NO322895B1 - Nye <alfa>-aminosyresulfonylforbindelser, fremgangsmate ved deres fremstilling og farmasoytiske sammensetninger inneholdende dem, samt deres anvendelse. - Google Patents
Nye <alfa>-aminosyresulfonylforbindelser, fremgangsmate ved deres fremstilling og farmasoytiske sammensetninger inneholdende dem, samt deres anvendelse. Download PDFInfo
- Publication number
- NO322895B1 NO322895B1 NO20021542A NO20021542A NO322895B1 NO 322895 B1 NO322895 B1 NO 322895B1 NO 20021542 A NO20021542 A NO 20021542A NO 20021542 A NO20021542 A NO 20021542A NO 322895 B1 NO322895 B1 NO 322895B1
- Authority
- NO
- Norway
- Prior art keywords
- formula
- compound
- group
- pyrrolidine
- amino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 61
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 5
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 126
- 150000001875 compounds Chemical class 0.000 claims description 48
- -1 1,3-thiazolidin-3-yl group Chemical group 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- 230000003287 optical effect Effects 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 238000011282 treatment Methods 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 206010028980 Neoplasm Diseases 0.000 claims description 7
- 201000011510 cancer Diseases 0.000 claims description 7
- 238000010511 deprotection reaction Methods 0.000 claims description 6
- 230000002265 prevention Effects 0.000 claims description 6
- 125000006239 protecting group Chemical group 0.000 claims description 5
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 4
- 206010027476 Metastases Diseases 0.000 claims description 4
- 206010052779 Transplant rejections Diseases 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 208000035475 disorder Diseases 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- 208000002705 Glucose Intolerance Diseases 0.000 claims description 3
- 206010018429 Glucose tolerance impaired Diseases 0.000 claims description 3
- 208000008589 Obesity Diseases 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 201000001421 hyperglycemia Diseases 0.000 claims description 3
- 210000000936 intestine Anatomy 0.000 claims description 3
- 235000020824 obesity Nutrition 0.000 claims description 3
- 238000005897 peptide coupling reaction Methods 0.000 claims description 3
- 201000001245 periodontitis Diseases 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 3
- 238000002271 resection Methods 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 238000002054 transplantation Methods 0.000 claims description 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 208000030507 AIDS Diseases 0.000 claims description 2
- GKCKDJKQDOSCPJ-AWEZNQCLSA-N n-[(4s)-4-amino-5-oxo-5-pyrrolidin-1-ylpentyl]cyclohexanesulfonamide Chemical compound C([C@H](N)C(=O)N1CCCC1)CCNS(=O)(=O)C1CCCCC1 GKCKDJKQDOSCPJ-AWEZNQCLSA-N 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 229940127003 anti-diabetic drug Drugs 0.000 claims 1
- 239000003472 antidiabetic agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 230000035876 healing Effects 0.000 claims 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 37
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 37
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 29
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 22
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 14
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 description 14
- 229960003104 ornithine Drugs 0.000 description 14
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 13
- 239000004472 Lysine Substances 0.000 description 13
- 102100025012 Dipeptidyl peptidase 4 Human genes 0.000 description 12
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 11
- MJWVCJUSRGLHFO-UHFFFAOYSA-N cyclohexanesulfonyl chloride Chemical compound ClS(=O)(=O)C1CCCCC1 MJWVCJUSRGLHFO-UHFFFAOYSA-N 0.000 description 11
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 10
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 10
- FCLZCOCSZQNREK-UHFFFAOYSA-N Pyrrolidine, hydrochloride Chemical compound Cl.C1CCNC1 FCLZCOCSZQNREK-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 239000004475 Arginine Substances 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 9
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 8
- QSJTUXCBPTVKQZ-JEDNCBNOSA-N (2s)-pyrrolidine-2-carbonitrile;hydrochloride Chemical compound Cl.N#C[C@@H]1CCCN1 QSJTUXCBPTVKQZ-JEDNCBNOSA-N 0.000 description 7
- 108010067722 Dipeptidyl Peptidase 4 Proteins 0.000 description 7
- PRSDPVKGJUBIAA-SCSAIBSYSA-N (4r)-1,3-thiazolidine-4-carbonitrile Chemical compound N#C[C@@H]1CSCN1 PRSDPVKGJUBIAA-SCSAIBSYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 101000930822 Giardia intestinalis Dipeptidyl-peptidase 4 Proteins 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- SJSSFUMSAFMFNM-NSHDSACASA-N (2s)-5-(diaminomethylideneamino)-2-(phenylmethoxycarbonylamino)pentanoic acid Chemical compound NC(N)=NCCC[C@@H](C(O)=O)NC(=O)OCC1=CC=CC=C1 SJSSFUMSAFMFNM-NSHDSACASA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- DTHNMHAUYICORS-KTKZVXAJSA-N Glucagon-like peptide 1 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 DTHNMHAUYICORS-KTKZVXAJSA-N 0.000 description 3
- 101800000224 Glucagon-like peptide 1 Proteins 0.000 description 3
- 102400000322 Glucagon-like peptide 1 Human genes 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000002779 inactivation Effects 0.000 description 3
- 238000004452 microanalysis Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- UAFUIWDKLIXSAZ-UHFFFAOYSA-N pyrrolidin-1-ium dichloride Chemical compound Cl.N1CCCC1.N1CCCC1.Cl UAFUIWDKLIXSAZ-UHFFFAOYSA-N 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QKMSMVGTLTVHLK-LBPRGKRZSA-N (2s)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(phenylmethoxycarbonylamino)propanoic acid Chemical compound CC(C)(C)OC(=O)N[C@H](C(O)=O)CNC(=O)OCC1=CC=CC=C1 QKMSMVGTLTVHLK-LBPRGKRZSA-N 0.000 description 2
- IILDIIAZNITTLB-ZDUSSCGKSA-N (2s)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-(phenylmethoxycarbonylamino)butanoic acid Chemical compound CC(C)(C)OC(=O)N[C@H](C(O)=O)CCNC(=O)OCC1=CC=CC=C1 IILDIIAZNITTLB-ZDUSSCGKSA-N 0.000 description 2
- WJKGPJRAGHSOLM-LBPRGKRZSA-N (2s)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-2-(phenylmethoxycarbonylamino)propanoic acid Chemical compound CC(C)(C)OC(=O)NC[C@@H](C(O)=O)NC(=O)OCC1=CC=CC=C1 WJKGPJRAGHSOLM-LBPRGKRZSA-N 0.000 description 2
- RRONHWAVOYADJL-HNNXBMFYSA-N (2s)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)OCC=1C=CC=CC=1)C1=CC=CC=C1 RRONHWAVOYADJL-HNNXBMFYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 241000713772 Human immunodeficiency virus 1 Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- WEDIIKBPDQQQJU-UHFFFAOYSA-N butane-1-sulfonyl chloride Chemical compound CCCCS(Cl)(=O)=O WEDIIKBPDQQQJU-UHFFFAOYSA-N 0.000 description 2
- REWZIICPWFGXJJ-UHFFFAOYSA-N cyclobutanesulfonyl chloride Chemical compound ClS(=O)(=O)C1CCC1 REWZIICPWFGXJJ-UHFFFAOYSA-N 0.000 description 2
- HZVKYZHPDGEECE-UHFFFAOYSA-N cyclopentanesulfonyl chloride Chemical compound ClS(=O)(=O)C1CCCC1 HZVKYZHPDGEECE-UHFFFAOYSA-N 0.000 description 2
- PFWWSGFPICCWGU-UHFFFAOYSA-N cyclopropanesulfonyl chloride Chemical compound ClS(=O)(=O)C1CC1 PFWWSGFPICCWGU-UHFFFAOYSA-N 0.000 description 2
- FRYHCSODNHYDPU-UHFFFAOYSA-N ethanesulfonyl chloride Chemical compound CCS(Cl)(=O)=O FRYHCSODNHYDPU-UHFFFAOYSA-N 0.000 description 2
- 230000028993 immune response Effects 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 210000004698 lymphocyte Anatomy 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- KPBSJEBFALFJTO-UHFFFAOYSA-N propane-1-sulfonyl chloride Chemical compound CCCS(Cl)(=O)=O KPBSJEBFALFJTO-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- SJSSFUMSAFMFNM-LLVKDONJSA-N (2r)-5-(diaminomethylideneazaniumyl)-2-(phenylmethoxycarbonylamino)pentanoate Chemical compound NC(N)=[NH+]CCC[C@H](C([O-])=O)NC(=O)OCC1=CC=CC=C1 SJSSFUMSAFMFNM-LLVKDONJSA-N 0.000 description 1
- BDHUTRNYBGWPBL-HNNXBMFYSA-N (2s)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-6-(phenylmethoxycarbonylamino)hexanoic acid Chemical compound CC(C)(C)OC(=O)N[C@H](C(O)=O)CCCCNC(=O)OCC1=CC=CC=C1 BDHUTRNYBGWPBL-HNNXBMFYSA-N 0.000 description 1
- HSBIRMRDQJMAEC-NSHDSACASA-N (2s)-3-[2-(diaminomethylideneamino)ethoxy]-2-(phenylmethoxycarbonylamino)propanoic acid Chemical compound NC(=N)NCCOC[C@@H](C(O)=O)NC(=O)OCC1=CC=CC=C1 HSBIRMRDQJMAEC-NSHDSACASA-N 0.000 description 1
- ONDKXCQPYFHZPA-ZDUSSCGKSA-N (2s)-4-[(2-methylpropan-2-yl)oxycarbonylamino]-2-(phenylmethoxycarbonylamino)butanoic acid Chemical compound CC(C)(C)OC(=O)NCC[C@@H](C(O)=O)NC(=O)OCC1=CC=CC=C1 ONDKXCQPYFHZPA-ZDUSSCGKSA-N 0.000 description 1
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- SZQMTCSQWUYUML-UHFFFAOYSA-N 2-(phenylmethoxycarbonylamino)butanoic acid Chemical compound CCC(C(O)=O)NC(=O)OCC1=CC=CC=C1 SZQMTCSQWUYUML-UHFFFAOYSA-N 0.000 description 1
- KMIYPXHRLLTWPY-RGMNGODLSA-N 2-[(2s)-2-amino-3-oxo-3-(1,3-thiazolidin-3-yl)propyl]-1-methylsulfonylguanidine;hydrochloride Chemical compound Cl.CS(=O)(=O)NC(=N)NC[C@H](N)C(=O)N1CCSC1 KMIYPXHRLLTWPY-RGMNGODLSA-N 0.000 description 1
- JPRPILLUCBMBEN-FJXQXJEOSA-N 2-[(3s)-3-amino-4-oxo-4-(1,3-thiazolidin-3-yl)butyl]-1-methylsulfonylguanidine;hydrochloride Chemical compound Cl.CS(=O)(=O)NC(=N)NCC[C@H](N)C(=O)N1CCSC1 JPRPILLUCBMBEN-FJXQXJEOSA-N 0.000 description 1
- NPYQLBSYOKUWDR-DMLYUBSXSA-N 2-[(5s)-5-amino-6-[(2s)-2-cyanopyrrolidin-1-yl]-6-oxohexyl]-1-cyclohexylsulfonylguanidine;hydrochloride Chemical compound Cl.C([C@H](N)C(=O)N1[C@@H](CCC1)C#N)CCCNC(=N)NS(=O)(=O)C1CCCCC1 NPYQLBSYOKUWDR-DMLYUBSXSA-N 0.000 description 1
- QUIODPLRWCFITI-ACMTZBLWSA-N 2-[(5s)-5-amino-6-[(2s)-2-cyanopyrrolidin-1-yl]-6-oxohexyl]-1-methylsulfonylguanidine;hydrochloride Chemical compound Cl.CS(=O)(=O)NC(=N)NCCCC[C@H](N)C(=O)N1CCC[C@H]1C#N QUIODPLRWCFITI-ACMTZBLWSA-N 0.000 description 1
- ZZEBEMKTBXCSOB-QPGQKYJFSA-N 2-[(5s)-5-amino-6-[(4r)-4-cyano-1,3-thiazolidin-3-yl]-6-oxohexyl]-1-cyclohexylsulfonylguanidine;dihydrochloride Chemical compound Cl.Cl.C([C@H](N)C(=O)N1[C@@H](CSC1)C#N)CCCNC(=N)NS(=O)(=O)C1CCCCC1 ZZEBEMKTBXCSOB-QPGQKYJFSA-N 0.000 description 1
- MQLUJSWCIAEROD-UXQCFNEQSA-N 2-[(5s)-5-amino-6-[(4r)-4-cyano-1,3-thiazolidin-3-yl]-6-oxohexyl]-1-methylsulfonylguanidine;hydrochloride Chemical compound Cl.CS(=O)(=O)NC(=N)NCCCC[C@H](N)C(=O)N1CSC[C@H]1C#N MQLUJSWCIAEROD-UXQCFNEQSA-N 0.000 description 1
- XCHYKGGTKWDTAK-WWPIYYJJSA-N 2-[(5s)-5-amino-6-oxo-6-(1,3-thiazolidin-3-yl)hexyl]-1-methylsulfonylguanidine;dihydrochloride Chemical compound Cl.Cl.CS(=O)(=O)NC(=N)NCCCC[C@H](N)C(=O)N1CCSC1 XCHYKGGTKWDTAK-WWPIYYJJSA-N 0.000 description 1
- DGXZZIKNFQHPGM-PPHPATTJSA-N 2-[(5s)-5-amino-6-oxo-6-pyrrolidin-1-ylhexyl]-1-methylsulfonylguanidine;hydrochloride Chemical compound Cl.CS(=O)(=O)NC(=N)NCCCC[C@H](N)C(=O)N1CCCC1 DGXZZIKNFQHPGM-PPHPATTJSA-N 0.000 description 1
- NIXSURWKCHUXQS-FVGYRXGTSA-N 2-[2-[(2s)-2-amino-3-oxo-3-pyrrolidin-1-ylpropoxy]ethyl]-1-methylsulfonylguanidine;hydrochloride Chemical compound Cl.CS(=O)(=O)NC(=N)NCCOC[C@H](N)C(=O)N1CCCC1 NIXSURWKCHUXQS-FVGYRXGTSA-N 0.000 description 1
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- SMROXEBMXNLLDT-RJUBDTSPSA-N CS(=O)(=O)NCCC[C@@H](C(=O)N1CSC[C@H]1C#N)N.Cl Chemical compound CS(=O)(=O)NCCC[C@@H](C(=O)N1CSC[C@H]1C#N)N.Cl SMROXEBMXNLLDT-RJUBDTSPSA-N 0.000 description 1
- LSPHULWDVZXLIL-UHFFFAOYSA-N Camphoric acid Natural products CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 description 1
- 108010012236 Chemokines Proteins 0.000 description 1
- 102000019034 Chemokines Human genes 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- 102100037362 Fibronectin Human genes 0.000 description 1
- 108010067306 Fibronectins Proteins 0.000 description 1
- 101800000221 Glucagon-like peptide 2 Proteins 0.000 description 1
- 102400000326 Glucagon-like peptide 2 Human genes 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 101000908391 Homo sapiens Dipeptidyl peptidase 4 Proteins 0.000 description 1
- 101000617130 Homo sapiens Stromal cell-derived factor 1 Proteins 0.000 description 1
- 102000004877 Insulin Human genes 0.000 description 1
- 108090001061 Insulin Proteins 0.000 description 1
- RDAJPNWCWKOWJO-DMLYUBSXSA-N N-[(5S)-5-amino-6-[(2S)-2-cyanopyrrolidin-1-yl]-6-oxohexyl]cyclohexanesulfonamide hydrochloride Chemical compound C1CCC(CC1)S(=O)(=O)NCCCC[C@@H](C(=O)N2CCC[C@H]2C#N)N.Cl RDAJPNWCWKOWJO-DMLYUBSXSA-N 0.000 description 1
- GFYQEJITANSXMM-ACMTZBLWSA-N N-[(5S)-5-amino-6-[(2S)-2-cyanopyrrolidin-1-yl]-6-oxohexyl]methanesulfonamide hydrochloride Chemical compound Cl.CS(=O)(=O)NCCCC[C@H](N)C(=O)N1CCC[C@H]1C#N GFYQEJITANSXMM-ACMTZBLWSA-N 0.000 description 1
- 108010022999 Serine Proteases Proteins 0.000 description 1
- 102000012479 Serine Proteases Human genes 0.000 description 1
- 208000004350 Strabismus Diseases 0.000 description 1
- 102100021669 Stromal cell-derived factor 1 Human genes 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 241000718541 Tetragastris balsamifera Species 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 235000008206 alpha-amino acids Nutrition 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- ROAMBJRNKIJPLZ-SFHVURJKSA-N benzyl n-[(4s)-4-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxo-5-pyrrolidin-1-ylpentyl]carbamate Chemical compound C([C@H](NC(=O)OC(C)(C)C)C(=O)N1CCCC1)CCNC(=O)OCC1=CC=CC=C1 ROAMBJRNKIJPLZ-SFHVURJKSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical compound CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 230000003399 chemotactic effect Effects 0.000 description 1
- 239000003593 chromogenic compound Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- FVRKMCXIWRIQLG-UHFFFAOYSA-N cyclohexanesulfonamide hydrochloride Chemical compound C1CCC(CC1)S(=O)(=O)N.Cl FVRKMCXIWRIQLG-UHFFFAOYSA-N 0.000 description 1
- BNZZPMGQCWZOPS-UHFFFAOYSA-N cyclohexylmethanesulfonyl chloride Chemical compound ClS(=O)(=O)CC1CCCCC1 BNZZPMGQCWZOPS-UHFFFAOYSA-N 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 230000003511 endothelial effect Effects 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- TWSALRJGPBVBQU-PKQQPRCHSA-N glucagon-like peptide 2 Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(O)=O)C(O)=O)[C@@H](C)CC)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)CC)C1=CC=CC=C1 TWSALRJGPBVBQU-PKQQPRCHSA-N 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229940125396 insulin Drugs 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000009401 metastasis Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- NLZOCHCDTJYKTM-FJXQXJEOSA-N n-[(2s)-2-amino-3-oxo-3-pyrrolidin-1-ylpropyl]methanesulfonamide;hydrochloride Chemical compound Cl.CS(=O)(=O)NC[C@H](N)C(=O)N1CCCC1 NLZOCHCDTJYKTM-FJXQXJEOSA-N 0.000 description 1
- MBRFBYLXGZXTKE-FJXQXJEOSA-N n-[(3s)-3-amino-4-oxo-4-(1,3-thiazolidin-3-yl)butyl]methanesulfonamide;hydrochloride Chemical compound Cl.CS(=O)(=O)NCC[C@H](N)C(=O)N1CCSC1 MBRFBYLXGZXTKE-FJXQXJEOSA-N 0.000 description 1
- CZRRBBVXXGSZDT-QRPNPIFTSA-N n-[(3s)-3-amino-4-oxo-4-pyrrolidin-1-ylbutyl]methanesulfonamide;hydrochloride Chemical compound Cl.CS(=O)(=O)NCC[C@H](N)C(=O)N1CCCC1 CZRRBBVXXGSZDT-QRPNPIFTSA-N 0.000 description 1
- AKCZECDAFRFMLG-SLHAJLBXSA-N n-[(4s)-4-amino-5-[(2s)-2-cyanopyrrolidin-1-yl]-5-oxopentyl]cyclohexanesulfonamide;hydrochloride Chemical compound Cl.C([C@H](N)C(=O)N1[C@@H](CCC1)C#N)CCNS(=O)(=O)C1CCCCC1 AKCZECDAFRFMLG-SLHAJLBXSA-N 0.000 description 1
- HCPOVDXDEPXWGD-IYPAPVHQSA-N n-[(4s)-4-amino-5-[(2s)-2-cyanopyrrolidin-1-yl]-5-oxopentyl]methanesulfonamide;hydrochloride Chemical compound Cl.CS(=O)(=O)NCCC[C@H](N)C(=O)N1CCC[C@H]1C#N HCPOVDXDEPXWGD-IYPAPVHQSA-N 0.000 description 1
- FSRRHPQGRDZFFG-ZOWNYOTGSA-N n-[(4s)-4-amino-5-oxo-5-(1,3-thiazolidin-3-yl)pentyl]cyclohexanesulfonamide;hydrochloride Chemical compound Cl.C([C@H](N)C(=O)N1CSCC1)CCNS(=O)(=O)C1CCCCC1 FSRRHPQGRDZFFG-ZOWNYOTGSA-N 0.000 description 1
- VCRMVENCRYTAKJ-QRPNPIFTSA-N n-[(4s)-4-amino-5-oxo-5-(1,3-thiazolidin-3-yl)pentyl]methanesulfonamide;hydrochloride Chemical compound Cl.CS(=O)(=O)NCCC[C@H](N)C(=O)N1CCSC1 VCRMVENCRYTAKJ-QRPNPIFTSA-N 0.000 description 1
- KJQYIDVHULQYQE-RSAXXLAASA-N n-[(4s)-4-amino-5-oxo-5-pyrrolidin-1-ylpentyl]-1-cyclohexylmethanesulfonamide;hydrochloride Chemical compound Cl.C([C@H](N)C(=O)N1CCCC1)CCNS(=O)(=O)CC1CCCCC1 KJQYIDVHULQYQE-RSAXXLAASA-N 0.000 description 1
- CWPDQPIRPULYBH-RSAXXLAASA-N n-[(4s)-4-amino-5-oxo-5-pyrrolidin-1-ylpentyl]-1-phenylmethanesulfonamide;hydrochloride Chemical compound Cl.C([C@H](N)C(=O)N1CCCC1)CCNS(=O)(=O)CC1=CC=CC=C1 CWPDQPIRPULYBH-RSAXXLAASA-N 0.000 description 1
- MSAGQCNIPAOFBT-YDALLXLXSA-N n-[(4s)-4-amino-5-oxo-5-pyrrolidin-1-ylpentyl]butane-1-sulfonamide;hydrochloride Chemical compound Cl.CCCCS(=O)(=O)NCCC[C@H](N)C(=O)N1CCCC1 MSAGQCNIPAOFBT-YDALLXLXSA-N 0.000 description 1
- ZBIMNJOHOARGAH-YDALLXLXSA-N n-[(4s)-4-amino-5-oxo-5-pyrrolidin-1-ylpentyl]cyclobutanesulfonamide;hydrochloride Chemical compound Cl.C([C@H](N)C(=O)N1CCCC1)CCNS(=O)(=O)C1CCC1 ZBIMNJOHOARGAH-YDALLXLXSA-N 0.000 description 1
- GUFXCGBQBRTMGS-UQKRIMTDSA-N n-[(4s)-4-amino-5-oxo-5-pyrrolidin-1-ylpentyl]cyclohexanesulfonamide;hydrochloride Chemical compound Cl.C([C@H](N)C(=O)N1CCCC1)CCNS(=O)(=O)C1CCCCC1 GUFXCGBQBRTMGS-UQKRIMTDSA-N 0.000 description 1
- IAPBONQZQXPBGS-ZOWNYOTGSA-N n-[(4s)-4-amino-5-oxo-5-pyrrolidin-1-ylpentyl]cyclopentanesulfonamide;hydrochloride Chemical compound Cl.C([C@H](N)C(=O)N1CCCC1)CCNS(=O)(=O)C1CCCC1 IAPBONQZQXPBGS-ZOWNYOTGSA-N 0.000 description 1
- KTCOKXDDPYVVEV-MERQFXBCSA-N n-[(4s)-4-amino-5-oxo-5-pyrrolidin-1-ylpentyl]cyclopropanesulfonamide;hydrochloride Chemical compound Cl.C([C@H](N)C(=O)N1CCCC1)CCNS(=O)(=O)C1CC1 KTCOKXDDPYVVEV-MERQFXBCSA-N 0.000 description 1
- FJTSTUVOYAJTCP-PPHPATTJSA-N n-[(4s)-4-amino-5-oxo-5-pyrrolidin-1-ylpentyl]ethanesulfonamide;hydrochloride Chemical compound Cl.CCS(=O)(=O)NCCC[C@H](N)C(=O)N1CCCC1 FJTSTUVOYAJTCP-PPHPATTJSA-N 0.000 description 1
- KNOOYHOJWRIROH-FVGYRXGTSA-N n-[(4s)-4-amino-5-oxo-5-pyrrolidin-1-ylpentyl]methanesulfonamide;hydrochloride Chemical compound Cl.CS(=O)(=O)NCCC[C@H](N)C(=O)N1CCCC1 KNOOYHOJWRIROH-FVGYRXGTSA-N 0.000 description 1
- AXBYFNUTLCGKEI-MERQFXBCSA-N n-[(4s)-4-amino-5-oxo-5-pyrrolidin-1-ylpentyl]propane-1-sulfonamide;hydrochloride Chemical compound Cl.CCCS(=O)(=O)NCCC[C@H](N)C(=O)N1CCCC1 AXBYFNUTLCGKEI-MERQFXBCSA-N 0.000 description 1
- GVKSKZGLZAYRFY-MERQFXBCSA-N n-[(4s)-4-amino-5-oxo-5-pyrrolidin-1-ylpentyl]propane-2-sulfonamide;hydrochloride Chemical compound Cl.CC(C)S(=O)(=O)NCCC[C@H](N)C(=O)N1CCCC1 GVKSKZGLZAYRFY-MERQFXBCSA-N 0.000 description 1
- DICKELUIJPEMJH-PBCQUBLHSA-N n-[(5s)-5-amino-6-[(4r)-4-cyano-1,3-thiazolidin-3-yl]-6-oxohexyl]cyclohexanesulfonamide;hydrochloride Chemical compound Cl.C([C@H](N)C(=O)N1[C@@H](CSC1)C#N)CCCNS(=O)(=O)C1CCCCC1 DICKELUIJPEMJH-PBCQUBLHSA-N 0.000 description 1
- AVMXYBPNIBECGF-ZJUUUORDSA-N n-[(5s)-5-amino-6-[(4r)-4-cyano-1,3-thiazolidin-3-yl]-6-oxohexyl]methanesulfonamide Chemical compound CS(=O)(=O)NCCCC[C@H](N)C(=O)N1CSC[C@H]1C#N AVMXYBPNIBECGF-ZJUUUORDSA-N 0.000 description 1
- OUDJFGDXYWYMPV-UQKRIMTDSA-N n-[(5s)-5-amino-6-oxo-6-(1,3-thiazolidin-3-yl)hexyl]cyclohexanesulfonamide;hydrochloride Chemical compound Cl.C([C@H](N)C(=O)N1CSCC1)CCCNS(=O)(=O)C1CCCCC1 OUDJFGDXYWYMPV-UQKRIMTDSA-N 0.000 description 1
- RJQTZXHHCZQAKP-FVGYRXGTSA-N n-[(5s)-5-amino-6-oxo-6-(1,3-thiazolidin-3-yl)hexyl]methanesulfonamide;hydrochloride Chemical compound Cl.CS(=O)(=O)NCCCC[C@H](N)C(=O)N1CCSC1 RJQTZXHHCZQAKP-FVGYRXGTSA-N 0.000 description 1
- ZYWZXHPPENLNGZ-JTQLQIEISA-N n-[(5s)-5-amino-6-oxo-6-pyrrolidin-1-ylhexyl]methanesulfonamide Chemical compound CS(=O)(=O)NCCCC[C@H](N)C(=O)N1CCCC1 ZYWZXHPPENLNGZ-JTQLQIEISA-N 0.000 description 1
- JBOTXFLBERMTLO-YDALLXLXSA-N n-[4-[(2s)-2-amino-3-oxo-3-(1,3-thiazolidin-3-yl)propyl]phenyl]methanesulfonamide;hydrochloride Chemical compound Cl.C1=CC(NS(=O)(=O)C)=CC=C1C[C@H](N)C(=O)N1CSCC1 JBOTXFLBERMTLO-YDALLXLXSA-N 0.000 description 1
- LBWWBLAMWYOMRA-ZOWNYOTGSA-N n-[4-[(2s)-2-amino-3-oxo-3-pyrrolidin-1-ylpropyl]phenyl]methanesulfonamide;hydrochloride Chemical compound Cl.C1=CC(NS(=O)(=O)C)=CC=C1C[C@H](N)C(=O)N1CCCC1 LBWWBLAMWYOMRA-ZOWNYOTGSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- OAHKWDDSKCRNFE-UHFFFAOYSA-N phenylmethanesulfonyl chloride Chemical compound ClS(=O)(=O)CC1=CC=CC=C1 OAHKWDDSKCRNFE-UHFFFAOYSA-N 0.000 description 1
- DRINJBFRTLBHNF-UHFFFAOYSA-N propane-2-sulfonyl chloride Chemical compound CC(C)S(Cl)(=O)=O DRINJBFRTLBHNF-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- VHYOPZSUMBAAKE-LBPRGKRZSA-N tert-butyl n-[(2s)-5-(methanesulfonamido)-1-oxo-1-pyrrolidin-1-ylpentan-2-yl]carbamate Chemical compound CS(=O)(=O)NCCC[C@H](NC(=O)OC(C)(C)C)C(=O)N1CCCC1 VHYOPZSUMBAAKE-LBPRGKRZSA-N 0.000 description 1
- CABKSFIFNHXOFP-LBPRGKRZSA-N tert-butyl n-[(2s)-6-amino-1-oxo-1-pyrrolidin-1-ylhexan-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@@H](CCCCN)C(=O)N1CCCC1 CABKSFIFNHXOFP-LBPRGKRZSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- 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
- C07D403/12—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 chain containing hetero atoms as chain links
-
- 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
-
- 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
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/04—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/06—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D277/06—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/10—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Immunology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Virology (AREA)
- Oncology (AREA)
- Endocrinology (AREA)
- Transplantation (AREA)
- Child & Adolescent Psychology (AREA)
- AIDS & HIV (AREA)
- Emergency Medicine (AREA)
- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0104142A FR2822826B1 (fr) | 2001-03-28 | 2001-03-28 | Nouveaux derives sulfonyles d'alpha-amino-acides, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20021542D0 NO20021542D0 (no) | 2002-03-27 |
| NO20021542L NO20021542L (no) | 2002-09-30 |
| NO322895B1 true NO322895B1 (no) | 2006-12-18 |
Family
ID=8861608
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20021542A NO322895B1 (no) | 2001-03-28 | 2002-03-27 | Nye <alfa>-aminosyresulfonylforbindelser, fremgangsmate ved deres fremstilling og farmasoytiske sammensetninger inneholdende dem, samt deres anvendelse. |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US6716843B2 (en:Method) |
| EP (1) | EP1245568B1 (en:Method) |
| JP (1) | JP3761827B2 (en:Method) |
| KR (1) | KR100457725B1 (en:Method) |
| CN (1) | CN1166633C (en:Method) |
| AR (1) | AR033620A1 (en:Method) |
| AT (1) | ATE316080T1 (en:Method) |
| AU (1) | AU780373B2 (en:Method) |
| BR (1) | BR0200982A (en:Method) |
| CA (1) | CA2379197C (en:Method) |
| DE (1) | DE60208763T2 (en:Method) |
| DK (1) | DK1245568T3 (en:Method) |
| EA (1) | EA004591B1 (en:Method) |
| ES (1) | ES2256421T3 (en:Method) |
| FR (1) | FR2822826B1 (en:Method) |
| HK (1) | HK1050357B (en:Method) |
| HU (1) | HUP0201088A3 (en:Method) |
| MX (1) | MXPA02002720A (en:Method) |
| NO (1) | NO322895B1 (en:Method) |
| NZ (1) | NZ518035A (en:Method) |
| PL (1) | PL353084A1 (en:Method) |
| PT (1) | PT1245568E (en:Method) |
| SI (1) | SI1245568T1 (en:Method) |
| ZA (1) | ZA200202525B (en:Method) |
Families Citing this family (58)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6946481B1 (en) * | 1994-08-19 | 2005-09-20 | Abbott Laboratories | Endothelin antagonists |
| GB0010183D0 (en) * | 2000-04-26 | 2000-06-14 | Ferring Bv | Inhibitors of dipeptidyl peptidase IV |
| EP1399433B1 (en) | 2001-06-27 | 2007-08-22 | Smithkline Beecham Corporation | Fluoropyrrolidines as dipeptidyl peptidase inhibitors |
| WO2003002530A2 (en) * | 2001-06-27 | 2003-01-09 | Smithkline Beecham Corporation | Pyrrolidines as dipeptidyl peptidase inhibitors |
| DE60222667T2 (de) | 2001-06-27 | 2008-07-17 | Smithkline Beecham Corp. | Fluorpyrrolidine als dipeptidylpeptidaseinhibitoren |
| EP1426366A4 (en) * | 2001-09-14 | 2004-12-08 | Mitsubishi Pharma Corp | THIAZOLIDE DERIVATIVES AND THEIR MEDICAL USE |
| JP4413863B2 (ja) * | 2002-11-07 | 2010-02-10 | メルク エンド カムパニー インコーポレーテッド | 糖尿病の治療又は予防のためのジペチジルペプチダーゼ阻害剤としてのフェニルアラニン誘導体 |
| EP1578414A4 (en) * | 2002-12-04 | 2007-10-24 | Merck & Co Inc | PHENYLALANINE DERIVATIVES ALSDIPEPTIDYL-PEPTIDASE INHIBITORS FOR THE TREATMENT OR PREVENTION OF DIABETES |
| US7550590B2 (en) * | 2003-03-25 | 2009-06-23 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| WO2004103993A1 (en) | 2003-05-14 | 2004-12-02 | Syrrx, Inc. | Dipeptidyl peptidase inhibitors |
| US7169926B1 (en) | 2003-08-13 | 2007-01-30 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| US20050070531A1 (en) * | 2003-08-13 | 2005-03-31 | Syrrx, Inc. | Dipeptidyl peptidase inhibitors |
| US7678909B1 (en) | 2003-08-13 | 2010-03-16 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| WO2005030751A2 (en) * | 2003-09-08 | 2005-04-07 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| WO2005026148A1 (en) * | 2003-09-08 | 2005-03-24 | Takeda San Diego, Inc. | Dipeptidyl peptidase inhibitors |
| KR20150028829A (ko) | 2003-11-17 | 2015-03-16 | 노파르티스 아게 | 디펩티딜 펩티다제 ⅳ 억제제의 용도 |
| BR122018014389B1 (pt) * | 2004-01-20 | 2023-04-25 | Novartis Ag | Processo para preparar comprimido farmacêutico por compressão direta |
| CN101618216B (zh) * | 2004-01-20 | 2012-01-04 | 诺瓦提斯公司 | 直接压片配方和方法 |
| US7732446B1 (en) | 2004-03-11 | 2010-06-08 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| CN102140090A (zh) * | 2004-03-15 | 2011-08-03 | 武田药品工业株式会社 | 二肽基肽酶抑制剂 |
| JP2008501714A (ja) * | 2004-06-04 | 2008-01-24 | 武田薬品工業株式会社 | ジペプチジルペプチダーゼインヒビター |
| WO2006019965A2 (en) | 2004-07-16 | 2006-02-23 | Takeda San Diego, Inc. | Dipeptidyl peptidase inhibitors |
| AU2005267093B2 (en) * | 2004-07-23 | 2009-10-01 | Nuada Llc | Peptidase inhibitors |
| JP2008524331A (ja) * | 2004-12-21 | 2008-07-10 | 武田薬品工業株式会社 | ジペプチジルペプチダーゼ阻害剤 |
| DOP2006000008A (es) * | 2005-01-10 | 2006-08-31 | Arena Pharm Inc | Terapia combinada para el tratamiento de la diabetes y afecciones relacionadas y para el tratamiento de afecciones que mejoran mediante un incremento de la concentración sanguínea de glp-1 |
| CN101277949A (zh) * | 2005-04-22 | 2008-10-01 | 阿兰托斯制药控股公司 | 二肽基肽酶-ⅳ抑制剂 |
| EP1917001A2 (en) * | 2005-08-11 | 2008-05-07 | F.Hoffmann-La Roche Ag | Pharmaceutical composition comprising a dpp-iv inhibitor |
| EP1760076A1 (en) | 2005-09-02 | 2007-03-07 | Ferring B.V. | FAP Inhibitors |
| WO2007033265A1 (en) * | 2005-09-14 | 2007-03-22 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors for treating diabetis |
| PL1931350T5 (pl) * | 2005-09-14 | 2021-11-15 | Takeda Pharmaceutical Company Limited | Podanie inhibitorów dipeptydylo-peptydazy |
| JP5027137B2 (ja) | 2005-09-14 | 2012-09-19 | 武田薬品工業株式会社 | ジペプチジルペプチダーゼ阻害剤の投与 |
| TW200745079A (en) * | 2005-09-16 | 2007-12-16 | Takeda Pharmaceuticals Co | Polymorphs of benzoate salt of 2-[[6-[(3R)-3-amino-1-piperidinyl]-3,4-dihydro-3-methyl-2,4-dioxo-1(2H)-pyrimidinyl]methyl]-benzonitrile and methods of use therefor |
| TW200745080A (en) * | 2005-09-16 | 2007-12-16 | Takeda Pharmaceuticals Co | Polymorphs of tartrate salt of 2-[2-(3-(R)-amino-piperidin-1-yl)-5-fluoro-6-oxo-6H-pyrimidin-1-ylmethyl]-benzonitrile and methods of use therefor |
| KR101368988B1 (ko) * | 2005-09-16 | 2014-02-28 | 다케다 야쿠힌 고교 가부시키가이샤 | 디펩티딜 펩티다제 억제제 |
| GB0526291D0 (en) | 2005-12-23 | 2006-02-01 | Prosidion Ltd | Therapeutic method |
| JP2009531456A (ja) * | 2006-03-28 | 2009-09-03 | 武田薬品工業株式会社 | （ｒ）−３−アミノピペリジン二塩酸塩の調製 |
| WO2007112347A1 (en) | 2006-03-28 | 2007-10-04 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| BRPI0710597A2 (pt) | 2006-04-11 | 2012-06-19 | Arena Pharm Inc | método de uso do receptor gpr119 para identificar compostos úteis para aumento da massa óssea em um indivìduo |
| PE20071221A1 (es) | 2006-04-11 | 2007-12-14 | Arena Pharm Inc | Agonistas del receptor gpr119 en metodos para aumentar la masa osea y para tratar la osteoporosis y otras afecciones caracterizadas por masa osea baja, y la terapia combinada relacionada a estos agonistas |
| US8324383B2 (en) | 2006-09-13 | 2012-12-04 | Takeda Pharmaceutical Company Limited | Methods of making polymorphs of benzoate salt of 2-[[6-[(3R)-3-amino-1-piperidinyl]-3,4-dihydro-3-methyl-2,4-dioxo-1(2H)-pyrimidinyl]methyl]-benzonitrile |
| PE20081150A1 (es) * | 2006-09-13 | 2008-10-03 | Takeda Pharmaceutical | Inhibidores de dipetidilpeptidasa |
| TW200838536A (en) * | 2006-11-29 | 2008-10-01 | Takeda Pharmaceutical | Polymorphs of succinate salt of 2-[6-(3-amino-piperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethy]-4-fluor-benzonitrile and methods of use therefor |
| US8093236B2 (en) | 2007-03-13 | 2012-01-10 | Takeda Pharmaceuticals Company Limited | Weekly administration of dipeptidyl peptidase inhibitors |
| EP2146210A1 (en) | 2008-04-07 | 2010-01-20 | Arena Pharmaceuticals, Inc. | Methods of using A G protein-coupled receptor to identify peptide YY (PYY) secretagogues and compounds useful in the treatment of conditions modulated by PYY |
| CN101684088B (zh) * | 2008-09-22 | 2011-05-11 | 天津药物研究院 | 氰甲基吡咯衍生物、其制备方法和用途 |
| AR077642A1 (es) | 2009-07-09 | 2011-09-14 | Arena Pharm Inc | Moduladores del metabolismo y el tratamiento de trastornos relacionados con el mismo |
| MX2012011631A (es) | 2010-04-06 | 2013-01-18 | Arena Pharm Inc | Moduladores del receptor gpr119 y el tratamiento de trastornos relacionados con el mismo. |
| JP5941916B2 (ja) | 2010-09-22 | 2016-06-29 | アリーナ ファーマシューティカルズ， インコーポレイテッド | Ｇｐｒ１１９レセプターのモジュレーターおよびそれに関連する障害の処置 |
| WO2012135570A1 (en) | 2011-04-01 | 2012-10-04 | Arena Pharmaceuticals, Inc. | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
| US20140066369A1 (en) | 2011-04-19 | 2014-03-06 | Arena Pharmaceuticals, Inc. | Modulators Of The GPR119 Receptor And The Treatment Of Disorders Related Thereto |
| US20140038889A1 (en) | 2011-04-22 | 2014-02-06 | Arena Pharmaceuticals, Inc. | Modulators Of The GPR119 Receptor And The Treatment Of Disorders Related Thereto |
| US20140051714A1 (en) | 2011-04-22 | 2014-02-20 | Arena Pharmaceuticals, Inc. | Modulators Of The GPR119 Receptor And The Treatment Of Disorders Related Thereto |
| WO2012170702A1 (en) | 2011-06-08 | 2012-12-13 | Arena Pharmaceuticals, Inc. | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
| WO2013055910A1 (en) | 2011-10-12 | 2013-04-18 | Arena Pharmaceuticals, Inc. | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
| WO2014074668A1 (en) | 2012-11-08 | 2014-05-15 | Arena Pharmaceuticals, Inc. | Modulators of gpr119 and the treatment of disorders related thereto |
| JP2018507914A (ja) | 2015-03-09 | 2018-03-22 | インテクリン・セラピューティクス・インコーポレイテッド | 非アルコール性脂肪肝疾患および／またはリポジストロフィーの処置のための方法 |
| WO2018162722A1 (en) | 2017-03-09 | 2018-09-13 | Deutsches Institut Für Ernährungsforschung Potsdam-Rehbrücke | Dpp-4 inhibitors for use in treating bone fractures |
| CN110996951A (zh) | 2017-04-03 | 2020-04-10 | 科赫罗斯生物科学股份有限公司 | 治疗进行性核上性麻痹的PPARγ激动剂 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0490379A3 (de) * | 1990-12-13 | 1992-06-24 | BERLIN-CHEMIE Aktiengesellschaft | Diaminosäurederivate und pharmazeutische Zusammensetzungen |
| IL111785A0 (en) * | 1993-12-03 | 1995-01-24 | Ferring Bv | Dp-iv inhibitors and pharmaceutical compositions containing them |
| TW492957B (en) * | 1996-11-07 | 2002-07-01 | Novartis Ag | N-substituted 2-cyanopyrrolidnes |
| US6110949A (en) * | 1999-06-24 | 2000-08-29 | Novartis Ag | N-(substituted glycyl)-4-cyanothiazolidines, pharmaceutical compositions containing them and their use in inhibiting dipeptidyl peptidase-IV |
-
2001
- 2001-03-28 FR FR0104142A patent/FR2822826B1/fr not_active Expired - Fee Related
-
2002
- 2002-03-13 MX MXPA02002720A patent/MXPA02002720A/es active IP Right Grant
- 2002-03-26 AR ARP020101090A patent/AR033620A1/es unknown
- 2002-03-27 NO NO20021542A patent/NO322895B1/no unknown
- 2002-03-27 JP JP2002087792A patent/JP3761827B2/ja not_active Expired - Fee Related
- 2002-03-27 PT PT02290755T patent/PT1245568E/pt unknown
- 2002-03-27 AT AT02290755T patent/ATE316080T1/de not_active IP Right Cessation
- 2002-03-27 NZ NZ518035A patent/NZ518035A/en unknown
- 2002-03-27 ES ES02290755T patent/ES2256421T3/es not_active Expired - Lifetime
- 2002-03-27 SI SI200230261T patent/SI1245568T1/sl unknown
- 2002-03-27 EA EA200200299A patent/EA004591B1/ru not_active IP Right Cessation
- 2002-03-27 DE DE60208763T patent/DE60208763T2/de not_active Expired - Fee Related
- 2002-03-27 BR BR0200982-0A patent/BR0200982A/pt not_active IP Right Cessation
- 2002-03-27 CN CNB021082286A patent/CN1166633C/zh not_active Expired - Fee Related
- 2002-03-27 DK DK02290755T patent/DK1245568T3/da active
- 2002-03-27 EP EP02290755A patent/EP1245568B1/fr not_active Expired - Lifetime
- 2002-03-28 PL PL02353084A patent/PL353084A1/xx not_active Application Discontinuation
- 2002-03-28 AU AU29350/02A patent/AU780373B2/en not_active Ceased
- 2002-03-28 HU HU0201088A patent/HUP0201088A3/hu unknown
- 2002-03-28 KR KR10-2002-0016984A patent/KR100457725B1/ko not_active Expired - Fee Related
- 2002-03-28 ZA ZA200202525A patent/ZA200202525B/xx unknown
- 2002-03-28 CA CA002379197A patent/CA2379197C/fr not_active Expired - Fee Related
- 2002-03-28 US US10/109,407 patent/US6716843B2/en not_active Expired - Fee Related
-
2003
- 2003-03-14 HK HK03101863.9A patent/HK1050357B/zh not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO322895B1 (no) | Nye <alfa>-aminosyresulfonylforbindelser, fremgangsmate ved deres fremstilling og farmasoytiske sammensetninger inneholdende dem, samt deres anvendelse. | |
| RU2072359C1 (ru) | Производные уксусной кислоты или их гидраты, или их сольваты, или их фармацевтически приемлемые соли | |
| NO322569B1 (no) | Nye <alfa>-aminosyreforbindelser, fremgangsmate ved deres fremstilling og farmasoytiske sammensetninger inneholdende dem | |
| NO314406B1 (no) | Nye peptidderivater, farmasöytisk preparat inneholdende slike derivater, deres anvendelse, fremgangsmåter for deres fremstilling, ogmellomprodukter | |
| ES2294103T3 (es) | Inhibidores de vih proteasa con base en derivados de aminoacidos. | |
| HU222353B1 (hu) | Az N-terminálison szulfonil- vagy szulfamoil-csoportokat tartalmazó dipeptid-(p-amido-benzil)-amidok és alkalmazásuk | |
| JPH0341091A (ja) | 酵素阻害性ペプチド誘導体 | |
| AU634417B2 (en) | Phosphonopyrrolidine- and piperidine-containing pseudopeptides of the statin type, a process for their preparation and their use as medicaments against retroviruses | |
| AU666532B2 (en) | Dithiolanylglycine-containing HIV protease inhibitors of the hydroxyethylene isostere type | |
| US7910556B2 (en) | PAR-2 agonist | |
| FR2594831A1 (fr) | Derives de proline, leur procede de preparation, composition pharmaceutique en comportant et procede d'inhibition de l'enzyme transformant l'angiotensine | |
| US8133864B2 (en) | PAR-2 agonist | |
| US6632826B1 (en) | Carbocyclic HIV protease inhibitors | |
| JPS62201899A (ja) | プロリン誘導体 | |
| JP2849810B2 (ja) | ヒト免疫不全ウイルス（ｈｉｖ）プロテアーゼ阻害化合物、その製造方法、及びそれを含む組成物 | |
| LT3681B (en) | N-acyl-alpha-amino acid derivatives, method for producting thereof,pharmaceutical compositions and preparing them |