JP2007519640A5 - - Google Patents
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- Publication number
- JP2007519640A5 JP2007519640A5 JP2006549182A JP2006549182A JP2007519640A5 JP 2007519640 A5 JP2007519640 A5 JP 2007519640A5 JP 2006549182 A JP2006549182 A JP 2006549182A JP 2006549182 A JP2006549182 A JP 2006549182A JP 2007519640 A5 JP2007519640 A5 JP 2007519640A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- compound
- halo
- orx
- nrxrx
- 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
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- 150000001875 compounds Chemical class 0.000 claims description 38
- 125000005843 halogen group Chemical group 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- -1 C 1 -C 4 -alkyl Chemical group 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 5
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- 239000004202 carbamide Substances 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- 229930194542 Keto Natural products 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000000468 ketone group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 229940002612 prodrug Drugs 0.000 claims description 2
- 239000000651 prodrug Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 5
- 208000031886 HIV Infections Diseases 0.000 claims 4
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 4
- 239000003795 chemical substances by application Substances 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- 102000002004 Cytochrome P-450 Enzyme System Human genes 0.000 claims 2
- 108010015742 Cytochrome P-450 Enzyme System Proteins 0.000 claims 2
- 241000725303 Human immunodeficiency virus Species 0.000 claims 2
- NCDNCNXCDXHOMX-UHFFFAOYSA-N Ritonavir Natural products C=1C=CC=CC=1CC(NC(=O)OCC=1SC=NC=1)C(O)CC(CC=1C=CC=CC=1)NC(=O)C(C(C)C)NC(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-UHFFFAOYSA-N 0.000 claims 2
- 239000003443 antiviral agent Substances 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- NCDNCNXCDXHOMX-XGKFQTDJSA-N ritonavir Chemical compound N([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1SC=NC=1)CC=1C=CC=CC=1)C(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-XGKFQTDJSA-N 0.000 claims 2
- 229960000311 ritonavir Drugs 0.000 claims 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 1
- 230000001747 exhibiting effect Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 230000035772 mutation Effects 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 229940124530 sulfonamide Drugs 0.000 claims 1
- 150000003456 sulfonamides Chemical class 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical class NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
- 150000003930 2-aminopyridines Chemical class 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N alpha-aminopyridine Natural products NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 150000002540 isothiocyanates Chemical class 0.000 description 2
- 150000002828 nitro derivatives Chemical class 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- WFJPRCMYUOOTNS-UHFFFAOYSA-N 2-isothiocyanatopyridine Chemical compound S=C=NC1=CC=CC=N1 WFJPRCMYUOOTNS-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- ATXXLNCPVSUCNK-UHFFFAOYSA-N 5-bromo-2-nitropyridine Chemical compound [O-][N+](=O)C1=CC=C(Br)C=N1 ATXXLNCPVSUCNK-UHFFFAOYSA-N 0.000 description 1
- WGOLHUGPTDEKCF-UHFFFAOYSA-N 5-bromopyridin-2-amine Chemical compound NC1=CC=C(Br)C=N1 WGOLHUGPTDEKCF-UHFFFAOYSA-N 0.000 description 1
- 0 C[C@@]1[C@@](*N)[C@@]1C Chemical compound C[C@@]1[C@@](*N)[C@@]1C 0.000 description 1
- 238000006969 Curtius rearrangement reaction Methods 0.000 description 1
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000003927 aminopyridines Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
- RAFNCPHFRHZCPS-UHFFFAOYSA-N di(imidazol-1-yl)methanethione Chemical compound C1=CN=CN1C(=S)N1C=CN=C1 RAFNCPHFRHZCPS-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- SVEUVITYHIHZQE-UHFFFAOYSA-N n-methylpyridin-2-amine Chemical compound CNC1=CC=CC=N1 SVEUVITYHIHZQE-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- IWOKCMBOJXYDEE-UHFFFAOYSA-N sulfinylmethane Chemical compound C=S=O IWOKCMBOJXYDEE-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0400021A SE0400021D0 (sv) | 2004-01-08 | 2004-01-08 | Non-nucleoside reverse transcriptase inhibitors |
| SE0400021-2 | 2004-01-08 | ||
| SE0400585-6 | 2004-03-09 | ||
| SE0400585A SE0400585D0 (sv) | 2004-03-09 | 2004-03-09 | NNRTI Antivirals |
| PCT/SE2004/002034 WO2005066131A1 (en) | 2004-01-08 | 2004-12-30 | Non-nucleotide reverse transcriptase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007519640A JP2007519640A (ja) | 2007-07-19 |
| JP2007519640A5 true JP2007519640A5 (OSRAM) | 2008-01-24 |
| JP4762917B2 JP4762917B2 (ja) | 2011-08-31 |
Family
ID=34752289
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006549182A Expired - Fee Related JP4762917B2 (ja) | 2004-01-08 | 2004-12-30 | 非ヌクレオシド逆転写酵素インヒビター |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US7915295B2 (OSRAM) |
| EP (1) | EP1701942B1 (OSRAM) |
| JP (1) | JP4762917B2 (OSRAM) |
| AT (1) | ATE451357T1 (OSRAM) |
| AU (1) | AU2004312284B2 (OSRAM) |
| BR (1) | BRPI0418306B8 (OSRAM) |
| CA (1) | CA2550187C (OSRAM) |
| DE (1) | DE602004024584D1 (OSRAM) |
| DK (1) | DK1701942T3 (OSRAM) |
| EA (1) | EA009700B1 (OSRAM) |
| ES (1) | ES2337794T3 (OSRAM) |
| IL (1) | IL176740A (OSRAM) |
| NZ (1) | NZ548367A (OSRAM) |
| SG (1) | SG149070A1 (OSRAM) |
| WO (1) | WO2005066131A1 (OSRAM) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1694700A (zh) * | 2002-09-05 | 2005-11-09 | 美迪维尔公司 | 非核苷逆转录酶抑制剂 |
| US7388008B2 (en) | 2004-08-02 | 2008-06-17 | Ambrilia Biopharma Inc. | Lysine based compounds |
| EP1877091B1 (en) * | 2005-04-27 | 2015-03-25 | TaiMed Biologics, Inc. | Method for improving pharmacokinetics of protease inhibitors and protease inhibitor precursors |
| WO2007062526A1 (en) | 2005-11-30 | 2007-06-07 | Ambrilia Biopharma Inc. | Lysine-based prodrugs of aspartyl protease inhibitors and processes for their preparation |
| GB0608876D0 (en) * | 2006-05-05 | 2006-06-14 | Medivir Ab | Combination therapy |
| WO2007136572A2 (en) * | 2006-05-15 | 2007-11-29 | Merck & Co., Inc. | Antidiabetic bicyclic compounds |
| CA2664118A1 (en) | 2006-09-21 | 2008-07-03 | Ambrilia Biopharma Inc. | Protease inhibitors |
| EP3250552B1 (en) * | 2015-01-30 | 2019-03-27 | Genentech, Inc. | Therapeutic compounds and uses thereof |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CZ299387B6 (cs) * | 1998-01-16 | 2008-07-09 | Medivir Ab | Antivirové slouceniny |
| WO1999051613A1 (en) | 1998-04-03 | 1999-10-14 | Medivir Ab | Prodrugs of phosphorous-containing pharmaceuticals |
| SE0100733D0 (sv) * | 2001-03-05 | 2001-03-05 | Medivir Ab | Non-nucleoside reverse transcriptase inhibitors |
| SE0102867D0 (sv) * | 2001-08-28 | 2001-08-28 | Medivir Ab | Non-nucleoside reverse transcriptase inhibitors |
| CN1694700A (zh) * | 2002-09-05 | 2005-11-09 | 美迪维尔公司 | 非核苷逆转录酶抑制剂 |
-
2004
- 2004-12-30 EP EP04809207A patent/EP1701942B1/en not_active Expired - Lifetime
- 2004-12-30 WO PCT/SE2004/002034 patent/WO2005066131A1/en not_active Ceased
- 2004-12-30 EA EA200601289A patent/EA009700B1/ru not_active IP Right Cessation
- 2004-12-30 SG SG200809639-8A patent/SG149070A1/en unknown
- 2004-12-30 BR BRPI0418306A patent/BRPI0418306B8/pt not_active IP Right Cessation
- 2004-12-30 AU AU2004312284A patent/AU2004312284B2/en not_active Ceased
- 2004-12-30 DE DE602004024584T patent/DE602004024584D1/de not_active Expired - Lifetime
- 2004-12-30 NZ NZ548367A patent/NZ548367A/en not_active IP Right Cessation
- 2004-12-30 CA CA2550187A patent/CA2550187C/en not_active Expired - Fee Related
- 2004-12-30 US US10/584,933 patent/US7915295B2/en not_active Expired - Fee Related
- 2004-12-30 AT AT04809207T patent/ATE451357T1/de not_active IP Right Cessation
- 2004-12-30 ES ES04809207T patent/ES2337794T3/es not_active Expired - Lifetime
- 2004-12-30 DK DK04809207.6T patent/DK1701942T3/da active
- 2004-12-30 JP JP2006549182A patent/JP4762917B2/ja not_active Expired - Fee Related
-
2006
- 2006-07-06 IL IL176740A patent/IL176740A/en not_active IP Right Cessation
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