DE3337207C2 - - Google Patents
Info
- Publication number
- DE3337207C2 DE3337207C2 DE3337207A DE3337207A DE3337207C2 DE 3337207 C2 DE3337207 C2 DE 3337207C2 DE 3337207 A DE3337207 A DE 3337207A DE 3337207 A DE3337207 A DE 3337207A DE 3337207 C2 DE3337207 C2 DE 3337207C2
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- hydrogen
- general formula
- methyl
- formula
- 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.)
- Expired - Lifetime
Links
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 19
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 15
- 150000002431 hydrogen Chemical group 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 238000011282 treatment Methods 0.000 claims description 11
- QWQWBHZHRMHXOC-UHFFFAOYSA-N 7-Hydroxy-6-methyl-2H-1-benzopyran-2-one Chemical compound C1=CC(=O)OC2=C1C=C(C)C(O)=C2 QWQWBHZHRMHXOC-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 229950005143 sitosterol Drugs 0.000 claims description 9
- -1 acetoxymethyl Chemical group 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 201000004681 Psoriasis Diseases 0.000 claims description 6
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 6
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 5
- 230000001413 cellular effect Effects 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- FWYIBGHGBOVPNL-UHFFFAOYSA-N scopoletin Natural products COC=1C=C2C=CC(OC2=C(C1)O)=O FWYIBGHGBOVPNL-UHFFFAOYSA-N 0.000 claims description 5
- 206010047642 Vitiligo Diseases 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 208000017520 skin disease Diseases 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 3
- 201000004384 Alopecia Diseases 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical group [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 claims description 2
- 231100000360 alopecia Toxicity 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 150000003840 hydrochlorides Chemical class 0.000 claims description 2
- 239000001632 sodium acetate Substances 0.000 claims description 2
- 235000017281 sodium acetate Nutrition 0.000 claims description 2
- XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 claims 1
- 229940061627 chloromethyl methyl ether Drugs 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 78
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 28
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- ZCCUUQDIBDJBTK-UHFFFAOYSA-N psoralen Chemical compound C1=C2OC(=O)C=CC2=CC2=C1OC=C2 ZCCUUQDIBDJBTK-UHFFFAOYSA-N 0.000 description 14
- 235000019439 ethyl acetate Nutrition 0.000 description 13
- 210000003491 skin Anatomy 0.000 description 13
- BUNGCZLFHHXKBX-UHFFFAOYSA-N 8-methoxypsoralen Natural products C1=CC(=O)OC2=C1C=C1CCOC1=C2OC BUNGCZLFHHXKBX-UHFFFAOYSA-N 0.000 description 12
- 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
- QXKHYNVANLEOEG-UHFFFAOYSA-N Methoxsalen Chemical compound C1=CC(=O)OC2=C1C=C1C=COC1=C2OC QXKHYNVANLEOEG-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- 229960004469 methoxsalen Drugs 0.000 description 12
- SQBBOVROCFXYBN-UHFFFAOYSA-N methoxypsoralen Natural products C1=C2OC(=O)C(OC)=CC2=CC2=C1OC=C2 SQBBOVROCFXYBN-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 108020004414 DNA Proteins 0.000 description 11
- 238000010992 reflux Methods 0.000 description 10
- 235000001671 coumarin Nutrition 0.000 description 9
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 238000002560 therapeutic procedure Methods 0.000 description 8
- VQDAXVSOTNGSJB-UHFFFAOYSA-N 7-hydroxy-4,6-dimethylchromen-2-one Chemical compound CC1=CC(=O)OC2=C1C=C(C)C(O)=C2 VQDAXVSOTNGSJB-UHFFFAOYSA-N 0.000 description 7
- 229960000956 coumarin Drugs 0.000 description 7
- 125000004494 ethyl ester group Chemical group 0.000 description 7
- PFVGXOYZQOJGGR-UHFFFAOYSA-N 6-methylfuro[2,3-h]chromen-2-one Chemical compound C1=CC(=O)OC2=C1C=C(C)C1=C2C=CO1 PFVGXOYZQOJGGR-UHFFFAOYSA-N 0.000 description 6
- UUMZSXINPVWGFX-UHFFFAOYSA-N 7-hydroxy-5,6-dimethylchromen-2-one Chemical compound O1C(=O)C=CC2=C(C)C(C)=C(O)C=C21 UUMZSXINPVWGFX-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 5
- 208000012641 Pigmentation disease Diseases 0.000 description 5
- 230000003902 lesion Effects 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 230000035755 proliferation Effects 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- NHVDNUKWBWGTLB-UHFFFAOYSA-N (5,6-dimethyl-2-oxochromen-7-yl) acetate Chemical compound O1C(=O)C=CC2=C1C=C(OC(=O)C)C(C)=C2C NHVDNUKWBWGTLB-UHFFFAOYSA-N 0.000 description 4
- AYHSRSLMDCLHKM-UHFFFAOYSA-N (6-methyl-2-oxochromen-7-yl) acetate Chemical compound O1C(=O)C=CC2=C1C=C(OC(=O)C)C(C)=C2 AYHSRSLMDCLHKM-UHFFFAOYSA-N 0.000 description 4
- FNYDIAAMUCQQDE-UHFFFAOYSA-N 4-methylbenzene-1,3-diol Chemical compound CC1=CC=C(O)C=C1O FNYDIAAMUCQQDE-UHFFFAOYSA-N 0.000 description 4
- UTPWWGUELZENOK-UHFFFAOYSA-N 8-acetyl-7-hydroxy-6-methylchromen-2-one Chemical compound C1=CC(=O)OC2=C1C=C(C)C(O)=C2C(=O)C UTPWWGUELZENOK-UHFFFAOYSA-N 0.000 description 4
- 230000006820 DNA synthesis Effects 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
- 230000001028 anti-proliverative effect Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000000314 lubricant Substances 0.000 description 4
- 229920002521 macromolecule Polymers 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 230000000258 photobiological effect Effects 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- TZCWEZGQPBVQDO-UHFFFAOYSA-N (4,6-dimethyl-2-oxochromen-7-yl) acetate Chemical compound O1C(=O)C=C(C)C2=C1C=C(OC(=O)C)C(C)=C2 TZCWEZGQPBVQDO-UHFFFAOYSA-N 0.000 description 3
- VWISGRNVMLSLCE-UHFFFAOYSA-N 6,8-dimethylfuro[2,3-h]chromen-2-one Chemical compound C1=CC(=O)OC2=C1C=C(C)C1=C2C=C(C)O1 VWISGRNVMLSLCE-UHFFFAOYSA-N 0.000 description 3
- HBBAUSZULSWDFX-UHFFFAOYSA-N 8-acetyl-7-hydroxy-4,6-dimethylchromen-2-one Chemical compound CC1=CC(=O)OC2=C1C=C(C)C(O)=C2C(=O)C HBBAUSZULSWDFX-UHFFFAOYSA-N 0.000 description 3
- YGNQEADUUIINCM-UHFFFAOYSA-N 8-acetyl-7-hydroxy-5,6-dimethylchromen-2-one Chemical compound C1=CC(=O)OC2=C1C(C)=C(C)C(O)=C2C(=O)C YGNQEADUUIINCM-UHFFFAOYSA-N 0.000 description 3
- 241000700198 Cavia Species 0.000 description 3
- 206010015150 Erythema Diseases 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 239000007832 Na2SO4 Substances 0.000 description 3
- 206010034972 Photosensitivity reaction Diseases 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 230000001588 bifunctional effect Effects 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 231100000024 genotoxic Toxicity 0.000 description 3
- 230000001738 genotoxic effect Effects 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 208000007578 phototoxic dermatitis Diseases 0.000 description 3
- 231100000018 phototoxicity Toxicity 0.000 description 3
- 230000019612 pigmentation Effects 0.000 description 3
- 150000003194 psoralenes Chemical class 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- VXGRJERITKFWPL-UHFFFAOYSA-N 4',5'-Dihydropsoralen Natural products C1=C2OC(=O)C=CC2=CC2=C1OCC2 VXGRJERITKFWPL-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 238000009193 PUVA therapy Methods 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007884 disintegrant Substances 0.000 description 2
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 2
- 229940043264 dodecyl sulfate Drugs 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 231100000321 erythema Toxicity 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 201000005962 mycosis fungoides Diseases 0.000 description 2
- 231100001085 no phototoxicity Toxicity 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 2
- 230000008832 photodamage Effects 0.000 description 2
- 231100000760 phototoxic Toxicity 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- YLLIGHVCTUPGEH-UHFFFAOYSA-M potassium;ethanol;hydroxide Chemical compound [OH-].[K+].CCO YLLIGHVCTUPGEH-UHFFFAOYSA-M 0.000 description 2
- 230000001185 psoriatic effect Effects 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- KZJWDPNRJALLNS-VJSFXXLFSA-N sitosterol Chemical class C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 KZJWDPNRJALLNS-VJSFXXLFSA-N 0.000 description 2
- 201000000849 skin cancer Diseases 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- MGZOXZPZHVOXQB-UHFFFAOYSA-N (2-oxochromen-7-yl) acetate Chemical class C1=CC(=O)OC2=CC(OC(=O)C)=CC=C21 MGZOXZPZHVOXQB-UHFFFAOYSA-N 0.000 description 1
- UWJQFFWGINJFJX-UHFFFAOYSA-N 2-(2-oxochromen-8-yl)acetaldehyde Chemical compound C1=CC(=O)OC2=C1C=CC=C2CC=O UWJQFFWGINJFJX-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- VRCYFMXDPGWEGA-UHFFFAOYSA-N 3-hydroxy-6-methyl-2H-chromen-2-one Chemical compound O1C(=O)C(O)=CC2=CC(C)=CC=C21 VRCYFMXDPGWEGA-UHFFFAOYSA-N 0.000 description 1
- RCNCKKACINZDOI-UHFFFAOYSA-N 4,5-dimethylbenzene-1,3-diol Chemical compound CC1=CC(O)=CC(O)=C1C RCNCKKACINZDOI-UHFFFAOYSA-N 0.000 description 1
- CJIJXIFQYOPWTF-UHFFFAOYSA-N 7-hydroxycoumarin Natural products O1C(=O)C=CC2=CC(O)=CC=C21 CJIJXIFQYOPWTF-UHFFFAOYSA-N 0.000 description 1
- 101100509371 Arabidopsis thaliana CHR11 gene Proteins 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 208000002177 Cataract Diseases 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 230000005778 DNA damage Effects 0.000 description 1
- 231100000277 DNA damage Toxicity 0.000 description 1
- 208000003468 Ehrlich Tumor Carcinoma Diseases 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 208000034693 Laceration Diseases 0.000 description 1
- 206010024380 Leukoderma Diseases 0.000 description 1
- 206010067125 Liver injury Diseases 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 208000000453 Skin Neoplasms Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000001574 biopsy Methods 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 108091092356 cellular DNA Proteins 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000035614 depigmentation Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 231100000234 hepatic damage Toxicity 0.000 description 1
- 238000010562 histological examination Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000008818 liver damage Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 231100000243 mutagenic effect Toxicity 0.000 description 1
- 230000003505 mutagenic effect Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000008196 pharmacological composition Substances 0.000 description 1
- 230000003300 photodamaging effect Effects 0.000 description 1
- 230000002165 photosensitisation Effects 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 201000008261 skin carcinoma Diseases 0.000 description 1
- 210000004927 skin cell Anatomy 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 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
- 238000011287 therapeutic dose Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- ORHBXUUXSCNDEV-UHFFFAOYSA-N umbelliferone Chemical compound C1=CC(=O)OC2=CC(O)=CC=C21 ORHBXUUXSCNDEV-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- 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
- A61P3/00—Drugs for disorders of the metabolism
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/16—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Dermatology (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT84148/82A IT1165797B (it) | 1982-10-18 | 1982-10-18 | Procedimento di preparazione di alchilangelicine esenti da psoraleni ed alchilangolicine ottenute col procedimento |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3337207A1 DE3337207A1 (de) | 1984-04-19 |
| DE3337207C2 true DE3337207C2 (en, 2012) | 1991-12-19 |
Family
ID=11324788
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19833337207 Granted DE3337207A1 (de) | 1982-10-18 | 1983-10-13 | Verfahren zur herstellung von psoralenfreien alkylangelicinen |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US5001147A (en, 2012) |
| JP (1) | JPH0633269B2 (en, 2012) |
| AT (1) | AT384810B (en, 2012) |
| AU (1) | AU559082B2 (en, 2012) |
| CA (1) | CA1228860A (en, 2012) |
| CH (1) | CH662566A5 (en, 2012) |
| DE (1) | DE3337207A1 (en, 2012) |
| ES (1) | ES8608523A1 (en, 2012) |
| FR (1) | FR2534585B1 (en, 2012) |
| GB (1) | GB2128997B (en, 2012) |
| IT (1) | IT1165797B (en, 2012) |
| ZA (1) | ZA837585B (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1967185A1 (en) * | 1999-12-23 | 2008-09-10 | Pfizer Products Inc. | Hydrogel-driven drug dosage form |
| CN101287493A (zh) * | 2005-08-18 | 2008-10-15 | 根马布股份公司 | 采用cd4结合肽和辐射的疗法 |
| ITVE20070005A1 (it) | 2007-01-25 | 2008-07-26 | Associazione Veneta Per La Lotta Alla Talassemia | Farmaco per la cura della talassemia, dell'anemia falciforme e di tutte le altre forme di anemia trattabili con questo, metodo di attivazione del farmaco, composizione farmaceutica avente come principio attivo il farmaco e metodo fotochemioterapico u |
| CN102177162B (zh) | 2008-10-21 | 2015-02-11 | 花王株式会社 | Nfat信号抑制剂以及育发剂 |
| CN105832720B (zh) * | 2016-05-03 | 2019-04-05 | 中国科学院新疆理化技术研究所 | 一种补骨脂素类化合物的用途 |
| CN116554190A (zh) * | 2023-05-06 | 2023-08-08 | 河南中烟工业有限责任公司 | 一种香柑醇的合成方法及应用 |
| CN116554191A (zh) * | 2023-05-06 | 2023-08-08 | 河南中烟工业有限责任公司 | 一种香柑内酯的合成方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI59598C (fi) * | 1977-10-03 | 1981-09-10 | Star Oy Ab | Nytt foerfarande foer framstaellning av i 9-staellningen eventuellt metoxisubstituerade 7h-furo(3,2-g)(1)bensopyran-7-oner |
| JPS55124775A (en) * | 1979-03-13 | 1980-09-26 | Elder Thomas C Inc | Alphaalower alkylfurocoumarin manufacture and intermediate oftained therefrom |
| US4216154A (en) * | 1979-03-15 | 1980-08-05 | Thomas C. Elder, Inc. | Process for making α-loweralkylfurocoumarins |
| IT1166343B (it) * | 1979-08-20 | 1987-04-29 | Francarosa Baccichetti | Furocumarina per la fotochemioterapia della fsoriasi e di altre malattie cutanee ad essa sensibili |
-
1982
- 1982-10-18 IT IT84148/82A patent/IT1165797B/it active
-
1983
- 1983-10-11 GB GB08327200A patent/GB2128997B/en not_active Expired
- 1983-10-12 ZA ZA837585A patent/ZA837585B/xx unknown
- 1983-10-13 DE DE19833337207 patent/DE3337207A1/de active Granted
- 1983-10-13 AU AU20141/83A patent/AU559082B2/en not_active Ceased
- 1983-10-14 CH CH5624/83A patent/CH662566A5/it not_active IP Right Cessation
- 1983-10-17 AT AT0370383A patent/AT384810B/de not_active IP Right Cessation
- 1983-10-17 CA CA000439121A patent/CA1228860A/en not_active Expired
- 1983-10-18 ES ES526910A patent/ES8608523A1/es not_active Expired
- 1983-10-18 FR FR8316604A patent/FR2534585B1/fr not_active Expired
- 1983-10-18 JP JP58195145A patent/JPH0633269B2/ja not_active Expired - Lifetime
-
1988
- 1988-05-16 US US07/194,180 patent/US5001147A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| FR2534585A1 (fr) | 1984-04-20 |
| JPH0633269B2 (ja) | 1994-05-02 |
| FR2534585B1 (fr) | 1986-12-19 |
| ZA837585B (en) | 1984-06-27 |
| DE3337207A1 (de) | 1984-04-19 |
| AT384810B (de) | 1988-01-11 |
| ATA370383A (de) | 1987-06-15 |
| ES8608523A1 (es) | 1986-07-16 |
| CA1228860A (en) | 1987-11-03 |
| IT1165797B (it) | 1987-04-29 |
| GB2128997A (en) | 1984-05-10 |
| AU559082B2 (en) | 1987-02-19 |
| US5001147A (en) | 1991-03-19 |
| GB8327200D0 (en) | 1983-11-09 |
| IT8284148A0 (it) | 1982-10-18 |
| CH662566A5 (it) | 1987-10-15 |
| JPS59104387A (ja) | 1984-06-16 |
| AU2014183A (en) | 1984-05-03 |
| ES526910A0 (es) | 1986-07-16 |
| GB2128997B (en) | 1985-12-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE3031164C2 (de) | Angelicine enthaltende Arzneimittel, Angelicine als solche sowie Verfahren zu deren Herstellung | |
| DE2858042C2 (de) | Rechtsdrehendes Isomer eines asymmetrischen Spirohydantoins sowie der Basensalze hiervon und ihre Verwendung | |
| EP0013983B1 (de) | Antineoplastische Mittel auf Basis von nicht oder nur geringfügig irritierenden und/oder promovierenden Diterpenalkoholen und Derivaten davon und deren Herstellung | |
| DE2549783C3 (de) | Triglyceride mit entzündungshemmender Wirkung | |
| DE3024855C2 (en, 2012) | ||
| DE3129750A1 (de) | 5'-aminoalkyl-4',4,8-trialkylpsoralene | |
| DE2003430C3 (de) | p-Benzoylphenoxyisobuttersäureester, ihre Herstellung und diese enthaltende Arzneimittel | |
| DE3033897C2 (en, 2012) | ||
| DE3033896C2 (en, 2012) | ||
| DE3033895C2 (en, 2012) | ||
| DE3337207C2 (en, 2012) | ||
| EP1763520B1 (de) | Verwendung von trisubstituierten benzopyranonen | |
| DD201903A5 (de) | Verfahren zur herstellung von derivaten des thienopyridonons | |
| DE2947624A1 (de) | Beta, gamma -dihydropolyprenylalkohol und diesen enthaltendes blutdrucksenkendes arzneimittel | |
| DE2850509A1 (de) | Antidermatophytisches mittel und verwendung desselben zur bekaempfung von dermatomycosen | |
| DE2007345A1 (de) | Neue substituierte Hexahydroimidazochinoline und deren Säureanlagerungssalze | |
| DE29923419U1 (de) | Neue Xanthonverbindungen und diese enthaltende Arzneimittel | |
| DE69609314T2 (de) | Amorph piretanide, polymorphe davon, verfahren zur dessen herstellung und ihre verwendung | |
| DE2253914C3 (de) | Chromon-3-acrylsaeuren, verfahren zu ihrer herstellung sowie diese verbindung enthaltende arzneimittel | |
| DE2632118B2 (de) | Apovincaminolester und Verfahren zu deren Herstellung und Arzneimittel | |
| DE3204630C2 (en, 2012) | ||
| EP0351720A2 (de) | Verwendung substituierter 3,4-Dihydro-2H-benzopyrane als Heilmittel gegen obstruktive Funktionsstörungen der Lunge | |
| EP0345598B1 (de) | Zytostatisch wirksame Anthracyclinderivate | |
| CH634076A5 (de) | Verfahren zur herstellung von vincaalkaloiden. | |
| DE1595870C3 (de) | Verfahren zur Herstellung von 3-(o-Methoxyphenoxy)-1,2-propandiolnicotinaten und deren Säureadditionssalzen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8328 | Change in the person/name/address of the agent |
Free format text: RECHTS- UND PATENTANWAELTE REBLE & KLOSE, 68165 MANNHEIM |
|
| 8339 | Ceased/non-payment of the annual fee |