Claims
- 1. A compound of the following formula: ##STR67## wherein
- R represents (a) 1-6C alkyl, (b) 7-15C aralkyl, (c) 7-15C heterocyclicalkyl, (d) 7-9C aryloxyalkyl, (e) 7-9C heterocyclicoxyalkyl, (f) 6-10C aryl, (g) 6-10C heterocyclic, (h) 1-6C alkoxy, (i) 7-15C aralkoxy, (j) 7-15C heterocyclicalkoxy, (k) 6-10C aryloxy, (l) 6-10C heterocyclicoxy, (m) carbamoyl, or (n) 2-7C carbalkoxy, each of said groups being unsubstituted or substituted by hydroxy, 1-6C alkanoyloxy, 1-3C alkoxy, 7-9C aralkoxy, 6-8C aryloxy, oxo, amino, 1-3C alkylamino, 1-5C alkanoylamino, nitro, 1-3C alkyl, 6-10C aryl, carboxy, protected carboxy, cyano or halo,
- X represents (a) halo, (b) hydroxy, (c) up to 5C acyloxy selected from the group of nitrooxy, sulfurous acyloxy, formyloxy, acetoxy, propionyloxy, trifluoroacetoxy, .beta.-hydroxypropionyloxy, .alpha.-haloacetyloxy, benzyloxy, nicotinoyloxy, carbamoyloxy, methoxycarbonyloxy, aminopropionyloxy, sulfenyloxy and sulfinyloxy, (d) 1-6C alkoxy, (e) thiocarbamoylthio, (f) 1-5 C alkylthio, (g) 6-9C arylthio, (h) 6-9C heterocyclicthio, or (i) 1-6C sulfinyl, the aryl portion of the groups R and X and the substituents thereof being selected from the group of phenyl and naphthyl and the heterocyclic portion of the groups R and X being selected from the group consisting of furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, oxadiazolyl, oxatriazolyl, thiazolyl, isothiazolyl, thiadiazolyl, thiatriazolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidyl, pyrazinyl, as-triazinyl, quinolyl, isoquinolinyl, and 2-benzothiazolyl, and COB is carboxy or protected carboxy conventional in the chemistry of penicillins and cephalosporins.
- 2. A compound claimed in claim 1, wherein R is benzyl, phenoxymethyl, or phenyl optionally substituted by methyl, ethyl, propyl, isopropyl, chloro, bromo, cyano, methoxy, ethoxy, propoxy, or nitro.
- 3. A compound claimed in claim 1, wherein X is hydroxy, chloro, bromo, iodo, nitroxy, sulfoxy, formyloxy, acetoxy, trifluoroacetoxy, trichloroacetoxy, propionyloxy, butyryloxy, phenylthio, methylthio, ethylthio, methyltetrazolylthio, 1-dimethylaminoethyltetrazolylthio, 1-carboxyethyltetrazolylthio, 1-carboxymethyltetrazolylthio, thiadiazolylthio, methylthiadiazolylthio, 1-methyl-5-hydroxy-6-oxo-1,6-dihydro-1,3,4-triazin-2-ylthio, phenylsulfinyl, or methylsulfinyl.
- 4. A compound claimed in claim 1, wherein X is hydroxy, chloro, bromo, iodo, or nitroxy.
- 5. A compound claimed in claim 1, wherein R is phenyl, methylphenyl, methoxyphenyl, chlorophenyl, nitrophenyl, cyanophenyl, benzyl, phenoxymethyl, methyl, ethyl, propyl, or butyl; and X is hydrogen, chloro, bromo, iodo, hydroxy, nitroxy, formyloxy, acetoxy, methylthio, ethylthio, phenylthio, methyltetrazolylthio, carboxymethyltetrazolylthio, thiadiazolylthio, methylthiadiazolylthio, triazolylthio, 1-methyl-5-hydroxy-6-oxo-1,6-dihydrotriazin-2-ylthio, or phenylsulfinyl, and COB is conventionally protected carboxy available in the chemistry of penicillins and cephalosporins.
- 6. A compound claimed in claim 1, wherein
- (1) R is phenyl, X is hydrogen, and COB is carboxy;
- (2) R is phenyl, X is chloro, and COB is carboxy;
- (3) R is phenyl, X is bromo, and COB is carboxy;
- (4) R is phenyl, X is iodo, and COB is carboxy;
- (5) R is phenyl, X is nitroxy, and COB is carboxy;
- (6) R is phenyl, X is formyloxy, and COB is carboxy;
- (7) R is phenyl, X is acetoxy, and COB is carboxy;
- (8) R is phenyl, X is methylthio, and COB is carboxy;
- (9) R is phenyl, X is ethylthio, and COB is carboxy;
- (10) R is phenyl, X is phenylthio, and COB is carboxy;
- (11) R is phenyl, X is methyltetrazolylthio, and COB is carboxy;
- (12) R is phenyl, X is 1-carboxymethyltetrazol-5-ylthio, and COB is carboxy;
- (13) R is phenyl, X is thiadiazol-5-ylthio, and COB is carboxy;
- (14) R is phenyl, X is methylthiadiazolylthio, and COB is carboxy;
- (15) R is phenyl, X is triazolylthio, COB is carboxy;
- (16) R is phenyl, X is 1-methyl-5-hydroxy-6-oxo-1,6-dihydrox-1,3,4-triazin-2-ylthio, and COB is carboxy;
- (17) R is phenyl, X is phenylsulfinyl, and COB is carboxy;
- (18) R is tolyl, X is hydrogen, and COB is carboxy;
- (19) R is tolyl, X is chloro, and COB is carboxy;
- (20) R is tolyl, X is bromo, and COB is carboxy;
- (21) R is tolyl, X is iodo, and COB is carboxy;
- (22) R is tolyl, X is hydroxy, and COB is carboxy;
- (23) R is tolyl, X is nitroxy, and COB is carboxy;
- (24) R is tolyl, X is formyloxy, and COB is carboxy;
- (25) R is tolyl, X is acetoxy, and COB is carboxy;
- (26) R is tolyl, X is methylthio, and COB is carboxy;
- (27) R is tolyl, X is ethylthio, and COB is carboxy;
- (28) R is tolyl, X is phenylthio, and COB is carboxy;
- (29) R is tolyl, X is 1-methyltetrazolylthio, and COB is carboxy;
- (30) R is tolyl, X is 1-carboxymethyltetrazol-5-ylthio, and COB is carboxy;
- (31) R is tolyl, X is thiadiazol-5-ylthio, and COB is carboxy;
- (32) R is tolyl, X is methylthiadiazolylthio, and COB is carboxy;
- (33) R is tolyl, X is triazol-4-ylthio, and COB is carboxy;
- (34) R is tolyl, X is 1-methyl-5-hydroxy-6-oxo-1,6-dihydro-1,3,4-triazin-2-ylthio, and COB is carboxy;
- (35) R is tolyl, X is phenylsulfinyl, and COB is carboxy;
- (36) R is methoxyphenyl, X is hydrogen, and COB is carboxy;
- (37) R is methoxyphenyl, X is chloro, and COB is carboxy;
- (38) R is methoxyphenyl, X is bromo, and COB is carboxy;
- (39) R is methoxyphenyl, X is iodo, and COB is carboxy;
- (40) R is methoxyphenyl, X is hydroxy, and COB is carboxy;
- (41) R is methoxyphenyl, X is nitroxy, and COB is carboxy;
- (42) R is methoxyphenyl, X is formyloxy, and COB is carboxy;
- (43) R is methoxyphenyl, X is acetoxy, and COB is carboxy;
- (44) R is methoxyphenyl, X is propionyloxy, and COB is carboxy;
- (45) R is methoxyphenyl, X is methylthio, and COB is carboxy;
- (46) R is methoxyphenyl, X is phenylthio, and COB is carboxy;
- (47) R is methoxyphenyl, X is methyltetrazolylthio, and COB is carboxy;
- (48) R is methoxyphenyl, X is 1-carboxymethyltetrazol-5-ylthio, and COB is carboxy;
- (49) R is methoxyphenyl, X is thiadiazolylthio, and COB is carboxy;
- (50) R is methoxyphenyl, X is methylthiadiazolylthio, and COB is carboxy;
- (51) R is methoxyphenyl, X is triazol-4-ylthio, and COB is carboxy;
- (52) R is methoxyphenyl, X is 1-methyl-5-hydroxy-6-oxo-1,6-dihydro-1,3,4-triazin-2-ylthio, and COB is carboxy;
- (53) R is methoxyphenyl, X is phenylsulfinyl, and COB is carboxy;
- (54) R is chlorophenyl, X is hydrogen, and COB is carboxy;
- (55) R is chlorophenyl, X is chloro, and COB is carboxy;
- (56) R is chlorophenyl, X is bromo, and COB is carboxy;
- (57) R is chlorophenyl, X is iodo, and COB is carboxy;
- (58) R is chlorophenyl, X is hydroxy, and COB is carboxy;
- (59) R is chlorophenyl, X is nitroxy, and COB is carboxy;
- (60) R is chlorophenyl, X is formyloxy, and COB is carboxy;
- (61) R is chlorophenyl, X is acetoxy, and COB is carboxy;
- (62) R is chlorophenyl, X is propylthio, and COB is carboxy;
- (63) R is chlorophenyl, X is phenylthio, and COB is carboxy;
- (64) R is chlorophenyl, X is methyltetrazolylthio, and COB is carboxy;
- (65) R is chlorophenyl, X is 1-carboxymethyltetrazolylthio, and COB is carboxy;
- (66) R is chlorophenyl, X is thiadiazolylthio, and COB is carboxy;
- (67) R is chlorophenyl, X is methylthiadiazolylthio, and COB is carboxy;
- (68) R is chlorophenyl, X is triazolylthio, and COB is carboxy;
- (69) R is chlorophenyl, X is 1-ethyl-5-hydroxy-6-oxo-1,6-dihydro-1,3,4-triazin-2-ylthio, and COB is carboxy,
- (70) R is chlorophenyl, X is phenylsulfinyl, and COB is carboxy;
- (71) R is nitrophenyl, X is hydrogen, and COB is carboxy;
- (72) R is nitrophenyl, X is chloro, and COB is carboxy;
- (73) R is nitrophenyl, X is bromo, and COB is carboxy;
- (74) R is nitrophenyl, X is bromo, and COB is carboxy;
- (75) R is nitrophenyl, X is iodo, and COB is carboxy;
- (76) R is nitrophenyl, X is hydroxy, and COB is carboxy;
- (77) R is nitrophenyl, X is nitroxy, and COB is carboxy;
- (78) R is nitrophenyl, X is formyloxy, and COB is carboxy;
- (79) R is nitrophenyl, X is acetoxy, and COB is carboxy;
- (80) R is nitrophenyl, X is methylthio, and COB is carboxy;
- (81) R is nitrophenyl, X is phenylthio, and COB is carboxy;
- (82) R is nitrophenyl, X is methyltetrazolylthio, and COB is carboxy;
- (83) R is nitrophenyl, X is 1-carboxymethyltetrazolylthio, and COB is carboxy;
- (84) R is nitrophenyl, X is thiadiazolylthio, and COB is carboxy;
- (85) R is nitrophenyl, X is methylthiadiazolylthio, and COB is carboxy;
- (86) R is nitrophenyl, X is triazolylthio, and COB is carboxy;
- (87) R is nitrophenyl, X is 1-methyl-5-hydroxy-6-oxo-1,6-dihydro-1,3,4-triazin-2-ylthio, and COB is carboxy;
- (88) R is nitrophenyl, X is phenylsulfinyl, and COB is carboxy;
- (89) R is cyanophenyl, X is hydrogen, and COB is carboxy;
- (90) R is cyanophenyl, X is chloro, and COB is carboxy;
- (91) R is cyanophenyl, X is bromo, and COB is carboxy;
- (92) R is cyanophenyl, X is iodo, and COB is carboxy;
- (93) R is cyanophenyl, X is hydroxy, and COB is carboxy;
- (94) R is cyanophenyl, X is nitroxy, and COB is carboxy;
- (95) R is cyanophenyl, X is formyloxy, and COB is carboxy;
- (96) R is cyanophenyl, X is acetoxy, and COB is carboxy;
- (97) R is cyanophenyl, X is methylthio, and COB is carboxy;
- (98) R is cyanophenyl, X is phenylthio, and COB is carboxy;
- (99) R is cyanophenyl, X is methyltetrazolylthio, and COB is carboxy;
- (100) R is cyanophenyl, X is 1-carboxymethyltetrazolylthio, and COB is carboxy;
- (101) R is cyanophenyl, X is thiadiazolylthio, and COB is carboxy;
- (102) R is cyanophenyl, X is methylthiadiazolylthio, and COB is carboxy;
- (103) R is cyanophenyl, X is triazolylthio, and COB is carboxy;
- (104) R is cyanophenyl, X is 1-methyl-5-hydroxy-6-oxo-1,6-dihydro-1,3,4-triazin-2-ylthio, and COB is carboxy;
- (105) R is cyanophenyl, X is phenylsulfinyl, and COB is carboxy;
- (106) R is benzyl, X is hydrogen, and COB is carboxy;
- (107) R is benzyl, X is chloro, and COB is carboxy;
- (108) R is benzyl, X is bromo, and COB is carboxy;
- (109) R is benzyl, X is iodo, and COB is carboxy;
- (110) R is benzyl, X is hydroxy, and COB is carboxy;
- (111) R is benzyl, X is nitroxy, and COB is carboxy;
- (112) R is benzyl, X is formyloxy, and COB is carboxy;
- (113) R is benzyl, X is acetoxy, and COB is carboxy;
- (114) R is benzyl, X is methylthio, and COB is carboxy;
- (115) R is benzyl, X is trifluoroacetoxy, and COB is carboxy;
- (116) R is benzyl, X is ethylthio, and COB is carboxy;
- (117) R is benzyl, X is phenylthio, and COB is carboxy;
- (118) R is benzyl, X is methyltetrazolylthio, and COB is carboxy;
- (119) R is benzyl, X is 1-carboxymethyltetrazolylthio, and COB is carboxy;
- (120) R is benzyl, X is thiadiazolylthio, and COB is carboxy;
- (121) R is benzyl, X is methylthiadiazolylthio, and COB is carboxy;
- (122) R is benzyl, X is triazolylthio, and COB is carboxy;
- (123) R is benzyl, X is 1-methyl-5-hydroxy-6-oxo-1,6-dihydro-1,3,4-triazin-2-ylthio, and COB is carboxy;
- (124) R is benzyl, X is phenylsulfinylthio, and COB is carboxy;
- (125) R is phenoxymethyl, X is hydrogen, and COB is carboxy;
- (126) R is phenoxymethyl, X is chloro, and COB is carboxy;
- (127) R is phenoxymethyl, X is bromo, and COB is carboxy;
- (128) R is phenoxymethyl, X is iodo, and COB is carboxy;
- (129) R is phenoxymethyl, X is hydroxy, and COB is carboxy;
- (130) R is phenoxymethyl, X is nitroxy, and COB is carboxy;
- (131) R is phenoxymethyl, X is formyloxy, and COB is carboxy;
- (132) R is phenoxymethyl, X is acetoxy, and COB is carboxy;
- (133) R is phenoxymethyl, X is methanesulfonyloxy, and COB is carboxy;
- (134) R is phenoxymethyl, X is methylthio, and COB is carboxy;
- (135) R is phenoxymethyl, X is phenylthio, and COB is carboxy;
- (136) R is phenoxymethyl, X is methyltetrazolylthio, and COB is carboxy;
- (137) R is phenoxymethyl, X is carboxymethyltetrazolylthio, and COB is carboxy;
- (138) R is phenoxymethyl, X is thiadiazolylthio, and COB is carboxy;
- (139) R is phenoxymethyl, X is methylthiadiazolylthio, and COB is carboxy;
- (140) R is phenoxymethyl, X is triazolylthio, and COB is carboxy;
- (141) R is phenoxymethyl, X is 1-methyl-5-hydroxy-6-oxo-1,6-dihydro-triazin-2-ylthio, and COB is carboxy;
- (142) R is phenoxymethyl, X is phenylsulfinyl, and COB is carboxy;
- (145) R is methyl, X is hydrogen, and COB is carboxy;
- (146) R is methyl, X is chloro, and COB is carboxy;
- (147) R is methyl, X is bromo, and COB is carboxy;
- (148) R is methyl, X is iodo, and COB is carboxy;
- (149) R is methyl, X is hydroxy, and COB is carboxy;
- (150) R is methyl, X is nitrooxy, and COB is carboxy;
- (151) R is methyl, X is formyloxy, and COB is carboxy;
- (152) R is methyl, X is methylthio, and COB is carboxy;
- (153) R is methyl, X is phenylthio, and COB is carboxy;
- (154) R is methyl, X is methyltetrazolylthio, and COB is carboxy;
- (155) R is methyl, X is thiadiazolylthio, and COB is carboxy;
- (156) R is methyl, X is methylthiadiazolylthio, and COB is carboxy;
- (157) R is methyl, X is 1-ethyl-5-hydroxy-6-oxo-1,6-dihydro-1,3,4-triazin-2-ylthio, and COB is carboxy;
- (158) R is methyl, X is phenylsulfinyl, and COB is carboxy;
- (159) R is isopropyl, X is chloro, and COB is carboxy;
- (160) R is isopropyl, X is iodo, and COB is carboxy;
- (161) R is isopropyl, X is hydroxy, and COB is carboxy;
- (162) R is t-butyl, X is hydroxy, and COB is carboxy;
- (163) R is t-butyl, X is chloro, and COB is carboxy; or
- (164) R is t-butyl, X is iodo, and COB is carboxy,
- or carboxy protected derivatives thereof in a form of conventional protecting groups available in the chemistry of penicillins and cephalosporins.
Priority Claims (2)
Number |
Date |
Country |
Kind |
52-1760 |
Jan 1977 |
JPX |
|
52-36613 |
Mar 1977 |
JPX |
|
Parent Case Info
This application is a division of application Ser. No. 868,422, filed Jan. 10, 1978 now U.S. Pat. No. 4,220,766.
US Referenced Citations (2)
Number |
Name |
Date |
Kind |
4159984 |
Yoshioka et al. |
Jul 1979 |
|
4183855 |
Yoshioka et al. |
Jan 1980 |
|
Divisions (1)
|
Number |
Date |
Country |
Parent |
868422 |
Jan 1978 |
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