JP2004523534A5 - - Google Patents
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- JP2004523534A5 JP2004523534A5 JP2002561010A JP2002561010A JP2004523534A5 JP 2004523534 A5 JP2004523534 A5 JP 2004523534A5 JP 2002561010 A JP2002561010 A JP 2002561010A JP 2002561010 A JP2002561010 A JP 2002561010A JP 2004523534 A5 JP2004523534 A5 JP 2004523534A5
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- JP
- Japan
- Prior art keywords
- amino
- substituted
- crr
- oxoethyl
- alkyl
- 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.)
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 274
- 125000000217 alkyl group Chemical group 0.000 claims 148
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 97
- 125000003342 alkenyl group Chemical group 0.000 claims 79
- 125000000304 alkynyl group Chemical group 0.000 claims 79
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 79
- -1 cyclic acetal Chemical class 0.000 claims 61
- 229910052799 carbon Inorganic materials 0.000 claims 50
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 49
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 49
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 48
- 125000005842 heteroatom Chemical group 0.000 claims 47
- 229910052739 hydrogen Inorganic materials 0.000 claims 47
- 125000002837 carbocyclic group Chemical group 0.000 claims 45
- 150000001875 compounds Chemical class 0.000 claims 39
- 229910052760 oxygen Inorganic materials 0.000 claims 35
- 229910052717 sulfur Inorganic materials 0.000 claims 34
- 125000000623 heterocyclic group Chemical group 0.000 claims 28
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 26
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 26
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 24
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 23
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 23
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 22
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 20
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 19
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 18
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 16
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 14
- 239000008194 pharmaceutical composition Substances 0.000 claims 13
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 13
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 11
- 208000035475 disorder Diseases 0.000 claims 11
- 239000003814 drug Substances 0.000 claims 11
- 201000001320 Atherosclerosis Diseases 0.000 claims 10
- 208000006673 asthma Diseases 0.000 claims 10
- 238000004519 manufacturing process Methods 0.000 claims 10
- 201000006417 multiple sclerosis Diseases 0.000 claims 10
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 9
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 8
- 230000000694 effects Effects 0.000 claims 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 7
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 6
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 6
- 206010001889 Alveolitis Diseases 0.000 claims 6
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 6
- 206010018364 Glomerulonephritis Diseases 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- 125000004429 atom Chemical group 0.000 claims 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 6
- 206010009887 colitis Diseases 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 201000001155 extrinsic allergic alveolitis Diseases 0.000 claims 6
- 208000022098 hypersensitivity pneumonitis Diseases 0.000 claims 6
- 201000008383 nephritis Diseases 0.000 claims 6
- 210000002966 serum Anatomy 0.000 claims 6
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 6
- 206010003210 Arteriosclerosis Diseases 0.000 claims 5
- 208000011775 arteriosclerosis disease Diseases 0.000 claims 5
- 125000001041 indolyl group Chemical group 0.000 claims 5
- PAMCRRDMORMCSM-UHFFFAOYSA-N n-(trifluoromethyl)benzamide Chemical compound FC(F)(F)NC(=O)C1=CC=CC=C1 PAMCRRDMORMCSM-UHFFFAOYSA-N 0.000 claims 5
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 5
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 4
- 102100021943 C-C motif chemokine 2 Human genes 0.000 claims 4
- 101710155857 C-C motif chemokine 2 Proteins 0.000 claims 4
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims 4
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 4
- 201000004681 Psoriasis Diseases 0.000 claims 4
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 4
- 208000029028 brain injury Diseases 0.000 claims 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims 4
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 229920006395 saturated elastomer Polymers 0.000 claims 4
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 3
- 206010029155 Nephropathy toxic Diseases 0.000 claims 3
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims 3
- 125000002541 furyl group Chemical group 0.000 claims 3
- 230000003589 nefrotoxic effect Effects 0.000 claims 3
- 231100000381 nephrotoxic Toxicity 0.000 claims 3
- 231100000417 nephrotoxicity Toxicity 0.000 claims 3
- 230000007694 nephrotoxicity Effects 0.000 claims 3
- 125000000335 thiazolyl group Chemical group 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- PHRABVHYUHIYGY-UHFFFAOYSA-N 1-methylnaphthalene Chemical group C1=CC=C2C([CH2])=CC=CC2=C1 PHRABVHYUHIYGY-UHFFFAOYSA-N 0.000 claims 2
- KQEVJJULGVHJOG-UHFFFAOYSA-N 2-amino-n-[2-[[5-amino-2-[(4-methylbenzenecarbothioyl)amino]cyclohexyl]amino]-2-oxoethyl]-5-(trifluoromethyl)benzamide Chemical compound C1=CC(C)=CC=C1C(=S)NC1C(NC(=O)CNC(=O)C=2C(=CC=C(C=2)C(F)(F)F)N)CC(N)CC1 KQEVJJULGVHJOG-UHFFFAOYSA-N 0.000 claims 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 2
- 206010002329 Aneurysm Diseases 0.000 claims 2
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- 102100031151 C-C chemokine receptor type 2 Human genes 0.000 claims 2
- 101710149815 C-C chemokine receptor type 2 Proteins 0.000 claims 2
- 102100023702 C-C motif chemokine 13 Human genes 0.000 claims 2
- 101710112613 C-C motif chemokine 13 Proteins 0.000 claims 2
- 102100032366 C-C motif chemokine 7 Human genes 0.000 claims 2
- 101710155834 C-C motif chemokine 7 Proteins 0.000 claims 2
- 102100034871 C-C motif chemokine 8 Human genes 0.000 claims 2
- 101710155833 C-C motif chemokine 8 Proteins 0.000 claims 2
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 2
- 102000009410 Chemokine receptor Human genes 0.000 claims 2
- 108050000299 Chemokine receptor Proteins 0.000 claims 2
- 102000019034 Chemokines Human genes 0.000 claims 2
- 108010012236 Chemokines Proteins 0.000 claims 2
- 208000011231 Crohn disease Diseases 0.000 claims 2
- 206010012289 Dementia Diseases 0.000 claims 2
- 208000031886 HIV Infections Diseases 0.000 claims 2
- 208000037357 HIV infectious disease Diseases 0.000 claims 2
- 206010019280 Heart failures Diseases 0.000 claims 2
- 101000978374 Mus musculus C-C motif chemokine 12 Proteins 0.000 claims 2
- 206010037660 Pyrexia Diseases 0.000 claims 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims 2
- 230000002526 effect on cardiovascular system Effects 0.000 claims 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 2
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- AEUKDPKXTPNBNY-XEYRWQBLSA-N mcp 2 Chemical compound C([C@@H](C(=O)N[C@@H](CS)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CS)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)NC(=O)CNC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC(C)C)NC(=O)[C@H](CS)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CS)NC(=O)[C@H](C)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)[C@@H](N)C(C)C)C(C)C)C1=CC=CC=C1 AEUKDPKXTPNBNY-XEYRWQBLSA-N 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 2
- 201000008482 osteoarthritis Diseases 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 claims 2
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 1
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 1
- 125000006183 2,4-dimethyl benzyl group Chemical group [H]C1=C(C([H])=C(C(=C1[H])C([H])([H])*)C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- JGRNJEIOFFUJJN-MOPGFXCFSA-N 2-amino-5-bromo-N-[2-oxo-2-[[(1R,2S)-2-[(4-sulfamoylbenzoyl)amino]cyclohexyl]amino]ethyl]benzamide Chemical compound NC1=CC=C(Br)C=C1C(=O)NCC(=O)N[C@H]1[C@@H](NC(=O)C=2C=CC(=CC=2)S(N)(=O)=O)CCCC1 JGRNJEIOFFUJJN-MOPGFXCFSA-N 0.000 claims 1
- GRJOMIXZIWHRPC-MOPGFXCFSA-N 2-amino-5-chloro-n-[2-oxo-2-[[(1r,2s)-2-[(4-sulfamoylbenzoyl)amino]cyclohexyl]amino]ethyl]benzamide Chemical compound NC1=CC=C(Cl)C=C1C(=O)NCC(=O)N[C@H]1[C@@H](NC(=O)C=2C=CC(=CC=2)S(N)(=O)=O)CCCC1 GRJOMIXZIWHRPC-MOPGFXCFSA-N 0.000 claims 1
- IXVALFDHDBPQMP-MOPGFXCFSA-N 2-amino-5-iodo-n-[2-oxo-2-[[(1r,2s)-2-[(4-sulfamoylbenzoyl)amino]cyclohexyl]amino]ethyl]benzamide Chemical compound NC1=CC=C(I)C=C1C(=O)NCC(=O)N[C@H]1[C@@H](NC(=O)C=2C=CC(=CC=2)S(N)(=O)=O)CCCC1 IXVALFDHDBPQMP-MOPGFXCFSA-N 0.000 claims 1
- YATXTAOUEJKHFP-UHFFFAOYSA-N 2-amino-n-[2-[[2-[(4-methylbenzenecarbothioyl)amino]-5-(methylcarbamoylamino)cyclohexyl]amino]-2-oxoethyl]-5-(trifluoromethyl)benzamide Chemical compound C=1C(C(F)(F)F)=CC=C(N)C=1C(=O)NCC(=O)NC1CC(NC(=O)NC)CCC1NC(=S)C1=CC=C(C)C=C1 YATXTAOUEJKHFP-UHFFFAOYSA-N 0.000 claims 1
- HJNDNLATIRTJPP-UHFFFAOYSA-N 2-amino-n-[2-[[2-[(4-methylbenzenecarbothioyl)amino]-5-(propan-2-ylamino)cyclohexyl]amino]-2-oxoethyl]-5-(trifluoromethyl)benzamide Chemical compound C=1C(C(F)(F)F)=CC=C(N)C=1C(=O)NCC(=O)NC1CC(NC(C)C)CCC1NC(=S)C1=CC=C(C)C=C1 HJNDNLATIRTJPP-UHFFFAOYSA-N 0.000 claims 1
- YNZGCCYOKCXCOU-VOMIJIAVSA-N 2-amino-n-[2-oxo-2-[[(1r,2s)-2-[(4-sulfamoylbenzoyl)amino]cyclohexyl]amino]ethyl]-5-(trifluoromethyl)benzamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.NC1=CC=C(C(F)(F)F)C=C1C(=O)NCC(=O)N[C@H]1[C@@H](NC(=O)C=2C=CC(=CC=2)S(N)(=O)=O)CCCC1 YNZGCCYOKCXCOU-VOMIJIAVSA-N 0.000 claims 1
- 125000006022 2-methyl-2-propenyl group Chemical group 0.000 claims 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 1
- 125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 claims 1
- KOJORKRSCAZBFG-MOPGFXCFSA-N 3-chloro-n-[2-oxo-2-[[(1r,2s)-2-[(4-sulfamoylbenzoyl)amino]cyclohexyl]amino]ethyl]benzamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C(=O)N[C@@H]1[C@H](NC(=O)CNC(=O)C=2C=C(Cl)C=CC=2)CCCC1 KOJORKRSCAZBFG-MOPGFXCFSA-N 0.000 claims 1
- 125000001999 4-Methoxybenzoyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C(*)=O 0.000 claims 1
- 125000002672 4-bromobenzoyl group Chemical group BrC1=CC=C(C(=O)*)C=C1 0.000 claims 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 claims 1
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- MSVXWTVIPGCDDS-RBUKOAKNSA-N 4-sulfamoyl-n-[(1r,2s)-2-[[2-[[2-(trifluoromethyl)phenyl]carbamoylamino]acetyl]amino]cyclohexyl]benzamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C(=O)N[C@H]1[C@@H](NC(=O)CNC(=O)NC=2C(=CC=CC=2)C(F)(F)F)CCCC1 MSVXWTVIPGCDDS-RBUKOAKNSA-N 0.000 claims 1
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims 1
- QMIWFQOVLFFHNH-SJORKVTESA-N C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C(N)=C1C(=O)NCC(=O)N[C@H]1[C@@H](NC(=O)C=2C=CC(=CC=2)S(N)(=O)=O)CCCC1 Chemical compound C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C(N)=C1C(=O)NCC(=O)N[C@H]1[C@@H](NC(=O)C=2C=CC(=CC=2)S(N)(=O)=O)CCCC1 QMIWFQOVLFFHNH-SJORKVTESA-N 0.000 claims 1
- DMARNKGJAIPFIW-YADHBBJMSA-N CC(C)(C)OC(=O)NC1=CC=C(I)C=C1C(=O)NCC(=O)N[C@H]1[C@@H](NC(=O)C=2C=CC(=CC=2)S(N)(=O)=O)CCCC1 Chemical compound CC(C)(C)OC(=O)NC1=CC=C(I)C=C1C(=O)NCC(=O)N[C@H]1[C@@H](NC(=O)C=2C=CC(=CC=2)S(N)(=O)=O)CCCC1 DMARNKGJAIPFIW-YADHBBJMSA-N 0.000 claims 1
- 102000004497 CCR2 Receptors Human genes 0.000 claims 1
- 108010017312 CCR2 Receptors Proteins 0.000 claims 1
- 102100025721 Cytosolic carboxypeptidase 2 Human genes 0.000 claims 1
- 101000932634 Homo sapiens Cytosolic carboxypeptidase 2 Proteins 0.000 claims 1
- 101001033011 Mus musculus Granzyme C Proteins 0.000 claims 1
- MTOJTGRFQGIZNN-MOPGFXCFSA-N NC1=CC=C([N+]([O-])=O)C=C1C(=O)NCC(=O)N[C@H]1[C@@H](NC(=O)C=2C=CC(=CC=2)S(N)(=O)=O)CCCC1 Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C(=O)NCC(=O)N[C@H]1[C@@H](NC(=O)C=2C=CC(=CC=2)S(N)(=O)=O)CCCC1 MTOJTGRFQGIZNN-MOPGFXCFSA-N 0.000 claims 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 125000003943 azolyl group Chemical group 0.000 claims 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- QDMFGTCNZGNFCS-UHFFFAOYSA-N benzyl n-[4-[(4-methylbenzenecarbothioyl)amino]-3-[[2-[[2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-(trifluoromethyl)benzoyl]amino]acetyl]amino]cyclohexyl]carbamate Chemical compound C1=CC(C)=CC=C1C(=S)NC1C(NC(=O)CNC(=O)C=2C(=CC=C(C=2)C(F)(F)F)NC(=O)OC(C)(C)C)CC(NC(=O)OCC=2C=CC=CC=2)CC1 QDMFGTCNZGNFCS-UHFFFAOYSA-N 0.000 claims 1
- KVVJWZJAEUUMFT-UHFFFAOYSA-N benzyl n-[4-[(4-methylbenzenecarbothioyl)amino]-3-[[2-[[3-(trifluoromethyl)benzoyl]amino]acetyl]amino]cyclohexyl]carbamate Chemical compound C1=CC(C)=CC=C1C(=S)NC1C(NC(=O)CNC(=O)C=2C=C(C=CC=2)C(F)(F)F)CC(NC(=O)OCC=2C=CC=CC=2)CC1 KVVJWZJAEUUMFT-UHFFFAOYSA-N 0.000 claims 1
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- NLTVZTBYOOLVML-RBUKOAKNSA-N n-[(1r,2s)-2-[[2-[(3-chlorophenyl)sulfonylamino]acetyl]amino]cyclohexyl]-4-sulfamoylbenzamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C(=O)N[C@H]1[C@@H](NC(=O)CNS(=O)(=O)C=2C=C(Cl)C=CC=2)CCCC1 NLTVZTBYOOLVML-RBUKOAKNSA-N 0.000 claims 1
- XCYMOUNFNWTXMG-BJKOFHAPSA-N n-[2-[[(1r,2s)-2-[(4-methylsulfanylphenyl)methylamino]cyclohexyl]amino]-2-oxoethyl]-2-(propan-2-ylamino)-5-(trifluoromethyl)benzamide Chemical compound C1=CC(SC)=CC=C1CN[C@@H]1[C@H](NC(=O)CNC(=O)C=2C(=CC=C(C=2)C(F)(F)F)NC(C)C)CCCC1 XCYMOUNFNWTXMG-BJKOFHAPSA-N 0.000 claims 1
- OZDRIOLUCRUWMO-ZWKOTPCHSA-N n-[2-[[(1s,2r)-2-[(4-iodobenzoyl)amino]cyclopentyl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=CC(C(=O)NCC(=O)N[C@@H]2[C@@H](CCC2)NC(=O)C=2C=CC(I)=CC=2)=C1 OZDRIOLUCRUWMO-ZWKOTPCHSA-N 0.000 claims 1
- VQIUVUAYHYCGFF-UHFFFAOYSA-N n-[2-[[2-(4-aminocyclohexyl)-2-[(4-methylsulfonylbenzoyl)amino]cyclohexyl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(=O)NC1(C2CCC(N)CC2)C(NC(=O)CNC(=O)C=2C=C(C=CC=2)C(F)(F)F)CCCC1 VQIUVUAYHYCGFF-UHFFFAOYSA-N 0.000 claims 1
- ITDLGYCAPKXEFW-UHFFFAOYSA-N n-[2-[[2-[(4-chlorophenyl)methylamino]-4-(dimethylamino)cyclohexyl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=C(Cl)C=CC=1CNC1CC(N(C)C)CCC1NC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 ITDLGYCAPKXEFW-UHFFFAOYSA-N 0.000 claims 1
- SBVCGWCNGNNQLQ-UHFFFAOYSA-N n-[2-[[2-[(4-methylbenzenecarbothioyl)amino]-2-(propan-2-ylamino)cyclohexyl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide Chemical compound C=1C=C(C)C=CC=1C(=S)NC1(NC(C)C)CCCCC1NC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 SBVCGWCNGNNQLQ-UHFFFAOYSA-N 0.000 claims 1
- JOAVWSUCPHJBCQ-UHFFFAOYSA-N n-[2-[[2-[(4-methylbenzenecarbothioyl)amino]-3-(propan-2-ylamino)cyclohexyl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide Chemical compound C=1C=C(C)C=CC=1C(=S)NC1C(NC(C)C)CCCC1NC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 JOAVWSUCPHJBCQ-UHFFFAOYSA-N 0.000 claims 1
- HPHSYTAPFBQDSG-UHFFFAOYSA-N n-[2-[[2-[(4-methylsulfanylphenyl)methylamino]cyclohexyl]amino]-2-oxoethyl]-2-(morpholin-4-ylcarbamoylamino)-5-(trifluoromethyl)benzamide Chemical compound C1=CC(SC)=CC=C1CNC1C(NC(=O)CNC(=O)C=2C(=CC=C(C=2)C(F)(F)F)NC(=O)NN2CCOCC2)CCCC1 HPHSYTAPFBQDSG-UHFFFAOYSA-N 0.000 claims 1
- OZHPLCDNNYIYQW-UHFFFAOYSA-N n-[2-[[2-[(4-methylsulfanylphenyl)methylamino]cyclohexyl]amino]-2-oxoethyl]-2-(propan-2-ylcarbamoylamino)-5-(trifluoromethyl)benzamide Chemical compound C1=CC(SC)=CC=C1CNC1C(NC(=O)CNC(=O)C=2C(=CC=C(C=2)C(F)(F)F)NC(=O)NC(C)C)CCCC1 OZHPLCDNNYIYQW-UHFFFAOYSA-N 0.000 claims 1
- LNYVCJQXGXCQPV-UHFFFAOYSA-N n-[2-[[3-amino-2-[(4-methylbenzenecarbothioyl)amino]cyclohexyl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide Chemical compound C1=CC(C)=CC=C1C(=S)NC1C(NC(=O)CNC(=O)C=2C=C(C=CC=2)C(F)(F)F)CCCC1N LNYVCJQXGXCQPV-UHFFFAOYSA-N 0.000 claims 1
- IFKXICQDWOXINA-UHFFFAOYSA-N n-[2-[[4-(dimethylamino)-2-[(4-methoxyphenyl)methylamino]cyclohexyl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(OC)=CC=C1CNC1C(NC(=O)CNC(=O)C=2C=C(C=CC=2)C(F)(F)F)CCC(N(C)C)C1 IFKXICQDWOXINA-UHFFFAOYSA-N 0.000 claims 1
- NAFLWGAAXGLECD-UHFFFAOYSA-N n-[2-[[4-(dimethylamino)-2-[(4-methylphenyl)methylamino]cyclohexyl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=C(C)C=CC=1CNC1CC(N(C)C)CCC1NC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 NAFLWGAAXGLECD-UHFFFAOYSA-N 0.000 claims 1
- GCWNTIKZHLAOSB-UHFFFAOYSA-N n-[2-[[4-(dimethylamino)-2-[(4-methylsulfanylphenyl)methylamino]cyclohexyl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(SC)=CC=C1CNC1C(NC(=O)CNC(=O)C=2C=C(C=CC=2)C(F)(F)F)CCC(N(C)C)C1 GCWNTIKZHLAOSB-UHFFFAOYSA-N 0.000 claims 1
- QQMIHKHBKHNREZ-UHFFFAOYSA-N n-[2-[[4-amino-2-[(4-methylbenzenecarbothioyl)amino]cyclohexyl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide Chemical compound C1=CC(C)=CC=C1C(=S)NC1C(NC(=O)CNC(=O)C=2C=C(C=CC=2)C(F)(F)F)CCC(N)C1 QQMIHKHBKHNREZ-UHFFFAOYSA-N 0.000 claims 1
- OFHZAXKFSTWRHZ-MOPGFXCFSA-N n-[2-oxo-2-[[(1r,2s)-2-[(4-sulfamoylbenzoyl)amino]cyclohexyl]amino]ethyl]-3-(trifluoromethoxy)benzamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C(=O)N[C@@H]1[C@H](NC(=O)CNC(=O)C=2C=C(OC(F)(F)F)C=CC=2)CCCC1 OFHZAXKFSTWRHZ-MOPGFXCFSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 claims 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 102000005962 receptors Human genes 0.000 claims 1
- 108020003175 receptors Proteins 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- KTRBQJOKNOSNAH-PKTZIBPZSA-N tert-butyl n-[2-[[2-[[(1r,2s)-2-[(4-methylsulfonylphenyl)carbamoylamino]cyclohexyl]amino]-2-oxoethyl]carbamoyl]-4-(trifluoromethyl)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(C(F)(F)F)C=C1C(=O)NCC(=O)N[C@H]1[C@@H](NC(=O)NC=2C=CC(=CC=2)S(C)(=O)=O)CCCC1 KTRBQJOKNOSNAH-PKTZIBPZSA-N 0.000 claims 1
- UXADBJUARZMTJS-YADHBBJMSA-N tert-butyl n-methyl-n-[2-[[2-oxo-2-[[(1r,2s)-2-[(4-sulfamoylbenzoyl)amino]cyclohexyl]amino]ethyl]carbamoyl]-4-(trifluoromethyl)phenyl]carbamate Chemical compound CC(C)(C)OC(=O)N(C)C1=CC=C(C(F)(F)F)C=C1C(=O)NCC(=O)N[C@H]1[C@@H](NC(=O)C=2C=CC(=CC=2)S(N)(=O)=O)CCCC1 UXADBJUARZMTJS-YADHBBJMSA-N 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
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| US25690400P | 2000-12-20 | 2000-12-20 | |
| PCT/US2001/050252 WO2002060859A2 (en) | 2000-12-20 | 2001-12-20 | Cyclic derivatives as modulators of chemokine receptor activity |
Publications (2)
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| JP2004523534A JP2004523534A (ja) | 2004-08-05 |
| JP2004523534A5 true JP2004523534A5 (https=) | 2005-12-22 |
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| EP (1) | EP1343751A2 (https=) |
| JP (1) | JP2004523534A (https=) |
| AR (1) | AR035773A1 (https=) |
| CA (1) | CA2432369A1 (https=) |
| HU (1) | HUP0303652A2 (https=) |
| WO (1) | WO2002060859A2 (https=) |
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| US6706712B2 (en) * | 2000-12-20 | 2004-03-16 | Bristol-Myers Squibb Pharma Company | Cyclic derivatives as modulators of chemokine receptor activity |
| WO2003000657A1 (en) | 2001-06-20 | 2003-01-03 | Daiichi Pharmaceutical Co., Ltd. | Diamine derivatives |
| JP2005502700A (ja) * | 2001-09-13 | 2005-01-27 | エフ．ホフマン−ラ ロシュ アーゲー | Ｃｃｒ−３受容体アンタゴニストｖ |
| WO2003075853A2 (en) * | 2002-03-08 | 2003-09-18 | Bristol-Myers Squibb Company | Cyclic derivatives as modulators of chemokine receptor activity |
| US7067538B2 (en) | 2002-08-09 | 2006-06-27 | Warner-Lambert Company, Llc | MCP-1 receptor antagonists and methods of use thereof |
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| TW200508224A (en) * | 2003-02-12 | 2005-03-01 | Bristol Myers Squibb Co | Cyclic derivatives as modulators of chemokine receptor activity |
| US7291615B2 (en) * | 2003-05-01 | 2007-11-06 | Bristol-Myers Squibb Company | Cyclic derivatives as modulators of chemokine receptor activity |
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| CN102459226B (zh) | 2009-04-17 | 2014-09-17 | 詹森药业有限公司 | Ccr2的4-氮杂环丁烷基-1-杂原子连接的-环己烷拮抗剂 |
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-
2001
- 2001-12-20 US US10/027,644 patent/US6706712B2/en not_active Expired - Lifetime
- 2001-12-20 AR ARP010105969A patent/AR035773A1/es unknown
- 2001-12-20 WO PCT/US2001/050252 patent/WO2002060859A2/en not_active Ceased
- 2001-12-20 EP EP01997125A patent/EP1343751A2/en not_active Withdrawn
- 2001-12-20 HU HU0303652A patent/HUP0303652A2/hu unknown
- 2001-12-20 CA CA002432369A patent/CA2432369A1/en not_active Abandoned
- 2001-12-20 JP JP2002561010A patent/JP2004523534A/ja active Pending
-
2003
- 2003-11-12 US US10/706,448 patent/US7045521B2/en not_active Expired - Lifetime
-
2005
- 2005-12-22 US US11/315,385 patent/US7572813B2/en not_active Expired - Lifetime
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