CA2505389C - Xanthine derivatives, the preparation thereof and their use as pharmaceutical compositions - Google Patents
Xanthine derivatives, the preparation thereof and their use as pharmaceutical compositions Download PDFInfo
- Publication number
- CA2505389C CA2505389C CA2505389A CA2505389A CA2505389C CA 2505389 C CA2505389 C CA 2505389C CA 2505389 A CA2505389 A CA 2505389A CA 2505389 A CA2505389 A CA 2505389A CA 2505389 C CA2505389 C CA 2505389C
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- CA
- Canada
- Prior art keywords
- group
- alkyl
- methyl
- amino
- benzo
- 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.)
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- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title description 16
- 229940083747 low-ceiling diuretics xanthine derivative Drugs 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims abstract description 44
- 150000003839 salts Chemical class 0.000 claims abstract description 32
- 229940002612 prodrug Drugs 0.000 claims abstract description 5
- 239000000651 prodrug Substances 0.000 claims abstract description 5
- -1 1,4-dihydro-quinazolinyl Chemical group 0.000 claims description 684
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 137
- 150000001875 compounds Chemical class 0.000 claims description 66
- 125000005605 benzo group Chemical group 0.000 claims description 48
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 37
- 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 37
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 36
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 28
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
- 229910052731 fluorine Inorganic materials 0.000 claims description 24
- 239000011737 fluorine Substances 0.000 claims description 24
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 24
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 24
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 23
- 239000000460 chlorine Substances 0.000 claims description 23
- 229910052801 chlorine Inorganic materials 0.000 claims description 23
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 22
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 claims description 21
- 229910052794 bromium Inorganic materials 0.000 claims description 17
- 125000006239 protecting group Chemical group 0.000 claims description 17
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 15
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 15
- 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
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 229910052740 iodine Inorganic materials 0.000 claims description 14
- 125000003277 amino group Chemical group 0.000 claims description 13
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
- 125000003282 alkyl amino group Chemical group 0.000 claims description 11
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 9
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 8
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 8
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 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 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- XSEAMCPQTZGEOJ-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-but-2-ynyl-1-(1,4-dihydroquinazolin-2-ylmethyl)-3-methylpurine-2,6-dione Chemical compound N=1C=2N(C)C(=O)N(CC=3NCC4=CC=CC=C4N=3)C(=O)C=2N(CC#CC)C=1N1CCCC(N)C1 XSEAMCPQTZGEOJ-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 6
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000005308 thiazepinyl group Chemical group S1N=C(C=CC=C1)* 0.000 claims description 5
- ZFJAEKNTWCKVJQ-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-1-(2,1,3-benzoxadiazol-5-ylmethyl)-7-but-2-ynyl-3-methylpurine-2,6-dione Chemical compound N=1C=2N(C)C(=O)N(CC3=CC4=NON=C4C=C3)C(=O)C=2N(CC#CC)C=1N1CCCC(N)C1 ZFJAEKNTWCKVJQ-UHFFFAOYSA-N 0.000 claims description 4
- YDWBSAMIOHUVDL-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-1-(benzo[c][1,8]naphthyridin-6-ylmethyl)-7-but-2-ynyl-3-methylpurine-2,6-dione Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC=C4C4=CC=CN=C4N=3)C(=O)C=2N(CC#CC)C=1N1CCCC(N)C1 YDWBSAMIOHUVDL-UHFFFAOYSA-N 0.000 claims description 4
- OQCYQTBTYPXVRI-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-1-(benzo[h][1,6]naphthyridin-5-ylmethyl)-7-but-2-ynyl-3-methylpurine-2,6-dione Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CN=C4C4=CC=CC=C4N=3)C(=O)C=2N(CC#CC)C=1N1CCCC(N)C1 OQCYQTBTYPXVRI-UHFFFAOYSA-N 0.000 claims description 4
- IIFWKNLPZOLJAK-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-but-2-ynyl-3-cyclopropyl-1-(phenanthridin-6-ylmethyl)purine-2,6-dione Chemical compound O=C1N(CC=2C3=CC=CC=C3C3=CC=CC=C3N=2)C(=O)C=2N(CC#CC)C(N3CC(N)CCC3)=NC=2N1C1CC1 IIFWKNLPZOLJAK-UHFFFAOYSA-N 0.000 claims description 4
- FOFYBZQYNQXNIE-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-but-2-ynyl-3-methyl-1-(1,2,3,4-tetrahydrophenanthridin-6-ylmethyl)purine-2,6-dione Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC=C4C=4CCCCC=4N=3)C(=O)C=2N(CC#CC)C=1N1CCCC(N)C1 FOFYBZQYNQXNIE-UHFFFAOYSA-N 0.000 claims description 4
- LJNCRERRKMEOMA-GOSISDBHSA-N 8-[(3r)-3-aminopiperidin-1-yl]-7-but-2-ynyl-3-methyl-1-(1h-perimidin-2-ylmethyl)purine-2,6-dione Chemical compound N=1C=2N(C)C(=O)N(CC=3NC=4C=CC=C5C=CC=C(C=45)N=3)C(=O)C=2N(CC#CC)C=1N1CCC[C@@H](N)C1 LJNCRERRKMEOMA-GOSISDBHSA-N 0.000 claims description 4
- HRIOVHDWMBVNRH-HXUWFJFHSA-N 8-[(3r)-3-aminopiperidin-1-yl]-7-but-2-ynyl-3-methyl-1-[(1-methylphenanthridin-6-yl)methyl]purine-2,6-dione Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC=C4C4=C(C)C=CC=C4N=3)C(=O)C=2N(CC#CC)C=1N1CCC[C@@H](N)C1 HRIOVHDWMBVNRH-HXUWFJFHSA-N 0.000 claims description 4
- RMBKAIRBRJOIJF-HXUWFJFHSA-N 8-[(3r)-3-aminopiperidin-1-yl]-7-but-2-ynyl-3-methyl-1-[(4-methylphenanthridin-6-yl)methyl]purine-2,6-dione Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC=C4C4=CC=CC(C)=C4N=3)C(=O)C=2N(CC#CC)C=1N1CCC[C@@H](N)C1 RMBKAIRBRJOIJF-HXUWFJFHSA-N 0.000 claims description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 4
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 4
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 4
- 125000004429 atom 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
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 150000001721 carbon Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 235000005985 organic acids Nutrition 0.000 claims description 4
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 4
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- XYYQUFIYMPYZQO-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-3-methyl-7-(3-methylbut-2-enyl)-1-[(3-oxoisoindol-1-ylidene)methyl]purine-2,6-dione Chemical compound N=1C=2N(C)C(=O)N(C=C3C4=CC=CC=C4C(=O)N3)C(=O)C=2N(CC=C(C)C)C=1N1CCCC(N)C1 XYYQUFIYMPYZQO-UHFFFAOYSA-N 0.000 claims description 3
- UJCXAPHOXHYFDJ-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-but-2-ynyl-1-(imidazo[2,1-a]isoquinolin-2-ylmethyl)-3-methylpurine-2,6-dione Chemical compound N=1C=2N(C)C(=O)N(CC=3N=C4C5=CC=CC=C5C=CN4C=3)C(=O)C=2N(CC#CC)C=1N1CCCC(N)C1 UJCXAPHOXHYFDJ-UHFFFAOYSA-N 0.000 claims description 3
- KOYKKFVARVTVBE-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-but-2-ynyl-3-methyl-1-(phenanthridin-6-ylmethyl)purine-2,6-dione Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC=C4C4=CC=CC=C4N=3)C(=O)C=2N(CC#CC)C=1N1CCCC(N)C1 KOYKKFVARVTVBE-UHFFFAOYSA-N 0.000 claims description 3
- YYCUOVCCKCVCIQ-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-but-2-ynyl-3-methyl-1-[(11-methylbenzo[b][1,4]benzodiazepin-6-yl)methyl]purine-2,6-dione Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC=C4N(C)C4=CC=CC=C4N=3)C(=O)C=2N(CC#CC)C=1N1CCCC(N)C1 YYCUOVCCKCVCIQ-UHFFFAOYSA-N 0.000 claims description 3
- AJGLBCXPISVKSC-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-but-2-ynyl-3-methyl-1-[(8-methylphenanthridin-6-yl)methyl]purine-2,6-dione Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC(C)=CC=C4C4=CC=CC=C4N=3)C(=O)C=2N(CC#CC)C=1N1CCCC(N)C1 AJGLBCXPISVKSC-UHFFFAOYSA-N 0.000 claims description 3
- OQQXXYWFEIGADR-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-but-2-ynyl-3-methyl-1-[[3-(trifluoromethyl)-3,4-dihydroisoquinolin-1-yl]methyl]purine-2,6-dione Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC=C4CC(N=3)C(F)(F)F)C(=O)C=2N(CC#CC)C=1N1CCCC(N)C1 OQQXXYWFEIGADR-UHFFFAOYSA-N 0.000 claims description 3
- WAYVDLYVFNWYST-QDLOVBKTSA-N 8-[(3R)-3-aminopiperidin-1-yl]-7-[(E)-but-2-enyl]-3-methyl-1-[(2-oxo-1,3-dihydro-1,4-benzodiazepin-5-yl)methyl]purine-2,6-dione Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC=C4NC(=O)CN=3)C(=O)C=2N(C/C=C/C)C=1N1CCC[C@@H](N)C1 WAYVDLYVFNWYST-QDLOVBKTSA-N 0.000 claims description 3
- IIFWKNLPZOLJAK-HXUWFJFHSA-N 8-[(3r)-3-aminopiperidin-1-yl]-7-but-2-ynyl-3-cyclopropyl-1-(phenanthridin-6-ylmethyl)purine-2,6-dione Chemical compound O=C1N(CC=2C3=CC=CC=C3C3=CC=CC=C3N=2)C(=O)C=2N(CC#CC)C(N3C[C@H](N)CCC3)=NC=2N1C1CC1 IIFWKNLPZOLJAK-HXUWFJFHSA-N 0.000 claims description 3
- KOYKKFVARVTVBE-LJQANCHMSA-N 8-[(3r)-3-aminopiperidin-1-yl]-7-but-2-ynyl-3-methyl-1-(phenanthridin-6-ylmethyl)purine-2,6-dione Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC=C4C4=CC=CC=C4N=3)C(=O)C=2N(CC#CC)C=1N1CCC[C@@H](N)C1 KOYKKFVARVTVBE-LJQANCHMSA-N 0.000 claims description 3
- KOYKKFVARVTVBE-IBGZPJMESA-N 8-[(3s)-3-aminopiperidin-1-yl]-7-but-2-ynyl-3-methyl-1-(phenanthridin-6-ylmethyl)purine-2,6-dione Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC=C4C4=CC=CC=C4N=3)C(=O)C=2N(CC#CC)C=1N1CCC[C@H](N)C1 KOYKKFVARVTVBE-IBGZPJMESA-N 0.000 claims description 3
- 208000008589 Obesity Diseases 0.000 claims description 3
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 3
- 235000020824 obesity Nutrition 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 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
- LVDPOWHAVPDMHP-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-1-(11h-benzo[c][1]benzazepin-6-ylmethyl)-7-but-2-ynyl-3-methylpurine-2,6-dione Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC=C4CC4=CC=CC=C4N=3)C(=O)C=2N(CC#CC)C=1N1CCCC(N)C1 LVDPOWHAVPDMHP-UHFFFAOYSA-N 0.000 claims description 2
- JIZNYPIAZNKEPY-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-3-methyl-7-(3-methylbut-2-enyl)-1-[(1-methyl-2,2-dioxo-2$l^{6},1-benzothiazin-4-yl)methyl]purine-2,6-dione Chemical compound C=1S(=O)(=O)N(C)C2=CC=CC=C2C=1CN(C(C=1N2CC=C(C)C)=O)C(=O)N(C)C=1N=C2N1CCCC(N)C1 JIZNYPIAZNKEPY-UHFFFAOYSA-N 0.000 claims description 2
- NPEHKMAXIRRIGE-UHFFFAOYSA-N 8-(3-aminopiperidin-1-yl)-7-but-2-ynyl-3-methyl-1-(pyrazolo[1,5-c]quinazolin-5-ylmethyl)purine-2,6-dione Chemical compound N=1C=2N(C)C(=O)N(CC=3N4N=CC=C4C4=CC=CC=C4N=3)C(=O)C=2N(CC#CC)C=1N1CCCC(N)C1 NPEHKMAXIRRIGE-UHFFFAOYSA-N 0.000 claims description 2
- AXEHMQLMYWEERM-GOSISDBHSA-N 8-[(3r)-3-aminopiperidin-1-yl]-1-(benzo[c][1,5]naphthyridin-6-ylmethyl)-7-but-2-ynyl-3-methylpurine-2,6-dione Chemical compound N=1C=2N(C)C(=O)N(CC=3C4=CC=CC=C4C4=NC=CC=C4N=3)C(=O)C=2N(CC#CC)C=1N1CCC[C@@H](N)C1 AXEHMQLMYWEERM-GOSISDBHSA-N 0.000 claims description 2
- 102000055006 Calcitonin Human genes 0.000 claims description 2
- 108060001064 Calcitonin Proteins 0.000 claims description 2
- 208000001132 Osteoporosis Diseases 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 206010003246 arthritis Diseases 0.000 claims description 2
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- 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
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- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Diabetes (AREA)
- Physical Education & Sports Medicine (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Transplantation (AREA)
- Emergency Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10251927A DE10251927A1 (de) | 2002-11-08 | 2002-11-08 | Neue Xanthinderivate, deren Herstellung und deren Verwendung als Arzneimittel |
| DE10251927.7 | 2002-11-08 | ||
| PCT/EP2003/012198 WO2004041820A1 (de) | 2002-11-08 | 2003-11-03 | Neue xanthinderivate, deren herstellung und deren verwendung als arzneimittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2505389A1 CA2505389A1 (en) | 2004-05-21 |
| CA2505389C true CA2505389C (en) | 2012-01-10 |
Family
ID=32115363
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2505389A Expired - Fee Related CA2505389C (en) | 2002-11-08 | 2003-11-03 | Xanthine derivatives, the preparation thereof and their use as pharmaceutical compositions |
Country Status (16)
| Country | Link |
|---|---|
| EP (2) | EP2228375A1 (https=) |
| JP (2) | JP4832758B2 (https=) |
| AR (1) | AR043060A1 (https=) |
| AT (1) | ATE469152T1 (https=) |
| AU (1) | AU2003293649A1 (https=) |
| CA (1) | CA2505389C (https=) |
| CY (1) | CY1110749T1 (https=) |
| DE (2) | DE10251927A1 (https=) |
| DK (1) | DK1562946T5 (https=) |
| ES (1) | ES2346432T3 (https=) |
| PE (1) | PE20040829A1 (https=) |
| PT (1) | PT1562946E (https=) |
| SI (1) | SI1562946T1 (https=) |
| TW (1) | TW200512210A (https=) |
| UY (1) | UY28069A1 (https=) |
| WO (1) | WO2004041820A1 (https=) |
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| US7569574B2 (en) | 2002-08-22 | 2009-08-04 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Purine derivatives, the preparation thereof and their use as pharmaceutical compositions |
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| US7351719B2 (en) | 2002-10-31 | 2008-04-01 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Amide compounds having MCH-antagonistic activity and medicaments comprising these compounds |
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| US7482337B2 (en) | 2002-11-08 | 2009-01-27 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Xanthine derivatives, 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 |
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| EP1368349B1 (de) * | 2001-02-24 | 2007-02-14 | Boehringer Ingelheim Pharma GmbH & Co.KG | Xanthinderivate, deren herstellung und deren verwendung als arzneimittel |
| AU2002331311A1 (en) * | 2001-09-19 | 2003-04-01 | Novo Nordisk A/S | Heterocyclic compounds that are inhibitors of the enzyme dpp-iv |
| ES2339112T3 (es) * | 2002-08-21 | 2010-05-17 | BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG | 8-(3-amino-piperidin-1-il)-xantinas,su preparacion y su uso como medicamentos. |
| DE10251927A1 (de) * | 2002-11-08 | 2004-05-19 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Xanthinderivate, deren Herstellung und deren Verwendung als Arzneimittel |
-
2002
- 2002-11-08 DE DE10251927A patent/DE10251927A1/de not_active Withdrawn
-
2003
- 2003-11-03 EP EP10158963A patent/EP2228375A1/de not_active Withdrawn
- 2003-11-03 ES ES03788995T patent/ES2346432T3/es not_active Expired - Lifetime
- 2003-11-03 PT PT03788995T patent/PT1562946E/pt unknown
- 2003-11-03 AT AT03788995T patent/ATE469152T1/de active
- 2003-11-03 CA CA2505389A patent/CA2505389C/en not_active Expired - Fee Related
- 2003-11-03 DK DK03788995.3T patent/DK1562946T5/da active
- 2003-11-03 EP EP03788995A patent/EP1562946B1/de not_active Expired - Lifetime
- 2003-11-03 AU AU2003293649A patent/AU2003293649A1/en not_active Abandoned
- 2003-11-03 JP JP2004548847A patent/JP4832758B2/ja not_active Expired - Fee Related
- 2003-11-03 WO PCT/EP2003/012198 patent/WO2004041820A1/de not_active Ceased
- 2003-11-03 DE DE50312747T patent/DE50312747D1/de not_active Expired - Lifetime
- 2003-11-03 SI SI200331855T patent/SI1562946T1/sl unknown
- 2003-11-06 PE PE2003001124A patent/PE20040829A1/es not_active Application Discontinuation
- 2003-11-07 AR ARP030104097A patent/AR043060A1/es unknown
- 2003-11-07 TW TW092131252A patent/TW200512210A/zh unknown
- 2003-11-07 UY UY28069A patent/UY28069A1/es not_active Application Discontinuation
-
2010
- 2010-08-20 CY CY20101100774T patent/CY1110749T1/el unknown
- 2010-10-19 JP JP2010234795A patent/JP2011012085A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| DK1562946T5 (da) | 2011-02-07 |
| DE10251927A1 (de) | 2004-05-19 |
| EP1562946B1 (de) | 2010-05-26 |
| PT1562946E (pt) | 2010-08-24 |
| TW200512210A (en) | 2005-04-01 |
| WO2004041820A1 (de) | 2004-05-21 |
| ATE469152T1 (de) | 2010-06-15 |
| AR043060A1 (es) | 2005-07-13 |
| EP1562946A1 (de) | 2005-08-17 |
| EP2228375A1 (de) | 2010-09-15 |
| UY28069A1 (es) | 2004-06-30 |
| CY1110749T1 (el) | 2015-06-10 |
| ES2346432T3 (es) | 2010-10-15 |
| JP2006512311A (ja) | 2006-04-13 |
| AU2003293649A1 (en) | 2004-06-07 |
| JP2011012085A (ja) | 2011-01-20 |
| DE50312747D1 (de) | 2010-07-08 |
| PE20040829A1 (es) | 2005-01-14 |
| SI1562946T1 (sl) | 2010-11-30 |
| DK1562946T3 (da) | 2010-09-20 |
| CA2505389A1 (en) | 2004-05-21 |
| JP4832758B2 (ja) | 2011-12-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20131105 |