NO335866B1 - Karbonatforbindelse - Google Patents
Karbonatforbindelse Download PDFInfo
- Publication number
- NO335866B1 NO335866B1 NO20110598A NO20110598A NO335866B1 NO 335866 B1 NO335866 B1 NO 335866B1 NO 20110598 A NO20110598 A NO 20110598A NO 20110598 A NO20110598 A NO 20110598A NO 335866 B1 NO335866 B1 NO 335866B1
- Authority
- NO
- Norway
- Prior art keywords
- general formula
- group
- hydrogen atom
- mmol
- alkyl
- Prior art date
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- -1 carbonate compound Chemical class 0.000 title claims abstract description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 abstract description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- NXLNNXIXOYSCMB-UHFFFAOYSA-N (4-nitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(OC(Cl)=O)C=C1 NXLNNXIXOYSCMB-UHFFFAOYSA-N 0.000 description 2
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- YNTOKMNHRPSGFU-UHFFFAOYSA-N n-Propyl carbamate Chemical compound CCCOC(N)=O YNTOKMNHRPSGFU-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical group ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- BPYUAAOXJAQFAX-UHFFFAOYSA-N 3-[5-(6-methoxynaphthalen-1-yl)-1,3-dioxan-2-yl]propan-1-amine Chemical compound C=1C=CC2=CC(OC)=CC=C2C=1C1COC(CCCN)OC1 BPYUAAOXJAQFAX-UHFFFAOYSA-N 0.000 description 1
- VSBPFIKNUJWISH-UHFFFAOYSA-N 3-[5-[6-(cyclopropylmethoxy)naphthalen-1-yl]-1,3-dioxan-2-yl]propan-1-amine Chemical compound C1OC(CCCN)OCC1C1=CC=CC2=CC(OCC3CC3)=CC=C12 VSBPFIKNUJWISH-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 101100229907 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) GPP2 gene Proteins 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
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
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Abstract
Oppfinnelsen vedrører en forbindelse med generelle formel (III) hvori R2 representerer en gruppe med generell formel CHR3CONHR4 hvori R3 representerer et hydrogenatom eller en metylgruppe og R4 representerer et hydrogenatom eller en (C1-C3) alkyl-, (C3-C5) cykloalkyl- eller (pyridin-4-yl) metylgruppe, og U representerer et hydrogenatom eller en nitrogruppe.
Description
Den foreliggende oppfinnelse angår en forbindelse som tilsvarer generell formel (III)
hvori
R.2 representerer en gruppe med generell formel CHR3CONHR4hvori R3representerer et hydrogenatom eller en metylgruppe, og
R4representerer et hydrogenatom eller en (C1-C3)alkyl-, (C3-C5) cykloalkyl- eller (pyridin-4-yl)metylgruppe, og U representerer et hydrogenatom eller en nitrogruppe.
Forbindelsene med den generelle formel (III) kan for eksempel anvendes som mellomprodukter for fremstilling av forbindelsene med den generelle formel (I)
hvori
Ri representerer en fenyl- eller naftalenylgruppe eventuelt substituert med ett eller flere halogenatomer eller hydroksyl-, cyano-, nitro-, (C1-C3)alkyl-, (Ci-C3)alkoksy-, trifluormetyl-, trifluormetoksy-, benzyloksy-, (C3-C6) cykloalkyl-O- eller (C3-C6) cykloalkyl (C1-C3) - alkoksygrupper,
R2representerer
enten en gruppe med generell formel CHR3CONHR4hvori R3representerer et hydrogenatom eller en metylgruppe og R4representerer et hydrogenatom eller en (C1-C3)alkyl-,
(C3-C5) cykloalkyl- eller (pyridin-4-yl)metylgruppe,
eller en 2,2,2-trifluoretylgruppe,
eller en (imidazol-2-yl)metylgruppe,
eller en (benzimidazol-2-yl)metylgruppe,
eller en fenylgruppe eventuelt substituert med ett eller flere halogenatomer eller cyano-, nitro-, (C1-C3) alkyl-, (C1-C3) alkoksy-, trifluormetyl- eller
trifluormetoksygrupper, og
n representerer et tall som varierer fra 1 til 3.
Forbindelsene med generell formel (I) kan omfatte ett eller flere asymmetriske karboner. De kan eksistere i form av enantiomerer eller diastereoisomerer. Forbindelsene med generell formel (I) kan også eksistere i form av cis- eller trans-stereoisomerer. Disse enantiomerer, diastereoisomerer og stereoisomerer kan også eksistere i form av deres blandinger, inkluderende de racemiske blandinger.
Forbindelsene med formel (I) kan eksistere i form av baser eller addisjonssalter med syrer.
Disse saltene er fordelaktige fremstilt med farmasøytisk akseptable syrer, men saltene av andre syrer kan anvendes, f.eks. for rensing eller isolering av forbindelsene med formel (I). Forbindelsene med generell formel (I) kan være i form av hydrater eller solvater, nemlig i form av assosiasjoner eller kombinasjoner med ett eller flere vannmolekyler eller med et løsningsmid-del.
I denne beskrivelse er:
- uttrykket " (Ct-Cz) hvor t og z kan ha verdiene 1 til 6" ment å bety en karbonkjede som kan ha fra t til z karbonatomer, f.eks. er " (C1-C3) " ment å bety en
karbonkjede som kan ha fra 1 til 3 karbonatomer, betegnelsen "alkyl" er ment å bety en rettkjedet eller forgrenet, mettet alifatisk gruppe; f.eks. representerer en (C1-C3)alkylgruppe en rettkjedet eller forgrenet karbonkjede med 1 til 3 karbonatomer,
mer spesielt et metyl, etyl, propyl eller isopropyl, betegnelsen "cykloalkyl" er ment å bety en cyklisk alkylgruppe; f.eks. representerer en (C3-C5)cykloalkylgruppe en cyklisk karbonkjede med 3 til 5 karbonatomer, mer spesielt et cyklopropyl, cyklobutyl
eller cyklopentyl,
betegnelsen "alkoksy" er ment å bety en alkyloksygruppe inneholdende en rettkjedet eller
forgrenet, mettet alifatisk kjede,
betegnelsen "halogenatom" er ment å bety et fluor, et
klor, et brom eller et jod.
En metode for fremstilling av forbindelsene med generell formel (I)(Skjema 1) består således i å reagere et amin med generell formel (II), hvori Ri og n er som definert i generell formel (I), med et karbonat med generell formel (III), hvori U representerer et hydrogenatom eller en nitrogruppe og R2er som definert i generell formel (III) som nevnt ovenfor, i et løsningsmiddel slik som toluen eller dikloretan, ved en temperatur mellom 0 og 80°C. Karbonatene med generell formel (III) kan fremstilles i samsvar med en hvilken som helst metode beskrevet i litteraturen, f.eks. ved å reagere en alkohol med generell formel HOR2med fenyl- eller 4-nitrofenylklorformiat, i nærvær av en base slik som trietylamin eller diisopropyletylamin.
Aminene med generell formel (II) kan fremstilles i samsvar med metodene for fremstilling som er beskrevet i patentsøknadene EP 0461958, WO 97/20836 og WO 98/55474, eventuelt tilpasset i samsvar med teknikker som er kjent for de fagkyndige i teknikken.
De etterfølgende eksempler illustrerer fremstillingen av noen forbindelser i henhold til oppfinnelsen. Mikroana-lysene, IR- og NMR-spektrene og/eller LC-MS
(væskekromatografi koblet til massespektroskopi)
bekrefter strukturene og renhetene til de oppnådde forbindelser.
Eksempel 1
lff-imidazol-2-ylmetyl- trans- 3- [5- (6-metoksynaftalen-1-yl) -1, 3-dioksan-2-yl]propylkarbamat
1.1 Fenyl - (1-trif enylmetyl-lJf-imidazol-2-yl)metylkarbonat
Ved å gå ut fra 3 g (8,80 mmol) 1-trifenylmetyl-lff-imidazol-2-metanol (J. Het. Chem., (1995), 32, 903-906) og 1,1 ml (8,80 mmol) fenyl-klorformiat, oppnås 3,9 g produkt, som anvendes umodifisert i det etterfølgende trinn.
1. 2 (1-trif enylmetyl-lff-imidazol-2-yl) metyl- trans- 3- [5-(6-metoksynaftalen-1-yl)-1,3-dioksan-2-yl]propylkarbamat
Ved å gå ut fra 2,5 g (8,28 mmol) trans-3-[5-(6-metoksynaftalen-l-yl)-1,3-dioksan-2-yl]propanamin og 3,8 g (8,28 mmol) fenyl-(1-trifenylmetyl-lff-imidazol-2-yl)metylkarbonat, oppnådd i trinn 1.1, oppnås 3,2 g av et faststoff i amorf form.
1. 3 lff-imidazol-2-ylmetyl- trans- 3- [5- ( 6-metoksynaf talen-l-yl) -1, 3-dioksan-2-yl]propylkarbamat
En oppløsning av 0,6 ml (2,83 mmol) trifluoreddiksyre i 2 ml diklormetan tilsettes, dråpevis, ved omgivelsestemperatur til en oppløsning av 1,9 g (2,83 mmol) (1-trifenylmetyl-lff-imidazol-2-yl) metyl- trans- 3- [5- (6-metoksynaftalen-l-yl)-1,3-dioksan-2-yl]propylkarbamat, oppnådd i trinn 1.2, i 150 ml diklormetan, og blandingen omrøres ved omgivelsestemperatur i 12 timer. Konsentrering utføres under redusert trykk, resten
tas opp med diklormetan og en mettet vandig natriumhydrogenkarbonatoppløsning, den organiske fase separeres, vaskes med en mettet vandig natriumklorid-oppløsning og tørkes over natriumsulfat, konsentrering utføres under redusert trykk, og resten renses ved kromatografi på silikagel, ved eluering med en 98/2/0,2 blanding av diklormetan, metanol og vandig ammoniakk. Etter rekrystallisering fra etylacetat, oppnås til sist 0,820 g rent produkt.
Smeltepunkt: 130-132°C.
<1>H NMR: (CDC13) 8 (ppm) 10.0 (bred m, 1H) ; 8.10 (d,
1H); 7.65 (d, 1H); 7.35 {dd, 1H); 7.25 (d, 1H); 7.15
(dd, 1H); 7.05 (dd, 1H); 7.00 (s, 2H); 5.15 (m+s, 3H) ;
4.70 (t, 1H); 4.30 (m, 2H); 3.95-3.90 (m, 6H); 3.30 (m, 2H); 1.85 (m, 4H).
Eksempel 2
2,2,2-trifluoretyl-trans-3-[5-(6-cyklopropyl-metoksynaftalen-l-yl)-1,3-dioksan-2-yl]propylkarbamat
0,075 ml (1,01 mmol) 2,2,2-trifluoretanol tilsettes, dråpevis og ved omgivelsestemperatur, til en suspensjon av 0,205 g (1,01 mmol) 4-nitrofenylklorformiat og 0,555 g (2,02 mmol) W,N-diisopropylaminoetylpolystyren (Ps-DIEA, 2% DVB, titer = 3,66 mmol/g) i 7,1 ml diklormetan. Blandingen omrøres med orbitalrysting og ved omgivelsestemperatur i 16 timer. Harpiksen filtreres gjennom en patron utstyrt med en sintret glasstrakt og skylling utføres med 4 ml diklormetan. Filtratet konsentreres under redusert trykk og den således oppnådde oljeaktige rest tas opp i 3,5 ml 1,2-dikloretan. 0,134 ml (0,78 mmol) W,N-diisopropyletylamin og 0,205 g (0,6 mmol) 3-[5-(6-cyklopropylmetoksynaftalen-l-yl)-1,3-dioksan-2-yl]propylamin tilsettes i rekkefølge. Denne reaksjonsblandingen oppvarmes ved 60°C i 16 timer. Etter avkjøling utføres vasking med 20 ml av en IN natriumhydroksydoppløsning. Fasene separeres og den organiske fasen filtreres gjennom en hydrofob sintret glasstrakt. Filtratet konsentreres under redusert trykk og resten renses ved kromatografi på silikagel, ved eluering med en 80/20 blanding av cykloheksan og etylacetat. Etter vasking i 5 ml diisopropyleter oppnås 0,076 g hvitt faststoff.
LC-MS: M+H = 468
Smeltepunkt: 105-107°C
XH NMR: (CDCI3) 6 (ppm) : 8.15 (d, 1H) ; 7.65 (d, 1H).;
7.35 (dd, 1H); 7.25 (m, 1H); 7.15 (d, 1H); 7.10 (d,
1H)'; 5.15 (bred m, 1H); 4.75 (t, 1H); 4.50 (q, 2H) ; 4.30 (dd, 2H); 4.10-3.80 (m, 5H); 3.40-3.20 (m, 2H);
1.90-1.65 (m, 4H); 1.45-1.20 (m, 1H); 0.75-0.60 (m, 2H); 0.50-0.35 (2H).
Claims (1)
1. Forbindelse,
karakterisert vedat den tilsvarer generell formel (III)
hvori
R.2representerer en gruppe med generell formel CHR3CONHR4hvori R3representerer et hydrogenatom eller en metylgruppe, og
R4representerer et hydrogenatom eller en (C1-C3)alkyl-, (C3-C5)cykloalkyl- eller (pyridin-4-yl)metylgruppe, og U representerer et hydrogenatom eller en nitrogruppe.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0210707A FR2843964B1 (fr) | 2002-08-29 | 2002-08-29 | Derives de dioxane-2-alkylcarbamates, leur preparation et leur application en therapeutique |
| PCT/FR2003/002590 WO2004020430A2 (fr) | 2002-08-29 | 2003-08-27 | Derives de dioxane-2-alkylcarbamates, leur preparation et leur application en therapeutique |
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| NO20110598L NO20110598L (no) | 2005-03-29 |
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| NO20110598A NO335866B1 (no) | 2002-08-29 | 2011-04-15 | Karbonatforbindelse |
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| CA2501506C (en) * | 2002-10-07 | 2014-02-11 | Daniele Piomelli | Modulation of anxiety through blockade of anandamide hydrolysis |
| FR2854633B1 (fr) * | 2003-05-07 | 2005-06-24 | Sanofi Synthelabo | Derives de piperidinyl-et piperazinyl-alkylcarbamates, leur preparation et leur application en therapeutique |
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| FR2941696B1 (fr) * | 2009-02-05 | 2011-04-15 | Sanofi Aventis | Derives d'azaspiranyl-alkylcarbamates d'heterocycles a 5 chainons, leur preparation et leur application en therapeutique |
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| KR101820541B1 (ko) | 2009-09-09 | 2018-02-28 | 다이닛본 스미토모 세이야꾸 가부시끼가이샤 | 8-옥소디히드로퓨린 유도체 |
| US8274566B2 (en) * | 2009-10-09 | 2012-09-25 | John Mezzalingua Associates, Inc. | Modulation analyzer and level measurement device |
| EP2545915A1 (en) | 2011-07-11 | 2013-01-16 | Sanofi | 2-amino-2-oxoethyl trans-3-[5-(6-methoxy-naphtalen-1-yl)-1,3-dioxan-2-yl]propyl-carbamate for use in the treatment of persistent cancer pain |
| EP2545914A1 (en) | 2011-07-11 | 2013-01-16 | Sanofi | 2-amino-2-oxoethyl trans-3-[5-(6-methoxy-naphtalen-1-yl)-1,3-dioxan-2-yl]propyl-carbamate for use in the treatment of persistent cancer pain |
| KR101653473B1 (ko) * | 2012-01-06 | 2016-09-01 | 어바이드 테라퓨틱스, 인크. | 카르바메이트 화합물 및 그의 제조 및 이용 방법 |
| CN114835726B (zh) * | 2022-03-24 | 2024-01-26 | 上海诺精生物科技有限公司 | 一类抑制肿瘤细胞干性的化合物及用途 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0461958B1 (fr) * | 1990-06-15 | 1994-09-14 | Synthelabo | Dérivés de 2-(aminoalkyl)-5-(arylalkyl)-1,3-dioxanes, leur préparation et leur application en thérapeutique |
| US5173506A (en) * | 1990-08-16 | 1992-12-22 | Schering Corporation | N-(mercaptoalkyl)ureas and carbamates |
| FR2742152B1 (fr) * | 1995-12-06 | 1998-01-16 | Synthelabo | Derives de 5-naphtalen-1-yl-1,3-dioxanes, leur preparation et leur application en therapeutique |
| AT403579B (de) * | 1995-12-07 | 1998-03-25 | Agrolinz Melamin Gmbh | Verfahren zur herstellung von hochreinem melamin |
| KR20010013435A (ko) | 1997-06-05 | 2001-02-26 | 고든 라이트 | 5-나프탈렌-1-일-1,3-디옥산 유도체, 제조 및 치료에의 이용 |
| KR20010042704A (ko) * | 1998-04-16 | 2001-05-25 | 데이비드 비. 맥윌리암스 | 인테그린이 인테그린 수용체에 결합하는 것을 억제하는ｎ,ｎ-이치환된 아미드 |
| FR2816938B1 (fr) * | 2000-11-22 | 2003-01-03 | Sanofi Synthelabo | Derives de 3-aroylindole, leur procede de preparation et les compositions pharmaceutiques en contenant |
| FR2843964B1 (fr) * | 2002-08-29 | 2004-10-01 | Sanofi Synthelabo | Derives de dioxane-2-alkylcarbamates, leur preparation et leur application en therapeutique |
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