JP2005506949A5 - - Google Patents
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- JP2005506949A5 JP2005506949A5 JP2002551518A JP2002551518A JP2005506949A5 JP 2005506949 A5 JP2005506949 A5 JP 2005506949A5 JP 2002551518 A JP2002551518 A JP 2002551518A JP 2002551518 A JP2002551518 A JP 2002551518A JP 2005506949 A5 JP2005506949 A5 JP 2005506949A5
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- JP
- Japan
- Prior art keywords
- amino
- methyl
- replaced
- crr
- 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 318
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 269
- 125000000217 alkyl group Chemical group 0.000 claims 204
- -1 cyclic acetal Chemical class 0.000 claims 173
- 125000002837 carbocyclic group Chemical group 0.000 claims 100
- 125000000304 alkynyl group Chemical group 0.000 claims 96
- 125000003342 alkenyl group Chemical group 0.000 claims 95
- 125000005842 heteroatom Chemical group 0.000 claims 85
- 229910052760 oxygen Inorganic materials 0.000 claims 85
- 229910052717 sulfur Inorganic materials 0.000 claims 85
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 63
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 52
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 52
- 229910052799 carbon Inorganic materials 0.000 claims 50
- 229910052739 hydrogen Inorganic materials 0.000 claims 50
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 44
- 125000000753 cycloalkyl group Chemical group 0.000 claims 44
- 125000000623 heterocyclic group Chemical group 0.000 claims 43
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 40
- 150000001875 compounds Chemical class 0.000 claims 35
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 35
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 34
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 32
- 125000002981 3-(trifluoromethyl)benzoyl group Chemical group FC(C=1C=C(C(=O)*)C=CC1)(F)F 0.000 claims 28
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 26
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 25
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 23
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 22
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 17
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 17
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 16
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 16
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 14
- 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 14
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 14
- 239000008194 pharmaceutical composition Substances 0.000 claims 14
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 14
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 13
- 230000002265 prevention Effects 0.000 claims 12
- 239000000203 mixture Substances 0.000 claims 11
- 201000001320 Atherosclerosis Diseases 0.000 claims 10
- 150000001408 amides Chemical class 0.000 claims 10
- 208000006673 asthma Diseases 0.000 claims 10
- 201000010099 disease Diseases 0.000 claims 10
- 208000037265 diseases, disorders, signs and symptoms 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
- 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 9
- 150000003951 lactams Chemical class 0.000 claims 9
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 8
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 8
- 230000000694 effects Effects 0.000 claims 8
- 125000001041 indolyl group Chemical group 0.000 claims 8
- 201000008383 nephritis Diseases 0.000 claims 8
- 125000004076 pyridyl group Chemical group 0.000 claims 8
- 125000004429 atom Chemical group 0.000 claims 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 7
- 125000000686 lactone group Chemical group 0.000 claims 7
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims 6
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims 6
- 206010001889 Alveolitis Diseases 0.000 claims 6
- 206010015150 Erythema Diseases 0.000 claims 6
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims 6
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 6
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 6
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 6
- 206010009887 colitis Diseases 0.000 claims 6
- 231100000321 erythema Toxicity 0.000 claims 6
- 201000001155 extrinsic allergic alveolitis Diseases 0.000 claims 6
- 125000002541 furyl group Chemical group 0.000 claims 6
- 208000022098 hypersensitivity pneumonitis Diseases 0.000 claims 6
- 125000002883 imidazolyl group Chemical group 0.000 claims 6
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 6
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 6
- 125000000842 isoxazolyl group Chemical group 0.000 claims 6
- 206010025135 lupus erythematosus Diseases 0.000 claims 6
- 230000003589 nefrotoxic effect Effects 0.000 claims 6
- 231100000381 nephrotoxic Toxicity 0.000 claims 6
- 125000002971 oxazolyl group Chemical group 0.000 claims 6
- 125000003373 pyrazinyl group Chemical group 0.000 claims 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 6
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 6
- 210000002966 serum Anatomy 0.000 claims 6
- 230000009885 systemic effect Effects 0.000 claims 6
- 125000003831 tetrazolyl group Chemical group 0.000 claims 6
- 125000000335 thiazolyl group Chemical group 0.000 claims 6
- 125000001544 thienyl group Chemical group 0.000 claims 6
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 5
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 5
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 5
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims 4
- 206010003210 Arteriosclerosis Diseases 0.000 claims 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 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
- 206010018364 Glomerulonephritis 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
- 208000011775 arteriosclerosis disease Diseases 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims 4
- 125000002757 morpholinyl group Chemical group 0.000 claims 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 4
- 125000003386 piperidinyl group Chemical group 0.000 claims 4
- 208000005069 pulmonary fibrosis Diseases 0.000 claims 4
- 239000000126 substance Substances 0.000 claims 4
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 4
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims 3
- 125000001624 naphthyl group Chemical group 0.000 claims 3
- 239000001294 propane Substances 0.000 claims 3
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims 3
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 2
- 206010065040 AIDS dementia complex Diseases 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
- 102000004497 CCR2 Receptors Human genes 0.000 claims 2
- 108010017312 CCR2 Receptors 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
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 2
- 239000005977 Ethylene Substances 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
- 206010037660 Pyrexia Diseases 0.000 claims 2
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims 2
- 208000029028 brain injury Diseases 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
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 claims 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims 2
- 150000002596 lactones Chemical class 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
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- PAMCRRDMORMCSM-UHFFFAOYSA-N n-(trifluoromethyl)benzamide Chemical compound FC(F)(F)NC(=O)C1=CC=CC=C1 PAMCRRDMORMCSM-UHFFFAOYSA-N 0.000 claims 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 201000008482 osteoarthritis Diseases 0.000 claims 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 2
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 claims 2
- IUGZYYHEZQQRHP-SFHVURJKSA-N (2s)-3-[(2,4-dimethylphenyl)methylamino]-2-[[2-[[3-(trifluoromethyl)benzoyl]amino]acetyl]amino]propanoic acid Chemical compound CC1=CC(C)=CC=C1CNC[C@@H](C(O)=O)NC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 IUGZYYHEZQQRHP-SFHVURJKSA-N 0.000 claims 1
- 125000000980 1H-indol-3-ylmethyl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C(C([H])([H])[*])C2=C1[H] 0.000 claims 1
- ZQPUIYWAGWJGCB-VWLOTQADSA-N 2-(butylamino)-n-[2-[[(2s)-1-(tert-butylamino)-3-[(2,4-dimethylphenyl)methylamino]-1-oxopropan-2-yl]amino]-2-oxoethyl]-5-(trifluoromethyl)benzamide Chemical compound CCCCNC1=CC=C(C(F)(F)F)C=C1C(=O)NCC(=O)N[C@H](C(=O)NC(C)(C)C)CNCC1=CC=C(C)C=C1C ZQPUIYWAGWJGCB-VWLOTQADSA-N 0.000 claims 1
- JJYNUAMIRAIFBQ-NRFANRHFSA-N 2-amino-n-[2-[[(2s)-1-(tert-butylamino)-3-[(2,4-dimethylphenyl)methylamino]-1-oxopropan-2-yl]amino]-2-oxoethyl]-5-(trifluoromethyl)benzamide Chemical compound CC1=CC(C)=CC=C1CNC[C@@H](C(=O)NC(C)(C)C)NC(=O)CNC(=O)C1=CC(C(F)(F)F)=CC=C1N JJYNUAMIRAIFBQ-NRFANRHFSA-N 0.000 claims 1
- VOVIAHPOWDMSIW-QHCPKHFHSA-N 2-amino-n-[2-[[(2s)-1-(tert-butylamino)-4-[(2,4-dimethylphenyl)methyl-methylamino]-1-oxobutan-2-yl]amino]-2-oxoethyl]-5-(trifluoromethyl)benzamide Chemical compound N([C@@H](CCN(C)CC=1C(=CC(C)=CC=1)C)C(=O)NC(C)(C)C)C(=O)CNC(=O)C1=CC(C(F)(F)F)=CC=C1N VOVIAHPOWDMSIW-QHCPKHFHSA-N 0.000 claims 1
- BVWYRWWDRBIVKJ-QFIPXVFZSA-N 2-amino-n-[2-[[(2s)-1-(tert-butylamino)-4-[(2,4-dimethylphenyl)methylamino]-1-oxobutan-2-yl]amino]-2-oxoethyl]-5-(trifluoromethyl)benzamide Chemical compound CC1=CC(C)=CC=C1CNCC[C@@H](C(=O)NC(C)(C)C)NC(=O)CNC(=O)C1=CC(C(F)(F)F)=CC=C1N BVWYRWWDRBIVKJ-QFIPXVFZSA-N 0.000 claims 1
- KWSFFNBRVWJEJK-INIZCTEOSA-N 2-amino-n-[2-[[(2s)-1-amino-3-[(4-bromophenyl)methylamino]-1-oxopropan-2-yl]amino]-2-oxoethyl]-5-(trifluoromethyl)benzamide Chemical compound C([C@@H](C(=O)N)NC(=O)CNC(=O)C=1C(=CC=C(C=1)C(F)(F)F)N)NCC1=CC=C(Br)C=C1 KWSFFNBRVWJEJK-INIZCTEOSA-N 0.000 claims 1
- HXOSNKMHCFTABH-FQEVSTJZSA-N 2-amino-n-[2-[[(2s)-3-[(4-bromo-2-methylphenyl)methylamino]-1-(tert-butylamino)-1-oxopropan-2-yl]amino]-2-oxoethyl]-5-(trifluoromethyl)benzamide Chemical compound CC1=CC(Br)=CC=C1CNC[C@@H](C(=O)NC(C)(C)C)NC(=O)CNC(=O)C1=CC(C(F)(F)F)=CC=C1N HXOSNKMHCFTABH-FQEVSTJZSA-N 0.000 claims 1
- WNDBBJRVNVBRDI-NDEPHWFRSA-N 3-(benzylamino)-n-[2-[[(2s)-1-(tert-butylamino)-3-[(2,4-dimethylphenyl)methylamino]-1-oxopropan-2-yl]amino]-2-oxoethyl]-5-(trifluoromethyl)benzamide Chemical compound CC1=CC(C)=CC=C1CNC[C@@H](C(=O)NC(C)(C)C)NC(=O)CNC(=O)C1=CC(NCC=2C=CC=CC=2)=CC(C(F)(F)F)=C1 WNDBBJRVNVBRDI-NDEPHWFRSA-N 0.000 claims 1
- ZEYAHFUIXMLOML-NRFANRHFSA-N 3-amino-n-[2-[[(2s)-1-(tert-butylamino)-3-[(2,4-dimethylphenyl)methylamino]-1-oxopropan-2-yl]amino]-2-oxoethyl]-5-(trifluoromethyl)benzamide Chemical compound CC1=CC(C)=CC=C1CNC[C@@H](C(=O)NC(C)(C)C)NC(=O)CNC(=O)C1=CC(N)=CC(C(F)(F)F)=C1 ZEYAHFUIXMLOML-NRFANRHFSA-N 0.000 claims 1
- LWEYMQQVLUOWLP-QFIPXVFZSA-N 3-amino-n-[2-[[(2s)-1-(tert-butylamino)-4-[(4-ethylphenyl)methylamino]-1-oxobutan-2-yl]amino]-2-oxoethyl]-5-(trifluoromethyl)benzamide Chemical compound C1=CC(CC)=CC=C1CNCC[C@@H](C(=O)NC(C)(C)C)NC(=O)CNC(=O)C1=CC(N)=CC(C(F)(F)F)=C1 LWEYMQQVLUOWLP-QFIPXVFZSA-N 0.000 claims 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 1
- 101000978374 Mus musculus C-C motif chemokine 12 Proteins 0.000 claims 1
- 208000030886 Traumatic Brain injury Diseases 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 210000004556 brain Anatomy 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- ZXYFWDUOJFDXFE-QHCPKHFHSA-N ethyl n-[3-[[2-[[(2s)-1-(tert-butylamino)-3-[(2,4-dimethylphenyl)methylamino]-1-oxopropan-2-yl]amino]-2-oxoethyl]carbamoyl]-5-(trifluoromethyl)phenyl]carbamate Chemical compound FC(F)(F)C1=CC(NC(=O)OCC)=CC(C(=O)NCC(=O)N[C@@H](CNCC=2C(=CC(C)=CC=2)C)C(=O)NC(C)(C)C)=C1 ZXYFWDUOJFDXFE-QHCPKHFHSA-N 0.000 claims 1
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 1
- 208000014674 injury Diseases 0.000 claims 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-M isobutyrate Chemical compound CC(C)C([O-])=O KQNPFQTWMSNSAP-UHFFFAOYSA-M 0.000 claims 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 claims 1
- GSINUEDWKBKBBC-HXUWFJFHSA-N n-[2-[[(2r)-2-[(2,4-dimethylphenyl)methylamino]-3-(ethylamino)-3-oxopropyl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide Chemical compound C([C@H](C(=O)NCC)NCC=1C(=CC(C)=CC=1)C)NC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 GSINUEDWKBKBBC-HXUWFJFHSA-N 0.000 claims 1
- JQTQSHYGYDYRLA-HXUWFJFHSA-N n-[2-[[(2r)-3-[(2,4-dimethylphenyl)methylamino]-1-(ethylamino)-1-oxopropan-2-yl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide Chemical compound C([C@H](C(=O)NCC)NC(=O)CNC(=O)C=1C=C(C=CC=1)C(F)(F)F)NCC1=CC=C(C)C=C1C JQTQSHYGYDYRLA-HXUWFJFHSA-N 0.000 claims 1
- KNCWDGUPSSDGDF-OAQYLSRUSA-N n-[2-[[(2r)-3-[(2,4-dimethylphenyl)methylamino]-1-[(1-hydroxy-2-methylpropan-2-yl)amino]-1-oxopropan-2-yl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide Chemical compound CC1=CC(C)=CC=C1CNC[C@H](C(=O)NC(C)(C)CO)NC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 KNCWDGUPSSDGDF-OAQYLSRUSA-N 0.000 claims 1
- WBXYZOVCGSOHBB-VWLOTQADSA-N n-[2-[[(2s)-1-(benzylamino)-3-[(2,4-dimethylphenyl)methylamino]-1-oxopropan-2-yl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide Chemical compound CC1=CC(C)=CC=C1CNC[C@@H](C(=O)NCC=1C=CC=CC=1)NC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 WBXYZOVCGSOHBB-VWLOTQADSA-N 0.000 claims 1
- LIWQUWGNWHRXDR-QFIPXVFZSA-N n-[2-[[(2s)-1-(cyclobutylamino)-3-[(2,4-dimethylphenyl)methylamino]-1-oxopropan-2-yl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide Chemical compound CC1=CC(C)=CC=C1CNC[C@@H](C(=O)NC1CCC1)NC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 LIWQUWGNWHRXDR-QFIPXVFZSA-N 0.000 claims 1
- HIKYYHMSDKVHTL-QFIPXVFZSA-N n-[2-[[(2s)-1-(tert-butylamino)-1-oxo-3-[(4-propan-2-ylphenyl)methylamino]propan-2-yl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide Chemical compound C1=CC(C(C)C)=CC=C1CNC[C@@H](C(=O)NC(C)(C)C)NC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 HIKYYHMSDKVHTL-QFIPXVFZSA-N 0.000 claims 1
- PVLOUXXXZOSIQQ-QFIPXVFZSA-N n-[2-[[(2s)-1-(tert-butylamino)-3-[(2,4-dimethylphenyl)methyl-methylamino]-1-oxopropan-2-yl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide Chemical compound N([C@@H](CN(C)CC=1C(=CC(C)=CC=1)C)C(=O)NC(C)(C)C)C(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 PVLOUXXXZOSIQQ-QFIPXVFZSA-N 0.000 claims 1
- VTNBYIKQXYVSCU-VWLOTQADSA-N n-[2-[[(2s)-1-(tert-butylamino)-3-[(2,4-dimethylphenyl)methylamino]-1-oxopropan-2-yl]amino]-2-oxoethyl]-2-(2-methylpropylamino)-5-(trifluoromethyl)benzamide Chemical compound CC(C)CNC1=CC=C(C(F)(F)F)C=C1C(=O)NCC(=O)N[C@H](C(=O)NC(C)(C)C)CNCC1=CC=C(C)C=C1C VTNBYIKQXYVSCU-VWLOTQADSA-N 0.000 claims 1
- ONYNFACZHHCTDA-QHCPKHFHSA-N n-[2-[[(2s)-1-(tert-butylamino)-3-[(2,4-dimethylphenyl)methylamino]-1-oxopropan-2-yl]amino]-2-oxoethyl]-2-(ethylamino)-5-(trifluoromethyl)benzamide Chemical compound CCNC1=CC=C(C(F)(F)F)C=C1C(=O)NCC(=O)N[C@H](C(=O)NC(C)(C)C)CNCC1=CC=C(C)C=C1C ONYNFACZHHCTDA-QHCPKHFHSA-N 0.000 claims 1
- VROGOHAHYOJKQR-QFIPXVFZSA-N n-[2-[[(2s)-1-(tert-butylamino)-3-[(2,4-dimethylphenyl)methylamino]-1-oxopropan-2-yl]amino]-2-oxoethyl]-2-(methylcarbamoylamino)-5-(trifluoromethyl)benzamide Chemical compound CNC(=O)NC1=CC=C(C(F)(F)F)C=C1C(=O)NCC(=O)N[C@H](C(=O)NC(C)(C)C)CNCC1=CC=C(C)C=C1C VROGOHAHYOJKQR-QFIPXVFZSA-N 0.000 claims 1
- OFWKNIMUUUFMJA-DEOSSOPVSA-N n-[2-[[(2s)-1-(tert-butylamino)-3-[(2,4-dimethylphenyl)methylamino]-1-oxopropan-2-yl]amino]-2-oxoethyl]-2-(propan-2-ylamino)-5-(trifluoromethyl)benzamide Chemical compound CC(C)NC1=CC=C(C(F)(F)F)C=C1C(=O)NCC(=O)N[C@H](C(=O)NC(C)(C)C)CNCC1=CC=C(C)C=C1C OFWKNIMUUUFMJA-DEOSSOPVSA-N 0.000 claims 1
- AWJUKDQERXTXHY-DEOSSOPVSA-N n-[2-[[(2s)-1-(tert-butylamino)-3-[(2,4-dimethylphenyl)methylamino]-1-oxopropan-2-yl]amino]-2-oxoethyl]-2-(propan-2-ylcarbamoylamino)-5-(trifluoromethyl)benzamide Chemical compound CC(C)NC(=O)NC1=CC=C(C(F)(F)F)C=C1C(=O)NCC(=O)N[C@H](C(=O)NC(C)(C)C)CNCC1=CC=C(C)C=C1C AWJUKDQERXTXHY-DEOSSOPVSA-N 0.000 claims 1
- MBHFMEXFXLGWPZ-DEOSSOPVSA-N n-[2-[[(2s)-1-(tert-butylamino)-3-[(2,4-dimethylphenyl)methylamino]-1-oxopropan-2-yl]amino]-2-oxoethyl]-2-(propylamino)-5-(trifluoromethyl)benzamide Chemical compound CCCNC1=CC=C(C(F)(F)F)C=C1C(=O)NCC(=O)N[C@H](C(=O)NC(C)(C)C)CNCC1=CC=C(C)C=C1C MBHFMEXFXLGWPZ-DEOSSOPVSA-N 0.000 claims 1
- JHAFSIDCLSAERO-VWLOTQADSA-N n-[2-[[(2s)-1-(tert-butylamino)-3-[(2,4-dimethylphenyl)methylamino]-1-oxopropan-2-yl]amino]-2-oxoethyl]-3-(2-methylpropylamino)-5-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC(NCC(C)C)=CC(C(=O)NCC(=O)N[C@@H](CNCC=2C(=CC(C)=CC=2)C)C(=O)NC(C)(C)C)=C1 JHAFSIDCLSAERO-VWLOTQADSA-N 0.000 claims 1
- USLMKTKWYUXICE-NRFANRHFSA-N n-[2-[[(2s)-1-(tert-butylamino)-3-[(2,4-dimethylphenyl)methylamino]-1-oxopropan-2-yl]amino]-2-oxoethyl]-3-(difluoromethyl)benzamide Chemical compound CC1=CC(C)=CC=C1CNC[C@@H](C(=O)NC(C)(C)C)NC(=O)CNC(=O)C1=CC=CC(C(F)F)=C1 USLMKTKWYUXICE-NRFANRHFSA-N 0.000 claims 1
- UGCKLKBKXFXRGZ-QFIPXVFZSA-N n-[2-[[(2s)-1-(tert-butylamino)-3-[(2,4-dimethylphenyl)methylamino]-1-oxopropan-2-yl]amino]-2-oxoethyl]-3-(methylamino)-5-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC(NC)=CC(C(=O)NCC(=O)N[C@@H](CNCC=2C(=CC(C)=CC=2)C)C(=O)NC(C)(C)C)=C1 UGCKLKBKXFXRGZ-QFIPXVFZSA-N 0.000 claims 1
- YZACLYAPEALTDY-DEOSSOPVSA-N n-[2-[[(2s)-1-(tert-butylamino)-3-[(2,4-dimethylphenyl)methylamino]-1-oxopropan-2-yl]amino]-2-oxoethyl]-3-(propylamino)-5-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC(NCCC)=CC(C(=O)NCC(=O)N[C@@H](CNCC=2C(=CC(C)=CC=2)C)C(=O)NC(C)(C)C)=C1 YZACLYAPEALTDY-DEOSSOPVSA-N 0.000 claims 1
- SBZAYKSXVNAATR-FQEVSTJZSA-N n-[2-[[(2s)-1-(tert-butylamino)-3-[(2-methylphenyl)methylamino]-1-oxopropan-2-yl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide Chemical compound CC1=CC=CC=C1CNC[C@@H](C(=O)NC(C)(C)C)NC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 SBZAYKSXVNAATR-FQEVSTJZSA-N 0.000 claims 1
- FRNSXNGJDFMFBE-NRFANRHFSA-N n-[2-[[(2s)-1-(tert-butylamino)-3-[(4-cyano-2-methylphenyl)methylamino]-1-oxopropan-2-yl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide Chemical compound CC1=CC(C#N)=CC=C1CNC[C@@H](C(=O)NC(C)(C)C)NC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 FRNSXNGJDFMFBE-NRFANRHFSA-N 0.000 claims 1
- CCCRXCYCHFZAEL-QFIPXVFZSA-N n-[2-[[(2s)-1-(tert-butylamino)-3-[(4-ethenyl-2-methylphenyl)methylamino]-1-oxopropan-2-yl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide Chemical compound CC1=CC(C=C)=CC=C1CNC[C@@H](C(=O)NC(C)(C)C)NC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 CCCRXCYCHFZAEL-QFIPXVFZSA-N 0.000 claims 1
- QRPKNKZUXDIPJG-QFIPXVFZSA-N n-[2-[[(2s)-1-(tert-butylamino)-3-[(4-ethyl-2-methylphenyl)methylamino]-1-oxopropan-2-yl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide Chemical compound CC1=CC(CC)=CC=C1CNC[C@@H](C(=O)NC(C)(C)C)NC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 QRPKNKZUXDIPJG-QFIPXVFZSA-N 0.000 claims 1
- RBTPLFXLAYIKKD-NRFANRHFSA-N n-[2-[[(2s)-1-(tert-butylamino)-3-[(4-ethylphenyl)methylamino]-1-oxopropan-2-yl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide Chemical compound C1=CC(CC)=CC=C1CNC[C@@H](C(=O)NC(C)(C)C)NC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 RBTPLFXLAYIKKD-NRFANRHFSA-N 0.000 claims 1
- JRQLJCVOBYNBHW-NRFANRHFSA-N n-[2-[[(2s)-1-(tert-butylamino)-3-[(4-methoxy-2-methylphenyl)methylamino]-1-oxopropan-2-yl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide Chemical compound CC1=CC(OC)=CC=C1CNC[C@@H](C(=O)NC(C)(C)C)NC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 JRQLJCVOBYNBHW-NRFANRHFSA-N 0.000 claims 1
- MZOVYGGMQJARQJ-FQEVSTJZSA-N n-[2-[[(2s)-1-(tert-butylamino)-3-[(4-methoxyphenyl)methylamino]-1-oxopropan-2-yl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide Chemical compound C1=CC(OC)=CC=C1CNC[C@@H](C(=O)NC(C)(C)C)NC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 MZOVYGGMQJARQJ-FQEVSTJZSA-N 0.000 claims 1
- MSSFMRMRFNNUBX-FQEVSTJZSA-N n-[2-[[(2s)-1-(tert-butylamino)-3-[(4-methylphenyl)methylamino]-1-oxopropan-2-yl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide Chemical compound C1=CC(C)=CC=C1CNC[C@@H](C(=O)NC(C)(C)C)NC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 MSSFMRMRFNNUBX-FQEVSTJZSA-N 0.000 claims 1
- GVPLREAHHSTSJS-FQEVSTJZSA-N n-[2-[[(2s)-1-(tert-butylamino)-3-[(4-methylsulfanylphenyl)methylamino]-1-oxopropan-2-yl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide Chemical compound C1=CC(SC)=CC=C1CNC[C@@H](C(=O)NC(C)(C)C)NC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 GVPLREAHHSTSJS-FQEVSTJZSA-N 0.000 claims 1
- OUQLHEYPUWVFQL-FQEVSTJZSA-N n-[2-[[(2s)-1-(tert-butylamino)-3-[(4-methylsulfonylphenyl)methylamino]-1-oxopropan-2-yl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide Chemical compound C([C@@H](C(=O)NC(C)(C)C)NC(=O)CNC(=O)C=1C=C(C=CC=1)C(F)(F)F)NCC1=CC=C(S(C)(=O)=O)C=C1 OUQLHEYPUWVFQL-FQEVSTJZSA-N 0.000 claims 1
- SYNQRMWRRDBJSC-SFHVURJKSA-N n-[2-[[(2s)-1-(tert-butylamino)-3-[(6-methoxypyridin-3-yl)methylamino]-1-oxopropan-2-yl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide Chemical compound C1=NC(OC)=CC=C1CNC[C@@H](C(=O)NC(C)(C)C)NC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 SYNQRMWRRDBJSC-SFHVURJKSA-N 0.000 claims 1
- RSVXEYXJYBBTOC-QFIPXVFZSA-N n-[2-[[(2s)-1-(tert-butylamino)-3-[[4-(dimethylamino)-2-methylphenyl]methylamino]-1-oxopropan-2-yl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide Chemical compound CC1=CC(N(C)C)=CC=C1CNC[C@@H](C(=O)NC(C)(C)C)NC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 RSVXEYXJYBBTOC-QFIPXVFZSA-N 0.000 claims 1
- MINWZMLSSYTQMV-NRFANRHFSA-N n-[2-[[(2s)-1-(tert-butylamino)-3-[[4-(dimethylamino)phenyl]methylamino]-1-oxopropan-2-yl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide Chemical compound C1=CC(N(C)C)=CC=C1CNC[C@@H](C(=O)NC(C)(C)C)NC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 MINWZMLSSYTQMV-NRFANRHFSA-N 0.000 claims 1
- GYWKVWRKXAGCMG-QFIPXVFZSA-N n-[2-[[(2s)-1-(tert-butylamino)-4-[(2,4-dimethylphenyl)methylamino]-1-oxobutan-2-yl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide Chemical compound CC1=CC(C)=CC=C1CNCC[C@@H](C(=O)NC(C)(C)C)NC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 GYWKVWRKXAGCMG-QFIPXVFZSA-N 0.000 claims 1
- KCLTXFAVDKVUKK-QFIPXVFZSA-N n-[2-[[(2s)-1-(tert-butylamino)-4-[(4-ethylphenyl)methylamino]-1-oxobutan-2-yl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide Chemical compound C1=CC(CC)=CC=C1CNCC[C@@H](C(=O)NC(C)(C)C)NC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 KCLTXFAVDKVUKK-QFIPXVFZSA-N 0.000 claims 1
- STJUEHWSZYBOFD-SFHVURJKSA-N n-[2-[[(2s)-1-amino-3-(1h-indol-3-ylmethylamino)-1-oxopropan-2-yl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide Chemical compound N([C@@H](CNCC=1C2=CC=CC=C2NC=1)C(=O)N)C(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 STJUEHWSZYBOFD-SFHVURJKSA-N 0.000 claims 1
- HTFCAKWNQNHBKJ-DEOSSOPVSA-N n-[2-[[(2s)-1-anilino-3-[(2,4-dimethylphenyl)methylamino]-1-oxopropan-2-yl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide Chemical compound CC1=CC(C)=CC=C1CNC[C@@H](C(=O)NC=1C=CC=CC=1)NC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 HTFCAKWNQNHBKJ-DEOSSOPVSA-N 0.000 claims 1
- SVGYEBVMEHPHCS-QFIPXVFZSA-N n-[2-[[(2s)-3-[(2,4-dimethylphenyl)methylamino]-1-(2-methylpropylamino)-1-oxopropan-2-yl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide Chemical compound C([C@@H](C(=O)NCC(C)C)NC(=O)CNC(=O)C=1C=C(C=CC=1)C(F)(F)F)NCC1=CC=C(C)C=C1C SVGYEBVMEHPHCS-QFIPXVFZSA-N 0.000 claims 1
- JQTQSHYGYDYRLA-FQEVSTJZSA-N n-[2-[[(2s)-3-[(2,4-dimethylphenyl)methylamino]-1-(ethylamino)-1-oxopropan-2-yl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide Chemical compound C([C@@H](C(=O)NCC)NC(=O)CNC(=O)C=1C=C(C=CC=1)C(F)(F)F)NCC1=CC=C(C)C=C1C JQTQSHYGYDYRLA-FQEVSTJZSA-N 0.000 claims 1
- KNCWDGUPSSDGDF-NRFANRHFSA-N n-[2-[[(2s)-3-[(2,4-dimethylphenyl)methylamino]-1-[(1-hydroxy-2-methylpropan-2-yl)amino]-1-oxopropan-2-yl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide Chemical compound CC1=CC(C)=CC=C1CNC[C@@H](C(=O)NC(C)(C)CO)NC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 KNCWDGUPSSDGDF-NRFANRHFSA-N 0.000 claims 1
- BBDNWXOVFUSDDU-NRFANRHFSA-N n-[2-[[(2s)-3-[(2,4-dimethylphenyl)methylamino]-1-[(1-methylcyclopropyl)amino]-1-oxopropan-2-yl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide Chemical compound CC1=CC(C)=CC=C1CNC[C@@H](C(=O)NC1(C)CC1)NC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 BBDNWXOVFUSDDU-NRFANRHFSA-N 0.000 claims 1
- BRRZJXMTXJQZFT-NRFANRHFSA-N n-[2-[[(2s)-3-[(2,4-dimethylphenyl)methylamino]-1-oxo-1-(propan-2-ylamino)propan-2-yl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide Chemical compound C([C@@H](C(=O)NC(C)C)NC(=O)CNC(=O)C=1C=C(C=CC=1)C(F)(F)F)NCC1=CC=C(C)C=C1C BRRZJXMTXJQZFT-NRFANRHFSA-N 0.000 claims 1
- VKEIRGOCEUAYTA-FQEVSTJZSA-N n-[2-[[(2s)-3-[(3-amino-4-methylphenyl)methylamino]-1-(tert-butylamino)-1-oxopropan-2-yl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(N)C(C)=CC=C1CNC[C@@H](C(=O)NC(C)(C)C)NC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 VKEIRGOCEUAYTA-FQEVSTJZSA-N 0.000 claims 1
- DSNRPHZPZPKEDF-FQEVSTJZSA-N n-[2-[[(2s)-3-[(4-bromo-2-methylphenyl)methylamino]-1-(tert-butylamino)-1-oxopropan-2-yl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide Chemical compound CC1=CC(Br)=CC=C1CNC[C@@H](C(=O)NC(C)(C)C)NC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 DSNRPHZPZPKEDF-FQEVSTJZSA-N 0.000 claims 1
- SIBIFTUPQFSVBV-IBGZPJMESA-N n-[2-[[(2s)-3-[(4-bromophenyl)methylamino]-1-(tert-butylamino)-1-oxopropan-2-yl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide Chemical compound C([C@@H](C(=O)NC(C)(C)C)NC(=O)CNC(=O)C=1C=C(C=CC=1)C(F)(F)F)NCC1=CC=C(Br)C=C1 SIBIFTUPQFSVBV-IBGZPJMESA-N 0.000 claims 1
- ASXQCRGLQIGFLC-SFHVURJKSA-N n-[2-[[(2s)-3-[(4-chlorophenyl)methylamino]-1-(ethylamino)-1-oxopropan-2-yl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide Chemical compound C([C@@H](C(=O)NCC)NC(=O)CNC(=O)C=1C=C(C=CC=1)C(F)(F)F)NCC1=CC=C(Cl)C=C1 ASXQCRGLQIGFLC-SFHVURJKSA-N 0.000 claims 1
- HHCXTVSNSLXIJU-QFIPXVFZSA-N n-[2-[[(2s)-4-[(2,4-dimethylphenyl)methyl-methylamino]-1-(ethylamino)-1-oxobutan-2-yl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide Chemical compound C([C@@H](C(=O)NCC)NC(=O)CNC(=O)C=1C=C(C=CC=1)C(F)(F)F)CN(C)CC1=CC=C(C)C=C1C HHCXTVSNSLXIJU-QFIPXVFZSA-N 0.000 claims 1
- IZWURKUUGCCQGO-NRFANRHFSA-N n-[2-[[(2s)-4-[(2,4-dimethylphenyl)methylamino]-1-(ethylamino)-1-oxobutan-2-yl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide Chemical compound C([C@@H](C(=O)NCC)NC(=O)CNC(=O)C=1C=C(C=CC=1)C(F)(F)F)CNCC1=CC=C(C)C=C1C IZWURKUUGCCQGO-NRFANRHFSA-N 0.000 claims 1
- RNGBECAFIOPBQI-VGSWGCGISA-N n-[2-[[(2s,3r)-3-[(2,4-dimethylphenyl)methylamino]-1-(ethylamino)-1-oxobutan-2-yl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide Chemical compound N([C@H](C(=O)NCC)[C@@H](C)NCC=1C(=CC(C)=CC=1)C)C(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 RNGBECAFIOPBQI-VGSWGCGISA-N 0.000 claims 1
- OYHVXDINLMMECT-VLIAUNLRSA-N n-[2-[[(2s,3r)-3-[(4-bromophenyl)methylamino]-1-(ethylamino)-1-oxobutan-2-yl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide Chemical compound N([C@H](C(=O)NCC)[C@@H](C)NCC=1C=CC(Br)=CC=1)C(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 OYHVXDINLMMECT-VLIAUNLRSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- IPWFJLQDVFKJDU-UHFFFAOYSA-N pentanamide Chemical compound CCCCC(N)=O IPWFJLQDVFKJDU-UHFFFAOYSA-N 0.000 claims 1
- DHHVAGZRUROJKS-UHFFFAOYSA-N phentermine Chemical compound CC(C)(N)CC1=CC=CC=C1 DHHVAGZRUROJKS-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- TWEGKTGMILCJSR-DEOSSOPVSA-N tert-butyl n-[2-[[2-[[(2s)-1-(tert-butylamino)-3-[(2,4-dimethylphenyl)methylamino]-1-oxopropan-2-yl]amino]-2-oxoethyl]carbamoyl]-4-(trifluoromethyl)phenyl]carbamate Chemical compound CC1=CC(C)=CC=C1CNC[C@@H](C(=O)NC(C)(C)C)NC(=O)CNC(=O)C1=CC(C(F)(F)F)=CC=C1NC(=O)OC(C)(C)C TWEGKTGMILCJSR-DEOSSOPVSA-N 0.000 claims 1
- IYOCTVFQXVEVKD-SANMLTNESA-N tert-butyl n-[2-[[2-[[(2s)-1-(tert-butylamino)-4-[(2,4-dimethylphenyl)methyl-methylamino]-1-oxobutan-2-yl]amino]-2-oxoethyl]carbamoyl]-4-(trifluoromethyl)phenyl]carbamate Chemical compound N([C@@H](CCN(C)CC=1C(=CC(C)=CC=1)C)C(=O)NC(C)(C)C)C(=O)CNC(=O)C1=CC(C(F)(F)F)=CC=C1NC(=O)OC(C)(C)C IYOCTVFQXVEVKD-SANMLTNESA-N 0.000 claims 1
- KNVYVYDCIKDXSF-VWLOTQADSA-N tert-butyl n-[2-[[2-[[(2s)-1-(tert-butylamino)-4-[(2,4-dimethylphenyl)methylamino]-1-oxobutan-2-yl]amino]-2-oxoethyl]carbamoyl]-4-(trifluoromethyl)phenyl]carbamate Chemical compound CC1=CC(C)=CC=C1CNCC[C@@H](C(=O)NC(C)(C)C)NC(=O)CNC(=O)C1=CC(C(F)(F)F)=CC=C1NC(=O)OC(C)(C)C KNVYVYDCIKDXSF-VWLOTQADSA-N 0.000 claims 1
- 230000008733 trauma Effects 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25685500P | 2000-12-20 | 2000-12-20 | |
| PCT/US2001/050619 WO2002050019A2 (en) | 2000-12-20 | 2001-12-20 | Diamines as modulators of chemokine receptor activity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005506949A JP2005506949A (ja) | 2005-03-10 |
| JP2005506949A5 true JP2005506949A5 (https=) | 2005-12-22 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002551518A Withdrawn JP2005506949A (ja) | 2000-12-20 | 2001-12-20 | ケモカイン受容体の調節剤としてのジアミン |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US6974836B2 (https=) |
| EP (1) | EP1351924A2 (https=) |
| JP (1) | JP2005506949A (https=) |
| AR (1) | AR035720A1 (https=) |
| AU (1) | AU2002241724A1 (https=) |
| CA (1) | CA2432908A1 (https=) |
| HU (1) | HUP0303540A2 (https=) |
| WO (1) | WO2002050019A2 (https=) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002050019A2 (en) | 2000-12-20 | 2002-06-27 | Bristol-Myers Squibb Pharma Co. | Diamines as modulators of chemokine receptor activity |
| US6706712B2 (en) | 2000-12-20 | 2004-03-16 | Bristol-Myers Squibb Pharma Company | Cyclic derivatives as modulators of chemokine receptor activity |
| WO2003075853A2 (en) | 2002-03-08 | 2003-09-18 | Bristol-Myers Squibb Company | Cyclic derivatives as modulators of chemokine receptor activity |
| US7338975B2 (en) * | 2003-02-12 | 2008-03-04 | Bristol-Myers Squibb Co. | Lactams as modulators of chemokine receptor activity |
| TW200508224A (en) | 2003-02-12 | 2005-03-01 | Bristol Myers Squibb Co | Cyclic derivatives as modulators of chemokine receptor activity |
| WO2004094386A1 (en) | 2003-03-28 | 2004-11-04 | Eli Lilly And Company | Isoquinoline-5-sulfonic acid amides as inhibitors of akt (protein kinase b) |
| US7291615B2 (en) | 2003-05-01 | 2007-11-06 | Bristol-Myers Squibb Company | Cyclic derivatives as modulators of chemokine receptor activity |
| US7230133B2 (en) | 2003-05-01 | 2007-06-12 | Bristol-Myers Squibb Company | Malonamides and malonamide derivatives as modulators of chemokine receptor activity |
| US7163937B2 (en) * | 2003-08-21 | 2007-01-16 | Bristol-Myers Squibb Company | Cyclic derivatives as modulators of chemokine receptor activity |
| US7863317B2 (en) * | 2003-08-21 | 2011-01-04 | Bristol-Myers Squibb Company | Lactams of alkylated acyclic diamine derivatives as modulators of chemokine receptor activity |
| US7378409B2 (en) * | 2003-08-21 | 2008-05-27 | Bristol-Myers Squibb Company | Substituted cycloalkylamine derivatives as modulators of chemokine receptor activity |
| US7317019B2 (en) | 2003-08-21 | 2008-01-08 | Bristol Myers Squibb Co. | N-alkylated diaminopropane derivatives as modulators of chemokine receptor activity |
| US20050043392A1 (en) * | 2003-08-21 | 2005-02-24 | Carter Percy H. | Lactams of alkylated acyclic diamine derivatives as modulators of chemokine receptor activity |
| EP1676837A4 (en) * | 2003-10-08 | 2008-09-10 | Teijin Pharma Ltd | METHOD FOR PRODUCING AN AMINOPYRROLIDINE DERIVATIVE AND AN INTERMEDIATE COMPOUND |
| US7449477B2 (en) | 2003-11-25 | 2008-11-11 | Eli Lilly And Company | 7-phenyl-isoquinoline-5-sulfonylamino derivatives as inhibitors of akt (protein kinase B) |
| US7381738B2 (en) | 2004-02-19 | 2008-06-03 | Bristol-Myers Squibb Company | Substituted bicycloalkylamine derivatives as modulators of chemokine receptor activity |
| US7288563B2 (en) | 2004-02-19 | 2007-10-30 | Bristol-Myers Squibb Company | Substituted bicycloalkylamine derivatives as modulators of chemokine receptor activity |
| US7479496B2 (en) | 2004-02-19 | 2009-01-20 | Bristol-Myers Squibb Company | Substituted spiro azabicyclics as modulators of chemokine receptor activity |
| US7230022B2 (en) | 2004-02-19 | 2007-06-12 | Bristol-Myers Squibb Company | Substituted fused bicyclic amines as modulators of chemokine receptor activity |
| SI1771463T1 (sl) * | 2004-07-16 | 2008-06-30 | Lonza Ag | Postopek za sintezo peptidov |
| EP1811991B1 (en) | 2004-11-10 | 2018-11-07 | Genzyme Corporation | Treatment of type 2 diabetes using inhibitors of glycosphingolipid synthesis |
| WO2006074265A2 (en) * | 2005-01-06 | 2006-07-13 | Merck & Co., Inc. | Drug combination therapy and pharmaceutical compositions for treating inflammatory disorders |
| SI2032134T1 (sl) | 2006-05-09 | 2015-10-30 | Genzyme Corporation | Postopki zdravljenja bolezni zamaščenih jeter, ki obsegajo inhibicijo sintezo glukosfingolipida |
| US7671062B2 (en) * | 2006-07-28 | 2010-03-02 | Bristol-Myers Squibb Company | Modulators of chemokine receptor activity, crystalline forms and process |
| US7687508B2 (en) * | 2006-07-28 | 2010-03-30 | Bristol-Myers Squibb Company | Cyclic derivatives as modulators of chemokine receptor activity |
| US7629351B2 (en) * | 2006-07-28 | 2009-12-08 | Bristol-Myers Squibb Company | N-((1R,2S,5R)-5-(tert-butylamino)-2-((S)-2-oxo-3-(6-(trifluoromethyl)quinazolin-4-ylamino) pyrrolidin-1-yl)cyclohexyl)acetamide and other modulators of chemokine receptor activity, crystalline forms and process |
| US20080076120A1 (en) * | 2006-09-14 | 2008-03-27 | Millennium Pharmaceuticals, Inc. | Methods for the identification, evaluation and treatment of patients having CC-Chemokine receptor 2 (CCR-2) mediated disorders |
| EP2594564B1 (en) * | 2007-05-31 | 2016-09-28 | Genzyme Corporation | 2-acylaminopropanol-type glucosylceramide synthase inhibitors |
| CN101888840A (zh) | 2007-10-05 | 2010-11-17 | 简詹姆公司 | 使用脑酰胺衍生物治疗多囊性肾疾病的方法 |
| CA2731685A1 (en) | 2008-07-28 | 2010-02-04 | Genzyme Corporation | Glucosylceramide synthase inhibition for the treatment of collapsing glomerulopathy and other glomerular disease |
| EP3078373A1 (en) | 2008-10-03 | 2016-10-12 | Genzyme Corporation | 2-acylaminopropanol-type glucosylceramide synthase inhibitor |
| US8383812B2 (en) * | 2009-10-13 | 2013-02-26 | Bristol-Myers Squibb Company | N-((1R,2S,5R)-5-(tert-butylamino)-2-((S)-3-(7-tert-butylpyrazolo[1,5-A][1,3,5]triazin-4-ylamino)-2-oxopyrrolidin-1-yl)cyclohexyl)acetamide, a dual modulator of chemokine receptor activity, crystalline forms and processes |
Family Cites Families (54)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US235836A (en) * | 1880-12-21 | Lathe-chuck | ||
| US43392A (en) * | 1864-07-05 | Improvement in excavators | ||
| US65147A (en) * | 1867-05-28 | winants and john f | ||
| US216434A (en) * | 1879-06-10 | Improvement in machines for making sheet-metal can-bodies | ||
| US235835A (en) * | 1880-12-21 | Alfred wilbue | ||
| US110736A (en) * | 1871-01-03 | Improvement in combined cultivators and planters | ||
| US54627A (en) * | 1866-05-08 | Improvement in hay-loaders | ||
| US54626A (en) * | 1866-05-08 | Improvement in spirit-levels | ||
| US186143A (en) * | 1877-01-09 | Improvement in combined wash-stand and bureau | ||
| DE3635907A1 (de) | 1986-10-22 | 1988-04-28 | Merck Patent Gmbh | Hydroxy-aminosaeurederivate |
| JP2867450B2 (ja) | 1989-08-17 | 1999-03-08 | 吉富製薬株式会社 | アルキレンビスアミド化合物 |
| CA2036781A1 (en) * | 1990-02-22 | 1991-08-23 | Fujio Antoku | Triamine derivatives and their acid-addition salts |
| GB9201755D0 (en) | 1992-01-28 | 1992-03-11 | British Bio Technology | Compounds |
| IL106197A (en) | 1992-07-30 | 1999-11-30 | Cor Therapeutics Inc | Agagonists for the rhombin receptors and pharmaceutical preparations containing them |
| US5538997A (en) * | 1993-03-12 | 1996-07-23 | Sandoz Ltd. | 2,4-diamino-3-hydroxycarboxylic acid derivatives |
| IT1270882B (it) | 1993-10-05 | 1997-05-13 | Isagro Srl | Oligopeptidi ad attivita' fungicida |
| US6306840B1 (en) | 1995-01-23 | 2001-10-23 | Biogen, Inc. | Cell adhesion inhibitors |
| EP0731107A1 (en) | 1995-02-13 | 1996-09-11 | Takeda Chemical Industries, Ltd. | Production of aldehyde derivatives |
| EP0824543A1 (en) | 1995-05-10 | 1998-02-25 | Chiroscience Limited | Peptide compounds which inhibit metalloproteinase and tnf liberation, and their therapeutic use |
| US5710171A (en) | 1995-05-24 | 1998-01-20 | Merck & Co., Inc. | Bisphenyl inhibitors of farnesyl-protein transferase |
| TW438591B (en) | 1995-06-07 | 2001-06-07 | Arris Pharm Corp | Reversible cysteine protease inhibitors |
| US5770620A (en) | 1995-06-19 | 1998-06-23 | Ontogen Corporation | Aryl acrylic acid derivatives useful as protein tyrosine phosphatase inhibitors |
| AU711104B2 (en) | 1995-06-22 | 1999-10-07 | Novo Nordisk A/S | Compounds with growth hormone releasing properties |
| US6100423A (en) | 1995-08-30 | 2000-08-08 | G. D. Searle & Co. | Amino benzenepropanoic acid compounds and derivatives thereof |
| IL123164A (en) | 1995-08-30 | 2001-03-19 | Searle & Co | Meta-guanidine urea thiourea or azacyclic amino benzoic acid derivatives and pharmaceutical compositions containing them |
| US5843904A (en) | 1995-12-20 | 1998-12-01 | Vertex Pharmaceuticals, Inc. | Inhibitors of interleukin-1βconverting enzyme |
| US6011052A (en) | 1996-04-30 | 2000-01-04 | Warner-Lambert Company | Pyrazolone derivatives as MCP-1 antagonists |
| US6686353B1 (en) * | 1996-05-20 | 2004-02-03 | Teijin Intellectual Property Center Limited | Diarylalkyl cyclic diamine derivatives as chemokine receptor antagonists |
| WO1998006703A1 (en) | 1996-08-14 | 1998-02-19 | Warner-Lambert Company | 2-phenyl benzimidazole derivatives as mcp-1 antagonists |
| GB9716657D0 (en) | 1997-08-07 | 1997-10-15 | Zeneca Ltd | Chemical compounds |
| GB9716656D0 (en) * | 1997-08-07 | 1997-10-15 | Zeneca Ltd | Chemical compounds |
| US6150378A (en) | 1997-10-07 | 2000-11-21 | Cephalon, Inc. | Peptidyl-containing α-ketoamide cysteine and serine protease inhibitors |
| SK285729B6 (sk) | 1997-11-18 | 2007-07-06 | Teijin Pharma Limited | Zlúčenina derivátov cyklických amínov a jej použitie |
| US6048861A (en) | 1997-12-17 | 2000-04-11 | Merck & Co., Inc. | Integrin receptor antagonists |
| US6028087A (en) | 1998-01-21 | 2000-02-22 | Smithkline Beecham Corporation | Platelet aggregation inhibiting compounds |
| GB9803228D0 (en) | 1998-02-17 | 1998-04-08 | Zeneca Ltd | Chemical compounds |
| GB9803226D0 (en) | 1998-02-17 | 1998-04-08 | Zeneca Ltd | Chemical compounds |
| US6541208B1 (en) | 1998-03-17 | 2003-04-01 | University Of Maryland Biotechnology Institute | Diagnostic method for distinguishing HIV-associated dementia from other forms of dementia |
| WO2000042071A2 (en) | 1999-01-12 | 2000-07-20 | Cambridge University Technical Services Ltd. | Compounds and methods to inhibit or augment an inflammatory response |
| GB9902461D0 (en) | 1999-02-05 | 1999-03-24 | Zeneca Ltd | Chemical compounds |
| AU4796700A (en) | 1999-05-13 | 2000-12-05 | Dupont Pharmaceuticals Research Laboratories, Inc. | Ureido-substituted cyclic amine derivatives and their use as drug |
| ATE277903T1 (de) | 1999-05-14 | 2004-10-15 | Bristol Myers Squibb Pharma Re | Zyklische aminderivate und ihre verwendung |
| WO2002050019A2 (en) | 2000-12-20 | 2002-06-27 | Bristol-Myers Squibb Pharma Co. | Diamines as modulators of chemokine receptor activity |
| US6706712B2 (en) | 2000-12-20 | 2004-03-16 | Bristol-Myers Squibb Pharma Company | Cyclic derivatives as modulators of chemokine receptor activity |
| WO2003075853A2 (en) | 2002-03-08 | 2003-09-18 | Bristol-Myers Squibb Company | Cyclic derivatives as modulators of chemokine receptor activity |
| TW200508224A (en) | 2003-02-12 | 2005-03-01 | Bristol Myers Squibb Co | Cyclic derivatives as modulators of chemokine receptor activity |
| US7338975B2 (en) * | 2003-02-12 | 2008-03-04 | Bristol-Myers Squibb Co. | Lactams as modulators of chemokine receptor activity |
| JP3655616B2 (ja) | 2003-03-19 | 2005-06-02 | ファナック株式会社 | 射出成形機 |
| US7230133B2 (en) | 2003-05-01 | 2007-06-12 | Bristol-Myers Squibb Company | Malonamides and malonamide 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 |
| US7163937B2 (en) | 2003-08-21 | 2007-01-16 | Bristol-Myers Squibb Company | Cyclic derivatives as modulators of chemokine receptor activity |
| US20050043392A1 (en) | 2003-08-21 | 2005-02-24 | Carter Percy H. | Lactams of alkylated acyclic diamine derivatives as modulators of chemokine receptor activity |
| US7378409B2 (en) | 2003-08-21 | 2008-05-27 | Bristol-Myers Squibb Company | Substituted cycloalkylamine derivatives as modulators of chemokine receptor activity |
| US7317019B2 (en) | 2003-08-21 | 2008-01-08 | Bristol Myers Squibb Co. | N-alkylated diaminopropane derivatives as modulators of chemokine receptor activity |
-
2001
- 2001-12-20 WO PCT/US2001/050619 patent/WO2002050019A2/en not_active Ceased
- 2001-12-20 JP JP2002551518A patent/JP2005506949A/ja not_active Withdrawn
- 2001-12-20 CA CA002432908A patent/CA2432908A1/en not_active Abandoned
- 2001-12-20 HU HU0303540A patent/HUP0303540A2/hu unknown
- 2001-12-20 EP EP01988415A patent/EP1351924A2/en not_active Withdrawn
- 2001-12-20 US US10/027,505 patent/US6974836B2/en not_active Expired - Lifetime
- 2001-12-20 AU AU2002241724A patent/AU2002241724A1/en not_active Abandoned
- 2001-12-20 AR ARP010105968A patent/AR035720A1/es unknown
-
2005
- 2005-07-14 US US11/181,436 patent/US7449493B2/en not_active Expired - Lifetime
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