CA2383298C - Nouveaux derives d'.alpha.-amino-acides, leur procede de preparation et les compositions pharmaceutiques qui les contiennent - Google Patents
Nouveaux derives d'.alpha.-amino-acides, leur procede de preparation et les compositions pharmaceutiques qui les contiennent Download PDFInfo
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- CA2383298C CA2383298C CA002383298A CA2383298A CA2383298C CA 2383298 C CA2383298 C CA 2383298C CA 002383298 A CA002383298 A CA 002383298A CA 2383298 A CA2383298 A CA 2383298A CA 2383298 C CA2383298 C CA 2383298C
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- cyano
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- amino
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- 239000008194 pharmaceutical composition Substances 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 7
- 150000001413 amino acids Chemical class 0.000 title 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 79
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 27
- 239000002253 acid Substances 0.000 claims abstract description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 16
- 238000011282 treatment Methods 0.000 claims abstract description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 13
- -1 when Y is CHNO2 Chemical group 0.000 claims abstract description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 201000010099 disease Diseases 0.000 claims abstract description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 8
- 230000003287 optical effect Effects 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 201000001421 hyperglycemia Diseases 0.000 claims abstract description 7
- 208000002705 Glucose Intolerance Diseases 0.000 claims abstract description 5
- 206010018429 Glucose tolerance impaired Diseases 0.000 claims abstract description 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 3
- 229940124213 Dipeptidyl peptidase 4 (DPP IV) inhibitor Drugs 0.000 claims abstract 5
- 239000003603 dipeptidyl peptidase IV inhibitor Substances 0.000 claims abstract 5
- 238000000034 method Methods 0.000 claims description 46
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
- 101000930822 Giardia intestinalis Dipeptidyl-peptidase 4 Proteins 0.000 claims description 7
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 208000008589 Obesity Diseases 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 238000010511 deprotection reaction Methods 0.000 claims description 5
- 239000003112 inhibitor Substances 0.000 claims description 5
- 235000020824 obesity Nutrition 0.000 claims description 5
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- 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 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000001408 amides Chemical group 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 239000008103 glucose Substances 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- FEEQIYWLPBNURB-QMMMGPOBSA-N 2-[(5s)-5-amino-6-oxo-6-(1,3-thiazolidin-3-yl)hexyl]-1-nitroguanidine Chemical compound [O-][N+](=O)NC(=N)NCCCC[C@H](N)C(=O)N1CCSC1 FEEQIYWLPBNURB-QMMMGPOBSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 230000001012 protector Effects 0.000 claims description 2
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- 102000016622 Dipeptidyl Peptidase 4 Human genes 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 230000003178 anti-diabetic effect Effects 0.000 claims 1
- 239000003472 antidiabetic agent Substances 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 31
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 238000004452 microanalysis Methods 0.000 description 16
- ALSCEGDXFJIYES-YFKPBYRVSA-N (2s)-pyrrolidine-2-carbonitrile Chemical compound N#C[C@@H]1CCCN1 ALSCEGDXFJIYES-YFKPBYRVSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 11
- 102100025012 Dipeptidyl peptidase 4 Human genes 0.000 description 10
- 229910052717 sulfur Inorganic materials 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 6
- BDHUTRNYBGWPBL-HNNXBMFYSA-N (2s)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-6-(phenylmethoxycarbonylamino)hexanoic acid Chemical compound CC(C)(C)OC(=O)N[C@H](C(O)=O)CCCCNC(=O)OCC1=CC=CC=C1 BDHUTRNYBGWPBL-HNNXBMFYSA-N 0.000 description 5
- QYYCZJUFHDLLOJ-AWEZNQCLSA-N (2s)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-(phenylmethoxycarbonylamino)pentanoic acid Chemical compound CC(C)(C)OC(=O)N[C@H](C(O)=O)CCCNC(=O)OCC1=CC=CC=C1 QYYCZJUFHDLLOJ-AWEZNQCLSA-N 0.000 description 4
- 108010067722 Dipeptidyl Peptidase 4 Proteins 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 101800000224 Glucagon-like peptide 1 Proteins 0.000 description 3
- 102100040918 Pro-glucagon Human genes 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- 230000007170 pathology Effects 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- NDMVQEZKACRLDP-NSHDSACASA-N (2s)-3-(4-aminophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)N[C@H](C(O)=O)CC1=CC=C(N)C=C1 NDMVQEZKACRLDP-NSHDSACASA-N 0.000 description 2
- PRSDPVKGJUBIAA-SCSAIBSYSA-N (4r)-1,3-thiazolidine-4-carbonitrile Chemical compound N#C[C@@H]1CSCN1 PRSDPVKGJUBIAA-SCSAIBSYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- FSUKJDXBTJCGHH-PPHPATTJSA-N 1-[(4s)-4-amino-5-oxo-5-pyrrolidin-1-ylpentyl]-3-cyano-2-methylguanidine;hydrochloride Chemical compound Cl.N#CN=C(NC)NCCC[C@H](N)C(=O)N1CCCC1 FSUKJDXBTJCGHH-PPHPATTJSA-N 0.000 description 2
- DOBNRQCCTDSSKV-YDALLXLXSA-N 2-[4-[(2s)-2-amino-3-oxo-3-pyrrolidin-1-ylpropyl]phenyl]-1-nitroguanidine;hydrochloride Chemical compound Cl.C([C@H](N)C(=O)N1CCCC1)C1=CC=C(NC(=N)N[N+]([O-])=O)C=C1 DOBNRQCCTDSSKV-YDALLXLXSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
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- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- SQVRNKJHWKZAKO-PFQGKNLYSA-N N-acetyl-beta-neuraminic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-PFQGKNLYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- QQZXQAJYFKBPGK-ACMTZBLWSA-N 2-[(6s)-6-amino-7-[(2s)-2-cyanopyrrolidin-1-yl]-7-oxoheptyl]-1-nitroguanidine;hydrochloride Chemical compound Cl.[O-][N+](=O)NC(=N)NCCCCC[C@H](N)C(=O)N1CCC[C@H]1C#N QQZXQAJYFKBPGK-ACMTZBLWSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
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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
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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
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D277/06—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Diabetes (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Engineering & Computer Science (AREA)
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- Obesity (AREA)
- Emergency Medicine (AREA)
- Molecular Biology (AREA)
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- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Tropical Medicine & Parasitology (AREA)
- AIDS & HIV (AREA)
- Child & Adolescent Psychology (AREA)
- Communicable Diseases (AREA)
- Biophysics (AREA)
- Oncology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0106375A FR2824825B1 (fr) | 2001-05-15 | 2001-05-15 | Nouveaux derives d'alpha-amino-acides, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR01.06375 | 2001-05-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2383298A1 CA2383298A1 (fr) | 2002-11-15 |
| CA2383298C true CA2383298C (fr) | 2008-01-29 |
Family
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Family Applications (1)
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| CA002383298A Expired - Fee Related CA2383298C (fr) | 2001-05-15 | 2002-05-10 | Nouveaux derives d'.alpha.-amino-acides, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US6706742B2 (enExample) |
| EP (1) | EP1258476B1 (enExample) |
| JP (1) | JP3798337B2 (enExample) |
| KR (1) | KR100460782B1 (enExample) |
| CN (1) | CN1164573C (enExample) |
| AR (1) | AR033735A1 (enExample) |
| AT (1) | ATE331705T1 (enExample) |
| AU (1) | AU780480B2 (enExample) |
| BR (1) | BR0201697A (enExample) |
| CA (1) | CA2383298C (enExample) |
| CY (1) | CY1105385T1 (enExample) |
| DE (1) | DE60212759T2 (enExample) |
| DK (1) | DK1258476T3 (enExample) |
| EA (1) | EA004865B1 (enExample) |
| ES (1) | ES2266422T3 (enExample) |
| FR (1) | FR2824825B1 (enExample) |
| HU (1) | HUP0201646A3 (enExample) |
| MX (1) | MXPA02004642A (enExample) |
| NO (1) | NO322569B1 (enExample) |
| NZ (1) | NZ518948A (enExample) |
| PL (1) | PL353910A1 (enExample) |
| PT (1) | PT1258476E (enExample) |
| SI (1) | SI1258476T1 (enExample) |
| ZA (1) | ZA200203867B (enExample) |
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| US7105526B2 (en) | 2002-06-28 | 2006-09-12 | Banyu Pharmaceuticals Co., Ltd. | Benzimidazole derivatives |
| EP1562897B1 (en) * | 2002-11-12 | 2009-09-16 | Merck & Co., Inc. | Phenylcarboxamide beta-secretase inhibitors for the treatment of alzheimer s disease |
| WO2004050022A2 (en) * | 2002-12-04 | 2004-06-17 | Merck & Co., Inc. | Phenylalanine derivatives as dipeptidyl peptidase inhibitors for the treatment or prevention of diabetes |
| US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
| US7550590B2 (en) * | 2003-03-25 | 2009-06-23 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| ZA200508439B (en) | 2003-05-05 | 2007-03-28 | Probiodrug Ag | Medical use of inhibitors of glutaminyl and glutamate cyclases |
| 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 |
| US7678909B1 (en) | 2003-08-13 | 2010-03-16 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| US7169926B1 (en) | 2003-08-13 | 2007-01-30 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| KR20060041309A (ko) * | 2003-08-13 | 2006-05-11 | 다케다 야쿠힌 고교 가부시키가이샤 | ４-피리미돈 유도체 및 펩티딜 펩티다제 저해제로서의 그의용도 |
| WO2005026148A1 (en) * | 2003-09-08 | 2005-03-24 | Takeda San Diego, Inc. | Dipeptidyl peptidase inhibitors |
| JP2007513058A (ja) * | 2003-09-08 | 2007-05-24 | 武田薬品工業株式会社 | ジペプチジルぺプチダーゼ阻害剤 |
| WO2005028438A1 (ja) | 2003-09-22 | 2005-03-31 | Banyu Pharmaceutical Co., Ltd. | 新規ピペリジン誘導体 |
| AU2004290897B2 (en) | 2003-11-17 | 2009-02-26 | Novartis Ag | Use of dipeptidyl peptidase IV inhibitors |
| WO2005058849A1 (en) * | 2003-12-15 | 2005-06-30 | Glenmark Pharmaceuticals Ltd. | New dipeptidyl peptidase in inhibitors; process for their preparation and compositions containing them |
| CN101262851A (zh) * | 2004-01-20 | 2008-09-10 | 诺瓦提斯公司 | 直接压片配方和方法 |
| ES2899417T3 (es) | 2004-01-20 | 2022-03-11 | Novartis Ag | Formulación y proceso de compresión directa |
| US7732446B1 (en) | 2004-03-11 | 2010-06-08 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| CN102134230B (zh) | 2004-03-15 | 2019-06-28 | 武田药品工业株式会社 | 二肽基肽酶抑制剂 |
| WO2005097759A1 (en) | 2004-03-29 | 2005-10-20 | Merck & Co., Inc. | Diaryltriazoles as inhibitors of 11-beta-hydroxysteroid dehydrogenase-1 |
| EP1734963A4 (en) | 2004-04-02 | 2008-06-18 | Merck & Co Inc | METHOD FOR TREATING PEOPLE WITH METABOLIC AND ANTHROPOMETRIC DISORDER |
| FR2870538B1 (fr) * | 2004-05-19 | 2006-07-14 | Servier Lab | Nouveaux derives de pyrrolidines et de thiazolidines, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| JP2008501714A (ja) * | 2004-06-04 | 2008-01-24 | 武田薬品工業株式会社 | ジペプチジルペプチダーゼインヒビター |
| BRPI0402260B1 (pt) | 2004-06-15 | 2015-02-18 | Botica Com Farmaceutica Ltda | Composição para produtos de higiene, cosméticos e perfumes. |
| WO2006019965A2 (en) | 2004-07-16 | 2006-02-23 | Takeda San Diego, Inc. | Dipeptidyl peptidase inhibitors |
| CA2574418A1 (en) * | 2004-07-23 | 2006-02-02 | Susan Marie Royalty | Peptidase inhibitors |
| ATE472531T1 (de) | 2004-08-06 | 2010-07-15 | Merck Sharp & Dohme | Sulfonylverbindungen als hemmer von 11-beta- hydroxysteroiddehydrogenase-1 |
| AU2005293266B2 (en) | 2004-10-12 | 2011-09-29 | Glenmark Pharmaceuticals S.A. | Novel dipeptidyl peptidase IV inhibitors, pharmaceutical compositions containing them, and process for their preparation |
| EP1828192B1 (en) * | 2004-12-21 | 2014-12-03 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| DOP2006000008A (es) | 2005-01-10 | 2006-08-31 | Arena Pharm Inc | Terapia combinada para el tratamiento de la diabetes y afecciones relacionadas y para el tratamiento de afecciones que mejoran mediante un incremento de la concentración sanguínea de glp-1 |
| ZA200707896B (en) * | 2005-03-14 | 2009-07-29 | High Point Pharma Llc | Benzazole derivatives, compositions, and methods of use as B-secretase inhibitors |
| BRPI0608469A2 (pt) | 2005-04-22 | 2010-01-05 | Alantos Pharmaceuticals Holding Inc | inibidores de dipeptidil peptidase-iv |
| WO2006129826A1 (ja) | 2005-05-30 | 2006-12-07 | Banyu Pharmaceutical Co., Ltd. | 新規ピペリジン誘導体 |
| MY152185A (en) | 2005-06-10 | 2014-08-29 | Novartis Ag | Modified release 1-[(3-hydroxy-adamant-1-ylamino)-acetyl]-pyrrolidine-2(s)-carbonitrile formulation |
| EP1916239A4 (en) | 2005-08-10 | 2009-10-21 | Banyu Pharma Co Ltd | PYRIDOLVERBINDUNG |
| KR20080030652A (ko) * | 2005-08-11 | 2008-04-04 | 에프. 호프만-라 로슈 아게 | Ｄｐｐ-ｉｖ 억제제를 포함하는 약학 조성물 |
| EP1921065B1 (en) | 2005-08-24 | 2010-10-20 | Banyu Pharmaceutical Co., Ltd. | Phenylpyridone derivative |
| EP1939194A4 (en) | 2005-09-07 | 2010-12-08 | Banyu Pharma Co Ltd | BICYCLIC AROMATIC SUBSTITUTED PYRIDONE DERIVATIVE |
| ATE532518T1 (de) | 2005-09-14 | 2011-11-15 | Takeda Pharmaceutical | Dipeptidyl-peptidase-hemmer zur behandlung von diabetes |
| GEP20135791B (en) * | 2005-09-14 | 2013-03-25 | Takeda Pharmaceutical | Use of dipeptidyl peptidase inhibitors |
| CA2622642C (en) * | 2005-09-16 | 2013-12-31 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| TW200745080A (en) * | 2005-09-16 | 2007-12-16 | Takeda Pharmaceuticals Co | Polymorphs of tartrate salt of 2-[2-(3-(R)-amino-piperidin-1-yl)-5-fluoro-6-oxo-6H-pyrimidin-1-ylmethyl]-benzonitrile and methods of use therefor |
| TW200745079A (en) * | 2005-09-16 | 2007-12-16 | Takeda Pharmaceuticals Co | Polymorphs of benzoate salt of 2-[[6-[(3R)-3-amino-1-piperidinyl]-3,4-dihydro-3-methyl-2,4-dioxo-1(2H)-pyrimidinyl]methyl]-benzonitrile and methods of use therefor |
| JOP20180109A1 (ar) * | 2005-09-29 | 2019-01-30 | Novartis Ag | تركيبة جديدة |
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| IL111785A0 (en) * | 1993-12-03 | 1995-01-24 | Ferring Bv | Dp-iv inhibitors and pharmaceutical compositions containing them |
| US6090786A (en) * | 1994-06-10 | 2000-07-18 | Fondatech Benelux N.V. | Serine proteases, their activity and their synthetic inhibitors |
| GB9504350D0 (en) * | 1995-03-04 | 1995-04-26 | Sod Conseils Rech Applic | Arginine derivatives |
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