SK7122002A3 - Process for the preparation of 6-methyl-2-(4-methyl-phenyl)- imidazo[1,2-a]pyrimidine-3-(n,n-dimethyl-acetamide) and intermediates - Google Patents

Process for the preparation of 6-methyl-2-(4-methyl-phenyl)- imidazo[1,2-a]pyrimidine-3-(n,n-dimethyl-acetamide) and intermediates Download PDF

Info

Publication number: SK7122002A3
Authority: SK; Slovakia
Prior art keywords: methyl; formula; phenyl; compound; imidazo
Prior art date: 1999-11-22

Application number

SK712-2002A

Other languages

English (en)

Slovak (sk)

Inventor

Laszlo Pongo

Jozsef Reiter

Gyula Simig

Peter Tompe

Fekete Valeria Hoffmanne

Endre Rivo

Laszlo Koncz

Donath Gyorgyi Vereczkeyne

Kalman Nagy

Original Assignee

Egyt Gyogyszervegyeszeti Gyar

Priority date (The priority date 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 date listed.)

1999-11-22

Filing date

2000-11-22

Publication date

2002-10-08

1999-11-22 Priority claimed from HU9904379A external-priority patent/HU227358B1/hu

1999-11-22 Priority claimed from HU9904377A external-priority patent/HUP9904377A2/hu

2000-11-22 Application filed by Egyt Gyogyszervegyeszeti Gyar filed Critical Egyt Gyogyszervegyeszeti Gyar

2002-10-08 Publication of SK7122002A3 publication Critical patent/SK7122002A3/sk

Links

238000000034 method Methods 0.000 title claims abstract description 48
230000008569 process Effects 0.000 title claims abstract description 28
238000002360 preparation method Methods 0.000 title claims abstract description 9
239000000543 intermediate Substances 0.000 title abstract description 3
150000001875 compounds Chemical class 0.000 claims abstract description 51
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims abstract description 22
239000002253 acid Substances 0.000 claims abstract description 12
150000003839 salts Chemical class 0.000 claims abstract description 12
125000000217 alkyl group Chemical group 0.000 claims abstract description 11
239000000010 aprotic solvent Substances 0.000 claims abstract description 5
150000002148 esters Chemical class 0.000 claims abstract description 5
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 48
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 28
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 27
238000006243 chemical reaction Methods 0.000 claims description 21
239000011541 reaction mixture Substances 0.000 claims description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 12
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
150000001242 acetic acid derivatives Chemical class 0.000 claims description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 7
150000001447 alkali salts Chemical class 0.000 claims description 6
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
239000012452 mother liquor Substances 0.000 claims description 5
239000003377 acid catalyst Substances 0.000 claims description 4
230000001476 alcoholic effect Effects 0.000 claims description 4
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
239000007858 starting material Substances 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
150000004820 halides Chemical class 0.000 claims description 3
230000002152 alkylating effect Effects 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical group 0.000 claims description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 2
229910000041 hydrogen chloride Inorganic materials 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
229910052794 bromium Chemical group 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
230000032050 esterification Effects 0.000 claims 1
238000005886 esterification reaction Methods 0.000 claims 1
239000000932 sedative agent Substances 0.000 abstract description 2
230000001624 sedative effect Effects 0.000 abstract description 2
238000002560 therapeutic procedure Methods 0.000 abstract 1
239000000047 product Substances 0.000 description 21
229910052739 hydrogen Inorganic materials 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 10
-1 alkali metal cyanide Chemical class 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
238000009835 boiling Methods 0.000 description 7
229940113088 dimethylacetamide Drugs 0.000 description 7
UVFOVSRWICIMNX-UHFFFAOYSA-N methyl 2-[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]acetate Chemical compound N1=C2C=CC(C)=CN2C(CC(=O)OC)=C1C1=CC=C(C)C=C1 UVFOVSRWICIMNX-UHFFFAOYSA-N 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000000921 elemental analysis Methods 0.000 description 6
239000002904 solvent Substances 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
239000007789 gas Substances 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 4
JHGHLTNIQXXXNV-UHFFFAOYSA-N 2-[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]acetic acid Chemical compound C1=CC(C)=CC=C1C1=C(CC(O)=O)N2C=C(C)C=CC2=N1 JHGHLTNIQXXXNV-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
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
239000002585 base Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
238000002844 melting Methods 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000000376 reactant Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
ZAFYATHCZYHLPB-UHFFFAOYSA-N zolpidem Chemical compound N1=C2C=CC(C)=CN2C(CC(=O)N(C)C)=C1C1=CC=C(C)C=C1 ZAFYATHCZYHLPB-UHFFFAOYSA-N 0.000 description 3
229960001475 zolpidem Drugs 0.000 description 3
AWEWSJJCANQFRB-UHFFFAOYSA-N 6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridine Chemical compound C1=CC(C)=CC=C1C1=CN(C=C(C)C=C2)C2=N1 AWEWSJJCANQFRB-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
230000009435 amidation Effects 0.000 description 2
238000007112 amidation reaction Methods 0.000 description 2
238000010533 azeotropic distillation Methods 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
239000002178 crystalline material Substances 0.000 description 2
RKFYYMREZGSLPU-UHFFFAOYSA-N ethyl 2-[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]acetate Chemical compound N1=C2C=CC(C)=CN2C(CC(=O)OCC)=C1C1=CC=C(C)C=C1 RKFYYMREZGSLPU-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
239000005457 ice water Substances 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
238000010561 standard procedure Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
231100000331 toxic Toxicity 0.000 description 2
230000002588 toxic effect Effects 0.000 description 2
XQRILQRMHDAYOF-UHFFFAOYSA-N 2,2-dimethoxy-n,n-dimethylacetamide Chemical compound COC(OC)C(=O)N(C)C XQRILQRMHDAYOF-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
QALOMISOPPEYLW-UHFFFAOYSA-N 2-[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]-3-phenylpropanoic acid Chemical compound C1=CC(C)=CC=C1C1=C(C(CC=2C=CC=CC=2)C(O)=O)N2C=C(C)C=CC2=N1 QALOMISOPPEYLW-UHFFFAOYSA-N 0.000 description 1
ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 1
XBPPLECAZBTMMK-UHFFFAOYSA-N 2-chloro-n,n-dimethylacetamide Chemical class CN(C)C(=O)CCl XBPPLECAZBTMMK-UHFFFAOYSA-N 0.000 description 1
CMBSSVKZOPZBKW-UHFFFAOYSA-N 5-methylpyridin-2-amine Chemical compound CC1=CC=C(N)N=C1 CMBSSVKZOPZBKW-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
KFUVOGWGMINXAJ-UHFFFAOYSA-N C1=CC(C)=CC=C1C1=C(CC(=O)OCC=2C=CC=CC=2)N2C=C(C)C=CC2=N1 Chemical compound C1=CC(C)=CC=C1C1=C(CC(=O)OCC=2C=CC=CC=2)N2C=C(C)C=CC2=N1 KFUVOGWGMINXAJ-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
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
GVGLGOZIDCSQPN-PVHGPHFFSA-N Heroin Chemical group O([C@H]1[C@H](C=C[C@H]23)OC(C)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4OC(C)=O GVGLGOZIDCSQPN-PVHGPHFFSA-N 0.000 description 1
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
239000001358 L(+)-tartaric acid Substances 0.000 description 1
235000011002 L(+)-tartaric acid Nutrition 0.000 description 1
FEWJPZIEWOKRBE-LWMBPPNESA-N L-(+)-Tartaric acid Natural products OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 description 1
238000006683 Mannich reaction Methods 0.000 description 1
OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
150000007960 acetonitrile Chemical class 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
230000002009 allergenic effect Effects 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000011109 contamination Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000008570 general process Effects 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000000203 mixture Substances 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
ZKSRNGXLVCJQCC-UHFFFAOYSA-N n,n-dimethyl-1-[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methanamine Chemical compound N1=C2C=CC(C)=CN2C(CN(C)C)=C1C1=CC=C(C)C=C1 ZKSRNGXLVCJQCC-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
LCFGKLYPSUEOBW-UHFFFAOYSA-N propan-2-yl 2-[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]acetate Chemical compound N1=C2C=CC(C)=CN2C(CC(=O)OC(C)C)=C1C1=CC=C(C)C=C1 LCFGKLYPSUEOBW-UHFFFAOYSA-N 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000011403 purification operation Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
239000013589 supplement Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pain & Pain Management (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Biomedical Technology (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

SK712-2002A 1999-11-22 2000-11-22 Process for the preparation of 6-methyl-2-(4-methyl-phenyl)- imidazo[1,2-a]pyrimidine-3-(n,n-dimethyl-acetamide) and intermediates SK7122002A3 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
HU9904379A HU227358B1 (en)	1999-11-22	1999-11-22	Novel process for the preparation of 6-methyl-2-(4-methyl-phenyl)-imidazo[1,2-a]pyrimidyne-3-(n,n-dimethyl-acetamide)
HU9904377A HUP9904377A2 (en)	1999-11-22	1999-11-22	6-methyl-2-(4-methyl-phenyl)-imidazole-[1,2-a]pyrimidine-3-acetic acid-esters and process for their preparation
PCT/HU2000/000120 WO2001038327A2 (en)	1999-11-22	2000-11-22	Process for the preparation of 6-methyl-2-(4-methyl-phenyl)-imidazo[1,2-a]pyrimidine-3-(n,n-dimethyl-acetamide) and intermediates

Publications (1)

Publication Number	Publication Date
SK7122002A3 true SK7122002A3 (en)	2002-10-08

Family

ID=90000034

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK712-2002A SK7122002A3 (en)	1999-11-22	2000-11-22	Process for the preparation of 6-methyl-2-(4-methyl-phenyl)- imidazo[1,2-a]pyrimidine-3-(n,n-dimethyl-acetamide) and intermediates

Country Status (15)

Country	Link
EP (1)	EP1259509B1 (ru)
JP (1)	JP2003518016A (ru)
KR (1)	KR100656636B1 (ru)
CN (1)	CN1227252C (ru)
AT (1)	ATE304540T1 (ru)
AU (1)	AU1873901A (ru)
CZ (1)	CZ300711B6 (ru)
DE (1)	DE60022684T2 (ru)
DK (1)	DK1259509T3 (ru)
ES (1)	ES2248154T3 (ru)
HR (1)	HRP20020471B1 (ru)
PL (1)	PL354366A1 (ru)
RU (1)	RU2254334C2 (ru)
SK (1)	SK7122002A3 (ru)
WO (1)	WO2001038327A2 (ru)

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2000
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Publication number	Publication date
RU2254334C2 (ru)	2005-06-20
WO2001038327A3 (en)	2002-09-12
CZ300711B6 (cs)	2009-07-22
DE60022684D1 (de)	2005-10-20
AU1873901A (en)	2001-06-04
ES2248154T3 (es)	2006-03-16
HRP20020471B1 (en)	2007-12-31
CZ20021713A3 (cs)	2002-08-14
HRP20020471A2 (en)	2005-10-31
EP1259509A1 (en)	2002-11-27
KR100656636B1 (ko)	2006-12-11
CN1413212A (zh)	2003-04-23
CN1227252C (zh)	2005-11-16
WO2001038327A2 (en)	2001-05-31
PL354366A1 (en)	2004-01-12
DK1259509T3 (da)	2006-01-16
DE60022684T2 (de)	2006-06-29
JP2003518016A (ja)	2003-06-03
ATE304540T1 (de)	2005-09-15
EP1259509B1 (en)	2005-09-14
KR20020052213A (ko)	2002-07-02

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