NZ531942A - N-substituted pyrrolidin derivatives as dipeptidyl peptidase IV inhibitors - Google Patents
N-substituted pyrrolidin derivatives as dipeptidyl peptidase IV inhibitorsInfo
- Publication number
- NZ531942A NZ531942A NZ531942A NZ53194202A NZ531942A NZ 531942 A NZ531942 A NZ 531942A NZ 531942 A NZ531942 A NZ 531942A NZ 53194202 A NZ53194202 A NZ 53194202A NZ 531942 A NZ531942 A NZ 531942A
- Authority
- NZ
- New Zealand
- Prior art keywords
- methyl
- phenyl
- pyridin
- acetyl
- carbonitrile
- Prior art date
Links
- -1 N-substituted pyrrolidin Chemical class 0.000 title claims abstract description 418
- 229940124213 Dipeptidyl peptidase 4 (DPP IV) inhibitor Drugs 0.000 title abstract description 3
- 239000003603 dipeptidyl peptidase IV inhibitor Substances 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 397
- 150000003839 salts Chemical class 0.000 claims abstract description 95
- 238000011282 treatment Methods 0.000 claims abstract description 76
- 108010067722 Dipeptidyl Peptidase 4 Proteins 0.000 claims abstract description 21
- 102100025012 Dipeptidyl peptidase 4 Human genes 0.000 claims abstract description 21
- 201000010099 disease Diseases 0.000 claims abstract description 21
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 21
- 238000011321 prophylaxis Methods 0.000 claims abstract description 18
- 208000002705 Glucose Intolerance Diseases 0.000 claims abstract description 17
- 201000009104 prediabetes syndrome Diseases 0.000 claims abstract description 17
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 9
- 125000001424 substituent group Chemical group 0.000 claims description 89
- 229910052736 halogen Inorganic materials 0.000 claims description 81
- 150000002367 halogens Chemical class 0.000 claims description 79
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 78
- 125000001072 heteroaryl group Chemical group 0.000 claims description 68
- 239000000203 mixture Substances 0.000 claims description 68
- 238000000034 method Methods 0.000 claims description 65
- 125000003118 aryl group Chemical group 0.000 claims description 59
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 59
- 239000000843 powder Substances 0.000 claims description 56
- 229910001868 water Inorganic materials 0.000 claims description 46
- 229910052739 hydrogen Inorganic materials 0.000 claims description 36
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
- 239000003921 oil Substances 0.000 claims description 35
- 238000002360 preparation method Methods 0.000 claims description 35
- 239000001257 hydrogen Substances 0.000 claims description 31
- ALSCEGDXFJIYES-UHFFFAOYSA-N pyrrolidine-2-carbonitrile Chemical compound N#CC1CCCN1 ALSCEGDXFJIYES-UHFFFAOYSA-N 0.000 claims description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 125000004076 pyridyl group Chemical group 0.000 claims description 23
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 18
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 18
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 15
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 14
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 13
- 125000000335 thiazolyl group Chemical group 0.000 claims description 13
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 125000001544 thienyl group Chemical group 0.000 claims description 12
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 10
- 239000002775 capsule Substances 0.000 claims description 9
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 9
- 208000001145 Metabolic Syndrome Diseases 0.000 claims description 8
- 208000008589 Obesity Diseases 0.000 claims description 8
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 8
- 235000020824 obesity Nutrition 0.000 claims description 8
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 8
- 230000001225 therapeutic effect Effects 0.000 claims description 8
- 208000011231 Crohn disease Diseases 0.000 claims description 7
- 206010009887 colitis Diseases 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 150000002431 hydrogen Chemical group 0.000 claims description 7
- 239000004615 ingredient Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000002971 oxazolyl group Chemical group 0.000 claims description 7
- 239000013543 active substance Substances 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 6
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 229920000159 gelatin Polymers 0.000 claims description 5
- 235000019322 gelatine Nutrition 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000006289 hydroxybenzyl group Chemical group 0.000 claims description 5
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
- 125000001041 indolyl group Chemical group 0.000 claims description 5
- QYRWMYNQCXSWLV-INIZCTEOSA-N (2s)-1-[2-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethylamino]acetyl]pyrrolidine-2-carbonitrile Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCNCC(=O)N1CCC[C@H]1C#N QYRWMYNQCXSWLV-INIZCTEOSA-N 0.000 claims description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 4
- 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 claims description 4
- 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 claims description 4
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
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- 239000001913 cellulose Substances 0.000 claims description 4
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- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 4
- 239000008101 lactose Substances 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 125000001425 triazolyl group Chemical group 0.000 claims description 4
- LHAUOAQRSGNEMT-SFHVURJKSA-N (2s)-1-[2-[2-[(5-phenylpyridin-2-yl)amino]ethylamino]acetyl]pyrrolidine-2-carbonitrile Chemical compound N1([C@@H](CCC1)C#N)C(=O)CNCCNC(N=C1)=CC=C1C1=CC=CC=C1 LHAUOAQRSGNEMT-SFHVURJKSA-N 0.000 claims description 3
- KBVUIBGUSADKSG-SFHVURJKSA-N (2s)-1-[2-[2-[[5-(3-methoxyphenyl)pyridin-2-yl]amino]ethylamino]acetyl]pyrrolidine-2-carbonitrile Chemical compound COC1=CC=CC(C=2C=NC(NCCNCC(=O)N3[C@@H](CCC3)C#N)=CC=2)=C1 KBVUIBGUSADKSG-SFHVURJKSA-N 0.000 claims description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000005872 benzooxazolyl group Chemical group 0.000 claims description 3
- 229920002678 cellulose Polymers 0.000 claims description 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
- 235000019359 magnesium stearate Nutrition 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000002757 morpholinyl group Chemical group 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- MMXPNIQJMULULS-INIZCTEOSA-N (2s)-1-[2-[2-[2-(4-fluorophenyl)-5-methyl-1,3-oxazol-4-yl]ethylamino]acetyl]pyrrolidine-2-carbonitrile Chemical compound CC=1OC(C=2C=CC(F)=CC=2)=NC=1CCNCC(=O)N1CCC[C@H]1C#N MMXPNIQJMULULS-INIZCTEOSA-N 0.000 claims description 2
- ITQZLPLJJPHVQI-QFIPXVFZSA-N (2s)-1-[2-[2-[5-methyl-2-(4-phenylmethoxyphenyl)-1,3-oxazol-4-yl]ethylamino]acetyl]pyrrolidine-2-carbonitrile Chemical compound CC=1OC(C=2C=CC(OCC=3C=CC=CC=3)=CC=2)=NC=1CCNCC(=O)N1CCC[C@H]1C#N ITQZLPLJJPHVQI-QFIPXVFZSA-N 0.000 claims description 2
- UGRDWVKNSOHGRX-INIZCTEOSA-N (2s)-1-[2-[2-[[4-(3-phenyl-1,2-oxazol-5-yl)-1,3-thiazol-2-yl]amino]ethylamino]acetyl]pyrrolidine-2-carbonitrile Chemical compound N1([C@@H](CCC1)C#N)C(=O)CNCCNC(SC=1)=NC=1C(ON=1)=CC=1C1=CC=CC=C1 UGRDWVKNSOHGRX-INIZCTEOSA-N 0.000 claims description 2
- BTQXXKSKFXDOPD-INIZCTEOSA-N (2s)-1-[2-[2-[[4-(4-cyanophenyl)-1,3-thiazol-2-yl]amino]ethylamino]acetyl]pyrrolidine-2-carbonitrile Chemical compound N1([C@@H](CCC1)C#N)C(=O)CNCCNC(SC=1)=NC=1C1=CC=C(C#N)C=C1 BTQXXKSKFXDOPD-INIZCTEOSA-N 0.000 claims description 2
- CYUYIJUNEAEWTE-IBGZPJMESA-N (2s)-1-[2-[2-[[5-(4-cyanophenyl)pyridin-2-yl]amino]ethylamino]acetyl]pyrrolidine-2-carbonitrile Chemical compound N1([C@@H](CCC1)C#N)C(=O)CNCCNC(N=C1)=CC=C1C1=CC=C(C#N)C=C1 CYUYIJUNEAEWTE-IBGZPJMESA-N 0.000 claims description 2
- 125000000972 4,5-dimethylthiazol-2-yl group Chemical group [H]C([H])([H])C1=C(N=C(*)S1)C([H])([H])[H] 0.000 claims description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
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- 239000003937 drug carrier Substances 0.000 claims description 2
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- 125000005493 quinolyl group Chemical group 0.000 claims description 2
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- 244000068988 Glycine max Species 0.000 claims 2
- 235000010469 Glycine max Nutrition 0.000 claims 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 claims 2
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- 229940057948 magnesium stearate Drugs 0.000 claims 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 claims 2
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 claims 2
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims 2
- VARXXRGAOGCJNM-KRWDZBQOSA-N (2s)-1-[2-[2-[[5-(2-methoxyphenyl)pyridin-2-yl]amino]ethylamino]acetyl]pyrrolidine-2-carbonitrile Chemical compound COC1=CC=CC=C1C(C=N1)=CC=C1NCCNCC(=O)N1[C@H](C#N)CCC1 VARXXRGAOGCJNM-KRWDZBQOSA-N 0.000 claims 1
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- CQVKMVQRSNNAGO-UHFFFAOYSA-N 2-[4-formyl-3-methyl-n-(2-methylsulfonyloxyethyl)anilino]ethyl methanesulfonate Chemical compound CC1=CC(N(CCOS(C)(=O)=O)CCOS(C)(=O)=O)=CC=C1C=O CQVKMVQRSNNAGO-UHFFFAOYSA-N 0.000 claims 1
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 claims 1
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- 201000007851 type 1 diabetes mellitus 20 Diseases 0.000 claims 1
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- RWEBPCTYBHXFPA-UHFFFAOYSA-N oxathiazinane-3-carboxylic acid Chemical compound OC(=O)N1CCCOS1 RWEBPCTYBHXFPA-UHFFFAOYSA-N 0.000 description 17
- 239000002243 precursor Substances 0.000 description 17
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- 125000004093 cyano group Chemical group *C#N 0.000 description 13
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
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- XDJCYKMWJCYQJM-UHFFFAOYSA-N tert-butyl n-(3-hydroxypropyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCCO XDJCYKMWJCYQJM-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 208000035408 type 1 diabetes mellitus 1 Diseases 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
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- 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
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- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- 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
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
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- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
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Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Biophysics (AREA)
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- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Molecular Biology (AREA)
- Botany (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyrrole Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01125338 | 2001-10-26 | ||
| EP02018227 | 2002-08-21 | ||
| PCT/EP2002/011711 WO2003037327A1 (en) | 2001-10-26 | 2002-10-18 | N-substituted pyrrolidin derivatives as dipeptidyl peptidase iv inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ531942A true NZ531942A (en) | 2006-09-29 |
Family
ID=26076751
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ531942A NZ531942A (en) | 2001-10-26 | 2002-10-18 | N-substituted pyrrolidin derivatives as dipeptidyl peptidase IV inhibitors |
Country Status (27)
| Country | Link |
|---|---|
| US (3) | US6861440B2 (https=) |
| EP (1) | EP1441719B1 (https=) |
| JP (1) | JP4171417B2 (https=) |
| KR (1) | KR100645671B1 (https=) |
| CN (1) | CN1713907B (https=) |
| AR (1) | AR036958A1 (https=) |
| AT (1) | ATE503477T1 (https=) |
| AU (1) | AU2002338902B2 (https=) |
| BR (1) | BR0213539A (https=) |
| CA (1) | CA2463709C (https=) |
| DE (1) | DE60239629D1 (https=) |
| EA (1) | EA007968B1 (https=) |
| GT (2) | GT200200220A (https=) |
| HR (1) | HRP20040344A2 (https=) |
| HU (1) | HUP0402107A3 (https=) |
| IL (2) | IL161158A0 (https=) |
| MA (1) | MA26342A1 (https=) |
| MX (1) | MXPA04003759A (https=) |
| NO (1) | NO20041709L (https=) |
| NZ (1) | NZ531942A (https=) |
| PA (1) | PA8557001A1 (https=) |
| PE (1) | PE20030704A1 (https=) |
| PL (1) | PL370551A1 (https=) |
| TN (1) | TNSN04073A1 (https=) |
| UY (1) | UY27518A1 (https=) |
| WO (1) | WO2003037327A1 (https=) |
| YU (1) | YU34404A (https=) |
Families Citing this family (151)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2296979T3 (es) | 2001-06-27 | 2008-05-01 | Smithkline Beecham Corporation | Fluoropirrolidinas como inhibidores de dipeptidil peptidasa. |
| GB0125445D0 (en) * | 2001-10-23 | 2001-12-12 | Ferring Bv | Protease Inhibitors |
| US6861440B2 (en) * | 2001-10-26 | 2005-03-01 | Hoffmann-La Roche Inc. | DPP IV inhibitors |
| US7407955B2 (en) | 2002-08-21 | 2008-08-05 | Boehringer Ingelheim Pharma Gmbh & Co., Kg | 8-[3-amino-piperidin-1-yl]-xanthines, the preparation thereof and their use as pharmaceutical compositions |
| JP2005170792A (ja) * | 2002-11-22 | 2005-06-30 | Mitsubishi Pharma Corp | L−プロリン誘導体およびその医薬としての用途。 |
| US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
| PT1595866T (pt) * | 2003-01-31 | 2016-09-14 | Sanwa Kagaku Kenkyusho Co | Cianopirrolidinas úteis para o tratamento entre outras de síndrome metabólica |
| US7550590B2 (en) | 2003-03-25 | 2009-06-23 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| JP4806628B2 (ja) | 2003-05-05 | 2011-11-02 | プロビオドルグ エージー | グルタミニルシクラーゼ阻害剤 |
| WO2004103993A1 (en) | 2003-05-14 | 2004-12-02 | Syrrx, Inc. | Dipeptidyl peptidase inhibitors |
| WO2004110436A1 (en) * | 2003-06-06 | 2004-12-23 | Merck & Co., Inc. | Fused indoles as dipeptidyl peptidase inhibitors for the treatment or prevention of diabetes |
| ES2355105T3 (es) * | 2003-06-20 | 2011-03-22 | F. Hoffmann-La Roche Ag | Pirido(2,1-a)isoquinolina como inhibidores de la dpp-iv. |
| 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 |
| US7678909B1 (en) | 2003-08-13 | 2010-03-16 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| US7790734B2 (en) | 2003-09-08 | 2010-09-07 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| WO2005030751A2 (en) * | 2003-09-08 | 2005-04-07 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| EP2338490A3 (en) | 2003-11-03 | 2012-06-06 | Probiodrug AG | Combinations useful for the treatment of neuronal disorders |
| KR20120008093A (ko) | 2003-11-17 | 2012-01-25 | 노파르티스 아게 | 디펩티딜 펩티다제 ⅳ 억제제의 용도 |
| DK1715893T3 (da) | 2004-01-20 | 2009-11-09 | Novartis Pharma Ag | Direkte kompressionsformulering og fremgangsmåde |
| US7230002B2 (en) | 2004-02-03 | 2007-06-12 | Glenmark Pharmaceuticals Ltd. | Dipeptidyl peptidase IV inhibitors; processes for their preparation and compositions thereof |
| US7304086B2 (en) | 2004-02-05 | 2007-12-04 | Probiodrug Ag | Inhibitors of glutaminyl cyclase |
| US7501426B2 (en) | 2004-02-18 | 2009-03-10 | Boehringer Ingelheim International Gmbh | 8-[3-amino-piperidin-1-yl]-xanthines, their preparation and their use as pharmaceutical compositions |
| EP1729774A4 (en) | 2004-03-09 | 2009-05-06 | Nat Health Research Institutes | PYRROLIDINE CONNECTIONS |
| US7732446B1 (en) | 2004-03-11 | 2010-06-08 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| CN102127057A (zh) | 2004-03-15 | 2011-07-20 | 武田药品工业株式会社 | 二肽基肽酶抑制剂 |
| US20080125403A1 (en) | 2004-04-02 | 2008-05-29 | Merck & Co., Inc. | Method of Treating Men with Metabolic and Anthropometric Disorders |
| CN1950349A (zh) * | 2004-05-04 | 2007-04-18 | 默克公司 | 作为用于治疗或预防糖尿病的二肽基肽酶-ⅳ抑制剂的1,2,4-噁二唑衍生物 |
| 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 |
| WO2006019965A2 (en) | 2004-07-16 | 2006-02-23 | Takeda San Diego, Inc. | Dipeptidyl peptidase inhibitors |
| ATE553077T1 (de) | 2004-07-23 | 2012-04-15 | Nuada Llc | Peptidaseinhibitoren |
| FR2873694B1 (fr) * | 2004-07-27 | 2006-12-08 | Merck Sante Soc Par Actions Si | Nouveaux aza-indoles inhibiteurs de la mtp et apob |
| BRPI0516340A (pt) | 2004-10-12 | 2008-09-16 | Glenmark Pharmaceuticals Sa | composto, composição farmacêutica, método para tratar uma condição que é regulada ou normalizada via inibição de dpp-iv, método para tratar um distúrbio metabólico, método para tratar diabete tipo ii, método para diminuir glicose no sangue, método para tratamento e profilaxia de uma doença, método para tratar toleráncia não prejudicada a glicose insulino-resistente, método para a manufatura de uma composição farmacêutica e processo para a preparação de compostos |
| DE102004054054A1 (de) | 2004-11-05 | 2006-05-11 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Verfahren zur Herstellung chiraler 8-(3-Amino-piperidin-1-yl)-xanthine |
| WO2006068978A2 (en) | 2004-12-21 | 2006-06-29 | Takeda Pharmaceutial 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 |
| EP1888571A2 (en) * | 2005-03-22 | 2008-02-20 | F. Hoffmann-Roche AG | New salt and polymorphs of a dpp-iv inhibitor |
| TWI357902B (en) * | 2005-04-01 | 2012-02-11 | Lg Life Science Ltd | Dipeptidyl peptidase-iv inhibiting compounds, meth |
| AU2006239929B2 (en) * | 2005-04-22 | 2011-11-03 | Alantos Pharmaceuticals Holding, Inc. | Dipeptidyl peptidase-IV inhibitors |
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