US3992371A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Penicillins substituted with heterocyclic and substituted phenyl groups
Assignee: Sumitomo Chemical Co Ltd
•
Filing: 1974-12-24
•
Granted: 1976-11-16
•
Expires: 1994-12-24
Abstract
Abstract Novel penicillins of the formula+q,10 WHEREIN C ¦ A¦ C represents a substituted or unsubstituted benzene or nitrogen atom-containing heteroaromatic ring which may be substituted, C ¦C ¦ CB represents a pyridine, pyrazine or pyridazine ring, X represents an oxygen or sulfur atom, Y represents a hydrogen atom or a loer alkoxycarbonyl or lower alkanoyl group, and R1, R2 and R3 are each a hydrogen or halogen atom or a nitro, lower alkylamino, di(lower)alkylamino, aine, lower alkoxycarbonylamino, lower alkanoylamino, amino(lower)alkyl, lower alkyl, lower alkoxy, hydroxyl, sulfamoyl, trifluoromethyl, lower alkylthio or lower alkylsulfonyl group, excluding the cases where all of R1, R2 and R3 are hydrogen atoms and where R1 is a hydroxyl group and R2 and R3 are each a hydrogen or halogen atom, and their nontoxic, pharmaceutically acceptable salts, which can be prepared by reacting a carboxylic acid of the formula: X-Y ¦ C¦ ¦C-COOH A¦ CB wherein C C ¦ ¦C A¦ ¦ C , CB, X and Y are each as defined above or its reactive derivative with a compound of the formula:+q,21 WHEREIN R1, R2 and R3 are each as defined above or its reactive derivative, and are ueful as antimicrobial agents against gram-positive and gram-negative bacteria including Pseudomonas.
Inventors
- 👤 Hisao Tobiki
- 👤 Hirotada Yamada
- 👤 Iwao Nakatsuka
- 👤 Kozo Shimago
- 👤 Shigeru Okano
- 👤 Takenari Nakagome
- 👤 Toshiaki Komatsu
- 👤 Akio Izawa
- 👤 Hiroshi Noguchi
- 👤 Yasuko Eda
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 03:37
CPC Classifications
C; C07; C07D; C07D471/00; C07D471/02; C07D471/04; C07D499/00
Claims Analysis
Total Claims: 45
Claim 1
Independent Claim
149 words
A penicillin of the formula: ##SPC22## wherein ##EQU5## is a benzene ring or a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, a pyrazole ring, a thiazole ring or an imidazole ring, R 4 is hydrogen, halogen, lower alkyl, lower alkoxy, lower alkylthio, hydroxyl, di(lower)alkylamino or lower alkanoylamino ##EQU6## is pyridine ring, a pyrazine ring or a pyridazine ring, X is oxygen or sulfur, Y is hydrogen, lower alkoxycarbonyl or lower alkanoyl and R 1 , R 2 and R 3 are each hydrogen, halogen, nitro, lower alkylamino, di(lower)alkylamino, amino, lower alkoxycarbonylamino, lower alkanoylamino, amino(lower)alkyl, lower alkyl, lower alkoxy, hydroxyl, sulfamoyl, trifluoromethyl, lower alkylthio or lower alkylsulfonyl, excluding the cases where all of R 1 , R 2 and R 3 are hydrogen and where R 1 is hydroxyl and R 2 and R 3 are each hydrogen or halogen, and non-toxic pharmaceutically acceptable salts thereof.
Claim 2
Dependent Claim
149 words
A penicillin of the formula: ##SPC22## wherein ##EQU5## is a benzene ring or a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, a pyrazole ring, a thiazole ring or an imidazole ring, R 4 is hydrogen, halogen, lower alkyl, lower alkoxy, lower alkylthio, hydroxyl, di(lower)alkylamino or lower alkanoylamino ##EQU6## is pyridine ring, a pyrazine ring or a pyridazine ring, X is oxygen or sulfur, Y is hydrogen, lower alkoxycarbonyl or lower alkanoyl and R 1 , R 2 and R 3 are each hydrogen, halogen, nitro, lower alkylamino, di(lower)alkylamino, amino, lower alkoxycarbonylamino, lower alkanoylamino, amino(lower)alkyl, lower alkyl, lower alkoxy, hydroxyl, sulfamoyl, trifluoromethyl, lower alkylthio or lower alkylsulfonyl, excluding the cases where all of R 1 , R 2 and R 3 are hydrogen and where R 1 is hydroxyl and R 2 and R 3 are each hydrogen or halogen, and non-toxic pharmaceutically acceptable salts thereof.
Claim 3
Dependent Claim
11 words
The penicillin of claim 1, wherein ##STR82## is a pyridine ring.
Claim 4
Dependent Claim
11 words
The penicillin of claim 2, wherein ##STR83## has no substituent thereon.
Claim 5
Dependent Claim
9 words
The penicillin of claim 1, wherein Y is hydrogen.
Claim 6
Dependent Claim
51 words
A penicillin of the formula: ##SPC23## wherein ##STR84## and ##STR85## are each a pyridine ring, R 4 is hydrogen, halogen, lower alkyl, lower alkoxy, lower alkylthio, hydroxyl, di(lower)alkylamino or lower alkanoylamino and R 5 and R 6 are each hydrogen, lower alkyl or lower alkanoyl, and non-toxic pharmaceutically acceptable salts thereof.
Claim 7
Dependent Claim
51 words
A penicillin of the formula: ##SPC23## wherein ##STR84## and ##STR85## are each a pyridine ring, R 4 is hydrogen, halogen, lower alkyl, lower alkoxy, lower alkylthio, hydroxyl, di(lower)alkylamino or lower alkanoylamino and R 5 and R 6 are each hydrogen, lower alkyl or lower alkanoyl, and non-toxic pharmaceutically acceptable salts thereof.
Claim 8
Dependent Claim
28 words
The penicillin of claim 5, wherein R 4 is hydrogen, methyl, methoxy or acetoamido, ##STR86## is 4-hydroxy-1,5-naphthyridine, R 5 is hydrogen and R 6 is hydrogen or acetyl.
Claim 9
Dependent Claim
61 words
A penicillin of the formula: ##SPC24## wherein ##STR87## and ##STR88## are each a pyridine ring, R 4 is hydrogen, halogen, lower alkyl, lower alkoxy, lower alkylthio, hydroxyl, di(lower)alkylamino or lower alkanoylamino, R 7 is hydrogen or lower alkyl, R 8 is lower alkyl, amino, lower alkanoylamino, hydroxyl or lower alkoxy, and R 9 is hydrogen, lower alkyl, lower alkoxy or hydroxyl.
Claim 10
Dependent Claim
61 words
A penicillin of the formula: ##SPC24## wherein ##STR87## and ##STR88## are each a pyridine ring, R 4 is hydrogen, halogen, lower alkyl, lower alkoxy, lower alkylthio, hydroxyl, di(lower)alkylamino or lower alkanoylamino, R 7 is hydrogen or lower alkyl, R 8 is lower alkyl, amino, lower alkanoylamino, hydroxyl or lower alkoxy, and R 9 is hydrogen, lower alkyl, lower alkoxy or hydroxyl.
Claim 11
Dependent Claim
41 words
The penicillin of claim 7, wherein ##STR89## is 4-hydroxy-1,5-naphthyridine, R 4 is hydrogen, methyl, methoxy or acetamido, R 7 is hydrogen or methyl, R 8 is methyl, methoxy, amino, acetamido or hydroxyl and R 9 is hydrogen, methyl, methoxy or hydroxyl.
Claim 12
Dependent Claim
7 words
D-.alpha.-(4-Hydroxy-1,5-naphthyridine-3-carboxamido)-m-aminobenzylpenicillin and non-toxic pharmaceutically acceptable salts thereof.
Claim 13
Dependent Claim
7 words
D-.alpha.-(4-Hydroxy-1,5-naphthyridine-3-carboxamido)-m-aminobenzylpenicillin and non-toxic pharmaceutically acceptable salts thereof.
Claim 14
Dependent Claim
7 words
D-α-(4-Hydroxy-1,5-naphthyridine-3-carboxamido)-p-aminobenzylpenicillin and non-toxic pharmaceutically acceptable salts thereof.
Claim 15
Dependent Claim
7 words
D-α-(4-Hydroxy-1,5-naphthyridine-3-carboxamido)-p-aminobenzylpenicillin and non-toxic pharmaceutically acceptable salts thereof.
Claim 16
Dependent Claim
7 words
D-α-(4-Hydroxy-1,5-naphthyridine-3-carboxamido)-p-methoxybenzylpenicillin and non-toxic pharmaceutically acceptable salts thereof.
Claim 17
Dependent Claim
7 words
D-α-(4-Hydroxy-1,5-naphthyridine-3-carboxamido)-p-methoxybenzylpenicillin and non-toxic pharmaceutically acceptable salts thereof.
Claim 18
Dependent Claim
7 words
D-α-(4-Hydroxycinnolin-3-carboxamido)-m-aminobenzylpenicillin and non-toxic pharmaceutically acceptable salts thereof.
Claim 19
Dependent Claim
7 words
D-α-(4-Hydroxycinnolin-3-carboxamido)-m-aminobenzylpenicillin and non-toxic pharmaceutically acceptable salts thereof.
Claim 20
Dependent Claim
7 words
D-α-(3-Hydroxyquinoxaline-2-carboxamido)-m-aminobenzylpenicillin and non-toxic pharmaceutically acceptable salts thereof.
Claim 21
Dependent Claim
7 words
D-α-(3-Hydroxyquinoxaline-2-carboxamido)-m-aminobenzylpenicillin and non-toxic pharmaceutically acceptable salts thereof.
Claim 22
Dependent Claim
7 words
D-α-(4-Hydroxyquinoline-3-carboxamido)-m-aminobenzylpenicillin and non-toxic pharmaceutically acceptable salts thereof.
Claim 23
Dependent Claim
7 words
D-α-(4-Hydroxyquinoline-3-carboxamido)-m-aminobenzylpenicillin and non-toxic pharmaceutically acceptable salts thereof.
Claim 24
Dependent Claim
7 words
D-α-(4-Hydroxy-8-methyl-1,8-naphthyridine-3-carboxamido)-m-aminobenzylpenicillin and non-toxic pharmaceutically acceptable salts thereof.
Claim 25
Dependent Claim
7 words
D-α-(4-Hydroxy-8-methyl-1,8-naphthyridine-3-carboxamido)-m-aminobenzylpenicillin and non-toxic pharmaceutically acceptable salts thereof.
Claim 26
Dependent Claim
7 words
D-α-(4-Hydroxy-6-methyl-1,5-naphthyridine-3-carboxamido)-m-aminobenzylpenicillin and non-toxic pharmaceutically acceptable salts thereof.
Claim 27
Dependent Claim
7 words
D-α-(4-Hydroxy-6-methyl-1,5-naphthyridine-3-carboxamido)-m-aminobenzylpenicillin and non-toxic pharmaceutically acceptable salts thereof.
Claim 28
Dependent Claim
7 words
D-α-(4-Hydroxy-6-dimethylamino-1,5-naphthyridine-3-carboxamido)-m-aminobenzylpenicillin and non-toxic pharmaceutically acceptable salts thereof.
Claim 29
Dependent Claim
7 words
D-α-(4-Hydroxy-6-dimethylamino-1,5-naphthyridine-3-carboxamido)-m-aminobenzylpenicillin and non-toxic pharmaceutically acceptable salts thereof.
Claim 30
Dependent Claim
7 words
D-α-(4-Hydroxy-6-acetamido-1,5-naphthyridine-3-carboxamido)-m-aminobenzylpenicillin and non-toxic pharmaceutically acceptable salts thereof.
Claim 31
Dependent Claim
7 words
D-α-(4-Hydroxy-6-acetamido-1,5-naphthyridine-3-carboxamido)-m-aminobenzylpenicillin and non-toxic pharmaceutically acceptable salts thereof.
Claim 32
Dependent Claim
7 words
D-α-(8-Hydroxypyrido[3,2-d]pyridine-7-carboxamido)-m-aminobenzylpenicillin and non-toxic pharmaceutically acceptable salts thereof.
Claim 33
Dependent Claim
7 words
D-α-(8-Hydroxypyrido[3,2-d]pyridine-7-carboxamido)-m-aminobenzylpenicillin and non-toxic pharmaceutically acceptable salts thereof.
Claim 34
Dependent Claim
7 words
D-α-(4-Mercapto-1,5-naphthyridine-3-carboxamido)-m-aminobenzylpenicillin and non-toxic pharmaceutically acceptable salts thereof.
Claim 35
Dependent Claim
7 words
D-α-(4-Mercapto-1,5-naphthyridine-3-carboxamido)-m-aminobenzylpenicillin and non-toxic pharmaceutically acceptable salts thereof.
Claim 36
Dependent Claim
7 words
D-α-(8-Hydroxy-3-methoxypyrido[2,3-b]pyrazine-7-carboxamido)-m-aminobenzylpenicillin and non-toxic pharmaceutically acceptable salts thereof.
Claim 37
Dependent Claim
7 words
D-α-(8-Hydroxy-3-methoxypyrido[2,3-b]pyrazine-7-carboxamido)-m-aminobenzylpenicillin and non-toxic pharmaceutically acceptable salts thereof.
Claim 38
Dependent Claim
7 words
D-α-(4-Hydroxythiazolo[5,4-b]pyridine-5-carboxamido)-m-aminobenzylpenicillin and non-toxic pharmaceutically acceptable salts thereof.
Claim 39
Dependent Claim
7 words
D-α-(4-Hydroxythiazolo[5,4-b]pyridine-5-carboxamido)-m-aminobenzylpenicillin and non-toxic pharmaceutically acceptable salts thereof.
Claim 40
Dependent Claim
7 words
D-α-(4-Hydroxy-1,5-naphthyridine-3-carboxamido)-p-hydroxy-m-methylbenzylpenicillin and non-toxic pharmaceutically acceptable salts thereof.
Claim 41
Dependent Claim
7 words
D-α-(4-Hydroxy-1,5-naphthyridine-3-carboxamido)-p-hydroxy-m-methylbenzylpenicillin and non-toxic pharmaceutically acceptable salts thereof.
Claim 42
Dependent Claim
7 words
D-α-(4-Hydroxy-1,5-naphthyridine-3-carboxamido)-p,m-dihydroxybenzylpenicillin and non-toxic pharmaceutically acceptable salts thereof.
Claim 43
Dependent Claim
7 words
D-α-(4-Hydroxy-1,5-naphthyridine-3-carboxamido)-p,m-dihydroxybenzylpenicillin and non-toxic pharmaceutically acceptable salts thereof.
Claim 44
Dependent Claim
7 words
D-α-(4-Hydroxy-1,5-naphthyridine-3-carboxamido)-p-hydroxy-m-methoxybenzylpenicillin and non-toxic pharmaceutically acceptable salts thereof.
Claim 45
Dependent Claim
7 words
D-α-(4-Hydroxy-1,5-naphthyridine-3-carboxamido)-p-hydroxy-m-methoxybenzylpenicillin and non-toxic pharmaceutically acceptable salts thereof.
References Cited (Backward Citations)
US2985648A
Cited
US3268513A
Cited
US3454557A
Cited
US3381001A
Cited
US3579501A
Cited
US3864329A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-11-16 | 1980-05-17 | 1980-11-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-11-16 | 1984-05-17 | 1984-11-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-11-16 | 1988-05-17 | 1988-11-16 | $7700.00 | Window Closed / Lapsed |