JP2005507380A5 - - Google Patents
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- JP2005507380A5 JP2005507380A5 JP2003521229A JP2003521229A JP2005507380A5 JP 2005507380 A5 JP2005507380 A5 JP 2005507380A5 JP 2003521229 A JP2003521229 A JP 2003521229A JP 2003521229 A JP2003521229 A JP 2003521229A JP 2005507380 A5 JP2005507380 A5 JP 2005507380A5
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- JP
- Japan
- Prior art keywords
- alkyl
- cyano
- substituted
- formula
- 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.)
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- 125000000217 alkyl group Chemical group 0.000 claims 124
- 125000004093 cyano group Chemical group *C#N 0.000 claims 50
- 125000001424 substituent group Chemical group 0.000 claims 39
- 239000000543 intermediate Substances 0.000 claims 34
- 150000001875 compounds Chemical class 0.000 claims 33
- 125000003545 alkoxy group Chemical group 0.000 claims 32
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 25
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 23
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 23
- -1 cyano , Carboxyl Chemical group 0.000 claims 20
- 125000005843 halogen group Chemical group 0.000 claims 19
- 239000002904 solvent Substances 0.000 claims 19
- 229920006395 saturated elastomer Polymers 0.000 claims 16
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 15
- 150000003839 salts Chemical class 0.000 claims 14
- 229910052739 hydrogen Inorganic materials 0.000 claims 13
- 239000001257 hydrogen Substances 0.000 claims 13
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 12
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 10
- 125000002619 bicyclic group Chemical group 0.000 claims 10
- 125000002950 monocyclic group Chemical group 0.000 claims 10
- 150000001204 N-oxides Chemical class 0.000 claims 9
- 150000001412 amines Chemical group 0.000 claims 8
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 8
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 7
- 229910052799 carbon Inorganic materials 0.000 claims 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 6
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 5
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims 5
- 150000001721 carbon Chemical group 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- YIBOMRUWOWDFLG-UHFFFAOYSA-N 4-[[4-[4-(2-cyanoethenyl)-2,6-dimethylanilino]pyrimidin-2-yl]amino]benzonitrile Chemical compound CC1=CC(C=CC#N)=CC(C)=C1NC1=CC=NC(NC=2C=CC(=CC=2)C#N)=N1 YIBOMRUWOWDFLG-UHFFFAOYSA-N 0.000 claims 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 4
- 239000002585 base Substances 0.000 claims 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 3
- 238000006546 Horner-Wadsworth-Emmons reaction Methods 0.000 claims 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 125000002837 carbocyclic group Chemical group 0.000 claims 3
- 239000003054 catalyst Substances 0.000 claims 3
- 239000003153 chemical reaction reagent Substances 0.000 claims 3
- 239000003937 drug carrier Substances 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims 2
- JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 claims 2
- 208000031886 HIV Infections Diseases 0.000 claims 2
- 208000037357 HIV infectious disease Diseases 0.000 claims 2
- 241000725303 Human immunodeficiency virus Species 0.000 claims 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 2
- 230000000798 anti-retroviral effect Effects 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims 2
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 claims 2
- 229910052698 phosphorus Inorganic materials 0.000 claims 2
- 239000011574 phosphorus Substances 0.000 claims 2
- 239000002243 precursor Substances 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- KYPOHTVBFVELTG-OWOJBTEDSA-N (e)-but-2-enedinitrile Chemical compound N#C\C=C\C#N KYPOHTVBFVELTG-OWOJBTEDSA-N 0.000 claims 1
- GFISDBXSWQMOND-UHFFFAOYSA-N 2,5-dimethoxyoxolane Chemical compound COC1CCC(OC)O1 GFISDBXSWQMOND-UHFFFAOYSA-N 0.000 claims 1
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 1
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical group [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims 1
- 101100240519 Caenorhabditis elegans nhr-13 gene Proteins 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 238000006485 reductive methylation reaction Methods 0.000 claims 1
- 150000003335 secondary amines Chemical class 0.000 claims 1
- KXCAEQNNTZANTK-UHFFFAOYSA-N stannane Chemical compound [SnH4] KXCAEQNNTZANTK-UHFFFAOYSA-N 0.000 claims 1
- 229910000080 stannane Inorganic materials 0.000 claims 1
- 239000000758 substrate Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 238000011426 transformation method Methods 0.000 claims 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 claims 1
- 125000004953 trihalomethyl group Chemical group 0.000 claims 1
- 0 CN(*)c1nc(*)ccn1 Chemical compound CN(*)c1nc(*)ccn1 0.000 description 6
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01203090 | 2001-08-13 | ||
| EP02077748 | 2002-06-10 | ||
| PCT/EP2002/008953 WO2003016306A1 (en) | 2001-08-13 | 2002-08-09 | Hiv inhibiting pyrimidines derivatives |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009259107A Division JP5247661B2 (ja) | 2001-08-13 | 2009-11-12 | Ｈｉｖ阻害性ピリミジン誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005507380A JP2005507380A (ja) | 2005-03-17 |
| JP2005507380A5 true JP2005507380A5 (enExample) | 2006-01-05 |
Family
ID=26076978
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003521229A Withdrawn JP2005507380A (ja) | 2001-08-13 | 2002-08-09 | Ｈｉｖ阻害性ピリミジン誘導体 |
| JP2009259107A Expired - Lifetime JP5247661B2 (ja) | 2001-08-13 | 2009-11-12 | Ｈｉｖ阻害性ピリミジン誘導体 |
| JP2011134088A Expired - Lifetime JP4838396B2 (ja) | 2001-08-13 | 2011-06-16 | Ｈｉｖ阻害性ピリミジン誘導体 |
| JP2011135468A Expired - Lifetime JP5539927B2 (ja) | 2001-08-13 | 2011-06-17 | Ｈｉｖ阻害性ピリミジン誘導体 |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009259107A Expired - Lifetime JP5247661B2 (ja) | 2001-08-13 | 2009-11-12 | Ｈｉｖ阻害性ピリミジン誘導体 |
| JP2011134088A Expired - Lifetime JP4838396B2 (ja) | 2001-08-13 | 2011-06-16 | Ｈｉｖ阻害性ピリミジン誘導体 |
| JP2011135468A Expired - Lifetime JP5539927B2 (ja) | 2001-08-13 | 2011-06-17 | Ｈｉｖ阻害性ピリミジン誘導体 |
Country Status (37)
Families Citing this family (152)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JO3429B1 (ar) | 2001-08-13 | 2019-10-20 | Janssen Pharmaceutica Nv | مشتقات برميدينات مثبطة فيروس الايدز |
| MY169670A (en) * | 2003-09-03 | 2019-05-08 | Tibotec Pharm Ltd | Combinations of a pyrimidine containing nnrti with rt inhibitors |
| US8101629B2 (en) * | 2001-08-13 | 2012-01-24 | Janssen Pharmaceutica N.V. | Salt of 4-[[4-[[4-(2-cyanoethenyl)-2,6-dimethylphenyl]amino]-2-pyrimidinyl]amino]benzonitrile |
| US7638522B2 (en) | 2001-08-13 | 2009-12-29 | Janssen Pharmaceutica N.V. | Salt of 4-[[4-[[4-(2-cyanoethenyl)-2,6-dimethylphenyl]amino]-2-pyrimidinyl]amino] benzonitrile |
| TWI329105B (en) | 2002-02-01 | 2010-08-21 | Rigel Pharmaceuticals Inc | 2,4-pyrimidinediamine compounds and their uses |
| PL212089B1 (pl) | 2002-03-13 | 2012-08-31 | Janssen Pharmaceutica Nv | Związki heterocykliczne jako inhibitory deacetylazy histonowej, kompozycja farmaceutyczna je zawierająca, ich zastosowanie, sposób wytwarzania, sposób wykrywania lub identyfikacji HDAC oraz kompozycja |
| AR039540A1 (es) | 2002-05-13 | 2005-02-23 | Tibotec Pharm Ltd | Compuestos microbicidas con contenido de pirimidina o triazina |
| JP2006514989A (ja) | 2002-07-29 | 2006-05-18 | ライジェル ファーマシューティカルズ | ２，４−ピリミジンジアミン化合物による自己免疫疾患の治療および予防方法 |
| CA2686429C (en) | 2002-08-09 | 2010-11-16 | Janssen Pharmaceutica N.V. | Processes for the preparation of 4-[[4-[[4-(2-cyanoethenyl)-2,6-dimethylphenyl]amino]-2-pyrimidinyl]amino]benzonitrile |
| MXPA05005547A (es) * | 2002-11-28 | 2005-07-26 | Schering Ag | Pirimidinas inhibidoras de chk, pdk y akt, su produccion y uso como agentes farmaceuticos. |
| HRP20050688B1 (hr) * | 2003-02-07 | 2017-03-24 | Janssen Pharmaceutica N.V. | Derivati pirimidina za sprječavanje hiv infekcije |
| WO2004074266A1 (en) | 2003-02-07 | 2004-09-02 | Janssen Pharmaceutica N.V. | Hiv inhibiting 1,2,4-triazines |
| CL2004000306A1 (es) | 2003-02-20 | 2005-04-08 | Tibotec Pharm Ltd | Compuestos derivados de pirimidina sustituidas con indano; proceso para su preparacion; composicion farmaceutica que lo comprende; combinacion farmaceutica; y su uso para el tratamiento o profilaxis de una enfermedad infecciosa. |
| EP1648467B1 (en) | 2003-07-17 | 2018-03-21 | Janssen Sciences Ireland UC | Process for preparing particles containing an antiviral |
| ES2421139T3 (es) | 2003-07-30 | 2013-08-29 | Rigel Pharmaceuticals, Inc. | Compuestos de 2,4-pirimidindiamina para su uso en el tratamiento o la prevención de enfermedades autoinmunitarias |
| BR122019017579B8 (pt) * | 2003-08-15 | 2021-07-27 | Novartis Ag | 2,4-pirimidinadiaminas, seus usos, combinação e composição farmacêutica |
| TWI365744B (en) * | 2003-09-03 | 2012-06-11 | Tibotec Pharm Ltd | Combinations of a pyrimidine containing nnrti with rt inhibitors |
| CN100475815C (zh) * | 2003-09-25 | 2009-04-08 | 詹森药业有限公司 | 抑制hiv复制的嘌呤衍生物 |
| EP2543376A1 (en) | 2004-04-08 | 2013-01-09 | Targegen, Inc. | Benzotriazine inhibitors of kinases |
| SG156687A1 (en) | 2004-07-28 | 2009-11-26 | Janssen Pharmaceutica Nv | Substituted indolyl alkyl amino derivatives as novel inhibitors of histone deacetylase |
| CA2575002C (en) | 2004-08-10 | 2015-01-20 | Janssen Pharmaceutica N.V. | Hiv inhibiting 1,2,4-triazin-6-one derivatives |
| EA014737B1 (ru) | 2004-08-25 | 2011-02-28 | Ардеа Байосайенсиз, Инк. | S-ТРИАЗОЛИЛ-α-МЕРКАПТОАЦЕТАНИЛИДЫ В КАЧЕСТВЕ ИНГИБИТОРА ОБРАТНОЙ ТРАНСКРИПТАЗЫ ВИЧ |
| WO2007050087A1 (en) | 2004-08-25 | 2007-05-03 | Ardea Biosciences, Inc. | N[S(4-aryl-triazol-3-yl)α -mercaptoacetyl]-p-amino benozoic acids AS HIV REVERSE TRANSCRIPTASE INHIBITORS |
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| KR101284361B1 (ko) * | 2004-09-02 | 2013-07-15 | 얀센 파마슈티카 엔.브이. | 4-((4-((4-(2-시아노에텐일)-2,6-디메틸페닐)아미노-2-피리미딘일)아미노)벤조니트릴의 하이드로클로라이드 |
| UA92467C2 (ru) * | 2004-09-02 | 2010-11-10 | Янссен Фармацевтика Н.В. | Гидрохлорид 4-[[4-[[4-(2-цианоэтенил)-2,6-диметилфенил]амино]-2-пиримидинил]амино]бензонитрила |
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| CA2580857A1 (en) | 2004-09-20 | 2006-09-28 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
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| CN101084212A (zh) | 2004-09-20 | 2007-12-05 | 泽农医药公司 | 杂环衍生物及其作为硬脂酰CoA去饱和酶介导剂的用途 |
| CN101083992A (zh) | 2004-09-20 | 2007-12-05 | 泽农医药公司 | 抑制人硬脂酰CoA去饱和酶的哒嗪衍生物 |
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| BRPI0515935B8 (pt) * | 2004-09-30 | 2021-05-25 | Janssen Sciences Ireland Uc | pirimidinas heterociclil- ou 5-carbo substituídas para inibição de hiv, e composição farmacêutica |
| CA2577467C (en) | 2004-09-30 | 2013-05-28 | Tibotec Pharmaceuticals Ltd. | Hiv inhibiting 5-heterocyclyl pyrimidines |
| US8946248B2 (en) | 2004-09-30 | 2015-02-03 | Janssen R&D Ireland | HIV inhibiting 5-substituted pyrimidines |
| DK1814878T3 (da) | 2004-11-24 | 2012-05-07 | Rigel Pharmaceuticals Inc | Spiro-2, 4-pyrimidindiamin-forbindelser og anvendelser deraf |
| PL1856135T3 (pl) | 2005-01-19 | 2010-05-31 | Rigel Pharmaceuticals Inc | Proleki związków 2,4-pirymidynodiaminy i ich zastosowanie |
| ES2548729T3 (es) | 2005-03-31 | 2015-10-20 | Santen Pharmaceutical Co., Ltd. | Nuevo compuesto cíclico que tiene grupo pirimidinilalquiltio |
| TWI457136B (zh) | 2005-04-04 | 2014-10-21 | Tibotec Pharm Ltd | Ｈｉｖ-感染之預防 |
| CN101233135B (zh) | 2005-05-05 | 2012-10-03 | 阿迪亚生命科学公司 | 用作非核苷反转录酶抑制剂治疗人免疫缺陷病毒的二芳基-嘌呤、二芳基-氮杂嘌呤和二芳基-脱氮嘌呤化合物 |
| HRP20131133T1 (hr) | 2005-05-26 | 2014-01-03 | Janssen R&D Ireland | Postupak za dobivanje 4-[(1,6-dihidro-6-okso-2-pirimidinil)amino benzonitrila |
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| AU2007206901B2 (en) * | 2006-01-20 | 2013-01-31 | Janssen Sciences Ireland Uc | Long term treatment of HIV- infection with TCM278 |
| CN101410394B (zh) | 2006-03-30 | 2012-02-08 | 泰博特克药品有限公司 | 抑制人免疫缺陷病毒的5-(羟基亚甲基和氨基亚甲基)取代的嘧啶 |
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| NZ590601A (en) | 2006-12-08 | 2011-09-30 | Irm Llc | Pyrimidine compounds especially 4-phenylamino-2-arylamino-pyrimidine derivatives and compositions as protein kinase inhibitors |
| KR101475091B1 (ko) | 2006-12-13 | 2014-12-22 | 에프. 호프만-라 로슈 아게 | 비뉴클레오시드 역전사 효소 억제제로서 2-(피페리딘-4-일)-4-페녹시- 또는 페닐아미노-피리미딘 유도체 |
| EP2114901B1 (en) | 2006-12-29 | 2014-04-09 | Janssen R&D Ireland | Hiv inhibiting 6-substituted pyrimidines |
| KR20090094084A (ko) | 2006-12-29 | 2009-09-03 | 티보텍 파마슈티칼즈 리미티드 | Ｈｉｖ를 억제하는 5,6-치환된 피리미딘 |
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| BRPI0810411B8 (pt) * | 2007-04-18 | 2021-05-25 | Pfizer Prod Inc | derivados de sulfonil amida para o tratamento de crescimento celular anormal, seu sos, bem como composição farmacêutica |
| ES2542153T3 (es) | 2007-05-30 | 2015-07-31 | F. Hoffmann-La Roche Ag | Inhibidores no nucleósidos de la transcriptasa inversa |
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