DE10238002A1 - Benzimidazolderivate - Google Patents
Benzimidazolderivate Download PDFInfo
- Publication number
- DE10238002A1 DE10238002A1 DE10238002A DE10238002A DE10238002A1 DE 10238002 A1 DE10238002 A1 DE 10238002A1 DE 10238002 A DE10238002 A DE 10238002A DE 10238002 A DE10238002 A DE 10238002A DE 10238002 A1 DE10238002 A1 DE 10238002A1
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- Germany
- Prior art keywords
- oxo
- diyl
- phenyl
- formula
- compounds
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 title 1
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 104
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 19
- 108010074860 Factor Xa Proteins 0.000 claims abstract description 15
- 238000011282 treatment Methods 0.000 claims abstract description 12
- 239000003112 inhibitor Substances 0.000 claims abstract description 4
- -1 pyrazin-1-yl Chemical group 0.000 claims description 550
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 65
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 57
- 239000000203 mixture Substances 0.000 claims description 54
- 239000012453 solvate Substances 0.000 claims description 49
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 48
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 44
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 44
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 38
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 38
- 125000000623 heterocyclic group Chemical group 0.000 claims description 35
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 27
- 229920006395 saturated elastomer Polymers 0.000 claims description 25
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 24
- HCUOEKSZWPGJIM-IYNMRSRQSA-N (e,2z)-2-hydroxyimino-6-methoxy-4-methyl-5-nitrohex-3-enamide Chemical compound COCC([N+]([O-])=O)\C(C)=C\C(=N\O)\C(N)=O HCUOEKSZWPGJIM-IYNMRSRQSA-N 0.000 claims description 23
- 229910052731 fluorine Inorganic materials 0.000 claims description 23
- 229930192474 thiophene Natural products 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 229910052801 chlorine Inorganic materials 0.000 claims description 20
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 19
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 19
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 19
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 19
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 19
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 19
- 229910052794 bromium Inorganic materials 0.000 claims description 19
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 19
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 19
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 19
- 125000004434 sulfur atom Chemical group 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 17
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 17
- 125000006239 protecting group Chemical group 0.000 claims description 17
- 125000004076 pyridyl group Chemical group 0.000 claims description 17
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 16
- 239000003814 drug Substances 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 208000007536 Thrombosis Diseases 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 8
- 108010054265 Factor VIIa Proteins 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 239000004305 biphenyl Substances 0.000 claims description 8
- 235000010290 biphenyl Nutrition 0.000 claims description 8
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 7
- 208000006011 Stroke Diseases 0.000 claims description 7
- 238000002399 angioplasty Methods 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000001634 furandiyl group Chemical group O1C(=C(C=C1)*)* 0.000 claims description 7
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- 208000010125 myocardial infarction Diseases 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 150000003254 radicals Chemical class 0.000 claims description 7
- 206010002383 Angina Pectoris Diseases 0.000 claims description 6
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 6
- 206010008190 Cerebrovascular accident Diseases 0.000 claims description 6
- 206010061218 Inflammation Diseases 0.000 claims description 6
- 206010022562 Intermittent claudication Diseases 0.000 claims description 6
- 206010027476 Metastases Diseases 0.000 claims description 6
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 6
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 6
- 229940079593 drug Drugs 0.000 claims description 6
- 230000004054 inflammatory process Effects 0.000 claims description 6
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 6
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 208000037803 restenosis Diseases 0.000 claims description 6
- 150000003536 tetrazoles Chemical class 0.000 claims description 6
- 208000019695 Migraine disease Diseases 0.000 claims description 5
- 125000000676 alkoxyimino group Chemical group 0.000 claims description 5
- 239000004615 ingredient Substances 0.000 claims description 5
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- JLXGEDHKNZOFGL-UHFFFAOYSA-N 2-[2-(5-chlorothiophen-2-yl)-3h-benzimidazol-5-yl]-n-[4-(3-oxomorpholin-4-yl)phenyl]acetamide Chemical compound S1C(Cl)=CC=C1C1=NC2=CC(CC(=O)NC=3C=CC(=CC=3)N3C(COCC3)=O)=CC=C2N1 JLXGEDHKNZOFGL-UHFFFAOYSA-N 0.000 claims description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 4
- 125000000464 thioxo group Chemical group S=* 0.000 claims description 4
- OHFMFUJGVXCEBF-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)-3h-benzimidazol-5-yl]-n-[3-methyl-4-(3-oxomorpholin-4-yl)phenyl]acetamide Chemical compound C=1C=C(N2C(COCC2)=O)C(C)=CC=1NC(=O)CC(C=C1N=2)=CC=C1NC=2C1=CC=C(Cl)C=C1 OHFMFUJGVXCEBF-UHFFFAOYSA-N 0.000 claims description 3
- LAKOQFRATQEDPO-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)-3h-benzimidazol-5-yl]-n-[4-(3-oxomorpholin-4-yl)phenyl]acetamide Chemical compound C1=CC(Cl)=CC=C1C1=NC2=CC(CC(=O)NC=3C=CC(=CC=3)N3C(COCC3)=O)=CC=C2N1 LAKOQFRATQEDPO-UHFFFAOYSA-N 0.000 claims description 3
- NDZLXVSVGYNDTC-UHFFFAOYSA-N 2-[2-(5-chloropyridin-2-yl)-3h-benzimidazol-5-yl]-n-[3-methyl-4-(3-oxomorpholin-4-yl)phenyl]acetamide Chemical compound C=1C=C(N2C(COCC2)=O)C(C)=CC=1NC(=O)CC(C=C1N=2)=CC=C1NC=2C1=CC=C(Cl)C=N1 NDZLXVSVGYNDTC-UHFFFAOYSA-N 0.000 claims description 3
- TWIGIXZMJGFYBB-UHFFFAOYSA-N 2-[2-(5-chlorothiophen-2-yl)-3h-benzimidazol-5-yl]-n-[4-(3-oxomorpholin-4-yl)phenyl]-3-phenylpropanamide Chemical compound S1C(Cl)=CC=C1C1=NC2=CC(C(CC=3C=CC=CC=3)C(=O)NC=3C=CC(=CC=3)N3C(COCC3)=O)=CC=C2N1 TWIGIXZMJGFYBB-UHFFFAOYSA-N 0.000 claims description 3
- 239000008186 active pharmaceutical agent Substances 0.000 claims description 3
- 208000021156 intermittent vascular claudication Diseases 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- CGGVIHLACFQGOH-UHFFFAOYSA-N 1-[4-(benzimidazol-1-ylamino)phenyl]piperidin-2-one Chemical compound O=C1N(CCCC1)C1=CC=C(C=C1)NN1C=NC2=C1C=CC=C2 CGGVIHLACFQGOH-UHFFFAOYSA-N 0.000 claims description 2
- SONYDGYZKVDEEN-UHFFFAOYSA-N 2-[[2-(5-chlorothiophen-2-yl)-3h-benzimidazol-5-yl]oxy]-n-[4-(3-oxomorpholin-4-yl)phenyl]acetamide Chemical compound S1C(Cl)=CC=C1C1=NC2=CC(OCC(=O)NC=3C=CC(=CC=3)N3C(COCC3)=O)=CC=C2N1 SONYDGYZKVDEEN-UHFFFAOYSA-N 0.000 claims description 2
- IYIGLWQQAMROOF-HHHXNRCGSA-N OSMI-1 Chemical compound COC1=C(C=CC=C1)[C@@H](NS(=O)(=O)C1=CC2=C(NC(=O)C=C2)C=C1)C(=O)N(CC1=CC=CO1)CC1=CC=CS1 IYIGLWQQAMROOF-HHHXNRCGSA-N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 206010027599 migraine Diseases 0.000 claims description 2
- DXDZGWWHEWUNOA-UHFFFAOYSA-N n-[2-(5-chlorothiophen-2-yl)-3h-benzimidazol-5-yl]-4-(2-oxopiperidin-1-yl)benzamide Chemical compound S1C(Cl)=CC=C1C1=NC2=CC(NC(=O)C=3C=CC(=CC=3)N3C(CCCC3)=O)=CC=C2N1 DXDZGWWHEWUNOA-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- DRTQHJPVMGBUCF-UCVXFZOQSA-N 1-[(2s,3s,4s,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione Chemical compound O[C@H]1[C@H](O)[C@H](CO)O[C@@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UCVXFZOQSA-N 0.000 claims 1
- IGFLLQNIGPBMTN-UHFFFAOYSA-N 1-[4-(aminomethyl)phenyl]piperidin-2-one Chemical compound C1=CC(CN)=CC=C1N1C(=O)CCCC1 IGFLLQNIGPBMTN-UHFFFAOYSA-N 0.000 claims 1
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 10
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
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- 125000002252 acyl group Chemical class 0.000 description 7
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- 238000005259 measurement Methods 0.000 description 4
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- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
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- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
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Classifications
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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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- A61K47/02—Inorganic compounds
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- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/19—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles lyophilised, i.e. freeze-dried, solutions or dispersions
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- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
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- A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
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- A61K9/2826—Sugars or sugar alcohols, e.g. sucrose; Derivatives thereof
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Ophthalmology & Optometry (AREA)
- Cardiology (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Neurosurgery (AREA)
- Inorganic Chemistry (AREA)
- Heart & Thoracic Surgery (AREA)
- Psychology (AREA)
- Oncology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Rheumatology (AREA)
- Diabetes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10238002A DE10238002A1 (de) | 2002-08-20 | 2002-08-20 | Benzimidazolderivate |
| RU2005108042/04A RU2005108042A (ru) | 2002-08-20 | 2003-07-04 | Производные бензимидазола |
| CNA038198355A CN1674893A (zh) | 2002-08-20 | 2003-07-04 | 苯并咪唑衍生物 |
| US10/525,001 US7566789B2 (en) | 2002-08-20 | 2003-07-04 | Benzimidazole derivatives |
| JP2004529997A JP4668614B2 (ja) | 2002-08-20 | 2003-07-04 | ベンズイミダゾール誘導体 |
| CA2496139A CA2496139C (en) | 2002-08-20 | 2003-07-04 | Benzimidazole derivatives |
| BR0313634-5A BR0313634A (pt) | 2002-08-20 | 2003-07-04 | Derivados de benzimidazol |
| AU2003250890A AU2003250890B2 (en) | 2002-08-20 | 2003-07-04 | Benzimidazole derivatives |
| EP03792176A EP1558247B1 (de) | 2002-08-20 | 2003-07-04 | Benzimidazolderivate |
| DE50309217T DE50309217D1 (en) | 2002-08-20 | 2003-07-04 | Benzimidazolderivate |
| AT03792176T ATE386518T1 (de) | 2002-08-20 | 2003-07-04 | Benzimidazolderivate |
| PCT/EP2003/007180 WO2004017963A1 (de) | 2002-08-20 | 2003-07-04 | Benzimidazolderivate |
| ES03792176T ES2303606T3 (es) | 2002-08-20 | 2003-07-04 | Derivados de bencimidazol. |
| ARP030103008A AR041024A1 (es) | 2002-08-20 | 2003-08-20 | Derivados de benzimidazol como inhibidores del factor de coagulacion xa |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10238002A DE10238002A1 (de) | 2002-08-20 | 2002-08-20 | Benzimidazolderivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE10238002A1 true DE10238002A1 (de) | 2004-03-04 |
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Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE10238002A Withdrawn DE10238002A1 (de) | 2002-08-20 | 2002-08-20 | Benzimidazolderivate |
| DE50309217T Expired - Lifetime DE50309217D1 (en) | 2002-08-20 | 2003-07-04 | Benzimidazolderivate |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE50309217T Expired - Lifetime DE50309217D1 (en) | 2002-08-20 | 2003-07-04 | Benzimidazolderivate |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US7566789B2 (enExample) |
| EP (1) | EP1558247B1 (enExample) |
| JP (1) | JP4668614B2 (enExample) |
| CN (1) | CN1674893A (enExample) |
| AR (1) | AR041024A1 (enExample) |
| AT (1) | ATE386518T1 (enExample) |
| AU (1) | AU2003250890B2 (enExample) |
| BR (1) | BR0313634A (enExample) |
| CA (1) | CA2496139C (enExample) |
| DE (2) | DE10238002A1 (enExample) |
| ES (1) | ES2303606T3 (enExample) |
| RU (1) | RU2005108042A (enExample) |
| WO (1) | WO2004017963A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11878968B2 (en) | 2021-07-09 | 2024-01-23 | Plexium, Inc. | Aryl compounds and pharmaceutical compositions that modulate IKZF2 |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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| DE10139060A1 (de) * | 2001-08-08 | 2003-02-20 | Merck Patent Gmbh | Phenylderivate |
-
2002
- 2002-08-20 DE DE10238002A patent/DE10238002A1/de not_active Withdrawn
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2003
- 2003-07-04 US US10/525,001 patent/US7566789B2/en not_active Expired - Fee Related
- 2003-07-04 BR BR0313634-5A patent/BR0313634A/pt not_active IP Right Cessation
- 2003-07-04 CN CNA038198355A patent/CN1674893A/zh active Pending
- 2003-07-04 EP EP03792176A patent/EP1558247B1/de not_active Expired - Lifetime
- 2003-07-04 RU RU2005108042/04A patent/RU2005108042A/ru not_active Application Discontinuation
- 2003-07-04 WO PCT/EP2003/007180 patent/WO2004017963A1/de not_active Ceased
- 2003-07-04 AT AT03792176T patent/ATE386518T1/de not_active IP Right Cessation
- 2003-07-04 AU AU2003250890A patent/AU2003250890B2/en not_active Ceased
- 2003-07-04 CA CA2496139A patent/CA2496139C/en not_active Expired - Fee Related
- 2003-07-04 DE DE50309217T patent/DE50309217D1/de not_active Expired - Lifetime
- 2003-07-04 JP JP2004529997A patent/JP4668614B2/ja not_active Expired - Fee Related
- 2003-07-04 ES ES03792176T patent/ES2303606T3/es not_active Expired - Lifetime
- 2003-08-20 AR ARP030103008A patent/AR041024A1/es unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11878968B2 (en) | 2021-07-09 | 2024-01-23 | Plexium, Inc. | Aryl compounds and pharmaceutical compositions that modulate IKZF2 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP4668614B2 (ja) | 2011-04-13 |
| US7566789B2 (en) | 2009-07-28 |
| ATE386518T1 (de) | 2008-03-15 |
| WO2004017963A1 (de) | 2004-03-04 |
| ES2303606T3 (es) | 2008-08-16 |
| US20050272740A1 (en) | 2005-12-08 |
| EP1558247A1 (de) | 2005-08-03 |
| AR041024A1 (es) | 2005-04-27 |
| AU2003250890B2 (en) | 2009-07-16 |
| CA2496139C (en) | 2011-12-13 |
| CN1674893A (zh) | 2005-09-28 |
| AU2003250890A1 (en) | 2004-03-11 |
| BR0313634A (pt) | 2005-06-21 |
| EP1558247B1 (de) | 2008-02-20 |
| RU2005108042A (ru) | 2005-11-20 |
| JP2006500369A (ja) | 2006-01-05 |
| DE50309217D1 (en) | 2008-04-03 |
| CA2496139A1 (en) | 2004-03-04 |
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