NO300206B1 - Fremgangsmåte for fremstilling av terapeutisk aktive benzosyrederivater, samt bisykliske amidforbindelser - Google Patents
Fremgangsmåte for fremstilling av terapeutisk aktive benzosyrederivater, samt bisykliske amidforbindelser Download PDFInfo
- Publication number
- NO300206B1 NO300206B1 NO914519A NO914519A NO300206B1 NO 300206 B1 NO300206 B1 NO 300206B1 NO 914519 A NO914519 A NO 914519A NO 914519 A NO914519 A NO 914519A NO 300206 B1 NO300206 B1 NO 300206B1
- Authority
- NO
- Norway
- Prior art keywords
- compound
- lower alkyl
- benzoic acid
- general formula
- formula
- Prior art date
Links
- -1 bicyclic amide compounds Chemical class 0.000 title claims abstract description 21
- 238000000034 method Methods 0.000 title claims description 32
- 238000002360 preparation method Methods 0.000 title claims description 6
- 150000001558 benzoic acid derivatives Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- 125000003118 aryl group Chemical group 0.000 claims abstract description 12
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 238000007257 deesterification reaction Methods 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 abstract description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract description 6
- 239000005711 Benzoic acid Substances 0.000 abstract description 3
- 238000002441 X-ray diffraction Methods 0.000 abstract description 3
- 229960001413 acetanilide Drugs 0.000 abstract description 3
- 235000010233 benzoic acid Nutrition 0.000 abstract description 3
- 125000001475 halogen functional group Chemical group 0.000 abstract 2
- 150000004820 halides Chemical class 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 239000013078 crystal Substances 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000000203 mixture Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000010586 diagram Methods 0.000 description 6
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 150000001448 anilines Chemical class 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 238000001308 synthesis method Methods 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 3
- HSTAGCWQAIXJQM-UHFFFAOYSA-N 2,5-dichloro-2,5-dimethylhexane Chemical compound CC(C)(Cl)CCC(C)(C)Cl HSTAGCWQAIXJQM-UHFFFAOYSA-N 0.000 description 2
- AMDKYPNODLTUMY-UHFFFAOYSA-N 5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-amine Chemical compound NC1=CC=C2C(C)(C)CCC(C)(C)C2=C1 AMDKYPNODLTUMY-UHFFFAOYSA-N 0.000 description 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 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
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 230000002140 halogenating effect Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- CUMBLUSSCDUGRG-UHFFFAOYSA-N n-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)acetamide Chemical compound CC1(C)CCC(C)(C)C=2C1=CC(NC(=O)C)=CC=2 CUMBLUSSCDUGRG-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- JRZGPXSSNPTNMA-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalen-1-amine Chemical class C1=CC=C2C(N)CCCC2=C1 JRZGPXSSNPTNMA-UHFFFAOYSA-N 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- ZWNMRZQYWRLGMM-UHFFFAOYSA-N 2,5-dimethylhexane-2,5-diol Chemical compound CC(C)(O)CCC(C)(C)O ZWNMRZQYWRLGMM-UHFFFAOYSA-N 0.000 description 1
- NTNUPCREDHXJEL-UHFFFAOYSA-N 2-methylbenzene-1,4-dicarbonyl chloride Chemical compound CC1=CC(C(Cl)=O)=CC=C1C(Cl)=O NTNUPCREDHXJEL-UHFFFAOYSA-N 0.000 description 1
- 229910016523 CuKa Inorganic materials 0.000 description 1
- 229910003074 TiCl4 Inorganic materials 0.000 description 1
- 229910021623 Tin(IV) bromide Inorganic materials 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical compound Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 229940023913 cation exchange resins Drugs 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 231100000042 hematotoxic Toxicity 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- CBBXAIYXFKPCMD-UHFFFAOYSA-N methyl 4-[(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)carbamoyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C(=O)NC1=CC=C2C(C)(C)CCC(C)(C)C2=C1 CBBXAIYXFKPCMD-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004971 nitroalkyl group Chemical group 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000004492 retinoid derivatives Chemical class 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LTSUHJWLSNQKIP-UHFFFAOYSA-J tin(iv) bromide Chemical compound Br[Sn](Br)(Br)Br LTSUHJWLSNQKIP-UHFFFAOYSA-J 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- UBZYKBZMAMTNKW-UHFFFAOYSA-J titanium tetrabromide Chemical compound Br[Ti](Br)(Br)Br UBZYKBZMAMTNKW-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/127—Liposomes
- A61K9/1271—Non-conventional liposomes, e.g. PEGylated liposomes, liposomes coated with polymers
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/14—Preparation of carboxylic acid amides by formation of carboxamide groups together with reactions not involving the carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C233/07—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/65—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (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)
- Developing Agents For Electrophotography (AREA)
- Paper (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7143390 | 1990-03-20 | ||
| PCT/JP1991/000350 WO1991014673A1 (en) | 1990-03-20 | 1991-03-15 | Novel process for producing benzoic acid derivative |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO914519D0 NO914519D0 (no) | 1991-11-19 |
| NO914519L NO914519L (no) | 1992-01-07 |
| NO300206B1 true NO300206B1 (no) | 1997-04-28 |
Family
ID=13460393
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO914519A NO300206B1 (no) | 1990-03-20 | 1991-11-19 | Fremgangsmåte for fremstilling av terapeutisk aktive benzosyrederivater, samt bisykliske amidforbindelser |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US5214202A (de) |
| EP (1) | EP0478787B1 (de) |
| JP (2) | JP3001632B2 (de) |
| KR (1) | KR960014911B1 (de) |
| AT (1) | ATE115946T1 (de) |
| AU (1) | AU628732B2 (de) |
| DE (1) | DE69106098T2 (de) |
| DK (1) | DK0478787T3 (de) |
| ES (1) | ES2069285T3 (de) |
| FI (1) | FI915445A0 (de) |
| GR (1) | GR3015138T3 (de) |
| HU (2) | HU210300B (de) |
| NO (1) | NO300206B1 (de) |
| WO (1) | WO1991014673A1 (de) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5264578A (en) | 1987-03-20 | 1993-11-23 | Allergan, Inc. | Disubstituted acetylenes bearing heterobicyclic groups and heteroaromatic or phenyl groups having retinoid like activity |
| US5648514A (en) | 1994-12-29 | 1997-07-15 | Allergan | Substituted acetylenes having retinoid-like biological activity |
| US5534641A (en) | 1994-12-29 | 1996-07-09 | Allergan | Acetylenes disubstituted with 2-tetrahydropyranoxyaryl and aryl or heteroaryl groups having retinoid-like biological activity |
| US5675033A (en) | 1995-06-06 | 1997-10-07 | Allergan | 2,4-pentadienoic acid derivatives having retinoid-like biological activity |
| US5917082A (en) | 1995-06-06 | 1999-06-29 | Allergan Sales, Inc. | 2,4-pentadienoic acid derivatives having retinoid-like biological activity |
| US6218128B1 (en) | 1997-09-12 | 2001-04-17 | Allergan Sales, Inc. | Methods of identifying compounds having nuclear receptor negative hormone and/or antagonist activities |
| US5776699A (en) * | 1995-09-01 | 1998-07-07 | Allergan, Inc. | Method of identifying negative hormone and/or antagonist activities |
| US5958954A (en) | 1995-09-01 | 1999-09-28 | Allergan Sales, Inc. | Synthesis and use of retinoid compounds having negative hormone and/or antagonist activities |
| US6008204A (en) | 1995-09-01 | 1999-12-28 | Allergan Sales, Inc. | Synthesis and use of retinoid compounds having negative hormone and/or antagonist activities |
| US5952345A (en) | 1995-09-01 | 1999-09-14 | Allergan Sales, Inc. | Synthesis and use of retinoid compounds having negative hormone and/or antagonist activities |
| US5675024A (en) | 1995-11-22 | 1997-10-07 | Allergan | Aryl or heteroaryl amides of tetrahydronaphthalene, chroman, thiochroman and 1,2,3,4,-tetrahydroquinoline carboxylic acids, having an electron withdrawing substituent in the aromatic or heteroaromatic moiety, having retinoid-like biological activity |
| US5763635A (en) | 1996-06-21 | 1998-06-09 | Allergan | Tetrahydronaphthalene derivatives substituted in the 8 position with alkyhidene groups having retinoid and/or retinoid antagonist-like biological activity |
| US5741896A (en) | 1996-06-21 | 1998-04-21 | Allergan | O- or S- substituted tetrahydronaphthalene derivatives having retinoid and/or retinoid antagonist-like biological activity |
| US5773594A (en) | 1996-06-21 | 1998-06-30 | Allergan | Alkyl or aryl substituted dihydronaphthalene derivatives having retinoid and/or retinoid antagonist-like biological activity |
| US6555690B2 (en) | 1996-06-21 | 2003-04-29 | Allergan, Inc. | Alkyl or aryl substituted dihydronaphthalene derivatives having retinoid and/or retinoid antagonist-like biological activity |
| US5728846A (en) | 1996-12-12 | 1998-03-17 | Allergan | Benzo 1,2-g!-chrom-3-ene and benzo 1,2-g!-thiochrom-3-ene derivatives |
| US6037488A (en) | 1997-04-19 | 2000-03-14 | Allergan Sales, Inc. | Trisubstituted phenyl derivatives having retinoid agonist, antagonist or inverse agonist type biological activity |
| US5919970A (en) | 1997-04-24 | 1999-07-06 | Allergan Sales, Inc. | Substituted diaryl or diheteroaryl methanes, ethers and amines having retinoid agonist, antagonist or inverse agonist type biological activity |
| DE60143166D1 (de) | 2000-09-01 | 2010-11-11 | Toko Pharmaceutical Ind Co Ltd | Verfahren zur herstellung von kristallen von benzoesäure-derivaten |
| US6620963B1 (en) | 2002-09-19 | 2003-09-16 | Allergan, Inc. | TRICYCLO[6.2.202,7]DODECA-2(7),3,5-TRIEN-4-CARBONYLAMINO-PHENYL AND TRICYCLO[6.2.202,7]DODECA-2(7),3,5-TRIEN-4-CARBONYLAMINO-HETEROARYL AND RELATED COMPOUNDS HAVING RARα RECEPTOR SELECTIVE BIOLOGICAL ACTIVITY |
| US6727277B1 (en) | 2002-11-12 | 2004-04-27 | Kansas State University Research Foundation | Compounds affecting cholesterol absorption |
| CN101200435B (zh) * | 2006-12-12 | 2011-12-07 | 江苏恒瑞医药股份有限公司 | 他米巴罗汀ⅱ型结晶的制备方法 |
| WO2008120711A1 (ja) | 2007-03-30 | 2008-10-09 | Tmrc Co., Ltd. | タミバロテンカプセル剤 |
| WO2009114966A1 (zh) * | 2008-03-19 | 2009-09-24 | 江苏恒瑞医药股份有限公司 | 他米巴罗汀ii型结晶的制备方法 |
| CN101665449B (zh) * | 2009-09-24 | 2012-12-12 | 山东大学 | 他米巴罗汀的水溶性前药及其制备方法与应用 |
| CN102633673A (zh) * | 2012-03-30 | 2012-08-15 | 上海共价化学科技有限公司 | 他米巴罗汀的合成方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2500157C2 (de) * | 1975-01-03 | 1983-09-15 | Hoechst Ag, 6230 Frankfurt | N-Acyl-4-(2-aminoäthyl)-benzoesäuren, deren Salze und Ester, Verfahren zu deren Herstellung und deren Verwendung |
| US4227014A (en) * | 1978-02-27 | 1980-10-07 | American Cyanamid Company | 4-[(Cycloalkyl or cycloalkenyl substituted)amino, alkylamino or alkenylamino]benzoic acids and salts thereof |
| DK214679A (da) * | 1978-06-09 | 1979-12-10 | Chugai Pharmaceutical Co Ltd | Terephthalsyremonoamid derivater fremgangsmaade til deres fremstilling samt antiallergiske midler indeholdende disse |
| JPS6176440A (ja) * | 1984-09-19 | 1986-04-18 | Koichi Shiyudo | 安息香酸誘導体 |
| US4808631A (en) * | 1986-11-07 | 1989-02-28 | Hoffmann-La Roche Inc. | Aromatic acid derivatives |
| US4989090A (en) * | 1989-04-05 | 1991-01-29 | Yves C. Faroudja | Television scan line doubler including temporal median filter |
-
1991
- 1991-03-15 DK DK91906248.9T patent/DK0478787T3/da active
- 1991-03-15 ES ES91906248T patent/ES2069285T3/es not_active Expired - Lifetime
- 1991-03-15 DE DE69106098T patent/DE69106098T2/de not_active Expired - Lifetime
- 1991-03-15 WO PCT/JP1991/000350 patent/WO1991014673A1/ja active IP Right Grant
- 1991-03-15 JP JP3505852A patent/JP3001632B2/ja not_active Expired - Lifetime
- 1991-03-15 AU AU74826/91A patent/AU628732B2/en not_active Ceased
- 1991-03-15 EP EP91906248A patent/EP0478787B1/de not_active Expired - Lifetime
- 1991-03-15 HU HU9202856A patent/HU210300B/hu not_active IP Right Cessation
- 1991-03-15 AT AT91906248T patent/ATE115946T1/de not_active IP Right Cessation
- 1991-03-15 KR KR1019910701646A patent/KR960014911B1/ko not_active IP Right Cessation
- 1991-03-15 US US07/778,985 patent/US5214202A/en not_active Expired - Lifetime
- 1991-03-15 HU HU913801A patent/HU208417B/hu not_active IP Right Cessation
- 1991-11-18 FI FI915445A patent/FI915445A0/fi unknown
- 1991-11-19 NO NO914519A patent/NO300206B1/no not_active IP Right Cessation
-
1995
- 1995-02-22 GR GR950400358T patent/GR3015138T3/el unknown
-
1999
- 1999-07-16 JP JP11203717A patent/JP3076569B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| NO914519L (no) | 1992-01-07 |
| HU208417B (en) | 1993-10-28 |
| KR960014911B1 (ko) | 1996-10-21 |
| HUT61272A (en) | 1992-12-28 |
| EP0478787A1 (de) | 1992-04-08 |
| HU913801D0 (en) | 1992-07-28 |
| HUT61270A (en) | 1992-12-28 |
| ES2069285T3 (es) | 1995-05-01 |
| DE69106098D1 (de) | 1995-02-02 |
| US5214202A (en) | 1993-05-25 |
| GR3015138T3 (en) | 1995-05-31 |
| KR920702342A (ko) | 1992-09-03 |
| HU9202856D0 (en) | 1992-11-30 |
| EP0478787B1 (de) | 1994-12-21 |
| JP2000034262A (ja) | 2000-02-02 |
| FI915445A0 (fi) | 1991-11-18 |
| JP3076569B2 (ja) | 2000-08-14 |
| ATE115946T1 (de) | 1995-01-15 |
| NO914519D0 (no) | 1991-11-19 |
| EP0478787A4 (en) | 1992-07-01 |
| DK0478787T3 (da) | 1995-02-20 |
| HU210300B (en) | 1995-03-28 |
| DE69106098T2 (de) | 1995-05-24 |
| WO1991014673A1 (en) | 1991-10-03 |
| JP3001632B2 (ja) | 2000-01-24 |
| AU628732B2 (en) | 1992-09-17 |
| AU7482691A (en) | 1991-10-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO300206B1 (no) | Fremgangsmåte for fremstilling av terapeutisk aktive benzosyrederivater, samt bisykliske amidforbindelser | |
| US2731471A (en) | Nxg hi | |
| IL22818A (en) | 4-Alcohol Acetic Acetic Acids and their History, Processes for Preparation and Pharmaceutical Preparations Containing Them | |
| US2676188A (en) | Acylated glycinamides | |
| US2856429A (en) | Process for the preparation of nitramines | |
| HU193589B (en) | Process for preparing fluorinated phtaloyl- and terephtaloyl compounds | |
| JP3907219B2 (ja) | ｏ−クロロメチル安息香酸クロリドの製造方法 | |
| US2753345A (en) | Substituted mercaptobenzoic acids and methods of preparing the same | |
| US2370015A (en) | Derivatives of tertiary amino aliphatic acids | |
| US3247224A (en) | 6h-[b, f] [1, 4, 5] dibenzo-oxathiazepins | |
| KR100217355B1 (ko) | 5-(3-부티릴-2,4,6-트리메틸)-2-(1-(에톡시이미노)프로필)-3-하이드록시싸이클로헥스-2-엔-1-온 제조방법 | |
| US2654778A (en) | Derivatives of cycloalkylbenzoylaralkanoic acids | |
| ES2729404T3 (es) | Proceso de hidrocloruro de fingolimod | |
| US3743668A (en) | Cyanoethylation of aminophenols | |
| NO132930B (de) | ||
| US2688015A (en) | Manufacture of sulfamerazine | |
| JPH06306042A (ja) | スルホベタインの製造方法 | |
| US2339914A (en) | Chemical compound | |
| Baizer et al. | Synthesis of isoniazid from citric acid | |
| US3609168A (en) | Thiadiazepines | |
| CA1214470A (en) | Process for the preparation of derivatives of 2- diethylamino-1-methyl ethyl cis-1-hydroxy- (bicyclohexyl)-2-carboxylate | |
| JPS5944359A (ja) | １−アゾリル−３，３−ジメチル−１−フエノキシブタン−２−オ−ルの製法 | |
| GB1561153A (en) | Process for the preparation of thiochroman derivatives | |
| US6548692B1 (en) | Method for preparing 1,2-dibromo-2,4-dicyanobutane | |
| KR960007801B1 (ko) | 비이온성 요오드 치환 x선 조영물의 제조방법 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |
Free format text: LAPSED IN SEPTEMBER 2002 |