BG108022A - Хетероциклични съединения, притежаващи антибактериална активност, метод за тяхното получаване и фармацевтични състави , които ги съдържат - Google Patents
Хетероциклични съединения, притежаващи антибактериална активност, метод за тяхното получаване и фармацевтични състави , които ги съдържат Download PDFInfo
- Publication number
- BG108022A BG108022A BG108022A BG10802203A BG108022A BG 108022 A BG108022 A BG 108022A BG 108022 A BG108022 A BG 108022A BG 10802203 A BG10802203 A BG 10802203A BG 108022 A BG108022 A BG 108022A
- Authority
- BG
- Bulgaria
- Prior art keywords
- alkyl
- oxo
- oxazolan
- salts
- phenyl
- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 22
- 238000000034 method Methods 0.000 title claims description 90
- 238000002360 preparation method Methods 0.000 title claims description 56
- 230000008569 process Effects 0.000 title claims description 34
- 230000000844 anti-bacterial effect Effects 0.000 title description 4
- 150000002391 heterocyclic compounds Chemical class 0.000 title description 2
- 150000003839 salts Chemical class 0.000 claims abstract description 335
- 239000012453 solvate Substances 0.000 claims abstract description 28
- 150000001875 compounds Chemical class 0.000 claims description 371
- -1 pyrrolidinylthiocarbonyl Chemical group 0.000 claims description 309
- 125000000217 alkyl group Chemical group 0.000 claims description 240
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 202
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 157
- 229910052739 hydrogen Inorganic materials 0.000 claims description 142
- 239000001257 hydrogen Substances 0.000 claims description 141
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 126
- 238000006243 chemical reaction Methods 0.000 claims description 123
- 125000003118 aryl group Chemical group 0.000 claims description 103
- 125000003545 alkoxy group Chemical group 0.000 claims description 83
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 77
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 72
- 125000004104 aryloxy group Chemical group 0.000 claims description 71
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 71
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 70
- 125000005843 halogen group Chemical group 0.000 claims description 70
- 229910052717 sulfur Inorganic materials 0.000 claims description 61
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 60
- 229910052760 oxygen Inorganic materials 0.000 claims description 59
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 51
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 51
- 239000001301 oxygen Substances 0.000 claims description 51
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 50
- 239000011593 sulfur Substances 0.000 claims description 50
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 49
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 48
- 125000005842 heteroatom Chemical group 0.000 claims description 47
- 239000002585 base Substances 0.000 claims description 46
- 230000003993 interaction Effects 0.000 claims description 46
- 125000000623 heterocyclic group Chemical group 0.000 claims description 45
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 44
- 239000000243 solution Substances 0.000 claims description 44
- 125000003282 alkyl amino group Chemical group 0.000 claims description 42
- 229910052736 halogen Inorganic materials 0.000 claims description 42
- 150000002367 halogens Chemical class 0.000 claims description 40
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 36
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 36
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 34
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 34
- 229910052731 fluorine Inorganic materials 0.000 claims description 34
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 34
- 239000011737 fluorine Substances 0.000 claims description 33
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 31
- 229910052757 nitrogen Inorganic materials 0.000 claims description 31
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 30
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 29
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 29
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 125000001072 heteroaryl group Chemical group 0.000 claims description 28
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 27
- 125000001769 aryl amino group Chemical group 0.000 claims description 27
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 27
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 27
- 239000012312 sodium hydride Substances 0.000 claims description 27
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 27
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 25
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 25
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 24
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 24
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 22
- HXIRTSKHPFRRKO-UHFFFAOYSA-N o-methyl carbamothioate Chemical compound COC(N)=S HXIRTSKHPFRRKO-UHFFFAOYSA-N 0.000 claims description 20
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical class [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 19
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 19
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 15
- 101100352021 Synechococcus sp. (strain ATCC 27144 / PCC 6301 / SAUG 1402/1) cpcB1 gene Proteins 0.000 claims description 15
- 239000002253 acid Chemical class 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- 101150107228 cpcB gene Proteins 0.000 claims description 15
- 101150031932 rpcB gene Proteins 0.000 claims description 15
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 14
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 14
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 14
- 125000004685 alkoxythiocarbonyl group Chemical group 0.000 claims description 14
- 125000002252 acyl group Chemical group 0.000 claims description 13
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 13
- 150000001540 azides Chemical class 0.000 claims description 13
- 125000001153 fluoro group Chemical group F* 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 12
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 12
- 229940024606 amino acid Drugs 0.000 claims description 12
- 235000001014 amino acid Nutrition 0.000 claims description 12
- 150000001413 amino acids Chemical class 0.000 claims description 12
- 239000011591 potassium Chemical class 0.000 claims description 12
- 229910052700 potassium Inorganic materials 0.000 claims description 12
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
- 229910052727 yttrium Inorganic materials 0.000 claims description 12
- XYVMOLOUBJBNBF-UHFFFAOYSA-N 3h-1,3-oxazol-2-one Chemical compound OC1=NC=CO1 XYVMOLOUBJBNBF-UHFFFAOYSA-N 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
- 150000001412 amines Chemical class 0.000 claims description 11
- GTCAXTIRRLKXRU-UHFFFAOYSA-N carbamic acid methyl ester Natural products COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims description 11
- ZWWAJMUJXCLKDI-UHFFFAOYSA-N ethylsulfanyl carbamate Chemical compound C(N)(=O)OSCC ZWWAJMUJXCLKDI-UHFFFAOYSA-N 0.000 claims description 11
- 150000002540 isothiocyanates Chemical class 0.000 claims description 11
- 208000035143 Bacterial infection Diseases 0.000 claims description 10
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical class [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 10
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 10
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 10
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 10
- 125000004122 cyclic group Chemical group 0.000 claims description 10
- ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine group Chemical group NC(=N)N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 10
- 229910052725 zinc Inorganic materials 0.000 claims description 10
- 239000011701 zinc Chemical class 0.000 claims description 10
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 9
- 125000004423 acyloxy group Chemical group 0.000 claims description 9
- 239000003085 diluting agent Substances 0.000 claims description 9
- ZBKFYXZXZJPWNQ-UHFFFAOYSA-N isothiocyanate group Chemical group [N-]=C=S ZBKFYXZXZJPWNQ-UHFFFAOYSA-N 0.000 claims description 9
- 125000000464 thioxo group Chemical group S=* 0.000 claims description 9
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 claims description 8
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 8
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical class C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 7
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- 238000007796 conventional method Methods 0.000 claims description 7
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- 239000000725 suspension Substances 0.000 claims description 7
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims description 6
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Chemical group CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 6
- DTVYJEZONVDDBF-UHFFFAOYSA-N OSN=[N+]=[N-] Chemical compound OSN=[N+]=[N-] DTVYJEZONVDDBF-UHFFFAOYSA-N 0.000 claims description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
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- 239000011575 calcium Chemical class 0.000 claims description 6
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Chemical group CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- 229910052742 iron Inorganic materials 0.000 claims description 6
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052720 vanadium Inorganic materials 0.000 claims description 6
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 5
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 5
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- 241000894006 Bacteria Species 0.000 claims description 5
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- 241000894007 species Species 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 1
- DUYAAUVXQSMXQP-UHFFFAOYSA-M thioacetate Chemical compound CC([S-])=O DUYAAUVXQSMXQP-UHFFFAOYSA-M 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 125000005505 thiomorpholino group Chemical group 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
- C07D263/22—Oxygen atoms attached in position 2 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to other ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
- C07D263/24—Oxygen atoms attached in position 2 with hydrocarbon radicals, substituted by oxygen atoms, attached to other ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN1124MA2000 | 2000-12-26 | ||
| IN15MA2001 | 2001-01-15 | ||
| PCT/IN2001/000227 WO2002051819A2 (en) | 2000-12-26 | 2001-12-26 | Heterocyclic compounds having antibacterial activity, process for their preparation and pharmaceutical compositions containing them |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BG108022A true BG108022A (bg) | 2004-09-30 |
Family
ID=26324889
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG108022A BG108022A (bg) | 2000-12-26 | 2003-07-22 | Хетероциклични съединения, притежаващи антибактериална активност, метод за тяхното получаване и фармацевтични състави , които ги съдържат |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US7030148B2 (da) |
| EP (1) | EP1345913A2 (da) |
| JP (1) | JP2004525876A (da) |
| KR (1) | KR20030063472A (da) |
| CN (1) | CN1656083A (da) |
| BG (1) | BG108022A (da) |
| BR (1) | BR0116571A (da) |
| CA (1) | CA2433138A1 (da) |
| CZ (1) | CZ20031799A3 (da) |
| EE (1) | EE200300254A (da) |
| HR (1) | HRP20030522A2 (da) |
| HU (1) | HUP0302580A2 (da) |
| IL (1) | IL156662A0 (da) |
| MX (1) | MXPA03005822A (da) |
| NO (1) | NO20032926L (da) |
| NZ (1) | NZ526716A (da) |
| PL (1) | PL363616A1 (da) |
| RU (1) | RU2322444C2 (da) |
| SK (1) | SK8202003A3 (da) |
| WO (1) | WO2002051819A2 (da) |
| YU (1) | YU52403A (da) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MXPA04002303A (es) | 2001-09-11 | 2004-06-29 | Astrazeneca Ab | Oxazolidinona y/o isoxazolina como agentes antibacterianos. |
| US20070004712A1 (en) * | 2001-12-21 | 2007-01-04 | Dr. Reddy's Laboratories Ltd. | Salts of novel heterocyclic compounds having antibacterial activity |
| US6914058B2 (en) * | 2002-01-18 | 2005-07-05 | Dr. Reddy's Laboratories, Limited | Antibacterial compounds: process for their preparation and pharmaceutical compositions containing them |
| DE10233817A1 (de) * | 2002-07-25 | 2004-02-12 | Aventis Pharma Deutschland Gmbh | Substituierte Diarylheterocyclen, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| US7141561B2 (en) | 2002-07-25 | 2006-11-28 | Sanofi-Aventis Deutschland Gmbh | Substituted diaryl heterocycles, process for their preparation and their use as medicaments |
| US20080214565A1 (en) * | 2003-04-07 | 2008-09-04 | Anita Mehta | Oxazolidinone Derivatives as Antimicrobials |
| KR20060113625A (ko) | 2003-07-02 | 2006-11-02 | 머크 앤드 캄파니 인코포레이티드 | 시클로프로필기 치환된 옥사졸리디논 항생제 및 그의유도체 |
| JP2007521283A (ja) * | 2003-07-02 | 2007-08-02 | メルク アンド カンパニー インコーポレーテッド | シクロプロピル基で置換されたオキサゾリジノン系抗生物質およびその誘導体 |
| WO2005035528A2 (en) * | 2003-10-14 | 2005-04-21 | Dr. Reddy's Laboratories Ltd. | Triazole derivatives as antibacterial agents |
| KR100854211B1 (ko) | 2003-12-18 | 2008-08-26 | 동아제약주식회사 | 신규한 옥사졸리디논 유도체, 그의 제조방법 및 이를유효성분으로 하는 항생제용 약학 조성물 |
| CA2602073A1 (en) * | 2005-02-24 | 2006-08-31 | Teva Pharmaceutical Industries Ltd. | Processes for the preparation of linezolid intermediate |
| ES2524922T3 (es) | 2005-05-10 | 2014-12-15 | Intermune, Inc. | Derivados de piridona para modular el sistema de proteína cinasa activada por estrés |
| EP2185549B1 (en) * | 2007-08-06 | 2018-10-03 | Micurx Pharmaceuticals, Inc. | Antimicrobial ortho-fluorophenyl oxazolidinones for treatment of bacterial infections |
| US8304413B2 (en) | 2008-06-03 | 2012-11-06 | Intermune, Inc. | Compounds and methods for treating inflammatory and fibrotic disorders |
| US9540322B2 (en) | 2008-08-18 | 2017-01-10 | Yale University | MIF modulators |
| EP2326631A4 (en) * | 2008-08-18 | 2012-03-21 | Univ Yale | MODULATORS OF MIF |
| US9643922B2 (en) | 2008-08-18 | 2017-05-09 | Yale University | MIF modulators |
| KR101739923B1 (ko) | 2009-02-03 | 2017-05-25 | 머크 샤프 앤드 돔 코포레이션 | Ｒ)-3-(4-(2-(2-메틸테트라졸-5-일)피리딘-5-일)-3-플루오로페닐)-5-히드록시메틸 옥사졸리딘-2-온 디히드로겐 포스페이트의 결정형 |
| CN101798302B (zh) * | 2009-02-06 | 2014-11-05 | 上海盟科药业有限公司 | 抗生素类药物1-(邻-氟苯基)二氢吡啶酮的合成及生产的方法和工艺 |
| WO2014045292A1 (en) * | 2012-09-20 | 2014-03-27 | Symed Labs Limited | Improved process for the preparation of linezolid intermediate |
| AR092742A1 (es) | 2012-10-02 | 2015-04-29 | Intermune Inc | Piridinonas antifibroticas |
| ES2900838T3 (es) | 2014-02-21 | 2022-03-18 | Shanghai Micurx Pharmaceutical Co Ltd | Profármacos de O-carbonil fosforamidato solubles en agua para administración terapéutica |
| CA2943363A1 (en) | 2014-04-02 | 2015-10-08 | Intermune, Inc. | Anti-fibrotic pyridinones |
| GB2550437B (en) * | 2016-05-20 | 2021-06-23 | Bugworks Res Inc | Heterocyclic compounds useful as anti-bacterial agents and method for production |
| US20210267953A1 (en) | 2018-07-25 | 2021-09-02 | Cadila Healthcare Limited | Substituted oxazolidinones for the treatment of mammalian infections |
| WO2020234636A1 (en) | 2019-05-17 | 2020-11-26 | Cadila Healthcare Limited | Novel compounds for the treatment of mammalian infections |
| CN110301433A (zh) * | 2019-07-25 | 2019-10-08 | 河南精怡达生物科技有限公司 | 一种含有微量元素组合的猪精液体外常温保存剂 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2987505A (en) * | 1958-03-04 | 1961-06-06 | Gen Aniline & Film Corp | Compositions of polymeric nu-vinyl-2-oxazolidone and halogens |
| US3651079A (en) | 1968-11-25 | 1972-03-21 | Colgate Palmolive Co | 1-aryl-5-hydroxyalkyl-hydantoins |
| GB1408010A (en) | 1972-11-20 | 1975-10-01 | Geistlich Soehne Ag | Sulphamoylphenyl-imidazolidinones |
| US4174958A (en) | 1978-01-09 | 1979-11-20 | Shell Oil Company | Anilide derivative herbicides |
| FR2571364B1 (fr) * | 1984-10-09 | 1987-07-17 | Oreal | Nouveau procede de preparation de nitroparaphenylenediamines n,n'-disubstituees, nouvelles oxazolidones utilisees dans ce procede, nouvelles nitroparaphenylenediamines n,n'-disubstituees obtenues selon ce procede et compositions tinctoriales contenant les nitroparaphenylenediamines n,n'-disubstituees obtenues selon ledit procede |
| MY115155A (en) | 1993-09-09 | 2003-04-30 | Upjohn Co | Substituted oxazine and thiazine oxazolidinone antimicrobials. |
| EP0788498B1 (en) | 1994-10-26 | 2001-08-16 | PHARMACIA & UPJOHN COMPANY | Phenyloxazolidinone antimicrobials |
| US6124334A (en) | 1995-02-03 | 2000-09-26 | Pharmacia & Upjohn Company | Hetero-aromatic ring substituted phenyloxazolidinone antimicrobials |
| GB9601666D0 (en) | 1996-01-27 | 1996-03-27 | Zeneca Ltd | Chemical compounds |
| US6087496A (en) * | 1998-05-22 | 2000-07-11 | G. D. Searle & Co. | Substituted pyrazoles suitable as p38 kinase inhibitors |
| JPH11322729A (ja) * | 1998-03-09 | 1999-11-24 | Hokuriku Seiyaku Co Ltd | ジチオカルバミド酸誘導体 |
| NZ516853A (en) | 1999-07-28 | 2003-11-28 | Upjohn Co | Oxazolidinones and their use as anti-infectives |
| GB0118407D0 (en) | 2001-07-27 | 2001-09-19 | Cipla Ltd | Oxazolidinone derivatives as antibacterial agents |
-
2001
- 2001-11-26 YU YU52403A patent/YU52403A/sh unknown
- 2001-12-21 US US10/032,392 patent/US7030148B2/en not_active Expired - Fee Related
- 2001-12-26 KR KR10-2003-7008637A patent/KR20030063472A/ko not_active Application Discontinuation
- 2001-12-26 NZ NZ526716A patent/NZ526716A/en unknown
- 2001-12-26 MX MXPA03005822A patent/MXPA03005822A/es not_active Application Discontinuation
- 2001-12-26 WO PCT/IN2001/000227 patent/WO2002051819A2/en active IP Right Grant
- 2001-12-26 JP JP2002552914A patent/JP2004525876A/ja not_active Withdrawn
- 2001-12-26 EE EEP200300254A patent/EE200300254A/xx unknown
- 2001-12-26 SK SK820-2003A patent/SK8202003A3/sk not_active Application Discontinuation
- 2001-12-26 IL IL15666201A patent/IL156662A0/xx unknown
- 2001-12-26 RU RU2003123104/04A patent/RU2322444C2/ru not_active IP Right Cessation
- 2001-12-26 PL PL01363616A patent/PL363616A1/xx not_active Application Discontinuation
- 2001-12-26 CN CNA018224210A patent/CN1656083A/zh active Pending
- 2001-12-26 CA CA002433138A patent/CA2433138A1/en not_active Abandoned
- 2001-12-26 BR BR0116571-2A patent/BR0116571A/pt not_active IP Right Cessation
- 2001-12-26 HU HU0302580A patent/HUP0302580A2/hu unknown
- 2001-12-26 CZ CZ20031799A patent/CZ20031799A3/cs unknown
- 2001-12-26 EP EP01995805A patent/EP1345913A2/en not_active Withdrawn
-
2003
- 2003-06-25 NO NO20032926A patent/NO20032926L/no unknown
- 2003-06-26 HR HR20030522A patent/HRP20030522A2/hr not_active Application Discontinuation
- 2003-07-22 BG BG108022A patent/BG108022A/bg unknown
- 2003-08-01 US US10/632,950 patent/US7183301B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US7030148B2 (en) | 2006-04-18 |
| WO2002051819A9 (en) | 2003-08-07 |
| HUP0302580A2 (hu) | 2003-11-28 |
| WO2002051819A2 (en) | 2002-07-04 |
| US20040059120A1 (en) | 2004-03-25 |
| NO20032926L (no) | 2003-08-25 |
| EP1345913A2 (en) | 2003-09-24 |
| JP2004525876A (ja) | 2004-08-26 |
| CA2433138A1 (en) | 2002-07-04 |
| MXPA03005822A (es) | 2004-05-04 |
| YU52403A (sh) | 2006-03-03 |
| IL156662A0 (en) | 2004-01-04 |
| US7183301B2 (en) | 2007-02-27 |
| BR0116571A (pt) | 2004-03-02 |
| SK8202003A3 (en) | 2004-07-07 |
| RU2003123104A (ru) | 2005-03-10 |
| PL363616A1 (en) | 2004-11-29 |
| CZ20031799A3 (cs) | 2004-02-18 |
| HRP20030522A2 (en) | 2005-06-30 |
| KR20030063472A (ko) | 2003-07-28 |
| NO20032926D0 (no) | 2003-06-25 |
| EE200300254A (et) | 2003-12-15 |
| RU2322444C2 (ru) | 2008-04-20 |
| US20030065175A1 (en) | 2003-04-03 |
| CN1656083A (zh) | 2005-08-17 |
| NZ526716A (en) | 2005-08-26 |
| WO2002051819A3 (en) | 2002-12-05 |
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