CH415587A - Verfahren zur Herstellung von N-alkylsubstituierten 3-Methoxy-4-carbamidomethoxyphenylessigsäurealkyl- und -alkenylestern - Google Patents
Verfahren zur Herstellung von N-alkylsubstituierten 3-Methoxy-4-carbamidomethoxyphenylessigsäurealkyl- und -alkenylesternInfo
- Publication number
- CH415587A CH415587A CH319466A CH319466A CH415587A CH 415587 A CH415587 A CH 415587A CH 319466 A CH319466 A CH 319466A CH 319466 A CH319466 A CH 319466A CH 415587 A CH415587 A CH 415587A
- Authority
- CH
- Switzerland
- Prior art keywords
- alkyl
- methoxy
- substituted
- carbamidomethoxyphenylacetic
- preparation
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 7
- 125000003342 alkenyl group Chemical group 0.000 title claims description 4
- 125000000217 alkyl group Chemical group 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical group COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 3
- 150000004702 methyl esters Chemical class 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 2
- -1 aliphatic alcohols Chemical class 0.000 claims description 2
- DIWVBIXQCNRCFE-UHFFFAOYSA-N DL-alpha-Methoxyphenylacetic acid Chemical class COC(C(O)=O)C1=CC=CC=C1 DIWVBIXQCNRCFE-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- 206010002091 Anaesthesia Diseases 0.000 description 7
- 230000037005 anaesthesia Effects 0.000 description 7
- 230000003444 anaesthetic effect Effects 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000004081 narcotic agent Substances 0.000 description 2
- 230000011514 reflex Effects 0.000 description 2
- SVNBLYILNKAFQM-UHFFFAOYSA-N 5-(cyclohexen-1-yl)-1,5-dimethyl-1,3-diazinane-2,4,6-trione;sodium Chemical compound [Na].O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 SVNBLYILNKAFQM-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000007656 barbituric acids Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 210000000080 chela (arthropods) Anatomy 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000003533 narcotic effect Effects 0.000 description 1
- GCDAJJAFUDTAOV-UHFFFAOYSA-N propyl 2-methoxy-2-phenylacetate Chemical compound CCCOC(=O)C(OC)C1=CC=CC=C1 GCDAJJAFUDTAOV-UHFFFAOYSA-N 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- RCOSUMRTSQULBK-UHFFFAOYSA-N sodium;propan-1-olate Chemical compound [Na+].CCC[O-] RCOSUMRTSQULBK-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000011477 surgical intervention Methods 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF31176A DE1134981B (de) | 1960-05-06 | 1960-05-06 | Verfahren zur Herstellung von N-substituierten 3-Methoxy-4-carbamidomethoxyphenylessigsaeurealkyl- und alkenylestern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH415587A true CH415587A (de) | 1966-06-30 |
Family
ID=7094083
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH319466A CH415587A (de) | 1960-05-06 | 1961-04-14 | Verfahren zur Herstellung von N-alkylsubstituierten 3-Methoxy-4-carbamidomethoxyphenylessigsäurealkyl- und -alkenylestern |
| CH444361A CH425762A (de) | 1960-05-06 | 1961-04-14 | Verfahren zur Herstellung von N-alkylsubstituierten 3-Methoxy-4-carbamidomethoxyphenylessigsäurealkyl- und alkenylestern |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH444361A CH425762A (de) | 1960-05-06 | 1961-04-14 | Verfahren zur Herstellung von N-alkylsubstituierten 3-Methoxy-4-carbamidomethoxyphenylessigsäurealkyl- und alkenylestern |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE603477A (da) |
| CH (2) | CH415587A (da) |
| DE (1) | DE1134981B (da) |
| DK (1) | DK104841C (da) |
| GB (1) | GB906250A (da) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1300545B (de) * | 1965-02-24 | 1969-08-07 | Bayer Ag | Verfahren zur Herstellung von in 5-Stellung substituierten 2-(N, N-Dialkyl- bzw. N-Alkyl-N-alkoxy-carbamoyl-methoxy)-benzoesaeureestern |
| IT1204778B (it) | 1986-02-04 | 1989-03-10 | Mazzarella Basilio | Formulazioni farmaceutiche iniettabili di principi attivi ad attivita' anestetica generale |
| CA2474262C (en) | 2002-01-25 | 2011-03-15 | Theravance, Inc. | Short-acting sedative hypnotic agents for anesthesia and sedation |
| JP4153949B2 (ja) * | 2002-05-09 | 2008-09-24 | セラヴァンス， インコーポレーテッド | 麻酔および鎮静についての短時間作用性鎮静催眠薬 |
| DK1648413T3 (da) | 2003-07-23 | 2010-01-11 | Theravance Inc | Farmaceutiske præparater af kortvirkende sedativt sövndyssende middel |
-
1960
- 1960-05-06 DE DEF31176A patent/DE1134981B/de active Pending
-
1961
- 1961-04-14 CH CH319466A patent/CH415587A/de unknown
- 1961-04-14 CH CH444361A patent/CH425762A/de unknown
- 1961-05-04 GB GB1628061A patent/GB906250A/en not_active Expired
- 1961-05-05 BE BE603477A patent/BE603477A/fr unknown
- 1961-05-05 DK DK186961A patent/DK104841C/da active
Also Published As
| Publication number | Publication date |
|---|---|
| BE603477A (fr) | 1961-11-06 |
| DK104841C (da) | 1966-07-11 |
| GB906250A (en) | 1962-09-19 |
| DE1134981B (de) | 1962-08-23 |
| CH425762A (de) | 1966-12-15 |
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