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 (https=) | 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 (153)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| JO3429B1 (ar) | 2001-08-13 | 2019-10-20 | Janssen Pharmaceutica Nv | مشتقات برميدينات مثبطة فيروس الايدز |
| 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 |
| MXPA04008797A (es) | 2002-03-13 | 2004-11-26 | Janssen Pharmaceutica Nv | Inhibidores de histona desacetilasa. |
| AR039540A1 (es) | 2002-05-13 | 2005-02-23 | Tibotec Pharm Ltd | Compuestos microbicidas con contenido de pirimidina o triazina |
| HRP20050089B1 (hr) | 2002-07-29 | 2015-06-19 | Rigel Pharmaceuticals | Upotreba 2,4 pirimidindiaminskog spoja za proizvodnju lijeka za lijeäśenje ili sprjeäśavanje autoimunosne bolesti |
| DK1529032T3 (da) * | 2002-08-09 | 2013-07-08 | Janssen Pharmaceutica Nv | Fremgangsmåder til fremstilling af 4-4-4-(2-cyanoethenyl)-2,6-dimethylphenyl)amino)-2-pyrimidinyl)aminobenzonitrill |
| JP2006508997A (ja) * | 2002-11-28 | 2006-03-16 | シエーリング アクチエンゲゼルシャフト | Ｃｈｋ−、Ｐｄｋ−およびＡｋｔ−阻害性ピリミジン、それらの製造および薬剤としての使用 |
| BRPI0407329A (pt) * | 2003-02-07 | 2006-01-10 | Janssen Pharmaceutica Nv | Derivados de pirimidina para a prevenção de infecção de hiv |
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| ES2667668T3 (es) | 2003-07-17 | 2018-05-14 | Janssen Sciences Ireland Uc | Procedimiento para preparar partículas que contienen un antiviral |
| WO2005012294A1 (en) | 2003-07-30 | 2005-02-10 | Rigel Pharmaceuticals, Inc. | 2,4-pyrimidinediamine compounds for use in the treatment or prevention of autoimmune diseases |
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