JP2006516121A5 - - Google Patents
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- JP2006516121A5 JP2006516121A5 JP2004559282A JP2004559282A JP2006516121A5 JP 2006516121 A5 JP2006516121 A5 JP 2006516121A5 JP 2004559282 A JP2004559282 A JP 2004559282A JP 2004559282 A JP2004559282 A JP 2004559282A JP 2006516121 A5 JP2006516121 A5 JP 2006516121A5
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- JP
- Japan
- Prior art keywords
- decane
- compound
- acetic acid
- acid
- ester
- 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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- 238000000034 method Methods 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 23
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- -1 dimethyl ethyl Chemical group 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 9
- 239000012458 free base Substances 0.000 claims description 8
- CJJMAWPEZKYJAP-UHFFFAOYSA-N 3-hydroxyadamantane-1-carboxylic acid Chemical compound C1C(C2)CC3CC2(O)CC1(C(=O)O)C3 CJJMAWPEZKYJAP-UHFFFAOYSA-N 0.000 claims description 7
- 239000012359 Methanesulfonyl chloride Substances 0.000 claims description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 239000002585 base Substances 0.000 claims description 6
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 6
- 239000003112 inhibitor Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- ZTFQAYLTBXTFDQ-UHFFFAOYSA-N CC(C)(C)OC(NCC)=O.CCCCCC Chemical compound CC(C)(C)OC(NCC)=O.CCCCCC ZTFQAYLTBXTFDQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 239000012044 organic layer Substances 0.000 claims description 4
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 claims description 3
- MZYSDTANDLESAJ-UHFFFAOYSA-N C1C(C2)CC3CC1(O)C(NC(=O)OC(C)(C)C)C2(CC(O)=O)C3 Chemical compound C1C(C2)CC3CC1(O)C(NC(=O)OC(C)(C)C)C2(CC(O)=O)C3 MZYSDTANDLESAJ-UHFFFAOYSA-N 0.000 claims description 3
- 102000016622 Dipeptidyl Peptidase 4 Human genes 0.000 claims description 3
- 101000930822 Giardia intestinalis Dipeptidyl-peptidase 4 Proteins 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 150000004682 monohydrates Chemical class 0.000 claims description 3
- 230000002194 synthesizing effect Effects 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 9
- 229910052783 alkali metal Inorganic materials 0.000 claims 9
- ZOFWFAZCJJJYCE-UHFFFAOYSA-N 2-amino-2-(3-hydroxy-1-adamantyl)acetic acid Chemical compound C1C(C2)CC3CC2(O)CC1(C(C(O)=O)N)C3 ZOFWFAZCJJJYCE-UHFFFAOYSA-N 0.000 claims 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 4
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical class C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 159000000000 sodium salts Chemical class 0.000 claims 4
- 239000000243 solution Substances 0.000 claims 4
- ZDKSDALJIXEHOP-ZETCQYMHSA-N tert-butyl (2s)-2-carbamoyl-2,3-dihydropyrrole-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1C=CC[C@H]1C(N)=O ZDKSDALJIXEHOP-ZETCQYMHSA-N 0.000 claims 4
- BGAMGLYMXSMZPL-UHFFFAOYSA-N 1-[(2-methylpropan-2-yl)oxycarbonyl]-2,3-dihydropyrrole-2-carboxylic acid Chemical compound CC(C)(C)OC(=O)N1C=CCC1C(O)=O BGAMGLYMXSMZPL-UHFFFAOYSA-N 0.000 claims 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- 238000005891 transamination reaction Methods 0.000 claims 3
- MCEWPPMUTVLMJG-YUPRTTJUSA-N (1s,3s,5s)-2-azabicyclo[3.1.0]hexane-3-carboxamide Chemical compound N1[C@H](C(=O)N)C[C@@H]2C[C@@H]21 MCEWPPMUTVLMJG-YUPRTTJUSA-N 0.000 claims 2
- NNINTIFNNLVVKH-BYPYZUCNSA-N (2s)-2-carbamoyl-2,3-dihydropyrrole-1-carboxylic acid Chemical compound NC(=O)[C@@H]1CC=CN1C(O)=O NNINTIFNNLVVKH-BYPYZUCNSA-N 0.000 claims 2
- GQBVPWDPTCICNW-UHFFFAOYSA-N 2-(1-adamantyl)-2-bromoacetic acid Chemical compound C1C(C2)CC3CC2CC1(C(Br)C(=O)O)C3 GQBVPWDPTCICNW-UHFFFAOYSA-N 0.000 claims 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 150000001340 alkali metals Chemical class 0.000 claims 2
- 238000005576 amination reaction Methods 0.000 claims 2
- 229910021529 ammonia Inorganic materials 0.000 claims 2
- 238000010276 construction Methods 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 125000004494 ethyl ester group Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 2
- 239000000047 product Substances 0.000 claims 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical class C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims 2
- MDTMETSJBLNDRH-UHFFFAOYSA-N 2,3-dihydropyrrole-1,2-dicarboxylic acid Chemical compound OC(=O)C1CC=CN1C(O)=O MDTMETSJBLNDRH-UHFFFAOYSA-N 0.000 claims 1
- WZEMCIVRSRWCLK-UHFFFAOYSA-N 2-bromo-2-(3-hydroxy-1-adamantyl)acetic acid Chemical compound C1C(C2)CC3CC2(O)CC1(C(Br)C(=O)O)C3 WZEMCIVRSRWCLK-UHFFFAOYSA-N 0.000 claims 1
- BMTZEAOGFDXDAD-UHFFFAOYSA-M 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium;chloride Chemical compound [Cl-].COC1=NC(OC)=NC([N+]2(C)CCOCC2)=N1 BMTZEAOGFDXDAD-UHFFFAOYSA-M 0.000 claims 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 1
- YNJAHVQRSAUUKL-UHFFFAOYSA-N CCNC(=O)O.CCCCCC Chemical compound CCNC(=O)O.CCCCCC YNJAHVQRSAUUKL-UHFFFAOYSA-N 0.000 claims 1
- 229940124213 Dipeptidyl peptidase 4 (DPP IV) inhibitor Drugs 0.000 claims 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 1
- 238000006932 Simmons-Smith cyclopropanation reaction Methods 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 239000000908 ammonium hydroxide Substances 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 239000012267 brine Substances 0.000 claims 1
- 230000031709 bromination Effects 0.000 claims 1
- 238000005893 bromination reaction Methods 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims 1
- PJGJQVRXEUVAFT-UHFFFAOYSA-N chloroiodomethane Chemical compound ClCI PJGJQVRXEUVAFT-UHFFFAOYSA-N 0.000 claims 1
- 238000005888 cyclopropanation reaction Methods 0.000 claims 1
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 claims 1
- 239000003603 dipeptidyl peptidase IV inhibitor Substances 0.000 claims 1
- 230000002255 enzymatic effect Effects 0.000 claims 1
- QPNJHVDIRZNKOX-LURJTMIESA-N ethyl (2s)-pyrrolidine-2-carboxylate Chemical compound CCOC(=O)[C@@H]1CCCN1 QPNJHVDIRZNKOX-LURJTMIESA-N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 238000005580 one pot reaction Methods 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 238000006722 reduction reaction Methods 0.000 claims 1
- 238000006268 reductive amination reaction Methods 0.000 claims 1
- 230000002829 reductive effect Effects 0.000 claims 1
- 239000012266 salt solution Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 238000007127 saponification reaction Methods 0.000 claims 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims 1
- PTEZWVYFPGDCKB-UHFFFAOYSA-N tert-butyl 2-azabicyclo[3.1.0]hexane-2-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC2CC12 PTEZWVYFPGDCKB-UHFFFAOYSA-N 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- JFUDIEFZSNQJBS-SHLRHQAISA-N (1s,3s,5s)-2-azabicyclo[3.1.0]hexane-3-carboxamide;hydrochloride Chemical compound Cl.N1[C@H](C(=O)N)C[C@@H]2C[C@@H]21 JFUDIEFZSNQJBS-SHLRHQAISA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- 102100025101 GATA-type zinc finger protein 1 Human genes 0.000 description 1
- 101710198884 GATA-type zinc finger protein 1 Proteins 0.000 description 1
- DTHNMHAUYICORS-KTKZVXAJSA-N Glucagon-like peptide 1 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 DTHNMHAUYICORS-KTKZVXAJSA-N 0.000 description 1
- IIUQXUPBYXSVRP-YIKQXJHESA-N NC(C(CC(C1)C2)(CC1C1)CC21O)C(N(C1[C@@]2(C3)[C@@H]1C2)[C@@H]3C#N)=O Chemical compound NC(C(CC(C1)C2)(CC1C1)CC21O)C(N(C1[C@@]2(C3)[C@@H]1C2)[C@@H]3C#N)=O IIUQXUPBYXSVRP-YIKQXJHESA-N 0.000 description 1
- 0 O[C@@]1*C2(CC2)CC1 Chemical compound O[C@@]1*C2(CC2)CC1 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US43181402P | 2002-12-09 | 2002-12-09 | |
| US60/431,814 | 2002-12-09 | ||
| PCT/US2003/038558 WO2004052850A2 (en) | 2002-12-09 | 2003-12-04 | Methods and compounds producing dipeptidyl peptidase iv inhibitors and intermediates thereof |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010181559A Division JP5511582B2 (ja) | 2002-12-09 | 2010-08-16 | ジペプチジルペプチダーゼｉｖインヒビターおよびその中間体を製造する方法および化合物 |
| JP2010181557A Division JP5345986B2 (ja) | 2002-12-09 | 2010-08-16 | ジペプチジルペプチダーゼｉｖインヒビターおよびその中間体を製造する方法および化合物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2006516121A JP2006516121A (ja) | 2006-06-22 |
| JP2006516121A5 true JP2006516121A5 (enExample) | 2007-01-25 |
| JP4886193B2 JP4886193B2 (ja) | 2012-02-29 |
Family
ID=32507798
Family Applications (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004559282A Expired - Fee Related JP4886193B2 (ja) | 2002-12-09 | 2003-12-04 | ジペプチジルペプチダーゼｉｖインヒビターおよびその中間体を製造する方法および化合物 |
| JP2010181557A Expired - Fee Related JP5345986B2 (ja) | 2002-12-09 | 2010-08-16 | ジペプチジルペプチダーゼｉｖインヒビターおよびその中間体を製造する方法および化合物 |
| JP2010181559A Expired - Fee Related JP5511582B2 (ja) | 2002-12-09 | 2010-08-16 | ジペプチジルペプチダーゼｉｖインヒビターおよびその中間体を製造する方法および化合物 |
| JP2013024598A Expired - Fee Related JP5730341B2 (ja) | 2002-12-09 | 2013-02-12 | ジペプチジルペプチダーゼｉｖインヒビターおよびその中間体を製造する方法および化合物 |
| JP2013168522A Expired - Fee Related JP5860007B2 (ja) | 2002-12-09 | 2013-08-14 | ジペプチジルペプチダーゼｉｖインヒビターおよびその中間体を製造する方法および化合物 |
| JP2015190071A Pending JP2016040282A (ja) | 2002-12-09 | 2015-09-28 | ジペプチジルペプチダーゼｉｖインヒビターおよびその中間体を製造する方法および化合物 |
Family Applications After (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010181557A Expired - Fee Related JP5345986B2 (ja) | 2002-12-09 | 2010-08-16 | ジペプチジルペプチダーゼｉｖインヒビターおよびその中間体を製造する方法および化合物 |
| JP2010181559A Expired - Fee Related JP5511582B2 (ja) | 2002-12-09 | 2010-08-16 | ジペプチジルペプチダーゼｉｖインヒビターおよびその中間体を製造する方法および化合物 |
| JP2013024598A Expired - Fee Related JP5730341B2 (ja) | 2002-12-09 | 2013-02-12 | ジペプチジルペプチダーゼｉｖインヒビターおよびその中間体を製造する方法および化合物 |
| JP2013168522A Expired - Fee Related JP5860007B2 (ja) | 2002-12-09 | 2013-08-14 | ジペプチジルペプチダーゼｉｖインヒビターおよびその中間体を製造する方法および化合物 |
| JP2015190071A Pending JP2016040282A (ja) | 2002-12-09 | 2015-09-28 | ジペプチジルペプチダーゼｉｖインヒビターおよびその中間体を製造する方法および化合物 |
Country Status (17)
| Country | Link |
|---|---|
| US (4) | US7420079B2 (enExample) |
| EP (5) | EP2505579B1 (enExample) |
| JP (6) | JP4886193B2 (enExample) |
| KR (1) | KR20050088309A (enExample) |
| CN (3) | CN1791401B (enExample) |
| AU (1) | AU2003297647A1 (enExample) |
| BR (1) | BR0317139A (enExample) |
| CA (1) | CA2508619A1 (enExample) |
| DK (4) | DK2505578T3 (enExample) |
| ES (4) | ES2525593T3 (enExample) |
| IL (1) | IL192912A0 (enExample) |
| MX (1) | MXPA05005970A (enExample) |
| PL (1) | PL377123A1 (enExample) |
| PT (4) | PT2505579E (enExample) |
| SI (4) | SI2505578T1 (enExample) |
| TW (2) | TW200914419A (enExample) |
| WO (1) | WO2004052850A2 (enExample) |
Families Citing this family (133)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0487425A (ja) * | 1990-07-31 | 1992-03-19 | Fujitsu Ltd | 回線切り替え装置 |
| PL367527A1 (en) | 2001-06-27 | 2005-02-21 | Smithkline Beecham Corporation | Fluoropyrrolidines as dipeptidyl peptidase inhibitors |
| US7420079B2 (en) * | 2002-12-09 | 2008-09-02 | Bristol-Myers Squibb Company | Methods and compounds for producing dipeptidyl peptidase IV inhibitors and intermediates thereof |
| KR20050122220A (ko) | 2003-03-25 | 2005-12-28 | 다케다 샌디에고, 인코포레이티드 | 디펩티딜 펩티다제 억제제 |
| US7638638B2 (en) | 2003-05-14 | 2009-12-29 | Takeda San Diego, Inc. | Dipeptidyl peptidase inhibitors |
| US6995183B2 (en) * | 2003-08-01 | 2006-02-07 | Bristol Myers Squibb Company | Adamantylglycine-based inhibitors of dipeptidyl peptidase IV and methods |
| US7790736B2 (en) | 2003-08-13 | 2010-09-07 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| CN1905876B (zh) | 2003-11-17 | 2010-06-09 | 诺瓦提斯公司 | 二肽基肽酶iv抑制剂的用途 |
| NZ578743A (en) | 2004-01-20 | 2011-04-29 | Novartis Ag | Direct compression formulation and process |
| TW200538122A (en) * | 2004-03-31 | 2005-12-01 | Bristol Myers Squibb Co | Process for preparing a dipeptidyl peptidase Ⅳ inhibitor and intermediates employed therein |
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| CA2337230A1 (en) | 1998-07-15 | 2000-01-27 | Bristol-Myers Squibb Company | Stereoselective reductive amination of ketones |
| US6395767B2 (en) * | 2000-03-10 | 2002-05-28 | Bristol-Myers Squibb Company | Cyclopropyl-fused pyrrolidine-based inhibitors of dipeptidyl peptidase IV and method |
| JP3942846B2 (ja) * | 2001-06-21 | 2007-07-11 | 独立行政法人科学技術振興機構 | 組織特異的トランスポーター阻害剤 |
| WO2004037181A2 (en) | 2002-10-23 | 2004-05-06 | Bristol-Myers Squibb Company | Glycinenitrile-based inhibitors of dipeptidyl peptidase iv and methods |
| US7420079B2 (en) * | 2002-12-09 | 2008-09-02 | Bristol-Myers Squibb Company | Methods and compounds for producing dipeptidyl peptidase IV inhibitors and intermediates thereof |
| US6995183B2 (en) | 2003-08-01 | 2006-02-07 | Bristol Myers Squibb Company | Adamantylglycine-based inhibitors of dipeptidyl peptidase IV and methods |
| CN1905876B (zh) | 2003-11-17 | 2010-06-09 | 诺瓦提斯公司 | 二肽基肽酶iv抑制剂的用途 |
| TW200538122A (en) * | 2004-03-31 | 2005-12-01 | Bristol Myers Squibb Co | Process for preparing a dipeptidyl peptidase Ⅳ inhibitor and intermediates employed therein |
| US7741082B2 (en) * | 2004-04-14 | 2010-06-22 | Bristol-Myers Squibb Company | Process for preparing dipeptidyl peptidase IV inhibitors and intermediates therefor |
| TW200536827A (en) * | 2004-05-04 | 2005-11-16 | Bristol Myers Squibb Co | Enzymatic ammonolysis process for the preparation of intermediates for DPP IV inhibitors |
| US7214702B2 (en) * | 2004-05-25 | 2007-05-08 | Bristol-Myers Squibb Company | Process for producing a dipeptidyl peptidase IV inhibitor |
-
2003
- 2003-11-18 US US10/716,012 patent/US7420079B2/en not_active Expired - Fee Related
- 2003-12-04 EP EP12162633.7A patent/EP2505579B1/en not_active Revoked
- 2003-12-04 CN CN2003801096317A patent/CN1791401B/zh not_active Expired - Fee Related
- 2003-12-04 DK DK12162626.1T patent/DK2505578T3/en active
- 2003-12-04 EP EP03812799.9A patent/EP1581487B1/en not_active Expired - Lifetime
- 2003-12-04 CN CN201010260709.7A patent/CN102070451B/zh not_active Expired - Fee Related
- 2003-12-04 DK DK12162633.7T patent/DK2505579T3/en active
- 2003-12-04 WO PCT/US2003/038558 patent/WO2004052850A2/en not_active Ceased
- 2003-12-04 PT PT121626337T patent/PT2505579E/pt unknown
- 2003-12-04 EP EP14175293.1A patent/EP2792672A3/en not_active Withdrawn
- 2003-12-04 BR BR0317139-6A patent/BR0317139A/pt not_active IP Right Cessation
- 2003-12-04 SI SI200332397T patent/SI2505578T1/sl unknown
- 2003-12-04 ES ES12162626.1T patent/ES2525593T3/es not_active Expired - Lifetime
- 2003-12-04 ES ES03812799.9T patent/ES2484915T3/es not_active Expired - Lifetime
- 2003-12-04 CA CA002508619A patent/CA2508619A1/en not_active Abandoned
- 2003-12-04 ES ES12162633.7T patent/ES2526138T3/es not_active Expired - Lifetime
- 2003-12-04 KR KR1020057010467A patent/KR20050088309A/ko not_active Ceased
- 2003-12-04 DK DK03812799.9T patent/DK1581487T3/da active
- 2003-12-04 ES ES12162624.6T patent/ES2494793T3/es not_active Expired - Lifetime
- 2003-12-04 PL PL377123A patent/PL377123A1/pl not_active Application Discontinuation
- 2003-12-04 EP EP12162626.1A patent/EP2505578B1/en not_active Expired - Lifetime
- 2003-12-04 PT PT121626261T patent/PT2505578E/pt unknown
- 2003-12-04 MX MXPA05005970A patent/MXPA05005970A/es unknown
- 2003-12-04 SI SI200332363T patent/SI1581487T1/sl unknown
- 2003-12-04 PT PT38127999T patent/PT1581487E/pt unknown
- 2003-12-04 CN CN201210268678.9A patent/CN102942482B/zh not_active Expired - Fee Related
- 2003-12-04 SI SI200332399T patent/SI2505579T1/sl unknown
- 2003-12-04 JP JP2004559282A patent/JP4886193B2/ja not_active Expired - Fee Related
- 2003-12-04 EP EP12162624.6A patent/EP2517706B1/en not_active Expired - Lifetime
- 2003-12-04 SI SI200332365T patent/SI2517706T1/sl unknown
- 2003-12-04 PT PT121626246T patent/PT2517706E/pt unknown
- 2003-12-04 DK DK12162624.6T patent/DK2517706T3/da active
- 2003-12-04 AU AU2003297647A patent/AU2003297647A1/en not_active Abandoned
- 2003-12-09 TW TW097142662A patent/TW200914419A/zh unknown
- 2003-12-09 TW TW092134725A patent/TW200512191A/zh unknown
-
2008
- 2008-07-20 IL IL192912A patent/IL192912A0/en unknown
- 2008-07-28 US US12/181,216 patent/US7705033B2/en not_active Expired - Fee Related
-
2010
- 2010-02-25 US US12/712,958 patent/US8278462B2/en not_active Expired - Fee Related
- 2010-08-16 JP JP2010181557A patent/JP5345986B2/ja not_active Expired - Fee Related
- 2010-08-16 JP JP2010181559A patent/JP5511582B2/ja not_active Expired - Fee Related
-
2012
- 2012-08-31 US US13/601,477 patent/US20130012723A1/en not_active Abandoned
-
2013
- 2013-02-12 JP JP2013024598A patent/JP5730341B2/ja not_active Expired - Fee Related
- 2013-08-14 JP JP2013168522A patent/JP5860007B2/ja not_active Expired - Fee Related
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2015
- 2015-09-28 JP JP2015190071A patent/JP2016040282A/ja active Pending
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