ZA200204422B - Branched substituted amino derivatives of 3-amino-1-phenyl-1H(1,2,4)triazol, methods for producing them and pharmaceutical compositions containing them. - Google Patents
Branched substituted amino derivatives of 3-amino-1-phenyl-1H(1,2,4)triazol, methods for producing them and pharmaceutical compositions containing them. Download PDFInfo
- Publication number
- ZA200204422B ZA200204422B ZA200204422A ZA200204422A ZA200204422B ZA 200204422 B ZA200204422 B ZA 200204422B ZA 200204422 A ZA200204422 A ZA 200204422A ZA 200204422 A ZA200204422 A ZA 200204422A ZA 200204422 B ZA200204422 B ZA 200204422B
- Authority
- ZA
- South Africa
- Prior art keywords
- cyclopropyl
- triazol
- alkyl
- propyl
- methylphenyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 33
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 9
- 150000001412 amines Chemical class 0.000 title description 11
- 150000001875 compounds Chemical class 0.000 claims description 111
- 125000000217 alkyl group Chemical group 0.000 claims description 66
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 38
- 238000002360 preparation method Methods 0.000 claims description 29
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 26
- -1 methylenedioxy Chemical group 0.000 claims description 26
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 150000004677 hydrates Chemical class 0.000 claims description 7
- 239000012453 solvate Substances 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- NLTHNJUIHGELQW-UHFFFAOYSA-N 1-(2-chloro-4-methoxy-5-methylphenyl)-n-[2-cyclopropyl-1-(4-fluorophenyl)ethyl]-5-methyl-n-prop-2-ynyl-1,2,4-triazol-3-amine;hydrochloride Chemical compound Cl.C1=C(C)C(OC)=CC(Cl)=C1N1C(C)=NC(N(CC#C)C(CC2CC2)C=2C=CC(F)=CC=2)=N1 NLTHNJUIHGELQW-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- LVBALXOUXZLSNB-FTBISJDPSA-N 1-(2-chloro-4-methoxy-5-methylphenyl)-n-[(1s)-2-cyclopropyl-1-(4-fluorophenyl)ethyl]-5-methyl-n-propyl-1,2,4-triazol-3-amine;hydrochloride Chemical compound Cl.C([C@H](N(CCC)C1=NN(C(C)=N1)C=1C(=CC(OC)=C(C)C=1)Cl)C=1C=CC(F)=CC=1)C1CC1 LVBALXOUXZLSNB-FTBISJDPSA-N 0.000 claims description 3
- YHFYDMODNSVAPO-JIDHJSLPSA-N 1-(2-chloro-4-methoxyphenyl)-n-[(1s)-2-cyclopropyl-1-(3-fluoro-4-methylphenyl)ethyl]-5-methyl-n-propyl-1,2,4-triazol-3-amine;hydrochloride Chemical compound Cl.C([C@H](N(CCC)C1=NN(C(C)=N1)C=1C(=CC(OC)=CC=1)Cl)C=1C=C(F)C(C)=CC=1)C1CC1 YHFYDMODNSVAPO-JIDHJSLPSA-N 0.000 claims description 3
- HWQKGVPWMDGCTJ-BOXHHOBZSA-N 5-cyclopropyl-1-(2,4-dichlorophenyl)-n-[(1r)-1-(4-fluorophenyl)-2-methoxyethyl]-n-propyl-1,2,4-triazol-3-amine;hydrochloride Chemical compound Cl.C1([C@H](COC)N(CCC)C2=NN(C(C3CC3)=N2)C=2C(=CC(Cl)=CC=2)Cl)=CC=C(F)C=C1 HWQKGVPWMDGCTJ-BOXHHOBZSA-N 0.000 claims description 3
- UMKBWCOXZVINFP-UHFFFAOYSA-N 5-cyclopropyl-n-[2-cyclopropyl-1-(3-fluoro-4-methylphenyl)ethyl]-1-(2,4-dichlorophenyl)-n-propyl-1,2,4-triazol-3-amine;hydrochloride Chemical compound Cl.N1=C(C2CC2)N(C=2C(=CC(Cl)=CC=2)Cl)N=C1N(CCC)C(C=1C=C(F)C(C)=CC=1)CC1CC1 UMKBWCOXZVINFP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- FXJFOIYJZQPVHA-UHFFFAOYSA-N n-[2-cyclopropyl-1-(4-fluorophenyl)ethyl]-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-methyl-n-propyl-1,2,4-triazol-3-amine;hydrochloride Chemical compound Cl.N1=C(C)N(C=2C(=CC(=CC=2Cl)C(F)(F)F)Cl)N=C1N(CCC)C(C=1C=CC(F)=CC=1)CC1CC1 FXJFOIYJZQPVHA-UHFFFAOYSA-N 0.000 claims description 3
- SLIZMVXWEHEBIK-BQAIUKQQSA-N 1-(2-chloro-4-methoxyphenyl)-n-[(1s)-2-cyclopropyl-1-(4-fluorophenyl)ethyl]-5-methyl-n-propyl-1,2,4-triazol-3-amine;hydrochloride Chemical compound Cl.C([C@H](N(CCC)C1=NN(C(C)=N1)C=1C(=CC(OC)=CC=1)Cl)C=1C=CC(F)=CC=1)C1CC1 SLIZMVXWEHEBIK-BQAIUKQQSA-N 0.000 claims description 2
- NEURYOYRKPFLKH-UHFFFAOYSA-N 2-chloro-1-isocyanato-4-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC=C(N=C=O)C(Cl)=C1 NEURYOYRKPFLKH-UHFFFAOYSA-N 0.000 claims description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- PWSFZDMKNKEILM-BDQAORGHSA-N 1-(2,4-dichlorophenyl)-5-ethyl-n-[(1s)-1-phenylbutyl]-n-propyl-1,2,4-triazol-3-amine;hydrochloride Chemical compound Cl.CCCN([C@@H](CCC)C=1C=CC=CC=1)C(=N1)N=C(CC)N1C1=CC=C(Cl)C=C1Cl PWSFZDMKNKEILM-BDQAORGHSA-N 0.000 claims 1
- MMOTXSKMMZEXOF-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-5-methyl-N-propyl-1,2,4-triazol-3-amine hydrochloride Chemical compound Cl.ClC1=C(C=CC(=C1)Cl)N1N=C(N=C1C)NCCC MMOTXSKMMZEXOF-UHFFFAOYSA-N 0.000 claims 1
- AJCMNLUWKLXWQG-UHFFFAOYSA-N 1-(2-chloro-4-methoxy-5-methylphenyl)-5-cyclopropyl-n-(2-cyclopropyl-1-phenylethyl)-n-prop-2-ynyl-1,2,4-triazol-3-amine;hydrochloride Chemical compound Cl.C1=C(C)C(OC)=CC(Cl)=C1N1C(C2CC2)=NC(N(CC#C)C(CC2CC2)C=2C=CC=CC=2)=N1 AJCMNLUWKLXWQG-UHFFFAOYSA-N 0.000 claims 1
- VTOYLWIFVFRYHF-UHFFFAOYSA-N 1-(2-chloro-4-methoxy-5-methylphenyl)-5-cyclopropyl-n-[2-cyclopropyl-1-(4-fluorophenyl)ethyl]-n-prop-2-ynyl-1,2,4-triazol-3-amine;hydrochloride Chemical compound Cl.C1=C(C)C(OC)=CC(Cl)=C1N1C(C2CC2)=NC(N(CC#C)C(CC2CC2)C=2C=CC(F)=CC=2)=N1 VTOYLWIFVFRYHF-UHFFFAOYSA-N 0.000 claims 1
- FVXJMWZVSNUDJY-UHFFFAOYSA-N 1-(2-chloro-4-methoxy-5-methylphenyl)-5-cyclopropyl-n-[2-cyclopropyl-1-(4-fluorophenyl)ethyl]-n-propyl-1,2,4-triazol-3-amine;hydrochloride Chemical compound Cl.N1=C(C2CC2)N(C=2C(=CC(OC)=C(C)C=2)Cl)N=C1N(CCC)C(C=1C=CC(F)=CC=1)CC1CC1 FVXJMWZVSNUDJY-UHFFFAOYSA-N 0.000 claims 1
- YKOUFOAKCBVIHB-BOXHHOBZSA-N 1-(2-chloro-4-methoxy-5-methylphenyl)-5-methyl-n-[(1s)-1-phenylbutyl]-n-propyl-1,2,4-triazol-3-amine;hydrochloride Chemical compound Cl.CCCN([C@@H](CCC)C=1C=CC=CC=1)C(=N1)N=C(C)N1C1=CC(C)=C(OC)C=C1Cl YKOUFOAKCBVIHB-BOXHHOBZSA-N 0.000 claims 1
- NHRBJOZXJOSLOZ-UHFFFAOYSA-N 1-methyl-N-propyl-1,2,4-triazol-3-amine hydrochloride Chemical compound Cl.CN1N=C(N=C1)NCCC NHRBJOZXJOSLOZ-UHFFFAOYSA-N 0.000 claims 1
- PZSMXSNSKGLUSK-FTBISJDPSA-N 5-cyclopropyl-1-(2,4-dichlorophenyl)-n-[(1s)-1-(4-methylphenyl)butyl]-n-propyl-1,2,4-triazol-3-amine;hydrochloride Chemical compound Cl.CCCN([C@@H](CCC)C=1C=CC(C)=CC=1)C(=NN1C=2C(=CC(Cl)=CC=2)Cl)N=C1C1CC1 PZSMXSNSKGLUSK-FTBISJDPSA-N 0.000 claims 1
- VJGNHJIBHPFWMZ-BOXHHOBZSA-N 5-cyclopropyl-1-(2,4-dichlorophenyl)-n-[(1s)-1-phenylbutyl]-n-propyl-1,2,4-triazol-3-amine;hydrochloride Chemical compound Cl.CCCN([C@@H](CCC)C=1C=CC=CC=1)C(=NN1C=2C(=CC(Cl)=CC=2)Cl)N=C1C1CC1 VJGNHJIBHPFWMZ-BOXHHOBZSA-N 0.000 claims 1
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- FMGRTADHNQGYEK-BOXHHOBZSA-N n-[(1s)-1-(1,3-benzodioxol-5-yl)-2-cyclopropylethyl]-1-(2,4-dichlorophenyl)-5-methyl-n-propyl-1,2,4-triazol-3-amine;hydrochloride Chemical compound Cl.C([C@H](N(CCC)C1=NN(C(C)=N1)C=1C(=CC(Cl)=CC=1)Cl)C=1C=C2OCOC2=CC=1)C1CC1 FMGRTADHNQGYEK-BOXHHOBZSA-N 0.000 claims 1
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- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/06—Drugs for disorders of the endocrine system of the anterior pituitary hormones, e.g. TSH, ACTH, FSH, LH, PRL, GH
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Reproductive Health (AREA)
- Endocrinology (AREA)
- Pain & Pain Management (AREA)
- Gynecology & Obstetrics (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Rheumatology (AREA)
- Diabetes (AREA)
- Nutrition Science (AREA)
- Pregnancy & Childbirth (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9915935A FR2802530B1 (fr) | 1999-12-17 | 1999-12-17 | Nouveaux derives amino substitues ramifies du 3-amino-1-phenyl-1h[1,2,4]triazole, procedes pour leur preparation et compositions pharmaceutiques les contenant |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200204422B true ZA200204422B (en) | 2003-11-26 |
Family
ID=9553380
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200204422A ZA200204422B (en) | 1999-12-17 | 2002-06-03 | Branched substituted amino derivatives of 3-amino-1-phenyl-1H(1,2,4)triazol, methods for producing them and pharmaceutical compositions containing them. |
Country Status (34)
| Country | Link |
|---|---|
| US (1) | US6806282B2 (pt) |
| EP (1) | EP1242389B1 (pt) |
| JP (1) | JP4146641B2 (pt) |
| KR (1) | KR100705525B1 (pt) |
| CN (1) | CN1293061C (pt) |
| AR (1) | AR031837A1 (pt) |
| AT (1) | ATE264847T1 (pt) |
| AU (1) | AU780711B2 (pt) |
| BR (1) | BR0017023A (pt) |
| CA (1) | CA2398772C (pt) |
| CO (1) | CO5251379A1 (pt) |
| CZ (1) | CZ302460B6 (pt) |
| DE (1) | DE60010126T2 (pt) |
| DK (1) | DK1242389T3 (pt) |
| EA (1) | EA004957B1 (pt) |
| EE (1) | EE04778B1 (pt) |
| ES (1) | ES2219436T3 (pt) |
| FR (1) | FR2802530B1 (pt) |
| HK (1) | HK1055947A1 (pt) |
| HU (1) | HUP0204080A3 (pt) |
| IL (2) | IL150037A0 (pt) |
| IS (1) | IS2315B (pt) |
| ME (1) | MEP12108A (pt) |
| MX (1) | MXPA02006033A (pt) |
| NO (1) | NO20022828L (pt) |
| PL (1) | PL203819B1 (pt) |
| PT (1) | PT1242389E (pt) |
| RS (1) | RS50289B (pt) |
| SK (1) | SK285994B6 (pt) |
| TR (2) | TR200401775T4 (pt) |
| TW (1) | TWI289554B (pt) |
| UA (1) | UA73333C2 (pt) |
| WO (1) | WO2001044207A2 (pt) |
| ZA (1) | ZA200204422B (pt) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7226920B2 (en) * | 2003-08-06 | 2007-06-05 | Vertex Pharmaceuticals Inc. | Aminotriazole compounds useful as inhibitors of protein kinases |
| JO3019B1 (ar) | 2006-04-19 | 2016-09-05 | Janssen Pharmaceutica Nv | ثلاثي مستبدل 4،2،1-ثلاثي زولات |
| JO2784B1 (en) | 2007-10-18 | 2014-03-15 | شركة جانسين فارماسوتيكا ان. في | 5,3,1 - Triazole substitute derivative |
| RU2474579C2 (ru) | 2007-10-18 | 2013-02-10 | Янссен Фармацевтика Нв | Тризамещенные 1,2,4-триазолы |
| AU2009226988B2 (en) | 2008-03-19 | 2013-05-23 | Janssen Pharmaceutica Nv | Trisubstituted 1, 2, 4 -triazoles as nicotinic acetylcholine receptor modulators |
| JP5486591B2 (ja) | 2008-05-09 | 2014-05-07 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | アセチルコリン受容体モジュレーターとしての三置換ピラゾール |
| US20130225583A1 (en) * | 2010-10-21 | 2013-08-29 | Gerald W. Shipps, Jr. | Substituted amino-triazolyl pde10 inhibitors |
| EP3096756B1 (en) | 2014-01-21 | 2024-06-12 | Neurocrine Biosciences, Inc. | Crf1 receptor antagonists for the treatment of congenital adrenal hyperplasia |
| CN104059027B (zh) * | 2014-07-01 | 2015-10-28 | 河北大学 | 一类含1,2,4-三唑的(e)-甲氧基亚氨基苯乙酸甲酯类化合物及其制备方法和用途 |
| MX2022002881A (es) * | 2019-09-25 | 2022-06-08 | Oncoarendi Therapeutics Sa | Proceso para la produccion de 5-(4-((2s,5s)-5-(4-clorobencil)-2-me tilmorfolino)piperidin-1-il)-1h-1,2,4-triazol-3-amina. |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3869167D1 (de) * | 1987-03-27 | 1992-04-23 | Kumiai Chemical Industry Co | Phenyltriazol-derivate und insectizid. |
| US5795905A (en) * | 1995-06-06 | 1998-08-18 | Neurocrine Biosciences, Inc. | CRF receptor antagonists and methods relating thereto |
| FR2763337B1 (fr) * | 1997-05-13 | 1999-08-20 | Sanofi Sa | Nouveaux derives du triazole, un procede pour leur preparation et compositions pharmaceutiques les contenant |
-
1999
- 1999-12-17 FR FR9915935A patent/FR2802530B1/fr not_active Expired - Fee Related
-
2000
- 2000-12-14 EP EP00988916A patent/EP1242389B1/fr not_active Expired - Lifetime
- 2000-12-14 SK SK850-2002A patent/SK285994B6/sk not_active IP Right Cessation
- 2000-12-14 AT AT00988916T patent/ATE264847T1/de active
- 2000-12-14 EE EEP200200331A patent/EE04778B1/xx not_active IP Right Cessation
- 2000-12-14 RS YUP-439/02A patent/RS50289B/sr unknown
- 2000-12-14 US US10/149,499 patent/US6806282B2/en not_active Expired - Lifetime
- 2000-12-14 TR TR2004/01775T patent/TR200401775T4/xx unknown
- 2000-12-14 ES ES00988916T patent/ES2219436T3/es not_active Expired - Lifetime
- 2000-12-14 MX MXPA02006033A patent/MXPA02006033A/es active IP Right Grant
- 2000-12-14 AU AU25259/01A patent/AU780711B2/en not_active Ceased
- 2000-12-14 CO CO00095200A patent/CO5251379A1/es not_active Application Discontinuation
- 2000-12-14 WO PCT/FR2000/003536 patent/WO2001044207A2/fr active IP Right Grant
- 2000-12-14 HU HU0204080A patent/HUP0204080A3/hu unknown
- 2000-12-14 EA EA200200523A patent/EA004957B1/ru not_active IP Right Cessation
- 2000-12-14 DK DK00988916T patent/DK1242389T3/da active
- 2000-12-14 BR BR0017023-2A patent/BR0017023A/pt active Search and Examination
- 2000-12-14 IL IL15003700A patent/IL150037A0/xx active IP Right Grant
- 2000-12-14 DE DE60010126T patent/DE60010126T2/de not_active Expired - Lifetime
- 2000-12-14 ME MEP-121/08A patent/MEP12108A/xx unknown
- 2000-12-14 CA CA2398772A patent/CA2398772C/fr not_active Expired - Fee Related
- 2000-12-14 UA UA2002064623A patent/UA73333C2/uk unknown
- 2000-12-14 PT PT00988916T patent/PT1242389E/pt unknown
- 2000-12-14 KR KR1020027007736A patent/KR100705525B1/ko not_active IP Right Cessation
- 2000-12-14 TR TR2002/01600T patent/TR200201600T2/xx unknown
- 2000-12-14 CZ CZ20022099A patent/CZ302460B6/cs not_active IP Right Cessation
- 2000-12-14 PL PL355811A patent/PL203819B1/pl not_active IP Right Cessation
- 2000-12-14 CN CNB00819078XA patent/CN1293061C/zh not_active Expired - Fee Related
- 2000-12-14 JP JP2001544697A patent/JP4146641B2/ja not_active Expired - Lifetime
- 2000-12-15 AR ARP000106666A patent/AR031837A1/es not_active Application Discontinuation
-
2001
- 2001-01-29 TW TW089126997A patent/TWI289554B/zh not_active IP Right Cessation
-
2002
- 2002-05-04 IL IL150037A patent/IL150037A/en not_active IP Right Cessation
- 2002-05-28 IS IS6402A patent/IS2315B/is unknown
- 2002-06-03 ZA ZA200204422A patent/ZA200204422B/en unknown
- 2002-06-13 NO NO20022828A patent/NO20022828L/no not_active Application Discontinuation
-
2003
- 2003-11-11 HK HK03108164A patent/HK1055947A1/xx not_active IP Right Cessation
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