JP2009534421A5 - - Google Patents
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- Publication number
- JP2009534421A5 JP2009534421A5 JP2009506795A JP2009506795A JP2009534421A5 JP 2009534421 A5 JP2009534421 A5 JP 2009534421A5 JP 2009506795 A JP2009506795 A JP 2009506795A JP 2009506795 A JP2009506795 A JP 2009506795A JP 2009534421 A5 JP2009534421 A5 JP 2009534421A5
- Authority
- JP
- Japan
- Prior art keywords
- chloro
- phenyl
- urea
- hydroxy
- piperidinylsulfonyl
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims 29
- -1 phenyloxy Chemical group 0.000 claims 14
- NGYNBSHYFOFVLS-LBPRGKRZSA-N 1-[4-chloro-2-hydroxy-3-[(3s)-piperidin-3-yl]sulfonylphenyl]-3-(3-fluoro-2-methylphenyl)urea Chemical compound CC1=C(F)C=CC=C1NC(=O)NC1=CC=C(Cl)C(S(=O)(=O)[C@@H]2CNCCC2)=C1O NGYNBSHYFOFVLS-LBPRGKRZSA-N 0.000 claims 8
- 201000010099 disease Diseases 0.000 claims 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
- 102000019034 Chemokines Human genes 0.000 claims 7
- 108010012236 Chemokines Proteins 0.000 claims 7
- 238000000034 method Methods 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 241000124008 Mammalia Species 0.000 claims 6
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 230000001404 mediated effect Effects 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- ZVDORRYGKFXKJT-JTQLQIEISA-N 1-(2-chloro-3-fluorophenyl)-3-[4-chloro-2-hydroxy-3-[(3s)-piperidin-3-yl]sulfonylphenyl]urea Chemical compound C1=CC(Cl)=C(S(=O)(=O)[C@@H]2CNCCC2)C(O)=C1NC(=O)NC1=CC=CC(F)=C1Cl ZVDORRYGKFXKJT-JTQLQIEISA-N 0.000 claims 4
- PKYWPWXABSTTKQ-JTQLQIEISA-N 1-[4-chloro-2-hydroxy-3-[(3s)-piperidin-3-yl]sulfonylphenyl]-3-(2-chloropyridin-3-yl)urea Chemical compound C1=CC(Cl)=C(S(=O)(=O)[C@@H]2CNCCC2)C(O)=C1NC(=O)NC1=CC=CN=C1Cl PKYWPWXABSTTKQ-JTQLQIEISA-N 0.000 claims 4
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 4
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 4
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 4
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 4
- 208000006673 asthma Diseases 0.000 claims 4
- ZVDORRYGKFXKJT-UHFFFAOYSA-N 1-(2-chloro-3-fluorophenyl)-3-(4-chloro-2-hydroxy-3-piperidin-3-ylsulfonylphenyl)urea Chemical compound C1=CC(Cl)=C(S(=O)(=O)C2CNCCC2)C(O)=C1NC(=O)NC1=CC=CC(F)=C1Cl ZVDORRYGKFXKJT-UHFFFAOYSA-N 0.000 claims 3
- YRHNFBLNHYMPER-UHFFFAOYSA-N 1-(4-chloro-2-hydroxy-3-piperidin-3-ylsulfonylphenyl)-3-(2,3-dichlorophenyl)urea Chemical compound C1=CC(Cl)=C(S(=O)(=O)C2CNCCC2)C(O)=C1NC(=O)NC1=CC=CC(Cl)=C1Cl YRHNFBLNHYMPER-UHFFFAOYSA-N 0.000 claims 3
- 206010040070 Septic Shock Diseases 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 229940124597 therapeutic agent Drugs 0.000 claims 3
- MUYNMIWSABCFMR-UHFFFAOYSA-N 1-(2-chloro-3-fluorophenyl)-3-(4-chloro-2-hydroxy-3-piperidin-4-ylsulfonylphenyl)urea Chemical compound C1=CC(Cl)=C(S(=O)(=O)C2CCNCC2)C(O)=C1NC(=O)NC1=CC=CC(F)=C1Cl MUYNMIWSABCFMR-UHFFFAOYSA-N 0.000 claims 2
- CRHQLGHPEWNKIT-SECBINFHSA-N 1-(2-chloro-3-fluorophenyl)-3-[4-chloro-2-hydroxy-3-[(3r)-pyrrolidin-3-yl]sulfonylphenyl]urea Chemical compound C1=CC(Cl)=C(S(=O)(=O)[C@H]2CNCC2)C(O)=C1NC(=O)NC1=CC=CC(F)=C1Cl CRHQLGHPEWNKIT-SECBINFHSA-N 0.000 claims 2
- CRHQLGHPEWNKIT-VIFPVBQESA-N 1-(2-chloro-3-fluorophenyl)-3-[4-chloro-2-hydroxy-3-[(3s)-pyrrolidin-3-yl]sulfonylphenyl]urea Chemical compound C1=CC(Cl)=C(S(=O)(=O)[C@@H]2CNCC2)C(O)=C1NC(=O)NC1=CC=CC(F)=C1Cl CRHQLGHPEWNKIT-VIFPVBQESA-N 0.000 claims 2
- PKYWPWXABSTTKQ-UHFFFAOYSA-N 1-(4-chloro-2-hydroxy-3-piperidin-3-ylsulfonylphenyl)-3-(2-chloropyridin-3-yl)urea Chemical compound C1=CC(Cl)=C(S(=O)(=O)C2CNCCC2)C(O)=C1NC(=O)NC1=CC=CN=C1Cl PKYWPWXABSTTKQ-UHFFFAOYSA-N 0.000 claims 2
- VSFXNIKJSPGYDK-UHFFFAOYSA-N 1-(4-chloro-2-hydroxy-3-piperidin-4-ylsulfonylphenyl)-3-(2-phenoxyphenyl)urea Chemical compound C1=CC(Cl)=C(S(=O)(=O)C2CCNCC2)C(O)=C1NC(=O)NC1=CC=CC=C1OC1=CC=CC=C1 VSFXNIKJSPGYDK-UHFFFAOYSA-N 0.000 claims 2
- OCOZZPSPYJQSBG-UHFFFAOYSA-N 1-(4-chloro-2-hydroxy-3-piperidin-4-ylsulfonylphenyl)-3-(3-fluoro-2-methylphenyl)urea Chemical compound CC1=C(F)C=CC=C1NC(=O)NC1=CC=C(Cl)C(S(=O)(=O)C2CCNCC2)=C1O OCOZZPSPYJQSBG-UHFFFAOYSA-N 0.000 claims 2
- RPNXJDDPJUHEGW-MRXNPFEDSA-N 1-[4-chloro-2-hydroxy-3-[(3r)-pyrrolidin-3-yl]sulfonylphenyl]-3-(2-phenoxyphenyl)urea Chemical compound C1=CC(Cl)=C(S(=O)(=O)[C@H]2CNCC2)C(O)=C1NC(=O)NC1=CC=CC=C1OC1=CC=CC=C1 RPNXJDDPJUHEGW-MRXNPFEDSA-N 0.000 claims 2
- RZKGHMMYGWXTOP-VIFPVBQESA-N 1-[4-chloro-2-hydroxy-3-[(3s)-pyrrolidin-3-yl]sulfonylphenyl]-3-(2-chloropyridin-3-yl)urea Chemical compound C1=CC(Cl)=C(S(=O)(=O)[C@@H]2CNCC2)C(O)=C1NC(=O)NC1=CC=CN=C1Cl RZKGHMMYGWXTOP-VIFPVBQESA-N 0.000 claims 2
- FCPRZCUSHXUJGN-NSHDSACASA-N 1-[4-chloro-2-hydroxy-3-[(3s)-pyrrolidin-3-yl]sulfonylphenyl]-3-(3-fluoro-2-methylphenyl)urea Chemical compound CC1=C(F)C=CC=C1NC(=O)NC1=CC=C(Cl)C(S(=O)(=O)[C@@H]2CNCC2)=C1O FCPRZCUSHXUJGN-NSHDSACASA-N 0.000 claims 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims 2
- BDQXHNOVHSZTRA-UHFFFAOYSA-N 4-[6-chloro-2-hydroxy-3-[(2-phenoxyphenyl)carbamoylamino]phenyl]sulfonylpiperidine-1-carboxylic acid Chemical compound C1CN(CCC1S(=O)(=O)C2=C(C=CC(=C2O)NC(=O)NC3=CC=CC=C3OC4=CC=CC=C4)Cl)C(=O)O BDQXHNOVHSZTRA-UHFFFAOYSA-N 0.000 claims 2
- NFAUHWLPKVMZBA-UHFFFAOYSA-N 4-[6-chloro-3-[(3-fluoro-2-methylphenyl)carbamoylamino]-2-hydroxyphenyl]sulfonylpiperidine-1-carboxylic acid Chemical compound CC1=C(C=CC=C1F)NC(=O)NC2=C(C(=C(C=C2)Cl)S(=O)(=O)C3CCN(CC3)C(=O)O)O NFAUHWLPKVMZBA-UHFFFAOYSA-N 0.000 claims 2
- AEAVECDTPGODQD-UHFFFAOYSA-N C1CN(C(=O)O)CCC1S(=O)(=O)C1=C(Cl)C=CC(NC(=O)NC=2C(=C(F)C=CC=2)Cl)=C1O Chemical compound C1CN(C(=O)O)CCC1S(=O)(=O)C1=C(Cl)C=CC(NC(=O)NC=2C(=C(F)C=CC=2)Cl)=C1O AEAVECDTPGODQD-UHFFFAOYSA-N 0.000 claims 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 2
- 102000012740 beta Adrenergic Receptors Human genes 0.000 claims 2
- 108010079452 beta Adrenergic Receptors Proteins 0.000 claims 2
- 239000004202 carbamide Substances 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 239000012948 isocyanate Substances 0.000 claims 2
- 150000002513 isocyanates Chemical class 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 150000003457 sulfones Chemical class 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- JPXNTZIAFODILH-UHFFFAOYSA-N 1-(2-chloro-3-fluorophenyl)-3-[4-chloro-2-hydroxy-3-(pyrrolidin-3-ylmethylsulfonyl)phenyl]urea Chemical compound C1=CC(Cl)=C(S(=O)(=O)CC2CNCC2)C(O)=C1NC(=O)NC1=CC=CC(F)=C1Cl JPXNTZIAFODILH-UHFFFAOYSA-N 0.000 claims 1
- MKXPBYCTEVMLQI-UHFFFAOYSA-N 1-(4-chloro-2-hydroxy-3-piperidin-3-ylsulfonylphenyl)-3-(2-ethylphenyl)urea Chemical compound CCC1=CC=CC=C1NC(=O)NC1=CC=C(Cl)C(S(=O)(=O)C2CNCCC2)=C1O MKXPBYCTEVMLQI-UHFFFAOYSA-N 0.000 claims 1
- OHCFLELUXQCVDQ-UHFFFAOYSA-N 1-(4-chloro-2-hydroxy-3-piperidin-3-ylsulfonylphenyl)-3-[2-(trifluoromethoxy)phenyl]urea Chemical compound C1=CC(Cl)=C(S(=O)(=O)C2CNCCC2)C(O)=C1NC(=O)NC1=CC=CC=C1OC(F)(F)F OHCFLELUXQCVDQ-UHFFFAOYSA-N 0.000 claims 1
- QBBZZDIQIBBIPR-UHFFFAOYSA-N 1-(4-chloro-2-hydroxy-3-piperidin-4-ylsulfonylphenyl)-3-(2,2-difluoro-1,3-benzodioxol-4-yl)urea Chemical compound OC1=C(NC(=O)NC=2C=3OC(F)(F)OC=3C=CC=2)C=CC(Cl)=C1S(=O)(=O)C1CCNCC1 QBBZZDIQIBBIPR-UHFFFAOYSA-N 0.000 claims 1
- AXDQQCQGTFACRR-UHFFFAOYSA-N 1-(4-chloro-2-hydroxy-3-piperidin-4-ylsulfonylphenyl)-3-(2-chloropyridin-3-yl)urea Chemical compound C1=CC(Cl)=C(S(=O)(=O)C2CCNCC2)C(O)=C1NC(=O)NC1=CC=CN=C1Cl AXDQQCQGTFACRR-UHFFFAOYSA-N 0.000 claims 1
- KEIVOVSJTKSMSG-UHFFFAOYSA-N 1-(4-chloro-2-hydroxy-3-piperidin-4-ylsulfonylphenyl)-3-(2-ethylphenyl)urea Chemical compound CCC1=CC=CC=C1NC(=O)NC1=CC=C(Cl)C(S(=O)(=O)C2CCNCC2)=C1O KEIVOVSJTKSMSG-UHFFFAOYSA-N 0.000 claims 1
- UDEAWUIUSZJSEN-UHFFFAOYSA-N 1-(4-chloro-2-hydroxy-3-piperidin-4-ylsulfonylphenyl)-3-[2-(trifluoromethoxy)phenyl]urea Chemical compound C1=CC(Cl)=C(S(=O)(=O)C2CCNCC2)C(O)=C1NC(=O)NC1=CC=CC=C1OC(F)(F)F UDEAWUIUSZJSEN-UHFFFAOYSA-N 0.000 claims 1
- YQTOITXLXNUIOQ-UHFFFAOYSA-N 1-[4-chloro-2-hydroxy-3-(pyrrolidin-3-ylmethylsulfonyl)phenyl]-3-(3-fluoro-2-methylphenyl)urea Chemical compound CC1=C(F)C=CC=C1NC(=O)NC1=CC=C(Cl)C(S(=O)(=O)CC2CNCC2)=C1O YQTOITXLXNUIOQ-UHFFFAOYSA-N 0.000 claims 1
- UCTMKTXPZVSONA-UHFFFAOYSA-N 1-[4-chloro-2-hydroxy-3-(pyrrolidin-3-ylmethylsulfonyl)phenyl]-3-[2-(trifluoromethoxy)phenyl]urea Chemical compound C1=CC(Cl)=C(S(=O)(=O)CC2CNCC2)C(O)=C1NC(=O)NC1=CC=CC=C1OC(F)(F)F UCTMKTXPZVSONA-UHFFFAOYSA-N 0.000 claims 1
- APBXDCDLFXRMCV-SECBINFHSA-N 1-[4-chloro-2-hydroxy-3-[(3r)-pyrrolidin-3-yl]sulfonylphenyl]-3-(2,2-difluoro-1,3-benzodioxol-4-yl)urea Chemical compound OC1=C(NC(=O)NC=2C=3OC(F)(F)OC=3C=CC=2)C=CC(Cl)=C1S(=O)(=O)[C@@H]1CCNC1 APBXDCDLFXRMCV-SECBINFHSA-N 0.000 claims 1
- NDGUODLRLFWGSS-CYBMUJFWSA-N 1-[4-chloro-2-hydroxy-3-[(3r)-pyrrolidin-3-yl]sulfonylphenyl]-3-(2-ethylphenyl)urea Chemical compound CCC1=CC=CC=C1NC(=O)NC1=CC=C(Cl)C(S(=O)(=O)[C@H]2CNCC2)=C1O NDGUODLRLFWGSS-CYBMUJFWSA-N 0.000 claims 1
- LMEJQAHYEIEWGL-SNVBAGLBSA-N 1-[4-chloro-2-hydroxy-3-[(3r)-pyrrolidin-3-yl]sulfonylphenyl]-3-[2-(trifluoromethoxy)phenyl]urea Chemical compound C1=CC(Cl)=C(S(=O)(=O)[C@H]2CNCC2)C(O)=C1NC(=O)NC1=CC=CC=C1OC(F)(F)F LMEJQAHYEIEWGL-SNVBAGLBSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 108010061300 CXCR3 Receptors Proteins 0.000 claims 1
- 102000011963 CXCR3 Receptors Human genes 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 206010012438 Dermatitis atopic Diseases 0.000 claims 1
- 241000709661 Enterovirus Species 0.000 claims 1
- 206010018364 Glomerulonephritis Diseases 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- NLHPNBSFRJFMCY-UHFFFAOYSA-N N1(CC=C1)S(=O)(=O)C=1C(=C(C=CC1Cl)NC(=O)NC1=C(C(=CC=C1)F)C)O Chemical compound N1(CC=C1)S(=O)(=O)C=1C(=C(C=CC1Cl)NC(=O)NC1=C(C(=CC=C1)F)C)O NLHPNBSFRJFMCY-UHFFFAOYSA-N 0.000 claims 1
- SKCWTVMBOUYHNQ-UHFFFAOYSA-N N1(CC=C1)S(=O)(=O)C=1C(=C(C=CC1Cl)NC(=O)NC1=C(C(=CC=C1)F)Cl)O Chemical compound N1(CC=C1)S(=O)(=O)C=1C(=C(C=CC1Cl)NC(=O)NC1=C(C(=CC=C1)F)Cl)O SKCWTVMBOUYHNQ-UHFFFAOYSA-N 0.000 claims 1
- AAHMLGDJQQXCOL-UHFFFAOYSA-N N1(CC=C1)S(=O)(=O)C=1C(=C(C=CC1Cl)NC(=O)NC=1C(=NC=CC1)Cl)O Chemical compound N1(CC=C1)S(=O)(=O)C=1C(=C(C=CC1Cl)NC(=O)NC=1C(=NC=CC1)Cl)O AAHMLGDJQQXCOL-UHFFFAOYSA-N 0.000 claims 1
- 208000001132 Osteoporosis Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 206010063837 Reperfusion injury Diseases 0.000 claims 1
- 206010040047 Sepsis Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims 1
- 208000007536 Thrombosis Diseases 0.000 claims 1
- 206010044248 Toxic shock syndrome Diseases 0.000 claims 1
- 231100000650 Toxic shock syndrome Toxicity 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 201000008937 atopic dermatitis Diseases 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 210000004204 blood vessel Anatomy 0.000 claims 1
- 239000003067 chemokine receptor CCR5 antagonist Substances 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 239000012467 final product Substances 0.000 claims 1
- 208000007565 gingivitis Diseases 0.000 claims 1
- 208000024908 graft versus host disease Diseases 0.000 claims 1
- 210000003958 hematopoietic stem cell Anatomy 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 210000003734 kidney Anatomy 0.000 claims 1
- 201000004792 malaria Diseases 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 239000002243 precursor Substances 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 239000002464 receptor antagonist Substances 0.000 claims 1
- 229940044551 receptor antagonist Drugs 0.000 claims 1
- 208000037803 restenosis Diseases 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 230000036303 septic shock Effects 0.000 claims 1
- 208000013223 septicemia Diseases 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 230000003612 virological effect Effects 0.000 claims 1
- 0 *c(c(S(*)(=O)=O)c1O)ccc1N Chemical compound *c(c(S(*)(=O)=O)c1O)ccc1N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US79388106P | 2006-04-21 | 2006-04-21 | |
| US60/793,881 | 2006-04-21 | ||
| PCT/US2007/067091 WO2007124424A2 (en) | 2006-04-21 | 2007-04-20 | Il-8 receptor antagonists |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009534421A JP2009534421A (ja) | 2009-09-24 |
| JP2009534421A5 true JP2009534421A5 (https=) | 2010-06-17 |
| JP5269763B2 JP5269763B2 (ja) | 2013-08-21 |
Family
ID=38625766
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009506795A Expired - Fee Related JP5269763B2 (ja) | 2006-04-21 | 2007-04-20 | Ｉｌ−８受容体アンタゴニスト |
Country Status (31)
| Country | Link |
|---|---|
| US (4) | US20090093451A1 (https=) |
| EP (1) | EP2009992B1 (https=) |
| JP (1) | JP5269763B2 (https=) |
| KR (1) | KR101376472B1 (https=) |
| CN (1) | CN101472477B (https=) |
| AR (1) | AR060562A1 (https=) |
| AU (1) | AU2007240365B2 (https=) |
| BR (1) | BRPI0710232B8 (https=) |
| CA (1) | CA2650009C (https=) |
| CL (1) | CL2007001142A1 (https=) |
| CR (1) | CR10391A (https=) |
| CY (1) | CY1113132T1 (https=) |
| DK (1) | DK2009992T3 (https=) |
| EA (1) | EA014958B1 (https=) |
| ES (1) | ES2389680T3 (https=) |
| HR (1) | HRP20120579T1 (https=) |
| IL (1) | IL194811A (https=) |
| JO (1) | JO2796B1 (https=) |
| MA (1) | MA30408B1 (https=) |
| MX (1) | MX2008013600A (https=) |
| MY (1) | MY145810A (https=) |
| NO (1) | NO341736B1 (https=) |
| NZ (1) | NZ572069A (https=) |
| PE (1) | PE20080077A1 (https=) |
| PL (1) | PL2009992T3 (https=) |
| PT (1) | PT2009992E (https=) |
| SI (1) | SI2009992T1 (https=) |
| TW (1) | TWI414517B (https=) |
| UA (1) | UA98456C2 (https=) |
| WO (1) | WO2007124424A2 (https=) |
| ZA (1) | ZA200808358B (https=) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200418812A (en) * | 2002-10-29 | 2004-10-01 | Smithkline Beecham Corp | IL-8 receptor antagonists |
| EP1812008A4 (en) * | 2004-10-20 | 2008-10-29 | Smithkline Beecham Corp | ANTAGONISTS OF THE IL-8 RECEPTOR |
| PL2009992T3 (pl) * | 2006-04-21 | 2012-11-30 | Glaxosmithkline Llc | Antagoniści receptora IL-8 |
| US8097626B2 (en) * | 2006-04-21 | 2012-01-17 | Glaxosmithkline Llc | IL-8 receptor antagonists |
| CL2007001829A1 (es) * | 2006-06-23 | 2008-01-25 | Smithkline Beecham Corp | P-toluensulfonato de n-[4-cloro-2-hidroxi-3-(piperazina-1-sulfonil)fenil]-n-(2-cloro-3-fluorofenil)urea;procedimiento de preparacion;composicion farmaceutica;combinacion farmaceutica;y uso en el tratamiento de una enfermedad mediada por la quiimioquina il-8, tales como asma y epoc. |
| KR20110093893A (ko) | 2008-11-11 | 2011-08-18 | 더 리젠츠 오브 더 유니버시티 오브 미시간 | 항-ｃｘｃｒ１ 조성물 및 방법 |
| US8648070B2 (en) * | 2010-12-17 | 2014-02-11 | Boehringer Ingelheim International Gmbh | Bicyclic ring system substituted sulfonamide functionalised phenols as medicaments |
| US8648118B2 (en) * | 2010-12-17 | 2014-02-11 | Boehringer Ingelheim International Gmbh | Bicyclic ring system substituted amide functionalised phenols as medicaments |
| GB201320021D0 (en) * | 2013-11-13 | 2013-12-25 | Glaxosmithkline Ip Dev Ltd | Novel Compounds |
| US20170100385A1 (en) * | 2014-05-12 | 2017-04-13 | Glaxosmithkline Intellectual Property (No. 2) Limited | Pharmaceutical compositions comprising danirixin for treating infectious diseases |
| CR20160557A (es) * | 2014-05-29 | 2017-01-20 | Glaxosmithkline Ip Dev Ltd | Compuestos derivados de 1-(ciclopent-2-en-1-il)-3-(2-hidroxi-3-(arilsulfonil)fenil)urea como inhibidores cxcr2 |
| RU2017106172A (ru) * | 2014-07-31 | 2018-08-28 | Глэксосмитклайн Интеллекчуал Проперти Дивелопмент Лимитед | Применение антагонистов cxcr2 для предотвращения и/или лечения периферической невропатии, вызванной химиотерапией (cipn) |
| CN105061582A (zh) * | 2015-07-15 | 2015-11-18 | 云南大学 | 树鼩cxcl8-cxcr1在类风湿关节炎治疗的应用 |
| BR112018011138A2 (pt) | 2015-11-30 | 2018-11-21 | Glaxosmithkline Intellectual Property (No. | formulações para administração intravenosa |
| US10660909B2 (en) | 2016-11-17 | 2020-05-26 | Syntrix Biosystems Inc. | Method for treating cancer using chemokine antagonists |
| CN111727184B (zh) * | 2018-01-11 | 2022-06-28 | 深圳嘉科生物科技有限公司 | Cxcr2拮抗剂 |
| WO2019165315A1 (en) | 2018-02-23 | 2019-08-29 | Syntrix Biosystems Inc. | Method for treating cancer using chemokine antagonists alone or in combination |
| US12577235B2 (en) | 2019-07-11 | 2026-03-17 | Shenzhen Optimum Biological Technology Co., Ltd | Crystalline form of CXCR2 antagonist and application thereof |
| CN112851635B (zh) * | 2019-11-28 | 2022-09-16 | 中国医学科学院药物研究所 | 环状砜类化合物及其制备方法、用途和药物组合物 |
| EP3868368A1 (en) * | 2020-02-21 | 2021-08-25 | Dompe' Farmaceutici S.P.A. | Cxcl8 (interleukin-8) activity inhibitor and corticosteroid combination and pharmaceutical composition and use thereof |
Family Cites Families (101)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1792156A (en) * | 1928-01-17 | 1931-02-10 | Gen Aniline Works Inc | 5-halogen-2-amino-1-alkyloxy and 1-aralkyloxy-benzenes and intermediate products thereof and process of preparing them |
| US2363074A (en) * | 1938-06-16 | 1944-11-21 | Geigy Ag J R | Halogen substituted acylamino sulphonic acids of the aromatic series and their manufacture |
| US2407309A (en) | 1942-02-04 | 1946-09-10 | Squibb & Sons Inc | Chemotherapeutic agents of the sulphonamide type |
| US2795610A (en) | 1955-03-31 | 1957-06-11 | Du Pont | Hydroxy-phenyl alkyl ureas |
| BE639588A (https=) | 1962-11-06 | |||
| US3996253A (en) * | 1966-01-11 | 1976-12-07 | Minnesota Mining And Manufacturing Company | Process for the preparation of color images |
| BE713279A (https=) | 1967-04-06 | 1968-08-16 | ||
| CH506240A (de) | 1969-02-04 | 1971-04-30 | Ciba Geigy Ag | Verwendung von N-Hydroxyphenyl-N'-phenylharnstoffen zur Bekämpfung schädlicher Mikroorganismen ausserhalb der Textilindustrie |
| SE370866B (https=) | 1968-03-21 | 1974-11-04 | Ciba Geigy Ag | |
| US3647819A (en) | 1969-09-19 | 1972-03-07 | Sterling Drug Inc | Indazolylphenylureas and indazolyl-phenylthioureas |
| FR2100943A1 (en) | 1970-07-23 | 1972-03-24 | Ici Ltd | O-carboylcarbanilides from anthranilic acid and substd - isocyanates - immuno-suppressive agents |
| US4048333A (en) * | 1971-08-23 | 1977-09-13 | Medizinska Akademia | Method for treating a picorna virus infection |
| DE2303761A1 (de) * | 1973-01-26 | 1974-08-01 | Henkel & Cie Gmbh | Neue n,n'-disubstituierte thioharnstoffe, deren herstellung sowie verwendung als antimikrobielle substanzen |
| US4008326A (en) | 1973-12-26 | 1977-02-15 | The Upjohn Company | Substituted ureas and thioureas and pharmaceutical compositions thereof |
| US3932434A (en) | 1974-08-30 | 1976-01-13 | Eli Lilly And Company | N-2-(6-hydroxybenzothiazolyl)-N'-phenyl (or substituted phenyl) ureas |
| JPS5598152A (en) | 1979-01-16 | 1980-07-25 | Hokko Chem Ind Co Ltd | Phenylurea derivative |
| DE2928485A1 (de) * | 1979-07-14 | 1981-01-29 | Bayer Ag | Verwendung von harnstoffderivaten als arzneimittel bei der behandlung von fettstoffwechselstoerungen |
| GB2079480B (en) | 1980-07-08 | 1984-05-16 | Kodak Ltd | Heat-activated photographic and thermal recording processes employing precursor compounds |
| US4608205A (en) * | 1983-03-09 | 1986-08-26 | American Cyanamid Company | Polyanionic benzene ureas |
| US4591604A (en) * | 1984-03-28 | 1986-05-27 | American Cyanamid Company | Method of inhibiting the complement system by administering multisulfonated naphthalene ureas |
| ATE98223T1 (de) | 1988-03-30 | 1993-12-15 | Warner Lambert Co | N-(((2,6-disubstituierte)phenyl>n'- arylalkyl> harnstoffe als antihypercholesterolemische und antiatherosclerotische mittel. |
| US5215570A (en) | 1988-10-20 | 1993-06-01 | Ciba-Geigy Corporation | Sulfamoylphenylureas |
| US5290814A (en) | 1988-11-21 | 1994-03-01 | Burroughs Wellcome Co. | Anti-atherosclerotic diaryl compounds |
| US5206234A (en) | 1990-10-22 | 1993-04-27 | Merck & Co., Inc. | Benzolactam analogs as antagonists of cck |
| JPH05294935A (ja) * | 1991-03-15 | 1993-11-09 | Green Cross Corp:The | アミノピリジン系化合物 |
| AU659861B2 (en) | 1991-09-10 | 1995-06-01 | Sansho Seiyaku Co., Ltd. | Preparation for promoting hair growth |
| NZ250916A (en) | 1993-02-27 | 1995-08-28 | Nihon Nohyaku Co Ltd | N-heteroaryl-n'-phenylureas, their use as acat inhibitors |
| DK41193D0 (da) | 1993-04-07 | 1993-04-07 | Neurosearch As | Ionkanalaabnere |
| US5312831A (en) | 1993-05-12 | 1994-05-17 | American Cyanamid Company | Urethanes and ureas that induce cytokine production |
| CA2123728A1 (en) | 1993-05-21 | 1994-11-22 | Noriyoshi Sueda | Urea derivatives and their use as acat inhibitors |
| US5547966A (en) | 1993-10-07 | 1996-08-20 | Bristol-Myers Squibb Company | Aryl urea and related compounds |
| US5401758A (en) * | 1993-10-07 | 1995-03-28 | Bristol-Myers Squibb Company | Pyridinyl cyanoguanidine compounds |
| US5441984A (en) * | 1994-01-06 | 1995-08-15 | Eli Lilly And Company | Urea, thiourea and guanidine derivatives |
| US5576335A (en) * | 1994-02-01 | 1996-11-19 | Nisshin Flour Milling Co., Ltd. | Urea derivatives and their use as ACAT inhibitors |
| DE4413265A1 (de) | 1994-04-16 | 1995-10-19 | Basf Ag | Hydroxyphenylharnstoffe |
| US5780483A (en) | 1995-02-17 | 1998-07-14 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
| JPH11503110A (ja) | 1995-02-17 | 1999-03-23 | スミスクライン・ビーチャム・コーポレイション | Ｉｌ−８受容体拮抗剤 |
| US6005008A (en) | 1996-02-16 | 1999-12-21 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
| US6262113B1 (en) | 1996-03-20 | 2001-07-17 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
| US6211373B1 (en) | 1996-03-20 | 2001-04-03 | Smithkline Beecham Corporation | Phenyl urea antagonists of the IL-8 receptor |
| EP0932405A4 (en) * | 1996-06-27 | 2001-10-17 | Smithkline Beckman Corp | IL-8 RECEPTOR ANTAGONISTS |
| EP0915653A1 (en) | 1996-06-27 | 1999-05-19 | Smithkline Beecham Corporation | Il-8 receptor antagonists |
| EP0907362A4 (en) | 1996-06-27 | 1999-12-01 | Smithkline Beecham Corp | IL-8 RECEPTOR ANTAGONISTS |
| CZ425598A3 (cs) | 1996-06-27 | 1999-08-11 | Smithkline Beecham Corporation | Antagonista IL-8 receptoru |
| US6271261B1 (en) | 1996-06-27 | 2001-08-07 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
| EP0957907A4 (en) | 1996-08-06 | 2001-08-16 | Smithkline Beecham Corp | IL-8 RECEPTOR ANTAGONISTS |
| JP2002513384A (ja) | 1996-08-06 | 2002-05-08 | スミスクライン・ビーチャム・コーポレイション | Ｉｌ―８受容体アンタゴニスト |
| WO1998005329A1 (en) | 1996-08-06 | 1998-02-12 | Smithkline Beecham Corporation | Il-8 receptor antagonists |
| JP2001527519A (ja) | 1996-08-15 | 2001-12-25 | スミスクライン・ビーチャム・コーポレイション | Ｉｌ―８レセプターアンタゴニスト |
| AR008290A1 (es) * | 1996-08-15 | 1999-12-29 | Smithkline Beecham Corp | Nuevos compuestos que contienen guanidina utiles como antagonistas de los receptores de il-8, composiciones farmaceuticas que los contienenprocedimiento para la preparacion de dichos compuestos y procedimiento para la preparacion de intermediarios. |
| WO1998006398A1 (en) | 1996-08-15 | 1998-02-19 | Smithkline Beecham Corporation | Il-8 receptor antagonists |
| WO1998006701A1 (en) | 1996-08-15 | 1998-02-19 | Smithkline Beecham Corporation | Il-8 receptor antagonists |
| JP2000516621A (ja) | 1996-08-15 | 2000-12-12 | スミスクライン・ビーチャム・コーポレイション | Ｉｌ―８レセプターアンタゴニスト |
| JP2001501918A (ja) | 1996-08-21 | 2001-02-13 | スミスクライン・ビーチャム・コーポレイション | Ｉｌ―８レセプターアンタゴニスト |
| US6300325B1 (en) * | 1997-01-23 | 2001-10-09 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
| US5929250A (en) | 1997-01-23 | 1999-07-27 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
| US6436927B1 (en) | 1997-02-12 | 2002-08-20 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
| AU8673198A (en) | 1997-07-29 | 1999-02-22 | Smithkline Beecham Corporation | Il-8 receptor antagonists |
| AR015426A1 (es) | 1997-09-05 | 2001-05-02 | Smithkline Beecham Corp | Compuestos de benzotiazol antagonistas del receptor de il-8, composicion farmaceutica que los contiene, su uso para la manufactura de un medicamento,procedimiento para su preparacion, compuestos intermediarios y procedimiento para su preparacion |
| AR015425A1 (es) * | 1997-09-05 | 2001-05-02 | Smithkline Beecham Corp | Compuestos de benzotiazol, composicion farmaceutica que los contiene, su uso en la manufactura de un medicamento, procedimiento para su preparacion,compuestos intermediarios y procedimiento para su preparacion |
| CA2318195A1 (en) | 1998-01-16 | 1999-07-22 | Deborah Lynne Bryan | Il-8 receptor antagonists |
| EP1047424A4 (en) | 1998-01-20 | 2002-05-22 | Smithkline Beecham Corp | IL-8 RECEPTOR ANTAGONISTS |
| WO2000006557A1 (en) | 1998-07-27 | 2000-02-10 | Smithkline Beecham Corporation | Novel process for making il-8 receptor antagonists |
| CA2341711A1 (en) | 1998-08-28 | 2000-03-09 | Smithkline Beecham Corporation | Process for making 2-amino-5-cyanophenol |
| EP1107948A4 (en) | 1998-08-28 | 2002-01-02 | Smithkline Beecham | IMPROVED SYNTHESIS OF 3-HYDROXY-4-AMINO-BENZONITRILE |
| DE69908156T2 (de) * | 1998-09-23 | 2003-12-24 | Tularik, Inc. | Arylsulfonanilid-harnstoffe |
| UY25842A1 (es) * | 1998-12-16 | 2001-04-30 | Smithkline Beecham Corp | Antagonistas de receptores de il-8 |
| WO2000069435A1 (en) | 1999-05-18 | 2000-11-23 | Smithkline Beecham Corporation | Il-8 receptor antagonists |
| WO2000072800A2 (en) | 1999-05-28 | 2000-12-07 | Smithkline Beecham Corporation | Il-8 receptor antagonists |
| AR029637A1 (es) | 1999-05-28 | 2003-07-10 | Smithkline Beecham Corp | Compuestos de guanidina, antagonistas de los receptores de la il-8, una composicion farmaceutica que los contiene y el uso de los mismos para la manufactura de un medicamento |
| US20030225125A1 (en) | 1999-06-16 | 2003-12-04 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
| US6372933B1 (en) | 1999-08-26 | 2002-04-16 | Smithkline Beecham Corporation | Process for preparing certain phenyl urea compounds |
| US6440993B1 (en) | 1999-10-12 | 2002-08-27 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
| WO2001064165A2 (en) | 2000-03-01 | 2001-09-07 | Smithkline Beecham Corporation | Il-8 receptor antagonists |
| JP2004504270A (ja) * | 2000-03-10 | 2004-02-12 | スミスクライン・ビーチャム・コーポレイション | Ｉｌ−８受容体アンタゴニスト |
| MY133845A (en) * | 2000-03-10 | 2007-11-30 | Smithkline Beecham Corp | Il-8 receptor antagonists |
| US6767922B2 (en) | 2000-03-14 | 2004-07-27 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
| US6664259B2 (en) | 2000-03-16 | 2003-12-16 | Smithkline Beecham Corporation | Il-8 receptor antagonists |
| CO5280089A1 (es) * | 2000-03-16 | 2003-05-30 | Smithkline Beecham Corp | Antagonistas del receptor il-8 |
| UY26627A1 (es) | 2000-03-24 | 2001-09-28 | Smithkline Beecham Corp | Antagonistas de receptores de il-8 |
| US6653310B2 (en) | 2000-04-07 | 2003-11-25 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
| US6432960B2 (en) | 2000-05-10 | 2002-08-13 | Bristol-Myers Squibb Company | Squarate derivatives of dihydropyridine NPY antagonists |
| CN1454204A (zh) | 2000-05-30 | 2003-11-05 | 史密丝克莱恩比彻姆公司 | Il－8受体拮抗剂 |
| JP2004520412A (ja) | 2001-01-16 | 2004-07-08 | スミスクライン・ビーチャム・コーポレイション | Ｉｌ−８受容体アンタゴニスト |
| DE60216229T2 (de) | 2001-01-16 | 2007-10-04 | Smithkline Beecham Corp. | Il-8-rezeptorantagonisten |
| WO2002076926A1 (en) | 2001-02-02 | 2002-10-03 | Schering Corporation | 3,4-di-substituted cyclobutene-1, 2-diones as cxc chemokine receptor antagonists |
| US20030204085A1 (en) | 2001-02-02 | 2003-10-30 | Taveras Arthur G. | 3, 4-Di-substituted cyclobutene-1,2-diones as CXC-chemokine receptor antagonists |
| EP1383488A2 (en) | 2001-03-30 | 2004-01-28 | SmithKline Beecham Corporation | Methods of synthesizing phenol-containing compounds |
| EP1414810B1 (en) | 2001-06-05 | 2006-08-30 | Boehringer Ingelheim Pharmaceuticals Inc. | 1,4-disubstituted benzo-fused cycloalkyl urea compounds |
| US20040038854A1 (en) | 2001-07-16 | 2004-02-26 | Dillon Susan B. | Use of il-8 receptor antagonists in the treatment of virus infections |
| US20030028042A1 (en) | 2002-08-30 | 2003-02-06 | Palovich Michael R. | Il8-receptor antagonists |
| US20030032802A1 (en) | 2002-08-30 | 2003-02-13 | Palovich Michael R. | IL8-receptor antagonists |
| US20030065170A1 (en) | 2002-09-05 | 2003-04-03 | Widdowson Katherine Louisa | Il-8 receptor antagonists |
| TW200418812A (en) | 2002-10-29 | 2004-10-01 | Smithkline Beecham Corp | IL-8 receptor antagonists |
| JP2006527201A (ja) | 2003-06-06 | 2006-11-30 | スミスクライン・ビーチャム・コーポレイション | Ｉｌ−８受容体アンタゴニスト |
| CN1984899B (zh) * | 2004-05-12 | 2011-07-27 | 先灵公司 | Cxcr1和cxcr2趋化因子拮抗剂 |
| EP1812008A4 (en) | 2004-10-20 | 2008-10-29 | Smithkline Beecham Corp | ANTAGONISTS OF THE IL-8 RECEPTOR |
| PL2009992T3 (pl) * | 2006-04-21 | 2012-11-30 | Glaxosmithkline Llc | Antagoniści receptora IL-8 |
| US8097626B2 (en) | 2006-04-21 | 2012-01-17 | Glaxosmithkline Llc | IL-8 receptor antagonists |
| CL2007001829A1 (es) | 2006-06-23 | 2008-01-25 | Smithkline Beecham Corp | P-toluensulfonato de n-[4-cloro-2-hidroxi-3-(piperazina-1-sulfonil)fenil]-n-(2-cloro-3-fluorofenil)urea;procedimiento de preparacion;composicion farmaceutica;combinacion farmaceutica;y uso en el tratamiento de una enfermedad mediada por la quiimioquina il-8, tales como asma y epoc. |
| WO2008070707A1 (en) | 2006-12-05 | 2008-06-12 | Smithkline Beecham Corporation | Il-8 receptor antagonists |
-
2007
- 2007-04-20 PL PL07761018T patent/PL2009992T3/pl unknown
- 2007-04-20 UA UAA200812360A patent/UA98456C2/uk unknown
- 2007-04-20 KR KR1020087028378A patent/KR101376472B1/ko not_active Expired - Fee Related
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- 2007-04-20 US US12/297,885 patent/US20090093451A1/en not_active Abandoned
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