NO791699L - Benzylpyrimidinforbindelser og fremgangsmaate til deres fremstilling - Google Patents

Benzylpyrimidinforbindelser og fremgangsmaate til deres fremstilling

Info

Publication number: NO791699L
Authority: NO; Norway
Prior art keywords: formula; group; acid; compound; compounds
Prior art date: 1978-05-24

Application number

NO791699A

Other languages

English (en)

Norwegian (no)

Inventor

Stanley Robert Morris Bushby

James Joseph Burgchall

Original Assignee

Wellcome Found

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.)

1978-05-24

Filing date

1979-05-23

Publication date

1979-11-27

1979-05-23 Application filed by Wellcome Found filed Critical Wellcome Found

1979-11-27 Publication of NO791699L publication Critical patent/NO791699L/no

Links

238000000034 method Methods 0.000 title claims description 13
238000002360 preparation method Methods 0.000 title description 13
OOLOAWZLPBDRJQ-UHFFFAOYSA-N 2-benzylpyrimidine Chemical class N=1C=CC=NC=1CC1=CC=CC=C1 OOLOAWZLPBDRJQ-UHFFFAOYSA-N 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 90
150000003839 salts Chemical class 0.000 claims description 19
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 17
125000000217 alkyl group Chemical group 0.000 claims description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
125000005843 halogen group Chemical group 0.000 claims description 12
125000003277 amino group Chemical group 0.000 claims description 11
238000007327 hydrogenolysis reaction Methods 0.000 claims description 10
239000000825 pharmaceutical preparation Substances 0.000 claims description 10
125000006239 protecting group Chemical group 0.000 claims description 9
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 5
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 claims description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
125000004414 alkyl thio group Chemical group 0.000 claims description 4
125000004659 aryl alkyl thio group Chemical group 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 4
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 3
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 3
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
150000002357 guanidines Chemical class 0.000 claims description 3
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 2
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 2
230000003197 catalytic effect Effects 0.000 claims description 2
235000015165 citric acid Nutrition 0.000 claims description 2
239000001530 fumaric acid Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
239000004310 lactic acid Substances 0.000 claims description 2
235000014655 lactic acid Nutrition 0.000 claims description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
239000011976 maleic acid Substances 0.000 claims description 2
238000002156 mixing Methods 0.000 claims description 2
KHPXUQMNIQBQEV-UHFFFAOYSA-N oxaloacetic acid Chemical compound OC(=O)CC(=O)C(O)=O KHPXUQMNIQBQEV-UHFFFAOYSA-N 0.000 claims description 2
150000002989 phenols Chemical class 0.000 claims description 2
235000011007 phosphoric acid Nutrition 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
229940107700 pyruvic acid Drugs 0.000 claims description 2
239000011975 tartaric acid Substances 0.000 claims description 2
235000002906 tartaric acid Nutrition 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 3
CEXKXUHVXAGOLB-UHFFFAOYSA-N 5-[[2-(3-bromoanilino)pyrimidin-4-yl]amino]-2-methylphenol Chemical compound C1=C(O)C(C)=CC=C1NC1=CC=NC(NC=2C=C(Br)C=CC=2)=N1 CEXKXUHVXAGOLB-UHFFFAOYSA-N 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 23
-1 s- butyl Chemical group 0.000 description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 15
239000000203 mixture Substances 0.000 description 13
239000000243 solution Substances 0.000 description 13
239000002904 solvent Substances 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 12
239000002244 precipitate Substances 0.000 description 11
239000000047 product Substances 0.000 description 10
229940124530 sulfonamide Drugs 0.000 description 9
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
239000008280 blood Substances 0.000 description 7
208000015181 infectious disease Diseases 0.000 description 7
150000003456 sulfonamides Chemical class 0.000 description 7
UUSSTJBDWHEZEH-UHFFFAOYSA-N 2,6-ditert-butyl-4-[(2,4-diaminopyrimidin-5-yl)methyl]phenol Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CC=2C(=NC(N)=NC=2)N)=C1 UUSSTJBDWHEZEH-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 6
239000002253 acid Substances 0.000 description 6
210000004369 blood Anatomy 0.000 description 6
239000003085 diluting agent Substances 0.000 description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
238000004809 thin layer chromatography Methods 0.000 description 6
238000005481 NMR spectroscopy Methods 0.000 description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
239000007787 solid Substances 0.000 description 5
IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 description 5
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 4
XHPZVBGIPQQTQW-UHFFFAOYSA-N 5-benzylpyrimidine-2,4-diamine Chemical class NC1=NC(N)=NC=C1CC1=CC=CC=C1 XHPZVBGIPQQTQW-UHFFFAOYSA-N 0.000 description 4
208000035143 Bacterial infection Diseases 0.000 description 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
241000588653 Neisseria Species 0.000 description 4
241000588652 Neisseria gonorrhoeae Species 0.000 description 4
241000588650 Neisseria meningitidis Species 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 4
238000005903 acid hydrolysis reaction Methods 0.000 description 4
208000022362 bacterial infectious disease Diseases 0.000 description 4
239000012362 glacial acetic acid Substances 0.000 description 4
238000001727 in vivo Methods 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
150000003230 pyrimidines Chemical class 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
229960001082 trimethoprim Drugs 0.000 description 4
ARFVBOLTPMSBQA-UHFFFAOYSA-N 2,6-ditert-butyl-4-[(2,4-dichloropyrimidin-5-yl)methyl]phenol Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CC=2C(=NC(Cl)=NC=2)Cl)=C1 ARFVBOLTPMSBQA-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
PJSFRIWCGOHTNF-UHFFFAOYSA-N Sulphormetoxin Chemical compound COC1=NC=NC(NS(=O)(=O)C=2C=CC(N)=CC=2)=C1OC PJSFRIWCGOHTNF-UHFFFAOYSA-N 0.000 description 3
206010052428 Wound Diseases 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
230000000844 anti-bacterial effect Effects 0.000 description 3
125000003710 aryl alkyl group Chemical group 0.000 description 3
230000037396 body weight Effects 0.000 description 3
239000002775 capsule Substances 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
239000000460 chlorine Chemical group 0.000 description 3
229910052801 chlorine Chemical group 0.000 description 3
239000000284 extract Substances 0.000 description 3
239000005457 ice water Substances 0.000 description 3
239000002054 inoculum Substances 0.000 description 3
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
239000007788 liquid Substances 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 3
230000000813 microbial effect Effects 0.000 description 3
244000005700 microbiome Species 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000000843 powder Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
238000012216 screening Methods 0.000 description 3
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229910000029 sodium carbonate Inorganic materials 0.000 description 3
229960002135 sulfadimidine Drugs 0.000 description 3
229960004673 sulfadoxine Drugs 0.000 description 3
ASWVTGNCAZCNNR-UHFFFAOYSA-N sulfamethazine Chemical compound CC1=CC(C)=NC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 ASWVTGNCAZCNNR-UHFFFAOYSA-N 0.000 description 3
210000002700 urine Anatomy 0.000 description 3
DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 2
CIIPVFHXQLZFRW-UHFFFAOYSA-N 3,5-ditert-butyl-4-phenylmethoxybenzaldehyde Chemical compound CC(C)(C)C1=CC(C=O)=CC(C(C)(C)C)=C1OCC1=CC=CC=C1 CIIPVFHXQLZFRW-UHFFFAOYSA-N 0.000 description 2
ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
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229930182555 Penicillin Natural products 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
208000027418 Wounds and injury Diseases 0.000 description 2
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
150000001241 acetals Chemical class 0.000 description 2
238000005576 amination reaction Methods 0.000 description 2
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230000000635 anti-gonococcal effect Effects 0.000 description 2
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230000001580 bacterial effect Effects 0.000 description 2
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150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
239000000969 carrier Substances 0.000 description 2
229940125898 compound 5 Drugs 0.000 description 2
238000001816 cooling Methods 0.000 description 2
125000004663 dialkyl amino group Chemical group 0.000 description 2
238000010790 dilution Methods 0.000 description 2
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238000000921 elemental analysis Methods 0.000 description 2
239000003480 eluent Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000008187 granular material Substances 0.000 description 2
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150000002431 hydrogen Chemical class 0.000 description 2
239000012535 impurity Substances 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
238000011534 incubation Methods 0.000 description 2
238000002347 injection Methods 0.000 description 2
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239000008101 lactose Substances 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
229940057948 magnesium stearate Drugs 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
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125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
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SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 2
BRBKOPJOKNSWSG-UHFFFAOYSA-N sulfaguanidine Chemical compound NC(=N)NS(=O)(=O)C1=CC=C(N)C=C1 BRBKOPJOKNSWSG-UHFFFAOYSA-N 0.000 description 2
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BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 2
JLKIGFTWXXRPMT-UHFFFAOYSA-N sulphamethoxazole Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 JLKIGFTWXXRPMT-UHFFFAOYSA-N 0.000 description 2
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229910052723 transition metal Inorganic materials 0.000 description 2
150000003624 transition metals Chemical class 0.000 description 2
PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 2
229940035893 uracil Drugs 0.000 description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
UPJYICBVQLMQHX-UHFFFAOYSA-N 2,6-dibutyl-4-[(2,4-diaminopyrimidin-5-yl)methyl]phenol Chemical compound CCCCC1=C(O)C(CCCC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 UPJYICBVQLMQHX-UHFFFAOYSA-N 0.000 description 1
YIUWMODAWJQHQO-UHFFFAOYSA-N 2,6-ditert-butyl-4-(dimethoxymethyl)phenol Chemical compound COC(OC)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 YIUWMODAWJQHQO-UHFFFAOYSA-N 0.000 description 1
KKHMDJKSHQFRCX-UHFFFAOYSA-N 3-amino-n-(2,4-dimethylpyrimidin-5-yl)benzenesulfonamide Chemical compound CC1=NC(C)=NC=C1NS(=O)(=O)C1=CC=CC(N)=C1 KKHMDJKSHQFRCX-UHFFFAOYSA-N 0.000 description 1
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XJPZKYIHCLDXST-UHFFFAOYSA-N 4,6-dichloropyrimidine Chemical compound ClC1=CC(Cl)=NC=N1 XJPZKYIHCLDXST-UHFFFAOYSA-N 0.000 description 1
VLYJATOLYFZNCF-UHFFFAOYSA-N 4-[(2,4-diaminopyrimidin-5-yl)methyl]-2-ethyl-6-propylphenol Chemical compound CCC1=C(O)C(CCC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 VLYJATOLYFZNCF-UHFFFAOYSA-N 0.000 description 1
NHZLNPMOSADWGC-UHFFFAOYSA-N 4-amino-N-(2-quinoxalinyl)benzenesulfonamide Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=CN=C(C=CC=C2)C2=N1 NHZLNPMOSADWGC-UHFFFAOYSA-N 0.000 description 1
OMGPUVFDBICMKD-UHFFFAOYSA-N 4-amino-n-(4-decoxy-5-methoxypyrimidin-2-yl)benzenesulfonamide Chemical compound C1=C(OC)C(OCCCCCCCCCC)=NC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 OMGPUVFDBICMKD-UHFFFAOYSA-N 0.000 description 1
AYGUVOUABVOICG-UHFFFAOYSA-N 5-[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-1h-pyrimidine-2,4-dione Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CC=2C(NC(=O)NC=2)=O)=C1 AYGUVOUABVOICG-UHFFFAOYSA-N 0.000 description 1
NTVMHTFWSNGDLC-UHFFFAOYSA-N 5-[(4-phenylmethoxyphenyl)methyl]pyrimidine-2,4-diamine Chemical compound NC1=NC(N)=NC=C1CC(C=C1)=CC=C1OCC1=CC=CC=C1 NTVMHTFWSNGDLC-UHFFFAOYSA-N 0.000 description 1
JDBGXEHEIRGOBU-UHFFFAOYSA-N 5-hydroxymethyluracil Chemical compound OCC1=CNC(=O)NC1=O JDBGXEHEIRGOBU-UHFFFAOYSA-N 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
241000194103 Bacillus pumilus Species 0.000 description 1
241000606125 Bacteroides Species 0.000 description 1
241000606124 Bacteroides fragilis Species 0.000 description 1
241000606123 Bacteroides thetaiotaomicron Species 0.000 description 1
241000606215 Bacteroides vulgatus Species 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
241000193403 Clostridium Species 0.000 description 1
241000193468 Clostridium perfringens Species 0.000 description 1
241000193449 Clostridium tetani Species 0.000 description 1
LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
241000605909 Fusobacterium Species 0.000 description 1
241000605952 Fusobacterium necrophorum Species 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
102000053187 Glucuronidase Human genes 0.000 description 1
108010060309 Glucuronidase Proteins 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 description 1
206010061218 Inflammation Diseases 0.000 description 1
238000006683 Mannich reaction Methods 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
206010062212 Neisseria infection Diseases 0.000 description 1
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
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241000206591 Peptococcus Species 0.000 description 1
241000191992 Peptostreptococcus Species 0.000 description 1
206010067268 Post procedural infection Diseases 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
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229920002472 Starch Polymers 0.000 description 1
102000005262 Sulfatase Human genes 0.000 description 1
NHUHCSRWZMLRLA-UHFFFAOYSA-N Sulfisoxazole Chemical compound CC1=NOC(NS(=O)(=O)C=2C=CC(N)=CC=2)=C1C NHUHCSRWZMLRLA-UHFFFAOYSA-N 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
241001147717 [Clostridium] sphenoides Species 0.000 description 1
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239000003377 acid catalyst Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000008272 agar Substances 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
230000002152 alkylating effect Effects 0.000 description 1
229960004050 aminobenzoic acid Drugs 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
230000001948 anti-meningococcal effect Effects 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
150000003935 benzaldehydes Chemical class 0.000 description 1
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
229940125782 compound 2 Drugs 0.000 description 1
229940126214 compound 3 Drugs 0.000 description 1
239000006071 cream Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
238000010828 elution Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
229940093471 ethyl oleate Drugs 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000003349 gelling agent Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
235000001727 glucose Nutrition 0.000 description 1
229960000789 guanidine hydrochloride Drugs 0.000 description 1
PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
229940060367 inert ingredients Drugs 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
208000014674 injury Diseases 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 description 1
230000017066 negative regulation of growth Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000002674 ointment Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000001575 pathological effect Effects 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
150000002960 penicillins Chemical class 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 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
229920001592 potato starch Polymers 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000010926 purge Methods 0.000 description 1
WRMCZHYLTVSDQU-UHFFFAOYSA-N pyrimidin-1-ium;acetate Chemical compound CC(O)=O.C1=CN=CN=C1 WRMCZHYLTVSDQU-UHFFFAOYSA-N 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000007901 soft capsule Substances 0.000 description 1
239000008234 soft water Substances 0.000 description 1
241000894007 species Species 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
ZZORFUFYDOWNEF-UHFFFAOYSA-N sulfadimethoxine Chemical compound COC1=NC(OC)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 ZZORFUFYDOWNEF-UHFFFAOYSA-N 0.000 description 1
229960000973 sulfadimethoxine Drugs 0.000 description 1
229960000654 sulfafurazole Drugs 0.000 description 1
QPPBRPIAZZHUNT-UHFFFAOYSA-N sulfamerazine Chemical compound CC1=CC=NC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 QPPBRPIAZZHUNT-UHFFFAOYSA-N 0.000 description 1
229960002597 sulfamerazine Drugs 0.000 description 1
KXRZBTAEDBELFD-UHFFFAOYSA-N sulfamethopyrazine Chemical compound COC1=NC=CN=C1NS(=O)(=O)C1=CC=C(N)C=C1 KXRZBTAEDBELFD-UHFFFAOYSA-N 0.000 description 1
CYFLXLSBHQBMFT-UHFFFAOYSA-N sulfamoxole Chemical compound O1C(C)=C(C)N=C1NS(=O)(=O)C1=CC=C(N)C=C1 CYFLXLSBHQBMFT-UHFFFAOYSA-N 0.000 description 1
229960002211 sulfapyridine Drugs 0.000 description 1
GECHUMIMRBOMGK-UHFFFAOYSA-N sulfapyridine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=CC=CC=N1 GECHUMIMRBOMGK-UHFFFAOYSA-N 0.000 description 1
229960003097 sulfaquinoxaline Drugs 0.000 description 1
108060007951 sulfatase Proteins 0.000 description 1
229960001544 sulfathiazole Drugs 0.000 description 1
JNMRHUJNCSQMMB-UHFFFAOYSA-N sulfathiazole Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CS1 JNMRHUJNCSQMMB-UHFFFAOYSA-N 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
230000008733 trauma Effects 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/30—Halogen atoms or nitro radicals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/63—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/63—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide
- A61K31/635—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide having a heterocyclic ring, e.g. sulfadiazine
- 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
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
- C07D239/49—Two nitrogen atoms with an aralkyl radical, or substituted aralkyl radical, attached in position 5, e.g. trimethoprim
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Oncology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Communicable Diseases (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

NO791699A 1978-05-24 1979-05-23 Benzylpyrimidinforbindelser og fremgangsmaate til deres fremstilling NO791699L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB2193878		1978-05-24

Publications (1)

Publication Number	Publication Date
NO791699L true NO791699L (no)	1979-11-27

Family

ID=10171323

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO791699A NO791699L (no)	1978-05-24	1979-05-23	Benzylpyrimidinforbindelser og fremgangsmaate til deres fremstilling

Country Status (12)

Country	Link
EP (1)	EP0006987A1 (fr)
JP (1)	JPS54154775A (fr)
AU (1)	AU4732579A (fr)
DK (1)	DK214479A (fr)
FI (1)	FI791638A7 (fr)
IL (1)	IL57375A0 (fr)
IT (1)	IT1117752B (fr)
MA (1)	MA18450A1 (fr)
MC (1)	MC1264A1 (fr)
NO (1)	NO791699L (fr)
PT (1)	PT69656A (fr)
ZW (1)	ZW9979A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0054756B1 (fr) *	1980-11-27	1986-07-23	The Wellcome Foundation Limited	Benzylpyrimidines antibactériennes
HU188588B (en) *	1982-08-13	1986-04-28	Egyt Gyogyszervegyeszeti Gyar	Process for the production of 2,4-diamino-5-benzyl-pyrimidine-derivatives
FR2652812A1 (fr) *	1989-10-09	1991-04-12	Rhone Poulenc Chimie	Procede de preparation de difluoro-2,2 benzodioxole-1,3.

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB875562A (en) *	1957-02-21	1961-08-23	Wellcome Found	Improvements in and relating to pyrimidine derivatives and the preparation thereof
GB1128234A (en) *	1966-02-19	1968-09-25	Wellcome Found	5-benzylpyrimidine derivatives and process for the preparation thereof
CH544053A (de) *	1966-05-09	1973-11-15	Hoffmann La Roche	Verfahren zur Herstellung von Sulfonamidderivaten
US3684810A (en) *	1970-03-11	1972-08-15	Hoffmann La Roche	Process for 2,4-diamino-5-(3,5-dimethoxy-4-hydroxybenzyl) pyrimidine
GB1375162A (fr) *	1970-10-22	1974-11-27
BE789904A (fr) *	1971-10-12	1973-04-10	Wellcome Found	Procedes de synthese organique
GB1413472A (en) *	1971-10-12	1975-11-12	Wellcome Found	2,4-diamino pyrimidines
DE2546667C3 (de) *	1975-10-17	1978-10-12	Ludwig Heumann & Co Gmbh, 8500 Nuernberg	2,4-DiamüH»-5-(3-methoxy-4-hydroxy-5-halogenbenzyl)-pyrimidine, und diese Verbindungen enthaltende Arzneimittel

1979
- 1979-05-23 ZW ZW99/79A patent/ZW9979A1/xx unknown
- 1979-05-23 AU AU47325/79A patent/AU4732579A/en not_active Abandoned
- 1979-05-23 MC MC791383A patent/MC1264A1/fr unknown
- 1979-05-23 NO NO791699A patent/NO791699L/no unknown
- 1979-05-23 MA MA18644A patent/MA18450A1/fr unknown
- 1979-05-23 IL IL57375A patent/IL57375A0/xx unknown
- 1979-05-23 DK DK214479A patent/DK214479A/da unknown
- 1979-05-23 JP JP6376279A patent/JPS54154775A/ja active Pending
- 1979-05-23 FI FI791638A patent/FI791638A7/fi not_active Application Discontinuation
- 1979-05-23 EP EP79101596A patent/EP0006987A1/fr not_active Withdrawn
- 1979-05-23 IT IT49150/79A patent/IT1117752B/it active
- 1979-05-23 PT PT69656A patent/PT69656A/pt unknown

Also Published As

Publication number	Publication date
JPS54154775A (en)	1979-12-06
EP0006987A1 (fr)	1980-01-23
DK214479A (da)	1979-11-25
FI791638A7 (fi)	1979-11-25
ZW9979A1 (en)	1980-12-24
IT7949150A0 (it)	1979-05-23
PT69656A (en)	1979-06-01
IT1117752B (it)	1986-02-24
IL57375A0 (en)	1979-09-30
AU4732579A (en)	1979-11-29
MC1264A1 (fr)	1980-03-28
MA18450A1 (fr)	1979-12-31

Publication	Publication Date	Title
US4587342A (en)	1986-05-06	2,4-diamino-(substituted-benzopyran(quinolyl,isoquinoly)methyl)pyrimidines useful as antibacterials
US4515948A (en)	1985-05-07	2,4-Diamino-5-(4-amino and 4-dimethylamino-3,5-dimethoxy benzyl)pyrimidines
AU2022200967A1 (en)	2022-03-03	Compositions and methods for treating infections
EP0103464B1 (fr)	1988-11-17	Diaminopyrimidines et leur préparation
US20120252791A1 (en)	2012-10-04	Heterocyclic GTP Cyclohydrolase 1 Inhibitors For the Treatment of Pain
US4992444A (en)	1991-02-12	Antifolate agents
NO812431L (no)	1982-01-18	Fremgangsmaate for fremstilling av terapeutisk aktive pyrimidin-2-on-derivater.
US4590271A (en)	1986-05-20	2,4-diamino-5-(substituted)pyrimidines, useful as antimicrobials
US8314092B2 (en)	2012-11-20	Substituted [(5H-pyrrolo[2,1-c][1,4]benzodiazepin-11-yl)piperazin-1-yl]-2,2-dimethylpropanoic acid compounds as dual activity H1 inverse agonists/5-HT2A antagonists
US4237289A (en)	1980-12-02	2,7-Diamino-8-methyl-5-substituted pyrido{2,3-d}pyrimidin-6-ones
EP0006987A1 (fr)	1980-01-23	2,4-Diamino-5-benzylpyrimidines, notamment pour le traitement médical d'infections microbiennes, compositions pharmaceutiques contenant ces composés et procédé pour la préparation de ces derniers
US4156725A (en)	1979-05-29	Bacteriostatic biologically active compositions
CH591457A5 (fr)	1977-09-15
US4073786A (en)	1978-02-14	2-Amino-4-hydroxy-6-hydroxymethyl-7,7-diethyl-7,8-dihydropteridine and the 7-spirocyclohexyl analogue thereof
US3963719A (en)	1976-06-15	6-Spirocycloalkylamino 5-nitropyrimidines
US4042589A (en)	1977-08-16	Pteridine compounds
RU2803938C2 (ru)	2023-09-22	Новое соединение бензимидазолона и его фармацевтическое применение
US3933820A (en)	1976-01-20	5-Nitropyrimidines
US3454575A (en)	1969-07-08	Quaternary 5-ammonium-methyl-4-amino-2 cycloaliphatylpyrimidine salts
US4260758A (en)	1981-04-07	Pyrazolo (3,4-d) pyrimidines and methods of making
KR790001021B1 (ko)	1979-08-20	설폰아미드의 제조방법
JPS5973573A (ja)	1984-04-25	ジアミノピリミジン化合物
JPH05247059A (ja)	1993-09-24	チアゼトキノリン−３−カルボン酸誘導体
NO135420B (fr)	1976-12-27
IL44123A (en)	1977-10-31	2-amino-4-hydroxy-7,8-dihydropteridine-6-carboxaldehyde derivatives their preparation and pharmaceutical compositions containing them