SE434948B - N-(6-(4-aminosulfonylfenyl)-1,2-dihydro-2-oxonikotinyl)-ampicillin eller -amoxicillin - Google Patents

N-(6-(4-aminosulfonylfenyl)-1,2-dihydro-2-oxonikotinyl)-ampicillin eller -amoxicillin

Info

Publication number: SE434948B
Authority: SE; Sweden
Prior art keywords: phenyl; dihydro; aminosulfonyl; acid; oxonicotinyl
Prior art date: 1977-06-03

Application number

SE7806493A

Other languages

English (en)

Swedish (sv)

Other versions

SE7806493L (sv

Inventor

J S Kaltenbronn

T H Haskell

L Doub

Original Assignee

Warner Lambert Co

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.)

1977-06-03

Filing date

1978-06-02

Publication date

1984-08-27

1978-06-02 Application filed by Warner Lambert Co filed Critical Warner Lambert Co

1978-12-04 Publication of SE7806493L publication Critical patent/SE7806493L/xx

1984-08-27 Publication of SE434948B publication Critical patent/SE434948B/sv

Links

-1 6- (4-AMINOSULPHONYLPHENYL) -1,2-DIHYDRO-2-OXONICOTINYL Chemical class 0.000 title claims description 57
229960000723 ampicillin Drugs 0.000 title claims description 32
229960003022 amoxicillin Drugs 0.000 title claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 86
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 47
159000000000 sodium salts Chemical class 0.000 claims description 43
150000001875 compounds Chemical class 0.000 claims description 42
239000002253 acid Substances 0.000 claims description 34
AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 claims description 26
150000003839 salts Chemical class 0.000 claims description 24
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 23
125000006263 dimethyl aminosulfonyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])S(*)(=O)=O 0.000 claims description 12
LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 9
LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 claims description 9
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
150000001413 amino acids Chemical class 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 7
125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 6
150000002333 glycines Chemical class 0.000 claims description 6
229930182555 Penicillin Natural products 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 claims description 4
229940049954 penicillin Drugs 0.000 claims description 4
JGSARLDLIJGVTE-UHFFFAOYSA-N 3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-UHFFFAOYSA-N 0.000 claims description 3
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Natural products NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 3
239000004471 Glycine Substances 0.000 claims description 3
NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 claims description 2
NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 claims description 2
230000000694 effects Effects 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
KHWGRLRCZSYJNT-UHFFFAOYSA-N 2-oxo-3h-pyridine-3-carboxylic acid Chemical compound OC(=O)C1C=CC=NC1=O KHWGRLRCZSYJNT-UHFFFAOYSA-N 0.000 claims 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 1
229910003844 NSO2 Inorganic materials 0.000 claims 1
230000003115 biocidal effect Effects 0.000 claims 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 114
239000000243 solution Substances 0.000 description 87
ZMXDDKWLCZADIW-UHFFFAOYSA-N Vilsmeier-Haack reagent Natural products CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 82
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 75
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 72
239000000203 mixture Substances 0.000 description 72
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 55
238000001914 filtration Methods 0.000 description 55
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 37
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 36
239000002244 precipitate Substances 0.000 description 34
229940086542 triethylamine Drugs 0.000 description 34
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 30
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 29
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 24
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 20
238000002425 crystallisation Methods 0.000 description 20
230000008025 crystallization Effects 0.000 description 20
239000007787 solid Substances 0.000 description 19
239000000725 suspension Substances 0.000 description 19
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 18
238000000034 method Methods 0.000 description 16
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 15
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 15
239000005457 ice water Substances 0.000 description 15
FXVDNCRTKXMSEZ-UHFFFAOYSA-N 4-acetylbenzenesulfonyl chloride Chemical compound CC(=O)C1=CC=C(S(Cl)(=O)=O)C=C1 FXVDNCRTKXMSEZ-UHFFFAOYSA-N 0.000 description 14
239000000047 product Substances 0.000 description 14
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 12
DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical compound NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 description 12
238000000354 decomposition reaction Methods 0.000 description 12
PUWCULQGLSPCMQ-UHFFFAOYSA-M sodium;4-acetylbenzenesulfonate Chemical compound [Na+].CC(=O)C1=CC=C(S([O-])(=O)=O)C=C1 PUWCULQGLSPCMQ-UHFFFAOYSA-M 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
238000002844 melting Methods 0.000 description 9
230000008018 melting Effects 0.000 description 9
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 8
238000001556 precipitation Methods 0.000 description 8
VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 8
238000003756 stirring Methods 0.000 description 8
150000007513 acids Chemical class 0.000 description 7
229910052757 nitrogen Inorganic materials 0.000 description 7
229960001760 dimethyl sulfoxide Drugs 0.000 description 6
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 5
CBJIMTSAKODBSL-UHFFFAOYSA-N 6-[4-[bis(2-hydroxyethyl)sulfamoyl]phenyl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=CC(S(=O)(=O)N(CCO)CCO)=CC=C1C1=CC=C(C(O)=O)C(=O)N1 CBJIMTSAKODBSL-UHFFFAOYSA-N 0.000 description 5
150000008064 anhydrides Chemical class 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 description 5
238000000746 purification Methods 0.000 description 5
239000002904 solvent Substances 0.000 description 5
239000007858 starting material Substances 0.000 description 5
KMZZPVGVHFZSSN-UHFFFAOYSA-N 6-[4-[bis(2-hydroxyethyl)sulfamoyl]phenyl]-1-methyl-2-oxopyridine-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)N(C)C(C=2C=CC(=CC=2)S(=O)(=O)N(CCO)CCO)=C1 KMZZPVGVHFZSSN-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
150000004820 halides Chemical class 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
BEAGOQUJDUYYBJ-UHFFFAOYSA-N 1-[4-[3-(hydroxymethyl)piperidin-1-yl]sulfonylphenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1S(=O)(=O)N1CC(CO)CCC1 BEAGOQUJDUYYBJ-UHFFFAOYSA-N 0.000 description 3
VYQQICURHGHIFH-UHFFFAOYSA-N 2-oxo-6-(2-sulfamoylphenyl)-1h-pyridine-3-carboxylic acid Chemical class NS(=O)(=O)C1=CC=CC=C1C1=CC=C(C(O)=O)C(=O)N1 VYQQICURHGHIFH-UHFFFAOYSA-N 0.000 description 3
FEUVWLKJJCVGFJ-UHFFFAOYSA-N 3-(chloromethyl)-6-(4-piperidin-1-ylsulfonylphenyl)-1h-pyridin-2-one Chemical compound N1C(=O)C(CCl)=CC=C1C1=CC=C(S(=O)(=O)N2CCCCC2)C=C1 FEUVWLKJJCVGFJ-UHFFFAOYSA-N 0.000 description 3
MMVNUSQPCYEOIA-UHFFFAOYSA-N 4-(5-cyano-6-oxo-1h-pyridin-2-yl)-n-pyridin-2-ylbenzenesulfonamide Chemical compound C1=C(C#N)C(=O)NC(C=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 MMVNUSQPCYEOIA-UHFFFAOYSA-N 0.000 description 3
TYCJOLCJQPFCGL-UHFFFAOYSA-N 4-[5-(chloromethyl)-6-oxo-1h-pyridin-2-yl]-n,n-diethylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N(CC)CC)=CC=C1C1=CC=C(CCl)C(=O)N1 TYCJOLCJQPFCGL-UHFFFAOYSA-N 0.000 description 3
LWUVBLHWSCEPTM-UHFFFAOYSA-N 4-acetyl-n,n-bis(2-hydroxyethyl)benzenesulfonamide Chemical compound CC(=O)C1=CC=C(S(=O)(=O)N(CCO)CCO)C=C1 LWUVBLHWSCEPTM-UHFFFAOYSA-N 0.000 description 3
OKAAHYQTIYWBEL-UHFFFAOYSA-N 4-acetyl-n,n-diethylbenzenesulfonamide Chemical compound CCN(CC)S(=O)(=O)C1=CC=C(C(C)=O)C=C1 OKAAHYQTIYWBEL-UHFFFAOYSA-N 0.000 description 3
JJTSRGOGIDQHGO-UHFFFAOYSA-N 4-acetyl-n,n-dimethylbenzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC=C(C(C)=O)C=C1 JJTSRGOGIDQHGO-UHFFFAOYSA-N 0.000 description 3
AQOINBRRKOIXQW-UHFFFAOYSA-N 4-acetyl-n-(2-hydroxyethyl)benzenesulfonamide Chemical compound CC(=O)C1=CC=C(S(=O)(=O)NCCO)C=C1 AQOINBRRKOIXQW-UHFFFAOYSA-N 0.000 description 3
DUJQWLBUQLZXAH-UHFFFAOYSA-N 4-acetyl-n-[2-(dimethylamino)ethyl]benzenesulfonamide Chemical compound CN(C)CCNS(=O)(=O)C1=CC=C(C(C)=O)C=C1 DUJQWLBUQLZXAH-UHFFFAOYSA-N 0.000 description 3
AROFFTSACLUEFT-UHFFFAOYSA-N 4-acetyl-n-pyridin-2-ylbenzenesulfonamide Chemical compound C1=CC(C(=O)C)=CC=C1S(=O)(=O)NC1=CC=CC=N1 AROFFTSACLUEFT-UHFFFAOYSA-N 0.000 description 3
UWJIKBPKBYVVPF-UHFFFAOYSA-N 4-acetyl-n-pyridin-3-ylbenzenesulfonamide Chemical compound C1=CC(C(=O)C)=CC=C1S(=O)(=O)NC1=CC=CN=C1 UWJIKBPKBYVVPF-UHFFFAOYSA-N 0.000 description 3
CSATVXJBGFVJES-UHFFFAOYSA-N 4-acetylbenzenesulfonamide Chemical class CC(=O)C1=CC=C(S(N)(=O)=O)C=C1 CSATVXJBGFVJES-UHFFFAOYSA-N 0.000 description 3
CQBDDGSYCNGDBO-UHFFFAOYSA-N 6-[4-[3-(hydroxymethyl)piperidin-1-yl]sulfonylphenyl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1C(CO)CCCN1S(=O)(=O)C1=CC=C(C=2NC(=O)C(C(O)=O)=CC=2)C=C1 CQBDDGSYCNGDBO-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
230000010933 acylation Effects 0.000 description 3
238000005917 acylation reaction Methods 0.000 description 3
239000003708 ampul Substances 0.000 description 3
230000037396 body weight Effects 0.000 description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
230000029087 digestion Effects 0.000 description 3
JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 description 3
125000006261 methyl amino sulfonyl group Chemical group [H]N(C([H])([H])[H])S(*)(=O)=O 0.000 description 3
238000005406 washing Methods 0.000 description 3
FGHDPJXLQVZPHF-HXUWFJFHSA-N (2R)-2-[[6-[4-(dimethylsulfamoyl)phenyl]-2-oxo-1H-pyridin-3-yl]methylamino]-2-phenylacetic acid Chemical compound CN(S(=O)(=O)C1=CC=C(C=C1)C=1NC(C(CN[C@@H](C(=O)O)C2=CC=CC=C2)=CC=1)=O)C FGHDPJXLQVZPHF-HXUWFJFHSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
MIBYJBHDWBZZDA-UHFFFAOYSA-N 1-(4-piperidin-1-ylsulfonylphenyl)ethanone Chemical compound C1=CC(C(=O)C)=CC=C1S(=O)(=O)N1CCCCC1 MIBYJBHDWBZZDA-UHFFFAOYSA-N 0.000 description 2
JYLJULSIFMBCJA-UHFFFAOYSA-N 1-(4-pyrrolidin-1-ylsulfonylphenyl)ethanone Chemical compound C1=CC(C(=O)C)=CC=C1S(=O)(=O)N1CCCC1 JYLJULSIFMBCJA-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
UEYQJQVBUVAELZ-UHFFFAOYSA-N 2-Hydroxynicotinic acid Chemical compound OC(=O)C1=CC=CN=C1O UEYQJQVBUVAELZ-UHFFFAOYSA-N 0.000 description 2
ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
LIHUTSFYFGCWQP-UHFFFAOYSA-N 2-cyano-n-methylacetamide Chemical compound CNC(=O)CC#N LIHUTSFYFGCWQP-UHFFFAOYSA-N 0.000 description 2
YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 2
MNTGZDFXQQMNCT-UHFFFAOYSA-N 2-oxo-6-(4-piperidin-1-ylsulfonylphenyl)-1h-pyridine-3-carbonitrile Chemical compound C1=C(C#N)C(=O)NC(C=2C=CC(=CC=2)S(=O)(=O)N2CCCCC2)=C1 MNTGZDFXQQMNCT-UHFFFAOYSA-N 0.000 description 2
XCVAZFHSHAOTEF-UHFFFAOYSA-N 2-oxo-6-(4-piperidin-1-ylsulfonylphenyl)-1h-pyridine-3-carboxylic acid Chemical compound N1C(=O)C(C(=O)O)=CC=C1C1=CC=C(S(=O)(=O)N2CCCCC2)C=C1 XCVAZFHSHAOTEF-UHFFFAOYSA-N 0.000 description 2
DASFCKHAAUILPP-UHFFFAOYSA-N 2-oxo-6-(4-pyrrolidin-1-ylsulfonylphenyl)-1h-pyridine-3-carbonitrile Chemical compound C1=C(C#N)C(=O)NC(C=2C=CC(=CC=2)S(=O)(=O)N2CCCC2)=C1 DASFCKHAAUILPP-UHFFFAOYSA-N 0.000 description 2
CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 2
HCSDAMGBOVWGEO-UHFFFAOYSA-N 3-oxo-3-phenylpropanal Chemical compound O=CCC(=O)C1=CC=CC=C1 HCSDAMGBOVWGEO-UHFFFAOYSA-N 0.000 description 2
HNIZFKHXDNJMAU-UHFFFAOYSA-N 4-(3-oxopropanoyl)-n-pyridin-3-ylbenzenesulfonamide Chemical compound C1=CC(C(=O)CC=O)=CC=C1S(=O)(=O)NC1=CC=CN=C1 HNIZFKHXDNJMAU-UHFFFAOYSA-N 0.000 description 2
USNIRSKYIVTFFP-UHFFFAOYSA-N 4-(5-cyano-6-oxo-1h-pyridin-2-yl)-n,n-bis(2-hydroxyethyl)benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N(CCO)CCO)=CC=C1C1=CC=C(C#N)C(=O)N1 USNIRSKYIVTFFP-UHFFFAOYSA-N 0.000 description 2
YJUBKPSCVNMQCR-UHFFFAOYSA-N 4-(5-cyano-6-oxo-1h-pyridin-2-yl)-n,n-diethylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N(CC)CC)=CC=C1C1=CC=C(C#N)C(=O)N1 YJUBKPSCVNMQCR-UHFFFAOYSA-N 0.000 description 2
NUOVAMAMGKFHRZ-UHFFFAOYSA-N 4-(5-cyano-6-oxo-1h-pyridin-2-yl)-n-[2-(dimethylamino)ethyl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NCCN(C)C)=CC=C1C1=CC=C(C#N)C(=O)N1 NUOVAMAMGKFHRZ-UHFFFAOYSA-N 0.000 description 2
NUNWFALUQJQMCQ-UHFFFAOYSA-N 4-(5-cyano-6-oxo-1h-pyridin-2-yl)-n-methylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NC)=CC=C1C1=CC=C(C#N)C(=O)N1 NUNWFALUQJQMCQ-UHFFFAOYSA-N 0.000 description 2
IEQZPAXMABXTJF-UHFFFAOYSA-N 4-[5-(chloromethyl)-6-oxo-1h-pyridin-2-yl]-n-methylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NC)=CC=C1C1=CC=C(CCl)C(=O)N1 IEQZPAXMABXTJF-UHFFFAOYSA-N 0.000 description 2
ZRQSFVDGIIYDFE-UHFFFAOYSA-N 4-[5-(chloromethyl)-6-oxo-1h-pyridin-2-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=CC=C(CCl)C(=O)N1 ZRQSFVDGIIYDFE-UHFFFAOYSA-N 0.000 description 2
JAYNQWDHBPWEMB-UHFFFAOYSA-N 4-acetyl-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(C(C)=O)C=C1 JAYNQWDHBPWEMB-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
241000208202 Linaceae Species 0.000 description 2
235000004431 Linum usitatissimum Nutrition 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
238000003436 Schotten-Baumann reaction Methods 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
239000003242 anti bacterial agent Substances 0.000 description 2
229940088710 antibiotic agent Drugs 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000003814 drug Substances 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
ZZIIUOALILJDIW-UHFFFAOYSA-N n,n-dimethyl-4-(3-oxopropanoyl)benzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC=C(C(=O)CC=O)C=C1 ZZIIUOALILJDIW-UHFFFAOYSA-N 0.000 description 2
WWECJGLXBSQKRF-UHFFFAOYSA-N n,n-dimethylformamide;methanol Chemical compound OC.CN(C)C=O WWECJGLXBSQKRF-UHFFFAOYSA-N 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
230000020477 pH reduction Effects 0.000 description 2
IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 2
229960002292 piperacillin Drugs 0.000 description 2
WCMIIGXFCMNQDS-IDYPWDAWSA-M piperacillin sodium Chemical compound [Na+].O=C1C(=O)N(CC)CCN1C(=O)N[C@H](C=1C=CC=CC=1)C(=O)N[C@@H]1C(=O)N2[C@@H](C([O-])=O)C(C)(C)S[C@@H]21 WCMIIGXFCMNQDS-IDYPWDAWSA-M 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000376 reactant Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000010992 reflux Methods 0.000 description 2
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
150000003462 sulfoxides Chemical class 0.000 description 2
150000003511 tertiary amides Chemical class 0.000 description 2
FBQULHKFVMKTJX-SNVBAGLBSA-N (2R)-2-phenyl-2-(trimethylsilylamino)acetic acid Chemical compound C[Si](C)(C)N[C@@H](C(O)=O)C1=CC=CC=C1 FBQULHKFVMKTJX-SNVBAGLBSA-N 0.000 description 1
GERXQFMVSQUXHT-BOUYBQKTSA-N (2s,5r,6r)-6-[[(2r)-2-[[(2r)-2-[[(2r)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-2-[(2r,4s)-4-carboxy-5,5-dimethyl-1,3-thiazolidin-2-yl]acetyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound N1[C@@H](C(O)=O)C(C)(C)S[C@@H]1[C@@H](C(=O)N[C@@H](C(=O)N[C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C=1C=CC(O)=CC=1)NC(=O)[C@H](N)C1=CC=C(O)C=C1 GERXQFMVSQUXHT-BOUYBQKTSA-N 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
UMELMYFEIWUROC-UHFFFAOYSA-N 2-oxo-1-phenylpyridine-3-carbonitrile Chemical compound O=C1C(C#N)=CC=CN1C1=CC=CC=C1 UMELMYFEIWUROC-UHFFFAOYSA-N 0.000 description 1
IXDWSPYXCCAUAW-UHFFFAOYSA-N 2-oxo-1-phenylpyridine-3-carboxylic acid Chemical compound O=C1C(C(=O)O)=CC=CN1C1=CC=CC=C1 IXDWSPYXCCAUAW-UHFFFAOYSA-N 0.000 description 1
ADFOBZKXAWJPCS-UHFFFAOYSA-N 2-oxo-6-(3-sulfamoylphenyl)-1h-pyridine-3-carboxylic acid Chemical compound NS(=O)(=O)C1=CC=CC(C=2NC(=O)C(C(O)=O)=CC=2)=C1 ADFOBZKXAWJPCS-UHFFFAOYSA-N 0.000 description 1
AVXANYAQORHOQG-UHFFFAOYSA-N 2-oxo-6-(4-pyrrolidin-1-ylsulfonylphenyl)-1h-pyridine-3-carboxylic acid Chemical compound N1C(=O)C(C(=O)O)=CC=C1C1=CC=C(S(=O)(=O)N2CCCC2)C=C1 AVXANYAQORHOQG-UHFFFAOYSA-N 0.000 description 1
FYVQYBXEIALPHD-UHFFFAOYSA-N 2-oxo-6-(4-sulfamoylphenyl)-1h-pyridine-3-carboxylic acid Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=CC=C(C(O)=O)C(=O)N1 FYVQYBXEIALPHD-UHFFFAOYSA-N 0.000 description 1
QHWPNANNWFBDGK-UHFFFAOYSA-N 2-oxo-6-[4-(pyridin-3-ylsulfamoyl)phenyl]-1h-pyridine-3-carboxylic acid Chemical compound N1C(=O)C(C(=O)O)=CC=C1C1=CC=C(S(=O)(=O)NC=2C=NC=CC=2)C=C1 QHWPNANNWFBDGK-UHFFFAOYSA-N 0.000 description 1
MPSMUYZSUNOJRK-UHFFFAOYSA-N 3-(3-oxopropanoyl)benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(C(=O)CC=O)=C1 MPSMUYZSUNOJRK-UHFFFAOYSA-N 0.000 description 1
ASKDIJJRYKMEMV-UHFFFAOYSA-N 3-(chloromethyl)-1h-pyridin-2-one Chemical compound ClCC1=CC=CNC1=O ASKDIJJRYKMEMV-UHFFFAOYSA-N 0.000 description 1
LVTYIZGEGIKAJJ-UHFFFAOYSA-N 3-(chloromethyl)-6-(4-pyrrolidin-1-ylsulfonylphenyl)-1h-pyridin-2-one Chemical compound N1C(=O)C(CCl)=CC=C1C1=CC=C(S(=O)(=O)N2CCCC2)C=C1 LVTYIZGEGIKAJJ-UHFFFAOYSA-N 0.000 description 1
ANUOTWKUFXJXHL-UHFFFAOYSA-N 3-[4-[3-(hydroxymethyl)piperidin-1-yl]sulfonylphenyl]-3-oxopropanal Chemical compound C1C(CO)CCCN1S(=O)(=O)C1=CC=C(C(=O)CC=O)C=C1 ANUOTWKUFXJXHL-UHFFFAOYSA-N 0.000 description 1
ZLZNHLVBJWGUCV-UHFFFAOYSA-N 3-acetylbenzenesulfonamide Chemical compound CC(=O)C1=CC=CC(S(N)(=O)=O)=C1 ZLZNHLVBJWGUCV-UHFFFAOYSA-N 0.000 description 1
IKJSGXZJYDUJBI-UHFFFAOYSA-N 3-oxo-3-(4-piperidin-1-ylsulfonylphenyl)propanal Chemical compound C1=CC(C(=O)CC=O)=CC=C1S(=O)(=O)N1CCCCC1 IKJSGXZJYDUJBI-UHFFFAOYSA-N 0.000 description 1
LYJZCEGNPBPUOT-UHFFFAOYSA-N 4-(3-oxopropanoyl)benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C(C(=O)CC=O)C=C1 LYJZCEGNPBPUOT-UHFFFAOYSA-N 0.000 description 1
OIPZZOCAGCAPPP-UHFFFAOYSA-N 4-(5-cyano-1-methyl-6-oxopyridin-2-yl)-n,n-bis(2-hydroxyethyl)benzenesulfonamide Chemical compound C1=C(C#N)C(=O)N(C)C(C=2C=CC(=CC=2)S(=O)(=O)N(CCO)CCO)=C1 OIPZZOCAGCAPPP-UHFFFAOYSA-N 0.000 description 1
JNMRXBQFGBHWAX-UHFFFAOYSA-N 4-(5-cyano-6-oxo-1h-pyridin-2-yl)-n,n-dimethylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N(C)C)=CC=C1C1=CC=C(C#N)C(=O)N1 JNMRXBQFGBHWAX-UHFFFAOYSA-N 0.000 description 1
IUYISIDJNQQBOM-UHFFFAOYSA-N 4-(5-cyano-6-oxo-1h-pyridin-2-yl)-n-(2-hydroxyethyl)benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NCCO)=CC=C1C1=CC=C(C#N)C(=O)N1 IUYISIDJNQQBOM-UHFFFAOYSA-N 0.000 description 1
WMSCZAFBAZSZAF-UHFFFAOYSA-N 4-(5-cyano-6-oxo-1h-pyridin-2-yl)-n-pyridin-3-ylbenzenesulfonamide Chemical compound C1=C(C#N)C(=O)NC(C=2C=CC(=CC=2)S(=O)(=O)NC=2C=NC=CC=2)=C1 WMSCZAFBAZSZAF-UHFFFAOYSA-N 0.000 description 1
MKACBULGEVLOCS-UHFFFAOYSA-N 4-[3-(2,3-dihydro-1H-imidazol-2-ylmethyl)-2-oxo-3H-pyridin-6-yl]-N,N-dimethylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N(C)C)=CC=C1C(C=C1)=NC(=O)C1CC1NC=CN1 MKACBULGEVLOCS-UHFFFAOYSA-N 0.000 description 1
RANNVDXODMYXPI-UHFFFAOYSA-N 4-[5-(2,3-dihydro-1H-imidazole-2-carbonyl)pyridin-2-yl]-N,N-dimethylbenzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC=C(C=C1)C2=NC=C(C=C2)C(=O)C3NC=CN3 RANNVDXODMYXPI-UHFFFAOYSA-N 0.000 description 1
PLUKIHFGTHNSQI-UHFFFAOYSA-N 4-[5-(chloromethyl)-1-methyl-6-oxopyridin-2-yl]-n,n-dimethylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N(C)C)=CC=C1C1=CC=C(CCl)C(=O)N1C PLUKIHFGTHNSQI-UHFFFAOYSA-N 0.000 description 1
AKMDYFLCXQMCQI-UHFFFAOYSA-N 4-[5-(chloromethyl)-6-oxo-1h-pyridin-2-yl]-n,n-dimethylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N(C)C)=CC=C1C1=CC=C(CCl)C(=O)N1 AKMDYFLCXQMCQI-UHFFFAOYSA-N 0.000 description 1
ASRXFDMMIZYKPD-UHFFFAOYSA-N 4-[5-(chloromethyl)-6-oxo-1h-pyridin-2-yl]-n-[2-(dimethylamino)ethyl]benzenesulfonamide;hydrochloride Chemical compound Cl.C1=CC(S(=O)(=O)NCCN(C)C)=CC=C1C1=CC=C(CCl)C(=O)N1 ASRXFDMMIZYKPD-UHFFFAOYSA-N 0.000 description 1
QCMSYPOJVUCDGG-UHFFFAOYSA-N 4-[5-(chloromethyl)-6-oxo-1h-pyridin-2-yl]-n-pyridin-2-ylbenzenesulfonamide Chemical compound N1C(=O)C(CCl)=CC=C1C1=CC=C(S(=O)(=O)NC=2N=CC=CC=2)C=C1 QCMSYPOJVUCDGG-UHFFFAOYSA-N 0.000 description 1
AJVQPCGBPWZYOG-UHFFFAOYSA-N 4-[5-(chloromethyl)-6-oxo-1h-pyridin-2-yl]-n-pyridin-3-ylbenzenesulfonamide;hydrochloride Chemical compound Cl.N1C(=O)C(CCl)=CC=C1C1=CC=C(S(=O)(=O)NC=2C=NC=CC=2)C=C1 AJVQPCGBPWZYOG-UHFFFAOYSA-N 0.000 description 1
KMADJPYFSWNRLR-UHFFFAOYSA-N 6-[4-(2-hydroxyethylsulfamoyl)phenyl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=CC(S(=O)(=O)NCCO)=CC=C1C1=CC=C(C(O)=O)C(=O)N1 KMADJPYFSWNRLR-UHFFFAOYSA-N 0.000 description 1
DXBWKNXRGNUVIK-UHFFFAOYSA-N 6-[4-(dimethylsulfamoyl)phenyl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=CC(S(=O)(=O)N(C)C)=CC=C1C1=CC=C(C(O)=O)C(=O)N1 DXBWKNXRGNUVIK-UHFFFAOYSA-N 0.000 description 1
DBQYCRXGAARPFW-UHFFFAOYSA-N 6-[4-(methylsulfamoyl)phenyl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=CC(S(=O)(=O)NC)=CC=C1C1=CC=C(C(O)=O)C(=O)N1 DBQYCRXGAARPFW-UHFFFAOYSA-N 0.000 description 1
LDXQGSMSURZJIL-UHFFFAOYSA-N 6-[4-[2-(dimethylamino)ethylsulfamoyl]phenyl]-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound C1=CC(S(=O)(=O)NCCN(C)C)=CC=C1C1=CC=C(C(O)=O)C(=O)N1 LDXQGSMSURZJIL-UHFFFAOYSA-N 0.000 description 1
YDBHZXMOOPDGHV-UHFFFAOYSA-N 6-[4-[3-(hydroxymethyl)piperidin-1-yl]sulfonylphenyl]-2-oxo-1H-pyridine-3-carbonitrile Chemical compound C1C(CO)CCCN1S(=O)(=O)C1=CC=C(C=2NC(=O)C(C#N)=CC=2)C=C1 YDBHZXMOOPDGHV-UHFFFAOYSA-N 0.000 description 1
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
241000238366 Cephalopoda Species 0.000 description 1
ZGUNAGUHMKGQNY-SSDOTTSWSA-N D-alpha-phenylglycine Chemical compound OC(=O)[C@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-SSDOTTSWSA-N 0.000 description 1
RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 1
RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
101100298295 Drosophila melanogaster flfl gene 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
101100156417 Mus musculus Lcn3 gene Proteins 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
241000589516 Pseudomonas Species 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
CBWUNQZJGJFJLZ-UHFFFAOYSA-N [Cl].Cl Chemical compound [Cl].Cl CBWUNQZJGJFJLZ-UHFFFAOYSA-N 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000000539 amino acid group Chemical group 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
229960004920 amoxicillin trihydrate Drugs 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000000872 buffer Substances 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
230000010339 dilation Effects 0.000 description 1
LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 1
YGNOYUCUPMACDT-UHFFFAOYSA-N dimethylsulfamic acid Chemical compound CN(C)S(O)(=O)=O YGNOYUCUPMACDT-UHFFFAOYSA-N 0.000 description 1
229940079593 drug Drugs 0.000 description 1
RPBAFSBGYDKNRG-NJBDSQKTSA-N epicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CCC=CC1 RPBAFSBGYDKNRG-NJBDSQKTSA-N 0.000 description 1
229960002457 epicillin Drugs 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000012458 free base Substances 0.000 description 1
229950006191 gluconic acid Drugs 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
229940126601 medicinal product Drugs 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
229940095102 methyl benzoate Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
FZVNLVQDRBONFD-UHFFFAOYSA-N n,n-bis(2-hydroxyethyl)-4-(3-oxopropanoyl)benzenesulfonamide Chemical compound OCCN(CCO)S(=O)(=O)C1=CC=C(C(=O)CC=O)C=C1 FZVNLVQDRBONFD-UHFFFAOYSA-N 0.000 description 1
QABWQXUCTRRAQN-UHFFFAOYSA-N n,n-diethyl-4-(3-oxopropanoyl)benzenesulfonamide Chemical compound CCN(CC)S(=O)(=O)C1=CC=C(C(=O)CC=O)C=C1 QABWQXUCTRRAQN-UHFFFAOYSA-N 0.000 description 1
HSOUUTYPIDHOCZ-UHFFFAOYSA-N n-(2-hydroxyethyl)-4-(3-oxopropanoyl)benzenesulfonamide Chemical compound OCCNS(=O)(=O)C1=CC=C(C(=O)CC=O)C=C1 HSOUUTYPIDHOCZ-UHFFFAOYSA-N 0.000 description 1
OMNWJKQHVVDBOS-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-(3-oxopropanoyl)benzenesulfonamide Chemical compound CN(C)CCNS(=O)(=O)C1=CC=C(C(=O)CC=O)C=C1 OMNWJKQHVVDBOS-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229960002715 nicotine Drugs 0.000 description 1
SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
150000002960 penicillins Chemical class 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
ZUFQCVZBBNZMKD-UHFFFAOYSA-M potassium 2-ethylhexanoate Chemical compound [K+].CCCCC(CC)C([O-])=O ZUFQCVZBBNZMKD-UHFFFAOYSA-M 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
230000006340 racemization Effects 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000006884 silylation reaction Methods 0.000 description 1
150000003385 sodium Chemical class 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
HEMHJVSKTPXQMS-UHFFFAOYSA-N sodium;hydrate Chemical compound O.[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-N 0.000 description 1
JBJWASZNUJCEKT-UHFFFAOYSA-M sodium;hydroxide;hydrate Chemical compound O.[OH-].[Na+] JBJWASZNUJCEKT-UHFFFAOYSA-M 0.000 description 1
239000012265 solid product Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
229960004659 ticarcillin Drugs 0.000 description 1
OHKOGUYZJXTSFX-KZFFXBSXSA-N ticarcillin Chemical compound C=1([C@@H](C(O)=O)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)C=CSC=1 OHKOGUYZJXTSFX-KZFFXBSXSA-N 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 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
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
239000008215 water for injection Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- 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
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring

Landscapes

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

SE7806493A 1977-06-03 1978-06-02 N-(6-(4-aminosulfonylfenyl)-1,2-dihydro-2-oxonikotinyl)-ampicillin eller -amoxicillin SE434948B (sv)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US05/803,004 US4101661A (en)	1977-06-03	1977-06-03	Novel antibacterial amide compounds and process means for producing the same

Publications (2)

Publication Number	Publication Date
SE7806493L SE7806493L (sv)	1978-12-04
SE434948B true SE434948B (sv)	1984-08-27

Family

ID=25185308

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
SE7806493A SE434948B (sv)	1977-06-03	1978-06-02	N-(6-(4-aminosulfonylfenyl)-1,2-dihydro-2-oxonikotinyl)-ampicillin eller -amoxicillin
SE8305009A SE8305009L (sv)	1977-06-03	1983-09-19	Sett att framstella antibakteriella amidforeningar

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
SE8305009A SE8305009L (sv)	1977-06-03	1983-09-19	Sett att framstella antibakteriella amidforeningar

Country Status (16)

Country	Link
US (2)	US4101661A (fr)
JP (1)	JPS5416496A (fr)
AU (1)	AU516082B2 (fr)
BE (1)	BE867778A (fr)
CA (1)	CA1097614A (fr)
CH (1)	CH633556A5 (fr)
DE (1)	DE2824341A1 (fr)
DK (1)	DK248278A (fr)
FR (1)	FR2392999A1 (fr)
GB (1)	GB1594049A (fr)
IE (1)	IE46918B1 (fr)
IT (1)	IT1104716B (fr)
NL (1)	NL7806038A (fr)
NZ (1)	NZ187461A (fr)
PH (1)	PH15761A (fr)
SE (2)	SE434948B (fr)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4198406A (en) *	1975-11-27	1980-04-15	Beecham Group Limited	Carbamoyl heterocyclicthio cephalosporins and pharmaceutical compositions formulated therewith
JPS545974A (en) *	1977-06-16	1979-01-17	Ajinomoto Co Inc	Imidazoledicaroboxylic acid derivatives
US4216215A (en) *	1978-11-06	1980-08-05	Pfizer Inc.	7[(Furanyl-2-acetamido)-2-acetamido]cephalosporin derivatives
JPS55129287A (en) *	1979-03-27	1980-10-06	Ajinomoto Co Inc	Imidazole-dicarboxylic acid derivative
JPS55136292A (en) *	1979-04-09	1980-10-23	Eisai Co Ltd	Cephalosporin derivative, its preparation, and antibacterial comprising it
JPS565487A (en) *	1979-06-26	1981-01-20	Eisai Co Ltd	Cephalosporin compound, its preparation, and antimicrobial comprising it
JPS5643288A (en) *	1979-09-18	1981-04-21	Meiji Seika Kaisha Ltd	Cephalosporin derivative and its preparation
JPS5651488A (en) *	1979-10-02	1981-05-09	Meiji Seika Kaisha Ltd	Penicillin derivative and its preparation
US4315858A (en) *	1980-09-24	1982-02-16	Warner-Lambert Company	Antibacterial amide compounds
US4315014A (en) *	1980-09-24	1982-02-09	Warner-Lambert Company	Antibacterial amide compounds and pharmaceutical composition containing the same
US6329372B1 (en) *	1998-01-27	2001-12-11	Celltech Therapeutics Limited	Phenylalanine derivatives
EP1465869B1 (fr) *	2001-12-21	2013-05-15	Exelixis Patent Company LLC	Modulateurs de lxr
US7482366B2 (en)	2001-12-21	2009-01-27	X-Ceptor Therapeutics, Inc.	Modulators of LXR

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1348985A (en)	1970-06-16	1974-03-27	Merck & Co Inc	Esters of cephalosporin compounds
US3873523A (en) *	1972-12-15	1975-03-25	Parke Davis & Co	Derivatives of ampicillin
US4006230A (en) *	1973-09-13	1977-02-01	Pfizer Inc.	7-D-(α-acylamino-arylacetamido)-cephalosporanic acid derivatives
ZA7546B (en) *	1974-01-21	1976-08-25	Parke Davis & Co	New antibacterial amide compounds and methods for their production
US3954734A (en) *	1974-01-21	1976-05-04	Parke, Davis & Company	Novel antibacterial amide compounds and process means for producing the same
US4053470A (en) *	1974-12-23	1977-10-11	Parke, Davis & Company	Substituted-1,2-dihydro-2-oxonicotinyl-cephalosporins

1977
- 1977-06-03 US US05/803,004 patent/US4101661A/en not_active Expired - Lifetime
- 1977-10-27 US US05/845,996 patent/US4137408A/en not_active Expired - Lifetime
1978
- 1978-05-31 AU AU36725/78A patent/AU516082B2/en not_active Expired
- 1978-05-31 GB GB25265/78A patent/GB1594049A/en not_active Expired
- 1978-06-02 IT IT49694/78A patent/IT1104716B/it active
- 1978-06-02 CA CA304,676A patent/CA1097614A/fr not_active Expired
- 1978-06-02 CH CH608478A patent/CH633556A5/fr not_active IP Right Cessation
- 1978-06-02 IE IE1111/78A patent/IE46918B1/en unknown
- 1978-06-02 JP JP6585078A patent/JPS5416496A/ja active Pending
- 1978-06-02 SE SE7806493A patent/SE434948B/sv unknown
- 1978-06-02 BE BE188294A patent/BE867778A/fr not_active IP Right Cessation
- 1978-06-02 PH PH21223A patent/PH15761A/en unknown
- 1978-06-02 FR FR7816541A patent/FR2392999A1/fr active Granted
- 1978-06-02 DK DK248278A patent/DK248278A/da not_active Application Discontinuation
- 1978-06-02 NL NL7806038A patent/NL7806038A/xx not_active Application Discontinuation
- 1978-06-02 DE DE19782824341 patent/DE2824341A1/de not_active Withdrawn
- 1978-06-02 NZ NZ187461A patent/NZ187461A/xx unknown
1983
- 1983-09-19 SE SE8305009A patent/SE8305009L/xx not_active Application Discontinuation

Also Published As

Publication number	Publication date
IT1104716B (it)	1985-10-28
AU516082B2 (en)	1981-05-14
PH15761A (en)	1983-03-22
FR2392999A1 (fr)	1978-12-29
CH633556A5 (fr)	1982-12-15
NL7806038A (nl)	1978-12-05
CA1097614A (fr)	1981-03-17
SE8305009D0 (sv)	1983-09-19
NZ187461A (en)	1982-05-25
SE8305009L (sv)	1983-09-19
IT7849694A0 (it)	1978-06-02
IE46918B1 (en)	1983-11-02
SE7806493L (sv)	1978-12-04
IE781111L (en)	1978-12-03
US4101661A (en)	1978-07-18
DE2824341A1 (de)	1978-12-21
JPS5416496A (en)	1979-02-07
US4137408A (en)	1979-01-30
AU3672578A (en)	1979-12-06
BE867778A (fr)	1978-10-02
GB1594049A (en)	1981-07-30
FR2392999B1 (fr)	1980-04-04
DK248278A (da)	1978-12-04

Publication	Publication Date	Title
EP0326891B1 (fr)	1994-08-03	Agents antibactériens
AU2001277754B2 (en)	2005-09-29	Proline derivatives and use thereof as drugs
FI112484B (fi)	2003-12-15	Menetelmä 2-(2-alkoksifenyyli)pyrido[3,2-d]pyrimidin-4(3H)-onijohdannaisten valmistamiseksi
SE434948B (sv)	1984-08-27	N-(6-(4-aminosulfonylfenyl)-1,2-dihydro-2-oxonikotinyl)-ampicillin eller -amoxicillin
JPH10506122A (ja)	1998-06-16	抗血栓剤あるいは抗凝血剤としてのアミノヘテロ環誘導体
IE850255L (en)	1985-08-17	Antibacterial quinoline and naphthyridine derivatives
NO178029B (no)	1995-10-02	Analogifremgangsmåte ved fremstilling av terapeutisk aktive pyrazolopyrimidinoner
AU8959998A (en)	1999-05-20	D-proline derivatives
KR20060119705A (ko)	2006-11-24	인다졸 유도체
US4735949A (en)	1988-04-05	Disubstituted-7-pyrrolidinonaphthyridine antibacterial agents
US4840956A (en)	1989-06-20	Novel disubstituted-7-pyrrolidinoquinoline antibacterial agents
EP0228845B1 (fr)	1990-12-12	Composés hétérocycliques contenant N, leurs procédés de préparation et compositions les contennant
US4382089A (en)	1983-05-03	Antibacterial amide compounds, compositions thereof and methods of using them
CZ94098A3 (cs)	1998-07-15	Tertahydrochinolinové deriváty, způsob jejich výroby a farmaceutický prostředek s jejich obsahem
WO2003051848A2 (fr)	2003-06-26	Derives d'acide imidazolidine acetique
EP3655394B1 (fr)	2023-11-22	Nouveaux dérivés d'albicidine, leur utilisation et leur synthèse
JP4208464B2 (ja)	2009-01-14	ナフチリジン−３−カルボン酸誘導体の製造法
JP4208463B2 (ja)	2009-01-14	キノロンカルボン酸誘導体の製造に関する中間体
AU699636B2 (en)	1998-12-10	Bicyclic amino group-substituted pyridonecarboxylic acid derivatives, esters thereof and salts thereof, and bicyclic amines useful as intermediates thereof
JPS63141969A (ja)	1988-06-14	新規イミダゾ−ル誘導体
PL182517B1 (pl)	2002-01-31	Tiopirydyny do zwalczania bakterii Helicobacter
NZ228087A (en)	1991-05-28	Imidazolinone derivatives; pharmaceutical compositions and preparatory processes
JPS62500873A (ja)	1987-04-09	セフアロスポリン誘導体の新規製造方法
JPS596851B2 (ja)	1984-02-15	ピペリジン誘導体
US20230348422A1 (en)	2023-11-02	Albicidin derivatives, their use and synthesis