KR20040041649A - 항염증제로서 유용한 스피로-히단토인 화합물 - Google Patents
항염증제로서 유용한 스피로-히단토인 화합물 Download PDFInfo
- Publication number
- KR20040041649A KR20040041649A KR10-2004-7004778A KR20047004778A KR20040041649A KR 20040041649 A KR20040041649 A KR 20040041649A KR 20047004778 A KR20047004778 A KR 20047004778A KR 20040041649 A KR20040041649 A KR 20040041649A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- substituted
- heteroaryl
- alkylene
- cyano
- 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.)
- Withdrawn
Links
- 229940121363 anti-inflammatory agent Drugs 0.000 title abstract description 7
- 239000002260 anti-inflammatory agent Substances 0.000 title abstract description 7
- QAHZIGHCEBUNGT-QMGFNSACSA-N (5r,6s,7s,8r,9r)-6,7,8-trihydroxy-9-(hydroxymethyl)-1,3-diazaspiro[4.5]decane-2,4-dione Chemical class O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)C[C@]11C(=O)NC(=O)N1 QAHZIGHCEBUNGT-QMGFNSACSA-N 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 284
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 88
- 150000003839 salts Chemical class 0.000 claims abstract description 47
- 229940002612 prodrug Drugs 0.000 claims abstract description 36
- 239000000651 prodrug Substances 0.000 claims abstract description 36
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 30
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 18
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 14
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 13
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 9
- 150000004677 hydrates Chemical class 0.000 claims abstract description 7
- 102100022339 Integrin alpha-L Human genes 0.000 claims abstract 3
- 108010064548 Lymphocyte Function-Associated Antigen-1 Proteins 0.000 claims abstract 3
- 125000000217 alkyl group Chemical group 0.000 claims description 518
- -1 heterocyclo Chemical group 0.000 claims description 165
- 229910052739 hydrogen Inorganic materials 0.000 claims description 125
- 125000002947 alkylene group Chemical group 0.000 claims description 83
- 238000000034 method Methods 0.000 claims description 82
- 229910052736 halogen Inorganic materials 0.000 claims description 78
- 125000003118 aryl group Chemical group 0.000 claims description 76
- 150000002367 halogens Chemical class 0.000 claims description 73
- 239000001257 hydrogen Substances 0.000 claims description 70
- 238000002360 preparation method Methods 0.000 claims description 68
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 65
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 62
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 61
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 55
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 53
- 125000003545 alkoxy group Chemical group 0.000 claims description 39
- 229910052799 carbon Inorganic materials 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 31
- 125000003342 alkenyl group Chemical group 0.000 claims description 29
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 29
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
- 125000004450 alkenylene group Chemical group 0.000 claims description 24
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 24
- 125000004474 heteroalkylene group Chemical group 0.000 claims description 24
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 23
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 22
- 125000001188 haloalkyl group Chemical group 0.000 claims description 22
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- 125000004076 pyridyl group Chemical group 0.000 claims description 19
- 125000005842 heteroatom Chemical group 0.000 claims description 18
- 125000001544 thienyl group Chemical group 0.000 claims description 18
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims description 17
- 125000002883 imidazolyl group Chemical group 0.000 claims description 16
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 16
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 16
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims description 15
- 125000004414 alkyl thio group Chemical group 0.000 claims description 15
- 208000027866 inflammatory disease Diseases 0.000 claims description 15
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 15
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 14
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 13
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 12
- 230000002757 inflammatory effect Effects 0.000 claims description 12
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 12
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 12
- 125000000335 thiazolyl group Chemical group 0.000 claims description 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
- 208000026278 immune system disease Diseases 0.000 claims description 11
- 125000005936 piperidyl group Chemical group 0.000 claims description 11
- 125000005864 sulfonamidyl group Chemical group 0.000 claims description 11
- 125000002252 acyl group Chemical group 0.000 claims description 10
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 10
- 230000001684 chronic effect Effects 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 239000000543 intermediate Substances 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
- 230000001154 acute effect Effects 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 125000001425 triazolyl group Chemical group 0.000 claims description 8
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 7
- 208000006673 asthma Diseases 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 125000004193 piperazinyl group Chemical group 0.000 claims description 7
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 7
- 208000011580 syndromic disease Diseases 0.000 claims description 7
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
- 125000005605 benzo group Chemical group 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- 125000002757 morpholinyl group Chemical group 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 239000012453 solvate Substances 0.000 claims description 6
- 208000023275 Autoimmune disease Diseases 0.000 claims description 5
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 5
- 241000124008 Mammalia Species 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 5
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 5
- 125000001041 indolyl group Chemical group 0.000 claims description 5
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 5
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 5
- 231100000419 toxicity Toxicity 0.000 claims description 5
- 230000001988 toxicity Effects 0.000 claims description 5
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 4
- 229930194542 Keto Natural products 0.000 claims description 4
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 230000006378 damage Effects 0.000 claims description 4
- 206010012601 diabetes mellitus Diseases 0.000 claims description 4
- 125000000468 ketone group Chemical group 0.000 claims description 4
- 125000005493 quinolyl group Chemical group 0.000 claims description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
- 230000001225 therapeutic effect Effects 0.000 claims description 4
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 3
- 241001465754 Metazoa Species 0.000 claims description 3
- 201000004681 Psoriasis Diseases 0.000 claims description 3
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 3
- 206010052779 Transplant rejections Diseases 0.000 claims description 3
- 201000010105 allergic rhinitis Diseases 0.000 claims description 3
- 125000005110 aryl thio group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 208000010668 atopic eczema Diseases 0.000 claims description 3
- 230000001363 autoimmune Effects 0.000 claims description 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 208000002551 irritable bowel syndrome Diseases 0.000 claims description 3
- 201000008482 osteoarthritis Diseases 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 3
- 208000026872 Addison Disease Diseases 0.000 claims description 2
- 208000024827 Alzheimer disease Diseases 0.000 claims description 2
- 240000000662 Anethum graveolens Species 0.000 claims description 2
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 2
- 201000001320 Atherosclerosis Diseases 0.000 claims description 2
- 208000023328 Basedow disease Diseases 0.000 claims description 2
- 206010006458 Bronchitis chronic Diseases 0.000 claims description 2
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 2
- 206010010741 Conjunctivitis Diseases 0.000 claims description 2
- 208000011231 Crohn disease Diseases 0.000 claims description 2
- 201000003883 Cystic fibrosis Diseases 0.000 claims description 2
- 201000004624 Dermatitis Diseases 0.000 claims description 2
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 2
- 206010012442 Dermatitis contact Diseases 0.000 claims description 2
- 208000007882 Gastritis Diseases 0.000 claims description 2
- 206010018366 Glomerulonephritis acute Diseases 0.000 claims description 2
- 208000015023 Graves' disease Diseases 0.000 claims description 2
- 208000030836 Hashimoto thyroiditis Diseases 0.000 claims description 2
- 208000005176 Hepatitis C Diseases 0.000 claims description 2
- 208000001132 Osteoporosis Diseases 0.000 claims description 2
- 206010033645 Pancreatitis Diseases 0.000 claims description 2
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims description 2
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims description 2
- 206010037423 Pulmonary oedema Diseases 0.000 claims description 2
- 206010063837 Reperfusion injury Diseases 0.000 claims description 2
- 206010039710 Scleroderma Diseases 0.000 claims description 2
- 208000021386 Sjogren Syndrome Diseases 0.000 claims description 2
- 208000006011 Stroke Diseases 0.000 claims description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 2
- 208000024780 Urticaria Diseases 0.000 claims description 2
- 206010046851 Uveitis Diseases 0.000 claims description 2
- 206010047115 Vasculitis Diseases 0.000 claims description 2
- 231100000851 acute glomerulonephritis Toxicity 0.000 claims description 2
- 201000008937 atopic dermatitis Diseases 0.000 claims description 2
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 206010006451 bronchitis Diseases 0.000 claims description 2
- 208000007451 chronic bronchitis Diseases 0.000 claims description 2
- 208000025302 chronic primary adrenal insufficiency Diseases 0.000 claims description 2
- 206010009887 colitis Diseases 0.000 claims description 2
- 208000010247 contact dermatitis Diseases 0.000 claims description 2
- 125000003073 divalent carboacyl group Chemical group 0.000 claims description 2
- 208000024908 graft versus host disease Diseases 0.000 claims description 2
- 210000003714 granulocyte Anatomy 0.000 claims description 2
- 208000002672 hepatitis B Diseases 0.000 claims description 2
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 201000006417 multiple sclerosis Diseases 0.000 claims description 2
- 208000010125 myocardial infarction Diseases 0.000 claims description 2
- 230000001338 necrotic effect Effects 0.000 claims description 2
- 208000005333 pulmonary edema Diseases 0.000 claims description 2
- 208000005069 pulmonary fibrosis Diseases 0.000 claims description 2
- 230000035939 shock Effects 0.000 claims description 2
- 230000009885 systemic effect Effects 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 24
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 8
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 7
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 7
- 206010015150 Erythema Diseases 0.000 claims 1
- 206010037660 Pyrexia Diseases 0.000 claims 1
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 claims 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims 1
- 231100000321 erythema Toxicity 0.000 claims 1
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- 239000003112 inhibitor Substances 0.000 abstract description 28
- 125000006574 non-aromatic ring group Chemical group 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 173
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- 239000000243 solution Substances 0.000 description 96
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
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Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32636101P | 2001-10-01 | 2001-10-01 | |
| US60/326,361 | 2001-10-01 | ||
| US35411302P | 2002-02-04 | 2002-02-04 | |
| US60/354,113 | 2002-02-04 | ||
| US40025902P | 2002-08-01 | 2002-08-01 | |
| US60/400,259 | 2002-08-01 | ||
| PCT/US2002/031283 WO2003029245A1 (en) | 2001-10-01 | 2002-09-30 | Spiro-hydantoin compounds useful as anti-inflammatory agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20040041649A true KR20040041649A (ko) | 2004-05-17 |
Family
ID=27406458
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| KR10-2004-7004778A Withdrawn KR20040041649A (ko) | 2001-10-01 | 2002-09-30 | 항염증제로서 유용한 스피로-히단토인 화합물 |
Country Status (23)
| Country | Link |
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| US (4) | US6977267B2 (https=) |
| EP (1) | EP1432700B1 (https=) |
| JP (1) | JP4394442B2 (https=) |
| KR (1) | KR20040041649A (https=) |
| CN (1) | CN1596253A (https=) |
| AR (1) | AR036663A1 (https=) |
| AT (1) | ATE447565T1 (https=) |
| BR (1) | BR0213025A (https=) |
| CA (1) | CA2462112A1 (https=) |
| DE (1) | DE60234264D1 (https=) |
| ES (1) | ES2339107T3 (https=) |
| GE (1) | GEP20063767B (https=) |
| HR (1) | HRP20040311A2 (https=) |
| HU (1) | HUP0402338A3 (https=) |
| IL (1) | IL160990A0 (https=) |
| IS (1) | IS7197A (https=) |
| MX (1) | MXPA04002993A (https=) |
| NO (1) | NO20041339L (https=) |
| NZ (1) | NZ531870A (https=) |
| PE (1) | PE20030845A1 (https=) |
| PL (1) | PL369337A1 (https=) |
| RS (1) | RS26604A (https=) |
| WO (1) | WO2003029245A1 (https=) |
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| CA1331757C (en) * | 1988-02-29 | 1994-08-30 | Janssen Pharmaceutica Naamloze Vennootschap | 5-lipoxygenase inhibiting 4-(4-phenyl-1-piperazinyl)phenols |
| US5346913A (en) * | 1992-05-26 | 1994-09-13 | Rohm And Haas Company | N-iodopropargyl hydantoin compounds, compositions, preparation, and use as antimicrobial agents |
| FR2694290B1 (fr) * | 1992-07-08 | 1994-09-02 | Roussel Uclaf | Nouvelles phénylimidazolidines éventuellement substituées, leur procédé de préparation, leur application comme médicaments et les compositions pharmaceutiques les renfermant. |
| TW521073B (en) * | 1994-01-05 | 2003-02-21 | Hoechst Marion Roussel Inc | New optionally substituted phenylimidazolidines, their preparation process, their use as anti-androgenic agent and the pharmaceutical compositions containing them |
| FR2741342B1 (fr) * | 1995-11-22 | 1998-02-06 | Roussel Uclaf | Nouvelles phenylimidazolidines fluorees ou hydroxylees, procede, intermediaires de preparation, application comme medicaments, nouvelle utilisation et compositions pharmaceutiques |
| US6890915B2 (en) | 2001-05-25 | 2005-05-10 | Bristol-Myers Squibb Pharma Company | Hydantoins and related heterocycles as inhibitors of matrix metalloproteinases and/or TNF-α converting enzyme (TACE) |
-
2002
- 2002-09-30 CA CA002462112A patent/CA2462112A1/en not_active Abandoned
- 2002-09-30 KR KR10-2004-7004778A patent/KR20040041649A/ko not_active Withdrawn
- 2002-09-30 HR HR20040311A patent/HRP20040311A2/hr not_active Application Discontinuation
- 2002-09-30 ES ES02800414T patent/ES2339107T3/es not_active Expired - Lifetime
- 2002-09-30 AT AT02800414T patent/ATE447565T1/de not_active IP Right Cessation
- 2002-09-30 WO PCT/US2002/031283 patent/WO2003029245A1/en not_active Ceased
- 2002-09-30 HU HU0402338A patent/HUP0402338A3/hu unknown
- 2002-09-30 RS YU26604A patent/RS26604A/sr unknown
- 2002-09-30 CN CNA028238540A patent/CN1596253A/zh active Pending
- 2002-09-30 PL PL02369337A patent/PL369337A1/xx not_active Application Discontinuation
- 2002-09-30 EP EP02800414A patent/EP1432700B1/en not_active Expired - Lifetime
- 2002-09-30 GE GE5595A patent/GEP20063767B/en unknown
- 2002-09-30 IL IL16099002A patent/IL160990A0/xx unknown
- 2002-09-30 MX MXPA04002993A patent/MXPA04002993A/es unknown
- 2002-09-30 BR BR0213025-4A patent/BR0213025A/pt not_active IP Right Cessation
- 2002-09-30 AR ARP020103695A patent/AR036663A1/es unknown
- 2002-09-30 NZ NZ531870A patent/NZ531870A/en unknown
- 2002-09-30 JP JP2003532494A patent/JP4394442B2/ja not_active Expired - Fee Related
- 2002-09-30 DE DE60234264T patent/DE60234264D1/de not_active Expired - Lifetime
- 2002-10-01 PE PE2002000971A patent/PE20030845A1/es not_active Application Discontinuation
- 2002-10-01 US US10/262,182 patent/US6977267B2/en not_active Expired - Lifetime
-
2004
- 2004-03-24 IS IS7197A patent/IS7197A/is unknown
- 2004-03-31 NO NO20041339A patent/NO20041339L/no not_active Application Discontinuation
- 2004-05-24 US US10/852,576 patent/US7078420B2/en not_active Expired - Lifetime
- 2004-06-16 US US10/869,292 patent/US20050004153A1/en not_active Abandoned
- 2004-06-16 US US10/869,289 patent/US20040259897A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| NO20041339D0 (no) | 2004-03-31 |
| CA2462112A1 (en) | 2003-04-10 |
| US20050004153A1 (en) | 2005-01-06 |
| GEP20063767B (en) | 2006-03-10 |
| EP1432700A1 (en) | 2004-06-30 |
| HUP0402338A2 (hu) | 2005-02-28 |
| DE60234264D1 (de) | 2009-12-17 |
| WO2003029245A1 (en) | 2003-04-10 |
| US20040259897A1 (en) | 2004-12-23 |
| US20040009998A1 (en) | 2004-01-15 |
| US6977267B2 (en) | 2005-12-20 |
| EP1432700A4 (en) | 2004-12-22 |
| US7078420B2 (en) | 2006-07-18 |
| AR036663A1 (es) | 2004-09-22 |
| CN1596253A (zh) | 2005-03-16 |
| BR0213025A (pt) | 2004-10-05 |
| RS26604A (sr) | 2006-12-15 |
| IL160990A0 (en) | 2004-08-31 |
| PL369337A1 (en) | 2005-04-18 |
| ES2339107T3 (es) | 2010-05-17 |
| MXPA04002993A (es) | 2004-07-15 |
| HRP20040311A2 (en) | 2005-02-28 |
| NZ531870A (en) | 2005-08-26 |
| JP2005510476A (ja) | 2005-04-21 |
| IS7197A (is) | 2004-03-24 |
| US20040248920A1 (en) | 2004-12-09 |
| JP4394442B2 (ja) | 2010-01-06 |
| NO20041339L (no) | 2004-05-24 |
| PE20030845A1 (es) | 2003-10-23 |
| HK1063467A1 (en) | 2004-12-31 |
| ATE447565T1 (de) | 2009-11-15 |
| HUP0402338A3 (en) | 2008-10-28 |
| EP1432700B1 (en) | 2009-11-04 |
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