CH545759A - Indane/tetralin carboxylic acid derivs anti-inflammatories - Google Patents
Indane/tetralin carboxylic acid derivs anti-inflammatoriesInfo
- Publication number
- CH545759A CH545759A CH545759DA CH545759A CH 545759 A CH545759 A CH 545759A CH 545759D A CH545759D A CH 545759DA CH 545759 A CH545759 A CH 545759A
- Authority
- CH
- Switzerland
- Prior art keywords
- parts
- mixture
- carboxylic acid
- volume
- sep
- Prior art date
Links
- -1 tetralin carboxylic acid Chemical class 0.000 title description 34
- 239000002260 anti-inflammatory agent Substances 0.000 title description 7
- 229940121363 anti-inflammatory agent Drugs 0.000 title description 6
- 230000003110 anti-inflammatory effect Effects 0.000 title description 5
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 title 2
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetraline Natural products C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 title 2
- 125000005843 halogen group Chemical group 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 46
- 238000002360 preparation method Methods 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 6
- 230000026030 halogenation Effects 0.000 claims description 4
- 238000005658 halogenation reaction Methods 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 abstract description 19
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 abstract description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract description 2
- 150000003839 salts Chemical class 0.000 abstract description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 5
- 101150047265 COR2 gene Proteins 0.000 abstract 1
- 101100467189 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) QCR2 gene Proteins 0.000 abstract 1
- 150000003997 cyclic ketones Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 109
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 76
- 239000013078 crystal Substances 0.000 description 59
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 57
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 51
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 44
- 238000002844 melting Methods 0.000 description 39
- 230000008018 melting Effects 0.000 description 39
- 239000000243 solution Substances 0.000 description 39
- 239000000460 chlorine Substances 0.000 description 37
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- 238000001816 cooling Methods 0.000 description 34
- 239000002904 solvent Substances 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 32
- 238000000921 elemental analysis Methods 0.000 description 31
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
- 239000010410 layer Substances 0.000 description 30
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- OIRAEJWYWSAQNG-UHFFFAOYSA-N Clidanac Chemical compound ClC=1C=C2C(C(=O)O)CCC2=CC=1C1CCCCC1 OIRAEJWYWSAQNG-UHFFFAOYSA-N 0.000 description 21
- 238000001953 recrystallisation Methods 0.000 description 21
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 17
- 229960004756 ethanol Drugs 0.000 description 17
- 235000019441 ethanol Nutrition 0.000 description 17
- 239000003208 petroleum Substances 0.000 description 17
- 238000003756 stirring Methods 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 15
- 239000005457 ice water Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 13
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 11
- BKEWDCUQDVDPHC-UHFFFAOYSA-N 5-cyclohexyl-2,3-dihydro-1h-indene-1-carboxylic acid Chemical compound C=1C=C2C(C(=O)O)CCC2=CC=1C1CCCCC1 BKEWDCUQDVDPHC-UHFFFAOYSA-N 0.000 description 10
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 10
- 229910052938 sodium sulfate Inorganic materials 0.000 description 10
- 235000011152 sodium sulphate Nutrition 0.000 description 10
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 9
- 238000010992 reflux Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 7
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 6
- 238000000862 absorption spectrum Methods 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 229910000497 Amalgam Inorganic materials 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 229910052725 zinc Inorganic materials 0.000 description 5
- 239000011701 zinc Substances 0.000 description 5
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 4
- 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 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- PYTBQLTVFVFKOW-UHFFFAOYSA-N 3-(4-cyclohexylphenyl)oxolane-2,5-dione Chemical compound O=C1OC(=O)CC1C1=CC=C(C2CCCCC2)C=C1 PYTBQLTVFVFKOW-UHFFFAOYSA-N 0.000 description 3
- IAIYUCIDTWPHKH-UHFFFAOYSA-N 5-cyclohexyl-3-oxo-1,2-dihydroindene-1-carboxylic acid Chemical compound C=1C=C2C(C(=O)O)CC(=O)C2=CC=1C1CCCCC1 IAIYUCIDTWPHKH-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 235000001258 Cinchona calisaya Nutrition 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000001754 anti-pyretic effect Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 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
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- RCTYPNKXASFOBE-UHFFFAOYSA-M chloromercury Chemical compound [Hg]Cl RCTYPNKXASFOBE-UHFFFAOYSA-M 0.000 description 3
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 150000002366 halogen compounds Chemical class 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 229960002895 phenylbutazone Drugs 0.000 description 3
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229960000948 quinine Drugs 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- UNBNFPZJBCKFKR-UHFFFAOYSA-N 2-(4-cyclohexylphenyl)acetonitrile Chemical compound C1=CC(CC#N)=CC=C1C1CCCCC1 UNBNFPZJBCKFKR-UHFFFAOYSA-N 0.000 description 2
- MMIMBTDQSGAEEU-UHFFFAOYSA-N 2-(4-cyclohexylphenyl)butanedioic acid Chemical compound C1=CC(C(C(O)=O)CC(=O)O)=CC=C1C1CCCCC1 MMIMBTDQSGAEEU-UHFFFAOYSA-N 0.000 description 2
- FILBTULDBQNHQR-UHFFFAOYSA-N 2-(4-cyclohexylphenyl)pentanedioic acid Chemical compound C1=CC(C(C(O)=O)CCC(=O)O)=CC=C1C1CCCCC1 FILBTULDBQNHQR-UHFFFAOYSA-N 0.000 description 2
- RKVKEZGFRSYYFO-UHFFFAOYSA-N 2-(4-propan-2-ylphenyl)butanedioic acid Chemical compound CC(C)C1=CC=C(C(CC(O)=O)C(O)=O)C=C1 RKVKEZGFRSYYFO-UHFFFAOYSA-N 0.000 description 2
- LQAVBVHGTCYZMO-UHFFFAOYSA-N 3-(4-cyclohexylphenyl)oxane-2,6-dione Chemical compound C1(CCCCC1)C1=CC=C(C=C1)C1C(=O)OC(CC1)=O LQAVBVHGTCYZMO-UHFFFAOYSA-N 0.000 description 2
- UZBORPHICIKJCC-UHFFFAOYSA-N 3-[4-(2-methylpropyl)phenyl]oxolane-2,5-dione Chemical compound C(C(C)C)C1=CC=C(C=C1)C1C(=O)OC(C1)=O UZBORPHICIKJCC-UHFFFAOYSA-N 0.000 description 2
- BSKOVKLKCOLAHV-UHFFFAOYSA-N 3-oxo-5-propan-2-yl-1,2-dihydroindene-1-carboxylic acid Chemical compound CC(C)C1=CC=C2C(C(O)=O)CC(=O)C2=C1 BSKOVKLKCOLAHV-UHFFFAOYSA-N 0.000 description 2
- HDBQKZNTGFUZQC-UHFFFAOYSA-N 5-(2-methylpropyl)-2,3-dihydro-1H-indene-1-carboxylic acid Chemical compound C(C(C)C)C=1C=C2CCC(C2=CC1)C(=O)O HDBQKZNTGFUZQC-UHFFFAOYSA-N 0.000 description 2
- FTWAHTXYAAZXJP-UHFFFAOYSA-N 5-(2-methylpropyl)-3-oxo-1,2-dihydroindene-1-carboxylic acid Chemical compound O=C1CC(C2=CC=C(C=C12)CC(C)C)C(=O)O FTWAHTXYAAZXJP-UHFFFAOYSA-N 0.000 description 2
- PEYNYKGOXRPLIS-UHFFFAOYSA-N 5-cyclohexyl-1-methyl-2,3-dihydroindene-1-carboxylic acid Chemical compound CC1(CCC2=CC(=CC=C12)C1CCCCC1)C(=O)O PEYNYKGOXRPLIS-UHFFFAOYSA-N 0.000 description 2
- ZVROSPVIIXITFH-UHFFFAOYSA-N 5-propan-2-yl-2,3-dihydro-1h-indene-1-carboxylic acid Chemical compound CC(C)C1=CC=C2C(C(O)=O)CCC2=C1 ZVROSPVIIXITFH-UHFFFAOYSA-N 0.000 description 2
- RICKFPIKPLNXSG-UHFFFAOYSA-N 6-bromo-5-cyclohexyl-2,3-dihydro-1H-indene-1-carboxylic acid Chemical compound BrC1=C(C=C2CCC(C2=C1)C(=O)O)C1CCCCC1 RICKFPIKPLNXSG-UHFFFAOYSA-N 0.000 description 2
- ZNJFSARNFDRMLW-UHFFFAOYSA-N 6-chloro-5-cyclohexyl-1-methyl-2,3-dihydroindene-1-carboxylic acid Chemical compound ClC1=C(C=C2CCC(C2=C1)(C(=O)O)C)C1CCCCC1 ZNJFSARNFDRMLW-UHFFFAOYSA-N 0.000 description 2
- QBGRGTVSLSYIQN-UHFFFAOYSA-N 6-cyclohexyl-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid Chemical compound C=1C=C2C(C(=O)O)CCCC2=CC=1C1CCCCC1 QBGRGTVSLSYIQN-UHFFFAOYSA-N 0.000 description 2
- KFSGDRYIPPTVPB-UHFFFAOYSA-N 6-cyclohexyl-4-oxo-2,3-dihydro-1h-naphthalene-1-carboxylic acid Chemical compound C=1C=C2C(C(=O)O)CCC(=O)C2=CC=1C1CCCCC1 KFSGDRYIPPTVPB-UHFFFAOYSA-N 0.000 description 2
- VCICFQBNKHGFFZ-UHFFFAOYSA-N 7-chloro-6-cyclohexyl-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCCC2=CC=1C1CCCCC1 VCICFQBNKHGFFZ-UHFFFAOYSA-N 0.000 description 2
- 101100244083 Arabidopsis thaliana PKL gene Proteins 0.000 description 2
- PUXHPXWVXRUTSJ-UHFFFAOYSA-N ClC1=C(C=C2CCC(C2=C1)C(=O)O)C(C)C Chemical compound ClC1=C(C=C2CCC(C2=C1)C(=O)O)C(C)C PUXHPXWVXRUTSJ-UHFFFAOYSA-N 0.000 description 2
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 239000000730 antalgic agent Substances 0.000 description 2
- 239000002221 antipyretic Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 150000003857 carboxamides Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- DMVRFQWRZQQKJO-UHFFFAOYSA-N ethyl 2-cyano-3-(4-cyclohexylphenyl)but-2-enoate Chemical compound C(#N)C(C(=O)OCC)=C(C)C1=CC=C(C=C1)C1CCCCC1 DMVRFQWRZQQKJO-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000002140 halogenating effect Effects 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 229960002523 mercuric chloride Drugs 0.000 description 2
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 2
- CPBGSLIVFJMDAK-UHFFFAOYSA-N methyl 5-cyclohexyl-2,3-dihydro-1h-indene-1-carboxylate Chemical compound C=1C=C2C(C(=O)OC)CCC2=CC=1C1CCCCC1 CPBGSLIVFJMDAK-UHFFFAOYSA-N 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 229910052755 nonmetal Inorganic materials 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 230000003637 steroidlike Effects 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- MSDQNIRGPBARGC-UHFFFAOYSA-N 1-(4-cyclohexylphenyl)ethanone Chemical compound C1=CC(C(=O)C)=CC=C1C1CCCCC1 MSDQNIRGPBARGC-UHFFFAOYSA-N 0.000 description 1
- MJZDBKQPOOWKRN-UHFFFAOYSA-N 2,3-dimethoxy-6-methyl-4-propan-2-ylnaphthalene-1-carbaldehyde Chemical compound C1=C(C)C=CC2=C(C=O)C(OC)=C(OC)C(C(C)C)=C21 MJZDBKQPOOWKRN-UHFFFAOYSA-N 0.000 description 1
- DMLDHVQWKHKLCP-UHFFFAOYSA-N 2-(4-cyclohexylphenyl)-2-methylbutanedioic acid Chemical compound CC(C(=O)O)(CC(=O)O)C1=CC=C(C=C1)C1CCCCC1 DMLDHVQWKHKLCP-UHFFFAOYSA-N 0.000 description 1
- QSHDPBIZBSOQPQ-UHFFFAOYSA-N 3-(4-propan-2-ylphenyl)oxolane-2,5-dione Chemical compound C1=CC(C(C)C)=CC=C1C1C(=O)OC(=O)C1 QSHDPBIZBSOQPQ-UHFFFAOYSA-N 0.000 description 1
- OQQYLHNEIIVBCG-UHFFFAOYSA-N 5-cyclohexyl-1-methyl-3-oxo-2H-indene-1-carboxylic acid Chemical compound CC1(CC(C2=CC(=CC=C12)C1CCCCC1)=O)C(=O)O OQQYLHNEIIVBCG-UHFFFAOYSA-N 0.000 description 1
- YZNOHIGDHJKRCI-UHFFFAOYSA-N 6-chloro-5-(2-methylpropyl)-2,3-dihydro-1H-indene-1-carboxylic acid Chemical compound ClC1=C(C=C2CCC(C2=C1)C(=O)O)CC(C)C YZNOHIGDHJKRCI-UHFFFAOYSA-N 0.000 description 1
- AZHWXUUAMKZRTB-UHFFFAOYSA-N 6-chloro-5-cyclohexyl-2,3-dihydro-1h-indene-1-carboxamide Chemical compound ClC=1C=C2C(C(=O)N)CCC2=CC=1C1CCCCC1 AZHWXUUAMKZRTB-UHFFFAOYSA-N 0.000 description 1
- RYPBRYOHPXRITH-UHFFFAOYSA-N 6-chloro-5-ethyl-2,3-dihydro-1H-indene-1-carboxylic acid Chemical compound ClC1=C(C=C2CCC(C2=C1)C(=O)O)CC RYPBRYOHPXRITH-UHFFFAOYSA-N 0.000 description 1
- PQRRUPYRMWXGNI-UHFFFAOYSA-N 7-chloro-6-cyclohexyl-1-methyl-3,4-dihydro-2h-naphthalene-1-carboxylic acid Chemical compound ClC=1C=C2C(C)(C(O)=O)CCCC2=CC=1C1CCCCC1 PQRRUPYRMWXGNI-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- DGQBFKPDZRJQFX-UHFFFAOYSA-N ClC1=C(C=C2CCC(C2=C1)(C(=O)O)CC)C1CCCCC1 Chemical compound ClC1=C(C=C2CCC(C2=C1)(C(=O)O)CC)C1CCCCC1 DGQBFKPDZRJQFX-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000009435 amidation Effects 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 1
- 229940125716 antipyretic agent Drugs 0.000 description 1
- 239000003435 antirheumatic agent Substances 0.000 description 1
- DAMJCWMGELCIMI-UHFFFAOYSA-N benzyl n-(2-oxopyrrolidin-3-yl)carbamate Chemical compound C=1C=CC=CC=1COC(=O)NC1CCNC1=O DAMJCWMGELCIMI-UHFFFAOYSA-N 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 150000004651 carbonic acid esters Chemical class 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000013211 curve analysis Methods 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004821 distillation 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
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000010575 fractional recrystallization Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- YQGZPEYSJMFQTE-UHFFFAOYSA-N methyl 6-chloro-5-cyclohexyl-2,3-dihydro-1h-indene-1-carboxylate Chemical compound ClC=1C=C2C(C(=O)OC)CCC2=CC=1C1CCCCC1 YQGZPEYSJMFQTE-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000003826 tablet Substances 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
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
- C07C57/34—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings containing more than one carboxyl group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3719969 | 1969-05-14 | ||
| JP10457669 | 1969-12-25 | ||
| JP3319570A JPS4920567B1 (en, 2012) | 1970-04-18 | 1970-04-18 | |
| JP3319470A JPS4920566B1 (en, 2012) | 1970-04-18 | 1970-04-18 | |
| CH721370A CH545261A (de) | 1969-05-14 | 1970-05-14 | Verfahren zur Herstellung von cyclischen Carbonsäuren bzw. Carbonsäurederivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH545759A true CH545759A (en) | 1974-02-15 |
Family
ID=27509300
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH545759D CH545759A (en) | 1969-05-14 | 1970-05-14 | Indane/tetralin carboxylic acid derivs anti-inflammatories |
| CH545760D CH545760A (en, 2012) | 1969-05-14 | 1970-05-14 | |
| CH545769D CH545769A (en, 2012) | 1969-05-14 | 1970-05-14 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH545760D CH545760A (en, 2012) | 1969-05-14 | 1970-05-14 | |
| CH545769D CH545769A (en, 2012) | 1969-05-14 | 1970-05-14 |
Country Status (1)
| Country | Link |
|---|---|
| CH (3) | CH545759A (en, 2012) |
-
1970
- 1970-05-14 CH CH545759D patent/CH545759A/de not_active IP Right Cessation
- 1970-05-14 CH CH545760D patent/CH545760A/xx not_active IP Right Cessation
- 1970-05-14 CH CH545769D patent/CH545769A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CH545769A (en, 2012) | 1974-02-15 |
| CH545760A (en, 2012) | 1974-02-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |