JPH0567134B2 - - Google Patents
Info
- Publication number
- JPH0567134B2 JPH0567134B2 JP61303761A JP30376186A JPH0567134B2 JP H0567134 B2 JPH0567134 B2 JP H0567134B2 JP 61303761 A JP61303761 A JP 61303761A JP 30376186 A JP30376186 A JP 30376186A JP H0567134 B2 JPH0567134 B2 JP H0567134B2
- Authority
- JP
- Japan
- Prior art keywords
- alkyl group
- formula
- carbon atoms
- general formula
- fatty acid
- 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 - Lifetime
Links
- 238000004519 manufacturing process Methods 0.000 claims description 19
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 16
- 239000000194 fatty acid Substances 0.000 claims description 16
- 229930195729 fatty acid Natural products 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 14
- -1 fatty acid halide Chemical class 0.000 claims description 13
- 150000004665 fatty acids Chemical class 0.000 claims description 9
- 150000005206 1,2-dihydroxybenzenes Chemical class 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims 9
- 125000004432 carbon atom Chemical group C* 0.000 claims 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 11
- 238000000921 elemental analysis Methods 0.000 description 10
- 238000002329 infrared spectrum Methods 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- ASXCXYNHCRSLLJ-UHFFFAOYSA-N (2-acetyloxy-4-propylphenyl) acetate Chemical compound CCCC1=CC=C(OC(C)=O)C(OC(C)=O)=C1 ASXCXYNHCRSLLJ-UHFFFAOYSA-N 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
- ZBCATMYQYDCTIZ-UHFFFAOYSA-N 4-methylcatechol Chemical compound CC1=CC=C(O)C(O)=C1 ZBCATMYQYDCTIZ-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- HFLGBNBLMBSXEM-UHFFFAOYSA-N 4-Ethyl-1,2-benzenediol Chemical compound CCC1=CC=C(O)C(O)=C1 HFLGBNBLMBSXEM-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- VJPNFMCNTKHVTR-UHFFFAOYSA-N 4-butyl-1,2-dimethoxybenzene Chemical compound CCCCC1=CC=C(OC)C(OC)=C1 VJPNFMCNTKHVTR-UHFFFAOYSA-N 0.000 description 3
- NEBQMYHKOREVAL-UHFFFAOYSA-N 4-ethyl-1,2-dimethoxybenzene Chemical compound CCC1=CC=C(OC)C(OC)=C1 NEBQMYHKOREVAL-UHFFFAOYSA-N 0.000 description 3
- SCTPZNJTGOGSQD-UHFFFAOYSA-N 4-propylbenzene-1,2-diol Chemical compound CCCC1=CC=C(O)C(O)=C1 SCTPZNJTGOGSQD-UHFFFAOYSA-N 0.000 description 3
- YXLFQKUIZVSIEP-UHFFFAOYSA-N Dihydromethyleugenol Chemical compound CCCC1=CC=C(OC)C(OC)=C1 YXLFQKUIZVSIEP-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 3
- 235000019345 sodium thiosulphate Nutrition 0.000 description 3
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 3
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 3
- 239000011592 zinc chloride Substances 0.000 description 3
- 235000005074 zinc chloride Nutrition 0.000 description 3
- NJXYTXADXSRFTJ-UHFFFAOYSA-N 1,2-Dimethoxy-4-vinylbenzene Chemical compound COC1=CC=C(C=C)C=C1OC NJXYTXADXSRFTJ-UHFFFAOYSA-N 0.000 description 2
- LAVPWYRENKSWJM-UHFFFAOYSA-N 4-butylbenzene-1,2-diol Chemical compound CCCCC1=CC=C(O)C(O)=C1 LAVPWYRENKSWJM-UHFFFAOYSA-N 0.000 description 2
- ZOXATXRUISPBNC-UHFFFAOYSA-N 4-ethyl-1,2-diacetoxybenzene Natural products CCC1=CC=C(OC(C)=O)C(OC(C)=O)=C1 ZOXATXRUISPBNC-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- LPMNWSNOKHEPJQ-UHFFFAOYSA-N [4-methyl-2-(2-methylpropanoyloxy)phenyl] 2-methylpropanoate Chemical compound CC(C)C(=O)OC1=CC=C(C)C=C1OC(=O)C(C)C LPMNWSNOKHEPJQ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 208000015122 neurodegenerative disease Diseases 0.000 description 2
- IPBVNPXQWQGGJP-UHFFFAOYSA-N phenyl acetate Chemical compound CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- GJZLJBJUIBIUQV-UHFFFAOYSA-N (2-acetyloxy-4-butylphenyl) acetate Chemical compound CCCCC1=CC=C(OC(C)=O)C(OC(C)=O)=C1 GJZLJBJUIBIUQV-UHFFFAOYSA-N 0.000 description 1
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-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
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229910010082 LiAlH Inorganic materials 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- NNWHUJCUHAELCL-UHFFFAOYSA-N cis-Methyl isoeugenol Natural products COC1=CC=C(C=CC)C=C1OC NNWHUJCUHAELCL-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000020335 dealkylation Effects 0.000 description 1
- 238000006900 dealkylation reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- NNWHUJCUHAELCL-SNAWJCMRSA-N trans-isomethyleugenol Chemical compound COC1=CC=C(\C=C\C)C=C1OC NNWHUJCUHAELCL-SNAWJCMRSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61303761A JPS63156751A (ja) | 1986-12-22 | 1986-12-22 | カテコール誘導体の製造方法 |
| FI874163A FI874163A (fi) | 1986-09-26 | 1987-09-23 | Katekolderivat samt preparat innehaollande desamma foer haemmande och botande av regressiva sjukdomar i det centrala nervsystemet. |
| NO874032A NO874032L (no) | 1986-09-26 | 1987-09-25 | Fremgangsmaate for fremstilling av terapeutisk aktive catecholderivater. |
| AU78956/87A AU603137B2 (en) | 1986-09-26 | 1987-09-25 | Catechol derivatives, and preventive and remedial preparations for regressive disorders in the central nervous system containing the same |
| DK505787A DK505787A (da) | 1986-09-26 | 1987-09-25 | Catecholderivater samt forebyggende og terapeutisk praeparat omfattende samme mod regressive sygdomme i centralnervesystemet |
| EP87308482A EP0261977B1 (fr) | 1986-09-26 | 1987-09-25 | Dérivés du catéchol et préparations préventives et médicinales pour le traitement de troubles régressifs dans le système nerveux central |
| NZ221933A NZ221933A (en) | 1986-09-26 | 1987-09-25 | Catechol derivatives and pharmaceutical compositions |
| DE8787308482T DE3777050D1 (de) | 1986-09-26 | 1987-09-25 | Catecholderivate und vorbeugende sowie heilende praeparate fuer regressive stoerungen im zentralnervensystem. |
| KR1019870010738A KR900001511B1 (ko) | 1986-09-26 | 1987-09-25 | 카테콜 유도체 및 그것을 함유하는 중추신경계 퇴행성질환의 진행방지 및 치료제 |
| US07/481,677 US4985458A (en) | 1986-09-26 | 1990-02-20 | Catechol diacetate derivatives for inducing the production of nerve growth factor to treat degenerative diseases in the central nervous system |
| US07/606,817 US5102906A (en) | 1986-09-26 | 1990-10-31 | Catechol derivatives, and preventive and remedial preparations for regressive disorders in the central nervous system containing the same |
| US07/801,866 US5214034A (en) | 1986-09-26 | 1991-12-03 | Catechol derivatives, and preventive and remedial preparations for regressive disorders in the central nervous system containing the same |
| NO921475A NO921475D0 (no) | 1986-09-26 | 1992-04-13 | Analogifremgangsmaate for fremstilling av terapeutisk aktive catecholderivater |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61303761A JPS63156751A (ja) | 1986-12-22 | 1986-12-22 | カテコール誘導体の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63156751A JPS63156751A (ja) | 1988-06-29 |
| JPH0567134B2 true JPH0567134B2 (fr) | 1993-09-24 |
Family
ID=17924954
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61303761A Granted JPS63156751A (ja) | 1986-09-26 | 1986-12-22 | カテコール誘導体の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63156751A (fr) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3631227A (en) * | 1970-02-27 | 1971-12-28 | Texaco Inc | Halocyclohexanone conversion to catechol diacetate |
-
1986
- 1986-12-22 JP JP61303761A patent/JPS63156751A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3631227A (en) * | 1970-02-27 | 1971-12-28 | Texaco Inc | Halocyclohexanone conversion to catechol diacetate |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63156751A (ja) | 1988-06-29 |
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