ZA200608489B - Tri (cyclo) substituted amide compounds - Google Patents
Tri (cyclo) substituted amide compounds Download PDFInfo
- Publication number
- ZA200608489B ZA200608489B ZA2006/08489A ZA200608489A ZA200608489B ZA 200608489 B ZA200608489 B ZA 200608489B ZA 2006/08489 A ZA2006/08489 A ZA 2006/08489A ZA 200608489 A ZA200608489 A ZA 200608489A ZA 200608489 B ZA200608489 B ZA 200608489B
- Authority
- ZA
- South Africa
- Prior art keywords
- pharmaceutically acceptable
- fluorothiazol
- acceptable salt
- alkyl
- propionamide
- Prior art date
Links
- -1 amide compounds Chemical class 0.000 title claims description 48
- 150000001875 compounds Chemical class 0.000 claims description 122
- 150000003839 salts Chemical class 0.000 claims description 60
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 36
- 229940080818 propionamide Drugs 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 206010012601 diabetes mellitus Diseases 0.000 claims description 23
- 238000002360 preparation method Methods 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
- 238000011282 treatment Methods 0.000 claims description 15
- 201000001421 hyperglycemia Diseases 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 230000004913 activation Effects 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 150000001408 amides Chemical class 0.000 claims description 9
- 239000003937 drug carrier Substances 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 230000000069 prophylactic effect Effects 0.000 claims description 9
- 230000001225 therapeutic effect Effects 0.000 claims description 9
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 239000003472 antidiabetic agent Substances 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 208000002705 Glucose Intolerance Diseases 0.000 claims description 4
- 206010018429 Glucose tolerance impaired Diseases 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 229940125708 antidiabetic agent Drugs 0.000 claims description 4
- VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical compound [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 claims description 4
- 201000009104 prediabetes syndrome Diseases 0.000 claims description 4
- 230000002265 prevention Effects 0.000 claims description 4
- 125000005330 8 membered heterocyclic group Chemical group 0.000 claims description 3
- DFCRJAVBZBKLAX-ZRRZQRFHSA-N (e)-n-(5-fluoro-1,3-thiazol-2-yl)-2-(4-methylsulfonylphenyl)-3-[(1s)-3-oxocyclopentyl]prop-2-enamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(\C(=O)NC=1SC(F)=CN=1)=C/[C@@H]1CC(=O)CC1 DFCRJAVBZBKLAX-ZRRZQRFHSA-N 0.000 claims description 2
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- RFWUNSYBDRUYQQ-MHWRWJLKSA-N (e)-n-(5-fluoro-1,3-thiazol-2-yl)-2-(4-methylsulfonylphenyl)-3-(4-oxocyclohexyl)prop-2-enamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(\C(=O)NC=1SC(F)=CN=1)=C/C1CCC(=O)CC1 RFWUNSYBDRUYQQ-MHWRWJLKSA-N 0.000 claims 1
- ZJNJADPHMHZKPY-OQLLNIDSSA-N (e)-n-(5-fluoro-1,3-thiazol-2-yl)-3-(3-hydroxycyclopentyl)-2-(4-methylsulfonylphenyl)prop-2-enamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(\C(=O)NC=1SC(F)=CN=1)=C/C1CC(O)CC1 ZJNJADPHMHZKPY-OQLLNIDSSA-N 0.000 claims 1
- 101100059652 Mus musculus Cetn1 gene Proteins 0.000 claims 1
- 101100059655 Mus musculus Cetn2 gene Proteins 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 52
- 239000000243 solution Substances 0.000 description 38
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 37
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 239000012190 activator Substances 0.000 description 27
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 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 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 235000019439 ethyl acetate Nutrition 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 12
- 239000012267 brine Substances 0.000 description 11
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 239000000543 intermediate Substances 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 229920006395 saturated elastomer Polymers 0.000 description 10
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000008280 blood Substances 0.000 description 9
- 210000004369 blood Anatomy 0.000 description 9
- 239000008103 glucose Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000000969 carrier Substances 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 125000000524 functional group Chemical group 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 231100000252 nontoxic Toxicity 0.000 description 7
- 230000003000 nontoxic effect Effects 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 6
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 102000030595 Glucokinase Human genes 0.000 description 5
- 108010021582 Glucokinase Proteins 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 238000003556 assay Methods 0.000 description 5
- 230000037396 body weight Effects 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 125000006239 protecting group Chemical group 0.000 description 5
- 238000000935 solvent evaporation Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical class NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 4
- HUUPNPWVDMNTAH-UHFFFAOYSA-N 5-fluoro-1,3-thiazol-2-amine Chemical compound NC1=NC=C(F)S1 HUUPNPWVDMNTAH-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
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- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
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- 102000010705 glucose-6-phosphate dehydrogenase activity proteins Human genes 0.000 description 4
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- 125000005842 heteroatom Chemical group 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 4
- 239000000314 lubricant Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
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- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 3
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- 229960002277 tolazamide Drugs 0.000 description 1
- OUDSBRTVNLOZBN-UHFFFAOYSA-N tolazamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NN1CCCCCC1 OUDSBRTVNLOZBN-UHFFFAOYSA-N 0.000 description 1
- 229960005371 tolbutamide Drugs 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 239000001226 triphosphate Substances 0.000 description 1
- 235000011178 triphosphate Nutrition 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 description 1
- 229960001641 troglitazone Drugs 0.000 description 1
- GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- 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
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
-
- 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
- A61P3/06—Antihyperlipidemics
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US56417104P | 2004-04-21 | 2004-04-21 | |
| US60107704P | 2004-08-12 | 2004-08-12 | |
| PCT/GB2005/050053 WO2005103021A1 (en) | 2004-04-21 | 2005-04-19 | Tri(cyclo) substituted amide compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200608489B true ZA200608489B (en) | 2008-06-25 |
Family
ID=34965439
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA2006/08489A ZA200608489B (en) | 2004-04-21 | 2006-10-11 | Tri (cyclo) substituted amide compounds |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US20080242869A1 (https=) |
| EP (1) | EP1740560A1 (https=) |
| JP (1) | JP2007533722A (https=) |
| KR (1) | KR20060134179A (https=) |
| AU (1) | AU2005235798A1 (https=) |
| BR (1) | BRPI0510163A (https=) |
| CA (1) | CA2563192A1 (https=) |
| EA (1) | EA012204B1 (https=) |
| IL (1) | IL178473A0 (https=) |
| MA (1) | MA28545B1 (https=) |
| MX (1) | MXPA06012008A (https=) |
| NO (1) | NO20065260L (https=) |
| NZ (1) | NZ550567A (https=) |
| WO (1) | WO2005103021A1 (https=) |
| ZA (1) | ZA200608489B (https=) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE0102299D0 (sv) | 2001-06-26 | 2001-06-26 | Astrazeneca Ab | Compounds |
| SE0102764D0 (sv) | 2001-08-17 | 2001-08-17 | Astrazeneca Ab | Compounds |
| BR0314864A (pt) | 2002-10-03 | 2005-08-02 | Novartis Ag | Compostos orgânicos |
| GB0226931D0 (en) | 2002-11-19 | 2002-12-24 | Astrazeneca Ab | Chemical compounds |
| US7781451B2 (en) | 2004-04-02 | 2010-08-24 | Novartis Ag | Thiazolopyridine derivatives, pharmaceut ical conditions containing them and methods of treating glucokinase mediated conditions |
| BRPI0509573A (pt) | 2004-04-02 | 2007-09-25 | Novartis Ag | derivados de sulfonamida-tiazolpiridina como ativadores de glicocinase úteis para o tratamento de diabetes do tipo 2 |
| KR100890695B1 (ko) * | 2004-08-12 | 2009-03-26 | 프로시디온 리미티드 | 치환된 페닐아세트아미드 및 글루코키나제 활성화제로서의그의 용도 |
| GB0418058D0 (en) * | 2004-08-12 | 2004-09-15 | Prosidion Ltd | Fluorination process |
| KR101346902B1 (ko) | 2005-07-09 | 2014-01-02 | 아스트라제네카 아베 | 당뇨병 치료에 있어 ｇｌｋ 활성화제로서 사용하기 위한헤테로아릴 벤즈아미드 유도체 |
| CA2624102A1 (en) | 2005-09-29 | 2007-04-12 | Sanofi-Aventis | Phenyl- and pyridinyl- 1, 2 , 4 - oxadiazolone derivatives, processes for their preparation and their use as pharmaceuticals |
| GT200600428A (es) | 2005-09-30 | 2007-05-21 | Compuestos organicos | |
| GT200600429A (es) | 2005-09-30 | 2007-04-30 | Compuestos organicos | |
| US20080293741A1 (en) * | 2005-11-03 | 2008-11-27 | Matthew Colin Thor Fyfe | Tricyclo Substituted Amides as Glucokinase Modulators |
| PE20080251A1 (es) | 2006-05-04 | 2008-04-25 | Boehringer Ingelheim Int | Usos de inhibidores de dpp iv |
| US7888504B2 (en) | 2006-07-06 | 2011-02-15 | Bristol-Myers Squibb Company | Glucokinase activators and methods of using same |
| US7910747B2 (en) | 2006-07-06 | 2011-03-22 | Bristol-Myers Squibb Company | Phosphonate and phosphinate pyrazolylamide glucokinase activators |
| KR20090025358A (ko) | 2006-07-24 | 2009-03-10 | 에프. 호프만-라 로슈 아게 | 글루코키나제 활성화제로서의 피라졸 |
| US7902248B2 (en) | 2006-12-14 | 2011-03-08 | Hoffmann-La Roche Inc. | Oxime glucokinase activators |
| TW200831081A (en) | 2006-12-25 | 2008-08-01 | Kyorin Seiyaku Kk | Glucokinase activator |
| JP5248477B2 (ja) * | 2007-03-07 | 2013-07-31 | 杏林製薬株式会社 | グルコキナーゼ活性化物質 |
| TW200934772A (en) * | 2008-01-15 | 2009-08-16 | Lilly Co Eli | Crystalline(R)-2-(4-cyclopropanesulphonyl-phenyl)-N-pyrazin-2-yl-3-(tetrahydropyran-4-yl)-propionamide |
| JP5287730B2 (ja) | 2008-01-18 | 2013-09-11 | アステラス製薬株式会社 | フェニルアセトアミド誘導体 |
| US8258134B2 (en) | 2008-04-16 | 2012-09-04 | Hoffmann-La Roche Inc. | Pyridazinone glucokinase activators |
| US7741327B2 (en) | 2008-04-16 | 2010-06-22 | Hoffmann-La Roche Inc. | Pyrrolidinone glucokinase activators |
| KR101608259B1 (ko) | 2008-04-28 | 2016-04-01 | 교린 세이야꾸 가부시키 가이샤 | 시클로펜틸아크릴산아미드 유도체 |
| KR20110018366A (ko) | 2008-05-16 | 2011-02-23 | 다케다 샌디에고, 인코포레이티드 | 글루코키나아제 활성제 |
| CA2745843A1 (en) * | 2008-12-08 | 2010-06-17 | Hamid Hoveyda | Compounds, pharmaceutical composition and methods for use in treating metabolic disorders |
| UA104742C2 (uk) | 2008-12-19 | 2014-03-11 | Эли Лилли Энд Компани | Похідні арилциклопропілацетаміду, застосовні як активатори глюкокінази |
| US8222416B2 (en) | 2009-12-14 | 2012-07-17 | Hoffmann-La Roche Inc. | Azaindole glucokinase activators |
| US20130281708A1 (en) | 2010-03-18 | 2013-10-24 | Takeda California, Inc. | Process for the Production of 2-Amino-5-Fluorothiazole |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6610846B1 (en) * | 1999-03-29 | 2003-08-26 | Hoffman-La Roche Inc. | Heteroaromatic glucokinase activators |
| PL350669A1 (en) * | 1999-03-29 | 2003-01-27 | Hoffmann La Roche | Glucokinase activators |
| US6353111B1 (en) * | 1999-12-15 | 2002-03-05 | Hoffmann-La Roche Inc. | Trans olefinic glucokinase activators |
| DK1282611T3 (da) * | 2000-05-08 | 2005-02-14 | Hoffmann La Roche | Substituerede phenylacetatamider og anvendelse deraf som glucokinaseaktivatorer |
| DE60111534T2 (de) * | 2000-07-20 | 2006-05-11 | F. Hoffmann-La Roche Ag | Alpha-acyl- und alpha-heteroatom-substituierte benzenacetamide verwendbar als glucokinase-aktivatoren |
| DE60117059T2 (de) * | 2000-12-06 | 2006-10-26 | F. Hoffmann-La Roche Ag | Kondensierte heteroaromatische glucokinaseaktivatoren |
| EP1501815B1 (en) * | 2002-04-26 | 2006-11-22 | F. Hoffmann-La Roche Ag | Substituted phenylacetamides and their use as glucokinase activators |
| PL378117A1 (pl) * | 2003-02-11 | 2006-03-06 | Prosidion Limited | Tricyklopodstawione związki amidowe |
-
2005
- 2005-04-19 MX MXPA06012008A patent/MXPA06012008A/es unknown
- 2005-04-19 JP JP2007508982A patent/JP2007533722A/ja not_active Withdrawn
- 2005-04-19 CA CA002563192A patent/CA2563192A1/en not_active Abandoned
- 2005-04-19 NZ NZ550567A patent/NZ550567A/en not_active IP Right Cessation
- 2005-04-19 EA EA200601747A patent/EA012204B1/ru not_active IP Right Cessation
- 2005-04-19 KR KR1020067022240A patent/KR20060134179A/ko not_active Ceased
- 2005-04-19 US US11/578,752 patent/US20080242869A1/en not_active Abandoned
- 2005-04-19 WO PCT/GB2005/050053 patent/WO2005103021A1/en not_active Ceased
- 2005-04-19 BR BRPI0510163-8A patent/BRPI0510163A/pt not_active IP Right Cessation
- 2005-04-19 EP EP05732317A patent/EP1740560A1/en not_active Withdrawn
- 2005-04-19 AU AU2005235798A patent/AU2005235798A1/en not_active Abandoned
-
2006
- 2006-10-05 IL IL178473A patent/IL178473A0/en unknown
- 2006-10-11 ZA ZA2006/08489A patent/ZA200608489B/en unknown
- 2006-10-20 MA MA29401A patent/MA28545B1/fr unknown
- 2006-11-15 NO NO20065260A patent/NO20065260L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| WO2005103021A1 (en) | 2005-11-03 |
| US20080242869A1 (en) | 2008-10-02 |
| KR20060134179A (ko) | 2006-12-27 |
| BRPI0510163A (pt) | 2007-10-02 |
| JP2007533722A (ja) | 2007-11-22 |
| EA200601747A1 (ru) | 2007-04-27 |
| MA28545B1 (fr) | 2007-04-03 |
| NO20065260L (no) | 2006-11-21 |
| EP1740560A1 (en) | 2007-01-10 |
| NZ550567A (en) | 2010-07-30 |
| AU2005235798A1 (en) | 2005-11-03 |
| IL178473A0 (en) | 2007-02-11 |
| MXPA06012008A (es) | 2007-01-25 |
| CA2563192A1 (en) | 2005-11-03 |
| EA012204B1 (ru) | 2009-08-28 |
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