DE1134981B - Verfahren zur Herstellung von N-substituierten 3-Methoxy-4-carbamidomethoxyphenylessigsaeurealkyl- und alkenylestern - Google Patents
Verfahren zur Herstellung von N-substituierten 3-Methoxy-4-carbamidomethoxyphenylessigsaeurealkyl- und alkenylesternInfo
- Publication number
- DE1134981B DE1134981B DEF31176A DEF0031176A DE1134981B DE 1134981 B DE1134981 B DE 1134981B DE F31176 A DEF31176 A DE F31176A DE F0031176 A DEF0031176 A DE F0031176A DE 1134981 B DE1134981 B DE 1134981B
- Authority
- DE
- Germany
- Prior art keywords
- methoxy
- general formula
- substituted
- molecular weight
- low molecular
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 9
- 125000003342 alkenyl group Chemical group 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- QRMZSPFSDQBLIX-UHFFFAOYSA-N homovanillic acid Chemical class COC1=CC(CC(O)=O)=CC=C1O QRMZSPFSDQBLIX-UHFFFAOYSA-N 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- 241000283973 Oryctolagus cuniculus Species 0.000 description 19
- 206010002091 Anaesthesia Diseases 0.000 description 17
- 230000037005 anaesthesia Effects 0.000 description 16
- 239000011734 sodium Substances 0.000 description 12
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 12
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 11
- 239000000203 mixture Substances 0.000 description 11
- 229910052708 sodium Inorganic materials 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
- 230000003444 anaesthetic effect Effects 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 235000009518 sodium iodide Nutrition 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- CQQUWTMMFMJEFE-UHFFFAOYSA-N 2-chloro-n,n-diethylacetamide Chemical compound CCN(CC)C(=O)CCl CQQUWTMMFMJEFE-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- -1 esters N-substituted glycolic acid amides Chemical class 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-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
- 229940035674 anesthetics Drugs 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000003193 general anesthetic agent Substances 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 229940090181 propyl acetate Drugs 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000011514 reflex Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 150000003388 sodium compounds Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000011477 surgical intervention Methods 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- JLIDRDJNLAWIKT-UHFFFAOYSA-N 1,2-dimethyl-3h-benzo[e]indole Chemical compound C1=CC=CC2=C(C(=C(C)N3)C)C3=CC=C21 JLIDRDJNLAWIKT-UHFFFAOYSA-N 0.000 description 1
- RMFCMEVNMFHDSL-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)ethanimidamide Chemical compound NC(=N)CC1=CC=C(Cl)C(Cl)=C1 RMFCMEVNMFHDSL-UHFFFAOYSA-N 0.000 description 1
- SHWUYQDIJUWTPM-UHFFFAOYSA-N 2-chloro-n-propylacetamide Chemical compound CCCNC(=O)CCl SHWUYQDIJUWTPM-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- CRZQGDNQQAALAY-UHFFFAOYSA-N Methyl benzeneacetate Chemical compound COC(=O)CC1=CC=CC=C1 CRZQGDNQQAALAY-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 230000002378 acidificating effect Effects 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
- 150000001408 amides Chemical class 0.000 description 1
- 150000007656 barbituric acids Chemical class 0.000 description 1
- DULCUDSUACXJJC-UHFFFAOYSA-N benzeneacetic acid ethyl ester Natural products CCOC(=O)CC1=CC=CC=C1 DULCUDSUACXJJC-UHFFFAOYSA-N 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
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical class NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000003533 narcotic effect Effects 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 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
- 150000003839 salts Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 231100000241 scar Toxicity 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- KOEYZXDDPUFWAE-UHFFFAOYSA-M sodium;1-methylpyrimidin-3-ide-2,4,6-trione Chemical compound [Na+].CN1C(=O)CC(=O)[N-]C1=O KOEYZXDDPUFWAE-UHFFFAOYSA-M 0.000 description 1
- RCOSUMRTSQULBK-UHFFFAOYSA-N sodium;propan-1-olate Chemical compound [Na+].CCC[O-] RCOSUMRTSQULBK-UHFFFAOYSA-N 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
- 238000010626 work up procedure Methods 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (6)
| 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 |
| CH444361A CH425762A (de) | 1960-05-06 | 1961-04-14 | Verfahren zur Herstellung von N-alkylsubstituierten 3-Methoxy-4-carbamidomethoxyphenylessigsäurealkyl- und alkenylestern |
| CH319466A CH415587A (de) | 1960-05-06 | 1961-04-14 | Verfahren zur Herstellung von N-alkylsubstituierten 3-Methoxy-4-carbamidomethoxyphenylessigsäurealkyl- und -alkenylestern |
| GB1628061A GB906250A (en) | 1960-05-06 | 1961-05-04 | N-alkyl-substituted 3-methoxy-4-carbamidomethoxy-phenylacetic acid esters |
| DK186961A DK104841C (da) | 1960-05-06 | 1961-05-05 | Fremgangsmåde til fremstilling af N-alkylsubstituerede 3-methoxy-4-carbamido-methoxyphenyleddikesyrealkyl- eller -alkenylestere. |
| BE603477A BE603477A (fr) | 1960-05-06 | 1961-05-05 | Procédé de fabrication d'esters alkyliques ou alkényliques d'acides 3-méthoxy-4-carbamidométhoxyphényl-acétiques, à substituants alkyle sur l'azote |
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 |
|---|---|
| DE1134981B true DE1134981B (de) | 1962-08-23 |
Family
ID=7094083
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF31176A Pending DE1134981B (de) | 1960-05-06 | 1960-05-06 | Verfahren zur Herstellung von N-substituierten 3-Methoxy-4-carbamidomethoxyphenylessigsaeurealkyl- und alkenylestern |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE603477A (fr) |
| CH (2) | CH415587A (fr) |
| DE (1) | DE1134981B (fr) |
| DK (1) | DK104841C (fr) |
| GB (1) | GB906250A (fr) |
Cited By (4)
| 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 |
| EP0236280A1 (fr) | 1986-02-04 | 1987-09-09 | Basilio Mazzarella | Formulations pharmaceutiques injectables de principes actifs à activité anesthésique générale |
| WO2004037750A3 (fr) * | 2002-01-25 | 2005-01-06 | Theravance Inc | Agents hypnotiques sedatifs a action courte pour l'anesthesie et la sedation |
| US7790766B2 (en) | 2003-07-23 | 2010-09-07 | Theravance, Inc. | Pharmaceutical compositions of short-acting sedative hypnotic agent |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
-
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 DK DK186961A patent/DK104841C/da active
- 1961-05-05 BE BE603477A patent/BE603477A/fr unknown
Cited By (9)
| 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 |
| EP0236280A1 (fr) | 1986-02-04 | 1987-09-09 | Basilio Mazzarella | Formulations pharmaceutiques injectables de principes actifs à activité anesthésique générale |
| WO2004037750A3 (fr) * | 2002-01-25 | 2005-01-06 | Theravance Inc | Agents hypnotiques sedatifs a action courte pour l'anesthesie et la sedation |
| US6887866B2 (en) | 2002-01-25 | 2005-05-03 | Theravance, Inc. | Short-acting sedative hypnotic agents for anesthesia and sedation |
| RU2315037C2 (ru) * | 2002-01-25 | 2008-01-20 | Тереванс, Инк. | Замещенные эфиры фенилуксусной кислоты в качестве короткодействующих седативных снотворных агентов для кратковременной анестезии и создания седативного эффекта, промежуточное соединение, фармацевтическая композиция и применение |
| US7514425B2 (en) | 2002-01-25 | 2009-04-07 | Theravance, Inc. | Short-acting sedative hypnotic agents for anesthesia and sedation |
| US7939689B2 (en) | 2002-01-25 | 2011-05-10 | Theravance, Inc. | Short-acting sedative hypnotic agents for anesthesia and sedation |
| US7790766B2 (en) | 2003-07-23 | 2010-09-07 | Theravance, Inc. | Pharmaceutical compositions of short-acting sedative hypnotic agent |
| US7981931B2 (en) | 2003-07-23 | 2011-07-19 | Theravance, Inc. | Pharmaceutical compositions of short-acting sedative hypnotic agent |
Also Published As
| Publication number | Publication date |
|---|---|
| BE603477A (fr) | 1961-11-06 |
| CH425762A (de) | 1966-12-15 |
| CH415587A (de) | 1966-06-30 |
| GB906250A (en) | 1962-09-19 |
| DK104841C (da) | 1966-07-11 |
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