TWI292712B - Aminoacetonitrile compounds for use in the control of endoparasites - Google Patents
Aminoacetonitrile compounds for use in the control of endoparasites Download PDFInfo
- Publication number
- TWI292712B TWI292712B TW090131306A TW90131306A TWI292712B TW I292712 B TWI292712 B TW I292712B TW 090131306 A TW090131306 A TW 090131306A TW 90131306 A TW90131306 A TW 90131306A TW I292712 B TWI292712 B TW I292712B
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- TW
- Taiwan
- Prior art keywords
- halogen
- alkyl
- group
- substituted
- substituents
- Prior art date
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- 244000079386 endoparasite Species 0.000 title claims 3
- 150000008361 aminoacetonitriles Chemical class 0.000 title 1
- -1 succinyloxy group Chemical group 0.000 claims description 43
- 125000001424 substituent group Chemical group 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 239000001257 hydrogen Substances 0.000 claims description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 32
- 229910052736 halogen Inorganic materials 0.000 claims description 30
- 239000004480 active ingredient Substances 0.000 claims description 29
- 150000002367 halogens Chemical class 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 16
- 241001465754 Metazoa Species 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 10
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 5
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
- 241000607479 Yersinia pestis Species 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
- 239000004615 ingredient Substances 0.000 claims description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
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- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 125000005554 pyridyloxy group Chemical group 0.000 claims 2
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- 235000003343 Brassica rupestris Nutrition 0.000 claims 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 1
- 150000001345 alkine derivatives Chemical class 0.000 claims 1
- RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical class [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 claims 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 claims 1
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- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Chemical group O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
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- 239000002689 soil Substances 0.000 claims 1
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- 229910021653 sulphate ion Inorganic materials 0.000 claims 1
- 239000013589 supplement Substances 0.000 claims 1
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- 238000002844 melting Methods 0.000 description 49
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
- 229910052698 phosphorus Inorganic materials 0.000 description 12
- 239000011574 phosphorus Substances 0.000 description 12
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- 229910052801 chlorine Inorganic materials 0.000 description 8
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 8
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- 241000238631 Hexapoda Species 0.000 description 5
- 230000000895 acaricidal effect Effects 0.000 description 5
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- 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
- A61K31/275—Nitriles; Isonitriles
-
- 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
- A61K31/275—Nitriles; Isonitriles
- A61K31/277—Nitriles; Isonitriles having a ring, e.g. verapamil
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
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- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Paper (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH24892000 | 2000-12-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI292712B true TWI292712B (en) | 2008-01-21 |
Family
ID=4569596
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW090131306A TWI292712B (en) | 2000-12-20 | 2001-12-18 | Aminoacetonitrile compounds for use in the control of endoparasites |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US7700656B2 (enExample) |
| EP (1) | EP1392281B1 (enExample) |
| JP (1) | JP2004521097A (enExample) |
| KR (1) | KR100850252B1 (enExample) |
| CN (1) | CN1531426A (enExample) |
| AR (1) | AR035523A1 (enExample) |
| AT (1) | ATE354360T1 (enExample) |
| AU (2) | AU2002234588B2 (enExample) |
| BR (1) | BR0116326A (enExample) |
| CA (1) | CA2432388C (enExample) |
| CY (1) | CY1106509T1 (enExample) |
| DE (1) | DE60126838T2 (enExample) |
| DK (1) | DK1392281T3 (enExample) |
| ES (1) | ES2281453T3 (enExample) |
| MX (1) | MXPA03005701A (enExample) |
| NZ (1) | NZ526538A (enExample) |
| PT (1) | PT1392281E (enExample) |
| RU (1) | RU2286775C2 (enExample) |
| TW (1) | TWI292712B (enExample) |
| WO (1) | WO2002049641A2 (enExample) |
| ZA (1) | ZA200304331B (enExample) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR035531A1 (es) * | 2001-01-22 | 2004-06-02 | Novartis Ag | Composicion para el control de plagas endoparasiticas en ganados y animales domesticos, un metodo para su control y el uso de dicha composicion para la preparacion de medicamentos |
| AR036054A1 (es) * | 2001-06-15 | 2004-08-04 | Novartis Ag | Uso de compuestos de aminoacetonitrilo para el control de plagas, una composicion y un proceso para dicho control y una composicion farmaceutica contra parasitos |
| WO2003004474A1 (en) * | 2001-07-06 | 2003-01-16 | Syngenta Participations Ag | Pesticidally active aminoacetonitriles |
| AR037746A1 (es) * | 2001-12-06 | 2004-12-01 | Novartis Ag | Compuestos derivados de amidoacetonitrilo, un procedimiento para su preparacion, un procedimiento para la preparacion de compuestos intermediarios, una composicion para combatir parasitos, un procedimiento para combatir dichos parasitos, y el empleo de dichos derivados para la preparacion de una com |
| AR039020A1 (es) * | 2002-03-21 | 2005-02-02 | Novartis Ag | Compuestos de aminoacetonitrilo |
| TW200400932A (en) * | 2002-06-19 | 2004-01-16 | Novartis Ag | Organic compounds |
| AR042420A1 (es) | 2002-09-11 | 2005-06-22 | Novartis Ag | Benzotriazolil- aminoacetonitril compuestos, proceso para su preparacion, metodo y uso de los mismos en el control de endo- y ecto-parasitos dentro y sobre ganado productor de sangre caliente y animales domesticos y plantas, y en la preparacion de una composicion farmaceutica |
| GB0402677D0 (en) * | 2003-11-06 | 2004-03-10 | Novartis Ag | Organic compounds |
| DE10358525A1 (de) * | 2003-12-13 | 2005-07-07 | Bayer Healthcare Ag | Endoparasitizide Mittel zur topischen Applikation |
| AR049391A1 (es) | 2004-06-10 | 2006-07-26 | Novartis Ag | Derivados de aminoacetonitrilo y su uso para controlar parasitos en animales de sangre caliente |
| WO2006043654A1 (ja) * | 2004-10-22 | 2006-04-27 | Nihon Nohyaku Co., Ltd. | アセトニトリル誘導体及び有害生物防除剤並びにその使用方法 |
| EP1812385B1 (en) * | 2004-11-09 | 2012-07-18 | Novartis AG | Process for the preparation of enantiomers of amidoacetonitrile compounds from their racemates |
| EP1910278A1 (en) * | 2005-07-25 | 2008-04-16 | Novartis AG | Amidonitrile compounds |
| DE102006025874A1 (de) | 2006-06-02 | 2007-12-06 | Bayer Cropscience Ag | Alkoxyalkyl-substituierte cyclische Ketoenole |
| WO2008062005A1 (en) * | 2006-11-24 | 2008-05-29 | Novartis Ag | The use of aminoacetonitril compounds in the control of endoparasites in warm- blood animals. |
| BRPI0807137A2 (pt) * | 2007-02-09 | 2014-04-15 | Pfizer Ltd | Agentes antiparasitários |
| JP5327876B2 (ja) * | 2007-02-21 | 2013-10-30 | ゾエティス・ユーケイ・リミテッド | ベンゾフラン抗寄生虫剤 |
| KR101472649B1 (ko) | 2007-05-15 | 2014-12-16 | 메리얼 리미티드 | 아릴로아졸-2-일 시아노에틸아미노 화합물, 이의 제조방법 및 이의 사용방법 |
| WO2010048191A1 (en) | 2008-10-21 | 2010-04-29 | Merial Limited | Thioamide compounds, method of making and method of using thereof |
| RS58508B1 (sr) | 2008-11-14 | 2019-04-30 | Merial Inc | Enantiomerno obogaćena paraziticidalna jedinjenja ariloazol-2-il cijanoetilamino |
| UY33282A (es) * | 2010-03-25 | 2011-09-30 | Novartis Ag | Composiciones endoparasiticidas |
| ES2625990T3 (es) * | 2011-03-02 | 2017-07-21 | The University Of Tokyo | Agente de control de endoparásitos |
| AR088984A1 (es) * | 2011-11-25 | 2014-07-23 | Bayer Ip Gmbh | Aril y/o heteroaril carboxamidas utiles como endoparasiticidas en animales o seres humanos |
| BR112014018875A8 (pt) | 2012-02-14 | 2017-07-11 | Nippon Soda Co | Composto de ariloxiacetamida ou sal do mesmo, pesticida, acaricida ou inseticida, e, agente de controle de ectoparasita |
| US9790176B2 (en) | 2012-08-06 | 2017-10-17 | Pitney Pharmaceuticals Pty Limited | Compounds for the treatment of mTOR pathway related diseases |
| US8822689B2 (en) | 2012-09-19 | 2014-09-02 | Merial Limited | Aryloazol-2-yl cyanoethylamino compounds, method of making and method of using thereof |
| AR094961A1 (es) | 2013-03-15 | 2015-09-09 | Lilly Co Eli | 1-hidroxi-benzooxaboroles como agentes antiparasitarios |
| EP2821412A1 (en) * | 2013-07-01 | 2015-01-07 | Universität Zürich | Organometallic 2-cyano-2-aminobenzoate-propyl derivates and their use as anthelmintics |
| WO2015037747A1 (en) * | 2013-09-13 | 2015-03-19 | Nihon Nohyaku Co., Ltd. | Anticancer agent comprising aminoacetonitrile compound as active ingredient |
| AU2016224395A1 (en) * | 2015-02-24 | 2017-08-31 | Pitney Pharmaceuticals Pty Limited | Anti cancer agent comprising aminoacetonitrile compound as active ingredient |
| EP3235815A1 (de) | 2016-04-19 | 2017-10-25 | Philipps-Universität Marburg | Wirkstoffe gegen parasitäre helminthen |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1520925A (fr) * | 1966-04-22 | 1968-04-12 | Abbott Lab | Nouveaux benzoylamino-nitriles |
| US3457294A (en) * | 1966-04-22 | 1969-07-22 | Abbott Lab | N-(substituted-benzoyl) aminoaceto- and aminopropionitriles |
| US4515731A (en) * | 1975-08-25 | 1985-05-07 | Monsanto Company | Asymmetric catalysis |
| GB8517279D0 (en) * | 1985-07-08 | 1985-08-14 | Ici Plc | Benzamide derivatives |
| JP2994182B2 (ja) * | 1992-07-23 | 1999-12-27 | 石原産業株式会社 | アミド系化合物又はその塩、それらの製造方法及びそれらを含有する有害動物防除剤 |
| US6239077B1 (en) * | 1998-05-01 | 2001-05-29 | Nihon Nohyaku Co., Ltd. | Aminoacetonitrile derivative agricultural and horticultural insecticide containing the same and use thereof |
| AR035531A1 (es) * | 2001-01-22 | 2004-06-02 | Novartis Ag | Composicion para el control de plagas endoparasiticas en ganados y animales domesticos, un metodo para su control y el uso de dicha composicion para la preparacion de medicamentos |
| EP1390344B1 (en) * | 2001-05-15 | 2006-12-27 | Novartis AG | Benzamidoacetonitrile derivatives and their use as antiparasitics |
| AR036054A1 (es) * | 2001-06-15 | 2004-08-04 | Novartis Ag | Uso de compuestos de aminoacetonitrilo para el control de plagas, una composicion y un proceso para dicho control y una composicion farmaceutica contra parasitos |
| WO2003004474A1 (en) * | 2001-07-06 | 2003-01-16 | Syngenta Participations Ag | Pesticidally active aminoacetonitriles |
| AR038156A1 (es) * | 2002-01-21 | 2004-12-29 | Novartis Ag | Compuestos de amidoacetonitrilo, proceso para su preparacion, composicion para controlar los parasitos, y uso de estos compuestos para preparar una composicion farmaceutica |
-
2001
- 2001-12-18 DE DE60126838T patent/DE60126838T2/de not_active Expired - Lifetime
- 2001-12-18 BR BR0116326-4A patent/BR0116326A/pt not_active IP Right Cessation
- 2001-12-18 EP EP01985421A patent/EP1392281B1/en not_active Expired - Lifetime
- 2001-12-18 CA CA2432388A patent/CA2432388C/en not_active Expired - Lifetime
- 2001-12-18 CN CNA018210155A patent/CN1531426A/zh active Pending
- 2001-12-18 NZ NZ526538A patent/NZ526538A/en not_active IP Right Cessation
- 2001-12-18 AT AT01985421T patent/ATE354360T1/de active
- 2001-12-18 JP JP2002550981A patent/JP2004521097A/ja active Pending
- 2001-12-18 TW TW090131306A patent/TWI292712B/zh not_active IP Right Cessation
- 2001-12-18 US US10/433,811 patent/US7700656B2/en not_active Expired - Lifetime
- 2001-12-18 RU RU2003122196/15A patent/RU2286775C2/ru active
- 2001-12-18 AR ARP010105864A patent/AR035523A1/es not_active Application Discontinuation
- 2001-12-18 AU AU2002234588A patent/AU2002234588B2/en not_active Expired
- 2001-12-18 MX MXPA03005701A patent/MXPA03005701A/es active IP Right Grant
- 2001-12-18 AU AU3458802A patent/AU3458802A/xx active Pending
- 2001-12-18 PT PT01985421T patent/PT1392281E/pt unknown
- 2001-12-18 ES ES01985421T patent/ES2281453T3/es not_active Expired - Lifetime
- 2001-12-18 DK DK01985421T patent/DK1392281T3/da active
- 2001-12-18 WO PCT/EP2001/014926 patent/WO2002049641A2/en not_active Ceased
- 2001-12-18 KR KR1020037007242A patent/KR100850252B1/ko not_active Expired - Fee Related
-
2003
- 2003-06-03 ZA ZA200304331A patent/ZA200304331B/en unknown
-
2007
- 2007-04-12 CY CY20071100511T patent/CY1106509T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE60126838T2 (de) | 2007-11-08 |
| US7700656B2 (en) | 2010-04-20 |
| US20040082624A1 (en) | 2004-04-29 |
| ATE354360T1 (de) | 2007-03-15 |
| CY1106509T1 (el) | 2012-01-25 |
| DK1392281T3 (da) | 2007-06-11 |
| WO2002049641A2 (en) | 2002-06-27 |
| MXPA03005701A (es) | 2003-10-06 |
| PT1392281E (pt) | 2007-05-31 |
| DE60126838D1 (de) | 2007-04-05 |
| AU2002234588B2 (en) | 2005-03-24 |
| BR0116326A (pt) | 2004-07-06 |
| AU3458802A (en) | 2002-07-01 |
| CN1531426A (zh) | 2004-09-22 |
| CA2432388A1 (en) | 2002-06-27 |
| CA2432388C (en) | 2010-06-08 |
| EP1392281A2 (en) | 2004-03-03 |
| RU2003122196A (ru) | 2005-03-20 |
| KR20030061414A (ko) | 2003-07-18 |
| KR100850252B1 (ko) | 2008-08-04 |
| ZA200304331B (en) | 2004-04-28 |
| ES2281453T3 (es) | 2007-10-01 |
| WO2002049641A3 (en) | 2003-12-04 |
| JP2004521097A (ja) | 2004-07-15 |
| NZ526538A (en) | 2005-12-23 |
| AR035523A1 (es) | 2004-06-02 |
| EP1392281B1 (en) | 2007-02-21 |
| RU2286775C2 (ru) | 2006-11-10 |
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| MM4A | Annulment or lapse of patent due to non-payment of fees |