JP2006506439A5 - - Google Patents
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- Publication number
- JP2006506439A5 JP2006506439A5 JP2004553861A JP2004553861A JP2006506439A5 JP 2006506439 A5 JP2006506439 A5 JP 2006506439A5 JP 2004553861 A JP2004553861 A JP 2004553861A JP 2004553861 A JP2004553861 A JP 2004553861A JP 2006506439 A5 JP2006506439 A5 JP 2006506439A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- amino
- compound
- alkoxy
- mono
- 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 59
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 59
- 150000003839 salts Chemical class 0.000 claims 59
- 229910052736 halogen Inorganic materials 0.000 claims 38
- 150000002367 halogens Chemical class 0.000 claims 38
- 125000001188 haloalkyl group Chemical group 0.000 claims 35
- 125000001424 substituent group Chemical group 0.000 claims 35
- 125000004438 haloalkoxy group Chemical group 0.000 claims 34
- 229910052739 hydrogen Inorganic materials 0.000 claims 27
- 239000001257 hydrogen Substances 0.000 claims 27
- -1 hydroxy, amino Chemical group 0.000 claims 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 22
- 125000004093 cyano group Chemical group *C#N 0.000 claims 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 16
- 150000003857 carboxamides Chemical class 0.000 claims 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims 11
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 10
- 125000003118 aryl group Chemical group 0.000 claims 9
- 229910052760 oxygen Inorganic materials 0.000 claims 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 8
- 229920006395 saturated elastomer Polymers 0.000 claims 8
- 229940124530 sulfonamide Drugs 0.000 claims 8
- 150000003456 sulfonamides Chemical class 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 125000004043 oxo group Chemical group O=* 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 6
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 5
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims 5
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 4
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 4
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 4
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims 4
- 125000004423 acyloxy group Chemical group 0.000 claims 4
- 125000006580 bicyclic heterocycloalkyl group Chemical group 0.000 claims 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 150000002431 hydrogen Chemical group 0.000 claims 4
- 125000006578 monocyclic heterocycloalkyl group Chemical group 0.000 claims 4
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 4
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 4
- 125000006164 6-membered heteroaryl group Chemical group 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 208000005176 Hepatitis C Diseases 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 238000003556 assay Methods 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 208000010710 hepatitis C virus infection Diseases 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000001841 imino group Chemical group [H]N=* 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
- 230000010076 replication Effects 0.000 claims 2
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
- ZYFODNCNVGRNQV-UHFFFAOYSA-N 2-methyl-n-[(3-phenylmethoxyphenyl)carbamothioyl]pyridine-3-carboxamide Chemical compound CC1=NC=CC=C1C(=O)NC(=S)NC1=CC=CC(OCC=2C=CC=CC=2)=C1 ZYFODNCNVGRNQV-UHFFFAOYSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
- 239000000443 aerosol Substances 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 239000006071 cream Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003814 drug 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
- 239000003889 eye drop Substances 0.000 claims 1
- 239000012530 fluid Substances 0.000 claims 1
- 239000000499 gel Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000001288 lysyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- RWHPHNDWWRLYDS-UHFFFAOYSA-N n-[(3-phenoxyphenyl)carbamothioyl]pyrazine-2-carboxamide Chemical compound C=1N=CC=NC=1C(=O)NC(=S)NC(C=1)=CC=CC=1OC1=CC=CC=C1 RWHPHNDWWRLYDS-UHFFFAOYSA-N 0.000 claims 1
- VHBCHIZHMPLFBO-UHFFFAOYSA-N n-[(3-phenylmethoxyphenyl)carbamothioyl]-2-pyridin-2-yloxyacetamide Chemical compound C=1C=CC(OCC=2C=CC=CC=2)=CC=1NC(=S)NC(=O)COC1=CC=CC=N1 VHBCHIZHMPLFBO-UHFFFAOYSA-N 0.000 claims 1
- QHVJRRFRSQHDCO-UHFFFAOYSA-N n-[(3-phenylmethoxyphenyl)carbamothioyl]-2-pyridin-3-yloxyacetamide Chemical compound C=1C=CC(OCC=2C=CC=CC=2)=CC=1NC(=S)NC(=O)COC1=CC=CN=C1 QHVJRRFRSQHDCO-UHFFFAOYSA-N 0.000 claims 1
- FEUDPOBDPXBYFK-UHFFFAOYSA-N n-[(4-pentoxyphenyl)carbamothioyl]-6-(trifluoromethyl)pyridine-3-carboxamide Chemical compound C1=CC(OCCCCC)=CC=C1NC(=S)NC(=O)C1=CC=C(C(F)(F)F)N=C1 FEUDPOBDPXBYFK-UHFFFAOYSA-N 0.000 claims 1
- JJVWMQKLDXKDIV-UHFFFAOYSA-N n-[(4-pentoxyphenyl)carbamothioyl]pyrazine-2-carboxamide Chemical compound C1=CC(OCCCCC)=CC=C1NC(=S)NC(=O)C1=CN=CC=N1 JJVWMQKLDXKDIV-UHFFFAOYSA-N 0.000 claims 1
- DNDGMOAXMLQILW-UHFFFAOYSA-N n-[(4-pentylphenyl)carbamothioyl]-3-propoxypyridine-2-carboxamide Chemical compound C1=CC(CCCCC)=CC=C1NC(=S)NC(=O)C1=NC=CC=C1OCCC DNDGMOAXMLQILW-UHFFFAOYSA-N 0.000 claims 1
- NMRQDGKIKFJXPB-UHFFFAOYSA-N n-[(4-pentylphenyl)carbamothioyl]-6-(trifluoromethyl)pyridine-3-carboxamide Chemical compound C1=CC(CCCCC)=CC=C1NC(=S)NC(=O)C1=CC=C(C(F)(F)F)N=C1 NMRQDGKIKFJXPB-UHFFFAOYSA-N 0.000 claims 1
- IUTODESYMOWBHQ-UHFFFAOYSA-N n-[(4-pentylphenyl)carbamothioyl]pyrazine-2-carboxamide Chemical compound C1=CC(CCCCC)=CC=C1NC(=S)NC(=O)C1=CN=CC=N1 IUTODESYMOWBHQ-UHFFFAOYSA-N 0.000 claims 1
- AYKHGGLHADXRBU-UHFFFAOYSA-N n-[[4-(1,3-benzothiazol-2-yl)phenyl]carbamothioyl]pyridine-3-carboxamide Chemical compound C=1C=C(C=2SC3=CC=CC=C3N=2)C=CC=1NC(=S)NC(=O)C1=CC=CN=C1 AYKHGGLHADXRBU-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000006187 pill Substances 0.000 claims 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 239000006188 syrup Substances 0.000 claims 1
- 235000020357 syrup Nutrition 0.000 claims 1
- 239000003826 tablet Substances 0.000 claims 1
- 0 ***C(N(*)C(N(*)c1ccc(*)nc1)=S)=O Chemical compound ***C(N(*)C(N(*)c1ccc(*)nc1)=S)=O 0.000 description 2
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US42763402P | 2002-11-19 | 2002-11-19 | |
| PCT/US2003/036809 WO2004046095A1 (en) | 2002-11-19 | 2003-11-18 | Substituted aryl thioureas and related compounds; inhibitors of viral replication |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006272359A Division JP2007084548A (ja) | 2002-11-19 | 2006-10-03 | 置換されたアリールチオウレアおよび関連化合物；ウイルス複製のインヒビター |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2006506439A JP2006506439A (ja) | 2006-02-23 |
| JP2006506439A5 true JP2006506439A5 (https=) | 2006-11-30 |
| JP4206382B2 JP4206382B2 (ja) | 2009-01-07 |
Family
ID=32326574
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004553861A Expired - Fee Related JP4206382B2 (ja) | 2002-11-19 | 2003-11-18 | 置換されたアリールチオウレアおよび関連化合物；ウイルス複製のインヒビター |
| JP2006272359A Pending JP2007084548A (ja) | 2002-11-19 | 2006-10-03 | 置換されたアリールチオウレアおよび関連化合物；ウイルス複製のインヒビター |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006272359A Pending JP2007084548A (ja) | 2002-11-19 | 2006-10-03 | 置換されたアリールチオウレアおよび関連化合物；ウイルス複製のインヒビター |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US7094807B2 (https=) |
| EP (1) | EP1562895A1 (https=) |
| JP (2) | JP4206382B2 (https=) |
| KR (1) | KR20050111306A (https=) |
| CN (1) | CN1738797A (https=) |
| AP (1) | AP2005003319A0 (https=) |
| AU (1) | AU2003295605A1 (https=) |
| BR (1) | BR0316397A (https=) |
| CA (1) | CA2506415A1 (https=) |
| EA (1) | EA200500846A1 (https=) |
| MX (1) | MXPA05005379A (https=) |
| NO (1) | NO20052546L (https=) |
| NZ (1) | NZ540033A (https=) |
| OA (1) | OA12961A (https=) |
| WO (1) | WO2004046095A1 (https=) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1738797A (zh) * | 2002-11-19 | 2006-02-22 | 阿基里昂药品公司 | 取代的芳基硫脲和相关的化合物,病毒复制的抑制剂 |
| AU2005326813B2 (en) * | 2002-11-19 | 2011-08-04 | Achillion Pharmaceuticals, Inc. | Substituted aryl acylthioureas and related compounds; inhibitors of viral replication |
| GB0500020D0 (en) | 2005-01-04 | 2005-02-09 | Novartis Ag | Organic compounds |
| TW200528459A (en) * | 2004-01-06 | 2005-09-01 | Achillion Pharmaceuticals Inc | Azabenzofuran substituted thioureas; inhibitors of viral replication |
| US7501510B2 (en) * | 2004-03-26 | 2009-03-10 | The University Of Hong Kong | Thiourea compositions and uses thereof |
| TW200600492A (en) * | 2004-05-18 | 2006-01-01 | Achillion Pharmaceuticals Inc | Substituted aryl acylthioureas and related compounds; inhibitors of viral replication |
| WO2006113650A1 (en) * | 2005-04-18 | 2006-10-26 | Khan Saeed R | Design and synthesis of novel tubulin polymerization inhibitors: bonzoylphenyluria (bpu) sulfur analogs |
| WO2007035895A2 (en) * | 2005-09-21 | 2007-03-29 | Cook Incorporated | Endoluminal stent graft delivery assembly |
| TWI329102B (en) * | 2006-08-15 | 2010-08-21 | Nat Health Research Institutes | Thiourea compounds and method for inhibiting hepatitis c virus infection |
| BRPI0721162A2 (pt) * | 2006-12-18 | 2014-04-01 | Achillion Pharmaceuticals Inc | Terapia combinada para o tratamento de infecções por hepatite c |
| WO2008124300A1 (en) | 2007-04-10 | 2008-10-16 | National Health Research Institutes | Hepatitis c virus inhibitors |
| TW200848016A (en) | 2007-06-08 | 2008-12-16 | Nat Health Research Institutes | Thiourea compound and composition of treating hepatitis C virus infection |
| TWI361808B (en) * | 2008-01-08 | 2012-04-11 | Nat Health Research Institutes | Imidazolidinone and imidazolidinethione derivatives |
| US8198284B2 (en) * | 2008-04-30 | 2012-06-12 | National Health Research Institutes | Treatment of neurodegenerative disorders with thiourea compounds |
| WO2010065668A1 (en) | 2008-12-03 | 2010-06-10 | Presidio Pharmaceuticals, Inc. | Inhibitors of hcv ns5a |
| FR2943056A1 (fr) * | 2009-03-16 | 2010-09-17 | Sanofi Aventis | Derives de n-°2-aza-bicyclo°2.1.1!hex-1-yl)-aryl-methyl!- heterobenzamide, leur preparation et leur application en therapeutique |
| CA2763140A1 (en) | 2009-05-29 | 2010-12-02 | Schering Corporation | Antiviral compounds composed of three linked aryl moieties to treat diseases such as hepatitis c |
| US8377639B2 (en) | 2009-06-26 | 2013-02-19 | University Of Massachusetts | Compounds for modulating RNA binding proteins and uses therefor |
| JP2013512246A (ja) | 2009-11-25 | 2013-04-11 | メルク・シャープ・アンド・ドーム・コーポレーション | ウイルス疾患治療に有用な縮合型三環式化合物およびその誘導体 |
| US20130156731A1 (en) | 2009-12-22 | 2013-06-20 | Kevin X. Chen | Fused tricyclic compounds and methods of use thereof for the treatment of viral diseas |
| EA201290882A1 (ru) | 2010-03-09 | 2013-04-30 | Мерк Шарп Энд Домэ Корп. | Конденсированные трициклические силильные соединения и способы их применения для лечения вирусных заболеваний |
| CA2797248A1 (en) * | 2010-04-23 | 2011-10-27 | University Of Rochester | Reducing transmission of sexually transmitted infections |
| WO2012018534A2 (en) | 2010-07-26 | 2012-02-09 | Schering Corporation | Substituted biphenylene compounds and methods of use thereof for the treatment of viral diseases |
| JP2013540122A (ja) | 2010-09-29 | 2013-10-31 | メルク・シャープ・エンド・ドーム・コーポレイション | 縮合四環式化合物誘導体およびウィルス疾患治療のためのそれの使用方法 |
| WO2012142075A1 (en) | 2011-04-13 | 2012-10-18 | Merck Sharp & Dohme Corp. | 2'-azido substituted nucleoside derivatives and methods of use thereof for the treatment of viral diseases |
| BR112013026345A2 (pt) | 2011-04-13 | 2019-04-24 | Merck Sharp & Dohe Corp. | composto, composição farmacêutica, uso de um composto, e, método para tratar um paciente infectado com hcv |
| WO2012162025A1 (en) * | 2011-05-20 | 2012-11-29 | President And Fellows Of Harvard College | Methods of selecting cancer patients for treatment with n,n'-diarylurea compounds and n,n'-diarylthiourea compounds |
| CN103826452B (zh) * | 2011-07-12 | 2017-02-01 | 陶氏益农公司 | 杀虫组合物及其相关方法 |
| WO2013033900A1 (en) | 2011-09-08 | 2013-03-14 | Merck Sharp & Dohme Corp. | Tetracyclic heterocycle compounds and methods of use thereof for the treatment of viral diseases |
| WO2013033899A1 (en) | 2011-09-08 | 2013-03-14 | Merck Sharp & Dohme Corp. | Substituted benzofuran compounds and methods of use thereof for the treatment of viral diseases |
| WO2013033901A1 (en) | 2011-09-08 | 2013-03-14 | Merck Sharp & Dohme Corp. | Heterocyclic-substituted benzofuran derivatives and methods of use thereof for the treatment of viral diseases |
| US20140378416A1 (en) | 2011-09-14 | 2014-12-25 | Michael P. Dwyer | Silyl-containing heterocyclic compounds and methods of use thereof for the treatment of viral diseases |
| WO2014011429A1 (en) * | 2012-07-09 | 2014-01-16 | Dow Agrosciences Llc | Pesticidal compositions and processes related thereto |
| US10188538B2 (en) | 2015-12-30 | 2019-01-29 | Cook Medical Technologies Llc | Hybrid trigger wire for endografts |
| EP3454862B1 (en) | 2016-05-10 | 2024-09-11 | C4 Therapeutics, Inc. | Spirocyclic degronimers for target protein degradation |
| EP4491236A3 (en) | 2016-05-10 | 2025-04-02 | C4 Therapeutics, Inc. | Heterocyclic degronimers for target protein degradation |
| CN109641874A (zh) | 2016-05-10 | 2019-04-16 | C4医药公司 | 用于靶蛋白降解的c3-碳连接的戊二酰亚胺降解决定子体 |
| CN109790143A (zh) | 2016-05-10 | 2019-05-21 | C4医药公司 | 用于靶蛋白降解的胺连接的c3-戊二酰亚胺降解决定子体 |
| CN110087469A (zh) * | 2016-12-21 | 2019-08-02 | 美国陶氏益农公司 | 具有某些杀虫效用的分子、以及与其相关的中间体、组合物、和方法 |
| EP4717317A2 (en) | 2017-06-20 | 2026-04-01 | C4 Therapeutics, Inc. | N/o-linked degrons and degronimers for protein degradation |
| US20190167670A1 (en) * | 2017-10-31 | 2019-06-06 | Nutech Ventures | Methods of treating or preventing zika virus infection |
| CN119735584B (zh) * | 2024-12-16 | 2025-10-14 | 东北农业大学 | 一种含有酰基硫脲和杂环结构的苯氧吡啶类化合物及其制备方法和应用 |
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-
2003
- 2003-11-18 CN CNA2003801087106A patent/CN1738797A/zh active Pending
- 2003-11-18 CA CA002506415A patent/CA2506415A1/en not_active Abandoned
- 2003-11-18 AP AP2005003319A patent/AP2005003319A0/xx unknown
- 2003-11-18 WO PCT/US2003/036809 patent/WO2004046095A1/en not_active Ceased
- 2003-11-18 AU AU2003295605A patent/AU2003295605A1/en not_active Abandoned
- 2003-11-18 EP EP03786803A patent/EP1562895A1/en not_active Withdrawn
- 2003-11-18 KR KR1020057009112A patent/KR20050111306A/ko not_active Withdrawn
- 2003-11-18 NZ NZ540033A patent/NZ540033A/en not_active IP Right Cessation
- 2003-11-18 MX MXPA05005379A patent/MXPA05005379A/es unknown
- 2003-11-18 EA EA200500846A patent/EA200500846A1/ru unknown
- 2003-11-18 JP JP2004553861A patent/JP4206382B2/ja not_active Expired - Fee Related
- 2003-11-18 BR BR0316397-0A patent/BR0316397A/pt not_active IP Right Cessation
- 2003-11-18 OA OA1200500150A patent/OA12961A/en unknown
- 2003-11-18 US US10/716,175 patent/US7094807B2/en not_active Expired - Fee Related
-
2004
- 2004-12-17 US US11/015,300 patent/US7476686B2/en not_active Expired - Fee Related
-
2005
- 2005-05-26 NO NO20052546A patent/NO20052546L/no not_active Application Discontinuation
-
2006
- 2006-10-03 JP JP2006272359A patent/JP2007084548A/ja active Pending
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