GB949729A - Substituted-piperidine carboxylic acid amide salts and their preparation - Google Patents
Substituted-piperidine carboxylic acid amide salts and their preparationInfo
- Publication number
- GB949729A GB949729A GB38223/61A GB3822361A GB949729A GB 949729 A GB949729 A GB 949729A GB 38223/61 A GB38223/61 A GB 38223/61A GB 3822361 A GB3822361 A GB 3822361A GB 949729 A GB949729 A GB 949729A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- compound
- reacting
- ethyl
- carboxylic acid
- 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.)
- Expired
Links
- -1 Substituted-piperidine carboxylic acid amide salts Chemical class 0.000 title abstract 9
- 238000002360 preparation method Methods 0.000 title abstract 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 150000002148 esters Chemical class 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 2
- HXEACLLIILLPRG-RXMQYKEDSA-N l-pipecolic acid Natural products OC(=O)[C@H]1CCCCN1 HXEACLLIILLPRG-RXMQYKEDSA-N 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 239000011707 mineral Substances 0.000 abstract 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 abstract 2
- HXEACLLIILLPRG-UHFFFAOYSA-N pipecolic acid Chemical compound OC(=O)C1CCCCN1 HXEACLLIILLPRG-UHFFFAOYSA-N 0.000 abstract 2
- ACJCVOSGLDUKHK-UHFFFAOYSA-N 5-ethylpiperidine-2-carbonyl chloride Chemical compound C(C)C1CCC(NC1)C(=O)Cl ACJCVOSGLDUKHK-UHFFFAOYSA-N 0.000 abstract 1
- UJSREKSIWDGDGP-UHFFFAOYSA-N 5-ethylpyridine-2-carboxylic acid hydrochloride Chemical compound Cl.C(C)C=1C=CC(=NC1)C(=O)O UJSREKSIWDGDGP-UHFFFAOYSA-N 0.000 abstract 1
- CCOXVYMCSPMMNE-UHFFFAOYSA-N 6-amino-2-chlorohexanoyl chloride Chemical compound ClC(C(=O)Cl)CCCCN CCOXVYMCSPMMNE-UHFFFAOYSA-N 0.000 abstract 1
- GBMMTXISGBKPJB-UHFFFAOYSA-N Cl.C(C)C1CCC(NC1)C(=O)O Chemical compound Cl.C(C)C1CCC(NC1)C(=O)O GBMMTXISGBKPJB-UHFFFAOYSA-N 0.000 abstract 1
- 150000000996 L-ascorbic acids Chemical class 0.000 abstract 1
- 235000011054 acetic acid Nutrition 0.000 abstract 1
- 150000001243 acetic acids Chemical class 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 229940124326 anaesthetic agent Drugs 0.000 abstract 1
- 230000003444 anaesthetic effect Effects 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 235000010323 ascorbic acid Nutrition 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- 235000010233 benzoic acid Nutrition 0.000 abstract 1
- 150000001559 benzoic acids Chemical class 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical group C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 abstract 1
- 239000012024 dehydrating agents Substances 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000012458 free base Substances 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 238000002347 injection Methods 0.000 abstract 1
- 239000007924 injection Substances 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- 150000002513 isocyanates Chemical class 0.000 abstract 1
- 150000002691 malonic acids Chemical class 0.000 abstract 1
- GVBHRBMWXDCRHZ-UHFFFAOYSA-N n-phenylpyridine-2-carboxamide Chemical compound C=1C=CC=NC=1C(=O)NC1=CC=CC=C1 GVBHRBMWXDCRHZ-UHFFFAOYSA-N 0.000 abstract 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 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)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention comprises acid-addition salts of compounds of the formula: <FORM:0949729/C2/1> (in which one of R1 and R2 is hydrogen and the other is methyl or ethyl, and R3, R4, R5, R6 and R7 are hydrogen atoms or methyl or ethyl radicals, the total number of carbon atoms in these radicals not exceeding four) and their preparation by (1) condensing the appropriate piperidine -2- carboxylic acid or the anhydride or an ester or halide thereof with the appropriate aniline compound or with the corresponding isocyanate; or (2) catalytically hydrogenating the corresponding pyridine -2- carboxylic acid anilide; or (3) reacting an ester of the appropriate piperidine -2- carboxylic acid or the corresponding pyridine compound with an organo magnesium halide compound of the appropriate aniline compound and, if necessary, hydrogenating the product; or (4) reacting 2-chloro -6-amino-caproic acid chloride, substituted in the 5- or 6-position with the substituent R1 or R2, with the appropriate aniline compound and ring-closing the product with a strong base; or (5) nitrosating a compound of the formula: <FORM:0949729/C2/2> (wherein R8 is an alkyl radical), reducing the product and reacting with an alkylene dihalide to give a compound of the formula: <FORM:0949729/C2/3> (wherein X is a halogen atom) and ring closing this with concomitant removal of the ester group in the presence of a mineral acid; or (6) reacting the appropriate pyridine -2- carboxylic acid with the appropriate aniline compound to produce the amine salt of the acid, heating the salt and treating with a dehydrating agent, and hydrogenating the product; and then converting the free base, if isolated, into the acid-addition salt. Detailed examples are given, salts with mineral acids and sulphamic, glycollic, citric, malonic, acetic, benzoic and ascorbic acids being described or referred to. 5-Ethyl-pipecolinic acid chloride is prepared by hydrogenating 5-ethyl-picolinic acid hydrochloride to give 5-ethyl-pipecolinic acid hydrochloride and reacting this with phosphorus pentachloride. The amide salts of the invention, which are anaesthetics, may be made up into injection solutions. Specifications 775,750,800,565 and 800,670 are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE1096760 | 1960-11-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB949729A true GB949729A (en) | 1964-02-19 |
Family
ID=20293137
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB38223/61A Expired GB949729A (en) | 1960-11-15 | 1961-10-25 | Substituted-piperidine carboxylic acid amide salts and their preparation |
Country Status (2)
| Country | Link |
|---|---|
| FR (1) | FR1599M (en) |
| GB (1) | GB949729A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4695576A (en) * | 1984-07-09 | 1987-09-22 | Astra Lake Medel Aktiebolag | L-N-n-propylpipecolic acid-2,6-xylidide |
| US4870086A (en) * | 1986-01-03 | 1989-09-26 | Astra Lakemedel Aktiebolag | Optically pure compound and a process for its preparation |
| US4904673A (en) * | 1988-01-14 | 1990-02-27 | Dr. Karl Thomae, Gmbh | Agent for treating bradycardia and bradyarrhythmia |
| EP0514341A1 (en) * | 1991-05-17 | 1992-11-19 | Sandoz Ltd. | Novel heterocylic anilides for weed control |
| WO2010084516A1 (en) * | 2009-01-23 | 2010-07-29 | Jubilant Organosys Limited | Process for producing optically active n-alkyl-piperidine-2-carboxanilide |
| CN104003930A (en) * | 2014-06-13 | 2014-08-27 | 山东阿如拉药物研究开发有限公司 | Method for preparing hydrochloric acid ropivacaine |
-
1961
- 1961-10-25 GB GB38223/61A patent/GB949729A/en not_active Expired
- 1961-11-14 FR FR878893A patent/FR1599M/en not_active Expired
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4695576A (en) * | 1984-07-09 | 1987-09-22 | Astra Lake Medel Aktiebolag | L-N-n-propylpipecolic acid-2,6-xylidide |
| US4870086A (en) * | 1986-01-03 | 1989-09-26 | Astra Lakemedel Aktiebolag | Optically pure compound and a process for its preparation |
| US4904673A (en) * | 1988-01-14 | 1990-02-27 | Dr. Karl Thomae, Gmbh | Agent for treating bradycardia and bradyarrhythmia |
| EP0514341A1 (en) * | 1991-05-17 | 1992-11-19 | Sandoz Ltd. | Novel heterocylic anilides for weed control |
| US5312799A (en) * | 1991-05-17 | 1994-05-17 | Sandoz Ltd. | Amides |
| WO2010084516A1 (en) * | 2009-01-23 | 2010-07-29 | Jubilant Organosys Limited | Process for producing optically active n-alkyl-piperidine-2-carboxanilide |
| CN104003930A (en) * | 2014-06-13 | 2014-08-27 | 山东阿如拉药物研究开发有限公司 | Method for preparing hydrochloric acid ropivacaine |
| CN104003930B (en) * | 2014-06-13 | 2016-06-08 | 山东金诃药物研究开发有限公司 | The preparation method of a kind of hydrochloric acid ropivacaine |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1599M (en) | 1962-12-03 |
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