JP2014506877A5 - - Google Patents
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- Publication number
- JP2014506877A5 JP2014506877A5 JP2013547843A JP2013547843A JP2014506877A5 JP 2014506877 A5 JP2014506877 A5 JP 2014506877A5 JP 2013547843 A JP2013547843 A JP 2013547843A JP 2013547843 A JP2013547843 A JP 2013547843A JP 2014506877 A5 JP2014506877 A5 JP 2014506877A5
- Authority
- JP
- Japan
- Prior art keywords
- fluoro
- amide
- indol
- carbamoyl
- chloro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- -1 hydroxy, amino Chemical group 0.000 claims 580
- 229910052739 hydrogen Inorganic materials 0.000 claims 109
- 239000001257 hydrogen Substances 0.000 claims 90
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 85
- SLJSRCNCQDNSEY-IMJSIDKUSA-N (2s,4s)-4-aminopyrrolidine-1,2-dicarboxylic acid Chemical compound N[C@H]1C[C@@H](C(O)=O)N(C(O)=O)C1 SLJSRCNCQDNSEY-IMJSIDKUSA-N 0.000 claims 71
- LYKWZKBLNOCJMA-UHFFFAOYSA-N (3-chloro-2-fluorophenyl)methanamine Chemical compound NCC1=CC=CC(Cl)=C1F LYKWZKBLNOCJMA-UHFFFAOYSA-N 0.000 claims 69
- 150000002431 hydrogen Chemical class 0.000 claims 67
- 229910052736 halogen Inorganic materials 0.000 claims 66
- GXFAYZBQUMULJS-DMTCNVIQSA-N (2s,4r)-4-fluoropyrrolidine-1,2-dicarboxylic acid Chemical compound OC(=O)[C@@H]1C[C@@H](F)CN1C(O)=O GXFAYZBQUMULJS-DMTCNVIQSA-N 0.000 claims 65
- 150000002367 halogens Chemical class 0.000 claims 65
- XEAZDLMCKFROGX-WDCZJNDASA-N (1r,3s,5r)-2-azabicyclo[3.1.0]hexane-2,3-dicarboxylic acid Chemical compound OC(=O)N1[C@H](C(=O)O)C[C@H]2C[C@H]21 XEAZDLMCKFROGX-WDCZJNDASA-N 0.000 claims 59
- 125000001424 substituent group Chemical group 0.000 claims 45
- 125000005843 halogen group Chemical group 0.000 claims 44
- 229910052799 carbon Inorganic materials 0.000 claims 43
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 37
- 229910052760 oxygen Inorganic materials 0.000 claims 33
- 125000000623 heterocyclic group Chemical group 0.000 claims 29
- OAWXZFGKDDFTGS-BYPYZUCNSA-N (2s)-pyrrolidine-1,2-dicarboxylic acid Chemical compound OC(=O)[C@@H]1CCCN1C(O)=O OAWXZFGKDDFTGS-BYPYZUCNSA-N 0.000 claims 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 27
- 125000000217 alkyl group Chemical group 0.000 claims 25
- 229910052757 nitrogen Inorganic materials 0.000 claims 25
- 229910052717 sulfur Inorganic materials 0.000 claims 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 23
- 150000001875 compounds Chemical class 0.000 claims 23
- 125000003545 alkoxy group Chemical group 0.000 claims 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims 20
- 125000001153 fluoro group Chemical group F* 0.000 claims 20
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims 20
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims 19
- 125000005842 heteroatom Chemical group 0.000 claims 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 18
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 16
- UVSHQGAAWFMJDK-VKHMYHEASA-N (2S)-1,3-thiazolidine-2,3-dicarboxylic acid Chemical compound OC(=O)[C@@H]1SCCN1C(O)=O UVSHQGAAWFMJDK-VKHMYHEASA-N 0.000 claims 15
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 15
- 150000001408 amides Chemical class 0.000 claims 14
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 14
- BJFPYGGTDAYECS-UHFFFAOYSA-N (3-chlorophenyl)methanamine Chemical compound NCC1=CC=CC(Cl)=C1 BJFPYGGTDAYECS-UHFFFAOYSA-N 0.000 claims 13
- 125000006413 ring segment Chemical group 0.000 claims 13
- 150000003536 tetrazoles Chemical class 0.000 claims 13
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 12
- 239000002253 acid Substances 0.000 claims 12
- 150000001204 N-oxides Chemical class 0.000 claims 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 10
- 125000004076 pyridyl group Chemical group 0.000 claims 10
- 125000004434 sulfur atom Chemical group 0.000 claims 10
- 150000001721 carbon Chemical group 0.000 claims 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 9
- 125000001072 heteroaryl group Chemical group 0.000 claims 9
- JWHOQZUREKYPBY-UHFFFAOYSA-N rubonic acid Natural products CC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CCC(=O)C(C)(C)C5CC(=O)C34C)C2C1)C(=O)O JWHOQZUREKYPBY-UHFFFAOYSA-N 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims 7
- 239000011593 sulfur Substances 0.000 claims 7
- LCJSRFXMMUVIJO-LYRGGWFBSA-N (1r,3s,5r)-2-[2-(3-acetylindol-1-yl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carboxylic acid Chemical compound C12=CC=CC=C2C(C(=O)C)=CN1CC(=O)N1[C@H](C(O)=O)C[C@H]2C[C@H]21 LCJSRFXMMUVIJO-LYRGGWFBSA-N 0.000 claims 6
- AWXDDXPSAPKTTK-DMTCNVIQSA-N (2s,3r)-3-hydroxypyrrolidine-1,2-dicarboxylic acid Chemical compound O[C@@H]1CCN(C(O)=O)[C@@H]1C(O)=O AWXDDXPSAPKTTK-DMTCNVIQSA-N 0.000 claims 6
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
- 239000005711 Benzoic acid Substances 0.000 claims 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 6
- 125000003342 alkenyl group Chemical group 0.000 claims 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 6
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- 239000001301 oxygen Substances 0.000 claims 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 6
- ZXNDWVDSVLPGNK-YUPRTTJUSA-N (1s,2s,5r)-3-azabicyclo[3.1.0]hexane-2,3-dicarboxylic acid Chemical compound C1N(C(O)=O)[C@H](C(=O)O)[C@H]2C[C@H]21 ZXNDWVDSVLPGNK-YUPRTTJUSA-N 0.000 claims 5
- UHTCLRWCFCIEDS-FFWSUHOLSA-N (2S,4S)-4-(aminomethyl)-4-fluoropyrrolidine-1,2-dicarboxylic acid Chemical compound NC[C@@]1(F)C[C@@H](C(O)=O)N(C(O)=O)C1 UHTCLRWCFCIEDS-FFWSUHOLSA-N 0.000 claims 5
- FJKLVSCNTJZZLB-MHTLYPKNSA-N (2s,4r)-4-fluoro-4-methylpyrrolidine-1,2-dicarboxylic acid Chemical compound C[C@@]1(F)C[C@@H](C(O)=O)N(C(O)=O)C1 FJKLVSCNTJZZLB-MHTLYPKNSA-N 0.000 claims 5
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 5
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 5
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 5
- 208000035475 disorder Diseases 0.000 claims 5
- 238000000034 method Methods 0.000 claims 5
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 5
- ZXNDWVDSVLPGNK-WDCZJNDASA-N (1r,2s,5s)-3-azabicyclo[3.1.0]hexane-2,3-dicarboxylic acid Chemical compound C1N(C(O)=O)[C@H](C(=O)O)[C@@H]2C[C@@H]21 ZXNDWVDSVLPGNK-WDCZJNDASA-N 0.000 claims 4
- OHZUCDHZOHSBPZ-UHFFFAOYSA-N (2,3-difluorophenyl)methanamine Chemical compound NCC1=CC=CC(F)=C1F OHZUCDHZOHSBPZ-UHFFFAOYSA-N 0.000 claims 4
- QMZKFOSMBYTKSY-WHFBIAKZSA-N (2S,4S)-4-(hydroxymethyl)pyrrolidine-1,2-dicarboxylic acid Chemical compound OC[C@H]1C[C@@H](C(O)=O)N(C(O)=O)C1 QMZKFOSMBYTKSY-WHFBIAKZSA-N 0.000 claims 4
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 4
- ZCJAYDKWZAWMPR-UHFFFAOYSA-N 1-chloro-2-fluorobenzene Chemical compound FC1=CC=CC=C1Cl ZCJAYDKWZAWMPR-UHFFFAOYSA-N 0.000 claims 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 4
- 241000051616 Ulmus minor Species 0.000 claims 4
- 206010064930 age-related macular degeneration Diseases 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 150000004702 methyl esters Chemical class 0.000 claims 4
- 125000004193 piperazinyl group Chemical group 0.000 claims 4
- 125000003386 piperidinyl group Chemical group 0.000 claims 4
- 125000001544 thienyl group Chemical group 0.000 claims 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 4
- HIOKSLZQCATFPU-UUEMRFSQSA-N (1R,3S,5S)-5-(hydroxymethyl)-2-azabicyclo[3.1.0]hexane-2,3-dicarboxylic acid Chemical compound C([C@H](N1C(O)=O)C(O)=O)[C@]2(CO)[C@H]1C2 HIOKSLZQCATFPU-UUEMRFSQSA-N 0.000 claims 3
- SVEKDOPPNJXIJM-DMTCNVIQSA-N (2s,3r)-3-aminopyrrolidine-1,2-dicarboxylic acid Chemical compound N[C@@H]1CCN(C(O)=O)[C@@H]1C(O)=O SVEKDOPPNJXIJM-DMTCNVIQSA-N 0.000 claims 3
- JHMMSHOPBJYVAA-RRQGHBQHSA-N (2s,3s,4s)-1-[2-(3-acetylindol-1-yl)acetyl]-4-fluoro-3-methoxypyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@@H]1[C@H](OC)[C@@H](F)CN1C(=O)CN1C2=CC=CC=C2C(C(C)=O)=C1 JHMMSHOPBJYVAA-RRQGHBQHSA-N 0.000 claims 3
- LSMBIAVEACWSEH-YGRLFVJLSA-N (2s,4r)-4-fluoro-1-[2-[3-(2-hydroxyacetyl)indol-1-yl]acetyl]pyrrolidine-2-carboxylic acid Chemical compound C12=CC=CC=C2C(C(=O)CO)=CN1CC(=O)N1C[C@H](F)C[C@H]1C(O)=O LSMBIAVEACWSEH-YGRLFVJLSA-N 0.000 claims 3
- VKKBGPPYRLLFIL-UHFFFAOYSA-N (3-chloro-2,6-difluorophenyl)methanamine Chemical compound NCC1=C(F)C=CC(Cl)=C1F VKKBGPPYRLLFIL-UHFFFAOYSA-N 0.000 claims 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 3
- HPJALMWOZYIZGE-UHFFFAOYSA-N 2-oxa-6-azaspiro[3.3]heptane Chemical compound C1NCC11COC1 HPJALMWOZYIZGE-UHFFFAOYSA-N 0.000 claims 3
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 3
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
- 206010061218 Inflammation Diseases 0.000 claims 3
- 102000000588 Interleukin-2 Human genes 0.000 claims 3
- 108010002350 Interleukin-2 Proteins 0.000 claims 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims 3
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- 125000002393 azetidinyl group Chemical group 0.000 claims 3
- UGUUDTWORXNLAK-UHFFFAOYSA-N azidoalcohol Chemical compound ON=[N+]=[N-] UGUUDTWORXNLAK-UHFFFAOYSA-N 0.000 claims 3
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 3
- 125000002837 carbocyclic group Chemical group 0.000 claims 3
- 230000024203 complement activation Effects 0.000 claims 3
- 230000000295 complement effect Effects 0.000 claims 3
- 125000003700 epoxy group Chemical group 0.000 claims 3
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 3
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 3
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims 3
- 230000004054 inflammatory process Effects 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 208000002780 macular degeneration Diseases 0.000 claims 3
- 230000001404 mediated effect Effects 0.000 claims 3
- 229940095102 methyl benzoate Drugs 0.000 claims 3
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 3
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 3
- 125000002757 morpholinyl group Chemical group 0.000 claims 3
- VCARPLHUPPGQJK-UHFFFAOYSA-N n-azidohydroxylamine Chemical group ONN=[N+]=[N-] VCARPLHUPPGQJK-UHFFFAOYSA-N 0.000 claims 3
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 claims 3
- 230000037361 pathway Effects 0.000 claims 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims 3
- WTWXLOUOFOXIFQ-MYINAIGISA-N (1R,3S,5S)-5-(methoxymethyl)-2-azabicyclo[3.1.0]hexane-2,3-dicarboxylic acid Chemical compound C([C@H](N1C(O)=O)C(O)=O)[C@]2(COC)[C@H]1C2 WTWXLOUOFOXIFQ-MYINAIGISA-N 0.000 claims 2
- WXBIYUHOPUIBHC-FBCQKBJTSA-N (1s,5r)-2-azabicyclo[3.1.0]hexane-1,2-dicarboxylic acid Chemical compound OC(=O)N1CC[C@@H]2C[C@]12C(O)=O WXBIYUHOPUIBHC-FBCQKBJTSA-N 0.000 claims 2
- LRFWYBZWRQWZIM-UHFFFAOYSA-N (2-fluorophenyl)methanamine Chemical compound NCC1=CC=CC=C1F LRFWYBZWRQWZIM-UHFFFAOYSA-N 0.000 claims 2
- NMXRFBXFBFIUOM-DMTCNVIQSA-N (2R,3R)-3-fluoropyrrolidine-1,2-dicarboxylic acid Chemical compound OC(=O)[C@@H]1[C@H](F)CCN1C(O)=O NMXRFBXFBFIUOM-DMTCNVIQSA-N 0.000 claims 2
- NMXRFBXFBFIUOM-IMJSIDKUSA-N (2R,3S)-3-fluoropyrrolidine-1,2-dicarboxylic acid Chemical compound OC(=O)[C@@H]1[C@@H](F)CCN1C(O)=O NMXRFBXFBFIUOM-IMJSIDKUSA-N 0.000 claims 2
- BSDTWIGMXYKJEV-NUNKFHFFSA-N (2S,3S,4S)-3-amino-4-fluoropyrrolidine-1,2-dicarboxylic acid Chemical compound N[C@@H]1[C@@H](F)CN(C(O)=O)[C@@H]1C(O)=O BSDTWIGMXYKJEV-NUNKFHFFSA-N 0.000 claims 2
- IYOXBCOLEAZKBF-VKHMYHEASA-N (2s)-4,4-difluoropyrrolidine-1,2-dicarboxylic acid Chemical compound OC(=O)[C@@H]1CC(F)(F)CN1C(O)=O IYOXBCOLEAZKBF-VKHMYHEASA-N 0.000 claims 2
- SMCWNPAVVQIDBM-YFKPBYRVSA-N (2s)-piperidine-1,2-dicarboxylic acid Chemical compound OC(=O)[C@@H]1CCCCN1C(O)=O SMCWNPAVVQIDBM-YFKPBYRVSA-N 0.000 claims 2
- BUPZCXUOXVKTKF-VAYJURFESA-N (2s,3s,4s)-4-fluoro-3-methoxypyrrolidine-1,2-dicarboxylic acid Chemical compound CO[C@@H]1[C@@H](F)CN(C(O)=O)[C@@H]1C(O)=O BUPZCXUOXVKTKF-VAYJURFESA-N 0.000 claims 2
- JCINQOYGBLWVGB-UHNVWZDZSA-N (2s,4s)-4-cyanopyrrolidine-1,2-dicarboxylic acid Chemical compound OC(=O)[C@@H]1C[C@H](C#N)CN1C(O)=O JCINQOYGBLWVGB-UHNVWZDZSA-N 0.000 claims 2
- HHDQVBSXYDRQGD-IMJSIDKUSA-N (2s,4s)-4-hydroxypyrrolidine-1,2-dicarboxylic acid Chemical compound O[C@H]1C[C@@H](C(O)=O)N(C(O)=O)C1 HHDQVBSXYDRQGD-IMJSIDKUSA-N 0.000 claims 2
- FCKBTVFCMVATOG-RITPCOANSA-N (2s,5r)-5-ethylpyrrolidine-1,2-dicarboxylic acid Chemical compound CC[C@@H]1CC[C@@H](C(O)=O)N1C(O)=O FCKBTVFCMVATOG-RITPCOANSA-N 0.000 claims 2
- PDXRPVFVFWBERR-UHNVWZDZSA-N (2s,5r)-5-methylpyrrolidine-1,2-dicarboxylic acid Chemical compound C[C@@H]1CC[C@@H](C(O)=O)N1C(O)=O PDXRPVFVFWBERR-UHNVWZDZSA-N 0.000 claims 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 2
- UQPXYEYBUROSJF-UHFFFAOYSA-N 1,6-diazaspiro[3.3]heptane Chemical compound N1CCC11CNC1 UQPXYEYBUROSJF-UHFFFAOYSA-N 0.000 claims 2
- ZWLWJCWOPCLRKQ-UHFFFAOYSA-N 1-hydroxytetrazole-5-carbonitrile Chemical compound ON1N=NN=C1C#N ZWLWJCWOPCLRKQ-UHFFFAOYSA-N 0.000 claims 2
- ZPJGOWOMUISLPL-UHFFFAOYSA-N 1-oxa-6-azaspiro[3.3]heptane Chemical compound O1CCC11CNC1 ZPJGOWOMUISLPL-UHFFFAOYSA-N 0.000 claims 2
- JXBKZAYVMSNKHA-UHFFFAOYSA-N 1h-tetrazol-1-ium-5-olate Chemical compound OC=1N=NNN=1 JXBKZAYVMSNKHA-UHFFFAOYSA-N 0.000 claims 2
- OTVAEFIXJLOWRX-UHFFFAOYSA-N 2,2-dichloro-n-[1,3-dihydroxy-1-(4-methylsulfonylphenyl)propan-2-yl]acetamide Chemical group CS(=O)(=O)C1=CC=C(C(O)C(CO)NC(=O)C(Cl)Cl)C=C1 OTVAEFIXJLOWRX-UHFFFAOYSA-N 0.000 claims 2
- UDSAJFSYJMHNFI-UHFFFAOYSA-N 2,6-diazaspiro[3.3]heptane Chemical compound C1NCC11CNC1 UDSAJFSYJMHNFI-UHFFFAOYSA-N 0.000 claims 2
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- PSEFWMGUIGBSMX-UHFFFAOYSA-N 3,4-dihydropyrazole-2,3-dicarboxylic acid Chemical compound OC(=O)C1CC=NN1C(O)=O PSEFWMGUIGBSMX-UHFFFAOYSA-N 0.000 claims 2
- JNZYADHPGVZMQK-UHFFFAOYSA-N 3-(aminomethyl)phenol Chemical compound NCC1=CC=CC(O)=C1 JNZYADHPGVZMQK-UHFFFAOYSA-N 0.000 claims 2
- TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 claims 2
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 2
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 206010020751 Hypersensitivity Diseases 0.000 claims 2
- IPQLKFAHUWJGQR-UHNVWZDZSA-N NC[C@H]1C[C@@H](C(O)=O)N(C(O)=O)C1 Chemical compound NC[C@H]1C[C@@H](C(O)=O)N(C(O)=O)C1 IPQLKFAHUWJGQR-UHNVWZDZSA-N 0.000 claims 2
- SVEKDOPPNJXIJM-IMJSIDKUSA-N N[C@H]1CCN(C(O)=O)[C@@H]1C(O)=O Chemical compound N[C@H]1CCN(C(O)=O)[C@@H]1C(O)=O SVEKDOPPNJXIJM-IMJSIDKUSA-N 0.000 claims 2
- BWOJKKSOJQRQGD-RNCFNFMXSA-N OC(=O)[C@@H]1C[C@@H](F)CN1C(=O)Cn1cc(C(=O)C(F)(F)F)c2ccccc12 Chemical compound OC(=O)[C@@H]1C[C@@H](F)CN1C(=O)Cn1cc(C(=O)C(F)(F)F)c2ccccc12 BWOJKKSOJQRQGD-RNCFNFMXSA-N 0.000 claims 2
- 206010035664 Pneumonia Diseases 0.000 claims 2
- 230000004913 activation Effects 0.000 claims 2
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 208000026935 allergic disease Diseases 0.000 claims 2
- 125000003368 amide group Chemical group 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 230000010410 reperfusion Effects 0.000 claims 2
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- UIANBHKOLNGHDL-KUHUBIRLSA-N methyl 3-[[[(2s,4r)-1-[(1-carbamoylindol-3-yl)carbamoyl]-4-fluoropyrrolidine-2-carbonyl]amino]methyl]-5-chloro-4-fluorobenzoate Chemical compound COC(=O)C1=CC(Cl)=C(F)C(CNC(=O)[C@H]2N(C[C@H](F)C2)C(=O)NC=2C3=CC=CC=C3N(C(N)=O)C=2)=C1 UIANBHKOLNGHDL-KUHUBIRLSA-N 0.000 claims 1
- CQAPYYDHWUBSTN-HVETUWLQSA-N methyl 3-acetyl-1-[2-[(1r,3s,5r)-3-[(3-chloro-2-fluorophenyl)methylcarbamoyl]-2-azabicyclo[3.1.0]hexan-2-yl]-2-oxoethyl]indole-7-carboxylate Chemical compound O=C([C@@H]1C[C@H]2C[C@H]2N1C(=O)CN1C=C(C=2C=CC=C(C1=2)C(=O)OC)C(C)=O)NCC1=CC=CC(Cl)=C1F CQAPYYDHWUBSTN-HVETUWLQSA-N 0.000 claims 1
- MRMIVRJUUNISKJ-IBGZPJMESA-N methyl 3-bromo-5-[[(2s)-3-[(1-carbamoylindol-3-yl)carbamoyl]-1,3-thiazolidine-2-carbonyl]amino]benzoate Chemical compound COC(=O)C1=CC(Br)=CC(NC(=O)[C@H]2N(CCS2)C(=O)NC=2C3=CC=CC=C3N(C(N)=O)C=2)=C1 MRMIVRJUUNISKJ-IBGZPJMESA-N 0.000 claims 1
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 claims 1
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
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- 206010028417 myasthenia gravis Diseases 0.000 claims 1
- 210000004165 myocardium Anatomy 0.000 claims 1
- NYCVFBXQMXSFTB-UHFFFAOYSA-N n'-[[3-(aminomethyl)-5-chloro-4-fluorophenyl]methyl]-n,n,n'-trimethylethane-1,2-diamine Chemical compound CN(C)CCN(C)CC1=CC(Cl)=C(F)C(CN)=C1 NYCVFBXQMXSFTB-UHFFFAOYSA-N 0.000 claims 1
- VWNZVZSGKAFOFR-UHFFFAOYSA-N n-[[3-(aminomethyl)-5-chloro-4-fluorophenyl]methyl]-2-methoxy-n-methylethanamine Chemical compound COCCN(C)CC1=CC(Cl)=C(F)C(CN)=C1 VWNZVZSGKAFOFR-UHFFFAOYSA-N 0.000 claims 1
- NWJUMMHVDMNYMJ-UHFFFAOYSA-N n-benzyl-1,1,1-trifluoromethanamine Chemical compound FC(F)(F)NCC1=CC=CC=C1 NWJUMMHVDMNYMJ-UHFFFAOYSA-N 0.000 claims 1
- HNBDRPTVWVGKBR-UHFFFAOYSA-N n-pentanoic acid methyl ester Natural products CCCCC(=O)OC HNBDRPTVWVGKBR-UHFFFAOYSA-N 0.000 claims 1
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- QVGXLLKOCUKJST-NJFSPNSNSA-N oxygen-18 atom Chemical compound [18O] QVGXLLKOCUKJST-NJFSPNSNSA-N 0.000 claims 1
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- NWQLSIVIGQZSIA-CABCVRRESA-N phenyl n-[[(2s,4r)-1-[(1-carbamoylindol-3-yl)carbamoyl]-4-fluoropyrrolidin-2-yl]methyl]carbamate Chemical compound C([C@@H]1C[C@@H](F)CN1C(=O)NC1=CN(C2=CC=CC=C21)C(=O)N)NC(=O)OC1=CC=CC=C1 NWQLSIVIGQZSIA-CABCVRRESA-N 0.000 claims 1
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- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
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- LBJQKYPPYSCCBH-UHFFFAOYSA-N spiro[3.3]heptane Chemical compound C1CCC21CCC2 LBJQKYPPYSCCBH-UHFFFAOYSA-N 0.000 claims 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
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- 2012-01-02 ES ES12700094.1T patent/ES2647664T3/es active Active
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- 2012-01-02 PE PE2013001512A patent/PE20140471A1/es not_active Application Discontinuation
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