IL27360A - 1,alpha,alpha-trimethyl-2-piperidylcarbinol diphenylacetate,process for the preparation thereof and its use as topical anesthetic - Google Patents
1,alpha,alpha-trimethyl-2-piperidylcarbinol diphenylacetate,process for the preparation thereof and its use as topical anestheticInfo
- Publication number
- IL27360A IL27360A IL2736067A IL2736067A IL27360A IL 27360 A IL27360 A IL 27360A IL 2736067 A IL2736067 A IL 2736067A IL 2736067 A IL2736067 A IL 2736067A IL 27360 A IL27360 A IL 27360A
- Authority
- IL
- Israel
- Prior art keywords
- diphenylacetate
- alpha
- acid addition
- piperidylcarbinol
- process according
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 17
- PYHXGXCGESYPCW-UHFFFAOYSA-M 2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(C(=O)[O-])C1=CC=CC=C1 PYHXGXCGESYPCW-UHFFFAOYSA-M 0.000 title claims description 10
- 230000003444 anaesthetic effect Effects 0.000 title description 5
- 230000000699 topical effect Effects 0.000 title description 4
- 238000002360 preparation method Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 11
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 8
- 238000005984 hydrogenation reaction Methods 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- MSYLETHDEIJMAF-UHFFFAOYSA-N 2,2-diphenylacetyl chloride Chemical compound C=1C=CC=CC=1C(C(=O)Cl)C1=CC=CC=C1 MSYLETHDEIJMAF-UHFFFAOYSA-N 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- DQTZOBGQFRIPRU-UHFFFAOYSA-N 2,2-diphenylacetic acid;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(C(=O)O)C1=CC=CC=C1 DQTZOBGQFRIPRU-UHFFFAOYSA-N 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 206010002091 Anaesthesia Diseases 0.000 description 8
- 238000001949 anaesthesia Methods 0.000 description 8
- 230000037005 anaesthesia Effects 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 229960004194 lidocaine Drugs 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000008034 disappearance Effects 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000011514 reflex Effects 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 206010035039 Piloerection Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 210000003141 lower extremity Anatomy 0.000 description 1
- 210000002988 lumbosacral plexus Anatomy 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 210000004877 mucosa Anatomy 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000005371 pilomotor reflex Effects 0.000 description 1
- RJUAEBLXGFKZMS-UHFFFAOYSA-N piperidin-1-ylmethanol Chemical compound OCN1CCCCC1 RJUAEBLXGFKZMS-UHFFFAOYSA-N 0.000 description 1
- PRAYXGYYVXRDDW-UHFFFAOYSA-N piperidin-2-ylmethanol Chemical compound OCC1CCCCN1 PRAYXGYYVXRDDW-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
- C08J9/06—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a chemical blowing agent
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/02—Preparation by ring-closure or hydrogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2327/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers
- C08J2327/02—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers not modified by chemical after-treatment
- C08J2327/04—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers not modified by chemical after-treatment containing chlorine atoms
- C08J2327/06—Homopolymers or copolymers of vinyl chloride
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
C O H E N Z E D E K & S P I S B A C H R E G D. PA TE NT A TT O R N E YS 24, LEVONTIN SIR., P. O. B. 1169 T E L - A V I V Ί 3 P A T E N T S & D E S I G N S O R D I N A N C E 1615V67 SPECIFICATION 1 · tt-TRIMETHYL-2—PIPERIDULCARBINOL DIPHENYLACETATE , PROCESS FOR THE PREPARATION THEREOF AND ITS USE AS TOPICAL ANAESTHETIC ¾?n o Tain Tina ia SOCIETA' FABfi-ACEUTICI ITALIA, an Italian Joint Stock Company, of 1/2, largo Guido Donegani, Milano, Italy, HEREBY DECLARE the nature of this invention and in what manner the same is to be performed to be particularly described and ascertained in and by the following statement: The invention relates to a new 2-piperidylcarbinol which has proved useful in therapy as a topical anaesthetic and to a process of preparing it.
The new compound of the invention is the diphenylacetate of l,ck , k -trimethyl-2-piperidylcarbinol and the process of preparation starts from k ,<λ -dimethyl-2-pyr idylcarbinol and comprises hydrogenating to the corresponding piperidylcarbinol, treating this compound with formaldehyde and hydrogen in the presence of a hydrogenat ion catalyst, and esterifying the oroduct to form the diphenylacetate. The non-toxic pharmaceutically acceptable acid addition salts of the new compounds of the invention are also active. These may be obtained by treatment with an acid in the usual manner. The invention includes pharmaceutical compositions containing one or more active compounds according to the invention in admixture with a pharmaceutically acceptable diluent.
This process is illustrated by the following reaction scheme: CH- H n- I II esterify The new compound of the invention shows an interesting topical anaesthetic activity which has been tested in comparison with that of Lidocaine (2-diet hyl-amino-2' ,6' -aceto-xylidMe ) , which is a most effective product used in the field. It has been demonstrated that at the same toxicity level a clearly higher anaesthetic activity is shown by the new compound of the invention. Because of its major pharmacological activity the new compound of the invention can be classified among those substances capable of blocking the transmission of the nervous centripetal impulses in nerve fibres. Such an activity has been tested by the following methods; a) Sur ac e ..anae. st he s ia : The technique of anaesthesia of the conjunctival mucosa in the rabbit based on the b) Infiltration anaesthesia : The technique of intradermic anaesthesia in the Guinea-pig based upon the disappearance of the horripilation reflex (Btilbring E., Wa^da J.: J.
Pharmacol, exp. Ther., 19^ , 8>, 78) was used. c) Conduction anaesthesia : The technique of anaesthesia of the lumbar plexus of the frog based on the disappearance of the defence reflex of the lower limbs (Bulbring E., Wajda ubl supra) was used.
In all cases adequate gradual concentrations of l,dt > <λ -trimethyl-2-piperidylcarbinol dipheylacetate , dissolved in a physiological sodium chloride solution (NaCl 9°/Q0 τ 7°/00 for amphibians) were used. The symbol °/Q0 means per thousand. Determinations were repeated on at least 6-10 animals in order to obtain statistically valid and valuable data. The statistic evaluation of the activity ratio was calculated by the method of "6-point biological essay" according to the 1st supplement to the Farmacopea Ufficiale Italiana, 7th edition 1965. In Table 1 are reported the effective concentrations (A) of 1,<λ ,ελ -trimethyl-2-piperidylcarbinol dipheaylacetate and the activity ratio (B) in comparison to Lidocaine taken as unity. The effective concentration of a substance is that necessary to produce total anaesthesia for at least 30 minutes in the subject under examination.
TABLS 1 From the above data the new compound of the invention appears active even at very low concentrations. In intradermic anaesthesia it is at least three times more ative than Lidocaine while in surface anaesthesia this ratio rises to about forty.
Acute o icity determined in the albino mouse by a single treatment by various admi istration routes is practicall; the same as that of Lidocaine subcutaneously administered.
The test has been carried out on groups of a least 10 subjects for each dosage and the relevant statistical calculation of LD^Q and of limits of utility has been carried out by the probits method (Burn J.H.: Biological Standardization - Oxford 1950). In Table 2 LD^0 (acute toxicity) data after subcutaneous and intravenous administratio of 1,· ,
The following Example illustrates the invention: EXAMPLE 1Τ Λ ,<Λ -trimethyl-2-pineridylc^arbiniOl, diphenylacetate 39.75 g of ck -dimethyl-2-pyridylcarbinol (prepared according to Chem. Ber., 1908, ίϋ, page LH03) are dissolved in 60 cc of ethanol. 1 g of Adams platinum is added and hydrogenat ion is carried out in an autoclave at 90°C under 60 atmospheres s h u caustic soda and extracted with diethyl ether. After evaporation of the ether 25 g of t -dimethyl-2-piperidylcarbinol are distilled in vacuo. The boiling point is 78-80°C under a pressure of 5 mm Hg.
To 9.7 g of this compound dissolved in 100 cc of ethanol 11 cc of 30 aqueous formaldehyde solution and 0.7 g of 10$ palladium on charcoal are added and hydrogenat ion is carried out at 110°C under a pressure of 60 atmospheres. After 20 hours the reaction mass is filtered, the alcohol is removed, and the remainder is distilled in vacuo, The fraction which distills between 70 and 75°C under a pressure of 2 mm Hg is collected. 6.5 g of 1,<Λ^ -trimethyl-2-piperidylcarbinol are obtained.
To 2 g of this last compound dissolved in 10 cc of pyridine 3 g of diphenylacetyl chloride are added. After 2 days the pyridine is evaporated off in vacuo, taken up with benzene and washed with a 10$ aqueous sodium hydroxide solution. The benzene solution is dried and chromatographed over a column of 60 g of silica gel. By elution 2.5 g of 1, c jck -trimethyl-2-piperidylcarbinol diphenylacetate are obtained, which on treatment with hydrochloric acid gives the corresponding hydrochloride in the form of a white crystalline powder, soluble in water and ethanol. Melting point: 177°C.
Claims (2)
1. particularly and ascertained the our and is to be that what A process of preparing carbinol diphenylacetate a acceptable acid addition salt thereof in which is hydrogenated to the corresponding this compound with formaldehyde and hydrogen in the presence of a hydrogenation esterifying the product to form the he ylacet and where appropriate treating with an acid to obtain a pharmaceutically acceptable acid addition A process according to Claim 1 in which the initial hydrogenation is carried out in the presence of Adams A process according to Claim 1 or
2. Claim 2 in which the treatment with formaldehyde and hydrogen is carried out in the oresence of palladium on A process according to any of the preceding claims in which esterificat ion is carried out with diphenylacetyl chloride A process of preparing carbinol diphenylacetate or a pharmaceutically of acceptable acid addition salt substant ially as hereinbefore described in the 1 carbinol diphenylacetate or a pharmaceutically acceptable acid addition salt thereof prepared by a process according to any of the preceding 1 diphenylacetate hydrochloride A pharmaceutical composition containing 1 diphenylacetate or a acid addition salt thereof in admixture with a tically acceptable Dated this 9th day of Box Attorneys for Applicants insufficientOCRQuality
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1408166 | 1966-02-03 | ||
| IT228666 | 1966-02-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL27360A true IL27360A (en) | 1971-01-28 |
Family
ID=26325232
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL2736067A IL27360A (en) | 1966-02-03 | 1967-01-30 | 1,alpha,alpha-trimethyl-2-piperidylcarbinol diphenylacetate,process for the preparation thereof and its use as topical anesthetic |
Country Status (11)
| Country | Link |
|---|---|
| BE (1) | BE693587A (en) |
| CH (1) | CH484905A (en) |
| DK (1) | DK118186B (en) |
| ES (1) | ES336375A1 (en) |
| FR (1) | FR6135M (en) |
| GB (1) | GB1110637A (en) |
| IL (1) | IL27360A (en) |
| NL (1) | NL6701022A (en) |
| NO (1) | NO122068B (en) |
| SE (1) | SE321474B (en) |
| YU (1) | YU32140B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE7607114L (en) | 1976-06-22 | 1977-12-23 | Bofors Ab | METHOD OF PREPARING THE HYDROCHLORIDE OF N-METHYLPIPERIDINE-2-CARBONIC ACID-2,6-XYLLIDIDE |
-
1967
- 1967-01-23 NL NL6701022A patent/NL6701022A/xx unknown
- 1967-01-30 NO NO16661667A patent/NO122068B/no unknown
- 1967-01-30 GB GB4503/67A patent/GB1110637A/en not_active Expired
- 1967-01-30 IL IL2736067A patent/IL27360A/en unknown
- 1967-01-31 YU YU18367A patent/YU32140B/en unknown
- 1967-01-31 FR FR93178A patent/FR6135M/fr not_active Expired
- 1967-01-31 DK DK54467A patent/DK118186B/en unknown
- 1967-02-01 SE SE139967A patent/SE321474B/xx unknown
- 1967-02-02 BE BE693587D patent/BE693587A/xx unknown
- 1967-02-02 CH CH151767A patent/CH484905A/en not_active IP Right Cessation
- 1967-02-02 ES ES336375A patent/ES336375A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE693587A (en) | 1967-08-02 |
| FR6135M (en) | 1968-06-24 |
| DK118186B (en) | 1970-07-20 |
| ES336375A1 (en) | 1968-04-01 |
| YU32140B (en) | 1974-04-30 |
| YU18367A (en) | 1973-08-31 |
| NL6701022A (en) | 1967-08-04 |
| SE321474B (en) | 1970-03-09 |
| CH484905A (en) | 1970-01-31 |
| GB1110637A (en) | 1968-04-24 |
| NO122068B (en) | 1971-05-18 |
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