CH369132A - Process for the preparation of nipecotinic acid amides - Google Patents
Process for the preparation of nipecotinic acid amidesInfo
- Publication number
- CH369132A CH369132A CH6283058A CH6283058A CH369132A CH 369132 A CH369132 A CH 369132A CH 6283058 A CH6283058 A CH 6283058A CH 6283058 A CH6283058 A CH 6283058A CH 369132 A CH369132 A CH 369132A
- Authority
- CH
- Switzerland
- Prior art keywords
- hexahydropyridine
- carboxylic acid
- acid amide
- methyl
- carbo
- Prior art date
Links
- 150000001408 amides Chemical class 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 5
- -1 1-n-octadecyl-hexahydropyridine-3-carboxylic acid amide Chemical compound 0.000 claims description 13
- 150000003839 salts Chemical group 0.000 claims description 7
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
- 235000005152 nicotinamide Nutrition 0.000 claims description 2
- 239000011570 nicotinamide Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- BVOCPVIXARZNQN-UHFFFAOYSA-N nipecotamide Chemical compound NC(=O)C1CCCNC1 BVOCPVIXARZNQN-UHFFFAOYSA-N 0.000 claims 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims 2
- 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 2
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229910003446 platinum oxide Inorganic materials 0.000 description 2
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OOSWYPPXWOIAFP-UHFFFAOYSA-N 1-dodecylpiperidine-3-carboxamide Chemical compound CCCCCCCCCCCCN1CCCC(C(N)=O)C1 OOSWYPPXWOIAFP-UHFFFAOYSA-N 0.000 description 1
- OFISITBDEXNBTC-UHFFFAOYSA-N 1-ethyl-n,n-dimethylpiperidine-3-carboxamide Chemical compound CCN1CCCC(C(=O)N(C)C)C1 OFISITBDEXNBTC-UHFFFAOYSA-N 0.000 description 1
- BGQZAHIRBZUDOL-UHFFFAOYSA-N 1-heptylpiperidine-3-carboxamide Chemical compound CCCCCCCN1CCCC(C(N)=O)C1 BGQZAHIRBZUDOL-UHFFFAOYSA-N 0.000 description 1
- VMYWLIVDQSXFQA-UHFFFAOYSA-N 1-pentylpiperidine-3-carboxamide Chemical compound CCCCCN1CCCC(C(N)=O)C1 VMYWLIVDQSXFQA-UHFFFAOYSA-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
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229960004909 aminosalicylic acid Drugs 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 1
- 229940124339 anthelmintic agent Drugs 0.000 description 1
- 239000000921 anthelmintic agent Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 229960004106 citric acid Drugs 0.000 description 1
- 150000001875 compounds Chemical group 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229960002598 fumaric acid Drugs 0.000 description 1
- 229960004275 glycolic acid Drugs 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- OIYHTABGPWSCIY-UHFFFAOYSA-N n,n,1-triethylpiperidine-3-carboxamide Chemical compound CCN(CC)C(=O)C1CCCN(CC)C1 OIYHTABGPWSCIY-UHFFFAOYSA-N 0.000 description 1
- GHJMFLHSVUMQMV-UHFFFAOYSA-N n,n,1-trimethylpiperidine-3-carboxamide Chemical compound CN(C)C(=O)C1CCCN(C)C1 GHJMFLHSVUMQMV-UHFFFAOYSA-N 0.000 description 1
- GOQVOSCJGILEEX-UHFFFAOYSA-N n,n-diethyl-1-methylpiperidine-3-carboxamide Chemical compound CCN(CC)C(=O)C1CCCN(C)C1 GOQVOSCJGILEEX-UHFFFAOYSA-N 0.000 description 1
- BPSVRSODUGNDNJ-UHFFFAOYSA-N n,n-dimethyl-1-propylpiperidine-3-carboxamide Chemical compound CCCN1CCCC(C(=O)N(C)C)C1 BPSVRSODUGNDNJ-UHFFFAOYSA-N 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07D211/36—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung von Nipecotinsäureamiden
Es wurde gefunden, dass Amide heterocyclischer Carbonsäuren der Formel
EMI1.1
in welcher Am eine substituierte oder unsubstituierte Aminogruppe und R einen Alkylrest bedeuten, der durch Sauerstoff, Schwefel, Sous, NH, N-Alkyl, CO-NH, CO-N-Alkyl, COO unterbrochen sein kann, sowie deren Säureadditionssalze wertvolle Desinfektionsmittel und Anthelmintica darstellen. Sie hemmen auch das Wachstum von Pilzen.
Als Reste Am kommen neben der unsubstituierten Aminogruppe NH2, vor allem die mono-oder dialkylierte Aminogruppe, die Pyrrolidinogruppe
EMI1.2
die Morpholino-oder Piperidinogruppe in Frage, wobei die Pyrrolidino-bzw. Morpholino-bzw. Piperidinogruppe auch ein-oder mehrfach alkyliert sein kann.
Gegenstand des vorliegenden Patentes ist daher ein Verfahren zur Herstellung der Nipecotinsäure- amide der Formel I, das dadurch gekennzeichnet ist, dass man ein quaternäres Salz eines Pyridin-3-carbonsäureamids der Formel
EMI1.3
der katalytischen Hydrierung unterwirft.
Das erhaltene Nipecotinsäureamid kxtm--ge- wünschtenfalls in ein Säureadditionssalz übergeführt werden.
Die Hydrierung erfolgt vorteilhaft in einem Lösungsmittel, wie z. B. Methanol oder Äthanol.
Als Katalysatoren kann man Raney-Nickel, Palladium-oder Platin-Katalysatoren verwenden. Mit Platinoxyd lässt sich die Reduktion sehr glatt und mit guter Ausbeute durchführen. Im allgemeinen wird unter Druck und bei gewöhnlicher Temperatur hydriert.
Zur Salzbildung eignen sich anorganische und organische untoxische Säuren.
Als anorganische Säuren kommen zur Salzbildung in Frage : Chlorwasserstoffsäure, Bromwasser stoffsäure, Schwefelsäure, Phosphorsäuren und Sulf- aminsäure. Als organische Säuren kommen in Frage : Essigäure, Glycolsäure, Citronensäure, Fumarsäure, Nicotinsäure, Salicylsäure, p-Amino-salicylsäure und andere mehr.
Beispiel
50 g 3-Carbamyl-l-n-heptyl-pyridinium-bromid werden in 500 cm3 Athanol mit 0,15 g Platinoxyd im Autoklaven bei 20 C unter 100 at. Wasserstoffdruck geschüttelt. Nach 8 Stunden ist die Hydrierung beendet. Der Katalysator wird abfiltriert und das Filtrat im Vakuum verdampft. Der Rückstand wird in Wasser gelöst, mit Kohle filtriert, und mit konz.
Natronlauge wird die Base gefällt. Diese wird abgesaugt, mit Wasser gewaschen und aus 10e/o, igem Athanol umkristallisiert. Man erhält 30 g an 1-n Heptyl-piperidin-3-carbonsäureamid. Die neue Verbindung bildet farblose Kristalle, die bei 99-100 C schmelzen.
Wie im Beispiel beschrieben, gewinnt man weiter die folgenden Verbindungen :
Fp. des
Hydro chlorides oC 1-Methyl-hexahydropyridin-3-carbonsäure- dimethylamid 178-180 1-Athyl-hexahydropyridin-3-carbonsäure- dimethylamid 205-206 1-n-Propyl-hexahydropyridin-3-carbonsäure- dimethylamid 178-179 1-Methyl-hexahydropyridin-3-carbonsäure- diäthylamid 149-150 1-Athyl-hexahydropyridin-3-carbonsäure- diäthylamid 80-82 I-n-Propyl-hexahydropyridin-3-carbonsäure- diäthylamid 145-147 1-Methyl-hexahydropyridin-3-carbonsäure- di-n-propylamid 113-115 <RTI
ID=2.14> 1-AthylLhexahydropyridin-3-carbonsäure- di-n-propylamid 110-111 1-n-Propyl-hexahydropyridin-3-carbonsäure- di-n-propylamid 116-117
Fp. der
Base C l-n-Butyl-hexahydropyridin-3-carbonsäure- amid 78-81 l-n-Pentyl-hexahydropyridin-3-carbonsäure- amid 92-94 1-i-Pentyl-hexahydropyridin-3-carbonsäure- amid 113-115 1-n-Hexyl-hexahydropyridin-3-carbonsäure- amid 99-101 l-n-Octyl-hexahydropyridin-3-carbonsäure amid 95-97 l-n-Nonyl-hexahydropyridin-3-carbonsäure amid 96-97 l-n-Decyl-hexahydropyridin-3-carbonsäure- amid 98-99 1-n-Undecyl-hexahydropyridin-3-carbon- säure-amid 100-101 <RTI
ID=2.25> 1-n-DodecylLhexahydropyridin-3-carbon- säure-amid 100-101 l-n-Tetradecyl-hexahydropyridin-3-carbon- saure-ami 96-98 1-n-Hexadecyl-hexahydropyridin-3-carbon- säure-amid 102-103
Process for the preparation of nipecotinic acid amides
It has been found that amides of heterocyclic carboxylic acids of the formula
EMI1.1
in which Am is a substituted or unsubstituted amino group and R is an alkyl radical which can be interrupted by oxygen, sulfur, Sous, NH, N-alkyl, CO-NH, CO-N-alkyl, COO, and their acid addition salts are valuable disinfectants and anthelmintics represent. They also inhibit the growth of fungi.
In addition to the unsubstituted amino group NH2, especially the mono- or dialkylated amino group, the pyrrolidino group are used as radicals Am
EMI1.2
the morpholino or piperidino group in question, the pyrrolidino or. Morpholino or. Piperidino group can also be alkylated one or more times.
The subject of the present patent is therefore a process for the preparation of the nipecotinic acid amides of the formula I, which is characterized in that a quaternary salt of a pyridine-3-carboxamide of the formula I is used
EMI1.3
subjected to catalytic hydrogenation.
The nipecotinic acid amide obtained kxtm - if desired, can be converted into an acid addition salt.
The hydrogenation is advantageously carried out in a solvent, such as. B. methanol or ethanol.
Raney nickel, palladium or platinum catalysts can be used as catalysts. With platinum oxide, the reduction can be carried out very smoothly and with good yield. In general, hydrogenation is carried out under pressure and at ordinary temperature.
Inorganic and organic non-toxic acids are suitable for salt formation.
The following inorganic acids are suitable for salt formation: hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acids and sulphamic acid. The following organic acids come into question: acetic acid, glycolic acid, citric acid, fumaric acid, nicotinic acid, salicylic acid, p-amino-salicylic acid and others.
example
50 g of 3-carbamyl-1-n-heptyl-pyridinium bromide are shaken in 500 cm3 of ethanol with 0.15 g of platinum oxide in an autoclave at 20 ° C. under 100 atm. Hydrogen pressure. The hydrogenation has ended after 8 hours. The catalyst is filtered off and the filtrate is evaporated in vacuo. The residue is dissolved in water, filtered with charcoal, and with conc.
Caustic soda is used to precipitate the base. This is filtered off with suction, washed with water and recrystallized from 10e / o strength ethanol. 30 g of 1-n heptyl-piperidine-3-carboxamide are obtained. The new compound forms colorless crystals that melt at 99-100 C.
As described in the example, the following connections are obtained:
Fp. Des
Hydro chlorides oC 1-methyl-hexahydropyridine-3-carboxylic acid dimethylamide 178-180 1-ethyl-hexahydropyridine-3-carboxylic acid dimethylamide 205-206 1-n-propyl-hexahydropyridine-3-carboxylic acid dimethylamide 178-179 1-methyl -hexahydropyridine-3-carboxylic acid diethylamide 149-150 1-ethyl-hexahydropyridine-3-carboxylic acid diethylamide 80-82 In-propyl-hexahydropyridine-3-carboxylic acid diethylamide 145-147 1-methyl-hexahydropyridine-3-carboxylic acid di -n-propylamide 113-115 <RTI
ID = 2.14> 1-EthylLhexahydropyridine-3-carboxylic acid-di-n-propylamide 110-111 1-n-Propyl-hexahydropyridine-3-carboxylic acid-di-n-propylamide 116-117
Fp. The
Base C In-butyl-hexahydropyridine-3-carboxylic acid amide 78-81 In-pentyl-hexahydropyridine-3-carboxylic acid amide 92-94 1-i-pentyl-hexahydropyridine-3-carboxylic acid amide 113-115 1-n- Hexyl-hexahydropyridine-3-carboxylic acid amide 99-101 In-octyl-hexahydropyridine-3-carboxylic acid amide 95-97 In-nonyl-hexahydropyridine-3-carboxylic acid amide 96-97 In-decyl-hexahydropyridine-3-carboxylic acid amide 98 -99 1-n-Undecyl-hexahydropyridine-3-carboxylic acid amide 100-101 <RTI
ID = 2.25> 1-n-dodecyl-hexahydropyridine-3-carboxylic acid amide 100-101 ln-tetradecyl-hexahydropyridine-3-carboxylic acid ami 96-98 1-n-hexadecyl-hexahydropyridine-3-carboxylic acid amid 102-103
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH6283058A CH369132A (en) | 1958-08-12 | 1958-08-12 | Process for the preparation of nipecotinic acid amides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH6283058A CH369132A (en) | 1958-08-12 | 1958-08-12 | Process for the preparation of nipecotinic acid amides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH369132A true CH369132A (en) | 1963-05-15 |
Family
ID=4524551
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH6283058A CH369132A (en) | 1958-08-12 | 1958-08-12 | Process for the preparation of nipecotinic acid amides |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH369132A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2085726A1 (en) * | 1970-03-20 | 1971-12-31 | Nelson Res & Dev | |
| EP0219934A1 (en) * | 1985-08-10 | 1987-04-29 | Beecham Group Plc | Process for the preparation of aryl-piperidine esters |
-
1958
- 1958-08-12 CH CH6283058A patent/CH369132A/en unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2085726A1 (en) * | 1970-03-20 | 1971-12-31 | Nelson Res & Dev | |
| EP0219934A1 (en) * | 1985-08-10 | 1987-04-29 | Beecham Group Plc | Process for the preparation of aryl-piperidine esters |
| US4861893A (en) * | 1985-08-10 | 1989-08-29 | Beecham Group Plc. | Chemical process |
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