Claims
- 1. A compound of the formula ##STR91## wherein A is amino substituted by
- (1) C.sub.1 to C.sub.10 alkanoyl,
- (2) C.sub.1 to C.sub.7 haloalkanoyl,
- (3) azidoacetyl, cyanoacetyl, trifluoromethylthioacetyl, cyanomethylthioacetyl, or (4-pyridon-1-yl)acetyl;
- (4) acyl group of the following formula:
- Ar--CO--
- wherein Ar is an aryl selected from furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, oxadiazolyl, oxatriazolyl, thiazolyl, isothiazolyl, thiadiazolyl, thiatriazolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, phenyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, dihydrophenyl, tetrahydrophenyl, tetrahydropyrimidyl, naphthyl, benzothiazolyl, indolyl, quinolyl, isoquinolyl, benzopyrimidyl, cinnolinyl, pyridopyrimidyl, or indanyl ring group;
- (5) acyl group of the following formula:
- Ar--CQQ'--CO--
- wherein Ar is as defined above and Q and Q' each is hydrogen or methyl;
- (6) acyl group of the following formula:
- Ar--G--CQQ'--CO--
- wherein Ar, Q, and Q' each is as defined above and G is oxygen, sulfur, or imino;
- (7) acyl group of the following formula: ##STR92## wherein Ar is as defined above and T.sup.1 is hydrogen or C.sub.1 to C.sub.6 alkyl;
- (8) acyl group of the following formula: ##STR93## wherein Ar is as defined above and T.sup.2 is one of (i) hydroxy or C.sub.1 to C.sub.10 acyloxy, (ii) carboxy or protected carboxy, (iii) sulfo or C.sub.1 to C.sub.5 alkoxysulfonyl, or a group of the formula: ##STR94## in which W.sup.1 and W.sup.2 each is hydrogen or a C.sub.1 to C.sub.15 aminosubstituent;
- (9) 5-aminoadipoyl, 5-aminoadipoyl protected at the amino or 5-aminoadipoyl protected at the carboxy;
- (10) acyl group of the following formula:
- L--O--CO--
- wherein L is an easily removable and unsubstituted or substituted C.sub.1 to C.sub.10 hydrocarbyl group; or
- (11) C.sub.1 to C.sub.20 optionally substituted hydrocarbyl, C.sub.3 to C.sub.10 organic silyl, or C.sub.1 to C.sub.10 sulfenyl, the carboxy protecting group B in said COB is C.sub.1 to C.sub.10 alkoxy, C.sub.1 to C.sub.6 haloalkoxy, C.sub.3 to C.sub.10 acylalkoxy, C.sub.3 to C.sub.10 alkoxyalkoxy, C.sub.2 to C.sub.10 aminoalkoxy, aryloxy, aralkoxy, C.sub.1 to C.sub.10 alkylsilyloxy, C.sub.1 to C.sub.10 alkylstannyloxy, C.sub.1 to C.sub.10 acyloxy, inorganic acyloxy, metal oxy of a group I, II, or III metal in the periodical table, C.sub.1 to C.sub.15 hydrocarbylammoniooxy, C.sub.1 to C.sub.10 hydrocarbylthio or mercapto, C.sub.1 to C.sub.5 alkylamino, di-C.sub.1 to C.sub.5 alkylamino, hydrazinyl, or azido;
- E is .beta.-hydrogen or .alpha.-methoxy;
- X is hydrogen, halo, hydroxy, C.sub.1 to C.sub.4 alkanoyloxy, substituted C.sub.1 to C.sub.4 alkanoyloxy, aroyloxy, carbonic acyloxy, C.sub.1 to C.sub.6 alkoxy, aralkoxy of the formula Ar--CH.sub.2 O-- or aryloxy of the formula Ar--O-- in which Ar is as defined above, mercapto, C.sub.1 to C.sub.5 alkanoylthio, aroylthio, C.sub.1 to C.sub.6 -alkylthio, aralkylthio, arylthio of the formula Ar--S-- in which Ar is as defined above, amino, azido, hydrazinyl, acetylamino, methylamino, pyridinium, picolinium, 4-carboxypyridinium, carbamoylpyridinium, hydroxymethylpyridinium, carboxymethylpyridinium, or chloropyridinium, COB is carboxy or protected carboxy, and
- Z is halo, hydroxy, alkanoyloxy, haloalkanoyloxy, arylsulfenyl, arylselenyl, arylsulfinyl, alkylsulfinyl, alkanesulfonyloxy, or arylsulfonyloxy.
- 2. A compound as claimed in claim 1, wherein A is benzoylamino, methylbenzoylamino, chlorobenzoylamino, nitrobenzoylamino, cyanobenzoylamino, phenoxyacetamido, phenylacetamido, diphenylmethoxycarbonylphenylacetamido, or amino;
- B is hydroxy, benzyloxy, tolylmethoxy, chlorobenzyloxy, diphenylmethoxy, naphthylmethoxy, t-butoxy, or trimethylsilyloxy;
- X is chloro, bromo, hydroxy, acetoxy, methanesulfonyloxy, methylthio, 1-methyltetrazol-5-ylthio, or hydrogen; and
- Z is chloro, bromo, hydroxy, or acetoxy.
- 3. A compound as claimed in claim 1, wherein
- A=benzoylamino, COB=carboxy, E=.beta.-hydrogen, and X=Z=chloro;
- A=benzamido, COB=carboxy, E=.beta.-hydrogen, and X=Z=bromine;
- A=benzamido, COB=benzyloxycarbonyl, E=.beta.-hydrogen, and X=Z=chlorine;
- A=benzamido, COB=benzyloxycarbonyl, E=.beta.-hydrogen, and X=Z=bromine;
- A=benzamido, COB=diphenylmethoxycarbonyl, E=.beta.-hydrogen, and X=hydrogen, and Z=hydroxy;
- A=benzamido, COB=diphenylmethoxycarbonyl, E=.beta.-hydrogen, X=hydrogen; and Z=.alpha.-acetoxy;
- A=benzamido, COB=diphenylmethoxycarbonyl, E=.beta.-hydrogen, X=hydrogen, and Z=bromine;
- A=benzamido, COB=diphenylmethoxycarbonyl, E=.beta.-hydrogen, and X=Z=hydroxy;
- A=benzamido, COB=diphenylmethoxycarbonyl, E=.beta.-hydrogen, X=acetoxy, and Z=hydroxy;
- A=benzamido, COB=diphenylmethoxycarbonyl, E=.beta.-hydrogen, X=hydroxy, and Z=methanesulfonyloxy,
- A=benzamido, COB=diphenylmethoxycarbonyl, E=.beta.-hydrogen, X=chlorine, and Z=hydroxy;
- A=benzamido, COB=diphenylmethoxycarbonyl, E=.beta.-hydrogen, and X=Z=chlorine;
- A=benzamido, COB=diphenylmethoxycarbonyl, E=.beta.-hydrogen, X=methylthio, and Z=chlorine;
- A=benzamido, COB=diphenylmethoxycarbonyl, E=.beta.-hydrogen, X=1-methyltetrazolylthio, and Z=hydroxy;
- A=benzamido, COB=diphenylmethoxycarbonyl, E=.beta.-hydrogen, X=1-methyltetrazolylthio, and Z=chlorine;
- A=benzamido, COB=diphenylmethoxycarbonyl, E=.beta.-hydrogen, X=bromine, and Z=hydroxy;
- A=benzamido, COB=diphenylmethoxycarbonyl, E=.beta.-hydrogen, and X=Z=bromine;
- A=p-methylbenzamido, COB=diphenylmethoxycarbonyl, E=.beta.-hydrogen, and X=Z=chlorine;
- A=p-chlorobenzamido, COB=diphenylmethoxycarbonyl, E=.beta.-hydrogen, and X=Z=chlorine;
- A=p-cyanobenzamido, COB=diphenylmethoxycarbonyl, E=.beta.-hydrogen, and X=Z=chlorine,
- A=p-nitrobenzamido, COB=diphenylmethoxycarbonyl, E=.beta.-hydrogen, and X=Z=chlorine;
- A=phenoxyacetamido, COB=diphenylmethoxycarbonyl, E=.beta.-hydrogen, and X=Z=chlorine;
- A=phenylacetamido, COB=t-butoxycarbonyl, E=.beta.-hydrogen, and X=Z=chlorine;
- A=phenylacetamido, COB=benzyloxycarbonyl, E=.beta.-hydrogen, and X=Z=chlorine;
- A=benzamido, COB=carboxy, E=.alpha.-methoxy, X=hydrogen, and Z=hydroxy;
- A=benzamido, COB=carboxy, E=.alpha.-methoxy, X=hydrogen, and Z=acetoxy;
- A=benzamido, COB=carboxy, E=.alpha.-methoxy, X=hydrogen, and Z=trifluoroacetoxy;
- A=benzamido, COB=benzyloxycarbonyl, E=.alpha.-methoxy, and X=Z=chlorine;
- A=benzamido, COB=benzyloxycarbonyl, E=.alpha.-methoxy, and X=Z=bromine;
- A=benzamido, COB=diphenylmethoxycarbonyl, E=.alpha.-methoxy, X=hydrogen, and Z=hydroxy;
- A=benzamido, COB=diphenylmethoxycarbonyl, E=.alpha.-methoxy, X=hydrogen, and Z=acetoxy;
- A=benzamido, COB=diphenylmethoxycarbonyl, E=.alpha.-methoxy, X=hydrogen, and Z=trifluoroacetoxy;
- A=benzamido, COB=diphenylmethoxycarbonyl, E=.alpha.-methoxy, and X=Z=chlorine;
- A=benzamido, COB=diphenylmethoxycarbonyl, E=.alpha.-methoxy, and X=Z=bromine;
- A=p-chlorobenzamido, COB=diphenylmethoxycarbonyl, E=.alpha.-methoxy, X=I-methyltetrazolylthio, and X=chlorine;
- A=p-cyanobenzamido, COB=diphenylmethoxycarbonyl, E=.alpha.-methoxy, X=1-methyltetrazolylthio, and Z=chlorine;
- A=p-nitrobenzamido, COB=diphenylmethoxycarbonyl, E=.alpha.-methoxy, X=1-methyltetrazolylthio, and X=chlorine;
- A=p-methylbenzamido, COB=diphenylmethoxycarbonyl, E=.alpha.-methoxy, X=1-methyltetrazolylthio, and Z=chlorine;
- A=p-chlorobenzamido, COB=diphenylmethoxycarbonyl, E=.alpha.-methoxy, and X=Z=chlorine,
- A=p-cyanobenzamido, COB=diphenylmethoxycarbonyl, E=.alpha.-methoxy, and X=Z=chlorine,
- A=p-nitrobenzamido, COB=diphenylmethoxycarbonyl, E=.alpha.-methoxy, and X=Z=chlorine;
- A=p-methylbenzamido, COB=diphenylmethoxycarbonyl, E=.alpha.-methoxy, and X=Z=chlorine;
- A=benzamido, COB=p-methylbenzyloxycarbonyl, E=.alpha.-methoxy, X=1-methyltetrazolylthio, and Z=chlorine;
- A=benzamido, COB=p-chlorobenzyloxycarbonyl, E=.alpha.-methoxy, X=1-methyltetrazolylthio, and Z=chlorine;
- A=benzamido, COB=naphthylmethoxycarbonyl, E=.alpha.-methoxy, X=1-methyltetrazolylthio, and Z=chlorine; or
- A=.alpha.-diphenylmethoxycarbonyl-phenylacetamido, COB=diphenylmethoxycarbonyl, E=.alpha.-methoxy, and X=Z=chlorine.
- 4. A compound according to claim 1 wherein
- A is benzoylamino,
- COB is carboxy,
- E is .beta.-hydrogen, and
- X and Z are chloro.
Priority Claims (2)
Number |
Date |
Country |
Kind |
52-15813 |
Feb 1977 |
JPX |
|
52-67025 |
Jun 1977 |
JPX |
|
Parent Case Info
This is a continuation-in-part of application Ser. No. 322,662, filed Nov. 18, 1981, (now U.S. Pat. No. 4,366,316) which is a continuation of application Ser. No. 72,600, filed Sept. 5, 1979 (now abandoned), which is a continuation of application Ser. No. 877,811, filed Feb. 14, 1978 (now abandoned).
US Referenced Citations (9)
Continuations (2)
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Number |
Date |
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Parent |
72600 |
Sep 1979 |
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Parent |
877811 |
Feb 1978 |
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Continuation in Parts (1)
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Number |
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322662 |
Nov 1981 |
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