CH651007A5 - Polyenverbindungen. - Google Patents
Polyenverbindungen. Download PDFInfo
- Publication number
- CH651007A5 CH651007A5 CH3889/82A CH388982A CH651007A5 CH 651007 A5 CH651007 A5 CH 651007A5 CH 3889/82 A CH3889/82 A CH 3889/82A CH 388982 A CH388982 A CH 388982A CH 651007 A5 CH651007 A5 CH 651007A5
- Authority
- CH
- Switzerland
- Prior art keywords
- methyl
- acid
- lower alkyl
- formula
- ethyl ester
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 206010028980 Neoplasm Diseases 0.000 claims description 6
- 238000011282 treatment Methods 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 230000002757 inflammatory effect Effects 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 230000003412 degenerative effect Effects 0.000 claims description 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
- 208000002874 Acne Vulgaris Diseases 0.000 claims description 2
- 201000004681 Psoriasis Diseases 0.000 claims description 2
- 208000025747 Rheumatic disease Diseases 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 206010000496 acne Diseases 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 230000003902 lesion Effects 0.000 claims description 2
- 230000003211 malignant effect Effects 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-O triphenylphosphanium Chemical compound C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-O 0.000 claims description 2
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims 1
- CMLCBUOUHXEBNT-UHFFFAOYSA-N CC1(C=2C=CC(=CC2C(CC1)(C)C)C(C(=O)N)=CC=CC=CC)C Chemical compound CC1(C=2C=CC(=CC2C(CC1)(C)C)C(C(=O)N)=CC=CC=CC)C CMLCBUOUHXEBNT-UHFFFAOYSA-N 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 230000009826 neoplastic cell growth Effects 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- -1 polyene compounds Chemical class 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- 230000000699 topical effect Effects 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 4
- 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 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 150000001733 carboxylic acid esters Chemical class 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 231100000252 nontoxic Toxicity 0.000 description 3
- 230000003000 nontoxic effect Effects 0.000 description 3
- 239000002674 ointment Substances 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- LQFXCMXTFFNUOQ-UHFFFAOYSA-N ethyl 4-methyl-6-oxohexa-2,4-dienoate Chemical compound CCOC(=O)C=CC(C)=CC=O LQFXCMXTFFNUOQ-UHFFFAOYSA-N 0.000 description 2
- RIPOKBXTWZSJQF-UHFFFAOYSA-N ethyl 6-acetyloxy-4-methylhexa-2,4-dienoate Chemical compound CCOC(=O)C=CC(C)=CCOC(C)=O RIPOKBXTWZSJQF-UHFFFAOYSA-N 0.000 description 2
- QONYVPVIAZDSLK-UHFFFAOYSA-N ethyl 6-hydroxy-4-methylhexa-2,4-dienoate Chemical compound CCOC(=O)C=CC(C)=CCO QONYVPVIAZDSLK-UHFFFAOYSA-N 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 208000003154 papilloma Diseases 0.000 description 2
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- 238000009121 systemic therapy Methods 0.000 description 2
- FKMJROWWQOJRJX-UHFFFAOYSA-M triphenyl(prop-2-enyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC=C)C1=CC=CC=C1 FKMJROWWQOJRJX-UHFFFAOYSA-M 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 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 1
- QRBJSGUWLNVUEA-UHFFFAOYSA-N 4-methyl-6-oxohexa-2,4-dienoic acid Chemical compound O=CC=C(C)C=CC(O)=O QRBJSGUWLNVUEA-UHFFFAOYSA-N 0.000 description 1
- ARSRBNBHOADGJU-UHFFFAOYSA-N 7,12-dimethyltetraphene Chemical compound C1=CC2=CC=CC=C2C2=C1C(C)=C(C=CC=C1)C1=C2C ARSRBNBHOADGJU-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 206010060999 Benign neoplasm Diseases 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 206010048768 Dermatosis Diseases 0.000 description 1
- QZKRHPLGUJDVAR-UHFFFAOYSA-K EDTA trisodium salt Chemical compound [Na+].[Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O QZKRHPLGUJDVAR-UHFFFAOYSA-K 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- 206010036030 Polyarthritis Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 208000007156 Spondylarthritis Diseases 0.000 description 1
- 201000002661 Spondylitis Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 235000019282 butylated hydroxyanisole Nutrition 0.000 description 1
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 1
- 229940043253 butylated hydroxyanisole Drugs 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000006003 cornification Effects 0.000 description 1
- 229940117173 croton oil Drugs 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- UCELODDDRLBTLL-UHFFFAOYSA-N ethyl 2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)octa-2,4,6-trienoate Chemical compound C(C)OC(C(=CC=CC=CC)C1=CC=2C(CCC(C=2C=C1)(C)C)(C)C)=O UCELODDDRLBTLL-UHFFFAOYSA-N 0.000 description 1
- ROSDRBHUPHJNOY-UHFFFAOYSA-N ethyl 4,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoate Chemical compound CCOC(=O)C=CC(C)=CC=C(C)C=CC1=C(C)CCCC1(C)C ROSDRBHUPHJNOY-UHFFFAOYSA-N 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000001503 joint Anatomy 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 210000002346 musculoskeletal system Anatomy 0.000 description 1
- KUIRIUAPFCJBHU-UHFFFAOYSA-N n-ethyl-4-methyl-7-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)octa-2,4,6-trienamide Chemical compound CC1(C)CCC(C)(C)C=2C1=CC(C(C)=CC=C(C)C=CC(=O)NCC)=CC=2 KUIRIUAPFCJBHU-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet 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
- 210000002435 tendon Anatomy 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
- CMSYDJVRTHCWFP-UHFFFAOYSA-N triphenylphosphane;hydrobromide Chemical compound Br.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 CMSYDJVRTHCWFP-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/74—Unsaturated compounds containing —CHO groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/46—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid
- C07C57/50—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid containing condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (20)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH3889/82A CH651007A5 (de) | 1982-06-24 | 1982-06-24 | Polyenverbindungen. |
| CA000430391A CA1276032C (fr) | 1982-06-24 | 1983-06-14 | Composes de polyene |
| NL8302136A NL8302136A (nl) | 1982-06-24 | 1983-06-15 | Polyeenverbindingen, werkwijze voor de bereiding ervan en farmaceutische preparaten, die deze polyeenverbindingen bevatten. |
| DE3321662A DE3321662A1 (de) | 1982-06-24 | 1983-06-15 | Polyenverbindungen |
| ZA834473A ZA834473B (en) | 1982-06-24 | 1983-06-17 | Polyene compounds |
| NZ204628A NZ204628A (en) | 1982-06-24 | 1983-06-17 | Polyene compounds and pharmaceutical compositions |
| IL69028A IL69028A0 (en) | 1982-06-24 | 1983-06-20 | Polyene compounds,their preparation and pharmaceutical compositions containing them |
| SE8303539A SE454984B (sv) | 1982-06-24 | 1983-06-20 | Polyenforeningar, forfarande for deras framstellning samt farmaceutiska preparat innehallande dessa |
| DK287083A DK159392C (da) | 1982-06-24 | 1983-06-21 | Analogifremgangsmaade til fremstilling af polyenforbindelser |
| IT8321721A IT1212753B (it) | 1982-06-24 | 1983-06-21 | Composti polienici,procedimento per la loro preparazione e preparati farmaceutici che li contengono |
| LU84870A LU84870A1 (de) | 1982-06-24 | 1983-06-22 | Polyenverbindungen |
| FR8310319A FR2529201B1 (fr) | 1982-06-24 | 1983-06-22 | Composes polyethyleniques, procede pour leur preparation et leurs utilisations therapeutiques, notamment en tant qu'agents antitumeurs |
| AT2305/83A AT392780B (de) | 1982-06-24 | 1983-06-23 | Verfahren zur herstellung von neuen saeurederivaten |
| JP58111979A JPS5910547A (ja) | 1982-06-24 | 1983-06-23 | ポリエン化合物 |
| IE1471/83A IE55285B1 (en) | 1982-06-24 | 1983-06-23 | Polyene compounds |
| PH29108A PH20070A (en) | 1982-06-24 | 1983-06-23 | Polyene compounds |
| GB08317129A GB2122200B (en) | 1982-06-24 | 1983-06-23 | Polyene compounds |
| BE0/211055A BE897118A (fr) | 1982-06-24 | 1983-06-23 | Composes polyethyleniques |
| AU16201/83A AU560027B2 (en) | 1982-06-24 | 1983-06-24 | Polyene compounds |
| GB08510717A GB2156351B (en) | 1982-06-24 | 1985-04-26 | An ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH3889/82A CH651007A5 (de) | 1982-06-24 | 1982-06-24 | Polyenverbindungen. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH651007A5 true CH651007A5 (de) | 1985-08-30 |
Family
ID=4265678
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH3889/82A CH651007A5 (de) | 1982-06-24 | 1982-06-24 | Polyenverbindungen. |
Country Status (19)
| Country | Link |
|---|---|
| JP (1) | JPS5910547A (fr) |
| AT (1) | AT392780B (fr) |
| AU (1) | AU560027B2 (fr) |
| BE (1) | BE897118A (fr) |
| CA (1) | CA1276032C (fr) |
| CH (1) | CH651007A5 (fr) |
| DE (1) | DE3321662A1 (fr) |
| DK (1) | DK159392C (fr) |
| FR (1) | FR2529201B1 (fr) |
| GB (2) | GB2122200B (fr) |
| IE (1) | IE55285B1 (fr) |
| IL (1) | IL69028A0 (fr) |
| IT (1) | IT1212753B (fr) |
| LU (1) | LU84870A1 (fr) |
| NL (1) | NL8302136A (fr) |
| NZ (1) | NZ204628A (fr) |
| PH (1) | PH20070A (fr) |
| SE (1) | SE454984B (fr) |
| ZA (1) | ZA834473B (fr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1203634B (it) * | 1984-08-13 | 1989-02-15 | Oreal | Derivati 1-sostituiti del 4-metossi-2,3,6-trimetilbenzene loro procedimento di preparazione e composizioni medicamentose e cosmetiche che li contengono |
| FR2621912B1 (fr) * | 1987-10-16 | 1990-03-02 | Oreal | Nouveaux derives du norbornane, leur procede de preparation et compositions cosmetique et medicamenteuse les contenant |
| DE4033568A1 (de) * | 1990-10-22 | 1992-04-23 | Henkel Kgaa | Bicyclische verbindungen mit antiseborrhoischer wirkung |
| DE69510203T2 (de) * | 1994-08-10 | 1999-12-23 | F. Hoffmann-La Roche Ag, Basel | Retinoesäure x-rezeptor liganden |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1070173B (de) * | 1959-12-03 | Badische Anilin- S. Soda-Fabrik Aktiengesellschaft, Ludwigshafen / Rhein | Verfahren zur Herstellung von 13-[2',6',6'-Trimethylcyclohexen-(l')-yl-(l')]-3,7,ll-trimethyltridecahexaen - (2,4,6,8,10,12) - säureil) bzw. deren Estern | |
| DE923252C (de) * | 1944-09-23 | 1955-02-07 | Schering Ag | Verfahren zur Herstellung einer Polyencarbonsaeure der Formel CHO |
| AT207831B (de) * | 1957-11-27 | 1960-02-25 | Hoffmann La Roche | Verfahren zur Herstellung von Polyencarbonsäureestern und deren Verseifungsprodukten |
| AT222103B (de) * | 1958-08-07 | 1962-07-10 | Bayer Ag | Verfahren zur Herstellung von 2-trans-β-Jonylidenessigsäure |
| CH529742A (de) * | 1970-02-02 | 1972-10-31 | Hoffmann La Roche | Verfahren zur Herstellung von Vitamin-A-Säureamiden |
| AT340903B (de) * | 1974-03-29 | 1978-01-10 | Hoffmann La Roche | Verfahren zur herstellung von neuen polyenverbindungen |
| DE2456959A1 (de) * | 1974-12-03 | 1976-06-16 | Basf Ag | 4-(e)- und 4-(z)-7-methyl-9-(2,6,6trimethyl-1-cyclohexen-1-yl)-nona-2,4,6,8tetraencarbonsaeure, ihre derivate und diese enthaltende zubereitungen |
| CH624373A5 (en) * | 1975-11-14 | 1981-07-31 | Hoffmann La Roche | Process for the preparation of polyene compounds |
| CA1111441A (fr) * | 1976-12-20 | 1981-10-27 | Werner Bollag | Composes a base de polyenes |
| LU77254A1 (fr) * | 1977-05-04 | 1979-01-18 | ||
| US4169103A (en) * | 1978-04-12 | 1979-09-25 | Hoffmann-La Roche Inc. | Nonatetraenoic acid derivatives |
| DE2843884A1 (de) * | 1978-10-07 | 1980-04-24 | Basf Ag | Mittel, enthaltend 2-(retinyliden)- malonsaeurederivate |
-
1982
- 1982-06-24 CH CH3889/82A patent/CH651007A5/de not_active IP Right Cessation
-
1983
- 1983-06-14 CA CA000430391A patent/CA1276032C/fr not_active Expired - Lifetime
- 1983-06-15 NL NL8302136A patent/NL8302136A/nl not_active Application Discontinuation
- 1983-06-15 DE DE3321662A patent/DE3321662A1/de active Granted
- 1983-06-17 ZA ZA834473A patent/ZA834473B/xx unknown
- 1983-06-17 NZ NZ204628A patent/NZ204628A/xx unknown
- 1983-06-20 SE SE8303539A patent/SE454984B/sv not_active IP Right Cessation
- 1983-06-20 IL IL69028A patent/IL69028A0/xx not_active IP Right Cessation
- 1983-06-21 IT IT8321721A patent/IT1212753B/it active
- 1983-06-21 DK DK287083A patent/DK159392C/da not_active IP Right Cessation
- 1983-06-22 FR FR8310319A patent/FR2529201B1/fr not_active Expired
- 1983-06-22 LU LU84870A patent/LU84870A1/de unknown
- 1983-06-23 JP JP58111979A patent/JPS5910547A/ja active Granted
- 1983-06-23 GB GB08317129A patent/GB2122200B/en not_active Expired
- 1983-06-23 BE BE0/211055A patent/BE897118A/fr not_active IP Right Cessation
- 1983-06-23 IE IE1471/83A patent/IE55285B1/en not_active IP Right Cessation
- 1983-06-23 AT AT2305/83A patent/AT392780B/de active
- 1983-06-23 PH PH29108A patent/PH20070A/en unknown
- 1983-06-24 AU AU16201/83A patent/AU560027B2/en not_active Ceased
-
1985
- 1985-04-26 GB GB08510717A patent/GB2156351B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| SE8303539L (sv) | 1983-12-25 |
| NZ204628A (en) | 1985-07-31 |
| GB2122200A (en) | 1984-01-11 |
| CA1276032C (fr) | 1990-11-06 |
| DE3321662C2 (fr) | 1992-11-26 |
| DE3321662A1 (de) | 1983-12-29 |
| GB2122200B (en) | 1986-05-08 |
| DK159392C (da) | 1991-03-04 |
| GB8317129D0 (en) | 1983-07-27 |
| AU560027B2 (en) | 1987-03-26 |
| GB2156351A (en) | 1985-10-09 |
| FR2529201A1 (fr) | 1983-12-30 |
| GB8510717D0 (en) | 1985-06-05 |
| GB2156351B (en) | 1986-05-14 |
| SE8303539D0 (sv) | 1983-06-20 |
| JPH0441134B2 (fr) | 1992-07-07 |
| NL8302136A (nl) | 1984-01-16 |
| AU1620183A (en) | 1984-01-05 |
| ATA230583A (de) | 1990-11-15 |
| IE831471L (en) | 1983-12-24 |
| LU84870A1 (de) | 1985-03-29 |
| IE55285B1 (en) | 1990-08-01 |
| ZA834473B (en) | 1984-03-28 |
| BE897118A (fr) | 1983-12-23 |
| IL69028A0 (en) | 1983-10-31 |
| FR2529201B1 (fr) | 1988-08-19 |
| DK159392B (da) | 1990-10-08 |
| IT1212753B (it) | 1989-11-30 |
| DK287083D0 (da) | 1983-06-21 |
| IT8321721A0 (it) | 1983-06-21 |
| PH20070A (en) | 1986-09-18 |
| AT392780B (de) | 1991-06-10 |
| SE454984B (sv) | 1988-06-13 |
| JPS5910547A (ja) | 1984-01-20 |
| DK287083A (da) | 1983-12-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUE | Assignment |
Owner name: F. HOFFMANN-LA ROCHE AG |
|
| PL | Patent ceased |