JP4499993B2 - Cxc−ケモカインレセプターリガンドとしての3,4−ジ−置換シクロブテン−1,2−ジオン - Google Patents
Cxc−ケモカインレセプターリガンドとしての3,4−ジ−置換シクロブテン−1,2−ジオン Download PDFInfo
- Publication number
- JP4499993B2 JP4499993B2 JP2002581381A JP2002581381A JP4499993B2 JP 4499993 B2 JP4499993 B2 JP 4499993B2 JP 2002581381 A JP2002581381 A JP 2002581381A JP 2002581381 A JP2002581381 A JP 2002581381A JP 4499993 B2 JP4499993 B2 JP 4499993B2
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- 0 CC(*=C)(c1cccc*1*)NI Chemical compound CC(*=C)(c1cccc*1*)NI 0.000 description 30
- JNYNGPWXFXCIPS-HXUWFJFHSA-N C#C[C@H](c1ccccc1)NC(C(C1=O)=O)=C1Nc1cccc(C(N(CC2)CCN2C(c2ccc[o]2)=O)=O)c1O Chemical compound C#C[C@H](c1ccccc1)NC(C(C1=O)=O)=C1Nc1cccc(C(N(CC2)CCN2C(c2ccc[o]2)=O)=O)c1O JNYNGPWXFXCIPS-HXUWFJFHSA-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
- GNDVWYNRSPQLAE-UHFFFAOYSA-O CC(C)C(C([NH2+]c1ccccc1)=O)NC(C(C1=O)=O)=C1Nc1cccc(C(N(C)C)=O)c1O Chemical compound CC(C)C(C([NH2+]c1ccccc1)=O)NC(C(C1=O)=O)=C1Nc1cccc(C(N(C)C)=O)c1O GNDVWYNRSPQLAE-UHFFFAOYSA-O 0.000 description 1
- YYLSZLYPALMDKM-UHFFFAOYSA-N CC(C)C(C)C(c1ccc(C)c(N)c1O)=O Chemical compound CC(C)C(C)C(c1ccc(C)c(N)c1O)=O YYLSZLYPALMDKM-UHFFFAOYSA-N 0.000 description 1
- YKNBHWMYFXOCEK-MXZBBBRTSA-N CC(C)[C@@H](C(N[C@H](C)c1ccccc1)=O)NC(C(C1=O)O)=C1Nc1cccc(C(N(C)C)=O)c1O Chemical compound CC(C)[C@@H](C(N[C@H](C)c1ccccc1)=O)NC(C(C1=O)O)=C1Nc1cccc(C(N(C)C)=O)c1O YKNBHWMYFXOCEK-MXZBBBRTSA-N 0.000 description 1
- GNDVWYNRSPQLAE-KRWDZBQOSA-N CC(C)[C@@H](C(Nc1ccccc1)=O)NC(C(C1=O)=O)=C1Nc(cccc1C(N(C)C)=O)c1O Chemical compound CC(C)[C@@H](C(Nc1ccccc1)=O)NC(C(C1=O)=O)=C1Nc(cccc1C(N(C)C)=O)c1O GNDVWYNRSPQLAE-KRWDZBQOSA-N 0.000 description 1
- JAIQLQSBSRNMAE-GFCCVEGCSA-N CC(C)[C@H](C(NC)=O)NC(C(C1=O)=O)=C1Nc1cccc(C(N(C)C)=O)c1O Chemical compound CC(C)[C@H](C(NC)=O)NC(C(C1=O)=O)=C1Nc1cccc(C(N(C)C)=O)c1O JAIQLQSBSRNMAE-GFCCVEGCSA-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
- CUCXLRRZCAACKA-IEIXJENWSA-N CC([C@@H]1C(C)C1)C(c1cc([N+]([O-])=O)c[s]1)=O Chemical compound CC([C@@H]1C(C)C1)C(c1cc([N+]([O-])=O)c[s]1)=O CUCXLRRZCAACKA-IEIXJENWSA-N 0.000 description 1
- RIQPESYCXIXLSN-UHFFFAOYSA-N CC1C=C(CC2CC2)SC1C(C(F)(F)F)=[NH+][O-]=C Chemical compound CC1C=C(CC2CC2)SC1C(C(F)(F)F)=[NH+][O-]=C RIQPESYCXIXLSN-UHFFFAOYSA-N 0.000 description 1
- FCGKUCDBZXMPMD-UHFFFAOYSA-N CCC(c1cc(Br)c[o]1)=O Chemical compound CCC(c1cc(Br)c[o]1)=O FCGKUCDBZXMPMD-UHFFFAOYSA-N 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
- DWIFTCOWGVWXDP-UHFFFAOYSA-N CCC1OC1c1cc(N)c[s]1 Chemical compound CCC1OC1c1cc(N)c[s]1 DWIFTCOWGVWXDP-UHFFFAOYSA-N 0.000 description 1
- DMBPAHYEKHGPJQ-UHFFFAOYSA-N CCCc1cc(Br)c[o]1 Chemical compound CCCc1cc(Br)c[o]1 DMBPAHYEKHGPJQ-UHFFFAOYSA-N 0.000 description 1
- IXKBGZHMTPSITL-UHFFFAOYSA-N CCOC(C(C1)NCCN1C(N(C)C)=O)=O Chemical compound CCOC(C(C1)NCCN1C(N(C)C)=O)=O IXKBGZHMTPSITL-UHFFFAOYSA-N 0.000 description 1
- QAFODUGVXFNLBE-RXMQYKEDSA-N CC[C@H](COC)N Chemical compound CC[C@H](COC)N QAFODUGVXFNLBE-RXMQYKEDSA-N 0.000 description 1
- ROSMJBLXJLMJLV-SSDOTTSWSA-N CC[C@H](Cc1ccc[s]1)N Chemical compound CC[C@H](Cc1ccc[s]1)N ROSMJBLXJLMJLV-SSDOTTSWSA-N 0.000 description 1
- AQFLVLHRZFLDDV-SECBINFHSA-N CC[C@H](c1ccccc1)N Chemical compound CC[C@H](c1ccccc1)N AQFLVLHRZFLDDV-SECBINFHSA-N 0.000 description 1
- NIRZVVBUKLWPGP-LJQANCHMSA-N CC[C@H](c1ccccc1)NC(C(C1=O)=O)=C1Nc1cccc(C(N(CC2)CCN2C(N(C)C)=O)=O)c1O Chemical compound CC[C@H](c1ccccc1)NC(C(C1=O)=O)=C1Nc1cccc(C(N(CC2)CCN2C(N(C)C)=O)=O)c1O NIRZVVBUKLWPGP-LJQANCHMSA-N 0.000 description 1
- AYQSQHIEGKKVNV-UHFFFAOYSA-N CN(C)C(c(cccc1NC(C(C2=O)=O)=C2NC2(CC2)c2ccccc2)c1O)=O Chemical compound CN(C)C(c(cccc1NC(C(C2=O)=O)=C2NC2(CC2)c2ccccc2)c1O)=O AYQSQHIEGKKVNV-UHFFFAOYSA-N 0.000 description 1
- DSOUXZULAXQUHE-UHFFFAOYSA-N CN(C)C(c1cccc(NC(C(C2=O)=O)=C2N)c1O)=O Chemical compound CN(C)C(c1cccc(NC(C(C2=O)=O)=C2N)c1O)=O DSOUXZULAXQUHE-UHFFFAOYSA-N 0.000 description 1
- SSVDFKAPLLJYBL-PYMCNQPYSA-N CN(C)C(c1cccc(NC(C(C2=O)=O)=C2N[C@H]2C=CCCC2COC)c1O)=O Chemical compound CN(C)C(c1cccc(NC(C(C2=O)=O)=C2N[C@H]2C=CCCC2COC)c1O)=O SSVDFKAPLLJYBL-PYMCNQPYSA-N 0.000 description 1
- ZCRKUBBODNBABQ-UHFFFAOYSA-N CN(C)C(c1cccc([N+]([O-])=O)c1N)=O Chemical compound CN(C)C(c1cccc([N+]([O-])=O)c1N)=O ZCRKUBBODNBABQ-UHFFFAOYSA-N 0.000 description 1
- XMULBBMFZCKQDO-ZFWWWQNUSA-N CN(C)CC(c(cccc1NC(C(C2=O)=O)=C2N[C@@H]2[C@H](COC)CCCC2)c1O)=O Chemical compound CN(C)CC(c(cccc1NC(C(C2=O)=O)=C2N[C@@H]2[C@H](COC)CCCC2)c1O)=O XMULBBMFZCKQDO-ZFWWWQNUSA-N 0.000 description 1
- IEABMNXBYJWGBK-UHFFFAOYSA-N CNC(c(cccc1N)c1O)=O Chemical compound CNC(c(cccc1N)c1O)=O IEABMNXBYJWGBK-UHFFFAOYSA-N 0.000 description 1
- LTNCYCKOTJDBMA-JTQLQIEISA-N C[C@@H](c1ccc[o]1)NC(C(C1=O)=O)=C1Nc1cccc(C(N(C)C)=O)c1O Chemical compound C[C@@H](c1ccc[o]1)NC(C(C1=O)=O)=C1Nc1cccc(C(N(C)C)=O)c1O LTNCYCKOTJDBMA-JTQLQIEISA-N 0.000 description 1
- CFDYWVSYVARQBL-UHFFFAOYSA-N Cc(cc1C(N(C)C)=O)c(C)c([N+]([O-])=O)c1O Chemical compound Cc(cc1C(N(C)C)=O)c(C)c([N+]([O-])=O)c1O CFDYWVSYVARQBL-UHFFFAOYSA-N 0.000 description 1
- NJESAXZANHETJV-UHFFFAOYSA-N Cc1ccc(C(O)=O)c(O)c1 Chemical compound Cc1ccc(C(O)=O)c(O)c1 NJESAXZANHETJV-UHFFFAOYSA-N 0.000 description 1
- DZCAUMADOBDJJH-UHFFFAOYSA-N NC(C(F)(F)F)c1ccccc1 Chemical compound NC(C(F)(F)F)c1ccccc1 DZCAUMADOBDJJH-UHFFFAOYSA-N 0.000 description 1
- RGZGRPPQZUQUCR-UHFFFAOYSA-N NC1(CCCCC1)c1ccccc1 Chemical compound NC1(CCCCC1)c1ccccc1 RGZGRPPQZUQUCR-UHFFFAOYSA-N 0.000 description 1
- JJPIVRWTAGQTPQ-UHFFFAOYSA-N Nc(c([N+]([O-])=O)ccc1)c1C(O)=O Chemical compound Nc(c([N+]([O-])=O)ccc1)c1C(O)=O JJPIVRWTAGQTPQ-UHFFFAOYSA-N 0.000 description 1
- HFZKYLQVHNTIIY-UHFFFAOYSA-N Nc(cccc1C(N(CC2)CCN2C(c2ccc[s]2)=O)=O)c1O Chemical compound Nc(cccc1C(N(CC2)CCN2C(c2ccc[s]2)=O)=O)c1O HFZKYLQVHNTIIY-UHFFFAOYSA-N 0.000 description 1
- MYDOHAKXVYFQDB-UHFFFAOYSA-N Nc(cccc1C(N2C(CO)CCC2)=O)c1O Chemical compound Nc(cccc1C(N2C(CO)CCC2)=O)c1O MYDOHAKXVYFQDB-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N Nc1ccccc1O Chemical compound Nc1ccccc1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- TUKWYJVGKNCDJJ-KPKJPENVSA-N O/N=C(/C(F)(F)F)\c1ccccc1 Chemical compound O/N=C(/C(F)(F)F)\c1ccccc1 TUKWYJVGKNCDJJ-KPKJPENVSA-N 0.000 description 1
- KZJRKRQSDZGHEC-UHFFFAOYSA-N O=C(C(F)(F)F)c1ccccc1 Chemical compound O=C(C(F)(F)F)c1ccccc1 KZJRKRQSDZGHEC-UHFFFAOYSA-N 0.000 description 1
- QIQITDHWZYEEPA-UHFFFAOYSA-N O=C(c1ccc[s]1)Cl Chemical compound O=C(c1ccc[s]1)Cl QIQITDHWZYEEPA-UHFFFAOYSA-N 0.000 description 1
- KUKGMDPEGDZCTL-UHFFFAOYSA-N O=C(c1ccc[s]1)N1CCNCC1 Chemical compound O=C(c1ccc[s]1)N1CCNCC1 KUKGMDPEGDZCTL-UHFFFAOYSA-N 0.000 description 1
- VSADUYUTKZHMIM-UHFFFAOYSA-N O=Cc1cc(-c2ccccc2)c[o]1 Chemical compound O=Cc1cc(-c2ccccc2)c[o]1 VSADUYUTKZHMIM-UHFFFAOYSA-N 0.000 description 1
- MRGBBKQOSUHKPF-UHFFFAOYSA-N O=Cc1cc(Br)c[o]1 Chemical compound O=Cc1cc(Br)c[o]1 MRGBBKQOSUHKPF-UHFFFAOYSA-N 0.000 description 1
- QXXHHHWXFHPNOS-UHFFFAOYSA-N OC(C1(CCCCC1)c1ccccc1)=O Chemical compound OC(C1(CCCCC1)c1ccccc1)=O QXXHHHWXFHPNOS-UHFFFAOYSA-N 0.000 description 1
- HVVNJUAVDAZWCB-RXMQYKEDSA-N OC[C@@H]1NCCC1 Chemical compound OC[C@@H]1NCCC1 HVVNJUAVDAZWCB-RXMQYKEDSA-N 0.000 description 1
- IQUPABOKLQSFBK-UHFFFAOYSA-N [O-][N+](c(cccc1)c1O)=O Chemical compound [O-][N+](c(cccc1)c1O)=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
- UDCSPPCIXFPUSU-UHFFFAOYSA-N [O-][N+](c(cccc1C(N(CC2)CCN2C(c2ccc[s]2)=O)=O)c1O)=O Chemical compound [O-][N+](c(cccc1C(N(CC2)CCN2C(c2ccc[s]2)=O)=O)c1O)=O UDCSPPCIXFPUSU-UHFFFAOYSA-N 0.000 description 1
- WWWFHFGUOIQNJC-UHFFFAOYSA-N [O-][N+](c1cccc(C(O)=O)c1O)=O Chemical compound [O-][N+](c1cccc(C(O)=O)c1O)=O WWWFHFGUOIQNJC-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
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- C07C225/20—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of the carbon skeleton
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- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/30—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having the nitrogen atom of the carboxamide group bound to hydrogen atoms or to acyclic carbon atoms
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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| US28402601P | 2001-04-16 | 2001-04-16 | |
| PCT/US2002/012681 WO2002083624A1 (en) | 2001-04-16 | 2002-04-15 | 3,4-di-substituted cyclobutene-1,2-diones as cxc-chemokine receptor ligands |
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| KR102710925B1 (ko) * | 2021-06-01 | 2024-09-27 | 부산대학교 산학협력단 | 신규 스퀘어아마이드 유도체 및 이의 용도 |
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| EP4686469A1 (en) * | 2024-07-31 | 2026-02-04 | Dompé farmaceutici SpA | Cxcl8 inhibitors for use in the treatment of diabetes-associated comorbidities |
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| JPH0692915A (ja) * | 1992-07-28 | 1994-04-05 | Sumitomo Metal Ind Ltd | 1,2−ジアミノシクロブテン−3,4−ジオン誘導体及びその用途 |
| GB9312210D0 (en) * | 1993-06-14 | 1993-07-28 | Smithkline Beecham Plc | Chemical compounds |
| GB9316111D0 (en) * | 1993-08-04 | 1993-09-22 | Pfizer Ltd | Benzopyrans |
| US5354763A (en) * | 1993-11-17 | 1994-10-11 | American Home Products Corporation | Substituted N-heteroaryl and N-aryl-1,2-diaminocyclobutene-3,4-diones |
| US5466712A (en) * | 1994-11-04 | 1995-11-14 | American Home Products Corporation | Substituted n-aryl-1,2-diaminocyclobutene-3,4-diones |
| AU686896B2 (en) * | 1994-11-16 | 1998-02-12 | American Home Products Corporation | Diaminocyclobutene-3,4-diones |
| CZ425698A3 (cs) * | 1996-06-27 | 1999-06-16 | Smithkline Beecham Corporation | Antagonista IL-8 receptoru |
| AU6250298A (en) * | 1997-01-30 | 1998-08-25 | American Home Products Corporation | Substituted hydroxy-anilino derivatives of cyclobutene-3,4-diones |
| US5840764A (en) * | 1997-01-30 | 1998-11-24 | American Home Products Corporation | Substituted hydroxy-anilino derivatives of cyclobutene-3,4-diones |
| US6211220B1 (en) * | 1998-11-23 | 2001-04-03 | Cell Pathways, Inc. | Method for treating neoplasia with amino or pyridylamino cyclobutene derivatives |
| EP1140792A1 (en) * | 1998-12-14 | 2001-10-10 | American Home Products Corporation | 3,4-diamino-3-cyclobutene-1,2-dione derivatives which inhibit leukocyte adhesion mediated by vla-4 |
| CZ20012185A3 (cs) * | 1998-12-16 | 2001-10-17 | Bayer Aktiengesellschaft | Nové bifenylové sloučeniny a sloučeniny analogické bifenylovým sloučeninám, způsob jejich přípravy, farmaceutické prostředky a pouľití těchto sloučenin a prostředků jako antagonistů integrinu |
| US6518283B1 (en) * | 1999-05-28 | 2003-02-11 | Celltech R&D Limited | Squaric acid derivatives |
| AR033803A1 (es) * | 2000-03-01 | 2004-01-07 | Smithkline Beecham Corp | Compuestos de dianilino escuarano, composiciones farmaceuticas que los comprenden, y el uso de los mismos en la fabricacion de medicamentos para tratar enfermedades mediadas por quimioquinas |
| MXPA02011868A (es) * | 2000-05-30 | 2003-04-10 | Smithkline Beecham Corp | Antagonistas de receptor de interleucina 8. |
| US20040048897A1 (en) * | 2001-01-16 | 2004-03-11 | Mccleland Brent | Il-8 receptor antagonists |
| CZ20032639A3 (cs) * | 2001-03-30 | 2004-04-14 | Smithkline Beecham Corporation | Způsoby přípravy sloučenin obsahujících fenol |
| US20040053953A1 (en) * | 2002-03-18 | 2004-03-18 | Schering Corporation | Treatment of chemokine mediated diseases |
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