UA78808C2 - 3(4-oxo-4h-chromen-2-yl)-(1h)-quinolin-4-on derivatives, method for their production and pharmaceutical composition - Google Patents
3(4-oxo-4h-chromen-2-yl)-(1h)-quinolin-4-on derivatives, method for their production and pharmaceutical composition Download PDFInfo
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- UA78808C2 UA78808C2 UAA200500487A UA2005000487A UA78808C2 UA 78808 C2 UA78808 C2 UA 78808C2 UA A200500487 A UAA200500487 A UA A200500487A UA 2005000487 A UA2005000487 A UA 2005000487A UA 78808 C2 UA78808 C2 UA 78808C2
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- Ukraine
- Prior art keywords
- branched
- linear
- formula
- compound
- alkyl
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- 238000000034 method Methods 0.000 title claims description 26
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 95
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 47
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 18
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 16
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 12
- 125000003118 aryl group Chemical group 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 8
- 239000002253 acid Substances 0.000 claims abstract description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052760 oxygen Chemical group 0.000 claims abstract description 7
- 239000001301 oxygen Chemical group 0.000 claims abstract description 7
- 230000003287 optical effect Effects 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 125000005085 alkoxycarbonylalkoxy group Chemical group 0.000 claims abstract description 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims abstract description 3
- 150000004677 hydrates Chemical class 0.000 claims abstract description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 15
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- 125000003277 amino group Chemical group 0.000 claims description 8
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
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- 229940100198 alkylating agent Drugs 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 229940045799 anthracyclines and related substance Drugs 0.000 description 1
- 230000001772 anti-angiogenic effect Effects 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 229940045719 antineoplastic alkylating agent nitrosoureas Drugs 0.000 description 1
- 230000001640 apoptogenic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
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- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
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- 210000004369 blood Anatomy 0.000 description 1
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- 210000004556 brain Anatomy 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical compound CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
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- 238000003776 cleavage reaction Methods 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
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- 239000012230 colorless oil Substances 0.000 description 1
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- 239000006071 cream Substances 0.000 description 1
- 229960004397 cyclophosphamide Drugs 0.000 description 1
- 239000000824 cytostatic agent Substances 0.000 description 1
- 230000001085 cytostatic effect Effects 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 231100000263 cytotoxicity test Toxicity 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229960004679 doxorubicin Drugs 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 description 1
- 229960005420 etoposide Drugs 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 210000004907 gland Anatomy 0.000 description 1
- 231100000226 haematotoxicity Toxicity 0.000 description 1
- 238000001794 hormone therapy Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- SXWRTZOXMUOJER-UHFFFAOYSA-N hydron;piperidin-4-one;chloride;hydrate Chemical compound O.Cl.O=C1CCNCC1 SXWRTZOXMUOJER-UHFFFAOYSA-N 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- VSGPVHSTVTXREH-UHFFFAOYSA-N quinolin-4-one Chemical compound C1=CC=C[C]2C(=O)C=CN=C21 VSGPVHSTVTXREH-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000001959 radiotherapy Methods 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000011477 surgical intervention Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229960001603 tamoxifen Drugs 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000005942 tetrahydropyridyl group Chemical group 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 210000003932 urinary bladder Anatomy 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
- FBUBVLUPUDBFME-UHFFFAOYSA-N xanthoxylline Natural products COC1=CC(O)=C(C(C)=O)C(OC)=C1 FBUBVLUPUDBFME-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07D405/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
-
- 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
- C07D405/14—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 three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0207536A FR2841243B1 (fr) | 2002-06-19 | 2002-06-19 | Nouveaux derives de 3-(4-oxo-4h-chromen-2yl)-(1h)-quinolein- 4-ones, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| PCT/FR2003/001849 WO2004000834A1 (fr) | 2002-06-19 | 2003-06-18 | Nouveaux derives de 3-(4-oxo-4h-chromen-2-yl)-(1h)-quinolein-4-ones, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA78808C2 true UA78808C2 (en) | 2007-04-25 |
Family
ID=29719853
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UAA200500487A UA78808C2 (en) | 2002-06-19 | 2003-06-18 | 3(4-oxo-4h-chromen-2-yl)-(1h)-quinolin-4-on derivatives, method for their production and pharmaceutical composition |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US7339061B2 (es) |
| EP (1) | EP1513833B1 (es) |
| JP (1) | JP4252035B2 (es) |
| KR (1) | KR100645138B1 (es) |
| CN (1) | CN1313462C (es) |
| AR (1) | AR040276A1 (es) |
| AT (1) | ATE323698T1 (es) |
| AU (1) | AU2003269003B2 (es) |
| BR (1) | BR0311956A (es) |
| CA (1) | CA2489136C (es) |
| DE (1) | DE60304703T2 (es) |
| DK (1) | DK1513833T3 (es) |
| EA (1) | EA008285B1 (es) |
| ES (1) | ES2263013T3 (es) |
| FR (1) | FR2841243B1 (es) |
| GE (1) | GEP20084296B (es) |
| HK (1) | HK1081191A1 (es) |
| MA (1) | MA27260A1 (es) |
| MX (1) | MXPA04012795A (es) |
| NO (1) | NO331618B1 (es) |
| NZ (1) | NZ537314A (es) |
| PL (1) | PL210722B1 (es) |
| PT (1) | PT1513833E (es) |
| UA (1) | UA78808C2 (es) |
| WO (1) | WO2004000834A1 (es) |
| ZA (1) | ZA200410048B (es) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007130499A2 (en) * | 2006-05-01 | 2007-11-15 | Virobay, Inc. | Antiviral agents |
| FR2912145B1 (fr) * | 2007-02-02 | 2009-03-06 | Servier Lab | Nouveaux derives tricycliques,leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| JP7033789B2 (ja) * | 2016-06-29 | 2022-03-11 | オトノミー，インク． | トリグリセリド耳用製剤とその使用 |
| RU2642426C1 (ru) * | 2017-03-21 | 2018-01-25 | Федеральное государственное бюджетное учреждение науки Институт органического синтеза им. И.Я. Постовского Уральского отделения Российской академии наук (ИОС УрО РАН) | 1-Этил-6-фтор-4-оксо-7-(8-этокси-2-оксо-2Н-хромен-3-ил)-1,4-дигидрохинолин-3-карбоновая кислота, обладающая противотуберкулезной активностью |
| CN112225744A (zh) * | 2020-08-31 | 2021-01-15 | 兰州大学 | 一种6H-苯并吡喃并[3,4-b]喹啉类化合物及其制备方法和用途 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0733743A (ja) * | 1993-07-22 | 1995-02-03 | Kyorin Pharmaceut Co Ltd | ２−アリール−４−キノリノール誘導体 |
| CA2182932A1 (en) * | 1995-08-10 | 1997-02-11 | Koju Watanabe | Chromone derivative, process for preparing same and pharmaceutical composition |
| TW349948B (en) * | 1995-10-31 | 1999-01-11 | Janssen Pharmaceutica Nv | Farnesyl transferase inhibiting 2-quinolone derivatives |
| DE19850131A1 (de) * | 1998-10-30 | 2000-05-04 | Merck Patent Gmbh | Chromenon- und Chromanonderivate |
-
2002
- 2002-06-19 FR FR0207536A patent/FR2841243B1/fr not_active Expired - Fee Related
-
2003
- 2003-06-18 WO PCT/FR2003/001849 patent/WO2004000834A1/fr active IP Right Grant
- 2003-06-18 MX MXPA04012795A patent/MXPA04012795A/es active IP Right Grant
- 2003-06-18 ES ES03750780T patent/ES2263013T3/es not_active Expired - Lifetime
- 2003-06-18 AT AT03750780T patent/ATE323698T1/de active
- 2003-06-18 PT PT03750780T patent/PT1513833E/pt unknown
- 2003-06-18 AU AU2003269003A patent/AU2003269003B2/en not_active Ceased
- 2003-06-18 PL PL372984A patent/PL210722B1/pl not_active IP Right Cessation
- 2003-06-18 BR BR0311956-4A patent/BR0311956A/pt not_active IP Right Cessation
- 2003-06-18 DE DE60304703T patent/DE60304703T2/de not_active Expired - Lifetime
- 2003-06-18 GE GEAP20038592A patent/GEP20084296B/en unknown
- 2003-06-18 EP EP03750780A patent/EP1513833B1/fr not_active Expired - Lifetime
- 2003-06-18 KR KR1020047020594A patent/KR100645138B1/ko not_active IP Right Cessation
- 2003-06-18 CN CNB038140500A patent/CN1313462C/zh not_active Expired - Fee Related
- 2003-06-18 CA CA2489136A patent/CA2489136C/fr not_active Expired - Fee Related
- 2003-06-18 DK DK03750780T patent/DK1513833T3/da active
- 2003-06-18 JP JP2004514935A patent/JP4252035B2/ja not_active Expired - Fee Related
- 2003-06-18 UA UAA200500487A patent/UA78808C2/uk unknown
- 2003-06-18 NZ NZ537314A patent/NZ537314A/en not_active IP Right Cessation
- 2003-06-18 EA EA200500028A patent/EA008285B1/ru not_active IP Right Cessation
- 2003-06-18 US US10/519,208 patent/US7339061B2/en not_active Expired - Fee Related
- 2003-06-19 AR ARP030102176A patent/AR040276A1/es active IP Right Grant
-
2004
- 2004-12-13 ZA ZA200410048A patent/ZA200410048B/xx unknown
- 2004-12-17 NO NO20045540A patent/NO331618B1/no not_active IP Right Cessation
-
2005
- 2005-01-18 MA MA28047A patent/MA27260A1/fr unknown
-
2006
- 2006-01-26 HK HK06101208A patent/HK1081191A1/xx not_active IP Right Cessation
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