CH619211A5 - Process for the preparation of 11-cis-13-desmethyl vitamin A acid and all-trans-13-desmethyl vitamin A acid and their derivatives - Google Patents

Process for the preparation of 11-cis-13-desmethyl vitamin A acid and all-trans-13-desmethyl vitamin A acid and their derivatives Download PDF

Info

Publication number: CH619211A5
Authority: CH; Switzerland
Prior art keywords: acid; vitamin; desmethyl; cis; formula
Prior art date: 1974-12-03

Application number

CH1559775A

Other languages

German (de)

English (en)

Inventor

Herbert Dr Scholz

Horst Dr Koenig

Joachim Dr Paust

Walter-Wielant Dr Wiersdorff

Wolfgang Dr Blechschmidt

Rolf Dr Kretzschmar

Enno Dr Christophers

Original Assignee

Basf Ag

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.)

1974-12-03

Filing date

1975-12-01

Publication date

1980-09-15

1975-12-01 Application filed by Basf Ag filed Critical Basf Ag

1980-09-15 Publication of CH619211A5 publication Critical patent/CH619211A5/de

Links

238000002360 preparation method Methods 0.000 title claims description 18
238000000034 method Methods 0.000 title claims description 17
229930002330 retinoic acid Natural products 0.000 title description 19
SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 title description 16
150000001875 compounds Chemical class 0.000 claims description 27
-1 carboxy-substituted phenoxy group Chemical group 0.000 claims description 20
239000000203 mixture Substances 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 8
150000002148 esters Chemical class 0.000 claims description 6
239000002585 base Substances 0.000 claims description 5
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 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
238000000926 separation method Methods 0.000 claims description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
229910001413 alkali metal ion Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims description 2
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 2
229940067157 phenylhydrazine Drugs 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
125000004423 acyloxy group Chemical group 0.000 claims 1
125000003545 alkoxy group Chemical group 0.000 claims 1
125000003277 amino group Chemical group 0.000 claims 1
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 1
125000000623 heterocyclic group Chemical group 0.000 claims 1
150000007522 mineralic acids Chemical group 0.000 claims 1
125000004433 nitrogen atom Chemical group N* 0.000 claims 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
150000007524 organic acids Chemical class 0.000 claims 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 62
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
239000000243 solution Substances 0.000 description 17
239000002253 acid Substances 0.000 description 14
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
239000003208 petroleum Substances 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
238000004458 analytical method Methods 0.000 description 9
239000013078 crystal Substances 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
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
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000012043 crude product Substances 0.000 description 6
238000001953 recrystallisation Methods 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
239000000499 gel Substances 0.000 description 5
238000001228 spectrum Methods 0.000 description 5
239000000126 substance Substances 0.000 description 5
230000009885 systemic effect Effects 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
238000004440 column chromatography Methods 0.000 description 4
230000007547 defect Effects 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
239000007858 starting material Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
230000006820 DNA synthesis Effects 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
235000021466 carotenoid Nutrition 0.000 description 3
150000001747 carotenoids Chemical class 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
230000012010 growth Effects 0.000 description 3
238000002329 infrared spectrum Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000003921 oil Substances 0.000 description 3
235000011118 potassium hydroxide Nutrition 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
DOLQYFPDPKPQSS-UHFFFAOYSA-N 3,4-dimethylaniline Chemical compound CC1=CC=C(N)C=C1C DOLQYFPDPKPQSS-UHFFFAOYSA-N 0.000 description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
101150041968 CDC13 gene Proteins 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-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
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-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
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products 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
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
206010052428 Wound Diseases 0.000 description 2
208000027418 Wounds and injury Diseases 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 2
239000002775 capsule Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000004359 castor oil Substances 0.000 description 2
235000019438 castor oil Nutrition 0.000 description 2
210000004027 cell Anatomy 0.000 description 2
238000004113 cell culture Methods 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
238000013375 chromatographic separation Methods 0.000 description 2
239000006071 cream Substances 0.000 description 2
239000010779 crude oil Substances 0.000 description 2
208000035475 disorder Diseases 0.000 description 2
238000001035 drying Methods 0.000 description 2
210000001339 epidermal cell Anatomy 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
JGEMYUOFGVHXKV-OWOJBTEDSA-N fumaraldehyde Chemical compound O=C\C=C\C=O JGEMYUOFGVHXKV-OWOJBTEDSA-N 0.000 description 2
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
CLUPOLFGIGLMIQ-UHFFFAOYSA-N heptane;propan-2-ol Chemical compound CC(C)O.CCCCCCC CLUPOLFGIGLMIQ-UHFFFAOYSA-N 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
238000010348 incorporation Methods 0.000 description 2
239000008101 lactose Substances 0.000 description 2
125000000896 monocarboxylic acid group Chemical group 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
229940068918 polyethylene glycol 400 Drugs 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
230000008929 regeneration Effects 0.000 description 2
238000011069 regeneration method Methods 0.000 description 2
229960004889 salicylic acid Drugs 0.000 description 2
239000011734 sodium Substances 0.000 description 2
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
239000002904 solvent Substances 0.000 description 2
230000004936 stimulating effect Effects 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
230000029663 wound healing Effects 0.000 description 2
CPEONABTMRSIKA-UHFFFAOYSA-N 1,4$l^{2}-oxazinane Chemical compound C1COCC[N]1 CPEONABTMRSIKA-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
208000002874 Acne Vulgaris Diseases 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
DWRXFEITVBNRMK-UHFFFAOYSA-N Beta-D-1-Arabinofuranosylthymine Natural products O=C1NC(=O)C(C)=CN1C1C(O)C(O)C(CO)O1 DWRXFEITVBNRMK-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
125000006414 CCl Chemical group ClC* 0.000 description 1
241000700199 Cavia porcellus Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
208000001840 Dandruff Diseases 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
239000005662 Paraffin oil Substances 0.000 description 1
241000101040 Pityriasis Species 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
201000004681 Psoriasis Diseases 0.000 description 1
241001303601 Rosacea Species 0.000 description 1
229920002125 Sokalan® Polymers 0.000 description 1
102000004142 Trypsin Human genes 0.000 description 1
108090000631 Trypsin Proteins 0.000 description 1
238000007239 Wittig reaction Methods 0.000 description 1
206010000496 acne Diseases 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
229960005274 benzocaine Drugs 0.000 description 1
IQFYYKKMVGJFEH-UHFFFAOYSA-N beta-L-thymidine Natural products O=C1NC(=O)C(C)=CN1C1OC(CO)C(O)C1 IQFYYKKMVGJFEH-UHFFFAOYSA-N 0.000 description 1
QHMBSVQNZZTUGM-ZWKOTPCHSA-N cannabidiol Chemical compound OC1=CC(CCCCC)=CC(O)=C1[C@H]1[C@H](C(C)=C)CCC(C)=C1 QHMBSVQNZZTUGM-ZWKOTPCHSA-N 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
235000014633 carbohydrates Nutrition 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
230000010261 cell growth Effects 0.000 description 1
230000019522 cellular metabolic process Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000006003 cornification Effects 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
150000001983 dialkylethers Chemical class 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
210000005069 ears Anatomy 0.000 description 1
239000003480 eluent Substances 0.000 description 1
210000002919 epithelial cell Anatomy 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000284 extract Substances 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
230000003179 granulation Effects 0.000 description 1
238000005469 granulation Methods 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
230000035876 healing Effects 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
206010021198 ichthyosis Diseases 0.000 description 1
230000001771 impaired effect Effects 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
239000011261 inert gas Substances 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
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([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
238000005567 liquid scintillation counting Methods 0.000 description 1
MCVVUJPXSBQTRZ-ONEGZZNKSA-N methyl (e)-but-2-enoate Chemical group COC(=O)\C=C\C MCVVUJPXSBQTRZ-ONEGZZNKSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
239000004584 polyacrylic acid Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Chemical group 0.000 description 1
229910001414 potassium ion Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[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 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
229960005205 prednisolone Drugs 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
239000003380 propellant Substances 0.000 description 1
238000004080 punching Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
229960000342 retinol acetate Drugs 0.000 description 1
239000011770 retinyl acetate Substances 0.000 description 1
201000004700 rosacea Diseases 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
229960001860 salicylate Drugs 0.000 description 1
150000003902 salicylic acid esters Chemical class 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910001415 sodium ion Inorganic materials 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
229940104230 thymidine Drugs 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
239000012588 trypsin Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/006—Antidandruff preparations
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/67—Vitamins
- A61K8/671—Vitamin A; Derivatives thereof, e.g. ester of vitamin A acid, ester of retinol, retinol, retinal
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/20—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by carboxyl groups or halides, anhydrides, or (thio)esters thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/24—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by six-membered non-aromatic rings, e.g. beta-carotene
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/09—Geometrical isomers
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Birds (AREA)
Epidemiology (AREA)
Dermatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH1559775A 1974-12-03 1975-12-01 Process for the preparation of 11-cis-13-desmethyl vitamin A acid and all-trans-13-desmethyl vitamin A acid and their derivatives CH619211A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19742456959 DE2456959A1 (de)	1974-12-03	1974-12-03	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

Publications (1)

Publication Number	Publication Date
CH619211A5 true CH619211A5 (en)	1980-09-15

Family

ID=5932289

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1559775A CH619211A5 (en)	1974-12-03	1975-12-01	Process for the preparation of 11-cis-13-desmethyl vitamin A acid and all-trans-13-desmethyl vitamin A acid and their derivatives

Country Status (7)

Country	Link
BE (1)	BE835902A (fr)
CH (1)	CH619211A5 (fr)
DE (1)	DE2456959A1 (fr)
FR (1)	FR2293193A1 (fr)
GB (1)	GB1526410A (fr)
SE (1)	SE413139B (fr)
ZA (1)	ZA757545B (fr)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2843811A1 (de) *	1978-10-07	1980-04-24	Basf Ag	Retinsaeure- und 7,8-dehydro-retinsaeure-n-(carboxy)-phenylamide
DE3177177D1 (de) *	1981-02-17	1990-06-13	Gail S Bazzano	Die verwendung von retinoiden und ihren derivaten zum erhoehen des wachstumsgrades von menschlichen haaren und zum erhoehen des wachstumsgrades des pelzes bei bestimmten pelztieren.
EP0093770B1 (fr) *	1981-11-09	1991-06-19	BAZZANO, Gail S	Utilisation de retinoides et minoxydile(2,4-diamino-6-piperidino-pyrimidine-3-oxyde)pour ameliorer le taux de croissance des cheveux et traiter certains types d'alopecies chez l'homme
CH651007A5 (de) *	1982-06-24	1985-08-30	Hoffmann La Roche	Polyenverbindungen.
US4539154A (en) *	1983-06-15	1985-09-03	Hoffmann-La Roche Inc.	Polyene compounds
US4743400A (en) *	1986-09-22	1988-05-10	Mcneilab, Inc.	Process for preparing retinoyl chlorides
US5780676A (en) *	1992-04-22	1998-07-14	Ligand Pharmaceuticals Incorporated	Compounds having selective activity for Retinoid X Receptors, and means for modulation of processes mediated by Retinoid X Receptors
US5962731A (en) *	1992-04-22	1999-10-05	Ligand Pharmaceuticals Incorporated	Compounds having selective activity for retinoid X receptors, and means for modulation of processes mediated by retinoid X receptors
US7655699B1 (en)	1992-04-22	2010-02-02	Eisai Inc.	Compounds having selective activity for retinoid X receptors, and means for modulation of processes mediated by retinoid X receptors
DE69324043T2 (de) *	1993-01-11	1999-07-01	Ligand Pharmaceuticals, Inc., San Diego, Calif.	Verbindungen mit selektiver wirkung fuer retinoid x rezeptoren, und mittel fuer steuerung fuer durch retinoid x rezeptoren bedingte prozesse
CA2178964A1 (fr) *	1993-12-15	1995-06-22	John A. Duffy	Nouveaux composes conjugues de retinoides et procedes de traitement du vieillissement de la peau
US20040242704A1 (en)	2003-03-14	2004-12-02	University Of Washington, Techtransfer - Invention Licensing	Stabilized mutant opsin proteins
US7566808B2 (en)	2004-02-17	2009-07-28	President And Fellows Of Harvard College	Management of ophthalmologic disorders, including macular degeneration
NZ552080A (en) *	2004-06-18	2011-03-31	Univ Washington	9-cis-retinyl esters and uses thereof
MX337656B (es)	2008-02-11	2016-03-14	Univ Washington	Metodos para el tratamiento y prevencion de disfuncion retinal relacionada con la edad.
MX2012003220A (es)	2009-09-15	2012-08-03	Quadra Logic Tech Inc	Formulaciones farmaceuticas que comprenden 9-cis-retinil esteres en un vehiculo de lipido.
KR101851249B1 (ko)	2010-04-19	2018-06-20	노벨리언 테라퓨틱스 인코포레이티드	내인성 레티노이드 결핍과 연관된 시각 장애의 치료 또는 완화를 위한 치료용 조성물, 제형 및 키트
KR102133608B1 (ko)	2012-03-01	2020-07-13	레티나제닉스, 엘엘씨	내인성 레티노이드 결핍증과 관련된 시각 장애에서 시각 기능의 개선을 위한 치료 요법 및 방법

1974
- 1974-12-03 DE DE19742456959 patent/DE2456959A1/de not_active Withdrawn
1975
- 1975-11-20 SE SE7513080A patent/SE413139B/sv unknown
- 1975-11-25 BE BE162142A patent/BE835902A/fr not_active IP Right Cessation
- 1975-12-01 CH CH1559775A patent/CH619211A5/de not_active IP Right Cessation
- 1975-12-02 GB GB49370/75A patent/GB1526410A/en not_active Expired
- 1975-12-02 ZA ZA00757545A patent/ZA757545B/xx unknown
- 1975-12-02 FR FR7536850A patent/FR2293193A1/fr active Granted

Also Published As

Publication number	Publication date
FR2293193A1 (fr)	1976-07-02
BE835902A (fr)	1976-05-25
ZA757545B (en)	1976-12-29
SE7513080L (sv)	1976-06-04
FR2293193B1 (fr)	1979-09-21
DE2456959A1 (de)	1976-06-16
GB1526410A (en)	1978-09-27
SE413139B (sv)	1980-04-21

Legal Events

Date	Code	Title	Description
1985-08-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE69633679T2 (de)	2006-02-09	Substituierte aryl-oder heteroarylamide mit retinoid-ähnlicher biologischer aktivität
DE3219244C2 (de)	1986-06-05	Sulfonatderivate, Verfahren zu ihrer Herstellung und diese Derivate enthaltende Arzneimittel
DE2402398C3 (de)	1981-07-23	Aromatische Carbonsäureamid-Derivate, Verfahren zu ihrer Herstellung und pharmazeutische Zusammensetzungen
DE2456959A1 (de)	1976-06-16	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
DD143902A5 (de)	1980-09-17	Verfahren zur herstellung von aminderivaten von glyzerin und propandiolen
DE1493955B2 (de)	1976-11-18	Sulfonanilide und verfahren zu ihrer herstellung
DD223439A5 (de)	1985-06-12	Verfahren zur herstellung von alkanolderivaten
EP0051819A2 (fr)	1982-05-19	Dérivés tétra substitués de benzène, leur préparation et préparations pharmaceutiques les contenant
DE2504045A1 (de)	1975-08-07	16,17 dihydro-apovincaminsaeureester, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
EP0009777B1 (fr)	1982-05-05	N-(carboxy)phényl amides de l'acide rétinoique et 7,8-déhydro-rétinoique, procédé de préparation et compositions pharmaceutiques les contenant
EP0033095B1 (fr)	1983-10-19	Dérivés 5-aminotétrazoliques des acides rétinoiques, leur préparation et compositions pharmaceutiques les contenant
CH507905A (de)	1971-05-31	Verfahren zur Herstellung der cis- bzw. trans-Isomere von Äthylenderivaten
DD211548A1 (de)	1984-07-18	Verfahren zur herstellung neuartiger alkan- und alkenderivate
EP0009776B1 (fr)	1982-07-28	N-monohydroxypropylamides, N-dihydroxypropylamides et leurs acetonoides de l'acide all-E et 13-Z rétinoique, procédé pour leur préparation et compositions pharmaceutiques les contenant
CH619213A5 (en)	1980-09-15	Process for the preparation of carbazole derivatives
DD139842A5 (de)	1980-01-23	Verfahren zur herstellung quaternaerer ammoniumsalze von phenylpropylaminen und phenylbutylaminen
DE10324496A1 (de)	2004-12-16	Targetorientierte Chemotherapie von Tumoren der Sexualorgane
DE2431292A1 (de)	1976-01-15	Neue carbazol-derivate
DE69303333T2 (de)	1996-11-21	Substituierte Benzoate-Derivate
EP0643045A1 (fr)	1995-03-15	Dérivés de quinoléine comme antagonistes de leukotriènes
DE2421541A1 (de)	1974-11-21	Cyclisierte benzylidensaeuren
DD144764A5 (de)	1980-11-05	Verfahren zur herstellung von r-n-(2-phenyl-2-hydroxyethyl)-3-phenylpropylaminen
DE2646213A1 (de)	1977-05-12	Aroylphenylnaphthaline und verfahren zu ihrer herstellung
EP0028609B1 (fr)	1983-07-27	Utilisation de dérivés de chloronitrophényle comme herbicides sélectifs et nouveaux dérivés de chloronitrophényle
AT251565B (de)	1967-01-10	Verfahren zur Herstellung von neuen Carbonsäuren