JPS58103365A - ｍ―ヒドロキシフェニル置換化合物製造用中間体 - Google Patents

ｍ―ヒドロキシフェニル置換化合物製造用中間体

Info

Publication number: JPS58103365A
Authority: JP; Japan
Prior art keywords: hydrogen; alkyl; formula; enyl; compound
Prior art date: 1981-12-02
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.): Granted

Application number

JP21258182A

Other languages

English (en)

Japanese (ja)

Other versions

JPH051259B2 (da

Inventor

ロビン・ジエラルド・シエパ−ド

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

John Wyeth and Brother Ltd

Original Assignee

John Wyeth and Brother Ltd

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.)

1981-12-02

Filing date

1982-12-02

Publication date

1983-06-20

1982-12-02 Application filed by John Wyeth and Brother Ltd filed Critical John Wyeth and Brother Ltd

1983-06-20 Publication of JPS58103365A publication Critical patent/JPS58103365A/ja

1993-01-07 Publication of JPH051259B2 publication Critical patent/JPH051259B2/ja

Status Granted legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims description 38
-1 M-hydroxyphenyl Chemical group 0.000 title claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 31
229910052739 hydrogen Inorganic materials 0.000 claims description 25
239000001257 hydrogen Substances 0.000 claims description 25
238000000034 method Methods 0.000 claims description 19
125000000962 organic group Chemical group 0.000 claims description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
125000003118 aryl group Chemical group 0.000 claims description 9
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
229910052794 bromium Inorganic materials 0.000 claims description 9
150000002431 hydrogen Chemical group 0.000 claims description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 6
125000000304 alkynyl group Chemical group 0.000 claims description 6
239000000460 chlorine Substances 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
239000003377 acid catalyst Substances 0.000 claims description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 4
229910000041 hydrogen chloride Inorganic materials 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
230000000269 nucleophilic effect Effects 0.000 claims description 4
230000003301 hydrolyzing effect Effects 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims 2
HFQGPJZLZGVGET-UHFFFAOYSA-N 1-methyl-3h-azepin-2-one Chemical compound CN1C=CC=CCC1=O HFQGPJZLZGVGET-UHFFFAOYSA-N 0.000 claims 1
150000001649 bromium compounds Chemical group 0.000 claims 1
125000006239 protecting group Chemical group 0.000 claims 1
125000004665 trialkylsilyl group Chemical group 0.000 claims 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 17
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
238000002844 melting Methods 0.000 description 10
230000008018 melting Effects 0.000 description 10
229960000583 acetic acid Drugs 0.000 description 9
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
229910000042 hydrogen bromide Inorganic materials 0.000 description 8
239000002904 solvent Substances 0.000 description 8
239000000243 solution Substances 0.000 description 7
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000000921 elemental analysis Methods 0.000 description 6
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
235000019439 ethyl acetate Nutrition 0.000 description 5
125000001424 substituent group Chemical group 0.000 description 5
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
150000001450 anions Chemical class 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 4
239000012044 organic layer Substances 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
239000007787 solid Substances 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
IBNKFKLIUOMAQB-UHFFFAOYSA-N 3-(3-hydroxyphenyl)-1-methylazepan-2-one Chemical compound O=C1N(C)CCCCC1C1=CC=CC(O)=C1 IBNKFKLIUOMAQB-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
230000031709 bromination Effects 0.000 description 3
238000005893 bromination reaction Methods 0.000 description 3
229940043279 diisopropylamine Drugs 0.000 description 3
125000000623 heterocyclic group Chemical group 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
150000003951 lactams Chemical class 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000012038 nucleophile Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
MFQSRAGDXYOERL-UHFFFAOYSA-N 2-bromo-3-methoxycyclohex-2-en-1-one Chemical compound COC1=C(Br)C(=O)CCC1 MFQSRAGDXYOERL-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
102000007527 Autoreceptors Human genes 0.000 description 2
108010071131 Autoreceptors Proteins 0.000 description 2
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
229940035676 analgesics Drugs 0.000 description 2
239000000730 antalgic agent Substances 0.000 description 2
230000003110 anti-inflammatory effect Effects 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
229960003638 dopamine Drugs 0.000 description 2
239000003480 eluent Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
230000026030 halogenation Effects 0.000 description 2
238000005658 halogenation reaction Methods 0.000 description 2
125000005842 heteroatom Chemical group 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
PLIQWXNVJOPJOT-UXMRNZNESA-N (2s)-2-amino-1-(2-diphenoxyphosphorylpyrrolidin-1-yl)-3-phenylpropan-1-one Chemical compound C([C@H](N)C(=O)N1C(CCC1)P(=O)(OC=1C=CC=CC=1)OC=1C=CC=CC=1)C1=CC=CC=C1 PLIQWXNVJOPJOT-UXMRNZNESA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
PYOFHCFMVFHGGF-UHFFFAOYSA-N 1-propylpiperidin-2-one Chemical compound CCCN1CCCCC1=O PYOFHCFMVFHGGF-UHFFFAOYSA-N 0.000 description 1
KPVZWLCTHWRRNK-UHFFFAOYSA-N 2-methoxycyclohex-2-en-1-one Chemical compound COC1=CCCCC1=O KPVZWLCTHWRRNK-UHFFFAOYSA-N 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
VFUGCQKESINERB-UHFFFAOYSA-N 3-(1-methyl-3-propylpyrrolidin-3-yl)phenol Chemical compound C=1C=CC(O)=CC=1C1(CCC)CCN(C)C1 VFUGCQKESINERB-UHFFFAOYSA-N 0.000 description 1
HTSNFXAICLXZMA-UHFFFAOYSA-N 3-(1-propyl-3-piperidinyl)phenol Chemical compound C1N(CCC)CCCC1C1=CC=CC(O)=C1 HTSNFXAICLXZMA-UHFFFAOYSA-N 0.000 description 1
HTMHIQSSYCFMSW-UHFFFAOYSA-N 3-(2-bromo-3-oxocyclohexen-1-yl)-1-methylazepan-2-one Chemical compound O=C1N(C)CCCCC1C1=C(Br)C(=O)CCC1 HTMHIQSSYCFMSW-UHFFFAOYSA-N 0.000 description 1
KZQTTZFOMAYISG-UHFFFAOYSA-N 3-(2-chloro-3-oxocyclohexen-1-yl)-1-methylazepan-2-one Chemical compound O=C1N(C)CCCCC1C1=C(Cl)C(=O)CCC1 KZQTTZFOMAYISG-UHFFFAOYSA-N 0.000 description 1
YVVPRKXQMOGYCL-UHFFFAOYSA-N 3-(2-chloro-3-oxocyclohexen-1-yl)-3-ethyl-1-methylazepan-2-one Chemical compound ClC=1C(=O)CCCC=1C1(CC)CCCCN(C)C1=O YVVPRKXQMOGYCL-UHFFFAOYSA-N 0.000 description 1
FXLAUIBPJLQPNB-UHFFFAOYSA-N 3-(azepan-1-yl)phenol Chemical compound OC1=CC=CC(N2CCCCCC2)=C1 FXLAUIBPJLQPNB-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
TWJZVJYUCAHEGB-UHFFFAOYSA-N 3-ethyl-1-methylazepan-2-one Chemical compound CCC1CCCCN(C)C1=O TWJZVJYUCAHEGB-UHFFFAOYSA-N 0.000 description 1
YFSJZMANJNLCOQ-UHFFFAOYSA-N 3-ethyl-3-(3-hydroxyphenyl)-1-methylazepan-2-one Chemical compound C=1C=CC(O)=CC=1C1(CC)CCCCN(C)C1=O YFSJZMANJNLCOQ-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
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 1
125000000174 L-prolyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])C(*)=O 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
238000007126 N-alkylation reaction Methods 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
239000000556 agonist Substances 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
238000005899 aromatization reaction Methods 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
125000002618 bicyclic heterocycle group Chemical group 0.000 description 1
230000005540 biological transmission Effects 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
VDQQXEISLMTGAB-UHFFFAOYSA-N chloramine T Chemical compound [Na+].CC1=CC=C(S(=O)(=O)[N-]Cl)C=C1 VDQQXEISLMTGAB-UHFFFAOYSA-N 0.000 description 1
238000005660 chlorination reaction Methods 0.000 description 1
125000000068 chlorophenyl group Chemical group 0.000 description 1
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000006704 dehydrohalogenation reaction Methods 0.000 description 1
201000010099 disease Diseases 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
239000010410 layer Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
ZDGGJQMSELMHLK-UHFFFAOYSA-N m-Trifluoromethylhippuric acid Chemical compound OC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 ZDGGJQMSELMHLK-UHFFFAOYSA-N 0.000 description 1
JLICHNCFTLFZJN-HNNXBMFYSA-N meptazinol Chemical compound C=1C=CC(O)=CC=1[C@@]1(CC)CCCCN(C)C1 JLICHNCFTLFZJN-HNNXBMFYSA-N 0.000 description 1
229960000365 meptazinol Drugs 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000003921 oil Substances 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
150000003053 piperidines Chemical class 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229950004859 profadol Drugs 0.000 description 1
150000003235 pyrrolidines Chemical class 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000005389 trialkylsiloxy group Chemical group 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1

Landscapes

Other In-Based Heterocyclic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Pyrrole Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP21258182A 1981-12-02 1982-12-02 ｍ―ヒドロキシフェニル置換化合物製造用中間体 Granted JPS58103365A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GB8136364		1981-12-02
GB8136364		1981-12-02
GB8220721		1982-07-16

Publications (2)

Publication Number	Publication Date
JPS58103365A true JPS58103365A (ja)	1983-06-20
JPH051259B2 JPH051259B2 (da)	1993-01-07

Family

ID=10526338

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP21258182A Granted JPS58103365A (ja)	1981-12-02	1982-12-02	ｍ―ヒドロキシフェニル置換化合物製造用中間体

Country Status (2)

Country	Link
JP (1)	JPS58103365A (da)
ZA (1)	ZA828437B (da)

1982
- 1982-11-16 ZA ZA828437A patent/ZA828437B/xx unknown
- 1982-12-02 JP JP21258182A patent/JPS58103365A/ja active Granted

Also Published As

Publication number	Publication date
ZA828437B (en)	1984-06-27
JPH051259B2 (da)	1993-01-07

Publication	Publication Date	Title
JPH06271571A (ja)	1994-09-27	インドール、インダゾール及びベンズイソオキサゾール化合物、それらの製法およびそれらを含有する製薬組成物
JPH0757748B2 (ja)	1995-06-21	３−アミノピペリジン誘導体及び関連する窒素含有複素環化合物
HU221193B1 (en)	2002-08-28	Neuroprotective indole, qinoline and benzoxazolone derivatives, pharmaceutical compositions comprising such compounds and process for producing them
JPS5916875A (ja)	1984-01-28	新規アリ−ルピペリジン誘導体の製造方法
EP0954521B1 (en)	2003-05-14	4- (thien-3-yl)methyl] imidazole derivatives having alpha2-adrenoceptor agonistic activity
IE63043B1 (en)	1995-03-22	Cyclic amides
JPS643186B2 (da)	1989-01-19
CA1156235A (en)	1983-11-01	1-(8-quinolyl)-2-pyrrolidinone
AU718719B2 (en)	2000-04-20	4-{(thien-2-yl)methyl}imidazole derivatives having alpha2-adrenoceptor agonistic activity
JPS58103365A (ja)	1983-06-20	ｍ―ヒドロキシフェニル置換化合物製造用中間体
HU192836B (en)	1987-07-28	Process for producing substituted azabicyclo-alkane derivatives and pharmaceutical compositions containing them
US4463177A (en)	1984-07-31	Process for making m-hydroxyphenyl substituted compounds
CA1142933A (en)	1983-03-15	Phenyl quinolizidines
US4167638A (en)	1979-09-11	Process for production of 8-NHR quinolines
US3936459A (en)	1976-02-03	1',4'-Dihydro-1-methyl-spiro [piperidine and pyrrolidine-2,3'(2'H)quinoline]-2'-one compounds
JPS6055510B2 (ja)	1985-12-05	４−（ｐ−フルオルベンゾイル）−１−〔３−（ｐ−フルオルベンゾイル）プロピル〕ピペリジンとその酸付加塩の製造方法
US4022792A (en)	1977-05-10	Methylidenepiperidines
JPH07121931B2 (ja)	1995-12-25	ベンゾ〔ｂ〕フラン誘導体
US4243589A (en)	1981-01-06	Triazolobenzazepines and processes for their production
GB2113676A (en)	1983-08-10	m-Hydroxyphenyl substituted compounds
JP3794696B2 (ja)	2006-07-05	フェニルイミダゾリジノン誘導体およびその製造法
US3419561A (en)	1968-12-31	2,3,4,4a,5,6,10b-heptahydro-1-oxaphenanthridines and production thereof
WO1986007591A1 (en)	1986-12-31	Catecholcarboxamides, process for their preparation, intermediates and a pharmaceutical preparation
NZ240624A (en)	1994-01-26	Preparation of a 3-alkylated indole; (2-nitrophenyl)acetaldehyde
US5095038A (en)	1992-03-10	Carbocyclic compounds useful as leukotriene antagonists