FR2659327A1 - Derives du benzisothiazolinone-1-dioxyde, utilisables comme inhibiteurs des elastases. - Google Patents
Derives du benzisothiazolinone-1-dioxyde, utilisables comme inhibiteurs des elastases. Download PDFInfo
- Publication number
- FR2659327A1 FR2659327A1 FR9002951A FR9002951A FR2659327A1 FR 2659327 A1 FR2659327 A1 FR 2659327A1 FR 9002951 A FR9002951 A FR 9002951A FR 9002951 A FR9002951 A FR 9002951A FR 2659327 A1 FR2659327 A1 FR 2659327A1
- Authority
- FR
- France
- Prior art keywords
- radical
- formula
- alkene
- alkane
- carbon atoms
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000003112 inhibitor Substances 0.000 title claims description 34
- 239000000203 mixture Substances 0.000 claims abstract description 40
- 102000016387 Pancreatic elastase Human genes 0.000 claims abstract description 38
- 108010067372 Pancreatic elastase Proteins 0.000 claims abstract description 38
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 33
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 21
- 125000001424 substituent group Chemical group 0.000 claims abstract description 16
- 239000002537 cosmetic Substances 0.000 claims abstract description 10
- 125000003118 aryl group Chemical group 0.000 claims abstract description 9
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims abstract 5
- -1 undecyl radicals Chemical class 0.000 claims description 40
- 150000001336 alkenes Chemical class 0.000 claims description 27
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 25
- 229920000098 polyolefin Polymers 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 230000002401 inhibitory effect Effects 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000002960 margaryl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002958 pentadecyl 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])C([H])([H])[H] 0.000 claims description 2
- 101150035983 str1 gene Proteins 0.000 claims description 2
- 125000002889 tridecyl 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])[H] 0.000 claims description 2
- 102100033174 Neutrophil elastase Human genes 0.000 abstract description 11
- 101000851058 Homo sapiens Neutrophil elastase Proteins 0.000 abstract description 9
- 150000002430 hydrocarbons Chemical class 0.000 abstract description 7
- 239000004215 Carbon black (E152) Substances 0.000 abstract description 4
- 229930195733 hydrocarbon Natural products 0.000 abstract description 4
- 229920006395 saturated elastomer Polymers 0.000 abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 description 39
- 102000016942 Elastin Human genes 0.000 description 14
- 108010014258 Elastin Proteins 0.000 description 14
- 210000004177 elastic tissue Anatomy 0.000 description 14
- 229920002549 elastin Polymers 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- 230000005764 inhibitory process Effects 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 210000003491 skin Anatomy 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 102000004190 Enzymes Human genes 0.000 description 11
- 108090000790 Enzymes Proteins 0.000 description 11
- 229940088598 enzyme Drugs 0.000 description 11
- 102000035195 Peptidases Human genes 0.000 description 9
- 108091005804 Peptidases Proteins 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000006071 cream Substances 0.000 description 9
- ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical class OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 description 8
- ODHCTXKNWHHXJC-GSVOUGTGSA-N Pyroglutamic acid Natural products OC(=O)[C@H]1CCC(=O)N1 ODHCTXKNWHHXJC-GSVOUGTGSA-N 0.000 description 8
- ODHCTXKNWHHXJC-UHFFFAOYSA-N acide pyroglutamique Natural products OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 description 8
- 239000003602 elastase inhibitor Substances 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 230000035515 penetration Effects 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 210000001519 tissue Anatomy 0.000 description 7
- 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 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000004365 Protease Substances 0.000 description 6
- 230000032683 aging Effects 0.000 description 6
- 239000000470 constituent Substances 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 229940122858 Elastase inhibitor Drugs 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 108090000765 processed proteins & peptides Proteins 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 230000000475 sunscreen effect Effects 0.000 description 5
- 239000000516 sunscreening agent Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 108090000190 Thrombin Proteins 0.000 description 4
- 108090000631 Trypsin Proteins 0.000 description 4
- 102000004142 Trypsin Human genes 0.000 description 4
- 239000007844 bleaching agent Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000003623 enhancer Substances 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 239000006210 lotion Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- 229960004072 thrombin Drugs 0.000 description 4
- 239000012588 trypsin Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 206010003210 Arteriosclerosis Diseases 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 206010014561 Emphysema Diseases 0.000 description 3
- 108010088842 Fibrinolysin Proteins 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 208000011775 arteriosclerosis disease Diseases 0.000 description 3
- 210000002808 connective tissue Anatomy 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 230000003246 elastolytic effect Effects 0.000 description 3
- 235000008524 evening primrose extract Nutrition 0.000 description 3
- 229940089020 evening primrose oil Drugs 0.000 description 3
- 239000010475 evening primrose oil Substances 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 239000003906 humectant Substances 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 239000004310 lactic acid Substances 0.000 description 3
- 235000014655 lactic acid Nutrition 0.000 description 3
- 230000007170 pathology Effects 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 229940012957 plasmin Drugs 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- 235000019833 protease Nutrition 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229940081974 saccharin Drugs 0.000 description 3
- 235000019204 saccharin Nutrition 0.000 description 3
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 3
- 238000007390 skin biopsy Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- YPUPEDVTHSWZHZ-JAMMHHFISA-N (1-ethoxy-1-oxobutan-2-yl) (2s)-5-oxopyrrolidine-2-carboxylate Chemical compound CCOC(=O)C(CC)OC(=O)[C@@H]1CCC(=O)N1 YPUPEDVTHSWZHZ-JAMMHHFISA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 108010028275 Leukocyte Elastase Proteins 0.000 description 2
- 108010028921 Lipopeptides Proteins 0.000 description 2
- 206010027476 Metastases Diseases 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 2
- 102000012479 Serine Proteases Human genes 0.000 description 2
- 108010022999 Serine Proteases Proteins 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 102000015395 alpha 1-Antitrypsin Human genes 0.000 description 2
- 108010050122 alpha 1-Antitrypsin Proteins 0.000 description 2
- 229940024142 alpha 1-antitrypsin Drugs 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000003899 bactericide agent Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000009089 cytolysis Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 210000004207 dermis Anatomy 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 229910001882 dioxygen Inorganic materials 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- 230000007071 enzymatic hydrolysis Effects 0.000 description 2
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 210000000265 leukocyte Anatomy 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 210000004072 lung Anatomy 0.000 description 2
- 210000002540 macrophage Anatomy 0.000 description 2
- 238000010907 mechanical stirring Methods 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 210000002381 plasma Anatomy 0.000 description 2
- 235000015277 pork Nutrition 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 102000004196 processed proteins & peptides Human genes 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 2
- 229940116351 sebacate Drugs 0.000 description 2
- 230000028327 secretion Effects 0.000 description 2
- 210000000434 stratum corneum Anatomy 0.000 description 2
- 239000012622 synthetic inhibitor Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 230000002792 vascular Effects 0.000 description 2
- DHRIKYBCMBYPNN-CRMOQAEOSA-N (1-ethoxy-3-hydroxy-1-oxobutan-2-yl) (2s)-5-oxopyrrolidine-2-carboxylate Chemical compound CCOC(=O)C(C(C)O)OC(=O)[C@@H]1CCC(=O)N1 DHRIKYBCMBYPNN-CRMOQAEOSA-N 0.000 description 1
- YKTDWYSPEKLULW-MQWKRIRWSA-N (1-oxo-1-propan-2-yloxypropan-2-yl) (2s)-5-oxopyrrolidine-2-carboxylate Chemical compound CC(C)OC(=O)C(C)OC(=O)[C@@H]1CCC(=O)N1 YKTDWYSPEKLULW-MQWKRIRWSA-N 0.000 description 1
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
- SXWIAEOZZQADEY-UHFFFAOYSA-N 1,3,5-triphenylbenzene Chemical compound C1=CC=CC=C1C1=CC(C=2C=CC=CC=2)=CC(C=2C=CC=CC=2)=C1 SXWIAEOZZQADEY-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 1
- HBXWUCXDUUJDRB-UHFFFAOYSA-N 1-octadecoxyoctadecane Chemical compound CCCCCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCCCC HBXWUCXDUUJDRB-UHFFFAOYSA-N 0.000 description 1
- PXFBZOLANLWPMH-UHFFFAOYSA-N 16-Epiaffinine Natural products C1C(C2=CC=CC=C2N2)=C2C(=O)CC2C(=CC)CN(C)C1C2CO PXFBZOLANLWPMH-UHFFFAOYSA-N 0.000 description 1
- IEQAICDLOKRSRL-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-dodecoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO IEQAICDLOKRSRL-UHFFFAOYSA-N 0.000 description 1
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
- TWYRZWVFWYSNBU-UHFFFAOYSA-N 2-amino-5-(diaminomethylideneamino)-n-(4-nitrophenyl)pentanamide Chemical compound NC(N)=NCCCC(N)C(=O)NC1=CC=C([N+]([O-])=O)C=C1 TWYRZWVFWYSNBU-UHFFFAOYSA-N 0.000 description 1
- YEMWTVRIHVDMPF-DTIOYNMSSA-N 2-ethylhexyl (2s)-5-oxopyrrolidine-2-carboxylate Chemical compound CCCCC(CC)COC(=O)[C@@H]1CCC(=O)N1 YEMWTVRIHVDMPF-DTIOYNMSSA-N 0.000 description 1
- LMKQNIJHUILJTN-GGYWPGCISA-N 2-hexyldecyl (2s)-5-oxopyrrolidine-2-carboxylate Chemical compound CCCCCCCCC(CCCCCC)COC(=O)[C@@H]1CCC(=O)N1 LMKQNIJHUILJTN-GGYWPGCISA-N 0.000 description 1
- GQATZTBBVSSQTP-AXDSSHIGSA-N 2-methylhexyl (2s)-5-oxopyrrolidine-2-carboxylate Chemical compound CCCCC(C)COC(=O)[C@@H]1CCC(=O)N1 GQATZTBBVSSQTP-AXDSSHIGSA-N 0.000 description 1
- ZPRPOWRPPXIVBL-UHFFFAOYSA-N 2-methylpropan-2-ol;propan-2-ol Chemical compound CC(C)O.CC(C)(C)O ZPRPOWRPPXIVBL-UHFFFAOYSA-N 0.000 description 1
- HQWLBRJUMWPIOA-WCSIJFPASA-N 2-octyldodecyl (2s)-5-oxopyrrolidine-2-carboxylate Chemical compound CCCCCCCCCCC(CCCCCCCC)COC(=O)[C@@H]1CCC(=O)N1 HQWLBRJUMWPIOA-WCSIJFPASA-N 0.000 description 1
- UNSAJINGUOTTRA-UHFFFAOYSA-N 3-(3-bromophenyl)prop-2-yn-1-ol Chemical compound OCC#CC1=CC=CC(Br)=C1 UNSAJINGUOTTRA-UHFFFAOYSA-N 0.000 description 1
- 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 description 1
- NAKFRQULMGLXBT-UHFFFAOYSA-N 6-methoxyquinolin-8-ol Chemical compound N1=CC=CC2=CC(OC)=CC(O)=C21 NAKFRQULMGLXBT-UHFFFAOYSA-N 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- ORILYTVJVMAKLC-UHFFFAOYSA-N Adamantane Natural products C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 1
- 235000019489 Almond oil Nutrition 0.000 description 1
- 102100033312 Alpha-2-macroglobulin Human genes 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- SESFRYSPDFLNCH-UHFFFAOYSA-N Benzyl benzoate Natural products C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 239000004358 Butane-1, 3-diol Substances 0.000 description 1
- BOGJCHLCGLXZMK-UHFFFAOYSA-N C(C(O)C)(=O)O.[Cl-].[NH4+].[OH-].[NH4+] Chemical compound C(C(O)C)(=O)O.[Cl-].[NH4+].[OH-].[NH4+] BOGJCHLCGLXZMK-UHFFFAOYSA-N 0.000 description 1
- PPUUBIOHKREJMK-UHFFFAOYSA-N C(C=1C(C(=O)O)=CC=CC1)(=O)OCCCCCCCCCCCC.C(CCC(=O)OCCCC)(=O)OCCCC Chemical compound C(C=1C(C(=O)O)=CC=CC1)(=O)OCCCCCCCCCCCC.C(CCC(=O)OCCCC)(=O)OCCCC PPUUBIOHKREJMK-UHFFFAOYSA-N 0.000 description 1
- JWBYFEAWVFQSNR-UHFFFAOYSA-N C(CCCCCCCC)(=O)OCC(CCCC)CC.C(C)OC(CCCCCCCCCCC)=O.C(CCCCCCCCCCCCCCC)(=O)OC(C)C Chemical compound C(CCCCCCCC)(=O)OCC(CCCC)CC.C(C)OC(CCCCCCCCCCC)=O.C(CCCCCCCCCCCCCCC)(=O)OC(C)C JWBYFEAWVFQSNR-UHFFFAOYSA-N 0.000 description 1
- SSGMCBNVVFQVDK-JVRIOXDDSA-N COC(COC([C@H]1NC(CC1)=O)=O)=O.N1[C@@H](CCC1=O)C(=O)OC(C(=O)O)C Chemical compound COC(COC([C@H]1NC(CC1)=O)=O)=O.N1[C@@H](CCC1=O)C(=O)OC(C(=O)O)C SSGMCBNVVFQVDK-JVRIOXDDSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 244000223760 Cinnamomum zeylanicum Species 0.000 description 1
- 241000557626 Corvus corax Species 0.000 description 1
- ALOUNLDAKADEEB-UHFFFAOYSA-N Dimethyl sebacate Natural products COC(=O)CCCCCCCCC(=O)OC ALOUNLDAKADEEB-UHFFFAOYSA-N 0.000 description 1
- NDJKXXJCMXVBJW-UHFFFAOYSA-N Heptadecane Natural products CCCCCCCCCCCCCCCCC NDJKXXJCMXVBJW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010061309 Neoplasm progression Diseases 0.000 description 1
- OARBDTMLQLTORK-UHFFFAOYSA-N O1CCCC1.O1CCOCC1.C(CC)O.OC(C(=O)O)CCCCCC.OC(C(=O)O)C.COC Chemical compound O1CCCC1.O1CCOCC1.C(CC)O.OC(C(=O)O)CCCCCC.OC(C(=O)O)C.COC OARBDTMLQLTORK-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 108010015078 Pregnancy-Associated alpha 2-Macroglobulins Proteins 0.000 description 1
- 239000004146 Propane-1,2-diol Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 206010039491 Sarcoma Diseases 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 206010064390 Tumour invasion Diseases 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 241000251539 Vertebrata <Metazoa> Species 0.000 description 1
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
- GXIGENABCSHNPA-UHFFFAOYSA-N [PH3]=O.C(C)N1C(CCC1)=O.CN1C(CCC1C)=O Chemical class [PH3]=O.C(C)N1C(CCC1)=O.CN1C(CCC1C)=O GXIGENABCSHNPA-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 239000008168 almond oil Substances 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000001204 arachidyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- XSIFPSYPOVKYCO-UHFFFAOYSA-N benzoic acid butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 description 1
- 229960002903 benzyl benzoate Drugs 0.000 description 1
- 238000001574 biopsy Methods 0.000 description 1
- IFVTZJHWGZSXFD-UHFFFAOYSA-N biphenylene Chemical group C1=CC=C2C3=CC=CC=C3C2=C1 IFVTZJHWGZSXFD-UHFFFAOYSA-N 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- 230000009400 cancer invasion Effects 0.000 description 1
- 210000000845 cartilage Anatomy 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 235000017803 cinnamon Nutrition 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- RGXWDWUGBIJHDO-UHFFFAOYSA-N decanoic acid ethyl ester Natural products CCCCCCCCCC(=O)OCC RGXWDWUGBIJHDO-UHFFFAOYSA-N 0.000 description 1
- 125000003074 decanoyl 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(*)=O 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- YWXABWYIMLHFSQ-ZDUSSCGKSA-N decyl (2s)-5-oxopyrrolidine-2-carboxylate Chemical compound CCCCCCCCCCOC(=O)[C@@H]1CCC(=O)N1 YWXABWYIMLHFSQ-ZDUSSCGKSA-N 0.000 description 1
- SASYSVUEVMOWPL-NXVVXOECSA-N decyl oleate Chemical compound CCCCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC SASYSVUEVMOWPL-NXVVXOECSA-N 0.000 description 1
- 230000007850 degeneration Effects 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- HSYPLAWXJSBGCS-UHFFFAOYSA-N dibenzyl decanedioate dibutyl benzene-1,2-dicarboxylate Chemical compound C(C=1C(C(=O)OCCCC)=CC=CC1)(=O)OCCCC.C(CCCCCCCCC(=O)OCC1=CC=CC=C1)(=O)OCC1=CC=CC=C1 HSYPLAWXJSBGCS-UHFFFAOYSA-N 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 229940031569 diisopropyl sebacate Drugs 0.000 description 1
- 229940014772 dimethyl sebacate Drugs 0.000 description 1
- VPIPLQPUOHAHJH-UHFFFAOYSA-N dioctyl hexanedioate;hexanedioic acid Chemical compound OC(=O)CCCCC(O)=O.CCCCCCCCOC(=O)CCCCC(=O)OCCCCCCCC VPIPLQPUOHAHJH-UHFFFAOYSA-N 0.000 description 1
- XWVQUJDBOICHGH-UHFFFAOYSA-N dioctyl nonanedioate Chemical compound CCCCCCCCOC(=O)CCCCCCCC(=O)OCCCCCCCC XWVQUJDBOICHGH-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000002901 elastaselike Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 210000002615 epidermis Anatomy 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 210000002950 fibroblast Anatomy 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 210000004195 gingiva Anatomy 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- OUGJWOSKKWKWRF-JTQLQIEISA-N heptyl (2s)-5-oxopyrrolidine-2-carboxylate Chemical compound CCCCCCCOC(=O)[C@@H]1CCC(=O)N1 OUGJWOSKKWKWRF-JTQLQIEISA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- ARBOVOVUTSQWSS-UHFFFAOYSA-N hexadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCC(Cl)=O ARBOVOVUTSQWSS-UHFFFAOYSA-N 0.000 description 1
- 229940100463 hexyl laurate Drugs 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- XZXIMDVKCYRCBQ-QHCPKHFHSA-N icosyl (2s)-5-oxopyrrolidine-2-carboxylate Chemical compound CCCCCCCCCCCCCCCCCCCCOC(=O)[C@@H]1CCC(=O)N1 XZXIMDVKCYRCBQ-QHCPKHFHSA-N 0.000 description 1
- 238000010191 image analysis Methods 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000009545 invasion Effects 0.000 description 1
- 229940093629 isopropyl isostearate Drugs 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 210000003041 ligament Anatomy 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 125000005645 linoleyl group Chemical group 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 230000036210 malignancy Effects 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 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
- 239000002480 mineral oil Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl 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])* 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 description 1
- QYVZEPLDLPYECM-XUTLUUPISA-N octadecyl (e)-3-(3,4-dihydroxyphenyl)prop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)\C=C\C1=CC=C(O)C(O)=C1 QYVZEPLDLPYECM-XUTLUUPISA-N 0.000 description 1
- YYZUSRORWSJGET-UHFFFAOYSA-N octanoic acid ethyl ester Natural products CCCCCCCC(=O)OCC YYZUSRORWSJGET-UHFFFAOYSA-N 0.000 description 1
- SXDPDVGGPOQXTM-NSHDSACASA-N octyl (2s)-5-oxopyrrolidine-2-carboxylate Chemical compound CCCCCCCCOC(=O)[C@@H]1CCC(=O)N1 SXDPDVGGPOQXTM-NSHDSACASA-N 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 231100000255 pathogenic effect Toxicity 0.000 description 1
- 230000009543 pathological alteration Effects 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 239000003961 penetration enhancing agent Substances 0.000 description 1
- 208000028169 periodontal disease Diseases 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
- ONQDVAFWWYYXHM-UHFFFAOYSA-M potassium lauryl sulfate Chemical compound [K+].CCCCCCCCCCCCOS([O-])(=O)=O ONQDVAFWWYYXHM-UHFFFAOYSA-M 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- IZHXNBPKBCUDOZ-LURJTMIESA-N propan-2-yl (2s)-5-oxopyrrolidine-2-carboxylate Chemical compound CC(C)OC(=O)[C@@H]1CCC(=O)N1 IZHXNBPKBCUDOZ-LURJTMIESA-N 0.000 description 1
- NEOZOXKVMDBOSG-UHFFFAOYSA-N propan-2-yl 16-methylheptadecanoate Chemical compound CC(C)CCCCCCCCCCCCCCC(=O)OC(C)C NEOZOXKVMDBOSG-UHFFFAOYSA-N 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000017854 proteolysis Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- ZCTQGTTXIYCGGC-UHFFFAOYSA-N salicylic acid benzyl ester Natural products OC1=CC=CC=C1C(=O)OCC1=CC=CC=C1 ZCTQGTTXIYCGGC-UHFFFAOYSA-N 0.000 description 1
- 230000018528 secretion by tissue Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 210000000329 smooth muscle myocyte Anatomy 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- MMKRHZKQPFCLLS-UHFFFAOYSA-N tetradecanoic acid ethyl ester Natural products CCCCCCCCCCCCCC(=O)OCC MMKRHZKQPFCLLS-UHFFFAOYSA-N 0.000 description 1
- PMWMXMYOKCFDIB-KRWDZBQOSA-N tetradecyl (2s)-5-oxopyrrolidine-2-carboxylate Chemical compound CCCCCCCCCCCCCCOC(=O)[C@@H]1CCC(=O)N1 PMWMXMYOKCFDIB-KRWDZBQOSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- OZOVXOAZDQCMAM-INIZCTEOSA-N tridecyl (2s)-5-oxopyrrolidine-2-carboxylate Chemical compound CCCCCCCCCCCCCOC(=O)[C@@H]1CCC(=O)N1 OZOVXOAZDQCMAM-INIZCTEOSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229960001322 trypsin Drugs 0.000 description 1
- 230000005751 tumor progression Effects 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- RCFUFEMQNKVAGF-UHFFFAOYSA-N undec-2-enoyl chloride Chemical compound CCCCCCCCC=CC(Cl)=O RCFUFEMQNKVAGF-UHFFFAOYSA-N 0.000 description 1
- XWCIHBWSVCHGIS-AWEZNQCLSA-N undecyl (2s)-5-oxopyrrolidine-2-carboxylate Chemical compound CCCCCCCCCCCOC(=O)[C@@H]1CCC(=O)N1 XWCIHBWSVCHGIS-AWEZNQCLSA-N 0.000 description 1
- 125000002948 undecyl 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])[H] 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
- C07D275/06—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to the ring sulfur atom
-
- 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
- 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
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- 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
- A61K2800/74—Biological properties of particular ingredients
- A61K2800/78—Enzyme modulators, e.g. Enzyme agonists
- A61K2800/782—Enzyme inhibitors; Enzyme antagonists
-
- 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
- A61Q19/08—Anti-ageing preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Chemistry (AREA)
- Dermatology (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Gerontology & Geriatric Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
- Medicines Containing Plant Substances (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Enzymes And Modification Thereof (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (17)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9002951A FR2659327A1 (fr) | 1990-03-08 | 1990-03-08 | Derives du benzisothiazolinone-1-dioxyde, utilisables comme inhibiteurs des elastases. |
| CA002037665A CA2037665A1 (en) | 1990-03-08 | 1991-03-06 | Benzisothiazolinone-1-dioxide derivatives as elastase inhibitors |
| AU72635/91A AU636013B2 (en) | 1990-03-08 | 1991-03-06 | Benzisothiazolinone-1-dioxide derivatives as elastase inhibitors |
| DE69126460T DE69126460T2 (de) | 1990-03-08 | 1991-03-07 | Benzisothiazolinon-1-dioxyde als Elastase-Inhibitoren |
| EP91301895A EP0446047B1 (en) | 1990-03-08 | 1991-03-07 | Benzisothiazolinone-1-dioxide derivatives as elastase inhibitors |
| MYPI91000361A MY106067A (en) | 1990-03-08 | 1991-03-07 | Benzisothiazolinone-1-dioxide derivatives as elastase inhibitors. |
| ES91301895T ES2102994T3 (es) | 1990-03-08 | 1991-03-07 | Derivados de benzisotiazolinona-1-dioxido como inhibidores de elastasa. |
| AT91301895T ATE154347T1 (de) | 1990-03-08 | 1991-03-07 | Benzisothiazolinon-1-dioxyde als elastase- inhibitoren |
| US07/666,093 US5338747A (en) | 1990-03-08 | 1991-03-07 | Benzoisothiazolinone-1-dioxide derivatives as elastase inhibitors |
| BR919100938A BR9100938A (pt) | 1990-03-08 | 1991-03-08 | Composicao que compreende um inibidor de elastase,derivados de 1-dioxido de benzisotiazolinona e processo para tratamento com cosmetico |
| KR91003708A KR960014782B1 (en) | 1990-03-08 | 1991-03-08 | Benzisothiazolinone 1-dioxide derivatives and elastase inhibitors composition comprising them |
| JP3125607A JPH04234863A (ja) | 1990-03-08 | 1991-03-08 | エラスターゼ阻害剤としてのベンゾイソチアゾリノン−１−ジオキシド誘導体 |
| ZA911728A ZA911728B (en) | 1990-03-08 | 1991-03-08 | Benzisothiazolinone-1-dioxide derivatives as elastase inhibitors |
| IN69/BOM/91A IN172035B (US08063081-20111122-C00044.png) | 1990-03-08 | 1991-03-08 | |
| TW080102851A TW200472B (US08063081-20111122-C00044.png) | 1990-03-08 | 1991-04-13 | |
| IDP185092A ID820B (id) | 1990-03-08 | 1992-01-29 | Turunan benzisotiazolinon-1-dioksid sebagai penghambat elastase |
| US08/230,048 US5411978A (en) | 1990-03-08 | 1994-04-19 | Benzisothiazolinone-1-dioxide derivatives as elastase inhibitors |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9002951A FR2659327A1 (fr) | 1990-03-08 | 1990-03-08 | Derives du benzisothiazolinone-1-dioxyde, utilisables comme inhibiteurs des elastases. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| FR2659327A1 true FR2659327A1 (fr) | 1991-09-13 |
Family
ID=9394523
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR9002951A Pending FR2659327A1 (fr) | 1990-03-08 | 1990-03-08 | Derives du benzisothiazolinone-1-dioxyde, utilisables comme inhibiteurs des elastases. |
Country Status (16)
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5306818A (en) * | 1990-11-01 | 1994-04-26 | Sterling Winthrop Inc. | Tetrahydro 2-saccharinylmerthyl aryl carboxylates |
| US5512589A (en) * | 1990-11-01 | 1996-04-30 | Sterling Winthrop Inc. | 2-saccharinylmethyl aryl carboxylates useful as proteolytic enzyme inhibitors and compositions and method of use thereof |
| US5250696A (en) * | 1990-11-01 | 1993-10-05 | Sterling Winthrop Inc. | 2-saccharinylmethyl aryl carboxylate |
| AU653279B2 (en) * | 1991-12-30 | 1994-09-22 | Sanofi | Novel 2-saccharinylmethyl heterocyclic carboxylates useful as proteolytic enzyme inhibitors and compositions and method of use thereof |
| TW226016B (US08063081-20111122-C00044.png) * | 1991-12-30 | 1994-07-01 | Sterling Winthrop Inc | |
| US6375948B1 (en) * | 1999-07-12 | 2002-04-23 | Kao Corporation | Treating method for suppressing hair growth |
| GB0129987D0 (en) * | 2001-12-14 | 2002-02-06 | Zylepsis Ltd | Skin compositions |
| US7361767B2 (en) | 2003-11-14 | 2008-04-22 | 3M Innovative Properties Company | N-sulfonyldicarboximide containing tethering compounds |
| US7943388B2 (en) | 2003-11-14 | 2011-05-17 | 3M Innovative Properties Company | Acoustic sensors and methods |
| US7423155B2 (en) | 2003-11-14 | 2008-09-09 | 3M Innovative Properties Company | N-sulfonyldicarboximide containing tethering compounds |
| EP1682525B1 (en) | 2003-11-14 | 2013-12-25 | 3M Innovative Properties Company | N-sulfonylaminocarbonyl containing compounds |
| US7169933B2 (en) | 2003-11-14 | 2007-01-30 | 3M Innovative Properties Company | N-sulfonylaminocarbonyl containing compounds |
| WO2005066121A2 (en) * | 2003-12-30 | 2005-07-21 | 3M Innovative Properties Company | Multifunctional amine capture agents |
| US7342082B2 (en) | 2004-12-17 | 2008-03-11 | 3M Innovative Properties Company | Soluble polymers as amine capture agents and methods |
| US7402678B2 (en) | 2004-12-17 | 2008-07-22 | 3M Innovative Properties Company | Multifunctional amine capture agents |
| US7544754B2 (en) * | 2005-09-30 | 2009-06-09 | 3M Innovative Properties Company | Crosslinked polymers with amine binding groups |
| US7544755B2 (en) | 2005-09-30 | 2009-06-09 | 3M Innovative Properties Company | Crosslinked polymers with amine binding groups |
| US7544756B2 (en) | 2005-09-30 | 2009-06-09 | 3M Innovative Properties Company | Crosslinked polymers with amine binding groups |
| US8034448B2 (en) * | 2008-08-19 | 2011-10-11 | Los Alamos National Security, Llc | Fibrous composites comprising carbon nanotubes and silica |
| CN102639575B (zh) | 2009-12-01 | 2018-07-27 | 路博润高级材料公司 | 水解稳定的多用途聚合物 |
| CN110121343B (zh) | 2016-09-12 | 2023-11-03 | 整体健康 | 用作gpr120调节剂的双环化合物 |
| US10800773B2 (en) | 2016-09-12 | 2020-10-13 | Integral Health, Inc. | Monocyclic compounds useful as GPR120 modulators |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4195023A (en) * | 1975-08-20 | 1980-03-25 | Merck & Co., Inc. | 2-(2-Furoyl)1,2-benzisothiazole-3-one, 2-(2-furoyl) saccharin, and 2-(2-thenoyl) saccharin |
| US4276298A (en) * | 1978-03-24 | 1981-06-30 | Merck & Co., Inc. | 2-Aryl-1,2-benzisothiazolinone-1,1-dioxides and their use as selective protease inhibitors |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2546164B1 (fr) * | 1983-05-16 | 1987-07-17 | Centre Nat Rech Scient | Nouveaux derives de peptides, leur preparation et leur application comme inhibiteurs de l'elastase |
-
1990
- 1990-03-08 FR FR9002951A patent/FR2659327A1/fr active Pending
-
1991
- 1991-03-06 AU AU72635/91A patent/AU636013B2/en not_active Ceased
- 1991-03-06 CA CA002037665A patent/CA2037665A1/en not_active Abandoned
- 1991-03-07 MY MYPI91000361A patent/MY106067A/en unknown
- 1991-03-07 US US07/666,093 patent/US5338747A/en not_active Expired - Fee Related
- 1991-03-07 ES ES91301895T patent/ES2102994T3/es not_active Expired - Lifetime
- 1991-03-07 EP EP91301895A patent/EP0446047B1/en not_active Expired - Lifetime
- 1991-03-07 AT AT91301895T patent/ATE154347T1/de not_active IP Right Cessation
- 1991-03-07 DE DE69126460T patent/DE69126460T2/de not_active Expired - Fee Related
- 1991-03-08 JP JP3125607A patent/JPH04234863A/ja active Pending
- 1991-03-08 KR KR91003708A patent/KR960014782B1/ko active IP Right Grant
- 1991-03-08 IN IN69/BOM/91A patent/IN172035B/en unknown
- 1991-03-08 ZA ZA911728A patent/ZA911728B/xx unknown
- 1991-03-08 BR BR919100938A patent/BR9100938A/pt not_active Application Discontinuation
- 1991-04-13 TW TW080102851A patent/TW200472B/zh active
-
1992
- 1992-01-29 ID IDP185092A patent/ID820B/id unknown
-
1994
- 1994-04-19 US US08/230,048 patent/US5411978A/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4195023A (en) * | 1975-08-20 | 1980-03-25 | Merck & Co., Inc. | 2-(2-Furoyl)1,2-benzisothiazole-3-one, 2-(2-furoyl) saccharin, and 2-(2-thenoyl) saccharin |
| US4276298A (en) * | 1978-03-24 | 1981-06-30 | Merck & Co., Inc. | 2-Aryl-1,2-benzisothiazolinone-1,1-dioxides and their use as selective protease inhibitors |
Non-Patent Citations (1)
| Title |
|---|
| JOURNAL OF THE CHEMICAL SOCIETY, 1957, pages 492-493, Londres, GB; E. STEPHEN et al.: "The preparation of 2-acyl-3-oxo-4 : 5-benzo-1 : 2-thiazole 1 : 1 - dioxides (N-acylsaccharins) for the identification of monocarboxylic acids" * |
Also Published As
| Publication number | Publication date |
|---|---|
| US5411978A (en) | 1995-05-02 |
| MY106067A (en) | 1995-03-31 |
| ATE154347T1 (de) | 1997-06-15 |
| US5338747A (en) | 1994-08-16 |
| KR910016330A (ko) | 1991-11-05 |
| JPH04234863A (ja) | 1992-08-24 |
| KR960014782B1 (en) | 1996-10-19 |
| CA2037665A1 (en) | 1991-09-09 |
| ZA911728B (en) | 1992-11-25 |
| DE69126460D1 (de) | 1997-07-17 |
| ES2102994T3 (es) | 1997-08-16 |
| BR9100938A (pt) | 1991-11-05 |
| TW200472B (US08063081-20111122-C00044.png) | 1993-02-21 |
| AU7263591A (en) | 1991-09-12 |
| IN172035B (US08063081-20111122-C00044.png) | 1993-03-20 |
| EP0446047A1 (en) | 1991-09-11 |
| AU636013B2 (en) | 1993-04-08 |
| EP0446047B1 (en) | 1997-06-11 |
| DE69126460T2 (de) | 1997-12-04 |
| ID820B (id) | 1996-07-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FR2659327A1 (fr) | Derives du benzisothiazolinone-1-dioxyde, utilisables comme inhibiteurs des elastases. | |
| JP3843943B2 (ja) | Ｎ−アシルアミノ−アミドファミリーの新規な化合物、それを含有する組成物及び用途 | |
| EP1893555B1 (fr) | Bioprecurseur a base de polyphenol | |
| US7838020B2 (en) | Cosmetic or dermatological composition comprising an association between a compound of the N-acylaminoamide family and at least one matrix metalloproteinase inhibitor | |
| CA1339085C (fr) | Compositions pharmaceutiques et cosmetiques a base de peroxyde de benzoyle et de sels d'ammonium quaternaires | |
| EP0664290A1 (fr) | Mono-et di-esters d'acide cinnamique ou de l'un de ses dérivés et de vitamine C, leur procédé de préparation et leur utilisation comme anti-oxydants dans des compositions cosmétiques, pharmaceutiques ou alimentaires | |
| FR2546164A1 (fr) | Nouveaux derives de peptides, leur preparation et leur application comme inhibiteurs de l'elastase | |
| EP1269988B1 (fr) | Composition cosmetique ou dermatologique comprenant des dérivés d'acylaminoamide | |
| FR2783517A1 (fr) | Nouveaux derives de l'acide 10-hyroxy-2-decenoique et utilisation dans une composition destinee a favoriser la desquamation de la peau, et composition le comprenant | |
| EP0968221B1 (fr) | Nouveaux derives de l'acide salicylique et leur utilisation dans les compositions cosmetiques ou dermatologiques | |
| EP1399113B1 (fr) | Composition cosmetique ou dermatologique comprenant des derives des n-acylaminoamides | |
| JP2010070496A (ja) | 毛髪および／または毛包強化因子産生促進剤 | |
| EP1837341A1 (fr) | Dérivé du glucose et de vitamine f, compositions le comprenant et utilisations pour améliorer l'état des poils et des cheveux | |
| CA2233219C (fr) | Utilisation d'acides carboxyliques porteurs d'une fonction soufree pour favoriser la desquamation de la peau ou stimuler le renouvellement epidermique | |
| EP1123692A2 (fr) | Utilisation de dérivés de polyaminoacides pour traiter la séborrhée et les désordres cutanés associés | |
| EP0677288B1 (fr) | Composition cosmétique ou pharmaceutique contenant un carbamate d'alkyle en tant qu'agent hydratant | |
| EP0819427A1 (fr) | Utilisation de l'iodo-3 propynyl-2 butylcarbamate dans une composition cosmétique et/ou dermatologique comme actif pour le traitement de la séborrhée | |
| FR2826273A1 (fr) | Composition contenant des derives d'acide salicylique et des derives lipophiles d'acide amine | |
| FR2672289A1 (fr) | Derives de dipeptides a groupement urethanne, utilisables comme agents hydratants et comme agents tensioactifs dans des compositions cosmetiques, pharmaceutiques ou alimentaires. | |
| JP2004091437A (ja) | 日焼け用の化粧料 | |
| FR2924601A1 (fr) | Composes diphosphate d'hydroquinone et leur utilisation pour depigmenter la peau. |