AR031837A1 - Derivados amino substituidos ramificados de 3-amino-1-fenil-1h [1, 2, 4] triazol, su utilizacion, procedimientos para su preparacion y composiciones farmaceuticas que los contienen - Google Patents
Derivados amino substituidos ramificados de 3-amino-1-fenil-1h [1, 2, 4] triazol, su utilizacion, procedimientos para su preparacion y composiciones farmaceuticas que los contienenInfo
- Publication number
- AR031837A1 AR031837A1 ARP000106666A ARP000106666A AR031837A1 AR 031837 A1 AR031837 A1 AR 031837A1 AR P000106666 A ARP000106666 A AR P000106666A AR P000106666 A ARP000106666 A AR P000106666A AR 031837 A1 AR031837 A1 AR 031837A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- cycloalkyl
- amino
- group
- derivatives
- Prior art date
Links
- -1 AMINO Chemical group 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 title abstract 2
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 21
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 8
- 229910052717 sulfur Inorganic materials 0.000 abstract 7
- 229910052760 oxygen Inorganic materials 0.000 abstract 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 229910003827 NRaRb Inorganic materials 0.000 abstract 2
- 125000003277 amino group Chemical group 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 2
- 229940079593 drug Drugs 0.000 abstract 2
- 239000003814 drug Substances 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 208000024827 Alzheimer disease Diseases 0.000 abstract 1
- 208000000103 Anorexia Nervosa Diseases 0.000 abstract 1
- 208000019901 Anxiety disease Diseases 0.000 abstract 1
- 206010006550 Bulimia nervosa Diseases 0.000 abstract 1
- 208000024172 Cardiovascular disease Diseases 0.000 abstract 1
- 208000018522 Gastrointestinal disease Diseases 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 230000036506 anxiety Effects 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 230000001419 dependent effect Effects 0.000 abstract 1
- 208000035475 disorder Diseases 0.000 abstract 1
- 230000002996 emotional effect Effects 0.000 abstract 1
- 206010015037 epilepsy Diseases 0.000 abstract 1
- 230000035558 fertility Effects 0.000 abstract 1
- 230000002496 gastric effect Effects 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 150000004677 hydrates Chemical class 0.000 abstract 1
- 208000026278 immune system disease Diseases 0.000 abstract 1
- 238000002483 medication Methods 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 230000007170 pathology Effects 0.000 abstract 1
- 208000020016 psychiatric disease Diseases 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 230000003938 response to stress Effects 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 230000001568 sexual effect Effects 0.000 abstract 1
- 239000012453 solvate Substances 0.000 abstract 1
- 125000004434 sulfur atom Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
- C07D249/14—Nitrogen atoms
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4196—1,2,4-Triazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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)
- Psychiatry (AREA)
- Gynecology & Obstetrics (AREA)
- Hospice & Palliative Care (AREA)
- Rheumatology (AREA)
- Diabetes (AREA)
- Pregnancy & Childbirth (AREA)
- Nutrition Science (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Derivados amino substituidos ramificados de 3-amino-1-fenil-1H[1,2,4] triazol de formula (1), en la cual: - R1 y R2 representan, cada uno independientemente del otro, un átomo de halogeno; un (C1-5)alquilo; un (C1-5)alcoxi; un grupo nitro, trifluorometilo o ciano; un grupo amino NRaRb en el cual Ra y Rb representan cada uno independientemente del otro, un hidrogeno, un (C1-3)alquilo, un CO(C1-3)alquilo, o bien en el cual Ra y Rb constituyen con el átomo de nitrogeno al que están enlazados, un heterociclo de 5 a 7 eslabones; un grupo S-R en el cual R representa un átomo de hidrogeno o un (C1-5)alquilo, pudiendo el átomo de azufre ser monooxidado o dioxidado; - R3 representa hidrogeno o es tal como se lo ha definido anteriormente para R1; - R4 representa hidrogeno; un halogeno; un (C1-5)alquilo; un (C3-5)cicloalquilo; un (C3-5)cicloalquil(C1-2)alquilo; un grupo Rc-X-(C1-2)alquilo en el cual Rc representa hidrogeno o un (C1-3)alquilo y X representa O, S, SO, SO2; - R5 representa un (C1-5)alquilo, un alquinilo de 3 a 5 átomos de carbono, un alquenilo de 3 a 5 átomos de carbono; un (C3-5)cicloalquil(C1-3)alquilo; un (C1-3)alquil-X(C0-3)alquilo en el cual X representa, O, S, SO, SO2; - R6 representa un grupo fenilo substituido por uno o varios radicales Z de los cuales al menos uno está en posicion 2 y Z representa un halogeno, un grupo nitro, trifluorometilo o ciano; un (C1-5)alquilo; un (C1-5)alquil-X- o (C1-3)alquil-X-(C1-2)alquilo en los cuales X representa O, S, SO o SO2; un hidroxi(C1-3)alquilo; un CORd o COORd donde Rd representa un (C1-3)alquilo o un (C3-5)cicloalquilo; - o bien R6 representa -CHR7R8 en el cual -R7 representa un (C3-5)cicloalquilo; un grupo fenilo que puede ser substituido en posicion 3, 4 y 5 por uno o varios radicales Z', con Z' que representa un halogeno, un grupo nitro, trifluorometilo o ciano; un (C1-5)alquilo; un(C1-5)alquil-X- o (C1-3)alquil-X-(C1-2)alquilo donde X representa O, S, SO o SO2; un hidroxi(C1-3)alquilo; un CORd o COORd en los cuales Rd es tal como se ha definido anteriormente; un metilendioxi, un etilendioxi; o bien un grupo piridilo eventualmente substituido por un grupo amino NRaRb tal como se ha definido precedentemente o por un radical Z' tal como se ha definido precedentemente; - R8 representa un (C1-6)alquilo; (C3-5)cicloalquilo; un (C3-5)cicloalquil(C1-3)alquilo; (C1-3)alquil-X-(C1-3)alquilo donde X representa O, S, SO o SO2; un (C3-5)cicloalquil(C1-2)alquil-X-(C1-3)alquilo donde X representa O, S, SO, SO2; así como sus sales de adicion farmacéuticamente aceptables, sus hidratos y/o solvatos. Los derivados de formula (1) encuentran especialmente sus aplicaciones como principios activos de medicamentos para disminuir la respuesta al estrés (comportamiento, estados emocionales, trastornos gastrointestinales y cardiovasculares, desordenes del sistema inmunitario) y más ampliamente en las patologías que implican al CRF, por ejemplo los desordenes psiquiátricos, la ansiedad, la depresion, la anorexia y la bulimia nerviosa, la epilepsia, los trastornos de la actividad sexual y de la fertilidad, la enfermedad de Alzheimer u otras. Utilizacion de los derivados de formula (1) para preparar medicamentos para prevenir y/o tratar las enfermedades CRF dependientes; procedimientos para preparar derivados de formula (1); y composiciones farmacéuticas que comprenden derivados de formula (1).
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 |
|---|---|
| AR031837A1 true AR031837A1 (es) | 2003-10-08 |
Family
ID=9553380
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP000106666A AR031837A1 (es) | 1999-12-17 | 2000-12-15 | Derivados amino substituidos ramificados de 3-amino-1-fenil-1h [1, 2, 4] triazol, su utilizacion, procedimientos para su preparacion y composiciones farmaceuticas que los contienen |
Country Status (33)
| Country | Link |
|---|---|
| US (1) | US6806282B2 (es) |
| EP (1) | EP1242389B1 (es) |
| JP (1) | JP4146641B2 (es) |
| KR (1) | KR100705525B1 (es) |
| CN (1) | CN1293061C (es) |
| AR (1) | AR031837A1 (es) |
| AT (1) | ATE264847T1 (es) |
| AU (1) | AU780711B2 (es) |
| BR (1) | BR0017023A (es) |
| CA (1) | CA2398772C (es) |
| CO (1) | CO5251379A1 (es) |
| CZ (1) | CZ302460B6 (es) |
| DE (1) | DE60010126T2 (es) |
| DK (1) | DK1242389T3 (es) |
| EA (1) | EA004957B1 (es) |
| EE (1) | EE04778B1 (es) |
| ES (1) | ES2219436T3 (es) |
| FR (1) | FR2802530B1 (es) |
| HU (1) | HUP0204080A3 (es) |
| IL (2) | IL150037A0 (es) |
| IS (1) | IS2315B (es) |
| ME (1) | MEP12108A (es) |
| MX (1) | MXPA02006033A (es) |
| NO (1) | NO20022828L (es) |
| PL (1) | PL203819B1 (es) |
| PT (1) | PT1242389E (es) |
| RS (1) | RS50289B (es) |
| SK (1) | SK285994B6 (es) |
| TR (2) | TR200201600T2 (es) |
| TW (1) | TWI289554B (es) |
| UA (1) | UA73333C2 (es) |
| WO (1) | WO2001044207A2 (es) |
| ZA (1) | ZA200204422B (es) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE455546T1 (de) * | 2003-08-06 | 2010-02-15 | Vertex Pharma | Aminotriazol-verbindungen als proteinkinase- hemmer |
| JO3019B1 (ar) | 2006-04-19 | 2016-09-05 | Janssen Pharmaceutica Nv | ثلاثي مستبدل 4،2،1-ثلاثي زولات |
| JP2011500625A (ja) | 2007-10-18 | 2011-01-06 | 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 | トリ置換された１，２，４−トリアゾール |
| JO2784B1 (en) | 2007-10-18 | 2014-03-15 | شركة جانسين فارماسوتيكا ان. في | 5,3,1 - Triazole substitute derivative |
| AR070936A1 (es) * | 2008-03-19 | 2010-05-12 | Janssen Pharmaceutica Nv | 1,2,4 -triazoles trisustituidos |
| 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 |
| KR20210064407A (ko) | 2014-01-21 | 2021-06-02 | 뉴로크린 바이오사이언시즈 인코퍼레이티드 | 선천성 부신 과형성 치료를 위한 ｃｒｆ1 수용체 길항제 |
| 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 |
| PL3984523T3 (pl) | 2018-12-07 | 2026-02-02 | Neurocrine Biosciences, Inc. | Antagonista receptora crf1, jego formulacje farmaceutyczne i postacie stałe do leczenia wrodzonego przerostu nadnerczy |
| JP7697933B2 (ja) * | 2019-09-25 | 2025-06-24 | オンコアレンディ セラピューティクス エス．エー． | ５－（４－（（２ｓ，５ｓ）－５－（４－クロロベンジル）－２－メチルモルホリノ）ピペリジン－１－イル）－１ｈ－１，２，４－トリアゾール－３－アミンの製造プロセス |
| US12383536B2 (en) | 2019-09-27 | 2025-08-12 | Neurocrine Biosciences, Inc. | CRF receptor antagonists and methods of use |
| ES3039926T3 (en) | 2019-12-04 | 2025-10-27 | Neurocrine Biosciences Inc | Crf receptor antagonists and methods of use |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0285893B1 (en) * | 1987-03-27 | 1992-03-18 | Kumiai Chemical Industry Co., Ltd. | Phenyltriazole derivative and insecticide |
| 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 MX MXPA02006033A patent/MXPA02006033A/es active IP Right Grant
- 2000-12-14 JP JP2001544697A patent/JP4146641B2/ja not_active Expired - Lifetime
- 2000-12-14 DK DK00988916T patent/DK1242389T3/da active
- 2000-12-14 CZ CZ20022099A patent/CZ302460B6/cs not_active IP Right Cessation
- 2000-12-14 TR TR2002/01600T patent/TR200201600T2/xx unknown
- 2000-12-14 AU AU25259/01A patent/AU780711B2/en not_active Ceased
- 2000-12-14 DE DE60010126T patent/DE60010126T2/de not_active Expired - Lifetime
- 2000-12-14 WO PCT/FR2000/003536 patent/WO2001044207A2/fr not_active Ceased
- 2000-12-14 IL IL15003700A patent/IL150037A0/xx active IP Right Grant
- 2000-12-14 EP EP00988916A patent/EP1242389B1/fr not_active Expired - Lifetime
- 2000-12-14 ES ES00988916T patent/ES2219436T3/es not_active Expired - Lifetime
- 2000-12-14 RS YUP-439/02A patent/RS50289B/sr unknown
- 2000-12-14 TR TR2004/01775T patent/TR200401775T4/xx unknown
- 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 KR KR1020027007736A patent/KR100705525B1/ko not_active Expired - Fee Related
- 2000-12-14 UA UA2002064623A patent/UA73333C2/uk unknown
- 2000-12-14 CN CNB00819078XA patent/CN1293061C/zh not_active Expired - Fee Related
- 2000-12-14 CA CA2398772A patent/CA2398772C/fr not_active Expired - Fee Related
- 2000-12-14 ME MEP-121/08A patent/MEP12108A/xx unknown
- 2000-12-14 SK SK850-2002A patent/SK285994B6/sk not_active IP Right Cessation
- 2000-12-14 CO CO00095200A patent/CO5251379A1/es not_active Application Discontinuation
- 2000-12-14 AT AT00988916T patent/ATE264847T1/de active
- 2000-12-14 PL PL355811A patent/PL203819B1/pl not_active IP Right Cessation
- 2000-12-14 EE EEP200200331A patent/EE04778B1/xx not_active IP Right Cessation
- 2000-12-14 US US10/149,499 patent/US6806282B2/en not_active Expired - Lifetime
- 2000-12-14 BR BR0017023-2A patent/BR0017023A/pt active Search and Examination
- 2000-12-14 PT PT00988916T patent/PT1242389E/pt unknown
- 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
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