HRP20110133T1 - Novi derivati 3-fenilpropanske kiseline kao aktivatori ppar-tipa receptora, postupak njihovog dobivanja i njihova upotreba u kozmetičkim ili farmaceutskim pripravcima - Google Patents
Novi derivati 3-fenilpropanske kiseline kao aktivatori ppar-tipa receptora, postupak njihovog dobivanja i njihova upotreba u kozmetičkim ili farmaceutskim pripravcima Download PDFInfo
- Publication number
- HRP20110133T1 HRP20110133T1 HR20110133T HRP20110133T HRP20110133T1 HR P20110133 T1 HRP20110133 T1 HR P20110133T1 HR 20110133 T HR20110133 T HR 20110133T HR P20110133 T HRP20110133 T HR P20110133T HR P20110133 T1 HRP20110133 T1 HR P20110133T1
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- Croatia
- Prior art keywords
- radical
- propyl
- phenyl
- propanoic acid
- methoxyphenyl
- Prior art date
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- 239000002537 cosmetic Substances 0.000 title claims 3
- XMIIGOLPHOKFCH-AKZCFXPHSA-N 3-phenylpropanoic acid Chemical class OC(=O)[13CH2][13CH2]C1=CC=CC=C1 XMIIGOLPHOKFCH-AKZCFXPHSA-N 0.000 title 1
- 230000003213 activating effect Effects 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- -1 alkoxy radical Chemical class 0.000 claims abstract 39
- 150000001875 compounds Chemical class 0.000 claims abstract 25
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 8
- 150000003254 radicals Chemical class 0.000 claims abstract 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract 5
- 150000002367 halogens Chemical class 0.000 claims abstract 5
- 150000003839 salts Chemical class 0.000 claims abstract 5
- 239000004721 Polyphenylene oxide Chemical class 0.000 claims abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 4
- 239000001257 hydrogen Substances 0.000 claims abstract 4
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims abstract 4
- XSXHWVKGUXMUQE-UHFFFAOYSA-N osmium dioxide Inorganic materials O=[Os]=O XSXHWVKGUXMUQE-UHFFFAOYSA-N 0.000 claims abstract 4
- 229920000570 polyether Chemical class 0.000 claims abstract 4
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract 3
- 239000002253 acid Substances 0.000 claims abstract 2
- 150000004677 hydrates Chemical class 0.000 claims abstract 2
- 239000012453 solvate Substances 0.000 claims abstract 2
- 208000002874 Acne Vulgaris Diseases 0.000 claims 11
- 206010000496 acne Diseases 0.000 claims 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 10
- 208000035475 disorder Diseases 0.000 claims 9
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 230000005855 radiation Effects 0.000 claims 3
- PECUAXSDHHOSTJ-UHFFFAOYSA-N 3-[3-butoxy-4-[3-(4-butylsulfonyloxy-3-methoxyphenyl)propyl]phenyl]propanoic acid Chemical compound CCCCOC1=CC(CCC(O)=O)=CC=C1CCCC1=CC=C(OS(=O)(=O)CCCC)C(OC)=C1 PECUAXSDHHOSTJ-UHFFFAOYSA-N 0.000 claims 2
- 201000004384 Alopecia Diseases 0.000 claims 2
- 206010003645 Atopy Diseases 0.000 claims 2
- 208000012641 Pigmentation disease Diseases 0.000 claims 2
- 230000032683 aging Effects 0.000 claims 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 231100000360 alopecia Toxicity 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 239000002585 base Substances 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 210000000987 immune system Anatomy 0.000 claims 2
- 230000037356 lipid metabolism Effects 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 230000035755 proliferation Effects 0.000 claims 2
- 208000017520 skin disease Diseases 0.000 claims 2
- 201000010153 skin papilloma Diseases 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 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 1
- PRNOKSMZKBISGQ-UHFFFAOYSA-N 3-[2-butoxy-4-[3-(4-butylsulfonyloxy-3-methoxyphenyl)propyl]phenyl]propanoic acid Chemical compound C1=C(CCC(O)=O)C(OCCCC)=CC(CCCC=2C=C(OC)C(OS(=O)(=O)CCCC)=CC=2)=C1 PRNOKSMZKBISGQ-UHFFFAOYSA-N 0.000 claims 1
- LAWRROCVVPXLIU-UHFFFAOYSA-N 3-[3-butoxy-4-[2-[4-[methyl-[2-(4-methylphenyl)ethylsulfonyl]amino]phenyl]ethoxy]phenyl]propanoic acid Chemical compound CCCCOC1=CC(CCC(O)=O)=CC=C1OCCC1=CC=C(N(C)S(=O)(=O)CCC=2C=CC(C)=CC=2)C=C1 LAWRROCVVPXLIU-UHFFFAOYSA-N 0.000 claims 1
- NQSRVPLYKKUMJE-UHFFFAOYSA-N 3-[3-butoxy-4-[3-(3-methoxy-4-methylsulfonyloxyphenyl)propyl]phenyl]propanoic acid Chemical compound CCCCOC1=CC(CCC(O)=O)=CC=C1CCCC1=CC=C(OS(C)(=O)=O)C(OC)=C1 NQSRVPLYKKUMJE-UHFFFAOYSA-N 0.000 claims 1
- DOYURSILWWZUDN-UHFFFAOYSA-N 3-[3-butoxy-4-[3-(3-methoxy-4-phenylmethoxyphenyl)propyl]phenyl]propanoic acid Chemical compound CCCCOC1=CC(CCC(O)=O)=CC=C1CCCC(C=C1OC)=CC=C1OCC1=CC=CC=C1 DOYURSILWWZUDN-UHFFFAOYSA-N 0.000 claims 1
- DRFRPLVKXHXLMG-UHFFFAOYSA-N 3-[3-butoxy-4-[3-(4-butoxy-3-methoxyphenyl)propyl]phenyl]propanoic acid Chemical compound C1=C(OC)C(OCCCC)=CC=C1CCCC1=CC=C(CCC(O)=O)C=C1OCCCC DRFRPLVKXHXLMG-UHFFFAOYSA-N 0.000 claims 1
- JOCJSDGVIMANTA-UHFFFAOYSA-N 3-[3-butoxy-4-[3-(4-ethoxy-3-methoxyphenyl)propyl]phenyl]propanoic acid Chemical compound CCCCOC1=CC(CCC(O)=O)=CC=C1CCCC1=CC=C(OCC)C(OC)=C1 JOCJSDGVIMANTA-UHFFFAOYSA-N 0.000 claims 1
- UMJMAVLTFMDFNX-UHFFFAOYSA-N 3-[3-butoxy-4-[3-(4-ethylsulfonyloxy-3-methoxyphenyl)propyl]phenyl]propanoic acid Chemical compound CCCCOC1=CC(CCC(O)=O)=CC=C1CCCC1=CC=C(OS(=O)(=O)CC)C(OC)=C1 UMJMAVLTFMDFNX-UHFFFAOYSA-N 0.000 claims 1
- CDPMOGOZZUMYRV-UHFFFAOYSA-N 3-[3-butoxy-4-[3-[4-(butylsulfonylamino)phenyl]propyl]phenyl]propanoic acid Chemical compound CCCCOC1=CC(CCC(O)=O)=CC=C1CCCC1=CC=C(NS(=O)(=O)CCCC)C=C1 CDPMOGOZZUMYRV-UHFFFAOYSA-N 0.000 claims 1
- SHPMZELYWTXGEP-UHFFFAOYSA-N 3-[4-[2-(3-chloro-4-ethoxyphenyl)ethoxy]-3-methoxyphenyl]propanoic acid Chemical compound C1=C(Cl)C(OCC)=CC=C1CCOC1=CC=C(CCC(O)=O)C=C1OC SHPMZELYWTXGEP-UHFFFAOYSA-N 0.000 claims 1
- MQOGIHYBTPWRPC-UHFFFAOYSA-N 3-[4-[2-[4-[(3-chlorobenzoyl)-methylamino]phenyl]ethoxy]-3-(2-ethoxyethoxy)phenyl]propanoic acid Chemical compound CCOCCOC1=CC(CCC(O)=O)=CC=C1OCCC1=CC=C(N(C)C(=O)C=2C=C(Cl)C=CC=2)C=C1 MQOGIHYBTPWRPC-UHFFFAOYSA-N 0.000 claims 1
- NOIXBTNVEJIFQB-UHFFFAOYSA-N 3-[4-[3-(3-chloro-4-hexylsulfonyloxyphenyl)propyl]-3-ethoxyphenyl]propanoic acid Chemical compound C1=C(Cl)C(OS(=O)(=O)CCCCCC)=CC=C1CCCC1=CC=C(CCC(O)=O)C=C1OCC NOIXBTNVEJIFQB-UHFFFAOYSA-N 0.000 claims 1
- ZONLWQITLBHWAS-UHFFFAOYSA-N 3-[4-[3-(4-butylsulfonyloxy-2-methoxyphenyl)propyl]-3-(2-ethoxyethoxy)phenyl]propanoic acid Chemical compound COC1=CC(OS(=O)(=O)CCCC)=CC=C1CCCC1=CC=C(CCC(O)=O)C=C1OCCOCC ZONLWQITLBHWAS-UHFFFAOYSA-N 0.000 claims 1
- HFHDMDAKQKAIKK-UHFFFAOYSA-N 3-[4-[3-(4-butylsulfonyloxy-3-methoxyphenyl)propyl]-2-[(3-methoxyphenyl)methoxy]phenyl]propanoic acid Chemical compound C1=C(OC)C(OS(=O)(=O)CCCC)=CC=C1CCCC1=CC=C(CCC(O)=O)C(OCC=2C=C(OC)C=CC=2)=C1 HFHDMDAKQKAIKK-UHFFFAOYSA-N 0.000 claims 1
- OIILNTKZZPPDJY-UHFFFAOYSA-N 3-[4-[3-(4-butylsulfonyloxy-3-methoxyphenyl)propyl]-3-(cyclopropylmethoxy)phenyl]propanoic acid Chemical compound C1=C(OC)C(OS(=O)(=O)CCCC)=CC=C1CCCC1=CC=C(CCC(O)=O)C=C1OCC1CC1 OIILNTKZZPPDJY-UHFFFAOYSA-N 0.000 claims 1
- XXOKYHJVQVWIAE-UHFFFAOYSA-N 3-[4-[3-(4-butylsulfonyloxy-3-methoxyphenyl)propyl]-3-[(3-fluorophenyl)methoxy]phenyl]propanoic acid Chemical compound C1=C(OC)C(OS(=O)(=O)CCCC)=CC=C1CCCC1=CC=C(CCC(O)=O)C=C1OCC1=CC=CC(F)=C1 XXOKYHJVQVWIAE-UHFFFAOYSA-N 0.000 claims 1
- UVLPCQGDJDZJED-UHFFFAOYSA-N 3-[4-[3-(4-butylsulfonyloxy-3-methoxyphenyl)propyl]-3-[(4-fluorophenyl)methoxy]phenyl]propanoic acid Chemical compound C1=C(OC)C(OS(=O)(=O)CCCC)=CC=C1CCCC1=CC=C(CCC(O)=O)C=C1OCC1=CC=C(F)C=C1 UVLPCQGDJDZJED-UHFFFAOYSA-N 0.000 claims 1
- HFPIZEKNUHOBIZ-UHFFFAOYSA-N 3-[4-[3-(4-butylsulfonyloxyphenyl)propyl]-3-hydroxyphenyl]propanoic acid Chemical compound C1=CC(OS(=O)(=O)CCCC)=CC=C1CCCC1=CC=C(CCC(O)=O)C=C1O HFPIZEKNUHOBIZ-UHFFFAOYSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- 206010000501 Acne conglobata Diseases 0.000 claims 1
- 206010003210 Arteriosclerosis Diseases 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 201000009030 Carcinoma Diseases 0.000 claims 1
- 206010008570 Chloasma Diseases 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 208000027932 Collagen disease Diseases 0.000 claims 1
- 208000002506 Darier Disease Diseases 0.000 claims 1
- 201000004624 Dermatitis Diseases 0.000 claims 1
- 206010020649 Hyperkeratosis Diseases 0.000 claims 1
- 208000031226 Hyperlipidaemia Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 208000003367 Hypopigmentation Diseases 0.000 claims 1
- 206010023347 Keratoacanthoma Diseases 0.000 claims 1
- 208000001126 Keratosis Diseases 0.000 claims 1
- 206010023369 Keratosis follicular Diseases 0.000 claims 1
- 208000003351 Melanosis Diseases 0.000 claims 1
- 206010028703 Nail psoriasis Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 206010033554 Palmoplantar keratoderma Diseases 0.000 claims 1
- 208000006994 Precancerous Conditions Diseases 0.000 claims 1
- 206010039710 Scleroderma Diseases 0.000 claims 1
- 206010039792 Seborrhoea Diseases 0.000 claims 1
- 206010040925 Skin striae Diseases 0.000 claims 1
- 208000031439 Striae Distensae Diseases 0.000 claims 1
- 206010042971 T-cell lymphoma Diseases 0.000 claims 1
- 208000027585 T-cell non-Hodgkin lymphoma Diseases 0.000 claims 1
- 206010047642 Vitiligo Diseases 0.000 claims 1
- 206010048222 Xerosis Diseases 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 208000011775 arteriosclerosis disease Diseases 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 208000010668 atopic eczema Diseases 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 208000035269 cancer or benign tumor Diseases 0.000 claims 1
- 210000000748 cardiovascular system Anatomy 0.000 claims 1
- 210000004027 cell Anatomy 0.000 claims 1
- 230000024245 cell differentiation Effects 0.000 claims 1
- 230000004663 cell proliferation Effects 0.000 claims 1
- 238000002512 chemotherapy Methods 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 230000004064 dysfunction Effects 0.000 claims 1
- 230000002500 effect on skin Effects 0.000 claims 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 208000009197 gingival hypertrophy Diseases 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 208000000069 hyperpigmentation Diseases 0.000 claims 1
- 230000003810 hyperpigmentation Effects 0.000 claims 1
- 230000003425 hypopigmentation Effects 0.000 claims 1
- 206010021198 ichthyosis Diseases 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 230000003780 keratinization Effects 0.000 claims 1
- 201000004607 keratosis follicularis Diseases 0.000 claims 1
- 230000003902 lesion Effects 0.000 claims 1
- 208000002741 leukoplakia Diseases 0.000 claims 1
- 206010025135 lupus erythematosus Diseases 0.000 claims 1
- 230000003211 malignant effect Effects 0.000 claims 1
- AZFBNCHYINKARG-UHFFFAOYSA-N methyl 3-[3-butoxy-4-[3-(4-ethoxy-3-fluorophenyl)propyl]phenyl]propanoate Chemical compound CCCCOC1=CC(CCC(=O)OC)=CC=C1CCCC1=CC=C(OCC)C(F)=C1 AZFBNCHYINKARG-UHFFFAOYSA-N 0.000 claims 1
- GSTDEMYDDQSCNH-UHFFFAOYSA-N methyl 3-[3-methoxy-4-[3-[4-(2-oxopropylamino)phenyl]propyl]phenyl]propanoate Chemical compound COC1=CC(CCC(=O)OC)=CC=C1CCCC1=CC=C(NCC(C)=O)C=C1 GSTDEMYDDQSCNH-UHFFFAOYSA-N 0.000 claims 1
- MISBWYAETLPCCT-UHFFFAOYSA-N methyl 3-[4-[3-(4-acetamidophenyl)propyl]-3-(2-methoxyethoxy)phenyl]propanoate Chemical compound COCCOC1=CC(CCC(=O)OC)=CC=C1CCCC1=CC=C(NC(C)=O)C=C1 MISBWYAETLPCCT-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 201000008743 palmoplantar keratosis Diseases 0.000 claims 1
- 208000003154 papilloma Diseases 0.000 claims 1
- 208000029211 papillomatosis Diseases 0.000 claims 1
- 230000007170 pathology Effects 0.000 claims 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 230000019612 pigmentation Effects 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 230000001185 psoriatic effect Effects 0.000 claims 1
- 230000001105 regulatory effect Effects 0.000 claims 1
- 230000000241 respiratory effect Effects 0.000 claims 1
- 201000004700 rosacea Diseases 0.000 claims 1
- 229930195734 saturated hydrocarbon Natural products 0.000 claims 1
- 210000001732 sebaceous gland Anatomy 0.000 claims 1
- 208000008742 seborrheic dermatitis Diseases 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
- 230000003612 virological effect Effects 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
- C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
- C07C309/66—Methanesulfonates
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Abstract
Spoj, naznačen time što ima opću formulu (I) niže: u kojoj:- R1 predstavlja hidroksilni radikal ili alkoksi radikal;- R2 predstavlja vodik, alkilni radikal, cikloalkilni radikal, izborno supstituirani aralkilni radikal ili polieterski radikal;- R3 predstavlja vodik, halogen, alkilni radikal ili alkoksi radikal;- R4 predstavlja alkilni radikal, izborno supstituirani arilni radikal ili izborno supstituirani aralkilni radikal;- X predstavlja atom kisika ili radikal CH2;- Y predstavlja atom kisika, radikal NR5 ili radikal OSO2, OCO, NR5CO ili NR5SO2;- R5 predstavlja atom vodika ili alkilni radikal; a također i njegove soli s farmaceutski prihvatljivom kiselinom ili bazom, njihovi farmaceutski prihvatljivi solvati i njihovi hidrati. Patent sadrži još 22 patentna zahtjeva.
Claims (23)
1. Spoj, naznačen time što ima opću formulu (I) niže:
[image]
u kojoj:
– R1 predstavlja hidroksilni radikal ili alkoksi radikal;
– R2 predstavlja vodik, alkilni radikal, cikloalkilni radikal, izborno supstituirani aralkilni radikal ili polieterski radikal;
– R3 predstavlja vodik, halogen, alkilni radikal ili alkoksi radikal;
– R4 predstavlja alkilni radikal, izborno supstituirani arilni radikal ili izborno supstituirani aralkilni radikal;
– X predstavlja atom kisika ili radikal CH2;
– Y predstavlja atom kisika, radikal NR5 ili radikal OSO2, OCO, NR5CO ili NR5SO2;
– R5 predstavlja atom vodika ili alkilni radikal;
a također i njegove soli s farmaceutski prihvatljivom kiselinom ili bazom, njihovi farmaceutski prihvatljivi solvati i njihovi hidrati.
2. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je u obliku soli s alkalnim ili zemnoalkalnim metalom ili soli s organskim aminom.
3. Spoj u skladu s patentnim zahtjevom 1, naznačen time što, kada nosi aminsku funkcionalnu skupinu, je u obliku soli s mineralnom ili organskom kiselinom.
4. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 3, naznačen time što navedeni alkilni radikal predstavlja nerazgranati ili razgranati zasićeni ugljikovodični lanac koji sadrži 1 do 12 atoma ugljika.
5. Spoj u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačen time što navedeni alkilni radikal se bira između metilnog, etilnog, propilnog, izopropilnog, butila, izobutilnog, tert-butilnog, pentilnog, izoamilnog, amilnog i heksilnog radikala.
6. Spoj u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačen time što navedeni cikloalkilni radikal predstavlja zasićeni prstenasti ugljikovodični lanac koji sadrži 3 do 7 atoma ugljika.
7. Spoj u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačen time što navedeni izborno supstituirani arilni radikal se bira između fenila i naftila, izborno supstituiranih s jednim ili više atoma ili atomskih skupina, koje se bira između alkila, alkoksi, halogena, hidroksila, cijano, trifluormetila i nitro.
8. Spoj u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačen time što navedeni izborno supstituirani aralkilni radikal se bira između benzila i fenetila, izborno supstituiranih s jednim ili više atoma ili atomskih skupina, koje se bira između alkila, alkoksi, halogena, hidroksila, cijano, trifluormetila i nitro.
9. Spoj u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačen time što navedeni atom halogena se bira između atoma fluora, klora, broma i joda.
10. Spoj u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačen time što navedeni alkoksi radikal se bira između metoksi, etoksi, izopropiloksi, n-propiloksi, tert-butoksi, n-butoksi, n-pentiloksi i n-heksiloksi radikala.
11. Spoj u skladu s bilo kojim od prethodnih patentnih zahtjeva, naznačen time što navedeni polieterski radikal se bira između radikala koji sadrže 1 do 7 atoma ugljika, prekinutih najmanje jednim atomom kisika, po mogućnosti metoksietoksi, etoksietoksi, metoksietil, etoksietil i metoksietoksietoksi radikala.
12. Spoj u skladu s patentnim zahtjevom 1, naznačen time što ga se bira iz skupine koju čine:
1. 3-{4-[3-(4-benziloksi-3-metoksifenil)propil]-3-butoksifenil}propanska kiselina
2. 3-{3-butoksi-4-[3-(4-etoksi-3-metoksifenil)propil]fenil}propanska kiselina
3. 3-{3-butoksi-4-[3-(4-butoksi-3-metoksifenil)propil]fenil}propanska kiselina
4. 3-{3-butoksi-4-[3-(4-metansulfoniloksi-3-metoksifenil)propil]fenil}propanska kiselina
5. 3-(4-{3-[4-(butan-1-sulfoniloksi)-3-metoksifenil]propil}-3-butoksifenil)propanska kiselina
6. 3-{3-butoksi-4-[3-(4-etansulfoniloksi-3-metoksifenil)propil]fenil)propanska kiselina
7. 3-[4-{3-[4-(butan-1-sulfoniloksi)-3-metoksifenil]propil}-3-(3-fluorbenziloksi)fenil]propanska kiselina
8. 3-[4-{3-[4-(butan-1-sulfoniloksi)-3-metoksifenil]propil}-3-(4-fluorbenziloksi)fenil]propanska kiselina
9. 3-(4-{3-[4-(butan-1-sulfoniloksi)-3-metoksifenil]propil}-3-ciklopropilmetoksifenil)propanska kiselina
10. 3-[4-{3-[4-(butan-1-sulfoniloksi)-3-metoksifenil]propil}-2-(3-metoksibenziloksi)fenil]propanska kiselina
11. 3-(4-{3-[4-(butan-1-sulfoniloksi)-3-metoksifenil]propil}-2-butoksifenil)propanska kiselina
12. metil-3-[4-[3-(4-acetilaminofenil)propil]-3-(2-metoksietoksi)fenil]propanoat
13. metil-3-(4-{3-[4-(acetilmetilamino)fenil]propil}-3-metoksifenil)propanoat
14. 3-(4-{3-[4-(butan-1-sulfoniloksi)fenil]propil}-3-hidroksifenil)propanska kiselina
15. 3-(4-{3-[4-(butan-1-sulfonilamino)fenil]propil}-3-butoksifenil)propanska kiselina
16. 3-[4-(2-{4-[(3-klorobenzoil)metilamino]fenil}etoksi)-3-(2-etoksietoksi)fenil]propanska kiselina
17. 3-[3-butoksi-4-(2-{4-[metil-(2-p-toliletansulfonil)amino]fenil}etoksi)fenil]propanska kiselina
18. 3-(4-{3-[4-(butan-1-sulfoniloksi)-3-metoksifenil]propil}-3-butoksifenil)propanska kiselina
19. metil-3-{3-butoksi-4-[3-(4-etoksi-3-fluorfenil)propil]fenil}propanoat
20. 3-[4-{3-[4-(butan-1-sulfoniloksi)-2-metoksifenil]propil}-3-(2-etoksietoksi)fenil]propanska kiselina
21. 3-(4-{3-[3-kloro-4-(heksan-1-sulfoniloksi)fenil]propil}-3-etoksifenil)propanska kiselina
22. 3-{4-[2-(3-kloro-4-etoksifenil)etoksi]-3-metoksifenil}propanska kiselina
23. 4-{3-[4-(2-karboksietil)-2-metoksifenil]propil}fenil-butirat.
13. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 12, naznačen time što ima najmanje jednu od sljedećih karakteristika:
– R1 je hidroksilni radikal,
– R2 predstavlja alkilni radikal ili polieterski radikal,
– R3 predstavlja atom vodika, alkoksi radikal ili halogen,
– R4 predstavlja alkilni radikal,
– X predstavlja atom kisika ili skupinu CH2,
– Y predstavlja skupinu -NR5SO2 ili skupinu -OSO2, gdje R5 je atom vodika ili alkilni radikal.
14. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 12, naznačen time što ima najmanje jednu od sljedećih karakteristika:
– R1 je hidroksilni radikal,
– R2 predstavlja niži alkilni radikal,
– R3 predstavlja niži alkoksi radikal,
– R4 predstavlja niži alkilni radikal,
– X predstavlja atom kisika ili skupinu CH2,
– Y predstavlja skupinu -OSO2.
15. Kozmetički pripravak, naznačen time što sadrži, u fiziološki prihvatljivoj podlozi, najmanje jedan od spojeva u skladu s bilo kojim od patentnih zahtjeva 1 do 14.
16. Pripravak u skladu s patentnim zahtjevom 15, naznačen time što koncentracija jednog ili više spojeva u skladu s bilo kojim od patentnih zahtjeva 1 do 14 je između 0,001 % i 3 %, težinski, u odnosu na ukupnu težinu pripravka.
17. Kozmetička upotreba pripravka u skladu s bilo kojim od patentnih zahtjeva 1 do 14 ili pripravka u skladu s bilo kojim od patentnih zahtjeva 15 i 16, naznačena time što navedeni pripravak je namijenjen higijeni tijela ili kose.
18. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 14, naznačen time što ga se upotrebljava kao medikament.
19. Upotreba spoja u skladu s bilo kojim od patentnih zahtjeva 1 do 14, naznačena time što je navedeni spoj namijenjen proizvodnji pripravka za reguliranje i/ili obnavljanje metabolizma lipida u koži.
20. Upotreba spoja u skladu s bilo kojim od patentnih zahtjeva 1 do 14, naznačena time što je navedeni spoj namijenjen proizvodnji pripravka za liječenje:
– dermatoloških poremećaja, povezanih s poremećajem keratinizacije, povezanim sa staničnom diferencijacijom i proliferacijom, osobito za liječenje običnih akni, komedonskih akni, polimorfnih akni, akni rozacea, nodulocističnih akni, acne conglobata, staračkih akni i sekundarih akni, poput solarnih akni, akni povezanih s lijekovima ili profesionalnih akni;
– ihtioze, ihtioziformnih stanja, Darierove bolesti, palmoplantarne keratoderme, leukoplakije i leukoplakiformnih stanja, i kutani ili mucous (buccal) lichen;
– dermatoloških poremećaja s upalnom imunoalergijskom komponentom, uz ili bez poremećaja stanične proliferacije, osobito kutane, mukozne ili psorijaze noktiju, psorijatičnog reumatizma, kutane atopije, poput ekzema, respiratorne atopija ili hipertrofije desni;
– dermalnih ili epidermalnih proliferacija, bilo dobroćudnih ili zloćudnih, te bilo virusnog podrijetla ili ne, osobito običnih bradavica, pljosnatih bradavica i veruciformne epidermodispalzije, oralne ili papilomatoze floride, limfoma T-stanica;
– proliferacija koje mogu biti inducirane ultraljubičastim zračenjem, osobito epitelioma bazalnih i spinalnih stanica;
– prekanceroznih lezija kože, osobito keratoakantoma;
– imunosnih dermatoza, osobito eritematoznog lupusa;
– imunosnih buloznih bolesti;
– kolagenskih bolesti, osobito skleroderme;
– dermatoloških ili općih poremećaja s imunološkom komponentom;
– poremećaja kože uzrokovanih izlaganjem UV zračenju, fotoinduciranog ili kronološkog starenja kože, aktiničnih pigmentacija i keratoze, ili bilo koje patologije povezane s kronološkim ili aktiničnim starenjem, osobito kseroze;
– poremećaja funkcije lojnih žlijezda, osobito hiperseboreje s aknama ili obične seboreje;
– poremećaja cikatrizacije ili strija;
– poremećaja pigmentacije, poput hiperpigmentacije, melazme, hipopigmentacije ili vitiliga;
– poremećaja metabolizma lipida, poput pretilosti, hiperlipidemije, ili dijabetesa neovisnog o inzulinu;
– upalnih poremećaja, poput artritisa;
– kanceroznih ili prekanceroznih stanja;
– alopecije različitog podrijetla, osobito alopecije uzrokovane kemoterapijom ili zračenjem;
– poremećaja imunosnog sustava, poput astme, dijabetesa tip I, multiple skleroze ili drugih selektivnih disfunkcija imunosnog sustava; i
– poremećaja kardiovaskularnog sustava, poput arterioskleroze ili hipertenzije.
21. Farmaceutski pripravak, naznačen time što sadrži, u fiziološki prihvatljivom mediju, najmanje jedan spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 14.
22. Pripravak u skladu s patentnim zahtjevom 21, naznačen time što koncentracija jednog ili više spojeva u skladu s bilo kojim od patentnih zahtjeva 1 do 14 je između 0,001 % i 10 %, težinski, u odnosu na ukupnu težinu pripravka.
23. Pripravak u skladu s patentnim zahtjevom 21, naznačen time što koncentracija jednog ili više spojeva u skladu s bilo kojim od patentnih zahtjeva 1 do 14 je između 0,01 % i 1 %, težinski, u odnosu na ukupnu težinu pripravka.
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FR0755476A FR2917084B1 (fr) | 2007-06-05 | 2007-06-05 | 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. |
PCT/FR2008/050996 WO2008152333A2 (fr) | 2007-06-05 | 2008-06-04 | Nouveaux dérivés d'acide 3-phényl propanoïque activateurs des récepteurs de type ppar, leur méthode de préparation et leur utilisation dans des compositions cosmétiques ou pharmaceutiques |
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ES2423793T3 (es) | 2008-05-26 | 2013-09-24 | Genfit | Compuestos agonistas de PPAR, preparación y usos para el tratamiento de la diabetes y/o dislipidemias |
FR2984730A1 (fr) * | 2011-12-22 | 2013-06-28 | Diverchim | Nouvelles compositions cosmetiques anti-age et depigmentantes |
CN103965048B (zh) * | 2014-05-06 | 2016-02-17 | 西北农林科技大学 | 反式肉桂酸酯类化合物及其合成方法和应用 |
Family Cites Families (17)
Publication number | Priority date | Publication date | Assignee | Title |
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FR2653119B1 (fr) * | 1989-10-18 | 1994-08-05 | Lipha | Nouveaux aryloxy alcoyl benzenes, leurs procedes de preparation et les compositions pharmaceutiques en renfermant. |
AU8750298A (en) * | 1997-08-28 | 1999-03-22 | Ono Pharmaceutical Co. Ltd. | Peroxisome proliferator-activated receptor controllers |
MA26634A1 (fr) * | 1998-06-04 | 2004-12-20 | Astra Ab | Nouveaux derives de l'acide 3-aryl propionique et analogues |
SE9904421D0 (sv) * | 1999-12-03 | 1999-12-03 | Astra Ab | New compounds |
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 |
MXPA04001253A (es) * | 2001-08-09 | 2004-06-03 | Ono Pharmaceutical Co | Derivados de acidos carboxilicos y agente farmaceutico que comprende los mismos como ingrediente activo. |
FR2833949B1 (fr) * | 2001-12-21 | 2005-08-05 | Galderma Res & Dev | NOUVEAUX LIGANDS ACTIVATEURS DES RECEPTEURS PPARy, LEUR PROCEDE DE PREPARATION ET LEUR UTILISATION EN MEDECINE HUMAINE AINSI QU'EN COSMETIQUE |
JP4594611B2 (ja) * | 2002-11-08 | 2010-12-08 | 武田薬品工業株式会社 | 受容体機能調節剤 |
US7615575B2 (en) * | 2003-02-13 | 2009-11-10 | Wellstat Therapeutics Corporation | Compounds for the treatment of metabolic disorders |
US7244763B2 (en) * | 2003-04-17 | 2007-07-17 | Warner Lambert Company Llc | Compounds that modulate PPAR activity and methods of preparation |
JP2007528362A (ja) * | 2003-08-14 | 2007-10-11 | 旭化成ファーマ株式会社 | 置換アリールアルカン酸誘導体及びその用途 |
CA2536089A1 (en) * | 2003-08-20 | 2005-03-03 | Eli Lilly And Company | Ppar modulators |
WO2006057448A1 (ja) * | 2004-11-26 | 2006-06-01 | Takeda Pharmaceutical Company Limited | アリールアルカン酸誘導体 |
AU2006287521A1 (en) * | 2005-09-07 | 2007-03-15 | Plexxikon, Inc. | PPARactive compounds |
FR2892412B1 (fr) * | 2005-10-26 | 2008-05-16 | Galderma Res & Dev | Composes biaromatiques modulateurs des ppars |
JP5243696B2 (ja) * | 2006-03-17 | 2013-07-24 | 田辺三菱製薬株式会社 | ベンゼン誘導体 |
FR2902789A1 (fr) * | 2006-06-21 | 2007-12-28 | Genfit Sa | Derives de 1,3-diphenylpropane substitues, preparations et utilisations |
-
2007
- 2007-06-05 FR FR0755476A patent/FR2917084B1/fr not_active Expired - Fee Related
-
2008
- 2008-06-04 AT AT08805936T patent/ATE490234T1/de active
- 2008-06-04 ES ES08805936T patent/ES2357183T3/es active Active
- 2008-06-04 SI SI200830111T patent/SI2155662T1/sl unknown
- 2008-06-04 JP JP2010510858A patent/JP2010529098A/ja active Pending
- 2008-06-04 DK DK08805936.5T patent/DK2155662T3/da active
- 2008-06-04 PL PL08805936T patent/PL2155662T3/pl unknown
- 2008-06-04 AU AU2008263668A patent/AU2008263668A1/en not_active Abandoned
- 2008-06-04 RU RU2009148335/04A patent/RU2009148335A/ru not_active Application Discontinuation
- 2008-06-04 WO PCT/FR2008/050996 patent/WO2008152333A2/fr active Application Filing
- 2008-06-04 EP EP08805936A patent/EP2155662B1/fr not_active Not-in-force
- 2008-06-04 CA CA002688239A patent/CA2688239A1/fr not_active Abandoned
- 2008-06-04 MX MX2009012841A patent/MX2009012841A/es active IP Right Grant
- 2008-06-04 PT PT08805936T patent/PT2155662E/pt unknown
- 2008-06-04 CN CN200880018900A patent/CN101679216A/zh active Pending
- 2008-06-04 DE DE602008003800T patent/DE602008003800D1/de active Active
- 2008-06-04 KR KR1020097025425A patent/KR20100028548A/ko not_active Application Discontinuation
- 2008-06-05 AR ARP080102388A patent/AR068974A1/es unknown
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2009
- 2009-12-07 US US12/632,159 patent/US7879907B2/en not_active Expired - Fee Related
-
2011
- 2011-01-27 CY CY20111100095T patent/CY1111495T1/el unknown
- 2011-02-24 HR HR20110133T patent/HRP20110133T1/hr unknown
Also Published As
Publication number | Publication date |
---|---|
SI2155662T1 (sl) | 2011-04-29 |
EP2155662A2 (fr) | 2010-02-24 |
JP2010529098A (ja) | 2010-08-26 |
RU2009148335A (ru) | 2011-07-20 |
CA2688239A1 (fr) | 2008-12-18 |
AU2008263668A1 (en) | 2008-12-18 |
ATE490234T1 (de) | 2010-12-15 |
WO2008152333A3 (fr) | 2009-02-19 |
FR2917084B1 (fr) | 2009-07-17 |
KR20100028548A (ko) | 2010-03-12 |
WO2008152333A9 (fr) | 2009-12-10 |
PL2155662T3 (pl) | 2011-04-29 |
US7879907B2 (en) | 2011-02-01 |
FR2917084A1 (fr) | 2008-12-12 |
EP2155662B1 (fr) | 2010-12-01 |
WO2008152333A2 (fr) | 2008-12-18 |
MX2009012841A (es) | 2009-12-11 |
ES2357183T3 (es) | 2011-04-19 |
DK2155662T3 (da) | 2011-02-21 |
DE602008003800D1 (de) | 2011-01-13 |
CN101679216A (zh) | 2010-03-24 |
PT2155662E (pt) | 2011-01-27 |
CY1111495T1 (el) | 2015-08-05 |
AR068974A1 (es) | 2009-12-23 |
US20100158843A1 (en) | 2010-06-24 |
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