BR112014027190B1 - Composto de pirrolobenzodiazepinas, sua composição farmacêutica e seu uso - Google Patents

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Publication number

BR112014027190B1

BR112014027190B1 BR112014027190-9A BR112014027190A BR112014027190B1 BR 112014027190 B1 BR112014027190 B1 BR 112014027190B1 BR 112014027190 A BR112014027190 A BR 112014027190A BR 112014027190 B1 BR112014027190 B1 BR 112014027190B1

Authority

BR

Brazil

Prior art keywords

nme

group

alkyl

petition

phenyl

Prior art date

2012-04-30

Links

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 85
• 239000008194 pharmaceutical composition Substances 0.000 title claims description 8
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 33
• 239000001257 hydrogen Substances 0.000 claims abstract description 17
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
• 150000003839 salts Chemical class 0.000 claims abstract description 15
• 239000012453 solvate Substances 0.000 claims abstract description 12
• 125000005549 heteroarylene group Chemical group 0.000 claims abstract description 8
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 7
• -1 4-ethoxy-phenyl Chemical group 0.000 claims description 96
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 52
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
• 229910052757 nitrogen Inorganic materials 0.000 claims description 22
• 229910052717 sulfur Inorganic materials 0.000 claims description 19
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 15
• 208000035143 Bacterial infection Diseases 0.000 claims description 14
• 208000022362 bacterial infectious disease Diseases 0.000 claims description 12
• 125000004432 carbon atom Chemical group C* 0.000 claims description 10
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 10
• 125000006592 (C2-C3) alkenyl group Chemical group 0.000 claims description 8
• 125000006593 (C2-C3) alkynyl group Chemical group 0.000 claims description 8
• 239000003814 drug Substances 0.000 claims description 8
• 125000004076 pyridyl group Chemical group 0.000 claims description 8
• 229940079593 drug Drugs 0.000 claims description 7
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 7
• 229910052760 oxygen Inorganic materials 0.000 claims description 7
• 125000001544 thienyl group Chemical group 0.000 claims description 6
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 4
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
• 125000001624 naphthyl group Chemical group 0.000 claims description 3
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 2
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 2
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
• 125000001931 aliphatic group Chemical group 0.000 claims description 2
• 238000004519 manufacturing process Methods 0.000 claims description 2
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
• 125000003118 aryl group Chemical group 0.000 abstract description 56
• 125000000623 heterocyclic group Chemical group 0.000 abstract description 48
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 7
• 150000001768 cations Chemical class 0.000 abstract description 6
• PIEXCQIOSMOEOU-UHFFFAOYSA-N 1-bromo-3-chloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Br)C(=O)N(Cl)C1=O PIEXCQIOSMOEOU-UHFFFAOYSA-N 0.000 abstract description 2
• 125000001475 halogen functional group Chemical group 0.000 abstract 2
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 74
• 125000006701 (C1-C7) alkyl group Chemical group 0.000 description 64
• 238000005481 NMR spectroscopy Methods 0.000 description 47
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 34
• 239000000243 solution Substances 0.000 description 34
• 125000001424 substituent group Chemical group 0.000 description 33
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
• 238000006243 chemical reaction Methods 0.000 description 31
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 28
• 235000019439 ethyl acetate Nutrition 0.000 description 28
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 24
• 239000000203 mixture Substances 0.000 description 24
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 22
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• 239000011541 reaction mixture Substances 0.000 description 21
• 238000004809 thin layer chromatography Methods 0.000 description 21
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 20
• 238000000034 method Methods 0.000 description 18
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 17
• 125000006413 ring segment Chemical group 0.000 description 17
• 125000003277 amino group Chemical group 0.000 description 16
• 239000007787 solid Substances 0.000 description 16
• 239000000126 substance Substances 0.000 description 16
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 15
• 238000011282 treatment Methods 0.000 description 15
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 14
• 239000003242 anti bacterial agent Substances 0.000 description 14
• 125000005843 halogen group Chemical group 0.000 description 14
• 229940088710 antibiotic agent Drugs 0.000 description 13
• 239000002904 solvent Substances 0.000 description 13
• 239000002253 acid Substances 0.000 description 12
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 12
• 235000019341 magnesium sulphate Nutrition 0.000 description 12
• 230000015572 biosynthetic process Effects 0.000 description 11
• 230000002829 reductive effect Effects 0.000 description 11
• 238000003756 stirring Methods 0.000 description 11
• 239000012267 brine Substances 0.000 description 10
• 238000010511 deprotection reaction Methods 0.000 description 10
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
• 229920006395 saturated elastomer Polymers 0.000 description 9
• 108020004414 DNA Proteins 0.000 description 8
• 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 8
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
• 125000004093 cyano group Chemical group *C#N 0.000 description 8
• 238000003818 flash chromatography Methods 0.000 description 8
• 150000002431 hydrogen Chemical class 0.000 description 8
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
• YMXFJTUQQVLJEN-UHFFFAOYSA-N pyrimidine Chemical compound C1=CN=CN=C1.C1=CN=CN=C1 YMXFJTUQQVLJEN-UHFFFAOYSA-N 0.000 description 8
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 7
• 229960000549 4-dimethylaminophenol Drugs 0.000 description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
• 230000000844 anti-bacterial effect Effects 0.000 description 7
• 239000012043 crude product Substances 0.000 description 7
• 125000004122 cyclic group Chemical group 0.000 description 7
• 201000010099 disease Diseases 0.000 description 7
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
• 150000002148 esters Chemical class 0.000 description 7
• 239000000543 intermediate Substances 0.000 description 7
• 239000000047 product Substances 0.000 description 7
• 238000002560 therapeutic procedure Methods 0.000 description 7
• QERYCTSHXKAMIS-UHFFFAOYSA-M thiophene-2-carboxylate Chemical compound [O-]C(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-M 0.000 description 7
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 6
• HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 6
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
• XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 6
• ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 6
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
• 230000008878 coupling Effects 0.000 description 6
• 238000010168 coupling process Methods 0.000 description 6
• 238000005859 coupling reaction Methods 0.000 description 6
• QWHNJUXXYKPLQM-UHFFFAOYSA-N dimethyl cyclopentane Natural products CC1(C)CCCC1 QWHNJUXXYKPLQM-UHFFFAOYSA-N 0.000 description 6
• 230000000694 effects Effects 0.000 description 6
• 238000002451 electron ionisation mass spectrometry Methods 0.000 description 6
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• 239000000284 extract Substances 0.000 description 6
• GHCAUEMXBSLMGU-UHFFFAOYSA-N oxadiazole;1,2,5-oxadiazole Chemical compound C=1C=NON=1.C1=CON=N1 GHCAUEMXBSLMGU-UHFFFAOYSA-N 0.000 description 6
• 238000003786 synthesis reaction Methods 0.000 description 6
• GIFDVQUOPKITFR-UHFFFAOYSA-N 1-methyl-4-[4-[(2-methylpropan-2-yl)oxycarbonylamino]phenyl]pyrrole-2-carboxylic acid Chemical compound C1=C(C(O)=O)N(C)C=C1C1=CC=C(NC(=O)OC(C)(C)C)C=C1 GIFDVQUOPKITFR-UHFFFAOYSA-N 0.000 description 5
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
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• 108010059993 Vancomycin Proteins 0.000 description 5
• 238000003556 assay Methods 0.000 description 5
• 230000001580 bacterial effect Effects 0.000 description 5
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 5
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• 238000002474 experimental method Methods 0.000 description 5
• 125000005842 heteroatom Chemical group 0.000 description 5
• RUZLIIJDZBWWSA-INIZCTEOSA-N methyl 2-[[(1s)-1-(7-methyl-2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)ethyl]amino]benzoate Chemical group COC(=O)C1=CC=CC=C1N[C@@H](C)C1=CC(C)=CN2C(=O)C=C(N3CCOCC3)N=C12 RUZLIIJDZBWWSA-INIZCTEOSA-N 0.000 description 5
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• SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 4
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