RU2008112683A - Ингибиторы fap - Google Patents
Ингибиторы fap Download PDFInfo
- Publication number
- RU2008112683A RU2008112683A RU2008112683/04A RU2008112683A RU2008112683A RU 2008112683 A RU2008112683 A RU 2008112683A RU 2008112683/04 A RU2008112683/04 A RU 2008112683/04A RU 2008112683 A RU2008112683 A RU 2008112683A RU 2008112683 A RU2008112683 A RU 2008112683A
- Authority
- RU
- Russia
- Prior art keywords
- pyrrolidine
- carbonitrile
- alkyl
- group
- aryl
- Prior art date
Links
- 239000003112 inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 35
- 125000003118 aryl group Chemical group 0.000 claims abstract 22
- 125000000217 alkyl group Chemical group 0.000 claims abstract 19
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 14
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 12
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 8
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000003709 fluoroalkyl group Chemical group 0.000 claims abstract 3
- 239000001301 oxygen Substances 0.000 claims abstract 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 2
- 150000003839 salts Chemical class 0.000 claims abstract 2
- 239000011593 sulfur Substances 0.000 claims abstract 2
- -1 (2S) -2- (2-Methoxybenzoylamino) -3-methylpentanoyl Chemical group 0.000 claims 10
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 206010016654 Fibrosis Diseases 0.000 claims 5
- 150000007649 L alpha amino acids Chemical class 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 208000019425 cirrhosis of liver Diseases 0.000 claims 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 230000007882 cirrhosis Effects 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- RGICCULPCWNRAB-UHFFFAOYSA-N 2-[2-(2-hexoxyethoxy)ethoxy]ethanol Chemical compound CCCCCCOCCOCCOCCO RGICCULPCWNRAB-UHFFFAOYSA-N 0.000 claims 2
- 208000016216 Choristoma Diseases 0.000 claims 2
- 206010027476 Metastases Diseases 0.000 claims 2
- 208000007502 anemia Diseases 0.000 claims 2
- 210000000601 blood cell Anatomy 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 238000002512 chemotherapy Methods 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 230000004761 fibrosis Effects 0.000 claims 2
- 230000003211 malignant effect Effects 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 208000004235 neutropenia Diseases 0.000 claims 2
- 210000000056 organ Anatomy 0.000 claims 2
- 230000008467 tissue growth Effects 0.000 claims 2
- 230000029663 wound healing Effects 0.000 claims 2
- BHPWUBNBWJDBRI-GJZGRUSLSA-N (2s)-1-[(2s)-1-(3-chlorobenzoyl)pyrrolidine-2-carbonyl]pyrrolidine-2-carbonitrile Chemical compound ClC1=CC=CC(C(=O)N2[C@@H](CCC2)C(=O)N2[C@@H](CCC2)C#N)=C1 BHPWUBNBWJDBRI-GJZGRUSLSA-N 0.000 claims 1
- VGPPINZLYPNBTM-HOCLYGCPSA-N (2s)-1-[(2s)-1-(3-methoxybenzoyl)pyrrolidine-2-carbonyl]pyrrolidine-2-carbonitrile Chemical compound COC1=CC=CC(C(=O)N2[C@@H](CCC2)C(=O)N2[C@@H](CCC2)C#N)=C1 VGPPINZLYPNBTM-HOCLYGCPSA-N 0.000 claims 1
- ZERXNNPHBAEGND-HOTGVXAUSA-N (2s)-1-[(2s)-1-benzoylpiperidine-2-carbonyl]pyrrolidine-2-carbonitrile Chemical compound C([C@H]1C(=O)N2[C@@H](CCC2)C#N)CCCN1C(=O)C1=CC=CC=C1 ZERXNNPHBAEGND-HOTGVXAUSA-N 0.000 claims 1
- DUAMOTNTPOWUPE-VWHLVEDXSA-N (2s)-1-[(2s)-2-(2-methoxybenzoyl)-1,3,3a,4,5,6,7,7a-octahydroindole-2-carbonyl]pyrrolidine-2-carbaldehyde Chemical compound COC1=CC=CC=C1C(=O)[C@@]1(C(=O)N2[C@@H](CCC2)C=O)NC2CCCCC2C1 DUAMOTNTPOWUPE-VWHLVEDXSA-N 0.000 claims 1
- HOGMKLFVXPLGIF-HKDCCESQSA-N (2s)-1-[(2s)-2-(4-methylbenzoyl)-1,3,3a,4,5,6,7,7a-octahydroindole-2-carbonyl]pyrrolidine-2-carbonitrile Chemical compound C1=CC(C)=CC=C1C(=O)[C@@]1(C(=O)N2[C@@H](CCC2)C#N)NC2CCCCC2C1 HOGMKLFVXPLGIF-HKDCCESQSA-N 0.000 claims 1
- DQLWFRJPQSKXMX-UWVGGRQHSA-N (2s)-2-[(2s)-2-cyano-4,4-difluoropyrrolidine-1-carbonyl]-n-ethylpyrrolidine-1-carboxamide Chemical compound CCNC(=O)N1CCC[C@H]1C(=O)N1[C@H](C#N)CC(F)(F)C1 DQLWFRJPQSKXMX-UWVGGRQHSA-N 0.000 claims 1
- HUCDGWFIFAEIHW-VSUJBEPISA-N (2s)-2-[(2s)-2-cyanopyrrolidine-1-carbonyl]-n-ethyl-1,3,3a,4,5,6,7,7a-octahydroindole-2-carboxamide Chemical compound O=C([C@@]1(NC2CCCCC2C1)C(=O)NCC)N1CCC[C@H]1C#N HUCDGWFIFAEIHW-VSUJBEPISA-N 0.000 claims 1
- HBSIJYHNQSYMFP-RYUDHWBXSA-N (2s)-2-[(2s)-2-cyanopyrrolidine-1-carbonyl]-n-propan-2-ylpyrrolidine-1-carboxamide Chemical compound CC(C)NC(=O)N1CCC[C@H]1C(=O)N1[C@H](C#N)CCC1 HBSIJYHNQSYMFP-RYUDHWBXSA-N 0.000 claims 1
- AZTYKQXGOBGTPX-RYUDHWBXSA-N (2s)-2-[(2s)-2-cyanopyrrolidine-1-carbonyl]-n-propylpyrrolidine-1-carbothioamide Chemical compound CCCNC(=S)N1CCC[C@H]1C(=O)N1[C@H](C#N)CCC1 AZTYKQXGOBGTPX-RYUDHWBXSA-N 0.000 claims 1
- FQULOSOYTBNLIJ-SHWKFHJASA-N (2s)-n-ethyl-2-[(2s)-2-formylpyrrolidine-1-carbonyl]-2,3,3a,4,5,6,7,7a-octahydroindole-1-carboxamide Chemical compound O=C([C@@H]1CC2CCCCC2N1C(=O)NCC)N1CCC[C@H]1C=O FQULOSOYTBNLIJ-SHWKFHJASA-N 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- JWFDLILYICVSFH-UHFFFAOYSA-N 1,1-dioxo-1,3-thiazolidine-4-carbonitrile Chemical compound O=S1(=O)CNC(C#N)C1 JWFDLILYICVSFH-UHFFFAOYSA-N 0.000 claims 1
- CBEFQPARQNDBRR-UWVGGRQHSA-N 1-[(2s)-1-[(2s)-2-cyano-4,4-difluoropyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]-3-ethylurea Chemical compound CCNC(=O)N[C@@H](C(C)C)C(=O)N1CC(F)(F)C[C@H]1C#N CBEFQPARQNDBRR-UWVGGRQHSA-N 0.000 claims 1
- HLNHLDNAGJUUKD-HOTGVXAUSA-N 1-[(2s)-1-[(2s)-2-cyanopyrrolidin-1-yl]-1-oxo-3-phenylpropan-2-yl]-3-propan-2-ylurea Chemical compound C([C@H](NC(=O)NC(C)C)C(=O)N1[C@@H](CCC1)C#N)C1=CC=CC=C1 HLNHLDNAGJUUKD-HOTGVXAUSA-N 0.000 claims 1
- CQPKYTAFAQYZBS-UWVGGRQHSA-N 1-[(2s)-1-[(2s)-2-cyanopyrrolidin-1-yl]-1-oxopropan-2-yl]-3-propan-2-ylurea Chemical compound CC(C)NC(=O)N[C@@H](C)C(=O)N1CCC[C@H]1C#N CQPKYTAFAQYZBS-UWVGGRQHSA-N 0.000 claims 1
- ZSCRPXVYYFXEHH-QWRGUYRKSA-N 1-[(2s)-1-[(2s)-2-cyanopyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]-3-ethylurea Chemical compound CCNC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C#N ZSCRPXVYYFXEHH-QWRGUYRKSA-N 0.000 claims 1
- FTTUJTGRYWOXDJ-BEEDKBRMSA-N 1-[(2s)-1-[(2s)-2-cyanopyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]-3-(2-phenylethyl)thiourea Chemical compound N([C@@H](C(C)CC)C(=O)N1[C@@H](CCC1)C#N)C(=S)NCCC1=CC=CC=C1 FTTUJTGRYWOXDJ-BEEDKBRMSA-N 0.000 claims 1
- BUNPRTJDEIFBRC-RAMGSTBQSA-N 1-[(2s)-1-[(2s)-2-cyanopyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]-3-ethylurea Chemical compound CCNC(=O)N[C@@H](C(C)CC)C(=O)N1CCC[C@H]1C#N BUNPRTJDEIFBRC-RAMGSTBQSA-N 0.000 claims 1
- WETHEFNJDNRLNI-HOTGVXAUSA-N 1-[(2s)-1-[(2s)-2-cyanopyrrolidin-1-yl]-4-methyl-1-oxopentan-2-yl]-3-cyclohexylurea Chemical compound N([C@@H](CC(C)C)C(=O)N1[C@@H](CCC1)C#N)C(=O)NC1CCCCC1 WETHEFNJDNRLNI-HOTGVXAUSA-N 0.000 claims 1
- DNZCDLDJXZSDAH-STQMWFEESA-N 1-[(2s)-1-[(2s)-2-cyanopyrrolidin-1-yl]-4-methyl-1-oxopentan-2-yl]-3-ethyl-1-methylurea Chemical compound CCNC(=O)N(C)[C@@H](CC(C)C)C(=O)N1CCC[C@H]1C#N DNZCDLDJXZSDAH-STQMWFEESA-N 0.000 claims 1
- QDPLHRWMRWAAAC-JKSUJKDBSA-N 1-benzyl-3-[(2s)-1-[(2s)-2-cyanopyrrolidin-1-yl]-3,3-dimethyl-1-oxobutan-2-yl]urea Chemical compound N([C@@H](C(C)(C)C)C(=O)N1[C@@H](CCC1)C#N)C(=O)NCC1=CC=CC=C1 QDPLHRWMRWAAAC-JKSUJKDBSA-N 0.000 claims 1
- RNQZZHMEFRITHS-VYIIXAMBSA-N 2-methoxy-n-[(2s)-3-methyl-1-oxo-1-pyrrolidin-1-ylpentan-2-yl]benzamide Chemical compound N([C@@H](C(C)CC)C(=O)N1CCCC1)C(=O)C1=CC=CC=C1OC RNQZZHMEFRITHS-VYIIXAMBSA-N 0.000 claims 1
- 239000004475 Arginine Substances 0.000 claims 1
- OAKKEQGCYJDXOZ-BWESVNLHSA-O CCC(C)[C@@H](C([S+](C1)CN[C@@H]1C#N)=O)NC(C1=CC=CC(OC)=C1)=O Chemical compound CCC(C)[C@@H](C([S+](C1)CN[C@@H]1C#N)=O)NC(C1=CC=CC(OC)=C1)=O OAKKEQGCYJDXOZ-BWESVNLHSA-O 0.000 claims 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims 1
- DNRDOVSZCGLLGT-TUJLOAKASA-N N([C@@H](C(C)CC)C(=O)S1(=O)C[C@H](NC1)C#N)C(=O)C1=CC=CC(OC)=C1 Chemical compound N([C@@H](C(C)CC)C(=O)S1(=O)C[C@H](NC1)C#N)C(=O)C1=CC=CC(OC)=C1 DNRDOVSZCGLLGT-TUJLOAKASA-N 0.000 claims 1
- PUHNKEIEKGBUJL-UWVGGRQHSA-N [(2r)-1-[(2s)-2-(ethylcarbamoylamino)-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid Chemical compound CCNC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1B(O)O PUHNKEIEKGBUJL-UWVGGRQHSA-N 0.000 claims 1
- ANPJLJNEFJVWOO-GJZGRUSLSA-N [(2r)-1-[(2s)-2-[(2-methoxybenzoyl)amino]-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid Chemical compound COC1=CC=CC=C1C(=O)N[C@@H](C(C)C)C(=O)N1[C@H](B(O)O)CCC1 ANPJLJNEFJVWOO-GJZGRUSLSA-N 0.000 claims 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 1
- 235000004279 alanine Nutrition 0.000 claims 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims 1
- DDHODFLDJUQHSX-SFTDATJTSA-N benzyl (4s)-4-[(4-chlorobenzoyl)amino]-5-[(2s)-2-cyanopyrrolidin-1-yl]-5-oxopentanoate Chemical compound C1=CC(Cl)=CC=C1C(=O)N[C@H](C(=O)N1[C@@H](CCC1)C#N)CCC(=O)OCC1=CC=CC=C1 DDHODFLDJUQHSX-SFTDATJTSA-N 0.000 claims 1
- QFDOFQHDZCGZJQ-ICSRJNTNSA-N benzyl n-[(2s)-3-[(2s)-2-cyanopyrrolidin-1-yl]-2-[(2-methoxybenzoyl)amino]-3-oxopropyl]carbamate Chemical compound COC1=CC=CC=C1C(=O)N[C@H](C(=O)N1[C@@H](CCC1)C#N)CNC(=O)OCC1=CC=CC=C1 QFDOFQHDZCGZJQ-ICSRJNTNSA-N 0.000 claims 1
- BAKBWMQUYIHULH-FPOVZHCZSA-N benzyl n-[(3s)-4-[(2s)-2-cyanopyrrolidin-1-yl]-3-[(2-methoxybenzoyl)amino]-4-oxobutyl]carbamate Chemical compound COC1=CC=CC=C1C(=O)N[C@H](C(=O)N1[C@@H](CCC1)C#N)CCNC(=O)OCC1=CC=CC=C1 BAKBWMQUYIHULH-FPOVZHCZSA-N 0.000 claims 1
- WBTNMOUDIQEVFC-GMAHTHKFSA-N benzyl n-[(4s)-5-[(2s)-2-cyanopyrrolidin-1-yl]-4-[(4-methoxybenzoyl)amino]-5-oxopentyl]carbamate Chemical compound C1=CC(OC)=CC=C1C(=O)N[C@H](C(=O)N1[C@@H](CCC1)C#N)CCCNC(=O)OCC1=CC=CC=C1 WBTNMOUDIQEVFC-GMAHTHKFSA-N 0.000 claims 1
- AQFRZEWKJVGQGN-UPVQGACJSA-N benzyl n-[(5s)-6-[(2s)-2-cyanopyrrolidin-1-yl]-5-[(3-methoxybenzoyl)amino]-6-oxohexyl]carbamate Chemical compound COC1=CC=CC(C(=O)N[C@@H](CCCCNC(=O)OCC=2C=CC=CC=2)C(=O)N2[C@@H](CCC2)C#N)=C1 AQFRZEWKJVGQGN-UPVQGACJSA-N 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000011159 matrix material Substances 0.000 claims 1
- FAUWKACRJDTPOA-JSGCOSHPSA-N methyl (3s)-4-[(2s)-2-cyanopyrrolidin-1-yl]-3-[(2-methoxybenzoyl)amino]-4-oxobutanoate Chemical compound N([C@@H](CC(=O)OC)C(=O)N1[C@@H](CCC1)C#N)C(=O)C1=CC=CC=C1OC FAUWKACRJDTPOA-JSGCOSHPSA-N 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- VCEGEGIPEXYJAI-HKUYNNGSSA-N n-[(1s)-2-[(2s)-2-cyanopyrrolidin-1-yl]-1-cyclohexyl-2-oxoethyl]-4-methoxybenzamide Chemical compound C1=CC(OC)=CC=C1C(=O)N[C@H](C(=O)N1[C@@H](CCC1)C#N)C1CCCCC1 VCEGEGIPEXYJAI-HKUYNNGSSA-N 0.000 claims 1
- PWTSYTVTZMZJGD-ROUUACIJSA-N n-[(1s)-2-[(2s)-2-cyanopyrrolidin-1-yl]-2-oxo-1-phenylethyl]cyclohexanecarboxamide Chemical compound O=C([C@@H](NC(=O)C1CCCCC1)C=1C=CC=CC=1)N1CCC[C@H]1C#N PWTSYTVTZMZJGD-ROUUACIJSA-N 0.000 claims 1
- UVUCACZVILCRPP-WFASDCNBSA-N n-[(2s)-1-[(2s)-2-cyano-4,4-difluoropyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]-2-methoxybenzamide Chemical compound COC1=CC=CC=C1C(=O)N[C@@H](C(C)C)C(=O)N1[C@H](C#N)CC(F)(F)C1 UVUCACZVILCRPP-WFASDCNBSA-N 0.000 claims 1
- RGZBPLPCOYHYKX-XGFYENRKSA-N n-[(2s)-1-[(2s)-2-cyanoazetidin-1-yl]-3-methyl-1-oxopentan-2-yl]-2-methoxybenzamide Chemical compound N([C@@H](C(C)CC)C(=O)N1[C@@H](CC1)C#N)C(=O)C1=CC=CC=C1OC RGZBPLPCOYHYKX-XGFYENRKSA-N 0.000 claims 1
- QVOUOWQMLYUBSG-UFFKYAFASA-N n-[(2s)-1-[(2s)-2-cyanopiperidin-1-yl]-3-methyl-1-oxopentan-2-yl]-2-methoxybenzamide Chemical compound N([C@@H](C(C)CC)C(=O)N1[C@@H](CCCC1)C#N)C(=O)C1=CC=CC=C1OC QVOUOWQMLYUBSG-UFFKYAFASA-N 0.000 claims 1
- IRXQLUZQSXKQTK-PMACEKPBSA-N n-[(2s)-1-[(2s)-2-cyanopyrrolidin-1-yl]-1-oxo-3-phenylmethoxypropan-2-yl]benzamide Chemical compound C([C@H](NC(=O)C=1C=CC=CC=1)C(=O)N1[C@@H](CCC1)C#N)OCC1=CC=CC=C1 IRXQLUZQSXKQTK-PMACEKPBSA-N 0.000 claims 1
- VJKYBUCABNMHNZ-HOTGVXAUSA-N n-[(2s)-1-[(2s)-2-cyanopyrrolidin-1-yl]-1-oxo-3-phenylpropan-2-yl]-2,2-dimethylpropanamide Chemical compound C([C@H](NC(=O)C(C)(C)C)C(=O)N1[C@@H](CCC1)C#N)C1=CC=CC=C1 VJKYBUCABNMHNZ-HOTGVXAUSA-N 0.000 claims 1
- NEKKARWFODQEBP-PMACEKPBSA-N n-[(2s)-1-[(2s)-2-cyanopyrrolidin-1-yl]-1-oxo-3-phenylpropan-2-yl]-n-methylcyclohexanecarboxamide Chemical compound C([C@H](N(C)C(=O)C1CCCCC1)C(=O)N1[C@@H](CCC1)C#N)C1=CC=CC=C1 NEKKARWFODQEBP-PMACEKPBSA-N 0.000 claims 1
- CNDNFODYJHUFBN-JSGCOSHPSA-N n-[(2s)-1-[(2s)-2-cyanopyrrolidin-1-yl]-1-oxopropan-2-yl]-n-methylcyclohexanecarboxamide Chemical compound CN([C@@H](C)C(=O)N1[C@@H](CCC1)C#N)C(=O)C1CCCCC1 CNDNFODYJHUFBN-JSGCOSHPSA-N 0.000 claims 1
- RANABWAAQNNYCJ-XJKSGUPXSA-N n-[(2s)-1-[(2s)-2-cyanopyrrolidin-1-yl]-3,3-dimethyl-1-oxobutan-2-yl]-2-methoxybenzamide Chemical compound COC1=CC=CC=C1C(=O)N[C@@H](C(C)(C)C)C(=O)N1[C@H](C#N)CCC1 RANABWAAQNNYCJ-XJKSGUPXSA-N 0.000 claims 1
- BUMFFFVUHIJEKL-HOCLYGCPSA-N n-[(2s)-1-[(2s)-2-cyanopyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]-3-methoxybenzamide Chemical compound COC1=CC=CC(C(=O)N[C@@H](C(C)C)C(=O)N2[C@@H](CCC2)C#N)=C1 BUMFFFVUHIJEKL-HOCLYGCPSA-N 0.000 claims 1
- MZHFTMRPFYCUDY-SPOOISQMSA-N n-[(2s)-1-[(2s)-2-cyanopyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)N[C@@H](C(C)CC)C(=O)N1CCC[C@H]1C#N MZHFTMRPFYCUDY-SPOOISQMSA-N 0.000 claims 1
- FJGNQUANKGZDDK-UFFKYAFASA-N n-[(2s)-1-[(2s)-2-cyanopyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]-2-methoxy-n-methylbenzamide Chemical compound CN([C@@H](C(C)CC)C(=O)N1[C@@H](CCC1)C#N)C(=O)C1=CC=CC=C1OC FJGNQUANKGZDDK-UFFKYAFASA-N 0.000 claims 1
- FAWMMKSJLIZZRH-HUUYTVAOSA-N n-[(2s)-1-[(2s)-2-cyanopyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]-2-methoxybenzamide Chemical compound N([C@@H](C(C)CC)C(=O)N1[C@@H](CCC1)C#N)C(=O)C1=CC=CC=C1OC FAWMMKSJLIZZRH-HUUYTVAOSA-N 0.000 claims 1
- DEGBUCDMCRUTQK-QJOPWCIASA-N n-[(2s)-1-[(2s)-2-cyanopyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]-3-methoxybenzamide Chemical compound N([C@@H](C(C)CC)C(=O)N1[C@@H](CCC1)C#N)C(=O)C1=CC=CC(OC)=C1 DEGBUCDMCRUTQK-QJOPWCIASA-N 0.000 claims 1
- AUPWEHXGXJUQRD-QJOPWCIASA-N n-[(2s)-1-[(2s)-2-cyanopyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]-4-methoxybenzamide Chemical compound N([C@@H](C(C)CC)C(=O)N1[C@@H](CCC1)C#N)C(=O)C1=CC=C(OC)C=C1 AUPWEHXGXJUQRD-QJOPWCIASA-N 0.000 claims 1
- DMJHBAIBXDJGJI-RDJZCZTQSA-N n-[(2s)-1-[(2s)-2-cyanopyrrolidin-1-yl]-4-methyl-1-oxopentan-2-yl]-3-methoxybenzamide Chemical compound COC1=CC=CC(C(=O)N[C@@H](CC(C)C)C(=O)N2[C@@H](CCC2)C#N)=C1 DMJHBAIBXDJGJI-RDJZCZTQSA-N 0.000 claims 1
- FWNKTVPLUJFYKD-HKUYNNGSSA-N n-[(2s)-1-[(2s)-2-formylpyrrolidin-1-yl]-1-oxo-3-phenylpropan-2-yl]-2-methoxybenzamide Chemical compound COC1=CC=CC=C1C(=O)N[C@H](C(=O)N1[C@@H](CCC1)C=O)CC1=CC=CC=C1 FWNKTVPLUJFYKD-HKUYNNGSSA-N 0.000 claims 1
- VNHAVDSIKIXKLU-BBRMVZONSA-N n-[(2s)-1-[(2s)-2-formylpyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]-2-methoxybenzamide Chemical compound COC1=CC=CC=C1C(=O)N[C@@H](C(C)C)C(=O)N1[C@H](C=O)CCC1 VNHAVDSIKIXKLU-BBRMVZONSA-N 0.000 claims 1
- PYOPMTPVNNGGLD-ZFWWWQNUSA-N n-[(2s)-5-amino-1-[(2s)-2-cyanopyrrolidin-1-yl]-1-oxopentan-2-yl]-2-methoxybenzamide Chemical compound COC1=CC=CC=C1C(=O)N[C@@H](CCCN)C(=O)N1[C@H](C#N)CCC1 PYOPMTPVNNGGLD-ZFWWWQNUSA-N 0.000 claims 1
- YIJFBSOVBVNTCM-HOCLYGCPSA-N n-[(2s)-6-amino-1-[(2s)-2-cyanopyrrolidin-1-yl]-1-oxohexan-2-yl]-2-methoxybenzamide Chemical compound COC1=CC=CC=C1C(=O)N[C@@H](CCCCN)C(=O)N1[C@H](C#N)CCC1 YIJFBSOVBVNTCM-HOCLYGCPSA-N 0.000 claims 1
- OQXQSKNSVJCHQM-LBPRGKRZSA-N n-[1-[(2s)-2-cyanopyrrolidin-1-yl]-2-methyl-1-oxopropan-2-yl]-2-methoxybenzamide Chemical compound COC1=CC=CC=C1C(=O)NC(C)(C)C(=O)N1[C@H](C#N)CCC1 OQXQSKNSVJCHQM-LBPRGKRZSA-N 0.000 claims 1
- MMEPVYJSHWWBSV-HNNXBMFYSA-N n-[2-[(2s)-2-cyanopyrrolidin-1-yl]-2-oxoethyl]-2-methoxy-n-(2-methylpropyl)benzamide Chemical compound COC1=CC=CC=C1C(=O)N(CC(C)C)CC(=O)N1[C@H](C#N)CCC1 MMEPVYJSHWWBSV-HNNXBMFYSA-N 0.000 claims 1
- HSIDTMLTVRFYGR-AWEZNQCLSA-N n-[2-[(2s)-2-cyanopyrrolidin-1-yl]-2-oxoethyl]naphthalene-1-carboxamide Chemical compound C=1C=CC2=CC=CC=C2C=1C(=O)NCC(=O)N1CCC[C@H]1C#N HSIDTMLTVRFYGR-AWEZNQCLSA-N 0.000 claims 1
- SPTJGQOVDKLVLF-SFHVURJKSA-N n-benzyl-n-[2-[(2s)-2-cyanopyrrolidin-1-yl]-2-oxoethyl]-2-methoxybenzamide Chemical compound COC1=CC=CC=C1C(=O)N(CC=1C=CC=CC=1)CC(=O)N1[C@H](C#N)CCC1 SPTJGQOVDKLVLF-SFHVURJKSA-N 0.000 claims 1
- ALSCEGDXFJIYES-UHFFFAOYSA-N pyrrolidine-2-carbonitrile Chemical compound N#CC1CCCN1 ALSCEGDXFJIYES-UHFFFAOYSA-N 0.000 claims 1
- 230000001629 suppression Effects 0.000 claims 1
- 102100030878 Cytochrome c oxidase subunit 1 Human genes 0.000 abstract 1
- 101000919849 Homo sapiens Cytochrome c oxidase subunit 1 Proteins 0.000 abstract 1
- 101000605122 Homo sapiens Prostaglandin G/H synthase 1 Proteins 0.000 abstract 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/06—Antianaemics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Dermatology (AREA)
- Communicable Diseases (AREA)
- Gastroenterology & Hepatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US71332405P | 2005-09-02 | 2005-09-02 | |
| EP05108049A EP1760076A1 (en) | 2005-09-02 | 2005-09-02 | FAP Inhibitors |
| US60/713,324 | 2005-09-02 | ||
| EP05108049.7 | 2005-09-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2008112683A true RU2008112683A (ru) | 2009-10-20 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2008112683/04A RU2008112683A (ru) | 2005-09-02 | 2006-08-31 | Ингибиторы fap |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8183280B2 (enExample) |
| EP (2) | EP1760076A1 (enExample) |
| JP (1) | JP2009507011A (enExample) |
| KR (1) | KR20080043383A (enExample) |
| AU (1) | AU2006336854A1 (enExample) |
| CA (1) | CA2627607A1 (enExample) |
| NO (1) | NO20081636L (enExample) |
| RU (1) | RU2008112683A (enExample) |
| WO (1) | WO2007085895A2 (enExample) |
| ZA (1) | ZA200802867B (enExample) |
Families Citing this family (55)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US7407955B2 (en) | 2002-08-21 | 2008-08-05 | Boehringer Ingelheim Pharma Gmbh & Co., Kg | 8-[3-amino-piperidin-1-yl]-xanthines, the preparation thereof and their use as pharmaceutical compositions |
| US7501426B2 (en) | 2004-02-18 | 2009-03-10 | Boehringer Ingelheim International Gmbh | 8-[3-amino-piperidin-1-yl]-xanthines, their preparation and their use as pharmaceutical compositions |
| DE102004054054A1 (de) | 2004-11-05 | 2006-05-11 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Verfahren zur Herstellung chiraler 8-(3-Amino-piperidin-1-yl)-xanthine |
| DE102005035891A1 (de) | 2005-07-30 | 2007-02-08 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | 8-(3-Amino-piperidin-1-yl)-xanthine, deren Herstellung und deren Verwendung als Arzneimittel |
| PE20110235A1 (es) | 2006-05-04 | 2011-04-14 | Boehringer Ingelheim Int | Combinaciones farmaceuticas que comprenden linagliptina y metmorfina |
| EA030606B1 (ru) | 2006-05-04 | 2018-08-31 | Бёрингер Ингельхайм Интернациональ Гмбх | Способы приготовления лекарственного средства, содержащего полиморфы |
| EP1852108A1 (en) | 2006-05-04 | 2007-11-07 | Boehringer Ingelheim Pharma GmbH & Co.KG | DPP IV inhibitor formulations |
| US8933201B2 (en) | 2006-06-07 | 2015-01-13 | The Board Of Regents Of The University Of Oklahoma | Substrates and inhibitors of antiplasmin cleaving enzyme and fibroblast activation protein and methods of use |
| CA2696579C (en) | 2007-08-17 | 2017-01-24 | Boehringer Ingelheim International Gmbh | Purine derivatives for use in the treatment of fab-related diseases |
| EP2071337A1 (en) * | 2007-12-10 | 2009-06-17 | F.Hoffmann-La Roche Ag | Seprase as a marker for cancer |
| EP2223115B1 (en) | 2007-12-10 | 2011-09-14 | Roche Diagnostics GmbH | Seprase as a marker for cancer |
| ES2515194T3 (es) * | 2008-03-05 | 2014-10-29 | National Health Research Institutes | Derivados de pirrolidina |
| PE20140960A1 (es) | 2008-04-03 | 2014-08-15 | Boehringer Ingelheim Int | Formulaciones que comprenden un inhibidor de dpp4 |
| KR20200118243A (ko) | 2008-08-06 | 2020-10-14 | 베링거 인겔하임 인터내셔날 게엠베하 | 메트포르민 요법이 부적합한 환자에서의 당뇨병 치료 |
| UY32030A (es) | 2008-08-06 | 2010-03-26 | Boehringer Ingelheim Int | "tratamiento para diabetes en pacientes inapropiados para terapia con metformina" |
| MX2011002558A (es) | 2008-09-10 | 2011-04-26 | Boehringer Ingelheim Int | Terapia de combinacion para el tratamiento de diabetes y estados relacionados. |
| CA2737941A1 (en) * | 2008-09-25 | 2010-04-01 | Molecular Insight Pharmaceuticals, Inc. | Selective seprase inhibitors |
| US20200155558A1 (en) | 2018-11-20 | 2020-05-21 | Boehringer Ingelheim International Gmbh | Treatment for diabetes in patients with insufficient glycemic control despite therapy with an oral antidiabetic drug |
| CN102256976A (zh) | 2008-12-23 | 2011-11-23 | 贝林格尔.英格海姆国际有限公司 | 有机化合物的盐形式 |
| TW201036975A (en) | 2009-01-07 | 2010-10-16 | Boehringer Ingelheim Int | Treatment for diabetes in patients with inadequate glycemic control despite metformin therapy |
| US20120053222A1 (en) * | 2009-01-23 | 2012-03-01 | Mark Gorrell | Novel Metabolic Disease Therapy |
| EA034869B1 (ru) | 2009-11-27 | 2020-03-31 | Бёрингер Ингельхайм Интернациональ Гмбх | Лечение генотипированных пациентов с диабетом ингибиторами дпп-4, такими как линаглиптин |
| KR101819609B1 (ko) | 2010-05-05 | 2018-01-17 | 베링거 인겔하임 인터내셔날 게엠베하 | 체중 감소 치료에 후속하는 dpp-4 억제제에 의한 순차적 병용 요법 |
| KR20230051307A (ko) | 2010-06-24 | 2023-04-17 | 베링거 인겔하임 인터내셔날 게엠베하 | 당뇨병 요법 |
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| US9555001B2 (en) | 2012-03-07 | 2017-01-31 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition and uses thereof |
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| JP6218811B2 (ja) | 2012-05-14 | 2017-10-25 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｓｉｒｓ及び／又は敗血症の治療に用いるｄｐｐ−４阻害薬としてのキサンチン誘導体 |
| WO2013174767A1 (en) | 2012-05-24 | 2013-11-28 | Boehringer Ingelheim International Gmbh | A xanthine derivative as dpp -4 inhibitor for use in modifying food intake and regulating food preference |
| CN104379181A (zh) * | 2012-06-29 | 2015-02-25 | 通用电气健康护理有限公司 | 对纤维变性成像 |
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| EP4147053A1 (en) | 2020-05-07 | 2023-03-15 | Institut Curie | Antxr1 as a biomarker of immunosuppressive fibroblast populations and its use for predicting response to immunotherapy |
| TW202239407A (zh) * | 2020-12-17 | 2022-10-16 | 瑞典商阿斯特捷利康公司 | Ｎ－（２－（４－氰基四氫噻唑－３－基）－２－側氧基乙基）－喹啉－４－甲醯胺 |
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| CN119562951A (zh) * | 2022-06-21 | 2025-03-04 | 阿斯利康(瑞典)有限公司 | N-(2-(4-氰基噻唑烷-3-基)-2-氧代乙基)-喹啉-4-甲酰胺 |
| IL317722A (en) * | 2022-06-21 | 2025-02-01 | Astrazeneca Ab | Solid state forms of N-(2-(4-cyanothiazolidin-3-yl)-2-oxoethyl)-6-morpholinoquinoline-4-carboxamide |
| EP4543869A1 (en) * | 2022-06-21 | 2025-04-30 | Astrazeneca AB | N-(2-(3-cyano-2-azabicyclo[3.1.0]hexan-2-yl)-2-oxoethyl)- quinoline-4-carboxamides |
| WO2025046043A1 (en) | 2023-08-31 | 2025-03-06 | Stichting Radboud Universitair Medisch Centrum | Endometriosis tracer |
| CN118955616B (zh) * | 2024-05-01 | 2025-09-02 | 杭州景嘉航生物医药科技有限公司 | 一种靶向结合成纤维细胞活化蛋白化合物及应用 |
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| CA2484551A1 (en) | 2002-04-30 | 2003-11-13 | Trustees Of Tufts College | Smart pro-drugs of serine protease inhibitors |
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| RU2310651C2 (ru) | 2002-08-30 | 2007-11-20 | Эйсай Ар Энд Ди Менеджмент Ко., Лтд. | Азотсодержащие ароматические производные, фармацевтическая композиция, их содержащая, способ лечения и применение |
| BRPI0612607A2 (pt) * | 2005-07-05 | 2010-12-07 | Tufts College | inibidores de alfa proteìna de ativação de fibroblasto |
-
2005
- 2005-09-02 EP EP05108049A patent/EP1760076A1/en not_active Withdrawn
-
2006
- 2006-08-31 KR KR1020087007975A patent/KR20080043383A/ko not_active Withdrawn
- 2006-08-31 CA CA002627607A patent/CA2627607A1/en not_active Abandoned
- 2006-08-31 RU RU2008112683/04A patent/RU2008112683A/ru not_active Application Discontinuation
- 2006-08-31 US US11/991,286 patent/US8183280B2/en not_active Expired - Fee Related
- 2006-08-31 JP JP2008528601A patent/JP2009507011A/ja active Pending
- 2006-08-31 EP EP06849433A patent/EP1919864A2/en not_active Withdrawn
- 2006-08-31 AU AU2006336854A patent/AU2006336854A1/en not_active Abandoned
- 2006-08-31 WO PCT/IB2006/003512 patent/WO2007085895A2/en not_active Ceased
-
2008
- 2008-04-01 ZA ZA200802867A patent/ZA200802867B/xx unknown
- 2008-04-02 NO NO20081636A patent/NO20081636L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP1919864A2 (en) | 2008-05-14 |
| ZA200802867B (en) | 2008-12-31 |
| WO2007085895A3 (en) | 2008-04-17 |
| KR20080043383A (ko) | 2008-05-16 |
| WO2007085895A2 (en) | 2007-08-02 |
| EP1760076A1 (en) | 2007-03-07 |
| JP2009507011A (ja) | 2009-02-19 |
| AU2006336854A1 (en) | 2007-08-02 |
| US20100081701A1 (en) | 2010-04-01 |
| CA2627607A1 (en) | 2007-08-02 |
| NO20081636L (no) | 2008-05-29 |
| US8183280B2 (en) | 2012-05-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA92 | Acknowledgement of application withdrawn (lack of supplementary materials submitted) |
Effective date: 20110610 |