NO311026B1 - Benzoxazinforbindelser, mellomprodukter for fremstilling av forbindelsene, anvendelse av forbindelsene samt farmasoytiskepreparater inneholdende disse og fremgangsmater for fremstillingav mellomprodukter og sluttprodukt - Google Patents

Info

Publication number

NO311026B1

NO311026B1 NO19982071A NO982071A NO311026B1 NO 311026 B1 NO311026 B1 NO 311026B1 NO 19982071 A NO19982071 A NO 19982071A NO 982071 A NO982071 A NO 982071A NO 311026 B1 NO311026 B1 NO 311026B1

Authority

NO

Norway

Prior art keywords

dihydro

oxo

ethyl

benzoxazine

phenoxy

Prior art date

1995-11-07

Links

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• 238000000034 method Methods 0.000 title claims abstract description 299
• 150000001875 compounds Chemical class 0.000 title claims abstract description 155
• 238000002360 preparation method Methods 0.000 title claims abstract description 15
• 239000000825 pharmaceutical preparation Substances 0.000 title claims description 7
• 239000000543 intermediate Substances 0.000 title description 208
• 150000005130 benzoxazines Chemical class 0.000 title description 4
• 239000007795 chemical reaction product Substances 0.000 title 1
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 30
• 125000004076 pyridyl group Chemical group 0.000 claims abstract description 16
• 208000035143 Bacterial infection Diseases 0.000 claims abstract description 8
• 208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 8
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
• 239000000460 chlorine Substances 0.000 claims description 88
• -1 hydroxy, amino, nitro, sulfonylamino Chemical group 0.000 claims description 80
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 70
• 229910052739 hydrogen Inorganic materials 0.000 claims description 49
• 239000001257 hydrogen Substances 0.000 claims description 47
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 44
• 229910052736 halogen Inorganic materials 0.000 claims description 27
• 150000002367 halogens Chemical class 0.000 claims description 27
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
• 239000003153 chemical reaction reagent Substances 0.000 claims description 23
• 150000002431 hydrogen Chemical class 0.000 claims description 20
• 239000002904 solvent Substances 0.000 claims description 16
• 125000000623 heterocyclic group Chemical group 0.000 claims description 13
• 150000003839 salts Chemical class 0.000 claims description 13
• 125000003545 alkoxy group Chemical group 0.000 claims description 12
• 238000004519 manufacturing process Methods 0.000 claims description 12
• 125000003118 aryl group Chemical group 0.000 claims description 11
• 125000006239 protecting group Chemical group 0.000 claims description 11
• 239000003242 anti bacterial agent Substances 0.000 claims description 10
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 10
• 150000002148 esters Chemical group 0.000 claims description 10
• 125000000217 alkyl group Chemical group 0.000 claims description 9
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
• 230000000694 effects Effects 0.000 claims description 9
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
• XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 6
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
• 229910052760 oxygen Chemical group 0.000 claims description 6
• 239000001301 oxygen Chemical group 0.000 claims description 6
• 229920006395 saturated elastomer Polymers 0.000 claims description 6
• 235000010290 biphenyl Nutrition 0.000 claims description 5
• 239000004305 biphenyl Substances 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 125000001624 naphthyl group Chemical group 0.000 claims description 5
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
• 239000000651 prodrug Chemical group 0.000 claims description 5
• 229940002612 prodrug Drugs 0.000 claims description 5
• PEQTWPXGHVVXGR-UHFFFAOYSA-N 2-[2-[4-[2-[4-[(3-chlorophenyl)methyl]-2,3-dihydro-1,4-benzoxazin-2-yl]ethoxy]phenyl]ethyl]guanidine Chemical group C1=CC(CCNC(=N)N)=CC=C1OCCC1OC2=CC=CC=C2N(CC=2C=C(Cl)C=CC=2)C1 PEQTWPXGHVVXGR-UHFFFAOYSA-N 0.000 claims description 4
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
• 125000001544 thienyl group Chemical group 0.000 claims description 4
• 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 3
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
• 241000124008 Mammalia Species 0.000 claims description 3
• 229910052801 chlorine Inorganic materials 0.000 claims description 3
• 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 3
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
• ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 claims description 2
• AFTLZUKZGUJHJD-UHFFFAOYSA-N 2-[2-[3-(2-aminoethyl)phenoxy]ethyl]-4-[(3-chlorophenyl)methyl]-1,4-benzoxazin-3-one Chemical group NCCC1=CC=CC(OCCC2C(N(CC=3C=C(Cl)C=CC=3)C3=CC=CC=C3O2)=O)=C1 AFTLZUKZGUJHJD-UHFFFAOYSA-N 0.000 claims description 2
• XYTUAOCLEGEKFE-UHFFFAOYSA-N 2-[2-[4-(3-aminopropyl)phenoxy]ethyl]-4-[(3-chlorophenyl)methyl]-1,4-benzoxazin-3-one Chemical group C1=CC(CCCN)=CC=C1OCCC1C(=O)N(CC=2C=C(Cl)C=CC=2)C2=CC=CC=C2O1 XYTUAOCLEGEKFE-UHFFFAOYSA-N 0.000 claims description 2
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• KSUJMWIHBHAWKU-UHFFFAOYSA-N 2-[2-[4-[2-[4-[(2-chlorophenyl)methyl]-7-nitro-3-oxo-1,4-benzoxazin-2-yl]ethoxy]phenyl]ethyl]guanidine;hydrochloride Chemical group Cl.C1=CC(CCNC(=N)N)=CC=C1OCCC1C(=O)N(CC=2C(=CC=CC=2)Cl)C2=CC=C([N+]([O-])=O)C=C2O1 KSUJMWIHBHAWKU-UHFFFAOYSA-N 0.000 claims description 2
• FZCZBCOJKQKMSH-UHFFFAOYSA-N 2-[2-[4-[2-[4-[(3,5-dichlorophenyl)methyl]-3-oxo-1,4-benzoxazin-2-yl]ethoxy]phenyl]ethyl]guanidine Chemical group C1=CC(CCNC(=N)N)=CC=C1OCCC1C(=O)N(CC=2C=C(Cl)C=C(Cl)C=2)C2=CC=CC=C2O1 FZCZBCOJKQKMSH-UHFFFAOYSA-N 0.000 claims description 2
• GKZORROYVNHIDV-UHFFFAOYSA-N 2-[2-[4-[2-[4-[(3-chlorophenyl)methyl]-7-methyl-3-oxo-1,4-benzoxazin-2-yl]ethoxy]phenyl]ethyl]guanidine Chemical group O=C1C(CCOC=2C=CC(CCNC(N)=N)=CC=2)OC2=CC(C)=CC=C2N1CC1=CC=CC(Cl)=C1 GKZORROYVNHIDV-UHFFFAOYSA-N 0.000 claims description 2
• LHTQFOLMNYNINE-UHFFFAOYSA-N 2-[2-[4-[2-[6,8-dichloro-4-[(3-chlorophenyl)methyl]-3-oxo-1,4-benzoxazin-2-yl]ethoxy]phenyl]ethyl]guanidine Chemical group C1=CC(CCNC(=N)N)=CC=C1OCCC1C(=O)N(CC=2C=C(Cl)C=CC=2)C2=CC(Cl)=CC(Cl)=C2O1 LHTQFOLMNYNINE-UHFFFAOYSA-N 0.000 claims description 2
• NJTXWHXHTPSMIL-UHFFFAOYSA-N 2-[2-[4-[2-[6-chloro-4-[(3-chlorophenyl)methyl]-3-oxo-1,4-benzoxazin-2-yl]ethoxy]phenyl]ethyl]guanidine Chemical group C1=CC(CCNC(=N)N)=CC=C1OCCC1C(=O)N(CC=2C=C(Cl)C=CC=2)C2=CC(Cl)=CC=C2O1 NJTXWHXHTPSMIL-UHFFFAOYSA-N 0.000 claims description 2
• SGVXWYRAXYUXMC-UHFFFAOYSA-N 2-[[4-[2-[4-[(2-chlorophenyl)methyl]-3-oxo-1,4-benzoxazin-2-yl]ethoxy]phenyl]methyl]guanidine Chemical group C1=CC(CNC(=N)N)=CC=C1OCCC1C(=O)N(CC=2C(=CC=CC=2)Cl)C2=CC=CC=C2O1 SGVXWYRAXYUXMC-UHFFFAOYSA-N 0.000 claims description 2
• BZMMDJUOTBZYAR-UHFFFAOYSA-N 2-[[4-[2-[4-[(3-chlorophenyl)methyl]-2,3-dihydro-1,4-benzoxazin-2-yl]ethoxy]phenyl]methyl]guanidine Chemical group C1=CC(CNC(=N)N)=CC=C1OCCC1OC2=CC=CC=C2N(CC=2C=C(Cl)C=CC=2)C1 BZMMDJUOTBZYAR-UHFFFAOYSA-N 0.000 claims description 2
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 2
• WHMWQSDQFVKZJR-UHFFFAOYSA-N 2-[2-[4-[2-[4-[(3-chlorophenyl)methyl]-3-oxopyrido[3,2-b][1,4]oxazin-2-yl]ethoxy]phenyl]ethyl]guanidine Chemical group C1=CC(CCNC(=N)N)=CC=C1OCCC1C(=O)N(CC=2C=C(Cl)C=CC=2)C2=NC=CC=C2O1 WHMWQSDQFVKZJR-UHFFFAOYSA-N 0.000 claims 1
• MQUFRUVUSXAXTF-UHFFFAOYSA-N 2-[2-[4-[2-[6-nitro-4-[(2-nitrophenyl)methyl]-3-oxo-1,4-benzoxazin-2-yl]ethoxy]phenyl]ethyl]guanidine Chemical group C1=CC(CCN=C(N)N)=CC=C1OCCC1C(=O)N(CC=2C(=CC=CC=2)[N+]([O-])=O)C2=CC([N+]([O-])=O)=CC=C2O1 MQUFRUVUSXAXTF-UHFFFAOYSA-N 0.000 claims 1
• 101100439663 Arabidopsis thaliana CHR7 gene Proteins 0.000 claims 1
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• 229910052717 sulfur Inorganic materials 0.000 claims 1
• 125000004434 sulfur atom Chemical group 0.000 claims 1
• SHASOVNNKCSWPT-UHFFFAOYSA-N 2h-pyrido[2,3-e]oxazine Chemical compound C1=CN=C2C=CNOC2=C1 SHASOVNNKCSWPT-UHFFFAOYSA-N 0.000 abstract description 5
• 230000000844 anti-bacterial effect Effects 0.000 abstract description 5
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