CA2508233C - New substituted imidazo-pyridinones and imidazo-pyridazinones, the preparation thereof and their use as pharmaceutical compositions - Google Patents
New substituted imidazo-pyridinones and imidazo-pyridazinones, the preparation thereof and their use as pharmaceutical compositions Download PDFInfo
- Publication number
- CA2508233C CA2508233C CA2508233A CA2508233A CA2508233C CA 2508233 C CA2508233 C CA 2508233C CA 2508233 A CA2508233 A CA 2508233A CA 2508233 A CA2508233 A CA 2508233A CA 2508233 C CA2508233 C CA 2508233C
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- CA
- Canada
- Prior art keywords
- group
- amino
- dihydro
- methyl
- piperidin
- 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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- 239000008194 pharmaceutical composition Substances 0.000 title claims description 7
- JXXWJMUPNZDILL-UHFFFAOYSA-N imidazo[4,5-b]pyridin-2-one Chemical class C1=CC=NC2=NC(=O)N=C21 JXXWJMUPNZDILL-UHFFFAOYSA-N 0.000 title abstract description 4
- HCYYBBFWNWACCL-UHFFFAOYSA-N imidazo[4,5-c]pyridazin-3-one Chemical class N1=NC(=O)C=C2N=CN=C21 HCYYBBFWNWACCL-UHFFFAOYSA-N 0.000 title abstract description 4
- 238000002360 preparation method Methods 0.000 title description 14
- 239000000203 mixture Substances 0.000 claims abstract description 57
- 150000003839 salts Chemical class 0.000 claims abstract description 32
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 191
- 125000006239 protecting group Chemical group 0.000 claims description 64
- -1 pyrrolylmethyl Chemical group 0.000 claims description 55
- 150000001875 compounds Chemical class 0.000 claims description 53
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 19
- 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 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 125000002950 monocyclic group Chemical group 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 150000007522 mineralic acids Chemical class 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000006842 cycloalkyleneimino group Chemical group 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 4
- DFITYIQEMIOJGR-UHFFFAOYSA-N 2-(3-aminopiperidin-1-yl)-3-but-2-ynyl-5-(naphthalen-1-ylmethyl)imidazo[4,5-d]pyridazin-4-one Chemical compound N=1C=2C=NN(CC=3C4=CC=CC=C4C=CC=3)C(=O)C=2N(CC#CC)C=1N1CCCC(N)C1 DFITYIQEMIOJGR-UHFFFAOYSA-N 0.000 claims description 3
- VSVOOAUXPJNGGB-UHFFFAOYSA-N 2-(3-aminopiperidin-1-yl)-3-but-2-ynyl-5-(quinoxalin-6-ylmethyl)imidazo[4,5-d]pyridazin-4-one Chemical compound N=1C=2C=NN(CC=3C=C4N=CC=NC4=CC=3)C(=O)C=2N(CC#CC)C=1N1CCCC(N)C1 VSVOOAUXPJNGGB-UHFFFAOYSA-N 0.000 claims description 3
- LKONEWRPHKAEAX-OAQYLSRUSA-N 2-[(3r)-3-aminopiperidin-1-yl]-3-[(2-chlorophenyl)methyl]-5-[(3-methylisoquinolin-1-yl)methyl]imidazo[4,5-d]pyridazin-4-one Chemical compound N=1C(C)=CC2=CC=CC=C2C=1CN(C(C=1N2CC=3C(=CC=CC=3)Cl)=O)N=CC=1N=C2N1CCC[C@@H](N)C1 LKONEWRPHKAEAX-OAQYLSRUSA-N 0.000 claims description 3
- TXXFMWDTLYERIF-LJQANCHMSA-N 2-[(3r)-3-aminopiperidin-1-yl]-3-but-2-ynyl-5-[(2,3-dimethylquinoxalin-6-yl)methyl]imidazo[4,5-d]pyridazin-4-one Chemical compound N=1C=2C=NN(CC=3C=C4N=C(C)C(C)=NC4=CC=3)C(=O)C=2N(CC#CC)C=1N1CCC[C@@H](N)C1 TXXFMWDTLYERIF-LJQANCHMSA-N 0.000 claims description 3
- XEHHGZMFZJRETB-QGZVFWFLSA-N 2-[(3r)-3-aminopiperidin-1-yl]-3-but-2-ynyl-5-[(4-methylphthalazin-1-yl)methyl]imidazo[4,5-d]pyridazin-4-one Chemical compound N=1C=2C=NN(CC=3C4=CC=CC=C4C(C)=NN=3)C(=O)C=2N(CC#CC)C=1N1CCC[C@@H](N)C1 XEHHGZMFZJRETB-QGZVFWFLSA-N 0.000 claims description 3
- HAKJUVBTRWXTRU-QGZVFWFLSA-N 2-[(3r)-3-aminopiperidin-1-yl]-3-but-2-ynyl-5-[(4-methylquinazolin-2-yl)methyl]imidazo[4,5-d]pyridazin-4-one Chemical compound N=1C=2C=NN(CC=3N=C4C=CC=CC4=C(C)N=3)C(=O)C=2N(CC#CC)C=1N1CCC[C@@H](N)C1 HAKJUVBTRWXTRU-QGZVFWFLSA-N 0.000 claims description 3
- LTYFBZKPWVJWBJ-OAHLLOKOSA-N 2-[(3r)-3-aminopiperidin-1-yl]-5-(2,1,3-benzothiadiazol-5-ylmethyl)-3-but-2-ynylimidazo[4,5-d]pyridazin-4-one Chemical compound N=1C=2C=NN(CC3=CC4=NSN=C4C=C3)C(=O)C=2N(CC#CC)C=1N1CCC[C@@H](N)C1 LTYFBZKPWVJWBJ-OAHLLOKOSA-N 0.000 claims description 3
- DCAKSIWUXGMRFT-GOSISDBHSA-N 2-[(3r)-3-aminopiperidin-1-yl]-5-[(4-bromonaphthalen-1-yl)methyl]-3-but-2-ynylimidazo[4,5-d]pyridazin-4-one Chemical compound N=1C=2C=NN(CC=3C4=CC=CC=C4C(Br)=CC=3)C(=O)C=2N(CC#CC)C=1N1CCC[C@@H](N)C1 DCAKSIWUXGMRFT-GOSISDBHSA-N 0.000 claims description 3
- MUFOTJYSFCKGKD-HXUWFJFHSA-N 4-[[2-[(3r)-3-aminopiperidin-1-yl]-3-but-2-ynyl-4-oxoimidazo[4,5-d]pyridazin-5-yl]methyl]naphthalene-1-carbonitrile Chemical compound N=1C=2C=NN(CC=3C4=CC=CC=C4C(C#N)=CC=3)C(=O)C=2N(CC#CC)C=1N1CCC[C@@H](N)C1 MUFOTJYSFCKGKD-HXUWFJFHSA-N 0.000 claims description 3
- SZRYBSWHNSZXGN-LJQANCHMSA-N 6-[[2-[(3r)-3-aminopiperidin-1-yl]-3-but-2-ynyl-4-oxoimidazo[4,5-d]pyridazin-5-yl]methyl]-1-methylquinolin-2-one Chemical compound N=1C=2C=NN(CC=3C=C4C=CC(=O)N(C)C4=CC=3)C(=O)C=2N(CC#CC)C=1N1CCC[C@@H](N)C1 SZRYBSWHNSZXGN-LJQANCHMSA-N 0.000 claims description 3
- 208000008589 Obesity Diseases 0.000 claims description 3
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- 150000001412 amines Chemical class 0.000 claims description 3
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- 235000020824 obesity Nutrition 0.000 claims description 3
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- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 2
- IZISCGFIOLCUSQ-UHFFFAOYSA-N 2-(3-aminopiperidin-1-yl)-3-but-2-ynyl-5-[(3-methylisoquinolin-1-yl)methyl]imidazo[4,5-d]pyridazin-4-one Chemical compound N=1C=2C=NN(CC=3C4=CC=CC=C4C=C(C)N=3)C(=O)C=2N(CC#CC)C=1N1CCCC(N)C1 IZISCGFIOLCUSQ-UHFFFAOYSA-N 0.000 claims description 2
- KFTCLRWRFNRDIO-MRXNPFEDSA-N 2-[(3r)-3-aminopiperidin-1-yl]-3-but-2-ynyl-5-(1,5-naphthyridin-2-ylmethyl)imidazo[4,5-d]pyridazin-4-one Chemical compound N=1C=2C=NN(CC=3N=C4C=CC=NC4=CC=3)C(=O)C=2N(CC#CC)C=1N1CCC[C@@H](N)C1 KFTCLRWRFNRDIO-MRXNPFEDSA-N 0.000 claims description 2
- IXVARICGYAWRCV-HXUWFJFHSA-N 2-[(3r)-3-aminopiperidin-1-yl]-3-but-2-ynyl-5-[(2,3,8-trimethylquinoxalin-6-yl)methyl]imidazo[4,5-d]pyridazin-4-one Chemical compound N=1C=2C=NN(CC=3C=C4N=C(C)C(C)=NC4=C(C)C=3)C(=O)C=2N(CC#CC)C=1N1CCC[C@@H](N)C1 IXVARICGYAWRCV-HXUWFJFHSA-N 0.000 claims description 2
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
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- BBBFJLBPOGFECG-VJVYQDLKSA-N calcitonin Chemical compound N([C@H](C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(N)=O)C(C)C)C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1 BBBFJLBPOGFECG-VJVYQDLKSA-N 0.000 claims description 2
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- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
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Landscapes
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
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Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10256264.4 | 2002-12-03 | ||
| DE2002156264 DE10256264A1 (de) | 2002-12-03 | 2002-12-03 | Neue substituierte Imidazo-pyridinone und Imidazo-pyridazinone, ihre Herstellung und ihre Verwendung als Arzneimittel |
| DE2003109927 DE10309927A1 (de) | 2003-03-07 | 2003-03-07 | Neue substituierte Imidazo-pyridinone und Imidazo-pyridazinone, ihre Herstellung und ihre Verwendung als Arzneimittel |
| DE10309927.1 | 2003-03-07 | ||
| PCT/EP2003/013648 WO2004050658A1 (de) | 2002-12-03 | 2003-12-03 | Neue substituierte imidazo-pyridinone und imidazo-pyridazinone, ihre herstellung und ihre verwendung als arzneimittel |
Publications (2)
| Publication Number | Publication Date |
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| CA2508233A1 CA2508233A1 (en) | 2004-06-17 |
| CA2508233C true CA2508233C (en) | 2012-01-31 |
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| CA2508233A Expired - Lifetime CA2508233C (en) | 2002-12-03 | 2003-12-03 | New substituted imidazo-pyridinones and imidazo-pyridazinones, the preparation thereof and their use as pharmaceutical compositions |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP1569936B1 (enExample) |
| JP (1) | JP4726493B2 (enExample) |
| AR (1) | AR042275A1 (enExample) |
| AT (1) | ATE425979T1 (enExample) |
| AU (1) | AU2003293757A1 (enExample) |
| CA (1) | CA2508233C (enExample) |
| DE (1) | DE50311318D1 (enExample) |
| ES (1) | ES2324294T3 (enExample) |
| PE (1) | PE20040759A1 (enExample) |
| TW (1) | TW200504067A (enExample) |
| UY (1) | UY28103A1 (enExample) |
| WO (1) | WO2004050658A1 (enExample) |
Families Citing this family (141)
| Publication number | Priority date | Publication date | Assignee | Title |
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| 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 |
| US7495005B2 (en) | 2002-08-22 | 2009-02-24 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Xanthine derivatives, their preparation and their use in pharmaceutical compositions |
| 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 |
| 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 |
| US7550590B2 (en) | 2003-03-25 | 2009-06-23 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| 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 |
| AU2003902828A0 (en) * | 2003-06-05 | 2003-06-26 | Fujisawa Pharmaceutical Co., Ltd. | Dpp-iv inhibitor |
| DE10327439A1 (de) * | 2003-06-18 | 2005-01-05 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Imidazopyridazinon- und Imidazopyridonderivate, deren Herstellung und deren Verwendung als Arzneimittel |
| US7566707B2 (en) | 2003-06-18 | 2009-07-28 | Boehringer Ingelheim International Gmbh | Imidazopyridazinone and imidazopyridone derivatives, the preparation thereof and their use as pharmaceutical compositions |
| US7678909B1 (en) | 2003-08-13 | 2010-03-16 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| WO2005016911A1 (en) | 2003-08-13 | 2005-02-24 | Takeda Pharmaceutical Company Limited | 4-pyrimidone derivatives and their use as peptidyl peptidase inhibitors |
| WO2005051949A1 (ja) * | 2003-11-26 | 2005-06-09 | Dainippon Sumitomo Pharma Co., Ltd. | 新規縮合イミダゾール誘導体 |
| DE10355304A1 (de) | 2003-11-27 | 2005-06-23 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue 8-(Piperazin-1-yl)-und 8-([1,4]Diazepan-1-yl)-xanthine, deren Herstellung und deren Verwendung als Arzneimittel |
| US7217711B2 (en) | 2003-12-17 | 2007-05-15 | Boehringer Ingelheim International Gmbh | Piperazin-1-yl and 2-([1,4]diazepan-1-yl)-imidazo[4,5-d]-pyridazin-4-ones, the preparation thereof and their use as pharmaceutical compositions |
| DE10359098A1 (de) * | 2003-12-17 | 2005-07-28 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue 2-(Piperazin-1-yl)- und 2-([1,4]Diazepan-1-yl)-imidazo[4,5-d]pyridazin-4-one, deren Herstellung und deren Verwendung als Arzneimittel |
| DE10360835A1 (de) * | 2003-12-23 | 2005-07-21 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Bicyclische Imidazolverbindungen, deren Herstellung und deren Verwendung als Arzneimittel |
| 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 |
| DE102004009039A1 (de) | 2004-02-23 | 2005-09-08 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | 8-[3-Amino-piperidin-1-yl]-xanthine, deren Herstellung und Verwendung als Arzneimittel |
| US7732446B1 (en) | 2004-03-11 | 2010-06-08 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| US7393847B2 (en) | 2004-03-13 | 2008-07-01 | Boehringer Ingleheim International Gmbh | Imidazopyridazinediones, their preparation and their use as pharmaceutical compositions |
| DE102004012366A1 (de) * | 2004-03-13 | 2005-09-29 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Imidazopyridazindione, deren Herstellung und deren Verwendung als Arzneimittel |
| US7179809B2 (en) | 2004-04-10 | 2007-02-20 | Boehringer Ingelheim International Gmbh | 2-Amino-imidazo[4,5-d]pyridazin-4-ones, their preparation and their use as pharmaceutical compositions |
| EP1740589A1 (de) * | 2004-04-10 | 2007-01-10 | Boehringer Ingelheim International GmbH | Neue 2-amino-imidazo[4,5-d]pyridazin-4-one und 2-amino-imidazo[4,5-c]pyridin-4-one, deren herstellung und deren verwendung als arzneimittel |
| DE102004022970A1 (de) * | 2004-05-10 | 2005-12-01 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Imidazolderivate, deren Herstellung und deren Verwendung als Intermediate zur Herstellung von Arzneimitteln und Pestiziden |
| US7439370B2 (en) | 2004-05-10 | 2008-10-21 | Boehringer Ingelheim International Gmbh | Imidazole derivatives, their preparation and their use as intermediates for the preparation of pharmaceutical compositions and pesticides |
| EP1753730A1 (en) | 2004-06-04 | 2007-02-21 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| DE102004030502A1 (de) * | 2004-06-24 | 2006-01-12 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Imidazole und Triazole, deren Herstellung und Verwendung als Arzneimittel |
| WO2006019965A2 (en) | 2004-07-16 | 2006-02-23 | Takeda San Diego, Inc. | Dipeptidyl peptidase inhibitors |
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- 2003-12-03 EP EP03789123A patent/EP1569936B1/de not_active Expired - Lifetime
- 2003-12-03 ES ES03789123T patent/ES2324294T3/es not_active Expired - Lifetime
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| EP1569936B1 (de) | 2009-03-18 |
| EP1569936A1 (de) | 2005-09-07 |
| JP4726493B2 (ja) | 2011-07-20 |
| AR042275A1 (es) | 2005-06-15 |
| UY28103A1 (es) | 2004-06-30 |
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