JP2014506877A5

JP2014506877A5 -

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Publication number: JP2014506877A5
Authority: JP; Japan
Prior art keywords: fluoro; amide; indol; carbamoyl; chloro
Prior art date: 2012-01-02
Legal status : Granted

Application number

JP2013547843A

Other languages

English (en)

Japanese (ja)

Other versions

JP2014506877A (ja

JP5921572B2 (ja

Filing date

2012-01-02

Publication date

2015-02-19

2012-01-02 Application filed filed Critical

2012-01-02 Priority claimed from PCT/EP2012/050005 external-priority patent/WO2012093101A1/en

2014-03-20 Publication of JP2014506877A publication Critical patent/JP2014506877A/ja

2015-02-19 Publication of JP2014506877A5 publication Critical patent/JP2014506877A5/ja

2016-05-24 Application granted granted Critical

2016-05-24 Publication of JP5921572B2 publication Critical patent/JP5921572B2/ja

Status Expired - Fee Related legal-status Critical Current

2032-01-02 Anticipated expiration legal-status Critical

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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
201000000596 systemic lupus erythematosus Diseases 0.000 claims 2
WTWXLOUOFOXIFQ-ATVXKPNKSA-N (1S,3S,5R)-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-ATVXKPNKSA-N 0.000 claims 1
PSHYTLBRFRTYSP-JLDZCNIISA-N (1r,2s,5s)-3-[2-(3-acetylpyrrolo[2,3-b]pyridin-1-yl)acetyl]-n-[(3-chloro-2-fluorophenyl)methyl]-3-azabicyclo[3.1.0]hexane-2-carboxamide Chemical compound O=C([C@@H]1[C@@H]2C[C@@H]2CN1C(=O)CN1C=C(C2=CC=CN=C21)C(=O)C)NCC1=CC=CC(Cl)=C1F PSHYTLBRFRTYSP-JLDZCNIISA-N 0.000 claims 1
SXTNOQAEMMAYBT-YAEBDLLGSA-N (1r,2s,5s)-3-[2-(3-acetylpyrrolo[2,3-c]pyridin-1-yl)acetyl]-n-[(3-chloro-2-fluorophenyl)methyl]-3-azabicyclo[3.1.0]hexane-2-carboxamide Chemical compound O=C([C@@H]1[C@@H]2C[C@@H]2CN1C(=O)CN1C=C(C2=CC=NC=C21)C(=O)C)NCC1=CC=CC(Cl)=C1F SXTNOQAEMMAYBT-YAEBDLLGSA-N 0.000 claims 1
FMKGOCAFOVIZQE-LNPFQXMTSA-N (1r,2s,5s)-3-[2-(3-acetylpyrrolo[3,2-c]pyridin-1-yl)acetyl]-n-[(3-chloro-2-fluorophenyl)methyl]-3-azabicyclo[3.1.0]hexane-2-carboxamide Chemical compound O=C([C@@H]1[C@@H]2C[C@@H]2CN1C(=O)CN1C=C(C2=CN=CC=C21)C(=O)C)NCC1=CC=CC(Cl)=C1F FMKGOCAFOVIZQE-LNPFQXMTSA-N 0.000 claims 1
SLJSXZAVVKCTHT-LZQZEXGQSA-N (1r,3s,5r)-2-[2-(1-acetylimidazo[1,5-a]pyridin-3-yl)acetyl]-n-[(3-chloro-2-fluorophenyl)methyl]-2-azabicyclo[3.1.0]hexane-3-carboxamide Chemical compound O=C([C@@H]1C[C@H]2C[C@H]2N1C(=O)CC1=NC(=C2C=CC=CN21)C(=O)C)NCC1=CC=CC(Cl)=C1F SLJSXZAVVKCTHT-LZQZEXGQSA-N 0.000 claims 1
QESHFNIHJQIFSV-RTOPAQNCSA-N (1r,3s,5r)-2-[2-(3-acetyl-5-hydroxyindol-1-yl)acetyl]-n-[(3-chloro-2-fluorophenyl)methyl]-2-azabicyclo[3.1.0]hexane-3-carboxamide Chemical compound O=C([C@@H]1C[C@H]2C[C@H]2N1C(=O)CN1C=C(C2=CC(O)=CC=C21)C(=O)C)NCC1=CC=CC(Cl)=C1F QESHFNIHJQIFSV-RTOPAQNCSA-N 0.000 claims 1
IQMIWZQTGCHIHJ-LPTQZCDUSA-N (1r,3s,5r)-2-[2-(3-acetyl-6-cyanopyrrolo[2,3-b]pyridin-1-yl)acetyl]-n-[(3-chloro-2-fluorophenyl)methyl]-2-azabicyclo[3.1.0]hexane-3-carboxamide Chemical compound O=C([C@@H]1C[C@H]2C[C@H]2N1C(=O)CN1C=C(C2=CC=C(N=C21)C#N)C(=O)C)NCC1=CC=CC(Cl)=C1F IQMIWZQTGCHIHJ-LPTQZCDUSA-N 0.000 claims 1
FHNOIFDKTULVDI-QPJICYPMSA-N (1r,3s,5r)-2-[2-(3-acetyl-6-hydroxyindol-1-yl)acetyl]-n-[(3-chloro-2-fluorophenyl)methyl]-2-azabicyclo[3.1.0]hexane-3-carboxamide Chemical compound O=C([C@@H]1C[C@H]2C[C@H]2N1C(=O)CN1C=C(C2=CC=C(O)C=C21)C(=O)C)NCC1=CC=CC(Cl)=C1F FHNOIFDKTULVDI-QPJICYPMSA-N 0.000 claims 1
DJEHGKDWMQPHEP-XRHWURSXSA-N (1r,3s,5r)-2-[2-(3-acetyl-6-phenylmethoxyindol-1-yl)acetyl]-n-[(3-chloro-2-fluorophenyl)methyl]-2-azabicyclo[3.1.0]hexane-3-carboxamide Chemical compound O=C([C@@H]1C[C@H]2C[C@H]2N1C(=O)CN1C=C(C2=CC=C(OCC=3C=CC=CC=3)C=C21)C(=O)C)NCC1=CC=CC(Cl)=C1F DJEHGKDWMQPHEP-XRHWURSXSA-N 0.000 claims 1
SKKPCXTZNWYSPR-OOBDGNPPSA-N (1r,3s,5r)-2-[2-(3-acetylpyrrolo[2,3-b]pyridin-1-yl)acetyl]-n-[(1s)-1-(3-chloro-2-fluorophenyl)-2-hydroxyethyl]-2-azabicyclo[3.1.0]hexane-3-carboxamide Chemical compound C1([C@@H](CO)NC(=O)[C@@H]2C[C@H]3C[C@H]3N2C(=O)CN2C=C(C3=CC=CN=C32)C(=O)C)=CC=CC(Cl)=C1F SKKPCXTZNWYSPR-OOBDGNPPSA-N 0.000 claims 1
HVIHNCSIZJUBRB-YSGRDPCXSA-N (1r,3s,5r)-2-[2-(3-acetylpyrrolo[2,3-b]pyridin-1-yl)acetyl]-n-[(3-chloro-2-fluorophenyl)methyl]-2-azabicyclo[3.1.0]hexane-3-carboxamide Chemical compound O=C([C@@H]1C[C@H]2C[C@H]2N1C(=O)CN1C=C(C2=CC=CN=C21)C(=O)C)NCC1=CC=CC(Cl)=C1F HVIHNCSIZJUBRB-YSGRDPCXSA-N 0.000 claims 1
ZOOJOYMGXHVSNF-XWIAVFTESA-N (1r,3s,5r)-2-[2-(3-acetylpyrrolo[2,3-b]pyridin-1-yl)acetyl]-n-[(5-chlorothiophen-2-yl)methyl]-2-azabicyclo[3.1.0]hexane-3-carboxamide Chemical compound O=C([C@@H]1C[C@H]2C[C@H]2N1C(=O)CN1C=C(C2=CC=CN=C21)C(=O)C)NCC1=CC=C(Cl)S1 ZOOJOYMGXHVSNF-XWIAVFTESA-N 0.000 claims 1
LAOKGDLPBZJLJQ-YSGRDPCXSA-N (1r,3s,5r)-2-[2-(3-acetylpyrrolo[2,3-c]pyridin-1-yl)acetyl]-n-[(3-chloro-2-fluorophenyl)methyl]-2-azabicyclo[3.1.0]hexane-3-carboxamide Chemical compound O=C([C@@H]1C[C@H]2C[C@H]2N1C(=O)CN1C=C(C2=CC=NC=C21)C(=O)C)NCC1=CC=CC(Cl)=C1F LAOKGDLPBZJLJQ-YSGRDPCXSA-N 0.000 claims 1
XTSQWDNDTJUOKT-YSGRDPCXSA-N (1r,3s,5r)-2-[2-(3-acetylpyrrolo[3,2-b]pyridin-1-yl)acetyl]-n-[(3-chloro-2-fluorophenyl)methyl]-2-azabicyclo[3.1.0]hexane-3-carboxamide Chemical compound O=C([C@@H]1C[C@H]2C[C@H]2N1C(=O)CN1C=C(C2=NC=CC=C21)C(=O)C)NCC1=CC=CC(Cl)=C1F XTSQWDNDTJUOKT-YSGRDPCXSA-N 0.000 claims 1
LYNXOJOQDHSCCM-LPTQZCDUSA-N (1r,3s,5r)-2-[2-(3-acetylpyrrolo[3,2-c]pyridin-1-yl)acetyl]-n-[(3-chloro-2-fluorophenyl)methyl]-2-azabicyclo[3.1.0]hexane-3-carboxamide Chemical compound O=C([C@@H]1C[C@H]2C[C@H]2N1C(=O)CN1C=C(C2=CN=CC=C21)C(=O)C)NCC1=CC=CC(Cl)=C1F LYNXOJOQDHSCCM-LPTQZCDUSA-N 0.000 claims 1
IUUOBEYNFHWBAU-LPTQZCDUSA-N (1r,3s,5r)-n-[(3-chloro-2-fluorophenyl)methyl]-2-[2-[3-(2-hydroxyacetyl)indol-1-yl]acetyl]-2-azabicyclo[3.1.0]hexane-3-carboxamide Chemical compound O=C([C@@H]1C[C@H]2C[C@H]2N1C(=O)CN1C=C(C2=CC=CC=C21)C(=O)CO)NCC1=CC=CC(Cl)=C1F IUUOBEYNFHWBAU-LPTQZCDUSA-N 0.000 claims 1
SXTNOQAEMMAYBT-YGJVYZRNSA-N (1s,2s,5r)-3-[2-(3-acetylpyrrolo[2,3-c]pyridin-1-yl)acetyl]-n-[(3-chloro-2-fluorophenyl)methyl]-3-azabicyclo[3.1.0]hexane-2-carboxamide Chemical compound O=C([C@@H]1[C@H]2C[C@H]2CN1C(=O)CN1C=C(C2=CC=NC=C21)C(=O)C)NCC1=CC=CC(Cl)=C1F SXTNOQAEMMAYBT-YGJVYZRNSA-N 0.000 claims 1
MSUUVBALUUPWGY-VRUMLPLGSA-N (1s,3s,5r)-4-[2-(3-acetylindol-1-yl)acetyl]-n-[(3-chloro-2-fluorophenyl)methyl]-1-(hydroxymethyl)-4-azabicyclo[3.1.0]hexane-3-carboxamide Chemical compound O=C([C@@H]1C[C@@]2(CO)C[C@H]2N1C(=O)CN1C=C(C2=CC=CC=C21)C(=O)C)NCC1=CC=CC(Cl)=C1F MSUUVBALUUPWGY-VRUMLPLGSA-N 0.000 claims 1
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DBQHLJOOMYBKNQ-UHFFFAOYSA-N (2,3-difluoro-4-methoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C(F)=C1F DBQHLJOOMYBKNQ-UHFFFAOYSA-N 0.000 claims 1
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KDDNKZCVYQDGKE-UHFFFAOYSA-N (2-chlorophenyl)methanamine Chemical compound NCC1=CC=CC=C1Cl KDDNKZCVYQDGKE-UHFFFAOYSA-N 0.000 claims 1
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HGMNTGNJUVQMAX-FQEVSTJZSA-N (2S)-1-[2-(3-formylindol-1-yl)acetyl]-N-[3-(trifluoromethoxy)phenyl]pyrrolidine-2-carboxamide Chemical compound FC(F)(F)OC1=CC=CC(NC(=O)[C@H]2N(CCC2)C(=O)CN2C3=CC=CC=C3C(C=O)=C2)=C1 HGMNTGNJUVQMAX-FQEVSTJZSA-N 0.000 claims 1
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HOZATCZBEQWFPV-RQJHMYQMSA-N (2S,3R)-3-(2-methoxyethylamino)pyrrolidine-1,2-dicarboxylic acid Chemical compound COCCN[C@@H]1CCN(C(O)=O)[C@@H]1C(O)=O HOZATCZBEQWFPV-RQJHMYQMSA-N 0.000 claims 1
IDAWWRNSZMLQEK-RITPCOANSA-N (2S,3R)-3-acetamidopyrrolidine-1,2-dicarboxylic acid Chemical compound CC(=O)N[C@@H]1CCN(C(O)=O)[C@@H]1C(O)=O IDAWWRNSZMLQEK-RITPCOANSA-N 0.000 claims 1
GLOBUKJGNIWACQ-YVZJFKFKSA-N (2S,3R,4S)-4-amino-3-hydroxypyrrolidine-1,2-dicarboxylic acid Chemical compound N[C@H]1CN(C(O)=O)[C@H](C(O)=O)[C@@H]1O GLOBUKJGNIWACQ-YVZJFKFKSA-N 0.000 claims 1
GLOBUKJGNIWACQ-UZBSEBFBSA-N (2S,3S,4R)-4-amino-3-hydroxypyrrolidine-1,2-dicarboxylic acid Chemical compound N[C@@H]1CN(C(O)=O)[C@H](C(O)=O)[C@H]1O GLOBUKJGNIWACQ-UZBSEBFBSA-N 0.000 claims 1
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UHTCLRWCFCIEDS-MHTLYPKNSA-N (2S,4R)-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-MHTLYPKNSA-N 0.000 claims 1
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RTMCNXDSXSHACI-RQJHMYQMSA-N (2S,4R)-4-[(dimethylamino)methyl]pyrrolidine-1,2-dicarboxylic acid Chemical compound CN(C)C[C@H]1C[C@@H](C(O)=O)N(C(O)=O)C1 RTMCNXDSXSHACI-RQJHMYQMSA-N 0.000 claims 1
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MDTRFWLINHRTJH-MHTLYPKNSA-N (2S,4R)-4-hydroxy-4-(hydroxymethyl)pyrrolidine-1,2-dicarboxylic acid Chemical compound OC[C@@]1(O)C[C@@H](C(O)=O)N(C(O)=O)C1 MDTRFWLINHRTJH-MHTLYPKNSA-N 0.000 claims 1
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IPQLKFAHUWJGQR-WHFBIAKZSA-N (2S,4S)-4-(aminomethyl)pyrrolidine-1,2-dicarboxylic acid Chemical compound NC[C@@H]1C[C@@H](C(O)=O)N(C(O)=O)C1 IPQLKFAHUWJGQR-WHFBIAKZSA-N 0.000 claims 1
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MFHGRSMAIMOMED-WHFBIAKZSA-N (2S,4S)-4-(methylamino)pyrrolidine-1,2-dicarboxylic acid Chemical compound CN[C@H]1C[C@@H](C(O)=O)N(C(O)=O)C1 MFHGRSMAIMOMED-WHFBIAKZSA-N 0.000 claims 1
VLITYUNEECNVNB-IMJSIDKUSA-N (2S,4S)-4-(trifluoromethyl)pyrrolidine-1,2-dicarboxylic acid Chemical compound OC(=O)[C@@H]1C[C@H](C(F)(F)F)CN1C(O)=O VLITYUNEECNVNB-IMJSIDKUSA-N 0.000 claims 1
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TUXPIGXWPLCUDJ-FFWSUHOLSA-N (2S,4S)-4-fluoro-4-(hydroxymethyl)pyrrolidine-1,2-dicarboxylic acid Chemical compound OC[C@]1(F)C[C@@H](C(O)=O)N(C(O)=O)C1 TUXPIGXWPLCUDJ-FFWSUHOLSA-N 0.000 claims 1
NJTYCLPSZJSBSA-XNCJUZBTSA-N (2S,4S)-4-fluoro-4-(methylaminomethyl)pyrrolidine-1,2-dicarboxylic acid Chemical compound CNC[C@@]1(F)C[C@@H](C(O)=O)N(C(O)=O)C1 NJTYCLPSZJSBSA-XNCJUZBTSA-N 0.000 claims 1
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MDTRFWLINHRTJH-FFWSUHOLSA-N (2S,4S)-4-hydroxy-4-(hydroxymethyl)pyrrolidine-1,2-dicarboxylic acid Chemical compound OC[C@]1(O)C[C@@H](C(O)=O)N(C(O)=O)C1 MDTRFWLINHRTJH-FFWSUHOLSA-N 0.000 claims 1
NMIGMIPMFGMJPK-RQJHMYQMSA-N (2S,5R)-5-(acetamidomethyl)pyrrolidine-1,2-dicarboxylic acid Chemical compound CC(=O)NC[C@H]1CC[C@@H](C(O)=O)N1C(O)=O NMIGMIPMFGMJPK-RQJHMYQMSA-N 0.000 claims 1
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FEGUXOCIYGFNIL-ZODMCCGTSA-N (2r,3s,4r)-1-[2-(3-acetylindol-1-yl)acetyl]-n-[(3-chloro-2-fluorophenyl)methyl]-4-(dimethylamino)-3-fluoropyrrolidine-2-carboxamide Chemical compound O=C([C@H]1N(C[C@H]([C@@H]1F)N(C)C)C(=O)CN1C2=CC=CC=C2C(C(C)=O)=C1)NCC1=CC=CC(Cl)=C1F FEGUXOCIYGFNIL-ZODMCCGTSA-N 0.000 claims 1
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LFEUADMCDRWDRA-UHNVWZDZSA-N (2s,3r)-3-methylpyrrolidine-1,2-dicarboxylic acid Chemical compound C[C@@H]1CCN(C(O)=O)[C@@H]1C(O)=O LFEUADMCDRWDRA-UHNVWZDZSA-N 0.000 claims 1
AWXDDXPSAPKTTK-IMJSIDKUSA-N (2s,3s)-3-hydroxypyrrolidine-1,2-dicarboxylic acid Chemical compound O[C@H]1CCN(C(O)=O)[C@@H]1C(O)=O AWXDDXPSAPKTTK-IMJSIDKUSA-N 0.000 claims 1
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RFQDTOPGWRIDBP-YUXAGFNASA-N (2s,3s,4s)-1-[2-(3-acetylpyrrolo[2,3-b]pyridin-1-yl)acetyl]-n-[(3-chloro-2-fluorophenyl)methyl]-4-fluoro-3-methoxypyrrolidine-2-carboxamide Chemical compound O=C([C@H]1N(C[C@H](F)[C@H]1OC)C(=O)CN1C2=NC=CC=C2C(C(C)=O)=C1)NCC1=CC=CC(Cl)=C1F RFQDTOPGWRIDBP-YUXAGFNASA-N 0.000 claims 1
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DXYNQSROMABIPK-YFKPBYRVSA-N (6S)-5-azaspiro[2.4]heptane-5,6-dicarboxylic acid Chemical compound C1N(C(O)=O)[C@H](C(=O)O)CC11CC1 DXYNQSROMABIPK-YFKPBYRVSA-N 0.000 claims 1
CXCIPKUYVKRZCX-UHFFFAOYSA-N 1-(3-isocyanatoindol-1-yl)ethanone Chemical compound C1=CC=C2N(C(=O)C)C=C(N=C=O)C2=C1 CXCIPKUYVKRZCX-UHFFFAOYSA-N 0.000 claims 1
CWZUTHDJLNZLCM-DFBGVHRSSA-N 1-[2-[(1r,3s,5r)-3-[(6-bromopyridin-2-yl)carbamoyl]-2-azabicyclo[3.1.0]hexan-2-yl]-2-oxoethyl]indazole-3-carboxamide Chemical compound O=C([C@@H]1C[C@H]2C[C@H]2N1C(=O)CN1N=C(C2=CC=CC=C21)C(=O)N)NC1=CC=CC(Br)=N1 CWZUTHDJLNZLCM-DFBGVHRSSA-N 0.000 claims 1
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125000003070 2-(2-chlorophenyl)ethyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
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125000000301 2-(3-chlorophenyl)ethyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
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SJQRHEXJJFVKGH-KUHUBIRLSA-N 2-[[[(2s,4r)-1-[(1-carbamoylindol-3-yl)carbamoyl]-4-fluoropyrrolidine-2-carbonyl]amino]methyl]benzoic acid Chemical compound O=C([C@@H]1C[C@@H](F)CN1C(=O)NC1=CN(C2=CC=CC=C21)C(=O)N)NCC1=CC=CC=C1C(O)=O SJQRHEXJJFVKGH-KUHUBIRLSA-N 0.000 claims 1
FCZGRSXGGUAWJZ-ZMZPIMSZSA-N 2-bromo-4-[[(2s,4r)-1-[(1-carbamoylindol-3-yl)carbamoyl]-4-fluoropyrrolidine-2-carbonyl]amino]benzoic acid Chemical compound O=C([C@@H]1C[C@@H](F)CN1C(=O)NC1=CN(C2=CC=CC=C21)C(=O)N)NC1=CC=C(C(O)=O)C(Br)=C1 FCZGRSXGGUAWJZ-ZMZPIMSZSA-N 0.000 claims 1
125000003635 2-dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 claims 1
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
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FXPLEXVSFQOHCJ-LPTQZCDUSA-N 3-[2-[(1r,3s,5r)-3-[(3-chloro-2-fluorophenyl)methylcarbamoyl]-2-azabicyclo[3.1.0]hexan-2-yl]-2-oxoethyl]-2-methylindole-1-carboxamide Chemical compound O=C([C@@H]1C[C@H]2C[C@H]2N1C(=O)CC1=C(N(C2=CC=CC=C21)C(N)=O)C)NCC1=CC=CC(Cl)=C1F FXPLEXVSFQOHCJ-LPTQZCDUSA-N 0.000 claims 1
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INXWTCYEKYNMTF-VEYWIMSWSA-N 3-[2-[(1r,3s,5r)-3-[(3-chloro-2-fluorophenyl)methylcarbamoyl]-2-azabicyclo[3.1.0]hexan-2-yl]-2-oxoethyl]-5-[2-(dimethylamino)ethoxy]indole-1-carboxamide Chemical compound O=C([C@@H]1C[C@H]2C[C@H]2N1C(=O)CC1=CN(C2=CC=C(C=C21)OCCN(C)C)C(N)=O)NCC1=CC=CC(Cl)=C1F INXWTCYEKYNMTF-VEYWIMSWSA-N 0.000 claims 1
XEJYIPYVHIOYDT-CNDZOEFASA-N 3-[2-[(1r,3s,5r)-3-[(3-chloro-2-fluorophenyl)methylcarbamoyl]-2-azabicyclo[3.1.0]hexan-2-yl]-2-oxoethyl]-6-(2-hydroxyethyl)indole-1-carboxamide Chemical compound O=C([C@@H]1C[C@H]2C[C@H]2N1C(=O)CC1=CN(C2=CC(CCO)=CC=C21)C(=O)N)NCC1=CC=CC(Cl)=C1F XEJYIPYVHIOYDT-CNDZOEFASA-N 0.000 claims 1
DRBINWXQKSMLPH-XMCHAPAWSA-N 3-[2-[(1r,3s,5r)-3-[(3-chloro-2-fluorophenyl)methylcarbamoyl]-2-azabicyclo[3.1.0]hexan-2-yl]-2-oxoethyl]indole-1-carboxamide Chemical compound O=C([C@@H]1C[C@H]2C[C@H]2N1C(=O)CC1=CN(C2=CC=CC=C21)C(=O)N)NCC1=CC=CC(Cl)=C1F DRBINWXQKSMLPH-XMCHAPAWSA-N 0.000 claims 1
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WTPGBDLFECAEKI-IEKZBVHVSA-N methyl 3-[[[(1r,3s,5r)-2-[2-(3-acetylindol-1-yl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonyl]amino]methyl]-5-chloro-4-fluorobenzoate Chemical compound COC(=O)C1=CC(Cl)=C(F)C(CNC(=O)[C@H]2N([C@@H]3C[C@@H]3C2)C(=O)CN2C3=CC=CC=C3C(C(C)=O)=C2)=C1 WTPGBDLFECAEKI-IEKZBVHVSA-N 0.000 claims 1
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
201000006417 multiple sclerosis Diseases 0.000 claims 1
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
201000008383 nephritis Diseases 0.000 claims 1
210000005036 nerve Anatomy 0.000 claims 1
235000020824 obesity Nutrition 0.000 claims 1
201000008482 osteoarthritis Diseases 0.000 claims 1
125000002971 oxazolyl group Chemical group 0.000 claims 1
QVGXLLKOCUKJST-NJFSPNSNSA-N oxygen-18 atom Chemical compound [18O] QVGXLLKOCUKJST-NJFSPNSNSA-N 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 claims 1
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
239000006187 pill Substances 0.000 claims 1
230000002980 postoperative effect Effects 0.000 claims 1
230000002062 proliferating effect Effects 0.000 claims 1
201000006301 pulmonary embolism and infarction Diseases 0.000 claims 1
208000005069 pulmonary fibrosis Diseases 0.000 claims 1
125000003373 pyrazinyl group Chemical group 0.000 claims 1
125000003226 pyrazolyl group Chemical group 0.000 claims 1
230000008929 regeneration Effects 0.000 claims 1
238000011069 regeneration method Methods 0.000 claims 1
230000004044 response Effects 0.000 claims 1
230000002207 retinal effect Effects 0.000 claims 1
208000004644 retinal vein occlusion Diseases 0.000 claims 1
231100000241 scar Toxicity 0.000 claims 1
LBJQKYPPYSCCBH-UHFFFAOYSA-N spiro[3.3]heptane Chemical compound C1CCC21CCC2 LBJQKYPPYSCCBH-UHFFFAOYSA-N 0.000 claims 1
208000011580 syndromic disease Diseases 0.000 claims 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
125000000335 thiazolyl group Chemical group 0.000 claims 1
230000017423 tissue regeneration Effects 0.000 claims 1
230000001988 toxicity Effects 0.000 claims 1
231100000419 toxicity Toxicity 0.000 claims 1
230000009529 traumatic brain injury Effects 0.000 claims 1

JP2013547843A 2011-01-04 2012-01-02 加齢性黄斑変性症（ａｍｄ）の処置に有用なインドール化合物またはそのアナログ Expired - Fee Related JP5921572B2 (ja)