CH675241A5 - - Google Patents
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- Publication number
- CH675241A5 CH675241A5 CH965/88A CH9658885A CH675241A5 CH 675241 A5 CH675241 A5 CH 675241A5 CH 965/88 A CH965/88 A CH 965/88A CH 9658885 A CH9658885 A CH 9658885A CH 675241 A5 CH675241 A5 CH 675241A5
- Authority
- CH
- Switzerland
- Prior art keywords
- radical
- mmol
- acid
- mixture
- methyl
- Prior art date
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- -1 alkyl radical Chemical class 0.000 claims description 81
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 76
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 30
- 150000003254 radicals Chemical class 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 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 15
- 238000000034 method Methods 0.000 claims description 15
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 5
- 239000000543 intermediate Substances 0.000 claims description 5
- 239000011777 magnesium Substances 0.000 claims description 5
- 229910052749 magnesium Inorganic materials 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- OVNRBNWMEZZXCZ-UHFFFAOYSA-N 1-(4-bromo-1-phenoxydecan-2-yl)adamantane Chemical compound C1C(C2)CC(C3)CC2CC13C(CC(Br)CCCCCC)COC1=CC=CC=C1 OVNRBNWMEZZXCZ-UHFFFAOYSA-N 0.000 claims description 3
- RVBGDVQDQKGZLH-UHFFFAOYSA-N 3-(1-adamantyl)-4-decoxybenzoic acid Chemical compound CCCCCCCCCCOC1=CC=C(C(O)=O)C=C1C1(C2)CC(C3)CC2CC3C1 RVBGDVQDQKGZLH-UHFFFAOYSA-N 0.000 claims description 3
- WXQUGIVHDANZTM-UHFFFAOYSA-N 3-tert-butyl-4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1C(C)(C)C WXQUGIVHDANZTM-UHFFFAOYSA-N 0.000 claims description 3
- COSZXTIQFMTDDH-UHFFFAOYSA-N 4-bromo-2-(2-methylundecan-2-yl)phenol Chemical compound CCCCCCCCCC(C)(C)C1=CC(Br)=CC=C1O COSZXTIQFMTDDH-UHFFFAOYSA-N 0.000 claims description 3
- YNUZPPIZFMKDLF-UHFFFAOYSA-N 4-methoxy-3-(2-methylundecan-2-yl)benzoic acid Chemical compound CCCCCCCCCC(C)(C)C1=CC(C(O)=O)=CC=C1OC YNUZPPIZFMKDLF-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- RWZRMETXJWTWQW-UHFFFAOYSA-N 3-(1-adamantyl)-4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1C1(C2)CC(C3)CC2CC3C1 RWZRMETXJWTWQW-UHFFFAOYSA-N 0.000 claims description 2
- LDJPRTLVJUWUJI-UHFFFAOYSA-N 4-bromo-1-methoxy-2-(2-methylundecan-2-yl)benzene Chemical compound CCCCCCCCCC(C)(C)C1=CC(Br)=CC=C1OC LDJPRTLVJUWUJI-UHFFFAOYSA-N 0.000 claims description 2
- MJRUSXKALHWNDH-UHFFFAOYSA-N 4-bromo-2-tert-butyl-1-methoxybenzene Chemical compound COC1=CC=C(Br)C=C1C(C)(C)C MJRUSXKALHWNDH-UHFFFAOYSA-N 0.000 claims description 2
- 150000001491 aromatic compounds Chemical class 0.000 claims description 2
- QQAMHHZQONQBFZ-UHFFFAOYSA-N 1-(5-bromo-2-methoxyphenyl)adamantane Chemical compound COC1=CC=C(Br)C=C1C1(C2)CC(C3)CC2CC3C1 QQAMHHZQONQBFZ-UHFFFAOYSA-N 0.000 claims 1
- UXBIXOXDACBTDG-UHFFFAOYSA-N 1-adamantyl radical Chemical compound C1C(C2)CC3C[C]1CC2C3 UXBIXOXDACBTDG-UHFFFAOYSA-N 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 201
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 140
- 239000000203 mixture Substances 0.000 description 140
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 111
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 72
- 239000003480 eluent Substances 0.000 description 63
- 150000002148 esters Chemical class 0.000 description 58
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 49
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 48
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 44
- 238000010992 reflux Methods 0.000 description 37
- 239000000377 silicon dioxide Substances 0.000 description 35
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 34
- 229910052799 carbon Inorganic materials 0.000 description 31
- 239000000047 product Substances 0.000 description 31
- 239000007787 solid Substances 0.000 description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 28
- 239000002904 solvent Substances 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 239000012074 organic phase Substances 0.000 description 23
- 239000000243 solution Substances 0.000 description 23
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 22
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 22
- 235000019341 magnesium sulphate Nutrition 0.000 description 22
- 150000004702 methyl esters Chemical class 0.000 description 22
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 238000004587 chromatography analysis Methods 0.000 description 15
- WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 14
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 14
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 13
- QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 12
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
- 239000008096 xylene Substances 0.000 description 9
- 239000004342 Benzoyl peroxide Substances 0.000 description 8
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 8
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
- 235000019400 benzoyl peroxide Nutrition 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 7
- 229940095102 methyl benzoate Drugs 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- 229910002092 carbon dioxide Inorganic materials 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 239000012047 saturated solution Substances 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- IOPLHGOSNCJOOO-UHFFFAOYSA-N methyl 3,4-diaminobenzoate Chemical compound COC(=O)C1=CC=C(N)C(N)=C1 IOPLHGOSNCJOOO-UHFFFAOYSA-N 0.000 description 5
- PGBFYLVIMDQYMS-UHFFFAOYSA-N Methyl thiophene-2-carboxylate Chemical compound COC(=O)C1=CC=CS1 PGBFYLVIMDQYMS-UHFFFAOYSA-N 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- GCSINTLJUNXLLU-UHFFFAOYSA-N methyl 3-hydroxy-4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C(O)=C1 GCSINTLJUNXLLU-UHFFFAOYSA-N 0.000 description 4
- OCZXDVNSNDITBS-UHFFFAOYSA-N methyl 4-amino-3-hydroxybenzoate Chemical compound COC(=O)C1=CC=C(N)C(O)=C1 OCZXDVNSNDITBS-UHFFFAOYSA-N 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 4
- 239000003643 water by type Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- YZWIJXIOKYNUBM-UHFFFAOYSA-N 1-methyl-2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)indole-6-carboxylic acid Chemical compound CC1(C)CCC(C)(C)C=2C1=CC(C=1N(C3=CC(=CC=C3C=1)C(O)=O)C)=CC=2 YZWIJXIOKYNUBM-UHFFFAOYSA-N 0.000 description 3
- OHWRYNVSRSLBFA-UHFFFAOYSA-N 2-(3-tert-butyl-4-methoxyphenyl)-1-benzofuran-6-carboxylic acid Chemical compound C1=C(C(C)(C)C)C(OC)=CC=C1C1=CC2=CC=C(C(O)=O)C=C2O1 OHWRYNVSRSLBFA-UHFFFAOYSA-N 0.000 description 3
- JHDMFXOMEAFDBN-UHFFFAOYSA-N 2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)-1,3-benzothiazole-6-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2SC(C=3C=C4C(C)(C)CCC(C4=CC=3)(C)C)=NC2=C1 JHDMFXOMEAFDBN-UHFFFAOYSA-N 0.000 description 3
- OLIRNPXPADPSPK-UHFFFAOYSA-N 2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)-1,3-benzoxazole-6-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2OC(C=3C=C4C(C)(C)CCC(C4=CC=3)(C)C)=NC2=C1 OLIRNPXPADPSPK-UHFFFAOYSA-N 0.000 description 3
- WNLMYNASWOULQY-UHFFFAOYSA-N 4-tert-butylbenzoyl chloride Chemical compound CC(C)(C)C1=CC=C(C(Cl)=O)C=C1 WNLMYNASWOULQY-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- CSENBIZAYBKPSB-UHFFFAOYSA-N methyl 4-methyl-3-sulfanylbenzoate Chemical compound COC(=O)C1=CC=C(C)C(S)=C1 CSENBIZAYBKPSB-UHFFFAOYSA-N 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- NYJXKHIVLGWPCF-UHFFFAOYSA-N 2-(1-adamantyl)-4-bromophenol Chemical compound OC1=CC=C(Br)C=C1C1(C2)CC(C3)CC2CC3C1 NYJXKHIVLGWPCF-UHFFFAOYSA-N 0.000 description 2
- YBCWQMCCLMMXNR-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-1-benzofuran-6-carboxylic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=CC2=CC=C(C(O)=O)C=C2O1 YBCWQMCCLMMXNR-UHFFFAOYSA-N 0.000 description 2
- SFHRYYFFKYGVBF-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-1-benzothiophene-6-carboxylic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=CC2=CC=C(C(O)=O)C=C2S1 SFHRYYFFKYGVBF-UHFFFAOYSA-N 0.000 description 2
- QEAHMFWPWFPKDV-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-1h-indole-6-carboxylic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=CC2=CC=C(C(O)=O)C=C2N1 QEAHMFWPWFPKDV-UHFFFAOYSA-N 0.000 description 2
- RJNORCOINJYWSD-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-3h-benzimidazole-5-carboxylic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NC2=CC=C(C(O)=O)C=C2N1 RJNORCOINJYWSD-UHFFFAOYSA-N 0.000 description 2
- VSZSQTFNGIIPGV-UHFFFAOYSA-N 2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)-3h-benzimidazole-5-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2NC(C=3C=C4C(C)(C)CCC(C4=CC=3)(C)C)=NC2=C1 VSZSQTFNGIIPGV-UHFFFAOYSA-N 0.000 description 2
- MGYZCPIJOGDOMH-UHFFFAOYSA-N 2-[3-(1-adamantyl)-4-methoxyphenyl]-1,3-benzoxazole-6-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2OC(C3=CC=C(C(=C3)C34CC5CC(CC(C5)C3)C4)OC)=NC2=C1 MGYZCPIJOGDOMH-UHFFFAOYSA-N 0.000 description 2
- UWRDZBFFOZGWAA-UHFFFAOYSA-N 2-[3-(1-adamantyl)-4-methoxyphenyl]-1-benzothiophene-6-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2SC(C3=CC=C(C(=C3)C34CC5CC(CC(C5)C3)C4)OC)=CC2=C1 UWRDZBFFOZGWAA-UHFFFAOYSA-N 0.000 description 2
- ZKIXVGOVWANWDU-UHFFFAOYSA-N 2-[4-methoxy-3-(2-methylundecan-2-yl)phenyl]-1-benzofuran-6-carboxylic acid Chemical compound C1=C(OC)C(C(C)(C)CCCCCCCCC)=CC(C=2OC3=CC(=CC=C3C=2)C(O)=O)=C1 ZKIXVGOVWANWDU-UHFFFAOYSA-N 0.000 description 2
- IIVWHGMLFGNMOW-UHFFFAOYSA-N 2-methylpropane Chemical compound C[C](C)C IIVWHGMLFGNMOW-UHFFFAOYSA-N 0.000 description 2
- PQBDMOAXTIEGDG-UHFFFAOYSA-N 3-(1-adamantyl)-4-[tert-butyl(dimethyl)silyl]oxybenzoic acid Chemical compound CC(C)(C)[Si](C)(C)OC1=CC=C(C(O)=O)C=C1C1(C2)CC(C3)CC2CC3C1 PQBDMOAXTIEGDG-UHFFFAOYSA-N 0.000 description 2
- MDRKJOPPZMFBCL-UHFFFAOYSA-N 3-(1-adamantyl)-4-methoxybenzoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1C1(C2)CC(C3)CC2CC3C1 MDRKJOPPZMFBCL-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
- FDCOHGHEADZEGF-OCEACIFDSA-N Glycerol 1,3-dihexadecanoate 2-(9Z-octadecenoate) Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCC\C=C\CCCCCCCC FDCOHGHEADZEGF-OCEACIFDSA-N 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- HDJLSECJEQSPKW-UHFFFAOYSA-N Methyl 2-Furancarboxylate Chemical compound COC(=O)C1=CC=CO1 HDJLSECJEQSPKW-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 125000000950 dibromo group Chemical group Br* 0.000 description 2
- MNNMTFSPSVOWSF-UHFFFAOYSA-N dicyclohexylazanium;chloride Chemical compound Cl.C1CCCCC1NC1CCCCC1 MNNMTFSPSVOWSF-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- NTBKCCAXKXJQIO-UHFFFAOYSA-N methyl 2-(4-tert-butylphenyl)-1-benzofuran-6-carboxylate Chemical compound O1C2=CC(C(=O)OC)=CC=C2C=C1C1=CC=C(C(C)(C)C)C=C1 NTBKCCAXKXJQIO-UHFFFAOYSA-N 0.000 description 2
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- 125000004429 atom Chemical group 0.000 description 1
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- 208000010668 atopic eczema Diseases 0.000 description 1
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
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- 239000000706 filtrate Substances 0.000 description 1
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- 238000003818 flash chromatography Methods 0.000 description 1
- ZQLCWPXBHUALQC-UHFFFAOYSA-N hydroxytoluic acid Natural products CC1=CC=C(C(O)=O)C=C1O ZQLCWPXBHUALQC-UHFFFAOYSA-N 0.000 description 1
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- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 229960005280 isotretinoin Drugs 0.000 description 1
- 208000029443 keratinization disease Diseases 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
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- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- LFIIYWXBDUBYFN-UHFFFAOYSA-N methyl 1-methyl-2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)indole-6-carboxylate Chemical compound CC1(C)CCC(C)(C)C=2C1=CC(C1=CC3=CC=C(C=C3N1C)C(=O)OC)=CC=2 LFIIYWXBDUBYFN-UHFFFAOYSA-N 0.000 description 1
- RXCFVYMIQCLNEX-UHFFFAOYSA-N methyl 2-(3-tert-butyl-4-methoxyphenyl)-1-benzofuran-6-carboxylate Chemical compound COC(=O)C=1C=CC2=C(OC(=C2)C2=CC(=C(C=C2)OC)C(C)(C)C)C=1 RXCFVYMIQCLNEX-UHFFFAOYSA-N 0.000 description 1
- TURKCUIZOJVXHF-UHFFFAOYSA-N methyl 2-(4,4-dimethyl-2,3-dihydrochromen-6-yl)-3h-benzimidazole-5-carboxylate Chemical compound O1CCC(C)(C)C2=CC(C3=NC4=CC=C(C=C4N3)C(=O)OC)=CC=C21 TURKCUIZOJVXHF-UHFFFAOYSA-N 0.000 description 1
- MCGIWJYNVJCZOZ-UHFFFAOYSA-N methyl 2-(4-tert-butylphenyl)-1-benzothiophene-6-carboxylate Chemical compound S1C2=CC(C(=O)OC)=CC=C2C=C1C1=CC=C(C(C)(C)C)C=C1 MCGIWJYNVJCZOZ-UHFFFAOYSA-N 0.000 description 1
- OZLLISZNPDFCPZ-UHFFFAOYSA-N methyl 2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)-1,3-benzothiazole-6-carboxylate Chemical compound CC1(C)CCC(C)(C)C=2C1=CC(C1=NC3=CC=C(C=C3S1)C(=O)OC)=CC=2 OZLLISZNPDFCPZ-UHFFFAOYSA-N 0.000 description 1
- YCKMKFUPELBBFN-UHFFFAOYSA-N methyl 2-[3-(1-adamantyl)-4-decoxyphenyl]-1,3-benzoxazole-6-carboxylate Chemical compound COC(=O)C1=CC2=C(N=C(O2)C2=CC(=C(C=C2)OCCCCCCCCCC)C23CC4CC(CC(C2)C4)C3)C=C1 YCKMKFUPELBBFN-UHFFFAOYSA-N 0.000 description 1
- POBDNKBXIYSCJW-UHFFFAOYSA-N methyl 2-[3-(1-adamantyl)-4-methoxyphenyl]-1,3-benzoxazole-6-carboxylate Chemical compound COC(=O)C1=CC2=C(N=C(O2)C2=CC(=C(C=C2)OC)C23CC4CC(CC(C2)C4)C3)C=C1 POBDNKBXIYSCJW-UHFFFAOYSA-N 0.000 description 1
- ZWPMFXHFRMSBMB-UHFFFAOYSA-N methyl 2-[3-(1-adamantyl)-4-methoxyphenyl]-1-benzofuran-6-carboxylate Chemical compound C1C(C2)CC(C3)CC2CC13C1=CC(C2=CC3=CC=C(C=C3O2)C(=O)OC)=CC=C1OC ZWPMFXHFRMSBMB-UHFFFAOYSA-N 0.000 description 1
- NTAKOWKFDHWBAB-UHFFFAOYSA-N methyl 2-[3-(1-adamantyl)-4-methoxyphenyl]-1-benzothiophene-6-carboxylate Chemical compound C1C(C2)CC(C3)CC2CC13C1=CC(C2=CC3=CC=C(C=C3S2)C(=O)OC)=CC=C1OC NTAKOWKFDHWBAB-UHFFFAOYSA-N 0.000 description 1
- ZDIBYVMYXUDPGP-UHFFFAOYSA-N methyl 3-(3-tert-butyl-4-methoxybenzoyl)oxy-4-methylbenzoate Chemical compound COC(C1=CC(=C(C=C1)C)OC(C1=CC(=C(C=C1)OC)C(C)(C)C)=O)=O ZDIBYVMYXUDPGP-UHFFFAOYSA-N 0.000 description 1
- XFUCJXXJYCZOQU-UHFFFAOYSA-N methyl 3-[3-(1-adamantyl)-4-methoxybenzoyl]oxy-4-aminobenzoate Chemical compound COC(C1=CC(=C(C=C1)N)OC(C1=CC(=C(C=C1)OC)C12CC3CC(CC(C1)C3)C2)=O)=O XFUCJXXJYCZOQU-UHFFFAOYSA-N 0.000 description 1
- USIMHUYIQQLUEE-UHFFFAOYSA-N methyl 3-[4-methoxy-3-(2-methylundecan-2-yl)benzoyl]oxy-4-methylbenzoate Chemical compound COC(C1=CC(=C(C=C1)C)OC(C1=CC(=C(C=C1)OC)C(CCCCCCCCC)(C)C)=O)=O USIMHUYIQQLUEE-UHFFFAOYSA-N 0.000 description 1
- RBJLLOQAKPYUQZ-UHFFFAOYSA-N methyl 3-[[3-(1-adamantyl)-4-methoxybenzoyl]amino]-4-aminobenzoate Chemical compound COC(C1=CC(=C(C=C1)N)NC(C1=CC(=C(C=C1)OC)C12CC3CC(CC(C1)C3)C2)=O)=O RBJLLOQAKPYUQZ-UHFFFAOYSA-N 0.000 description 1
- FWSJCIAXGYJVAR-UHFFFAOYSA-N methyl 4-(bromomethyl)-3-(3-tert-butyl-4-methoxybenzoyl)oxybenzoate Chemical compound COC(C1=CC(=C(C=C1)CBr)OC(C1=CC(=C(C=C1)OC)C(C)(C)C)=O)=O FWSJCIAXGYJVAR-UHFFFAOYSA-N 0.000 description 1
- JEMOAWGFCLAAAG-UHFFFAOYSA-N methyl 4-[3-(1-adamantyl)-4-methoxybenzoyl]sulfanyl-4-(bromomethyl)cyclohexa-1,5-diene-1-carboxylate Chemical compound COC(C1=CCC(C=C1)(CBr)SC(C1=CC(=C(C=C1)OC)C12CC3CC(CC(C1)C3)C2)=O)=O JEMOAWGFCLAAAG-UHFFFAOYSA-N 0.000 description 1
- GFKDINNLIYHHGD-UHFFFAOYSA-N methyl 4-[3-(1-adamantyl)-4-methoxybenzoyl]sulfanyl-4-methylcyclohexa-1,5-diene-1-carboxylate Chemical compound COC(C1=CCC(C=C1)(C)SC(C1=CC(=C(C=C1)OC)C12CC3CC(CC(C1)C3)C2)=O)=O GFKDINNLIYHHGD-UHFFFAOYSA-N 0.000 description 1
- ZLSRHAGLDDUOEG-UHFFFAOYSA-N methyl 4-[[3-(1-adamantyl)-4-decoxybenzoyl]amino]-3-hydroxybenzoate Chemical compound COC(C1=CC(=C(C=C1)NC(C1=CC(=C(C=C1)OCCCCCCCCCC)C12CC3CC(CC(C1)C3)C2)=O)O)=O ZLSRHAGLDDUOEG-UHFFFAOYSA-N 0.000 description 1
- GATYLMISKZUKAT-UHFFFAOYSA-N methyl 4-amino-3-[(4,4-dimethyl-2,3-dihydrochromene-6-carbonyl)amino]benzoate Chemical compound COC(C1=CC(=C(C=C1)N)NC(=O)C=1C=CC2=C(C(CCO2)(C)C)C=1)=O GATYLMISKZUKAT-UHFFFAOYSA-N 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 1
- LPNBBFKOUUSUDB-UHFFFAOYSA-M p-toluate Chemical compound CC1=CC=C(C([O-])=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-M 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- KYKNRZGSIGMXFH-ZVGUSBNCSA-M potassium bitartrate Chemical compound [K+].OC(=O)[C@H](O)[C@@H](O)C([O-])=O KYKNRZGSIGMXFH-ZVGUSBNCSA-M 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000001472 potassium tartrate Substances 0.000 description 1
- 229940111695 potassium tartrate Drugs 0.000 description 1
- 235000011005 potassium tartrates Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000012256 powdered iron Substances 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 239000001433 sodium tartrate Substances 0.000 description 1
- 229960002167 sodium tartrate Drugs 0.000 description 1
- 235000011004 sodium tartrates Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 229960001727 tretinoin Drugs 0.000 description 1
- 238000007514 turning Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D263/57—Aryl or substituted aryl radicals
-
- 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
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/14—Decongestants or antiallergics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
- C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Ophthalmology & Optometry (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Cosmetics (AREA)
- Indole Compounds (AREA)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
LU85544A LU85544A1 (fr) | 1984-09-19 | 1984-09-19 | Derives heterocycliques aromatiques,leur procede de preparation et leur application dans les domaines therapeutique et cosmetique |
Publications (1)
Publication Number | Publication Date |
---|---|
CH675241A5 true CH675241A5 (en, 2012) | 1990-09-14 |
Family
ID=19730321
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH4050/85A CH665841A5 (fr) | 1984-09-19 | 1985-09-18 | Derives heterocycliques aromatiques et compositions therapeutiques et cosmetiques les contenant. |
CH965/88A CH675241A5 (en, 2012) | 1984-09-19 | 1985-09-18 |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH4050/85A CH665841A5 (fr) | 1984-09-19 | 1985-09-18 | Derives heterocycliques aromatiques et compositions therapeutiques et cosmetiques les contenant. |
Country Status (21)
Country | Link |
---|---|
US (3) | US4740519A (en, 2012) |
JP (1) | JPH0784437B2 (en, 2012) |
AR (1) | AR243504A1 (en, 2012) |
AT (2) | AT395714B (en, 2012) |
AU (2) | AU578310B2 (en, 2012) |
BE (2) | BE903254A (en, 2012) |
CA (2) | CA1256804A (en, 2012) |
CH (2) | CH665841A5 (en, 2012) |
DE (2) | DE3546907C2 (en, 2012) |
DK (1) | DK169475B1 (en, 2012) |
ES (1) | ES8608487A1 (en, 2012) |
FR (1) | FR2570377B1 (en, 2012) |
GB (3) | GB2164648B (en, 2012) |
GR (1) | GR852270B (en, 2012) |
IT (1) | IT1209663B (en, 2012) |
LU (1) | LU85544A1 (en, 2012) |
MX (1) | MX166783B (en, 2012) |
NL (1) | NL192878C (en, 2012) |
PT (1) | PT81132B (en, 2012) |
SE (2) | SE461466B (en, 2012) |
ZA (1) | ZA857158B (en, 2012) |
Families Citing this family (174)
Publication number | Priority date | Publication date | Assignee | Title |
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US4448006A (en) | 1981-05-28 | 1984-05-15 | Donn Incorporated | Grid ceiling structure and method of converting |
LU86258A1 (fr) * | 1986-01-21 | 1987-09-03 | Rech Dermatologiques C I R D S | Composes benzamido aromatique,leur procede de preparation et leur utilisation en medecine humaine ou veterinaire et en cosmetique |
FR2603280B1 (fr) * | 1986-08-29 | 1988-10-28 | Cird | Nouveau compose marque au tritium, sa preparation et son application notamment dans la determination de l'affinite des retinoides pour leur recepteur cellulaire |
NZ223237A (en) * | 1987-01-22 | 1991-03-26 | Shiseido Co Ltd | Hair growth promoting agent and compositions |
US5149705A (en) * | 1987-03-13 | 1992-09-22 | Allergan, Inc. | Acetylenes disubstituted with a heteroaromatic group and a tetralin group and having retinoid like activity |
US5602130A (en) * | 1987-03-20 | 1997-02-11 | Allergan | Disubstituted acetylenes bearing heteroaromatic and heterobicyclic groups having retinoid like activity |
US5264578A (en) * | 1987-03-20 | 1993-11-23 | Allergan, Inc. | Disubstituted acetylenes bearing heterobicyclic groups and heteroaromatic or phenyl groups having retinoid like activity |
US5234926A (en) * | 1987-03-20 | 1993-08-10 | Allergan, Inc. | Disubstituted acetylenes bearing heteroaromatic and heterobicyclic groups having retinoid like activity |
FR2614618B1 (fr) * | 1987-04-30 | 1989-07-07 | Cird | Derives heterocycliques polycycliques, leur procede de preparation et leur utilisation en medecine humaine et veterinaire |
LU87038A1 (fr) * | 1987-11-04 | 1989-06-14 | Oreal | Esters aromatiques d'antibiotiques macrolidiques et lincosamidiques,leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant |
KR0139216B1 (ko) * | 1988-04-11 | 1998-05-01 | 제임스 엠. 캐내지 | 레티노이드 유사활성을 갖는 페놀 또는 벤조산의 테트랄린 에스테르 |
US5366986A (en) * | 1988-04-15 | 1994-11-22 | T Cell Sciences, Inc. | Compounds which inhibit complement and/or suppress immune activity |
US5173499A (en) * | 1988-04-15 | 1992-12-22 | T Cell Sciences, Inc. | Compounds which inhibit complement and/or suppress immune activity |
US5506247A (en) * | 1988-04-15 | 1996-04-09 | T Cell Sciences, Inc. | Compounds that inhibit complement and/or suppress immune activity |
DE3830054A1 (de) * | 1988-09-03 | 1990-03-15 | Boehringer Mannheim Gmbh | Phenylamide - verfahren zu ihrer herstellung sowie diese verbindungen enthaltende arzneimittel |
US5166170A (en) * | 1989-07-03 | 1992-11-24 | Hoechst-Roussel Pharmaceuticals Incorporated | 2-(aminoaryl) indoles and indolines as topical antiinflammatory agents for the treatment of skin disorders |
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US5272156A (en) * | 1989-09-19 | 1993-12-21 | Allergan, Inc. | Acetylenes disubstituted with a heteroaromatic group and a 2-substituted 1,2,3,4-tetrahydroquinolinyl group having retinoid-like activity |
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US5162546A (en) * | 1989-09-19 | 1992-11-10 | Allergan, Inc. | Acetylenes disubstituted with a phenyl group and a 2-substituted chromanyl, thiochromanyl or 1,2,3,4-tetrahydroquinolinyl group having retinoid-like activity |
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CA2105379A1 (en) * | 1991-03-26 | 1992-09-27 | Roshantha A. S. Chandraratna | Chromans and thiochromans with heteroarylethynyl substituents at the 7-position having retinoid-like biological activity |
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FR2677020B1 (fr) * | 1991-05-31 | 1993-08-27 | Cird Galderma | Composes derives de benzimidazole, leur procede de preparation et leur utilisation dans les domaines therapeutique et cosmetique. |
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US5399586A (en) * | 1993-03-11 | 1995-03-21 | Allergan, Inc. | Treatment of mammals afflicted with tumors with compounds having RXR retinoid receptor agonist activity |
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CA2117413C (en) * | 1993-07-30 | 2006-11-21 | Neil Geach | Herbicidal isoxazole-4-yl-methanone derivatives |
GB9317949D0 (en) * | 1993-08-28 | 1993-10-13 | Stevens Malcolm F G | Benzothiazole compounds |
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DE59509233D1 (de) * | 1994-02-24 | 2001-06-13 | Haarmann & Reimer Gmbh | Kosmetische und dermatologische zubereitungen, enthaltend phenylen-1,4-bisbenzimidiazolesulfonsäuren |
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- 1985-09-18 AU AU47559/85A patent/AU578310B2/en not_active Expired
- 1985-09-18 AR AR85301653A patent/AR243504A1/es active
- 1985-09-18 CA CA000491026A patent/CA1256804A/fr not_active Expired
- 1985-09-18 NL NL8502557A patent/NL192878C/nl not_active IP Right Cessation
- 1985-09-18 IT IT8522180A patent/IT1209663B/it active
- 1985-09-18 CH CH965/88A patent/CH675241A5/fr not_active IP Right Cessation
- 1985-09-18 JP JP60207724A patent/JPH0784437B2/ja not_active Expired - Fee Related
- 1985-09-18 ES ES547750A patent/ES8608487A1/es not_active Expired
- 1985-09-18 AT AT0271885A patent/AT395714B/de not_active IP Right Cessation
- 1985-09-18 ZA ZA857158A patent/ZA857158B/xx unknown
- 1985-09-18 CA CA000491024A patent/CA1256862A/fr not_active Expired
- 1985-09-19 GB GB8523203A patent/GB2164648B/en not_active Expired
- 1985-10-01 MX MX009009A patent/MX166783B/es unknown
-
1986
- 1986-03-13 US US06/839,269 patent/US4740519A/en not_active Expired - Lifetime
- 1986-03-14 BE BE0/216415A patent/BE904421A/fr not_active IP Right Cessation
- 1986-09-22 AU AU62995/86A patent/AU593838B2/en not_active Expired
-
1987
- 1987-09-30 GB GB878722903A patent/GB8722903D0/en active Pending
- 1987-11-27 GB GB8727803A patent/GB2197320B/en not_active Expired
-
1988
- 1988-03-16 SE SE8800949A patent/SE502470C2/sv not_active IP Right Cessation
- 1988-03-24 US US07/172,494 patent/US4920140A/en not_active Expired - Lifetime
-
1989
- 1989-11-02 US US07/430,286 patent/US5059621A/en not_active Expired - Lifetime
-
1992
- 1992-03-05 AT AT0042192A patent/AT401514B/de not_active IP Right Cessation
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