CN1918138B - 作为cxc-和cc-趋化因子受体配体的噻二唑化合物 - Google Patents
作为cxc-和cc-趋化因子受体配体的噻二唑化合物 Download PDFInfo
- Publication number
- CN1918138B CN1918138B CN2004800416952A CN200480041695A CN1918138B CN 1918138 B CN1918138 B CN 1918138B CN 2004800416952 A CN2004800416952 A CN 2004800416952A CN 200480041695 A CN200480041695 A CN 200480041695A CN 1918138 B CN1918138 B CN 1918138B
- Authority
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- China
- Prior art keywords
- compound
- disease
- alkyl
- acceptable salt
- pharmacy acceptable
- 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.)
- Expired - Fee Related
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- 0 **C(*)(Cc1ccc[o]1)C1**1 Chemical compound **C(*)(Cc1ccc[o]1)C1**1 0.000 description 61
- PWROLWSTJYICMD-QMMMGPOBSA-N CC[C@@H]1C2(CC2)CCC1 Chemical compound CC[C@@H]1C2(CC2)CCC1 PWROLWSTJYICMD-QMMMGPOBSA-N 0.000 description 3
- JWDPVDWHUOLXMP-JTQLQIEISA-N CC(C)c1c[o]c([C@H](C)C(C)(C)C)c1 Chemical compound CC(C)c1c[o]c([C@H](C)C(C)(C)C)c1 JWDPVDWHUOLXMP-JTQLQIEISA-N 0.000 description 2
- VJEYJFQUNNZKPG-UHFFFAOYSA-N CCC(C)(C)C(c1ccc(C)[o]1)=O Chemical compound CCC(C)(C)C(c1ccc(C)[o]1)=O VJEYJFQUNNZKPG-UHFFFAOYSA-N 0.000 description 2
- YFNPBJCEYXSVSE-WAYWQWQTSA-N C/C(/C(N(C)C)=O)=C(\C)/O Chemical compound C/C(/C(N(C)C)=O)=C(\C)/O YFNPBJCEYXSVSE-WAYWQWQTSA-N 0.000 description 1
- CLUPMXZISUFRFS-UHFFFAOYSA-N C=C(c1ccccn1)O Chemical compound C=C(c1ccccn1)O CLUPMXZISUFRFS-UHFFFAOYSA-N 0.000 description 1
- CWXPZXBSDSIRCS-UHFFFAOYSA-N CC(C)(C)OC(N1CCNCC1)=O Chemical compound CC(C)(C)OC(N1CCNCC1)=O CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 1
- WRPRUMKDYSXSJT-SECBINFHSA-N CC(C)[C@@H](C)c1ccc(C)[o]1 Chemical compound CC(C)[C@@H](C)c1ccc(C)[o]1 WRPRUMKDYSXSJT-SECBINFHSA-N 0.000 description 1
- QPCIJPLFCMSOET-UHFFFAOYSA-N CC(C1)C1(c1cc(Br)c[o]1)N Chemical compound CC(C1)C1(c1cc(Br)c[o]1)N QPCIJPLFCMSOET-UHFFFAOYSA-N 0.000 description 1
- GTDRESDILUXBCB-WAYWQWQTSA-N CC/C(/O)=C(\C)/C#N Chemical compound CC/C(/O)=C(\C)/C#N GTDRESDILUXBCB-WAYWQWQTSA-N 0.000 description 1
- BZVXCKWUSHXULA-UHFFFAOYSA-N CCC(C)(C)Cc1c(C)cc(C)[o]1 Chemical compound CCC(C)(C)Cc1c(C)cc(C)[o]1 BZVXCKWUSHXULA-UHFFFAOYSA-N 0.000 description 1
- TUPIWILQIFLURY-LLVKDONJSA-N CCC(C)(C)[C@@H](c1ccc(C)[o]1)[O]#C Chemical compound CCC(C)(C)[C@@H](c1ccc(C)[o]1)[O]#C TUPIWILQIFLURY-LLVKDONJSA-N 0.000 description 1
- ACSGLWMNCXQJTE-UHFFFAOYSA-N CCC(C)c1cc(Br)c[o]1 Chemical compound CCC(C)c1cc(Br)c[o]1 ACSGLWMNCXQJTE-UHFFFAOYSA-N 0.000 description 1
- QAFODUGVXFNLBE-UHFFFAOYSA-O CCC(COC)[NH3+] Chemical compound CCC(COC)[NH3+] QAFODUGVXFNLBE-UHFFFAOYSA-O 0.000 description 1
- OFSHZUAPHDPMEB-UHFFFAOYSA-N CCC(c1cc(Br)c[o]1)O Chemical compound CCC(c1cc(Br)c[o]1)O OFSHZUAPHDPMEB-UHFFFAOYSA-N 0.000 description 1
- BEDIRFLXVVIIRR-UHFFFAOYSA-N CCN(Cc1ccccc1)S(c([s]cc1N)c1O)(=O)=O Chemical compound CCN(Cc1ccccc1)S(c([s]cc1N)c1O)(=O)=O BEDIRFLXVVIIRR-UHFFFAOYSA-N 0.000 description 1
- DDJPFCUYLOVMIL-UHFFFAOYSA-N CCNS(c([s]cc1N)c1O)(=O)=O Chemical compound CCNS(c([s]cc1N)c1O)(=O)=O DDJPFCUYLOVMIL-UHFFFAOYSA-N 0.000 description 1
- YJNRDOADOJBVBU-UHFFFAOYSA-N CCc(cc1)c(C(N(C)C)=O)c(O)c1N Chemical compound CCc(cc1)c(C(N(C)C)=O)c(O)c1N YJNRDOADOJBVBU-UHFFFAOYSA-N 0.000 description 1
- NCOFLMXQZYTYLD-SECBINFHSA-N CCc1c[o]c([C@H](C)C(C)=C)c1 Chemical compound CCc1c[o]c([C@H](C)C(C)=C)c1 NCOFLMXQZYTYLD-SECBINFHSA-N 0.000 description 1
- IRZLHHVOEATNFE-UHFFFAOYSA-N CCc1cc(Br)c[o]1 Chemical compound CCc1cc(Br)c[o]1 IRZLHHVOEATNFE-UHFFFAOYSA-N 0.000 description 1
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N CCc1ccccc1 Chemical compound CCc1ccccc1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
- VLLMILLTHUWJHA-UHFFFAOYSA-N CN(C)C(c1cccc(N)c1O)=O Chemical compound CN(C)C(c1cccc(N)c1O)=O VLLMILLTHUWJHA-UHFFFAOYSA-N 0.000 description 1
- VUHWGTQVICTOSY-UHFFFAOYSA-N CN(C)C(c1cccc([NH+](C)[O-])c1O)=O Chemical compound CN(C)C(c1cccc([NH+](C)[O-])c1O)=O VUHWGTQVICTOSY-UHFFFAOYSA-N 0.000 description 1
- XTKYIVXIXHGKAY-MRVPVSSYSA-N C[C@@H](c1cc(C)c[o]1)C#C Chemical compound C[C@@H](c1cc(C)c[o]1)C#C XTKYIVXIXHGKAY-MRVPVSSYSA-N 0.000 description 1
- QBIIBHIOOJOMAO-VIFPVBQESA-N C[C@H](C(C)(C)C)c(cc1)cc2c1OCO2 Chemical compound C[C@H](C(C)(C)C)c(cc1)cc2c1OCO2 QBIIBHIOOJOMAO-VIFPVBQESA-N 0.000 description 1
- ZZLNWVFWWYBHKF-SECBINFHSA-N C[C@H](C(C)=C)c1ccc(C)[o]1 Chemical compound C[C@H](C(C)=C)c1ccc(C)[o]1 ZZLNWVFWWYBHKF-SECBINFHSA-N 0.000 description 1
- YTQHLILQJBHOIQ-UHFFFAOYSA-N C[n]1c(C(N(CC2)CCN2C(c(cccc2N)c2O)=O)=O)ccc1 Chemical compound C[n]1c(C(N(CC2)CCN2C(c(cccc2N)c2O)=O)=O)ccc1 YTQHLILQJBHOIQ-UHFFFAOYSA-N 0.000 description 1
- ORKRXHSVNNRQFY-UHFFFAOYSA-N C[n]1c(C(N(CC2)CCN2C(c(cccc2[N+]([O-])=O)c2O)=O)=O)ccc1 Chemical compound C[n]1c(C(N(CC2)CCN2C(c(cccc2[N+]([O-])=O)c2O)=O)=O)ccc1 ORKRXHSVNNRQFY-UHFFFAOYSA-N 0.000 description 1
- DTSCVYQDGZJOEN-UHFFFAOYSA-N C[n]1c(C(N2CCNCC2)=O)ccc1 Chemical compound C[n]1c(C(N2CCNCC2)=O)ccc1 DTSCVYQDGZJOEN-UHFFFAOYSA-N 0.000 description 1
- ILAOVOOZLVGAJF-UHFFFAOYSA-N C[n]1c(C(O)=O)ccc1 Chemical compound C[n]1c(C(O)=O)ccc1 ILAOVOOZLVGAJF-UHFFFAOYSA-N 0.000 description 1
- FCMRHMPITHLLLA-UHFFFAOYSA-N Cc(cccc1[N+]([O-])=O)c1N Chemical compound Cc(cccc1[N+]([O-])=O)c1N FCMRHMPITHLLLA-UHFFFAOYSA-N 0.000 description 1
- OEDOPVDNHPZCCY-SNVBAGLBSA-N Cc1c(C)[o]c([C@@H](C#C)N(C)C)c1 Chemical compound Cc1c(C)[o]c([C@@H](C#C)N(C)C)c1 OEDOPVDNHPZCCY-SNVBAGLBSA-N 0.000 description 1
- YCWILCGZIWHGNA-UHFFFAOYSA-N Cc1ccc(C(N)[Cs])[s]1 Chemical compound Cc1ccc(C(N)[Cs])[s]1 YCWILCGZIWHGNA-UHFFFAOYSA-N 0.000 description 1
- OUDFNZMQXZILJD-UHFFFAOYSA-N Cc1ccc(C=O)[o]1 Chemical compound Cc1ccc(C=O)[o]1 OUDFNZMQXZILJD-UHFFFAOYSA-N 0.000 description 1
- XQQBUAPQHNYYRS-UHFFFAOYSA-N Cc1ccc[s]1 Chemical compound Cc1ccc[s]1 XQQBUAPQHNYYRS-UHFFFAOYSA-N 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Cc1ccccc1 Chemical compound Cc1ccccc1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- GCBXAQLZTBLSGE-UHFFFAOYSA-N NC(C1(CC1)c1ccccc1)=O Chemical compound NC(C1(CC1)c1ccccc1)=O GCBXAQLZTBLSGE-UHFFFAOYSA-N 0.000 description 1
- KLKQAOHZFHBEIQ-UHFFFAOYSA-N NC(CO)c1ccc[s]1 Chemical compound NC(CO)c1ccc[s]1 KLKQAOHZFHBEIQ-UHFFFAOYSA-N 0.000 description 1
- HISATYPVSUKHDT-SSDOTTSWSA-N NC([C@@H](C1=CCCC=C1)O)=O Chemical compound NC([C@@H](C1=CCCC=C1)O)=O HISATYPVSUKHDT-SSDOTTSWSA-N 0.000 description 1
- DSIBSRXKQRYPJP-UHFFFAOYSA-N NC(c1ccn[o]1)=O Chemical compound NC(c1ccn[o]1)=O DSIBSRXKQRYPJP-UHFFFAOYSA-N 0.000 description 1
- SCXLAOWWYRPSPJ-SSDOTTSWSA-N Nc(cccc1C(N(CC2)C[C@@H]2O)=O)c1O Chemical compound Nc(cccc1C(N(CC2)C[C@@H]2O)=O)c1O SCXLAOWWYRPSPJ-SSDOTTSWSA-N 0.000 description 1
- SCXLAOWWYRPSPJ-ZETCQYMHSA-N Nc(cccc1C(N(CC2)C[C@H]2O)=O)c1O Chemical compound Nc(cccc1C(N(CC2)C[C@H]2O)=O)c1O SCXLAOWWYRPSPJ-ZETCQYMHSA-N 0.000 description 1
- OTFFCAGPSWJBDK-UHFFFAOYSA-N Nc1c2[nH]ncc2ccc1 Chemical compound Nc1c2[nH]ncc2ccc1 OTFFCAGPSWJBDK-UHFFFAOYSA-N 0.000 description 1
- WMIAAIKLMVXOHG-UHFFFAOYSA-N Nc1cccc(C(N(CC2)CCN2C(c2ncccc2)=O)=O)c1O Chemical compound Nc1cccc(C(N(CC2)CCN2C(c2ncccc2)=O)=O)c1O WMIAAIKLMVXOHG-UHFFFAOYSA-N 0.000 description 1
- MYDOHAKXVYFQDB-MRVPVSSYSA-N Nc1cccc(C(N2[C@@H](CO)CCC2)=O)c1O Chemical compound Nc1cccc(C(N2[C@@H](CO)CCC2)=O)c1O MYDOHAKXVYFQDB-MRVPVSSYSA-N 0.000 description 1
- JIDDDPVQQUHACU-RXMQYKEDSA-N O=C[C@@H]1NCCC1 Chemical compound O=C[C@@H]1NCCC1 JIDDDPVQQUHACU-RXMQYKEDSA-N 0.000 description 1
- ZNWWGQXNEYXGBB-UHFFFAOYSA-N OC(c1cccc(N=O)c1O)=O Chemical compound OC(c1cccc(N=O)c1O)=O ZNWWGQXNEYXGBB-UHFFFAOYSA-N 0.000 description 1
- JHHZLHWJQPUNKB-BYPYZUCNSA-N O[C@@H]1CNCC1 Chemical compound O[C@@H]1CNCC1 JHHZLHWJQPUNKB-BYPYZUCNSA-N 0.000 description 1
- RXWKFVJUUIALMG-ZETCQYMHSA-N [O-][N+](c(cccc1C(N(CC2)C[C@H]2O)=O)c1O)=O Chemical compound [O-][N+](c(cccc1C(N(CC2)C[C@H]2O)=O)c1O)=O RXWKFVJUUIALMG-ZETCQYMHSA-N 0.000 description 1
- PQCAUHUKTBHUSA-UHFFFAOYSA-N [O-][N+](c1cccc2c1[nH]nc2)=O Chemical compound [O-][N+](c1cccc2c1[nH]nc2)=O PQCAUHUKTBHUSA-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
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| PCT/US2004/042060 WO2005066147A1 (en) | 2003-12-19 | 2004-12-16 | Thiadiazoles as cxc- and cc- chemokine receptor ligands |
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| WO2010050445A1 (ja) * | 2008-10-27 | 2010-05-06 | 武田薬品工業株式会社 | 二環性化合物 |
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| CA2783699C (en) | 2009-12-08 | 2019-01-15 | Case Western Reserve University | Primary amine compounds for treating ocular disorders |
| US20130085133A1 (en) * | 2010-02-08 | 2013-04-04 | Sourthern Research Institute Office of Commercialization and Intellectual Prop. | Anti-viral treatment and assay to screenfor anti-viral agent |
| MX354212B (es) | 2010-03-10 | 2018-02-19 | Incyte Corp | Derivados de piperidin-4-il azetidina como inhibidores de janus cinasa 1 (jak1). |
| US20110288107A1 (en) | 2010-05-21 | 2011-11-24 | Bhavnish Parikh | Topical formulation for a jak inhibitor |
| CA2818542A1 (en) | 2010-11-19 | 2012-05-24 | Incyte Corporation | Cyclobutyl substituted pyrrolopyridine and pyrrolopyrimidine derivatives as jak inhibitors |
| EP2640725B1 (en) | 2010-11-19 | 2015-01-07 | Incyte Corporation | Heterocyclic-substituted pyrrolopyridines and pyrrolopyrimidines as jak inhibitors |
| WO2012177606A1 (en) | 2011-06-20 | 2012-12-27 | Incyte Corporation | Azetidinyl phenyl, pyridyl or pyrazinyl carboxamide derivatives as jak inhibitors |
| TW201313721A (zh) | 2011-08-18 | 2013-04-01 | Incyte Corp | 作為jak抑制劑之環己基氮雜環丁烷衍生物 |
| UA111854C2 (uk) | 2011-09-07 | 2016-06-24 | Інсайт Холдінгс Корпорейшн | Способи і проміжні сполуки для отримання інгібіторів jak |
| WO2013173720A1 (en) | 2012-05-18 | 2013-11-21 | Incyte Corporation | Piperidinylcyclobutyl substituted pyrrolopyridine and pyrrolopyrimidine derivatives as jak inhibitors |
| US8865723B2 (en) | 2012-10-25 | 2014-10-21 | Tetra Discovery Partners Llc | Selective PDE4 B inhibition and improvement in cognition in subjects with brain injury |
| ES2880814T3 (es) | 2012-11-15 | 2021-11-25 | Incyte Holdings Corp | Formas de dosificación de liberación sostenida de ruxolitinib |
| EP3489239B1 (en) | 2013-03-06 | 2021-09-15 | Incyte Holdings Corporation | Processes and intermediates for making a jak inhibitor |
| TWI789516B (zh) | 2013-08-07 | 2023-01-11 | 美商英塞特公司 | Jak1抑制劑之持續釋放劑型 |
| US9763992B2 (en) | 2014-02-13 | 2017-09-19 | Father Flanagan's Boys' Home | Treatment of noise induced hearing loss |
| WO2015184305A1 (en) | 2014-05-30 | 2015-12-03 | Incyte Corporation | TREATMENT OF CHRONIC NEUTROPHILIC LEUKEMIA (CNL) AND ATYPICAL CHRONIC MYELOID LEUKEMIA (aCML) BY INHIBITORS OF JAK1 |
| AR113922A1 (es) | 2017-12-08 | 2020-07-01 | Incyte Corp | Terapia de combinación de dosis baja para el tratamiento de neoplasias mieloproliferativas |
| HRP20220510T1 (hr) | 2018-01-30 | 2022-05-27 | Incyte Corporation | Postupci za pripravu (1-(3-fluoro-2-(trifluorometil)izonikotinil) piperidin-4-ona) |
| HUE067471T2 (hu) | 2018-03-30 | 2024-10-28 | Incyte Corp | Gennyes verejtékmirigy-gyulladás kezelése jak inhibitorok alkalmazásával |
| US11833155B2 (en) | 2020-06-03 | 2023-12-05 | Incyte Corporation | Combination therapy for treatment of myeloproliferative neoplasms |
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- 2004-12-16 WO PCT/US2004/042060 patent/WO2005066147A1/en not_active Ceased
- 2004-12-16 DE DE602004016211T patent/DE602004016211D1/de not_active Expired - Lifetime
- 2004-12-16 US US11/013,753 patent/US7338968B2/en not_active Expired - Fee Related
- 2004-12-16 CA CA002550189A patent/CA2550189A1/en not_active Abandoned
- 2004-12-16 CN CN2004800416952A patent/CN1918138B/zh not_active Expired - Fee Related
- 2004-12-16 ES ES04814266T patent/ES2308299T3/es not_active Expired - Lifetime
- 2004-12-16 EP EP04814266A patent/EP1694659B8/en not_active Expired - Lifetime
- 2004-12-16 TW TW093139212A patent/TW200528450A/zh unknown
- 2004-12-16 JP JP2006545364A patent/JP4939229B2/ja not_active Expired - Fee Related
- 2004-12-16 MX MXPA06007076A patent/MXPA06007076A/es active IP Right Grant
- 2004-12-16 MY MYPI20045183A patent/MY139808A/en unknown
- 2004-12-17 AR ARP040104753A patent/AR046791A1/es not_active Application Discontinuation
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2007
- 2007-09-26 US US11/861,870 patent/US7786149B2/en not_active Expired - Fee Related
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2011
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Also Published As
| Publication number | Publication date |
|---|---|
| ES2308299T3 (es) | 2008-12-01 |
| ATE406356T1 (de) | 2008-09-15 |
| AR046791A1 (es) | 2005-12-21 |
| EP1694659A1 (en) | 2006-08-30 |
| US7338968B2 (en) | 2008-03-04 |
| MXPA06007076A (es) | 2006-08-31 |
| JP4939229B2 (ja) | 2012-05-23 |
| DE602004016211D1 (en) | 2008-10-09 |
| US7786149B2 (en) | 2010-08-31 |
| EP1694659B8 (en) | 2008-10-08 |
| MY139808A (en) | 2009-10-30 |
| US20060223864A1 (en) | 2006-10-05 |
| WO2005066147A1 (en) | 2005-07-21 |
| CA2550189A1 (en) | 2005-07-21 |
| JP2007514746A (ja) | 2007-06-07 |
| HK1087711A1 (en) | 2006-10-20 |
| CN1918138A (zh) | 2007-02-21 |
| JP2011093943A (ja) | 2011-05-12 |
| TW200528450A (en) | 2005-09-01 |
| EP1694659B1 (en) | 2008-08-27 |
| US20080090823A1 (en) | 2008-04-17 |
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