JP2019011381A5 - - Google Patents
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- Publication number
- JP2019011381A5 JP2019011381A5 JP2018204025A JP2018204025A JP2019011381A5 JP 2019011381 A5 JP2019011381 A5 JP 2019011381A5 JP 2018204025 A JP2018204025 A JP 2018204025A JP 2018204025 A JP2018204025 A JP 2018204025A JP 2019011381 A5 JP2019011381 A5 JP 2019011381A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- acid
- methyl
- tryptophanate
- ethyl
- 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
Links
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- 229910052799 carbon Inorganic materials 0.000 claims description 30
- 239000008194 pharmaceutical composition Substances 0.000 claims description 30
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 28
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 28
- 239000000651 prodrug Substances 0.000 claims description 28
- 229940002612 prodrug Drugs 0.000 claims description 28
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 23
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 22
- 150000003839 salts Chemical group 0.000 claims description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 18
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 18
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 18
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 18
- 230000007935 neutral effect Effects 0.000 claims description 17
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 16
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 16
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 14
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 14
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- NIXKBAZVOQAHGC-UHFFFAOYSA-N phenylmethanesulfonic acid Chemical compound OS(=O)(=O)CC1=CC=CC=C1 NIXKBAZVOQAHGC-UHFFFAOYSA-N 0.000 claims description 14
- ZADWXFSZEAPBJS-SNVBAGLBSA-N (2r)-2-amino-3-(1-methylindol-3-yl)propanoic acid Chemical compound C1=CC=C2N(C)C=C(C[C@@H](N)C(O)=O)C2=C1 ZADWXFSZEAPBJS-SNVBAGLBSA-N 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- -1 2- (dimethylamino) ethyl 1-methyl-D-tryptophanate Chemical compound 0.000 claims description 10
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 8
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 8
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 8
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 8
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 8
- 229950009034 indoximod Drugs 0.000 claims description 8
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 7
- ZLEAOBRWCNVHAQ-GUYCJALGSA-N (2S,4S)-2,4-diamino-2-[(1-methylindol-3-yl)methyl]-6-methylsulfanyl-3-oxohexanoic acid Chemical compound N[C@@H](CCSC)C(=O)[C@@](N)(CC1=CN(C2=CC=CC=C12)C)C(=O)O ZLEAOBRWCNVHAQ-GUYCJALGSA-N 0.000 claims description 6
- QGXSIUQBLFORDX-KSSFIOAISA-N (2S,4S)-2,4-diamino-6-methyl-2-[(1-methylindol-3-yl)methyl]-3-oxoheptanoic acid Chemical compound N[C@@H](CC(C)C)C(=O)[C@@](N)(CC1=CN(C2=CC=CC=C12)C)C(=O)O QGXSIUQBLFORDX-KSSFIOAISA-N 0.000 claims description 6
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims description 6
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 6
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 6
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 6
- 235000011054 acetic acid Nutrition 0.000 claims description 6
- 235000003704 aspartic acid Nutrition 0.000 claims description 6
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims description 6
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 6
- 235000015165 citric acid Nutrition 0.000 claims description 6
- 239000012458 free base Substances 0.000 claims description 6
- 239000001530 fumaric acid Substances 0.000 claims description 6
- 235000011087 fumaric acid Nutrition 0.000 claims description 6
- 235000013922 glutamic acid Nutrition 0.000 claims description 6
- 239000004220 glutamic acid Substances 0.000 claims description 6
- 239000004310 lactic acid Substances 0.000 claims description 6
- 235000014655 lactic acid Nutrition 0.000 claims description 6
- 239000011976 maleic acid Substances 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 239000011975 tartaric acid Substances 0.000 claims description 6
- 235000002906 tartaric acid Nutrition 0.000 claims description 6
- AUZJUHQKHCWXEX-KSSFIOAISA-N (2S,4S)-2,4,8-triamino-2-[(1-methylindol-3-yl)methyl]-3-oxooctanoic acid Chemical compound N[C@@H](CCCCN)C(=O)[C@@](N)(CC1=CN(C2=CC=CC=C12)C)C(=O)O AUZJUHQKHCWXEX-KSSFIOAISA-N 0.000 claims description 4
- HISMFAKLLCXFAP-UWJYYQICSA-N (2S,4S)-2,4-diamino-2-[(1-methylindol-3-yl)methyl]-3-oxo-5-phenylpentanoic acid Chemical compound N[C@@H](CC1=CC=CC=C1)C(=O)[C@@](N)(CC1=CN(C2=CC=CC=C12)C)C(=O)O HISMFAKLLCXFAP-UWJYYQICSA-N 0.000 claims description 4
- INCDWUAFGVRRRA-GLGOKHISSA-N CN1C=C(C[C@@H](N)C(=O)OCC(CO)O)C2=CC=CC=C12 Chemical compound CN1C=C(C[C@@H](N)C(=O)OCC(CO)O)C2=CC=CC=C12 INCDWUAFGVRRRA-GLGOKHISSA-N 0.000 claims description 4
- NHNGRCQKZLBCTE-UONOGXRCSA-N N[C@@H](CCCC(=O)O)C(=O)N[C@H](CC1=CN(C2=CC=CC=C12)C)C(=O)O Chemical compound N[C@@H](CCCC(=O)O)C(=O)N[C@H](CC1=CN(C2=CC=CC=C12)C)C(=O)O NHNGRCQKZLBCTE-UONOGXRCSA-N 0.000 claims description 4
- 235000010323 ascorbic acid Nutrition 0.000 claims description 4
- 239000011668 ascorbic acid Substances 0.000 claims description 4
- 229960005070 ascorbic acid Drugs 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 239000002775 capsule Substances 0.000 claims description 4
- VPDDSBCKUAFOIS-GFCCVEGCSA-N ethyl (2R)-2-amino-3-(1-methylindol-3-yl)propanoate Chemical compound CN1C=C(C[C@@H](N)C(=O)OCC)C2=CC=CC=C12 VPDDSBCKUAFOIS-GFCCVEGCSA-N 0.000 claims description 4
- KMSKYVDBQZIXDU-LLVKDONJSA-N methyl (2r)-2-amino-3-(1-methylindol-3-yl)propanoate Chemical compound C1=CC=C2C(C[C@@H](N)C(=O)OC)=CN(C)C2=C1 KMSKYVDBQZIXDU-LLVKDONJSA-N 0.000 claims description 4
- 235000006408 oxalic acid Nutrition 0.000 claims description 4
- AXXDSAWEUYJWGP-QGZVFWFLSA-N (2R)-2-amino-2-[(1-methylindol-3-yl)methyl]-3-[(2-methylpropan-2-yl)oxy]-3-oxopropanoic acid Chemical compound C1=CC=C2N(C)C=C(C[C@@](N)(C(O)=O)C(=O)OC(C)(C)C)C2=C1 AXXDSAWEUYJWGP-QGZVFWFLSA-N 0.000 claims description 3
- 239000006187 pill Substances 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 239000003826 tablet Substances 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 8
- YQVMINCAVFKWRM-SJCJKPOMSA-N (2S,4S)-2,4,7-triamino-2-[(1-methylindol-3-yl)methyl]-3,7-dioxoheptanoic acid Chemical compound N[C@@H](CCC(N)=O)C(=O)[C@@](N)(CC1=CN(C2=CC=CC=C12)C)C(=O)O YQVMINCAVFKWRM-SJCJKPOMSA-N 0.000 claims 2
- MSRQENDYNWLTCU-GYOIFBIXSA-N (2S,4S,5S)-2,4-diamino-5-methyl-2-[(1-methylindol-3-yl)methyl]-3-oxoheptanoic acid Chemical compound N[C@@H]([C@@H](C)CC)C(=O)[C@@](N)(CC1=CN(C2=CC=CC=C12)C)C(=O)O MSRQENDYNWLTCU-GYOIFBIXSA-N 0.000 claims 2
- MUYHGWPFILPMDR-CYBMUJFWSA-N CN1C=C(C[C@@H](N)C(=O)OC(C)C)C2=CC=CC=C12 Chemical compound CN1C=C(C[C@@H](N)C(=O)OC(C)C)C2=CC=CC=C12 MUYHGWPFILPMDR-CYBMUJFWSA-N 0.000 claims 2
- 229910019142 PO4 Inorganic materials 0.000 description 16
- 229910006069 SO3H Inorganic materials 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 6
- 239000010452 phosphate Substances 0.000 description 6
- 150000001450 anions Chemical class 0.000 description 5
- 206010028980 Neoplasm Diseases 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
- 206010062016 Immunosuppression Diseases 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 2
- WXTSKOFJNRRBHP-DLBZAZTESA-N N[C@@H](CC(C)C)C(=O)N[C@H](CC1=CN(C2=CC=CC=C12)C)C(=O)OCC Chemical compound N[C@@H](CC(C)C)C(=O)N[C@H](CC1=CN(C2=CC=CC=C12)C)C(=O)OCC WXTSKOFJNRRBHP-DLBZAZTESA-N 0.000 description 2
- RNKZTSCYRPXRSK-LSDHHAIUSA-N N[C@@H](CCC(N)=O)C(=O)N[C@H](CC1=CN(C2=CC=CC=C12)C)C(=O)OCC Chemical compound N[C@@H](CCC(N)=O)C(=O)N[C@H](CC1=CN(C2=CC=CC=C12)C)C(=O)OCC RNKZTSCYRPXRSK-LSDHHAIUSA-N 0.000 description 2
- MGJILDWFUXXIKT-JKSUJKDBSA-N N[C@@H](CCSC)C(=O)N[C@H](CC1=CN(C2=CC=CC=C12)C)C(=O)OCC Chemical compound N[C@@H](CCSC)C(=O)N[C@H](CC1=CN(C2=CC=CC=C12)C)C(=O)OCC MGJILDWFUXXIKT-JKSUJKDBSA-N 0.000 description 2
- SZMQSLZCPBJELC-XCRHUMRWSA-N N[C@@H]([C@@H](C)CC)C(=O)N[C@H](CC1=CN(C2=CC=CC=C12)C)C(=O)OCC Chemical compound N[C@@H]([C@@H](C)CC)C(=O)N[C@H](CC1=CN(C2=CC=CC=C12)C)C(=O)OCC SZMQSLZCPBJELC-XCRHUMRWSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 2
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 2
- 150000001449 anionic compounds Chemical class 0.000 description 2
- 229940009098 aspartate Drugs 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- SABMRGRNFNZJMW-LJQANCHMSA-N ethyl (2R)-2-(benzylamino)-3-(1-methylindol-3-yl)propanoate Chemical compound C(C1=CC=CC=C1)N[C@H](CC1=CN(C2=CC=CC=C12)C)C(=O)OCC SABMRGRNFNZJMW-LJQANCHMSA-N 0.000 description 2
- 229930195712 glutamate Natural products 0.000 description 2
- 230000001506 immunosuppresive effect Effects 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 150000002891 organic anions Chemical class 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 2
- 229940095064 tartrate Drugs 0.000 description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 2
- QIVBCDIJIAJPQS-UHFFFAOYSA-M tryptophanate Chemical compound C1=CC=C2C(CC(N)C([O-])=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-M 0.000 description 2
- 229940116269 uric acid Drugs 0.000 description 2
- OHPBREBKPBFZCY-CYBMUJFWSA-N (2r)-3-(1-methylindol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound C1=CC=C2N(C)C=C(C[C@@H](NC(=O)OC(C)(C)C)C(O)=O)C2=C1 OHPBREBKPBFZCY-CYBMUJFWSA-N 0.000 description 1
- 208000031886 HIV Infections Diseases 0.000 description 1
- 150000001767 cationic compounds Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 102000006639 indoleamine 2,3-dioxygenase Human genes 0.000 description 1
- 108020004201 indoleamine 2,3-dioxygenase Proteins 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 206010022000 influenza Diseases 0.000 description 1
- 229910001411 inorganic cation Inorganic materials 0.000 description 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2021088493A JP2021121633A (ja) | 2015-07-24 | 2021-05-26 | １−メチル−ｄ−トリプトファンの塩及びプロドラッグ |
| JP2023037970A JP2023060349A (ja) | 2015-07-24 | 2023-03-10 | １－メチル－ｄ－トリプトファンの塩及びプロドラッグ |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562196671P | 2015-07-24 | 2015-07-24 | |
| US62/196,671 | 2015-07-24 | ||
| US201662305748P | 2016-03-09 | 2016-03-09 | |
| US62/305,748 | 2016-03-09 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017561946A Division JP6842429B2 (ja) | 2015-07-24 | 2016-06-02 | １−メチル−ｄ−トリプトファンの塩及びプロドラッグ |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021088493A Division JP2021121633A (ja) | 2015-07-24 | 2021-05-26 | １−メチル−ｄ−トリプトファンの塩及びプロドラッグ |
| JP2023037970A Division JP2023060349A (ja) | 2015-07-24 | 2023-03-10 | １－メチル－ｄ－トリプトファンの塩及びプロドラッグ |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019011381A JP2019011381A (ja) | 2019-01-24 |
| JP2019011381A5 true JP2019011381A5 (https=) | 2019-12-19 |
| JP7286299B2 JP7286299B2 (ja) | 2023-06-05 |
Family
ID=57836622
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017561946A Active JP6842429B2 (ja) | 2015-07-24 | 2016-06-02 | １−メチル−ｄ−トリプトファンの塩及びプロドラッグ |
| JP2018204025A Active JP7286299B2 (ja) | 2015-07-24 | 2018-10-30 | １－メチル－ｄ－トリプトファンの塩及びプロドラッグ |
| JP2021088493A Pending JP2021121633A (ja) | 2015-07-24 | 2021-05-26 | １−メチル−ｄ−トリプトファンの塩及びプロドラッグ |
| JP2023037970A Withdrawn JP2023060349A (ja) | 2015-07-24 | 2023-03-10 | １－メチル－ｄ－トリプトファンの塩及びプロドラッグ |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017561946A Active JP6842429B2 (ja) | 2015-07-24 | 2016-06-02 | １−メチル−ｄ−トリプトファンの塩及びプロドラッグ |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021088493A Pending JP2021121633A (ja) | 2015-07-24 | 2021-05-26 | １−メチル−ｄ−トリプトファンの塩及びプロドラッグ |
| JP2023037970A Withdrawn JP2023060349A (ja) | 2015-07-24 | 2023-03-10 | １－メチル－ｄ－トリプトファンの塩及びプロドラッグ |
Country Status (24)
| Country | Link |
|---|---|
| US (4) | US9732035B2 (https=) |
| EP (4) | EP4659747A2 (https=) |
| JP (4) | JP6842429B2 (https=) |
| KR (2) | KR20180086300A (https=) |
| CN (2) | CN111004167B (https=) |
| AU (1) | AU2016298471C1 (https=) |
| BR (1) | BR112018000225A2 (https=) |
| CA (3) | CA2992016C (https=) |
| CL (1) | CL2018000082A1 (https=) |
| CO (1) | CO2017013724A2 (https=) |
| CR (1) | CR20180023A (https=) |
| DO (1) | DOP2018000011A (https=) |
| EA (1) | EA201792256A1 (https=) |
| EC (1) | ECSP18002561A (https=) |
| ES (3) | ES2923184T3 (https=) |
| HK (2) | HK1247844A1 (https=) |
| IL (2) | IL255625B (https=) |
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Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP4659747A2 (en) | 2015-07-24 | 2025-12-10 | Lumos Pharma, Inc. | Salts and prodrugs of 1-methyl-d-tryptophan |
| CN109400517A (zh) * | 2017-08-17 | 2019-03-01 | 上海时莱生物技术有限公司 | 1-甲基-色氨酸类化合物及其制备方法和用途 |
| JP2020534289A (ja) | 2017-09-14 | 2020-11-26 | ランケナー インスティテュート フォー メディカル リサーチ | がんの治療のための方法および組成物 |
| CN109646683A (zh) * | 2019-02-27 | 2019-04-19 | 武汉理工大学 | 一种1-mt-羧甲基壳聚糖药物的制备方法 |
| AU2020384481B2 (en) | 2019-11-12 | 2025-12-11 | Nammi Therapeutics, Inc. | Formulated and/or co-formulated liposome compositions containing IDO antagonist prodrugs useful in the treatment of cancer and methods thereof |
| KR20230066582A (ko) | 2020-09-10 | 2023-05-16 | 남미 테라퓨틱스, 인크. | 암의 치료에 유용한 pd-1 길항제 전구약물을 함유하는 제제화된 및/또는 공동-제제화된 리포솜 조성물 및 그의 방법 |
| KR20250029575A (ko) | 2023-08-23 | 2025-03-05 | 한국과학기술원 | 카메라 시스템의 동적 환경에 강인한 자기 위치 추정 장치 및 그 방법 |
Family Cites Families (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US14139A (en) | 1856-01-22 | Method oe ventilating railroad-cabs | ||
| GB1330573A (en) | 1970-09-12 | 1973-09-19 | Ajinomoto Kk | Optical resolution of dl-tryptophan derivatives |
| US4072691A (en) | 1974-01-12 | 1978-02-07 | Tanabe Seiyaku Co., Ltd. | Process for the resolution of DL-6-chlorotryptophan |
| US5185157A (en) | 1990-05-02 | 1993-02-09 | Caston John C | Treatment of refractory Eosinophilia-Myalgia Syndrome with L-tryptophan composition |
| WO1996011927A1 (en) | 1994-10-12 | 1996-04-25 | Abbott Laboratories | Endothelin antagonists |
| US6451840B1 (en) | 1997-12-05 | 2002-09-17 | Medical College Of Georgia Research Institute, Inc. | Regulation of T cell-mediated immunity by tryptophan |
| KR100523119B1 (ko) * | 2000-03-16 | 2005-10-20 | 에프. 호프만-라 로슈 아게 | Ｉｐ 길항제로서의 카복실산 유도체 |
| ES2307758T3 (es) * | 2001-06-05 | 2008-12-01 | Lilly Icos Llc | Derivados de pirazino (1',2':1,6)pirido(3,4-b)indol 1,4-diona. |
| US7714139B2 (en) | 2003-03-27 | 2010-05-11 | Lankenau Institute For Medcial Research | IDO inhibitors and methods of use |
| US7598287B2 (en) | 2003-04-01 | 2009-10-06 | Medical College Of Georgia Research Institute, Inc. | Use of inhibitors of indoleamine-2,3-dioxygenase in combination with other therapeutic modalities |
| JO2625B1 (en) * | 2003-06-24 | 2011-11-01 | ميرك شارب اند دوم كوربوريشن | Phosphoric acid salts of dipeptidyl betidase inhibitor 4 |
| JPWO2005073180A1 (ja) | 2003-12-25 | 2008-01-10 | 株式会社クレハ | ヒドロキサム酸誘導体、及び該誘導体を含むａｇｅ生成阻害剤 |
| PL1879573T3 (pl) | 2005-05-10 | 2013-05-31 | Incyte Holdings Corp | Modulatory 2,3-dioksygenazy indoloaminy i sposoby ich zastosowania |
| WO2007081878A2 (en) * | 2006-01-07 | 2007-07-19 | Medical College Of Georgia Research Institute, Inc. | Indoleamine 2,3-dioxygenase pathways in the generation of regulatory t cells |
| US7705022B2 (en) | 2005-10-27 | 2010-04-27 | Lankenau Institute For Medical Research | IDO inhibitors and methods of use thereof |
| US8450351B2 (en) | 2005-12-20 | 2013-05-28 | Incyte Corporation | N-hydroxyamidinoheterocycles as modulators of indoleamine 2,3-dioxygenase |
| CA2569204A1 (en) | 2006-11-28 | 2008-05-28 | Apotex Technologies Inc. | Crystalline d-isoglutamyl-d-tryptophan and the mono ammonium salt of d-isoglutamyl-d-tryptophan |
| WO2008100562A2 (en) * | 2007-02-14 | 2008-08-21 | Medical College Of Georgia Research Institute, Inc. | Indoleamine 2,3-dioxygenase, pd-1/pd-l pathways, and ctla4 pathways in the activation of regulatory t cells |
| US8389568B2 (en) | 2007-03-16 | 2013-03-05 | Lankenau Institute For Medical Research | IDO inhibitors and methods of use thereof |
| US10047066B2 (en) | 2007-11-30 | 2018-08-14 | Newlink Genetics Corporation | IDO inhibitors |
| ATE514671T1 (de) * | 2008-02-01 | 2011-07-15 | Firmenich & Cie | Substituierte cyclohexenone |
| CA2722159C (en) | 2008-04-24 | 2016-04-05 | Newlink Genetics Corporation | Substituted phenylimidazole compounds and their use as ido inhibitors |
| JP5465720B2 (ja) | 2008-07-08 | 2014-04-09 | インサイト・コーポレイション | インドールアミン２，３−ジオキシゲナーゼの阻害剤としての１，２，５−オキサジアゾール |
| HUE030465T2 (hu) | 2009-05-13 | 2017-05-29 | Antivirális vegyületek | |
| EP2493862B1 (en) * | 2009-10-28 | 2016-10-05 | Newlink Genetics Corporation | Imidazole derivatives as ido inhibitors |
| US20130142815A1 (en) * | 2010-02-09 | 2013-06-06 | Georiga Health Sciences Univ. Research Inst., Inc. | Alpha-methyl-tryptophan as an inhibitor of indoleamine dioxygenase |
| NO2694640T3 (https=) | 2011-04-15 | 2018-03-17 | ||
| JO3353B1 (ar) | 2012-04-20 | 2019-03-13 | Ono Pharmaceutical Co | شكل صلب معزول من أحادي هيدروكلوريد أناموريلين بنسبة مولارية منخفضة من الكلوريد: أناموريلين ومحتوى منخفض من مذيب عضوي متبقي |
| KR20150087400A (ko) | 2012-11-20 | 2015-07-29 | 버텍스 파마슈티칼스 인코포레이티드 | 인돌아민 2,3-디옥시게나제의 억제제로서 유용한 화합물 |
| WO2014141110A2 (en) | 2013-03-14 | 2014-09-18 | Curadev Pharma Pvt. Ltd. | Aminonitriles as kynurenine pathway inhibitors |
| KR20150126623A (ko) | 2013-03-14 | 2015-11-12 | 뉴링크 제네틱스 코퍼레이션 | 트립토판 대사로 인한 면역억제의 억제제로서의 삼환식 화합물 |
| SG11201507395PA (en) | 2013-03-14 | 2015-10-29 | Curadev Pharma Private Ltd | Inhibitors of the kynurenine pathway |
| EA031470B1 (ru) | 2013-03-15 | 2019-01-31 | Бристол-Майерс Сквибб Компани | Ингибиторы ido |
| EP2970114B1 (en) | 2013-03-15 | 2019-05-15 | Bristol-Myers Squibb Company | Ido inhibitors |
| MX2015017486A (es) | 2013-07-01 | 2016-03-21 | Squibb Bristol Myers Co | Inhibidores de indolamina 2,3-dioxigenasa (dio). |
| ES2707961T3 (es) | 2013-07-11 | 2019-04-08 | Bristol Myers Squibb Co | Inhibidores de IDO |
| EP4659747A2 (en) | 2015-07-24 | 2025-12-10 | Lumos Pharma, Inc. | Salts and prodrugs of 1-methyl-d-tryptophan |
| CO2018009382A2 (es) | 2016-03-09 | 2018-09-20 | Univ Emory | Eliminación del virus de la hepatitis b con agentes antivirales |
| WO2018006035A1 (en) | 2016-06-30 | 2018-01-04 | Timpson Electrical & Aerial Services, LLC | High voltage training device and system and method thereof |
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