UY25041A1 - Derivados de macrolidos c-4" sustituidos - Google Patents
Derivados de macrolidos c-4" sustituidosInfo
- Publication number
- UY25041A1 UY25041A1 UY25041A UY25041A UY25041A1 UY 25041 A1 UY25041 A1 UY 25041A1 UY 25041 A UY25041 A UY 25041A UY 25041 A UY25041 A UY 25041A UY 25041 A1 UY25041 A1 UY 25041A1
- Authority
- UY
- Uruguay
- Prior art keywords
- infections
- groups
- formula
- compounds
- hydroxy
- Prior art date
Links
- 239000003120 macrolide antibiotic agent Substances 0.000 title abstract 4
- 229940041033 macrolides Drugs 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 4
- 208000022362 bacterial infectious disease Diseases 0.000 abstract 3
- 229910052799 carbon Inorganic materials 0.000 abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 3
- 208000035143 Bacterial infection Diseases 0.000 abstract 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- 239000003242 anti bacterial agent Substances 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical class O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 abstract 1
- 206010018364 Glomerulonephritis Diseases 0.000 abstract 1
- 241000124008 Mammalia Species 0.000 abstract 1
- 208000010315 Mastoiditis Diseases 0.000 abstract 1
- DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical group S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 abstract 1
- 206010031252 Osteomyelitis Diseases 0.000 abstract 1
- 206010033078 Otitis media Diseases 0.000 abstract 1
- 201000007100 Pharyngitis Diseases 0.000 abstract 1
- 206010035664 Pneumonia Diseases 0.000 abstract 1
- 206010037294 Puerperal pyrexia Diseases 0.000 abstract 1
- 206010057190 Respiratory tract infections Diseases 0.000 abstract 1
- 208000019802 Sexually transmitted disease Diseases 0.000 abstract 1
- 206010062255 Soft tissue infection Diseases 0.000 abstract 1
- 208000006374 Uterine Cervicitis Diseases 0.000 abstract 1
- 206010000269 abscess Diseases 0.000 abstract 1
- 230000001154 acute effect Effects 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 239000003904 antiprotozoal agent Substances 0.000 abstract 1
- 229960004099 azithromycin Drugs 0.000 abstract 1
- MQTOSJVFKKJCRP-BICOPXKESA-N azithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)N(C)C[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 MQTOSJVFKKJCRP-BICOPXKESA-N 0.000 abstract 1
- 206010006451 bronchitis Diseases 0.000 abstract 1
- 206010008323 cervicitis Diseases 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 208000035475 disorder Diseases 0.000 abstract 1
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 abstract 1
- 208000015181 infectious disease Diseases 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000002971 oxazolyl group Chemical group 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 230000003389 potentiating effect Effects 0.000 abstract 1
- 125000006239 protecting group Chemical group 0.000 abstract 1
- 208000020029 respiratory tract infectious disease Diseases 0.000 abstract 1
- 201000003068 rheumatic fever Diseases 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 201000009890 sinusitis Diseases 0.000 abstract 1
- 206010040872 skin infection Diseases 0.000 abstract 1
- 206010044008 tonsillitis Diseases 0.000 abstract 1
- 208000000143 urethritis Diseases 0.000 abstract 1
- 208000019206 urinary tract infection Diseases 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- 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
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Tropical Medicine & Parasitology (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
Esta invención se refiere a los nuevos derivados de macrólidos C-4" sustituidos que son útiles como agentes antibacterianos y antiprotozoos en mamíferos, incluyendo al hombre. Tales antibióticos macrólidos incluyen varios derivados de la eritromicina A como la azitromicina. Esta invención refiere a los compuestos macrólidos, de fórmula (I), y sus sales farmacéuticamente aceptables. Dichos compuestos son potentes agentes antibacterianos que pueden usarse para tratar diversas infecciones bacterianas y trastornos relacionados con las mismas. La invención también refiere las composiciones farmacéuticas que los contienen y a los métodos para el tratamiento de las infecciones bacterianas mediante la administración de los mismos. También refiere los métodos para la preparación y los productos intermedios útiles para dicha preparación. Compuestos de fórmula (I), en la que: X es CH(NR9R10), C(O), C(=NOR9), CH2NR9 ó N-alquilo-CH2 en los que la primera línea de cada uno de los anteriores grupos X está unida la carbono C10 y la última línea de cada grupo está unida al carbono C8 del compuesto de fórmula (I); R1 es H, hidroxi o metoxi; R2 es hidroxi; R3 es alquilo, alquenilo, alquinilo, ciano, CH2S(O)nR8, en el que n es un número entero entre 0 y 2, CH2OR8, CH2N(OR9)R8, CH2NR8R15, (CH2)m-arilo, ó (CH2)m-heteroarilo, en el que m es un número entero entre 0 y 4 y en los que los anteriores grupos R3 están opcionalmente sustituidos en 1 a 3 grupos R16; ó R2 y R3 están unidos formando un anillo oxazolilo; R4 es H, C(O)R9, C(O)OR9, C(O)NR9R10 ó un grupo protector de hidroxi. Útiles para trastornos relacionados con dichas infecciones que incluyen: neumonía, otitis media, sinusitis, bronquitis, tonsilitis y mastoiditis; faringitis, fiebre reumática y glomerulonefritis; infecciones del tracto respiratorio; infecciones de la piel y del tejido blando, abscesos y osteomielitis y fiebre puerperal; infecciones del tracto urinario agudas sin complicaciones; uretritis y cervicitis, y enfermedades de trasmisión sexual, entre otras.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4998097P | 1997-06-11 | 1997-06-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UY25041A1 true UY25041A1 (es) | 2000-09-29 |
Family
ID=21962765
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UY25041A UY25041A1 (es) | 1997-06-11 | 1998-06-11 | Derivados de macrolidos c-4" sustituidos |
Country Status (39)
| Country | Link |
|---|---|
| EP (1) | EP0988309B1 (es) |
| JP (1) | JP3262806B2 (es) |
| KR (1) | KR100369959B1 (es) |
| CN (1) | CN1145636C (es) |
| AP (1) | AP1189A (es) |
| AR (1) | AR013085A1 (es) |
| AT (1) | ATE310742T1 (es) |
| AU (1) | AU745006C (es) |
| BG (1) | BG64357B1 (es) |
| BR (1) | BR9810097A (es) |
| CA (1) | CA2293397C (es) |
| CO (1) | CO4950584A1 (es) |
| DE (1) | DE69832486T2 (es) |
| DZ (1) | DZ2515A1 (es) |
| EA (1) | EA002440B1 (es) |
| ES (1) | ES2251081T3 (es) |
| GT (1) | GT199800075A (es) |
| HN (1) | HN1998000074A (es) |
| HR (1) | HRP980315A2 (es) |
| HU (1) | HUP0004076A3 (es) |
| ID (1) | ID24530A (es) |
| IL (1) | IL132808A (es) |
| IS (1) | IS1979B (es) |
| MA (1) | MA24563A1 (es) |
| MY (1) | MY133027A (es) |
| NO (1) | NO315560B1 (es) |
| NZ (1) | NZ500652A (es) |
| OA (1) | OA11226A (es) |
| PA (1) | PA8452001A1 (es) |
| PE (1) | PE79999A1 (es) |
| PL (1) | PL337497A1 (es) |
| SK (1) | SK168299A3 (es) |
| TN (1) | TNSN98084A1 (es) |
| TW (2) | TWI224106B (es) |
| UA (1) | UA70298A (es) |
| UY (1) | UY25041A1 (es) |
| WO (1) | WO1998056801A1 (es) |
| YU (1) | YU62999A (es) |
| ZA (1) | ZA985016B (es) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6339063B1 (en) | 1997-09-10 | 2002-01-15 | Merck & Co., Inc. | 9a-azalides as veterinary antimicrobial agents |
| EP1779853A3 (en) * | 1997-09-10 | 2010-01-27 | Merial Ltd. | 9a-azalides as veterinary antimicrobial agents |
| AU731842B2 (en) * | 1997-09-10 | 2001-04-05 | Merck & Co., Inc. | 9a-azalides as veterinary antimicrobial agents |
| AP9801420A0 (en) * | 1998-01-02 | 1998-12-31 | Pfizer Prod Inc | Novel macrolides. |
| US6043227A (en) * | 1998-08-19 | 2000-03-28 | Pfizer Inc. | C11 carbamates of macrolide antibacterials |
| EP1437360A3 (en) * | 1998-08-19 | 2005-04-06 | Pfizer Products Inc. | C11 Carbamates of macrolide antibacterials |
| US6100240A (en) * | 1998-10-09 | 2000-08-08 | Pfizer Inc | Macrolide derivatives |
| SK5812001A3 (en) | 1998-11-03 | 2001-12-03 | Pfizer Prod Inc | Novel macrolide antibiotics |
| CA2292359C (en) * | 1999-01-28 | 2004-09-28 | Pfizer Products Inc. | Novel azalides and methods of making same |
| CA2380455C (en) * | 1999-08-24 | 2009-06-02 | Abbott Laboratories | 9a-azalides with antibacterial activity |
| US6764996B1 (en) | 1999-08-24 | 2004-07-20 | Abbott Laboratories | 9a-azalides with antibacterial activity |
| BRPI0017013B8 (pt) * | 2000-01-27 | 2022-11-16 | Pfizer Prod Inc | composição de antibiótico azalídeo e método para sua obtenção |
| BR0209241A (pt) * | 2001-04-27 | 2004-06-15 | Pfizer Prod Inc | Processo para preparação de derivados de9-deoxo-9a-aza-9a-homoeritromicina a 4-substituida |
| JP2003040782A (ja) * | 2001-05-31 | 2003-02-13 | Pfizer Prod Inc | アザリド抗生物質組成物 |
| PL374646A1 (en) * | 2002-07-08 | 2005-10-31 | Pliva-Istrazivacki Institutt D.O.O. | Novel nonsteroidal anti-inflammatory substances, compositions and methods for their use |
| DE60327341D1 (de) | 2002-07-08 | 2009-06-04 | Glaxosmithkline Zagreb | Hybridmoleküle von makroliden mit steroidalen/nicht-steroidalen antientzündlich aktiven molekülen |
| NZ537717A (en) | 2002-07-08 | 2006-04-28 | Pliva Istrazivacki Inst D | New compounds, compositions and methods for treatment of inflammatory diseases and conditions |
| AR043050A1 (es) | 2002-09-26 | 2005-07-13 | Rib X Pharmaceuticals Inc | Compuestos heterociclicos bifuncionales y metodos para preparar y usar los mismos |
| CA2529817C (en) * | 2003-03-10 | 2013-02-12 | Optimer Pharmaceuticals, Inc. | Novel antibacterial agents |
| WO2005030227A1 (en) | 2003-09-23 | 2005-04-07 | Enanta Pharmaceuticals, Inc. | 9a, 11-3C-BICYCLIC 9a-AZALIDE DERIVATIVES |
| JP5383037B2 (ja) | 2004-02-27 | 2014-01-08 | リブ−エックス ファーマシューティカルズ，インコーポレイテッド | 大環状化合物およびそれらを製造し使用する方法 |
| US8293715B2 (en) | 2007-08-06 | 2012-10-23 | Taisho Pharmaceutical Co., Ltd. | 10a-Azalide compound crosslinked at 10a- and 12-positions |
| AU2008316830B2 (en) | 2007-10-25 | 2016-03-17 | Cempra Pharmaceuticals, Inc. | Process for the preparation of macrolide antibacterial agents |
| US8299035B2 (en) | 2008-05-15 | 2012-10-30 | Taisho Pharmaceutucal Co., Ltd. | 10a-azalide compound having 4-membered ring structure |
| WO2010048600A1 (en) | 2008-10-24 | 2010-04-29 | Cempra Pharmaceuticals, Inc. | Methods for treating resistant diseases using triazole containing macrolides |
| US9937194B1 (en) | 2009-06-12 | 2018-04-10 | Cempra Pharmaceuticals, Inc. | Compounds and methods for treating inflammatory diseases |
| EP2619214B1 (en) * | 2010-09-20 | 2014-12-24 | Novartis AG | Novel process for the preparation of 9-deoxo-9a-aza-9a-homoerythromycin a modified in the c-4'' of the cladinose ring by an epoxide group |
| AR085286A1 (es) * | 2011-02-21 | 2013-09-18 | Taisho Pharmaceutical Co Ltd | Derivado de macrolido sustituido en la posicion c-4 |
| WO2013148891A1 (en) | 2012-03-27 | 2013-10-03 | Cempra Pharmaceuticals, Inc. | Parenteral formulations for administering macrolide antibiotics |
| JP5857008B2 (ja) * | 2012-08-20 | 2016-02-10 | 大正製薬株式会社 | Ｃ−４”位置換マクロライド誘導体を含有する医薬 |
| CN105246334A (zh) | 2013-04-04 | 2016-01-13 | 哈佛大学的校长及成员们 | 大环内酯及其制备和使用方法 |
| CN105669798B (zh) * | 2013-08-23 | 2019-07-26 | 普莱柯生物工程股份有限公司 | 一种大环内酯类化合物 |
| CN103965273B (zh) * | 2013-08-23 | 2016-05-25 | 普莱柯生物工程股份有限公司 | 一种大环内酯类化合物 |
| AR102810A1 (es) | 2014-08-18 | 2017-03-29 | Taisho Pharmaceutical Co Ltd | Derivado de macrólido sustituido en la posición c-4 |
| HK1242920A1 (zh) | 2014-10-08 | 2018-07-06 | 哈佛大学的校长及成员们 | 14-元酮内酯及其制备和使用方法 |
| WO2016154591A1 (en) | 2015-03-25 | 2016-09-29 | President And Fellows Of Harvard College | Macrolides with modified desosamine sugars and uses thereof |
| CN108003207B (zh) | 2017-12-19 | 2019-05-10 | 海门慧聚药业有限公司 | 制备泰拉霉素的方法 |
| US11771677B2 (en) * | 2020-03-12 | 2023-10-03 | Zoetis Services Llc | Immunomodulating urea azalides |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4150220A (en) * | 1977-02-04 | 1979-04-17 | Pfizer Inc. | Semi-synthetic 4"-erythromycin A derivatives |
| SE445223B (sv) * | 1977-02-04 | 1986-06-09 | Pfizer | Sett att framstella 4"-amino-erytomylin-a-derivat |
| YU43006B (en) * | 1981-03-06 | 1989-02-28 | Pliva Pharm & Chem Works | Process for preparing n-methyl-11-aza-10-deoxo-10-dihydro erythromycin and derivatives thereof |
| US4474768A (en) * | 1982-07-19 | 1984-10-02 | Pfizer Inc. | N-Methyl 11-aza-10-deoxo-10-dihydro-erytromycin A, intermediates therefor |
| DE3475073D1 (en) * | 1983-09-06 | 1988-12-15 | Pfizer | Azahomoerythromycin b derivatives and intermediates thereof |
| US4512982A (en) * | 1984-04-13 | 1985-04-23 | Pfizer Inc. | 9α-Aza-9α-homoerythromycin compounds, pharmaceutical composition and therapeutic method |
| CA2064634C (en) * | 1991-04-04 | 1998-08-04 | James V. Heck | 9-deoxo-8a-aza-8a-homoerythromycin a derivatives modified at the 4"- and8a-positions |
| US5441939A (en) * | 1994-03-04 | 1995-08-15 | Pfizer Inc. | 3"-desmethoxy derivatives of erythromycin and azithromycin |
| US5412982A (en) * | 1994-03-10 | 1995-05-09 | Potts; James K. | Windsock support |
-
1998
- 1998-05-20 HN HN1998000074A patent/HN1998000074A/es unknown
- 1998-05-22 PA PA19988452001A patent/PA8452001A1/es unknown
- 1998-05-25 SK SK1682-99A patent/SK168299A3/sk unknown
- 1998-05-25 AU AU72281/98A patent/AU745006C/en not_active Ceased
- 1998-05-25 ES ES98919414T patent/ES2251081T3/es not_active Expired - Lifetime
- 1998-05-25 CN CNB988060493A patent/CN1145636C/zh not_active Expired - Fee Related
- 1998-05-25 AT AT98919414T patent/ATE310742T1/de not_active IP Right Cessation
- 1998-05-25 CA CA002293397A patent/CA2293397C/en not_active Expired - Fee Related
- 1998-05-25 PL PL98337497A patent/PL337497A1/xx unknown
- 1998-05-25 WO PCT/IB1998/000799 patent/WO1998056801A1/en not_active Ceased
- 1998-05-25 HU HU0004076A patent/HUP0004076A3/hu unknown
- 1998-05-25 DE DE69832486T patent/DE69832486T2/de not_active Expired - Fee Related
- 1998-05-25 BR BR9810097-1A patent/BR9810097A/pt not_active IP Right Cessation
- 1998-05-25 KR KR10-1999-7011643A patent/KR100369959B1/ko not_active Expired - Fee Related
- 1998-05-25 EP EP98919414A patent/EP0988309B1/en not_active Expired - Lifetime
- 1998-05-25 JP JP50192999A patent/JP3262806B2/ja not_active Expired - Fee Related
- 1998-05-25 IL IL13280898A patent/IL132808A/en not_active IP Right Cessation
- 1998-05-25 EA EA199901014A patent/EA002440B1/ru not_active IP Right Cessation
- 1998-05-25 NZ NZ500652A patent/NZ500652A/en unknown
- 1998-05-25 ID IDW991565A patent/ID24530A/id unknown
- 1998-05-25 YU YU62999A patent/YU62999A/sh unknown
- 1998-05-25 UA UA99126737A patent/UA70298A/uk unknown
- 1998-06-04 AP APAP/P/1998/001254A patent/AP1189A/en active
- 1998-06-08 PE PE1998000469A patent/PE79999A1/es not_active Application Discontinuation
- 1998-06-08 GT GT199800075A patent/GT199800075A/es unknown
- 1998-06-08 TW TW087109085A patent/TWI224106B/zh active
- 1998-06-08 TW TW093111859A patent/TW200418871A/zh unknown
- 1998-06-09 AR ARP980102704A patent/AR013085A1/es active IP Right Grant
- 1998-06-09 MY MYPI98002563A patent/MY133027A/en unknown
- 1998-06-10 ZA ZA9805016A patent/ZA985016B/xx unknown
- 1998-06-10 CO CO98033231A patent/CO4950584A1/es unknown
- 1998-06-10 TN TNTNSN98084A patent/TNSN98084A1/fr unknown
- 1998-06-10 MA MA25106A patent/MA24563A1/fr unknown
- 1998-06-10 DZ DZ980125A patent/DZ2515A1/xx active
- 1998-06-11 UY UY25041A patent/UY25041A1/es not_active IP Right Cessation
- 1998-06-11 HR HR60/049,980A patent/HRP980315A2/hr not_active Application Discontinuation
-
1999
- 1999-11-16 IS IS5250A patent/IS1979B/is unknown
- 1999-12-03 OA OA9900270A patent/OA11226A/en unknown
- 1999-12-08 BG BG103969A patent/BG64357B1/bg unknown
- 1999-12-10 NO NO19996107A patent/NO315560B1/no unknown
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| Date | Code | Title | Description |
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| VENC | Patent expired |
Effective date: 20180611 |