JP2007508347A5 - - Google Patents
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- Publication number
- JP2007508347A5 JP2007508347A5 JP2006534704A JP2006534704A JP2007508347A5 JP 2007508347 A5 JP2007508347 A5 JP 2007508347A5 JP 2006534704 A JP2006534704 A JP 2006534704A JP 2006534704 A JP2006534704 A JP 2006534704A JP 2007508347 A5 JP2007508347 A5 JP 2007508347A5
- Authority
- JP
- Japan
- Prior art keywords
- pro
- ile
- pyrrolidine
- inhibitor
- valinyl
- 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.)
- Granted
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- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 34
- 239000003112 inhibitor Substances 0.000 claims description 18
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 8
- -1 N-valylprolyl Chemical group 0.000 claims description 7
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical group OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 claims description 4
- 208000017227 ADan amyloidosis Diseases 0.000 claims description 4
- 206010009944 Colon cancer Diseases 0.000 claims description 4
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 4
- 201000000194 ITM2B-related cerebral amyloid angiopathy 2 Diseases 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 4
- 108090000623 proteins and genes Proteins 0.000 claims description 4
- 208000023697 ABri amyloidosis Diseases 0.000 claims description 3
- 206010019375 Helicobacter infections Diseases 0.000 claims description 3
- 201000000162 ITM2B-related cerebral amyloid angiopathy 1 Diseases 0.000 claims description 3
- 239000000758 substrate Substances 0.000 claims description 3
- GEIXJNSDCIKYHU-IXDGSTSKSA-N (2s)-2-amino-n-[(2s)-1-[(2s)-2-[2-[(2,6-dichlorophenyl)methylsulfanyl]acetyl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]propanamide Chemical compound C[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)CSCC1=C(Cl)C=CC=C1Cl GEIXJNSDCIKYHU-IXDGSTSKSA-N 0.000 claims description 2
- QFKUSGBKEGSBMQ-XJPBFQKESA-N (2s)-2-amino-n-[(2s)-3-methyl-1-oxo-1-[(2s)-2-(pyridine-2-carbonyl)pyrrolidin-1-yl]butan-2-yl]propanamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)C1=CC=CC=N1 QFKUSGBKEGSBMQ-XJPBFQKESA-N 0.000 claims description 2
- WMXVRMCSOQSWAK-YPFLJBJZSA-N (2s)-n-[(2s)-1-[(2s)-2-acetylpyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]-1-[(2s)-2-amino-3-methylbutanoyl]pyrrolidine-2-carboxamide;hydrobromide Chemical compound Br.CC(C)[C@H](N)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)C)C(=O)N1[C@H](C(C)=O)CCC1 WMXVRMCSOQSWAK-YPFLJBJZSA-N 0.000 claims description 2
- VCODUTUPBPSXRA-LBRAPMIBSA-N (2s)-n-[(2s)-1-[(2s)-2-acetylpyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]-2-aminopropanamide;hydrobromide Chemical compound Br.C[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(C)=O VCODUTUPBPSXRA-LBRAPMIBSA-N 0.000 claims description 2
- 206010061825 Duodenal neoplasm Diseases 0.000 claims description 2
- 206010054184 Small intestine carcinoma Diseases 0.000 claims description 2
- 201000008629 Zollinger-Ellison syndrome Diseases 0.000 claims description 2
- GEAXDQGWIUNDBZ-NPLJWMOXSA-N [2-[(2s)-1-[(2s)-2-[[(2s)-2-aminopropanoyl]amino]-3-methylbutanoyl]pyrrolidin-2-yl]-2-oxoethyl] acetate;hydrobromide Chemical compound Br.C[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)COC(C)=O GEAXDQGWIUNDBZ-NPLJWMOXSA-N 0.000 claims description 2
- WJESOXUZZQVMIS-JSWFFFCJSA-N [2-[(2s)-1-[(2s)-2-[[(2s)-2-aminopropanoyl]amino]-3-methylbutanoyl]pyrrolidin-2-yl]-2-oxoethyl] benzoate;hydrobromide Chemical compound Br.C[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)COC(=O)C1=CC=CC=C1 WJESOXUZZQVMIS-JSWFFFCJSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 201000000312 duodenum cancer Diseases 0.000 claims description 2
- 201000000052 gastrinoma Diseases 0.000 claims description 2
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 claims description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 5
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims 3
- 235000018102 proteins Nutrition 0.000 claims 3
- 102000004169 proteins and genes Human genes 0.000 claims 3
- 102000016622 Dipeptidyl Peptidase 4 Human genes 0.000 claims 2
- 102000004190 Enzymes Human genes 0.000 claims 2
- 108090000790 Enzymes Proteins 0.000 claims 2
- 101000930822 Giardia intestinalis Dipeptidyl-peptidase 4 Proteins 0.000 claims 2
- 101000967820 Homo sapiens Inactive dipeptidyl peptidase 10 Proteins 0.000 claims 2
- 102100040449 Inactive dipeptidyl peptidase 10 Human genes 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 235000001014 amino acid Nutrition 0.000 claims 2
- 150000001413 amino acids Chemical class 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- AHBLWCWWXZJIIR-UHFFFAOYSA-N (1-cyclohexyl-3,3-dimethyl-1-oxobutan-2-yl)azanium;chloride Chemical compound [Cl-].CC(C)(C)C([NH3+])C(=O)C1CCCCC1 AHBLWCWWXZJIIR-UHFFFAOYSA-N 0.000 claims 1
- OIFZBOXCSQOOQR-UHFFFAOYSA-N (1-cyclopentyl-3,3-dimethyl-1-oxobutan-2-yl)azanium;chloride Chemical compound [Cl-].CC(C)(C)C([NH3+])C(=O)C1CCCC1 OIFZBOXCSQOOQR-UHFFFAOYSA-N 0.000 claims 1
- NGHKPFDSWWVQRM-UHFFFAOYSA-N (1-cyclopentyl-3-methyl-1-oxobutan-2-yl)azanium;chloride Chemical compound [Cl-].CC(C)C([NH3+])C(=O)C1CCCC1 NGHKPFDSWWVQRM-UHFFFAOYSA-N 0.000 claims 1
- QOMLWUOJCBLHPI-UHFFFAOYSA-N (1-cyclopentyl-3-methyl-1-oxopentan-2-yl)azanium;chloride Chemical compound [Cl-].CCC(C)C([NH3+])C(=O)C1CCCC1 QOMLWUOJCBLHPI-UHFFFAOYSA-N 0.000 claims 1
- XGNBIYXILDDDQR-DTWKUNHWSA-N (2s)-1-[(2s)-2-amino-3,3-dimethylbutanoyl]pyrrolidine-2-carbonitrile Chemical compound CC(C)(C)[C@H](N)C(=O)N1CCC[C@H]1C#N XGNBIYXILDDDQR-DTWKUNHWSA-N 0.000 claims 1
- IVBVTDXOGUNDHC-LURJTMIESA-N (2s)-2-amino-1-pyrrolidin-1-ylpropan-1-one Chemical compound C[C@H](N)C(=O)N1CCCC1 IVBVTDXOGUNDHC-LURJTMIESA-N 0.000 claims 1
- RICKQPKTSOSCOF-HKUYNNGSSA-N (3s)-2-[(2s)-2-amino-3-(1h-indol-3-yl)propanoyl]-3,4-dihydro-1h-isoquinoline-3-carboxylic acid Chemical compound C1C2=CC=CC=C2C[C@@H](C(O)=O)N1C(=O)[C@@H](N)CC1=CNC2=CC=CC=C12 RICKQPKTSOSCOF-HKUYNNGSSA-N 0.000 claims 1
- VFFZWMWTUSXDCB-ZDUSSCGKSA-N 6-[2-[[2-[(2s)-2-cyanopyrrolidin-1-yl]-2-oxoethyl]amino]ethylamino]pyridine-3-carbonitrile Chemical compound N1([C@@H](CCC1)C#N)C(=O)CNCCNC1=CC=C(C#N)C=N1 VFFZWMWTUSXDCB-ZDUSSCGKSA-N 0.000 claims 1
- 101710134735 Attractin Proteins 0.000 claims 1
- 102100027936 Attractin Human genes 0.000 claims 1
- DVJHOFUPFHOGCJ-UHFFFAOYSA-N B(O)(O)O.Br Chemical compound B(O)(O)O.Br DVJHOFUPFHOGCJ-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 108090001081 Dipeptidases Proteins 0.000 claims 1
- 102000004860 Dipeptidases Human genes 0.000 claims 1
- 102100036966 Dipeptidyl aminopeptidase-like protein 6 Human genes 0.000 claims 1
- 102100020751 Dipeptidyl peptidase 2 Human genes 0.000 claims 1
- 101000804935 Homo sapiens Dipeptidyl aminopeptidase-like protein 6 Proteins 0.000 claims 1
- MLSUZXHSNRBDCI-CYDGBPFRSA-N Ile-Pro-Val Chemical compound CC[C@H](C)[C@@H](C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)C)C(=O)O)N MLSUZXHSNRBDCI-CYDGBPFRSA-N 0.000 claims 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims 1
- FZBGMXYQPACKNC-HJWJTTGWSA-N Phe-Pro-Ile Chemical compound [H]N[C@@H](CC1=CC=CC=C1)C(=O)N1CCC[C@H]1C(=O)N[C@@H]([C@@H](C)CC)C(O)=O FZBGMXYQPACKNC-HJWJTTGWSA-N 0.000 claims 1
- GZGFSPWOMUKKCV-NAKRPEOUSA-N Ser-Pro-Ile Chemical compound CC[C@H](C)[C@@H](C(O)=O)NC(=O)[C@@H]1CCCN1C(=O)[C@@H](N)CO GZGFSPWOMUKKCV-NAKRPEOUSA-N 0.000 claims 1
- VTMGKRABARCZAX-OSUNSFLBSA-N Thr-Pro-Ile Chemical compound CC[C@H](C)[C@@H](C(O)=O)NC(=O)[C@@H]1CCCN1C(=O)[C@@H](N)[C@@H](C)O VTMGKRABARCZAX-OSUNSFLBSA-N 0.000 claims 1
- VCGOTJGGBXEBFO-FDARSICLSA-N Trp-Pro-Ile Chemical compound [H]N[C@@H](CC1=CNC2=C1C=CC=C2)C(=O)N1CCC[C@H]1C(=O)N[C@@H]([C@@H](C)CC)C(O)=O VCGOTJGGBXEBFO-FDARSICLSA-N 0.000 claims 1
- QSPOLEBZTMESFY-SRVKXCTJSA-N Val-Pro-Val Chemical compound CC(C)[C@H](N)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)C)C(O)=O QSPOLEBZTMESFY-SRVKXCTJSA-N 0.000 claims 1
- 102100039662 Xaa-Pro dipeptidase Human genes 0.000 claims 1
- XXXHSQBVHSJQKS-UHFFFAOYSA-N amino benzoate Chemical compound NOC(=O)C1=CC=CC=C1 XXXHSQBVHSJQKS-UHFFFAOYSA-N 0.000 claims 1
- 230000002860 competitive effect Effects 0.000 claims 1
- 239000012050 conventional carrier Substances 0.000 claims 1
- CSURFXBOHQPUPW-UHFFFAOYSA-N cyclopentyl(1,2,3,4-tetrahydroisoquinolin-2-ium-3-yl)methanone;chloride Chemical compound [Cl-].C1C2=CC=CC=C2C[NH2+]C1C(=O)C1CCCC1 CSURFXBOHQPUPW-UHFFFAOYSA-N 0.000 claims 1
- 108090000212 dipeptidyl peptidase II Proteins 0.000 claims 1
- 235000013922 glutamic acid Nutrition 0.000 claims 1
- 239000004220 glutamic acid Substances 0.000 claims 1
- 102000003642 glutaminyl-peptide cyclotransferase Human genes 0.000 claims 1
- 108010081484 glutaminyl-peptide cyclotransferase Proteins 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 108010066823 proline dipeptidase Proteins 0.000 claims 1
- 230000000284 resting effect Effects 0.000 claims 1
- SYOKIDBDQMKNDQ-XWTIBIIYSA-N vildagliptin Chemical compound C1C(O)(C2)CC(C3)CC1CC32NCC(=O)N1CCC[C@H]1C#N SYOKIDBDQMKNDQ-XWTIBIIYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 239000012636 effector Substances 0.000 description 6
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 241000124008 Mammalia Species 0.000 description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
- 102400000921 Gastrin Human genes 0.000 description 2
- 108010052343 Gastrins Proteins 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 208000005718 Stomach Neoplasms Diseases 0.000 description 2
- 125000000539 amino acid group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 206010017758 gastric cancer Diseases 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 229960001340 histamine Drugs 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 230000001575 pathological effect Effects 0.000 description 2
- 238000002953 preparative HPLC Methods 0.000 description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 2
- 230000004936 stimulating effect Effects 0.000 description 2
- 201000011549 stomach cancer Diseases 0.000 description 2
- 208000011580 syndromic disease Diseases 0.000 description 2
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 206010003840 Autonomic nervous system imbalance Diseases 0.000 description 1
- 208000012639 Balance disease Diseases 0.000 description 1
- 206010012289 Dementia Diseases 0.000 description 1
- 201000010374 Down Syndrome Diseases 0.000 description 1
- 208000030814 Eating disease Diseases 0.000 description 1
- 208000019454 Feeding and Eating disease Diseases 0.000 description 1
- 239000007821 HATU Substances 0.000 description 1
- 241000590002 Helicobacter pylori Species 0.000 description 1
- 101000610640 Homo sapiens U4/U6 small nuclear ribonucleoprotein Prp3 Proteins 0.000 description 1
- 102000015636 Oligopeptides Human genes 0.000 description 1
- 108010038807 Oligopeptides Proteins 0.000 description 1
- 206010062519 Poor quality sleep Diseases 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- 101001110823 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) 60S ribosomal protein L6-A Proteins 0.000 description 1
- 101000712176 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) 60S ribosomal protein L6-B Proteins 0.000 description 1
- 230000024932 T cell mediated immunity Effects 0.000 description 1
- 239000012317 TBTU Substances 0.000 description 1
- 206010044688 Trisomy 21 Diseases 0.000 description 1
- 102100040374 U4/U6 small nuclear ribonucleoprotein Prp3 Human genes 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- WVUPDWZYVPBWKO-NKGQWRHHSA-N [2-[(2s)-1-[(2s)-2-[(2-aminoacetyl)amino]-3-methylbutanoyl]pyrrolidin-2-yl]-2-oxoethyl] benzoate;hydrobromide Chemical compound Br.NCC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)COC(=O)C1=CC=CC=C1 WVUPDWZYVPBWKO-NKGQWRHHSA-N 0.000 description 1
- CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 1
- 230000009858 acid secretion Effects 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 230000024245 cell differentiation Effects 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- AOXOCDRNSPFDPE-UKEONUMOSA-N chembl413654 Chemical compound C([C@H](C(=O)NCC(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@H](CCSC)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](C)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)CNC(=O)[C@@H](N)CCC(O)=O)C1=CC=C(O)C=C1 AOXOCDRNSPFDPE-UKEONUMOSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 235000014632 disordered eating Nutrition 0.000 description 1
- 208000000718 duodenal ulcer Diseases 0.000 description 1
- 230000008482 dysregulation Effects 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 210000003038 endothelium Anatomy 0.000 description 1
- 230000037149 energy metabolism Effects 0.000 description 1
- 230000008556 epithelial cell proliferation Effects 0.000 description 1
- 125000000404 glutamine group Chemical group N[C@@H](CCC(N)=O)C(=O)* 0.000 description 1
- 229940037467 helicobacter pylori Drugs 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000013632 homeostatic process Effects 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 230000028996 humoral immune response Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 208000000509 infertility Diseases 0.000 description 1
- 230000036512 infertility Effects 0.000 description 1
- 231100000535 infertility Toxicity 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 230000023404 leukocyte cell-cell adhesion Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000009826 neoplastic cell growth Effects 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000003248 secreting effect Effects 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51203803P | 2003-10-15 | 2003-10-15 | |
| US60/512,038 | 2003-10-15 | ||
| PCT/EP2004/011630 WO2005039548A2 (en) | 2003-10-15 | 2004-10-15 | Use of effectors of glutaminyl and glutamate cyclases |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014213807A Division JP2015057400A (ja) | 2003-10-15 | 2014-10-20 | グルタミニル、及びグルタミン酸シクラーゼのエフェクターの使用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007508347A JP2007508347A (ja) | 2007-04-05 |
| JP2007508347A5 true JP2007508347A5 (enExample) | 2007-12-06 |
| JP5707014B2 JP5707014B2 (ja) | 2015-04-22 |
Family
ID=34520046
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006534704A Expired - Fee Related JP5707014B2 (ja) | 2003-10-15 | 2004-10-15 | グルタミニル、及びグルタミン酸シクラーゼのエフェクターの使用 |
| JP2014213807A Withdrawn JP2015057400A (ja) | 2003-10-15 | 2014-10-20 | グルタミニル、及びグルタミン酸シクラーゼのエフェクターの使用 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014213807A Withdrawn JP2015057400A (ja) | 2003-10-15 | 2014-10-20 | グルタミニル、及びグルタミン酸シクラーゼのエフェクターの使用 |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US7462599B2 (enExample) |
| EP (2) | EP1675578B9 (enExample) |
| JP (2) | JP5707014B2 (enExample) |
| KR (3) | KR20120007079A (enExample) |
| CN (2) | CN1867324A (enExample) |
| AU (1) | AU2004283461B2 (enExample) |
| BR (1) | BRPI0415409A (enExample) |
| CA (1) | CA2542419C (enExample) |
| DK (1) | DK1675578T3 (enExample) |
| EA (1) | EA010108B1 (enExample) |
| IL (1) | IL174372A (enExample) |
| MX (1) | MXPA06003998A (enExample) |
| NZ (1) | NZ546322A (enExample) |
| WO (1) | WO2005039548A2 (enExample) |
Families Citing this family (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE462432T1 (de) * | 2003-05-05 | 2010-04-15 | Probiodrug Ag | Glutaminylcyclase-hemmer |
| DE602004026712D1 (de) * | 2003-05-05 | 2010-06-02 | Probiodrug Ag | Medizinische verwendung von hemmern von glutaminyl und glutamatcyclasen |
| US8338120B2 (en) | 2003-05-05 | 2012-12-25 | Probiodrug Ag | Method of treating inflammation with glutaminyl cyclase inhibitors |
| NZ546322A (en) | 2003-10-15 | 2008-11-28 | Probiodrug Ag | Use of effectors of glutaminyl and glutamate cyclases |
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- 2004-10-15 BR BRPI0415409-6A patent/BRPI0415409A/pt not_active IP Right Cessation
- 2004-10-15 CN CNA2004800302025A patent/CN1867324A/zh active Pending
- 2004-10-15 DK DK04765975.0T patent/DK1675578T3/da active
- 2004-10-15 EA EA200600618A patent/EA010108B1/ru not_active IP Right Cessation
- 2004-10-15 EP EP04765975.0A patent/EP1675578B9/en not_active Expired - Lifetime
- 2004-10-15 WO PCT/EP2004/011630 patent/WO2005039548A2/en not_active Ceased
- 2004-10-15 EP EP10177029A patent/EP2289498A1/en not_active Withdrawn
- 2004-10-15 KR KR1020117031195A patent/KR20120007079A/ko not_active Ceased
- 2004-10-15 CN CN2011102597085A patent/CN102302781A/zh active Pending
- 2004-10-15 JP JP2006534704A patent/JP5707014B2/ja not_active Expired - Fee Related
- 2004-10-15 AU AU2004283461A patent/AU2004283461B2/en not_active Ceased
- 2004-10-15 KR KR1020127024628A patent/KR101313975B1/ko not_active Expired - Fee Related
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- 2004-10-15 MX MXPA06003998A patent/MXPA06003998A/es active IP Right Grant
- 2004-10-15 KR KR1020067007310A patent/KR101121882B1/ko not_active Expired - Fee Related
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2006
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2008
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2014
- 2014-10-20 JP JP2014213807A patent/JP2015057400A/ja not_active Withdrawn
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