RU2005119173A - Ациклические пиразольные соединения - Google Patents
Ациклические пиразольные соединения Download PDFInfo
- Publication number
- RU2005119173A RU2005119173A RU2005119173/04A RU2005119173A RU2005119173A RU 2005119173 A RU2005119173 A RU 2005119173A RU 2005119173/04 A RU2005119173/04 A RU 2005119173/04A RU 2005119173 A RU2005119173 A RU 2005119173A RU 2005119173 A RU2005119173 A RU 2005119173A
- Authority
- RU
- Russia
- Prior art keywords
- alkyl
- heterocyclyl
- heteroaryl
- aryl
- carbon
- Prior art date
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- -1 Acyclic pyrazole compounds Chemical class 0.000 title claims 49
- 229910052799 carbon Inorganic materials 0.000 claims 100
- 125000003118 aryl group Chemical group 0.000 claims 90
- 125000001072 heteroaryl group Chemical group 0.000 claims 65
- 125000000623 heterocyclic group Chemical group 0.000 claims 65
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 64
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 59
- 125000003710 aryl alkyl group Chemical group 0.000 claims 58
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 50
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 49
- 125000002877 alkyl aryl group Chemical group 0.000 claims 45
- 125000002950 monocyclic group Chemical group 0.000 claims 42
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 42
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 35
- 229910052739 hydrogen Inorganic materials 0.000 claims 30
- 229910052757 nitrogen Inorganic materials 0.000 claims 30
- 150000001875 compounds Chemical class 0.000 claims 27
- 229910052736 halogen Inorganic materials 0.000 claims 20
- 150000002367 halogens Chemical class 0.000 claims 20
- 125000000217 alkyl group Chemical group 0.000 claims 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 19
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 16
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 15
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 15
- 208000035475 disorder Diseases 0.000 claims 14
- 125000001424 substituent group Chemical group 0.000 claims 14
- 229910052760 oxygen Inorganic materials 0.000 claims 11
- 229910052717 sulfur Inorganic materials 0.000 claims 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 10
- 230000002401 inhibitory effect Effects 0.000 claims 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 8
- 230000006378 damage Effects 0.000 claims 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 5
- 208000027418 Wounds and injury Diseases 0.000 claims 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 5
- 208000014674 injury Diseases 0.000 claims 5
- 239000001301 oxygen Substances 0.000 claims 5
- 239000011593 sulfur Substances 0.000 claims 5
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 4
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 4
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 4
- 108060008682 Tumor Necrosis Factor Proteins 0.000 claims 4
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 230000001404 mediated effect Effects 0.000 claims 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 3
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 125000004103 aminoalkyl group Chemical group 0.000 claims 3
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 201000004624 Dermatitis Diseases 0.000 claims 2
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 2
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 208000010668 atopic eczema Diseases 0.000 claims 2
- 210000002808 connective tissue Anatomy 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- 208000030533 eye disease Diseases 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 230000001225 therapeutic effect Effects 0.000 claims 2
- 210000001519 tissue Anatomy 0.000 claims 2
- DMTVLHOJTLJUHG-UHFFFAOYSA-N 2-(2-aminoethyl)-5-(2-quinolin-3-ylpyridin-4-yl)pyrazole-3-carboxylic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(C(O)=O)N(CCN)N=C1C1=CC=NC(C=2C=C3C=CC=CC3=NC=2)=C1 DMTVLHOJTLJUHG-UHFFFAOYSA-N 0.000 claims 1
- FBUFDEIWIUCPAH-UHDJGPCESA-N 2-(2-aminoethyl)-5-[2-[(e)-2-phenylethenyl]pyridin-4-yl]pyrazole-3-carboxylic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(C(O)=O)N(CCN)N=C1C1=CC=NC(\C=C\C=2C=CC=CC=2)=C1 FBUFDEIWIUCPAH-UHDJGPCESA-N 0.000 claims 1
- GUXZPWFWFJSWPE-UHFFFAOYSA-N 2-(2-aminoethyl)-5-[2-[4-(hydroxymethyl)phenyl]pyridin-4-yl]pyrazole-3-carboxylic acid;dihydrochloride Chemical compound Cl.Cl.C1=C(C(O)=O)N(CCN)N=C1C1=CC=NC(C=2C=CC(CO)=CC=2)=C1 GUXZPWFWFJSWPE-UHFFFAOYSA-N 0.000 claims 1
- STHQHYXWUOHSKC-UHFFFAOYSA-N 2-(3-aminopropyl)-5-(2-quinolin-3-ylpyridin-4-yl)pyrazole-3-carboxylic acid;dihydrochloride Chemical compound Cl.Cl.C1=C(C(O)=O)N(CCCN)N=C1C1=CC=NC(C=2C=C3C=CC=CC3=NC=2)=C1 STHQHYXWUOHSKC-UHFFFAOYSA-N 0.000 claims 1
- YMUBHZPDPYZUOR-UHFFFAOYSA-N 2-(3-aminopropyl)-5-[2-(3-nitrophenyl)pyridin-4-yl]pyrazole-3-carboxylic acid;dihydrochloride Chemical compound Cl.Cl.C1=C(C(O)=O)N(CCCN)N=C1C1=CC=NC(C=2C=C(C=CC=2)[N+]([O-])=O)=C1 YMUBHZPDPYZUOR-UHFFFAOYSA-N 0.000 claims 1
- INZWSXZYNJIFSJ-UHFFFAOYSA-N 6-(aminomethyl)-2-(2-quinolin-3-ylpyridin-4-yl)-6,7-dihydro-5h-pyrazolo[1,5-a]pyrazin-4-one Chemical compound C1=CC=CC2=CC(C=3N=CC=C(C=3)C3=NN4CC(NC(=O)C4=C3)CN)=CN=C21 INZWSXZYNJIFSJ-UHFFFAOYSA-N 0.000 claims 1
- GGRWZJIJWLJCQA-UHFFFAOYSA-N 6-(hydroxymethyl)-2-(2-quinolin-3-ylpyridin-4-yl)-6,7-dihydro-5h-pyrazolo[1,5-a]pyrazin-4-one Chemical compound C1=CC=CC2=CC(C=3N=CC=C(C=3)C3=NN4CC(NC(=O)C4=C3)CO)=CN=C21 GGRWZJIJWLJCQA-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000032467 Aplastic anaemia Diseases 0.000 claims 1
- 208000027496 Behcet disease Diseases 0.000 claims 1
- 208000009137 Behcet syndrome Diseases 0.000 claims 1
- 206010006811 Bursitis Diseases 0.000 claims 1
- 241000222122 Candida albicans Species 0.000 claims 1
- 206010007134 Candida infections Diseases 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 1
- 208000035473 Communicable disease Diseases 0.000 claims 1
- 206010010741 Conjunctivitis Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 201000003883 Cystic fibrosis Diseases 0.000 claims 1
- 206010012289 Dementia Diseases 0.000 claims 1
- 208000030814 Eating disease Diseases 0.000 claims 1
- 208000017701 Endocrine disease Diseases 0.000 claims 1
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 1
- 208000007882 Gastritis Diseases 0.000 claims 1
- 201000005569 Gout Diseases 0.000 claims 1
- 206010018634 Gouty Arthritis Diseases 0.000 claims 1
- 206010019233 Headaches Diseases 0.000 claims 1
- 206010019973 Herpes virus infection Diseases 0.000 claims 1
- 208000017604 Hodgkin disease Diseases 0.000 claims 1
- 208000010747 Hodgkins lymphoma Diseases 0.000 claims 1
- 206010020751 Hypersensitivity Diseases 0.000 claims 1
- 208000012659 Joint disease Diseases 0.000 claims 1
- 208000003456 Juvenile Arthritis Diseases 0.000 claims 1
- 206010059176 Juvenile idiopathic arthritis Diseases 0.000 claims 1
- 208000000913 Kidney Calculi Diseases 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 208000019695 Migraine disease Diseases 0.000 claims 1
- 206010027603 Migraine headaches Diseases 0.000 claims 1
- 208000007101 Muscle Cramp Diseases 0.000 claims 1
- 208000023178 Musculoskeletal disease Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 206010029148 Nephrolithiasis Diseases 0.000 claims 1
- 206010029164 Nephrotic syndrome Diseases 0.000 claims 1
- 208000025157 Oral disease Diseases 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 206010034960 Photophobia Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 206010037423 Pulmonary oedema Diseases 0.000 claims 1
- 206010038910 Retinitis Diseases 0.000 claims 1
- 206010038923 Retinopathy Diseases 0.000 claims 1
- 201000001880 Sexual dysfunction Diseases 0.000 claims 1
- 206010040744 Sinus headache Diseases 0.000 claims 1
- 208000005392 Spasm Diseases 0.000 claims 1
- 208000006045 Spondylarthropathies Diseases 0.000 claims 1
- 208000007107 Stomach Ulcer Diseases 0.000 claims 1
- 208000014151 Stomatognathic disease Diseases 0.000 claims 1
- 206010042674 Swelling Diseases 0.000 claims 1
- 208000000491 Tendinopathy Diseases 0.000 claims 1
- 206010043255 Tendonitis Diseases 0.000 claims 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 206010046851 Uveitis Diseases 0.000 claims 1
- 206010046914 Vaginal infection Diseases 0.000 claims 1
- 201000008100 Vaginitis Diseases 0.000 claims 1
- 208000036142 Viral infection Diseases 0.000 claims 1
- 230000009692 acute damage Effects 0.000 claims 1
- 208000038016 acute inflammation Diseases 0.000 claims 1
- 230000006022 acute inflammation Effects 0.000 claims 1
- 208000026935 allergic disease Diseases 0.000 claims 1
- 230000000172 allergic effect Effects 0.000 claims 1
- 230000033115 angiogenesis Effects 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 206010006451 bronchitis Diseases 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 201000003984 candidiasis Diseases 0.000 claims 1
- 210000003169 central nervous system Anatomy 0.000 claims 1
- 208000018631 connective tissue disease Diseases 0.000 claims 1
- 230000001054 cortical effect Effects 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 208000032625 disorder of ear Diseases 0.000 claims 1
- 235000014632 disordered eating Nutrition 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 208000020694 gallbladder disease Diseases 0.000 claims 1
- 210000001035 gastrointestinal tract Anatomy 0.000 claims 1
- 208000007565 gingivitis Diseases 0.000 claims 1
- 231100000869 headache Toxicity 0.000 claims 1
- 208000014951 hematologic disease Diseases 0.000 claims 1
- 125000004404 heteroalkyl group Chemical group 0.000 claims 1
- 230000009610 hypersensitivity Effects 0.000 claims 1
- 208000026278 immune system disease Diseases 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 208000002551 irritable bowel syndrome Diseases 0.000 claims 1
- 210000004185 liver Anatomy 0.000 claims 1
- 208000019423 liver disease Diseases 0.000 claims 1
- 230000002175 menstrual effect Effects 0.000 claims 1
- 230000002503 metabolic effect Effects 0.000 claims 1
- DOTMOQHOJINYBL-UHFFFAOYSA-N molecular nitrogen;molecular oxygen Chemical compound N#N.O=O DOTMOQHOJINYBL-UHFFFAOYSA-N 0.000 claims 1
- 208000030194 mouth disease Diseases 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 206010028417 myasthenia gravis Diseases 0.000 claims 1
- 208000031225 myocardial ischemia Diseases 0.000 claims 1
- 230000001613 neoplastic effect Effects 0.000 claims 1
- 230000000926 neurological effect Effects 0.000 claims 1
- 150000002829 nitrogen Chemical group 0.000 claims 1
- 208000036236 obstetric disease Diseases 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 230000036407 pain Effects 0.000 claims 1
- 231100000572 poisoning Toxicity 0.000 claims 1
- 230000000607 poisoning effect Effects 0.000 claims 1
- 201000006292 polyarteritis nodosa Diseases 0.000 claims 1
- 208000005987 polymyositis Diseases 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 208000020016 psychiatric disease Diseases 0.000 claims 1
- 208000005333 pulmonary edema Diseases 0.000 claims 1
- 208000023504 respiratory system disease Diseases 0.000 claims 1
- 201000003068 rheumatic fever Diseases 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 201000000306 sarcoidosis Diseases 0.000 claims 1
- 231100000872 sexual dysfunction Toxicity 0.000 claims 1
- 208000017520 skin disease Diseases 0.000 claims 1
- 201000005671 spondyloarthropathy Diseases 0.000 claims 1
- 210000002784 stomach Anatomy 0.000 claims 1
- 230000008961 swelling Effects 0.000 claims 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 1
- 201000004415 tendinitis Diseases 0.000 claims 1
- 206010043778 thyroiditis Diseases 0.000 claims 1
- 208000004371 toothache Diseases 0.000 claims 1
- 208000019553 vascular disease Diseases 0.000 claims 1
- 230000009385 viral infection Effects 0.000 claims 1
- 230000029663 wound healing Effects 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US43496202P | 2002-12-20 | 2002-12-20 | |
| US60/434,962 | 2002-12-20 |
Publications (1)
| Publication Number | Publication Date |
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| RU2005119173A true RU2005119173A (ru) | 2006-02-27 |
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| RU2005119173/04A RU2005119173A (ru) | 2002-12-20 | 2003-12-19 | Ациклические пиразольные соединения |
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| US (3) | US20040152739A1 (https=) |
| EP (2) | EP1572682A4 (https=) |
| JP (2) | JP2006514043A (https=) |
| KR (1) | KR20050104339A (https=) |
| CN (1) | CN1747949A (https=) |
| AU (2) | AU2003301226A1 (https=) |
| BR (2) | BR0317430A (https=) |
| CA (2) | CA2509565A1 (https=) |
| IL (1) | IL169177A0 (https=) |
| MX (2) | MXPA05006568A (https=) |
| NO (1) | NO20053396L (https=) |
| PL (1) | PL377461A1 (https=) |
| RU (1) | RU2005119173A (https=) |
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| US6211361B1 (en) * | 1999-07-20 | 2001-04-03 | State Of Oregon Acting By And Through The Oregon State Board Of Higher Education On Behalf Of Oregon, State Univeristy | Method for making debromohymenialdisine and analogs thereof |
| KR20010111298A (ko) * | 2000-02-05 | 2001-12-17 | 버텍스 파마슈티칼스 인코포레이티드 | Erk의 억제제로서 유용한 피라졸 조성물 |
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- 2003-12-19 JP JP2004563888A patent/JP2006514043A/ja not_active Withdrawn
- 2003-12-19 KR KR1020057011474A patent/KR20050104339A/ko not_active Withdrawn
- 2003-12-19 WO PCT/US2003/040811 patent/WO2004058762A1/en not_active Ceased
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- 2003-12-19 US US10/742,072 patent/US20040209897A1/en not_active Abandoned
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- 2003-12-19 RU RU2005119173/04A patent/RU2005119173A/ru not_active Application Discontinuation
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2005
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| PL377461A1 (pl) | 2006-02-06 |
| CN1747949A (zh) | 2006-03-15 |
| NO20053396L (no) | 2005-09-12 |
| WO2004058762A1 (en) | 2004-07-15 |
| AU2003297431A1 (en) | 2004-07-22 |
| NO20053396D0 (no) | 2005-07-13 |
| CA2510298A1 (en) | 2004-07-15 |
| JP2006514043A (ja) | 2006-04-27 |
| IL169177A0 (en) | 2007-07-04 |
| JP2006511583A (ja) | 2006-04-06 |
| ZA200504898B (en) | 2006-11-29 |
| AU2003301226A1 (en) | 2004-07-22 |
| KR20050104339A (ko) | 2005-11-02 |
| EP1572682A4 (en) | 2008-01-23 |
| MXPA05006569A (es) | 2005-09-22 |
| CA2509565A1 (en) | 2004-07-15 |
| AU2003301226A2 (en) | 2004-07-22 |
| WO2004058176A3 (en) | 2004-09-16 |
| EP1572693A1 (en) | 2005-09-14 |
| EP1572682A2 (en) | 2005-09-14 |
| US20040152739A1 (en) | 2004-08-05 |
| US20040209897A1 (en) | 2004-10-21 |
| BR0317430A (pt) | 2005-10-25 |
| BR0317525A (pt) | 2005-11-16 |
| US20080113971A1 (en) | 2008-05-15 |
| WO2004058176A2 (en) | 2004-07-15 |
| MXPA05006568A (es) | 2005-09-22 |
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| FA92 | Acknowledgement of application withdrawn (lack of supplementary materials submitted) |
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