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
Links
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- 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
- 235000019260 propionic acid Nutrition 0.000 claims description 9
- 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
- 230000035755 proliferation Effects 0.000 claims description 6
- 230000005855 radiation Effects 0.000 claims description 6
- 208000017520 skin disease Diseases 0.000 claims description 6
- 208000012641 Pigmentation disease Diseases 0.000 claims description 5
- 235000010290 biphenyl Nutrition 0.000 claims description 5
- 239000004305 biphenyl Substances 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 206010003645 Atopy Diseases 0.000 claims description 4
- 235000011054 acetic acid Nutrition 0.000 claims description 4
- 229960000583 acetic acid Drugs 0.000 claims description 4
- 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 230000003780 keratinization Effects 0.000 claims description 4
- 230000037356 lipid metabolism Effects 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 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
- 201000010153 skin papilloma Diseases 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 3
- 208000027932 Collagen disease Diseases 0.000 claims description 3
- 206010049422 Precancerous skin lesion Diseases 0.000 claims description 3
- 230000002500 effect on skin Effects 0.000 claims description 3
- 208000026278 immune system disease Diseases 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 230000002757 inflammatory effect Effects 0.000 claims description 3
- 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
- 230000003287 optical effect Effects 0.000 claims description 3
- 230000007170 pathology Effects 0.000 claims description 3
- 230000001105 regulatory effect Effects 0.000 claims description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 2
- KRTGJZMJJVEKRX-UHFFFAOYSA-N 2-phenylethan-1-yl Chemical compound [CH2]CC1=CC=CC=C1 KRTGJZMJJVEKRX-UHFFFAOYSA-N 0.000 claims description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- LUQVCHRDAGWYMG-UHFFFAOYSA-N 4-phenylbenzamide Chemical compound C1=CC(C(=O)N)=CC=C1C1=CC=CC=C1 LUQVCHRDAGWYMG-UHFFFAOYSA-N 0.000 claims description 2
- 206010000501 Acne conglobata Diseases 0.000 claims description 2
- 206010000511 Acne occupational Diseases 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 201000009030 Carcinoma Diseases 0.000 claims description 2
- 206010008570 Chloasma Diseases 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 201000004624 Dermatitis Diseases 0.000 claims description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 2
- 206010013786 Dry skin Diseases 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 208000003367 Hypopigmentation Diseases 0.000 claims description 2
- 206010023347 Keratoacanthoma Diseases 0.000 claims description 2
- 206010025323 Lymphomas Diseases 0.000 claims description 2
- 208000003351 Melanosis Diseases 0.000 claims description 2
- 206010033554 Palmoplantar keratoderma Diseases 0.000 claims description 2
- 201000004681 Psoriasis Diseases 0.000 claims description 2
- 206010039710 Scleroderma Diseases 0.000 claims description 2
- 206010039792 Seborrhoea Diseases 0.000 claims description 2
- 206010040925 Skin striae Diseases 0.000 claims description 2
- 208000031439 Striae Distensae Diseases 0.000 claims description 2
- 241000934136 Verruca Species 0.000 claims description 2
- 206010047642 Vitiligo Diseases 0.000 claims description 2
- 208000000260 Warts Diseases 0.000 claims description 2
- 206010048222 Xerosis Diseases 0.000 claims description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 2
- 208000010668 atopic eczema Diseases 0.000 claims description 2
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 208000035269 cancer or benign tumor Diseases 0.000 claims description 2
- 230000024245 cell differentiation Effects 0.000 claims description 2
- 230000004663 cell proliferation Effects 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 201000004196 common wart Diseases 0.000 claims description 2
- 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
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- 230000037336 dry skin Effects 0.000 claims description 2
- 201000004306 epidermodysplasia verruciformis Diseases 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 208000009197 gingival hypertrophy Diseases 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 claims description 2
- 208000000069 hyperpigmentation Diseases 0.000 claims description 2
- 230000003810 hyperpigmentation Effects 0.000 claims description 2
- 230000003425 hypopigmentation Effects 0.000 claims description 2
- 230000001900 immune effect Effects 0.000 claims description 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 206010025135 lupus erythematosus Diseases 0.000 claims description 2
- 230000003211 malignant effect Effects 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 208000003154 papilloma Diseases 0.000 claims description 2
- 230000019612 pigmentation Effects 0.000 claims description 2
- 230000001185 psoriatic effect Effects 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 230000000241 respiratory effect Effects 0.000 claims description 2
- 201000004700 rosacea Diseases 0.000 claims description 2
- 230000003612 virological effect Effects 0.000 claims description 2
- 150000003751 zinc Chemical class 0.000 claims description 2
- 101000975474 Homo sapiens Keratin, type I cytoskeletal 10 Proteins 0.000 claims 1
- 102100023970 Keratin, type I cytoskeletal 10 Human genes 0.000 claims 1
- 208000001126 Keratosis Diseases 0.000 claims 1
- JEEBMQGSBVJRNC-UHFFFAOYSA-N n-[[2-cyclopentyl-5-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenyl]phenyl]methyl]-n-methylpropanamide Chemical compound CCC(=O)N(C)CC1=CC(C=2C=CC(CC3C(NC(=O)S3)=O)=CC=2)=CC=C1C1CCCC1 JEEBMQGSBVJRNC-UHFFFAOYSA-N 0.000 claims 1
- YLUSDNYWBRAVHI-UHFFFAOYSA-N n-[[3-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenyl]phenyl]methyl]-3-methoxy-n-methylnaphthalene-2-carboxamide Chemical compound COC1=CC2=CC=CC=C2C=C1C(=O)N(C)CC(C=1)=CC=CC=1C(C=C1)=CC=C1CC1SC(=O)NC1=O YLUSDNYWBRAVHI-UHFFFAOYSA-N 0.000 claims 1
- 125000006611 nonyloxy group Chemical group 0.000 claims 1
- 201000008743 palmoplantar keratosis Diseases 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 162
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 90
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 87
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 76
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- 239000000377 silicon dioxide Substances 0.000 description 43
- 238000004587 chromatography analysis Methods 0.000 description 42
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 36
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 34
- 239000000843 powder Substances 0.000 description 31
- 238000000746 purification Methods 0.000 description 31
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- 230000008018 melting Effects 0.000 description 28
- 238000002844 melting Methods 0.000 description 28
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 27
- 239000000047 product Substances 0.000 description 27
- 239000012429 reaction media Substances 0.000 description 27
- 102000005962 receptors Human genes 0.000 description 26
- 108020003175 receptors Proteins 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- LFHICSPZNBDEQT-UHFFFAOYSA-N 5-[[4-[3-(methylaminomethyl)phenyl]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound CNCC1=CC=CC(C=2C=CC(CC3C(NC(=O)S3)=O)=CC=2)=C1 LFHICSPZNBDEQT-UHFFFAOYSA-N 0.000 description 22
- 239000012074 organic phase Substances 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 18
- 235000019341 magnesium sulphate Nutrition 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000003921 oil Substances 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 238000001704 evaporation Methods 0.000 description 10
- 230000008020 evaporation Effects 0.000 description 10
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000556 agonist Substances 0.000 description 9
- 239000002609 medium Substances 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 230000004913 activation Effects 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000001914 filtration Methods 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 150000003857 carboxamides Chemical class 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000002674 ointment Substances 0.000 description 5
- 125000006239 protecting group Chemical group 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- 230000000699 topical effect Effects 0.000 description 5
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 4
- 101150014691 PPARA gene Proteins 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- FGNWYHWXXOYCMV-IBGZPJMESA-N methyl (2s)-2-ethoxy-3-[4-[3-(methylaminomethyl)phenyl]phenyl]propanoate Chemical compound C1=CC(C[C@H](OCC)C(=O)OC)=CC=C1C1=CC=CC(CNC)=C1 FGNWYHWXXOYCMV-IBGZPJMESA-N 0.000 description 4
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 4
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 4
- 229960002216 methylparaben Drugs 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 230000023603 positive regulation of transcription initiation, DNA-dependent Effects 0.000 description 4
- 210000003491 skin Anatomy 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 238000001665 trituration Methods 0.000 description 4
- VXWBQOJISHAKKM-UHFFFAOYSA-N (4-formylphenyl)boronic acid Chemical compound OB(O)C1=CC=C(C=O)C=C1 VXWBQOJISHAKKM-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- NWMGHHXYQCNVNQ-UHFFFAOYSA-N 4-[4-(2-methoxyethoxymethoxy)phenyl]benzoic acid Chemical compound C1=CC(OCOCCOC)=CC=C1C1=CC=C(C(O)=O)C=C1 NWMGHHXYQCNVNQ-UHFFFAOYSA-N 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- XKXHYNDSWZPZOL-UHFFFAOYSA-N 5-[[4-[3-(methylamino)phenyl]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound CNC1=CC=CC(C=2C=CC(CC3C(NC(=O)S3)=O)=CC=2)=C1 XKXHYNDSWZPZOL-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 description 3
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000003213 activating effect Effects 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 230000004069 differentiation Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 150000002632 lipids Chemical class 0.000 description 3
- 239000006210 lotion Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000004005 microsphere Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002077 nanosphere Substances 0.000 description 3
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 description 3
- RAIYODFGMLZUDF-UHFFFAOYSA-N piperidin-1-ium;acetate Chemical compound CC([O-])=O.C1CC[NH2+]CC1 RAIYODFGMLZUDF-UHFFFAOYSA-N 0.000 description 3
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 239000001117 sulphuric acid Substances 0.000 description 3
- 235000011149 sulphuric acid Nutrition 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- BJNPOFRPHNDRHC-UHFFFAOYSA-N tert-butyl n-(3-bromophenyl)-n-methylcarbamate Chemical compound CC(C)(C)OC(=O)N(C)C1=CC=CC(Br)=C1 BJNPOFRPHNDRHC-UHFFFAOYSA-N 0.000 description 3
- VDFBCTSISJDKNW-UHFFFAOYSA-N tert-butyl n-(3-bromophenyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=CC(Br)=C1 VDFBCTSISJDKNW-UHFFFAOYSA-N 0.000 description 3
- SQMSFZOHCLXAAC-UHFFFAOYSA-N tert-butyl n-[[3-(4-formylphenyl)phenyl]methyl]-n-methylcarbamate Chemical compound CC(C)(C)OC(=O)N(C)CC1=CC=CC(C=2C=CC(C=O)=CC=2)=C1 SQMSFZOHCLXAAC-UHFFFAOYSA-N 0.000 description 3
- LCWCQKZAPAAOBS-UHFFFAOYSA-N tert-butyl n-[[3-(4-formylphenyl)phenyl]methyl]carbamate Chemical compound CC(C)(C)OC(=O)NCC1=CC=CC(C=2C=CC(C=O)=CC=2)=C1 LCWCQKZAPAAOBS-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 2-ethoxyacetyl chloride Chemical compound CCOCC(Cl)=O ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- HKOSFZXROYRVJT-UHFFFAOYSA-N 3-bromo-n-methylaniline Chemical compound CNC1=CC=CC(Br)=C1 HKOSFZXROYRVJT-UHFFFAOYSA-N 0.000 description 2
- DHYHYLGCQVVLOQ-UHFFFAOYSA-N 3-bromoaniline Chemical compound NC1=CC=CC(Br)=C1 DHYHYLGCQVVLOQ-UHFFFAOYSA-N 0.000 description 2
- SNMJJYKFDGZVBO-UHFFFAOYSA-N 3-cyclopentyl-n-[[3-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenyl]phenyl]methyl]-n-methylpropanamide Chemical compound C1CCCC1CCC(=O)N(C)CC(C=1)=CC=CC=1C(C=C1)=CC=C1CC1SC(=O)NC1=O SNMJJYKFDGZVBO-UHFFFAOYSA-N 0.000 description 2
- WLPWLMWEWXCJCO-UHFFFAOYSA-N 4-[3-(methylamino)phenyl]benzaldehyde Chemical compound CNC1=CC=CC(C=2C=CC(C=O)=CC=2)=C1 WLPWLMWEWXCJCO-UHFFFAOYSA-N 0.000 description 2
- OZCULFZQSHFJNI-UHFFFAOYSA-N 4-benzoylbenzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1C(=O)C1=CC=CC=C1 OZCULFZQSHFJNI-UHFFFAOYSA-N 0.000 description 2
- MIEJPWILCQAQKT-UHFFFAOYSA-N 4-methylsulfanylbenzoyl chloride Chemical compound CSC1=CC=C(C(Cl)=O)C=C1 MIEJPWILCQAQKT-UHFFFAOYSA-N 0.000 description 2
- JPVUWCPKMYXOKW-UHFFFAOYSA-N 4-phenylbenzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1C1=CC=CC=C1 JPVUWCPKMYXOKW-UHFFFAOYSA-N 0.000 description 2
- 201000004384 Alopecia Diseases 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- 101100202237 Danio rerio rxrab gene Proteins 0.000 description 2
- 101100309320 Danio rerio rxrga gene Proteins 0.000 description 2
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 2
- 241000792859 Enema Species 0.000 description 2
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 2
- YZGQDNOIGFBYKF-UHFFFAOYSA-N Ethoxyacetic acid Chemical compound CCOCC(O)=O YZGQDNOIGFBYKF-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 208000008589 Obesity Diseases 0.000 description 2
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- 101150050070 RXRA gene Proteins 0.000 description 2
- 102000034527 Retinoid X Receptors Human genes 0.000 description 2
- 108010038912 Retinoid X Receptors Proteins 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 231100000360 alopecia Toxicity 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 238000013270 controlled release Methods 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 206010012601 diabetes mellitus Diseases 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000007920 enema Substances 0.000 description 2
- 229940095399 enema Drugs 0.000 description 2
- PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 210000000987 immune system Anatomy 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 2
- 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- QNKLWUXRTDHVJE-MOPGFXCFSA-N methyl (2s,3r)-2-ethoxy-3-hydroxy-3-[4-[3-(methylaminomethyl)phenyl]phenyl]propanoate Chemical compound C1=CC([C@@H](O)[C@H](OCC)C(=O)OC)=CC=C1C1=CC=CC(CNC)=C1 QNKLWUXRTDHVJE-MOPGFXCFSA-N 0.000 description 2
- HUSGVMZBHBQVDS-UHFFFAOYSA-N methyl 4-[4-(2-methoxyethoxymethoxy)phenyl]benzoate Chemical compound C1=CC(OCOCCOC)=CC=C1C1=CC=C(C(=O)OC)C=C1 HUSGVMZBHBQVDS-UHFFFAOYSA-N 0.000 description 2
- GJWKBQWFEKLMNY-UHFFFAOYSA-N methyl 6-(2-methoxyethoxymethoxy)naphthalene-2-carboxylate Chemical compound C1=C(C(=O)OC)C=CC2=CC(OCOCCOC)=CC=C21 GJWKBQWFEKLMNY-UHFFFAOYSA-N 0.000 description 2
- UKZOPQRTQJERQC-UHFFFAOYSA-N methyl 6-hydroxynaphthalene-2-carboxylate Chemical compound C1=C(O)C=CC2=CC(C(=O)OC)=CC=C21 UKZOPQRTQJERQC-UHFFFAOYSA-N 0.000 description 2
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 2
- 235000013336 milk Nutrition 0.000 description 2
- 210000004080 milk Anatomy 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- PTCHWYSGCYPWNS-UHFFFAOYSA-N n-[[3-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenyl]phenyl]methyl]-4-(4-hydroxyphenyl)-n-methylbenzamide Chemical compound C=1C=C(C=2C=CC(O)=CC=2)C=CC=1C(=O)N(C)CC(C=1)=CC=CC=1C(C=C1)=CC=C1CC1SC(=O)NC1=O PTCHWYSGCYPWNS-UHFFFAOYSA-N 0.000 description 2
- MCXCFDILJKEBQI-UHFFFAOYSA-N n-[[3-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenyl]phenyl]methyl]-6-(2-methoxyethoxymethoxy)-n-methylnaphthalene-2-carboxamide Chemical compound C1=CC2=CC(OCOCCOC)=CC=C2C=C1C(=O)N(C)CC(C=1)=CC=CC=1C(C=C1)=CC=C1CC1SC(=O)NC1=O MCXCFDILJKEBQI-UHFFFAOYSA-N 0.000 description 2
- VZUCFNRDGXICTL-UHFFFAOYSA-N n-[[3-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenyl]phenyl]methyl]-6-(methoxymethoxy)-n-methylnaphthalene-2-carboxamide Chemical compound C1=CC2=CC(OCOC)=CC=C2C=C1C(=O)N(C)CC(C=1)=CC=CC=1C(C=C1)=CC=C1CC1SC(=O)NC1=O VZUCFNRDGXICTL-UHFFFAOYSA-N 0.000 description 2
- UIYYENMNPWIGJY-UHFFFAOYSA-N n-[[3-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenyl]phenyl]methyl]-n,1-dimethylpyrrole-2-carboxamide Chemical compound C=1C=CN(C)C=1C(=O)N(C)CC(C=1)=CC=CC=1C(C=C1)=CC=C1CC1SC(=O)NC1=O UIYYENMNPWIGJY-UHFFFAOYSA-N 0.000 description 2
- MADAJELNELBZMM-UHFFFAOYSA-N n-[[3-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenyl]phenyl]methyl]-n-methyl-4-phenoxybenzamide Chemical compound C=1C=C(OC=2C=CC=CC=2)C=CC=1C(=O)N(C)CC(C=1)=CC=CC=1C(C=C1)=CC=C1CC1SC(=O)NC1=O MADAJELNELBZMM-UHFFFAOYSA-N 0.000 description 2
- SLUYSNVLBONVIA-UHFFFAOYSA-N n-[[3-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenyl]phenyl]methyl]-n-methyl-6-nonoxynaphthalene-2-carboxamide Chemical compound C1=CC2=CC(OCCCCCCCCC)=CC=C2C=C1C(=O)N(C)CC(C=1)=CC=CC=1C(C=C1)=CC=C1CC1SC(=O)NC1=O SLUYSNVLBONVIA-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 235000020824 obesity Nutrition 0.000 description 2
- 229940100692 oral suspension Drugs 0.000 description 2
- 210000002824 peroxisome Anatomy 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 2
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 2
- 239000008213 purified water Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- BSEVOUCZQOLENZ-UHFFFAOYSA-N tert-butyl n-[(3-bromophenyl)methyl]carbamate Chemical compound CC(C)(C)OC(=O)NCC1=CC=CC(Br)=C1 BSEVOUCZQOLENZ-UHFFFAOYSA-N 0.000 description 2
- AZPVBDDRNAXHKY-UHFFFAOYSA-N tert-butyl n-[[3-[4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenyl]phenyl]methyl]-n-methylcarbamate Chemical compound CC(C)(C)OC(=O)N(C)CC1=CC=CC(C=2C=CC(C=C3C(NC(=O)S3)=O)=CC=2)=C1 AZPVBDDRNAXHKY-UHFFFAOYSA-N 0.000 description 2
- DENPQNAWGQXKCU-UHFFFAOYSA-N thiophene-2-carboxamide Chemical compound NC(=O)C1=CC=CS1 DENPQNAWGQXKCU-UHFFFAOYSA-N 0.000 description 2
- QAIPRVGONGVQAS-DUXPYHPUSA-N trans-caffeic acid Chemical compound OC(=O)\C=C\C1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-DUXPYHPUSA-N 0.000 description 2
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- XMAYWYJOQHXEEK-OZXSUGGESA-N (2R,4S)-ketoconazole Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OC[C@@H]1O[C@@](CN2C=NC=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 XMAYWYJOQHXEEK-OZXSUGGESA-N 0.000 description 1
- MBRMLTXQHSESKF-PMERELPUSA-N (2s)-2-ethoxy-3-[4-[3-[[methyl-(4-phenylbenzoyl)amino]methyl]phenyl]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1C1=CC=CC(CN(C)C(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)=C1 MBRMLTXQHSESKF-PMERELPUSA-N 0.000 description 1
- NUPNHQQEHFYYQV-LJAQVGFWSA-N (2s)-2-ethoxy-3-[4-[3-[[methyl-(6-oxo-6-phenylhexanoyl)amino]methyl]phenyl]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1C1=CC=CC(CN(C)C(=O)CCCCC(=O)C=2C=CC=CC=2)=C1 NUPNHQQEHFYYQV-LJAQVGFWSA-N 0.000 description 1
- UGEQUCUBWNAUJS-UHFFFAOYSA-N (3-bromophenyl)methanamine;hydrochloride Chemical compound Cl.NCC1=CC=CC(Br)=C1 UGEQUCUBWNAUJS-UHFFFAOYSA-N 0.000 description 1
- ZGEWSBOBVHATME-UHFFFAOYSA-N (3-bromophenyl)methyl n-methylcarbamate Chemical compound CNC(=O)OCC1=CC=CC(Br)=C1 ZGEWSBOBVHATME-UHFFFAOYSA-N 0.000 description 1
- OJOFMLDBXPDXLQ-VIFPVBQESA-N (4s)-4-benzyl-1,3-oxazolidin-2-one Chemical compound C1OC(=O)N[C@H]1CC1=CC=CC=C1 OJOFMLDBXPDXLQ-VIFPVBQESA-N 0.000 description 1
- ACEAELOMUCBPJP-UHFFFAOYSA-N (E)-3,4,5-trihydroxycinnamic acid Natural products OC(=O)C=CC1=CC(O)=C(O)C(O)=C1 ACEAELOMUCBPJP-UHFFFAOYSA-N 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- BIAAQBNMRITRDV-UHFFFAOYSA-N 1-(chloromethoxy)-2-methoxyethane Chemical compound COCCOCCl BIAAQBNMRITRDV-UHFFFAOYSA-N 0.000 description 1
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
- MUQQOIASYSGTRI-UHFFFAOYSA-N 1-[3-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenyl]phenyl]-1-methyl-3-(4-phenylmethoxyphenyl)urea Chemical compound C=1C=CC(C=2C=CC(CC3C(NC(=O)S3)=O)=CC=2)=CC=1N(C)C(=O)NC(C=C1)=CC=C1OCC1=CC=CC=C1 MUQQOIASYSGTRI-UHFFFAOYSA-N 0.000 description 1
- ONWWUHDPNASBBO-UHFFFAOYSA-N 1-[3-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenyl]phenyl]-1-methyl-3-naphthalen-2-ylurea Chemical compound C=1C=C2C=CC=CC2=CC=1NC(=O)N(C)C(C=1)=CC=CC=1C(C=C1)=CC=C1CC1SC(=O)NC1=O ONWWUHDPNASBBO-UHFFFAOYSA-N 0.000 description 1
- ANLZSIKMPGVPNG-UHFFFAOYSA-N 1-[3-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenyl]phenyl]-3-(4-hexoxyphenyl)-1-methylurea Chemical compound C1=CC(OCCCCCC)=CC=C1NC(=O)N(C)C1=CC=CC(C=2C=CC(CC3C(NC(=O)S3)=O)=CC=2)=C1 ANLZSIKMPGVPNG-UHFFFAOYSA-N 0.000 description 1
- BDQNKCYCTYYMAA-UHFFFAOYSA-N 1-isocyanatonaphthalene Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1 BDQNKCYCTYYMAA-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- WQVBZJXNXCEFJN-UHFFFAOYSA-N 2-benzoylbenzamide Chemical compound NC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 WQVBZJXNXCEFJN-UHFFFAOYSA-N 0.000 description 1
- PNCWHIAZZSDHPU-UHFFFAOYSA-N 2-benzylsulfanylethanamine Chemical compound NCCSCC1=CC=CC=C1 PNCWHIAZZSDHPU-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- UOBYKYZJUGYBDK-UHFFFAOYSA-N 2-naphthoic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CC=C21 UOBYKYZJUGYBDK-UHFFFAOYSA-N 0.000 description 1
- AOPRXJXHLWYPQR-UHFFFAOYSA-N 2-phenoxyacetamide Chemical compound NC(=O)COC1=CC=CC=C1 AOPRXJXHLWYPQR-UHFFFAOYSA-N 0.000 description 1
- PKUPAJQAJXVUEK-UHFFFAOYSA-N 2-phenoxyacetyl chloride Chemical compound ClC(=O)COC1=CC=CC=C1 PKUPAJQAJXVUEK-UHFFFAOYSA-N 0.000 description 1
- UOCUSOBVEHOMMB-UHFFFAOYSA-N 2h-1$l^{6},2,3-benzothiadiazine 1,1-dioxide Chemical compound C1=CC=C2S(=O)(=O)NN=CC2=C1 UOCUSOBVEHOMMB-UHFFFAOYSA-N 0.000 description 1
- SZQVEGOXJYTLLB-UHFFFAOYSA-N 3-cyclopentylpropanoyl chloride Chemical compound ClC(=O)CCC1CCCC1 SZQVEGOXJYTLLB-UHFFFAOYSA-N 0.000 description 1
- JRXXEXVXTFEBIY-UHFFFAOYSA-N 3-ethoxypropanoic acid Chemical compound CCOCCC(O)=O JRXXEXVXTFEBIY-UHFFFAOYSA-N 0.000 description 1
- ZIMGGGWCDYVHOY-UHFFFAOYSA-N 3-hydroxy-2-imino-6-(1-piperidinyl)-4-pyrimidinamine Chemical compound N=C1N(O)C(N)=CC(N2CCCCC2)=N1 ZIMGGGWCDYVHOY-UHFFFAOYSA-N 0.000 description 1
- ODSWJRJRSPPRKL-UHFFFAOYSA-N 3-methyl-4-phenylbenzamide Chemical compound CC1=CC(C(N)=O)=CC=C1C1=CC=CC=C1 ODSWJRJRSPPRKL-UHFFFAOYSA-N 0.000 description 1
- QVDWWVXWMVFTCW-UHFFFAOYSA-N 4,5-diphenylimidazolidine Chemical compound N1CNC(C=2C=CC=CC=2)C1C1=CC=CC=C1 QVDWWVXWMVFTCW-UHFFFAOYSA-N 0.000 description 1
- HCPBURTZSXRGBN-UHFFFAOYSA-N 4-(4-propylphenyl)benzoic acid Chemical compound C1=CC(CCC)=CC=C1C1=CC=C(C(O)=O)C=C1 HCPBURTZSXRGBN-UHFFFAOYSA-N 0.000 description 1
- QQPITISQTIASAX-UHFFFAOYSA-N 4-(dimethylamino)-n-[[3-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenyl]phenyl]methyl]-n-methylnaphthalene-1-carboxamide Chemical compound C12=CC=CC=C2C(N(C)C)=CC=C1C(=O)N(C)CC(C=1)=CC=CC=1C(C=C1)=CC=C1CC1SC(=O)NC1=O QQPITISQTIASAX-UHFFFAOYSA-N 0.000 description 1
- LZQKNRRVTOJUHQ-UHFFFAOYSA-N 4-(dimethylamino)naphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(N(C)C)=CC=C(C(O)=O)C2=C1 LZQKNRRVTOJUHQ-UHFFFAOYSA-N 0.000 description 1
- FGBMTYMCUWFSRX-UHFFFAOYSA-N 4-[[3-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenyl]phenyl]methyl-methylcarbamoyl]benzoic acid Chemical compound C=1C=C(C(O)=O)C=CC=1C(=O)N(C)CC(C=1)=CC=CC=1C(C=C1)=CC=C1CC1SC(=O)NC1=O FGBMTYMCUWFSRX-UHFFFAOYSA-N 0.000 description 1
- HNZCPKFSKNEPKO-UHFFFAOYSA-N 4-benzoyl-n-[[3-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenyl]phenyl]methyl]-n-methylbenzamide Chemical compound C=1C=C(C(=O)C=2C=CC=CC=2)C=CC=1C(=O)N(C)CC(C=1)=CC=CC=1C(C=C1)=CC=C1CC1SC(=O)NC1=O HNZCPKFSKNEPKO-UHFFFAOYSA-N 0.000 description 1
- IFQUPKAISSPFTE-UHFFFAOYSA-N 4-benzoylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(=O)C1=CC=CC=C1 IFQUPKAISSPFTE-UHFFFAOYSA-N 0.000 description 1
- UZCXCVNBSPOTNE-UHFFFAOYSA-N 4-benzyl-3-(2-ethoxyacetyl)-1,3-oxazolidin-2-one Chemical compound C1OC(=O)N(C(=O)COCC)C1CC1=CC=CC=C1 UZCXCVNBSPOTNE-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- KWHCPERWLHBLOT-UHFFFAOYSA-N 4-methylsulfanylbenzoic acid Chemical compound CSC1=CC=C(C(O)=O)C=C1 KWHCPERWLHBLOT-UHFFFAOYSA-N 0.000 description 1
- AJBWNNKDUMXZLM-UHFFFAOYSA-N 4-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=C(C(O)=O)C=C1 AJBWNNKDUMXZLM-UHFFFAOYSA-N 0.000 description 1
- RYAQFHLUEMJOMF-UHFFFAOYSA-N 4-phenoxybenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OC1=CC=CC=C1 RYAQFHLUEMJOMF-UHFFFAOYSA-N 0.000 description 1
- RLSYGQXSWGVQMH-UHFFFAOYSA-N 5-[(4-phenylphenyl)methyl]-1,3-thiazolidine-2,4-dione Chemical group S1C(=O)NC(=O)C1CC1=CC=C(C=2C=CC=CC=2)C=C1 RLSYGQXSWGVQMH-UHFFFAOYSA-N 0.000 description 1
- IFFFNYYVBLDXEE-UHFFFAOYSA-N 5-[[4-[3-(methylamino)phenyl]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound CNC1=CC=CC(C=2C=CC(C=C3C(NC(=O)S3)=O)=CC=2)=C1 IFFFNYYVBLDXEE-UHFFFAOYSA-N 0.000 description 1
- XUDWMWHYTBAJHF-UHFFFAOYSA-N 6-(2-methoxyethoxymethoxy)naphthalene-2-carboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(OCOCCOC)=CC=C21 XUDWMWHYTBAJHF-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- YADSXVONQHIUDP-UHFFFAOYSA-N 6-(methoxymethoxy)naphthalene-2-carboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(OCOC)=CC=C21 YADSXVONQHIUDP-UHFFFAOYSA-N 0.000 description 1
- KAUQJMHLAFIZDU-UHFFFAOYSA-N 6-Hydroxy-2-naphthoic acid Chemical compound C1=C(O)C=CC2=CC(C(=O)O)=CC=C21 KAUQJMHLAFIZDU-UHFFFAOYSA-N 0.000 description 1
- QCEQBCRMCWRRGT-UHFFFAOYSA-N 6-hexoxynaphthalene-2-carboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(OCCCCCC)=CC=C21 QCEQBCRMCWRRGT-UHFFFAOYSA-N 0.000 description 1
- SKTKMAWOMQFTNS-UHFFFAOYSA-N 6-methoxycarbonylnaphthalene-2-carboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)OC)=CC=C21 SKTKMAWOMQFTNS-UHFFFAOYSA-N 0.000 description 1
- FPTQSHHQJNVVMR-UHFFFAOYSA-N 6-nonoxynaphthalene-2-carboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(OCCCCCCCCC)=CC=C21 FPTQSHHQJNVVMR-UHFFFAOYSA-N 0.000 description 1
- AIEMSTCGCMIJTI-UHFFFAOYSA-N 6-oxo-6-phenylhexanoic acid Chemical compound OC(=O)CCCCC(=O)C1=CC=CC=C1 AIEMSTCGCMIJTI-UHFFFAOYSA-N 0.000 description 1
- FPJJVIAKWJHUMA-UHFFFAOYSA-N 6-propoxynaphthalene-2-carboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(OCCC)=CC=C21 FPJJVIAKWJHUMA-UHFFFAOYSA-N 0.000 description 1
- DOQWHEUDAHLEPT-UHFFFAOYSA-N 7-oxo-7-phenylheptanoic acid Chemical compound OC(=O)CCCCCC(=O)C1=CC=CC=C1 DOQWHEUDAHLEPT-UHFFFAOYSA-N 0.000 description 1
- JBCSSQIVAPZCQY-UHFFFAOYSA-N 7-phenylheptanamide Chemical compound NC(=O)CCCCCCC1=CC=CC=C1 JBCSSQIVAPZCQY-UHFFFAOYSA-N 0.000 description 1
- 229910002016 Aerosil® 200 Inorganic materials 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 239000004255 Butylated hydroxyanisole Substances 0.000 description 1
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 description 1
- 108010036949 Cyclosporine Proteins 0.000 description 1
- 102000004127 Cytokines Human genes 0.000 description 1
- 108090000695 Cytokines Proteins 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 208000031226 Hyperlipidaemia Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 102000004310 Ion Channels Human genes 0.000 description 1
- 108090000862 Ion Channels Proteins 0.000 description 1
- 150000000996 L-ascorbic acids Chemical class 0.000 description 1
- 239000012448 Lithium borohydride Substances 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- ZFMITUMMTDLWHR-UHFFFAOYSA-N Minoxidil Chemical compound NC1=[N+]([O-])C(N)=CC(N2CCCCC2)=N1 ZFMITUMMTDLWHR-UHFFFAOYSA-N 0.000 description 1
- 229920000881 Modified starch Polymers 0.000 description 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
- BXDZOYLPNAIDOC-UHFFFAOYSA-N N-[5-[(5-tert-butyl-1,3-oxazol-2-yl)methylsulfanyl]-1,3-thiazol-2-yl]-1-[2-[2-[2-[2-[2-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]amino]ethoxy]ethoxy]ethoxy]ethylamino]-2-oxoethyl]piperidine-4-carboxamide Chemical compound CC(C)(C)c1cnc(CSc2cnc(NC(=O)C3CCN(CC(=O)NCCOCCOCCOCCNc4cccc5C(=O)N(C6CCC(=O)NC6=O)C(=O)c45)CC3)s2)o1 BXDZOYLPNAIDOC-UHFFFAOYSA-N 0.000 description 1
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methylthiourea Natural products CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 1
- 229930193140 Neomycin Natural products 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 102000016978 Orphan receptors Human genes 0.000 description 1
- 108070000031 Orphan receptors Proteins 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 102000023984 PPAR alpha Human genes 0.000 description 1
- CXOFVDLJLONNDW-UHFFFAOYSA-N Phenytoin Chemical compound N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 CXOFVDLJLONNDW-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 102000004257 Potassium Channel Human genes 0.000 description 1
- 208000006994 Precancerous Conditions Diseases 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- GBFLZEXEOZUWRN-VKHMYHEASA-N S-carboxymethyl-L-cysteine Chemical compound OC(=O)[C@@H](N)CSCC(O)=O GBFLZEXEOZUWRN-VKHMYHEASA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 238000003120 Steady-Glo Luciferase Assay System Methods 0.000 description 1
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- QJJXYPPXXYFBGM-LFZNUXCKSA-N Tacrolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1\C=C(/C)[C@@H]1[C@H](C)[C@@H](O)CC(=O)[C@H](CC=C)/C=C(C)/C[C@H](C)C[C@H](OC)[C@H]([C@H](C[C@H]2C)OC)O[C@@]2(O)C(=O)C(=O)N2CCCC[C@H]2C(=O)O1 QJJXYPPXXYFBGM-LFZNUXCKSA-N 0.000 description 1
- 239000004098 Tetracycline Substances 0.000 description 1
- 235000018936 Vitellaria paradoxa Nutrition 0.000 description 1
- 241001135917 Vitellaria paradoxa Species 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 208000009621 actinic keratosis Diseases 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- MIBQYWIOHFTKHD-UHFFFAOYSA-N adamantane-1-carbonyl chloride Chemical compound C1C(C2)CC3CC2CC1(C(=O)Cl)C3 MIBQYWIOHFTKHD-UHFFFAOYSA-N 0.000 description 1
- 210000001789 adipocyte Anatomy 0.000 description 1
- 150000001299 aldehydes Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- NUZWLKWWNNJHPT-UHFFFAOYSA-N anthralin Chemical compound C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O NUZWLKWWNNJHPT-UHFFFAOYSA-N 0.000 description 1
- 239000000058 anti acne agent Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000002682 anti-psoriatic effect Effects 0.000 description 1
- 229940124340 antiacne agent Drugs 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229960002255 azelaic acid Drugs 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- IANQTJSKSUMEQM-UHFFFAOYSA-N benzofuran Natural products C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- VBICKXHEKHSIBG-UHFFFAOYSA-N beta-monoglyceryl stearate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 235000019282 butylated hydroxyanisole Nutrition 0.000 description 1
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 1
- 229940043253 butylated hydroxyanisole Drugs 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 1
- 229940074360 caffeic acid Drugs 0.000 description 1
- 235000004883 caffeic acid Nutrition 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- 235000021466 carotenoid Nutrition 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 229960001265 ciclosporin Drugs 0.000 description 1
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 description 1
- QAIPRVGONGVQAS-UHFFFAOYSA-N cis-caffeic acid Natural products OC(=O)C=CC1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-UHFFFAOYSA-N 0.000 description 1
- KDLRVYVGXIQJDK-AWPVFWJPSA-N clindamycin Chemical compound CN1C[C@H](CCC)C[C@H]1C(=O)N[C@H]([C@H](C)Cl)[C@@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](SC)O1 KDLRVYVGXIQJDK-AWPVFWJPSA-N 0.000 description 1
- 229960002227 clindamycin Drugs 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- 229960001334 corticosteroids Drugs 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
- 229930182912 cyclosporin Natural products 0.000 description 1
- 238000006264 debenzylation reaction Methods 0.000 description 1
- 239000007854 depigmenting agent Substances 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 229960004042 diazoxide Drugs 0.000 description 1
- OVVMHZRGSHTZDB-UHFFFAOYSA-N dibutylboron Chemical compound CCCC[B]CCCC OVVMHZRGSHTZDB-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- ODCCJTMPMUFERV-UHFFFAOYSA-N ditert-butyl carbonate Chemical compound CC(C)(C)OC(=O)OC(C)(C)C ODCCJTMPMUFERV-UHFFFAOYSA-N 0.000 description 1
- 229960002311 dithranol Drugs 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000007876 drug discovery Methods 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 210000001339 epidermal cell Anatomy 0.000 description 1
- 229960003276 erythromycin Drugs 0.000 description 1
- 239000000262 estrogen Substances 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000019264 food flavour enhancer Nutrition 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000003862 glucocorticoid Substances 0.000 description 1
- 229940075507 glyceryl monostearate Drugs 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000003102 growth factor Substances 0.000 description 1
- 230000003659 hair regrowth Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 239000000017 hydrogel Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000008309 hydrophilic cream Substances 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 229960004337 hydroquinone Drugs 0.000 description 1
- 229910052588 hydroxylapatite Inorganic materials 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000004968 inflammatory condition Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 210000002510 keratinocyte Anatomy 0.000 description 1
- 229960004125 ketoconazole Drugs 0.000 description 1
- BEJNERDRQOWKJM-UHFFFAOYSA-N kojic acid Chemical compound OCC1=CC(=O)C(O)=CO1 BEJNERDRQOWKJM-UHFFFAOYSA-N 0.000 description 1
- 229960004705 kojic acid Drugs 0.000 description 1
- WZNJWVWKTVETCG-UHFFFAOYSA-N kojic acid Natural products OC(=O)C(N)CN1C=CC(=O)C(O)=C1 WZNJWVWKTVETCG-UHFFFAOYSA-N 0.000 description 1
- 229940099367 lanolin alcohols Drugs 0.000 description 1
- 230000004322 lipid homeostasis Effects 0.000 description 1
- 239000008308 lipophilic cream Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 238000003670 luciferase enzyme activity assay Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 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
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 229960003632 minoxidil Drugs 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 230000003020 moisturizing effect Effects 0.000 description 1
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 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
- ZWSWLEWDPNTXSX-UHFFFAOYSA-N n-[[3-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenyl]phenyl]methyl]-n-methyl-6-oxo-6-phenylhexanamide Chemical compound C=1C=CC=CC=1C(=O)CCCCC(=O)N(C)CC(C=1)=CC=CC=1C(C=C1)=CC=C1CC1SC(=O)NC1=O ZWSWLEWDPNTXSX-UHFFFAOYSA-N 0.000 description 1
- 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
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 229940057910 shea butter Drugs 0.000 description 1
- 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)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Cosmetics (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Agricultural Chemicals And Associated Chemicals (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 (de) |
| JP (1) | JP2005518394A (de) |
| KR (1) | KR20040072676A (de) |
| CN (1) | CN100360512C (de) |
| AT (1) | ATE338753T1 (de) |
| AU (1) | AU2002364985A1 (de) |
| BR (1) | BR0214239A (de) |
| CA (1) | CA2468796C (de) |
| CY (1) | CY1106255T1 (de) |
| DE (1) | DE60214595T2 (de) |
| DK (1) | DK1458697T3 (de) |
| ES (1) | ES2272820T3 (de) |
| FR (1) | FR2833949B1 (de) |
| HU (1) | HUP0402616A3 (de) |
| MX (1) | MXPA04006051A (de) |
| PL (1) | PL372881A1 (de) |
| PT (1) | PT1458697E (de) |
| RU (1) | RU2323212C2 (de) |
| WO (1) | WO2003055867A1 (de) |
| ZA (1) | ZA200403797B (de) |
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 |
| JPWO2002098840A1 (ja) | 2001-06-04 | 2004-09-16 | エーザイ株式会社 | カルボン酸誘導体及びその塩もしくはそのエステルからなる医薬 |
| MXPA05005334A (es) * | 2002-11-25 | 2005-11-17 | Galderma Res & Dev | Compuestos bifenilo activadores de los receptores de tipo receptores activados de la proliferacion de peroxisoma gamma y su uso en composiciones cosmeticas o farmaceuticas. |
| EP1651226B1 (de) * | 2003-07-11 | 2010-02-24 | 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. |
| WO2005097127A2 (en) | 2004-04-02 | 2005-10-20 | Merck & Co., Inc. | Method of treating men with metabolic and anthropometric disorders |
| JPWO2006016637A1 (ja) * | 2004-08-11 | 2008-05-01 | 杏林製薬株式会社 | 新規環状アミノ安息香酸誘導体 |
| 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 |
| MX2007001942A (es) * | 2004-08-17 | 2007-05-09 | Galderma Res & Dev | Nuevos compuestos biaromaticos activadores de los receptores del tipo receptor activado del proliferador de peroxisoma (ppar) y su uso en composiciones cosmeticas o farmaceuticas. |
| KR20070042553A (ko) * | 2004-08-17 | 2007-04-23 | 갈데르마 리써어치 앤드 디벨로프먼트 | Ｐｐａｒ 유형의 수용체를 활성화시키는 신규 이방향족화합물 및 화장용 또는 약학 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 |
| 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 |
| CA2587545C (en) * | 2004-11-19 | 2013-10-22 | Galderma Research & Development, S.N.C. | Novel compounds that modulate ppar.gamma. type receptors, and use thereof in cosmetic or pharmaceutical compositions |
| 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 |
| 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 |
| EA020466B1 (ru) | 2007-06-04 | 2014-11-28 | Синерджи Фармасьютикалз Инк. | Агонисты гуанилатциклазы, пригодные для лечения желудочно-кишечных нарушений, воспаления, рака и других заболеваний |
| 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. |
| 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. |
| IE20070928A1 (en) * | 2007-12-21 | 2009-09-30 | Giuliani Int Ltd | Multi target ligands |
| EP2810951B1 (de) | 2008-06-04 | 2017-03-15 | Synergy Pharmaceuticals Inc. | Für die Behandlung von gastrointestinalen Erkrankungen, Entzündungen, Krebs und anderen Erkrankungen geeignete Agonisten von Guanylatcyclase |
| ES2624828T3 (es) | 2008-07-16 | 2017-07-17 | Synergy Pharmaceuticals Inc. | Agonistas de la guanilato ciclasa útiles para el tratamiento de trastornos gastrointestinales, inflamación, cáncer y otros |
| 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 |
| US20130156720A1 (en) | 2010-08-27 | 2013-06-20 | 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 |
| CA2905438A1 (en) | 2013-03-15 | 2014-09-25 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase and their uses |
| CA2905435A1 (en) | 2013-03-15 | 2014-09-25 | Synergy Pharmaceuticals Inc. | Compositions useful for the treatment of gastrointestinal disorders |
| PT3004138T (pt) | 2013-06-05 | 2024-06-18 | Bausch Health Ireland Ltd | Agonistas ultrapuros de guanilato ciclase c, método de produção e utilização dos mesmos |
| CN118184545A (zh) * | 2023-03-22 | 2024-06-14 | 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 |
| EP1067109B1 (de) * | 1998-03-10 | 2009-12-09 | Ono Pharmaceutical Co., Ltd. | Carbonsäurederivate und medikamente die diese als aktiven wirkstoff enthalten |
| HUP0202520A3 (en) * | 1999-08-23 | 2004-11-29 | Kyorin Seiyaku Kk | Substituted benzylthiazolidine-2,4-dione derivatives and pharmaceutical compositions containing them |
| 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 ES ES02805790T patent/ES2272820T3/es not_active Expired - Lifetime
- 2002-12-09 PT PT02805790T patent/PT1458697E/pt unknown
- 2002-12-09 MX MXPA04006051A patent/MXPA04006051A/es active IP Right Grant
- 2002-12-09 JP JP2003556398A patent/JP2005518394A/ja not_active Withdrawn
- 2002-12-09 HU HU0402616A patent/HUP0402616A3/hu unknown
- 2002-12-09 EP EP02805790A patent/EP1458697B1/de not_active Expired - Lifetime
- 2002-12-09 PL PL02372881A patent/PL372881A1/xx not_active Application Discontinuation
- 2002-12-09 AT AT02805790T patent/ATE338753T1/de not_active IP Right Cessation
- 2002-12-09 AU AU2002364985A patent/AU2002364985A1/en not_active Abandoned
- 2002-12-09 WO PCT/FR2002/004232 patent/WO2003055867A1/fr active IP Right Grant
- 2002-12-09 DE DE60214595T patent/DE60214595T2/de not_active Expired - Lifetime
- 2002-12-09 RU RU2004122394/04A patent/RU2323212C2/ru not_active IP Right Cessation
- 2002-12-09 DK DK02805790T patent/DK1458697T3/da active
- 2002-12-09 CN CNB028254899A patent/CN100360512C/zh not_active Expired - Fee Related
- 2002-12-09 BR BR0214239-2A patent/BR0214239A/pt not_active IP Right Cessation
- 2002-12-09 CA CA2468796A patent/CA2468796C/fr not_active Expired - Fee Related
- 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 |
|---|---|
| ATE338753T1 (de) | 2006-09-15 |
| AU2002364985A1 (en) | 2003-07-15 |
| MXPA04006051A (es) | 2004-09-27 |
| RU2323212C2 (ru) | 2008-04-27 |
| FR2833949B1 (fr) | 2005-08-05 |
| DK1458697T3 (da) | 2007-01-15 |
| EP1458697A1 (de) | 2004-09-22 |
| PT1458697E (pt) | 2007-01-31 |
| HUP0402616A2 (hu) | 2005-03-29 |
| HUP0402616A3 (en) | 2009-01-28 |
| FR2833949A1 (fr) | 2003-06-27 |
| WO2003055867A1 (fr) | 2003-07-10 |
| JP2005518394A (ja) | 2005-06-23 |
| DE60214595D1 (de) | 2006-10-19 |
| BR0214239A (pt) | 2004-09-21 |
| EP1458697B1 (de) | 2006-09-06 |
| CA2468796C (fr) | 2012-07-17 |
| PL372881A1 (en) | 2005-08-08 |
| CN1639138A (zh) | 2005-07-13 |
| CA2468796A1 (fr) | 2003-07-10 |
| DE60214595T2 (de) | 2007-09-13 |
| CN100360512C (zh) | 2008-01-09 |
| KR20040072676A (ko) | 2004-08-18 |
| CY1106255T1 (el) | 2011-06-08 |
| RU2004122394A (ru) | 2005-03-27 |
| ES2272820T3 (es) | 2007-05-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US7294639B2 (en) | Biaromatic ligand activators of PPARγ receptors | |
| ZA200403797B (en) | Biphenylmethyl-thiazolidinediones and analogues and their use as PPAR-gamma activators. | |
| AU2001285981B2 (en) | Biphenyl derivatives and their use as PPAR-GAMMA receptor activators | |
| US7807669B2 (en) | Biaromatic compounds which activate PPARγ type receptors and cosmetic/pharmaceutical compositions comprised thereof | |
| AU2005274277A1 (en) | Novel biaromatic compounds which activate receptors of PPAR type and their use in cosmetic or pharmaceutical compositions | |
| JP2672268B2 (ja) | 新規なアミド誘導された二芳香族化合物、これらを含む調剤用及び化粧用組成物並びにこれらの用途 | |
| AU745699B2 (en) | (Poly) thiaalkynoic compounds and their derivatives, compositions comprising them and their use | |
| US5935585A (en) | Biaromatic amido compounds and pharmaceutical/cosmetic compositions comprised thereof | |
| US20070207175A1 (en) | Biaromatic compound activators of PPARgamma receptors and cosmetic/pharmaceutical compositions comprised thereof | |
| ZA200504205B (en) | Biaromatic compounds which activate ppar-gama typereceptors, and use thereof in cosmetic or pharmac eutical compositions. | |
| US20080004274A1 (en) | Novel biaromatic compounds that modulate PPAR type receptors and cosmetic/pharmaceutical compositions comprised thereof | |
| CA2506523C (en) | Novel biaromatic compounds which activate ppar-gamma type receptors, and use thereof in cosmetic or pharmaceutical compositions | |
| US7829588B2 (en) | Modulators of the PPAR-type receptors and pharmaceutical/cosmetic applications thereof | |
| FR2836683A1 (fr) | NOUVEAUX LIGANDS ACTIVATEURS DES RECEPTEURS PPARy, LEUR PROCEDE DE PREPARATION ET LEUR UTILISATION EN MEDECINE HUMAINE AINSI QU'EN COSMETIQUE |