SK8052003A3 - 1,4-Disubstituted piperazine derivatives useful as uro-selective alpha1-adrenoceptor blockers - Google Patents
1,4-Disubstituted piperazine derivatives useful as uro-selective alpha1-adrenoceptor blockers Download PDFInfo
- Publication number
- SK8052003A3 SK8052003A3 SK805-2003A SK8052003A SK8052003A3 SK 8052003 A3 SK8052003 A3 SK 8052003A3 SK 8052003 A SK8052003 A SK 8052003A SK 8052003 A3 SK8052003 A3 SK 8052003A3
- Authority
- SK
- Slovakia
- Prior art keywords
- compound
- propyl
- dione
- isoindole
- piperazin
- Prior art date
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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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Description
obore budú zrejmé určité modifikácie a ekvivalenty, ktoré sú zahrnuté v rozsahu vynálezu.
Claims (10)
1. 1,4-Disubstituovaný piperazínový derivát všeobecného vzorca I kde A je priamy alebo rozvetvený C1-C4 alkylový reťazec; R je 3-fenyl-2-propén-1 yl, benzyl, substituovaný benzyl, fenyl, mono- alebo disubstituovaná fenylová skupina substituovaná substituentmi nezávisle vybranými zo skupiny pozostávajúcej z halogénu, hydroxy skupiny, Ci-Cgalkylu, Ci-Cealkoxy, trifluórmetylu, nitro a trifluóralkoxy skupiny alebo (dihalogéndifenyl)metylu;
jeho farmaceutický prijateľné soli, amidy, enantioméry, diastereoméry, N-oxidy, proliečivá, metabolity alebo ich polymorfné formy.
2. 1,4-Disubstituovaný piperazínový derivát podľa nároku 1, vyznačujúci sa tým, že halogén je vybraný zo skupiny pozostávajúcej z chlór, fluór, jód skupiny; C1- Οβ alkyl je vybraný zo skupiny pozostávajúcej z metylu, etylu, a-propylu, izopropylu, butylu, terc.butylu; a C1-C6 alkoxy môže byť vybraný zo skupiny pozostávajúcej z metoxy, etoxy, a-propoxy, izopropoxy a hexyloxy skupiny.
3. 1,4-Disubstituovaný piperazínový derivát podľa nároku 1, vyznačujúci sa tým, že je vybraný zo skupiny pozostávajúcej z:
- 2-[3-{4-(2-metoxyfenyl)piperazin-1-yl}propyl]-3a,4,7,7atetrahydro-1H-izoindol-1,3(2H)-dión (zlúčenina 01).
Γ * c C * C P e , < r r r
-22- ý : r7' ' : . 7 c Γ f
2-[3-{4-(3-chlórfenyl)piperazin-1-yl}propyl]-3a,4,7,7a-tetrahydro-1Hizoindol-1,3(2H)-dión (zlúčenina 02).
2-(3-( 4-(2-metylfenyl)piperazin-1-yl)propyl]-3a,4,7,7a-tetrahydro-1Hizoindol-1,3(2H)-dión (zlúčenina 03).
2-[3-(4-(4-fluórfenyl)piperazin-1-yl}propyl]-3a,4,7,7a-tetrahydro-1Hizoindol-1,3(2H)-dión (zlúčenina 04).
2-[3-{4-(3-trifluórmetylfenyl)piperazin-1-yl}propyl]-3a,4,7,7atetrahydro-1H-izoindol-1,3(2H)-dión (zlúčenina 05).
2-[3-(4-(2-fluórfenyl)piperazin-1-yl}propyl]-3a,4l7,7a-tetrahydro-1Hizoindol-1,3(2H)-dión (zlúčenina 06).
2-(3-(4-(3,4-dimetylfenyl)piperazin-1-yl}propyl]-3a, 4,7,7a-tetrahydro1H-izoindol-1,3(2H)-dión (zlúčenina 07).
2-[3-{4-(2-metoxy-5-fliiórŤenyl)piperazin-1-yl}propyl]-3a,4,7,7atetrahydro-1H-izoindol-1,3(2H)-dión (zlúčenina 08).
2-[3-{4-(2-etylfenyl)piperazin-1-yl}propyl]-3a,4,7,7a--tetrahydro-1Hizoindol-1,3(2H)-dión (zlúčenina 09).
2-(3-(4-(2,4-difluórfenyl)piperazin-1-yl}propyl]-3a,4,7,7a-tetrahydro1H-izoindol-1,3(2H)-dión (zlúčenina 10).
2-[3-(4-(2-etoxyfenyl)piperazin-1-yl}propyl]-3a,4,7,7a-tetrahydro-1 Hizoindol-1,3(2H)-dión (zlúčenina 11).
2-[3-{4-(2-metyl-5-chlórfenyl)piperazin-1-yl}propyl]-3a,4,7,7a-tetrahydro-1H-izoindol-1,3(2H)-dión (zlúčenina 12).
2-[3-(4-(fenyl)piperazin-1-yl}propyl]-3a,4,7,7a-tetrahydro-1H-izoindol1,3(2H)-dión (zlúčenina 13).
2-[3-{4-(benzyl)piperazin-1 -yl}propyl]-3a,4,7,7a-tetrahydro-1 Hizoindol-1,3(2H)-dión (zlúčenina 14).
2-[3-(4-(3-fenyl-2-propen-1-yl)piperazin-1-yl}propyl]-3a,4,7,7atetrahydro-1H-izoindol-1,3(2H)-dión (zlúčenina 15).
2-[3-(4-(4-nitrofenyl)piperazin-1-yl}propyl]-3a,4,7,7a-tetrahydro-1Hizoindol-1,3(2H)-dión (zlúčenina 16).
2-[3-(4-(3-chlór-4-metylfenyl)piperazin-1-yl}propyl]-3a,4,7,7atetrahydro-1H-izoindol-1,3(2H)-dión (zlúčenina 17).
-232-[3-{4-(4-fluór-2-metoxyfenyl)piperazin-1-yl}propyl]-3a,4,7,7atetrahydro-1 H-izoindol-1,3(2H)-dión (zlúčenina 18).
2-[3-{4-(bis-4-fluórfenyl)metylpiperazin-1-yl}propyl]-3a,4,7,7atetrahydro-1 H-izoindol-1,3(2H)-dión (zlúčenina 19).
2-[3-{4-(2,4-dichlórfenyl)piperazin-1-yl}propyl]-3a,4,7,7a-tetrahydro1 H-izoindol-1,3(2H)-dión (zlúčenina 20).
2-[3-{4-(2,4-dimetoxyfenyl)piperazin-1-yl}propyl]-3a,4,7,7a-tetrahydro1 H-izoindol-1,3(2H)-dión (zlúčenina 21).
2-[3-{4-(2,6-dimetylfenyl)piperazin-1-yl}propyl]-3a,4,7,7a-tetrahydro1 H-izoindol-1,3(2H)-dión (zlúčenina 22).
2-[3-{ 4-(2-izopropoxyfenyl)piperazin-1 -yl}propyl]-3a,4,7,7a-tetrahydro1 H-izoindol-1,3(2H)-dión (zlúčenina 23).
2-[3-{4-(2-propoxyfenyl)piperazin-1-yl}propyl]-3a,4,7,7a-tetrahydro-1 H-izoindol-1,3(2H)-dión (zlúčenina 24).
2-[3-{4-(2-n-hexyloxyfenyl)piperazin-1 -yl}propyl]-3a,4,7,7a-tetrahydro1 H-izoindol-1,3(2H)-dión (zlúčenina 25).
2-[3-{4-(2,5-dimetoxyfenyl)piperazin-1-yl}propyl]-3a,4,7,7a-tetrahydro1 H-izoindol-1,3(2H)-dión (zlúčenina 26).
2-[3-{4-(4-terc.butylfenyl)piperazin-1-yl}propyl]-3a,4,7,7a-tetrahydro1 H-izoindol-1,3(2H)-dión (zlúčenina 27).
2-[3-{4-(2-metoxy-6-hydroxyfenyl)piperazin-1-yl}propyl]-3a,4,7,7atetrahydro-1 H-izoindol-1,3(2H)-dión (zlúčenina 28).
2-[3-{4-(2-metoxyfenyl)piperazin-1-yl}-3-metylpropyl]-3a,4,7,7atetrahydro-1 H-izoindol-1,3(2H)-dión (zlúčenina 29).
2-[3-{ 4-(2-metoxyfenyl)piperazin-1 -yl} -2-metylpropyl]-3a,4,7,7atetrahydro-1 H-izoindol-1,3(2H)-dión (zlúčenina 30).
2-[3-{4-(2-etoxyfenyl)piperazin-1-yl}-3-metylpropyl]-3a,4,7,7atetrahydro-1 H-izoindol-1,3(2H)-dión (zlúčenina 31).
4. 1,4-Disubstituovaný piperazínový derivát podľa nároku 1 na použitie na selektívny ancdgonný účinok na cu - adrenergné receptory u cicavca.
5. 1,4-Disubstituovaný piperazínový derivát podľa nároku 1 na použitie pri liečbe benígnej prostastickej hyperplázie u cicavca.
6. Farmaceutická kompozícia, vyznačujúca sa tým, že obsahuje 1,4-disubstituovaný piperazínový derivát všeobecného vzorca 1 a farmaceutický prijateľný nosič.
7. Farmaceutická kompozícia podľa nároku 6 na použitie na selektívny antagonný účinok na ai - adrenergné receptory.
8. Farmaceutická kompozície podľa nároku 6 na použitie pri liečbe benígnej prostastickej hyperplázie u cicavca.
9. Spôsob prípravy 1,4-disubstituovaného piperazínového derivátu všeobecného vzorca I kde A je priamy alebo rozvetvený C1-C4 alkylový reťazec; R je 3-fenyl-2-propen-1yl, benzyl, substituovaný benzyl, fenyl, mono- alebo disubstituovaná fenylová skupina substituovaná substituentmi nezávisle vybranými zo skupiny pozostávajúcej z halogénu, hydroxy skupiny, C1 - Cô alkylu, C1 - Οβ alkoxy, trifluórmetyl, nitro a trifluóralkoxy skupiny alebo (dihalogéndifenyl)metylu, alebo jeho farmaceutický prijateľné soli, amidov, enantiomérov, diastereomérov, N-oxidov, proliečiv, metabolitov alebo ich polymorfných foriem, vyznačujúci sa tým, že sa nechá reagovať zlúčenina všeobecného vzorca II s piperazínovým derivátom všeobecného vzorca III, ako je zobrazené v schéme I, kde A a R sú definované vyššie.
e r # derivátu všeobecného
-25- q·'
10. Spôsob prípravy 1,4-disubstituovaného piperazínového vzorca I (I), kde A je priamy alebo rozvetvený C1-C4 alkylový reťazec; R je 3-fenyl-2-propen-1yl, benzyl, substituovaný benzyl, fenyl, mono- alebo disubstituovaná fenylová skupina substituovaná substituentmi nezávisle vybranými zo skupiny pozostávajúcej z halogénu, hydroxy skupiny, Ci-C6alkylu, Ci-Cealkoxy, trifluórmetyl, nitro a trifluóralkoxy skupiny alebo (dihalogéndifenyl)metylu; alebo jeho farmaceutický prijateľných solí, amidov, enantiomérov, diastereomérov, N-oxidov, proliečiv, metabolitov alebo ich polymorfných foriem, vyznačujúci sa tým, že sa nechá reagovať 1-(®-halogénalkyl)cis-3a, 4,7,7a-tetrahydroftalimidu všeobecného vzorca IV, kde A je definované vyššie, so zlúčeninou všeobecného vzorca V, kde R je definované vyššie, ako uvádza schéma II.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN1097DE2000 | 2000-11-30 | ||
| PCT/IB2001/002261 WO2002044151A1 (en) | 2000-11-30 | 2001-11-29 | 1,4-disubstituted piperazine derivatives useful as uro-selective $g(a)1-adrenoceptor blockers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK8052003A3 true SK8052003A3 (en) | 2003-12-02 |
Family
ID=11097130
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK805-2003A SK8052003A3 (en) | 2000-11-30 | 2001-11-29 | 1,4-Disubstituted piperazine derivatives useful as uro-selective alpha1-adrenoceptor blockers |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US6914064B2 (sk) |
| EP (1) | EP1339682A1 (sk) |
| JP (1) | JP2004514711A (sk) |
| KR (1) | KR20030068164A (sk) |
| CN (1) | CN1230423C (sk) |
| AP (1) | AP2003002810A0 (sk) |
| AR (1) | AR035930A1 (sk) |
| AU (2) | AU2231502A (sk) |
| BG (1) | BG107943A (sk) |
| BR (1) | BR0115865A (sk) |
| CA (1) | CA2430343A1 (sk) |
| CZ (1) | CZ20031698A3 (sk) |
| DO (1) | DOP2001000296A (sk) |
| EA (1) | EA006941B1 (sk) |
| EE (1) | EE200300250A (sk) |
| HU (1) | HUP0400545A3 (sk) |
| MA (1) | MA26064A1 (sk) |
| MX (1) | MXPA03004850A (sk) |
| NZ (1) | NZ526226A (sk) |
| OA (1) | OA12537A (sk) |
| PA (1) | PA8534001A1 (sk) |
| PL (1) | PL362210A1 (sk) |
| SK (1) | SK8052003A3 (sk) |
| WO (1) | WO2002044151A1 (sk) |
| ZA (1) | ZA200304242B (sk) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003084928A1 (en) * | 2002-04-08 | 2003-10-16 | Ranbaxy Laboratories Limited | Alpha, omega-dicarboximide derivatives as useful uro-selective α1α adrenoceptor blockers |
| AU2003278403A1 (en) * | 2003-10-15 | 2005-05-05 | Ranbaxy Laboratories Limited | 1-alkylpiperazinyl-pyrrolidin-2, 5-dione derivatives as adrenergic receptor antagonist |
| EP1746998A1 (en) * | 2004-03-22 | 2007-01-31 | Ranbaxy Laboratories, Ltd. | Combination therapy for lower urinary tract symptoms |
| WO2005113498A1 (en) * | 2004-05-19 | 2005-12-01 | Ranbaxy Laboratories Limited | Adrenergic receptor antagonists |
| EP1758583A2 (en) * | 2004-05-31 | 2007-03-07 | Ranbaxy Laboratories Limited | Arylpiperazine derivatives useful as adrenergic receptor antagonists |
| WO2006018815A1 (en) * | 2004-08-16 | 2006-02-23 | Ranbaxy Laboratories Limited | Piperazine derivatives as adrenergic receptor antagonists |
| WO2006051399A1 (en) * | 2004-11-11 | 2006-05-18 | Ranbaxy Laboratories Limited | Piperazine derivatives useful as adrenergic receptor antagonists |
| WO2006051374A2 (en) * | 2004-11-11 | 2006-05-18 | Ranbaxy Laboratories Limited | Arylpiperazines useful as adrenergic receptor antagonists |
| WO2006092710A1 (en) * | 2005-03-02 | 2006-09-08 | Ranbaxy Laboratories Limited | Metabolites of 2-{3-[4-(2-isopropoxyphenyl) piperazin-1-yl]-propyl}-3a,4,7,7a-tetrahydro-1h-isoindole-1,3-(2h)-dione |
| WO2006117760A1 (en) * | 2005-05-03 | 2006-11-09 | Ranbaxy Laboratories Limited | Adrenergic receptor antagonists |
| WO2007029156A2 (en) * | 2005-09-05 | 2007-03-15 | Ranbaxy Laboratories Limited | Isoindoledione derivatives as adrenergic receptor antagonists |
| WO2007039809A1 (en) * | 2005-10-05 | 2007-04-12 | Ranbaxy Laboratories Limited | Metabolites of 2- {3-[4-(5-fluoro-2-isopropoxy-phenyl)-piperazin-1-yl]-propyl} -5,6-dihydroxy-hexahydro-isoindole-1,3-dione |
| JP5701213B2 (ja) | 2008-10-10 | 2015-04-15 | インスティチュート オブ ファーマコロジー アンド トキシコロジー アカデミー オブ ミリタリー メディカル サイエンシズ ピー．エル．エー．チャイナ | 新規なドーパミンｄ３受容体リガンド、その調製及び使用 |
| US9227944B2 (en) | 2008-10-10 | 2016-01-05 | Institute Of Pharmacology And Toxicology Academy Of Military Science P.L.A. China | Dopamine D3 receptor ligands and preparation and medical uses of the same |
| EP2416760A4 (en) | 2009-05-05 | 2014-01-22 | Tekmira Pharmaceuticals Corp | LIPID COMPOSITIONS |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57197265A (en) * | 1981-05-29 | 1982-12-03 | Eisai Co Ltd | Carboxylic acid imide derivative, its preparation and medicament containing the same |
| JPS5936661A (ja) * | 1982-08-26 | 1984-02-28 | Eisai Co Ltd | カルボン酸イミド誘導体およびその製造方法ならびにそれを含有する医薬 |
| JPS5976059A (ja) * | 1982-10-21 | 1984-04-28 | Sumitomo Chem Co Ltd | 環状イミド誘導体及びその酸付加塩 |
| JPS5995267A (ja) * | 1982-11-25 | 1984-06-01 | Eisai Co Ltd | カルボン酸イミド誘導体およびその製造方法 |
| US4524206A (en) * | 1983-09-12 | 1985-06-18 | Mead Johnson & Company | 1-Heteroaryl-4-(2,5-pyrrolidinedion-1-yl)alkyl)piperazine derivatives |
| AT387773B (de) * | 1983-09-12 | 1989-03-10 | Bristol Myers Co | Verfahren zur herstellung von 1-heteroaryl-4-((2,5-pyrrolidindion-1-yl)aklyl) iperazin-derivaten |
| JPS60204784A (ja) | 1984-03-29 | 1985-10-16 | Eisai Co Ltd | カルボン酸イミド誘導体 |
| JP2918899B2 (ja) | 1989-03-09 | 1999-07-12 | 住友製薬株式会社 | 環状イミド誘導体の製造方法 |
| US5688795A (en) * | 1994-11-08 | 1997-11-18 | Syntex (U.S.A.) Inc. | 3-(4-phenylpiperazin-1-yl)propyl-amino, thio and oxy!-pyridine, pyrimidine and benzene derivatives as α1 -adrenoceptor antagonists |
| EP0748800B1 (en) * | 1995-06-09 | 2001-05-09 | F. Hoffmann-La Roche Ag | Pyrimidinedione, pyrimidinetrione, triazinedione derivatives as alpha-1-adrenergic receptor antagonists |
| WO1998037893A1 (fr) | 1997-02-26 | 1998-09-03 | Sumitomo Pharmaceuticals Co., Ltd. | Antagoniste du recepteur dopaminergique d4 |
| ATE250033T1 (de) * | 1997-05-12 | 2003-10-15 | Ortho Mcneil Pharm Inc | Arylsubstituierte piperazine die bei der behandlung von gutartiger prostatischer hyperlasie nützlich sind |
| US6083950A (en) * | 1997-11-13 | 2000-07-04 | Ranbaxy Laboratories Limited | 1-(4-arylpiperazin-1-yl)-ω-[n-(α,ω-dicarboximido)]-alka nes useful as uro-selective α1-adrenoceptor blockers |
-
2001
- 2001-11-29 PA PA20018534001A patent/PA8534001A1/es unknown
- 2001-11-29 NZ NZ526226A patent/NZ526226A/en unknown
- 2001-11-29 CA CA002430343A patent/CA2430343A1/en not_active Abandoned
- 2001-11-29 EA EA200300620A patent/EA006941B1/ru not_active IP Right Cessation
- 2001-11-29 SK SK805-2003A patent/SK8052003A3/sk not_active Application Discontinuation
- 2001-11-29 EP EP01998540A patent/EP1339682A1/en not_active Withdrawn
- 2001-11-29 CZ CZ20031698A patent/CZ20031698A3/cs unknown
- 2001-11-29 JP JP2002546521A patent/JP2004514711A/ja not_active Withdrawn
- 2001-11-29 CN CNB018220460A patent/CN1230423C/zh not_active Expired - Fee Related
- 2001-11-29 EE EEP200300250A patent/EE200300250A/xx unknown
- 2001-11-29 AU AU2231502A patent/AU2231502A/xx active Pending
- 2001-11-29 OA OA1200300149A patent/OA12537A/en unknown
- 2001-11-29 WO PCT/IB2001/002261 patent/WO2002044151A1/en active IP Right Grant
- 2001-11-29 AU AU2002222315A patent/AU2002222315B2/en not_active Ceased
- 2001-11-29 AP APAP/P/2003/002810A patent/AP2003002810A0/en unknown
- 2001-11-29 KR KR10-2003-7007305A patent/KR20030068164A/ko not_active Application Discontinuation
- 2001-11-29 BR BR0115865-1A patent/BR0115865A/pt not_active IP Right Cessation
- 2001-11-29 HU HU0400545A patent/HUP0400545A3/hu unknown
- 2001-11-29 PL PL01362210A patent/PL362210A1/xx not_active Application Discontinuation
- 2001-11-29 MX MXPA03004850A patent/MXPA03004850A/es unknown
- 2001-11-30 US US09/998,115 patent/US6914064B2/en not_active Expired - Fee Related
- 2001-11-30 AR ARP010105588A patent/AR035930A1/es not_active Application Discontinuation
- 2001-11-30 DO DO2001000296A patent/DOP2001000296A/es unknown
-
2003
- 2003-05-30 MA MA27188A patent/MA26064A1/fr unknown
- 2003-05-30 ZA ZA200304242A patent/ZA200304242B/en unknown
- 2003-06-25 BG BG107943A patent/BG107943A/bg unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN1230423C (zh) | 2005-12-07 |
| EE200300250A (et) | 2003-10-15 |
| KR20030068164A (ko) | 2003-08-19 |
| BR0115865A (pt) | 2003-12-23 |
| AR035930A1 (es) | 2004-07-28 |
| BG107943A (bg) | 2004-08-31 |
| CA2430343A1 (en) | 2002-06-06 |
| US20020156085A1 (en) | 2002-10-24 |
| ZA200304242B (en) | 2004-03-02 |
| MA26064A1 (fr) | 2004-04-01 |
| PA8534001A1 (es) | 2002-12-11 |
| AU2002222315B2 (en) | 2007-06-21 |
| DOP2001000296A (es) | 2003-03-15 |
| HUP0400545A2 (hu) | 2004-07-28 |
| WO2002044151A1 (en) | 2002-06-06 |
| EP1339682A1 (en) | 2003-09-03 |
| OA12537A (en) | 2006-06-05 |
| PL362210A1 (en) | 2004-10-18 |
| JP2004514711A (ja) | 2004-05-20 |
| CZ20031698A3 (cs) | 2003-11-12 |
| NZ526226A (en) | 2004-05-28 |
| HUP0400545A3 (en) | 2007-05-02 |
| EA006941B1 (ru) | 2006-06-30 |
| US6914064B2 (en) | 2005-07-05 |
| AP2003002810A0 (en) | 2003-06-30 |
| AU2231502A (en) | 2002-06-11 |
| CN1486300A (zh) | 2004-03-31 |
| MXPA03004850A (es) | 2004-01-26 |
| EA200300620A1 (ru) | 2003-12-25 |
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