JP2004523490A5 - - Google Patents
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- JP2004523490A5 JP2004523490A5 JP2002546496A JP2002546496A JP2004523490A5 JP 2004523490 A5 JP2004523490 A5 JP 2004523490A5 JP 2002546496 A JP2002546496 A JP 2002546496A JP 2002546496 A JP2002546496 A JP 2002546496A JP 2004523490 A5 JP2004523490 A5 JP 2004523490A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- compound
- amino
- dichlorophenyl
- alkenyl
- 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.)
- Pending
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- -1 C 1 -C 4 alkylthio Chemical group 0.000 claims 50
- 125000003342 alkenyl group Chemical group 0.000 claims 47
- 150000001875 compounds Chemical class 0.000 claims 47
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 38
- 229910052760 oxygen Inorganic materials 0.000 claims 36
- 125000000217 alkyl group Chemical group 0.000 claims 35
- 229910052717 sulfur Inorganic materials 0.000 claims 35
- 229920006395 saturated elastomer Polymers 0.000 claims 29
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 28
- 125000000304 alkynyl group Chemical group 0.000 claims 26
- 229910052757 nitrogen Inorganic materials 0.000 claims 25
- 125000001424 substituent group Chemical group 0.000 claims 23
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical group O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 20
- 125000000623 heterocyclic group Chemical group 0.000 claims 19
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 17
- 125000004043 oxo group Chemical group O=* 0.000 claims 15
- VVNCNSJFMMFHPL-VKHMYHEASA-N D-penicillamine Chemical group CC(C)(S)[C@@H](N)C(O)=O VVNCNSJFMMFHPL-VKHMYHEASA-N 0.000 claims 14
- 125000003118 aryl group Chemical group 0.000 claims 11
- 239000008194 pharmaceutical composition Substances 0.000 claims 11
- 239000002585 base Substances 0.000 claims 10
- 239000003085 diluting agent Substances 0.000 claims 10
- 125000005843 halogen group Chemical group 0.000 claims 10
- 125000005842 heteroatom Chemical group 0.000 claims 10
- 239000000546 pharmaceutical excipient Substances 0.000 claims 10
- 125000002619 bicyclic group Chemical group 0.000 claims 9
- 125000004432 carbon atom Chemical group C* 0.000 claims 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims 9
- 125000002950 monocyclic group Chemical group 0.000 claims 9
- 125000000165 tricyclic carbocycle group Chemical group 0.000 claims 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 7
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 6
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 6
- 125000003282 alkyl amino group Chemical group 0.000 claims 6
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims 6
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims 6
- 125000001769 aryl amino group Chemical group 0.000 claims 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 6
- 125000004802 cyanophenyl group Chemical group 0.000 claims 6
- 230000003647 oxidation Effects 0.000 claims 6
- 238000007254 oxidation reaction Methods 0.000 claims 6
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 5
- 239000003795 chemical substances by application Substances 0.000 claims 5
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims 3
- 150000001412 amines Chemical class 0.000 claims 3
- 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 3
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 3
- 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 3
- 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 claims 2
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims 2
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims 2
- 201000004384 Alopecia Diseases 0.000 claims 2
- ZYUZLEUJKZZXNN-UHFFFAOYSA-N C1=CC(CC(N)C(O)=O)=CC=C1OS(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 Chemical group C1=CC(CC(N)C(O)=O)=CC=C1OS(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 ZYUZLEUJKZZXNN-UHFFFAOYSA-N 0.000 claims 2
- 208000001840 Dandruff Diseases 0.000 claims 2
- 241001674048 Phthiraptera Species 0.000 claims 2
- 239000000654 additive Substances 0.000 claims 2
- 230000000996 additive effect Effects 0.000 claims 2
- 229940035674 anesthetics Drugs 0.000 claims 2
- 239000000058 anti acne agent Substances 0.000 claims 2
- 239000003242 anti bacterial agent Substances 0.000 claims 2
- 230000001142 anti-diarrhea Effects 0.000 claims 2
- 239000002260 anti-inflammatory agent Substances 0.000 claims 2
- 229940121363 anti-inflammatory agent Drugs 0.000 claims 2
- 229940124340 antiacne agent Drugs 0.000 claims 2
- 229940088710 antibiotic agent Drugs 0.000 claims 2
- 229940125714 antidiarrheal agent Drugs 0.000 claims 2
- 239000003793 antidiarrheal agent Substances 0.000 claims 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 2
- 239000003139 biocide Substances 0.000 claims 2
- 239000003193 general anesthetic agent Substances 0.000 claims 2
- 239000007952 growth promoter Substances 0.000 claims 2
- 239000000118 hair dye Substances 0.000 claims 2
- 208000024963 hair loss Diseases 0.000 claims 2
- 230000003676 hair loss Effects 0.000 claims 2
- 239000003112 inhibitor Substances 0.000 claims 2
- 239000003410 keratolytic agent Substances 0.000 claims 2
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 claims 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 2
- 229920002554 vinyl polymer Polymers 0.000 claims 2
- ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 claims 1
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 claims 1
- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 claims 1
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 claims 1
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 claims 1
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 claims 1
- IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 claims 1
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 claims 1
- LJIOTBMDLVHTBO-CUYJMHBOSA-N (2s)-2-amino-n-[(1r,2r)-1-cyano-2-[4-[4-(4-methylpiperazin-1-yl)sulfonylphenyl]phenyl]cyclopropyl]butanamide Chemical compound CC[C@H](N)C(=O)N[C@]1(C#N)C[C@@H]1C1=CC=C(C=2C=CC(=CC=2)S(=O)(=O)N2CCN(C)CC2)C=C1 LJIOTBMDLVHTBO-CUYJMHBOSA-N 0.000 claims 1
- STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 claims 1
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 claims 1
- UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 claims 1
- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 claims 1
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 claims 1
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 claims 1
- VALSAKIMMYEMHC-UHFFFAOYSA-N 1-[3,5-bis(trifluoromethyl)phenyl]-3-[2-[[3,5-bis(trifluoromethyl)phenyl]carbamothioylamino]cyclohexyl]thiourea Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(NC(=S)NC2C(CCCC2)NC(=S)NC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)=C1 VALSAKIMMYEMHC-UHFFFAOYSA-N 0.000 claims 1
- AKQBDUFMEAVBPB-UHFFFAOYSA-N 1-[3-[2,2-bis(4-chlorophenyl)ethenyl]phenyl]-3-(3,5-dichlorophenyl)thiourea Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC(Cl)=CC=1)=CC1=CC=CC(NC(=S)NC=2C=C(Cl)C=C(Cl)C=2)=C1 AKQBDUFMEAVBPB-UHFFFAOYSA-N 0.000 claims 1
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 claims 1
- DMENPCXKXUTTGM-UHFFFAOYSA-N 1-[[3-[[3,5-bis(trifluoromethyl)phenyl]methoxy]benzoyl]amino]-3-(3,5-dichlorophenyl)urea Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(COC=2C=C(C=CC=2)C(=O)NNC(=O)NC=2C=C(Cl)C=C(Cl)C=2)=C1 DMENPCXKXUTTGM-UHFFFAOYSA-N 0.000 claims 1
- PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 claims 1
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 claims 1
- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- AHNOVNYOUPQVRX-UHFFFAOYSA-N 3,5-dichlorobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 AHNOVNYOUPQVRX-UHFFFAOYSA-N 0.000 claims 1
- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 claims 1
- BGAJNPLDJJBRHK-UHFFFAOYSA-N 3-[2-[5-(3-chloro-4-propan-2-yloxyphenyl)-1,3,4-thiadiazol-2-yl]-3-methyl-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl]propanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NN=C(N2C(=C3CN(CCC(O)=O)CCC3=N2)C)S1 BGAJNPLDJJBRHK-UHFFFAOYSA-N 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- VPAPSEYKVPULKR-UHFFFAOYSA-N 6-[3-(trifluoromethyl)phenyl]pyridine-3-carboxylic acid Chemical group N1=CC(C(=O)O)=CC=C1C1=CC=CC(C(F)(F)F)=C1 VPAPSEYKVPULKR-UHFFFAOYSA-N 0.000 claims 1
- BQXUPNKLZNSUMC-YUQWMIPFSA-N CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 Chemical compound CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 BQXUPNKLZNSUMC-YUQWMIPFSA-N 0.000 claims 1
- GAMXFERFIAARTK-UHFFFAOYSA-N Clc1cccc(Cl)c1NNC=O Chemical compound Clc1cccc(Cl)c1NNC=O GAMXFERFIAARTK-UHFFFAOYSA-N 0.000 claims 1
- 229940126639 Compound 33 Drugs 0.000 claims 1
- 229940127007 Compound 39 Drugs 0.000 claims 1
- CYESCLHCWJKRKM-UHFFFAOYSA-N DCPU Natural products NC(=O)NC1=CC=C(Cl)C(Cl)=C1 CYESCLHCWJKRKM-UHFFFAOYSA-N 0.000 claims 1
- DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical compound S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 claims 1
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 claims 1
- ZNSPHKJFQDEABI-NZQKXSOJSA-N Nc1nc(O[C@H](c2ccc(Cl)cc2-c2ccccc2)C(F)(F)F)cc(n1)N1CCC2(CN[C@@H](C2)C(O)=O)CC1 Chemical compound Nc1nc(O[C@H](c2ccc(Cl)cc2-c2ccccc2)C(F)(F)F)cc(n1)N1CCC2(CN[C@@H](C2)C(O)=O)CC1 ZNSPHKJFQDEABI-NZQKXSOJSA-N 0.000 claims 1
- PNUZDKCDAWUEGK-CYZMBNFOSA-N Sitafloxacin Chemical compound C([C@H]1N)N(C=2C(=C3C(C(C(C(O)=O)=CN3[C@H]3[C@H](C3)F)=O)=CC=2F)Cl)CC11CC1 PNUZDKCDAWUEGK-CYZMBNFOSA-N 0.000 claims 1
- LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 claims 1
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 claims 1
- PSLUFJFHTBIXMW-WYEYVKMPSA-N [(3r,4ar,5s,6s,6as,10s,10ar,10bs)-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-6-(2-pyridin-2-ylethylcarbamoyloxy)-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-5-yl] acetate Chemical compound O([C@@H]1[C@@H]([C@]2(O[C@](C)(CC(=O)[C@]2(O)[C@@]2(C)[C@@H](O)CCC(C)(C)[C@@H]21)C=C)C)OC(=O)C)C(=O)NCCC1=CC=CC=N1 PSLUFJFHTBIXMW-WYEYVKMPSA-N 0.000 claims 1
- MYKKOQUUFBGQQS-UHFFFAOYSA-N [3-[(3,5-dichlorobenzoyl)amino]phenyl] 2,3,4,5,6-pentafluorobenzenesulfonate Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1S(=O)(=O)OC1=CC=CC(NC(=O)C=2C=C(Cl)C=C(Cl)C=2)=C1 MYKKOQUUFBGQQS-UHFFFAOYSA-N 0.000 claims 1
- XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 claims 1
- KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 229940125904 compound 1 Drugs 0.000 claims 1
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- 229940127573 compound 38 Drugs 0.000 claims 1
- 229940126540 compound 41 Drugs 0.000 claims 1
- 229940125936 compound 42 Drugs 0.000 claims 1
- 229940125898 compound 5 Drugs 0.000 claims 1
- LMKPHJYTFHAGHK-UHFFFAOYSA-N cyclodrine Chemical compound C1CCCC1(O)C(C(=O)OCCN(CC)CC)C1=CC=CC=C1 LMKPHJYTFHAGHK-UHFFFAOYSA-N 0.000 claims 1
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 claims 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 claims 1
- RENRQMCACQEWFC-UGKGYDQZSA-N lnp023 Chemical compound C1([C@H]2N(CC=3C=4C=CNC=4C(C)=CC=3OC)CC[C@@H](C2)OCC)=CC=C(C(O)=O)C=C1 RENRQMCACQEWFC-UGKGYDQZSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- LIOIEZMXBWILQR-UHFFFAOYSA-N n-(3,5-dichloroanilino)formamide Chemical compound ClC1=CC(Cl)=CC(NNC=O)=C1 LIOIEZMXBWILQR-UHFFFAOYSA-N 0.000 claims 1
- BRRRAHQHZQXNPK-UHFFFAOYSA-N n-(3,5-dichlorophenyl)-n-[3-[(3,5-dichlorophenyl)carbamothioylamino]cyclopentyl]formamide Chemical compound ClC1=CC(Cl)=CC(NC(=S)NC2CC(CC2)N(C=O)C=2C=C(Cl)C=C(Cl)C=2)=C1 BRRRAHQHZQXNPK-UHFFFAOYSA-N 0.000 claims 1
- KMCIUMDVNKSTOI-UHFFFAOYSA-N n-[3-[5-(3,4-dichloroanilino)-1,3,4-oxadiazol-2-yl]phenyl]-5-phenylpentanamide Chemical compound C1=C(Cl)C(Cl)=CC=C1NC1=NN=C(C=2C=C(NC(=O)CCCCC=3C=CC=CC=3)C=CC=2)O1 KMCIUMDVNKSTOI-UHFFFAOYSA-N 0.000 claims 1
- NBXCSVYPBLSJLT-UHFFFAOYSA-N n-[3-[5-(3,4-dichloroanilino)-1,3,4-thiadiazol-2-yl]phenyl]-5-phenylpentanamide Chemical compound C1=C(Cl)C(Cl)=CC=C1NC1=NN=C(C=2C=C(NC(=O)CCCCC=3C=CC=CC=3)C=CC=2)S1 NBXCSVYPBLSJLT-UHFFFAOYSA-N 0.000 claims 1
- RUQYMWMCSNFYOI-UHFFFAOYSA-N n-[3-[[(3,4-dichlorophenyl)carbamothioylamino]carbamoyl]phenyl]-5-phenylpentanamide Chemical compound C1=C(Cl)C(Cl)=CC=C1NC(=S)NNC(=O)C1=CC=CC(NC(=O)CCCCC=2C=CC=CC=2)=C1 RUQYMWMCSNFYOI-UHFFFAOYSA-N 0.000 claims 1
- ABHSJKQOOHUWIM-UHFFFAOYSA-N n-[3-[[(3,4-dichlorophenyl)carbamothioylamino]carbamoyl]phenyl]-7-phenylheptanamide Chemical compound C1=C(Cl)C(Cl)=CC=C1NC(=S)NNC(=O)C1=CC=CC(NC(=O)CCCCCCC=2C=CC=CC=2)=C1 ABHSJKQOOHUWIM-UHFFFAOYSA-N 0.000 claims 1
- IZHGHKUQSOSVDD-UHFFFAOYSA-N n-[3-[bis[(3,5-dichlorophenyl)sulfonyl]amino]phenyl]-n-(3,5-dichlorophenyl)formamide Chemical compound ClC1=CC(Cl)=CC(N(C=O)C=2C=C(C=CC=2)N(S(=O)(=O)C=2C=C(Cl)C=C(Cl)C=2)S(=O)(=O)C=2C=C(Cl)C=C(Cl)C=2)=C1 IZHGHKUQSOSVDD-UHFFFAOYSA-N 0.000 claims 1
- ZYPQHUVZQJCQAC-UHFFFAOYSA-N n-[4-[[(3,4-dichlorophenyl)carbamothioylamino]carbamoyl]phenyl]-5-phenylpentanamide Chemical compound C1=C(Cl)C(Cl)=CC=C1NC(=S)NNC(=O)C(C=C1)=CC=C1NC(=O)CCCCC1=CC=CC=C1 ZYPQHUVZQJCQAC-UHFFFAOYSA-N 0.000 claims 1
- PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
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| DE10121003A1 (de) | 2001-04-28 | 2002-12-19 | Aventis Pharma Gmbh | Anthranilsäureamide, Verfahren zur Herstellung, ihrer Verwendung als Medikament sowie sie enthaltende pharmazeutische Zubereitungen |
| MXPA02010231A (es) * | 2001-11-27 | 2004-12-13 | Warner Lambert Co | Inhibidores aminotransferasa dependientes de aminoacidos de cadena ramificada y su uso en el tratamiento de las enfermedades neurodegenerativas. |
| EP1402888A1 (en) * | 2002-09-18 | 2004-03-31 | Jerini AG | The use of substituted carbocyclic compounds as rotamases inhibitors |
| SI2656854T1 (sl) | 2003-02-04 | 2015-09-30 | Cornell Research Foundation, Inc. | Uporabe aromatsko-kationskega peptida |
| US20040192738A1 (en) * | 2003-03-18 | 2004-09-30 | Aventis Pharma Deutschland Gmbh | 2-(Butyl-1-sulfonylamino)-N-[1(R)-(6-methoxypyridin-3-yl)propyl] benzamide, its use as a medicament, and pharmaceutical preparations comprising it |
| CA2531485C (en) * | 2003-07-07 | 2013-03-26 | Merck Patent Gmbh | Malonamide derivatives |
| TW200510305A (en) * | 2003-07-25 | 2005-03-16 | Wyeth Corp | Process for the preparation of CPLA2 inhibitors |
| BRPI0415179A (pt) | 2003-10-07 | 2006-11-28 | Renovis Inc | derivados de amida como ligandos de canal de ìon e composições farmacêuticas e métodos de empregar as mesmas |
| CA2851972C (en) | 2004-01-23 | 2015-06-23 | Cornell Research Foundation, Inc. | Methods for reducing oxidative damage |
| WO2006078986A2 (en) * | 2005-01-21 | 2006-07-27 | Vertex Pharmaceuticals Incorporated | Quorum sensing modulators |
| US7576099B2 (en) | 2005-02-28 | 2009-08-18 | Renovis, Inc. | Amide derivatives as ion-channel ligands and pharmaceutical compositions and methods of using the same |
| US7312181B2 (en) * | 2005-04-08 | 2007-12-25 | Cropsolution, Inc. | Acylated thiosemicarbazides as herbicides |
| US7915304B2 (en) * | 2006-10-24 | 2011-03-29 | Congenia S.R.L. | Phenyl substituted maleimides as medicaments for blocking degenerative tissue damages by inhibiting MPT |
| US8063034B2 (en) * | 2007-01-29 | 2011-11-22 | Santen Pharmaceutical Co., Ltd. | Oxadiazole derivatives and thiadiazole derivatives having neovascularization inhibitory activity |
| US8273900B2 (en) | 2008-08-07 | 2012-09-25 | Novartis Ag | Organic compounds |
| US8697911B2 (en) | 2010-07-07 | 2014-04-15 | Boehringer Ingelheim International Gmbh | Rho kinase inhibitors |
| US9079880B2 (en) | 2010-07-07 | 2015-07-14 | Boehringer Ingelheim International Gmbh | Rho kinase inhibitors |
| EP2630144B1 (en) | 2010-10-19 | 2016-09-07 | Boehringer Ingelheim International GmbH | Rho kinase inhibitors |
| WO2013066836A1 (en) * | 2011-10-31 | 2013-05-10 | Glaxosmithkline Llc | Compounds and methods |
| US9216954B2 (en) * | 2012-01-27 | 2015-12-22 | National University Corporation University Of Toyama | Serine racemase inhibitor |
| CA2866910A1 (en) | 2012-03-20 | 2013-09-26 | Adamed Sp. Z O.O. | Sulphonamide derivatives of benzylamine for the treatment of cns diseases |
| US9296754B2 (en) | 2013-03-15 | 2016-03-29 | Novartis Ag | Compounds and compositions for the treatment of parasitic diseases |
| US9233961B2 (en) | 2013-03-15 | 2016-01-12 | Novartis Ag | Compounds and compositions for the treatment of parasitic diseases |
| CA2904794C (en) | 2013-03-15 | 2021-11-23 | Peter Walter | Modulators of the eif2alpha pathway |
| US9186361B2 (en) | 2013-03-15 | 2015-11-17 | Novartis Ag | Compounds and compositions for the treatment of parasitic diseases |
| DK3054936T5 (da) | 2013-10-10 | 2024-03-18 | Eastern Virginia Medical School | 4-((2-hydroxy-3-methoxybenzyl)amino) benzensulfonamid derivater som 12-lipoxygenase inhibitorer |
| TWI674263B (zh) | 2013-12-19 | 2019-10-11 | 瑞士商諾華公司 | 用於治療寄生蟲疾病之化合物及組合物 |
| CN104557691B (zh) * | 2014-12-11 | 2017-10-24 | 中国农业大学 | 一种3‑胺酰双酰肼衍生物及其制备方法和应用 |
| WO2017160709A1 (en) * | 2016-03-14 | 2017-09-21 | West Virginia University | Water soluble haloanilide calcium-release calcium channel inhibitory compounds and methods to control bone erosion and inflammation associated with arthritides |
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| NL254871A (https=) * | 1959-08-14 | |||
| US3062813A (en) * | 1960-05-13 | 1962-11-06 | Pennsalt Chemicals Corp | Novel synthesis of sulfonamides |
| GB1075166A (en) * | 1965-06-01 | 1967-07-12 | Monsanto Chemicals | Fluorinated aromatic diamides |
| ZA98825B (en) * | 1997-02-27 | 1998-10-19 | Guilford Pharm Inc | Method of using neurotrophic carbamates and ureas |
| WO2001017953A1 (en) * | 1999-09-08 | 2001-03-15 | Guilford Pharmaceuticals Inc. | Non-peptidic cyclophilin binding compounds and their use |
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2001
- 2001-11-28 CA CA002430409A patent/CA2430409A1/en not_active Abandoned
- 2001-11-28 WO PCT/US2001/044449 patent/WO2002044126A2/en not_active Ceased
- 2001-11-28 AU AU2002225767A patent/AU2002225767A1/en not_active Abandoned
- 2001-11-28 US US09/994,927 patent/US20020127605A1/en not_active Abandoned
- 2001-11-28 JP JP2002546496A patent/JP2004523490A/ja active Pending
- 2001-11-28 EP EP01995251A patent/EP1339668A2/en not_active Withdrawn
- 2001-11-28 MX MXPA03004821A patent/MXPA03004821A/es unknown
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