HRP20110044T2 - Supstituirani glicinamidi s antitrombotičkim i faktor-xa inhibirajućim djelovanjem - Google Patents
Supstituirani glicinamidi s antitrombotičkim i faktor-xa inhibirajućim djelovanjem Download PDFInfo
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- HRP20110044T2 HRP20110044T2 HR20110044T HRP20110044T HRP20110044T2 HR P20110044 T2 HRP20110044 T2 HR P20110044T2 HR 20110044 T HR20110044 T HR 20110044T HR P20110044 T HRP20110044 T HR P20110044T HR P20110044 T2 HRP20110044 T2 HR P20110044T2
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- Prior art keywords
- alkyl
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- methyl
- substituted
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- 230000002401 inhibitory effect Effects 0.000 title claims 3
- 108010074860 Factor Xa Proteins 0.000 title claims 2
- 230000002785 anti-thrombosis Effects 0.000 title 1
- 239000003146 anticoagulant agent Substances 0.000 title 1
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims abstract 60
- -1 C1-5-alkyloxy Chemical group 0.000 claims abstract 50
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract 37
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract 24
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract 24
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 24
- 125000005842 heteroatom Chemical group 0.000 claims abstract 23
- 229910052799 carbon Inorganic materials 0.000 claims abstract 21
- 229910052731 fluorine Inorganic materials 0.000 claims abstract 21
- 229910052801 chlorine Inorganic materials 0.000 claims abstract 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 19
- 239000011737 fluorine Substances 0.000 claims abstract 17
- 239000000460 chlorine Substances 0.000 claims abstract 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 15
- 150000001875 compounds Chemical class 0.000 claims abstract 14
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 13
- 125000004434 sulfur atom Chemical group 0.000 claims abstract 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract 12
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims abstract 12
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 claims abstract 12
- 125000001424 substituent group Chemical group 0.000 claims abstract 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims abstract 9
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims abstract 8
- 125000006560 (C1-C5)alkylcarbonylamino group Chemical group 0.000 claims abstract 7
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract 6
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims abstract 6
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims abstract 5
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract 5
- 125000001841 imino group Chemical group [H]N=* 0.000 claims abstract 5
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims abstract 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract 5
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 4
- 125000001174 sulfone group Chemical group 0.000 claims abstract 4
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims abstract 4
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims abstract 3
- YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 claims abstract 3
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims abstract 3
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims abstract 3
- HTFFABIIOAKIBH-UHFFFAOYSA-N diazinane Chemical compound C1CCNNC1 HTFFABIIOAKIBH-UHFFFAOYSA-N 0.000 claims abstract 3
- 150000003462 sulfoxides Chemical class 0.000 claims abstract 3
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 claims abstract 3
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims abstract 2
- OYELEBBISJGNHJ-UHFFFAOYSA-N 1,3-oxazinan-2-one Chemical group O=C1NCCCO1 OYELEBBISJGNHJ-UHFFFAOYSA-N 0.000 claims abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000003566 oxetanyl group Chemical group 0.000 claims abstract 2
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 28
- 125000004432 carbon atom Chemical group C* 0.000 claims 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 22
- 229910052760 oxygen Inorganic materials 0.000 claims 22
- 229910052757 nitrogen Inorganic materials 0.000 claims 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 19
- 239000001301 oxygen Substances 0.000 claims 17
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 15
- 150000003839 salts Chemical class 0.000 claims 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 14
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 13
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 13
- 125000001072 heteroaryl group Chemical group 0.000 claims 11
- 229910052794 bromium Inorganic materials 0.000 claims 10
- 125000004122 cyclic group Chemical group 0.000 claims 10
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 9
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 9
- 239000000203 mixture Substances 0.000 claims 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 239000011593 sulfur Chemical group 0.000 claims 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 5
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 5
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 5
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 229910019142 PO4 Inorganic materials 0.000 claims 5
- 150000001450 anions Chemical class 0.000 claims 5
- 229940050390 benzoate Drugs 0.000 claims 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 5
- 229940001468 citrate Drugs 0.000 claims 5
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 5
- 150000002825 nitriles Chemical class 0.000 claims 5
- 239000010452 phosphate Substances 0.000 claims 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 5
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 claims 5
- 229960001860 salicylate Drugs 0.000 claims 5
- 229940086735 succinate Drugs 0.000 claims 5
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims 5
- 229940095064 tartrate Drugs 0.000 claims 5
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 4
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 4
- 125000002950 monocyclic group Chemical group 0.000 claims 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000003277 amino group Chemical group 0.000 claims 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 229910052740 iodine Inorganic materials 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 3
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 2
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims 2
- 125000006562 (C1-C5) alkyloxycarbonylamino group Chemical group 0.000 claims 2
- NQPJDJVGBDHCAD-UHFFFAOYSA-N 1,3-diazinan-2-one Chemical compound OC1=NCCCN1 NQPJDJVGBDHCAD-UHFFFAOYSA-N 0.000 claims 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims 2
- MJYFVDNMTKLGTH-UHFFFAOYSA-N 4-bromo-6-(3,4-dichlorophenyl)sulfanyl-1-[[4-(dimethylcarbamoyl)phenyl]methyl]indole-2-carboxylic acid Chemical group BrC1=C2C=C(N(C2=CC(=C1)SC1=CC(=C(C=C1)Cl)Cl)CC1=CC=C(C=C1)C(N(C)C)=O)C(=O)O MJYFVDNMTKLGTH-UHFFFAOYSA-N 0.000 claims 2
- QZLSBOVWPHXCLT-UHFFFAOYSA-N 5-chlorothiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(Cl)S1 QZLSBOVWPHXCLT-UHFFFAOYSA-N 0.000 claims 2
- 125000006164 6-membered heteroaryl group Chemical group 0.000 claims 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 2
- 125000006845 C1-5-alkyloxycarbonyl-C1-5-alkyl group Chemical group 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 claims 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 2
- 239000012634 fragment Substances 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000001041 indolyl group Chemical group 0.000 claims 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- LZOZLBFZGFLFBV-UHFFFAOYSA-N sulfene Chemical compound C=S(=O)=O LZOZLBFZGFLFBV-UHFFFAOYSA-N 0.000 claims 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 2
- 150000003457 sulfones Chemical class 0.000 claims 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- XSROQCDVUIHRSI-UHFFFAOYSA-N thietane Chemical compound C1CSC1 XSROQCDVUIHRSI-UHFFFAOYSA-N 0.000 claims 2
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 2
- QQQFINBDFQCCOH-MRXNPFEDSA-N (2r)-2-[(5-chlorothiophene-2-carbonyl)amino]-n-(3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)pentanediamide Chemical compound N([C@H](CCC(N)=O)C(=O)NC1=CC=C2CCN(CCC2=C1)C)C(=O)C1=CC=C(Cl)S1 QQQFINBDFQCCOH-MRXNPFEDSA-N 0.000 claims 1
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims 1
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims 1
- UYYMNSZVKFZMOQ-UHFFFAOYSA-N 2-[(5-chlorothiophene-2-carbonyl)amino]-n',n',2-trimethyl-n-(3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)pentanediamide Chemical compound C=1C=C2CCN(C)CCC2=CC=1NC(=O)C(C)(CCC(=O)N(C)C)NC(=O)C1=CC=C(Cl)S1 UYYMNSZVKFZMOQ-UHFFFAOYSA-N 0.000 claims 1
- 125000004011 3 membered carbocyclic group Chemical group 0.000 claims 1
- YHRFCYISKLEPGY-UHFFFAOYSA-N 3-[(5-bromothiophene-2-carbonyl)amino]-n-(3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)oxolane-3-carboxamide Chemical compound C1=C2CCN(C)CCC2=CC=C1NC(=O)C1(NC(=O)C=2SC(Br)=CC=2)CCOC1 YHRFCYISKLEPGY-UHFFFAOYSA-N 0.000 claims 1
- UQKNTIBWQPBQBG-UHFFFAOYSA-N 3-[(5-chlorothiophene-2-carbonyl)amino]-n-(3,5-dimethyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)oxolane-3-carboxamide Chemical compound C1=C2C(C)CN(C)CCC2=CC=C1NC(=O)C1(NC(=O)C=2SC(Cl)=CC=2)CCOC1 UQKNTIBWQPBQBG-UHFFFAOYSA-N 0.000 claims 1
- PWSABEGPJIZOOJ-UHFFFAOYSA-N 3-[(5-chlorothiophene-2-carbonyl)amino]-n-(3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)oxolane-3-carboxamide Chemical compound C1=C2CCN(C)CCC2=CC=C1NC(=O)C1(NC(=O)C=2SC(Cl)=CC=2)CCOC1 PWSABEGPJIZOOJ-UHFFFAOYSA-N 0.000 claims 1
- 125000001845 4 membered carbocyclic group Chemical group 0.000 claims 1
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims 1
- GUQKDDUEGDDDMS-UHFFFAOYSA-N 5-bromo-n-[1-[(3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)carbamoyl]cyclopent-3-en-1-yl]thiophene-2-carboxamide Chemical compound C1=C2CCN(C)CCC2=CC=C1NC(=O)C1(NC(=O)C=2SC(Br)=CC=2)CC=CC1 GUQKDDUEGDDDMS-UHFFFAOYSA-N 0.000 claims 1
- PIANXTCDSYQSBJ-UHFFFAOYSA-N 5-bromo-n-[1-[(3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)carbamoyl]cyclopentyl]thiophene-2-carboxamide Chemical compound C1=C2CCN(C)CCC2=CC=C1NC(=O)C1(NC(=O)C=2SC(Br)=CC=2)CCCC1 PIANXTCDSYQSBJ-UHFFFAOYSA-N 0.000 claims 1
- SOENFIOVHBENKE-UHFFFAOYSA-N 5-bromo-n-[2-methyl-1-[(3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)amino]-1-oxopropan-2-yl]thiophene-2-carboxamide Chemical compound C1=C2CCN(C)CCC2=CC=C1NC(=O)C(C)(C)NC(=O)C1=CC=C(Br)S1 SOENFIOVHBENKE-UHFFFAOYSA-N 0.000 claims 1
- AOLZAARSPDGAAJ-UHFFFAOYSA-N 5-bromo-n-[4-hydroxy-2-methyl-1-[(3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)amino]-1-oxobutan-2-yl]thiophene-2-carboxamide Chemical compound C1=C2CCN(C)CCC2=CC=C1NC(=O)C(C)(CCO)NC(=O)C1=CC=C(Br)S1 AOLZAARSPDGAAJ-UHFFFAOYSA-N 0.000 claims 1
- DQRAVYGMSIBUPH-JOCHJYFZSA-N 5-chloro-n-[(2r)-1-[(3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)amino]-1-oxo-3-phenylmethoxypropan-2-yl]thiophene-2-carboxamide Chemical compound C([C@H](C(=O)NC1=CC=C2CCN(CCC2=C1)C)NC(=O)C=1SC(Cl)=CC=1)OCC1=CC=CC=C1 DQRAVYGMSIBUPH-JOCHJYFZSA-N 0.000 claims 1
- SRNMNAAITRBPTO-OAQYLSRUSA-N 5-chloro-n-[(2r)-1-[(3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)amino]-1-oxo-3-phenylpropan-2-yl]thiophene-2-carboxamide Chemical compound C([C@H](C(=O)NC1=CC=C2CCN(CCC2=C1)C)NC(=O)C=1SC(Cl)=CC=1)C1=CC=CC=C1 SRNMNAAITRBPTO-OAQYLSRUSA-N 0.000 claims 1
- AAZSZWJDGMPJGD-HSZRJFAPSA-N 5-chloro-n-[(2r)-1-[(3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)amino]-1-oxo-4-phenylmethoxybutan-2-yl]thiophene-2-carboxamide Chemical compound C([C@H](C(=O)NC1=CC=C2CCN(CCC2=C1)C)NC(=O)C=1SC(Cl)=CC=1)COCC1=CC=CC=C1 AAZSZWJDGMPJGD-HSZRJFAPSA-N 0.000 claims 1
- SLFVOWFFTVXJJW-OAQYLSRUSA-N 5-chloro-n-[(2r)-3-(4-hydroxyphenyl)-1-[(3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)amino]-1-oxopropan-2-yl]thiophene-2-carboxamide Chemical compound C([C@H](C(=O)NC1=CC=C2CCN(CCC2=C1)C)NC(=O)C=1SC(Cl)=CC=1)C1=CC=C(O)C=C1 SLFVOWFFTVXJJW-OAQYLSRUSA-N 0.000 claims 1
- OXTVNTVYFDLONJ-OAQYLSRUSA-N 5-chloro-n-[(2r)-3-cyclohexyl-1-[(3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)amino]-1-oxopropan-2-yl]thiophene-2-carboxamide Chemical compound C([C@H](C(=O)NC1=CC=C2CCN(CCC2=C1)C)NC(=O)C=1SC(Cl)=CC=1)C1CCCCC1 OXTVNTVYFDLONJ-OAQYLSRUSA-N 0.000 claims 1
- ZWZAOQAZNRKYHO-HXUWFJFHSA-N 5-chloro-n-[(2r)-3-hydroxy-2-methyl-1-[(3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)amino]-1-oxopropan-2-yl]thiophene-2-carboxamide Chemical compound N([C@](C)(CO)C(=O)NC1=CC=C2CCN(CCC2=C1)C)C(=O)C1=CC=C(Cl)S1 ZWZAOQAZNRKYHO-HXUWFJFHSA-N 0.000 claims 1
- WMGKBMCSLINNTJ-UHFFFAOYSA-N 5-chloro-n-[1-(1-methylpyrazol-3-yl)-2-[(3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)amino]-2-oxoethyl]thiophene-2-carboxamide Chemical compound C1=C2CCN(C)CCC2=CC=C1NC(=O)C(C1=NN(C)C=C1)NC(=O)C1=CC=C(Cl)S1 WMGKBMCSLINNTJ-UHFFFAOYSA-N 0.000 claims 1
- PAHIXXGMCRKLFQ-UHFFFAOYSA-N 5-chloro-n-[1-[(3,5-dimethyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)amino]-2-methyl-1-oxopropan-2-yl]thiophene-2-carboxamide Chemical compound C1=C2C(C)CN(C)CCC2=CC=C1NC(=O)C(C)(C)NC(=O)C1=CC=C(Cl)S1 PAHIXXGMCRKLFQ-UHFFFAOYSA-N 0.000 claims 1
- OFJNLQKHFGHJLS-UHFFFAOYSA-N 5-chloro-n-[1-[(3-ethyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)amino]-2-methyl-1-oxopropan-2-yl]thiophene-2-carboxamide Chemical compound C1=C2CCN(CC)CCC2=CC=C1NC(=O)C(C)(C)NC(=O)C1=CC=C(Cl)S1 OFJNLQKHFGHJLS-UHFFFAOYSA-N 0.000 claims 1
- JYSNPALTYZYRCG-UHFFFAOYSA-N 5-chloro-n-[1-[(3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)amino]-1-oxo-3-propan-2-yloxypropan-2-yl]thiophene-2-carboxamide Chemical compound C=1C=C2CCN(C)CCC2=CC=1NC(=O)C(COC(C)C)NC(=O)C1=CC=C(Cl)S1 JYSNPALTYZYRCG-UHFFFAOYSA-N 0.000 claims 1
- WTLOAGCHIJGEII-UHFFFAOYSA-N 5-chloro-n-[1-[(3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)carbamoyl]cyclobutyl]thiophene-2-carboxamide Chemical compound C1=C2CCN(C)CCC2=CC=C1NC(=O)C1(NC(=O)C=2SC(Cl)=CC=2)CCC1 WTLOAGCHIJGEII-UHFFFAOYSA-N 0.000 claims 1
- DHVSCIPCMUZSJF-UHFFFAOYSA-N 5-chloro-n-[1-[(3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)carbamoyl]cyclohexyl]thiophene-2-carboxamide Chemical compound C1=C2CCN(C)CCC2=CC=C1NC(=O)C1(NC(=O)C=2SC(Cl)=CC=2)CCCCC1 DHVSCIPCMUZSJF-UHFFFAOYSA-N 0.000 claims 1
- QUPORHUUBPXMGT-UHFFFAOYSA-N 5-chloro-n-[1-[(3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)carbamoyl]cyclopentyl]thiophene-2-carboxamide Chemical compound C1=C2CCN(C)CCC2=CC=C1NC(=O)C1(NC(=O)C=2SC(Cl)=CC=2)CCCC1 QUPORHUUBPXMGT-UHFFFAOYSA-N 0.000 claims 1
- DDCVNQUQOYBDMZ-UHFFFAOYSA-N 5-chloro-n-[2-methyl-1-[(3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)amino]-1-oxo-3-phenylmethoxypropan-2-yl]thiophene-2-carboxamide Chemical compound C1=C2CCN(C)CCC2=CC=C1NC(=O)C(C)(NC(=O)C=1SC(Cl)=CC=1)COCC1=CC=CC=C1 DDCVNQUQOYBDMZ-UHFFFAOYSA-N 0.000 claims 1
- ZUXFJJYXPHTZLC-UHFFFAOYSA-N 5-chloro-n-[2-methyl-1-[(3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)amino]-1-oxopropan-2-yl]thiophene-2-carboxamide Chemical compound C1=C2CCN(C)CCC2=CC=C1NC(=O)C(C)(C)NC(=O)C1=CC=C(Cl)S1 ZUXFJJYXPHTZLC-UHFFFAOYSA-N 0.000 claims 1
- AUKFRIHKUXBARC-UHFFFAOYSA-N 5-chloro-n-[3,4-dimethoxy-1-[(3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)carbamoyl]cyclopentyl]thiophene-2-carboxamide Chemical compound C1C(OC)C(OC)CC1(C(=O)NC=1C=C2CCN(C)CCC2=CC=1)NC(=O)C1=CC=C(Cl)S1 AUKFRIHKUXBARC-UHFFFAOYSA-N 0.000 claims 1
- RGXQEBKAOVRQEU-UHFFFAOYSA-N 5-chloro-n-[3-(4-hydroxy-3-nitrophenyl)-1-[(3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)amino]-1-oxopropan-2-yl]thiophene-2-carboxamide Chemical compound C1=C2CCN(C)CCC2=CC=C1NC(=O)C(NC(=O)C=1SC(Cl)=CC=1)CC1=CC=C(O)C([N+]([O-])=O)=C1 RGXQEBKAOVRQEU-UHFFFAOYSA-N 0.000 claims 1
- OORLYDNDMDKZPJ-UHFFFAOYSA-N 5-chloro-n-[3-(4-hydroxyphenyl)-2-methyl-1-[(3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)amino]-1-oxopropan-2-yl]thiophene-2-carboxamide Chemical compound C1=C2CCN(C)CCC2=CC=C1NC(=O)C(C)(NC(=O)C=1SC(Cl)=CC=1)CC1=CC=C(O)C=C1 OORLYDNDMDKZPJ-UHFFFAOYSA-N 0.000 claims 1
- UVZULTZGKRNIRY-UHFFFAOYSA-N 5-chloro-n-[3-[(3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)carbamoyl]thiolan-3-yl]thiophene-2-carboxamide Chemical compound C1=C2CCN(C)CCC2=CC=C1NC(=O)C1(NC(=O)C=2SC(Cl)=CC=2)CCSC1 UVZULTZGKRNIRY-UHFFFAOYSA-N 0.000 claims 1
- RNUCQRKEDRWJGP-UHFFFAOYSA-N 5-chloro-n-[3-ethoxy-1-[(3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)amino]-1-oxopropan-2-yl]thiophene-2-carboxamide Chemical compound C=1C=C2CCN(C)CCC2=CC=1NC(=O)C(COCC)NC(=O)C1=CC=C(Cl)S1 RNUCQRKEDRWJGP-UHFFFAOYSA-N 0.000 claims 1
- BPOFITJOVOYEAY-UHFFFAOYSA-N 5-chloro-n-[3-methoxy-1-[(3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)amino]-1-oxopropan-2-yl]thiophene-2-carboxamide Chemical compound C=1C=C2CCN(C)CCC2=CC=1NC(=O)C(COC)NC(=O)C1=CC=C(Cl)S1 BPOFITJOVOYEAY-UHFFFAOYSA-N 0.000 claims 1
- ZYXHMDXLRXPUKO-UHFFFAOYSA-N 5-chloro-n-[4-methoxy-1-[(3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)amino]-1-oxobutan-2-yl]thiophene-2-carboxamide Chemical compound C=1C=C2CCN(C)CCC2=CC=1NC(=O)C(CCOC)NC(=O)C1=CC=C(Cl)S1 ZYXHMDXLRXPUKO-UHFFFAOYSA-N 0.000 claims 1
- HUXBTNRAOCKBGU-UHFFFAOYSA-N 5-ethynyl-n-[2-methyl-1-[(3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)amino]-1-oxopropan-2-yl]thiophene-2-carboxamide Chemical compound C1=C2CCN(C)CCC2=CC=C1NC(=O)C(C)(C)NC(=O)C1=CC=C(C#C)S1 HUXBTNRAOCKBGU-UHFFFAOYSA-N 0.000 claims 1
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 1
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims 1
- 125000001960 7 membered carbocyclic group Chemical group 0.000 claims 1
- 108010022999 Serine Proteases Proteins 0.000 claims 1
- 102000012479 Serine Proteases Human genes 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 238000001311 chemical methods and process Methods 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims 1
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- HTCYVYLCNDZLLU-QGZVFWFLSA-N n-[(2r)-3-acetamido-1-[(3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)amino]-1-oxopropan-2-yl]-5-chlorothiophene-2-carboxamide Chemical compound N([C@H](CNC(C)=O)C(=O)NC1=CC=C2CCN(CCC2=C1)C)C(=O)C1=CC=C(Cl)S1 HTCYVYLCNDZLLU-QGZVFWFLSA-N 0.000 claims 1
- ZLPJCTYKOZEMRS-OAQYLSRUSA-N n-[(2r)-3-benzamido-1-[(3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-yl)amino]-1-oxopropan-2-yl]-5-bromothiophene-2-carboxamide Chemical compound C([C@H](C(=O)NC1=CC=C2CCN(CCC2=C1)C)NC(=O)C=1SC(Br)=CC=1)NC(=O)C1=CC=CC=C1 ZLPJCTYKOZEMRS-OAQYLSRUSA-N 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 239000000758 substrate Substances 0.000 claims 1
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
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- 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
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—Bridged systems
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP05014270 | 2005-06-30 | ||
| PCT/EP2006/063611 WO2007003536A1 (de) | 2005-06-30 | 2006-06-28 | Substituierte glycinamide mit antithrombotischer und faktor xa-inhibierender wirkung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HRP20110044T1 HRP20110044T1 (en) | 2011-02-28 |
| HRP20110044T2 true HRP20110044T2 (hr) | 2012-02-29 |
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| HR20110044T HRP20110044T2 (hr) | 2005-06-30 | 2011-01-21 | Supstituirani glicinamidi s antitrombotičkim i faktor-xa inhibirajućim djelovanjem |
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| EP (1) | EP1899330B9 (ru) |
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| BR (1) | BRPI0612580A8 (ru) |
| CA (1) | CA2613059C (ru) |
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| EC (1) | ECSP078058A (ru) |
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| MX (1) | MX2007016253A (ru) |
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| NZ (1) | NZ565440A (ru) |
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| WO2006041773A2 (en) | 2004-10-04 | 2006-04-20 | Millennium Pharmaceuticals, Inc. | Lactam compounds useful as protein kinase inhibitors |
| PE20080145A1 (es) | 2006-03-21 | 2008-02-11 | Janssen Pharmaceutica Nv | Tetrahidro-pirimidoazepinas como moduladores de trpv1 |
| US20090312306A1 (en) * | 2006-07-20 | 2009-12-17 | Guangri Sun | Tetrahydro-5h-pyrido[2,3-d]azepines as 5-ht2c ligands |
| PE20081834A1 (es) * | 2006-12-31 | 2009-01-16 | Boehringer Ingelheim Int | Proceso para la sintesis de derivados de acido 3-amino-tetrahidrofuran-3-carboxilico y uso de los mismos como medicamentos |
| EP1975165A1 (de) | 2007-03-27 | 2008-10-01 | Boehringer Ingelheim Pharma GmbH & Co. KG | Substituierte Pyrrolidinamide, deren Herstellung und deren Verwendung als Arzneimittel |
| EP2220079A2 (en) * | 2007-11-15 | 2010-08-25 | Boehringer Ingelheim International GmbH | Substituted amides, manufacturing and use thereof as medicaments |
| PE20091102A1 (es) | 2007-12-17 | 2009-07-25 | Janssen Pharmaceutica Nv | Moduladores imidazolo-, oxazolo-, y tiazolopirimidina del trpv1 |
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| JP2012517997A (ja) * | 2009-02-17 | 2012-08-09 | Ｍｓｄ株式会社 | １，４−ベンゾジアゼピン−２−オン誘導体 |
| EP2552479A4 (en) | 2010-03-30 | 2015-03-04 | Sinai School Medicine | INFLUENZA VIRUS VACCINES AND USES THEREOF |
| JP6498439B2 (ja) | 2011-09-20 | 2019-04-17 | アイカーン スクール オブ メディシン アット マウント サイナイ | インフルエンザウイルスワクチン及びその使用 |
| MX2015007755A (es) | 2012-12-18 | 2016-01-14 | Icahn School Med Mount Sinai | Vacunas contra virus de la influenza y sus usos. |
| CN108892661B (zh) * | 2014-02-07 | 2023-03-14 | 艾克赛特赫拉制药有限责任公司 | 治疗化合物和组合物 |
| CN105622511B (zh) * | 2014-11-03 | 2018-01-23 | 北京瑞都医药科技有限公司 | 一种减肥药物及其制备方法 |
| EP3078378B1 (en) | 2015-04-08 | 2020-06-24 | Vaiomer | Use of factor xa inhibitors for regulating glycemia |
| CR20200640A (es) | 2018-07-05 | 2021-02-15 | Bayer Ag | Substituted thiophenecarboxamides and analogues as antibacterials agents |
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| ATE303988T1 (de) | 1999-06-14 | 2005-09-15 | Lilly Co Eli | Inhibitoren von serin proteasen |
| DE19962924A1 (de) * | 1999-12-24 | 2001-07-05 | Bayer Ag | Substituierte Oxazolidinone und ihre Verwendung |
| EP1307203A4 (en) | 2000-03-21 | 2005-08-17 | Smithkline Beecham Corp | PROTEINASE INHIBITOR |
| DE10063008A1 (de) | 2000-12-16 | 2002-06-20 | Merck Patent Gmbh | Carbonsäureamidderivate |
| US20040157828A1 (en) | 2001-05-17 | 2004-08-12 | Ren Xie | Protease inhibitors |
| JP2004300133A (ja) * | 2002-11-19 | 2004-10-28 | Takeda Chem Ind Ltd | アミン誘導体 |
| PE20040837A1 (es) | 2002-11-19 | 2004-12-24 | Takeda Chemical Industries Ltd | Compuestos de amina |
| DE10254336A1 (de) | 2002-11-21 | 2004-06-03 | Merck Patent Gmbh | Carbonsäureamide |
| US7250415B2 (en) | 2003-06-04 | 2007-07-31 | Bristol-Myers Squibb Company | 1,1-Disubstitutedcycloalkyl-, glycinamidyl-, sulfonyl-amidino-, and tetrahydropyrimidinyl-containing diaminoalkyl, β-aminoacids, α-aminoacids and derivatives thereof as factor Xa inhibitors |
| JP2007537181A (ja) * | 2004-05-13 | 2007-12-20 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 置換されたチオフェン−カルボン酸アミド、医薬品の形態におけるこれらの製造及び使用 |
| WO2005111013A1 (de) | 2004-05-13 | 2005-11-24 | Boehringer Ingelheim International Gmbh | Substituierte thiophen-2-carbonsäureamide, deren herstellung und deren verwendung als arzneimittel |
| WO2005111029A1 (de) | 2004-05-13 | 2005-11-24 | Boehringer Ingelheim International Gmbh | Neue substituierte thiophencarbonsäureamide, deren herstellung und deren verwendung als arzneimittel |
| DE102004047840A1 (de) * | 2004-09-29 | 2006-03-30 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue substituierte Thiophencarbonsäureamide, deren Herstellung und deren Verwendung als Arzneimittel |
| PE20081834A1 (es) | 2006-12-31 | 2009-01-16 | Boehringer Ingelheim Int | Proceso para la sintesis de derivados de acido 3-amino-tetrahidrofuran-3-carboxilico y uso de los mismos como medicamentos |
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