ZA200403797B - Biphenylmethyl-thiazolidinediones and analogues and their use as PPAR-gamma activators. - Google Patents
Biphenylmethyl-thiazolidinediones and analogues and their use as PPAR-gamma activators. Download PDFInfo
- Publication number
- ZA200403797B ZA200403797B ZA200403797A ZA200403797A ZA200403797B ZA 200403797 B ZA200403797 B ZA 200403797B ZA 200403797 A ZA200403797 A ZA 200403797A ZA 200403797 A ZA200403797 A ZA 200403797A ZA 200403797 B ZA200403797 B ZA 200403797B
- Authority
- ZA
- South Africa
- Prior art keywords
- ylmethyl
- biphenyl
- radical
- dioxothiazolidin
- methyl
- Prior art date
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- 239000012190 activator Substances 0.000 title description 5
- 102000000536 PPAR gamma Human genes 0.000 title 1
- 108010016731 PPAR gamma Proteins 0.000 title 1
- 229940123464 Thiazolidinedione Drugs 0.000 title 1
- -1 alkyl radical Chemical class 0.000 claims description 144
- 239000000203 mixture Substances 0.000 claims description 102
- 150000001875 compounds Chemical class 0.000 claims description 83
- 150000003254 radicals Chemical class 0.000 claims description 69
- 125000004432 carbon atom Chemical group C* 0.000 claims description 63
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
- 206010000496 acne Diseases 0.000 claims description 22
- 150000005840 aryl radicals Chemical class 0.000 claims description 22
- 208000002874 Acne Vulgaris Diseases 0.000 claims description 18
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 18
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 18
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 14
- 229920000570 polyether Polymers 0.000 claims description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 claims description 13
- 238000011282 treatment Methods 0.000 claims description 13
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 10
- 208000035475 disorder Diseases 0.000 claims description 10
- 125000000524 functional group Chemical group 0.000 claims description 10
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 10
- 239000002537 cosmetic Substances 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
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- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 230000032683 aging Effects 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
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- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 4
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- HKPCOWRPTJDTEE-UHFFFAOYSA-N methyl 8-[[3-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenyl]phenyl]methyl-methylamino]-8-oxooctanoate Chemical compound COC(=O)CCCCCCC(=O)N(C)CC1=CC=CC(C=2C=CC(CC3C(NC(=O)S3)=O)=CC=2)=C1 HKPCOWRPTJDTEE-UHFFFAOYSA-N 0.000 claims description 3
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- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 2
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- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 2
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- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
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- 208000010668 atopic eczema Diseases 0.000 claims description 2
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
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- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
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- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
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- JXDSRMCJXDDDDB-PKTZIBPZSA-N methyl (2s,3r)-2-ethoxy-3-hydroxy-3-[4-[3-[[[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]methyl]phenyl]phenyl]propanoate Chemical compound C1=CC([C@@H](O)[C@H](OCC)C(=O)OC)=CC=C1C1=CC=CC(CNCC(=O)OC(C)(C)C)=C1 JXDSRMCJXDDDDB-PKTZIBPZSA-N 0.000 description 1
- ZUUUAAZQEMFVSN-UHFFFAOYSA-N methyl 10-chloro-10-oxodecanoate Chemical compound COC(=O)CCCCCCCCC(Cl)=O ZUUUAAZQEMFVSN-UHFFFAOYSA-N 0.000 description 1
- PSVKXUNDHJADJL-UHFFFAOYSA-N methyl 4-[[3-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenyl]phenyl]methyl-methylcarbamoyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C(=O)N(C)CC1=CC=CC(C=2C=CC(CC3C(NC(=O)S3)=O)=CC=2)=C1 PSVKXUNDHJADJL-UHFFFAOYSA-N 0.000 description 1
- CVXXHXPNTZBZEL-UHFFFAOYSA-N methyl 4-carbonochloridoylbenzoate Chemical compound COC(=O)C1=CC=C(C(Cl)=O)C=C1 CVXXHXPNTZBZEL-UHFFFAOYSA-N 0.000 description 1
- SDIFAOJBUROTEX-UHFFFAOYSA-N methyl 6-[[3-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenyl]phenyl]methyl-methylcarbamoyl]naphthalene-2-carboxylate Chemical compound C1=CC2=CC(C(=O)OC)=CC=C2C=C1C(=O)N(C)CC(C=1)=CC=CC=1C(C=C1)=CC=C1CC1SC(=O)NC1=O SDIFAOJBUROTEX-UHFFFAOYSA-N 0.000 description 1
- RKUPOLBFJIEWBZ-UHFFFAOYSA-N methyl 8-chloro-8-oxooctanoate Chemical compound COC(=O)CCCCCCC(Cl)=O RKUPOLBFJIEWBZ-UHFFFAOYSA-N 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- XGEGHDBEHXKFPX-NJFSPNSNSA-N methylurea Chemical compound [14CH3]NC(N)=O XGEGHDBEHXKFPX-NJFSPNSNSA-N 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
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- 229960003632 minoxidil Drugs 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
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- 201000006417 multiple sclerosis Diseases 0.000 description 1
- FEABOKUGIXTQQV-UHFFFAOYSA-N n-[[3-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenyl]phenyl]methyl]-3-hydroxy-n-methylnaphthalene-2-carboxamide Chemical compound C=1C2=CC=CC=C2C=C(O)C=1C(=O)N(C)CC(C=1)=CC=CC=1C(C=C1)=CC=C1CC1SC(=O)NC1=O FEABOKUGIXTQQV-UHFFFAOYSA-N 0.000 description 1
- GIILARRWKFJPMK-UHFFFAOYSA-N n-[[3-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenyl]phenyl]methyl]-6-hexoxy-n-methylnaphthalene-2-carboxamide Chemical compound C1=CC2=CC(OCCCCCC)=CC=C2C=C1C(=O)N(C)CC(C=1)=CC=CC=1C(C=C1)=CC=C1CC1SC(=O)NC1=O GIILARRWKFJPMK-UHFFFAOYSA-N 0.000 description 1
- BNIGZUYFUBMOMG-UHFFFAOYSA-N n-[[3-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenyl]phenyl]methyl]-n-methyl-2-phenoxyacetamide Chemical compound C=1C=CC=CC=1OCC(=O)N(C)CC(C=1)=CC=CC=1C(C=C1)=CC=C1CC1SC(=O)NC1=O BNIGZUYFUBMOMG-UHFFFAOYSA-N 0.000 description 1
- UEXZVVLJGSCVRI-UHFFFAOYSA-N n-[[3-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenyl]phenyl]methyl]-n-methyl-4-methylsulfanylbenzamide Chemical compound C1=CC(SC)=CC=C1C(=O)N(C)CC1=CC=CC(C=2C=CC(CC3C(NC(=O)S3)=O)=CC=2)=C1 UEXZVVLJGSCVRI-UHFFFAOYSA-N 0.000 description 1
- KBGMAYZPPITFRT-UHFFFAOYSA-N n-[[3-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenyl]phenyl]methyl]-n-methyl-4-methylsulfonylbenzamide Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1C(=O)N(C)CC(C=1)=CC=CC=1C(C=C1)=CC=C1CC1SC(=O)NC1=O KBGMAYZPPITFRT-UHFFFAOYSA-N 0.000 description 1
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- MPNDJASJOVFABI-UHFFFAOYSA-N n-[[3-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenyl]phenyl]methyl]-n-methyladamantane-1-carboxamide Chemical compound C1C(C2)CC(C3)CC2CC13C(=O)N(C)CC(C=1)=CC=CC=1C(C=C1)=CC=C1CC1SC(=O)NC1=O MPNDJASJOVFABI-UHFFFAOYSA-N 0.000 description 1
- OGQIVJFAAQTKOW-UHFFFAOYSA-N n-[[3-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenyl]phenyl]methyl]-n-methylnaphthalene-1-carboxamide Chemical compound C=1C=CC2=CC=CC=C2C=1C(=O)N(C)CC(C=1)=CC=CC=1C(C=C1)=CC=C1CC1SC(=O)NC1=O OGQIVJFAAQTKOW-UHFFFAOYSA-N 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N n-hexadecyl alcohol Natural products CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- SLFZKCPNPDDSFA-UHFFFAOYSA-N n-methyl-4-phenylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=CC=CC=C1 SLFZKCPNPDDSFA-UHFFFAOYSA-N 0.000 description 1
- UMLLRLQOVCOLAJ-UHFFFAOYSA-N n-methyladamantane-1-carboxamide Chemical compound C1C(C2)CC3CC2CC1(C(=O)NC)C3 UMLLRLQOVCOLAJ-UHFFFAOYSA-N 0.000 description 1
- BWFORQSNSQQHSY-UHFFFAOYSA-N n-methylnaphthalene-2-carboxamide Chemical compound C1=CC=CC2=CC(C(=O)NC)=CC=C21 BWFORQSNSQQHSY-UHFFFAOYSA-N 0.000 description 1
- NSNPSJGHTQIXDO-UHFFFAOYSA-N naphthalene-1-carbonyl chloride Chemical compound C1=CC=C2C(C(=O)Cl)=CC=CC2=C1 NSNPSJGHTQIXDO-UHFFFAOYSA-N 0.000 description 1
- XNLBCXGRQWUJLU-UHFFFAOYSA-N naphthalene-2-carbonyl chloride Chemical compound C1=CC=CC2=CC(C(=O)Cl)=CC=C21 XNLBCXGRQWUJLU-UHFFFAOYSA-N 0.000 description 1
- 229960004927 neomycin Drugs 0.000 description 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- XYJRXVWERLGGKC-UHFFFAOYSA-D pentacalcium;hydroxide;triphosphate Chemical compound [OH-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O XYJRXVWERLGGKC-UHFFFAOYSA-D 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 108091008725 peroxisome proliferator-activated receptors alpha Proteins 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 229960002036 phenytoin Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 108020001213 potassium channel Proteins 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- BHMBVRSPMRCCGG-OUTUXVNYSA-N prostaglandin D2 Chemical compound CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)[C@@H](O)CC1=O BHMBVRSPMRCCGG-OUTUXVNYSA-N 0.000 description 1
- UQOQENZZLBSFKO-POPPZSFYSA-N prostaglandin J2 Chemical compound CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)C=CC1=O UQOQENZZLBSFKO-POPPZSFYSA-N 0.000 description 1
- NPCOQXAVBJJZBQ-UHFFFAOYSA-N reduced coenzyme Q9 Natural products COC1=C(O)C(C)=C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)C(O)=C1OC NPCOQXAVBJJZBQ-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000001403 relative X-ray reflectometry Methods 0.000 description 1
- 108090000064 retinoic acid receptors Proteins 0.000 description 1
- 102000003702 retinoic acid receptors Human genes 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
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- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229940037128 systemic glucocorticoids Drugs 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- DJNHISMHPSMPBN-UHFFFAOYSA-N tert-butyl n-[(3-bromophenyl)methyl]-n-methylcarbamate Chemical compound CC(C)(C)OC(=O)N(C)CC1=CC=CC(Br)=C1 DJNHISMHPSMPBN-UHFFFAOYSA-N 0.000 description 1
- FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 1
- GXBYDOACMRLODD-UHFFFAOYSA-N tert-butyl n-[[3-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenyl]phenyl]methyl]-n-methylcarbamate Chemical compound CC(C)(C)OC(=O)N(C)CC1=CC=CC(C=2C=CC(CC3C(NC(=O)S3)=O)=CC=2)=C1 GXBYDOACMRLODD-UHFFFAOYSA-N 0.000 description 1
- PSNWQJDNRWBMCE-UHFFFAOYSA-N tert-butyl n-[[3-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenyl]phenyl]methyl]carbamate Chemical compound CC(C)(C)OC(=O)NCC1=CC=CC(C=2C=CC(CC3C(NC(=O)S3)=O)=CC=2)=C1 PSNWQJDNRWBMCE-UHFFFAOYSA-N 0.000 description 1
- MYBABIGTNUHVFP-UHFFFAOYSA-N tert-butyl n-[[3-[4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenyl]phenyl]methyl]carbamate Chemical compound CC(C)(C)OC(=O)NCC1=CC=CC(C=2C=CC(C=C3C(NC(=O)S3)=O)=CC=2)=C1 MYBABIGTNUHVFP-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- 229940040944 tetracyclines Drugs 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical group COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- AALUTIYNYXEFNT-UHFFFAOYSA-N trimethylsilane hydroiodide Chemical compound C[SiH](C)C.I AALUTIYNYXEFNT-UHFFFAOYSA-N 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
- 229940040064 ubiquinol Drugs 0.000 description 1
- QNTNKSLOFHEFPK-UPTCCGCDSA-N ubiquinol-10 Chemical compound COC1=C(O)C(C)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=C1OC QNTNKSLOFHEFPK-UPTCCGCDSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/416—Quaternary ammonium compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4986—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with sulfur as the only hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/08—Antiseborrheics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/007—Preparations for dry skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/06—Preparations for care of the skin for countering cellulitis
-
- 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
-
- 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
- C07D277/34—Oxygen atoms
-
- 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
- C07D417/12—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 linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/70—Biological properties of the composition as a whole
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Cosmetics (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0116750A FR2833949B1 (fr) | 2001-12-21 | 2001-12-21 | NOUVEAUX LIGANDS ACTIVATEURS DES RECEPTEURS PPARy, LEUR PROCEDE DE PREPARATION ET LEUR UTILISATION EN MEDECINE HUMAINE AINSI QU'EN COSMETIQUE |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200403797B true ZA200403797B (en) | 2004-12-22 |
Family
ID=8870902
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200403797A ZA200403797B (en) | 2001-12-21 | 2004-05-18 | Biphenylmethyl-thiazolidinediones and analogues and their use as PPAR-gamma activators. |
Country Status (20)
| Country | Link |
|---|---|
| EP (1) | EP1458697B1 (pt) |
| JP (1) | JP2005518394A (pt) |
| KR (1) | KR20040072676A (pt) |
| CN (1) | CN100360512C (pt) |
| AT (1) | ATE338753T1 (pt) |
| AU (1) | AU2002364985A1 (pt) |
| BR (1) | BR0214239A (pt) |
| CA (1) | CA2468796C (pt) |
| CY (1) | CY1106255T1 (pt) |
| DE (1) | DE60214595T2 (pt) |
| DK (1) | DK1458697T3 (pt) |
| ES (1) | ES2272820T3 (pt) |
| FR (1) | FR2833949B1 (pt) |
| HU (1) | HUP0402616A3 (pt) |
| MX (1) | MXPA04006051A (pt) |
| PL (1) | PL372881A1 (pt) |
| PT (1) | PT1458697E (pt) |
| RU (1) | RU2323212C2 (pt) |
| WO (1) | WO2003055867A1 (pt) |
| ZA (1) | ZA200403797B (pt) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI311133B (en) | 2001-04-20 | 2009-06-21 | Eisai R&D Man Co Ltd | Carboxylic acid derivativeand the salt thereof |
| EP1394147A4 (en) * | 2001-06-04 | 2007-10-24 | Eisai R&D Man Co Ltd | CARBOXYLENE DERIVATIVE AND A SALT OR AN ESTER CONTAINING MEDICINE |
| KR20050086828A (ko) * | 2002-11-25 | 2005-08-30 | 갈데르마 리써어치 앤드 디벨로프먼트,에스.엔.씨. | Ｐｐａｒ-감마 형 수용체를 활성화시키는 비페닐 화합물,및 미용 또는 약학 조성물에서의 이의 용도 |
| ATE458485T1 (de) * | 2003-07-11 | 2010-03-15 | Proteologics Inc | Ubiquitin-ligase-hemmer und verwandte verfahren |
| FR2862870A1 (fr) * | 2003-12-01 | 2005-06-03 | Galderma Res & Dev | Utilisation d'activateurs de recepteurs ppar en cosmetique et dermatologie. |
| EP1734963A4 (en) | 2004-04-02 | 2008-06-18 | Merck & Co Inc | METHOD FOR TREATING PEOPLE WITH METABOLIC AND ANTHROPOMETRIC DISORDER |
| AU2005272389B2 (en) * | 2004-08-11 | 2011-08-04 | Kyorin Pharmaceutical Co., Ltd. | Novel cyclic aminobenzoic acid derivative |
| JP2008509965A (ja) * | 2004-08-17 | 2008-04-03 | ガルデルマ・リサーチ・アンド・デヴェロップメント | Ｐｐａｒ型受容体を活性化する新規な二芳香族化合物およびその化粧品組成物または医薬組成物における使用 |
| FR2874378B1 (fr) * | 2004-08-17 | 2006-10-27 | Galderma Res & Dev | Nouveaux composes bi-aromatiques activateurs des recepteurs de type ppar et leur utilisation dans des compositions cosmetiques ou pharmaceutiques |
| KR20070047308A (ko) * | 2004-08-17 | 2007-05-04 | 갈데르마 리써어치 앤드 디벨로프먼트 | Ｐｐａｒ 유형 수용체를 활성화시키는 신규 이방향족화합물, 및 미용 또는 약학적 조성물에서의 그의 용도 |
| FR2874379B1 (fr) * | 2004-08-17 | 2006-10-27 | Galderma Res & Dev | Nouveaux composes bi-aromatiques activateurs des recepteurs de type ppar et leur utilisation dans des compositions cosmetiques ou pharmaceutiques |
| JP2008520619A (ja) * | 2004-11-19 | 2008-06-19 | ガルデルマ・リサーチ・アンド・デヴェロップメント | ＰＰＡＲγ受容体を調節する新規化合物並びに化粧品または製薬組成物中におけるその使用 |
| FR2878247B1 (fr) | 2004-11-19 | 2008-10-03 | Galderma Res & Dev | Nouveaux composes modulateurs des recepteurs de type ppary et leur utilisation dans des compositions cosmetiques ou pharmaceutiques |
| FR2887444A1 (fr) * | 2005-06-28 | 2006-12-29 | Oreal | Composes benzylidene-1,3-thiazolidine-2,4-diones, leurs utilisations et compositions pour stimuler ou induire la pousse des fibres keratiniques et/ou freiner leur chute et/ou augmenter leur densite. |
| FR2892412B1 (fr) | 2005-10-26 | 2008-05-16 | Galderma Res & Dev | Composes biaromatiques modulateurs des ppars |
| EA020466B1 (ru) | 2007-06-04 | 2014-11-28 | Синерджи Фармасьютикалз Инк. | Агонисты гуанилатциклазы, пригодные для лечения желудочно-кишечных нарушений, воспаления, рака и других заболеваний |
| US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
| FR2917084B1 (fr) * | 2007-06-05 | 2009-07-17 | Galderma Res & Dev | Nouveaux derives d'acide 3-phenyl propanoique activateurs des recpteurs de type ppar, leur methode de preparation et leur utilisation dans des compositions cosmetiques ou pharmaceutiques. |
| FR2917086B1 (fr) * | 2007-06-05 | 2009-07-17 | Galderma Res & Dev | Nouveaux derives d'acide 3-phenyl acrylique activateurs des recepteurs de type ppar, leur methode de preparation et leur utilisation dans des compositions cosmetiques ou pharmaceutiques. |
| IE20070928A1 (en) * | 2007-12-21 | 2009-09-30 | Giuliani Int Ltd | Multi target ligands |
| CA2930674A1 (en) | 2008-06-04 | 2009-12-10 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| JP2011528375A (ja) | 2008-07-16 | 2011-11-17 | シナジー ファーマシューティカルズ インコーポレイテッド | 胃腸障害、炎症、癌、およびその他の障害の治療のために有用なグアニル酸シクラーゼのアゴニスト |
| CN101774941A (zh) * | 2009-01-13 | 2010-07-14 | 浙江九洲药业股份有限公司 | 2-酰基氨基-3-联苯基丙酸的制备及拆分方法 |
| WO2012027331A1 (en) | 2010-08-27 | 2012-03-01 | Ironwood Pharmaceuticals, Inc. | Compositions and methods for treating or preventing metabolic syndrome and related diseases and disorders |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| JP2016514670A (ja) | 2013-03-15 | 2016-05-23 | シナジー ファーマシューティカルズ インコーポレイテッド | 他の薬物と組み合わせたグアニル酸シクラーゼ受容体アゴニスト |
| AU2014235215A1 (en) | 2013-03-15 | 2015-10-01 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase and their uses |
| US10011637B2 (en) | 2013-06-05 | 2018-07-03 | Synergy Pharmaceuticals, Inc. | Ultra-pure agonists of guanylate cyclase C, method of making and using same |
| CN118206542A (zh) * | 2023-03-22 | 2024-06-18 | 沈阳药科大学 | 一种化合物及其制备方法和在制备sEH抑制剂与PPARs激动剂中的应用 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2767525B1 (fr) * | 1997-08-21 | 1999-11-12 | Cird Galderma | Derives biphenyliques substitues par un radical aromatique ou heteroaromatique et compositions pharmaceutiques et cosmetiques les contenant |
| US6506757B1 (en) * | 1998-03-10 | 2003-01-14 | Ono Pharmaceutical Co., Ltd. | Carboxylic acid derivatives and drugs containing the same as the active ingredient |
| WO2001014349A1 (fr) * | 1999-08-23 | 2001-03-01 | Kyorin Pharmaceutical Co., Ltd. | Derives de benzylthiazolidine-2,4-dione substitues |
| FR2812876B1 (fr) * | 2000-08-08 | 2002-09-27 | Galderma Res & Dev | Nouveaux composes bi-aromatiques activateurs des recepteurs de type ppar-gamma et leur utilisation dans des compositions cosmetiques ou pharmaceutiques |
-
2001
- 2001-12-21 FR FR0116750A patent/FR2833949B1/fr not_active Expired - Fee Related
-
2002
- 2002-12-09 CN CNB028254899A patent/CN100360512C/zh not_active Expired - Fee Related
- 2002-12-09 CA CA2468796A patent/CA2468796C/fr not_active Expired - Fee Related
- 2002-12-09 AT AT02805790T patent/ATE338753T1/de not_active IP Right Cessation
- 2002-12-09 PL PL02372881A patent/PL372881A1/xx not_active Application Discontinuation
- 2002-12-09 MX MXPA04006051A patent/MXPA04006051A/es active IP Right Grant
- 2002-12-09 BR BR0214239-2A patent/BR0214239A/pt not_active IP Right Cessation
- 2002-12-09 JP JP2003556398A patent/JP2005518394A/ja not_active Withdrawn
- 2002-12-09 WO PCT/FR2002/004232 patent/WO2003055867A1/fr active IP Right Grant
- 2002-12-09 AU AU2002364985A patent/AU2002364985A1/en not_active Abandoned
- 2002-12-09 HU HU0402616A patent/HUP0402616A3/hu unknown
- 2002-12-09 DE DE60214595T patent/DE60214595T2/de not_active Expired - Lifetime
- 2002-12-09 EP EP02805790A patent/EP1458697B1/fr not_active Expired - Lifetime
- 2002-12-09 ES ES02805790T patent/ES2272820T3/es not_active Expired - Lifetime
- 2002-12-09 PT PT02805790T patent/PT1458697E/pt unknown
- 2002-12-09 DK DK02805790T patent/DK1458697T3/da active
- 2002-12-09 RU RU2004122394/04A patent/RU2323212C2/ru not_active IP Right Cessation
- 2002-12-09 KR KR10-2004-7009903A patent/KR20040072676A/ko not_active Application Discontinuation
-
2004
- 2004-05-18 ZA ZA200403797A patent/ZA200403797B/en unknown
-
2006
- 2006-11-23 CY CY20061101695T patent/CY1106255T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2005518394A (ja) | 2005-06-23 |
| DK1458697T3 (da) | 2007-01-15 |
| PT1458697E (pt) | 2007-01-31 |
| HUP0402616A2 (hu) | 2005-03-29 |
| HUP0402616A3 (en) | 2009-01-28 |
| ES2272820T3 (es) | 2007-05-01 |
| FR2833949A1 (fr) | 2003-06-27 |
| PL372881A1 (en) | 2005-08-08 |
| WO2003055867A1 (fr) | 2003-07-10 |
| CA2468796A1 (fr) | 2003-07-10 |
| RU2004122394A (ru) | 2005-03-27 |
| CY1106255T1 (el) | 2011-06-08 |
| EP1458697B1 (fr) | 2006-09-06 |
| FR2833949B1 (fr) | 2005-08-05 |
| DE60214595T2 (de) | 2007-09-13 |
| EP1458697A1 (fr) | 2004-09-22 |
| MXPA04006051A (es) | 2004-09-27 |
| RU2323212C2 (ru) | 2008-04-27 |
| CA2468796C (fr) | 2012-07-17 |
| KR20040072676A (ko) | 2004-08-18 |
| BR0214239A (pt) | 2004-09-21 |
| ATE338753T1 (de) | 2006-09-15 |
| AU2002364985A1 (en) | 2003-07-15 |
| DE60214595D1 (de) | 2006-10-19 |
| CN100360512C (zh) | 2008-01-09 |
| CN1639138A (zh) | 2005-07-13 |
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