CH437252A - Verfahren zur Herstellung von Catechol-O-methyltransferase-Inhibitoren - Google Patents
Verfahren zur Herstellung von Catechol-O-methyltransferase-InhibitorenInfo
- Publication number
- CH437252A CH437252A CH12163A CH12163A CH437252A CH 437252 A CH437252 A CH 437252A CH 12163 A CH12163 A CH 12163A CH 12163 A CH12163 A CH 12163A CH 437252 A CH437252 A CH 437252A
- Authority
- CH
- Switzerland
- Prior art keywords
- converted
- hydroxyl groups
- per
- catechol
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 239000003543 catechol methyltransferase inhibitor Substances 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-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 3
- 238000007112 amidation reaction Methods 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 238000007127 saponification reaction Methods 0.000 claims 1
- 241001465754 Metazoa Species 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- PFDFJMIGPOJBQV-UHFFFAOYSA-N 2-(3,4-dihydroxyphenyl)acetamide Chemical compound NC(=O)CC1=CC=C(O)C(O)=C1 PFDFJMIGPOJBQV-UHFFFAOYSA-N 0.000 description 4
- DIVQKHQLANKJQO-UHFFFAOYSA-N 3-methoxytyramine Chemical compound COC1=CC(CCN)=CC=C1O DIVQKHQLANKJQO-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 4
- 210000004556 brain Anatomy 0.000 description 4
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 4
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- VYELVKLTNGETIC-UHFFFAOYSA-N 2-(3,4-diacetyloxyphenyl)acetic acid Chemical compound CC(=O)OC1=CC=C(CC(O)=O)C=C1OC(C)=O VYELVKLTNGETIC-UHFFFAOYSA-N 0.000 description 2
- QTVFVCXTCTWSJC-UHFFFAOYSA-N 2-[3,4-bis(phenylmethoxy)phenyl]acetamide Chemical compound C=1C=CC=CC=1COC1=CC(CC(=O)N)=CC=C1OCC1=CC=CC=C1 QTVFVCXTCTWSJC-UHFFFAOYSA-N 0.000 description 2
- CFFZDZCDUFSOFZ-UHFFFAOYSA-N 3,4-Dihydroxy-phenylacetic acid Chemical compound OC(=O)CC1=CC=C(O)C(O)=C1 CFFZDZCDUFSOFZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 102000010909 Monoamine Oxidase Human genes 0.000 description 2
- 108010062431 Monoamine oxidase Proteins 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DMMPXIUSVODADD-UHFFFAOYSA-N [2-acetyloxy-4-(2-chloro-2-oxoethyl)phenyl] acetate Chemical compound CC(=O)OC1=CC=C(CC(Cl)=O)C=C1OC(C)=O DMMPXIUSVODADD-UHFFFAOYSA-N 0.000 description 2
- TXHIDIHEXDFONW-UHFFFAOYSA-N benzene;propan-2-one Chemical compound CC(C)=O.C1=CC=CC=C1 TXHIDIHEXDFONW-UHFFFAOYSA-N 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 150000003943 catecholamines Chemical class 0.000 description 2
- 229960003638 dopamine Drugs 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229940079877 pyrogallol Drugs 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- KMDJMBYENOYYCY-UHFFFAOYSA-N 2-(3,4-dihydroxyphenyl)propanamide Chemical compound NC(=O)C(C)C1=CC=C(O)C(O)=C1 KMDJMBYENOYYCY-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- KVAFNOAGIQWNSJ-UHFFFAOYSA-N 2-[3,4-bis(phenylmethoxy)phenyl]acetic acid Chemical compound C=1C=CC=CC=1COC1=CC(CC(=O)O)=CC=C1OCC1=CC=CC=C1 KVAFNOAGIQWNSJ-UHFFFAOYSA-N 0.000 description 1
- SRDYQFMSZNVVMU-UHFFFAOYSA-N 2-[3,4-bis(phenylmethoxy)phenyl]acetyl chloride Chemical compound C=1C=CC=CC=1COC1=CC(CC(=O)Cl)=CC=C1OCC1=CC=CC=C1 SRDYQFMSZNVVMU-UHFFFAOYSA-N 0.000 description 1
- NOIIUHRQUVNIDD-UHFFFAOYSA-N 3-[[oxo(pyridin-4-yl)methyl]hydrazo]-N-(phenylmethyl)propanamide Chemical compound C=1C=CC=CC=1CNC(=O)CCNNC(=O)C1=CC=NC=C1 NOIIUHRQUVNIDD-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 1
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 229940123685 Monoamine oxidase inhibitor Drugs 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 229910017974 NH40H Inorganic materials 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 206010070863 Toxicity to various agents Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 229940124630 bronchodilator Drugs 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 1
- 229960001317 isoprenaline Drugs 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 239000002899 monoamine oxidase inhibitor Substances 0.000 description 1
- 229960003057 nialamide Drugs 0.000 description 1
- 238000007833 oxidative deamination reaction Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE467/62A SE314060B (en, 2012) | 1962-01-17 | 1962-01-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH437252A true CH437252A (de) | 1967-06-15 |
Family
ID=20256618
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH12163A CH437252A (de) | 1962-01-17 | 1963-01-07 | Verfahren zur Herstellung von Catechol-O-methyltransferase-Inhibitoren |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE626897A (en, 2012) |
| CH (1) | CH437252A (en, 2012) |
| DK (1) | DK103472C (en, 2012) |
| FR (1) | FR2526M (en, 2012) |
| GB (1) | GB1007769A (en, 2012) |
| SE (1) | SE314060B (en, 2012) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4448730A (en) * | 1981-03-24 | 1984-05-15 | Riet Bartholomeus Van T | Hydroxybenzohydroxamic acids, benzamides and esters and related compounds as ribonucleotide reductase inhibitors |
| US4460602A (en) * | 1981-06-30 | 1984-07-17 | The Procter & Gamble Company | Urea derivatives |
| US4443473A (en) * | 1981-06-30 | 1984-04-17 | The Procter & Gamble Company | Carbamate derivatives |
| US4424205A (en) * | 1982-03-18 | 1984-01-03 | The Procter & Gamble Company | Hydroxyphenylacetamides having analgesic and anti-irritant activity |
| US4493848A (en) * | 1983-07-14 | 1985-01-15 | The Procter & Gamble Company | Compositions and methods useful for producing analgesia |
| US4544668A (en) * | 1983-07-14 | 1985-10-01 | The Procter & Gamble Company | Compounds and compositions useful for producing analgesia |
| US4564633A (en) * | 1983-07-14 | 1986-01-14 | The Procter & Gamble Company | Compositions and methods useful for producing analgesia |
| US5013759A (en) * | 1985-06-10 | 1991-05-07 | The Procter & Gamble Company | Compounds and compositions having anti-inflammatory and analgesic activity |
| US5220064A (en) * | 1986-11-26 | 1993-06-15 | Warner-Lambert Company | Substituted 4'-hydroxyphenylacetic acid derivatives having antiinflammatory and analgesic activity |
| US8557229B2 (en) | 2010-03-26 | 2013-10-15 | The Procter & Gamble Company | Hair removal method and hair removal kit |
-
0
- BE BE626897D patent/BE626897A/xx unknown
-
1962
- 1962-01-17 SE SE467/62A patent/SE314060B/xx unknown
-
1963
- 1963-01-07 CH CH12163A patent/CH437252A/de unknown
- 1963-01-08 DK DK6163AA patent/DK103472C/da active
- 1963-01-17 FR FR921697A patent/FR2526M/fr not_active Expired
- 1963-01-17 GB GB2192/63A patent/GB1007769A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2526M (fr) | 1964-05-11 |
| SE314060B (en, 2012) | 1969-09-01 |
| BE626897A (en, 2012) | |
| GB1007769A (en) | 1965-10-22 |
| DK103472C (da) | 1966-01-10 |
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