GB1578041A - Benzofurans and benzoxepins - Google Patents
Benzofurans and benzoxepins Download PDFInfo
- Publication number
- GB1578041A GB1578041A GB20208/77A GB2020877A GB1578041A GB 1578041 A GB1578041 A GB 1578041A GB 20208/77 A GB20208/77 A GB 20208/77A GB 2020877 A GB2020877 A GB 2020877A GB 1578041 A GB1578041 A GB 1578041A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- formula
- benzofuran
- cyclohexyl
- chloro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001907 coumarones Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 81
- 238000000034 method Methods 0.000 claims description 23
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- -1 5 Chloro 6 cyclohexyl 3methyl benzofuran Chemical compound 0.000 claims description 7
- ANMAOLTWUVGEOW-UHFFFAOYSA-N 6-cyclohexyl-2,3-dihydro-1-benzofuran Chemical compound C1=C2OCCC2=CC=C1C1CCCCC1 ANMAOLTWUVGEOW-UHFFFAOYSA-N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- IANQTJSKSUMEQM-UHFFFAOYSA-N benzofuran Natural products C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 5
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 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
- HBEDSQVIWPRPAY-UHFFFAOYSA-N dihydro-benzofuran Natural products C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 4
- LWZYUACNWRVDDJ-UHFFFAOYSA-N 1-benzoxepine Chemical compound O1C=CC=CC2=CC=CC=C12 LWZYUACNWRVDDJ-UHFFFAOYSA-N 0.000 claims description 3
- WWRVHMRDUBEFAD-UHFFFAOYSA-N 5-methyl-6-phenyl-1-benzofuran Chemical compound CC1=CC=2C=COC=2C=C1C1=CC=CC=C1 WWRVHMRDUBEFAD-UHFFFAOYSA-N 0.000 claims description 3
- FJNMWNNSLOQQPZ-UHFFFAOYSA-N 5-methyl-6-phenyl-2,3-dihydro-1-benzofuran Chemical compound CC1=CC=2CCOC=2C=C1C1=CC=CC=C1 FJNMWNNSLOQQPZ-UHFFFAOYSA-N 0.000 claims description 3
- SAWBGBYFPGTKDV-UHFFFAOYSA-N 6-cyclohexyl-3-methyl-1-benzofuran Chemical compound C=1C=C2C(C)=COC2=CC=1C1CCCCC1 SAWBGBYFPGTKDV-UHFFFAOYSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- PCPTZBJKLBTDFX-UHFFFAOYSA-N 6-(2-methylpropyl)-2,3-dihydro-1-benzofuran Chemical compound CC(C)CC1=CC=C2CCOC2=C1 PCPTZBJKLBTDFX-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 230000002140 halogenating effect Effects 0.000 claims description 2
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- ZRXHLJNBNWVNIM-UHFFFAOYSA-N 3-methyl-1-benzofuran Chemical compound C1=CC=C2C(C)=COC2=C1 ZRXHLJNBNWVNIM-UHFFFAOYSA-N 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- MEPSCQQLANVMTL-UHFFFAOYSA-N 2-cyclohexyl-5-methyl-1-benzofuran Chemical compound C=1C2=CC(C)=CC=C2OC=1C1CCCCC1 MEPSCQQLANVMTL-UHFFFAOYSA-N 0.000 claims 1
- HXMZLDUBSSPQIB-UHFFFAOYSA-N 2-phenyl-1-benzofuran Chemical compound O1C2=CC=CC=C2C=C1C1=CC=CC=C1 HXMZLDUBSSPQIB-UHFFFAOYSA-N 0.000 claims 1
- WZBZLXHSUKNNEF-UHFFFAOYSA-N 2-propan-2-yl-1-benzofuran Chemical compound C1=CC=C2OC(C(C)C)=CC2=C1 WZBZLXHSUKNNEF-UHFFFAOYSA-N 0.000 claims 1
- KCZQNAOFWQGLCN-UHFFFAOYSA-N 5-methyl-1-benzofuran Chemical compound CC1=CC=C2OC=CC2=C1 KCZQNAOFWQGLCN-UHFFFAOYSA-N 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 72
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- 229940073584 methylene chloride Drugs 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 20
- 239000000203 mixture Substances 0.000 description 19
- 238000003756 stirring Methods 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 239000011734 sodium Substances 0.000 description 12
- 239000012074 organic phase Substances 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical group [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 239000001632 sodium acetate Chemical group 0.000 description 4
- 235000017281 sodium acetate Nutrition 0.000 description 4
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- MQTSWENWISBBJE-UHFFFAOYSA-N 2-(2-bromoethyl)-4-chloro-5-cyclohexylphenol Chemical compound C1=C(CCBr)C(O)=CC(C2CCCCC2)=C1Cl MQTSWENWISBBJE-UHFFFAOYSA-N 0.000 description 3
- BHXUMQIZMPWSGZ-UHFFFAOYSA-N 2-(4-bromobutyl)-4-chloro-5-cyclohexylphenol Chemical compound C1=C(CCCCBr)C(O)=CC(C2CCCCC2)=C1Cl BHXUMQIZMPWSGZ-UHFFFAOYSA-N 0.000 description 3
- UOPLZFMNEQJKSE-UHFFFAOYSA-N 2-(4-cyclohexyl-2-methoxyphenyl)acetic acid Chemical compound C1=C(CC(O)=O)C(OC)=CC(C2CCCCC2)=C1 UOPLZFMNEQJKSE-UHFFFAOYSA-N 0.000 description 3
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 206010030113 Oedema Diseases 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- UMTPMELFHLMDPL-UHFFFAOYSA-N (6-cyclohexyl-2,3-dihydro-1-benzofuran-5-yl)methanol Chemical compound OCC1=CC=2CCOC=2C=C1C1CCCCC1 UMTPMELFHLMDPL-UHFFFAOYSA-N 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 description 2
- LFLKITSXQSAZJR-UHFFFAOYSA-N 1-cyclohexyl-3-methoxybenzene Chemical compound COC1=CC=CC(C2CCCCC2)=C1 LFLKITSXQSAZJR-UHFFFAOYSA-N 0.000 description 2
- HDLINBFTJNGRQA-UHFFFAOYSA-N 2-(5-chloro-4-cyclohexyl-2-methoxyphenyl)ethanol Chemical compound C1=C(CCO)C(OC)=CC(C2CCCCC2)=C1Cl HDLINBFTJNGRQA-UHFFFAOYSA-N 0.000 description 2
- OEFNIERZNJHFMV-UHFFFAOYSA-N 4-(4-cyclohexyl-2-methoxyphenyl)-4-hydroxybutanoic acid Chemical compound C1=C(C(O)CCC(O)=O)C(OC)=CC(C2CCCCC2)=C1 OEFNIERZNJHFMV-UHFFFAOYSA-N 0.000 description 2
- NICSRQLMSAAZFD-UHFFFAOYSA-N 4-(4-cyclohexyl-2-methoxyphenyl)-4-oxobutanoic acid Chemical compound C1=C(C(=O)CCC(O)=O)C(OC)=CC(C2CCCCC2)=C1 NICSRQLMSAAZFD-UHFFFAOYSA-N 0.000 description 2
- QIBPPZAARPQHSB-UHFFFAOYSA-N 4-(4-cyclohexyl-2-methoxyphenyl)butanoic acid Chemical compound C1=C(CCCC(O)=O)C(OC)=CC(C2CCCCC2)=C1 QIBPPZAARPQHSB-UHFFFAOYSA-N 0.000 description 2
- DSOSDRDRRHYKTL-UHFFFAOYSA-N 6-cyclohexyl-3-methyl-2,3-dihydro-1-benzofuran Chemical compound C=1C=C2C(C)COC2=CC=1C1CCCCC1 DSOSDRDRRHYKTL-UHFFFAOYSA-N 0.000 description 2
- HBKAEKDPRRBTIG-UHFFFAOYSA-N 6-cyclohexyl-5-methyl-2,3-dihydro-1-benzofuran Chemical compound CC1=CC=2CCOC=2C=C1C1CCCCC1 HBKAEKDPRRBTIG-UHFFFAOYSA-N 0.000 description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 2
- 239000007818 Grignard reagent Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- GRTGGSXWHGKRSB-UHFFFAOYSA-N dichloromethyl methyl ether Chemical compound COC(Cl)Cl GRTGGSXWHGKRSB-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 150000002222 fluorine compounds Chemical class 0.000 description 2
- 150000004795 grignard reagents Chemical class 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- KCFGRFSWFMDUQI-UHFFFAOYSA-N methyl 2-(4-cyclohexyl-2-methoxyphenyl)acetate Chemical compound C1=C(OC)C(CC(=O)OC)=CC=C1C1CCCCC1 KCFGRFSWFMDUQI-UHFFFAOYSA-N 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
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- AOUMEQXJBFLDMS-UHFFFAOYSA-N (2-cyclohexyl-2,3-dihydro-1-benzofuran-5-yl)methanol Chemical compound C1C2=CC(CO)=CC=C2OC1C1CCCCC1 AOUMEQXJBFLDMS-UHFFFAOYSA-N 0.000 description 1
- QMDIZIDCORWBJK-UHFFFAOYSA-N 1,3-dichloro-2-(1,3-dichloropropan-2-yloxy)propane Chemical compound ClCC(CCl)OC(CCl)CCl QMDIZIDCORWBJK-UHFFFAOYSA-N 0.000 description 1
- KQMIWCAOEFUBQK-UHFFFAOYSA-N 1-methoxy-3-phenylbenzene Chemical group COC1=CC=CC(C=2C=CC=CC=2)=C1 KQMIWCAOEFUBQK-UHFFFAOYSA-N 0.000 description 1
- MPNFMCAOBNNFJF-UHFFFAOYSA-N 2,3-diphenyl-1-benzofuran Chemical compound C1=CC=CC=C1C1=C(C=2C=CC=CC=2)C2=CC=CC=C2O1 MPNFMCAOBNNFJF-UHFFFAOYSA-N 0.000 description 1
- AWJHGKJOVOYVPN-UHFFFAOYSA-N 2-(2-bromoethyl)-5-cyclohexyl-4-methylphenol Chemical compound CC1=CC(CCBr)=C(O)C=C1C1CCCCC1 AWJHGKJOVOYVPN-UHFFFAOYSA-N 0.000 description 1
- YZDGROPVYQGZTK-UHFFFAOYSA-N 3-methyl-2,3-dihydro-1-benzofuran Chemical compound C1=CC=C2C(C)COC2=C1 YZDGROPVYQGZTK-UHFFFAOYSA-N 0.000 description 1
- LHIFAYXODYLAHN-UHFFFAOYSA-N 5-chloro-6-cyclohexyl-1-benzofuran Chemical compound ClC1=CC=2C=COC=2C=C1C1CCCCC1 LHIFAYXODYLAHN-UHFFFAOYSA-N 0.000 description 1
- SYZAEHSQPKWSPY-UHFFFAOYSA-N 5-chloro-6-cyclohexyl-2,3-dihydro-1-benzofuran Chemical compound ClC1=CC=2CCOC=2C=C1C1CCCCC1 SYZAEHSQPKWSPY-UHFFFAOYSA-N 0.000 description 1
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- UJBMXQZUNSBOTC-UHFFFAOYSA-N 5-chloro-6-phenyl-1-benzofuran Chemical compound ClC1=CC=2C=COC=2C=C1C1=CC=CC=C1 UJBMXQZUNSBOTC-UHFFFAOYSA-N 0.000 description 1
- HKLHUMUOWXLIBE-UHFFFAOYSA-N 5-chloro-6-phenyl-2,3-dihydro-1-benzofuran Chemical compound ClC1=CC=2CCOC=2C=C1C1=CC=CC=C1 HKLHUMUOWXLIBE-UHFFFAOYSA-N 0.000 description 1
- DYDVKHQRBFLSFE-UHFFFAOYSA-N 5-chloro-6-propan-2-yl-2,3-dihydro-1-benzofuran Chemical compound C1=C(Cl)C(C(C)C)=CC2=C1CCO2 DYDVKHQRBFLSFE-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- IDBPQBZSIQLJNJ-UHFFFAOYSA-N 6-cyclohexyl-5-methyl-1-benzofuran Chemical compound CC1=CC=2C=COC=2C=C1C1CCCCC1 IDBPQBZSIQLJNJ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- 241000206575 Chondrus crispus Species 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- 206010011732 Cyst Diseases 0.000 description 1
- 206010015150 Erythema Diseases 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 206010018691 Granuloma Diseases 0.000 description 1
- 102000003960 Ligases Human genes 0.000 description 1
- 108090000364 Ligases Proteins 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- UUIQMZJEGPQKFD-UHFFFAOYSA-N Methyl butyrate Chemical compound CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000001760 anti-analgesic effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 210000001772 blood platelet Anatomy 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- SURLGNKAQXKNSP-DBLYXWCISA-N chlorin Chemical compound C\1=C/2\N/C(=C\C3=N/C(=C\C=4NC(/C=C\5/C=CC/1=N/5)=CC=4)/C=C3)/CC\2 SURLGNKAQXKNSP-DBLYXWCISA-N 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 108010011222 cyclo(Arg-Pro) Proteins 0.000 description 1
- 208000031513 cyst Diseases 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 231100000321 erythema Toxicity 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000155 melt Substances 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
- NFCFHFOKISITAW-UHFFFAOYSA-N methyl 2-(5-chloro-4-cyclohexyl-2-methoxyphenyl)acetate Chemical compound C1=C(OC)C(CC(=O)OC)=CC(Cl)=C1C1CCCCC1 NFCFHFOKISITAW-UHFFFAOYSA-N 0.000 description 1
- SJWZJQFNEWTBLZ-UHFFFAOYSA-N methyl 4-(5-chloro-4-cyclohexyl-2-methoxyphenyl)butanoate Chemical compound C1=C(OC)C(CCCC(=O)OC)=CC(Cl)=C1C1CCCCC1 SJWZJQFNEWTBLZ-UHFFFAOYSA-N 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical compound O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/62—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/72—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings and other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans 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 carbon atoms of the hetero ring
- C07D307/83—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
- C07D313/02—Seven-membered rings
- C07D313/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D313/08—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with one six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH612576A CH623045A5 (en) | 1976-05-17 | 1976-05-17 | Process for the preparation of novel 2,3-dihydrobenzofurans and 2,3,4,5-tetrahydro-1-benzoxepins |
| CH774176A CH622256A5 (en) | 1976-06-17 | 1976-06-17 | Process for the preparation of novel benzofurans |
| CH1492976 | 1976-11-26 | ||
| CH1492876 | 1976-11-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1578041A true GB1578041A (en) | 1980-10-29 |
Family
ID=27428971
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB20208/77A Expired GB1578041A (en) | 1976-05-17 | 1977-05-13 | Benzofurans and benzoxepins |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4232039A (OSRAM) |
| JP (1) | JPS52139055A (OSRAM) |
| AU (1) | AU513952B2 (OSRAM) |
| CA (1) | CA1097667A (OSRAM) |
| DE (1) | DE2720321A1 (OSRAM) |
| DK (1) | DK202177A (OSRAM) |
| ES (1) | ES458818A1 (OSRAM) |
| FI (1) | FI771466A7 (OSRAM) |
| FR (1) | FR2360588A1 (OSRAM) |
| GB (1) | GB1578041A (OSRAM) |
| IL (1) | IL52105A (OSRAM) |
| NZ (1) | NZ184123A (OSRAM) |
| PH (1) | PH13933A (OSRAM) |
| PT (1) | PT66551B (OSRAM) |
| SE (1) | SE7705339L (OSRAM) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0143952A1 (en) * | 1983-10-12 | 1985-06-12 | Merck & Co. Inc. | Substituted cinnamyl-2,3-dihydrobenzopyrans and cinnamylphenols useful as anti-inflammatory agents |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0652861B1 (fr) * | 1993-05-26 | 1997-09-03 | Firmenich Sa | Composes aromatiques nouveaux et leur utilisation en parfumerie |
| DE19808261A1 (de) * | 1998-02-27 | 1999-10-28 | Bayer Ag | Arylphenylsubstituierte cyclische Ketoenole |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2548704A (en) * | 1949-08-17 | 1951-04-10 | Dow Chemical Co | Substituted 2,3-dihydro-2-methylbenzofurans |
| US3808236A (en) | 1970-03-24 | 1974-04-30 | Anvar | 2-nitro-benzofuran derivatives |
-
1977
- 1977-05-06 DE DE19772720321 patent/DE2720321A1/de not_active Withdrawn
- 1977-05-09 SE SE7705339A patent/SE7705339L/xx unknown
- 1977-05-09 DK DK202177A patent/DK202177A/da not_active Application Discontinuation
- 1977-05-09 FI FI771466A patent/FI771466A7/fi not_active Application Discontinuation
- 1977-05-13 PH PH19770A patent/PH13933A/en unknown
- 1977-05-13 GB GB20208/77A patent/GB1578041A/en not_active Expired
- 1977-05-16 CA CA278,487A patent/CA1097667A/en not_active Expired
- 1977-05-16 JP JP5624977A patent/JPS52139055A/ja active Pending
- 1977-05-16 PT PT66551A patent/PT66551B/pt unknown
- 1977-05-16 IL IL52105A patent/IL52105A/xx unknown
- 1977-05-16 ES ES458818A patent/ES458818A1/es not_active Expired
- 1977-05-17 AU AU25194/77A patent/AU513952B2/en not_active Expired
- 1977-05-17 NZ NZ184123A patent/NZ184123A/xx unknown
- 1977-05-17 FR FR7715037A patent/FR2360588A1/fr active Granted
-
1978
- 1978-04-14 US US05/896,481 patent/US4232039A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0143952A1 (en) * | 1983-10-12 | 1985-06-12 | Merck & Co. Inc. | Substituted cinnamyl-2,3-dihydrobenzopyrans and cinnamylphenols useful as anti-inflammatory agents |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2360588A1 (fr) | 1978-03-03 |
| FI771466A7 (OSRAM) | 1977-11-18 |
| AU513952B2 (en) | 1981-01-15 |
| DK202177A (da) | 1977-11-18 |
| IL52105A0 (en) | 1977-07-31 |
| PT66551A (fr) | 1977-06-01 |
| SE7705339L (sv) | 1977-11-18 |
| PH13933A (en) | 1980-11-04 |
| US4232039A (en) | 1980-11-04 |
| PT66551B (fr) | 1979-10-22 |
| IL52105A (en) | 1981-02-27 |
| DE2720321A1 (de) | 1977-12-01 |
| AU2519477A (en) | 1978-11-23 |
| FR2360588B1 (OSRAM) | 1980-02-01 |
| CA1097667A (en) | 1981-03-17 |
| NZ184123A (en) | 1979-12-11 |
| ES458818A1 (es) | 1978-11-01 |
| JPS52139055A (en) | 1977-11-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |