DK175205B1 - Fremgangsmåde til fremstilling af 1-adamantan-derivater - Google Patents
Fremgangsmåde til fremstilling af 1-adamantan-derivater Download PDFInfo
- Publication number
- DK175205B1 DK175205B1 DK198904413A DK441389A DK175205B1 DK 175205 B1 DK175205 B1 DK 175205B1 DK 198904413 A DK198904413 A DK 198904413A DK 441389 A DK441389 A DK 441389A DK 175205 B1 DK175205 B1 DK 175205B1
- Authority
- DK
- Denmark
- Prior art keywords
- process according
- methoxy
- methyl ester
- solvent
- acid methyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title claims description 19
- 229940052761 dopaminergic adamantane derivative Drugs 0.000 title claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 24
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- 239000002904 solvent Substances 0.000 claims abstract description 15
- 150000001491 aromatic compounds Chemical class 0.000 claims abstract description 7
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 46
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 24
- ZYLRDAOEBRPIGT-UHFFFAOYSA-N 1-adamantyl acetate Chemical compound C1C(C2)CC3CC2CC1(OC(=O)C)C3 ZYLRDAOEBRPIGT-UHFFFAOYSA-N 0.000 claims description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- -1 4-bromoanisole 4-bromophenol Chemical compound 0.000 claims description 7
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 4
- JCXVWUFYQSPUJQ-UHFFFAOYSA-N 1-adamantyl formate Chemical group C1C(C2)CC3CC2CC1(OC=O)C3 JCXVWUFYQSPUJQ-UHFFFAOYSA-N 0.000 claims description 2
- NXWTWYULZRDBSA-UHFFFAOYSA-N 2-fluoro-4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1F NXWTWYULZRDBSA-UHFFFAOYSA-N 0.000 claims description 2
- DTVVBPILCSNPCH-UHFFFAOYSA-N COC=1C=C2C=CC(=CC2=CC1)Br.OC=1C=C2C=CC(=CC2=CC1)Br.COC1=CC=C(C=C1)C=1C=C2C=CC(=CC2=CC1)C(=O)OC.OC1=CC=C(C=C1)C=1C=C2C=CC(=CC2=CC1)C(=O)OC Chemical compound COC=1C=C2C=CC(=CC2=CC1)Br.OC=1C=C2C=CC(=CC2=CC1)Br.COC1=CC=C(C=C1)C=1C=C2C=CC(=CC2=CC1)C(=O)OC.OC1=CC=C(C=C1)C=1C=C2C=CC(=CC2=CC1)C(=O)OC DTVVBPILCSNPCH-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 claims description 2
- 239000004914 cyclooctane Substances 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 229930192474 thiophene Natural products 0.000 claims description 2
- MVLMNZBWGSNOIM-UHFFFAOYSA-N 1-adamantyl propanoate Chemical compound C1C(C2)CC3CC2CC1(OC(=O)CC)C3 MVLMNZBWGSNOIM-UHFFFAOYSA-N 0.000 claims 1
- YXRKNKUIVVBXLP-UHFFFAOYSA-N 4-methoxybenzoic acid methyl 4-methoxybenzoate Chemical compound COC1=CC=C(C(O)=O)C=C1.COC(=O)C1=CC=C(OC)C=C1 YXRKNKUIVVBXLP-UHFFFAOYSA-N 0.000 claims 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 238000003756 stirring Methods 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 239000012043 crude product Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000007787 solid Substances 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 229940075894 denatured ethanol Drugs 0.000 description 8
- 238000001035 drying Methods 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- ORILYTVJVMAKLC-UHFFFAOYSA-N Adamantane Natural products C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- VLLNJDMHDJRNFK-UHFFFAOYSA-N adamantan-1-ol Chemical compound C1C(C2)CC3CC2CC1(O)C3 VLLNJDMHDJRNFK-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- QJPJQTDYNZXKQF-UHFFFAOYSA-N 4-bromoanisole Chemical compound COC1=CC=C(Br)C=C1 QJPJQTDYNZXKQF-UHFFFAOYSA-N 0.000 description 2
- NIFAOMSJMGEFTQ-UHFFFAOYSA-N 4-methoxybenzenethiol Chemical compound COC1=CC=C(S)C=C1 NIFAOMSJMGEFTQ-UHFFFAOYSA-N 0.000 description 2
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- DDIZAANNODHTRB-UHFFFAOYSA-N methyl p-anisate Chemical compound COC(=O)C1=CC=C(OC)C=C1 DDIZAANNODHTRB-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- VQHPRVYDKRESCL-UHFFFAOYSA-N 1-bromoadamantane Chemical compound C1C(C2)CC3CC2CC1(Br)C3 VQHPRVYDKRESCL-UHFFFAOYSA-N 0.000 description 1
- OZNXTQSXSHODFR-UHFFFAOYSA-N 1-chloroadamantane Chemical compound C1C(C2)CC3CC2CC1(Cl)C3 OZNXTQSXSHODFR-UHFFFAOYSA-N 0.000 description 1
- 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 1
- AYFJBMBVXWNYLT-UHFFFAOYSA-N 2-bromo-6-methoxynaphthalene Chemical compound C1=C(Br)C=CC2=CC(OC)=CC=C21 AYFJBMBVXWNYLT-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 1
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 1
- KCSHBBPHLJOPRK-UHFFFAOYSA-N 5-(1-adamantyl)-6-bromonaphthalen-2-ol Chemical compound C12(CC3CC(CC(C1)C3)C2)C1=C(C=CC2=CC(=CC=C12)O)Br KCSHBBPHLJOPRK-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 241000132536 Cirsium Species 0.000 description 1
- DADIDNFWHSBAGZ-UHFFFAOYSA-N FC1=C(C(=O)O)C=CC(=C1)O.FC1=C(C(=O)OC)C=CC(=C1)OC.COC1=CC=C(C(=O)OC)C=C1.COC1=CC=C(C(=O)O)C=C1.BrC1=CC=C(C=C1)O.BrC1=CC=C(C=C1)OC Chemical compound FC1=C(C(=O)O)C=CC(=C1)O.FC1=C(C(=O)OC)C=CC(=C1)OC.COC1=CC=C(C(=O)OC)C=C1.COC1=CC=C(C(=O)O)C=C1.BrC1=CC=C(C=C1)O.BrC1=CC=C(C=C1)OC DADIDNFWHSBAGZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000022563 Rema Species 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- LUGWXJMLFWEDAK-UHFFFAOYSA-N methyl 3-(1-adamantyl)-4-methoxybenzoate Chemical compound COC(=O)C1=CC=C(OC)C(C23CC4CC(CC(C4)C2)C3)=C1 LUGWXJMLFWEDAK-UHFFFAOYSA-N 0.000 description 1
- YDMAEOFIFQUGFM-UHFFFAOYSA-N methyl 6-(4-hydroxyphenyl)naphthalene-2-carboxylate Chemical compound C1=CC2=CC(C(=O)OC)=CC=C2C=C1C1=CC=C(O)C=C1 YDMAEOFIFQUGFM-UHFFFAOYSA-N 0.000 description 1
- LLKKPBJYOHZIFI-UHFFFAOYSA-N methyl 6-(4-methoxyphenyl)naphthalene-2-carboxylate Chemical compound C1=CC2=CC(C(=O)OC)=CC=C2C=C1C1=CC=C(OC)C=C1 LLKKPBJYOHZIFI-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/06—Preparation of carboxylic acid amides from nitriles by transformation of cyano groups into carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/14—Preparation of carboxylic acid amides by formation of carboxamide groups together with reactions not involving the carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/16—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by condensation involving hydroxy groups of phenols or alcohols or the ether or mineral ester group derived therefrom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
- C07C2603/74—Adamantanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8811706 | 1988-09-07 | ||
| FR8811706A FR2636061B1 (fr) | 1988-09-07 | 1988-09-07 | Procede de preparation de derives de l'adamantane-1 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK441389D0 DK441389D0 (da) | 1989-09-06 |
| DK441389A DK441389A (da) | 1990-03-08 |
| DK175205B1 true DK175205B1 (da) | 2004-07-12 |
Family
ID=9369798
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK198904413A DK175205B1 (da) | 1988-09-07 | 1989-09-06 | Fremgangsmåde til fremstilling af 1-adamantan-derivater |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US5015758A (de) |
| EP (1) | EP0358574B1 (de) |
| JP (1) | JP2669906B2 (de) |
| AT (1) | ATE85790T1 (de) |
| AU (1) | AU615331B2 (de) |
| CA (1) | CA1312075C (de) |
| DE (1) | DE68904940T2 (de) |
| DK (1) | DK175205B1 (de) |
| ES (1) | ES2054063T3 (de) |
| FI (1) | FI93349C (de) |
| FR (1) | FR2636061B1 (de) |
| IE (1) | IE63829B1 (de) |
| NO (1) | NO170847C (de) |
| NZ (1) | NZ230575A (de) |
| PT (1) | PT91640B (de) |
| ZA (1) | ZA896814B (de) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5146025A (en) * | 1989-02-28 | 1992-09-08 | Mitsubishi Gas Chemical Company, Inc. | Naphthalene compounds |
| GB9306751D0 (en) * | 1993-03-31 | 1993-05-26 | Autotype Int Ltd | Gamma radiation detection |
| JP3114570B2 (ja) * | 1995-05-26 | 2000-12-04 | オムロン株式会社 | 静電容量型圧力センサ |
| US6462064B1 (en) * | 1996-07-08 | 2002-10-08 | Galderma Research & Development S.N.C. | Apoptosis inducing adamantyl derivatives and their usage as anti-cancer agents, especially for cervical cancers and dysplasias |
| WO2002057201A2 (en) * | 2001-01-19 | 2002-07-25 | Chevron U.S.A. Inc. | Polymerizable higher diamondoid derivatives |
| US7306674B2 (en) * | 2001-01-19 | 2007-12-11 | Chevron U.S.A. Inc. | Nucleation of diamond films using higher diamondoids |
| US6858700B2 (en) | 2001-01-19 | 2005-02-22 | Chervon U.S.A. Inc. | Polymerizable higher diamondoid derivatives |
| US7795468B2 (en) | 2001-01-19 | 2010-09-14 | Chevron U.S.A. Inc. | Functionalized higher diamondoids |
| US7273598B2 (en) * | 2001-01-19 | 2007-09-25 | Chevron U.S.A. Inc. | Diamondoid-containing materials for passivating layers in integrated circuit devices |
| US6783589B2 (en) * | 2001-01-19 | 2004-08-31 | Chevron U.S.A. Inc. | Diamondoid-containing materials in microelectronics |
| US7312562B2 (en) * | 2004-02-04 | 2007-12-25 | Chevron U.S.A. Inc. | Heterodiamondoid-containing field emission devices |
| US20080031909A1 (en) | 2004-12-10 | 2008-02-07 | Dsm Ip Assets B.V. | Encapsulated Cosmetic Materials |
| CN1696100B (zh) * | 2005-06-01 | 2010-11-24 | 黑龙江福和华星制药集团股份有限公司 | 痤疮治疗药阿达帕林的新型简捷合成方法 |
| US8119834B2 (en) * | 2005-06-17 | 2012-02-21 | Medichem, S.A. | Process for the preparation of adapalene and related compounds |
| RU2309933C1 (ru) * | 2006-07-11 | 2007-11-10 | Государственное образовательное учреждение высшего профессионального образования Волгоградский государственный технический университет (ВолгГТУ) | Способ получения адамантилсодержащих производных нафталина |
| CN100588643C (zh) * | 2006-11-02 | 2010-02-10 | 南京航空航天大学 | 一种含有二取代金刚烷基的维甲酸类化合物制备方法 |
| EP2065032A1 (de) | 2007-11-27 | 2009-06-03 | Galderma Research & Development | Verfahren zur Herstellung von Adapalen-Gelen |
| JP5396120B2 (ja) * | 2009-03-26 | 2014-01-22 | 出光興産株式会社 | アダマンタン誘導体 |
| RU2458905C1 (ru) * | 2011-06-17 | 2012-08-20 | Федеральное Государственное Бюджетное Учреждение Науки Институт Химии И Химической Технологии Сибирского Отделения Российской Академии Наук (Иххт Со Ран) | Способ получения адамантилсодержащих производных галоидфенолов |
| CA3002752A1 (en) | 2015-10-26 | 2017-05-04 | Oti Lumionics Inc. | Method for patterning a coating on a surface and device including a patterned coating |
| CN118215324B (zh) | 2016-12-02 | 2025-08-15 | Oti照明公司 | 包括设置在发射区域上面的导电涂层的器件及其方法 |
| CN116583131A (zh) | 2017-04-26 | 2023-08-11 | Oti照明公司 | 用于图案化表面上覆层的方法和包括图案化覆层的装置 |
| WO2018211460A1 (en) | 2017-05-17 | 2018-11-22 | Oti Lumionics Inc. | Method for selectively depositing a conductive coating over a patterning coating and device including a conductive coating |
| US11751415B2 (en) | 2018-02-02 | 2023-09-05 | Oti Lumionics Inc. | Materials for forming a nucleation-inhibiting coating and devices incorporating same |
| WO2019215591A1 (en) | 2018-05-07 | 2019-11-14 | Oti Lumionics Inc. | Method for providing an auxiliary electrode and device including an auxiliary electrode |
| JP2022508040A (ja) | 2018-11-23 | 2022-01-19 | オーティーアイ ルミオニクス インコーポレーテッド | 光透過領域を含むオプトエレクトロニクスデバイス |
| KR20250160226A (ko) | 2019-03-07 | 2025-11-11 | 오티아이 루미오닉스 인크. | 핵생성 억제 코팅물 형성용 재료 및 이를 포함하는 디바이스 |
| CN113950630A (zh) | 2019-04-18 | 2022-01-18 | Oti照明公司 | 用于形成成核抑制涂层的材料和结合所述成核抑制涂层的装置 |
| US12069938B2 (en) | 2019-05-08 | 2024-08-20 | Oti Lumionics Inc. | Materials for forming a nucleation-inhibiting coating and devices incorporating same |
| KR20240134240A (ko) | 2019-06-26 | 2024-09-06 | 오티아이 루미오닉스 인크. | 광 회절 특성을 갖는 광 투과 영역을 포함하는 광전자 디바이스 |
| CN114342068A (zh) | 2019-08-09 | 2022-04-12 | Oti照明公司 | 包含辅助电极和分区的光电子装置 |
| KR102931641B1 (ko) | 2019-12-24 | 2026-02-26 | 오티아이 루미오닉스 인크. | 캡핑 층을 포함하는 발광 장치 및 그 제조방법 |
| US11985841B2 (en) | 2020-12-07 | 2024-05-14 | Oti Lumionics Inc. | Patterning a conductive deposited layer using a nucleation inhibiting coating and an underlying metallic coating |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS494460B1 (de) * | 1970-12-23 | 1974-02-01 | ||
| US4087410A (en) * | 1976-06-14 | 1978-05-02 | Eli Lilly And Company | 5-(Tertiary alkyl) resorcinol preparation and intermediates therefor |
| LU85849A1 (fr) * | 1985-04-11 | 1986-11-05 | Cird | Derives benzonaphtaleniques,leur procede de preparation et leur application dans les domaines pharmaceutiques et cosmetiques |
-
1988
- 1988-09-07 FR FR8811706A patent/FR2636061B1/fr not_active Expired - Lifetime
-
1989
- 1989-09-06 PT PT91640A patent/PT91640B/pt not_active IP Right Cessation
- 1989-09-06 AU AU41065/89A patent/AU615331B2/en not_active Expired
- 1989-09-06 FI FI894217A patent/FI93349C/fi active IP Right Grant
- 1989-09-06 IE IE285889A patent/IE63829B1/en not_active IP Right Cessation
- 1989-09-06 NO NO893585A patent/NO170847C/no not_active IP Right Cessation
- 1989-09-06 ZA ZA896814A patent/ZA896814B/xx unknown
- 1989-09-06 US US07/403,280 patent/US5015758A/en not_active Expired - Lifetime
- 1989-09-06 CA CA000610413A patent/CA1312075C/fr not_active Expired - Lifetime
- 1989-09-06 NZ NZ230575A patent/NZ230575A/en unknown
- 1989-09-06 JP JP1232678A patent/JP2669906B2/ja not_active Expired - Lifetime
- 1989-09-06 DK DK198904413A patent/DK175205B1/da not_active IP Right Cessation
- 1989-09-07 ES ES89402446T patent/ES2054063T3/es not_active Expired - Lifetime
- 1989-09-07 DE DE8989402446T patent/DE68904940T2/de not_active Expired - Lifetime
- 1989-09-07 EP EP89402446A patent/EP0358574B1/de not_active Expired - Lifetime
- 1989-09-07 AT AT89402446T patent/ATE85790T1/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0358574A1 (de) | 1990-03-14 |
| CA1312075C (fr) | 1992-12-29 |
| AU615331B2 (en) | 1991-09-26 |
| PT91640B (pt) | 1995-05-31 |
| FI93349B (fi) | 1994-12-15 |
| NO893585D0 (no) | 1989-09-06 |
| ATE85790T1 (de) | 1993-03-15 |
| NO170847B (no) | 1992-09-07 |
| FI93349C (fi) | 1995-03-27 |
| FI894217A0 (fi) | 1989-09-06 |
| AU4106589A (en) | 1990-03-15 |
| FI894217L (fi) | 1990-03-08 |
| NZ230575A (en) | 1991-03-26 |
| IE892858L (en) | 1990-03-07 |
| US5015758A (en) | 1991-05-14 |
| NO893585L (no) | 1990-03-08 |
| JPH02124835A (ja) | 1990-05-14 |
| PT91640A (pt) | 1990-03-30 |
| IE63829B1 (en) | 1995-06-14 |
| FR2636061A1 (fr) | 1990-03-09 |
| DK441389A (da) | 1990-03-08 |
| ES2054063T3 (es) | 1994-08-01 |
| ZA896814B (en) | 1990-06-27 |
| JP2669906B2 (ja) | 1997-10-29 |
| DE68904940D1 (de) | 1993-03-25 |
| DE68904940T2 (de) | 1993-08-26 |
| DK441389D0 (da) | 1989-09-06 |
| EP0358574B1 (de) | 1993-02-17 |
| NO170847C (no) | 1992-12-16 |
| FR2636061B1 (fr) | 1990-11-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DK175205B1 (da) | Fremgangsmåde til fremstilling af 1-adamantan-derivater | |
| DK159680B (da) | Cycliske imider til anvendelse ved fremstilling af cycliske aminosyrer | |
| SU508199A3 (ru) | Способ получени производных морфолина | |
| JPH0217170A (ja) | 酸の製造方法 | |
| US3200151A (en) | Arylaminoalkyl guanidines | |
| US3953490A (en) | Preparation of (3-trifluoromethylphenoxy)(4-chlorophenyl)acetonitrile | |
| FI73677B (fi) | Foerfarande foer framstaellning av nya, terapeutiskt anvaendbara 3-metylflavon-8-karboxylsyraestrar. | |
| JPH01305078A (ja) | 新規なヘテロアロチノイド誘導体 | |
| DK141531B (da) | Analogifremgangsmåde til fremstilling af 1-metyl-9,10-dihydro-d-lysergsyreallylamid eller syreadditionssalte deraf. | |
| US4104305A (en) | 1-Aminotricyclo (4.3.1.12,5) undecane and salts thereof | |
| Srivastava et al. | Dihydroisocoumarins. IV. Reaction with N-Bromosuccinimide. A New Route to Some Isocoumarin Syntheses | |
| US3803202A (en) | Process for the production of 2-cyano-3,4,5,6-tetrahalogenbenzoic acid alkyl esters | |
| TW593291B (en) | Process for making N-alkyl bis(thiazolyl) sulfenimides | |
| CN112645863A (zh) | 二吡咯甲烯-1-酮类化合物及其制备方法 | |
| US2778829A (en) | New 5:6-dihydro-benzo (c) cinnoline derivatives and a process for their preparation | |
| US619549A (en) | Werke | |
| US3542849A (en) | Process for the preparation of n-aryl-alpha-amino carboxylic acid esters | |
| US3742043A (en) | 2-(alpha,alpha-bis(trifluoromethyl)benzyloxy) acetic acid and esters thereof | |
| FI69628C (fi) | Nytt foerfarande foer framstaellning av apovinkaminsyraestrar | |
| US4153729A (en) | Therapeutically useful cysteinol and homocysteinol derivatives | |
| SU374304A1 (ru) | СПОСОБ ПОЛУЧЕНИЯ СОВКАИНА — ГИДРОХЛОРИДА уЗ-ДИЭТИЛАМИНОЭТИЛАМИДА 2-БУТОКСИЦИНХОНИНОВОЙ | |
| KR850000427B1 (ko) | 피롤 유도체의 제조방법 | |
| US2216155A (en) | Aryl amino compounds | |
| SU475763A3 (ru) | Способ получени -замещенных феноксиуксусных кислот и их производных | |
| McBay et al. | The Comparative Reactivites of p-Isopropylbenzoic Acid and Acetic Acid Toward the Methyl Free Radical |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUP | Patent expired |