ZA200503104B - Phenyl substituted piperidine compounds for use as PPAR activators - Google Patents
Phenyl substituted piperidine compounds for use as PPAR activators Download PDFInfo
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- ZA200503104B ZA200503104B ZA200503104A ZA200503104A ZA200503104B ZA 200503104 B ZA200503104 B ZA 200503104B ZA 200503104 A ZA200503104 A ZA 200503104A ZA 200503104 A ZA200503104 A ZA 200503104A ZA 200503104 B ZA200503104 B ZA 200503104B
- Authority
- ZA
- South Africa
- Prior art keywords
- methyl
- phenyl
- piperidin
- phenoxy
- alkyl
- Prior art date
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims description 19
- 239000012190 activator Substances 0.000 title description 4
- 150000003053 piperidines Chemical class 0.000 title description 2
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 title 1
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 title 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 76
- 125000000217 alkyl group Chemical group 0.000 claims description 67
- 150000001875 compounds Chemical class 0.000 claims description 51
- 125000003545 alkoxy group Chemical group 0.000 claims description 48
- 125000005843 halogen group Chemical group 0.000 claims description 41
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 34
- 235000019260 propionic acid Nutrition 0.000 claims description 32
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 31
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 29
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 24
- 125000003282 alkyl amino group Chemical group 0.000 claims description 24
- -1 hydroxyaminocarbonyl Chemical group 0.000 claims description 24
- 239000011593 sulfur Substances 0.000 claims description 24
- 229910052717 sulfur Inorganic materials 0.000 claims description 24
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 22
- 229910052799 carbon Inorganic materials 0.000 claims description 22
- 125000005842 heteroatom Chemical group 0.000 claims description 22
- 229910052760 oxygen Inorganic materials 0.000 claims description 22
- 239000001301 oxygen Substances 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 21
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 20
- 229920006395 saturated elastomer Polymers 0.000 claims description 20
- 125000001153 fluoro group Chemical group F* 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 16
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 13
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 239000000651 prodrug Substances 0.000 claims description 10
- 229940002612 prodrug Drugs 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 206010012601 diabetes mellitus Diseases 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 9
- 125000003386 piperidinyl group Chemical group 0.000 claims description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 8
- 125000002619 bicyclic group Chemical group 0.000 claims description 8
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
- 201000001320 Atherosclerosis Diseases 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
- 125000002837 carbocyclic group Chemical group 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 239000003112 inhibitor Substances 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 4
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
- JQWVWVPUELTURY-LBPRGKRZSA-N (3r)-3-[3-(2-carboxypropan-2-yloxy)phenyl]piperidine-1-carboxylic acid Chemical compound OC(=O)C(C)(C)OC1=CC=CC([C@@H]2CN(CCC2)C(O)=O)=C1 JQWVWVPUELTURY-LBPRGKRZSA-N 0.000 claims description 3
- DJXBOEOWRNXBIT-UHFFFAOYSA-N 2-methyl-2-[3-[1-(4-propan-2-ylphenoxy)carbonylpiperidin-3-yl]phenoxy]propanoic acid Chemical compound C1=CC(C(C)C)=CC=C1OC(=O)N1CC(C=2C=C(OC(C)(C)C(O)=O)C=CC=2)CCC1 DJXBOEOWRNXBIT-UHFFFAOYSA-N 0.000 claims description 3
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- 206010020772 Hypertension Diseases 0.000 claims description 3
- 208000008589 Obesity Diseases 0.000 claims description 3
- 208000007536 Thrombosis Diseases 0.000 claims description 3
- MOVRKLZUVNCBIP-RFZYENFJSA-N cortancyl Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)CC2=O MOVRKLZUVNCBIP-RFZYENFJSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 235000020824 obesity Nutrition 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 3
- ULVQKCCUGBHUJX-IBGZPJMESA-N 2-methyl-2-[3-[(3r)-1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbonyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound C1([C@H]2CCCN(C2)C(=O)C=2SC(=NC=2C)C=2C=CC(=CC=2)C(F)(F)F)=CC=CC(OC(C)(C)C(O)=O)=C1 ULVQKCCUGBHUJX-IBGZPJMESA-N 0.000 claims description 2
- 208000002705 Glucose Intolerance Diseases 0.000 claims description 2
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- 208000001145 Metabolic Syndrome Diseases 0.000 claims description 2
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- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 2
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 229940125753 fibrate Drugs 0.000 claims description 2
- 208000006575 hypertriglyceridemia Diseases 0.000 claims description 2
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 2
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- 239000002253 acid Substances 0.000 claims 3
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- 229940122498 Gene expression inhibitor Drugs 0.000 claims 2
- 108010000775 Hydroxymethylglutaryl-CoA synthase Proteins 0.000 claims 2
- 102100028888 Hydroxymethylglutaryl-CoA synthase, cytoplasmic Human genes 0.000 claims 2
- 229940119502 Squalene cyclase inhibitor Drugs 0.000 claims 2
- 229940123185 Squalene epoxidase inhibitor Drugs 0.000 claims 2
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims 1
- FQENSPUPQFQRPQ-NSHDSACASA-N (3r)-3-(3-carboxy-4-methylphenyl)piperidine-1-carboxylic acid Chemical compound C1=C(C(O)=O)C(C)=CC=C1[C@@H]1CN(C(O)=O)CCC1 FQENSPUPQFQRPQ-NSHDSACASA-N 0.000 claims 1
- JQWVWVPUELTURY-GFCCVEGCSA-N (3s)-3-[3-(2-carboxypropan-2-yloxy)phenyl]piperidine-1-carboxylic acid Chemical compound OC(=O)C(C)(C)OC1=CC=CC([C@H]2CN(CCC2)C(O)=O)=C1 JQWVWVPUELTURY-GFCCVEGCSA-N 0.000 claims 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims 1
- YABYZEHDUYSKQO-UHFFFAOYSA-N 2-[2-methyl-5-[1-[[4-(trifluoromethyl)phenyl]methoxycarbonyl]piperidin-3-yl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C)=CC=C1C1CN(C(=O)OCC=2C=CC(=CC=2)C(F)(F)F)CCC1 YABYZEHDUYSKQO-UHFFFAOYSA-N 0.000 claims 1
- HSEKAJDCQVYQHU-INIZCTEOSA-N 2-fluoro-5-[(3r)-1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbonyl]piperidin-3-yl]benzoic acid Chemical compound C1([C@H]2CCCN(C2)C(=O)C=2SC(=NC=2C)C=2C=CC(=CC=2)C(F)(F)F)=CC=C(F)C(C(O)=O)=C1 HSEKAJDCQVYQHU-INIZCTEOSA-N 0.000 claims 1
- HSEKAJDCQVYQHU-MRXNPFEDSA-N 2-fluoro-5-[(3s)-1-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbonyl]piperidin-3-yl]benzoic acid Chemical compound C1([C@@H]2CCCN(C2)C(=O)C=2SC(=NC=2C)C=2C=CC(=CC=2)C(F)(F)F)=CC=C(F)C(C(O)=O)=C1 HSEKAJDCQVYQHU-MRXNPFEDSA-N 0.000 claims 1
- QGFRHYZBADTZDK-LJQANCHMSA-N 2-methyl-2-[2-methyl-5-[(3s)-1-[[4-(trifluoromethyl)phenyl]methoxycarbonyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC=C1[C@H]1CN(C(=O)OCC=2C=CC(=CC=2)C(F)(F)F)CCC1 QGFRHYZBADTZDK-LJQANCHMSA-N 0.000 claims 1
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- VQRZVXMYBJYLNT-QFIPXVFZSA-N 2-methyl-2-[3-[(3r)-1-[(4-propan-2-ylphenyl)methylcarbamoyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound C1=CC(C(C)C)=CC=C1CNC(=O)N1C[C@@H](C=2C=C(OC(C)(C)C(O)=O)C=CC=2)CCC1 VQRZVXMYBJYLNT-QFIPXVFZSA-N 0.000 claims 1
- CSLFIHDRJSTULR-JOCHJYFZSA-N 2-methyl-2-[3-[(3s)-1-[(4-propan-2-ylphenyl)methoxycarbonyl]piperidin-3-yl]phenoxy]propanoic acid Chemical compound C1=CC(C(C)C)=CC=C1COC(=O)N1C[C@H](C=2C=C(OC(C)(C)C(O)=O)C=CC=2)CCC1 CSLFIHDRJSTULR-JOCHJYFZSA-N 0.000 claims 1
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- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07—ORGANIC CHEMISTRY
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
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Landscapes
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PL (1) | PL378268A1 (pt) |
PT (1) | PT1567493E (pt) |
SI (1) | SI1567493T1 (pt) |
TN (1) | TNSN05146A1 (pt) |
TW (1) | TW200424172A (pt) |
UA (1) | UA83202C2 (pt) |
UY (1) | UY28097A1 (pt) |
WO (1) | WO2004048334A1 (pt) |
ZA (1) | ZA200503104B (pt) |
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PL378268A1 (pl) * | 2002-11-26 | 2006-03-20 | Pfizer Products Inc. | Aktywatory PPAR |
WO2005115389A2 (en) * | 2004-05-25 | 2005-12-08 | Pfizer Products Inc. | Specific ppar agonists for treating negative energy balance |
MXPA06013674A (es) * | 2004-05-25 | 2007-02-13 | Pfizer Prod Inc | Nuevo uso. |
KR20070050475A (ko) | 2004-08-11 | 2007-05-15 | 교린 세이야꾸 가부시키 가이샤 | 신규 환상 아미노 안식향산 유도체 |
ATE439347T1 (de) * | 2004-11-23 | 2009-08-15 | Warner Lambert Co | 7-(2h-pyrazol-3-yl)-3,5-dihydroxy-heptansäure- derivate als hmg-co-a-reductase-inhibitoren zur behandlung von lipidemia |
EP1862464A4 (en) * | 2005-03-23 | 2010-08-25 | Kyorin Seiyaku Kk | NEW CYCLIC AMINOPHENYL ALKANIC ACID DERIVATIVE |
GB0510141D0 (en) * | 2005-05-18 | 2005-06-22 | Addex Pharmaceuticals Sa | Novel compounds B3 |
CA2621164A1 (en) * | 2005-08-26 | 2007-03-01 | Shionogi & Co., Ltd. | Derivative having ppar agonistic activity |
WO2007120605A2 (en) * | 2006-04-11 | 2007-10-25 | Los Angeles Biomedical Research Institute At Harbor-Ucla Medical Center | Treatment for nicotine-induced lung disease using peroxisome proliferator-activated receptor gamma agonists |
ES2357992T3 (es) * | 2006-12-01 | 2011-05-04 | Actelion Pharmaceuticals Ltd. | Derivados de 3-heteroaril(amino o amido)-1-(bifenil o feniltiazolil)carbonilpiperidina como inhibidores del receptor de orexina. |
WO2009011872A1 (en) * | 2007-07-17 | 2009-01-22 | Merck & Co., Inc. | Soluble epoxide hydrolase inhibitors, compositions containing such compounds and methods of treatment |
UA105758C2 (uk) | 2007-07-19 | 2014-06-25 | Х. Луннбек А/С | 5-членні гетероциклічні аміди та споріднені сполуки |
TW201006816A (en) | 2008-05-15 | 2010-02-16 | Organon Nv | Hexafluoroisopropanol derivatives |
FR2935511B1 (fr) | 2008-08-28 | 2010-12-10 | Oberthur Technologies | Procede d'echange de donnees entre deux entites electroniques |
FR2935510B1 (fr) | 2008-08-28 | 2010-12-10 | Oberthur Technologies | Procede d'echange de donnees entre deux entites electroniques |
UA107938C2 (en) | 2009-08-12 | 2015-03-10 | Syngenta Participations Ag | Heterocycles with microbicidal properties |
US8716482B2 (en) * | 2009-09-25 | 2014-05-06 | Merck Sharp & Dohme Corp. | Substituted aminopiperidines as dipeptidyl peptidase-IV inhibitors for the treatment of diabetes |
TWI513695B (zh) | 2009-10-27 | 2015-12-21 | Merck Sharp & Dohme | (1,1,1,3,3,3-六氟-2-羥基丙-2-基)苯基衍生物 |
EP2363825B1 (fr) | 2010-03-04 | 2016-04-27 | Inside Secure | Procédé pour conduire une transaction au moyen d'un dispositif NFC |
EP2680874A2 (en) | 2011-03-04 | 2014-01-08 | Pfizer Inc | Edn3-like peptides and uses thereof |
GB201314286D0 (en) | 2013-08-08 | 2013-09-25 | Takeda Pharmaceutical | Therapeutic Compounds |
RU2615769C2 (ru) * | 2015-07-29 | 2017-04-11 | Федеральное Государственное Бюджетное Образовательное Учреждение Высшего Образования "Уфимский Государственный Университет Экономики И Сервиса" | Средство для ингибирования фермента альфа-амилазы |
WO2021055936A1 (en) * | 2019-09-20 | 2021-03-25 | H. Lee Moffitt Cancer Center And Research Institute, Inc. | Small-molecule inhibitors for the β-catenin/b-cell lymphoma 9 protein−protein interaction |
WO2024022521A1 (zh) * | 2022-07-28 | 2024-02-01 | 南通环聚泰生物科技有限公司 | 靶向BCL9/β-连环蛋白互相作用的小分子化合物 |
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-
2003
- 2003-11-14 PL PL378268A patent/PL378268A1/pl not_active Application Discontinuation
- 2003-11-14 UA UAA200505008A patent/UA83202C2/ru unknown
- 2003-11-14 ES ES03811832T patent/ES2321509T3/es not_active Expired - Lifetime
- 2003-11-14 MX MXPA05005583A patent/MXPA05005583A/es active IP Right Grant
- 2003-11-14 CA CA002507465A patent/CA2507465C/en not_active Expired - Fee Related
- 2003-11-14 SI SI200331552T patent/SI1567493T1/sl unknown
- 2003-11-14 JP JP2004554809A patent/JP4029091B2/ja not_active Expired - Fee Related
- 2003-11-14 KR KR1020077012457A patent/KR100875318B1/ko not_active IP Right Cessation
- 2003-11-14 EP EP03811832A patent/EP1567493B1/en not_active Expired - Lifetime
- 2003-11-14 WO PCT/IB2003/005235 patent/WO2004048334A1/en active Application Filing
- 2003-11-14 DE DE60326752T patent/DE60326752D1/de not_active Expired - Lifetime
- 2003-11-14 NZ NZ539546A patent/NZ539546A/en unknown
- 2003-11-14 EA EA200500629A patent/EA008928B1/ru not_active IP Right Cessation
- 2003-11-14 DK DK03811832T patent/DK1567493T3/da active
- 2003-11-14 CN CNB200380104275XA patent/CN100439337C/zh not_active Expired - Fee Related
- 2003-11-14 KR KR1020057009389A patent/KR100760055B1/ko not_active IP Right Cessation
- 2003-11-14 AT AT03811832T patent/ATE425966T1/de not_active IP Right Cessation
- 2003-11-14 AU AU2003276596A patent/AU2003276596B8/en not_active Ceased
- 2003-11-14 BR BR0316521-3A patent/BR0316521A/pt not_active IP Right Cessation
- 2003-11-14 PT PT03811832T patent/PT1567493E/pt unknown
- 2003-11-24 US US10/720,942 patent/US7199243B2/en not_active Expired - Fee Related
- 2003-11-24 AR ARP030104332A patent/AR042131A1/es unknown
- 2003-11-25 PE PE2003001197A patent/PE20040699A1/es not_active Application Discontinuation
- 2003-11-25 TW TW092133036A patent/TW200424172A/zh unknown
- 2003-11-26 NL NL1024881A patent/NL1024881C2/nl not_active IP Right Cessation
- 2003-11-26 GT GT200300258A patent/GT200300258A/es unknown
- 2003-11-26 UY UY28097A patent/UY28097A1/es not_active Application Discontinuation
-
2005
- 2005-04-18 ZA ZA200503104A patent/ZA200503104B/en unknown
- 2005-04-20 IS IS7816A patent/IS7816A/is unknown
- 2005-05-16 HR HR20050437A patent/HRP20050437A2/hr not_active Application Discontinuation
- 2005-05-19 CO CO05048657A patent/CO5570701A2/es not_active Application Discontinuation
- 2005-05-26 MA MA28299A patent/MA27532A1/fr unknown
- 2005-05-26 TN TNP2005000146A patent/TNSN05146A1/fr unknown
- 2005-06-15 NO NO20052921A patent/NO20052921L/no not_active Application Discontinuation
-
2006
- 2006-03-20 HK HK06103485.0A patent/HK1083502A1/xx not_active IP Right Cessation
-
2007
- 2007-03-30 US US11/694,337 patent/US20070191429A1/en not_active Abandoned
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