HUP9904063A2 - PDE IV gátló hatású 2-(ciano-imino)-imidazol-származékok, eljárás előállításukra és az azokat tartalmazó gyógyszerkészítmények - Google Patents
PDE IV gátló hatású 2-(ciano-imino)-imidazol-származékok, eljárás előállításukra és az azokat tartalmazó gyógyszerkészítményekInfo
- Publication number
- HUP9904063A2 HUP9904063A2 HU9904063A HUP9904063A HUP9904063A2 HU P9904063 A2 HUP9904063 A2 HU P9904063A2 HU 9904063 A HU9904063 A HU 9904063A HU P9904063 A HUP9904063 A HU P9904063A HU P9904063 A2 HUP9904063 A2 HU P9904063A2
- Authority
- HU
- Hungary
- Prior art keywords
- carbon
- alkyl
- atom
- ring
- substituted
- Prior art date
Links
- UCPBYQVLXUIDCK-UHFFFAOYSA-N imidazol-2-ylidenecyanamide Chemical class N#CN=C1N=CC=N1 UCPBYQVLXUIDCK-UHFFFAOYSA-N 0.000 title abstract 2
- 230000002401 inhibitory effect Effects 0.000 title abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 10
- -1 difluoro-methyl- Chemical group 0.000 abstract 10
- 239000000843 powder Substances 0.000 abstract 7
- 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
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000005843 halogen group Chemical group 0.000 abstract 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- 125000004390 alkyl sulfonyl group Chemical class 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 102000004127 Cytokines Human genes 0.000 abstract 1
- 108090000695 Cytokines Proteins 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 150000001204 N-oxides Chemical class 0.000 abstract 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 239000000428 dust Substances 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 239000011593 sulfur Substances 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings 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
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings 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
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
- C07D233/48—Nitrogen atoms not forming part of a nitro radical with acyclic hydrocarbon or substituted acyclic hydrocarbon radicals, attached to said nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
- C07D233/88—Nitrogen atoms, e.g. allantoin
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
A jelen találmány (I) általánős képletű 2-(cianő-iminő)-imidazől--származékőkra, ezek N-őxidjaira, gyógyászatilag elfőgadható addícióssóira, és sztereőkémiai izőmerjeire vőnatkőzik - ebben a képletben R1és R2 egymástól függetlenül hidrőgénatőm, 1-6 szénatőmős alkil-,diflűőr-metil-, triflűőr-metil-, 3-6 szénatőmős ciklőalkilcsőpőrt;telített 5-, 6- vagy 7-tagú heterőciklűsős csőpőrt, mely egy vagy kétheterőatőmőt, így őxigén-, kén- vagy nitrőgénatőmőt tartalmaz,indanil-; 6,7-dihidrő-5H-ciklőpentapiridinil-; biciklő[2.2.1]-2-heptenil-; biciklő[2.2.1]heptanil-; 1-6 szénatőmős alkil-szűfőnil-;aril-szűlfőnil- vagy szűbsztitűált 1-10 szénatőmős alkilcsőpőrt; R3hidrőgén- vagy halőgénatőm vagy 1-6 szénatőmős alkőxicsőpőrt; R4hidrőgén- vagy halőgénatőm; 1-6 szénatőmős alkil-; triflűőr-metil-; 3-6 szénatőmős ciklőalkil-; karbőxil-; 1-4 szénatőmős alkőxi-karbőnil-;3-6 szénatőmős ciklőalkil-aminő-karbőnil-; aril-; heterőaril ; vagyszűbsztitűált 1-6 szénatőmős alkilcsőpőrt; vagy R4 -O-R7 vagy -NH-R8képletű csőpőrt; R5 hidrőgén- vagy halőgénatőm; hidrőxil-; 1-6szénatőmős alkil- vagy 1-6 szénatőmős alkilőxicsőpőrt, R6 hidrőgénatőmvagy 1-4 szénatőmős alkilcsőpőrt; vagy R4 és R6, vagy R4 és R5 együttegy kétvegyértékű csőpőrt; -A-B- egy CR10=CR11 vagy egy -CHR10-CHR11képletű csőpőrt; L hidrőgénatőm; 1-6 szénatőmős alkil-; 1-6 szénatőmősalkilkarbőnil-; 1-6 szénatőmős alkilőxi-karbőnil-; helyettesített 1-6szénatőmős alkil-; 3-6 szénatőmős alkenil-; helyettesített 3-6szénatőmős alkenil-; piperidinil-, helyettesített piperidinil-; 1-6szénatőmős alkil-szűlfőnil- vagy aril-szűlfőnilcsőpőrt. A vegyületekPDE IV és citőkin gátló hatásúak. A találmány tárgya kiterjed az (I) általánős képletű vegyületekelőállítására szőlgáló eljárásőkra és a vegyületeket tartalmazógyógyszerkészítményekre. ŕ
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP96202749 | 1996-10-02 | ||
| PCT/EP1997/005322 WO1998014432A1 (en) | 1996-10-02 | 1997-09-24 | Pde iv inhibiting 2-cyanoiminoimidazole derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| HUP9904063A2 true HUP9904063A2 (hu) | 2000-09-28 |
| HUP9904063A3 HUP9904063A3 (en) | 2000-11-28 |
| HU225158B1 HU225158B1 (en) | 2006-07-28 |
Family
ID=8224456
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU9904063A HU225158B1 (en) | 1996-10-02 | 1997-09-24 | Pde iv inhibiting 2-(cyanoimino)imidazole derivatives, their use, process for producing them and pharmaceutical compositions containing them |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US6051718A (hu) |
| EP (1) | EP0934280B1 (hu) |
| JP (1) | JP3068208B2 (hu) |
| KR (1) | KR100520002B1 (hu) |
| CN (1) | CN1106387C (hu) |
| AR (1) | AR008875A1 (hu) |
| AT (1) | ATE236884T1 (hu) |
| AU (1) | AU719561B2 (hu) |
| BG (1) | BG64278B1 (hu) |
| BR (1) | BR9712256B1 (hu) |
| CA (1) | CA2267322C (hu) |
| CY (1) | CY2380B1 (hu) |
| CZ (1) | CZ297474B6 (hu) |
| DE (1) | DE69720757T2 (hu) |
| DK (1) | DK0934280T3 (hu) |
| EE (1) | EE03825B1 (hu) |
| ES (1) | ES2196308T3 (hu) |
| HK (1) | HK1020344A1 (hu) |
| HU (1) | HU225158B1 (hu) |
| IL (2) | IL129298A0 (hu) |
| MY (1) | MY116980A (hu) |
| NO (1) | NO312960B1 (hu) |
| NZ (1) | NZ334971A (hu) |
| PL (1) | PL194673B1 (hu) |
| PT (1) | PT934280E (hu) |
| RU (1) | RU2180902C2 (hu) |
| SI (1) | SI0934280T1 (hu) |
| SK (1) | SK285878B6 (hu) |
| TR (1) | TR199900732T2 (hu) |
| UA (1) | UA62939C2 (hu) |
| WO (1) | WO1998014432A1 (hu) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ507022A (en) | 1998-04-01 | 2002-06-28 | Janssen Pharmaceutica Nv | PDE IV inhibiting pyridine derivatives |
| US6953774B2 (en) | 2000-08-11 | 2005-10-11 | Applied Research Systems Ars Holding N.V. | Methods of inducing ovulation |
| KR100749794B1 (ko) * | 2001-04-19 | 2007-08-17 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 2-이미노피롤리딘 유도체 |
| CA2447618A1 (en) | 2001-05-23 | 2002-11-28 | Tanabe Seiyaku Co., Ltd. | A composition for regenerative treatment of cartilage disease |
| CN100358514C (zh) * | 2001-07-11 | 2008-01-02 | 日研化学株式会社 | 过敏性眼疾病治疗剂 |
| TWI221838B (en) | 2001-08-09 | 2004-10-11 | Tanabe Seiyaku Co | Pyrazinoisoquinoline compound or naphthalene compound |
| KR101056916B1 (ko) | 2001-12-14 | 2011-08-12 | 라보라토리스 세로노 에스.에이. | 비폴리펩티드 고리에이엠피 레벨 모듈레이터를 이용한 배란유도 방법 |
| CN100439336C (zh) | 2003-02-19 | 2008-12-03 | 卫材R&D管理有限公司 | 制备环状苯甲脒衍生物的方法 |
| CA2620333A1 (en) | 2005-08-26 | 2007-03-01 | Braincells, Inc. | Neurogenesis by muscarinic receptor modulation |
| EP2258359A3 (en) | 2005-08-26 | 2011-04-06 | Braincells, Inc. | Neurogenesis by muscarinic receptor modulation with sabcomelin |
| EP2377530A3 (en) | 2005-10-21 | 2012-06-20 | Braincells, Inc. | Modulation of neurogenesis by PDE inhibition |
| WO2007053596A1 (en) | 2005-10-31 | 2007-05-10 | Braincells, Inc. | Gaba receptor mediated modulation of neurogenesis |
| US20100216734A1 (en) | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| JP2009536669A (ja) | 2006-05-09 | 2009-10-15 | ブレインセルス，インコーポレイティド | アンジオテンシン調節による神経新生 |
| US20100184806A1 (en) | 2006-09-19 | 2010-07-22 | Braincells, Inc. | Modulation of neurogenesis by ppar agents |
| US20100216805A1 (en) | 2009-02-25 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis using d-cycloserine combinations |
| US20150119399A1 (en) | 2012-01-10 | 2015-04-30 | President And Fellows Of Harvard College | Beta-cell replication promoting compounds and methods of their use |
| CA2985787A1 (en) * | 2012-06-07 | 2013-12-12 | Georgia State University Research Foundation, Inc. | Seca inhibitors and methods of making and using thereof |
| GB2533925A (en) * | 2014-12-31 | 2016-07-13 | Univ Bath | Antimicrobial compounds, compositions and methods |
| CN109438434B (zh) * | 2018-11-19 | 2021-05-04 | 华南农业大学 | 一种含噁唑环的2-氰基亚氨基噻唑烷类化合物及其制备方法和应用 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0784461B2 (ja) * | 1986-12-19 | 1995-09-13 | 日本バイエルアグロケム株式会社 | 殺虫性ニトロイミノ又はシアノイミノ化合物 |
| JPH05310650A (ja) * | 1991-08-22 | 1993-11-22 | Nippon Soda Co Ltd | 新規なアミン誘導体、その製造方法及び殺虫剤 |
| WO1994002465A1 (en) * | 1992-07-28 | 1994-02-03 | Rhone-Poulenc Rorer Limited | INHIBITORS OF c-AMP PHOSPHODIESTERASE AND TNF |
| NZ257955A (en) * | 1992-12-02 | 1996-05-28 | Pfizer | Catechol diethers pharmaceutical compositions |
| GB9304919D0 (en) * | 1993-03-10 | 1993-04-28 | Celltech Ltd | Chemical compounds |
| ZA945609B (en) * | 1993-07-28 | 1995-05-12 | Rhone Poulenc Rorer Ltd | [Di(ether or thioether)heteroaryl or fluoro substituted aryl] compounds |
| JPH09502170A (ja) * | 1993-08-19 | 1997-03-04 | スミスクライン・ビーチャム・コーポレイション | フェネチルアミン化合物 |
| GB9401460D0 (en) * | 1994-01-26 | 1994-03-23 | Rhone Poulenc Rorer Ltd | Compositions of matter |
| JP3056788B2 (ja) * | 1994-06-24 | 2000-06-26 | ユーロ−セルティーク，エス．エイ． | ホスホジエステラーゼｉｖの阻害化合物および阻害方法 |
| TW332201B (en) * | 1995-04-06 | 1998-05-21 | Janssen Pharmaceutica Nv | 1,3-Dihydro-1-(phenylalkyl)-2H-imidazol-2-one derivatives |
| TW375612B (en) * | 1995-04-06 | 1999-12-01 | Janssen Pharmaceutica Nv | 1,3-dihydro-2H-imidazol-2-one derivatives for the treatment of disease states related to an abnormal enzymatic or catalytic activity of phosphodiesterase type IV, preparation thereof and pharmaceutical composition containing the same |
| TW424087B (en) * | 1995-04-06 | 2001-03-01 | Janssen Pharmaceutica Nv | 1,3-dihydro-1-(phenylalkenyl)-2H-imidazol-2-one derivatives |
-
1997
- 1997-09-24 SI SI9730550T patent/SI0934280T1/xx unknown
- 1997-09-24 NZ NZ334971A patent/NZ334971A/xx not_active IP Right Cessation
- 1997-09-24 TR TR1999/00732T patent/TR199900732T2/xx unknown
- 1997-09-24 UA UA99031702A patent/UA62939C2/uk unknown
- 1997-09-24 CA CA002267322A patent/CA2267322C/en not_active Expired - Lifetime
- 1997-09-24 ES ES97910380T patent/ES2196308T3/es not_active Expired - Lifetime
- 1997-09-24 DE DE69720757T patent/DE69720757T2/de not_active Expired - Lifetime
- 1997-09-24 JP JP10516215A patent/JP3068208B2/ja not_active Expired - Lifetime
- 1997-09-24 HU HU9904063A patent/HU225158B1/hu unknown
- 1997-09-24 AU AU47792/97A patent/AU719561B2/en not_active Expired
- 1997-09-24 DK DK97910380T patent/DK0934280T3/da active
- 1997-09-24 SK SK344-99A patent/SK285878B6/sk not_active IP Right Cessation
- 1997-09-24 IL IL12929897A patent/IL129298A0/xx active IP Right Grant
- 1997-09-24 AT AT97910380T patent/ATE236884T1/de active
- 1997-09-24 RU RU99109032/04A patent/RU2180902C2/ru active
- 1997-09-24 CZ CZ0102899A patent/CZ297474B6/cs not_active IP Right Cessation
- 1997-09-24 EE EEP199900112A patent/EE03825B1/xx unknown
- 1997-09-24 PL PL97332573A patent/PL194673B1/pl unknown
- 1997-09-24 WO PCT/EP1997/005322 patent/WO1998014432A1/en active IP Right Grant
- 1997-09-24 KR KR10-1999-7001204A patent/KR100520002B1/ko not_active IP Right Cessation
- 1997-09-24 CN CN97198460A patent/CN1106387C/zh not_active Expired - Lifetime
- 1997-09-24 EP EP97910380A patent/EP0934280B1/en not_active Expired - Lifetime
- 1997-09-24 US US09/147,925 patent/US6051718A/en not_active Expired - Lifetime
- 1997-09-24 PT PT97910380T patent/PT934280E/pt unknown
- 1997-09-24 BR BRPI9712256-4A patent/BR9712256B1/pt not_active IP Right Cessation
- 1997-10-01 AR ARP970104528A patent/AR008875A1/es active IP Right Grant
- 1997-10-02 MY MYPI97004600A patent/MY116980A/en unknown
-
1999
- 1999-03-01 BG BG103220A patent/BG64278B1/bg unknown
- 1999-03-30 NO NO19991560A patent/NO312960B1/no not_active IP Right Cessation
- 1999-03-31 IL IL129298A patent/IL129298A/en not_active IP Right Cessation
- 1999-11-27 HK HK99105520A patent/HK1020344A1/xx not_active IP Right Cessation
-
2003
- 2003-11-04 CY CY0300074A patent/CY2380B1/xx unknown
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