CA2692758A1 - Intermediaire synthetique cristallin utilise dans la preparation d'un inhibiteur de la ddp-iv et son procede de purification - Google Patents

Intermediaire synthetique cristallin utilise dans la preparation d'un inhibiteur de la ddp-iv et son procede de purification Download PDF

Info

Publication number: CA2692758A1
Authority: CA; Canada
Prior art keywords: compound; crystalline form; formula; tetrahydrofuran; solution
Prior art date: 2007-07-12
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.): Abandoned

Application number

CA 2692758

Other languages

English (en)

Inventor

Zhen-Ping Wu

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Phenomix Corp

Original Assignee

Phenomix Corporation

Zhen-Ping Wu

Priority date (The priority date 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 date listed.)

2007-07-12

Filing date

2008-07-11

Publication date

2009-01-15

2008-07-11 Application filed by Phenomix Corporation, Zhen-Ping Wu filed Critical Phenomix Corporation

2009-01-15 Publication of CA2692758A1 publication Critical patent/CA2692758A1/fr

Status Abandoned legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 34
238000002360 preparation method Methods 0.000 title claims abstract description 13
239000003112 inhibitor Substances 0.000 title abstract description 10
238000000746 purification Methods 0.000 title description 7
102100025012 Dipeptidyl peptidase 4 Human genes 0.000 claims abstract description 23
108010067722 Dipeptidyl Peptidase 4 Proteins 0.000 claims abstract 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 90
150000001875 compounds Chemical class 0.000 claims description 87
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 48
238000002425 crystallisation Methods 0.000 claims description 14
230000008025 crystallization Effects 0.000 claims description 14
239000002904 solvent Substances 0.000 claims description 12
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 11
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 10
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 10
230000002401 inhibitory effect Effects 0.000 claims description 9
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 8
239000012453 solvate Substances 0.000 claims description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
230000002378 acidificating effect Effects 0.000 claims description 7
239000012736 aqueous medium Substances 0.000 claims description 7
238000006243 chemical reaction Methods 0.000 claims description 6
238000004821 distillation Methods 0.000 claims description 6
HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 claims description 6
238000001035 drying Methods 0.000 claims description 5
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 4
239000006227 byproduct Substances 0.000 claims description 4
239000012535 impurity Substances 0.000 claims description 4
238000000634 powder X-ray diffraction Methods 0.000 claims description 4
239000011975 tartaric acid Substances 0.000 claims description 4
235000002906 tartaric acid Nutrition 0.000 claims description 4
238000001816 cooling Methods 0.000 claims description 3
238000004108 freeze drying Methods 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
238000005984 hydrogenation reaction Methods 0.000 claims description 2
239000002243 precursor Substances 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims description 2
238000001694 spray drying Methods 0.000 claims description 2
238000002329 infrared spectrum Methods 0.000 claims 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 claims 1
-1 IV Chemical class 0.000 description 29
101000930822 Giardia intestinalis Dipeptidyl-peptidase 4 Proteins 0.000 description 23
239000000243 solution Substances 0.000 description 17
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
239000000543 intermediate Substances 0.000 description 10
239000000203 mixture Substances 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
239000012071 phase Substances 0.000 description 9
238000004128 high performance liquid chromatography Methods 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 7
150000003892 tartrate salts Chemical class 0.000 description 7
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 6
238000005481 NMR spectroscopy Methods 0.000 description 6
238000002474 experimental method Methods 0.000 description 6
239000000463 material Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
239000000047 product Substances 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
239000008346 aqueous phase Substances 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000008367 deionised water Substances 0.000 description 4
229910021641 deionized water Inorganic materials 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
238000003756 stirring Methods 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
102000004190 Enzymes Human genes 0.000 description 3
108090000790 Enzymes Proteins 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000002178 crystalline material Substances 0.000 description 3
238000000113 differential scanning calorimetry Methods 0.000 description 3
238000000605 extraction Methods 0.000 description 3
239000012065 filter cake Substances 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
235000018102 proteins Nutrition 0.000 description 3
102000004169 proteins and genes Human genes 0.000 description 3
108090000623 proteins and genes Proteins 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000001228 spectrum Methods 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
101150041968 CDC13 gene Proteins 0.000 description 2
108010016626 Dipeptides Proteins 0.000 description 2
102100036968 Dipeptidyl peptidase 8 Human genes 0.000 description 2
101710087011 Dipeptidyl peptidase 8 Proteins 0.000 description 2
102100036969 Dipeptidyl peptidase 9 Human genes 0.000 description 2
101710087005 Dipeptidyl peptidase 9 Proteins 0.000 description 2
101710198884 GATA-type zinc finger protein 1 Proteins 0.000 description 2
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 2
102400000322 Glucagon-like peptide 1 Human genes 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 2
241000124008 Mammalia Species 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
125000005620 boronic acid group Chemical group 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
230000008878 coupling Effects 0.000 description 2
238000010168 coupling process Methods 0.000 description 2
238000005859 coupling reaction Methods 0.000 description 2
239000013058 crude material Substances 0.000 description 2
206010012601 diabetes mellitus Diseases 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000004817 gas chromatography Methods 0.000 description 2
239000008103 glucose Substances 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
230000008569 process Effects 0.000 description 2
230000003595 spectral effect Effects 0.000 description 2
239000012622 synthetic inhibitor Substances 0.000 description 2
MOILFCKRQFQVFS-BDNRQGISSA-N (1r,3s,4r,5r)-4,6,6-trimethylbicyclo[3.1.1]heptane-3,4-diol Chemical compound C1[C@@H]2C(C)(C)[C@H]1C[C@H](O)[C@@]2(O)C MOILFCKRQFQVFS-BDNRQGISSA-N 0.000 description 1
MOILFCKRQFQVFS-OORONAJNSA-N (1s,3r,4s,5s)-4,6,6-trimethylbicyclo[3.1.1]heptane-3,4-diol Chemical compound C1[C@H]2C(C)(C)[C@@H]1C[C@@H](O)[C@]2(O)C MOILFCKRQFQVFS-OORONAJNSA-N 0.000 description 1
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
PJUPKRYGDFTMTM-UHFFFAOYSA-N 1-hydroxybenzotriazole;hydrate Chemical compound O.C1=CC=C2N(O)N=NC2=C1 PJUPKRYGDFTMTM-UHFFFAOYSA-N 0.000 description 1
MOILFCKRQFQVFS-UHFFFAOYSA-N 4,6,6-trimethylbicyclo[3.1.1]heptane-3,4-diol Chemical compound C1C2C(C)(C)C1CC(O)C2(O)C MOILFCKRQFQVFS-UHFFFAOYSA-N 0.000 description 1
102000003779 Dipeptidyl-peptidases and tripeptidyl-peptidases Human genes 0.000 description 1
108090000194 Dipeptidyl-peptidases and tripeptidyl-peptidases Proteins 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
238000004566 IR spectroscopy Methods 0.000 description 1
101500016415 Lophius americanus Glucagon-like peptide 1 Proteins 0.000 description 1
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 1
229940124639 Selective inhibitor Drugs 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
238000000862 absorption spectrum Methods 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000004913 activation Effects 0.000 description 1
125000003295 alanine group Chemical group N[C@@H](C)C(=O)* 0.000 description 1
235000001014 amino acid Nutrition 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
210000004027 cell Anatomy 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
210000002950 fibroblast Anatomy 0.000 description 1
239000012467 final product Substances 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
230000006872 improvement Effects 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
229940011051 isopropyl acetate Drugs 0.000 description 1
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
PSACHCMMPFMFAJ-UHFFFAOYSA-N nmm n-methylmorpholine Chemical compound CN1CCOCC1.CN1CCOCC1 PSACHCMMPFMFAJ-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
230000003132 peptidolytic effect Effects 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
CQMHKCYAPOVFMJ-UHFFFAOYSA-N phenylboronic acid 2,6,6-trimethylbicyclo[3.1.1]heptane-1,2-diol Chemical compound OB(O)C1=CC=CC=C1.C1C2(O)C(C)(C)C1CCC2(O)C CQMHKCYAPOVFMJ-UHFFFAOYSA-N 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
230000036470 plasma concentration Effects 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
239000008213 purified water Substances 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
239000013557 residual solvent Substances 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000010956 selective crystallization Methods 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

CA 2692758 2007-07-12 2008-07-11 Intermediaire synthetique cristallin utilise dans la preparation d'un inhibiteur de la ddp-iv et son procede de purification Abandoned CA2692758A1 (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US95922607P	2007-07-12	2007-07-12
US60/959,226		2007-07-12
PCT/US2008/069833 WO2009009751A1 (fr)	2007-07-12	2008-07-11	Intermédiaire synthétique cristallin utilisé dans la préparation d'un inhibiteur de la ddp-iv et son procédé de purification

Publications (1)

Publication Number	Publication Date
CA2692758A1 true CA2692758A1 (fr)	2009-01-15

Family

ID=40229094

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2692758 Abandoned CA2692758A1 (fr)	2007-07-12	2008-07-11	Intermediaire synthetique cristallin utilise dans la preparation d'un inhibiteur de la ddp-iv et son procede de purification

Country Status (8)

Country	Link
US (1)	US20100204484A1 (fr)
EP (1)	EP2175727A4 (fr)
AR (1)	AR068187A1 (fr)
CA (1)	CA2692758A1 (fr)
CL (1)	CL2008002044A1 (fr)
MX (1)	MX2010000501A (fr)
TW (1)	TW200927144A (fr)
WO (1)	WO2009009751A1 (fr)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
UY32030A (es)	2008-08-06	2010-03-26	Boehringer Ingelheim Int	"tratamiento para diabetes en pacientes inapropiados para terapia con metformina"
JP5906086B2 (ja)	2008-08-15	2016-04-20	ベーリンガーインゲルハイムインターナショナルゲゼルシャフトミットベシュレンクテルハフツング	Ｆａｂ関連疾患の治療に用いるためのプリン誘導体
TW201036975A (en)	2009-01-07	2010-10-16	Boehringer Ingelheim Int	Treatment for diabetes in patients with inadequate glycemic control despite metformin therapy
TWI466672B (zh)	2009-01-29	2015-01-01	Boehringer Ingelheim Int	小兒科病人糖尿病之治療
CN106177958A (zh)	2009-02-13	2016-12-07	勃林格殷格翰国际有限公司	包含dpp‑4抑制剂(利拉列汀)任选地组合其它抗糖尿病药的抗糖尿病药物
JP2013512229A (ja)	2009-11-27	2013-04-11	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	遺伝子型が同定された糖尿病患者のリナグリプチン等のｄｄｐ−ｉｖ阻害薬による治療
WO2011113947A1 (fr)	2010-03-18	2011-09-22	Boehringer Ingelheim International Gmbh	Combinaisons d'agonistes de gpr119 et d'inhibiteurs de dpp-iv, linagliptine, pour le traitement du diabète et d'états apparentés
NZ602921A (en)	2010-05-05	2016-01-29	Boehringer Ingelheim Int	Combination therapy comprising the administration of a glp-1 receptor agonist and a ddp-4 inhibitor
MX2012014247A (es)	2010-06-24	2013-01-18	Boehringer Ingelheim Int	Terapia para la diabetes.
WO2012170702A1 (fr)	2011-06-08	2012-12-13	Arena Pharmaceuticals, Inc.	Modulateurs du récepteur gpr119 et traitement de troubles associés à celui-ci
WO2013174767A1 (fr)	2012-05-24	2013-11-28	Boehringer Ingelheim International Gmbh	Dérivé de xanthine en tant qu'inhibiteur de la dpp-4 à utiliser dans la modification de l'apport alimentaire et dans la régulation des préférences alimentaires

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3496163A (en) *	1965-02-08	1970-02-17	Upjohn Co	7-halo-7-deoxylincomycins and process for preparing the same
US5329012A (en) *	1987-10-29	1994-07-12	The Research Foundation Of State University Of New York	Bis(acyloxmethyl)imidazole compounds
US20100087658A1 (en) *	1996-08-06	2010-04-08	Phenomix Corporation	Methods and intermediates for synthesis of selective dpp-iv inhibitors
US20040077605A1 (en) *	2001-06-20	2004-04-22	Salvati Mark E.	Fused heterocyclic succinimide compounds and analogs thereof, modulators of nuclear hormone receptor function
US7317109B2 (en) *	2003-11-12	2008-01-08	Phenomix Corporation	Pyrrolidine compounds and methods for selective inhibition of dipeptidyl peptidase-IV
US7576121B2 (en) *	2003-11-12	2009-08-18	Phenomix Corporation	Pyrrolidine compounds and methods for selective inhibition of dipeptidyl peptidase-IV
EP1919485A4 (fr) *	2005-08-01	2011-03-23	Phenomix Corp	Procedes de preparation d'acides boroniques heterocycliques et de derives de ceux-ci
WO2007038676A2 (fr) *	2005-09-28	2007-04-05	Teva Pharmaceutical Industries Ltd.	Formes polymorphiques de ladostigil tartrate

2008
- 2008-07-11 MX MX2010000501A patent/MX2010000501A/es not_active Application Discontinuation
- 2008-07-11 US US12/668,405 patent/US20100204484A1/en not_active Abandoned
- 2008-07-11 TW TW097126510A patent/TW200927144A/zh unknown
- 2008-07-11 CL CL2008002044A patent/CL2008002044A1/es unknown
- 2008-07-11 EP EP08826302A patent/EP2175727A4/fr not_active Withdrawn
- 2008-07-11 CA CA 2692758 patent/CA2692758A1/fr not_active Abandoned
- 2008-07-11 AR ARP080102995A patent/AR068187A1/es unknown
- 2008-07-11 WO PCT/US2008/069833 patent/WO2009009751A1/fr active Application Filing

Also Published As

Publication number	Publication date
US20100204484A1 (en)	2010-08-12
TW200927144A (en)	2009-07-01
EP2175727A1 (fr)	2010-04-21
MX2010000501A (es)	2011-05-25
WO2009009751A1 (fr)	2009-01-15
CL2008002044A1 (es)	2009-01-16
EP2175727A4 (fr)	2011-05-25
AR068187A1 (es)	2009-11-11

Legal Events

Date	Code	Title	Description
2013-07-08	EEER	Examination request	Effective date: 20130618
2016-03-08	FZDE	Discontinued	Effective date: 20160126

Publication	Publication Date	Title
CA2692758A1 (fr)	2009-01-15	Intermediaire synthetique cristallin utilise dans la preparation d'un inhibiteur de la ddp-iv et son procede de purification
EP0340064A1 (fr)	1989-11-02	Benzodiazépines, leur procédé et intermédiaires de préparation et leurs applications en thérapeutique
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