_active Expired - Fee Related
- 1999-08-03 PL PL99345999A patent/PL345999A1/xx not_active Application Discontinuation
- 1999-08-03 YU YU8601A patent/YU8601A/sh unknown
- 1999-08-03 MY MYPI99003297A patent/MY121447A/en unknown
- 1999-08-03 CA CA002339007A patent/CA2339007A1/en not_active Abandoned
- 1999-08-03 JP JP2000563621A patent/JP3807938B2/ja not_active Expired - Fee Related
- 1999-08-03 TR TR2001/00261T patent/TR200100261T2/xx unknown
- 1999-08-03 UA UA2001010591A patent/UA72890C2/xx unknown
- 1999-08-03 AU AU51685/99A patent/AU748177B2/en not_active Ceased
- 1999-08-03 KR KR1020017001460A patent/KR100571944B1/ko not_active Expired - Fee Related
- 1999-08-03 ES ES99936672T patent/ES2200535T3/es not_active Expired - Lifetime
- 1999-08-03 EE EEP200100070A patent/EE04274B1/xx not_active IP Right Cessation
- 1999-08-03 EA EA200100096A patent/EA003205B1/ru not_active IP Right Cessation
- 1999-08-03 PT PT99936672T patent/PT1102747E/pt unknown
- 1999-08-03 CN CN99810182A patent/CN1114592C/zh not_active Expired - Fee Related
- 1999-08-04 CO CO99049286A patent/CO5070576A1/es unknown
- 1999-08-04 TW TW088113235A patent/TW527354B/zh not_active IP Right Cessation
2001
- 2001-01-23 IS IS5821A patent/IS5821A/is unknown
- 2001-02-01 NO NO20010553A patent/NO320645B1/no unknown
2003
- 2003-08-28 US US10/651,313 patent/US7041679B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
MY121447A (en)	2006-01-28
EE200100070A (et)	2002-06-17
KR100571944B1 (ko)	2006-04-18
CN1314888A (zh)	2001-09-26
JP3807938B2 (ja)	2006-08-09
EA200100096A1 (ru)	2001-08-27
HUP0103134A3 (en)	2003-03-28
DK1102747T3 (da)	2003-09-29
ES2200535T3 (es)	2004-03-01
TW527354B (en)	2003-04-11
CA2339007A1 (en)	2000-02-17
NO20010553D0 (no)	2001-02-01
EA003205B1 (ru)	2003-02-27
NZ509561A (en)	2002-10-25
TR200100261T2 (tr)	2001-06-21
DE69908951D1 (de)	2003-07-24
BR9913357A (pt)	2001-05-15
IS5821A (is)	2001-01-23
PT1102747E (pt)	2003-09-30
FR2782082B3 (fr)	2000-09-22
DE69908951T2 (de)	2004-05-19
UA72890C2 (en)	2005-05-16
EP1102747A1 (de)	2001-05-30
DZ3074A1 (fr)	2004-07-20
HUP0103134A2 (en)	2002-06-29
EP1102747B1 (de)	2003-06-18
WO2000007987A1 (fr)	2000-02-17
JP2002522419A (ja)	2002-07-23
US7041679B2 (en)	2006-05-09
KR20010072220A (ko)	2001-07-31
AU748177B2 (en)	2002-05-30
PL345999A1 (en)	2002-01-14
CO5070576A1 (es)	2001-08-28
EE04274B1 (et)	2004-04-15
YU8601A (sh)	2003-07-07
US20040044215A1 (en)	2004-03-04
FR2782082A1 (fr)	2000-02-11
NO20010553L (no)	2001-04-05
AU5168599A (en)	2000-02-28
NO320645B1 (no)	2006-01-09
ATE243197T1 (de)	2003-07-15
AR019953A1 (es)	2002-03-27
CN1114592C (zh)	2003-07-16
HK1035535A1 (en)	2001-11-30

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