NO782027L - PROCEDURE FOR PREPARING NEW IMIDAZOLINE DERIVATIVES - Google Patents
PROCEDURE FOR PREPARING NEW IMIDAZOLINE DERIVATIVESInfo
- Publication number
- NO782027L NO782027L NO782027A NO782027A NO782027L NO 782027 L NO782027 L NO 782027L NO 782027 A NO782027 A NO 782027A NO 782027 A NO782027 A NO 782027A NO 782027 L NO782027 L NO 782027L
- Authority
- NO
- Norway
- Prior art keywords
- imidazoline
- imidazoline derivatives
- procedure
- hydrochloride
- compounds
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 229940083254 peripheral vasodilators imidazoline derivative Drugs 0.000 title claims description 6
- 150000002462 imidazolines Chemical class 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 claims description 6
- YFBPRBZDQSMTKG-UHFFFAOYSA-N 2-(chloromethyl)-4,5-dihydroimidazole Chemical compound ClCC1=NCCN1 YFBPRBZDQSMTKG-UHFFFAOYSA-N 0.000 claims description 4
- VLLSCJFPVSQXDM-UHFFFAOYSA-N 2-phenoxyacetonitrile Chemical class N#CCOC1=CC=CC=C1 VLLSCJFPVSQXDM-UHFFFAOYSA-N 0.000 claims description 4
- GRMJZZBFHKTYDJ-UHFFFAOYSA-N 2-(phenoxymethyl)-4,5-dihydro-1h-imidazole Chemical compound N=1CCNC=1COC1=CC=CC=C1 GRMJZZBFHKTYDJ-UHFFFAOYSA-N 0.000 claims description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 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 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 230000021962 pH elevation Effects 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- 230000000694 effects Effects 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000005526 vasoconstrictor agent Substances 0.000 description 4
- -1 (2-Cyclobutyl-phenoxy)-2-methyl-imidazoline Chemical compound 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- 210000000709 aorta Anatomy 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- CNIIGCLFLJGOGP-UHFFFAOYSA-N 2-(1-naphthalenylmethyl)-4,5-dihydro-1H-imidazole Chemical compound C=1C=CC2=CC=CC=C2C=1CC1=NCCN1 CNIIGCLFLJGOGP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000013081 microcrystal Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 206010039083 rhinitis Diseases 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- OHMZXXMZIISZCI-UHFFFAOYSA-N 1-(naphthalen-1-ylmethyl)-4,5-dihydroimidazole Chemical compound C1(=CC=CC2=CC=CC=C12)CN1C=NCC1 OHMZXXMZIISZCI-UHFFFAOYSA-N 0.000 description 1
- DCAIEYUJOVJWCG-UHFFFAOYSA-N 2-cyclobutylphenol Chemical compound OC1=CC=CC=C1C1CCC1 DCAIEYUJOVJWCG-UHFFFAOYSA-N 0.000 description 1
- MVRPPTGLVPEMPI-UHFFFAOYSA-N 2-cyclohexylphenol Chemical compound OC1=CC=CC=C1C1CCCCC1 MVRPPTGLVPEMPI-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010047139 Vasoconstriction Diseases 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000002517 constrictor effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- LBAQSKZHMLAFHH-UHFFFAOYSA-N ethoxyethane;hydron;chloride Chemical compound Cl.CCOCC LBAQSKZHMLAFHH-UHFFFAOYSA-N 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229960005016 naphazoline Drugs 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 201000009890 sinusitis Diseases 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000025033 vasoconstriction 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
- 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
- C07D233/20—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 substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D233/22—Radicals substituted by oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
"Fremgangsmåte for fremstilling av nye imidazolinderivater". "Procedure for the preparation of new imidazoline derivatives".
Foreliggende oppfinnelse vedrører en fremgangsmåte for fremstilling av nye imidazolinderivater med terapeutisk virkning. The present invention relates to a method for the production of new imidazoline derivatives with therapeutic effect.
Imidazolinderivater med terapeutisk virkning er tidligere be-skrevet . Imidazoline derivatives with therapeutic effect have previously been described.
Den foreliggende oppfinnelse vedrører en fremgangsmåte for fremstilling av terapeutisk aktive imidazolinderivater med formel (I) The present invention relates to a method for the production of therapeutically active imidazoline derivatives of formula (I)
hvori R står for cyclobutyl, cyclopentyle eller cyclohexyl, samt deres syreaddisjonssalter med farmasøytisk tålbare syrer, og det særegne ved fremgangsmåten i henhold til oppfinnelsen er at forbindelsene (I) oppnås ved reaksjon mellom en fenol (II) eller dens natriumsalt og hydrokloridet av2-klormetyl-imidazolin (III) ved hjelp av følgende reaksjonsskjema eller ved reaksjon mellom et substituert fenoksyacetonitril (IV) in which R stands for cyclobutyl, cyclopentyl or cyclohexyl, as well as their acid addition salts with pharmaceutically acceptable acids, and the peculiarity of the method according to the invention is that the compounds (I) are obtained by reaction between a phenol (II) or its sodium salt and the hydrochloride of 2-chloromethyl -imidazoline (III) by means of the following reaction scheme or by reaction between a substituted phenoxyacetonitrile (IV)
med monotosylatet av etylen-diamin slik at man oppnår, to- with the monotosylate of ethylene diamine so that one obtains, two-
sylatet av 2-fenoksymetyl-imidazolinet med formel (I) og forbindelsen (I) frigis fra tosylatet ved alkalinisering. the sylate of the 2-phenoxymethyl-imidazoline of formula (I) and the compound (I) is released from the tosylate by alkalinization.
Reaksjonen 1 gjennomføres i et polart løsningsmiddel som en alkohol, først ved omgivelsenes temperatur og deretter ved tilbakeløps-temperaturen for løsningsmidlet. Reaction 1 is carried out in a polar solvent such as an alcohol, first at the ambient temperature and then at the reflux temperature for the solvent.
Reaksjonen 2 gjennomføres i et løsningsmiddel som ortodiklor-benzen, under nitrogen, ved forhøyet temperatur (omtrent 180°C). Reaction 2 is carried out in a solvent such as orthodichlorobenzene, under nitrogen, at an elevated temperature (approximately 180°C).
Det oppnådde tosylat alkaliniseres ved hjelp av fortynnet am-monium-hydroksyd løsning. The obtained tosylate is alkalinized using a dilute ammonium hydroxide solution.
Forbindelsene som fremstilles ved fremgangsmåten i henhold til oppfinnelsen er vasokonstriktorer. The compounds produced by the method according to the invention are vasoconstrictors.
De følgende eksempler illustrerer oppfinnelsen, analysene og spektra IR og RMN har bekreftet strukturen for forbindelsene. The following examples illustrate the invention, the analyzes and spectra IR and RMN have confirmed the structure of the compounds.
Eksempel 1. (2-cyklopen_tyl-f enoksy)-2-metyl-imidazolin og dets Example 1. (2-cyclopen_tyl-phenoxy)-2-methyl-imidazoline and dets
hydroklorid.hydrochloride.
Til en løsning av natrium etylat (100 ml absolutt etanol og 2,3 g natrium) tilsettes litt etter litt 8,1 g (0,0506 mol) ortocyklo-pentyl-fenol. Det omrøres i 30 min. Det tilsettes deretter i små porsjoner 7,5 g (0,05 mol) av hydrokloridet av 2-klormetyl-imidazolin. Reaksjonen får gå i 2 timer ved omgivelsenes temperatur og deretter anordnes tilbakeløp i 1 time. Etter en natt avsuges det dannede salt på filter, vaskes med varm etanol, opp-løsningen inndampes og den resterende olje vaskes med vann, eks-traheres med kloroform, tørkes og inndampes. Det oppnås en olje som krystalliserer. Denne omkrystalliseres fra hexan. Det oppnås fargeløse krystaller. Utbytte: 28 %. Smeltepunkt,= 112-113°C. To a solution of sodium ethylate (100 ml of absolute ethanol and 2.3 g of sodium) 8.1 g (0.0506 mol) of orthocyclopentylphenol are added little by little. It is stirred for 30 min. 7.5 g (0.05 mol) of the hydrochloride of 2-chloromethyl-imidazoline are then added in small portions. The reaction is allowed to run for 2 hours at ambient temperature and then reflux is arranged for 1 hour. After one night, the formed salt is filtered off with suction, washed with hot ethanol, the solution is evaporated and the remaining oil is washed with water, extracted with chloroform, dried and evaporated. An oil is obtained which crystallizes. This is recrystallized from hexane. Colorless crystals are obtained. Yield: 28%. Melting point,= 112-113°C.
Hydrokloridet oppnås ved tilsetning av saltsur eter. De ufargede mikrokrystaller smelter fra 167°C. The hydrochloride is obtained by adding hydrochloric acid ether. The colorless microcrystals melt from 167°C.
" Eksempel 2. (2-cyklobutyl-fenoksy)-2-metyl-imidazolin og dets hydroklorid. " Example 2. (2-Cyclobutyl-phenoxy)-2-methyl-imidazoline and its hydrochloride.
Reaksjonen gjennomføres på samme måte som i eksempel 1 med å gå ut fra o-cyklobutyl-fenol. The reaction is carried out in the same way as in example 1, starting from o-cyclobutyl phenol.
Hydrokloridet (fargeløse mikrokrystaller) smelter ved 204°C. The hydrochloride (colorless microcrystals) melts at 204°C.
Basen smelter ved 126°C.The base melts at 126°C.
Eksempel 3. (2-cyklohexyl-fenoksy)-2-metyl-imidazolin og dets Example 3. (2-cyclohexyl-phenoxy)-2-methyl-imidazoline and dets
hydroklorid.hydrochloride.
På samme måte som i eksempel 1 oppnås ved å gå ut fra o-cyklohexyl-fenol, hydrokloridet av (2-cyklohexyl-fenoksy)-2-metyl-imidazolin som smelter ved 252-254°C. In the same way as in example 1, starting from o-cyclohexyl-phenol, the hydrochloride of (2-cyclohexyl-phenoxy)-2-methyl-imidazoline is obtained which melts at 252-254°C.
Forbindelsene er blitt underkastet farmakologisk prøvning for å bestemme deres vasokonstriktoriske aktivitet. The compounds have been subjected to pharmacological testing to determine their vasoconstrictor activity.
1. Innvirkning på isolert aorta fra kanin.1. Effect on isolated rabbit aorta.
De konstriktoriske virkninger av forbindelsene ble studert på isolert aorta fra kanin (Furchgott et Bhadrakom, 19 53, J. Pharma-col. Exp. Ther. 108, 129) i kumulative doser (IO<-11>Ml<-1>til 10 Ml ■*") og de respektive pD£er beregnet som midlerePD2(n=4) for hver forbindelse. The constrictor effects of the compounds were studied on isolated rabbit aorta (Furchgott et Bhadrakom, 1953, J. Pharma-col. Exp. Ther. 108, 129) in cumulative doses (10<-11>Ml<-1> to 10 Ml ■*") and the respective pD£ are calculated as mean PD2(n=4) for each compound.
Forbindelsene i henhold til oppfinnelsen sammentrekker isolert aorta fra kanin. 2. Innvirkninger på aortatrykk i amyelerte rotter. Modifikasjonene på aortatrykket og hjertefrekvensen av amyélérte rotter ble studert, etter intravenøs tilførsel av økende doser av forbindelsen (0,25 til 16 ,ug kg ^) . De midlere kurver (n=5) for dose/effekt ble tegnet opp og aktivitetsforholdene beregnet. Forbindelsene frembringer enøkning i aortatrykket uten at dette følges av noen økning av hjertefrekvensen. Denne hypertensjon, som tilskrives en vasokonstriksjon, viser at forbindelsene er vasokonstriktorer. The compounds according to the invention contract isolated rabbit aorta. 2. Effects on aortic pressure in amyelated rats. The modifications in aortic pressure and heart rate of amyelated rats were studied after intravenous administration of increasing doses of the compound (0.25 to 16 µg kg^). The mean curves (n=5) for dose/effect were plotted and the activity ratios calculated. The compounds produce an increase in aortic pressure without this being followed by any increase in heart rate. This hypertension, which is attributed to a vasoconstriction, shows that the compounds are vasoconstrictors.
Resultatene er samlet i tabell II. Forbindelsene er sammen-lignet med nafazolin eller (1-naftyl-metyl)-2-imidazolin. The results are summarized in Table II. The compounds are compared with naphazoline or (1-naphthyl-methyl)-2-imidazoline.
De ovenstående resultater viser at forbindelsene er vasokonstriktorer. De kan anvendes ved behandling av rinologiske forstyrrelser som følger med tett nese og særlig da med coryza, riniter, sinu-siter, etc. The above results show that the compounds are vasoconstrictors. They can be used in the treatment of rhinological disorders that accompany a stuffy nose and especially when coryza, rhinitis, sinusitis, etc.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7717990A FR2394532A1 (en) | 1977-06-13 | 1977-06-13 | IMIDAZOLINE DERIVATIVES AND THEIR THERAPEUTIC APPLICATION |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO782027L true NO782027L (en) | 1978-12-14 |
Family
ID=9192012
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO782027A NO782027L (en) | 1977-06-13 | 1978-06-09 | PROCEDURE FOR PREPARING NEW IMIDAZOLINE DERIVATIVES |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS545975A (en) |
| AU (1) | AU515492B2 (en) |
| BE (1) | BE867984A (en) |
| CA (1) | CA1094566A (en) |
| CH (1) | CH635081A5 (en) |
| DE (1) | DE2825388A1 (en) |
| DK (1) | DK258778A (en) |
| FR (1) | FR2394532A1 (en) |
| GB (1) | GB1572689A (en) |
| IE (1) | IE46988B1 (en) |
| IT (1) | IT1095286B (en) |
| LU (1) | LU79794A1 (en) |
| NL (1) | NL7806269A (en) |
| NO (1) | NO782027L (en) |
| NZ (1) | NZ187507A (en) |
| SE (1) | SE7806740L (en) |
| ZA (1) | ZA783327B (en) |
-
1977
- 1977-06-13 FR FR7717990A patent/FR2394532A1/en active Granted
-
1978
- 1978-05-23 GB GB21685/78A patent/GB1572689A/en not_active Expired
- 1978-06-09 DK DK258778A patent/DK258778A/en unknown
- 1978-06-09 JP JP7028878A patent/JPS545975A/en active Pending
- 1978-06-09 IE IE1169/78A patent/IE46988B1/en unknown
- 1978-06-09 LU LU79794A patent/LU79794A1/en unknown
- 1978-06-09 IT IT24416/78A patent/IT1095286B/en active
- 1978-06-09 NL NL7806269A patent/NL7806269A/en not_active Application Discontinuation
- 1978-06-09 AU AU36994/78A patent/AU515492B2/en not_active Expired
- 1978-06-09 DE DE19782825388 patent/DE2825388A1/en not_active Withdrawn
- 1978-06-09 BE BE188459A patent/BE867984A/en unknown
- 1978-06-09 CA CA305,122A patent/CA1094566A/en not_active Expired
- 1978-06-09 ZA ZA00783327A patent/ZA783327B/en unknown
- 1978-06-09 CH CH632778A patent/CH635081A5/en not_active IP Right Cessation
- 1978-06-09 NO NO782027A patent/NO782027L/en unknown
- 1978-06-09 SE SE7806740A patent/SE7806740L/en unknown
- 1978-06-09 NZ NZ187507A patent/NZ187507A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1572689A (en) | 1980-07-30 |
| BE867984A (en) | 1978-12-11 |
| IE46988B1 (en) | 1983-11-16 |
| AU515492B2 (en) | 1981-04-09 |
| IT7824416A0 (en) | 1978-06-09 |
| CH635081A5 (en) | 1983-03-15 |
| FR2394532A1 (en) | 1979-01-12 |
| AU3699478A (en) | 1979-12-13 |
| IT1095286B (en) | 1985-08-10 |
| DE2825388A1 (en) | 1979-01-04 |
| CA1094566A (en) | 1981-01-27 |
| SE7806740L (en) | 1978-12-14 |
| NZ187507A (en) | 1979-10-25 |
| NL7806269A (en) | 1978-12-15 |
| JPS545975A (en) | 1979-01-17 |
| IE781169L (en) | 1978-12-13 |
| DK258778A (en) | 1978-12-14 |
| ZA783327B (en) | 1979-06-27 |
| LU79794A1 (en) | 1978-11-28 |
| FR2394532B1 (en) | 1980-01-18 |
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