JP2005515169A5 - - Google Patents
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- Publication number
- JP2005515169A5 JP2005515169A5 JP2003539655A JP2003539655A JP2005515169A5 JP 2005515169 A5 JP2005515169 A5 JP 2005515169A5 JP 2003539655 A JP2003539655 A JP 2003539655A JP 2003539655 A JP2003539655 A JP 2003539655A JP 2005515169 A5 JP2005515169 A5 JP 2005515169A5
- Authority
- JP
- Japan
- Prior art keywords
- oxide
- pyridine
- dimethylphenyl
- methylsulfonyl
- pharmaceutical composition
- 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.)
- Pending
Links
- -1 thiopheneyl Chemical group 0.000 claims 36
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims 22
- 239000008194 pharmaceutical composition Substances 0.000 claims 21
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 19
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 14
- 150000003839 salts Chemical class 0.000 claims 12
- 125000004432 carbon atom Chemical group C* 0.000 claims 8
- 125000000524 functional group Chemical group 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 239000002253 acid Substances 0.000 claims 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 5
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 5
- 241001430294 unidentified retrovirus Species 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- MNCMBBIFTVWHIP-UHFFFAOYSA-N 1-anthracen-9-yl-2,2,2-trifluoroethanone Chemical group C1=CC=C2C(C(=O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 MNCMBBIFTVWHIP-UHFFFAOYSA-N 0.000 claims 3
- WSYIZLFZUDANGU-UHFFFAOYSA-N 2-[(2,5-dimethylphenyl)methylsulfonyl]-3-methyl-1-oxidopyridin-1-ium Chemical compound CC1=CC=C(C)C(CS(=O)(=O)C=2[N+](=CC=CC=2C)[O-])=C1 WSYIZLFZUDANGU-UHFFFAOYSA-N 0.000 claims 3
- LAFFJYCRWZMNTE-UHFFFAOYSA-N 2-[1-(2,5-dimethylphenyl)ethylsulfanyl]-4-methylquinoline Chemical compound C=1C(C)=C2C=CC=CC2=NC=1SC(C)C1=CC(C)=CC=C1C LAFFJYCRWZMNTE-UHFFFAOYSA-N 0.000 claims 3
- FWCIAKGQQGGJNZ-UHFFFAOYSA-N 2-[1-(2,5-dimethylphenyl)octylsulfonyl]-1-oxidopyridin-1-ium Chemical compound C=1C=CC=[N+]([O-])C=1S(=O)(=O)C(CCCCCCC)C1=CC(C)=CC=C1C FWCIAKGQQGGJNZ-UHFFFAOYSA-N 0.000 claims 3
- PSMJATBJEWJPHE-UHFFFAOYSA-N 2-benzylsulfonyl-1-oxidopyridin-1-ium Chemical compound [O-][N+]1=CC=CC=C1S(=O)(=O)CC1=CC=CC=C1 PSMJATBJEWJPHE-UHFFFAOYSA-N 0.000 claims 3
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 3
- 208000031886 HIV Infections Diseases 0.000 claims 3
- 241000701027 Human herpesvirus 6 Species 0.000 claims 3
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 3
- HVFPEQUCXFQLBO-UHFFFAOYSA-N 2-[1-(2,5-dimethylphenyl)ethylsulfonyl]-3-methyl-1-oxidopyridin-1-ium Chemical compound CC=1C=CC=[N+]([O-])C=1S(=O)(=O)C(C)C1=CC(C)=CC=C1C HVFPEQUCXFQLBO-UHFFFAOYSA-N 0.000 claims 2
- RWNISPVLLBWJBU-UHFFFAOYSA-N 2-sulfonyl-1h-pyridine Chemical compound O=S(=O)=C1C=CC=CN1 RWNISPVLLBWJBU-UHFFFAOYSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 241000701024 Human betaherpesvirus 5 Species 0.000 claims 2
- 241000725303 Human immunodeficiency virus Species 0.000 claims 2
- 241000713772 Human immunodeficiency virus 1 Species 0.000 claims 2
- 241000713340 Human immunodeficiency virus 2 Species 0.000 claims 2
- 206010038997 Retroviral infections Diseases 0.000 claims 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 2
- 239000004305 biphenyl Chemical group 0.000 claims 2
- 235000010290 biphenyl Nutrition 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- 208000015181 infectious disease Diseases 0.000 claims 2
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- 125000005936 piperidyl group Chemical group 0.000 claims 2
- 230000010076 replication Effects 0.000 claims 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- SXWZVSFIRKYQLQ-UHFFFAOYSA-N 1-oxido-2-[(2,4,6-trimethylphenyl)methylsulfinyl]pyridin-1-ium Chemical compound CC1=CC(C)=CC(C)=C1CS(=O)C1=CC=CC=[N+]1[O-] SXWZVSFIRKYQLQ-UHFFFAOYSA-N 0.000 claims 1
- SSLBIHNCJQZGGS-UHFFFAOYSA-N 2-[(2,5-dimethylphenyl)methylsulfanyl]pyridine Chemical compound CC1=CC=C(C)C(CSC=2N=CC=CC=2)=C1 SSLBIHNCJQZGGS-UHFFFAOYSA-N 0.000 claims 1
- ODBZRVDFVMOCMZ-UHFFFAOYSA-N 2-[(2,5-dimethylphenyl)methylsulfonyl]-1-oxidopyridin-1-ium Chemical compound CC1=CC=C(C)C(CS(=O)(=O)C=2[N+](=CC=CC=2)[O-])=C1 ODBZRVDFVMOCMZ-UHFFFAOYSA-N 0.000 claims 1
- OWSRSELEDVCYPO-UHFFFAOYSA-N 2-[(4-chloro-3-nitrophenyl)methylsulfonyl]-1-oxidopyridin-1-ium Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(CS(=O)(=O)C=2[N+](=CC=CC=2)[O-])=C1 OWSRSELEDVCYPO-UHFFFAOYSA-N 0.000 claims 1
- GJUPDGQXHGLTGK-UHFFFAOYSA-N 2-[[4-(2,2-dichlorocyclopropyl)phenyl]methylsulfonyl]-1-oxidopyridin-1-ium Chemical compound [O-][N+]1=CC=CC=C1S(=O)(=O)CC1=CC=C(C2C(C2)(Cl)Cl)C=C1 GJUPDGQXHGLTGK-UHFFFAOYSA-N 0.000 claims 1
- HOFCENCCZVWZEG-UHFFFAOYSA-N 2-benzylsulfinyl-1-oxidopyridin-1-ium Chemical compound [O-][N+]1=CC=CC=C1S(=O)CC1=CC=CC=C1 HOFCENCCZVWZEG-UHFFFAOYSA-N 0.000 claims 1
- 206010011831 Cytomegalovirus infection Diseases 0.000 claims 1
- 208000037357 HIV infectious disease Diseases 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/021,453 US7064139B2 (en) | 2001-10-29 | 2001-10-29 | Method for treating retroviral infections |
| PCT/US2002/031836 WO2003037311A2 (en) | 2001-10-29 | 2002-10-03 | Method for treating retroviral infections |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005515169A JP2005515169A (ja) | 2005-05-26 |
| JP2005515169A5 true JP2005515169A5 (https=) | 2005-12-22 |
Family
ID=21804307
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003539655A Pending JP2005515169A (ja) | 2001-10-29 | 2002-10-03 | レトロウイルス感染の治療方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (3) | US7064139B2 (https=) |
| JP (1) | JP2005515169A (https=) |
| CN (1) | CN1602194A (https=) |
| AU (1) | AU2002330239B2 (https=) |
| BR (1) | BR0213742A (https=) |
| CA (1) | CA2464303A1 (https=) |
| MX (1) | MXPA04004058A (https=) |
| WO (1) | WO2003037311A2 (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RS50589B (sr) * | 2003-12-23 | 2010-05-07 | H. Lundbeck A/S. | 2-(1h-indolilsulfanil)-benzil amin derivati kao ssri |
| AR052308A1 (es) * | 2004-07-16 | 2007-03-14 | Lundbeck & Co As H | Derivados de 2-(1h-indolilsulfanil)-arilamina y una composicion farmaceutica que contiene al compuesto |
| AR054393A1 (es) * | 2005-06-17 | 2007-06-20 | Lundbeck & Co As H | Derivados de benzo(b)furano y benzo(b)tiofeno, composiciones farmaceuticas que los contienen y su uso en la fabricacion de un medicamento para el tratamiento de enfermedades mediadas por la inhibicion de la reabsorcion de neurotransmisores de amina biogenicos. |
| US7629473B2 (en) * | 2005-06-17 | 2009-12-08 | H. Lundbeck A/S | 2-(1H-indolylsulfanyl)-aryl amine derivatives |
| JP2010512333A (ja) * | 2006-12-07 | 2010-04-22 | ヘルシン ヘルスケア ソシエテ アノニム | 塩酸パロノセトロンの結晶及び非晶質形 |
| CN106674099A (zh) * | 2016-12-22 | 2017-05-17 | 江苏燎原环保科技股份有限公司 | 一种二［2‑(n‑氧化物‑吡啶基‑2‑硫基)乙基］胺的制备方法 |
| CN106674100A (zh) * | 2016-12-22 | 2017-05-17 | 江苏燎原环保科技股份有限公司 | 一种三［2‑(n‑氧化物‑吡啶基‑2‑硫基)乙基］胺的制备方法 |
| CN108956809B (zh) * | 2018-06-04 | 2021-03-23 | 四川科伦药物研究院有限公司 | 一种检测1-(1-氯乙基)-2,3-二甲苯有关物质的方法 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1268772A (en) * | 1968-03-15 | 1972-03-29 | Glaxo Lab Ltd | NOVEL alpha-CARBOLINE DERIVATIVES, THE PREPARATION THEREOF AND COMPOSITIONS CONTAINING THE SAME |
| US3960542A (en) * | 1975-03-17 | 1976-06-01 | Uniroyal Inc. | Herbicidal 2-sulfinyl and 2-sulfonyl pyridine N-oxide derivatives |
| JPS52125170A (en) * | 1976-04-12 | 1977-10-20 | Yoshitomi Pharmaceut Ind Ltd | Pyridine derivatives |
| GB2039218B (en) * | 1978-11-30 | 1983-07-27 | Wyeth John & Brother Ltd | Pharmaceutical compositions |
| US4371537A (en) * | 1981-08-13 | 1983-02-01 | The Dow Chemical Company | Sulfur-substituted phenoxypyridines having antiviral activity |
| US4616087A (en) * | 1982-05-21 | 1986-10-07 | The Dow Chemical Company | 2,5-bis alkyl sulfonyl and 2,5-bis alkyl thio substituted-pyridines |
| US5268389A (en) * | 1989-10-16 | 1993-12-07 | Uniroyal Chemical Company, Inc. | Thiocarboxylate ester compounds compositions containing the same |
| WO1992006683A1 (en) * | 1990-10-22 | 1992-04-30 | Research Corporation Technologies, Inc. | Aryl and heteroaryl compounds having anti-retrovirus activity |
| WO1995029897A1 (en) * | 1994-04-29 | 1995-11-09 | G.D. Searle & Co. | METHOD OF USING (H+/K+) ATPase INHIBITORS AS ANTIVIRAL AGENTS |
| FR2737496B1 (fr) * | 1995-07-31 | 1997-12-19 | Centre Nat Rech Scient | 4-aryl-thio-pyridin-2(1h)-ones, medicaments les contenant et leurs utilisations dans le traitement de maladies liees aux vih 1 et 2 |
| US5770613A (en) * | 1995-09-29 | 1998-06-23 | Geron Corporation | Telomerase inhibitors |
| US5696151A (en) * | 1995-11-30 | 1997-12-09 | Uniroyal Chemical Company, Inc. | Compounds useful for the inhibition of the replication of HIV-1 and HIV-1 mutants |
| WO1998017267A1 (en) * | 1996-10-23 | 1998-04-30 | Zymogenetics, Inc. | Compositions and methods for treating bone deficit conditions |
| DE69831506T2 (de) * | 1997-12-22 | 2006-06-29 | Pharmacia & Upjohn Co. Llc, Kalamazoo | 4-hydroxychinolin-3-carboxamide und hydrazide als antivirale wirkstoffe |
| JP2000302760A (ja) * | 1999-02-17 | 2000-10-31 | Hokuriku Seiyaku Co Ltd | ２−メルカプトキノリン誘導体 |
| WO2000064894A1 (en) * | 1999-04-23 | 2000-11-02 | Takeda Chemical Industries, Ltd. | 5-pyridyl-1,3-azole compounds, process for producing the same and use thereof |
| US6316472B1 (en) * | 1999-05-13 | 2001-11-13 | Merck Frosst Canada & Co. | Heterosubstituted pyridine derivatives as PDE 4 inhibitors |
| MXPA02001160A (es) * | 1999-08-04 | 2002-07-02 | Millennium Pharm Inc | Compuestos que se unen a los receptores para melanocortina-4, y metodo de uso de estos. |
| US6498254B1 (en) * | 2001-10-29 | 2002-12-24 | Uniroyal Chemical Company, Inc. | Antiretroviral compounds and compositions |
-
2001
- 2001-10-29 US US10/021,453 patent/US7064139B2/en not_active Expired - Fee Related
-
2002
- 2002-10-03 MX MXPA04004058A patent/MXPA04004058A/es not_active Application Discontinuation
- 2002-10-03 JP JP2003539655A patent/JP2005515169A/ja active Pending
- 2002-10-03 AU AU2002330239A patent/AU2002330239B2/en not_active Expired - Fee Related
- 2002-10-03 CA CA002464303A patent/CA2464303A1/en not_active Abandoned
- 2002-10-03 WO PCT/US2002/031836 patent/WO2003037311A2/en not_active Ceased
- 2002-10-03 CN CNA028216873A patent/CN1602194A/zh active Pending
- 2002-10-03 BR BRPI0213742-9A patent/BR0213742A/pt not_active IP Right Cessation
-
2003
- 2003-12-19 US US10/740,696 patent/US20040132778A1/en not_active Abandoned
- 2003-12-19 US US10/740,869 patent/US20040204451A1/en not_active Abandoned
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