UA80296C2 - Imidazolopyridines and methods of making and using the same - Google Patents
Imidazolopyridines and methods of making and using the same Download PDFInfo
- Publication number
- UA80296C2 UA80296C2 UAA200503149A UA2005003149A UA80296C2 UA 80296 C2 UA80296 C2 UA 80296C2 UA A200503149 A UAA200503149 A UA A200503149A UA 2005003149 A UA2005003149 A UA 2005003149A UA 80296 C2 UA80296 C2 UA 80296C2
- Authority
- UA
- Ukraine
- Prior art keywords
- methylpyridin
- imidazo
- pyridin
- pyrimidin
- aminopyrimidin
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 32
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical class C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 145
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 38
- 201000010099 disease Diseases 0.000 claims abstract description 20
- 230000003176 fibrotic effect Effects 0.000 claims abstract description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 231
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 187
- 125000000217 alkyl group Chemical group 0.000 claims description 164
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 115
- 150000001412 amines Chemical class 0.000 claims description 107
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 95
- -1 hydroxy, amino, nitro, cyano, guanidino, amidino, carboxy, sulfo, mercapto Chemical class 0.000 claims description 75
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 74
- 125000001072 heteroaryl group Chemical group 0.000 claims description 61
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 56
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 claims description 47
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 46
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 44
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 42
- 125000003545 alkoxy group Chemical group 0.000 claims description 37
- 150000001408 amides Chemical class 0.000 claims description 33
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 32
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 30
- 125000003118 aryl group Chemical group 0.000 claims description 30
- 210000004027 cell Anatomy 0.000 claims description 29
- 125000004414 alkyl thio group Chemical group 0.000 claims description 28
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 28
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 27
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 27
- 125000002252 acyl group Chemical group 0.000 claims description 26
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 24
- 150000002367 halogens Chemical class 0.000 claims description 23
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 21
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
- 206010016654 Fibrosis Diseases 0.000 claims description 20
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 20
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims description 20
- AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 claims description 19
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 18
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 18
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 18
- 208000035475 disorder Diseases 0.000 claims description 17
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 16
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 16
- 230000004761 fibrosis Effects 0.000 claims description 16
- 125000001188 haloalkyl group Chemical group 0.000 claims description 16
- 229960003966 nicotinamide Drugs 0.000 claims description 16
- 235000005152 nicotinamide Nutrition 0.000 claims description 16
- 239000011570 nicotinamide Substances 0.000 claims description 16
- 125000000304 alkynyl group Chemical group 0.000 claims description 15
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 14
- 206010028980 Neoplasm Diseases 0.000 claims description 13
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 13
- HVLUYXIJZLDNIS-UHFFFAOYSA-N 2-thiophen-2-ylethanamine Chemical compound NCCC1=CC=CS1 HVLUYXIJZLDNIS-UHFFFAOYSA-N 0.000 claims description 12
- GMPKIPWJBDOURN-UHFFFAOYSA-N Methoxyamine Chemical compound CON GMPKIPWJBDOURN-UHFFFAOYSA-N 0.000 claims description 12
- 150000004702 methyl esters Chemical class 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 230000019491 signal transduction Effects 0.000 claims description 12
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 12
- 238000011282 treatment Methods 0.000 claims description 12
- JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 claims description 11
- 102000010834 Extracellular Matrix Proteins Human genes 0.000 claims description 11
- 108010037362 Extracellular Matrix Proteins Proteins 0.000 claims description 11
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 11
- 230000015572 biosynthetic process Effects 0.000 claims description 11
- HWDVTQAXQJQROO-UHFFFAOYSA-N cyclopropylazanide Chemical compound [NH-]C1CC1 HWDVTQAXQJQROO-UHFFFAOYSA-N 0.000 claims description 11
- 210000002744 extracellular matrix Anatomy 0.000 claims description 11
- 125000005224 heteroarylcarbonylamino group Chemical group 0.000 claims description 11
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 10
- 125000004104 aryloxy group Chemical group 0.000 claims description 10
- 239000012634 fragment Substances 0.000 claims description 10
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 10
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 9
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 9
- 125000004122 cyclic group Chemical group 0.000 claims description 9
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 9
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 230000002401 inhibitory effect Effects 0.000 claims description 9
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 claims description 9
- 235000019260 propionic acid Nutrition 0.000 claims description 9
- 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 9
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 8
- ZXKINMCYCKHYFR-UHFFFAOYSA-N aminooxidanide Chemical compound [O-]N ZXKINMCYCKHYFR-UHFFFAOYSA-N 0.000 claims description 8
- 239000004202 carbamide Substances 0.000 claims description 8
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 8
- 125000005169 cycloalkylcarbonylamino group Chemical group 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 210000004185 liver Anatomy 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 7
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 claims description 7
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 7
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 7
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 7
- 125000003435 aroyl group Chemical group 0.000 claims description 7
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 7
- 210000004072 lung Anatomy 0.000 claims description 7
- 108090000623 proteins and genes Proteins 0.000 claims description 7
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 claims description 7
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 6
- 125000005126 aryl alkyl carbonyl amino group Chemical group 0.000 claims description 6
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 6
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 6
- 230000001404 mediated effect Effects 0.000 claims description 6
- 230000002018 overexpression Effects 0.000 claims description 6
- RGUUBRUFWMBQOW-UHFFFAOYSA-N 2-amino-1-pyridin-3-ylethanone Chemical compound NCC(=O)C1=CC=CN=C1 RGUUBRUFWMBQOW-UHFFFAOYSA-N 0.000 claims description 5
- 238000009825 accumulation Methods 0.000 claims description 5
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- BBEQQKBWUHCIOU-UHFFFAOYSA-N 5-(dimethylamino)-1-naphthalenesulfonic acid(dansyl acid) Chemical compound C1=CC=C2C(N(C)C)=CC=CC2=C1S(O)(=O)=O BBEQQKBWUHCIOU-UHFFFAOYSA-N 0.000 claims description 4
- 239000005711 Benzoic acid Substances 0.000 claims description 4
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims description 4
- 206010027476 Metastases Diseases 0.000 claims description 4
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 4
- 125000005163 aryl sulfanyl group Chemical group 0.000 claims description 4
- 235000010233 benzoic acid Nutrition 0.000 claims description 4
- 210000003445 biliary tract Anatomy 0.000 claims description 4
- 230000007882 cirrhosis Effects 0.000 claims description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 125000005114 heteroarylalkoxy group Chemical group 0.000 claims description 4
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 4
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims description 4
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 4
- IPOVLZSJBYKHHU-UHFFFAOYSA-N piperidin-3-ylmethanamine Chemical compound NCC1CCCNC1 IPOVLZSJBYKHHU-UHFFFAOYSA-N 0.000 claims description 4
- FVUKYCZRWSQGAS-UHFFFAOYSA-N 3-carbamoylbenzoic acid Chemical compound NC(=O)C1=CC=CC(C(O)=O)=C1 FVUKYCZRWSQGAS-UHFFFAOYSA-N 0.000 claims description 3
- NOQGZXFMHARMLW-UHFFFAOYSA-N Daminozide Chemical compound CN(C)NC(=O)CCC(O)=O NOQGZXFMHARMLW-UHFFFAOYSA-N 0.000 claims description 3
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- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
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- YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical compound NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
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- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Ophthalmology & Optometry (AREA)
- Heart & Thoracic Surgery (AREA)
- Gastroenterology & Hepatology (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40881202P | 2002-09-06 | 2002-09-06 | |
| PCT/US2003/027721 WO2004021989A2 (en) | 2002-09-06 | 2003-09-05 | Imidazolopyridines and methods of making and using the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA80296C2 true UA80296C2 (en) | 2007-09-10 |
Family
ID=31978685
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UAA200503149A UA80296C2 (en) | 2002-09-06 | 2003-05-09 | Imidazolopyridines and methods of making and using the same |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US20060135517A1 (de) |
| EP (1) | EP1546112A4 (de) |
| JP (1) | JP2006502164A (de) |
| KR (1) | KR20050035296A (de) |
| CN (1) | CN1694871B (de) |
| AR (1) | AR041206A1 (de) |
| AU (1) | AU2003270318B2 (de) |
| BR (1) | BR0314052A (de) |
| CA (1) | CA2497968A1 (de) |
| EA (1) | EA010426B1 (de) |
| GE (1) | GEP20074165B (de) |
| MX (1) | MXPA05002442A (de) |
| MY (1) | MY139566A (de) |
| NO (1) | NO20051493L (de) |
| NZ (1) | NZ539068A (de) |
| PL (1) | PL375691A1 (de) |
| RS (1) | RS20050199A (de) |
| UA (1) | UA80296C2 (de) |
| WO (1) | WO2004021989A2 (de) |
| ZA (1) | ZA200501853B (de) |
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| PA8595001A1 (es) * | 2003-03-04 | 2004-09-28 | Pfizer Prod Inc | Nuevos compuestos heteroaromaticos condensados que son inhibidores del factor de crecimiento transforante (tgf) |
| WO2006004194A1 (ja) * | 2004-07-02 | 2006-01-12 | Nishimoto, Tomo | TGFβ2を標的としたアルツハイマー病治療薬のスクリーニング法 |
| US7718801B2 (en) | 2004-08-31 | 2010-05-18 | Banyu Pharmaceutical Co., Ltd. | Substituted imidazole derivative |
| EP1786802A1 (de) * | 2004-08-31 | 2007-05-23 | Biogen Idec MA, Inc. | Pyrimidinylimidazole als tgf-beta-hemmer |
| JP2008516962A (ja) * | 2004-10-15 | 2008-05-22 | バイオジェン・アイデック・エムエイ・インコーポレイテッド | 血管傷害を治療する方法 |
| WO2006070943A1 (ja) * | 2004-12-28 | 2006-07-06 | Takeda Pharmaceutical Company Limited | 縮合イミダゾール化合物およびその用途 |
| KR101300831B1 (ko) | 2005-03-21 | 2013-08-30 | 에스*바이오 피티이 리미티드 | 이미다조[1,2-ａ]피리딘 유도체, 이의 제조 방법 및 그의약학적 용도 |
| US7666880B2 (en) | 2005-03-21 | 2010-02-23 | S*Bio Pte Ltd. | Imidazo[1,2-A]pyridine derivatives: preparation and pharmaceutical applications |
| US20070155738A1 (en) | 2005-05-20 | 2007-07-05 | Alantos Pharmaceuticals, Inc. | Heterobicyclic metalloprotease inhibitors |
| WO2007028051A2 (en) | 2005-09-02 | 2007-03-08 | Abbott Laboratories | Novel imidazo based heterocycles |
| EP1973914A2 (de) * | 2005-12-22 | 2008-10-01 | Biogen Idec MA Inc. | Modulatoren des transformierenden wachstumsfaktors |
| DE102005061840A1 (de) * | 2005-12-23 | 2007-06-28 | Merck Patent Gmbh | Triazolderivate |
| US7563797B2 (en) | 2006-08-28 | 2009-07-21 | Forest Laboratories Holding Limited | Substituted imidazo(1,2-A)pyrimidines and imidazo(1,2-A) pyridines as cannabinoid receptor ligands |
| ES2647472T3 (es) | 2006-10-03 | 2017-12-21 | Genzyme Corporation | Anticuerpos contra TGF-BETA para uso en el tratamiento de lactantes con riesgo de desarrollar displasia broncopulmonar |
| US7977336B2 (en) | 2006-12-28 | 2011-07-12 | Banyu Pharmaceutical Co. Ltd | Aminopyrimidine derivatives as PLK1 inhibitors |
| US8188272B2 (en) | 2007-03-21 | 2012-05-29 | Bristol-Myers Squibb Company | Fused heterocyclic compounds useful as kinase modulators |
| WO2008133192A1 (ja) * | 2007-04-19 | 2008-11-06 | Takeda Pharmaceutical Company Limited | 縮合イミダゾール化合物およびその用途 |
| JP5640005B2 (ja) | 2008-07-14 | 2014-12-10 | ギリアード サイエンシーズ， インコーポレイテッド | Ｈｄａｃおよび／またはｃｄｋ阻害剤としてのイミダゾシルピリジン化合物 |
| NZ590320A (en) | 2008-07-14 | 2012-12-21 | Gilead Sciences Inc | Fused heterocyclyc inhibitors of histone deacetylase and/or cyclin-dependent kinases |
| CA2728228A1 (en) | 2008-07-14 | 2010-01-21 | Gilead Sciences, Inc. | Oxindolyl inhibitor compounds |
| CN102164604A (zh) | 2008-07-24 | 2011-08-24 | 百时美施贵宝公司 | 用作激酶调节剂的稠合杂环化合物 |
| MX2011001090A (es) | 2008-07-28 | 2011-03-15 | Gilead Sciences Inc | Compuestos de inhibidor de desacetilasa de histona de cicloalquilideno y heterocicloalquilideno. |
| PE20120325A1 (es) * | 2009-05-19 | 2012-04-12 | Dow Agrosciences Llc | Aminopirimidinas sustituidas con arilo como agentes fungicidas |
| MX2011012629A (es) * | 2009-05-27 | 2012-03-06 | Abbott Lab | Inhibidores de actividad de cinasa tipo pirimidina. |
| WO2010144371A1 (en) | 2009-06-08 | 2010-12-16 | Gilead Colorado, Inc. | Alkanoylamino benzamide aniline hdac inihibitor compounds |
| MX2011013166A (es) | 2009-06-08 | 2012-01-30 | Gilead Sciences Inc | Compuestos inhibidores de hdac de cicloalquilcarbamatobenzamida-an ilina. |
| EA020847B1 (ru) | 2009-10-30 | 2015-02-27 | Янссен Фармацевтика Нв | ПРОИЗВОДНЫЕ ИМИДАЗО[1,2-b]ПИРИДАЗИНА И ИХ ПРИМЕНЕНИЕ В КАЧЕСТВЕ ИНГИБИТОРОВ PDE10 |
| JP5543980B2 (ja) * | 2009-12-18 | 2014-07-09 | 田辺三菱製薬株式会社 | 新規抗血小板薬 |
| AR080754A1 (es) | 2010-03-09 | 2012-05-09 | Janssen Pharmaceutica Nv | Derivados de imidazo (1,2-a) pirazina y su uso como inhibidores de pde10 |
| JP5959330B2 (ja) * | 2011-06-17 | 2016-08-02 | 田辺三菱製薬株式会社 | 新規抗血小板薬 |
| WO2013000924A1 (en) | 2011-06-27 | 2013-01-03 | Janssen Pharmaceutica Nv | 1-ARYL-4-METHYL-[1,2,4]TRIAZOLO[4,3-a]QUINOXALINE DERIVATIVES |
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2003
- 2003-05-09 UA UAA200503149A patent/UA80296C2/uk unknown
- 2003-09-05 US US10/526,653 patent/US20060135517A1/en not_active Abandoned
- 2003-09-05 NZ NZ539068A patent/NZ539068A/en unknown
- 2003-09-05 BR BR0314052-0A patent/BR0314052A/pt not_active IP Right Cessation
- 2003-09-05 GE GEAP20038732A patent/GEP20074165B/en unknown
- 2003-09-05 CN CN038248662A patent/CN1694871B/zh not_active Expired - Fee Related
- 2003-09-05 EP EP03752004A patent/EP1546112A4/de not_active Withdrawn
- 2003-09-05 EA EA200500453A patent/EA010426B1/ru not_active IP Right Cessation
- 2003-09-05 MX MXPA05002442A patent/MXPA05002442A/es active IP Right Grant
- 2003-09-05 CA CA002497968A patent/CA2497968A1/en not_active Abandoned
- 2003-09-05 KR KR1020057003871A patent/KR20050035296A/ko not_active Withdrawn
- 2003-09-05 AU AU2003270318A patent/AU2003270318B2/en not_active Ceased
- 2003-09-05 WO PCT/US2003/027721 patent/WO2004021989A2/en not_active Ceased
- 2003-09-05 RS YUP-2005/0199A patent/RS20050199A/sr unknown
- 2003-09-05 PL PL03375691A patent/PL375691A1/xx not_active Application Discontinuation
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- 2003-09-08 AR ARP030103249A patent/AR041206A1/es not_active Application Discontinuation
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|---|---|
| NO20051493D0 (no) | 2005-03-21 |
| US20060135517A1 (en) | 2006-06-22 |
| AR041206A1 (es) | 2005-05-11 |
| WO2004021989A3 (en) | 2004-09-23 |
| GEP20074165B (en) | 2007-07-25 |
| CA2497968A1 (en) | 2004-03-18 |
| RS20050199A (sr) | 2007-08-03 |
| NO20051493L (no) | 2005-03-21 |
| JP2006502164A (ja) | 2006-01-19 |
| MXPA05002442A (es) | 2005-09-30 |
| KR20050035296A (ko) | 2005-04-15 |
| EP1546112A2 (de) | 2005-06-29 |
| AU2003270318B2 (en) | 2010-01-14 |
| ZA200501853B (en) | 2005-11-30 |
| CN1694871B (zh) | 2010-06-16 |
| NZ539068A (en) | 2006-10-27 |
| BR0314052A (pt) | 2005-07-05 |
| EP1546112A4 (de) | 2006-06-07 |
| WO2004021989A2 (en) | 2004-03-18 |
| AU2003270318A1 (en) | 2004-03-29 |
| CN1694871A (zh) | 2005-11-09 |
| PL375691A1 (en) | 2005-12-12 |
| MY139566A (en) | 2009-10-30 |
| EA200500453A1 (ru) | 2005-10-27 |
| EA010426B1 (ru) | 2008-08-29 |
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