LV13736B - Method for manufacturing 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphtoic acid - Google Patents

Method for manufacturing 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphtoic acid Download PDF

Info

Publication number: LV13736B
Authority: LV; Latvia
Prior art keywords: group; adamantyl; reaction; compound; aryl
Prior art date: 2006-12-28

Application number

LVP-06-149A

Other languages

English (en)

Latvian (lv)

Inventor

Vjaceslavs Tribulovics

Ivars Kalvins

Aleksandrs Cernobrovijs

Vladimirs Labeiss

Original Assignee

Vjaceslavs Tribulovics

Ivars Kalvins

Aleksandrs Cernobrovijs

Vladimirs Labeiss

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.)

2006-12-28

Filing date

2006-12-28

Publication date

2008-09-20

2006-12-28 Application filed by Vjaceslavs Tribulovics, Ivars Kalvins, Aleksandrs Cernobrovijs, Vladimirs Labeiss filed Critical Vjaceslavs Tribulovics

2006-12-28 Priority to LVP-06-149A priority Critical patent/LV13736B/lv

2007-12-28 Priority to UAA200907981A priority patent/UA97509C2/ru

2007-12-28 Priority to AT07870214T priority patent/ATE551316T1/de

2007-12-28 Priority to EP07870214A priority patent/EP2139839B1/de

2007-12-28 Priority to US12/448,672 priority patent/US8119835B2/en

2007-12-28 Priority to PCT/EP2007/064643 priority patent/WO2008086942A2/en

2007-12-28 Priority to EA200900897A priority patent/EA200900897A1/ru

2008-09-20 Publication of LV13736B publication Critical patent/LV13736B/lv

Links

238000000034 method Methods 0.000 title claims description 32
238000004519 manufacturing process Methods 0.000 title abstract description 4
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims abstract description 18
229910000073 phosphorus hydride Inorganic materials 0.000 claims abstract description 9
239000007795 chemical reaction product Substances 0.000 claims abstract description 8
238000006243 chemical reaction Methods 0.000 claims description 35
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 26
VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 claims description 19
239000003054 catalyst Substances 0.000 claims description 16
125000000217 alkyl group Chemical group 0.000 claims description 13
239000003446 ligand Substances 0.000 claims description 12
238000002360 preparation method Methods 0.000 claims description 12
239000011541 reaction mixture Substances 0.000 claims description 11
RYXZOQOZERSHHQ-UHFFFAOYSA-N [2-(2-diphenylphosphanylphenoxy)phenyl]-diphenylphosphane Chemical compound C=1C=CC=C(P(C=2C=CC=CC=2)C=2C=CC=CC=2)C=1OC1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RYXZOQOZERSHHQ-UHFFFAOYSA-N 0.000 claims description 9
150000001875 compounds Chemical class 0.000 claims description 9
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 7
239000000203 mixture Substances 0.000 claims description 7
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 4
229910052744 lithium Inorganic materials 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
CYPYTURSJDMMMP-UHFFFAOYSA-N 1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1.C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1.C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1 CYPYTURSJDMMMP-UHFFFAOYSA-N 0.000 claims description 3
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 3
229910052763 palladium Inorganic materials 0.000 claims description 3
239000000047 product Substances 0.000 claims description 3
WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims 7
229910052739 hydrogen Inorganic materials 0.000 claims 6
239000003795 chemical substances by application Substances 0.000 claims 4
229910052700 potassium Inorganic materials 0.000 claims 4
229910052708 sodium Inorganic materials 0.000 claims 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
239000011734 sodium Substances 0.000 claims 3
239000012442 inert solvent Substances 0.000 claims 2
150000007529 inorganic bases Chemical class 0.000 claims 2
BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 claims 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims 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 claims 1
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
229910019142 PO4 Inorganic materials 0.000 claims 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims 1
150000001242 acetic acid derivatives Chemical class 0.000 claims 1
235000021317 phosphate Nutrition 0.000 claims 1
150000003013 phosphoric acid derivatives Chemical class 0.000 claims 1
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Substances [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims 1
235000011056 potassium acetate Nutrition 0.000 claims 1
235000011181 potassium carbonates Nutrition 0.000 claims 1
239000001632 sodium acetate Substances 0.000 claims 1
235000017281 sodium acetate Nutrition 0.000 claims 1
235000011182 sodium carbonates Nutrition 0.000 claims 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
239000008096 xylene Substances 0.000 claims 1
LZCDAPDGXCYOEH-UHFFFAOYSA-N adapalene Chemical compound C1=C(C(O)=O)C=CC2=CC(C3=CC=C(C(=C3)C34CC5CC(CC(C5)C3)C4)OC)=CC=C21 LZCDAPDGXCYOEH-UHFFFAOYSA-N 0.000 abstract description 16
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 abstract description 14
238000003786 synthesis reaction Methods 0.000 abstract description 13
230000015572 biosynthetic process Effects 0.000 abstract description 12
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract description 7
150000002170 ethers Chemical class 0.000 abstract description 2
230000007062 hydrolysis Effects 0.000 abstract description 2
238000006460 hydrolysis reaction Methods 0.000 abstract description 2
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical class OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 abstract 2
238000006161 Suzuki-Miyaura coupling reaction Methods 0.000 abstract 1
239000004327 boric acid Substances 0.000 abstract 1
238000005580 one pot reaction Methods 0.000 abstract 1
238000000926 separation method Methods 0.000 abstract 1
-1 1-ADAMANTYL Chemical class 0.000 description 34
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 20
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 18
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
FPZOBRFHRPQGAA-UHFFFAOYSA-N [3-(1-adamantyl)-4-methoxyphenyl]boronic acid Chemical compound COC1=CC=C(B(O)O)C=C1C1(C2)CC(C3)CC2CC3C1 FPZOBRFHRPQGAA-UHFFFAOYSA-N 0.000 description 10
229910052786 argon Inorganic materials 0.000 description 10
239000012467 final product Substances 0.000 description 10
238000003756 stirring Methods 0.000 description 9
239000002244 precipitate Substances 0.000 description 7
KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 5
LZPWAYBEOJRFAX-UHFFFAOYSA-N 4,4,5,5-tetramethyl-1,3,2$l^{2}-dioxaborolane Chemical compound CC1(C)O[B]OC1(C)C LZPWAYBEOJRFAX-UHFFFAOYSA-N 0.000 description 5
229960002916 adapalene Drugs 0.000 description 5
238000010992 reflux Methods 0.000 description 5
101150003085 Pdcl gene Proteins 0.000 description 4
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
239000007789 gas Substances 0.000 description 4
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 4
238000003466 welding Methods 0.000 description 4
208000002874 Acne Vulgaris Diseases 0.000 description 3
206010000496 acne Diseases 0.000 description 3
230000003197 catalytic effect Effects 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
239000013078 crystal Substances 0.000 description 3
238000011065 in-situ storage Methods 0.000 description 3
238000002955 isolation Methods 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 2
KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 2
239000010410 layer Substances 0.000 description 2
PGXNMQBGOVUZNC-UHFFFAOYSA-N methyl 6-[3-(1-adamantyl)-4-methoxyphenyl]naphthalene-2-carboxylate Chemical compound C1C(C2)CC(C3)CC2CC13C1=CC(C2=CC3=CC=C(C=C3C=C2)C(=O)OC)=CC=C1OC PGXNMQBGOVUZNC-UHFFFAOYSA-N 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N methyl phenyl ether Natural products COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
150000003003 phosphines Chemical class 0.000 description 2
239000002904 solvent Substances 0.000 description 2
150000003751 zinc Chemical class 0.000 description 2
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
MZZSSQYTKSTPQO-UHFFFAOYSA-N 2-[3-(1-adamantyl)-4-methoxyphenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound C1=C(C23CC4CC(CC(C4)C2)C3)C(OC)=CC=C1B1OC(C)(C)C(C)(C)O1 MZZSSQYTKSTPQO-UHFFFAOYSA-N 0.000 description 1
BMIBJCFFZPYJHF-UHFFFAOYSA-N 2-methoxy-5-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Chemical compound COC1=NC=C(C)C=C1B1OC(C)(C)C(C)(C)O1 BMIBJCFFZPYJHF-UHFFFAOYSA-N 0.000 description 1
QJPJQTDYNZXKQF-UHFFFAOYSA-N 4-bromoanisole Chemical compound COC1=CC=C(Br)C=C1 QJPJQTDYNZXKQF-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
101100384273 Dictyostelium discoideum clua gene Proteins 0.000 description 1
239000007818 Grignard reagent Substances 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
238000010934 O-alkylation reaction Methods 0.000 description 1
239000002253 acid Substances 0.000 description 1
125000002015 acyclic group Chemical group 0.000 description 1
VLLNJDMHDJRNFK-UHFFFAOYSA-N adamantan-1-ol Chemical compound C1C(C2)CC3CC2CC1(O)C3 VLLNJDMHDJRNFK-UHFFFAOYSA-N 0.000 description 1
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
239000003513 alkali Substances 0.000 description 1
230000002152 alkylating effect Effects 0.000 description 1
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 description 1
230000001093 anti-cancer Effects 0.000 description 1
239000012300 argon atmosphere Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910000085 borane Inorganic materials 0.000 description 1
ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical class OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
239000012267 brine Substances 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
150000004795 grignard reagents Chemical class 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
238000009776 industrial production Methods 0.000 description 1
238000011068 loading method Methods 0.000 description 1
208000030159 metabolic disease Diseases 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
150000002901 organomagnesium compounds Chemical class 0.000 description 1
150000002902 organometallic compounds Chemical class 0.000 description 1
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
208000017520 skin disease Diseases 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
239000000725 suspension Substances 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
229960001727 tretinoin Drugs 0.000 description 1

Classifications

- 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
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
- 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

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

LVP-06-149A 2006-12-28 2006-12-28 Method for manufacturing 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphtoic acid LV13736B (en)

Priority Applications (7)

Application Number	Priority Date	Filing Date	Title
LVP-06-149A LV13736B (en)	2006-12-28	2006-12-28	Method for manufacturing 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphtoic acid
UAA200907981A UA97509C2 (ru)	2006-12-28	2007-12-28	Способ получения 6-[3-(1-адамантил)-4-метоксифенил]-2-нафтойной кислоты
AT07870214T ATE551316T1 (de)	2006-12-28	2007-12-28	Verfahren zur herstellung von 6-ä3-(1-adamantyl)- 4-methoxyphenylü-2-naphtoesäure
EP07870214A EP2139839B1 (de)	2006-12-28	2007-12-28	Verfahren zur herstellung von 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphtoesäure
US12/448,672 US8119835B2 (en)	2006-12-28	2007-12-28	Method for preparation of 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphtoic acid
PCT/EP2007/064643 WO2008086942A2 (en)	2006-12-28	2007-12-28	A method for preparation of 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphtoic acid
EA200900897A EA200900897A1 (ru)	2006-12-28	2007-12-28	Способ производства 6-[3-(1-адамантил)-4-метоксифенил]-2-нафтойной кислоты

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LVP-06-149A LV13736B (en)	2006-12-28	2006-12-28	Method for manufacturing 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphtoic acid

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LV13736B true LV13736B (en)	2008-09-20

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US (1)	US8119835B2 (de)
EP (1)	EP2139839B1 (de)
AT (1)	ATE551316T1 (de)
EA (1)	EA200900897A1 (de)
LV (1)	LV13736B (de)
UA (1)	UA97509C2 (de)
WO (1)	WO2008086942A2 (de)

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US20140163283A1 (en) *	2011-07-07	2014-06-12	Universite Catholique De Louvain	Method of carrying out cc-coupling reactions using oxide supported pd-catalysts
ES2909884T3 (es)	2013-08-20	2022-05-10	Univ Washington Through Its Center For Commercialization	Inhibidores nuevos y específicos de la hidroxilasa del ácido retinoico del citocromo P450 26
US11278025B2 (en)	2017-05-17	2022-03-22	The General Hospital Corporation	Antibiotic compounds
CN111333496B (zh) *	2020-05-02	2023-10-13	武汉诺安药业有限公司	一种阿达帕林的制备方法

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US6225481B1 (en)	1997-08-28	2001-05-01	Advanced Life Sciences, Inc.	Robustaflavone, intermediates and analogues and method for preparation thereof
JP2979139B2 (ja)	1998-03-11	1999-11-15	東北大学長	Ｌ−パラボロノフェニルアラニンの製造方法
AR037714A1 (es) *	2001-12-06	2004-12-01	Maxia Pharmaceuticals Inc	Derivados de tiazolidinona y oxazolidinona 2-sustituidos para la inhibicion de fosfatasas y el tratamiento de cancer
WO2005108338A1 (en)	2004-05-03	2005-11-17	Auspex Pharmaceuticals	Novel therapeutic agents for the treatment of cancer, metabolic diseases and skin disorders
ITMI20050550A1 (it) *	2005-04-01	2006-10-02	Dipharma Spa	Procedimento per la preparazione di adapalene

2006
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- 2007-12-28 UA UAA200907981A patent/UA97509C2/ru unknown
- 2007-12-28 AT AT07870214T patent/ATE551316T1/de active
- 2007-12-28 EP EP07870214A patent/EP2139839B1/de active Active
- 2007-12-28 WO PCT/EP2007/064643 patent/WO2008086942A2/en not_active Ceased
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Also Published As

Publication number	Publication date
ATE551316T1 (de)	2012-04-15
US20100076219A1 (en)	2010-03-25
WO2008086942A3 (en)	2008-11-06
EP2139839A2 (de)	2010-01-06
EA200900897A1 (ru)	2010-02-26
UA97509C2 (ru)	2012-02-27
EP2139839B1 (de)	2012-03-28
WO2008086942A2 (en)	2008-07-24
US8119835B2 (en)	2012-02-21

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