JPS61267541A - 抗脂血剤 - Google Patents
抗脂血剤Info
- Publication number
- JPS61267541A JPS61267541A JP61002624A JP262486A JPS61267541A JP S61267541 A JPS61267541 A JP S61267541A JP 61002624 A JP61002624 A JP 61002624A JP 262486 A JP262486 A JP 262486A JP S61267541 A JPS61267541 A JP S61267541A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- formulas
- lower alkoxy
- ring
- tables
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
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- 150000001875 compounds Chemical class 0.000 claims description 97
- 125000003545 alkoxy group Chemical group 0.000 claims description 74
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 50
- 150000003839 salts Chemical class 0.000 claims description 36
- 239000000126 substance Substances 0.000 claims description 34
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 230000002829 reductive effect Effects 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 150000002790 naphthalenes Chemical class 0.000 claims description 13
- 239000004480 active ingredient Substances 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 238000005886 esterification reaction Methods 0.000 claims description 3
- 238000007273 lactonization reaction Methods 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 9
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- 235000012000 cholesterol Nutrition 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 108010023302 HDL Cholesterol Proteins 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- VHILMKFSCRWWIJ-UHFFFAOYSA-N dimethyl acetylenedicarboxylate Chemical compound COC(=O)C#CC(=O)OC VHILMKFSCRWWIJ-UHFFFAOYSA-N 0.000 description 8
- 150000002596 lactones Chemical class 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
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- 238000005406 washing Methods 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 125000005530 alkylenedioxy group Chemical group 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 239000000047 product Substances 0.000 description 5
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- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 4
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- 238000001035 drying Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 4
- 150000002466 imines Chemical class 0.000 description 4
- 210000004185 liver Anatomy 0.000 description 4
- 229940098779 methanesulfonic acid Drugs 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 108010010234 HDL Lipoproteins Proteins 0.000 description 3
- 102000015779 HDL Lipoproteins Human genes 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 208000031226 Hyperlipidaemia Diseases 0.000 description 3
- 108010007622 LDL Lipoproteins Proteins 0.000 description 3
- 102000007330 LDL Lipoproteins Human genes 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
- 238000010306 acid treatment Methods 0.000 description 3
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- STRNXFOUBFLVIN-UHFFFAOYSA-N diethyl but-2-ynedioate Chemical compound CCOC(=O)C#CC(=O)OCC STRNXFOUBFLVIN-UHFFFAOYSA-N 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 230000001965 increasing effect Effects 0.000 description 3
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- 150000007522 mineralic acids Chemical class 0.000 description 3
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- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000004576 sand Substances 0.000 description 3
- RANYXVFYAIGDFE-UHFFFAOYSA-N 1,2,3-trimethoxynaphthalene Chemical compound C1=CC=C2C(OC)=C(OC)C(OC)=CC2=C1 RANYXVFYAIGDFE-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
- NQMUGNMMFTYOHK-UHFFFAOYSA-N 1-methoxynaphthalene Chemical compound C1=CC=C2C(OC)=CC=CC2=C1 NQMUGNMMFTYOHK-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
- 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
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
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- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
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- 238000002474 experimental method Methods 0.000 description 1
- 208000010706 fatty liver disease Diseases 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229910021505 gold(III) hydroxide Inorganic materials 0.000 description 1
- WDZVNNYQBQRJRX-UHFFFAOYSA-K gold(iii) hydroxide Chemical compound O[Au](O)O WDZVNNYQBQRJRX-UHFFFAOYSA-K 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 208000019423 liver disease Diseases 0.000 description 1
- 230000005976 liver dysfunction Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 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 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
- 239000003381 stabilizer Substances 0.000 description 1
- 231100000240 steatosis hepatitis Toxicity 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000012360 testing method Methods 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
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 239000002023 wood 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)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Obesity (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)
- Medicinal Preparation (AREA)
- Lubricants (AREA)
- Fats And Perfumes (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicines Containing Plant Substances (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60-3090 | 1985-01-10 | ||
| JP309085 | 1985-01-10 |
Related Child Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP31035588A Division JPH06724B2 (ja) | 1988-12-08 | 1988-12-08 | ナフタレン誘導体 |
| JP63310354A Division JPH0272170A (ja) | 1985-01-10 | 1988-12-08 | ナフトエ酸ラクトン誘導体 |
| JP63310353A Division JPH0272136A (ja) | 1985-01-10 | 1988-12-08 | ナフタレン誘導体、その製法及びその合成中間体 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS61267541A true JPS61267541A (ja) | 1986-11-27 |
Family
ID=11547645
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61002624A Pending JPS61267541A (ja) | 1985-01-10 | 1986-01-08 | 抗脂血剤 |
| JP63310353A Pending JPH0272136A (ja) | 1985-01-10 | 1988-12-08 | ナフタレン誘導体、その製法及びその合成中間体 |
| JP63310354A Granted JPH0272170A (ja) | 1985-01-10 | 1988-12-08 | ナフトエ酸ラクトン誘導体 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63310353A Pending JPH0272136A (ja) | 1985-01-10 | 1988-12-08 | ナフタレン誘導体、その製法及びその合成中間体 |
| JP63310354A Granted JPH0272170A (ja) | 1985-01-10 | 1988-12-08 | ナフトエ酸ラクトン誘導体 |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US4771072A (en]) |
| EP (1) | EP0188248B1 (en]) |
| JP (3) | JPS61267541A (en]) |
| KR (1) | KR890001884B1 (en]) |
| CN (1) | CN1006464B (en]) |
| AT (1) | ATE54441T1 (en]) |
| AU (1) | AU584153B2 (en]) |
| BG (2) | BG45383A3 (en]) |
| DD (1) | DD270529A5 (en]) |
| DE (1) | DE3672501D1 (en]) |
| ES (2) | ES8705837A1 (en]) |
| FI (1) | FI87557C (en]) |
| HU (1) | HU196737B (en]) |
| IL (1) | IL91117A0 (en]) |
| MY (1) | MY101268A (en]) |
| NO (1) | NO170760C (en]) |
| PH (1) | PH22105A (en]) |
| PT (1) | PT81814B (en]) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7629381B2 (en) | 2001-06-19 | 2009-12-08 | Axelar Ab | Use of specific cyklolignans |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US5281720A (en) * | 1991-02-28 | 1994-01-25 | Merck Frosst Canada, Inc. | Pyranylphenyl hydroxyalkylnaphthoic acids 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 |
| EP0501579A1 (en) * | 1991-02-28 | 1992-09-02 | Merck Frosst Canada Inc. | Naphthalene lactones 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 |
| 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 |
| US5252599A (en) * | 1992-08-27 | 1993-10-12 | Merck Frosst Canada, Inc. | Heteroarylnaphthalene hydroxy acids as inhibitors of leukotriene biosynthesis |
| US5428060A (en) * | 1992-08-27 | 1995-06-27 | Merck Frosst Canada, Inc. | Heteroarylnaphthalene lactones as inhibitors of leukotriene biosynthesis |
| US5350744A (en) * | 1992-08-27 | 1994-09-27 | Merck Frosst Canada, Inc. | Phenylnaphthalene lactones as inhibitors of leukotriene biosynthesis |
| US5426109A (en) * | 1992-08-27 | 1995-06-20 | Merck Frosst Canada, Inc. | Phenylnaphthalene hydroxy acids |
| 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. |
| CA2341540A1 (en) | 1998-08-25 | 2000-03-02 | Yale University | Inhibition and treatment of hepatitis b virus and flavivirus by helioxanthin and its analogs |
| MXPA01012493A (es) | 1999-06-01 | 2003-09-10 | Univ Texas Southwestern Med Ct | Metodo para tratar la perdida capilar con el uso de derivados de eter difenilico. |
| AR018699A1 (es) | 1999-06-01 | 2001-11-28 | Procter & Gamble | Metodo para el tratamiento de la perdida del cabello el cual comprende administrar una composicion que comprende un compuesto el cual no afecta al corazon |
| US6680344B1 (en) | 1999-06-01 | 2004-01-20 | The University Of Texas Southwestern Medical Center | Method of treating hair loss using diphenylmethane derivatives |
| AU2002328569B9 (en) * | 2001-08-28 | 2005-10-27 | Sankyo Company, Limited | Medicinal compositions containing angiotensin II receptor antagonist |
| 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 |
| CN107375932B (zh) | 2011-10-28 | 2021-12-21 | 夏尔人类遗传性治疗公司 | 用于治疗小儿胆汁淤积性肝病的胆汁酸再循环抑制剂 |
| JP6217939B2 (ja) | 2011-10-28 | 2017-10-25 | ルメナ ファーマシューティカルズ エルエルシー | 高胆汁血症および胆汁うっ滞性肝疾患の処置のための胆汁酸再利用阻害剤 |
| US20140275090A1 (en) | 2013-03-15 | 2014-09-18 | Lumena Pharmaceuticals, Inc. | Bile acid recycling inhibitors for treatment of primary sclerosing cholangitis and inflammatory bowel disease |
| US20140271734A1 (en) | 2013-03-15 | 2014-09-18 | Lumena Pharmaceuticals, Inc. | Bile acid recycling inhibitors for treatment of barrett's esophagus and gastroesophageal reflux disease |
| US20170119806A1 (en) * | 2014-03-31 | 2017-05-04 | 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 |
| BR112021015809A2 (pt) | 2019-02-12 | 2022-01-18 | Mirum Pharmaceuticals Inc | Resposta dependente de genótipo e dose a um asbti em pacientes com deficiência de bomba de exportação de sal biliar |
-
1985
- 1985-12-30 ES ES550578A patent/ES8705837A1/es not_active Expired
- 1985-12-30 US US06/814,805 patent/US4771072A/en not_active Expired - Fee Related
- 1985-12-30 NO NO855355A patent/NO170760C/no unknown
- 1985-12-31 AU AU51751/85A patent/AU584153B2/en not_active Ceased
-
1986
- 1986-01-08 PH PH33266A patent/PH22105A/en unknown
- 1986-01-08 JP JP61002624A patent/JPS61267541A/ja active Pending
- 1986-01-09 BG BG073061A patent/BG45383A3/xx unknown
- 1986-01-09 FI FI860089A patent/FI87557C/fi not_active IP Right Cessation
- 1986-01-09 KR KR1019860000074A patent/KR890001884B1/ko not_active Expired
- 1986-01-09 BG BG082397A patent/BG45385A3/xx unknown
- 1986-01-09 PT PT81814A patent/PT81814B/pt not_active IP Right Cessation
- 1986-01-09 HU HU8690A patent/HU196737B/hu not_active IP Right Cessation
- 1986-01-10 DE DE8686100282T patent/DE3672501D1/de not_active Expired - Lifetime
- 1986-01-10 AT AT86100282T patent/ATE54441T1/de not_active IP Right Cessation
- 1986-01-10 CN CN86100090A patent/CN1006464B/zh not_active Expired
- 1986-01-10 EP EP86100282A patent/EP0188248B1/en not_active Expired - Lifetime
- 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 JP63310353A patent/JPH0272136A/ja active Pending
- 1988-12-08 JP JP63310354A patent/JPH0272170A/ja active Granted
-
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
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7629381B2 (en) | 2001-06-19 | 2009-12-08 | Axelar Ab | Use of specific cyklolignans |
| US7662851B2 (en) | 2001-06-19 | 2010-02-16 | Axelar Ab | Use of specific cyklolignans |
| US7709526B2 (en) | 2001-06-19 | 2010-05-04 | Biovitrum Ab | Use of cyclolignans and new cyclolignans |
| US8389747B2 (en) | 2001-06-19 | 2013-03-05 | Axelar Ab | Use of specific cyklolignans |
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