JP2005538099A5 - - Google Patents
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- Publication number
- JP2005538099A5 JP2005538099A5 JP2004523926A JP2004523926A JP2005538099A5 JP 2005538099 A5 JP2005538099 A5 JP 2005538099A5 JP 2004523926 A JP2004523926 A JP 2004523926A JP 2004523926 A JP2004523926 A JP 2004523926A JP 2005538099 A5 JP2005538099 A5 JP 2005538099A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- phenyl
- optionally substituted
- pharmaceutically acceptable
- amino
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims description 26
- 150000002148 esters Chemical class 0.000 claims description 18
- 238000001727 in vivo Methods 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- 239000012453 solvate Substances 0.000 claims description 17
- -1 hydroxy, amino Chemical group 0.000 claims description 10
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 5
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 5
- 208000001132 Osteoporosis Diseases 0.000 claims description 5
- 201000004681 Psoriasis Diseases 0.000 claims description 5
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 5
- 201000010105 allergic rhinitis Diseases 0.000 claims description 5
- 208000006673 asthma Diseases 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 201000008482 osteoarthritis Diseases 0.000 claims description 5
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims 21
- 125000000217 alkyl group Chemical group 0.000 claims 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 17
- 125000005843 halogen group Chemical group 0.000 claims 15
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 9
- 239000003814 drug Substances 0.000 claims 8
- 125000001072 heteroaryl group Chemical group 0.000 claims 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 201000011510 cancer Diseases 0.000 claims 4
- 125000004452 carbocyclyl group Chemical group 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 208000002551 irritable bowel syndrome Diseases 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 2
- 238000002648 combination therapy Methods 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- DLXZKQCNTIPINT-SNVBAGLBSA-N 2-[(3-chloro-2-fluorophenyl)methylsulfanyl]-4-(dimethylsulfamoylamino)-6-[[(2r)-1-hydroxypropan-2-yl]amino]pyrimidine Chemical compound OC[C@@H](C)NC1=CC(NS(=O)(=O)N(C)C)=NC(SCC=2C(=C(Cl)C=CC=2)F)=N1 DLXZKQCNTIPINT-SNVBAGLBSA-N 0.000 claims 1
- 102000009410 Chemokine receptor Human genes 0.000 claims 1
- 108050000299 Chemokine receptor Proteins 0.000 claims 1
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 230000009286 beneficial effect Effects 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- KSNXUQRPDJFHTM-LLVKDONJSA-N n-[2-[(2,3-difluorophenyl)methylsulfanyl]-6-[[(2r)-1-hydroxypropan-2-yl]amino]pyrimidin-4-yl]azetidine-1-sulfonamide Chemical compound N=1C(SCC=2C(=C(F)C=CC=2)F)=NC(N[C@@H](CO)C)=CC=1NS(=O)(=O)N1CCC1 KSNXUQRPDJFHTM-LLVKDONJSA-N 0.000 claims 1
- CWSXHDBZSCOEHO-GFCCVEGCSA-N n-[2-[(2,3-difluorophenyl)methylsulfanyl]-6-[[(2r)-1-hydroxypropan-2-yl]amino]pyrimidin-4-yl]morpholine-4-sulfonamide Chemical compound N=1C(SCC=2C(=C(F)C=CC=2)F)=NC(N[C@@H](CO)C)=CC=1NS(=O)(=O)N1CCOCC1 CWSXHDBZSCOEHO-GFCCVEGCSA-N 0.000 claims 1
- ZYCHLELHVSMDDI-CYBMUJFWSA-N n-[2-[(2,3-difluorophenyl)methylsulfanyl]-6-[[(2r)-1-hydroxypropan-2-yl]amino]pyrimidin-4-yl]piperidine-1-sulfonamide Chemical compound N=1C(SCC=2C(=C(F)C=CC=2)F)=NC(N[C@@H](CO)C)=CC=1NS(=O)(=O)N1CCCCC1 ZYCHLELHVSMDDI-CYBMUJFWSA-N 0.000 claims 1
- PXRZFKNGQMUYCZ-GFCCVEGCSA-N n-[2-[(2,3-difluorophenyl)methylsulfanyl]-6-[[(2r)-1-hydroxypropan-2-yl]amino]pyrimidin-4-yl]pyrrolidine-1-sulfonamide Chemical compound N=1C(SCC=2C(=C(F)C=CC=2)F)=NC(N[C@@H](CO)C)=CC=1NS(=O)(=O)N1CCCC1 PXRZFKNGQMUYCZ-GFCCVEGCSA-N 0.000 claims 1
- CPHHZSHNSQNQHU-UHFFFAOYSA-N n-[2-[(3-chloro-2-fluorophenyl)methylsulfanyl]-6-(1-hydroxypropan-2-ylamino)pyrimidin-4-yl]-1,2-dimethylimidazole-4-sulfonamide Chemical compound N=1C(SCC=2C(=C(Cl)C=CC=2)F)=NC(NC(CO)C)=CC=1NS(=O)(=O)C1=CN(C)C(C)=N1 CPHHZSHNSQNQHU-UHFFFAOYSA-N 0.000 claims 1
- MSDQKJCHBXZYQG-UHFFFAOYSA-N n-[2-[(3-chloro-2-fluorophenyl)methylsulfanyl]-6-(1-hydroxypropan-2-ylamino)pyrimidin-4-yl]morpholine-4-sulfonamide Chemical compound N=1C(SCC=2C(=C(Cl)C=CC=2)F)=NC(NC(CO)C)=CC=1NS(=O)(=O)N1CCOCC1 MSDQKJCHBXZYQG-UHFFFAOYSA-N 0.000 claims 1
- NRRSGTIRDLBPLB-LLVKDONJSA-N n-[2-[(3-chloro-2-fluorophenyl)methylsulfanyl]-6-[[(2r)-1-hydroxypropan-2-yl]amino]pyrimidin-4-yl]-1-methylimidazole-4-sulfonamide Chemical compound N=1C(SCC=2C(=C(Cl)C=CC=2)F)=NC(N[C@@H](CO)C)=CC=1NS(=O)(=O)C1=CN(C)C=N1 NRRSGTIRDLBPLB-LLVKDONJSA-N 0.000 claims 1
- RGVHAQJTGULLAX-LLVKDONJSA-N n-[2-[(3-chloro-2-fluorophenyl)methylsulfanyl]-6-[[(2r)-1-hydroxypropan-2-yl]amino]pyrimidin-4-yl]azetidine-1-sulfonamide Chemical compound N=1C(SCC=2C(=C(Cl)C=CC=2)F)=NC(N[C@@H](CO)C)=CC=1NS(=O)(=O)N1CCC1 RGVHAQJTGULLAX-LLVKDONJSA-N 0.000 claims 1
- SNCCUTVKNBUBRR-SECBINFHSA-N n-[2-[(3-chloro-2-fluorophenyl)methylsulfanyl]-6-[[(2r)-1-hydroxypropan-2-yl]amino]pyrimidin-4-yl]methanesulfonamide Chemical compound OC[C@@H](C)NC1=CC(NS(C)(=O)=O)=NC(SCC=2C(=C(Cl)C=CC=2)F)=N1 SNCCUTVKNBUBRR-SECBINFHSA-N 0.000 claims 1
- GDXCPTRUEQIEME-LLVKDONJSA-N n-[6-[[(2r)-1-hydroxypropan-2-yl]amino]-2-[(2,3,4-trifluorophenyl)methylsulfanyl]pyrimidin-4-yl]morpholine-4-sulfonamide Chemical compound N=1C(SCC=2C(=C(F)C(F)=CC=2)F)=NC(N[C@@H](CO)C)=CC=1NS(=O)(=O)N1CCOCC1 GDXCPTRUEQIEME-LLVKDONJSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- 230000000269 nucleophilic effect Effects 0.000 claims 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229940002612 prodrug Drugs 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 125000000565 sulfonamide group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 0 *c(c(*)n1)c(NS(*)(=O)=O)nc1S* Chemical compound *c(c(*)n1)c(NS(*)(=O)=O)nc1S* 0.000 description 4
- 125000003368 amide group Chemical group 0.000 description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- 150000003456 sulfonamides Chemical class 0.000 description 2
- GIWQSPITLQVMSG-UHFFFAOYSA-N 1,2-dimethylimidazole Chemical compound CC1=NC=CN1C GIWQSPITLQVMSG-UHFFFAOYSA-N 0.000 description 1
- 125000003821 2-(trimethylsilyl)ethoxymethyl group Chemical group [H]C([H])([H])[Si](C([H])([H])[H])(C([H])([H])[H])C([H])([H])C(OC([H])([H])[*])([H])[H] 0.000 description 1
- YBTOOWRPRJWNRP-OAHLLOKOSA-N C[C@H](CO)Nc1nc(SCc2ccccc2)nc(NS(c(cc2)ccc2C(C)=O)(=O)=O)c1 Chemical compound C[C@H](CO)Nc1nc(SCc2ccccc2)nc(NS(c(cc2)ccc2C(C)=O)(=O)=O)c1 YBTOOWRPRJWNRP-OAHLLOKOSA-N 0.000 description 1
- JLHCJIPCKQROCQ-OAHLLOKOSA-N C[C@H](CO)Nc1nc(SCc2ccccc2)nc(NS(c(cc2)ccc2S(C)(O)=O)(O)=O)c1 Chemical compound C[C@H](CO)Nc1nc(SCc2ccccc2)nc(NS(c(cc2)ccc2S(C)(O)=O)(O)=O)c1 JLHCJIPCKQROCQ-OAHLLOKOSA-N 0.000 description 1
- PFVQCYNNBVLTDV-OAHLLOKOSA-N C[C@H](CO)Nc1nc(SCc2ccccc2)nc(NS(c(cccc2)c2S(C)(=O)=O)(O)=O)c1 Chemical compound C[C@H](CO)Nc1nc(SCc2ccccc2)nc(NS(c(cccc2)c2S(C)(=O)=O)(O)=O)c1 PFVQCYNNBVLTDV-OAHLLOKOSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0217431.6A GB0217431D0 (en) | 2002-07-27 | 2002-07-27 | Novel compounds |
| PCT/GB2003/003175 WO2004011443A1 (en) | 2002-07-27 | 2003-07-23 | Pyrimidyl sulphone amide derivatives as chemokine receptor modulators |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005538099A JP2005538099A (ja) | 2005-12-15 |
| JP2005538099A5 true JP2005538099A5 (enExample) | 2006-09-07 |
| JP4619782B2 JP4619782B2 (ja) | 2011-01-26 |
Family
ID=9941220
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004523926A Expired - Fee Related JP4619782B2 (ja) | 2002-07-27 | 2003-07-23 | ケモカインレセプター活性調節因子としてのピリミジルスルホンアミド誘導体 |
Country Status (25)
| Country | Link |
|---|---|
| US (2) | US7582644B2 (enExample) |
| EP (1) | EP1527051B1 (enExample) |
| JP (1) | JP4619782B2 (enExample) |
| KR (2) | KR20110033313A (enExample) |
| CN (1) | CN100345829C (enExample) |
| AR (1) | AR040700A1 (enExample) |
| AU (1) | AU2003281684B2 (enExample) |
| BR (1) | BR0312967A (enExample) |
| CA (1) | CA2493785C (enExample) |
| CO (1) | CO5680479A2 (enExample) |
| EG (1) | EG25893A (enExample) |
| ES (1) | ES2392965T3 (enExample) |
| GB (1) | GB0217431D0 (enExample) |
| IL (1) | IL166290A0 (enExample) |
| IS (1) | IS7697A (enExample) |
| MX (1) | MXPA05000960A (enExample) |
| MY (1) | MY139561A (enExample) |
| NO (1) | NO330531B1 (enExample) |
| NZ (1) | NZ537914A (enExample) |
| PL (1) | PL375400A1 (enExample) |
| RU (1) | RU2342366C2 (enExample) |
| TW (1) | TWI340038B (enExample) |
| UA (1) | UA80283C2 (enExample) |
| WO (1) | WO2004011443A1 (enExample) |
| ZA (1) | ZA200500791B (enExample) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0217431D0 (en) | 2002-07-27 | 2002-09-04 | Astrazeneca Ab | Novel compounds |
| ATE381546T1 (de) | 2002-08-24 | 2008-01-15 | Astrazeneca Ab | Pyrimidinderivate als modulatoren der aktivitut von chemokinrezeptoren |
| GB0401269D0 (en) * | 2004-01-21 | 2004-02-25 | Astrazeneca Ab | Compounds |
| US7230022B2 (en) | 2004-02-19 | 2007-06-12 | Bristol-Myers Squibb Company | Substituted fused bicyclic amines as modulators of chemokine receptor activity |
| US7381738B2 (en) | 2004-02-19 | 2008-06-03 | Bristol-Myers Squibb Company | Substituted bicycloalkylamine derivatives as modulators of chemokine receptor activity |
| US7288563B2 (en) | 2004-02-19 | 2007-10-30 | Bristol-Myers Squibb Company | Substituted bicycloalkylamine derivatives as modulators of chemokine receptor activity |
| US7479496B2 (en) | 2004-02-19 | 2009-01-20 | Bristol-Myers Squibb Company | Substituted spiro azabicyclics as modulators of chemokine receptor activity |
| MX2007002240A (es) | 2004-08-28 | 2007-04-20 | Astrazeneca Ab | Derivados de pirimidinosulfonamida como moduladores del receptor quimiocina. |
| US20060178388A1 (en) | 2005-02-04 | 2006-08-10 | Wrobleski Stephen T | Phenyl-substituted pyrimidine compounds useful as kinase inhibitors |
| KR20080021030A (ko) * | 2005-05-16 | 2008-03-06 | 버텍스 파마슈티칼스 인코포레이티드 | 이온 채널 조절인자로서의 바이사이클릭 유도체 |
| GB0526255D0 (en) | 2005-12-22 | 2006-02-01 | Novartis Ag | Organic compounds |
| KR101585848B1 (ko) * | 2007-11-16 | 2016-01-15 | 애브비 인코포레이티드 | 관절염의 치료 방법 |
| US9273077B2 (en) | 2008-05-21 | 2016-03-01 | Ariad Pharmaceuticals, Inc. | Phosphorus derivatives as kinase inhibitors |
| CN102105150B (zh) | 2008-05-21 | 2014-03-12 | 阿里亚德医药股份有限公司 | 用作激酶抑制剂的磷衍生物 |
| WO2009151910A2 (en) * | 2008-05-25 | 2009-12-17 | Wyeth | Combination product of receptor tyrosine kinase inhibitor and fatty acid synthase inhibitor for treating cancer |
| JP2011528030A (ja) * | 2008-07-16 | 2011-11-10 | アストラゼネカ・アクチエボラーグ | ピリミジルスルホンアミド誘導体およびケモカイン介在疾患処置のためのその使用 |
| BR112012017756A2 (pt) | 2009-12-23 | 2016-04-19 | Ironwood Pharmaceuticals Inc | moduladores crth2 |
| WO2012009137A1 (en) | 2010-07-12 | 2012-01-19 | Ironwood Pharmaceuticals, Inc. | Crth2 modulators |
| WO2012009134A1 (en) | 2010-07-12 | 2012-01-19 | Ironwood Pharmaceuticals, Inc. | Crth2 modulators |
| SG186859A1 (en) | 2010-07-13 | 2013-02-28 | Astrazeneca Ab | New crystalline forms of n-[2-[[(2,3-difluoropheny)methyl)thio]-6-{[(1r,2s)-2,3-dihydroxy-1- methylpropyl]oxy}-4-pyrimidinyl]-1-azetidinesulfonamide |
| KR101884010B1 (ko) | 2011-05-04 | 2018-07-31 | 어리어드 파마슈티칼스, 인코포레이티드 | Egfr-유도된 암의 세포 증식을 억제하는 화합물 |
| PE20181069A1 (es) | 2011-07-12 | 2018-07-04 | Astrazeneca Ab | N-(6-((2r,3s)-3,4-dihidroxibutan-2-iloxi)-2-(4-fluorobenciltio)pirimidin-4-il)-3-metilacetidina-1-sulfonamida como modulador del receptor de quimiocina |
| US20150166591A1 (en) | 2012-05-05 | 2015-06-18 | Ariad Pharmaceuticals, Inc. | Methods and compositions for raf kinase mediated diseases |
| US9611283B1 (en) | 2013-04-10 | 2017-04-04 | Ariad Pharmaceuticals, Inc. | Methods for inhibiting cell proliferation in ALK-driven cancers |
| TW201512171A (zh) | 2013-04-19 | 2015-04-01 | Pfizer Ltd | 化學化合物 |
| JP6779992B2 (ja) | 2015-10-09 | 2020-11-04 | アッヴィ・エス・ア・エール・エル | Ｎ−スルホニル化ピラゾロ［３，４−ｂ］ピリジン−６−カルボキサミドおよび使用法 |
| AU2017231832B2 (en) | 2016-03-11 | 2021-11-11 | Ardea Biosciences, Inc. | CXCR-2 inhibitors for treating crystal arthropathy disorders |
| GB201807898D0 (en) | 2018-05-15 | 2018-06-27 | Kancera Ab | New processes and products with increased chiral purity |
| WO2025219950A1 (en) | 2024-04-18 | 2025-10-23 | Astrazeneca Ab | Small molecule cx3cr1 modulators |
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| GB9900334D0 (en) | 1999-01-07 | 1999-02-24 | Angiogene Pharm Ltd | Tricylic vascular damaging agents |
| GB9900752D0 (en) | 1999-01-15 | 1999-03-03 | Angiogene Pharm Ltd | Benzimidazole vascular damaging agents |
| AU5108000A (en) | 1999-06-10 | 2001-01-02 | Yamanouchi Pharmaceutical Co., Ltd. | Novel nitrogen-contaiing heterocyclic derivatives or salts thereof |
| SE9903544D0 (sv) * | 1999-10-01 | 1999-10-01 | Astra Pharma Prod | Novel compounds |
| GB2359078A (en) | 2000-02-11 | 2001-08-15 | Astrazeneca Uk Ltd | Pharmaceutically active pyrimidine derivatives |
| EP1257555B1 (en) * | 2000-02-11 | 2003-12-03 | AstraZeneca AB | Pyrimidine compounds and their use as modulators of chemokine receptor activity |
| IL152682A0 (en) | 2000-05-31 | 2003-06-24 | Astrazeneca Ab | Indole derivatives with vascular damaging activity |
| JP2004502766A (ja) | 2000-07-07 | 2004-01-29 | アンギオジェン・ファーマシューティカルズ・リミテッド | 血管損傷剤としてのコルヒノール誘導体 |
| CA2410562A1 (en) | 2000-07-07 | 2002-01-31 | Angiogene Pharmaceuticals Limited | Colchinol derivatives as angiogenesis inhibitors |
| CN1326841C (zh) | 2000-09-25 | 2007-07-18 | 埃科特莱茵药品有限公司 | 具有内皮素拮抗剂活性的芳烷烃－磺胺类化合物 |
| US20030130264A1 (en) | 2001-02-16 | 2003-07-10 | Tularik Inc. | Methods of using pyrimidine-based antiviral agents |
| TWI328007B (en) | 2002-01-16 | 2010-08-01 | Astrazeneca Ab | Novel compounds |
| GB0217431D0 (en) * | 2002-07-27 | 2002-09-04 | Astrazeneca Ab | Novel compounds |
| ATE381546T1 (de) | 2002-08-24 | 2008-01-15 | Astrazeneca Ab | Pyrimidinderivate als modulatoren der aktivitut von chemokinrezeptoren |
| MX2007002240A (es) | 2004-08-28 | 2007-04-20 | Astrazeneca Ab | Derivados de pirimidinosulfonamida como moduladores del receptor quimiocina. |
-
2002
- 2002-07-27 GB GBGB0217431.6A patent/GB0217431D0/en not_active Ceased
-
2003
- 2003-07-23 CA CA2493785A patent/CA2493785C/en not_active Expired - Fee Related
- 2003-07-23 CN CNB038221497A patent/CN100345829C/zh not_active Expired - Fee Related
- 2003-07-23 MX MXPA05000960A patent/MXPA05000960A/es active IP Right Grant
- 2003-07-23 AU AU2003281684A patent/AU2003281684B2/en not_active Ceased
- 2003-07-23 US US10/522,871 patent/US7582644B2/en not_active Expired - Fee Related
- 2003-07-23 PL PL03375400A patent/PL375400A1/xx not_active Application Discontinuation
- 2003-07-23 NZ NZ537914A patent/NZ537914A/en not_active IP Right Cessation
- 2003-07-23 UA UAA200500513A patent/UA80283C2/uk unknown
- 2003-07-23 ES ES03740844T patent/ES2392965T3/es not_active Expired - Lifetime
- 2003-07-23 KR KR1020117006101A patent/KR20110033313A/ko not_active Ceased
- 2003-07-23 JP JP2004523926A patent/JP4619782B2/ja not_active Expired - Fee Related
- 2003-07-23 WO PCT/GB2003/003175 patent/WO2004011443A1/en not_active Ceased
- 2003-07-23 RU RU2005101406/04A patent/RU2342366C2/ru not_active IP Right Cessation
- 2003-07-23 BR BR0312967-5A patent/BR0312967A/pt not_active IP Right Cessation
- 2003-07-23 EP EP03740844A patent/EP1527051B1/en not_active Expired - Lifetime
- 2003-07-23 KR KR1020057001454A patent/KR101074626B1/ko not_active Expired - Fee Related
- 2003-07-25 MY MYPI20032818A patent/MY139561A/en unknown
- 2003-07-25 TW TW092120405A patent/TWI340038B/zh not_active IP Right Cessation
- 2003-07-25 AR AR20030102688A patent/AR040700A1/es unknown
- 2003-07-28 EG EG2003070726A patent/EG25893A/xx active
-
2005
- 2005-01-13 IL IL16629005A patent/IL166290A0/xx unknown
- 2005-01-24 CO CO05005309A patent/CO5680479A2/es not_active Application Discontinuation
- 2005-01-26 ZA ZA200500791A patent/ZA200500791B/en unknown
- 2005-02-17 IS IS7697A patent/IS7697A/is unknown
- 2005-02-25 NO NO20051042A patent/NO330531B1/no not_active IP Right Cessation
-
2009
- 2009-07-24 US US12/508,934 patent/US8106063B2/en not_active Expired - Fee Related
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