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 |
| WO2004018435A1 (en) | 2002-08-24 | 2004-03-04 | Astrazeneca Ab | Pyrimidine derivatives as modulators of chemokine receptor activity |
| GB0401269D0 (en) * | 2004-01-21 | 2004-02-25 | Astrazeneca Ab | Compounds |
| US7288563B2 (en) | 2004-02-19 | 2007-10-30 | Bristol-Myers Squibb Company | Substituted bicycloalkylamine derivatives 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 |
| US7479496B2 (en) | 2004-02-19 | 2009-01-20 | Bristol-Myers Squibb Company | Substituted spiro azabicyclics as modulators of chemokine receptor activity |
| US7230022B2 (en) | 2004-02-19 | 2007-06-12 | Bristol-Myers Squibb Company | Substituted fused bicyclic amines as modulators of chemokine receptor activity |
| RU2408587C2 (ru) | 2004-08-24 | 2011-01-10 | Астразенека Аб | Производные пиримидинсульфонамида в качестве модуляторов рецепторов хемокинов |
| US20060178388A1 (en) | 2005-02-04 | 2006-08-10 | Wrobleski Stephen T | Phenyl-substituted pyrimidine compounds useful as kinase inhibitors |
| MX2007014486A (es) * | 2005-05-16 | 2008-02-12 | Vertex Pharma | Derivados biciclicos como moduladores de canales ionicos. |
| GB0526255D0 (en) | 2005-12-22 | 2006-02-01 | Novartis Ag | Organic compounds |
| NZ601350A (en) * | 2007-11-16 | 2013-08-30 | Abbvie Inc | Method of treating arthritis |
| MX2010012703A (es) | 2008-05-21 | 2010-12-21 | Ariad Pharma Inc | Derivados fosforosos como inhibidores de cinasa. |
| US9273077B2 (en) | 2008-05-21 | 2016-03-01 | Ariad Pharmaceuticals, Inc. | Phosphorus derivatives as kinase inhibitors |
| WO2009151910A2 (en) * | 2008-05-25 | 2009-12-17 | Wyeth | Combination product of receptor tyrosine kinase inhibitor and fatty acid synthase inhibitor for treating cancer |
| KR20110031462A (ko) * | 2008-07-16 | 2011-03-28 | 아스트라제네카 아베 | 피리미딜 술폰아미드 유도체 및 케모카인 매개 질환의 치료를 위한 그의 용도 |
| CN102822163B (zh) | 2009-12-23 | 2016-01-20 | 艾恩伍德医药品股份有限公司 | Crth2调节剂 |
| US20130259830A1 (en) | 2010-07-12 | 2013-10-03 | Ironwood Pharmaceuticals, Inc. | Crth2 modulators |
| WO2012009137A1 (en) | 2010-07-12 | 2012-01-19 | Ironwood Pharmaceuticals, Inc. | Crth2 modulators |
| WO2012007748A1 (en) | 2010-07-13 | 2012-01-19 | 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 |
| BR112013027734A2 (pt) | 2011-05-04 | 2017-08-08 | Ariad Pharma Inc | compostos para a inibição de proliferação celular em cânceres impulsionados pelo egfr, método e composição farmacêutica |
| MX342874B (es) | 2011-07-12 | 2016-10-17 | Astrazeneca Ab | N-(6-((2r,3s)-3,4-dihidroxibutan-2-iloxi)-2-(4-fluorobenciltio)pi rimidin-4-il)-3-metilacetidina-1-sulfonamida como modulador del receptor de quimiocina. |
| AU2013204563B2 (en) | 2012-05-05 | 2016-05-19 | Takeda Pharmaceutical Company Limited | Compounds for inhibiting cell proliferation in EGFR-driven cancers |
| 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 |
| KR20180083323A (ko) | 2015-10-09 | 2018-07-20 | 애브비 에스.에이.알.엘. | N-설포닐화 피라졸로[3,4-b]피리딘-6-카복스아미드 및 사용 방법 |
| EP3426253A4 (en) | 2016-03-11 | 2019-11-06 | Ardea Biosciences, Inc. | CXCR-2 INHIBITORS FOR THE TREATMENT OF CRYSTALARTHROPATHIES |
| 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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| WO2000076980A1 (en) | 1999-06-10 | 2000-12-21 | 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 |
| NZ522074A (en) | 2000-05-31 | 2004-06-25 | Astrazeneca Ab | Indole derivatives with vascular damaging activity |
| CA2410562A1 (en) | 2000-07-07 | 2002-01-31 | Angiogene Pharmaceuticals Limited | Colchinol derivatives as angiogenesis inhibitors |
| 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 |
| JP2004509874A (ja) | 2000-09-25 | 2004-04-02 | アクテリオン ファマシューティカルズ リミテッド | 新規なアリールアルカン−スルフォンアミド類 |
| AU2002258400A1 (en) | 2001-02-16 | 2002-08-28 | 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 |
| WO2004018435A1 (en) | 2002-08-24 | 2004-03-04 | Astrazeneca Ab | Pyrimidine derivatives as modulators of chemokine receptor activity |
| RU2408587C2 (ru) | 2004-08-24 | 2011-01-10 | Астразенека Аб | Производные пиримидинсульфонамида в качестве модуляторов рецепторов хемокинов |
-
2002
- 2002-07-27 GB GBGB0217431.6A patent/GB0217431D0/en not_active Ceased
-
2003
- 2003-07-23 UA UAA200500513A patent/UA80283C2/uk unknown
- 2003-07-23 RU RU2005101406/04A patent/RU2342366C2/ru not_active IP Right Cessation
- 2003-07-23 AU AU2003281684A patent/AU2003281684B2/en not_active Ceased
- 2003-07-23 CN CNB038221497A patent/CN100345829C/zh not_active Expired - Fee Related
- 2003-07-23 JP JP2004523926A patent/JP4619782B2/ja not_active Expired - Fee Related
- 2003-07-23 US US10/522,871 patent/US7582644B2/en not_active Expired - Fee Related
- 2003-07-23 KR KR1020117006101A patent/KR20110033313A/ko not_active Ceased
- 2003-07-23 PL PL03375400A patent/PL375400A1/xx not_active Application Discontinuation
- 2003-07-23 CA CA2493785A patent/CA2493785C/en not_active Expired - Fee Related
- 2003-07-23 EP EP03740844A patent/EP1527051B1/en not_active Expired - Lifetime
- 2003-07-23 NZ NZ537914A patent/NZ537914A/en not_active IP Right Cessation
- 2003-07-23 KR KR1020057001454A patent/KR101074626B1/ko not_active Expired - Fee Related
- 2003-07-23 WO PCT/GB2003/003175 patent/WO2004011443A1/en not_active Ceased
- 2003-07-23 BR BR0312967-5A patent/BR0312967A/pt not_active IP Right Cessation
- 2003-07-23 ES ES03740844T patent/ES2392965T3/es not_active Expired - Lifetime
- 2003-07-23 MX MXPA05000960A patent/MXPA05000960A/es active IP Right Grant
- 2003-07-25 AR AR20030102688A patent/AR040700A1/es unknown
- 2003-07-25 MY MYPI20032818A patent/MY139561A/en unknown
- 2003-07-25 TW TW092120405A patent/TWI340038B/zh not_active IP Right Cessation
- 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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