HUP0302747A2 - Szubsztituált azolok, eljárás az előállításukra és ezeket tartalmazó gyógyszerkészítmények - Google Patents
Szubsztituált azolok, eljárás az előállításukra és ezeket tartalmazó gyógyszerkészítmények Download PDFInfo
- Publication number
- HUP0302747A2 HUP0302747A2 HU0302747A HUP0302747A HUP0302747A2 HU P0302747 A2 HUP0302747 A2 HU P0302747A2 HU 0302747 A HU0302747 A HU 0302747A HU P0302747 A HUP0302747 A HU P0302747A HU P0302747 A2 HUP0302747 A2 HU P0302747A2
- Authority
- HU
- Hungary
- Prior art keywords
- group
- fluorophenyl
- amino
- pyrimidyl
- alkyl
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 7
- 238000000034 method Methods 0.000 title claims description 31
- 239000000825 pharmaceutical preparation Substances 0.000 title abstract 2
- 150000003851 azoles Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 178
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 127
- 125000001424 substituent group Chemical group 0.000 claims abstract description 86
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 60
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 59
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 54
- 125000005843 halogen group Chemical group 0.000 claims abstract description 52
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 48
- -1 cyano- Chemical class 0.000 claims abstract description 40
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 39
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 29
- 125000003118 aryl group Chemical group 0.000 claims abstract description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 25
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 24
- 239000002253 acid Substances 0.000 claims abstract description 23
- 150000002148 esters Chemical class 0.000 claims abstract description 23
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- 125000004475 heteroaralkyl group Chemical group 0.000 claims abstract description 16
- 108060008682 Tumor Necrosis Factor Proteins 0.000 claims abstract description 15
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 14
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 13
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 13
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 13
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims abstract description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 11
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 10
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims abstract description 6
- 125000002971 oxazolyl group Chemical group 0.000 claims abstract description 4
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical group NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 3
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 claims abstract 2
- 150000002460 imidazoles Chemical class 0.000 claims description 35
- 125000003277 amino group Chemical group 0.000 claims description 27
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 26
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- 150000002367 halogens Chemical class 0.000 claims description 19
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 15
- 239000002243 precursor Substances 0.000 claims description 14
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 12
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 12
- 125000003368 amide group Chemical group 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000003386 piperidinyl group Chemical group 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000002757 morpholinyl group Chemical group 0.000 claims description 7
- 125000004193 piperazinyl group Chemical group 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 6
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 6
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
- 150000007942 carboxylates Chemical class 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- 229920002554 vinyl polymer Polymers 0.000 claims description 6
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 5
- 206010061218 Inflammation Diseases 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 230000004054 inflammatory process Effects 0.000 claims description 5
- HEYFMIPJWRNZOJ-UHFFFAOYSA-N 4-[4-bromo-2-[3-(trifluoromethyl)phenyl]imidazol-1-yl]-n-cyclopentylpyrimidin-2-amine Chemical compound FC(F)(F)C1=CC=CC(C=2N(C=C(Br)N=2)C=2N=C(NC3CCCC3)N=CC=2)=C1 HEYFMIPJWRNZOJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 4
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 4
- 229960003444 immunosuppressant agent Drugs 0.000 claims description 4
- 230000001861 immunosuppressant effect Effects 0.000 claims description 4
- 239000003018 immunosuppressive agent Substances 0.000 claims description 4
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 4
- SDEWHSLEPTWRAI-UHFFFAOYSA-N 4-[1-[2-(cyclohexylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)imidazol-4-yl]-1-methylpiperidin-4-ol Chemical compound C1CN(C)CCC1(O)C1=CN(C=2N=C(NC3CCCCC3)N=CC=2)C(C=2C=CC(F)=CC=2)=N1 SDEWHSLEPTWRAI-UHFFFAOYSA-N 0.000 claims description 3
- NTPLIHVIDFWRGV-UHFFFAOYSA-N 4-[1-[2-(cyclopentylamino)pyrimidin-4-yl]-2-[3-(trifluoromethyl)phenyl]imidazol-4-yl]-1-methylpiperidin-4-ol Chemical compound C1CN(C)CCC1(O)C1=CN(C=2N=C(NC3CCCC3)N=CC=2)C(C=2C=C(C=CC=2)C(F)(F)F)=N1 NTPLIHVIDFWRGV-UHFFFAOYSA-N 0.000 claims description 3
- YNFVASWJENHSNL-UHFFFAOYSA-N 4-[1-[2-(cyclopropylamino)pyrimidin-4-yl]-2-[3-(trifluoromethyl)phenyl]imidazol-4-yl]-1-methylpiperidin-4-ol Chemical compound C1CN(C)CCC1(O)C1=CN(C=2N=C(NC3CC3)N=CC=2)C(C=2C=C(C=CC=2)C(F)(F)F)=N1 YNFVASWJENHSNL-UHFFFAOYSA-N 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- BLNLTPFOJOESQM-SFHVURJKSA-N 4-[2-(4-fluorophenyl)-4-pyridin-4-ylimidazol-1-yl]-n-[(1s)-1-phenylethyl]pyrimidin-2-amine Chemical compound N([C@@H](C)C=1C=CC=CC=1)C(N=1)=NC=CC=1N1C=C(C=2C=CN=CC=2)N=C1C1=CC=C(F)C=C1 BLNLTPFOJOESQM-SFHVURJKSA-N 0.000 claims description 2
- HPTDTEXEPXTGON-KRWDZBQOSA-N 4-[2-(4-fluorophenyl)-4-thiophen-3-ylimidazol-1-yl]-n-[(1s)-1-phenylethyl]pyrimidin-2-amine Chemical compound N([C@@H](C)C=1C=CC=CC=1)C(N=1)=NC=CC=1N1C=C(C2=CSC=C2)N=C1C1=CC=C(F)C=C1 HPTDTEXEPXTGON-KRWDZBQOSA-N 0.000 claims description 2
- WQFMURNIPAFPJC-KRWDZBQOSA-N 4-[4-(4-fluorophenyl)-2-piperazin-1-yl-1,3-oxazol-5-yl]-n-[(1s)-1-phenylethyl]pyrimidin-2-amine Chemical compound N([C@@H](C)C=1C=CC=CC=1)C(N=1)=NC=CC=1C=1OC(N2CCNCC2)=NC=1C1=CC=C(F)C=C1 WQFMURNIPAFPJC-KRWDZBQOSA-N 0.000 claims description 2
- YYEFWHDWSRRIOJ-UHFFFAOYSA-N 4-[4-bromo-2-[4-(fluoromethyl)phenyl]imidazol-1-yl]-n-cyclohexylpyrimidin-2-amine Chemical compound C1=CC(CF)=CC=C1C1=NC(Br)=CN1C1=CC=NC(NC2CCCCC2)=N1 YYEFWHDWSRRIOJ-UHFFFAOYSA-N 0.000 claims description 2
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- SWRKLVQDHBENAP-IBGZPJMESA-N ethyl 4-[4-(4-fluorophenyl)-5-[2-[[(1s)-1-phenylethyl]amino]pyrimidin-4-yl]-1,3-oxazol-2-yl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1C1=NC(C=2C=CC(F)=CC=2)=C(C=2N=C(N[C@@H](C)C=3C=CC=CC=3)N=CC=2)O1 SWRKLVQDHBENAP-IBGZPJMESA-N 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- YHXGGIIVEZOFIA-KRWDZBQOSA-N 4-[2-(4-fluorophenyl)-4-thiophen-2-ylimidazol-1-yl]-n-[(1s)-1-phenylethyl]pyrimidin-2-amine Chemical compound N([C@@H](C)C=1C=CC=CC=1)C(N=1)=NC=CC=1N1C=C(C=2SC=CC=2)N=C1C1=CC=C(F)C=C1 YHXGGIIVEZOFIA-KRWDZBQOSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 abstract description 11
- 201000010099 disease Diseases 0.000 abstract description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 11
- 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 abstract description 6
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- 125000004399 C1-C4 alkenyl group Chemical group 0.000 abstract 1
- 229940043355 kinase inhibitor Drugs 0.000 abstract 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 76
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 71
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 60
- 238000005160 1H NMR spectroscopy Methods 0.000 description 56
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- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 44
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 26
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 25
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
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- MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 description 12
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
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Landscapes
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- Health & Medical Sciences (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Pharmacology & Pharmacy (AREA)
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- Engineering & Computer Science (AREA)
- Immunology (AREA)
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- Diabetes (AREA)
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- Pulmonology (AREA)
- Hematology (AREA)
- Neurology (AREA)
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- Endocrinology (AREA)
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- Obesity (AREA)
- Urology & Nephrology (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9908531.8A GB9908531D0 (en) | 1999-04-14 | 1999-04-14 | Organic compounds |
| GBGB9908532.6A GB9908532D0 (en) | 1999-04-14 | 1999-04-14 | Organic compounds |
| PCT/EP2000/003290 WO2000063204A2 (en) | 1999-04-14 | 2000-04-12 | Substituted azoles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HUP0302747A2 true HUP0302747A2 (hu) | 2003-12-29 |
Family
ID=26315413
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU0302747A HUP0302747A2 (hu) | 1999-04-14 | 2000-04-12 | Szubsztituált azolok, eljárás az előállításukra és ezeket tartalmazó gyógyszerkészítmények |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US6579874B2 (https=) |
| EP (1) | EP1224180B1 (https=) |
| JP (1) | JP2003503311A (https=) |
| KR (1) | KR20010108504A (https=) |
| CN (1) | CN1378544A (https=) |
| AR (1) | AR023465A1 (https=) |
| AT (1) | ATE244236T1 (https=) |
| AU (1) | AU4295300A (https=) |
| BR (1) | BR0010598A (https=) |
| CA (1) | CA2370417A1 (https=) |
| CO (1) | CO5170501A1 (https=) |
| CZ (1) | CZ20013696A3 (https=) |
| DE (1) | DE60003709T2 (https=) |
| DK (1) | DK1224180T3 (https=) |
| ES (1) | ES2202114T3 (https=) |
| HU (1) | HUP0302747A2 (https=) |
| IL (1) | IL145836A0 (https=) |
| MX (1) | MXPA01010434A (https=) |
| NO (1) | NO20014987L (https=) |
| PE (1) | PE20010031A1 (https=) |
| PL (1) | PL364789A1 (https=) |
| PT (1) | PT1224180E (https=) |
| SK (1) | SK14562001A3 (https=) |
| TR (1) | TR200102967T2 (https=) |
| WO (1) | WO2000063204A2 (https=) |
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| PE20060777A1 (es) | 2004-12-24 | 2006-10-06 | Boehringer Ingelheim Int | Derivados de indolinona para el tratamiento o la prevencion de enfermedades fibroticas |
| EP3143926B1 (en) * | 2006-02-08 | 2020-07-01 | The General Hospital Corporation | Methods, arrangements and systems for obtaining information associated with an anatomical sample using optical microscopy |
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| ES2320955B1 (es) | 2007-03-02 | 2010-03-16 | Laboratorios Almirall S.A. | Nuevos derivados de 3-((1,2,4)triazolo(4,3-a)piridin-7-il)benzamida. |
| ES2329639B1 (es) | 2007-04-26 | 2010-09-23 | Laboratorios Almirall S.A. | Nuevos derivados de 4,8-difenilpoliazanaftaleno. |
| BRPI0810719A8 (pt) * | 2007-04-30 | 2016-03-08 | Abbott Lab | Inibidores da enzima diacilglicerol o-acetiltansferase tipo 1 |
| EP1992344A1 (en) | 2007-05-18 | 2008-11-19 | Institut Curie | P38 alpha as a therapeutic target in pathologies linked to FGFR3 mutation |
| JP5581219B2 (ja) | 2008-01-25 | 2014-08-27 | ミレニアム ファーマシューティカルズ， インコーポレイテッド | チオフェンおよびホスファチジルイノシトール３−キナーゼ（ｐｉ３ｋ）阻害薬としてのその使用 |
| EP2108641A1 (en) | 2008-04-11 | 2009-10-14 | Laboratorios Almirall, S.A. | New substituted spiro[cycloalkyl-1,3'-indo]-2'(1'H)-one derivatives and their use as p38 mitogen-activated kinase inhibitors |
| EP2113503A1 (en) | 2008-04-28 | 2009-11-04 | Laboratorios Almirall, S.A. | New substituted indolin-2-one derivatives and their use as p39 mitogen-activated kinase inhibitors |
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| US8796314B2 (en) | 2009-01-30 | 2014-08-05 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| US9090601B2 (en) | 2009-01-30 | 2015-07-28 | Millennium Pharmaceuticals, Inc. | Thiazole derivatives |
| CN102438993A (zh) * | 2009-05-19 | 2012-05-02 | 陶氏益农公司 | 用于控制真菌的化合物和方法 |
| EP2322176A1 (en) | 2009-11-11 | 2011-05-18 | Almirall, S.A. | New 7-phenyl-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one derivatives |
| MX2013001660A (es) | 2010-08-11 | 2013-06-03 | Millenium Pharmaceuticals Inc | Heteroarilos y usos de los mismos. |
| WO2012021611A1 (en) | 2010-08-11 | 2012-02-16 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| US8859768B2 (en) | 2010-08-11 | 2014-10-14 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| TW201307309A (zh) | 2010-10-13 | 2013-02-16 | Millennium Pharm Inc | 雜芳基化合物及其用途 |
| AR086113A1 (es) | 2011-04-30 | 2013-11-20 | Abbott Lab | Isoxazolinas como agentes terapeuticos |
| WO2017151409A1 (en) | 2016-02-29 | 2017-09-08 | University Of Florida Research Foundation, Incorporated | Chemotherapeutic methods |
| WO2018159650A1 (ja) * | 2017-02-28 | 2018-09-07 | 東レ株式会社 | グアニジン誘導体及びその医薬用途 |
| WO2021138391A1 (en) | 2019-12-30 | 2021-07-08 | Tyra Biosciences, Inc. | Indazole compounds |
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|---|---|---|---|---|
| JPH09505055A (ja) * | 1993-11-08 | 1997-05-20 | スミスクライン・ビーチャム・コーポレイション | サイトカイン媒介疾患治療用オキサゾール |
| IL118544A (en) * | 1995-06-07 | 2001-08-08 | Smithkline Beecham Corp | History of imidazole, the process for their preparation and the pharmaceutical preparations containing them |
| US5739143A (en) * | 1995-06-07 | 1998-04-14 | Smithkline Beecham Corporation | Imidazole compounds and compositions |
| WO1997005877A1 (en) * | 1995-08-10 | 1997-02-20 | Merck & Co., Inc. | 2-substituted aryl pyrroles, compositions containing such compounds and methods of use |
| US6492516B1 (en) * | 1999-05-14 | 2002-12-10 | Merck & Co., Inc. | Compounds having cytokine inhibitory activity |
-
2000
- 2000-04-11 CO CO00026470A patent/CO5170501A1/es not_active Application Discontinuation
- 2000-04-12 DE DE60003709T patent/DE60003709T2/de not_active Expired - Fee Related
- 2000-04-12 SK SK1456-2001A patent/SK14562001A3/sk unknown
- 2000-04-12 EP EP00922630A patent/EP1224180B1/en not_active Expired - Lifetime
- 2000-04-12 PT PT00922630T patent/PT1224180E/pt unknown
- 2000-04-12 DK DK00922630T patent/DK1224180T3/da active
- 2000-04-12 TR TR2001/02967T patent/TR200102967T2/xx unknown
- 2000-04-12 HU HU0302747A patent/HUP0302747A2/hu unknown
- 2000-04-12 BR BR0010598-8A patent/BR0010598A/pt not_active IP Right Cessation
- 2000-04-12 JP JP2000612294A patent/JP2003503311A/ja active Pending
- 2000-04-12 CN CN00807552A patent/CN1378544A/zh active Pending
- 2000-04-12 ES ES00922630T patent/ES2202114T3/es not_active Expired - Lifetime
- 2000-04-12 IL IL14583600A patent/IL145836A0/xx unknown
- 2000-04-12 AU AU42953/00A patent/AU4295300A/en not_active Abandoned
- 2000-04-12 CZ CZ20013696A patent/CZ20013696A3/cs unknown
- 2000-04-12 PL PL00364789A patent/PL364789A1/xx not_active Application Discontinuation
- 2000-04-12 PE PE2000000337A patent/PE20010031A1/es not_active Application Discontinuation
- 2000-04-12 MX MXPA01010434A patent/MXPA01010434A/es unknown
- 2000-04-12 AR ARP000101686A patent/AR023465A1/es unknown
- 2000-04-12 KR KR1020017013086A patent/KR20010108504A/ko not_active Withdrawn
- 2000-04-12 AT AT00922630T patent/ATE244236T1/de not_active IP Right Cessation
- 2000-04-12 WO PCT/EP2000/003290 patent/WO2000063204A2/en not_active Ceased
- 2000-04-12 CA CA002370417A patent/CA2370417A1/en not_active Abandoned
-
2001
- 2001-10-12 US US09/975,913 patent/US6579874B2/en not_active Expired - Fee Related
- 2001-10-12 NO NO20014987A patent/NO20014987L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| SK14562001A3 (sk) | 2002-03-05 |
| DE60003709T2 (de) | 2004-12-23 |
| AR023465A1 (es) | 2002-09-04 |
| TR200102967T2 (tr) | 2002-01-21 |
| US6579874B2 (en) | 2003-06-17 |
| CA2370417A1 (en) | 2000-10-26 |
| IL145836A0 (en) | 2002-07-25 |
| PL364789A1 (en) | 2004-12-13 |
| DE60003709D1 (de) | 2003-08-07 |
| CO5170501A1 (es) | 2002-06-27 |
| MXPA01010434A (es) | 2002-03-27 |
| NO20014987L (no) | 2001-12-14 |
| WO2000063204A3 (en) | 2002-05-23 |
| EP1224180B1 (en) | 2003-07-02 |
| ATE244236T1 (de) | 2003-07-15 |
| KR20010108504A (ko) | 2001-12-07 |
| PE20010031A1 (es) | 2001-02-23 |
| DK1224180T3 (da) | 2003-10-20 |
| JP2003503311A (ja) | 2003-01-28 |
| AU4295300A (en) | 2000-11-02 |
| NO20014987D0 (no) | 2001-10-12 |
| PT1224180E (pt) | 2003-11-28 |
| US20020049220A1 (en) | 2002-04-25 |
| EP1224180A2 (en) | 2002-07-24 |
| ES2202114T3 (es) | 2004-04-01 |
| CN1378544A (zh) | 2002-11-06 |
| CZ20013696A3 (cs) | 2002-02-13 |
| WO2000063204A2 (en) | 2000-10-26 |
| BR0010598A (pt) | 2002-02-05 |
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