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
- 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
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- 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
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- 201000006301 pulmonary embolism and infarction Diseases 0.000 claims 1
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- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 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
- 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
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Families Citing this family (116)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2867226B1 (en) * | 2012-06-28 | 2018-11-14 | Novartis AG | Complement pathway modulators and uses thereof |
| ES2647124T3 (es) | 2012-06-28 | 2017-12-19 | Novartis Ag | Derivados de pirrolidina y su uso como moduladores de la ruta del complemento |
| WO2014002053A1 (en) * | 2012-06-28 | 2014-01-03 | Novartis Ag | Pyrrolidine derivatives and their use as complement pathway modulators |
| JP6154897B2 (ja) * | 2012-06-28 | 2017-06-28 | ノバルティス アーゲー | ピロリジン誘導体、および補体経路調節因子としてのその使用 |
| US9487483B2 (en) * | 2012-06-28 | 2016-11-08 | Novartis Ag | Complement pathway modulators and uses thereof |
| CA2876993A1 (en) * | 2012-06-28 | 2014-01-03 | Novartis Ag | Pyrrolidine derivatives and their use as complement pathway modulators |
| WO2014005150A1 (en) * | 2012-06-29 | 2014-01-03 | Novartis Ag | Crystalline forms of l-(2-((lr,3s,5r)-3-( (2 -fluoro-3 - (trifluoromethoxy) phenyl) carbamoyl) - 2 -azabicycl o [3.1.0] hexan- 2 -yl) - 2 -oxoethyl) - 5 -methyl - 1h - pyrazolo [3, 4 -c] pyridine - 3 - carboxami de and salts thereof |
| WO2014002059A1 (en) * | 2012-06-29 | 2014-01-03 | Novartis Ag | CRYSTALLINE FORMS OF 1-(2-((1R,3S,5R)-3-(((R)-1-(3-chloro-2-fluorophenyl)ethyl)carbamoyl)-2-azabicyclo[3.1.0]hexan-2-yl)-2-oxoethyl)-1Hpyrazolo[3,4-c]pyridine-3-carboxamide |
| JP6238980B2 (ja) * | 2012-07-12 | 2017-11-29 | ノバルティス アーゲー | 補体経路モジュレーターおよびその使用 |
| EP3444238B1 (en) * | 2012-07-27 | 2021-12-08 | Sato Pharmaceutical Co., Ltd. | Process for preparing difluoromethylene compounds |
| JO3425B1 (ar) | 2013-07-15 | 2019-10-20 | Novartis Ag | مشتقات البابيريدينيل-اندول واستخدامها كعامل متمم لمثبطات b |
| CN104341360A (zh) * | 2013-07-31 | 2015-02-11 | 南京长澳医药科技有限公司 | 一种卢非酰胺的制备方法 |
| HK1219872A1 (zh) * | 2013-09-02 | 2017-04-21 | 保罗．里德 | 新的皮膚護理製劑 |
| US20160264536A1 (en) | 2013-10-23 | 2016-09-15 | Takeda Pharmaceutical Company Limited | Heterocyclic compound |
| EP2883876A1 (en) | 2013-12-16 | 2015-06-17 | Actelion Pharmaceuticals Ltd. | Stereoselective synthesis of substituted pyrrolidines |
| EA201691727A1 (ru) | 2014-02-25 | 2017-01-30 | Ачиллион Фармасьютикалс, Инк. | Фосфонатные соединения для лечения опосредованных комплементом нарушений |
| EA038607B1 (ru) * | 2014-09-05 | 2021-09-22 | Ачиллион Фармасьютикалс, Инк. | Арильные, гетероарильные и гетероциклические соединения для лечения опосредованных комплементом расстройств |
| WO2016088082A1 (en) | 2014-12-05 | 2016-06-09 | Novartis Ag | Amidomethyl-biaryl derivatives complement factor d inhibitors and uses thereof |
| AR105808A1 (es) | 2015-08-26 | 2017-11-08 | Achillion Pharmaceuticals Inc | Compuestos de amida para el tratamiento de trastornos médicos |
| WO2017035409A1 (en) * | 2015-08-26 | 2017-03-02 | Achillion Pharmaceuticals, Inc. | Aryl, heteroaryl, and heterocyclic compounds for treatment of immune and inflammatory disorders |
| US10000516B2 (en) | 2015-08-26 | 2018-06-19 | Achillion Pharmaceuticals, Inc. | Phosphonate compounds for treatment of medical disorders |
| ES2908479T3 (es) | 2015-08-26 | 2022-04-29 | Achillion Pharmaceuticals Inc | Compuestos para el tratamiento de trastornos inmunitarios e inflamatorios |
| WO2017035361A1 (en) | 2015-08-26 | 2017-03-02 | Achillion Pharmaceuticals, Inc. | Disubstituted compounds for the treatment of medical disorders |
| AR105809A1 (es) | 2015-08-26 | 2017-11-08 | Achillion Pharmaceuticals Inc | Compuestos para el tratamiento de trastornos médicos |
| WO2017035405A1 (en) | 2015-08-26 | 2017-03-02 | Achillion Pharmaceuticals, Inc. | Amino compounds for treatment of immune and inflammatory disorders |
| WO2017035417A1 (en) * | 2015-08-26 | 2017-03-02 | Achillion Pharmaceuticals, Inc. | Phosphonate compounds for treatment of immune and inflammatory disorders |
| US10385097B2 (en) | 2015-08-26 | 2019-08-20 | Achillion Pharmaceuticals, Inc. | Ether compounds for treatment of medical disorders |
| WO2017035413A2 (en) * | 2015-08-26 | 2017-03-02 | Achillion Pharmaceuticals, Inc. | Carbamate, ester, and ketone compounds for treatment of immune and inflammatory disorders |
| AR106018A1 (es) * | 2015-08-26 | 2017-12-06 | Achillion Pharmaceuticals Inc | Compuestos de arilo, heteroarilo y heterocíclicos para el tratamiento de trastornos médicos |
| WO2017035401A1 (en) * | 2015-08-26 | 2017-03-02 | Achillion Pharmaceuticals, Inc. | Amide compounds for treatment of immune and inflammatory disorders |
| WO2017035348A1 (en) * | 2015-08-26 | 2017-03-02 | Achillion Pharmaceuticals, Inc. | Alkyne compounds for treatment of medical disorders |
| WO2017035418A1 (en) * | 2015-08-26 | 2017-03-02 | Achillion Pharmaceuticals, Inc. | Disubstituted compounds for treatment of immune and inflammatory disorders |
| WO2017035352A1 (en) * | 2015-08-26 | 2017-03-02 | Achillion Pharmaceuticals, Inc. | Carbamate, ester, and ketone compounds for treatment of medical disorders |
| WO2017035415A1 (en) * | 2015-08-26 | 2017-03-02 | Achillion Pharmaceuticals, Inc. | Alkyne compounds for treatment of immune and inflammatory disorders |
| WO2017035351A1 (en) | 2015-08-26 | 2017-03-02 | Achillion Pharmaceuticals, Inc. | Amino compounds for treatment of medical disorders |
| WO2017035411A1 (en) * | 2015-08-26 | 2017-03-02 | Achillion Pharmaceuticals, Inc. | Ether compounds for treatment of immune and inflammatory disorders |
| US20170107216A1 (en) | 2015-10-19 | 2017-04-20 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| AU2016358100B2 (en) | 2015-11-19 | 2021-05-27 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| WO2017098328A2 (en) * | 2015-12-11 | 2017-06-15 | Lifesci Phamaceuticals, Inc. | Therapeutic inhibitory compounds |
| TW201726623A (zh) | 2015-12-17 | 2017-08-01 | 英塞特公司 | 作為免疫調節劑之雜環化合物 |
| TWI850624B (zh) | 2015-12-22 | 2024-08-01 | 美商英塞特公司 | 作為免疫調節劑之雜環化合物 |
| CA3011819A1 (en) | 2016-01-20 | 2017-07-27 | Vitrisa Therapeutics, Inc. | Compositions and methods for inhibiting factor d |
| TWI854164B (zh) | 2016-02-01 | 2024-09-01 | 美商百歐克斯製藥公司 | 苯并吡唑化合物及其類似物 |
| EP3423469A1 (en) | 2016-03-04 | 2019-01-09 | H. Hoffnabb-La Roche Ag | New trifluoromethylpropanamide derivatives as htra1 inhibitors |
| WO2017148967A1 (en) | 2016-03-04 | 2017-09-08 | F. Hoffmann-La Roche Ag | New difluoroketamide derivatives as htra1 inhibitors |
| TW201808950A (zh) | 2016-05-06 | 2018-03-16 | 英塞特公司 | 作為免疫調節劑之雜環化合物 |
| US20170342060A1 (en) | 2016-05-26 | 2017-11-30 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| DK3472167T3 (da) | 2016-06-20 | 2022-09-05 | Incyte Corp | Heterocykliske forbindelser som immunomodulatorer |
| WO2017222914A1 (en) | 2016-06-21 | 2017-12-28 | Inception 4, Inc. | Carbocyclic prolinamide derivatives |
| EP3939591A1 (en) | 2016-06-27 | 2022-01-19 | Achillion Pharmaceuticals, Inc. | Quinazoline and indole compounds to treat medical disorders |
| EP3484866B1 (en) | 2016-07-14 | 2022-09-07 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| US20190292155A1 (en) * | 2016-07-15 | 2019-09-26 | Lifesci Pharmaceuticals, Inc. | Therapeutic inhibitory compounds |
| CN109415330A (zh) | 2016-07-18 | 2019-03-01 | 豪夫迈·罗氏有限公司 | 作为htra1抑制剂的新型二氟酮酰胺衍生物 |
| CN109563084A (zh) * | 2016-08-23 | 2019-04-02 | 豪夫迈·罗氏有限公司 | 作为htra1抑制剂的新型三氟甲基丙酰胺衍生物 |
| CN109661389A (zh) | 2016-08-23 | 2019-04-19 | 豪夫迈·罗氏有限公司 | 作为htra1抑制剂的新型二氟酮酰胺衍生物 |
| EP3504198B1 (en) | 2016-08-29 | 2023-01-25 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| WO2018049214A1 (en) | 2016-09-09 | 2018-03-15 | Incyte Corporation | Pyrazolopyridine derivatives as hpk1 modulators and uses thereof for the treatment of cancer |
| TWI771319B (zh) | 2016-09-09 | 2022-07-21 | 美商英塞特公司 | 吡唑并吡啶化合物及其用途 |
| AR109595A1 (es) | 2016-09-09 | 2018-12-26 | Incyte Corp | Compuestos de pirazolopirimidina y usos de estos como inhibidores de hpk1 |
| GB2554071A (en) * | 2016-09-14 | 2018-03-28 | Univ Dundee | Small molecules |
| CN106588818B (zh) * | 2016-11-30 | 2019-07-26 | 兰州大学 | 一种医药中间体2,6-二氟-3-吗啉苯基甲胺及其制备方法 |
| CN108203434B (zh) * | 2016-12-20 | 2022-02-25 | 中国科学院上海药物研究所 | 一种制备索利那新的不对称合成方法 |
| ES2929193T3 (es) | 2016-12-22 | 2022-11-25 | Incyte Corp | Derivados de tetrahidro imidazo[4,5-c]piridina como inductores de la internalización de PD-L1 |
| EP3558973B1 (en) | 2016-12-22 | 2021-09-15 | Incyte Corporation | Pyridine derivatives as immunomodulators |
| IL295660A (en) | 2016-12-22 | 2022-10-01 | Incyte Corp | Benzooxazole derivatives as immunomodulators |
| ES2874756T3 (es) | 2016-12-22 | 2021-11-05 | Incyte Corp | Derivados de triazolo[1,5-A]piridina como inmunomoduladores |
| EP3558963B1 (en) | 2016-12-22 | 2022-03-23 | Incyte Corporation | Bicyclic heteroaromatic compounds as immunomodulators |
| WO2018136827A1 (en) | 2017-01-20 | 2018-07-26 | Vitrisa Therapeutics, Inc. | Stem-loop compositions and methods for inhibiting factor d |
| WO2018152220A1 (en) | 2017-02-15 | 2018-08-23 | Incyte Corporation | Pyrazolopyridine compounds and uses thereof |
| WO2018160892A1 (en) | 2017-03-01 | 2018-09-07 | Achillion Pharmaceuticals, Inc. | Macrocyclic compounds for treatment of medical disorders |
| WO2018160891A1 (en) | 2017-03-01 | 2018-09-07 | Achillion Pharmaceutical, Inc. | Pharmaceutical compounds for treatment of medical disorders |
| AU2018227849B2 (en) | 2017-03-01 | 2022-04-28 | Achillion Pharmaceuticals, Inc. | Aryl, heteroaryl, and heterocyclic pharmaceutical compounds for treatment of medical disorders |
| CN111163767A (zh) | 2017-08-02 | 2020-05-15 | 艾其林医药公司 | 治疗阵发性睡眠性血红蛋白尿症的治疗方案 |
| US10722495B2 (en) | 2017-09-08 | 2020-07-28 | Incyte Corporation | Cyanoindazole compounds and uses thereof |
| US10800761B2 (en) | 2018-02-20 | 2020-10-13 | Incyte Corporation | Carboxamide compounds and uses thereof |
| WO2019164847A1 (en) | 2018-02-20 | 2019-08-29 | Incyte Corporation | Indazole compounds and uses thereof |
| US10745388B2 (en) | 2018-02-20 | 2020-08-18 | Incyte Corporation | Indazole compounds and uses thereof |
| RS64055B1 (sr) | 2018-03-30 | 2023-04-28 | Incyte Corp | Heterociklična jedinjenja kao imunomodulatori |
| US11299473B2 (en) | 2018-04-13 | 2022-04-12 | Incyte Corporation | Benzimidazole and indole compounds and uses thereof |
| EP4219492B1 (en) | 2018-05-11 | 2024-11-27 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| KR20210016545A (ko) | 2018-05-29 | 2021-02-16 | 오메로스 코포레이션 | Masp-2 억제제 및 사용 방법 |
| WO2019236884A1 (en) | 2018-06-07 | 2019-12-12 | Disarm Therapeutics, Inc. | Inhibitors of sarm1 |
| US10899755B2 (en) | 2018-08-08 | 2021-01-26 | Incyte Corporation | Benzothiazole compounds and uses thereof |
| JP7538113B2 (ja) | 2018-08-20 | 2024-08-21 | アキリオン ファーマシューティカルズ，インコーポレーテッド | 補体ｄ因子の医学的障害の治療のための医薬化合物 |
| WO2020051532A2 (en) | 2018-09-06 | 2020-03-12 | Achillion Pharmaceuticals, Inc. | Macrocyclic compounds for the treatment of medical disorders |
| EP3847174A4 (en) | 2018-09-06 | 2022-06-15 | Achillion Pharmaceuticals, Inc. | MORPHIC FORMS OF COMPLEMENT D FACTOR INHIBITORS |
| MA53726A (fr) | 2018-09-25 | 2022-05-11 | Incyte Corp | Composés pyrazolo[4,3-d]pyrimidine en tant que modulateurs des alk2 et/ou fgfr |
| JP2022502500A (ja) * | 2018-09-25 | 2022-01-11 | アキリオン ファーマシューティカルズ， インコーポレーテッド | 補体因子ｄ阻害剤の形態 |
| JP7471300B2 (ja) * | 2018-12-17 | 2024-04-19 | アキリオン ファーマシューティカルズ， インコーポレーテッド | 補体介在性疾患を治療するための的を絞った投与 |
| CA3123215C (en) | 2018-12-19 | 2024-04-02 | Disarm Therapeutics, Inc. | Inhibitors of sarm1 in combination with neuroprotective agents |
| EP3941462A4 (en) | 2019-03-22 | 2023-04-05 | Achillion Pharmaceuticals, Inc. | PHARMACEUTICAL COMPOUNDS FOR THE TREATMENT OF COMPLEMENT-MEDIED DISEASES |
| PE20221419A1 (es) | 2019-08-06 | 2022-09-20 | Incyte Corp | Formas solidas de un inhibidor de hpk1 |
| JP7665593B2 (ja) | 2019-08-09 | 2025-04-21 | インサイト・コーポレイション | Ｐｄ－１／ｐｄ－ｌ１阻害剤の塩 |
| EP4037773A1 (en) | 2019-09-30 | 2022-08-10 | Incyte Corporation | Pyrido[3,2-d]pyrimidine compounds as immunomodulators |
| BR112022009031A2 (pt) | 2019-11-11 | 2022-10-11 | Incyte Corp | Sais e formas cristalinas de um inibidor de pd-1/pd-l1 |
| WO2021113682A1 (en) | 2019-12-04 | 2021-06-10 | Omeros Corporation | Masp-2 inhibitors and methods of use |
| EP4069676A1 (en) * | 2019-12-04 | 2022-10-12 | Omeros Corporation | Masp-2 inhibitors and methods of use |
| CN115362162A (zh) * | 2020-02-20 | 2022-11-18 | 艾其林医药公司 | 用于治疗补体因子d介导的障碍的杂芳基化合物 |
| AR121715A1 (es) * | 2020-04-03 | 2022-06-29 | Biocryst Pharm Inc | Pirrolopirimidinaminas como inhibidores del sistema del complemento |
| CN115666578A (zh) | 2020-05-12 | 2023-01-31 | 阿雷克森制药公司 | 补体因子d抑制剂单独或结合抗c5抗体治疗阵发性睡眠性血红蛋白尿的用途 |
| JP7787164B2 (ja) | 2020-09-23 | 2025-12-16 | アキリオン ファーマシューティカルズ， インコーポレーテッド | 補体媒介性障害の治療のための医薬化合物 |
| WO2022099018A1 (en) | 2020-11-06 | 2022-05-12 | Incyte Corporation | Process of preparing a pd-1/pd-l1 inhibitor |
| EP4240739A1 (en) | 2020-11-06 | 2023-09-13 | Incyte Corporation | Process for making a pd-1/pd-l1 inhibitor and salts and crystalline forms thereof |
| US11760756B2 (en) | 2020-11-06 | 2023-09-19 | Incyte Corporation | Crystalline form of a PD-1/PD-L1 inhibitor |
| MX2023009857A (es) | 2021-03-15 | 2024-01-03 | Maze Therapeutics Inc | Inhibidores de la glucogeno sintasa 1 (gys1) y metodos de uso de los mismos. |
| CN112898273B (zh) * | 2021-03-30 | 2022-05-31 | 海南锦瑞制药有限公司 | 伏立康唑的合成方法及应用 |
| CN113372223B (zh) * | 2021-05-20 | 2022-10-28 | 宁波职业技术学院 | 一种2-氟-3-溴-苄胺的制备方法 |
| EP4362933A4 (en) * | 2021-06-30 | 2025-06-04 | Apellis Pharmaceuticals, Inc. | COMPLEMENT INHIBITION |
| US20250090528A1 (en) * | 2021-10-18 | 2025-03-20 | Alexion Pharmaceuticals, Inc. | Use of complement factor d inhibitor for treatment of lupus nephritis and immunoglobulin a nephropathy |
| EP4174077A1 (en) * | 2021-10-27 | 2023-05-03 | Merck Patent GmbH | Electronic switching device |
| CN114105790A (zh) * | 2021-12-14 | 2022-03-01 | 无锡捷化医药科技有限公司 | 一种3-氨基-4,5-二溴苯甲酸甲酯的制备方法 |
| CN118556060A (zh) * | 2021-12-15 | 2024-08-27 | 阿雷克森制药公司 | 补体因子d抑制剂的合成方法 |
| CN119095831A (zh) * | 2022-03-25 | 2024-12-06 | 瓦斯塞拉股份有限公司 | 3-苯基异噁唑衍生物和含有其作为活性成分的用于预防或治疗眼部疾病的药物组合物 |
| WO2023200364A1 (ru) * | 2022-04-15 | 2023-10-19 | Общество С Ограниченной Ответственностью "Промомед Рус" | Способы получения (1r,2s,5s)-n-[(1s)-1-циано-2-[(3s)-2-оксопирролидин-3-ил]этил]-3-[(2s)-3,3-диметил-2-[(2,2,2-трифторацетил)амино]бутаноил]-6,6-диметил-3-азабицикло[3.1.0]гексан-2-карбоксамида |
| WO2024141011A1 (zh) * | 2022-12-31 | 2024-07-04 | 深圳晶泰科技有限公司 | 补体因子b抑制剂及其药物组合物和应用 |
| WO2025199107A1 (en) | 2024-03-19 | 2025-09-25 | Alexion Pharmaceuticals, Inc. | Risk evaluation and management strategy involving patient follow-ups relating to the use or discontinuation of a complement inhibitor |
Family Cites Families (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT72878B (en) | 1980-04-24 | 1983-03-29 | Merck & Co Inc | Process for preparing mannich-base hydroxamic acid pro-drugs for the improved delivery of non-steroidal anti-inflammatory agents |
| US5164372A (en) | 1989-04-28 | 1992-11-17 | Fujisawa Pharmaceutical Company, Ltd. | Peptide compounds having substance p antagonism, processes for preparation thereof and pharmaceutical composition comprising the same |
| GB9206757D0 (en) | 1992-03-27 | 1992-05-13 | Ferring Bv | Novel peptide receptor ligands |
| EP0610487B1 (de) | 1992-09-03 | 1999-11-10 | Boehringer Ingelheim Pharma KG | Neue aminosäurederivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende pharmazeutische zusammensetzungen |
| US5661161A (en) | 1994-09-29 | 1997-08-26 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
| US5756528A (en) | 1995-06-06 | 1998-05-26 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
| EA200001246A1 (ru) | 1998-06-03 | 2001-08-27 | Джи Пи Ай Нил Холдингс, Инк. | Карбамиды и карбаматы n-гетероциклических карбоновых кислот и изостер карбоновых кислот |
| WO1999062484A1 (en) | 1998-06-03 | 1999-12-09 | Gpi Nil Holdings, Inc. | Small molecule carbamate or urea hair growth compositions and uses |
| CA2334204A1 (en) | 1998-06-03 | 1999-12-09 | Gpi Nil Holdings, Inc. | Heterocyclic ester and amide hair growth compositions and uses |
| US7338976B1 (en) | 1998-08-14 | 2008-03-04 | Gpi Nil Holdings, Inc. | Heterocyclic esters or amides for vision and memory disorders |
| US6653304B2 (en) * | 2000-02-11 | 2003-11-25 | Bristol-Myers Squibb Co. | Cannabinoid receptor modulators, their processes of preparation, and use of cannabinoid receptor modulators for treating respiratory and non-respiratory diseases |
| CA2321348A1 (en) | 2000-09-27 | 2002-03-27 | Blaise Magloire N'zemba | Aromatic derivatives with hiv integrase inhibitory properties |
| EP1326848A1 (en) | 2000-10-19 | 2003-07-16 | Naeja Pharmaceutical Inc. | Dihydropyrimidine derivatives as cysteine protease inhibitors |
| US7030141B2 (en) | 2001-11-29 | 2006-04-18 | Christopher Franklin Bigge | Inhibitors of factor Xa and other serine proteases involved in the coagulation cascade |
| US6933316B2 (en) | 2001-12-13 | 2005-08-23 | National Health Research Institutes | Indole compounds |
| NL1021590C1 (nl) | 2002-10-05 | 2004-04-06 | Johannes Antonius Josep Visser | Oogstinrichting voor het oogsten van gewassen en sorteerinrichting. |
| EP1581503A4 (en) | 2002-11-08 | 2007-07-25 | Merck & Co Inc | OPHTHALMIC COMPOSITIONS FOR THE TREATMENT OF OCCULAR HYPERTONIA |
| AU2003302084A1 (en) | 2002-11-15 | 2004-06-15 | Bristol-Myers Squibb Company | Open chain prolyl urea-related modulators of androgen receptor function |
| SG2012000667A (en) | 2003-01-08 | 2015-03-30 | Univ Washington | Antibacterial agents |
| WO2004062607A2 (en) | 2003-01-13 | 2004-07-29 | Ying Zhang | Use of weak acids or their precursors for the treatment of tuberculosis (tb) and drug resistant tb |
| US7223785B2 (en) | 2003-01-22 | 2007-05-29 | Boehringer Ingelheim International Gmbh | Viral polymerase inhibitors |
| CA2514733A1 (en) | 2003-02-28 | 2004-09-16 | Transform Pharmaceuticals, Inc. | Pharmaceutical co-crystal compositions of drugs such as carbamazepine, celecoxib, olanzapine, itraconazole, topiramate, modafinil, 5-fluorouracil, hydrochlorothiazide, acetaminophen, aspirin, flurbiprofen, phenytoin and ibuprofen |
| US7122557B2 (en) | 2003-03-18 | 2006-10-17 | Bristol-Myers Squibb Company | Sulfonyl-amidino-containing and tetrahydropyrimidino-containing compounds as factor Xa inhibitors |
| BRPI0408420A (pt) | 2003-04-03 | 2006-03-21 | Merck Patent Gmbh | compostos de carbonila |
| US7959919B2 (en) | 2003-11-19 | 2011-06-14 | Novelmed Therapeutics, Inc. | Method of inhibiting factor B-mediated complement activation |
| AU2005212369B2 (en) | 2004-02-10 | 2011-06-23 | Musc Foundation For Research Development | Inhibition of factor B, the alternative complement pathway and methods related thereto |
| US7417063B2 (en) | 2004-04-13 | 2008-08-26 | Bristol-Myers Squibb Company | Bicyclic heterocycles useful as serine protease inhibitors |
| DE102004045796A1 (de) | 2004-09-22 | 2006-03-23 | Merck Patent Gmbh | Arzneimittel enthaltend Carbonylverbindungen sowie deren Verwendung |
| FR2876692B1 (fr) | 2004-10-19 | 2007-02-23 | Sanofi Aventis Sa | Derives de 2-amido-4-phenylthiazole, leur preparation et leur application en therapeutique |
| WO2006090192A1 (en) | 2005-02-28 | 2006-08-31 | Tseti, Ioulia | Medicaments for alzheimer |
| GB0510139D0 (en) | 2005-05-18 | 2005-06-22 | Addex Pharmaceuticals Sa | Novel compounds B1 |
| WO2006127550A1 (en) | 2005-05-23 | 2006-11-30 | Merck & Co., Inc. | Proline bis-amide orexin receptor antagonists |
| CN101277950B (zh) | 2005-08-02 | 2013-03-27 | 弗特克斯药品有限公司 | 丝氨酸蛋白酶抑制剂 |
| BRPI0617186A2 (pt) | 2005-10-08 | 2011-07-19 | Potentia Pharmaceuticals Inc | uso de análogo de compstatina, implante ocular, micropartìcula ou nanopartìcula, composição, composto multivalente, ácido nucléico, vetor de expressão, célula hospedeira recombinante, proteìna de fusão e método de produção e teste |
| WO2007070600A2 (en) | 2005-12-12 | 2007-06-21 | Genelabs Technologies, Inc. | N-(5-membered heteroaromatic ring)-amido anti-viral compounds |
| CA3009846C (en) | 2006-03-08 | 2021-08-31 | David Epstein | Complement binding aptamers and anti-c5 agents useful in the treatment of ocular disorders |
| US7718693B2 (en) * | 2006-07-06 | 2010-05-18 | Glaxo Group Limited | Receptor antagonists and their methods of use |
| WO2008036967A2 (en) | 2006-09-22 | 2008-03-27 | Reddy Us Therapeutics, Inc. | Novel heterocyclic compounds as lasy activators |
| SI2097455T1 (sl) | 2006-11-02 | 2015-03-31 | Genentech, Inc. | Humanizirana protitelesa proti faktorju tipa d |
| EP2099778A2 (en) | 2006-11-21 | 2009-09-16 | Smithkline Beecham Corporation | Amido anti-viral compounds |
| EP1988098A1 (en) | 2007-04-27 | 2008-11-05 | AEterna Zentaris GmbH | Novel Tetrahydrocarbazole Derivatives as Ligands of G-protein Coupled Receptors |
| AR066660A1 (es) | 2007-05-23 | 2009-09-02 | Genentech Inc | Prevencion y tratamiento de condiciones del ojo asociadas con su complemento |
| WO2009106980A2 (en) | 2008-02-29 | 2009-09-03 | Pfizer Inc. | Indazole derivatives |
| KR101353857B1 (ko) | 2008-08-22 | 2014-01-21 | 노파르티스 아게 | Ｃｄｋ 억제제로서 피롤로피리미딘 화합물 |
| US8362020B2 (en) | 2009-12-30 | 2013-01-29 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
-
2012
- 2012-01-02 WO PCT/EP2012/050005 patent/WO2012093101A1/en not_active Ceased
- 2012-01-02 PE PE2013001512A patent/PE20140471A1/es not_active Application Discontinuation
- 2012-01-02 CA CA2823665A patent/CA2823665A1/en not_active Abandoned
- 2012-01-02 EP EP12700094.1A patent/EP2661433B1/en not_active Not-in-force
- 2012-01-02 MA MA36128A patent/MA34837B1/fr unknown
- 2012-01-02 BR BR112013017316A patent/BR112013017316A2/pt not_active IP Right Cessation
- 2012-01-02 SG SG2013051669A patent/SG191844A1/en unknown
- 2012-01-02 US US13/342,161 patent/US9085555B2/en active Active
- 2012-01-02 PL PL12700094T patent/PL2661433T3/pl unknown
- 2012-01-02 ES ES12700094.1T patent/ES2647664T3/es active Active
- 2012-01-02 AP AP2013006986A patent/AP2013006986A0/xx unknown
- 2012-01-02 AU AU2012204920A patent/AU2012204920B2/en not_active Ceased
- 2012-01-02 KR KR1020137020527A patent/KR20140027090A/ko not_active Ceased
- 2012-01-02 PH PH1/2013/501436A patent/PH12013501436A1/en unknown
- 2012-01-02 JP JP2013547843A patent/JP5921572B2/ja not_active Expired - Fee Related
- 2012-01-02 CN CN201280011428.5A patent/CN103402996B/zh not_active Expired - Fee Related
- 2012-01-02 PT PT127000941T patent/PT2661433T/pt unknown
- 2012-01-02 MX MX2013007867A patent/MX347391B/es active IP Right Grant
- 2012-01-02 EA EA201391000A patent/EA023259B1/ru not_active IP Right Cessation
- 2012-01-03 TW TW101100198A patent/TW201242959A/zh unknown
- 2012-01-03 AR ARP120100007A patent/AR084768A1/es unknown
- 2012-01-03 UY UY0001033858A patent/UY33858A/es not_active Application Discontinuation
-
2013
- 2013-06-24 ZA ZA2013/04684A patent/ZA201304684B/en unknown
- 2013-06-26 TN TNP2013000275A patent/TN2013000275A1/fr unknown
- 2013-06-26 CL CL2013001891A patent/CL2013001891A1/es unknown
- 2013-07-02 CU CU2013000094A patent/CU20130094A7/es unknown
- 2013-07-02 CO CO13155727A patent/CO6791608A2/es active IP Right Grant
- 2013-07-02 CR CR20130333A patent/CR20130333A/es unknown
- 2013-07-02 GT GT201300174A patent/GT201300174A/es unknown
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