NZ524599A - Fatty acid analogues for the treatment of proliferative skin disorders related to keratinocyte differentiation and proliferation - Google Patents
Fatty acid analogues for the treatment of proliferative skin disorders related to keratinocyte differentiation and proliferationInfo
- Publication number
- NZ524599A NZ524599A NZ524599A NZ52459901A NZ524599A NZ 524599 A NZ524599 A NZ 524599A NZ 524599 A NZ524599 A NZ 524599A NZ 52459901 A NZ52459901 A NZ 52459901A NZ 524599 A NZ524599 A NZ 524599A
- Authority
- NZ
- New Zealand
- Prior art keywords
- carbon
- alkyl
- use according
- alkene
- proliferation
- Prior art date
Links
- 230000004069 differentiation Effects 0.000 title claims abstract description 28
- 210000002510 keratinocyte Anatomy 0.000 title claims abstract description 27
- 238000011282 treatment Methods 0.000 title claims abstract description 23
- 230000035755 proliferation Effects 0.000 title claims abstract description 20
- 230000002062 proliferating effect Effects 0.000 title claims abstract description 16
- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 15
- 239000000194 fatty acid Substances 0.000 title claims abstract description 15
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 15
- 150000004665 fatty acids Chemical class 0.000 title claims abstract description 15
- 208000017520 skin disease Diseases 0.000 title claims abstract description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 30
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 30
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- 125000006686 (C1-C24) alkyl group Chemical group 0.000 claims abstract description 8
- 150000001336 alkenes Chemical group 0.000 claims abstract description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 6
- 230000002265 prevention Effects 0.000 claims abstract description 6
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims abstract description 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims abstract description 5
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 5
- 150000001345 alkine derivatives Chemical group 0.000 claims abstract description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 5
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 230000005764 inhibitory process Effects 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 2
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 2
- IPBCWPPBAWQYOO-UHFFFAOYSA-N 2-(tetradecylthio)acetic acid Chemical compound CCCCCCCCCCCCCCSCC(O)=O IPBCWPPBAWQYOO-UHFFFAOYSA-N 0.000 claims description 38
- 210000003491 skin Anatomy 0.000 claims description 15
- 201000004681 Psoriasis Diseases 0.000 claims description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 230000006698 induction Effects 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 229940002612 prodrug Drugs 0.000 claims description 4
- 239000000651 prodrug Substances 0.000 claims description 4
- LUQGQZIVDLUXLE-UHFFFAOYSA-N CCCCCCCCCCCCCCCC(O)=[Se] Chemical compound CCCCCCCCCCCCCCCC(O)=[Se] LUQGQZIVDLUXLE-UHFFFAOYSA-N 0.000 claims description 3
- 238000011200 topical administration Methods 0.000 claims description 2
- 206010021198 ichthyosis Diseases 0.000 claims 3
- 208000023095 Autosomal dominant epidermolytic ichthyosis Diseases 0.000 claims 1
- 201000004624 Dermatitis Diseases 0.000 claims 1
- 206010012438 Dermatitis atopic Diseases 0.000 claims 1
- 206010012442 Dermatitis contact Diseases 0.000 claims 1
- 201000009040 Epidermolytic Hyperkeratosis Diseases 0.000 claims 1
- 206010020649 Hyperkeratosis Diseases 0.000 claims 1
- 208000001126 Keratosis Diseases 0.000 claims 1
- 208000001913 Lamellar ichthyosis Diseases 0.000 claims 1
- 208000002029 allergic contact dermatitis Diseases 0.000 claims 1
- 201000008937 atopic dermatitis Diseases 0.000 claims 1
- 201000000751 autosomal recessive congenital ichthyosis Diseases 0.000 claims 1
- 208000033286 epidermolytic ichthyosis Diseases 0.000 claims 1
- 208000001875 irritant dermatitis Diseases 0.000 claims 1
- 230000003211 malignant effect Effects 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 230000014509 gene expression Effects 0.000 description 35
- 210000004027 cell Anatomy 0.000 description 26
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 description 23
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 description 23
- 239000003446 ligand Substances 0.000 description 21
- 230000000694 effects Effects 0.000 description 13
- 108090000623 proteins and genes Proteins 0.000 description 13
- 108020004999 messenger RNA Proteins 0.000 description 12
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 10
- 239000001110 calcium chloride Substances 0.000 description 10
- 235000011148 calcium chloride Nutrition 0.000 description 10
- 229910001628 calcium chloride Inorganic materials 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 102000049320 CD36 Human genes 0.000 description 9
- 108010045374 CD36 Antigens Proteins 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 description 6
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 6
- 231100000673 dose–response relationship Toxicity 0.000 description 6
- 210000002615 epidermis Anatomy 0.000 description 6
- 239000003550 marker Substances 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- 241000124008 Mammalia Species 0.000 description 4
- 239000012190 activator Substances 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- HQMNCQVAMBCHCO-DJRRULDNSA-N etretinate Chemical compound CCOC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)C=C(OC)C(C)=C1C HQMNCQVAMBCHCO-DJRRULDNSA-N 0.000 description 4
- 229960002199 etretinate Drugs 0.000 description 4
- 230000003902 lesion Effects 0.000 description 4
- 239000011669 selenium Substances 0.000 description 4
- 230000000699 topical effect Effects 0.000 description 4
- 238000001262 western blot Methods 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 238000002965 ELISA Methods 0.000 description 3
- 238000000134 MTT assay Methods 0.000 description 3
- 231100000002 MTT assay Toxicity 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 108060008539 Transglutaminase Proteins 0.000 description 3
- 239000003242 anti bacterial agent Substances 0.000 description 3
- 210000000270 basal cell Anatomy 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000004663 cell proliferation Effects 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 102000007236 involucrin Human genes 0.000 description 3
- 108010033564 involucrin Proteins 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000003389 potentiating effect Effects 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 230000001185 psoriatic effect Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000002560 therapeutic procedure Methods 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- 229940125379 topical corticosteroid Drugs 0.000 description 3
- 102000003601 transglutaminase Human genes 0.000 description 3
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 2
- 102100023970 Keratin, type I cytoskeletal 10 Human genes 0.000 description 2
- 229920001213 Polysorbate 20 Polymers 0.000 description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 102000004142 Trypsin Human genes 0.000 description 2
- 108090000631 Trypsin Proteins 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 230000001028 anti-proliverative effect Effects 0.000 description 2
- 229940121375 antifungal agent Drugs 0.000 description 2
- 239000003429 antifungal agent Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 230000033228 biological regulation Effects 0.000 description 2
- 230000032823 cell division Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
- 235000012000 cholesterol Nutrition 0.000 description 2
- 230000001684 chronic effect Effects 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000002316 cosmetic surgery Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 239000002612 dispersion medium Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 210000005175 epidermal keratinocyte Anatomy 0.000 description 2
- 239000012894 fetal calf serum Substances 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 238000010820 immunofluorescence microscopy Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000000411 inducer Substances 0.000 description 2
- 230000001939 inductive effect Effects 0.000 description 2
- 239000007951 isotonicity adjuster Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 2
- -1 other retinoids Chemical compound 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 2
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 2
- 238000003757 reverse transcription PCR Methods 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 239000012588 trypsin Substances 0.000 description 2
- 230000003827 upregulation Effects 0.000 description 2
- 230000035899 viability Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- 206010001382 Adrenal suppression Diseases 0.000 description 1
- 235000011330 Armoracia rusticana Nutrition 0.000 description 1
- 240000003291 Armoracia rusticana Species 0.000 description 1
- 206010003694 Atrophy Diseases 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- 206010015150 Erythema Diseases 0.000 description 1
- 206010019851 Hepatotoxicity Diseases 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 102100022905 Keratin, type II cytoskeletal 1 Human genes 0.000 description 1
- 108010070514 Keratin-1 Proteins 0.000 description 1
- 108010065038 Keratin-10 Proteins 0.000 description 1
- 108010076876 Keratins Proteins 0.000 description 1
- 206010048649 Koebner phenomenon Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 101150014691 PPARA gene Proteins 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 102000003992 Peroxidases Human genes 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 208000003251 Pruritus Diseases 0.000 description 1
- 206010040844 Skin exfoliation Diseases 0.000 description 1
- 101710172711 Structural protein Proteins 0.000 description 1
- 210000001744 T-lymphocyte Anatomy 0.000 description 1
- 206010043087 Tachyphylaxis Diseases 0.000 description 1
- 230000001594 aberrant effect Effects 0.000 description 1
- 239000003070 absorption delaying agent Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000037444 atrophy Effects 0.000 description 1
- 230000037365 barrier function of the epidermis Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000007975 buffered saline Substances 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000022131 cell cycle Effects 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 210000002421 cell wall Anatomy 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 210000000080 chela (arthropods) Anatomy 0.000 description 1
- 229960004926 chlorobutanol Drugs 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- 229960001334 corticosteroids Drugs 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000001086 cytosolic effect Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 210000004207 dermis Anatomy 0.000 description 1
- 230000035618 desquamation Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- 230000009699 differential effect Effects 0.000 description 1
- 230000006806 disease prevention Effects 0.000 description 1
- 108010007093 dispase Proteins 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 210000001339 epidermal cell Anatomy 0.000 description 1
- 210000000981 epithelium Anatomy 0.000 description 1
- 231100000321 erythema Toxicity 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 230000005713 exacerbation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 230000007686 hepatotoxicity Effects 0.000 description 1
- 231100000304 hepatotoxicity Toxicity 0.000 description 1
- 206010020718 hyperplasia Diseases 0.000 description 1
- 230000003463 hyperproliferative effect Effects 0.000 description 1
- 230000028993 immune response Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000007803 itching Effects 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 238000007449 liver function test Methods 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 125000001421 myristyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000000440 neutrophil Anatomy 0.000 description 1
- 231100000065 noncytotoxic Toxicity 0.000 description 1
- 230000002020 noncytotoxic effect Effects 0.000 description 1
- 230000037311 normal skin Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 108040007629 peroxidase activity proteins Proteins 0.000 description 1
- 238000002135 phase contrast microscopy Methods 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- KYEKHFSRAXRJBR-UHFFFAOYSA-M potassium;selenocyanate Chemical compound [K+].[Se-]C#N KYEKHFSRAXRJBR-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000007115 recruitment Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000013568 regulation of keratinocyte differentiation Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 210000004761 scalp Anatomy 0.000 description 1
- 210000001991 scapula Anatomy 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 150000003408 sphingolipids Chemical class 0.000 description 1
- 210000000130 stem cell Anatomy 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- QTENRWWVYAAPBI-YCRXJPFRSA-N streptomycin sulfate Chemical compound OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](N=C(N)N)[C@H](O)[C@@H](N=C(N)N)[C@H](O)[C@H]1O.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](N=C(N)N)[C@H](O)[C@@H](N=C(N)N)[C@H](O)[C@H]1O QTENRWWVYAAPBI-YCRXJPFRSA-N 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 231100000462 teratogen Toxicity 0.000 description 1
- 239000003439 teratogenic agent Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
-
- 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
- A61P17/06—Antipsoriatics
-
- 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
- A61P17/00—Drugs for dermatological disorders
- A61P17/12—Keratolytics, e.g. wart or anti-corn preparations
-
- 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
- A61P17/16—Emollients or protectives, e.g. against radiation
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
Landscapes
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Toxicology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO20004844A NO20004844L (no) | 2000-09-27 | 2000-09-27 | Fettsyre analoger for behandling av proliferative hudsykdommer |
| PCT/NO2001/000393 WO2002026218A2 (en) | 2000-09-27 | 2001-09-27 | Fatty acid analogues for the treatment of proliferative skin disorders |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ524599A true NZ524599A (en) | 2004-11-26 |
Family
ID=19911618
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ524599A NZ524599A (en) | 2000-09-27 | 2001-09-27 | Fatty acid analogues for the treatment of proliferative skin disorders related to keratinocyte differentiation and proliferation |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US7230029B2 (enExample) |
| EP (1) | EP1324756B1 (enExample) |
| JP (1) | JP2004509917A (enExample) |
| KR (1) | KR100905336B1 (enExample) |
| CN (1) | CN100579521C (enExample) |
| AT (1) | ATE418974T1 (enExample) |
| AU (2) | AU2001294419B2 (enExample) |
| BR (1) | BR0114137A (enExample) |
| CA (1) | CA2421729A1 (enExample) |
| DE (1) | DE60137243D1 (enExample) |
| ES (1) | ES2317938T3 (enExample) |
| MX (1) | MXPA03002629A (enExample) |
| NO (1) | NO20004844L (enExample) |
| NZ (1) | NZ524599A (enExample) |
| RU (1) | RU2276602C2 (enExample) |
| WO (1) | WO2002026218A2 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NO328803B1 (no) | 2000-03-03 | 2010-05-18 | Thia Medica | Nye fettsyreanaloger |
| JP5008258B2 (ja) | 2002-06-20 | 2012-08-22 | アイシー・ベック・リミテッド | 含硫黄ホスホリピド誘導体 |
| FR2850869B1 (fr) * | 2003-02-12 | 2005-03-25 | Genfit S A | Utilisations d'aminopropanediols acyles et de leurs analogues azotes et sulfures |
| ES2660700T3 (es) * | 2004-07-19 | 2018-03-23 | Bergen Teknologioverføring As | Composición que comprende aceites vegetales y/o de pescado y entidades de ácidos grasos no oxidables |
| EP2120916A4 (en) * | 2007-02-05 | 2010-07-28 | Children Youth And Women S Hea | MODULATORS FOR THE PROLIFERATION OF T CELLS DEPENDENT OF ANTIGEN |
| US8602833B2 (en) | 2009-08-06 | 2013-12-10 | May Patents Ltd. | Puzzle with conductive path |
| US11330714B2 (en) | 2011-08-26 | 2022-05-10 | Sphero, Inc. | Modular electronic building systems with magnetic interconnections and methods of using the same |
| US9019718B2 (en) | 2011-08-26 | 2015-04-28 | Littlebits Electronics Inc. | Modular electronic building systems with magnetic interconnections and methods of using the same |
| US9597607B2 (en) | 2011-08-26 | 2017-03-21 | Littlebits Electronics Inc. | Modular electronic building systems with magnetic interconnections and methods of using the same |
| USD732475S1 (en) | 2012-11-19 | 2015-06-23 | Littlebits Electronics Inc. | Connector for modular electronic building system |
| AU2014229506B2 (en) | 2013-03-11 | 2017-04-13 | Nobesita As | Natural lipids containing non-oxidizable fatty acids |
| CN105498622B (zh) * | 2015-12-10 | 2017-10-17 | 江南大学 | 一种含硒表面活性剂及其制备方法和应用 |
| WO2018065918A1 (en) | 2016-10-04 | 2018-04-12 | Mary Kay Inc. | Methods and compositions for treating striae distensae |
| AU2019340475B2 (en) * | 2018-09-14 | 2025-04-17 | Université de Lausanne | Methods for modulating regulatory T cells and inhibiting tumor growth |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU618517B2 (en) * | 1986-12-23 | 1992-01-02 | Eugene J. Van Scott | Additives enhancing topical actions of therapeutic agents |
| DE19516705C2 (de) * | 1995-05-06 | 1997-10-02 | Beiersdorf Ag | Gegen Bakterien, Mycota und Viren wirksame Substanzen |
| RU2123334C1 (ru) * | 1997-03-05 | 1998-12-20 | Тихоокеанский научно-исследовательский рыбохозяйственный центр | Способ лечения псориаза |
| AU7240398A (en) * | 1998-05-08 | 1999-11-29 | Rolf Berge | Use of non-beta-oxidizable fatty acid analogues for treatment of syndrome-x conditions |
| FR2792312B1 (fr) * | 1999-04-15 | 2001-06-08 | Oreal | Composes (poly)thia-alcynoiques et leurs derives, compositions les comprenant et leur utilisation |
| AUPQ291499A0 (en) * | 1999-09-17 | 1999-10-07 | Women's And Children's Hospital Adelaide | Novel nitro and sulphur containing compounds |
| NO328803B1 (no) * | 2000-03-03 | 2010-05-18 | Thia Medica | Nye fettsyreanaloger |
-
2000
- 2000-09-27 NO NO20004844A patent/NO20004844L/no not_active Application Discontinuation
-
2001
- 2001-09-27 BR BR0114137-6A patent/BR0114137A/pt not_active Application Discontinuation
- 2001-09-27 AT AT01975050T patent/ATE418974T1/de not_active IP Right Cessation
- 2001-09-27 CN CN01816441A patent/CN100579521C/zh not_active Expired - Fee Related
- 2001-09-27 JP JP2002530048A patent/JP2004509917A/ja active Pending
- 2001-09-27 CA CA002421729A patent/CA2421729A1/en not_active Abandoned
- 2001-09-27 RU RU2003107685/15A patent/RU2276602C2/ru not_active IP Right Cessation
- 2001-09-27 MX MXPA03002629A patent/MXPA03002629A/es active IP Right Grant
- 2001-09-27 KR KR1020037004396A patent/KR100905336B1/ko not_active Expired - Fee Related
- 2001-09-27 NZ NZ524599A patent/NZ524599A/en unknown
- 2001-09-27 AU AU2001294419A patent/AU2001294419B2/en not_active Ceased
- 2001-09-27 EP EP01975050A patent/EP1324756B1/en not_active Expired - Lifetime
- 2001-09-27 AU AU9441901A patent/AU9441901A/xx active Pending
- 2001-09-27 WO PCT/NO2001/000393 patent/WO2002026218A2/en not_active Ceased
- 2001-09-27 ES ES01975050T patent/ES2317938T3/es not_active Expired - Lifetime
- 2001-09-27 DE DE60137243T patent/DE60137243D1/de not_active Expired - Lifetime
- 2001-09-27 US US10/363,963 patent/US7230029B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ES2317938T3 (es) | 2009-05-01 |
| EP1324756B1 (en) | 2008-12-31 |
| US7230029B2 (en) | 2007-06-12 |
| NO20004844D0 (no) | 2000-09-27 |
| WO2002026218A2 (en) | 2002-04-04 |
| AU2001294419B2 (en) | 2005-12-01 |
| ATE418974T1 (de) | 2009-01-15 |
| MXPA03002629A (es) | 2004-05-24 |
| JP2004509917A (ja) | 2004-04-02 |
| BR0114137A (pt) | 2003-08-12 |
| CA2421729A1 (en) | 2002-04-04 |
| NO20004844L (no) | 2002-05-10 |
| KR20030036843A (ko) | 2003-05-09 |
| KR100905336B1 (ko) | 2009-07-01 |
| CN1466453A (zh) | 2004-01-07 |
| RU2276602C2 (ru) | 2006-05-20 |
| US20040019108A1 (en) | 2004-01-29 |
| DE60137243D1 (de) | 2009-02-12 |
| WO2002026218A3 (en) | 2002-06-13 |
| HK1060692A1 (zh) | 2004-08-20 |
| CN100579521C (zh) | 2010-01-13 |
| EP1324756A2 (en) | 2003-07-09 |
| AU9441901A (en) | 2002-04-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP1324756B1 (en) | Fatty acid analogues for the treatment of proliferative skin disorders | |
| Sidell | Retinoic acid-induced growth inhibition and morphologic differentiation of human neuroblastoma cells in vitro | |
| AU2001294419A1 (en) | Fatty acid analogues for the treatment of proliferative skin disorders | |
| Santos et al. | Multidisciplinary utilization of dimethyl sulfoxide: pharmacological, cellular, and molecular aspects | |
| US4743597A (en) | Composition comprising an oxygenated cholesterol and use thereof for topical treatment of diseases | |
| US9192592B2 (en) | Use of 2,5-dihydroxybenzene derivatives for treating dermatitis | |
| US9018195B2 (en) | Use of 2,5-dihydroxybenzene sulfonic acid compounds for treating skin photoaging | |
| JP2002510618A (ja) | 皮膚科症状の治療へのポリアミンの使用 | |
| CA2200480C (en) | New use of prostaglandins | |
| ES2214635T3 (es) | Uso de compuestos de quelatos de 3-hidroxi-4-pirona para el tratamiento de enfermedades que pueden mejorar inhibiendo la hiperproliferacion de queratinocitos. | |
| EP0289506A1 (en) | Lipoxygenase inhibitors | |
| Gibson et al. | Muscle protein synthesis in patients with rheumatoid arthritis: effect of chronic corticosteroid therapy on prostaglandin F2α availability | |
| AU2006338583B2 (en) | Methods and compositions for bactericide, bacteriostatic and anti-inflammation | |
| JP2004532230A (ja) | Ppar−ガンマアクチベーターを使用する瘢痕化および関連状態の処置 | |
| US3689667A (en) | C22 acid and its salts to promote wound healing | |
| JPH11501611A (ja) | 過角化及びプロテアーゼによって媒介される疾患の治療のための方法 | |
| Touvay et al. | Characterization of platelet activating factor (PAF)-acether-induced contractions of guinea-pig lung strips by selected inhibitors of arachidonic acid metabolism and by PAF-acether antagonists | |
| HK1060692B (en) | Fatty acid analogues for the treatment of proliferative skin disorders | |
| CA2124852A1 (en) | Use of a known chemical compound for the production of a pharmaceutical composition for topical application | |
| NO324555B1 (no) | Anvendelse av fettsyreanaloger for a hindre og/eller behandle proliferative hudsykdommer. | |
| KR940021055A (ko) | 비환상 폴리이소프레노이드계 세포분화유도제 | |
| WO2009015366A2 (en) | Use of thyroid hormone conversion inhibitors to treat hyperproliferative disorders | |
| Cunliffe | Vitamin a in Dermatology | |
| WO2006019353A9 (en) | Composition and method for the treatement of psoriasis | |
| HK1065941B (en) | Use of a nicotinic acid alkyl ester containing an alkyl chain from 8 to 22 carbon atoms for the preparation of a medicament for increasing leptin levels in a subject |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PSEA | Patent sealed | ||
| RENW | Renewal (renewal fees accepted) | ||
| RENW | Renewal (renewal fees accepted) |