IE32544B1 - Halocinnamoyl piperidines and morpholines and pharmaceutical compositions containing them - Google Patents
Halocinnamoyl piperidines and morpholines and pharmaceutical compositions containing themInfo
- Publication number
- IE32544B1 IE32544B1 IE1470/68A IE147068A IE32544B1 IE 32544 B1 IE32544 B1 IE 32544B1 IE 1470/68 A IE1470/68 A IE 1470/68A IE 147068 A IE147068 A IE 147068A IE 32544 B1 IE32544 B1 IE 32544B1
- Authority
- IE
- Ireland
- Prior art keywords
- halocinnamoyl
- morpholines
- piperidines
- pharmaceutical compositions
- lower alkyl
- Prior art date
Links
- 150000002780 morpholines Chemical class 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 150000003053 piperidines Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 230000001741 anti-phlogistic effect Effects 0.000 abstract 2
- 230000001754 anti-pyretic effect Effects 0.000 abstract 2
- 239000002221 antipyretic Substances 0.000 abstract 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 abstract 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 abstract 1
- 206010030113 Oedema Diseases 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 239000002260 anti-inflammatory agent Substances 0.000 abstract 1
- 229940125716 antipyretic agent Drugs 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 229930016911 cinnamic acid Natural products 0.000 abstract 1
- 235000013985 cinnamic acid Nutrition 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 abstract 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract 1
- 229960002895 phenylbutazone Drugs 0.000 abstract 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 abstract 1
- -1 piperidino, 4-hydroxypiperidino Chemical group 0.000 abstract 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
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/64—Acyl halides
- C07C57/72—Acyl halides containing six-membered aromatic rings
-
- 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
- C07C59/56—Unsaturated compounds containing hydroxy or O-metal groups containing halogen
-
- 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
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/224—Phosphorus triamides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4056—Esters of arylalkanephosphonic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/535—Organo-phosphoranes
- C07F9/5352—Phosphoranes containing the structure P=C-
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5407—Acyclic saturated phosphonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5456—Arylalkanephosphonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/58—Pyridine rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
ANTIPHLOGISTIC AND ANTIPYRETIC CINNAMIC ACID AMIDES G3A- Are new compounds of formula (I): (where R1 is Br or I and R2 is piperidino, 4-hydroxypiperidino or morpholino). Prepared by (a) reacting (II): (where X is OH, NH2, NH(lower alkyl) or N(lower alkyl)2 or a reactive residue, e.g. halogen, alkoxy or acyloxy) with H-R, or a reactive deriv. thereof or (b) olefinating (IV) with (V): (where A is (R3O)2P-CH2- in which R3 is lower alkyl, or (R4)3P=CH- in which R4 is aryl or alkyl), the reaction being carried out in the presence of a base when A is (R3O)2P-CH2-. Use is as antiphlogistics and antipyretics (better than phenylbutazone in kaolin- and carrageenin-oedema tests).
[DE1814625A1]
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT1091167A AT280283B (en) | 1967-12-01 | 1967-12-01 | Process for the preparation of new cinnamic acid amides |
| AT1075668A AT281822B (en) | 1968-11-05 | 1968-11-05 | Process for the production of new cinnamic acid amides |
| AT1075568A AT281821B (en) | 1968-11-05 | 1968-11-05 | Process for the production of new cinnamic acid amides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE32544L IE32544L (en) | 1969-06-01 |
| IE32544B1 true IE32544B1 (en) | 1973-09-05 |
Family
ID=27151184
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1470/68A IE32544B1 (en) | 1967-12-01 | 1968-12-02 | Halocinnamoyl piperidines and morpholines and pharmaceutical compositions containing them |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE724746A (en) |
| ES (1) | ES360959A1 (en) |
| FR (2) | FR1593868A (en) |
| GB (1) | GB1190680A (en) |
| IE (1) | IE32544B1 (en) |
| IL (1) | IL31191A (en) |
| NL (1) | NL6816625A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4824842A (en) * | 1985-02-14 | 1989-04-25 | Kyowa Hakko Kogyo Kabushiki Kaisha | Cinnamoyl piperidines and thiomorpholine and cerebral protection compositions |
| EP4277896A1 (en) * | 2021-01-14 | 2023-11-22 | B.G. Negev Technologies and Applications Ltd., at Ben-Gurion University | Anti-quorum sensing, anti-biofilm, and inflammation attenuating compounds, compositions, and methods of using same |
-
1968
- 1968-11-21 NL NL6816625A patent/NL6816625A/xx unknown
- 1968-11-29 BE BE724746D patent/BE724746A/xx unknown
- 1968-11-29 FR FR1593868D patent/FR1593868A/fr not_active Expired
- 1968-11-30 ES ES360959A patent/ES360959A1/en not_active Expired
- 1968-12-01 IL IL31191A patent/IL31191A/en unknown
- 1968-12-02 GB GB57154/68A patent/GB1190680A/en not_active Expired
- 1968-12-02 IE IE1470/68A patent/IE32544B1/en unknown
-
1969
- 1969-01-24 FR FR183229A patent/FR8274M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1814625A1 (en) | 1970-05-21 |
| FR1593868A (en) | 1970-07-10 |
| ES360959A1 (en) | 1970-10-16 |
| GB1190680A (en) | 1970-05-06 |
| BE724746A (en) | 1969-05-29 |
| FR8274M (en) | 1970-11-02 |
| IL31191A0 (en) | 1969-02-27 |
| IE32544L (en) | 1969-06-01 |
| NL6816625A (en) | 1969-06-03 |
| IL31191A (en) | 1972-09-28 |
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