MXPA02001944A - Rutas sinteticas para la preparacion de inhibidores de proteasa de rinovirus. - Google Patents
Rutas sinteticas para la preparacion de inhibidores de proteasa de rinovirus.Info
- Publication number
- MXPA02001944A MXPA02001944A MXPA02001944A MXPA02001944A MXPA02001944A MX PA02001944 A MXPA02001944 A MX PA02001944A MX PA02001944 A MXPA02001944 A MX PA02001944A MX PA02001944 A MXPA02001944 A MX PA02001944A MX PA02001944 A MXPA02001944 A MX PA02001944A
- Authority
- MX
- Mexico
- Prior art keywords
- group
- formula
- compound
- cycloalkyl
- independently
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- 239000000543 intermediate Substances 0.000 title claims abstract description 11
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- 241000709661 Enterovirus Species 0.000 title claims abstract description 4
- 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 title claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 185
- 241000709664 Picornaviridae Species 0.000 claims abstract description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 89
- 238000006243 chemical reaction Methods 0.000 claims description 66
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 52
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 47
- 230000008569 process Effects 0.000 claims description 44
- 125000003118 aryl group Chemical group 0.000 claims description 34
- 125000001072 heteroaryl group Chemical group 0.000 claims description 34
- 239000011541 reaction mixture Substances 0.000 claims description 28
- -1 Boc group Chemical group 0.000 claims description 25
- 125000004429 atom Chemical group 0.000 claims description 15
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
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- XGIUDIMNNMKGDE-UHFFFAOYSA-N bis(trimethylsilyl)azanide Chemical compound C[Si](C)(C)[N-][Si](C)(C)C XGIUDIMNNMKGDE-UHFFFAOYSA-N 0.000 claims description 4
- AQTUACKQXJNHFQ-LURJTMIESA-N (2s)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanedioic acid Chemical compound CC(C)(C)OC(=O)N[C@H](C(O)=O)CCC(O)=O AQTUACKQXJNHFQ-LURJTMIESA-N 0.000 claims description 3
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- 101100173726 Arabidopsis thaliana OR23 gene Proteins 0.000 claims 3
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- BOPGDPNILDQYTO-NNYOXOHSSA-N nicotinamide-adenine dinucleotide Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 BOPGDPNILDQYTO-NNYOXOHSSA-N 0.000 description 1
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 239000000816 peptidomimetic Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- DYUMLJSJISTVPV-UHFFFAOYSA-N phenyl propanoate Chemical class CCC(=O)OC1=CC=CC=C1 DYUMLJSJISTVPV-UHFFFAOYSA-N 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical class CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UORVCLMRJXCDCP-UHFFFAOYSA-N propynoic acid Chemical class OC(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-N 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical class OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 101150018444 sub2 gene Proteins 0.000 description 1
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical class OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/24—Stationary reactors without moving elements inside
- B01J19/2415—Tubular reactors
- B01J19/2435—Loop-type reactors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/24—Stationary reactors without moving elements inside
- B01J19/2475—Membrane reactors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
- C07C303/28—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids by reaction of hydroxy compounds with sulfonic acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more 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
- C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00051—Controlling the temperature
- B01J2219/00074—Controlling the temperature by indirect heating or cooling employing heat exchange fluids
- B01J2219/00087—Controlling the temperature by indirect heating or cooling employing heat exchange fluids with heat exchange elements outside the reactor
- B01J2219/00099—Controlling the temperature by indirect heating or cooling employing heat exchange fluids with heat exchange elements outside the reactor the reactor being immersed in the heat exchange medium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00051—Controlling the temperature
- B01J2219/00159—Controlling the temperature controlling multiple zones along the direction of flow, e.g. pre-heating and after-cooling
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Peptides Or Proteins (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Enzymes And Modification Thereof (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15035899P | 1999-08-24 | 1999-08-24 | |
| PCT/US2000/023033 WO2001014329A1 (fr) | 1999-08-24 | 2000-08-23 | Voies de synthese permettant de preparer des inhibiteurs de proteases de rhinovirus et intermediaires cles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA02001944A true MXPA02001944A (es) | 2002-10-31 |
Family
ID=22534156
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA02001944A MXPA02001944A (es) | 1999-08-24 | 2000-08-23 | Rutas sinteticas para la preparacion de inhibidores de proteasa de rinovirus. |
Country Status (20)
| Country | Link |
|---|---|
| EP (1) | EP1206450A1 (fr) |
| JP (1) | JP2003507453A (fr) |
| KR (1) | KR20020046283A (fr) |
| CN (1) | CN1168713C (fr) |
| AR (1) | AR025380A1 (fr) |
| AU (1) | AU770221B2 (fr) |
| BR (1) | BR0013306A (fr) |
| CA (1) | CA2376452A1 (fr) |
| CO (1) | CO5200782A1 (fr) |
| CZ (1) | CZ2002632A3 (fr) |
| HK (1) | HK1049336B (fr) |
| HU (1) | HUP0203365A3 (fr) |
| IL (1) | IL147674A0 (fr) |
| MX (1) | MXPA02001944A (fr) |
| PE (1) | PE20010517A1 (fr) |
| PL (1) | PL353997A1 (fr) |
| TW (1) | TWI245040B (fr) |
| UY (1) | UY26307A1 (fr) |
| WO (1) | WO2001014329A1 (fr) |
| ZA (1) | ZA200200504B (fr) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20010043004A (ko) | 1998-04-30 | 2001-05-25 | 개리 이. 프라이드만 | 피코르나 바이러스 억제 화합물, 그의 제조 방법 및 용도 |
| CN1372566A (zh) | 1999-08-04 | 2002-10-02 | 阿格罗尼制药公司 | 抗细小核糖核酸病毒的化合物和组合物,它们的药物用途,及其合成原料 |
| PA8507801A1 (es) | 1999-12-03 | 2002-08-26 | Agouron Pharma | Compuestos y composiciones antipicornavirales, sus usos farmaceuticos y los materiales para su sintesis |
| PE20011277A1 (es) | 2000-04-14 | 2002-01-07 | Agouron Pharma | Compuestos y composiciones antipicornavirales, sus usos farmaceuticos y los materiales para su sintesis |
| BR0111727A (pt) | 2000-06-14 | 2003-05-27 | Agouron Pharma | Compostos e composições antipicornavirais, seus usos farmacêuticos, e materiais para a sua sìntese |
| CN1309712C (zh) * | 2004-04-02 | 2007-04-11 | 中国科学院上海有机化学研究所 | Ag7088类化合物的关键中间体的前体及其合成方法 |
| WO2021176369A1 (fr) | 2020-03-06 | 2021-09-10 | Pfizer Inc. | Procédés d'inhibition de la réplication du sras-cov-2 et de traitement de la maladie à coronavirus 2019 |
| CN115260074B (zh) * | 2022-08-02 | 2024-06-21 | 爱斯特(成都)生物制药股份有限公司 | 一种口服抗病毒药物Paxlovid中间体的制备方法 |
| CN115322130B (zh) * | 2022-08-02 | 2024-05-14 | 南京正济医药研究有限公司 | 制备(s)-2-(boc-氨基)-3-[(s)-2-氧代-3-吡咯烷基]丙酸甲酯 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GT199700061A (es) * | 1996-05-14 | 1998-11-04 | Procedimiento para la obtencion de "compuestos antipicornavirales y metodos para su uso y preparacion". | |
| EP0975588B1 (fr) * | 1997-03-28 | 2003-09-03 | Agouron Pharmaceuticals, Inc. | Composes anti-picornavirus, compositions contenant ces composes et leurs procedes d'utilisation |
| US5962487A (en) * | 1997-12-16 | 1999-10-05 | Agouron Pharmaceuticals, Inc. | Antipicornaviral compounds and methods for their use and preparation |
| KR20010043004A (ko) * | 1998-04-30 | 2001-05-25 | 개리 이. 프라이드만 | 피코르나 바이러스 억제 화합물, 그의 제조 방법 및 용도 |
-
2000
- 2000-08-22 PE PE2000000854A patent/PE20010517A1/es not_active Application Discontinuation
- 2000-08-23 IL IL14767400A patent/IL147674A0/xx unknown
- 2000-08-23 CZ CZ2002632A patent/CZ2002632A3/cs unknown
- 2000-08-23 BR BR0013306-0A patent/BR0013306A/pt not_active IP Right Cessation
- 2000-08-23 CA CA002376452A patent/CA2376452A1/fr not_active Abandoned
- 2000-08-23 EP EP00955831A patent/EP1206450A1/fr not_active Withdrawn
- 2000-08-23 CN CNB008118779A patent/CN1168713C/zh not_active Expired - Fee Related
- 2000-08-23 KR KR1020027002322A patent/KR20020046283A/ko not_active Ceased
- 2000-08-23 HK HK03101461.5A patent/HK1049336B/zh not_active IP Right Cessation
- 2000-08-23 UY UY26307A patent/UY26307A1/es not_active Application Discontinuation
- 2000-08-23 JP JP2001518419A patent/JP2003507453A/ja active Pending
- 2000-08-23 PL PL00353997A patent/PL353997A1/xx not_active Application Discontinuation
- 2000-08-23 HU HU0203365A patent/HUP0203365A3/hu unknown
- 2000-08-23 WO PCT/US2000/023033 patent/WO2001014329A1/fr not_active Ceased
- 2000-08-23 MX MXPA02001944A patent/MXPA02001944A/es active IP Right Grant
- 2000-08-23 AU AU67971/00A patent/AU770221B2/en not_active Ceased
- 2000-08-24 AR ARP000104401A patent/AR025380A1/es unknown
- 2000-08-24 CO CO00063457A patent/CO5200782A1/es not_active Application Discontinuation
- 2000-10-24 TW TW089117083A patent/TWI245040B/zh active
-
2002
- 2002-01-21 ZA ZA200200504A patent/ZA200200504B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN1168713C (zh) | 2004-09-29 |
| PE20010517A1 (es) | 2001-05-16 |
| EP1206450A1 (fr) | 2002-05-22 |
| IL147674A0 (en) | 2002-08-14 |
| HK1049336A1 (en) | 2003-05-09 |
| HK1049336B (zh) | 2005-05-20 |
| TWI245040B (en) | 2005-12-11 |
| CO5200782A1 (es) | 2002-09-27 |
| PL353997A1 (en) | 2003-12-15 |
| JP2003507453A (ja) | 2003-02-25 |
| WO2001014329A1 (fr) | 2001-03-01 |
| AR025380A1 (es) | 2002-11-20 |
| CA2376452A1 (fr) | 2001-03-01 |
| ZA200200504B (en) | 2003-03-26 |
| CN1374947A (zh) | 2002-10-16 |
| BR0013306A (pt) | 2002-05-28 |
| UY26307A1 (es) | 2001-04-30 |
| HUP0203365A3 (en) | 2003-12-29 |
| HUP0203365A2 (hu) | 2003-02-28 |
| AU770221B2 (en) | 2004-02-19 |
| KR20020046283A (ko) | 2002-06-20 |
| AU6797100A (en) | 2001-03-19 |
| CZ2002632A3 (cs) | 2003-04-16 |
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