NO770084L - Analogifremgangsm}te for fremstilling av indankarboksylsyrederivater med antiinflammatorisk, analgetisk og antipyretisk virkning. - Google Patents
Analogifremgangsm}te for fremstilling av indankarboksylsyrederivater med antiinflammatorisk, analgetisk og antipyretisk virkning.Info
- Publication number
- NO770084L NO770084L NO770084A NO770084A NO770084L NO 770084 L NO770084 L NO 770084L NO 770084 A NO770084 A NO 770084A NO 770084 A NO770084 A NO 770084A NO 770084 L NO770084 L NO 770084L
- Authority
- NO
- Norway
- Prior art keywords
- ppm
- protons
- residues
- multiplet
- aromatic
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 20
- 230000001754 anti-pyretic effect Effects 0.000 title claims description 7
- 230000000202 analgesic effect Effects 0.000 title claims description 6
- 230000003110 anti-inflammatory effect Effects 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 5
- JBQMFBWTKWOSQX-UHFFFAOYSA-N 2,3-dihydro-1h-indene-1-carboxylic acid Chemical class C1=CC=C2C(C(=O)O)CCC2=C1 JBQMFBWTKWOSQX-UHFFFAOYSA-N 0.000 title description 2
- 125000003118 aryl group Chemical group 0.000 claims description 70
- 239000002253 acid Substances 0.000 claims description 46
- 150000002148 esters Chemical class 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 17
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- -1 aroyl halide Chemical class 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 6
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 239000011787 zinc oxide Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 3
- 239000013067 intermediate product Substances 0.000 claims 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 1
- 238000002329 infrared spectrum Methods 0.000 description 46
- 238000002844 melting Methods 0.000 description 37
- 230000008018 melting Effects 0.000 description 37
- 150000002576 ketones Chemical class 0.000 description 33
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 29
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 26
- 239000000203 mixture Substances 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- 238000009835 boiling Methods 0.000 description 21
- 238000010992 reflux Methods 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 150000004702 methyl esters Chemical class 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 239000000243 solution Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- WOAAHXNXOSCQFP-UHFFFAOYSA-N 5-benzoyl-2,3-dihydro-1h-indene-2-carboxylic acid Chemical compound C1=C2CC(C(=O)O)CC2=CC=C1C(=O)C1=CC=CC=C1 WOAAHXNXOSCQFP-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 230000002378 acidificating effect Effects 0.000 description 7
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 206010061218 Inflammation Diseases 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 206010030113 Oedema Diseases 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000001603 reducing effect Effects 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2,2'-azo-bis-isobutyronitrile Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- XUDCMQBOWOLYCF-UHFFFAOYSA-N 2,3-dihydro-1h-indene-2-carboxylic acid Chemical compound C1=CC=C2CC(C(=O)O)CC2=C1 XUDCMQBOWOLYCF-UHFFFAOYSA-N 0.000 description 2
- MTGIUHYHWLXUHB-UHFFFAOYSA-N 5-(4-methoxybenzoyl)-2,3-dihydro-1h-indene-2-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC=C(CC(C2)C(O)=O)C2=C1 MTGIUHYHWLXUHB-UHFFFAOYSA-N 0.000 description 2
- OEFWPAIUPVVVNE-UHFFFAOYSA-N 5-benzoyl-2,3-dihydro-1h-indene-2-carbonyl chloride Chemical compound C1=C2CC(C(=O)Cl)CC2=CC=C1C(=O)C1=CC=CC=C1 OEFWPAIUPVVVNE-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 compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 2
- 239000007818 Grignard reagent Substances 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 235000010418 carrageenan Nutrition 0.000 description 2
- 229920001525 carrageenan Polymers 0.000 description 2
- 150000004795 grignard reagents Chemical class 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 235000011837 pasties Nutrition 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- MTOCKFSRHDGQAZ-UHFFFAOYSA-N (3,4-dimethylphenyl)-(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC=C(C)C(C)=C1 MTOCKFSRHDGQAZ-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- RAGSWDIQBBZLLL-UHFFFAOYSA-N 2-chloroethyl(diethyl)azanium;chloride Chemical compound Cl.CCN(CC)CCCl RAGSWDIQBBZLLL-UHFFFAOYSA-N 0.000 description 1
- RIWPNUBHLJVNPT-UHFFFAOYSA-N 2-ethoxycarbonyl-5-(4-methoxybenzoyl)-1,3-dihydroindene-2-carboxylic acid Chemical compound C1=C2CC(C(=O)OCC)(C(O)=O)CC2=CC=C1C(=O)C1=CC=C(OC)C=C1 RIWPNUBHLJVNPT-UHFFFAOYSA-N 0.000 description 1
- QOGHRLGTXVMRLM-UHFFFAOYSA-N 4-bromo-1,2-dimethylbenzene Chemical group CC1=CC=C(Br)C=C1C QOGHRLGTXVMRLM-UHFFFAOYSA-N 0.000 description 1
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical group COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 1
- NXPZODWVOGXKTJ-UHFFFAOYSA-N 5-(2-chlorobenzoyl)-2,3-dihydro-1h-indene-2-carboxylic acid Chemical compound C1=C2CC(C(=O)O)CC2=CC=C1C(=O)C1=CC=CC=C1Cl NXPZODWVOGXKTJ-UHFFFAOYSA-N 0.000 description 1
- HFJXBIDWBHVMAM-UHFFFAOYSA-N 5-(2-methylbenzoyl)-2,3-dihydro-1h-indene-2-carboxylic acid Chemical compound CC1=CC=CC=C1C(=O)C1=CC=C(CC(C2)C(O)=O)C2=C1 HFJXBIDWBHVMAM-UHFFFAOYSA-N 0.000 description 1
- VLYBZFIBLQBSJA-UHFFFAOYSA-N 5-(3-chlorobenzoyl)-2,3-dihydro-1h-indene-2-carboxylic acid Chemical compound C1=C2CC(C(=O)O)CC2=CC=C1C(=O)C1=CC=CC(Cl)=C1 VLYBZFIBLQBSJA-UHFFFAOYSA-N 0.000 description 1
- VZRWNQSPIKCKLT-UHFFFAOYSA-N 5-(3-methoxybenzoyl)-2,3-dihydro-1h-indene-2-carboxylic acid Chemical compound COC1=CC=CC(C(=O)C=2C=C3CC(CC3=CC=2)C(O)=O)=C1 VZRWNQSPIKCKLT-UHFFFAOYSA-N 0.000 description 1
- KFPYSUQOTOAFQW-UHFFFAOYSA-N 5-(3-methylbenzoyl)-2,3-dihydro-1h-indene-2-carboxylic acid Chemical compound CC1=CC=CC(C(=O)C=2C=C3CC(CC3=CC=2)C(O)=O)=C1 KFPYSUQOTOAFQW-UHFFFAOYSA-N 0.000 description 1
- GUAYTFRCWMRPCA-UHFFFAOYSA-N 5-(4-aminobenzoyl)-2,3-dihydro-1h-indene-2-carboxylic acid Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=C(CC(C2)C(O)=O)C2=C1 GUAYTFRCWMRPCA-UHFFFAOYSA-N 0.000 description 1
- PPVLLUOEVCCUFF-UHFFFAOYSA-N 5-(4-chlorobenzoyl)-2,3-dihydro-1h-indene-2-carboxylic acid Chemical compound C1=C2CC(C(=O)O)CC2=CC=C1C(=O)C1=CC=C(Cl)C=C1 PPVLLUOEVCCUFF-UHFFFAOYSA-N 0.000 description 1
- OORACZSUNFYTCW-UHFFFAOYSA-N 5-(cyclohexanecarbonyl)-2,3-dihydro-1h-indene-2-carboxylic acid Chemical compound C1=C2CC(C(=O)O)CC2=CC=C1C(=O)C1CCCCC1 OORACZSUNFYTCW-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 206010015150 Erythema Diseases 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 208000007101 Muscle Cramp Diseases 0.000 description 1
- OVRNDRQMDRJTHS-FMDGEEDCSA-N N-acetyl-beta-D-glucosamine Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-FMDGEEDCSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 1
- 208000005392 Spasm Diseases 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- MXMOTZIXVICDSD-UHFFFAOYSA-N anisoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1 MXMOTZIXVICDSD-UHFFFAOYSA-N 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000001760 anti-analgesic effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 229940125716 antipyretic agent Drugs 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 150000001851 cinnamic acid derivatives Chemical class 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 231100000321 erythema Toxicity 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- OSCTXCOERRNGLW-UHFFFAOYSA-N idrocilamide Chemical compound OCCNC(=O)C=CC1=CC=CC=C1 OSCTXCOERRNGLW-UHFFFAOYSA-N 0.000 description 1
- 150000002468 indanes Chemical class 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- RMOPJLIMRSAIMD-UHFFFAOYSA-N methyl 2,3-dihydro-1h-indene-2-carboxylate Chemical compound C1=CC=C2CC(C(=O)OC)CC2=C1 RMOPJLIMRSAIMD-UHFFFAOYSA-N 0.000 description 1
- UGYZXECHIWTSSB-UHFFFAOYSA-N methyl 5-(4-nitrobenzoyl)-2,3-dihydro-1h-indene-2-carboxylate Chemical compound C1=C2CC(C(=O)OC)CC2=CC=C1C(=O)C1=CC=C([N+]([O-])=O)C=C1 UGYZXECHIWTSSB-UHFFFAOYSA-N 0.000 description 1
- GULPVDQOZGYEJH-UHFFFAOYSA-N methyl 5-(pyridine-3-carbonyl)-2,3-dihydro-1h-indene-2-carboxylate Chemical compound C1=C2CC(C(=O)OC)CC2=CC=C1C(=O)C1=CC=CN=C1 GULPVDQOZGYEJH-UHFFFAOYSA-N 0.000 description 1
- NLIJFVFTCQODAW-UHFFFAOYSA-N methyl 5-benzoyl-2,3-dihydro-1h-indene-2-carboxylate Chemical compound C1=C2CC(C(=O)OC)CC2=CC=C1C(=O)C1=CC=CC=C1 NLIJFVFTCQODAW-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- 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
- C07C45/004—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with organometalhalides
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- 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
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
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- 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
- C07C45/63—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 introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
- C07C49/784—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic with all keto groups bound to a non-condensed ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
-
- 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
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/28—Halogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pain & Pain Management (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (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)
- Pyridine Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7600552A FR2337551A1 (fr) | 1976-01-12 | 1976-01-12 | Nouveaux acides carboxyliques derives de l'indane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO770084L true NO770084L (no) | 1977-07-13 |
Family
ID=9167788
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO770084A NO770084L (no) | 1976-01-12 | 1977-01-11 | Analogifremgangsm}te for fremstilling av indankarboksylsyrederivater med antiinflammatorisk, analgetisk og antipyretisk virkning. |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4269848A (xx) |
| JP (1) | JPS52118454A (xx) |
| AT (1) | AT350544B (xx) |
| AU (1) | AU510933B2 (xx) |
| BE (1) | BE849285A (xx) |
| CA (1) | CA1088943A (xx) |
| CH (1) | CH617173A5 (xx) |
| DD (1) | DD129549A5 (xx) |
| DE (1) | DE2656750C2 (xx) |
| DK (1) | DK144882C (xx) |
| ES (1) | ES454901A1 (xx) |
| FR (1) | FR2337551A1 (xx) |
| GB (1) | GB1520089A (xx) |
| HU (1) | HU172980B (xx) |
| IE (1) | IE44758B1 (xx) |
| IL (1) | IL51205A (xx) |
| MX (1) | MX4227E (xx) |
| NL (1) | NL7700287A (xx) |
| NO (1) | NO770084L (xx) |
| NZ (1) | NZ182995A (xx) |
| SE (1) | SE7700200L (xx) |
| SU (1) | SU688121A3 (xx) |
| ZA (1) | ZA7741B (xx) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2407924A2 (fr) * | 1977-11-08 | 1979-06-01 | Lipha Lyonnaise Indle Pharmace | Acides carboxyliques derives de l'indane utilisables notamment comme medicaments |
| US4224341A (en) | 1976-01-12 | 1980-09-23 | Lipha, Lyonnaise Industrielle Pharmaceutique | 5-Substituted indan-2 carboxylic acid and functional derivatives |
| US5149705A (en) * | 1987-03-13 | 1992-09-22 | Allergan, Inc. | Acetylenes disubstituted with a heteroaromatic group and a tetralin group and having retinoid like activity |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3953500A (en) * | 1973-08-11 | 1976-04-27 | Takeda Chemical Industries, Ltd. | Benzalicyclic carboxylic acid derivative |
| DE2438380C2 (de) | 1973-08-11 | 1986-06-05 | Takeda Chemical Industries, Ltd., Osaka | 4-Benzoylindan-1-carbonsäuren, 4-Benzylindan-1-carbonsäuren, 4-Benzoylindan-1-carbonitrile, 4-Benzoylindan-1-one, 1-Carbamoylindan-4-carbonsäure, 1-Cyano-indan-4-carbonsäure und funktionelle Derivate der Carbonsäuren |
| CH601166A5 (xx) | 1974-02-14 | 1978-06-30 | Ciba Geigy Ag |
-
1976
- 1976-01-12 FR FR7600552A patent/FR2337551A1/fr active Granted
- 1976-12-10 BE BE173155A patent/BE849285A/xx not_active IP Right Cessation
- 1976-12-15 DE DE2656750A patent/DE2656750C2/de not_active Expired
- 1976-12-20 CH CH1603376A patent/CH617173A5/fr not_active IP Right Cessation
- 1976-12-31 CA CA269,025A patent/CA1088943A/en not_active Expired
-
1977
- 1977-01-03 IL IL51205A patent/IL51205A/xx unknown
- 1977-01-04 ZA ZA770041A patent/ZA7741B/xx unknown
- 1977-01-06 NZ NZ182995A patent/NZ182995A/xx unknown
- 1977-01-07 GB GB656/77A patent/GB1520089A/en not_active Expired
- 1977-01-07 AU AU21152/77A patent/AU510933B2/en not_active Expired
- 1977-01-08 ES ES454901A patent/ES454901A1/es not_active Expired
- 1977-01-10 IE IE41/77A patent/IE44758B1/en unknown
- 1977-01-10 MX MX775322U patent/MX4227E/es unknown
- 1977-01-11 DD DD7700196890A patent/DD129549A5/xx unknown
- 1977-01-11 DK DK9477A patent/DK144882C/da active
- 1977-01-11 SE SE7700200A patent/SE7700200L/xx not_active Application Discontinuation
- 1977-01-11 HU HU77LI00000304A patent/HU172980B/hu unknown
- 1977-01-11 NO NO770084A patent/NO770084L/no unknown
- 1977-01-12 NL NL7700287A patent/NL7700287A/xx not_active Application Discontinuation
- 1977-01-12 JP JP228177A patent/JPS52118454A/ja active Pending
- 1977-01-12 SU SU772439854A patent/SU688121A3/ru active
- 1977-01-12 AT AT12377A patent/AT350544B/de not_active IP Right Cessation
-
1978
- 1978-01-27 US US05/873,075 patent/US4269848A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DD129549A5 (de) | 1978-01-25 |
| US4269848A (en) | 1981-05-26 |
| DK144882B (da) | 1982-06-28 |
| DE2656750A1 (de) | 1977-07-14 |
| BE849285A (fr) | 1977-06-10 |
| CA1088943A (en) | 1980-11-04 |
| DK9477A (da) | 1977-07-13 |
| MX4227E (es) | 1982-02-18 |
| FR2337551A1 (fr) | 1977-08-05 |
| JPS52118454A (en) | 1977-10-04 |
| ATA12377A (de) | 1978-11-15 |
| IE44758B1 (en) | 1982-03-24 |
| NL7700287A (nl) | 1977-07-14 |
| DE2656750C2 (de) | 1982-11-04 |
| DK144882C (da) | 1983-01-17 |
| FR2337551B1 (xx) | 1978-11-03 |
| AT350544B (de) | 1979-06-11 |
| SU688121A3 (ru) | 1979-09-25 |
| NZ182995A (en) | 1979-10-25 |
| GB1520089A (en) | 1978-08-02 |
| SE7700200L (sv) | 1977-07-13 |
| IE44758L (en) | 1977-07-12 |
| IL51205A (en) | 1981-01-30 |
| AU2115277A (en) | 1978-07-13 |
| IL51205A0 (en) | 1977-03-31 |
| ES454901A1 (es) | 1977-12-01 |
| HU172980B (hu) | 1979-01-28 |
| CH617173A5 (xx) | 1980-05-14 |
| ZA7741B (en) | 1977-11-30 |
| AU510933B2 (en) | 1980-07-24 |
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