CH528508A - Halo-cinnamamide derivs - Google Patents
Halo-cinnamamide derivsInfo
- Publication number
- CH528508A CH528508A CH718972A CH718972A CH528508A CH 528508 A CH528508 A CH 528508A CH 718972 A CH718972 A CH 718972A CH 718972 A CH718972 A CH 718972A CH 528508 A CH528508 A CH 528508A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- formula
- produced
- cinnamic acid
- piperidide
- Prior art date
Links
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims abstract description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 3
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 3
- 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 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 8
- APEJMQOBVMLION-UHFFFAOYSA-N cinnamamide Chemical class NC(=O)C=CC1=CC=CC=C1 APEJMQOBVMLION-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- ZROGHFJYTNYOOQ-UHFFFAOYSA-N 3-(4-bromophenyl)-1-piperidin-1-ylprop-2-en-1-one Chemical compound C1=CC(Br)=CC=C1C=CC(=O)N1CCCCC1 ZROGHFJYTNYOOQ-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- CPEONABTMRSIKA-UHFFFAOYSA-N 1,4$l^{2}-oxazinane Chemical group C1COCC[N]1 CPEONABTMRSIKA-UHFFFAOYSA-N 0.000 claims description 2
- KRTMKXWOJHDSHE-UHFFFAOYSA-N 3-(3-bromophenyl)-1-piperidin-1-ylprop-2-en-1-one Chemical compound BrC1=CC=CC(C=CC(=O)N2CCCCC2)=C1 KRTMKXWOJHDSHE-UHFFFAOYSA-N 0.000 claims description 2
- MCECGULZPWFNLB-UHFFFAOYSA-N 3-(4-iodophenyl)-1-morpholin-4-ylprop-2-en-1-one Chemical compound IC1=CC=C(C=CC(=O)N2CCOCC2)C=C1 MCECGULZPWFNLB-UHFFFAOYSA-N 0.000 claims description 2
- QIDNQWYDBMVLOU-UHFFFAOYSA-N 3-(4-iodophenyl)-1-piperidin-1-ylprop-2-en-1-one Chemical compound IC1=CC=C(C=CC(=O)N2CCCCC2)C=C1 QIDNQWYDBMVLOU-UHFFFAOYSA-N 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract 1
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- NSWLMOHUXYULKL-UHFFFAOYSA-N 2-chloro-1-piperidin-1-ylethanone Chemical compound ClCC(=O)N1CCCCC1 NSWLMOHUXYULKL-UHFFFAOYSA-N 0.000 description 1
- REJKLNFPNCDEQR-UHFFFAOYSA-N 3-(3-bromophenyl)-1-morpholin-4-ylprop-2-en-1-one Chemical compound BrC1=CC=CC(C=CC(=O)N2CCOCC2)=C1 REJKLNFPNCDEQR-UHFFFAOYSA-N 0.000 description 1
- QVNBHWCGNNVOLL-UHFFFAOYSA-N 3-(3-iodophenyl)-1-morpholin-4-ylprop-2-en-1-one Chemical compound IC=1C=C(C=CC(=O)N2CCOCC2)C=CC1 QVNBHWCGNNVOLL-UHFFFAOYSA-N 0.000 description 1
- HCVJBKSLBZHWJL-UHFFFAOYSA-N 3-(3-iodophenyl)-1-piperidin-1-ylprop-2-en-1-one Chemical compound IC1=CC=CC(C=CC(=O)N2CCCCC2)=C1 HCVJBKSLBZHWJL-UHFFFAOYSA-N 0.000 description 1
- QWQHHPOXLXYYOF-UHFFFAOYSA-N 3-(4-bromophenyl)-1-morpholin-4-ylprop-2-en-1-one Chemical compound C1=CC(Br)=CC=C1C=CC(=O)N1CCOCC1 QWQHHPOXLXYYOF-UHFFFAOYSA-N 0.000 description 1
- ZRYZBQLXDKPBDU-UHFFFAOYSA-N 4-bromobenzaldehyde Chemical compound BrC1=CC=C(C=O)C=C1 ZRYZBQLXDKPBDU-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229960002895 phenylbutazone Drugs 0.000 description 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 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 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
-
- 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
- C07F9/59—Hydrogenated 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)
Abstract
Title derivs. of formula (I) (where R1 is Br or I and R2 is piperidino or morpholino) are prepd. by eliminating the O atom from a cpd. of formula (II) with triphenylphosphine in the presence of hydroquinone at elevated temp.
Description
Verfahren zur Herstellung neuer Zimtsäureamide 1 Die Erfindung betrifft ein Verfahren zur Herstellung neuer Zimtsäureamide der Formel 1
EMI0001.0002
worin R1 ein Brom- oder Jodatom und R2 einen Piperi- dino- oder Morpholinorest bedeuten, das dadurch gekenn zeichnet ist, dass man aus einer Verbindung der Formel 2
EMI0001.0007
mit Triphenylphosphin in Gegenwart von Hydrochinon bei erhöhter Temperatur das Sauerstoffatom abspaltet.
Die erfindungsgemäss hergestellten neuen Zimtsäure- amide der Formel 1 besitzen wertvolle pharmakologische Eigenschaften, insbesondere eine antiphlogistische und an- tipyretische Wirkung.
Im Kaolin- und Carrageenin-Oedem-Test an der Rat te sind die Verbindungen der Formel 1 dem Phenylbuta- zon bezüglich der therapeutischen Breite überlegen.
Beispiel 4-Brom-zimtsäurepiperidid 280 mg (0,9 mMol) ss-(4-Bromphenyl)-glycidsäurepi- peridid (Fp. 85-90 C, hergestellt durch Umsetzung von 4-Brombenzaldehyd und Chloressigsäurepiperidid in Ge genwart von Natriumamid), 252 mg (1,0 mMol) Triphe- nylphosphin und 33 mg Hydrochinon werden gemischt und 30 Minuten in einem Bad von 170 C unter gelegentli chem Umschütteln erhitzt. Nach Abkühlen wird das Reaktionsgemisch in Chloroform aufgenommen, zweimal mit wässeriger Sodalösung und einmal mit Wasser ge waschen.
Die über Natriumsulfat getrocknete Choloform- lösung wird bei 10 Torr eingedampft. Bei Filtration des Rückstandes über eine Säule mit 80 g Kieselgel in Benzol/ Aceton = 10: 2 wird eine Fraktion mit 30 mg (11 /o d.Th.) 4-Brom-zimtsäurepiperidid vom Fp. 131-133 C (aus Petroläther) erhalten.
Analog wurden folgende Verbindungen hergestellt:
EMI0001.0024
3-Brom-zimtsäurepiperidid, <SEP> Fp. <SEP> 95 <SEP> - <SEP> 99 C
<tb> 4-Brom-zimtsäuremorpholid, <SEP> Fp. <SEP> 142 <SEP> - <SEP> 144 C
<tb> 3-Brom-zimtsäuremorpholid, <SEP> Fp. <SEP> 80 <SEP> - <SEP> 81 C
<tb> 4-Jod-zimtsäurepiperidid, <SEP> Fp. <SEP> 134 <SEP> - <SEP> 135 C
<tb> 3-Jod-zimtsäurepiperidid, <SEP> Fp. <SEP> 109 <SEP> - <SEP> 110 C
<tb> 4-Jod-zimtsäuremorpholid, <SEP> Fp. <SEP> 175 <SEP> - <SEP> 177 C
<tb> 3-Jod-zimtsäuremorpholid, <SEP> Fp. <SEP> 100- <SEP> 101 C Die erfindungsgemäss hergestellten Verbindungen der Formel 1 lassen sich nach an sich bekannten Methoden in übliche pharmazeutische Anwendungsformen, gege benenfalls in Kombination mit anderen Wirksubstanzen, einarbeiten.
Die Einzeldosis beträgt bei Erwachsenen 200,00 mg - 600,00 mg, bevorzugt 300,00 mg - 400,00 mg und die Tagesdosis 400,00 mg -<B>1</B>200,00 mg, bevorzugt 600,00 mg - 800,00 mg.
Process for the production of new cinnamic acid amides 1 The invention relates to a process for the production of new cinnamic acid amides of formula 1
EMI0001.0002
where R1 is a bromine or iodine atom and R2 is a piperidino or morpholino radical, which is characterized in that a compound of the formula 2
EMI0001.0007
splitting off the oxygen atom with triphenylphosphine in the presence of hydroquinone at elevated temperature.
The new cinnamic acid amides of formula 1 prepared according to the invention have valuable pharmacological properties, in particular an anti-inflammatory and antipyretic effect.
In the kaolin and carrageenin edema test on the rat, the compounds of formula 1 are superior to phenylbutazone with regard to the therapeutic range.
Example 4-Bromo-cinnamic acid piperidide 280 mg (0.9 mmol) ss- (4-bromophenyl) -glycidic acid piperidide (melting point 85-90 ° C., prepared by reacting 4-bromobenzaldehyde and chloroacetic acid piperidide in the presence of sodium amide), 252 mg (1.0 mmol) of triphenylphosphine and 33 mg of hydroquinone are mixed and heated for 30 minutes in a bath at 170 ° C. with occasional shaking. After cooling, the reaction mixture is taken up in chloroform, washed twice with aqueous soda solution and once with water.
The choloform solution, dried over sodium sulfate, is evaporated at 10 torr. When the residue is filtered through a column with 80 g of silica gel in benzene / acetone = 10: 2, a fraction with 30 mg (11 / o of theory) of 4-bromocinnamic acid piperidide of melting point 131-133 C (from petroleum ether) receive.
The following connections were made in the same way:
EMI0001.0024
3-bromo-cinnamic acid piperidide, <SEP> m.p. <SEP> 95 <SEP> - <SEP> 99 C
<tb> 4-Bromo-cinnamic acid morpholide, <SEP> mp. <SEP> 142 <SEP> - <SEP> 144 C
<tb> 3-Bromo-cinnamic acid morpholide, <SEP> melting point <SEP> 80 <SEP> - <SEP> 81 C
<tb> 4-iodo-cinnamic acid piperidide, <SEP> mp. <SEP> 134 <SEP> - <SEP> 135 C
<tb> 3-iodo-cinnamic acid piperidide, <SEP> mp. <SEP> 109 <SEP> - <SEP> 110 C
<tb> 4-iodo-cinnamic acid morpholide, <SEP> melting point <SEP> 175 <SEP> - <SEP> 177 C
<tb> 3-iodocinnamic acid morpholide, <SEP> melting point <SEP> 100- <SEP> 101 C The compounds of formula 1 prepared according to the invention can be converted into customary pharmaceutical forms by methods known per se, possibly in combination with other active substances , incorporate.
The single dose for adults is 200.00 mg - 600.00 mg, preferably 300.00 mg - 400.00 mg and the daily dose 400.00 mg - 1 200.00 mg, preferably 600.00 mg mg - 800.00 mg.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT1075768A AT285606B (en) | 1968-11-05 | 1968-11-05 | Process for the production of new cinnamic acid amides |
| CH343371 | 1968-11-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH528508A true CH528508A (en) | 1972-09-30 |
Family
ID=25606129
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1442671A CH516556A (en) | 1968-11-05 | 1968-11-29 | Process for the production of new cinnamic acid amides |
| CH1442571A CH516555A (en) | 1968-11-05 | 1968-11-29 | Process for the production of new cinnamic acid amides |
| CH718972A CH528508A (en) | 1968-11-05 | 1968-11-29 | Halo-cinnamamide derivs |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1442671A CH516556A (en) | 1968-11-05 | 1968-11-29 | Process for the production of new cinnamic acid amides |
| CH1442571A CH516555A (en) | 1968-11-05 | 1968-11-29 | Process for the production of new cinnamic acid amides |
Country Status (1)
| Country | Link |
|---|---|
| CH (3) | CH516556A (en) |
-
1968
- 1968-11-29 CH CH1442671A patent/CH516556A/en not_active IP Right Cessation
- 1968-11-29 CH CH1442571A patent/CH516555A/en not_active IP Right Cessation
- 1968-11-29 CH CH718972A patent/CH528508A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CH516556A (en) | 1971-12-15 |
| CH516555A (en) | 1971-12-15 |
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