DE2704365C2 - Zimtsäureamide, Verfahren zu ihrer Herstellung und pharmazeutische Zubereitungen, welche diese Verbindungen enthalten - Google Patents
Zimtsäureamide, Verfahren zu ihrer Herstellung und pharmazeutische Zubereitungen, welche diese Verbindungen enthaltenInfo
- Publication number
- DE2704365C2 DE2704365C2 DE2704365A DE2704365A DE2704365C2 DE 2704365 C2 DE2704365 C2 DE 2704365C2 DE 2704365 A DE2704365 A DE 2704365A DE 2704365 A DE2704365 A DE 2704365A DE 2704365 C2 DE2704365 C2 DE 2704365C2
- Authority
- DE
- Germany
- Prior art keywords
- compounds
- acid
- general formula
- trans
- acid amide
- 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
- 150000001875 compounds Chemical class 0.000 title claims description 35
- 238000000034 method Methods 0.000 title claims description 14
- 239000000825 pharmaceutical preparation Substances 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001408 amides Chemical class 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 9
- APEJMQOBVMLION-UHFFFAOYSA-N cinnamamide Chemical compound NC(=O)C=CC1=CC=CC=C1 APEJMQOBVMLION-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 241000282326 Felis catus Species 0.000 description 15
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- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
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- 239000004606 Fillers/Extenders Substances 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical class NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-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
- 235000021355 Stearic acid Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
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- 239000007900 aqueous suspension Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
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- OFZCIYFFPZCNJE-UHFFFAOYSA-N carisoprodol Chemical compound NC(=O)OCC(C)(CCC)COC(=O)NC(C)C OFZCIYFFPZCNJE-UHFFFAOYSA-N 0.000 description 2
- 229960004587 carisoprodol Drugs 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
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- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
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- KSBWHDDGWSYETA-SNAWJCMRSA-N (E)-3-(trifluoromethyl)cinnamic acid Chemical compound OC(=O)\C=C\C1=CC=CC(C(F)(F)F)=C1 KSBWHDDGWSYETA-SNAWJCMRSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/11—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/09—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an acyclic unsaturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/48—Unsaturated compounds containing hydroxy or O-metal groups containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/612—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety
- C07C69/618—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety having unsaturation outside the six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (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)
- Indole Compounds (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB416976 | 1976-02-03 | ||
| GB4168/76A GB1568401A (en) | 1976-02-03 | 1976-02-03 | Biologically active amides |
| GB417076 | 1976-02-03 | ||
| US71213476A | 1976-08-06 | 1976-08-06 | |
| US71213576A | 1976-08-06 | 1976-08-06 | |
| US71231876A | 1976-08-06 | 1976-08-06 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2704365A1 DE2704365A1 (de) | 1977-08-04 |
| DE2704365C2 true DE2704365C2 (de) | 1986-03-20 |
Family
ID=27546490
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2704365A Expired DE2704365C2 (de) | 1976-02-03 | 1977-02-02 | Zimtsäureamide, Verfahren zu ihrer Herstellung und pharmazeutische Zubereitungen, welche diese Verbindungen enthalten |
Country Status (20)
| Country | Link |
|---|---|
| JP (1) | JPS6056700B2 (enExample) |
| AR (1) | AR218865A1 (enExample) |
| AT (1) | AT363926B (enExample) |
| BE (1) | BE851020A (enExample) |
| CA (1) | CA1109076A (enExample) |
| CH (1) | CH634551A5 (enExample) |
| CS (2) | CS245756B2 (enExample) |
| DD (1) | DD130349A5 (enExample) |
| DE (1) | DE2704365C2 (enExample) |
| DK (1) | DK43177A (enExample) |
| FI (1) | FI69625C (enExample) |
| FR (1) | FR2340303A1 (enExample) |
| GB (1) | GB1568401A (enExample) |
| GR (1) | GR66474B (enExample) |
| HU (1) | HU175435B (enExample) |
| IE (1) | IE44862B1 (enExample) |
| IL (1) | IL51373A (enExample) |
| NL (1) | NL7701088A (enExample) |
| PL (2) | PL119314B1 (enExample) |
| SE (2) | SE436870B (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0714871B2 (ja) * | 1989-02-02 | 1995-02-22 | 大正製薬株式会社 | 筋弛緩剤 |
| DE19931116A1 (de) * | 1999-07-06 | 2001-01-11 | Bayer Ag | Verfahren zur Herstellung von Phenethylaminen und neue chemische Verbindungen |
| CN104513172B (zh) * | 2013-09-30 | 2018-02-02 | 天士力医药集团股份有限公司 | 含有三氟甲基的酰胺生物碱、制备方法及其药物用途 |
| CN104432097B (zh) * | 2014-12-16 | 2016-08-17 | 广州渔夫堡医药科技有限公司 | 一种缓解体力疲劳的天然增补剂 |
-
1976
- 1976-02-03 GB GB4168/76A patent/GB1568401A/en not_active Expired
-
1977
- 1977-02-02 FI FI770365A patent/FI69625C/fi not_active IP Right Cessation
- 1977-02-02 IE IE212/77A patent/IE44862B1/en unknown
- 1977-02-02 CH CH125377A patent/CH634551A5/de not_active IP Right Cessation
- 1977-02-02 JP JP52010599A patent/JPS6056700B2/ja not_active Expired
- 1977-02-02 BE BE174605A patent/BE851020A/xx not_active IP Right Cessation
- 1977-02-02 FR FR7702865A patent/FR2340303A1/fr active Granted
- 1977-02-02 PL PL1977214782A patent/PL119314B1/pl unknown
- 1977-02-02 SE SE7701107A patent/SE436870B/xx not_active IP Right Cessation
- 1977-02-02 DK DK43177A patent/DK43177A/da not_active Application Discontinuation
- 1977-02-02 AT AT0065277A patent/AT363926B/de not_active IP Right Cessation
- 1977-02-02 AR AR266409A patent/AR218865A1/es active
- 1977-02-02 DD DD7700197200A patent/DD130349A5/xx not_active IP Right Cessation
- 1977-02-02 GR GR52690A patent/GR66474B/el unknown
- 1977-02-02 HU HU77WE549A patent/HU175435B/hu not_active IP Right Cessation
- 1977-02-02 PL PL1977195740A patent/PL119716B1/pl not_active IP Right Cessation
- 1977-02-02 IL IL51373A patent/IL51373A/xx unknown
- 1977-02-02 NL NL7701088A patent/NL7701088A/xx not_active Application Discontinuation
- 1977-02-02 DE DE2704365A patent/DE2704365C2/de not_active Expired
- 1977-02-02 CS CS77695A patent/CS245756B2/cs unknown
- 1977-02-02 CA CA270,904A patent/CA1109076A/en not_active Expired
- 1977-02-02 CS CS777652A patent/CS245758B2/cs unknown
-
1983
- 1983-01-28 SE SE8300432A patent/SE8300432L/sv not_active Application Discontinuation
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2340303A1 (fr) | 1977-09-02 |
| PL195740A1 (pl) | 1979-05-07 |
| SE436870B (sv) | 1985-01-28 |
| DE2704365A1 (de) | 1977-08-04 |
| DK43177A (da) | 1977-08-04 |
| CH634551A5 (en) | 1983-02-15 |
| AR218865A1 (es) | 1980-07-15 |
| DD130349A5 (de) | 1978-03-22 |
| GB1568401A (en) | 1980-05-29 |
| PL119716B1 (en) | 1982-01-30 |
| FI69625B (fi) | 1985-11-29 |
| JPS6056700B2 (ja) | 1985-12-11 |
| ATA65277A (de) | 1981-02-15 |
| HU175435B (hu) | 1980-07-28 |
| SE8300432D0 (sv) | 1983-01-28 |
| FI69625C (fi) | 1986-03-10 |
| GR66474B (enExample) | 1981-03-23 |
| AT363926B (de) | 1981-09-10 |
| IL51373A (en) | 1981-12-31 |
| SE7701107L (sv) | 1977-08-04 |
| PL119314B1 (en) | 1981-12-31 |
| NL7701088A (nl) | 1977-08-05 |
| JPS52116437A (en) | 1977-09-29 |
| FI770365A7 (enExample) | 1977-08-04 |
| IE44862L (en) | 1977-08-03 |
| IE44862B1 (en) | 1982-04-21 |
| CS245758B2 (en) | 1986-10-16 |
| CS245756B2 (en) | 1986-10-16 |
| BE851020A (fr) | 1977-08-02 |
| SE8300432L (sv) | 1983-01-28 |
| CA1109076A (en) | 1981-09-15 |
| IL51373A0 (en) | 1977-04-29 |
| FR2340303B1 (enExample) | 1979-04-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |