MXPA06013537A

MXPA06013537A - 3-??4-{(alcanoil 6- substituidas) piridin-3-il}-3 -fenil!-5-(1h-1, 2, 3-triazol -1-ilmetil)-1, 3-oxazolidin- 2-onas como agentes antibacterianos.

3-??4-{(alcanoil 6- substituidas) piridin-3-il}-3 -fenil!-5-(1h-1, 2, 3-triazol -1-ilmetil)-1, 3-oxazolidin- 2-onas como agentes antibacterianos.

Info

Publication number: MXPA06013537A
Authority: MX; Mexico
Prior art keywords: compound; formula; mmol; pharmaceutically acceptable; group
Prior art date: 2004-05-25

Application number

MXPA06013537A

Other languages

English (en)

Spanish (es)

Inventor

Michael Barry Gravestock

Fei Zhou

Folkert Reck

Original Assignee

Astrazeneca Ab

Priority date

2004-05-25

Filing date

2005-05-24

Publication date

2007-01-26

2004-05-25 Priority claimed from GB0411593A external-priority patent/GB0411593D0/en

2005-01-05 Priority claimed from GB0500054A external-priority patent/GB0500054D0/en

2005-05-24 Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab

2007-01-26 Publication of MXPA06013537A publication Critical patent/MXPA06013537A/es

Links

239000003242 anti bacterial agent Substances 0.000 title claims description 15
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 title description 5
125000001589 carboacyl group Chemical class 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 203
150000003839 salts Chemical class 0.000 claims abstract description 63
238000000034 method Methods 0.000 claims abstract description 50
239000000651 prodrug Substances 0.000 claims abstract description 45
229940002612 prodrug Drugs 0.000 claims abstract description 45
230000008569 process Effects 0.000 claims abstract description 28
-1 cyano, methyl Chemical group 0.000 claims description 149
125000000217 alkyl group Chemical group 0.000 claims description 69
150000002148 esters Chemical class 0.000 claims description 59
238000001727 in vivo Methods 0.000 claims description 49
238000006243 chemical reaction Methods 0.000 claims description 48
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 48
229910052757 nitrogen Inorganic materials 0.000 claims description 47
125000001424 substituent group Chemical group 0.000 claims description 47
229910052739 hydrogen Inorganic materials 0.000 claims description 40
239000001257 hydrogen Substances 0.000 claims description 39
125000003545 alkoxy group Chemical group 0.000 claims description 35
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 33
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 20
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 20
229910052794 bromium Inorganic materials 0.000 claims description 20
125000006239 protecting group Chemical group 0.000 claims description 19
125000001153 fluoro group Chemical group F* 0.000 claims description 17
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
229910052717 sulfur Inorganic materials 0.000 claims description 17
230000000844 anti-bacterial effect Effects 0.000 claims description 16
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 16
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
238000002360 preparation method Methods 0.000 claims description 15
239000008194 pharmaceutical composition Substances 0.000 claims description 14
125000003282 alkyl amino group Chemical group 0.000 claims description 13
IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical group O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 12
125000000623 heterocyclic group Chemical group 0.000 claims description 12
239000000460 chlorine Chemical group 0.000 claims description 11
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 10
241001465754 Metazoa Species 0.000 claims description 10
229910052799 carbon Inorganic materials 0.000 claims description 10
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
239000003795 chemical substances by application Substances 0.000 claims description 10
229910052801 chlorine Inorganic materials 0.000 claims description 10
125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 9
239000003814 drug Substances 0.000 claims description 9
238000004519 manufacturing process Methods 0.000 claims description 9
230000015572 biosynthetic process Effects 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
229920006395 saturated elastomer Polymers 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 7
125000005842 heteroatom Chemical group 0.000 claims description 7
125000002883 imidazolyl group Chemical group 0.000 claims description 7
241000894006 Bacteria Species 0.000 claims description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
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230000007062 hydrolysis Effects 0.000 claims description 6
238000006460 hydrolysis reaction Methods 0.000 claims description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
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125000001309 chloro group Chemical group Cl* 0.000 claims description 5
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 5
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 5
125000004434 sulfur atom Chemical group 0.000 claims description 5
150000001721 carbon Chemical group 0.000 claims description 4
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125000000753 cycloalkyl group Chemical group 0.000 claims description 4
239000003085 diluting agent Substances 0.000 claims description 4
125000002534 ethynyl group Chemical class [H]C#C* 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
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229910052760 oxygen Inorganic materials 0.000 claims description 4
150000003852 triazoles Chemical group 0.000 claims description 4
DVSMAFFYUWLENL-UHFFFAOYSA-N 3-(azidomethyl)-1,3-oxazolidin-2-one Chemical class [N-]=[N+]=NCN1CCOC1=O DVSMAFFYUWLENL-UHFFFAOYSA-N 0.000 claims description 3
241000192125 Firmicutes Species 0.000 claims description 3
230000029936 alkylation Effects 0.000 claims description 3
238000005804 alkylation reaction Methods 0.000 claims description 3
125000000304 alkynyl group Chemical group 0.000 claims description 3
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239000012038 nucleophile Substances 0.000 claims description 3
230000003647 oxidation Effects 0.000 claims description 3
238000007254 oxidation reaction Methods 0.000 claims description 3
150000002923 oximes Chemical class 0.000 claims description 3
NVZIFMAZKAYQJR-UHFFFAOYSA-N 3-(aminomethyl)-1,3-oxazolidin-2-one Chemical class NCN1CCOC1=O NVZIFMAZKAYQJR-UHFFFAOYSA-N 0.000 claims description 2
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 2
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150000001298 alcohols Chemical class 0.000 claims description 2
150000001299 aldehydes Chemical class 0.000 claims description 2
150000007942 carboxylates Chemical class 0.000 claims description 2
238000006352 cycloaddition reaction Methods 0.000 claims description 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
150000004795 grignard reagents Chemical class 0.000 claims description 2
125000001475 halogen functional group Chemical group 0.000 claims description 2
150000002443 hydroxylamines Chemical class 0.000 claims description 2
239000012948 isocyanate Substances 0.000 claims description 2
150000002513 isocyanates Chemical class 0.000 claims description 2
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239000002131 composite material Substances 0.000 claims 1
150000002460 imidazoles Chemical class 0.000 claims 1
208000035143 Bacterial infection Diseases 0.000 abstract 1
208000022362 bacterial infectious disease Diseases 0.000 abstract 1
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239000000543 intermediate Substances 0.000 description 117
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239000000047 product Substances 0.000 description 73
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 51
239000007787 solid Substances 0.000 description 50
239000000203 mixture Substances 0.000 description 49
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 46
239000000243 solution Substances 0.000 description 46
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 42
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
239000000741 silica gel Substances 0.000 description 34
229910002027 silica gel Inorganic materials 0.000 description 34
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 33
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 32
238000004587 chromatography analysis Methods 0.000 description 32
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 31
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
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125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 29
238000005481 NMR spectroscopy Methods 0.000 description 28
235000019439 ethyl acetate Nutrition 0.000 description 28
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 26
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LLPKQRMDOFYSGZ-UHFFFAOYSA-N 2,5-dimethyl-1h-imidazole Chemical compound CC1=CN=C(C)N1 LLPKQRMDOFYSGZ-UHFFFAOYSA-N 0.000 description 16
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BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
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