AU700602B2 - Novel 1-ar(alk)yl-imidazolin-2-ones containing a disubstituted amine radical in the 4th position, having an anti-convulsive effect, and process for their production - Google Patents
Novel 1-ar(alk)yl-imidazolin-2-ones containing a disubstituted amine radical in the 4th position, having an anti-convulsive effect, and process for their production Download PDFInfo
- Publication number
- AU700602B2 AU700602B2 AU67375/96A AU6737596A AU700602B2 AU 700602 B2 AU700602 B2 AU 700602B2 AU 67375/96 A AU67375/96 A AU 67375/96A AU 6737596 A AU6737596 A AU 6737596A AU 700602 B2 AU700602 B2 AU 700602B2
- Authority
- AU
- Australia
- Prior art keywords
- chlorophenyl
- morpholinoimidazolin
- phenyl
- alkyl
- imidazolin
- 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
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
- C07D233/88—Nitrogen atoms, e.g. allantoin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pain & Pain Management (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
According to the present invention, these novel compounds are 1-ar(alk)ylimidazolin-2-ones of the general formula 1 I, pki~ ii it AMENDED SHEET 2
(CH
2
H
0- NN m=O, 1, 2,3,4,5 in which X hydrogen, Cl-C 4 -alkyl, Cl-C 4 -alkoxy, trifluoronethyl or halogen
R
1 and R 2 =Cl-0 4 -alkyl, cycloalkyl or heteroalkyl where the alkyl group in each case contains 5-7 carbon atoff [sic] atoms or
R
1 and R 2 together are an alkylene group having 2-6 carbon atoms in which a -CR 2 group can be replaced by oxygen,- nitrogen or sulfur.
The number of CH 2 groups is either 0 (1-arylimidazolin- 2-ones) or 1 (l-aralkylimidazolin-2-ones).
Examples of compounds of the general formula I [sic] which may be mentioned are: l-phenyl-4 -morpholinoimidazolin-2-one 1- (4-methoxy) -4-piperidinoimidazolin-2-one 1- (4-chlorophenyl) -4-morpholinoimidazolin-2-one 1- (4-chlorophenyl) -4-piperidinoimidazolin-2-one 1- (4-chlorophenyl) -4-dimethylaminoimidazolin-2-one 1- (4-bromophenyl) -4-morpholinoimidazolin-2-one 1- (3-chiorophenyl) -4-morpholinoimidazolin-2-one 1- (4-chiorophenyl) -4-hexamethyleneiminoimidazolin-2-one 1- (4-chlorophenyl) (4-methylpiperazino) imidazolin-2one 1- (4-methylphenyl) -4-morpholinoimidazolin-2-one 1- (4-chiorophenyl) (cyclohexylmethylamino) imidazolin- 2-one 1- (4-fluorophenyl) -4-morpholinoimidazolin-2-one l-benzyl-4-morpholinoimidazolin-2-one x AMENDED SHEET WO 97/09314 PCT/EP96/03295 According to the present invention, the compounds of the general formula 1 can be prepared by a novel process by reaction of the compounds of the general formula 2
H
N.H n 0,1 (X)m m= 0,1,2,3,4,5 in which X hydrogen, Ci-C 4 -alkyl, Ci-C 4 -alkoxy, trifluoromethyl or halogen, with a secondary amine.
The preparation of the compounds of the formula 1 can alternatively be carried out in a solvent or in excess secondary amine at temperatures between 50 0 C and 160 0
C.
Suitable solvents are preferably aromatic hydrocarbons, for example benzene, toluene, chlorobenzene or dichlorobenzene.
The reaction is preferably carried out in the presence of water-binding substances such as zeolites or sodium sulfate. The reaction can be accelerated by addition of generally customary condensation catalysts such as 4-toluenesulfonic acid.
The compounds according to the invention are suitable for the preparation of pharmaceutical compositions. The pharmaceutical compositions can contain one or more of the compounds according to the invention. The customary pharmaceutical excipients and auxiliaries can be used to prepare the pharmaceutical preparations.
The medicaments can be administered parenterally (for example intravenously, intramuscularly or subcutaneous- Sly) or orally.
i l WO 97/09314 4 PCT/EP96/03295 The administration forms can be prepared by processes which are generally known and customary in pharmaceutical practice.
The compounds according to the invention have strong anticonvulsive actions.
They were tested for their anticonvulsive action in vivo after i.p. administration to mice or rats (p.o.
administration) according to the internationally customary standard (Pharmac. Weekblad, Sc.Ed. 14, 132 (1992) and Antiepileptic Drugs, Third Ed., Raven Press, New York (1989) (Table 1).
For example, for the compound 2 (1-(4-chlorophenyl)-4morpholinoimidazolin-2-one) in the rat the EDso for the maximum electroshock was determined to be 21 mg/kg, the ED 50 in the s.c. pentetrazole test was determined to be 16 mg/kg and the NT 50 for the neurotoxicity was determined to be 400 mg/kg. In comparison to this, known antiepileptics are active either in the maximum electroshock model or in the pentetrazole test or, in the case of relatively high activity, are severely neurotoxic in the PTZ test.
i~v'W/; 4 WO 97/09314 Table 1 PCT/EP96/03295 Comp ound tcordn Log p 2 Test 3)Dose 4 Action 5 Examples MES 100 1 0.64 100 MES 300 2 1.48 30 MES 100 100 3 2.29 PTZ 100 100 MES 300 4 0.48 PTZ 300 MES 300 100 2.17 300 100 MES 300 100 6 1.61 100 MES 300 100 7 1.53 PTZ 100 100 MES 300 8 1.45 PTZ 100 100 MES 100 9 0.97 PTZ 100 100 MES 300 1.28 300 MES 300 100 11 2.56 PTZ 300 WOo 97/09314 PCT/EP96/03295 Comparison substance Test 3 Dose 4 Action 5 MES 100 100 Carbamazepine PTZ 100 0 MES 100 0 Valproate PTZ 100 Notes for Table 1: 1) For numbering of examples the compounds see working 2) Octanol/water partition coefficient 3) MES maximum pentetrazole electroshock, PTZ s.c.
4) in mg/kg in of the protected animals The preparation of the novel compounds of the general formula 1 will be illustrated in greater detail with the aid of working examples.
Working Examples General procedure for the preparation of the compounds of the formula 1 according to Table 1, Examples 1-11.
Variant A 0.05 mol of 1-arylimidazolin-2,4-dione of the general formula 2 [lacuna] 200 mg of 4-toluenesulfonic acid [lacuna] added to 100 ml of an appropriate secondary amine. The mixture is then heated under reflux in a Soxhlet extractor, the extraction thimble previously being filled with about 25 g of a water- WO 97/09314 7 PCT/EP96/03295 binding solid (calc. sodium sulfate, magnesium sulfate, NaOH, KOH, zeolites are suitable). After a reaction time of 8 to 30 hours, the solution is filtered hot and distilled to approximately half the volume in a rotary evaporator. The clear solution is cooled in an ice bath and the crystal magma obtained is separated off from the amine. Starting substance contained in the crude product is extracted with 50 ml of hot acetone. The product is recrystallized from n-propanol.
About 0.02 mol of unreacted l-arylimidazolin-2,4-dione can be recovered from the separated amine.
Variant B 0.05 mol of l-aralkylimidazolin-2,4-dione of the general formula 2 is reacted with a sec. amine as described under A. After a reaction time of 8 to hours, the solution is filtered hot and then concentrated to dryness in a rotary evaporator. 50 ml of methylene chloride and 50 ml of 2N HC1 are added to the residue. The organic phase is separated off and the aqueous phase is extracted a further two times with methylene chloride. The aqueous phase isolated is rendered alkaline with 50 ml of 10% strength NaOH and the l-4-amino-l-aralkylimidazolin-2-one [sic] is extracted with 100 ml of methylene chloride. The ether extracts are dried over sodium sulfate. After distilling off the methylene chloride, the crude product is recrystallized from ethanol or acetone.
Variant C 0.05 mol of 1-ar(alk)ylimidazolin-2,4-dione of the general formula 2 is reacted with 100 ml of dimethylammonium dimethylcarbamate as described under A and B. After a reaction time of 40 hours, the mixture is worked up according to variant A or B.
i: i N
I*
WO 97/09314 PCT/EP96/03295 H Table 2 1) recovered starting material was taken into account when calculating the yield
Claims (8)
1. Novel compounds of the general formula 1 -(CH 2 H H N H n=0, 1 m 0, 1, 2, 3,4, in which X hydrogen, CI-C 4 -alkyl, CI-C 4 -alkoxy, trifluoromethyl or halogen RI and R 2 CI-C 4 -alkyl, cycloalkyl or heteroalkyl where the alkyl group in each case contains 5-7 carbon atoms or RI and R 2 together are an alkylene group having 2-6 carbon atoms in which a -CH 2 group can be replaced by oxygen, nitrogen or sulfur.
2. Compounds according to claim 1, 1 -phenyl-4-morpholinoimidazolin-2-one 1 -(4-methoxy)-4-piperidinoimidazolin-2-one 1 -(4-chlorophenyl)-4-inorpholinoimidazolin-2-one 1 -(4-chlorophenyl)-4-piperidinoimidazolin-2-one 1 -(4-chlorophenyl)-4-dimethylaminoimidazolin-2-one -(4-bromophenyl)-4-morpholinoimidazolin-2-one 1 -chlorophenyl)-4-morpholinoimidazolin-2-one 1 -(4-chlorophenyl)-4-hexamethyleneiminoimidazolin-2-one V900. 20 1 -(4-chlorophenyl)-4-(4-methylpiperazino)imidazolin-2-one 1 -(4-methylphenyl)-4-morpholinoimidazolin-2-one 1 -(4-chlorophenyl)-4-(cyclohexylmethylamino)imidazolin-2-one *1 -(4-fluorophenyl)-4-morpholinoimidazolin-2-one 1 -benzyl-4-morpholinoimidazolin-2-one
3. A 4-amino-i -(phenyl or phenalkyl)-1 ,5-dihydroimidazol-2-one derivative, substantially as hereinbefore described with reference to any one of the Examples.
4. Process for the preparation of the compounds of the general formula 1, characterised in that a compound of the general formula 2 [n:\libc]03345:MEF n 0, 1 m=0, 1,2,3,4,5 in which X hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, trifluoromethyl or halogen is reacted with a secondary amine HNR 1 R 2 at temperatures between 50 0 C and 160 0 C, R 1 and R 2 having the meaning indicated.
A process for the preparation of a 4-amino-l-(phenyl or dihydroimidazol-2-one derivative, substantially as hereinbefore described with reference to any one of the Examples.
6. A 4-amino-l-(phenyl or phenalkyl)-l,5-dihydroimidazol-2-one derivative prepared by the process of claim 4 or claim
7. A pharmaceutical composition comprising an effective amount of at least one compound according to any one of claims 1 to 3 or 6 together with a pharmaceutically acceptable carrier, diluent or adjuvant therefor.
8. A method for the treatment or prophylaxis of epileptic disorders in a mammal requiring said treatment or prophylaxis, which method comprises administering to said mammal an effective amount of at least one compound according to any one of claims 1 to 3 or 6 or of a composition according to claim 7. Dated 3 April, 1998 20 Arzneimittelwerk Dresden GmbH Patent Attorneys for the Applicant/Nominated Person SPRUSON FERGUSON [n:\libc]03345:MEF
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19532668 | 1995-09-05 | ||
| DE19532668A DE19532668A1 (en) | 1995-09-05 | 1995-09-05 | Novel, anticonvulsant 1-ar (alk) yl-imidazolin-2-ones which contain a disubstituted amine radical in the 4-position, and process for their preparation |
| PCT/EP1996/003295 WO1997009314A1 (en) | 1995-09-05 | 1996-07-26 | Novel 1-ar(alk)yl-imidazolin-2-ones containing a disubstituted amine radical in the 4th position, having an anti-convulsive effect, and process for their production |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU6737596A AU6737596A (en) | 1997-03-27 |
| AU700602B2 true AU700602B2 (en) | 1999-01-07 |
Family
ID=7771261
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU67375/96A Expired AU700602B2 (en) | 1995-09-05 | 1996-07-26 | Novel 1-ar(alk)yl-imidazolin-2-ones containing a disubstituted amine radical in the 4th position, having an anti-convulsive effect, and process for their production |
Country Status (32)
| Country | Link |
|---|---|
| EP (1) | EP0863880B1 (en) |
| JP (1) | JP4030578B2 (en) |
| CN (1) | CN1103762C (en) |
| AR (1) | AR003502A1 (en) |
| AT (1) | ATE254606T1 (en) |
| AU (1) | AU700602B2 (en) |
| BG (1) | BG63917B1 (en) |
| BR (1) | BR9610359A (en) |
| CA (1) | CA2184871C (en) |
| CZ (1) | CZ291839B6 (en) |
| DE (2) | DE19532668A1 (en) |
| DK (1) | DK0863880T3 (en) |
| EA (1) | EA000535B1 (en) |
| EE (1) | EE03562B1 (en) |
| ES (1) | ES2208758T3 (en) |
| FR (1) | FR13C0049I2 (en) |
| GE (1) | GEP20022652B (en) |
| HK (1) | HK1015776A1 (en) |
| HU (1) | HU225956B1 (en) |
| IL (1) | IL123333A (en) |
| LT (1) | LT4482B (en) |
| LU (1) | LU92263I2 (en) |
| NO (1) | NO313829B1 (en) |
| NZ (1) | NZ315624A (en) |
| PL (1) | PL188287B1 (en) |
| PT (1) | PT863880E (en) |
| SK (1) | SK284868B6 (en) |
| TR (1) | TR199800476T1 (en) |
| TW (1) | TW422838B (en) |
| UA (1) | UA46790C2 (en) |
| WO (1) | WO1997009314A1 (en) |
| ZA (1) | ZA967014B (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19721580A1 (en) * | 1997-05-23 | 1998-11-26 | Dresden Arzneimittel | Use of 1-ar (alk) yl-imidazolin-2-one for the treatment of anxiety and tension |
| US20050070537A1 (en) * | 2002-10-10 | 2005-03-31 | Chris Rundfeldt | Use of dihydroimidazolones for the treatment of dogs |
| CN101254189A (en) * | 2003-07-11 | 2008-09-03 | 埃尔比昂股份公司 | Method of treating or preventing central nervous system disorders with compounds having selectivity for the alpha 3 subunit of the benzodiazepine receptor |
| EP2093218A1 (en) * | 2008-02-22 | 2009-08-26 | Ruggero Fariello | Arylalkyl substituted imidazolidinones |
| BR112014003117A2 (en) | 2011-08-12 | 2017-06-13 | Boehringer Ingelheim Vetmedica Gmbh | funny (if) current inhibitors for use in a method of treatment and prevention of feline heart failure |
| US9820988B2 (en) | 2014-03-24 | 2017-11-21 | Boehringer Ingelheim Vetmedica Gmbh | Treatment of epileptic disorders in feline animals |
| IT202100000782A1 (en) | 2021-01-18 | 2022-07-18 | Procos Spa | PROCESS FOR THE SYNTHESIS OF IMEPITOIN |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE790380A (en) | 1971-10-21 | 1973-04-20 | American Cyanamid Co | NEW (P-CHLORO) PHENYL-1 METHYL-3 IMIDAZOLIDINES, 2,4-DISUBSTITUTIONS USEFUL IN PARTICULAR AS ANTIALDOSTERONE DIURETIC AGENTS AND THEIR PREPARATION PROCESS |
| US4044021A (en) * | 1971-10-21 | 1977-08-23 | American Cyanamid Company | Tetrasubstituted imidazolidine diuretics useful in the treatment of hyperaldosteronism |
| US3932452A (en) * | 1975-02-07 | 1976-01-13 | Morton-Norwich Products, Inc. | 1-Arylmethyl-2-imidazolidinones |
-
1995
- 1995-09-05 DE DE19532668A patent/DE19532668A1/en not_active Ceased
-
1996
- 1996-07-26 JP JP51080097A patent/JP4030578B2/en not_active Expired - Lifetime
- 1996-07-26 CN CN96197801A patent/CN1103762C/en not_active Expired - Lifetime
- 1996-07-26 TR TR1998/00476T patent/TR199800476T1/en unknown
- 1996-07-26 PT PT96927607T patent/PT863880E/en unknown
- 1996-07-26 UA UA98041717A patent/UA46790C2/en unknown
- 1996-07-26 GE GEAP19964221A patent/GEP20022652B/en unknown
- 1996-07-26 BR BR9610359A patent/BR9610359A/en active IP Right Grant
- 1996-07-26 EA EA199800271A patent/EA000535B1/en not_active IP Right Cessation
- 1996-07-26 CZ CZ1998661A patent/CZ291839B6/en not_active IP Right Cessation
- 1996-07-26 DK DK96927607T patent/DK0863880T3/en active
- 1996-07-26 PL PL96325413A patent/PL188287B1/en unknown
- 1996-07-26 WO PCT/EP1996/003295 patent/WO1997009314A1/en active IP Right Grant
- 1996-07-26 NZ NZ315624A patent/NZ315624A/en not_active IP Right Cessation
- 1996-07-26 IL IL12333396A patent/IL123333A/en not_active IP Right Cessation
- 1996-07-26 ES ES96927607T patent/ES2208758T3/en not_active Expired - Lifetime
- 1996-07-26 DE DE59610827T patent/DE59610827D1/en not_active Expired - Lifetime
- 1996-07-26 AU AU67375/96A patent/AU700602B2/en not_active Expired
- 1996-07-26 AT AT96927607T patent/ATE254606T1/en active
- 1996-07-26 EP EP96927607A patent/EP0863880B1/en not_active Expired - Lifetime
- 1996-07-26 EE EE9800063A patent/EE03562B1/en unknown
- 1996-07-26 SK SK216-98A patent/SK284868B6/en not_active IP Right Cessation
- 1996-07-26 HU HU9802941A patent/HU225956B1/en unknown
- 1996-08-19 ZA ZA967014A patent/ZA967014B/en unknown
- 1996-09-03 TW TW085110749A patent/TW422838B/en not_active IP Right Cessation
- 1996-09-04 AR ARP960104226A patent/AR003502A1/en active IP Right Grant
- 1996-09-05 CA CA002184871A patent/CA2184871C/en not_active Expired - Lifetime
-
1998
- 1998-02-27 BG BG102287A patent/BG63917B1/en unknown
- 1998-03-02 NO NO19980906A patent/NO313829B1/en not_active IP Right Cessation
- 1998-04-03 LT LT98-047A patent/LT4482B/en not_active IP Right Cessation
-
1999
- 1999-03-01 HK HK99100827A patent/HK1015776A1/en not_active IP Right Cessation
-
2013
- 2013-08-07 LU LU92263C patent/LU92263I2/en unknown
- 2013-08-13 FR FR13C0049C patent/FR13C0049I2/en active Active
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| PC | Assignment registered |
Owner name: ELBION AG Free format text: FORMER OWNER WAS: ARZNEIMITTELWERK DRESDEN GMBH |