ES2308017T3 - Nuevos derivados de purina, su produccion, y su uso como medicamentos. - Google Patents
Nuevos derivados de purina, su produccion, y su uso como medicamentos. Download PDFInfo
- Publication number
- ES2308017T3 ES2308017T3 ES03792343T ES03792343T ES2308017T3 ES 2308017 T3 ES2308017 T3 ES 2308017T3 ES 03792343 T ES03792343 T ES 03792343T ES 03792343 T ES03792343 T ES 03792343T ES 2308017 T3 ES2308017 T3 ES 2308017T3
- Authority
- ES
- Spain
- Prior art keywords
- group
- alkyl
- amino
- piperidin
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 25
- 239000003814 drug Substances 0.000 title claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 94
- 239000000203 mixture Substances 0.000 claims abstract description 38
- 150000003839 salts Chemical class 0.000 claims abstract description 31
- 229940002612 prodrug Drugs 0.000 claims abstract description 7
- 239000000651 prodrug Substances 0.000 claims abstract description 7
- 229940083251 peripheral vasodilators purine derivative Drugs 0.000 claims abstract description 6
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 4
- 125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 claims abstract description 4
- -1 pyrrolidin-1-ylcarbonyl Chemical group 0.000 claims description 469
- 125000000217 alkyl group Chemical group 0.000 claims description 205
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 72
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 71
- 239000002253 acid Substances 0.000 claims description 63
- 125000003277 amino group Chemical group 0.000 claims description 50
- 125000003545 alkoxy group Chemical group 0.000 claims description 47
- 125000003282 alkyl amino group Chemical group 0.000 claims description 47
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 44
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 42
- 125000003342 alkenyl group Chemical group 0.000 claims description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
- 125000001624 naphthyl group Chemical group 0.000 claims description 28
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 28
- 125000004429 atom Chemical group 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 22
- 229910052731 fluorine Inorganic materials 0.000 claims description 22
- 229910052801 chlorine Inorganic materials 0.000 claims description 21
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 20
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 20
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 20
- 239000000460 chlorine Substances 0.000 claims description 19
- 239000000126 substance Substances 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 239000011737 fluorine Substances 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 17
- 125000000304 alkynyl group Chemical group 0.000 claims description 17
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 16
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 16
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 14
- 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 description 14
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 14
- 229910052794 bromium Inorganic materials 0.000 claims description 14
- 125000002541 furyl group Chemical group 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 14
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 125000001544 thienyl group Chemical group 0.000 claims description 12
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000001153 fluoro group Chemical group F* 0.000 claims description 11
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 229910052740 iodine Inorganic materials 0.000 claims description 9
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
- 125000006563 (C1-3) alkylaminocarbonyl group Chemical group 0.000 claims description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 8
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 8
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 8
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 7
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 7
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 6
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 6
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 6
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 125000006576 di-(C1-C3-alkyl)-aminocarbonyl group Chemical group 0.000 claims description 6
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000001326 naphthylalkyl group Chemical group 0.000 claims description 6
- 150000003212 purines Chemical class 0.000 claims description 6
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 5
- 150000001721 carbon Chemical group 0.000 claims description 5
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 5
- 229940079593 drug Drugs 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 4
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 4
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 4
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- FDGQSTZJBFJUBT-UHFFFAOYSA-N hypoxanthine Chemical group O=C1NC=NC2=C1NC=N2 FDGQSTZJBFJUBT-UHFFFAOYSA-N 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- AHRPGBIQGOKCEJ-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-1-[(4-methoxynaphthalen-1-yl)methyl]-7-(3-methylbut-2-enyl)purin-6-one Chemical compound C12=CC=CC=C2C(OC)=CC=C1CN(C(C=1N2CC=C(C)C)=O)C=NC=1N=C2N1CCCC(N)C1 AHRPGBIQGOKCEJ-UHFFFAOYSA-N 0.000 claims description 3
- RNRPZHYVLILOGM-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-2-methyl-7-(3-methylbut-2-enyl)-1-(naphthalen-1-ylmethyl)purin-6-one Chemical compound N=1C=2N=C(C)N(CC=3C4=CC=CC=C4C=CC=3)C(=O)C=2N(CC=C(C)C)C=1N1CCCC(N)C1 RNRPZHYVLILOGM-UHFFFAOYSA-N 0.000 claims description 3
- PNOSIUFCRSQTOB-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-(3-methylbut-2-enyl)-1-(naphthalen-1-ylmethyl)purin-6-one Chemical compound N=1C=2N=CN(CC=3C4=CC=CC=C4C=CC=3)C(=O)C=2N(CC=C(C)C)C=1N1CCCC(N)C1 PNOSIUFCRSQTOB-UHFFFAOYSA-N 0.000 claims description 3
- KYDFKPMXUILEAA-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-benzyl-1-phenacylpurin-6-one Chemical compound C1C(N)CCCN1C(N1CC=2C=CC=CC=2)=NC2=C1C(=O)N(CC(=O)C=1C=CC=CC=1)C=N2 KYDFKPMXUILEAA-UHFFFAOYSA-N 0.000 claims description 3
- KXEVVOQPEOZACT-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-benzyl-2-(benzylamino)-1-methylpurin-6-one Chemical compound N=1C=2N=C(N3CC(N)CCC3)N(CC=3C=CC=CC=3)C=2C(=O)N(C)C=1NCC1=CC=CC=C1 KXEVVOQPEOZACT-UHFFFAOYSA-N 0.000 claims description 3
- 208000008589 Obesity Diseases 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
- 235000020824 obesity Nutrition 0.000 claims description 3
- 125000006595 (C1-C3) alkylsulfinyl group Chemical group 0.000 claims description 2
- 125000006594 (C1-C3) alkylsulfony group Chemical group 0.000 claims description 2
- 125000006602 (C1-C3) alkylsulfonylamino group Chemical group 0.000 claims description 2
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 2
- MLEOPWDMSPGAJV-UHFFFAOYSA-N 2-amino-8-(3-aminopiperidin-1-yl)-7-benzyl-1-methylpurin-6-one Chemical compound C=1C=CC=CC=1CN1C=2C(=O)N(C)C(N)=NC=2N=C1N1CCCC(N)C1 MLEOPWDMSPGAJV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- LNUIDEMUMXLMOV-UHFFFAOYSA-N 7-[(4-fluorophenyl)methyl]-8-(piperidin-4-ylmethyl)-3h-purin-6-one Chemical compound C=1C=C(F)C=CC=1CN1C=2C(O)=NC=NC=2N=C1CC1CCNCC1 LNUIDEMUMXLMOV-UHFFFAOYSA-N 0.000 claims description 2
- VEJJMWUFHYIMLI-UHFFFAOYSA-N 7-[(4-fluorophenyl)methyl]-8-[(1-methylpiperidin-4-yl)methyl]-3h-purin-6-one Chemical compound C1CN(C)CCC1CC(N1CC=2C=CC(F)=CC=2)=NC2=C1C(=O)NC=N2 VEJJMWUFHYIMLI-UHFFFAOYSA-N 0.000 claims description 2
- KXZCVZCPENDTBZ-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-1-methyl-7-(3-methylbut-2-enyl)-2-(2-phenylethyl)purin-6-one Chemical compound CN1C(=O)C=2N(CC=C(C)C)C(N3CC(N)CCC3)=NC=2N=C1CCC1=CC=CC=C1 KXZCVZCPENDTBZ-UHFFFAOYSA-N 0.000 claims description 2
- IHELHBZSOOCKJI-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-benzyl-1,2-dimethylpurin-6-one Chemical compound C=1C=CC=CC=1CN1C=2C(=O)N(C)C(C)=NC=2N=C1N1CCCC(N)C1 IHELHBZSOOCKJI-UHFFFAOYSA-N 0.000 claims description 2
- VLBIYRJVPOZOET-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-benzyl-1-methyl-2-(2-phenylethylamino)purin-6-one Chemical compound N=1C=2N=C(N3CC(N)CCC3)N(CC=3C=CC=CC=3)C=2C(=O)N(C)C=1NCCC1=CC=CC=C1 VLBIYRJVPOZOET-UHFFFAOYSA-N 0.000 claims description 2
- FWURZHRNHYFNNY-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-benzyl-1-methyl-2-(methylamino)purin-6-one Chemical compound C=1C=CC=CC=1CN1C=2C(=O)N(C)C(NC)=NC=2N=C1N1CCCC(N)C1 FWURZHRNHYFNNY-UHFFFAOYSA-N 0.000 claims description 2
- LIQQAKDINRZTHI-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-benzyl-1-methyl-2-piperidin-1-ylpurin-6-one Chemical compound C=1C=CC=CC=1CN1C=2C(=O)N(C)C(N3CCCCC3)=NC=2N=C1N1CCCC(N)C1 LIQQAKDINRZTHI-UHFFFAOYSA-N 0.000 claims description 2
- KHCNZQNITHNYGN-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-benzyl-1-methylpurin-6-one Chemical compound C=1C=CC=CC=1CN1C=2C(=O)N(C)C=NC=2N=C1N1CCCC(N)C1 KHCNZQNITHNYGN-UHFFFAOYSA-N 0.000 claims description 2
- JRQQCSZVFBUCTP-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-benzyl-2-(cyclohexylmethylamino)-1-methylpurin-6-one Chemical compound N=1C=2N=C(N3CC(N)CCC3)N(CC=3C=CC=CC=3)C=2C(=O)N(C)C=1NCC1CCCCC1 JRQQCSZVFBUCTP-UHFFFAOYSA-N 0.000 claims description 2
- MUJRWAFVKMBLQJ-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-benzyl-2-(dimethylamino)-1-methylpurin-6-one Chemical compound C=1C=CC=CC=1CN1C=2C(=O)N(C)C(N(C)C)=NC=2N=C1N1CCCC(N)C1 MUJRWAFVKMBLQJ-UHFFFAOYSA-N 0.000 claims description 2
- WRFSHVCQKQZCJT-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-benzyl-2-[(4-fluorophenyl)methylamino]-1-methylpurin-6-one Chemical compound N=1C=2N=C(N3CC(N)CCC3)N(CC=3C=CC=CC=3)C=2C(=O)N(C)C=1NCC1=CC=C(F)C=C1 WRFSHVCQKQZCJT-UHFFFAOYSA-N 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 208000001132 Osteoporosis Diseases 0.000 claims description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- 125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 claims description 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 2
- 125000005055 alkyl alkoxy group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000005277 alkyl imino group Chemical group 0.000 claims description 2
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
- 125000002431 aminoalkoxy group Chemical group 0.000 claims description 2
- 125000005122 aminoalkylamino group Chemical group 0.000 claims description 2
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- 206010003246 arthritis Diseases 0.000 claims description 2
- 125000004273 azetidin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 2
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 2
- 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 125000004981 cycloalkylmethyl group Chemical group 0.000 claims description 2
- 125000005171 cycloalkylsulfanyl group Chemical group 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 2
- 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
- 238000002483 medication Methods 0.000 claims description 2
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 2
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 claims description 2
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 125000000464 thioxo group Chemical group S=* 0.000 claims description 2
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- RBMHFWWPPNCWDN-UHFFFAOYSA-N 7-[(4-fluorophenyl)methyl]-8-(piperidin-4-ylamino)-3h-purin-6-one Chemical compound C=1C=C(F)C=CC=1CN1C=2C(O)=NC=NC=2N=C1NC1CCNCC1 RBMHFWWPPNCWDN-UHFFFAOYSA-N 0.000 claims 1
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- AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 description 1
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- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
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- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000018 receptor agonist Substances 0.000 description 1
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- UNAANXDKBXWMLN-UHFFFAOYSA-N sibutramine Chemical compound C=1C=C(Cl)C=CC=1C1(C(N(C)C)CC(C)C)CCC1 UNAANXDKBXWMLN-UHFFFAOYSA-N 0.000 description 1
- 229960004425 sibutramine Drugs 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
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- RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 230000019100 sperm motility Effects 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
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- 230000000638 stimulation Effects 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- KRRBFUJMQBDDPR-UHFFFAOYSA-N tetrabutylazanium;cyanide Chemical compound N#[C-].CCCC[N+](CCCC)(CCCC)CCCC KRRBFUJMQBDDPR-UHFFFAOYSA-N 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 description 1
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- 206010043778 thyroiditis Diseases 0.000 description 1
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- 231100000331 toxic Toxicity 0.000 description 1
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/28—Oxygen atom
- C07D473/30—Oxygen atom attached in position 6, e.g. hypoxanthine
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Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Medicinal Chemistry (AREA)
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- Diabetes (AREA)
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- Immunology (AREA)
- Rheumatology (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Psychiatry (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Endocrinology (AREA)
- Pain & Pain Management (AREA)
- Virology (AREA)
- Urology & Nephrology (AREA)
- Reproductive Health (AREA)
- Obesity (AREA)
- Communicable Diseases (AREA)
- Hospice & Palliative Care (AREA)
- Pulmonology (AREA)
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- Cardiology (AREA)
- Emergency Medicine (AREA)
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10238477A DE10238477A1 (de) | 2002-08-22 | 2002-08-22 | Neue Purinderivate, deren Herstellung und deren Verwendung als Arzneimittel |
| DE10238477 | 2002-08-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2308017T3 true ES2308017T3 (es) | 2008-12-01 |
Family
ID=31197237
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES03792343T Expired - Lifetime ES2308017T3 (es) | 2002-08-22 | 2003-08-16 | Nuevos derivados de purina, su produccion, y su uso como medicamentos. |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP1532150B1 (https=) |
| JP (1) | JP2006502144A (https=) |
| AT (1) | ATE398128T1 (https=) |
| AU (1) | AU2003258621A1 (https=) |
| CA (1) | CA2496211A1 (https=) |
| DE (2) | DE10238477A1 (https=) |
| ES (1) | ES2308017T3 (https=) |
| WO (1) | WO2004018469A1 (https=) |
Families Citing this family (85)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7407955B2 (en) | 2002-08-21 | 2008-08-05 | Boehringer Ingelheim Pharma Gmbh & Co., Kg | 8-[3-amino-piperidin-1-yl]-xanthines, the preparation thereof and their use as pharmaceutical compositions |
| DE10254304A1 (de) * | 2002-11-21 | 2004-06-03 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Xanthinderivate, deren Herstellung und deren Verwendung als Arzneimittel |
| CA2518465A1 (en) * | 2003-03-25 | 2004-10-14 | Takeda San Diego, Inc. | Dipeptidyl peptidase inhibitors |
| JPWO2004096806A1 (ja) * | 2003-04-30 | 2006-07-13 | 大日本住友製薬株式会社 | 縮合イミダゾール誘導体 |
| WO2004098591A2 (en) | 2003-05-05 | 2004-11-18 | Probiodrug Ag | Inhibitors of glutaminyl cyclase and their use in the treatment of neurological diseases |
| JP2007511467A (ja) | 2003-05-14 | 2007-05-10 | タケダ サン ディエゴ インコーポレイテッド | ジペプチジルペプチダーゼインヒビター |
| KR20060041309A (ko) | 2003-08-13 | 2006-05-11 | 다케다 야쿠힌 고교 가부시키가이샤 | ４-피리미돈 유도체 및 펩티딜 펩티다제 저해제로서의 그의용도 |
| DE10348022A1 (de) * | 2003-10-15 | 2005-05-25 | Imtm Gmbh | Neue Dipeptidylpeptidase IV-Inhibitoren zur funktionellen Beeinflussung unterschiedlicher Zellen und zur Behandlung immunologischer, entzündlicher, neuronaler und anderer Erkrankungen |
| US7501426B2 (en) | 2004-02-18 | 2009-03-10 | Boehringer Ingelheim International Gmbh | 8-[3-amino-piperidin-1-yl]-xanthines, their preparation and their use as pharmaceutical compositions |
| DE102004030502A1 (de) | 2004-06-24 | 2006-01-12 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Imidazole und Triazole, deren Herstellung und Verwendung als Arzneimittel |
| JP4797021B2 (ja) * | 2004-10-01 | 2011-10-19 | メルク・シャープ・エンド・ドーム・コーポレイション | 糖尿病の治療または予防用のジペプチジルペプチダ−ゼ−ｉｖ阻害剤としてのアミノピペリジン |
| DE102004054054A1 (de) | 2004-11-05 | 2006-05-11 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Verfahren zur Herstellung chiraler 8-(3-Amino-piperidin-1-yl)-xanthine |
| AU2005309606B2 (en) * | 2004-11-29 | 2011-01-06 | Merck Sharp & Dohme Corp. | Fused aminopiperidines as dipeptidyl peptidase-IV inhibitors for the treatment or prevention of diabetes |
| 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 |
| JP5075125B2 (ja) * | 2005-08-26 | 2012-11-14 | メルク・シャープ・エンド・ドーム・コーポレイション | 糖尿病の治療又は予防用ジペプチジルペプチダーゼｉｖ阻害剤としての縮合アミノピペリジン |
| MY147393A (en) | 2005-09-14 | 2012-11-30 | Takeda Pharmaceutical | Administration of dipeptidyl peptidase inhibitors |
| CA2622642C (en) | 2005-09-16 | 2013-12-31 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| CA2631737C (en) * | 2005-12-14 | 2013-03-26 | Merck & Co., Inc. | Fused aminopiperidines as dipeptidyl peptidase-4 inhibitors for the treatment or prevention of diabetes |
| GB0526291D0 (en) | 2005-12-23 | 2006-02-01 | Prosidion Ltd | Therapeutic method |
| WO2007112347A1 (en) | 2006-03-28 | 2007-10-04 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| US7833730B2 (en) | 2006-04-11 | 2010-11-16 | Arena Pharmaceuticals, Inc. | Methods of using GPR119 to identify compounds useful for increasing bone mass in an individual |
| 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 |
| EP2540725A1 (de) | 2006-05-04 | 2013-01-02 | Boehringer Ingelheim International GmbH | Polymorphe von 1-((4-Methyl-chinazolin-2-yl)methyl)-3-methyl-7-(2-butin-1-yl)-8-(3-(R)-amino-piperidin-1-yl)xanthin |
| EP1852108A1 (en) | 2006-05-04 | 2007-11-07 | Boehringer Ingelheim Pharma GmbH & Co.KG | DPP IV inhibitor formulations |
| PE20080251A1 (es) | 2006-05-04 | 2008-04-25 | Boehringer Ingelheim Int | Usos de inhibidores de dpp iv |
| US8278345B2 (en) | 2006-11-09 | 2012-10-02 | Probiodrug Ag | Inhibitors of glutaminyl cyclase |
| 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 |
| ATE554085T1 (de) | 2006-11-30 | 2012-05-15 | Probiodrug Ag | Neue inhibitoren von glutaminylcyclase |
| EP2142514B1 (en) | 2007-04-18 | 2014-12-24 | Probiodrug AG | Thiourea derivatives as glutaminyl cyclase inhibitors |
| CL2008002427A1 (es) | 2007-08-16 | 2009-09-11 | Boehringer Ingelheim Int | Composicion farmaceutica que comprende 1-cloro-4-(b-d-glucopiranos-1-il)-2-[4-((s)-tetrahidrofurano-3-iloxi)bencil]-benceno combinado con 1-[(4-metilquinazolin-2-il)metil]-3-metil-7-(2-butin-1-il)-8-(3-(r)-aminopiperidin-1-il)xantina; y su uso para tratar diabetes mellitus tipo 2. |
| PE20091730A1 (es) | 2008-04-03 | 2009-12-10 | Boehringer Ingelheim Int | Formulaciones que comprenden un inhibidor de dpp4 |
| EP2108960A1 (en) | 2008-04-07 | 2009-10-14 | Arena Pharmaceuticals, Inc. | Methods of using A G protein-coupled receptor to identify peptide YY (PYY) secretagogues and compounds useful in the treatment of conditons modulated by PYY |
| CA2724715A1 (en) | 2008-05-22 | 2009-11-26 | Amgen Inc. | Heterocycles as protein kinase inhibitors |
| UY32030A (es) | 2008-08-06 | 2010-03-26 | Boehringer Ingelheim Int | "tratamiento para diabetes en pacientes inapropiados para terapia con metformina" |
| BRPI0916997A2 (pt) | 2008-08-06 | 2020-12-15 | Boehringer Ingelheim International Gmbh | Inibidor de dpp-4 e seu uso |
| NZ604091A (en) | 2008-08-15 | 2014-08-29 | Boehringer Ingelheim Int | Purin derivatives for use in the treatment of fab-related diseases |
| US20200155558A1 (en) | 2018-11-20 | 2020-05-21 | Boehringer Ingelheim International Gmbh | Treatment for diabetes in patients with insufficient glycemic control despite therapy with an oral antidiabetic drug |
| CN102256976A (zh) | 2008-12-23 | 2011-11-23 | 贝林格尔.英格海姆国际有限公司 | 有机化合物的盐形式 |
| AR074990A1 (es) | 2009-01-07 | 2011-03-02 | Boehringer Ingelheim Int | Tratamiento de diabetes en pacientes con un control glucemico inadecuado a pesar de la terapia con metformina |
| AR075204A1 (es) | 2009-01-29 | 2011-03-16 | Boehringer Ingelheim Int | Inhibidores de dpp-4 y composiciones farmaceuticas que los comprenden, utiles para tratar enfermedades metabolicas en pacientes pediatricos, particularmente diabetes mellitus tipo 2 |
| AU2010212823B2 (en) | 2009-02-13 | 2016-01-28 | Boehringer Ingelheim International Gmbh | Antidiabetic medications comprising a DPP-4 inhibitor (linagliptin) optionally in combination with other antidiabetics |
| JP5685550B2 (ja) | 2009-02-13 | 2015-03-18 | 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 | Ｓｇｌｔ２阻害剤、ｄｐｐ−ｉｖ阻害剤、更に必要により抗糖尿病薬を含む医薬組成物及びその使用 |
| AR077642A1 (es) | 2009-07-09 | 2011-09-14 | Arena Pharm Inc | Moduladores del metabolismo y el tratamiento de trastornos relacionados con el mismo |
| JP5934645B2 (ja) | 2009-09-11 | 2016-06-15 | プロビオドルグ エージー | グルタミニルシクラーゼ阻害剤としてのヘテロ環式誘導体 |
| NZ598170A (en) | 2009-10-02 | 2014-06-27 | Boehringer Ingelheim Int | Pharmaceutical compositions comprising bi-1356 and metformin |
| EP2499142B1 (en) * | 2009-11-09 | 2016-09-21 | Advinus Therapeutics Limited | Substituted fused pyrimidine compounds, its preparation and uses thereof |
| KR20240090632A (ko) | 2009-11-27 | 2024-06-21 | 베링거 인겔하임 인터내셔날 게엠베하 | 리나글립틴과 같은 ｄｐｐ－ｉｖ 억제제를 사용한 유전자형 검사된 당뇨병 환자의 치료 |
| JP6026284B2 (ja) | 2010-03-03 | 2016-11-16 | プロビオドルグ エージー | グルタミニルシクラーゼの阻害剤 |
| NZ602312A (en) | 2010-03-10 | 2014-02-28 | Probiodrug Ag | Heterocyclic inhibitors of glutaminyl cyclase (qc, ec 2.3.2.5) |
| EP2547339A1 (en) | 2010-03-18 | 2013-01-23 | Boehringer Ingelheim International GmbH | Combination of a gpr119 agonist and the dpp-iv inhibitor linagliptin for use in the treatment of diabetes and related conditions |
| CA2795513A1 (en) | 2010-04-06 | 2011-10-13 | Arena Pharmaceuticals, Inc. | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
| WO2011131748A2 (en) | 2010-04-21 | 2011-10-27 | Probiodrug Ag | Novel inhibitors |
| AR082091A1 (es) | 2010-05-05 | 2012-11-14 | Boehringer Ingelheim Int | Composiciones farmaceuticas que comprenden pioglitazona y linagliptina y procedimiento de preparacion |
| CN102946875A (zh) | 2010-05-05 | 2013-02-27 | 贝林格尔.英格海姆国际有限公司 | 组合疗法 |
| WO2011161161A1 (en) | 2010-06-24 | 2011-12-29 | Boehringer Ingelheim International Gmbh | Diabetes therapy |
| EP3323818A1 (en) | 2010-09-22 | 2018-05-23 | Arena Pharmaceuticals, Inc. | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
| AR083878A1 (es) | 2010-11-15 | 2013-03-27 | Boehringer Ingelheim Int | Terapia antidiabetica vasoprotectora y cardioprotectora, linagliptina, metodo de tratamiento |
| EP2686313B1 (en) | 2011-03-16 | 2016-02-03 | Probiodrug AG | Benzimidazole derivatives as inhibitors of glutaminyl cyclase |
| US20140018371A1 (en) | 2011-04-01 | 2014-01-16 | Arena Pharmaceuticals, Inc. | Modulators Of The GPR119 Receptor And The Treatment Of Disorders Related Thereto |
| WO2012145361A1 (en) | 2011-04-19 | 2012-10-26 | 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 |
| EP2729468A4 (en) * | 2011-07-05 | 2015-03-18 | Merck Sharp & Dohme | Tricyclic heterocycles useful as dipeptidyl peptidase-iv inhibitors |
| US8883800B2 (en) | 2011-07-15 | 2014-11-11 | Boehringer Ingelheim International Gmbh | Substituted quinazolines, the preparation thereof and the use thereof in pharmaceutical compositions |
| WO2013055910A1 (en) | 2011-10-12 | 2013-04-18 | Arena Pharmaceuticals, Inc. | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
| CN103130819B (zh) * | 2011-12-01 | 2016-01-20 | 中国科学院上海药物研究所 | 噻吩[3,2-d]并嘧啶-4-酮类化合物、其制备方法、药物组合物及用途 |
| US20130172244A1 (en) | 2011-12-29 | 2013-07-04 | Thomas Klein | Subcutaneous therapeutic use of dpp-4 inhibitor |
| US9555001B2 (en) | 2012-03-07 | 2017-01-31 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition and uses thereof |
| JP6218811B2 (ja) | 2012-05-14 | 2017-10-25 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｓｉｒｓ及び／又は敗血症の治療に用いるｄｐｐ−４阻害薬としてのキサンチン誘導体 |
| JP6224084B2 (ja) | 2012-05-14 | 2017-11-01 | 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 | 糸球体上皮細胞関連障害及び／又はネフローゼ症候群の治療に用いるｄｐｐ−４阻害薬としてのキサンチン誘導体 |
| JP6374862B2 (ja) | 2012-05-24 | 2018-08-15 | 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 | 自己免疫性糖尿病、特に、ｌａｄａの治療に使用するためのｄｐｐ−４阻害剤としてのキサンチン誘導体 |
| WO2013174767A1 (en) | 2012-05-24 | 2013-11-28 | Boehringer Ingelheim International Gmbh | A xanthine derivative as dpp -4 inhibitor for use in modifying food intake and regulating food preference |
| US20150246117A1 (en) | 2012-09-24 | 2015-09-03 | Ulf Eriksson | Treatment of type 2 diabetes and related conditions |
| WO2014074668A1 (en) | 2012-11-08 | 2014-05-15 | Arena Pharmaceuticals, Inc. | Modulators of gpr119 and the treatment of disorders related thereto |
| EP3744327A1 (en) | 2013-03-15 | 2020-12-02 | Boehringer Ingelheim International GmbH | Use of linagliptin in cardio- and renoprotective antidiabetic therapy |
| EP3110449B1 (en) | 2014-02-28 | 2023-06-28 | Boehringer Ingelheim International GmbH | Medical use of a dpp-4 inhibitor |
| EA201791982A1 (ru) | 2015-03-09 | 2020-02-17 | Интекрин Терапьютикс, Инк. | Способы лечения неалкогольной жировой болезни печени и/или липодистрофии |
| CN109310697A (zh) | 2016-06-10 | 2019-02-05 | 勃林格殷格翰国际有限公司 | 利格列汀和二甲双胍的组合 |
| US11285180B2 (en) | 2016-12-06 | 2022-03-29 | Inserm (Institut National De La Sante Et De La Recherche Medicale) | Methods of enhancing the potency of incretin-based drugs in subjects in need thereof |
| JP2020515639A (ja) | 2017-04-03 | 2020-05-28 | コヒラス・バイオサイエンシズ・インコーポレイテッド | 進行性核上性麻痺の処置のためのＰＰＡＲγアゴニスト |
| ES2812698T3 (es) | 2017-09-29 | 2021-03-18 | Probiodrug Ag | Inhibidores de glutaminil ciclasa |
| RU2020133727A (ru) * | 2018-03-21 | 2022-04-21 | Сучжоу Пухе Биофарма Ко., Лтд. | Ингибиторы shp2 и их применение |
| EP4608388A1 (en) | 2022-10-25 | 2025-09-03 | Starrock Pharma Inc. | Combinatorial, and rotational combinatorial therapies for obesity and other diseases |
| WO2025227129A2 (en) | 2024-04-25 | 2025-10-30 | Starrock Pharma Llc | Delivery vehicles comprising proglucagon derived polypeptides and anabolic polypeptides and uses thereof |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8515934D0 (en) * | 1985-06-24 | 1985-07-24 | Janssen Pharmaceutica Nv | (4-piperidinomethyl and-hetero)purines |
| AU1688599A (en) * | 1998-01-05 | 1999-07-26 | Eisai Co. Ltd. | Purine derivatives and adenosine a2 receptor antagonists serving as preventives/remedies for diabetes |
| AU2001268958B2 (en) * | 2000-07-04 | 2006-03-09 | Novo Nordisk A/S | Heterocyclic compounds, which are inhibitors of the enzyme dpp-iv |
-
2002
- 2002-08-22 DE DE10238477A patent/DE10238477A1/de not_active Withdrawn
-
2003
- 2003-08-16 AU AU2003258621A patent/AU2003258621A1/en not_active Abandoned
- 2003-08-16 DE DE50309979T patent/DE50309979D1/de not_active Expired - Lifetime
- 2003-08-16 WO PCT/EP2003/009100 patent/WO2004018469A1/de not_active Ceased
- 2003-08-16 CA CA002496211A patent/CA2496211A1/en not_active Abandoned
- 2003-08-16 AT AT03792343T patent/ATE398128T1/de active
- 2003-08-16 JP JP2004530172A patent/JP2006502144A/ja active Pending
- 2003-08-16 EP EP03792343A patent/EP1532150B1/de not_active Expired - Lifetime
- 2003-08-16 ES ES03792343T patent/ES2308017T3/es not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP1532150A1 (de) | 2005-05-25 |
| DE10238477A1 (de) | 2004-03-04 |
| EP1532150B1 (de) | 2008-06-11 |
| CA2496211A1 (en) | 2004-03-04 |
| WO2004018469A1 (de) | 2004-03-04 |
| DE50309979D1 (de) | 2008-07-24 |
| JP2006502144A (ja) | 2006-01-19 |
| ATE398128T1 (de) | 2008-07-15 |
| AU2003258621A1 (en) | 2004-03-11 |
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