EP1362038A1 - Neue alkyl-phenylimino-imidazolidin-derivate zur behandlung der harninkontinenz - Google Patents
Neue alkyl-phenylimino-imidazolidin-derivate zur behandlung der harninkontinenzInfo
- Publication number
- EP1362038A1 EP1362038A1 EP02704665A EP02704665A EP1362038A1 EP 1362038 A1 EP1362038 A1 EP 1362038A1 EP 02704665 A EP02704665 A EP 02704665A EP 02704665 A EP02704665 A EP 02704665A EP 1362038 A1 EP1362038 A1 EP 1362038A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- iminoimidazolidine
- phen
- isopropyl
- methyl
- tert
- 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.)
- Withdrawn
Links
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
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
-
- 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
- C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/10—Drugs for disorders of the urinary system of the bladder
Definitions
- New alkyl phenvimino imidazolidine derivatives for the treatment of urinary incontinence
- the present invention comprises m-alkyl-phenylimino-imidazolidine derivatives with a new substituent pattern on the phenyl ring and their use for the production of medicaments, in particular for the treatment of urinary incontinence.
- the compounds described in the context of the present invention belong to the class of m-alkyl-phenylimino-imidazolidines. Similar compounds are known from the prior art.
- WO 96/32939 which is hereby incorporated by reference in its entirety, discloses phenylimino-imidazoles. These include those in which the phenyl ring has, inter alia, amino, amido, imido, halo, heteroaryl, cycloalkyl and alkyl substituents.
- the compounds described there are considered to be alpha-1 L agonists and can advantageously be used in this capacity for the treatment of urinary incontinence.
- Incontinence is an involuntary loss of urine, i.e. a bladder weakness.
- the various manifestations of urinary incontinence include urge incontinence, reflex incontinence, overflow incontinence and stress or stress incontinence.
- One of the most common forms of urinary incontinence is stress incontinence or stress incontinence. This affects women in particular after more or less difficult births. The reason for this is that pregnancy and childbirth can easily weaken the pelvic floor.
- Other causes of incontinence can include innervation disorders of the pelvic floor, an inborn urethra that is too short, or injuries to the sphincter.
- alpha-1L agonists in the treatment of urinary incontinence is advantageous because they act selectively on the bladder adrenoceptors and thus exert a significant influence on the urethertonization without significantly influencing the cardiovascular system.
- alpha 2 agonists such as clonidine would have a positive effect on night incontinence (Urology, 43 (3) (1994) 324-327).
- clonidine in particular there is a contrary observation that this substance can even promote incontinence (Clin. Biol. Res. 78 (1981) 101-103).
- Jpn. J. Pharmacol. 58 (4) (1992) 339-346 The authors find that clonidine has no clear influence on bladder function, but phenylethanolamines, such as phenylephrine, midodrine or ST 1059, which are similar to adrenaline, are all alpha 1 agonists.
- EP-A-0416 841 also deals with the influence of alpha agonists on bladder function. It describes that alpha 1 adrenoceptor blocking substances could be used to treat bladder occlusion. The observations according to US-A-4226 773 also point in this direction. According to this document, pyrrazolylimino-imidazole derivatives can be used to promote urination. Other alpha 1 adrenergic imidazoles such as thiophene pyrroles can also be used to treat urinary incontinence (EP-A-0599 697).
- one of the objects of the present invention comprises finding new alpha-1L agonists from the class of the phenyimino-imidazolidines which act selectively on the bladder without significantly affecting the cardiovascular system and have favorable properties with regard to bioavailability or metabolism ,
- the m-alkyl-phenyliminimidazolidines according to the invention fulfill the object of the present invention and are therefore particularly suitable for the treatment of urinary incontinence.
- alkyl-phenylimino-imidazolidines with branched alkyl radicals are known from the prior art.
- WO 92/21349 discloses a number of
- Phenyliminiimidazolidine derivatives for ophthalmic use. The de
- 1929950 describes i.a. the 2'-bromo, 5'-chloro, 4'-tert-butyl-phenylimini-2-imidazolidine and DE 0116768 the 2,6-dichloro-4'-tert-butyl-phenyliminoimidazolidine.
- EP 0035393 also deals with alkylphenylimino-imidazolidines, but not for human medical use, but for the production of
- alkyl-phenylimino-2-imidazolidine derivatives according to the invention are notable for the fact that at least one of the two possible meta positions to the imino group contains a branched C 3 -C 6 -alkyl radical, such as, for example, isopropyl, isobutyl, tertiary Butyl, isopentyl, neopentyl. It is preferably an isopropyl and / or a tertiary butyl group.
- the preferred compounds according to the invention are described by the general formula I:
- Ri or R 5 independently of one another H, F, Cl, Br, CH 2 F, CHF 2 , CF 3 , Me or OMe are R 2 , R 4 : each independently of one another H, iPr, tert.Bu, F, Cl, Br,
- R 5 is OMe
- Rt or R 5 are independently of one another H, F, Cl, Br, CF 3 , Me or OMe are R 2 , R 4 : are each independently of one another H, iPr, tert.Bu and / or Me, wherein at least one of R 2 or R is iPr or tert.Bu R 3 is : H, F, Cl, Br or Me.
- R 2 iPr or tert.Bu
- R 3 H, Br or CI
- R 4 H
- R 5 H, Cl, Br or OMe.
- R 2 iPr or tert.Bu
- R 3 is H, Cl or Br
- R 5 H, Cl or OMe.
- R 2 is preferably iPr, tert-Bu, while R is preferably H. Also preferred for all cases, R 1 is different from OMe.
- phen-1'-yl-2-imidazolidine is understood to mean compounds having the following structural element:
- the atoms of the imidazole ring are numbered 1, 2, 3, etc., number 1 being assigned to one nitrogen atom and number 3 assigned to the other nitrogen atom. Accordingly, the imino group is attached to the carbon atom to which the number 2 is assigned.
- the atoms of the phenyl ring are numbered 1 ', 2', 3 'etc., whereby the carbon atom of the phenyl ring which is bonded to the imino group is referred to throughout as 1' and the atom carrying the branched alkyl substituent in the meta position than 3 '.
- Butyl-6'-methoxy-phen-1'-yl-2-iminoimidazolidine 2 which is preferably present as a free base
- Preferred among these compounds are: 3'-isopropyl-2'-methyl-phen-1'-yl-2-iminoimidazolidine ,_, 3'tert. Butyl-6'-methoxy-phen-1'-yl-2-iminoimidazolidine 2, 6'-chloro-3'-isopropyl-2'-methyl-phen-1'-yl-2-iminoimidazolidine 3,4'-chloro -3'-isopropyl-2'-methyl-phen-1'-yI-2-iminoimidazolidine 4, 6'-bromo-3'-isopropyl-2'-methyl-phen-1'-yl-2-iminoimidazolidine 5, 6'-bromo-3'-tert-butyl-phen-1'-yl-2-iminoimidazolidine 6, 4'-bromo-3'-isopropyl-2'-methyl-1'-phenyl-2-iminoimidazolidine 7 ,
- 3'-isopropyl-2'-methyl-phen-1'-yl-2-iminoimidazolidine 1, 3'tert are particularly preferred.
- 4'-bromo-3'-isopropyl-2'-methyl-phen-1'-yl-2-iminoimidazolidine 7.
- Preferred compounds also include each of the following: 4 ', 5'-dichloro-3'-isopropyl-2'-methylene-phen-1' -vl-2-iminoimidazolidine 19, 2'-chloro-3'-tert .butyl-6'-methoxy-phen-1'-yl-2-iminoimidazolidine 42, 5'-chloro-3'-isopropvl-2'-methvl-phen-1'-vl-2-iminoimidazolidine 27,
- Examples 1, 3, 4, 5 and 7 to 29 relate to structures with an isopropyl radical in the meta position
- examples 2, 6 and 30 to 45 relate to structures with a tert-butyl radical in the meta position, which in turn form preferred groups.
- Suitable acids can be both inorganic and organic in nature.
- Hydrochloric acid hydrobromic acid, sulfuric acid, phosphoric acid, fumaric acid, citric acid, lactic acid, acetic acid, propionic acid, malic acid, succinic acid, amino acid, in particular glutamic acid or aspartic acid, carbohydrate acids and acids derived from carbohydrates.
- Such salts can be important both for the pharmaceutical preparation, increase the stability, in particular long-term stability, of the compound and / or lead to an increase in bioavailability.
- Hydrochloride salts are preferred, depending on the compound, the monohydrochlorides or dihydrochlorides. The same applies to the preferred compounds.
- the compounds according to the invention mentioned are particularly notable for their pharmacological properties with regard to bioavailability and / or their metabolism. It goes without saying that the most preferred compounds are those which are highly effective and bioavailable with little metabolic degradation. Another feature that is important for the selection of particularly suitable compounds for the treatment of urinary incontinence is the selectivity with which the corresponding compound acts on the bladder function without to significantly influence other body functions, especially the cardiovascular system.
- the present invention also includes their use for the production of medicaments and pharmaceutical preparations.
- preparations include all formulations which are suitable for medical use. This includes e.g. Solutions, suspensions, aerosols, powders, tablets, coated tablets, suppositories, creams etc.
- the compounds according to the invention can be used medically for the treatment of diseases, particularly for diseases of the bladder, in particular in the case of urinary incontinence.
- the use of the compounds according to the invention for the treatment of stress incontinence is most preferred.
- Another aspect of the present invention relates to processes for the preparation of the compounds mentioned, their pharmacologically acceptable acid addition salts and / or pharmaceutical preparations, and the use of the compound described for the preparation of further pharmacologically active derivatives thereof.
- test substances were administered orally to a group of 8 male fasting rats.
- animals from an identical second group were administered the test substances intravenously.
- 1 ml of blood samples were taken from the animals of both groups after defined times after administration (10 minutes, 30 minutes, 1 hour, 2 hours and 4 hours, the animals of the oral group additionally after 6 hours).
- the blood samples taken per group were mixed (8 ml).
- the plasma became Further processing of the content of the corresponding test substances in the blood for the respective time determined by HPLC (High Performance Liquid Chromatography) according to standard methods and related to the two groups.
- HPLC High Performance Liquid Chromatography
- the enzyme CYP2D6 was allowed to act on the test substances. After 30 minutes, it was checked how much of the test substance used had been broken down by the enzyme.
- the decomposition rate is checked under the action of the HLM enzyme / 60 minutes.
- the mixture is stirred for 4 hours without external heat (RT) and then mixed with 100 ml of methylene chloride and 100 ml of water.
- the aqueous phase is separated off and extracted twice with 75 ml of methylene chloride.
- the combined organic phases are washed with water, dried and concentrated under reduced pressure.
- the product is purified by chromatography (silica gel, eluent: cyclohexane / ethyl acetate (3/1)). 3.4 g of 3-isopropenyl-2-methyl-aniline are obtained as a clear yellow oil.
- the water phase is neutralized with 12 ml of NaOH (1 M) and extracted with 2x40 ml of ethyl acetate.
- the organic phases are separated again.
- the water phase is made basic with 10 ml of NaOH (1 M) and extracted with 2x40 ml of ethyl acetate. All 3 organic phases are combined, dried and concentrated under reduced pressure.
- the product is isolated by chromatography (silica gel, eluent: methylene chloride / methanol / ammonia (9/1/1%)). 0.85 g of 3'-terf-butyl-6'-mehoxy-phen-1'-yl-2-iminoimidazolidine are obtained as a white powder, mp. 172-174 ° C. 6'-bromo-3'-tert-butyl-phen-1'-yl-2-iminoimidazolidine 6
- Solid substance is suctioned off, washed with petroleum ether and dried.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Urology & Nephrology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10106214A DE10106214A1 (de) | 2001-02-10 | 2001-02-10 | Neue Alkyl-phenylimino-imidazolidin-Derivate zur Behandlung der Harninkontinenz |
DE10106214 | 2001-02-10 | ||
PCT/EP2002/000576 WO2002064570A1 (de) | 2001-02-10 | 2002-01-22 | Neue alkyl-phenylimino-imidazolidin-derivate zur behandlung der harninkontinenz |
Publications (1)
Publication Number | Publication Date |
---|---|
EP1362038A1 true EP1362038A1 (de) | 2003-11-19 |
Family
ID=7673601
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP02704665A Withdrawn EP1362038A1 (de) | 2001-02-10 | 2002-01-22 | Neue alkyl-phenylimino-imidazolidin-derivate zur behandlung der harninkontinenz |
Country Status (21)
Country | Link |
---|---|
EP (1) | EP1362038A1 (hu) |
JP (1) | JP2004517963A (hu) |
KR (1) | KR20030076653A (hu) |
CN (1) | CN1491216A (hu) |
AR (1) | AR035226A1 (hu) |
BG (1) | BG108036A (hu) |
BR (1) | BR0206949A (hu) |
CA (1) | CA2437809A1 (hu) |
CZ (1) | CZ20032146A3 (hu) |
DE (1) | DE10106214A1 (hu) |
EA (1) | EA200300835A1 (hu) |
EC (1) | ECSP034700A (hu) |
EE (1) | EE200300379A (hu) |
HU (1) | HUP0303004A3 (hu) |
IL (1) | IL157297A0 (hu) |
MX (1) | MXPA03007127A (hu) |
NO (1) | NO20033368D0 (hu) |
PL (1) | PL362149A1 (hu) |
SK (1) | SK10132003A3 (hu) |
WO (1) | WO2002064570A1 (hu) |
ZA (1) | ZA200305609B (hu) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100378097C (zh) * | 2003-05-09 | 2008-04-02 | 弗·哈夫曼-拉罗切有限公司 | 作为α-1肾上腺素能激动剂的甲基吲哚和甲基吡咯并吡啶 |
JP4168086B1 (ja) * | 2008-04-16 | 2008-10-22 | 国立大学法人福井大学 | イミダゾリン誘導体 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3202660A (en) * | 1961-10-09 | 1965-08-24 | Boehringer Sohn Ingelheim | Process for the preparation of 3-arylamino-1, 3-diazacycloalkenes |
HU192986B (en) * | 1984-05-23 | 1987-08-28 | Egyt Gyogyszervegyeszeti Gyar | Process for production of imidasodiline derivatives |
DE19514579A1 (de) * | 1995-04-20 | 1996-10-24 | Boehringer Ingelheim Kg | Verwendung von alpha¶1¶¶L¶-Agonisten zur Behandlung der Harninkontinenz |
FR2761061B1 (fr) * | 1997-03-20 | 1999-04-23 | Synthelabo | Derives de benzenesulfonamide, leur preparation et leur application en therapeutique |
SG72827A1 (en) * | 1997-06-23 | 2000-05-23 | Hoffmann La Roche | Phenyl-and aminophenyl-alkylsulfonamide and urea derivatives |
-
2001
- 2001-02-10 DE DE10106214A patent/DE10106214A1/de not_active Withdrawn
-
2002
- 2002-01-22 EP EP02704665A patent/EP1362038A1/de not_active Withdrawn
- 2002-01-22 MX MXPA03007127A patent/MXPA03007127A/es unknown
- 2002-01-22 KR KR10-2003-7010280A patent/KR20030076653A/ko not_active Application Discontinuation
- 2002-01-22 CZ CZ20032146A patent/CZ20032146A3/cs unknown
- 2002-01-22 JP JP2002564503A patent/JP2004517963A/ja active Pending
- 2002-01-22 BR BR0206949-0A patent/BR0206949A/pt active Pending
- 2002-01-22 PL PL36214902A patent/PL362149A1/xx not_active Application Discontinuation
- 2002-01-22 EE EEP200300379A patent/EE200300379A/xx unknown
- 2002-01-22 IL IL15729702A patent/IL157297A0/xx unknown
- 2002-01-22 CN CNA02804570XA patent/CN1491216A/zh active Pending
- 2002-01-22 CA CA002437809A patent/CA2437809A1/en not_active Abandoned
- 2002-01-22 HU HU0303004A patent/HUP0303004A3/hu unknown
- 2002-01-22 EA EA200300835A patent/EA200300835A1/ru unknown
- 2002-01-22 WO PCT/EP2002/000576 patent/WO2002064570A1/de not_active Application Discontinuation
- 2002-01-22 SK SK1013-2003A patent/SK10132003A3/sk unknown
- 2002-02-08 AR ARP020100417A patent/AR035226A1/es not_active Withdrawn
-
2003
- 2003-07-21 ZA ZA200305609A patent/ZA200305609B/en unknown
- 2003-07-22 EC EC2003004700A patent/ECSP034700A/es unknown
- 2003-07-28 NO NO20033368A patent/NO20033368D0/no not_active Application Discontinuation
- 2003-07-28 BG BG108036A patent/BG108036A/bg active Pending
Non-Patent Citations (1)
Title |
---|
See references of WO02064570A1 * |
Also Published As
Publication number | Publication date |
---|---|
CA2437809A1 (en) | 2002-08-22 |
WO2002064570A1 (de) | 2002-08-22 |
SK10132003A3 (sk) | 2004-02-03 |
AR035226A1 (es) | 2004-05-05 |
MXPA03007127A (es) | 2003-11-18 |
HUP0303004A3 (en) | 2004-07-28 |
CN1491216A (zh) | 2004-04-21 |
BG108036A (bg) | 2004-12-30 |
NO20033368L (no) | 2003-07-28 |
NO20033368D0 (no) | 2003-07-28 |
EE200300379A (et) | 2003-12-15 |
EA200300835A1 (ru) | 2004-02-26 |
KR20030076653A (ko) | 2003-09-26 |
DE10106214A1 (de) | 2002-08-14 |
JP2004517963A (ja) | 2004-06-17 |
HUP0303004A2 (hu) | 2003-12-29 |
ECSP034700A (es) | 2003-08-29 |
CZ20032146A3 (cs) | 2003-12-17 |
BR0206949A (pt) | 2004-02-25 |
IL157297A0 (en) | 2004-02-19 |
PL362149A1 (en) | 2004-10-18 |
ZA200305609B (en) | 2004-04-29 |
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