DD270529A5 - Verfahren zur herstellung von naphthalinderivaten - Google Patents

Verfahren zur herstellung von naphthalinderivaten Download PDF

Info

Publication number: DD270529A5
Authority: DD; German Democratic Republic
Prior art keywords: ring; lower alkoxy; hydroxy; hydrogen atom; compound
Prior art date: 1985-01-10

Application number

DD88312249A

Other languages

German (de)

English (en)

Inventor

Tameo Iwasaki

Kohki Takashima

Original Assignee

��@��@��K@��Kk��

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.)

1985-01-10

Filing date

1988-01-15

Publication date

1989-08-02

1988-01-15 Application filed by ��@��@��K@��Kk�� filed Critical ��@��@��K@��Kk��

1989-08-02 Publication of DD270529A5 publication Critical patent/DD270529A5/de

Links

238000000034 method Methods 0.000 title claims description 10
238000002360 preparation method Methods 0.000 title abstract description 6
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical class C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 title description 3
150000003839 salts Chemical class 0.000 claims abstract description 17
150000001875 compounds Chemical class 0.000 claims description 37
125000003545 alkoxy group Chemical group 0.000 claims description 35
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
125000000217 alkyl group Chemical group 0.000 claims description 19
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
125000004432 carbon atom Chemical group C* 0.000 claims description 10
230000002829 reductive effect Effects 0.000 claims description 8
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 4
238000007273 lactonization reaction Methods 0.000 claims description 2
150000002790 naphthalenes Chemical class 0.000 abstract description 10
206010003210 Arteriosclerosis Diseases 0.000 abstract description 5
208000011775 arteriosclerosis disease Diseases 0.000 abstract description 5
238000011321 prophylaxis Methods 0.000 abstract description 4
208000031226 Hyperlipidaemia Diseases 0.000 abstract description 3
230000000055 hyoplipidemic effect Effects 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 52
-1 4,4 '- ((1-methylethylidene) bis (thio) bis (2,5-bis (1,1-dimethylethyl) phenol)) Chemical compound 0.000 description 25
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
239000000203 mixture Substances 0.000 description 21
210000002966 serum Anatomy 0.000 description 20
239000013078 crystal Substances 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
239000000243 solution Substances 0.000 description 14
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
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
241000700159 Rattus Species 0.000 description 8
239000002253 acid Substances 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
235000005911 diet Nutrition 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
WJUFSDZVCOTFON-UHFFFAOYSA-N veratraldehyde Chemical compound COC1=CC=C(C=O)C=C1OC WJUFSDZVCOTFON-UHFFFAOYSA-N 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
108010023302 HDL Cholesterol Proteins 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
230000037213 diet Effects 0.000 description 5
VHILMKFSCRWWIJ-UHFFFAOYSA-N dimethyl acetylenedicarboxylate Chemical compound COC(=O)C#CC(=O)OC VHILMKFSCRWWIJ-UHFFFAOYSA-N 0.000 description 5
230000000694 effects Effects 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
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 4
150000001555 benzenes Chemical group 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-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
239000008194 pharmaceutical composition Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
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 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
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
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
238000001816 cooling Methods 0.000 description 3
238000000354 decomposition reaction Methods 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
229910052739 hydrogen Inorganic materials 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
150000002596 lactones Chemical class 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
239000002244 precipitate 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
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 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
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 2
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 2
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 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
XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 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
241001465754 Metazoa Species 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
208000034189 Sclerosis Diseases 0.000 description 2
239000002671 adjuvant Substances 0.000 description 2
125000005530 alkylenedioxy group Chemical group 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 description 2
238000000151 deposition 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
235000019253 formic acid Nutrition 0.000 description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
239000007924 injection Substances 0.000 description 2
238000002347 injection Methods 0.000 description 2
229910010272 inorganic material Inorganic materials 0.000 description 2
239000011147 inorganic material Substances 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
229910052744 lithium Inorganic materials 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
229940098779 methanesulfonic acid Drugs 0.000 description 2
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
150000007524 organic acids Chemical class 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
230000000704 physical effect Effects 0.000 description 2
150000003242 quaternary ammonium salts Chemical class 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
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
238000002560 therapeutic procedure Methods 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
BWFRHSRQIKGLLM-UHFFFAOYSA-N 2-bromo-3,4-dimethoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(Br)=C1OC BWFRHSRQIKGLLM-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
125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
PXHRXDBHCHYICT-UHFFFAOYSA-N 4-[(3,4-dimethoxyphenyl)-hydroxymethyl]-1,3-benzodioxole-5-carbaldehyde Chemical compound C1=C(OC)C(OC)=CC=C1C(O)C1=C(OCO2)C2=CC=C1C=O PXHRXDBHCHYICT-UHFFFAOYSA-N 0.000 description 1
WDANSDASCKBVKH-UHFFFAOYSA-N 4-propan-2-yloxybenzaldehyde Chemical compound CC(C)OC1=CC=C(C=O)C=C1 WDANSDASCKBVKH-UHFFFAOYSA-N 0.000 description 1
JYYUOLRCRQQGEQ-UHFFFAOYSA-N C1=C(OC)C(OC)=CC=C1C(O)C1=C(Cl)C(Cl)=CC=C1C=O Chemical compound C1=C(OC)C(OC)=CC=C1C(O)C1=C(Cl)C(Cl)=CC=C1C=O JYYUOLRCRQQGEQ-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
241000790917 Dioxys <bee> Species 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
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
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
239000012448 Lithium borohydride Substances 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
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
150000007513 acids Chemical class 0.000 description 1
150000001299 aldehydes Chemical class 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
150000001447 alkali salts Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 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
UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical class [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 description 1
KZMGYPLQYOPHEL-UHFFFAOYSA-N boron trifluoride etherate Substances FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 1
UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 1
NNTOJPXOCKCMKR-UHFFFAOYSA-N boron;pyridine Chemical compound [B].C1=CC=NC=C1 NNTOJPXOCKCMKR-UHFFFAOYSA-N 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229960005069 calcium Drugs 0.000 description 1
235000001465 calcium Nutrition 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
229960001714 calcium phosphate Drugs 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
229940107170 cholestyramine resin Drugs 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
230000003247 decreasing effect Effects 0.000 description 1
230000008021 deposition Effects 0.000 description 1
230000000378 dietary effect Effects 0.000 description 1
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 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
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
FEALDEJRWNETKP-UHFFFAOYSA-N dimethyl 4-(3,4-dimethoxyphenyl)-1-hydroxy-6-methylnaphthalene-2,3-dicarboxylate Chemical compound COC(=O)C=1C(C(=O)OC)=C(O)C2=CC=C(C)C=C2C=1C1=CC=C(OC)C(OC)=C1 FEALDEJRWNETKP-UHFFFAOYSA-N 0.000 description 1
RSHYRACMZOBDGB-UHFFFAOYSA-N dimethyl 4-(3,4-dipropoxyphenyl)-1-hydroxy-5,6,7-trimethoxynaphthalene-2,3-dicarboxylate Chemical compound 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
SABMKICAAHGWHD-UHFFFAOYSA-N dimethyl 5,6-dichloro-4-(3,4-dimethoxyphenyl)-1-hydroxynaphthalene-2,3-dicarboxylate Chemical compound COC(=O)C=1C(C(=O)OC)=C(O)C2=CC=C(Cl)C(Cl)=C2C=1C1=CC=C(OC)C(OC)=C1 SABMKICAAHGWHD-UHFFFAOYSA-N 0.000 description 1
IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical group COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 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
239000000706 filtrate Substances 0.000 description 1
239000008187 granular material Substances 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
150000004678 hydrides Chemical class 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
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
108010022197 lipoprotein cholesterol Proteins 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
DPQLKYMWTKSNFS-UHFFFAOYSA-N methyl 5-hydroxybenzo[f][1,3]benzodioxole-8-carboxylate Chemical compound C1=C2C(C(=O)OC)=CC=C(O)C2=CC2=C1OCO2 DPQLKYMWTKSNFS-UHFFFAOYSA-N 0.000 description 1
PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 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
239000006187 pill Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920001451 polypropylene glycol Polymers 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
229920001592 potato starch Polymers 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
230000000069 prophylactic effect Effects 0.000 description 1
125000001453 quaternary ammonium group Chemical group 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
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007909 solid dosage form Substances 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
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 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
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/94—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of polycyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of six-membered aromatic rings
- 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
- C07D307/92—Naphthofurans; Hydrogenated naphthofurans
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/33—Polycyclic acids
- C07C63/337—Polycyclic acids with carboxyl groups bound to condensed ring systems
- C07C63/34—Polycyclic acids with carboxyl groups bound to condensed ring systems containing two condensed rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
- C07C65/24—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups polycyclic
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/70—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with ring systems containing two or more relevant rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Diabetes (AREA)
Vascular Medicine (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Hematology (AREA)
Obesity (AREA)
Urology & Nephrology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Furan Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Medicines Containing Plant Substances (AREA)
Medicinal Preparation (AREA)
Saccharide Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Lubricants (AREA)
Fats And Perfumes (AREA)

DD88312249A 1985-01-10 1988-01-15 Verfahren zur herstellung von naphthalinderivaten DD270529A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP309085		1985-01-10

Publications (1)

Publication Number	Publication Date
DD270529A5 true DD270529A5 (de)	1989-08-02

Family

ID=11547645

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD88312249A DD270529A5 (de)	1985-01-10	1988-01-15	Verfahren zur herstellung von naphthalinderivaten

Country Status (18)

Country	Link
US (2)	US4771072A (es)
EP (1)	EP0188248B1 (es)
JP (3)	JPS61267541A (es)
KR (1)	KR890001884B1 (es)
CN (1)	CN1006464B (es)
AT (1)	ATE54441T1 (es)
AU (1)	AU584153B2 (es)
BG (2)	BG45383A3 (es)
DD (1)	DD270529A5 (es)
DE (1)	DE3672501D1 (es)
ES (2)	ES8705837A1 (es)
FI (1)	FI87557C (es)
HU (1)	HU196737B (es)
IL (1)	IL91117A0 (es)
MY (1)	MY101268A (es)
NO (1)	NO170760C (es)
PH (1)	PH22105A (es)
PT (1)	PT81814B (es)

Families Citing this family (35)

* Cited by examiner, † Cited by third party
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US4644072A (en) *	1985-04-12	1987-02-17	Bristol-Myers Company	Intermediates for the production of epipodophyllotoxin and related compounds and processes for the preparation and use thereof
US5011948A (en) *	1985-04-12	1991-04-30	Bristol-Myers Company	Intermediates for the production of epipodophyllotoxin and related compounds and processes for the preparation and use thereof
JPS6310746A (ja) *	1986-07-01	1988-01-18	Tanabe Seiyaku Co Ltd	ナフタレン誘導体
AT388372B (de) *	1987-10-08	1989-06-12	Tanabe Seiyaku Co	Neue naphthalinderivate und sie enthaltende pharmazeutika
JPH01135766A (ja) *	1987-11-20	1989-05-29	Tanabe Seiyaku Co Ltd	ビフェニル誘導体
PH26342A (en) *	1988-11-29	1992-04-29	Univ Texas	Microbial cellulose modified during synthesis
MY105057A (en) *	1989-01-27	1994-07-30	Tanabe Seiyaku Co	A process for preparing naphthalene derivatives
US5003087A (en) *	1989-02-03	1991-03-26	Tanabe Seiyaku Co., Ltd.	Process for preparing a naphthalene derivative and a synthetic intermediate thereof
EP0501579A1 (en) *	1991-02-28	1992-09-02	Merck Frosst Canada Inc.	Naphthalene lactones as inhibitors of leukotriene biosynthesis
EP0501578A1 (en) *	1991-02-28	1992-09-02	Merck Frosst Canada Inc.	Pyranylphenyl hydroxyalkylnaphthoic acids as inhibitors of leukotriene biosynthesis
US5227399A (en) *	1991-02-28	1993-07-13	Merck Frosst Canada, Inc.	Pyranylphenyl naphthalene lactones as inhibitors of leukotriene biosynthesis
US5281720A (en) *	1991-02-28	1994-01-25	Merck Frosst Canada, Inc.	Pyranylphenyl hydroxyalkylnaphthoic acids as inhibitors of leukotriene biosynthesis
ES2091488T3 (es) *	1991-10-17	1996-11-01	Shionogi & Co	Analogo de lignano, su produccion y medicamento hipolipidemico.
US5308852A (en) *	1992-06-29	1994-05-03	Merck Frosst Canada, Inc.	Heteroarylnaphthalenes as inhibitors of leukotriene biosynthesis
US5426109A (en) *	1992-08-27	1995-06-20	Merck Frosst Canada, Inc.	Phenylnaphthalene hydroxy acids
US5428060A (en) *	1992-08-27	1995-06-27	Merck Frosst Canada, Inc.	Heteroarylnaphthalene lactones as inhibitors of leukotriene biosynthesis
US5252599A (en) *	1992-08-27	1993-10-12	Merck Frosst Canada, Inc.	Heteroarylnaphthalene hydroxy acids as inhibitors of leukotriene biosynthesis
US5350744A (en) *	1992-08-27	1994-09-27	Merck Frosst Canada, Inc.	Phenylnaphthalene lactones as inhibitors of leukotriene biosynthesis
CA2121060C (en) *	1993-04-16	2004-04-06	Sachio Mori	Preparation of lignan analogues
ID18046A (id) *	1996-08-20	1998-02-19	Takeda Chemical Industries Ltd	Senyawa siklik campuran, pembuatan dan penngunaannya.
US6306899B1 (en)	1998-08-25	2001-10-23	Yale University	Inhibition and treatment of Hepatitis B virus and Flavivirus by Helioxanthin and its analogs
MXPA01012494A (es)	1999-06-01	2002-07-02	Univ Texas Southwestern Med Ct	Metodo para tratar perdida capilar con el uso de compuestos sulfonil tiromimeticos.
US6680344B1 (en)	1999-06-01	2004-01-20	The University Of Texas Southwestern Medical Center	Method of treating hair loss using diphenylmethane derivatives
AU3507700A (en)	1999-06-01	2000-12-18	University Of Texas Southwestern Medical Center, The	Method of treating hair loss using diphenylether derivatives
SE0102168D0 (sv) *	2001-06-19	2001-06-19	Karolinska Innovations Ab	New use and new compounds
HUP0401696A2 (hu) *	2001-08-28	2004-11-29	Sankyo Co., Ltd.	Angiotenzin-II receptor antagonistát tartalmazó gyógyászati készítmény
GB0307918D0 (en)	2003-04-05	2003-05-14	Astrazeneca Ab	Therapeutic use
WO2011150286A2 (en)	2010-05-26	2011-12-01	Satiogen Pharmaceuticals,Inc.	Bile acid recycling inhibitors and satiogens for treatment of diabetes, obesity, and inflammatory gastrointestinal conditions
BR112014010223B8 (pt)	2011-10-28	2021-02-23	Lumena Pharmaceuticals Llc	uso de uma composição compreendendo inibidores de reciclagem de ácido de bílis e forma de dosagem pediátrica
EP3278796A1 (en)	2011-10-28	2018-02-07	Lumena Pharmaceuticals LLC	Bile acid recycling inhibitors for treatment of hypercholemia and cholestatic liver disease
RU2015139732A (ru)	2013-03-15	2017-04-24	ЛУМЕНА ФАРМАСЬЮТИКАЛС ЭлЭлСи	Ингибиторы рециркуляции желчных кислот для лечения пищевода барретта и гастроэзофагеальной рефлюксной болезни
CN105228607A (zh)	2013-03-15	2016-01-06	鲁美纳医药公司	用于治疗原发性硬化性胆管炎和炎性肠病的胆汁酸再循环抑制剂
WO2015153653A1 (en) *	2014-03-31	2015-10-08	Ohio State Innovation Foundation	Arylnaphthalene lactone derivatives and methods of making and using thereof
US10682367B2 (en)	2016-02-26	2020-06-16	Ohio State Innovation Foundation	Antitumor arylnaphthalene ligand glycosides
AU2020223022A1 (en)	2019-02-12	2021-09-02	Mirum Pharmaceuticals, Inc.	Methods for increasing growth in pediatric subjects having cholestatic liver disease

1985
- 1985-12-30 NO NO855355A patent/NO170760C/no unknown
- 1985-12-30 US US06/814,805 patent/US4771072A/en not_active Expired - Fee Related
- 1985-12-30 ES ES550578A patent/ES8705837A1/es not_active Expired
- 1985-12-31 AU AU51751/85A patent/AU584153B2/en not_active Ceased
1986
- 1986-01-08 JP JP61002624A patent/JPS61267541A/ja active Pending
- 1986-01-08 PH PH33266A patent/PH22105A/en unknown
- 1986-01-09 BG BG073061A patent/BG45383A3/xx unknown
- 1986-01-09 PT PT81814A patent/PT81814B/pt not_active IP Right Cessation
- 1986-01-09 FI FI860089A patent/FI87557C/fi not_active IP Right Cessation
- 1986-01-09 BG BG082397A patent/BG45385A3/xx unknown
- 1986-01-09 HU HU8690A patent/HU196737B/hu not_active IP Right Cessation
- 1986-01-09 KR KR1019860000074A patent/KR890001884B1/ko not_active Expired
- 1986-01-10 CN CN86100090A patent/CN1006464B/zh not_active Expired
- 1986-01-10 AT AT86100282T patent/ATE54441T1/de not_active IP Right Cessation
- 1986-01-10 EP EP86100282A patent/EP0188248B1/en not_active Expired - Lifetime
- 1986-01-10 DE DE8686100282T patent/DE3672501D1/de not_active Expired - Fee Related
- 1986-09-03 ES ES557052A patent/ES8801239A1/es not_active Expired
1987
- 1987-07-15 MY MYPI87001017A patent/MY101268A/en unknown
1988
- 1988-01-15 DD DD88312249A patent/DD270529A5/de not_active IP Right Cessation
- 1988-12-08 JP JP63310354A patent/JPH0272170A/ja active Granted
- 1988-12-08 JP JP63310353A patent/JPH0272136A/ja active Pending
1989
- 1989-07-26 IL IL91117A patent/IL91117A0/xx unknown
1990
- 1990-01-02 US US07/459,859 patent/US5070103A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
EP0188248B1 (en)	1990-07-11
US4771072A (en)	1988-09-13
ATE54441T1 (de)	1990-07-15
PH22105A (en)	1988-06-01
FI87557B (fi)	1992-10-15
EP0188248A2 (en)	1986-07-23
NO170760B (no)	1992-08-24
NO170760C (no)	1992-12-02
BG45385A3 (bg)	1989-05-15
JPH0272170A (ja)	1990-03-12
EP0188248A3 (en)	1986-12-17
ES550578A0 (es)	1987-05-16
KR860005778A (ko)	1986-08-13
FI87557C (fi)	1993-01-25
AU5175185A (en)	1986-07-17
ES8801239A1 (es)	1987-12-16
PT81814A (en)	1986-02-01
IL91117A0 (en)	1990-03-19
JPH0549668B2 (es)	1993-07-26
CN1006464B (zh)	1990-01-17
MY101268A (en)	1991-08-17
CN86100090A (zh)	1986-08-20
PT81814B (pt)	1988-07-29
AU584153B2 (en)	1989-05-18
BG45383A3 (bg)	1989-05-15
ES557052A0 (es)	1987-12-16
FI860089A0 (fi)	1986-01-09
HUT42428A (en)	1987-07-28
ES8705837A1 (es)	1987-05-16
DE3672501D1 (de)	1990-08-16
FI860089L (fi)	1986-07-11
JPS61267541A (ja)	1986-11-27
JPH0272136A (ja)	1990-03-12
HU196737B (en)	1989-01-30
KR890001884B1 (ko)	1989-05-29
US5070103A (en)	1991-12-03
NO855355L (no)	1986-07-11

Publication	Publication Date	Title
DD270529A5 (de)	1989-08-02	Verfahren zur herstellung von naphthalinderivaten
DE2130393B2 (de)	1980-06-12	6,7-Dihrdroxy -5,6,7,8-tetrahydronaphthyloxyaminopropanole und ihre Salze mit Säuren sowie ihre Verwendung bei der Bekämpfung von Herzerkrankungen
DE1643262A1 (de)	1972-04-20	Neue 1-Phenoxy-2-hydroxy-3-alkylaminopropane und Verfahren zu ihrer Herstellung
AT388372B (de)	1989-06-12	Neue naphthalinderivate und sie enthaltende pharmazeutika
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
DE68917357T2 (de)	1995-01-26	Derivate der Coffeinsäure und pharmazeutische Zusammensetzungen, die sie enthalten.
DD144763A5 (de)	1980-11-05	Verfahren zur herstellung von phenethanolaminen
DE2415697A1 (de)	1974-10-17	Alkylphenylbenzopyrane
DE2401374A1 (de)	1974-07-18	Tetrahydronaphthyloxyaminderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparate
DE2743166A1 (de)	1978-03-30	2-(3-phenyl-2-amino-propionyloxy)- essigsaeurederivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
DE2733305A1 (de)	1978-01-26	Neue phenoxyhydroxypropylamine, verfahren zu ihrer herstellung und ihre therapeutische anwendung
EP0002672B1 (de)	1981-08-26	Substituierte Pyrrolidine, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel
DE2929760C2 (es)	1987-05-27
DE2245518A1 (de)	1973-04-26	Arylidencyclanone und ihre herstellung und verwendung zur inhibierung der wirkung von androgenen
DE3151201A1 (de)	1983-07-28	Substituierte phenoxyalkanolamine und phenoxyalkanol-cycloalkylamine, verfahren zu ihrer herstellung, diese verbindungen enthaltende pharmazeutische zubereitungen und zwischenprodukte
DE2416491A1 (de)	1974-10-24	Heterocyclische ester von alkylphenylbenzopyranen
DD261786A5 (de)	1988-11-09	Verfahren zur herstellung von naphthalinderivaten
DE3125059A1 (de)	1983-01-05	Dioxybenzoletherderivate, diese enthaltende arzneimittel, verfahren zu ihrer herstellung und ihre verwendung
DE2462966C2 (de)	1983-12-29	Derivate des 3-Amino-4-acetyl-5-methylpyrrols und diese enthaltende pharmazeutische Zubereitungen
DD300542A5 (de)	1992-06-17	Chemische verbindungen
DE3925477A1 (de)	1990-02-08	Neue verbindungen der 3-isoxazolidinon-, 2h-1,2-oxazin-3-(4h)-on- und 3-isoxazepinon-serien
DE2834107A1 (de)	1979-02-22	Benzylalkoholderivate, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische mittel
DE2640884A1 (de)	1977-03-24	Neue entzuendungshemmende l-oxo-isoindolin-derivate 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
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