NO123610B - - Google Patents
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- Publication number
- NO123610B NO123610B NO5064/69A NO506469A NO123610B NO 123610 B NO123610 B NO 123610B NO 5064/69 A NO5064/69 A NO 5064/69A NO 506469 A NO506469 A NO 506469A NO 123610 B NO123610 B NO 123610B
- Authority
- NO
- Norway
- Prior art keywords
- pyrimidinyl
- lower alkyl
- formula
- imidazolium
- alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- UNCQVRBWJWWJBF-UHFFFAOYSA-N 2-chloropyrimidine Chemical compound ClC1=NC=CC=N1 UNCQVRBWJWWJBF-UHFFFAOYSA-N 0.000 claims description 5
- -1 1-substituted-imidazole Chemical class 0.000 claims description 4
- SVBKPTSULMPPLC-UHFFFAOYSA-M 2-(3-methylimidazol-3-ium-1-yl)pyrimidine chloride Chemical compound [Cl-].C[N+]1=CN(C=C1)C1=NC=CC=N1 SVBKPTSULMPPLC-UHFFFAOYSA-M 0.000 claims description 3
- 150000005695 2-halopyrimidines Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 230000002218 hypoglycaemic effect Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- NPZNQGNWMDRMGV-UHFFFAOYSA-M 2-(2,3-dimethylimidazol-3-ium-1-yl)pyrimidine;chloride Chemical compound [Cl-].C1=C[N+](C)=C(C)N1C1=NC=CC=N1 NPZNQGNWMDRMGV-UHFFFAOYSA-M 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- GIWQSPITLQVMSG-UHFFFAOYSA-N 1,2-dimethylimidazole Chemical compound CC1=NC=CN1C GIWQSPITLQVMSG-UHFFFAOYSA-N 0.000 description 1
- KKKDZZRICRFGSD-UHFFFAOYSA-N 1-benzylimidazole Chemical compound C1=CN=CN1CC1=CC=CC=C1 KKKDZZRICRFGSD-UHFFFAOYSA-N 0.000 description 1
- RZVPFDOTMFYQHR-UHFFFAOYSA-N 2-chloro-4,6-dimethylpyrimidine Chemical compound CC1=CC(C)=NC(Cl)=N1 RZVPFDOTMFYQHR-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- ZSJLQEPLLKMAKR-UHFFFAOYSA-N Streptozotocin Natural products O=NN(C)C(=O)NC1C(O)OC(CO)C(O)C1O ZSJLQEPLLKMAKR-UHFFFAOYSA-N 0.000 description 1
- 206010070863 Toxicity to various agents Diseases 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
- 150000004693 imidazolium salts Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- ZSJLQEPLLKMAKR-GKHCUFPYSA-N streptozocin Chemical compound O=NN(C)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O ZSJLQEPLLKMAKR-GKHCUFPYSA-N 0.000 description 1
- 229960001052 streptozocin Drugs 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000003826 tablet Substances 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
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- C07D233/56—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
Analogifremgangsmåte ved fremstilling
av terapeutisk aktive imidazoliumsalter.
Foreliggende oppfinnelse angår fremgangsmåter ved fremstilling av l-(alkyl eller aralkyl)-3-(2-pyrimidinyl)-imidazoliumsalter som oppviser hypoglycemiske egenskaper.
Fremgangsmåteforbindelsene har formelen:
hvor R^" er laverealkyl, fortrinnsvis med 1-5 carbonatomer, som er rettkjedet eller forgrenet, eller.fenyl-laverealkyl som benzyl, fenethyl og lignende, og R , R-<*>, R og R^ som er like eller forskjellige, er hydrogen eller lavere alkyl som er
rettkjedet .eller forgrenet, og har 1-5 carbonatomer, og X er en hvilken som helst farmakologisk godtagbar anion, innbefattende f.eks. brom, klor, jod og lignende.
Fremgangsmåteforbindelsene kan fremstilles ved omsetning av
et 2-halogenpyrimidin med det nbdvendige 1-alkyl- eller 1-aralkyl-imidazol. 2-halogensubstituenten er fortrinnsvis kl.or eller brom. Reaksjonen utfores fortrinnsvis i nærvær av et opplosningsmiddel, idet en lavere alkohol som methanol, ethanol, isopropanol, butanol og lignende, er helt tilfredsstillende, skjont andre passende opp-losningsmidler som acetonitril eller dimethylformamid kan anvendes istedet. Reaksjonen lettes også ved oppvarmning til temperaturer opptil og innbefattende tilbakelopstemperaturen for reaksjonsblandingen.
Fremgangsmåteforbindelsene oppviser hypoglycemisk aktivitet
og er derfor nyttige til å senke unormalt hoyt blodsukkernivå hos varmblodige dyr som det fremgår av deres effektivitet til å senke blodsukkernivåene når de administreres til rotter som er gjort diabetiske ved forutgående behandling med streptozotocin. Senkning av blodsukkernivåene i dette forsdkssystem utfores ved doser som ikke gir gross-toksiske symptomer, og er bevist på potensiell klinisk anvendbarhet til dette formål.
Fremgangsmåteforbindelsene kan administreres i enhetsdose-former inneholdende fra ca. 50 mg til ca. 150 mg pr. enhetsdose for administrasjon oralt eller parenteralt. Eksempler på egnede doserings-former innbefatter tabletter, kapsler, piller, pulvere, granuler, tynne plater, etc, som kan fremstilles ved konvensjonelle metoder.
Fremgangsmåteforbindelsene kan også administreres oralt
eller parenteralt fordelt på 2 - h doser daglig.
Eksempel 1
l- methyl- 3-( 2- pyrimidinyl)- imidazolium- klorid
En blanding av 2,^-6 g (0,03 mol) 1-methylimidazol, 3, hk g (0,03 mol) 2-klorpyrimidin og 10 ml isopropylalkohol oppvarmes
under tilbakelop og omroring i 30 timer. Reaksjonsopplosningen be-handles med 25 ml ethylacetat for å felle 1,8 mg (31$) produkt i form av et hvitt fast stoff. Omkrystallisasjon fra acetonitril gir l-methyl-3-(2-pyrimidinyl)-imidazolium-klorid i form av hvite staver med sm.p. 221-222°C.
Analyse beregnet for CgH^ClN^:
C 48,86; H 4,61; N 28,49;
Funnet: C 48,91; H4,59; N28,4l.
Ved i ovenstående reaksjon å erstatte 2-klorpyrimidin med 2-klor-4,6-dimethylpyrimidin fikk man l-methyl-3-(4,6-dimethyl-2- pyrimidinyl)-imidazoliumklorid med sm.p. 244 - 247°C (spalt.). Denne forbindelse viste seg ved prøvning å ha god hypoglycemisk akt ivitet.
Eks empe1 2
1, 2- dimethyl- 3-( 2- pyrimidinyl)- imidazolium- klorid
En oppløsning av 3,2 g (0,033 mol) 1,2-dimethy1imidazol og 3,44 g (0,03 mol) 2-klorpyrimidin i 5 ml isopropylalkohol ble kokt under tilbakeløp i 17 timer. Reaksjonsblandingen ble avkjølt for å bringe produktet til å krystallisere. Produktet ble oppsamlet og omkrystallisert fra isopropanol hvilket ga 2,1 g (33%) 1,2-dimethyl-3- (2-pyrimidinyl)-imidazolium-klorid med sm.p. 267,5-268,5°C (spalt-ning) .
Analyse beregnet for C^H^CIN^:
C 51,31; H 5,26; N 26,60;
Funnet: C 51,51; H 5,20; N 26,55.
Eksempel 3
1-benzyl-3-(2-pyrimidinyl)-imidazoliumklorid • 3/4 H,,0
En blanding av 4,75 9 (0,03 mol) 1-benzylimidazol, 3,44 9 (0,03 mol) 2-klorpyrimidin og IO ml isopropylalkohol ble oppvarmet under tilbakeløp og omrøring i 24 timer. Reaksjonsoppløsningen ble behandlet med 75 ml ethylacetat for å felle 4,00 g (49%) produkt i form av et hvitt fast stoff. Omkrystallisasjon fra acetonitril ga produktet i form av hvite prismer som smeltet ved 135 - 136°C. Efter tørring ved 82°C i 5 timer hadde smeltepunktet steget til 190 - 192°C~ Elementæranalyse og NMR-spektrum viste at dette var 1-benzyl-3^(2-pyrimidinyl)-imidazolium-klorid inneholdende 3/4 mol hydrat-vann.
Analyse beregnet for C^H^CIN^ • 3/4 ^ 2°:
C 58,74; H 5,11; N 19,57;
Funnet: C 58,75; h 5,37; N 19,35.
Ved å følge fremgangsmåten beskrevet i eksempel 1, men ved å anvende 2-halogenpyrimidin- og 1-substituert-imidazolreaktantene angitt i tabell 1 fåes ytterligere l-(alkyl eller aralkyl)-3-(2--pyrimidinyl)-imidazolium kvartære salter med substituentene R 1, R 2,
3 h 5
R , R og R som angitt i tabell I.
Claims (2)
1. Analogifremgangsmåte ved fremstilling av terapeutisk aktive l-(alkyl eller aralkyl)-3-(2-pyrimidinyl)-imidazoliumsalter av formelen:
hvor R1 er laverealkyl eller fenyllaverealkyl, R2, R^, R^ og R-', som er like eller forskjellige, er hydrogen eller laverealkyl, og X er et farmakologisk godtagbart halogenid, karakterisert ved at en reaksjonsblanding av et 2-halogenpyrimidin av formelen: 3 4 5
hvor R , R og R-^ er som ovenfor angitt, og en 1-substituert-imidazol av formelen: 1 2
hvor R og R er som ovenfor angitt, oppvarmes.
2. Fremgangsmåte ifølge krav 1 til fremstilling av 1-methyl-3-(2-pyrimidinyl)-imidazolium-klorid, karakterisert ved at en blanding av 1-methylimidazol og 2-klorpyrimidin oppvarmes i nærvær av et oppløsnings - middel.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US78636968A | 1968-12-23 | 1968-12-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO123610B true NO123610B (no) | 1971-12-20 |
Family
ID=25138387
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO5064/69A NO123610B (no) | 1968-12-23 | 1969-12-22 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3557114A (no) |
| BE (1) | BE743510A (no) |
| BR (1) | BR6914814D0 (no) |
| CH (1) | CH522660A (no) |
| DE (1) | DE1964282A1 (no) |
| ES (1) | ES374692A1 (no) |
| FR (1) | FR2026902B1 (no) |
| GB (1) | GB1252847A (no) |
| IL (1) | IL33538A (no) |
| NL (1) | NL6918402A (no) |
| NO (1) | NO123610B (no) |
| SE (1) | SE353722B (no) |
| ZA (1) | ZA698862B (no) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE43313B1 (en) | 1975-09-03 | 1981-01-28 | Pfizer | Quaternary salts as hypoglycemic agents |
| EP0421266A1 (de) * | 1989-10-06 | 1991-04-10 | BASF Aktiengesellschaft | Azolylpyrimidin- und -triazinderivate und sie enthaltende Mittel |
| US5916891A (en) | 1992-01-13 | 1999-06-29 | Smithkline Beecham Corporation | Pyrimidinyl imidazoles |
| ZA9610687B (en) * | 1995-12-22 | 1997-09-29 | Smithkline Beecham Corp | Novel synthesis. |
| US6046208A (en) * | 1996-01-11 | 2000-04-04 | Smithkline Beecham Corporation | Substituted imidazole compounds |
| AP9700912A0 (en) | 1996-01-11 | 1997-01-31 | Smithkline Beecham Corp | Novel cycloalkyl substituted imidazoles |
| US5977103A (en) * | 1996-01-11 | 1999-11-02 | Smithkline Beecham Corporation | Substituted imidazole compounds |
| US5929076A (en) * | 1997-01-10 | 1999-07-27 | Smithkline Beecham Corporation | Cycloalkyl substituted imidazoles |
| US6239279B1 (en) * | 1998-12-16 | 2001-05-29 | Smithkline Beecham Corporation | Synthesis for 4-aryl-5-pyrimidine imidazole substituted derivatives |
-
1968
- 1968-12-23 US US786369A patent/US3557114A/en not_active Expired - Lifetime
-
1969
- 1969-12-05 BR BR214814/69A patent/BR6914814D0/pt unknown
- 1969-12-08 NL NL6918402A patent/NL6918402A/xx unknown
- 1969-12-15 IL IL33538A patent/IL33538A/en unknown
- 1969-12-18 SE SE17485/69A patent/SE353722B/xx unknown
- 1969-12-18 ES ES374692A patent/ES374692A1/es not_active Expired
- 1969-12-19 GB GB1252847D patent/GB1252847A/en not_active Expired
- 1969-12-22 BE BE743510D patent/BE743510A/xx unknown
- 1969-12-22 NO NO5064/69A patent/NO123610B/no unknown
- 1969-12-22 DE DE19691964282 patent/DE1964282A1/de active Pending
- 1969-12-22 CH CH1903269A patent/CH522660A/de not_active IP Right Cessation
- 1969-12-22 ZA ZA698862*A patent/ZA698862B/xx unknown
- 1969-12-22 FR FR696944342A patent/FR2026902B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH522660A (de) | 1972-06-30 |
| BR6914814D0 (pt) | 1973-03-08 |
| SE353722B (no) | 1973-02-12 |
| ZA698862B (en) | 1971-07-28 |
| IL33538A0 (en) | 1970-02-19 |
| NL6918402A (no) | 1970-06-25 |
| FR2026902B1 (no) | 1973-08-10 |
| ES374692A1 (es) | 1972-01-01 |
| US3557114A (en) | 1971-01-19 |
| FR2026902A1 (no) | 1970-09-25 |
| IL33538A (en) | 1972-08-30 |
| GB1252847A (no) | 1971-11-10 |
| BE743510A (no) | 1970-06-22 |
| DE1964282A1 (de) | 1970-07-09 |
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