DD261786A5 - Verfahren zur herstellung von naphthalinderivaten - Google Patents

Verfahren zur herstellung von naphthalinderivaten Download PDF

Info

Publication number: DD261786A5
Authority: DD; German Democratic Republic
Prior art keywords: ring; lower alkoxy; formula; hydrogen atom; benzene ring
Prior art date: 1985-01-11

Application number

DD28610686A

Other languages

German (de)

English (en)

Inventor

Tameo Iwasaki

Kohki Takashima

Original Assignee

Tanabe Seiyaku Co. Ltd.,Jp

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.)

1985-01-11

Filing date

1986-01-10

Publication date

1988-11-09

1986-01-10 Application filed by Tanabe Seiyaku Co. Ltd.,Jp filed Critical Tanabe Seiyaku Co. Ltd.,Jp

1988-11-09 Publication of DD261786A5 publication Critical patent/DD261786A5/de

Links

238000002360 preparation method Methods 0.000 title claims abstract description 5
238000000034 method Methods 0.000 title claims description 13
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical class C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 title 1
150000003839 salts Chemical class 0.000 claims abstract description 24
150000002790 naphthalenes Chemical class 0.000 claims abstract description 15
125000003545 alkoxy group Chemical group 0.000 claims description 49
-1 aldehyde compound Chemical class 0.000 claims description 48
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 19
125000000217 alkyl group Chemical group 0.000 claims description 19
125000004432 carbon atom Chemical group C* 0.000 claims description 12
150000001555 benzenes Chemical group 0.000 claims description 9
DTCYXOLBEPGOHV-UHFFFAOYSA-N dimethyl 4-(3,4-dimethoxyphenyl)-1-hydroxy-5,6,7-trimethoxynaphthalene-2,3-dicarboxylate Chemical compound COC(=O)C=1C(C(=O)OC)=C(O)C2=CC(OC)=C(OC)C(OC)=C2C=1C1=CC=C(OC)C(OC)=C1 DTCYXOLBEPGOHV-UHFFFAOYSA-N 0.000 claims description 5
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 5
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 4
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
XLVKBGZAHXFDRM-UHFFFAOYSA-N diethyl 4-(3,4-dimethoxyphenyl)-1-hydroxy-5,6,7-trimethoxynaphthalene-2,3-dicarboxylate Chemical compound CCOC(=O)C=1C(C(=O)OCC)=C(O)C2=CC(OC)=C(OC)C(OC)=C2C=1C1=CC=C(OC)C(OC)=C1 XLVKBGZAHXFDRM-UHFFFAOYSA-N 0.000 claims description 2
206010003210 Arteriosclerosis Diseases 0.000 abstract description 5
208000011775 arteriosclerosis disease Diseases 0.000 abstract description 5
230000000055 hyoplipidemic effect Effects 0.000 abstract description 3
238000011321 prophylaxis Methods 0.000 abstract description 3
208000031226 Hyperlipidaemia Diseases 0.000 abstract description 2
238000011282 treatment Methods 0.000 abstract description 2
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 58
150000001875 compounds Chemical class 0.000 description 45
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
239000000203 mixture Substances 0.000 description 23
210000002966 serum Anatomy 0.000 description 22
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 16
239000000243 solution Substances 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
239000002904 solvent Substances 0.000 description 12
108010010234 HDL Lipoproteins Proteins 0.000 description 10
102000015779 HDL Lipoproteins Human genes 0.000 description 10
235000012000 cholesterol Nutrition 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
VHILMKFSCRWWIJ-UHFFFAOYSA-N dimethyl acetylenedicarboxylate Chemical compound COC(=O)C#CC(=O)OC VHILMKFSCRWWIJ-UHFFFAOYSA-N 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
241000700159 Rattus Species 0.000 description 8
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
239000013078 crystal Substances 0.000 description 8
WJUFSDZVCOTFON-UHFFFAOYSA-N veratraldehyde Chemical compound COC1=CC=C(C=O)C=C1OC WJUFSDZVCOTFON-UHFFFAOYSA-N 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
235000005911 diet Nutrition 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
108010023302 HDL Cholesterol Proteins 0.000 description 6
230000037213 diet Effects 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
KIRMKSWFOVIEPB-UHFFFAOYSA-N 2-bromo-1-(dimethoxymethyl)-3,4,5-trimethoxybenzene Chemical compound COC(OC)C1=CC(OC)=C(OC)C(OC)=C1Br KIRMKSWFOVIEPB-UHFFFAOYSA-N 0.000 description 5
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
230000000694 effects Effects 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
210000004185 liver Anatomy 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
239000008194 pharmaceutical composition Substances 0.000 description 5
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
125000005530 alkylenedioxy group Chemical group 0.000 description 4
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 4
WQUCNWOIPGCTCL-UHFFFAOYSA-N 5-bromo-6-(dimethoxymethyl)-1,3-benzodioxole Chemical compound C1=C(Br)C(C(OC)OC)=CC2=C1OCO2 WQUCNWOIPGCTCL-UHFFFAOYSA-N 0.000 description 3
201000001320 Atherosclerosis Diseases 0.000 description 3
108010007622 LDL Lipoproteins Proteins 0.000 description 3
102000007330 LDL Lipoproteins Human genes 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
108010062497 VLDL Lipoproteins Proteins 0.000 description 3
239000002671 adjuvant Substances 0.000 description 3
239000003524 antilipemic agent Substances 0.000 description 3
210000004369 blood Anatomy 0.000 description 3
239000008280 blood Substances 0.000 description 3
230000037396 body weight Effects 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
229940079593 drug Drugs 0.000 description 3
239000003814 drug Substances 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
229910010272 inorganic material Inorganic materials 0.000 description 3
239000011147 inorganic material Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
239000006188 syrup Substances 0.000 description 3
235000020357 syrup Nutrition 0.000 description 3
SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
SWTCCCJQNPGXLQ-UHFFFAOYSA-N 1-(1-butoxyethoxy)butane Chemical compound CCCCOC(C)OCCCC SWTCCCJQNPGXLQ-UHFFFAOYSA-N 0.000 description 2
SSTRYEXQYQGGAS-UHFFFAOYSA-N 3,4-diethoxybenzaldehyde Chemical compound CCOC1=CC=C(C=O)C=C1OCC SSTRYEXQYQGGAS-UHFFFAOYSA-N 0.000 description 2
IBGBGRVKPALMCQ-UHFFFAOYSA-N 3,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1O IBGBGRVKPALMCQ-UHFFFAOYSA-N 0.000 description 2
IOKYUTCABAXWAK-UHFFFAOYSA-N 3,4-dipropoxybenzaldehyde Chemical compound CCCOC1=CC=C(C=O)C=C1OCCC IOKYUTCABAXWAK-UHFFFAOYSA-N 0.000 description 2
WMPDAIZRQDCGFH-UHFFFAOYSA-N 3-methoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1 WMPDAIZRQDCGFH-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
208000035150 Hypercholesterolemia Diseases 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
150000001447 alkali salts Chemical class 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
125000004744 butyloxycarbonyl group Chemical group 0.000 description 2
159000000007 calcium salts Chemical class 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
239000000969 carrier Substances 0.000 description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
238000001816 cooling Methods 0.000 description 2
STRNXFOUBFLVIN-UHFFFAOYSA-N diethyl but-2-ynedioate Chemical compound CCOC(=O)C#CC(=O)OCC STRNXFOUBFLVIN-UHFFFAOYSA-N 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
125000001153 fluoro group Chemical group F* 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
239000007924 injection Substances 0.000 description 2
238000002347 injection Methods 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000008297 liquid dosage form Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
125000004742 propyloxycarbonyl group Chemical group 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
NRHMKIHPTBHXPF-TUJRSCDTSA-M sodium cholate Chemical compound [Na+].C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC([O-])=O)C)[C@@]2(C)[C@@H](O)C1 NRHMKIHPTBHXPF-TUJRSCDTSA-M 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
VLRUOGHIEVUWEB-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)-n-cyclohexylmethanimine Chemical compound C1=C2OCOC2=CC=C1C=NC1CCCCC1 VLRUOGHIEVUWEB-UHFFFAOYSA-N 0.000 description 1
MISTZQJSHHTDCF-UHFFFAOYSA-N 1-(1-propoxyethoxy)propane Chemical compound CCCOC(C)OCCC MISTZQJSHHTDCF-UHFFFAOYSA-N 0.000 description 1
DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
PCYGLFXKCBFGPC-UHFFFAOYSA-N 3,4-Dihydroxy hydroxymethyl benzene Natural products OCC1=CC=C(O)C(O)=C1 PCYGLFXKCBFGPC-UHFFFAOYSA-N 0.000 description 1
MDWHWNRETVPUMN-UHFFFAOYSA-N 3,4-di(propan-2-yloxy)benzaldehyde Chemical compound CC(C)OC1=CC=C(C=O)C=C1OC(C)C MDWHWNRETVPUMN-UHFFFAOYSA-N 0.000 description 1
VAMZHXWLGRQSJS-UHFFFAOYSA-N 3-ethoxy-4-methoxybenzaldehyde Chemical compound CCOC1=CC(C=O)=CC=C1OC VAMZHXWLGRQSJS-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
BERFDQAMXIBOHM-UHFFFAOYSA-N 4-Ethoxy-3-methoxybenzaldehyde Chemical compound CCOC1=CC=C(C=O)C=C1OC BERFDQAMXIBOHM-UHFFFAOYSA-N 0.000 description 1
CSQUXTSIDQURDV-UHFFFAOYSA-N 6-bromo-1,3-benzodioxole-5-carbaldehyde Chemical compound C1=C(C=O)C(Br)=CC2=C1OCO2 CSQUXTSIDQURDV-UHFFFAOYSA-N 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
239000004166 Lanolin Substances 0.000 description 1
102000004895 Lipoproteins Human genes 0.000 description 1
108090001030 Lipoproteins Proteins 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
208000034189 Sclerosis Diseases 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
210000000702 aorta abdominal Anatomy 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
208000004670 arteriolosclerosis Diseases 0.000 description 1
WPUJEWVVTKLMQI-UHFFFAOYSA-N benzene;ethoxyethane Chemical compound CCOCC.C1=CC=CC=C1 WPUJEWVVTKLMQI-UHFFFAOYSA-N 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
235000010216 calcium carbonate Nutrition 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
229940107170 cholestyramine resin Drugs 0.000 description 1
KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 description 1
229960001214 clofibrate Drugs 0.000 description 1
239000003240 coconut oil Substances 0.000 description 1
235000019864 coconut oil Nutrition 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
239000002285 corn oil Substances 0.000 description 1
235000005687 corn oil Nutrition 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000008021 deposition Effects 0.000 description 1
229960000633 dextran sulfate Drugs 0.000 description 1
230000000378 dietary effect Effects 0.000 description 1
RKXILMKIGHFPDW-UHFFFAOYSA-N diethyl 8-[3,4-di(propan-2-yloxy)phenyl]-5-hydroxybenzo[f][1,3]benzodioxole-6,7-dicarboxylate Chemical compound CCOC(=O)C=1C(C(=O)OCC)=C(O)C2=CC=3OCOC=3C=C2C=1C1=CC=C(OC(C)C)C(OC(C)C)=C1 RKXILMKIGHFPDW-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
IUFZGMCIRGDCNK-UHFFFAOYSA-N dimethyl 1-(3,4-dimethoxyphenyl)-4,7-dihydroxy-6-methoxynaphthalene-2,3-dicarboxylate Chemical compound COC(=O)C=1C(C(=O)OC)=C(O)C2=CC(OC)=C(O)C=C2C=1C1=CC=C(OC)C(OC)=C1 IUFZGMCIRGDCNK-UHFFFAOYSA-N 0.000 description 1
UUWYMYFARXLEDO-UHFFFAOYSA-N dimethyl 1-(3,4-dimethoxyphenyl)-4-hydroxy-6-methoxy-7-phenylmethoxynaphthalene-2,3-dicarboxylate Chemical compound C1=C2C(C=3C=C(OC)C(OC)=CC=3)=C(C(=O)OC)C(C(=O)OC)=C(O)C2=CC(OC)=C1OCC1=CC=CC=C1 UUWYMYFARXLEDO-UHFFFAOYSA-N 0.000 description 1
DQOCYKDRQPFAIG-UHFFFAOYSA-N dimethyl 4-(3,4-diethoxyphenyl)-1-hydroxy-5,6,7-trimethoxynaphthalene-2,3-dicarboxylate Chemical compound C1=C(OCC)C(OCC)=CC=C1C1=C(C(=O)OC)C(C(=O)OC)=C(O)C2=CC(OC)=C(OC)C(OC)=C12 DQOCYKDRQPFAIG-UHFFFAOYSA-N 0.000 description 1
RSHYRACMZOBDGB-UHFFFAOYSA-N dimethyl 4-(3,4-dipropoxyphenyl)-1-hydroxy-5,6,7-trimethoxynaphthalene-2,3-dicarboxylate Chemical group C1=C(OCCC)C(OCCC)=CC=C1C1=C(C(=O)OC)C(C(=O)OC)=C(O)C2=CC(OC)=C(OC)C(OC)=C12 RSHYRACMZOBDGB-UHFFFAOYSA-N 0.000 description 1
MRXBEVDBTITKEJ-UHFFFAOYSA-N dimethyl 4-(4-ethoxy-3-methoxyphenyl)-1-hydroxy-5,6,7-trimethoxynaphthalene-2,3-dicarboxylate Chemical compound C1=C(OC)C(OCC)=CC=C1C1=C(C(=O)OC)C(C(=O)OC)=C(O)C2=CC(OC)=C(OC)C(OC)=C12 MRXBEVDBTITKEJ-UHFFFAOYSA-N 0.000 description 1
SARUOVJBYMEGTM-UHFFFAOYSA-N dimethyl 4-hydroxy-6,7,8-trimethoxynaphthalene-1,2-dicarboxylate Chemical compound C1=C(OC)C(OC)=C(OC)C2=C(C(=O)OC)C(C(=O)OC)=CC(O)=C21 SARUOVJBYMEGTM-UHFFFAOYSA-N 0.000 description 1
HXCZXOCAGHYCIV-UHFFFAOYSA-N dimethyl 5-hydroxy-8-(3-methoxyphenyl)benzo[f][1,3]benzodioxole-6,7-dicarboxylate Chemical compound COC(=O)C=1C(C(=O)OC)=C(O)C2=CC=3OCOC=3C=C2C=1C1=CC=CC(OC)=C1 HXCZXOCAGHYCIV-UHFFFAOYSA-N 0.000 description 1
XRTYQIGEIQCLDT-UHFFFAOYSA-N dimethyl 5-hydroxy-8-(4-methoxyphenyl)benzo[f][1,3]benzodioxole-6,7-dicarboxylate Chemical compound COC(=O)C=1C(C(=O)OC)=C(O)C2=CC=3OCOC=3C=C2C=1C1=CC=C(OC)C=C1 XRTYQIGEIQCLDT-UHFFFAOYSA-N 0.000 description 1
WHGUGJFBBKVAFK-UHFFFAOYSA-N dimethyl 8-(3,4-diethoxyphenyl)-5-hydroxybenzo[f][1,3]benzodioxole-6,7-dicarboxylate Chemical compound C1=C(OCC)C(OCC)=CC=C1C(C1=C2)=C(C(=O)OC)C(C(=O)OC)=C(O)C1=CC1=C2OCO1 WHGUGJFBBKVAFK-UHFFFAOYSA-N 0.000 description 1
BAKAWBUEFCXCDT-UHFFFAOYSA-N dimethyl 9-(3,4-dimethoxyphenyl)-6-hydroxybenzo[g][1,3]benzodioxole-7,8-dicarboxylate Chemical compound COC(=O)C=1C(C(=O)OC)=C(O)C2=CC=C3OCOC3=C2C=1C1=CC=C(OC)C(OC)=C1 BAKAWBUEFCXCDT-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
201000005577 familial hyperlipidemia Diseases 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
208000027700 hepatic dysfunction Diseases 0.000 description 1
239000003906 humectant Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
230000003516 hyperlipidaemic effect Effects 0.000 description 1
238000011835 investigation Methods 0.000 description 1
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000019388 lanolin Nutrition 0.000 description 1
229940039717 lanolin Drugs 0.000 description 1
239000010410 layer Substances 0.000 description 1
108010022197 lipoprotein cholesterol Proteins 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
IMAKHNTVDGLIRY-UHFFFAOYSA-N methyl prop-2-ynoate Chemical compound COC(=O)C#C IMAKHNTVDGLIRY-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
UKOVZLWSUZKTRL-UHFFFAOYSA-N naphthalid Chemical class C1=CC(C(=O)OC2)=C3C2=CC=CC3=C1 UKOVZLWSUZKTRL-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
FYPMFJGVHOHGLL-UHFFFAOYSA-N probucol Chemical compound C=1C(C(C)(C)C)=C(O)C(C(C)(C)C)=CC=1SC(C)(C)SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 FYPMFJGVHOHGLL-UHFFFAOYSA-N 0.000 description 1
229960003912 probucol Drugs 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000004062 sedimentation Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
241000894007 species Species 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical class C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
239000000341 volatile oil Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C14/00—Coating by vacuum evaporation, by sputtering or by ion implantation of the coating forming material
- C23C14/22—Coating by vacuum evaporation, by sputtering or by ion implantation of the coating forming material characterised by the process of coating
- C23C14/48—Ion implantation

Landscapes

Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Mechanical Engineering (AREA)
Metallurgy (AREA)
Organic Chemistry (AREA)
Physical Vapour Deposition (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Inorganic Compounds Of Heavy Metals (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

DD28610686A 1985-01-11 1986-01-10 Verfahren zur herstellung von naphthalinderivaten DD261786A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP306085A JPS61163264A (ja)	1985-01-11	1985-01-11	白金族金属の酸化膜形成法

Publications (1)

Publication Number	Publication Date
DD261786A5 true DD261786A5 (de)	1988-11-09

Family

ID=11546779

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD28610686A DD261786A5 (de)	1985-01-11	1986-01-10	Verfahren zur herstellung von naphthalinderivaten

Country Status (5)

Country	Link
JP (1)	JPS61163264A (da)
DD (1)	DD261786A5 (da)
DE (1)	DE3600575C2 (da)
DK (1)	DK9886A (da)
SU (2)	SU1581217A3 (da)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0305300B1 (en) *	1987-08-28	1996-04-24	Sumitomo Electric Industries Limited	A method for producing a superconducting article
KR0172772B1 (ko) *	1995-05-17	1999-03-30	김주용	반도체 장치의 확산장벽용 산화루테늄막 형성 방법
JP2009107773A (ja) *	2007-10-30	2009-05-21	Mitsubishi Electric Corp	プリンタ装置
RU2551655C1 (ru) *	2014-05-15	2015-05-27	Федеральное государственное бюджетное учреждение науки Новосибирский институт органической химии им. Н.Н. Ворожцова Сибирского отделения Российской академии наук (НИОХ СО РАН)	Способ получения (3-гидроксипропил)нафтолов

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5331971A (en) *	1976-09-06	1978-03-25	Nippon Telegr & Teleph Corp <Ntt>	Forming method of metal oxide film or semiconductor oxide film

1985
- 1985-01-11 JP JP306085A patent/JPS61163264A/ja active Pending
1986
- 1986-01-09 SU SU864013137A patent/SU1581217A3/ru active
- 1986-01-09 DK DK9886A patent/DK9886A/da not_active Application Discontinuation
- 1986-01-10 DE DE19863600575 patent/DE3600575C2/de not_active Expired
- 1986-01-10 DD DD28610686A patent/DD261786A5/de unknown
- 1986-11-13 SU SU864028493A patent/SU1577697A3/ru active

Also Published As

Publication number	Publication date
DE3600575C2 (de)	1987-03-19
DK9886D0 (da)	1986-01-09
SU1577697A3 (ru)	1990-07-07
SU1581217A3 (ru)	1990-07-23
JPS61163264A (ja)	1986-07-23
DE3600575A1 (de)	1986-07-17
DK9886A (da)	1986-07-11

Publication	Publication Date	Title
DD270529A5 (de)	1989-08-02	Verfahren zur herstellung von naphthalinderivaten
AT388372B (de)	1989-06-12	Neue naphthalinderivate und sie enthaltende pharmazeutika
DE2624693A1 (de)	1977-07-14	Isochromanderivate und verfahren zu deren herstellung
DE2165260A1 (de)	1972-07-27	Verfahren zur Herstellung von N-substituierten Dibenzo eckige Klammer auf b,f eckige Klammer zu thiepin-10-methylaminen und zugehörige neue Zwischenprodukte
CH633249A5 (de)	1982-11-30	Verfahren zur herstellung von neuen polyprenylderivaten.
DE2716189A1 (de)	1977-10-27	Phenoxypropionsaeurederivate, verfahren zu ihrer herstellung und ihre verwendung als oder in therapeutischen und herbiciden mitteln
DE2415697A1 (de)	1974-10-17	Alkylphenylbenzopyrane
DE2637098A1 (de)	1977-02-24	Phenoxyalkylcarbonsaeurederivate und verfahren zu ihrer herstellung
DD145104A5 (de)	1980-11-19	Verfahren zur herstellung von polyalkoxyphenylpyrrolidone
DD261786A5 (de)	1988-11-09	Verfahren zur herstellung von naphthalinderivaten
DE3014813A1 (de)	1980-11-13	2-hydroxy-5-(1-hydroxy-2-piperazinylethyl)benzoesaeure-derivate
DE2929760A1 (de)	1980-02-07	2-acyl-6-aminomethylphenolderivate, verfahren zu ihrer herstellung und sie enthaltende derivate
DE2131330A1 (de)	1972-01-05	Imidazo-[1,2-a]-benzimidazolderivate und Verfahren zur Herstellung derselben
DE2416491A1 (de)	1974-10-24	Heterocyclische ester von alkylphenylbenzopyranen
DE2517020A1 (de)	1975-11-06	Alkanolaminderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE2462460C3 (de)	1980-02-14	In 8-Stellung des Chinolinrings substituierte 2-(4-Chinolylamino)-benzoesäure-2-(4-phenylpiperazino)-äthylester, Verfahren zu deren Herstellung und Arzneimittel, welche diese enthalten
DE2914166A1 (de)	1980-10-23	Arylsubstituierte furane und verfahren zu ihrer herstellung
EP0158312B1 (de)	1990-09-12	1-[Cyclohexyl]-3,4-di-[hydro]-isochinolinderivate, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
DE2735589A1 (de)	1979-02-15	1-phenyl-1-methoxy-2-amino-aethan- derivate und verfahren zu ihrer herstellung
DE2509797C2 (de)	1985-07-18	Phthalimidine, deren physiologisch verträgliche Säureadditionssalze, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE3107594A1 (de)	1982-02-11	Neue piperazin-verbindungen, verfahren zu ihrer herstellung und ihre verwendung
DE2412798A1 (de)	1974-09-26	Neue phenylpropylaminderivate und verfahren zu ihrer herstellung
CH627743A5 (de)	1982-01-29	Verfahren zur herstellung neuer substituierter arylalkylamine.
CH581656A5 (da)	1976-11-15
EP0064026B1 (de)	1985-07-03	Neue dioxaheterocyclische Verbindungen, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Zusammensetzungen