HRP20010759A2 - Novel synthesis of piperazine ring - Google Patents
Novel synthesis of piperazine ring Download PDFInfo
- Publication number
- HRP20010759A2 HRP20010759A2 HR20010759A HRP20010759A HRP20010759A2 HR P20010759 A2 HRP20010759 A2 HR P20010759A2 HR 20010759 A HR20010759 A HR 20010759A HR P20010759 A HRP20010759 A HR P20010759A HR P20010759 A2 HRP20010759 A2 HR P20010759A2
- Authority
- HR
- Croatia
- Prior art keywords
- acid
- group
- formula
- compound
- aryl
- Prior art date
Links
- 125000004193 piperazinyl group Chemical group 0.000 title description 5
- 230000015572 biosynthetic process Effects 0.000 title description 4
- 238000003786 synthesis reaction Methods 0.000 title description 4
- 238000000034 method Methods 0.000 claims description 56
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 30
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 12
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 10
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 10
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 9
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 9
- 239000012312 sodium hydride Substances 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 8
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 8
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims description 5
- LEEANUDEDHYDTG-UHFFFAOYSA-N 1,2-dimethoxypropane Chemical compound COCC(C)OC LEEANUDEDHYDTG-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 claims description 4
- 229910000105 potassium hydride Inorganic materials 0.000 claims description 4
- 239000008096 xylene Substances 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- 150000002170 ethers Chemical class 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 239000011630 iodine Substances 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims 6
- 238000006460 hydrolysis reaction Methods 0.000 claims 6
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 claims 3
- RONZAEMNMFQXRA-UHFFFAOYSA-N mirtazapine Chemical compound C1C2=CC=CN=C2N2CCN(C)CC2C2=CC=CC=C21 RONZAEMNMFQXRA-UHFFFAOYSA-N 0.000 description 9
- 229960001785 mirtazapine Drugs 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 239000000935 antidepressant agent Substances 0.000 description 4
- 229940005513 antidepressants Drugs 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- IRMBVBDXXYXPEW-UHFFFAOYSA-N 1-methyl-3-phenylpiperazine Chemical compound C1N(C)CCNC1C1=CC=CC=C1 IRMBVBDXXYXPEW-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- 230000001430 anti-depressive effect Effects 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- DHUHYBBSQWQGSN-UHFFFAOYSA-N 2-(4-methyl-2-phenylpiperazin-1-yl)pyridine-3-carbonitrile Chemical compound C1N(C)CCN(C=2C(=CC=CN=2)C#N)C1C1=CC=CC=C1 DHUHYBBSQWQGSN-UHFFFAOYSA-N 0.000 description 2
- HTCVSFZWADPKPB-UHFFFAOYSA-N 2-piperazin-1-yl-1h-azepine Chemical class C1CNCCN1C1=CC=CC=CN1 HTCVSFZWADPKPB-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000012896 selective serotonin reuptake inhibitor Substances 0.000 description 2
- 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- DQFQCHIDRBIESA-UHFFFAOYSA-N 1-benzazepine Chemical compound N1C=CC=CC2=CC=CC=C12 DQFQCHIDRBIESA-UHFFFAOYSA-N 0.000 description 1
- KUSNCWLQRVMIRN-UHFFFAOYSA-N 2-chloro-n-(2-chloroethyl)-n-methyl-2-phenylethanamine Chemical compound ClCCN(C)CC(Cl)C1=CC=CC=C1 KUSNCWLQRVMIRN-UHFFFAOYSA-N 0.000 description 1
- JAUPUQRPBNDMDT-UHFFFAOYSA-N 2-chloropyridine-3-carbonitrile Chemical compound ClC1=NC=CC=C1C#N JAUPUQRPBNDMDT-UHFFFAOYSA-N 0.000 description 1
- 208000020401 Depressive disease Diseases 0.000 description 1
- 229940123685 Monoamine oxidase inhibitor Drugs 0.000 description 1
- 229910018954 NaNH2 Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002899 monoamine oxidase inhibitor Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 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
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
- -1 tricyclics Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13004899P | 1999-04-19 | 1999-04-19 | |
| PCT/US2000/009418 WO2000063185A1 (en) | 1999-04-19 | 2000-04-07 | Novel synthesis of piperazine ring |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20010759A2 true HRP20010759A2 (en) | 2003-02-28 |
Family
ID=22442818
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20010759A HRP20010759A2 (en) | 1999-04-19 | 2001-10-18 | Novel synthesis of piperazine ring |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US6339156B1 (ja) |
| EP (1) | EP1178972A4 (ja) |
| JP (1) | JP2002542234A (ja) |
| KR (1) | KR20020015313A (ja) |
| CN (1) | CN1355793A (ja) |
| AU (1) | AU777105B2 (ja) |
| CA (1) | CA2370389A1 (ja) |
| CZ (1) | CZ20013698A3 (ja) |
| HK (1) | HK1042696A1 (ja) |
| HR (1) | HRP20010759A2 (ja) |
| HU (1) | HUP0200808A3 (ja) |
| IL (1) | IL146024A0 (ja) |
| PL (1) | PL351395A1 (ja) |
| RU (1) | RU2001128228A (ja) |
| SK (1) | SK14802001A3 (ja) |
| TR (1) | TR200103035T2 (ja) |
| WO (1) | WO2000063185A1 (ja) |
| YU (1) | YU74201A (ja) |
| ZA (1) | ZA200108480B (ja) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002542234A (ja) * | 1999-04-19 | 2002-12-10 | テバ ファーマシューティカル インダストリーズ リミティド | ピペラジン環の新規合成 |
| WO2001025185A1 (fr) | 1999-09-30 | 2001-04-12 | Sumika Fine Chemicals Co., Ltd. | Procede de production de derive de piperazine |
| AU6474200A (en) * | 1999-12-13 | 2001-06-18 | Sumika Fine Chemicals Co., Ltd. | Process for the preparation of a pyridinemethanol compound |
| HUP0401921A3 (en) | 2001-09-14 | 2008-03-28 | Medichem Sa | Intermediate compounds for the preparation of mirtazapine and the production methods thereof |
| US7041826B2 (en) * | 2003-06-02 | 2006-05-09 | Aurobindo Pharma Ltd. | Process for preparing 1-methyl-3-phenylpiperazine using a novel intermediate |
| US20090275749A1 (en) * | 2005-09-26 | 2009-11-05 | Hiroshi Maeda | Production method of optically active piperazine compound |
| CN101440067B (zh) * | 2007-11-21 | 2010-08-25 | 上海津力化工有限公司 | 一种药物中间体1-甲基-3-苯基哌嗪的制备方法 |
| CN102649779A (zh) * | 2012-04-20 | 2012-08-29 | 山东鲁药制药有限公司 | 一种药物中间体1-甲基-3-苯基哌嗪的合成方法 |
| AU2016222550B2 (en) | 2015-02-27 | 2020-07-16 | Dechra Limited | Stimulation of appetite, management of weight loss, and treatment of anorexia in dogs and cats |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2891063A (en) * | 1959-06-16 | Piperazine derivatives and process of | ||
| US2830056A (en) * | 1958-04-08 | Chj oh | ||
| US2507408A (en) * | 1948-03-05 | 1950-05-09 | Rhone Poulenc Sa | 1-alkylsulfonyl-4-alkyl piperazines |
| GB1181322A (en) * | 1967-06-29 | 1970-02-11 | Chugai Pharmaceutical Co Ltd | Piperazine Derivatives and processes for preparing the same |
| US4217452A (en) * | 1974-02-09 | 1980-08-12 | Akzona Incorporated | Synthesis for the preparation of tetracyclic compounds |
| NL179906C (nl) * | 1974-02-09 | 1986-12-01 | Akzo Nv | Werkwijze voor het bereiden van 1,2,3,4,10,14b-hexahydrodibenzo(c,f)pyrazino (1,2-a)azepine derivaten. |
| NL189199C (nl) | 1975-04-05 | 1993-02-01 | Akzo Nv | Werkwijze ter bereiding van farmaceutische preparaten met werking op het centraal zenuwstelsel op basis van benz(aryl)azepinederivaten, de verkregen gevormde farmaceutische preparaten, alsmede werkwijze ter bereiding van de toe te passen benz(aryl)azepinederivaten. |
| FR2585702B1 (fr) * | 1985-07-31 | 1989-03-03 | Lafon Labor | Derives de phenyl-piperazine, procede de preparation et utilisation en therapeutique |
| US4918190A (en) * | 1986-08-06 | 1990-04-17 | Ube Industries, Ltd. | Crystalline complex compounds of propargyl alcohols and tertiary diamines, and process of separation and purification of propargyl alcohols using the same |
| US4935515A (en) * | 1988-02-23 | 1990-06-19 | American Home Products Corporation | 2,3,4,5-tetrahydro-1H-[1,2,5]triazocino(1,2-a)[1,2,4]benzotriazin-7(8H)-ones, thiones and derivatives |
| JP2002542234A (ja) * | 1999-04-19 | 2002-12-10 | テバ ファーマシューティカル インダストリーズ リミティド | ピペラジン環の新規合成 |
-
2000
- 2000-04-07 JP JP2000612277A patent/JP2002542234A/ja active Pending
- 2000-04-07 CA CA002370389A patent/CA2370389A1/en not_active Abandoned
- 2000-04-07 KR KR1020017013280A patent/KR20020015313A/ko not_active Application Discontinuation
- 2000-04-07 HU HU0200808A patent/HUP0200808A3/hu unknown
- 2000-04-07 SK SK1480-2001A patent/SK14802001A3/sk unknown
- 2000-04-07 IL IL14602400A patent/IL146024A0/xx unknown
- 2000-04-07 US US09/545,011 patent/US6339156B1/en not_active Expired - Fee Related
- 2000-04-07 AU AU42190/00A patent/AU777105B2/en not_active Ceased
- 2000-04-07 WO PCT/US2000/009418 patent/WO2000063185A1/en not_active Application Discontinuation
- 2000-04-07 CZ CZ20013698A patent/CZ20013698A3/cs unknown
- 2000-04-07 YU YU74201A patent/YU74201A/sh unknown
- 2000-04-07 CN CN00809049A patent/CN1355793A/zh active Pending
- 2000-04-07 EP EP00921933A patent/EP1178972A4/en not_active Withdrawn
- 2000-04-07 TR TR2001/03035T patent/TR200103035T2/xx unknown
- 2000-04-07 RU RU2001128228/04A patent/RU2001128228A/ru not_active Application Discontinuation
- 2000-04-07 PL PL00351395A patent/PL351395A1/xx not_active Application Discontinuation
-
2001
- 2001-08-24 US US09/939,406 patent/US6852855B2/en not_active Expired - Fee Related
- 2001-10-16 ZA ZA200108480A patent/ZA200108480B/xx unknown
- 2001-10-18 HR HR20010759A patent/HRP20010759A2/hr not_active Application Discontinuation
-
2002
- 2002-05-13 HK HK02103576.4A patent/HK1042696A1/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN1355793A (zh) | 2002-06-26 |
| EP1178972A1 (en) | 2002-02-13 |
| EP1178972A4 (en) | 2002-06-12 |
| IL146024A0 (en) | 2002-07-25 |
| RU2001128228A (ru) | 2003-07-20 |
| HUP0200808A3 (en) | 2002-12-28 |
| HK1042696A1 (zh) | 2002-08-23 |
| SK14802001A3 (sk) | 2002-07-02 |
| AU777105B2 (en) | 2004-09-30 |
| US20020035256A1 (en) | 2002-03-21 |
| WO2000063185A1 (en) | 2000-10-26 |
| US6852855B2 (en) | 2005-02-08 |
| HUP0200808A2 (hu) | 2002-11-28 |
| PL351395A1 (en) | 2003-04-07 |
| AU4219000A (en) | 2000-11-02 |
| ZA200108480B (en) | 2003-01-29 |
| YU74201A (sh) | 2004-05-12 |
| CZ20013698A3 (cs) | 2002-05-15 |
| US6339156B1 (en) | 2002-01-15 |
| CA2370389A1 (en) | 2000-10-26 |
| KR20020015313A (ko) | 2002-02-27 |
| JP2002542234A (ja) | 2002-12-10 |
| TR200103035T2 (tr) | 2002-01-21 |
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