CH623045A5 - Process for the preparation of novel 2,3-dihydrobenzofurans and 2,3,4,5-tetrahydro-1-benzoxepins - Google Patents

Process for the preparation of novel 2,3-dihydrobenzofurans and 2,3,4,5-tetrahydro-1-benzoxepins Download PDF

Info

Publication number: CH623045A5
Authority: CH; Switzerland
Prior art keywords: formula; group; compounds; cyclohexyl; carbon atoms
Prior art date: 1976-05-17

Application number

CH612576A

Other languages

German (de)

English (en)

Inventor

Annemarie Dr Closse

Walter Dr Haefliger

Daniel Dr Hauser

Original Assignee

Sandoz Ag

Priority date (The priority date 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 date listed.)

1976-05-17

Filing date

1976-05-17

Publication date

1981-05-15

1976-05-17 Application filed by Sandoz Ag filed Critical Sandoz Ag

1976-05-17 Priority to CH612576A priority Critical patent/CH623045A5/de

1977-05-06 Priority to DE19772720321 priority patent/DE2720321A1/de

1977-05-09 Priority to DK202177A priority patent/DK202177A/da

1977-05-09 Priority to FI771466A priority patent/FI771466A7/fi

1977-05-09 Priority to SE7705339A priority patent/SE7705339L/xx

1977-05-13 Priority to NL7705304A priority patent/NL7705304A/xx

1977-05-13 Priority to GB20208/77A priority patent/GB1578041A/en

1977-05-13 Priority to PH19770A priority patent/PH13933A/en

1977-05-16 Priority to BE177631A priority patent/BE854702A/fr

1977-05-16 Priority to ES458818A priority patent/ES458818A1/es

1977-05-16 Priority to CA278,487A priority patent/CA1097667A/fr

1977-05-16 Priority to IL52105A priority patent/IL52105A/xx

1977-05-16 Priority to JP5624977A priority patent/JPS52139055A/ja

1977-05-16 Priority to PT66551A priority patent/PT66551B/fr

1977-05-17 Priority to NZ184123A priority patent/NZ184123A/xx

1977-05-17 Priority to AU25194/77A priority patent/AU513952B2/en

1977-05-17 Priority to FR7715037A priority patent/FR2360588A1/fr

1977-05-17 Priority to ZA00772934A priority patent/ZA772934B/xx

1978-04-14 Priority to US05/896,481 priority patent/US4232039A/en

1981-05-15 Publication of CH623045A5 publication Critical patent/CH623045A5/de

Links

238000002360 preparation method Methods 0.000 title claims abstract description 6
238000000034 method Methods 0.000 title claims description 15
HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical class C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 title claims description 3
150000001875 compounds Chemical class 0.000 claims abstract description 42
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 15
125000000217 alkyl group Chemical group 0.000 claims abstract description 14
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 9
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
229910052736 halogen Inorganic materials 0.000 claims abstract description 7
150000002367 halogens Chemical class 0.000 claims abstract description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
239000001257 hydrogen Substances 0.000 claims abstract description 6
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
230000000202 analgesic effect Effects 0.000 claims abstract description 3
230000002456 anti-arthritic effect Effects 0.000 claims abstract description 3
230000003110 anti-inflammatory effect Effects 0.000 claims abstract description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 54
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 claims description 12
238000003756 stirring Methods 0.000 claims description 12
238000000655 nuclear magnetic resonance spectrum Methods 0.000 claims description 11
239000000203 mixture Substances 0.000 claims description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 9
239000000741 silica gel Substances 0.000 claims description 9
229910002027 silica gel Inorganic materials 0.000 claims description 9
238000006243 chemical reaction Methods 0.000 claims description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
239000007858 starting material Substances 0.000 claims description 8
238000012360 testing method Methods 0.000 claims description 8
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
239000000460 chlorine Substances 0.000 claims description 6
229910052801 chlorine Inorganic materials 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 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
229910015845 BBr3 Inorganic materials 0.000 claims description 5
229910052794 bromium Inorganic materials 0.000 claims description 5
238000007363 ring formation reaction Methods 0.000 claims description 5
SYZAEHSQPKWSPY-UHFFFAOYSA-N 5-chloro-6-cyclohexyl-2,3-dihydro-1-benzofuran Chemical compound ClC1=CC=2CCOC=2C=C1C1CCCCC1 SYZAEHSQPKWSPY-UHFFFAOYSA-N 0.000 claims description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 4
230000037396 body weight Effects 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
239000001632 sodium acetate Substances 0.000 claims description 4
235000017281 sodium acetate Nutrition 0.000 claims description 4
239000012279 sodium borohydride Substances 0.000 claims description 4
229910000033 sodium borohydride Inorganic materials 0.000 claims description 4
FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 3
229910010084 LiAlH4 Inorganic materials 0.000 claims description 3
239000012280 lithium aluminium hydride Substances 0.000 claims description 3
229940014800 succinic anhydride Drugs 0.000 claims description 3
NGCRXXLKJAAUQQ-UHFFFAOYSA-N undec-5-ene Chemical compound CCCCCC=CCCCC NGCRXXLKJAAUQQ-UHFFFAOYSA-N 0.000 claims description 3
XXOQJWXDRPURJK-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1-benzoxepine Chemical compound O1CCCCC2=CC=CC=C21 XXOQJWXDRPURJK-UHFFFAOYSA-N 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
208000009386 Experimental Arthritis Diseases 0.000 claims description 2
241000124008 Mammalia Species 0.000 claims description 2
241001465754 Metazoa Species 0.000 claims description 2
239000013543 active substance Substances 0.000 claims description 2
230000029936 alkylation Effects 0.000 claims description 2
238000005804 alkylation reaction Methods 0.000 claims description 2
230000001754 anti-pyretic effect Effects 0.000 claims description 2
239000002221 antipyretic Substances 0.000 claims description 2
239000000679 carrageenan Substances 0.000 claims description 2
229940113118 carrageenan Drugs 0.000 claims description 2
235000010418 carrageenan Nutrition 0.000 claims description 2
229920001525 carrageenan Polymers 0.000 claims description 2
239000000969 carrier Substances 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
239000003814 drug Substances 0.000 claims description 2
230000000694 effects Effects 0.000 claims description 2
230000032050 esterification Effects 0.000 claims description 2
238000005886 esterification reaction Methods 0.000 claims description 2
230000026030 halogenation Effects 0.000 claims description 2
238000005658 halogenation reaction Methods 0.000 claims description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
125000000468 ketone group Chemical group 0.000 claims description 2
239000007788 liquid Substances 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
150000007530 organic bases Chemical group 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
230000000144 pharmacologic effect Effects 0.000 claims description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
239000007787 solid Substances 0.000 claims description 2
239000002904 solvent Substances 0.000 claims description 2
239000000126 substance Substances 0.000 claims description 2
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 claims description 2
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 1
206010030113 Oedema Diseases 0.000 claims 1
230000002401 inhibitory effect Effects 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 14
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000007832 Na2SO4 Substances 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
239000012074 organic phase Substances 0.000 description 6
229910052938 sodium sulfate Inorganic materials 0.000 description 6
235000011152 sodium sulphate Nutrition 0.000 description 6
239000000243 solution Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
-1 formyl compound Chemical class 0.000 description 5
239000000047 product Substances 0.000 description 5
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000002585 base Substances 0.000 description 4
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
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
239000005457 ice water Substances 0.000 description 3
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
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
238000001816 cooling Methods 0.000 description 2
239000007789 gas Substances 0.000 description 2
239000011261 inert gas Substances 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
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 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
LFLKITSXQSAZJR-UHFFFAOYSA-N 1-cyclohexyl-3-methoxybenzene Chemical compound COC1=CC=CC(C2CCCCC2)=C1 LFLKITSXQSAZJR-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
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 1
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 1
KWPQTFXULUUCGD-UHFFFAOYSA-N 3,4,5,7,8,9,10,10a-octahydropyrido[1,2-a][1,4]diazepine Chemical compound C1CCN=CC2CCCCN21 KWPQTFXULUUCGD-UHFFFAOYSA-N 0.000 description 1
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 1
OTSKCCJXSOCZKL-UHFFFAOYSA-N 4-(5-chloro-4-cyclohexyl-2-methoxyphenyl)butan-1-ol Chemical compound C1=C(CCCCO)C(OC)=CC(C2CCCCC2)=C1Cl OTSKCCJXSOCZKL-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
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 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
ANMAOLTWUVGEOW-UHFFFAOYSA-N 6-cyclohexyl-2,3-dihydro-1-benzofuran Chemical compound C1=C2OCCC2=CC=C1C1CCCCC1 ANMAOLTWUVGEOW-UHFFFAOYSA-N 0.000 description 1
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 1
MKASODOQIFLITP-UHFFFAOYSA-N 7-chloro-8-phenyl-2,3,4,5-tetrahydro-1-benzoxepine Chemical compound ClC1=CC=2CCCCOC=2C=C1C1=CC=CC=C1 MKASODOQIFLITP-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
230000003501 anti-edematous effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
235000014121 butter Nutrition 0.000 description 1
239000001582 butter acid Substances 0.000 description 1
SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 1
USPLDBATMHXKKD-UHFFFAOYSA-N dichloromethane;pentane Chemical compound ClCCl.CCCCC USPLDBATMHXKKD-UHFFFAOYSA-N 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000011541 reaction mixture Substances 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
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/24—Halogenated derivatives
- C07C39/42—Halogenated derivatives containing six-membered aromatic rings and other rings
- 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
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal 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

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH612576A 1976-05-17 1976-05-17 Process for the preparation of novel 2,3-dihydrobenzofurans and 2,3,4,5-tetrahydro-1-benzoxepins CH623045A5 (en)

Priority Applications (19)

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
DE19772720321 DE2720321A1 (de)	1976-05-17	1977-05-06	Neue benzofuran- und benzoxepinderivate
DK202177A DK202177A (da)	1976-05-17	1977-05-09	Fremgangsmade til fremstilling af organiske forbindelser
FI771466A FI771466A7 (fr)	1976-05-17	1977-05-09
SE7705339A SE7705339L (sv)	1976-05-17	1977-05-09	Nya organiska foreningar, deras framstellning och anvendning
NL7705304A NL7705304A (en)	1976-05-17	1977-05-13	Benzofuran and benzoxepin derivs. - as antiinflammatories, analgesics, antipyretics etc.
GB20208/77A GB1578041A (en)	1976-05-17	1977-05-13	Benzofurans and benzoxepins
PH19770A PH13933A (en)	1976-05-17	1977-05-13	Benzofuran derivatives
BE177631A BE854702A (fr)	1976-05-17	1977-05-16	Nouveaux composes heterocycliques, leur preparation et leur application comme medicaments
ES458818A ES458818A1 (es)	1976-05-17	1977-05-16	Procedimiento para la produccion de derivados de benzofura- no.
CA278,487A CA1097667A (fr)	1976-05-17	1977-05-16	Derives du benzo-furane
IL52105A IL52105A (en)	1976-05-17	1977-05-16	Benzofuran and benzoxepin derivatives, their preparation and pharmaceutical compositions containing them
JP5624977A JPS52139055A (en)	1976-05-17	1977-05-16	Improvement in organic compound
PT66551A PT66551B (fr)	1976-05-17	1977-05-16	Procede pour la preparation d'une composition pharmaceutique avec des nouveaux composes organiques
NZ184123A NZ184123A (en)	1976-05-17	1977-05-17	Benzofuran derivatives and pharmaceutical compositions
AU25194/77A AU513952B2 (en)	1976-05-17	1977-05-17	Benzofuran and benzoxepin derivatives
FR7715037A FR2360588A1 (fr)	1976-05-17	1977-05-17	Nouveaux composes 1,2-alkyleneoxy-benzemiques, leur preparation et leur application comme medicaments
ZA00772934A ZA772934B (en)	1976-05-17	1977-05-17	Improvements in or relating to organic compounds
US05/896,481 US4232039A (en)	1976-05-17	1978-04-14	Phenyl- or cycloalkyl-benzo-oxacyclic compounds

Applications Claiming Priority (1)

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

Publications (1)

Publication Number	Publication Date
CH623045A5 true CH623045A5 (en)	1981-05-15

Family

ID=4304671

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
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

Country Status (3)

Country	Link
BE (1)	BE854702A (fr)
CH (1)	CH623045A5 (fr)
ZA (1)	ZA772934B (fr)

1976
- 1976-05-17 CH CH612576A patent/CH623045A5/de not_active IP Right Cessation
1977
- 1977-05-16 BE BE177631A patent/BE854702A/fr unknown
- 1977-05-17 ZA ZA00772934A patent/ZA772934B/xx unknown

Also Published As

Publication number	Publication date
BE854702A (fr)	1977-11-16
ZA772934B (en)	1978-12-27

Legal Events

Date	Code	Title	Description
1982-01-29	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE19723722A1 (de)	1998-12-10	Nichtsteroidale Gestagene
DE2628475A1 (de)	1977-01-13	Halogensubstituierte 5-aroylpyrrol- 2-essigsaeure-derivate
DE69021902T2 (de)	1996-05-23	1-Benzyl-3-hydroxymethylindazol-Äther mit aliphatischen 2-Hydroxysäuren.
CH494730A (de)	1970-08-15	Verfahren zur Herstellung von Dibenzocyclopentenen
EP0496238A1 (fr)	1992-07-29	Benzoxazépines et benzothiazépines substituées, procédé pour leur préparation et leur application comme medicaments
US4699925A (en)	1987-10-13	Biphenylylpropionic acid derivative and pharmaceutical composition containing the same
EP0106800A1 (fr)	1984-04-25	Furannes
DE2854877A1 (de)	1979-06-28	N-substituierte omega-thiobutyramide, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
DE2812353A1 (de)	1978-09-28	Oxazol- und thiazol-alkansaeureverbindungen, verfahren zu ihrer herstellung und sie enthaltendes pharmazeutisches mittel
CH623045A5 (en)	1981-05-15	Process for the preparation of novel 2,3-dihydrobenzofurans and 2,3,4,5-tetrahydro-1-benzoxepins
CH542837A (de)	1973-10-15	Verfahren zur Herstellung von neuen Aryloxy- und Arylthioalkansäuren, ihren Salzen und funktionellen Derivaten
EP0350437A1 (fr)	1990-01-10	Phénylhétérocycles disubstitués en 3,4 et leur utilisation
CH591415A5 (en)	1977-09-15	3-(Tri-substd. benzoyl) propionic acids - as relaxants or spasmolytics for the gall bladder
DE2558356A1 (de)	1976-07-08	Dehydrobiotinverbindungen
DD208798A5 (de)	1984-04-11	Verfahren zur herstellung von phenol-derivate
DE2720321A1 (de)	1977-12-01	Neue benzofuran- und benzoxepinderivate
DE3520104A1 (de)	1985-12-12	Naphthoxazine, ihre herstellung und verwendung
DE2803544A1 (de)	1979-08-02	Neue benzofuran- und benzoxepinderivate
CH622256A5 (en)	1981-03-31	Process for the preparation of novel benzofurans
GB2212153A (en)	1989-07-19	Phenyl hydroxamic acids
DE2043048C3 (de)	1974-06-27	d-2-(Methylmercapto-2-naphthyl> propanal, Verfahren zu dessen Herstellung und dieses enthaltende Heilmittel
AT259553B (de)	1968-01-25	Verfahren zur Herstellung von Indolderivaten
EP0007516B1 (fr)	1981-10-28	7-Alpha-méthyl-oestrogènes, procédé pour leur préparation et leur utilisation dans des transformations ultérieures
AT256844B (de)	1967-09-11	Verfahren zur Herstellung von neuen 6,11-Dihydrodibenzo-[b,e]-thiepinen
AT336003B (de)	1977-04-12	Verfahren zur herstellung neuer 3-(4-biphenylyl)-buttersauren, ihrer ester, amide und salze