NO20005506L - Substituerte beta-aminosyre-inhibitorer for metionin- aminopeptidase-2 - Google Patents
Substituerte beta-aminosyre-inhibitorer for metionin- aminopeptidase-2Info
- Publication number
- NO20005506L NO20005506L NO20005506A NO20005506A NO20005506L NO 20005506 L NO20005506 L NO 20005506L NO 20005506 A NO20005506 A NO 20005506A NO 20005506 A NO20005506 A NO 20005506A NO 20005506 L NO20005506 L NO 20005506L
- Authority
- NO
- Norway
- Prior art keywords
- amino
- cyclohexyl
- hydroxy
- butanamide
- hydroxybutanamide
- Prior art date
Links
- 108090000192 Methionyl aminopeptidases Proteins 0.000 title description 16
- 102100023174 Methionine aminopeptidase 2 Human genes 0.000 title description 15
- 239000003112 inhibitor Substances 0.000 title description 6
- 150000001576 beta-amino acids Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 362
- -1 (2RS,3R)-3-amino-2-hydroxy-4-cyclohexyl Chemical group 0.000 claims description 199
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 74
- 125000000217 alkyl group Chemical group 0.000 claims description 70
- 150000001408 amides Chemical class 0.000 claims description 53
- 238000000034 method Methods 0.000 claims description 51
- IPWFJLQDVFKJDU-UHFFFAOYSA-N pentanamide Chemical compound CCCCC(N)=O IPWFJLQDVFKJDU-UHFFFAOYSA-N 0.000 claims description 50
- 125000003118 aryl group Chemical group 0.000 claims description 49
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 43
- 150000002148 esters Chemical class 0.000 claims description 31
- 125000000623 heterocyclic group Chemical group 0.000 claims description 29
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 23
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical compound FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 claims description 19
- 229940079593 drug Drugs 0.000 claims description 19
- 239000003814 drug Substances 0.000 claims description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 19
- 125000004423 acyloxy group Chemical group 0.000 claims description 18
- 229960003767 alanine Drugs 0.000 claims description 18
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
- 229920001774 Perfluoroether Polymers 0.000 claims description 16
- 239000000651 prodrug Substances 0.000 claims description 16
- 229940002612 prodrug Drugs 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 125000002252 acyl group Chemical group 0.000 claims description 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
- 230000033115 angiogenesis Effects 0.000 claims description 13
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 13
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 12
- 125000004104 aryloxy group Chemical group 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- 239000002243 precursor Substances 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- JTEJPPKMYBDEMY-UHFFFAOYSA-N 5-Methoxytryptamine Natural products COC1=CC=C2NC=C(CCN)C2=C1 JTEJPPKMYBDEMY-UHFFFAOYSA-N 0.000 claims description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 7
- 125000000266 alpha-aminoacyl group Chemical group 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 7
- 125000006239 protecting group Chemical group 0.000 claims description 7
- XZKDNZNWHYYWCJ-KWCCSABGSA-N (3r)-3-amino-2-hydroxy-n-[2-(4-methoxyphenyl)ethyl]-5-methylsulfanylpentanamide Chemical compound COC1=CC=C(CCNC(=O)C(O)[C@H](N)CCSC)C=C1 XZKDNZNWHYYWCJ-KWCCSABGSA-N 0.000 claims description 6
- 241000124008 Mammalia Species 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 229940097276 5-methoxytryptamine Drugs 0.000 claims description 5
- VWKZILYMAAVEEM-JHJMLUEUSA-N (3r)-3-amino-2-hydroxy-5-methylsulfanyl-n-(2-pyridin-3-ylethyl)pentanamide Chemical compound CSCC[C@@H](N)C(O)C(=O)NCCC1=CC=CN=C1 VWKZILYMAAVEEM-JHJMLUEUSA-N 0.000 claims description 4
- SFAAWUWQUWJOJN-JHJMLUEUSA-N (3r)-3-amino-2-hydroxy-5-methylsulfanyl-n-(2-pyridin-4-ylethyl)pentanamide Chemical compound CSCC[C@@H](N)C(O)C(=O)NCCC1=CC=NC=C1 SFAAWUWQUWJOJN-JHJMLUEUSA-N 0.000 claims description 4
- GOYBDMYTXSNRFJ-CNZKWPKMSA-N (3r)-3-amino-2-hydroxy-5-methylsulfanylpentanoic acid Chemical compound CSCC[C@@H](N)C(O)C(O)=O GOYBDMYTXSNRFJ-CNZKWPKMSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 4
- XDCVVGSBJOBLEX-VYJHHOQDSA-N n-[(2r)-2-amino-3-hydroxy-4-(4-phenylbutanoyl)cyclohexyl]butanamide Chemical compound OC1[C@H](N)C(NC(=O)CCC)CCC1C(=O)CCCC1=CC=CC=C1 XDCVVGSBJOBLEX-VYJHHOQDSA-N 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229940124530 sulfonamide Drugs 0.000 claims description 4
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
- ZIGMWDSIQNYHNS-MRTLOADZSA-N (3r)-3-amino-2-hydroxy-4-phenyl-n-(4-phenylbutyl)butanamide Chemical compound C([C@@H](N)C(O)C(=O)NCCCCC=1C=CC=CC=1)C1=CC=CC=C1 ZIGMWDSIQNYHNS-MRTLOADZSA-N 0.000 claims description 3
- CCMIKIMUXWEVRC-JHJMLUEUSA-N (3r)-3-amino-2-hydroxy-5-methylsulfanyl-n-(2-pyridin-2-ylethyl)pentanamide Chemical compound CSCC[C@@H](N)C(O)C(=O)NCCC1=CC=CC=N1 CCMIKIMUXWEVRC-JHJMLUEUSA-N 0.000 claims description 3
- SJBYPFPOTSNMTP-GICMACPYSA-N (3r)-3-amino-2-hydroxy-5-methylsulfanyl-n-(4-phenylbutyl)pentanamide Chemical compound CSCC[C@@H](N)C(O)C(=O)NCCCCC1=CC=CC=C1 SJBYPFPOTSNMTP-GICMACPYSA-N 0.000 claims description 3
- IFCLPXHQPYBNRT-MRTLOADZSA-N (3r)-3-amino-2-hydroxy-5-methylsulfanyl-n-[2-(4-phenoxyphenyl)ethyl]pentanamide Chemical compound C1=CC(CCNC(=O)C(O)[C@H](N)CCSC)=CC=C1OC1=CC=CC=C1 IFCLPXHQPYBNRT-MRTLOADZSA-N 0.000 claims description 3
- PIUYYIOQTPBRGI-KWCCSABGSA-N (3r)-3-amino-2-hydroxy-n-methyl-5-methylsulfanyl-n-(2-phenylethyl)pentanamide Chemical compound CSCC[C@@H](N)C(O)C(=O)N(C)CCC1=CC=CC=C1 PIUYYIOQTPBRGI-KWCCSABGSA-N 0.000 claims description 3
- KNQYFKCOYGSUBU-NQRDHLDYSA-N (3r)-3-amino-4-cyclohexyl-1-(2,6-dimethylmorpholin-4-yl)-2-hydroxybutan-1-one Chemical compound C1C(C)OC(C)CN1C(=O)C(O)[C@H](N)CC1CCCCC1 KNQYFKCOYGSUBU-NQRDHLDYSA-N 0.000 claims description 3
- QKEFLDQOSNHMOP-LMDPOFIKSA-N (3r)-3-amino-4-cyclohexyl-2-hydroxy-n-(1,2,3,4-tetrahydronaphthalen-1-yl)butanamide Chemical compound C([C@@H](N)C(O)C(=O)NC1C2=CC=CC=C2CCC1)C1CCCCC1 QKEFLDQOSNHMOP-LMDPOFIKSA-N 0.000 claims description 3
- PDNRLTWXUWVOJL-GICMACPYSA-N (3r)-3-amino-4-cyclohexyl-2-hydroxy-n-(2,4,4-trimethylpentan-2-yl)butanamide Chemical compound CC(C)(C)CC(C)(C)NC(=O)C(O)[C@H](N)CC1CCCCC1 PDNRLTWXUWVOJL-GICMACPYSA-N 0.000 claims description 3
- ANCKEWDBYVPDDH-XPCCGILXSA-N (3r)-3-amino-4-cyclohexyl-2-hydroxy-n-(2-methoxy-5-methylphenyl)butanamide Chemical compound COC1=CC=C(C)C=C1NC(=O)C(O)[C@H](N)CC1CCCCC1 ANCKEWDBYVPDDH-XPCCGILXSA-N 0.000 claims description 3
- XGBWLCHEOPEJOM-JBZHPUCOSA-N (3r)-3-amino-4-cyclohexyl-2-hydroxy-n-(2-methoxy-5-nitrophenyl)butanamide Chemical compound COC1=CC=C([N+]([O-])=O)C=C1NC(=O)C(O)[C@H](N)CC1CCCCC1 XGBWLCHEOPEJOM-JBZHPUCOSA-N 0.000 claims description 3
- JLQPMTHKVHTEFF-LCQOSCCDSA-N (3r)-3-amino-4-cyclohexyl-2-hydroxy-n-(2-methoxy-5-phenylphenyl)butanamide Chemical compound C([C@@H](N)C(O)C(=O)NC1=CC(=CC=C1OC)C=1C=CC=CC=1)C1CCCCC1 JLQPMTHKVHTEFF-LCQOSCCDSA-N 0.000 claims description 3
- LJUWUNJEQLDFHE-PLEWWHCXSA-N (3r)-3-amino-4-cyclohexyl-2-hydroxy-n-(2-methoxydibenzofuran-3-yl)butanamide Chemical compound C([C@@H](N)C(O)C(=O)NC1=CC2=C(C3=CC=CC=C3O2)C=C1OC)C1CCCCC1 LJUWUNJEQLDFHE-PLEWWHCXSA-N 0.000 claims description 3
- FVICCILWXLFSPV-JBZHPUCOSA-N (3r)-3-amino-4-cyclohexyl-2-hydroxy-n-(2-methoxyphenyl)butanamide Chemical compound COC1=CC=CC=C1NC(=O)C(O)[C@H](N)CC1CCCCC1 FVICCILWXLFSPV-JBZHPUCOSA-N 0.000 claims description 3
- ZXJWHQKDYBBLEH-IURRXHLWSA-N (3r)-3-amino-4-cyclohexyl-2-hydroxy-n-(2-methyl-5-nitrophenyl)butanamide Chemical compound CC1=CC=C([N+]([O-])=O)C=C1NC(=O)C(O)[C@H](N)CC1CCCCC1 ZXJWHQKDYBBLEH-IURRXHLWSA-N 0.000 claims description 3
- RKTJALSLXLIPEW-IURRXHLWSA-N (3r)-3-amino-4-cyclohexyl-2-hydroxy-n-(2-methylphenyl)butanamide Chemical compound CC1=CC=CC=C1NC(=O)C(O)[C@H](N)CC1CCCCC1 RKTJALSLXLIPEW-IURRXHLWSA-N 0.000 claims description 3
- PFNNCGBMFLGNJZ-ITUIMRKVSA-N (3r)-3-amino-4-cyclohexyl-2-hydroxy-n-(2-phenoxyphenyl)butanamide Chemical compound C([C@@H](N)C(O)C(=O)NC=1C(=CC=CC=1)OC=1C=CC=CC=1)C1CCCCC1 PFNNCGBMFLGNJZ-ITUIMRKVSA-N 0.000 claims description 3
- VLDFVAQMWJOPAF-TZHYSIJRSA-N (3r)-3-amino-4-cyclohexyl-2-hydroxy-n-(2-phenylethyl)butanamide Chemical compound C([C@@H](N)C(O)C(=O)NCCC=1C=CC=CC=1)C1CCCCC1 VLDFVAQMWJOPAF-TZHYSIJRSA-N 0.000 claims description 3
- MDSFSHNDHMUWCC-XPCCGILXSA-N (3r)-3-amino-4-cyclohexyl-2-hydroxy-n-(3,4,5-trimethoxyphenyl)butanamide Chemical compound COC1=C(OC)C(OC)=CC(NC(=O)C(O)[C@H](N)CC2CCCCC2)=C1 MDSFSHNDHMUWCC-XPCCGILXSA-N 0.000 claims description 3
- XLAPNMKCRFDRJZ-LDCVWXEPSA-N (3r)-3-amino-4-cyclohexyl-2-hydroxy-n-(3-methoxy-4-methylphenyl)butanamide Chemical compound C1=C(C)C(OC)=CC(NC(=O)C(O)[C@H](N)CC2CCCCC2)=C1 XLAPNMKCRFDRJZ-LDCVWXEPSA-N 0.000 claims description 3
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- SPCHJCDXXRJBTF-HRDQMINSSA-N (3r)-3-amino-4-cyclohexyl-2-hydroxy-n-(3-methylbutan-2-yl)butanamide Chemical compound CC(C)C(C)NC(=O)C(O)[C@H](N)CC1CCCCC1 SPCHJCDXXRJBTF-HRDQMINSSA-N 0.000 claims description 3
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- ZNQXNULNKQNTKN-IURRXHLWSA-N (3r)-3-amino-4-cyclohexyl-2-hydroxy-n-(4-iodo-2-methylphenyl)butanamide Chemical compound CC1=CC(I)=CC=C1NC(=O)C(O)[C@H](N)CC1CCCCC1 ZNQXNULNKQNTKN-IURRXHLWSA-N 0.000 claims description 3
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- XGCYRJOPFQATIA-AAFJCEBUSA-N (3r)-3-amino-4-cyclohexyl-2-hydroxy-n-(4-methylphenyl)butanamide Chemical compound C1=CC(C)=CC=C1NC(=O)C(O)[C@H](N)CC1CCCCC1 XGCYRJOPFQATIA-AAFJCEBUSA-N 0.000 claims description 3
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- SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 1
- NESRXFGQJARQNM-OWYFMNJBSA-N graphinone Chemical compound O=C([C@H]([C@]1(O)[C@]2(C)[C@H](O2)CC=C(C)C)OC)CC[C@@]21CO2 NESRXFGQJARQNM-OWYFMNJBSA-N 0.000 description 1
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- 239000003906 humectant Substances 0.000 description 1
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- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
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- 239000007927 intramuscular injection Substances 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000741 isoleucyl group Chemical group [H]N([H])C(C(C([H])([H])[H])C([H])([H])C([H])([H])[H])C(=O)O* 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 229950003188 isovaleryl diethylamide Drugs 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 125000001998 leucyl group Chemical group 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
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- 210000004185 liver Anatomy 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
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- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
- 208000002780 macular degeneration Diseases 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
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- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
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- 239000012528 membrane Substances 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 125000002073 methionyl group Chemical group 0.000 description 1
- 108010016686 methionyl-alanyl-serine Proteins 0.000 description 1
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- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- CEMZBWPSKYISTN-YFKPBYRVSA-N methyl (2s)-2-amino-3-methylbutanoate Chemical compound COC(=O)[C@@H](N)C(C)C CEMZBWPSKYISTN-YFKPBYRVSA-N 0.000 description 1
- TVZNFYXAPXOARC-LURJTMIESA-N methyl (2s)-2-aminohexanoate Chemical compound CCCC[C@H](N)C(=O)OC TVZNFYXAPXOARC-LURJTMIESA-N 0.000 description 1
- YXMMTUJDQTVJEN-WDSKDSINSA-N methyl (2s,3s)-2-amino-3-methylpentanoate Chemical compound CC[C@H](C)[C@H](N)C(=O)OC YXMMTUJDQTVJEN-WDSKDSINSA-N 0.000 description 1
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 1
- NLWBJPPMPLPZIE-UHFFFAOYSA-N methyl 4-(bromomethyl)benzoate Chemical compound COC(=O)C1=CC=C(CBr)C=C1 NLWBJPPMPLPZIE-UHFFFAOYSA-N 0.000 description 1
- ORESWLWJNGSSQI-UYUUDJTFSA-N methyl 4-[[(3r)-3-amino-4-cyclohexyl-2-hydroxybutanoyl]amino]thiophene-3-carboxylate;hydrochloride Chemical compound Cl.COC(=O)C1=CSC=C1NC(=O)C(O)[C@H](N)CC1CCCCC1 ORESWLWJNGSSQI-UYUUDJTFSA-N 0.000 description 1
- BUFZZXCVOFBHLS-UHFFFAOYSA-N methyl 4-aminothiophene-3-carboxylate Chemical compound COC(=O)C1=CSC=C1N BUFZZXCVOFBHLS-UHFFFAOYSA-N 0.000 description 1
- QVDXUKJJGUSGLS-LURJTMIESA-N methyl L-leucinate Chemical compound COC(=O)[C@@H](N)CC(C)C QVDXUKJJGUSGLS-LURJTMIESA-N 0.000 description 1
- VSDUZFOSJDMAFZ-VIFPVBQESA-N methyl L-phenylalaninate Chemical compound COC(=O)[C@@H](N)CC1=CC=CC=C1 VSDUZFOSJDMAFZ-VIFPVBQESA-N 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
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- 125000002950 monocyclic group Chemical group 0.000 description 1
- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
- FMASTMURQSHELY-UHFFFAOYSA-N n-(4-fluoro-2-methylphenyl)-3-methyl-n-[(2-methyl-1h-indol-4-yl)methyl]pyridine-4-carboxamide Chemical compound C1=CC=C2NC(C)=CC2=C1CN(C=1C(=CC(F)=CC=1)C)C(=O)C1=CC=NC=C1C FMASTMURQSHELY-UHFFFAOYSA-N 0.000 description 1
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- STJJVNNQIAHWNN-UCLNMNFYSA-N n-[(2r)-2-amino-3-hydroxy-4-(4-phenylbutanoyl)cyclohexyl]butanamide;hydrochloride Chemical compound Cl.OC1[C@H](N)C(NC(=O)CCC)CCC1C(=O)CCCC1=CC=CC=C1 STJJVNNQIAHWNN-UCLNMNFYSA-N 0.000 description 1
- HIPXPABRMMYVQD-UHFFFAOYSA-N n-benzylbutan-1-amine Chemical compound CCCCNCC1=CC=CC=C1 HIPXPABRMMYVQD-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- NNKPHNTWNILINE-UHFFFAOYSA-N n-cyclopropyl-3-fluoro-4-methyl-5-[3-[[1-[2-[2-(methylamino)ethoxy]phenyl]cyclopropyl]amino]-2-oxopyrazin-1-yl]benzamide Chemical compound CNCCOC1=CC=CC=C1C1(NC=2C(N(C=3C(=C(F)C=C(C=3)C(=O)NC3CC3)C)C=CN=2)=O)CC1 NNKPHNTWNILINE-UHFFFAOYSA-N 0.000 description 1
- FPKGTVXPIULTIP-UHFFFAOYSA-N n-ethyl-1,3-benzodioxol-5-amine Chemical compound CCNC1=CC=C2OCOC2=C1 FPKGTVXPIULTIP-UHFFFAOYSA-N 0.000 description 1
- XWCCTMBMQUCLSI-UHFFFAOYSA-N n-ethyl-n-propylpropan-1-amine Chemical compound CCCN(CC)CCC XWCCTMBMQUCLSI-UHFFFAOYSA-N 0.000 description 1
- MQRIUFVBEVFILS-UHFFFAOYSA-N n-methyl-1-naphthalen-1-ylmethanamine Chemical compound C1=CC=C2C(CNC)=CC=CC2=C1 MQRIUFVBEVFILS-UHFFFAOYSA-N 0.000 description 1
- OLLZXQIFCRIRMH-UHFFFAOYSA-N n-methylbutanamide Chemical compound CCCC(=O)NC OLLZXQIFCRIRMH-UHFFFAOYSA-N 0.000 description 1
- NVSYANRBXPURRQ-UHFFFAOYSA-N naphthalen-1-ylmethanamine Chemical compound C1=CC=C2C(CN)=CC=CC2=C1 NVSYANRBXPURRQ-UHFFFAOYSA-N 0.000 description 1
- OPECTNGATDYLSS-UHFFFAOYSA-N naphthalene-2-sulfonyl chloride Chemical compound C1=CC=CC2=CC(S(=O)(=O)Cl)=CC=C21 OPECTNGATDYLSS-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
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- 230000010046 negative regulation of endothelial cell proliferation Effects 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 1
- 231100000344 non-irritating Toxicity 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- QNIVIMYXGGFTAK-UHFFFAOYSA-N octodrine Chemical compound CC(C)CCCC(C)N QNIVIMYXGGFTAK-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
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- 229940041678 oral spray Drugs 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 150000002905 orthoesters Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
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- 125000002971 oxazolyl group Chemical group 0.000 description 1
- YNOGYQAEJGADFJ-UHFFFAOYSA-N oxolan-2-ylmethanamine Chemical compound NCC1CCCO1 YNOGYQAEJGADFJ-UHFFFAOYSA-N 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 1
- WXWCDTXEKCVRRO-UHFFFAOYSA-N para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 description 1
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- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- BUQPIKAEKYNDAS-UHFFFAOYSA-N phenacyl 2-[4-(bromomethyl)phenyl]acetate Chemical compound C1=CC(CBr)=CC=C1CC(=O)OCC(=O)C1=CC=CC=C1 BUQPIKAEKYNDAS-UHFFFAOYSA-N 0.000 description 1
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- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 125000000405 phenylalanyl group Chemical group 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 125000005633 phthalidyl group Chemical group 0.000 description 1
- 125000005543 phthalimide group Chemical group 0.000 description 1
- 125000001557 phthalyl group Chemical group C(=O)(O)C1=C(C(=O)*)C=CC=C1 0.000 description 1
- 230000037081 physical activity Effects 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- LWMPFIOTEAXAGV-UHFFFAOYSA-N piperidin-1-amine Chemical class NN1CCCCC1 LWMPFIOTEAXAGV-UHFFFAOYSA-N 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- LZMJNVRJMFMYQS-UHFFFAOYSA-N poseltinib Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(OC=C2)C2=N1 LZMJNVRJMFMYQS-UHFFFAOYSA-N 0.000 description 1
- LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- SBMSLRMNBSMKQC-UHFFFAOYSA-N pyrrolidin-1-amine Chemical class NN1CCCC1 SBMSLRMNBSMKQC-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007634 remodeling Methods 0.000 description 1
- 239000003340 retarding agent Substances 0.000 description 1
- 210000001525 retina Anatomy 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
- 125000002072 seryl group Chemical group 0.000 description 1
- 229930004725 sesquiterpene Natural products 0.000 description 1
- 150000004354 sesquiterpene derivatives Chemical class 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000011006 sodium potassium tartrate Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- UDYFLDICVHJSOY-UHFFFAOYSA-N sulfur trioxide-pyridine complex Substances O=S(=O)=O.C1=CC=NC=C1 UDYFLDICVHJSOY-UHFFFAOYSA-N 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- SJMDMGHPMLKLHQ-UHFFFAOYSA-N tert-butyl 2-aminoacetate Chemical compound CC(C)(C)OC(=O)CN SJMDMGHPMLKLHQ-UHFFFAOYSA-N 0.000 description 1
- QQWYQAQQADNEIC-RVDMUPIBSA-N tert-butyl [(z)-[cyano(phenyl)methylidene]amino] carbonate Chemical compound CC(C)(C)OC(=O)O\N=C(/C#N)C1=CC=CC=C1 QQWYQAQQADNEIC-RVDMUPIBSA-N 0.000 description 1
- NUZPFVAHOYILMB-MRVPVSSYSA-N tert-butyl [[(2R)-1-hydroxypropan-2-yl]-propanoylamino] carbonate Chemical compound C(C)(C)(C)OC(=O)ON([C@H](C)CO)C(CC)=O NUZPFVAHOYILMB-MRVPVSSYSA-N 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- LFKDJXLFVYVEFG-UHFFFAOYSA-N tert-butyl carbamate Chemical group CC(C)(C)OC(N)=O LFKDJXLFVYVEFG-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BVWMROSCGYTJLB-ZDUSSCGKSA-N tert-butyl n-[(2s)-1-benzylsulfanyl-3-oxopropan-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@@H](C=O)CSCC1=CC=CC=C1 BVWMROSCGYTJLB-ZDUSSCGKSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- 150000003549 thiazolines Chemical class 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- FKKJJPMGAWGYPN-UHFFFAOYSA-N thiophen-2-ylmethanamine Chemical compound NCC1=CC=CS1 FKKJJPMGAWGYPN-UHFFFAOYSA-N 0.000 description 1
- 125000001239 threonyl group Chemical group 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 229940035339 tri-chlor Drugs 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- VSRBKQFNFZQRBM-UHFFFAOYSA-N tuaminoheptane Chemical compound CCCCCC(C)N VSRBKQFNFZQRBM-UHFFFAOYSA-N 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 230000005740 tumor formation Effects 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- QFKMMXYLAPZKIB-UHFFFAOYSA-N undecan-1-amine Chemical compound CCCCCCCCCCCN QFKMMXYLAPZKIB-UHFFFAOYSA-N 0.000 description 1
- 241000701447 unidentified baculovirus Species 0.000 description 1
- 125000002114 valyl group Chemical group 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 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
- C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—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 one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
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- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/58—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring 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 atoms of the carbocyclic ring
- C07D317/66—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/38—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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
- C07C2603/74—Adamantanes
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Enzymes And Modification Thereof (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US7171498A | 1998-05-01 | 1998-05-01 | |
PCT/US1999/009641 WO1999057098A2 (en) | 1998-05-01 | 1999-04-30 | Substituted beta-amino acid inhibitors of methionine aminopeptidase-2 |
US09/303,807 US6242494B1 (en) | 1998-05-01 | 1999-04-30 | Substituted β-amino acid inhibitors of methionine aminopeptidase-2 |
Publications (2)
Publication Number | Publication Date |
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NO20005506D0 NO20005506D0 (no) | 2000-11-01 |
NO20005506L true NO20005506L (no) | 2000-12-29 |
Family
ID=26752577
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO20005506A NO20005506L (no) | 1998-05-01 | 2000-11-01 | Substituerte beta-aminosyre-inhibitorer for metionin- aminopeptidase-2 |
Country Status (5)
Country | Link |
---|---|
BG (1) | BG104981A (sk) |
BR (1) | BR9910092A (sk) |
NO (1) | NO20005506L (sk) |
SK (1) | SK16282000A3 (sk) |
WO (1) | WO1999057098A2 (sk) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9929297D0 (en) * | 1999-12-11 | 2000-02-02 | Glaxo Group Ltd | Process |
US20020002152A1 (en) | 2000-04-14 | 2002-01-03 | Craig Richard A. | Hydrazide and alkoxyamide angiogenesis inhibitors |
CN100357283C (zh) * | 2002-04-02 | 2007-12-26 | 中国科学院上海药物研究所 | 一类甲硫氨酰氨肽酶抑制剂 |
US7030262B2 (en) | 2002-08-06 | 2006-04-18 | Abbott Laboratories | 3-Amino-2-hydroxyalkanoic acids and their prodrugs |
EP1546087A1 (en) * | 2002-08-06 | 2005-06-29 | Abbott Laboratories | 3-amino-2-hrydroxyalkanoic acids and their prodrugs |
CN1688557A (zh) * | 2002-10-09 | 2005-10-26 | 辉瑞产品公司 | 用于治疗神经变性疾病的噻唑化合物 |
WO2005009344A2 (en) | 2003-06-05 | 2005-02-03 | Elan Pharmaceuticals, Inc. | Acylated amino acid amidyl pyrazoles and related compounds |
US10646463B2 (en) | 2016-01-11 | 2020-05-12 | Syndevrx, Inc. | Treatment for tumors driven by metabolic dysfunction |
CN113453721A (zh) | 2018-10-26 | 2021-09-28 | 辛德弗雷克斯公司 | Metap2抑制剂的生物标志物及其应用 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1510477A (en) * | 1975-07-22 | 1978-05-10 | Microbial Chem Res Found | Peptides and to amino acid intermediates thereof |
US5442044A (en) * | 1991-01-04 | 1995-08-15 | Pfizer Inc. | Orally active renin inhibitors |
-
1999
- 1999-04-30 WO PCT/US1999/009641 patent/WO1999057098A2/en not_active Application Discontinuation
- 1999-04-30 SK SK1628-2000A patent/SK16282000A3/sk unknown
- 1999-04-30 BR BR9910092-4A patent/BR9910092A/pt not_active Application Discontinuation
-
2000
- 2000-11-01 NO NO20005506A patent/NO20005506L/no not_active Application Discontinuation
- 2000-11-24 BG BG104981A patent/BG104981A/xx unknown
Also Published As
Publication number | Publication date |
---|---|
WO1999057098A2 (en) | 1999-11-11 |
BR9910092A (pt) | 2002-01-22 |
NO20005506D0 (no) | 2000-11-01 |
BG104981A (en) | 2001-07-31 |
SK16282000A3 (sk) | 2001-05-10 |
WO1999057098A3 (en) | 2000-07-27 |
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