IL106347A - Pharmaceutical compositions of noble derivatives of phenolic thioetherum for the treatment of pigmented diseases, such compounds and their use - Google Patents

Pharmaceutical compositions of noble derivatives of phenolic thioetherum for the treatment of pigmented diseases, such compounds and their use

Info

Publication number: IL106347A
Authority: IL; Israel
Prior art keywords: compound; cap; compounds; formula; melanoma
Prior art date: 1992-07-15

Application number

IL10634793A

Other languages

English (en)

Hebrew (he)

Other versions

IL106347A0 (en

Original Assignee

Univ Alberta

Priority date (The priority date 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 date listed.)

1992-07-15

Filing date

1993-07-14

Publication date

1999-07-14

1992-07-15 Priority claimed from GB929215066A external-priority patent/GB9215066D0/en

1993-07-14 Application filed by Univ Alberta filed Critical Univ Alberta

1993-11-15 Publication of IL106347A0 publication Critical patent/IL106347A0/xx

1999-07-14 Publication of IL106347A publication Critical patent/IL106347A/en

Links

150000001875 compounds Chemical class 0.000 title claims description 107
125000002252 acyl group Chemical group 0.000 title abstract description 5
208000012641 Pigmentation disease Diseases 0.000 title description 5
150000003568 thioethers Chemical class 0.000 title description 2
201000001441 melanoma Diseases 0.000 claims abstract description 52
238000011282 treatment Methods 0.000 claims abstract description 24
210000002752 melanocyte Anatomy 0.000 claims abstract description 23
241001465754 Metazoa Species 0.000 claims abstract description 13
230000008099 melanin synthesis Effects 0.000 claims abstract description 9
230000000903 blocking effect Effects 0.000 claims abstract description 7
238000000034 method Methods 0.000 claims description 17
102000003425 Tyrosinase Human genes 0.000 claims description 12
108060008724 Tyrosinase Proteins 0.000 claims description 12
210000001519 tissue Anatomy 0.000 claims description 12
238000001727 in vivo Methods 0.000 claims description 11
239000008194 pharmaceutical composition Substances 0.000 claims description 9
230000000699 topical effect Effects 0.000 claims description 9
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
239000005864 Sulphur Substances 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
239000012857 radioactive material Substances 0.000 claims description 6
230000002285 radioactive effect Effects 0.000 claims description 5
238000009825 accumulation Methods 0.000 claims description 4
230000008569 process Effects 0.000 claims description 4
230000005855 radiation Effects 0.000 claims description 4
238000003745 diagnosis Methods 0.000 claims description 3
230000002401 inhibitory effect Effects 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
229910052738 indium Inorganic materials 0.000 claims description 2
APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 claims description 2
230000037353 metabolic pathway Effects 0.000 claims description 2
229910052713 technetium Inorganic materials 0.000 claims description 2
GKLVYJBZJHMRIY-UHFFFAOYSA-N technetium atom Chemical compound [Tc] GKLVYJBZJHMRIY-UHFFFAOYSA-N 0.000 claims description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
125000004354 sulfur functional group Chemical group 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 33
-1 thioester amines Chemical class 0.000 abstract description 16
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 13
238000011127 radiochemotherapy Methods 0.000 abstract description 9
208000035475 disorder Diseases 0.000 abstract description 5
230000000485 pigmenting effect Effects 0.000 abstract description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 61
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 30
LGHNHPRURDSNNK-UHFFFAOYSA-N 4-(2-aminoethylsulfanyl)phenol Chemical compound NCCSC1=CC=C(O)C=C1 LGHNHPRURDSNNK-UHFFFAOYSA-N 0.000 description 26
230000000694 effects Effects 0.000 description 21
239000000243 solution Substances 0.000 description 19
229960003742 phenol Drugs 0.000 description 14
230000003127 anti-melanomic effect Effects 0.000 description 13
238000006243 chemical reaction Methods 0.000 description 13
241000699666 Mus <mouse, genus> Species 0.000 description 12
239000003795 chemical substances by application Substances 0.000 description 12
239000003480 eluent Substances 0.000 description 12
239000007924 injection Substances 0.000 description 12
238000002347 injection Methods 0.000 description 12
238000007912 intraperitoneal administration Methods 0.000 description 12
FDPFDQAWKAWHMY-UHFFFAOYSA-N n-[2-(4-hydroxyphenyl)sulfanylethyl]acetamide Chemical compound CC(=O)NCCSC1=CC=C(O)C=C1 FDPFDQAWKAWHMY-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 12
241000699670 Mus sp. Species 0.000 description 11
230000015572 biosynthetic process Effects 0.000 description 10
231100000135 cytotoxicity Toxicity 0.000 description 10
230000003013 cytotoxicity Effects 0.000 description 10
238000003786 synthesis reaction Methods 0.000 description 10
230000001988 toxicity Effects 0.000 description 10
231100000419 toxicity Toxicity 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000013543 active substance Substances 0.000 description 9
210000004027 cell Anatomy 0.000 description 9
239000007854 depigmenting agent Substances 0.000 description 9
239000002904 solvent Substances 0.000 description 9
FVXLRXHSPYGEFL-QMMMGPOBSA-N (2r)-2-amino-3-(4-hydroxyphenyl)sulfanylpropanoic acid Chemical compound OC(=O)[C@@H](N)CSC1=CC=C(O)C=C1 FVXLRXHSPYGEFL-QMMMGPOBSA-N 0.000 description 8
XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
230000037396 body weight Effects 0.000 description 8
230000035614 depigmentation Effects 0.000 description 8
201000010099 disease Diseases 0.000 description 8
210000003491 skin Anatomy 0.000 description 8
239000000758 substrate Substances 0.000 description 8
206010008570 Chloasma Diseases 0.000 description 7
208000003351 Melanosis Diseases 0.000 description 7
238000004128 high performance liquid chromatography Methods 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
206010028980 Neoplasm Diseases 0.000 description 6
125000003118 aryl group Chemical group 0.000 description 6
125000001589 carboacyl group Chemical group 0.000 description 6
210000004072 lung Anatomy 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
208000000453 Skin Neoplasms Diseases 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
239000000969 carrier Substances 0.000 description 5
OOTFVKOQINZBBF-UHFFFAOYSA-N cystamine Chemical compound CCSSCCN OOTFVKOQINZBBF-UHFFFAOYSA-N 0.000 description 5
229940099500 cystamine Drugs 0.000 description 5
239000003814 drug Substances 0.000 description 5
239000000843 powder Substances 0.000 description 5
238000000163 radioactive labelling Methods 0.000 description 5
125000000446 sulfanediyl group Chemical group *S* 0.000 description 5
239000003643 water by type Substances 0.000 description 5
102000010909 Monoamine Oxidase Human genes 0.000 description 4
108010062431 Monoamine oxidase Proteins 0.000 description 4
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
239000006071 cream Substances 0.000 description 4
210000004209 hair Anatomy 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000006210 lotion Substances 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
238000011160 research Methods 0.000 description 4
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
235000001674 Agaricus brunnescens Nutrition 0.000 description 3
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
239000012346 acetyl chloride Substances 0.000 description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
239000011575 calcium Substances 0.000 description 3
238000002512 chemotherapy Methods 0.000 description 3
238000001816 cooling Methods 0.000 description 3
208000035250 cutaneous malignant susceptibility to 1 melanoma Diseases 0.000 description 3
210000003780 hair follicle Anatomy 0.000 description 3
238000000338 in vitro Methods 0.000 description 3
239000011630 iodine Substances 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
210000004185 liver Anatomy 0.000 description 3
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
210000000056 organ Anatomy 0.000 description 3
239000000546 pharmaceutical excipient Substances 0.000 description 3
239000000049 pigment Substances 0.000 description 3
230000003389 potentiating effect Effects 0.000 description 3
238000000746 purification Methods 0.000 description 3
238000000926 separation method Methods 0.000 description 3
238000010898 silica gel chromatography Methods 0.000 description 3
201000000849 skin cancer Diseases 0.000 description 3
239000000126 substance Substances 0.000 description 3
230000000475 sunscreen effect Effects 0.000 description 3
239000000516 sunscreening agent Substances 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
231100000331 toxic Toxicity 0.000 description 3
230000002588 toxic effect Effects 0.000 description 3
241000700199 Cavia porcellus Species 0.000 description 2
102000004190 Enzymes Human genes 0.000 description 2
108090000790 Enzymes Proteins 0.000 description 2
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
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 2
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 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
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
238000002835 absorbance Methods 0.000 description 2
230000021736 acetylation Effects 0.000 description 2
238000006640 acetylation reaction Methods 0.000 description 2
RGCKGOZRHPZPFP-UHFFFAOYSA-N alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 2
FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
238000000211 autoradiogram Methods 0.000 description 2
238000000376 autoradiography Methods 0.000 description 2
230000009286 beneficial effect Effects 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
FUWUEFKEXZQKKA-UHFFFAOYSA-N beta-thujaplicin Chemical compound CC(C)C=1C=CC=C(O)C(=O)C=1 FUWUEFKEXZQKKA-UHFFFAOYSA-N 0.000 description 2
239000000872 buffer Substances 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
230000006835 compression Effects 0.000 description 2
238000007906 compression Methods 0.000 description 2
239000002537 cosmetic Substances 0.000 description 2
238000005947 deacylation reaction Methods 0.000 description 2
230000003247 decreasing effect Effects 0.000 description 2
DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
210000002615 epidermis Anatomy 0.000 description 2
VFPFQHQNJCMNBZ-UHFFFAOYSA-N ethyl gallate Chemical compound CCOC(=O)C1=CC(O)=C(O)C(O)=C1 VFPFQHQNJCMNBZ-UHFFFAOYSA-N 0.000 description 2
238000011156 evaluation Methods 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
230000003325 follicular Effects 0.000 description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 2
208000000069 hyperpigmentation Diseases 0.000 description 2
230000003810 hyperpigmentation Effects 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
229940102223 injectable solution Drugs 0.000 description 2
210000000936 intestine Anatomy 0.000 description 2
239000002207 metabolite Substances 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
210000004694 pigment cell Anatomy 0.000 description 2
238000012746 preparative thin layer chromatography Methods 0.000 description 2
230000002441 reversible effect Effects 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 2
238000010561 standard procedure Methods 0.000 description 2
229940124597 therapeutic agent Drugs 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
239000004408 titanium dioxide Substances 0.000 description 2
DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 description 1
QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 1
GKQHIYSTBXDYNQ-UHFFFAOYSA-M 1-dodecylpyridin-1-ium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+]1=CC=CC=C1 GKQHIYSTBXDYNQ-UHFFFAOYSA-M 0.000 description 1
UMEKPPOFCOUEDT-UHFFFAOYSA-N 1-icosanoylglycerol Chemical compound CCCCCCCCCCCCCCCCCCCC(=O)OCC(O)CO UMEKPPOFCOUEDT-UHFFFAOYSA-N 0.000 description 1
KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 1
BFPYWIDHMRZLRN-UHFFFAOYSA-N 17alpha-ethynyl estradiol Natural products OC1=CC=C2C3CCC(C)(C(CC4)(O)C#C)C4C3CCC2=C1 BFPYWIDHMRZLRN-UHFFFAOYSA-N 0.000 description 1
NYEZZYQZRQDLEH-UHFFFAOYSA-N 2-ethyl-4,5-dihydro-1,3-oxazole Chemical compound CCC1=NCCO1 NYEZZYQZRQDLEH-UHFFFAOYSA-N 0.000 description 1
IHZXTIBMKNSJCJ-UHFFFAOYSA-N 3-{[(4-{[4-(dimethylamino)phenyl](4-{ethyl[(3-sulfophenyl)methyl]amino}phenyl)methylidene}cyclohexa-2,5-dien-1-ylidene)(ethyl)azaniumyl]methyl}benzene-1-sulfonate Chemical compound C=1C=C(C(=C2C=CC(C=C2)=[N+](C)C)C=2C=CC(=CC=2)N(CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S(O)(=O)=O)=C1 IHZXTIBMKNSJCJ-UHFFFAOYSA-N 0.000 description 1
CYDQOEWLBCCFJZ-UHFFFAOYSA-N 4-(4-fluorophenyl)oxane-4-carboxylic acid Chemical compound C=1C=C(F)C=CC=1C1(C(=O)O)CCOCC1 CYDQOEWLBCCFJZ-UHFFFAOYSA-N 0.000 description 1
BXAVKNRWVKUTLY-UHFFFAOYSA-N 4-sulfanylphenol Chemical compound OC1=CC=C(S)C=C1 BXAVKNRWVKUTLY-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 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
241000922351 Anoma Species 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
239000004255 Butylated hydroxyanisole Substances 0.000 description 1
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-NJFSPNSNSA-N Carbon-14 Chemical compound [14C] OKTJSMMVPCPJKN-NJFSPNSNSA-N 0.000 description 1
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241000700198 Cavia Species 0.000 description 1
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KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
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BFPYWIDHMRZLRN-SLHNCBLASA-N Ethinyl estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 BFPYWIDHMRZLRN-SLHNCBLASA-N 0.000 description 1
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WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 1
WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 1
239000004166 Lanolin Substances 0.000 description 1
206010058467 Lung neoplasm malignant Diseases 0.000 description 1
231100000002 MTT assay Toxicity 0.000 description 1
238000000134 MTT assay Methods 0.000 description 1
206010027458 Metastases to lung Diseases 0.000 description 1
125000003047 N-acetyl group Chemical group 0.000 description 1
206010029260 Neuroblastoma Diseases 0.000 description 1
239000000020 Nitrocellulose Substances 0.000 description 1
206010051246 Photodermatosis Diseases 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
206010040825 Skin depigmentation Diseases 0.000 description 1
206010040880 Skin irritation Diseases 0.000 description 1
101100073357 Streptomyces halstedii sch2 gene Proteins 0.000 description 1
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MECHNRXZTMCUDQ-UHFFFAOYSA-N Vitamin D2 Natural products C1CCC2(C)C(C(C)C=CC(C)C(C)C)CCC2C1=CC=C1CC(O)CCC1=C MECHNRXZTMCUDQ-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/24—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/25—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/0404—Lipids, e.g. triglycerides; Polycationic carriers
- A61K51/0406—Amines, polyamines, e.g. spermine, spermidine, amino acids, (bis)guanidines
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
- C07C323/40—Y being a hydrogen or a carbon atom
- C07C323/41—Y being a hydrogen or an acyclic carbon atom

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Physics & Mathematics (AREA)
Medicinal Chemistry (AREA)
Optics & Photonics (AREA)
Biophysics (AREA)
Epidemiology (AREA)
Animal Behavior & Ethology (AREA)
Molecular Biology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Cosmetics (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

IL10634793A 1992-07-15 1993-07-14 Pharmaceutical compositions of noble derivatives of phenolic thioetherum for the treatment of pigmented diseases, such compounds and their use IL106347A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB929215066A GB9215066D0 (en)	1992-07-15	1992-07-15	Radio imaging and radio-therapy compounds
CA 2082252 CA2082252A1 (en)	1992-07-15	1992-11-05	Diacyl derivatives of phenolic thioether amines useful in treating pigmentation disorders

Publications (2)

Publication Number	Publication Date
IL106347A0 IL106347A0 (en)	1993-11-15
IL106347A true IL106347A (en)	1999-07-14

Family

ID=25675647

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL10634793A IL106347A (en)	1992-07-15	1993-07-14	Pharmaceutical compositions of noble derivatives of phenolic thioetherum for the treatment of pigmented diseases, such compounds and their use

Country Status (12)

Country	Link
US (2)	US5925332A (de)
EP (1)	EP0650473B1 (de)
JP (1)	JPH07508996A (de)
AT (1)	ATE153656T1 (de)
AU (1)	AU672021B2 (de)
DE (1)	DE69311114T2 (de)
DK (1)	DK0650473T3 (de)
ES (1)	ES2102041T3 (de)
GR (1)	GR3023992T3 (de)
HK (1)	HK1000731A1 (de)
IL (1)	IL106347A (de)
WO (1)	WO1994002456A1 (de)

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US6552060B1 (en)	1997-08-11	2003-04-22	Prolx Pharmaceuticals, Inc.	Asymmetric disulfides and methods of using same
US20030176512A1 (en) *	1998-08-11	2003-09-18	Kirkpatrick D. Lynn	Asymmetric disulfides and methods of using same
US5981076A (en) *	1996-12-09	1999-11-09	3M Innovative Properties Company	UV protected syndiotactic polystyrene overlay films
JP2003206237A (ja) *	1999-10-08	2003-07-22	Shiseido Co Ltd	皮膚免疫機能調節剤
AU2001243334A1 (en) *	2000-02-29	2001-09-12	Integriderm, Inc.	Inhibitors of melanocyte tyrosinase as topical skin lighteners
US20050214441A1 (en) *	2002-09-27	2005-09-29	Ian Ray	Method for rendering fingerprints visible
EP1402816A1 (de) *	2002-09-27	2004-03-31	Communauté Européenne de l'Energie Atomique (EURATOM)	Verfahren zur Sichtbarmachung von Fingerabdrücken
AU2005334836B2 (en)	2005-07-28	2012-04-12	Academisch Ziekenhuis Leiden H.O.D.N. Lumc	Sensitization of immune system against haptenized melanoma antigens

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5283342A (en) *	1992-06-09	1994-02-01	Neorx Corporation	Biotinylated small molecules
US4183927A (en) *	1976-08-16	1980-01-15	The Dow Chemical Company	Substituted phenylthioalkylamines and compositions thereof
US4155907A (en) *	1976-08-16	1979-05-22	The Dow Chemical Company	Method for inhibiting ADP-induced platelet aggregation using phenylthioalkylamines
CA2015197C (en) *	1990-04-23	1999-08-24	The Governors Of The University Of Alberta	Phenolic amine depigmenting and antimelanoma agents
US5395611A (en) *	1990-04-24	1995-03-07	The Governors Of The University Of Alberta	Phenolic amine depigmenting and antimelanoma agents

1993
- 1993-07-14 AU AU45554/93A patent/AU672021B2/en not_active Ceased
- 1993-07-14 IL IL10634793A patent/IL106347A/en not_active IP Right Cessation
- 1993-07-14 US US08/367,194 patent/US5925332A/en not_active Expired - Fee Related
- 1993-07-14 DE DE69311114T patent/DE69311114T2/de not_active Expired - Fee Related
- 1993-07-14 ES ES93915605T patent/ES2102041T3/es not_active Expired - Lifetime
- 1993-07-14 HK HK97102345A patent/HK1000731A1/en not_active IP Right Cessation
- 1993-07-14 WO PCT/CA1993/000292 patent/WO1994002456A1/en not_active Ceased
- 1993-07-14 DK DK93915605.5T patent/DK0650473T3/da active
- 1993-07-14 AT AT93915605T patent/ATE153656T1/de not_active IP Right Cessation
- 1993-07-14 EP EP93915605A patent/EP0650473B1/de not_active Expired - Lifetime
- 1993-07-14 JP JP6504045A patent/JPH07508996A/ja active Pending
1996
- 1996-08-27 US US08/708,125 patent/US5756068A/en not_active Expired - Fee Related
1997
- 1997-07-02 GR GR970401649T patent/GR3023992T3/el unknown

Also Published As

Publication number	Publication date
WO1994002456A1 (en)	1994-02-03
EP0650473A1 (de)	1995-05-03
JPH07508996A (ja)	1995-10-05
DK0650473T3 (da)	1997-08-25
DE69311114D1 (de)	1997-07-03
GR3023992T3 (en)	1997-10-31
US5756068A (en)	1998-05-26
AU672021B2 (en)	1996-09-19
AU4555493A (en)	1994-02-14
ATE153656T1 (de)	1997-06-15
EP0650473B1 (de)	1997-05-28
US5925332A (en)	1999-07-20
IL106347A0 (en)	1993-11-15
HK1000731A1 (en)	1998-04-24
DE69311114T2 (de)	1997-09-18
ES2102041T3 (es)	1997-07-16

Legal Events

Date	Code	Title
1999-11-30	FF	Patent granted
2000-06-29	KB	Patent renewed
2004-03-28	RH1	Patent not in force

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US5138089A (en)	1992-08-11	Chromophores, sunscreen compositions and methods for preventing sunburn
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EP0251398A2 (de)	1988-01-07	Chromophore, Sonnenschutzpräparate und Verfahren zur Verhütung des Sonnenbrandes
US5925332A (en)	1999-07-20	Radioimaging and radiochemotherapy phenolic thioether amines and acyl derivatives thereof for use in diagnosing and treating pigmentation disorders
CA2137897A1 (fr)	1995-06-16	Composes bi-aromatiques derives d'amide, compositions pharmaceutiques et cosmetiques les contenant et utilisations
HK1000731B (en)	1998-04-24	Radioimaging and radiochemotherapy phenolic thioether amines and acyl derivatives thereof for use in diagnosing and treating pigmentation disorders
US5160731A (en)	1992-11-03	Sunscreen agents, sunscreen compositions and methods for preventing sunburn
AU651823B2 (en)	1994-08-04	Phenolic amine depigmenting and antimelanoma agents
US5395611A (en)	1995-03-07	Phenolic amine depigmenting and antimelanoma agents
JPH10147558A (ja)	1998-06-02	ポリアルキレンポリアミンのベンジル置換誘導体及び化粧品及び薬理学的組成物でのそれらの使用
FR2737204A1 (fr)	1997-01-31	Derives de n,n'-di(aralkyl)n,n'-di(carboxylakyl)alkylene di- ou triamine et de n-(aralkyl)n'-(carboxyalkyl) n,n'-di(carboxyalkyl)alkylene di- ou triamine et leur utilisation en pharmacie et en cosmetique
CA2140293A1 (en)	1994-02-03	Radioimaging and radiochemotherapy phenolic thioether amines and acyl derivatives thereof for use in diagnosing and treating pigmentation disorders
CA2082252A1 (en)	1994-01-16	Diacyl derivatives of phenolic thioether amines useful in treating pigmentation disorders
US5243064A (en)	1993-09-07	Chromophores, sunscreen compositions and methods for preventing sunburn
US5871755A (en)	1999-02-16	Dehydroalanine derivatives for protecting the skin, the mucous membranes and/or the hair from oxidative stress, cosmetic or dermatological compositions containing them
HK1000730B (en)	1998-04-24	Phenolic amine depigmenting and antimelanoma agents
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Park et al.	2001	Synthesis of iodine‐123 labeled quercetin and catechin as radical seeking agents
JPH06227958A (ja)	1994-08-16	皮膚外用剤
FR2573755A1 (fr)	1986-05-30	Derives polysubstitues du naphtalene, leur procede de preparation et leur application dans les domaines pharmaceutique et cosmetique
JPH0977718A (ja)	1997-03-25	安息香酸誘導体及びこれを含有する皮膚外用剤
JPS61189296A (ja)	1986-08-22	グルタチオン誘導体及びこれを含有する皮膚外用剤