US 5,401,729 AGranted

7-(substituted)-9-[(substituted glycyl)amido]-6-demethyl-6-deoxytetracyclines

AssigneeAmerican Cyanamid Company

InventorsPhaik-Eng Sum, Ving J. Lee, Raymond T. Testa

Life of this patent

Estimating the term…

Abstract

The invention provides compounds of the formula: ##STR1## wherein R, R.sup.3, R.sup.4 and W are defined in the specification. These compounds are useful as antibiotic agents.

Claims18

Dependent claims

A compound selected from the group consisting of:

[4S- (4alpha,12aalpha)]-9-[[[(Cyclopropylmethyl)amino]acetyl]amino]-4-, 7-bis(dimethylamino)-1,4,4a,5,5a,6,11, 12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide dihydrochloride;
[4S-(4alpha,12aalpha)]-9-[[[(2,2-diethoxyethyl)amino]acetyl]amino]-4,7-bis( dimethylamino)-1,4,4a,5,5a,6,11, 12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide dihydrochloride;
[4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-1,4,4a,5,5a, 6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-9-[[[2-(methoxyethyl)amino]ace tyl]amino]-1,11-dioxo-2-naphthacenecarboxamide dihydrochloride;
[4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydr o-3,10,12,12a-tetrahydroxy-9-[[[(3-methoxypropyl)amino]acetyl]amino]-1,11-d ioxo-2-naphthacenecarboxamide dihydrochloride;
[4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-9-[[(heptylamino)acetyl]amino ]-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naph thacenecarboxamide dihydrochloride;
[4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-1,4,4a, 5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-9-[[(undecylam ino)acetyl]amino]-2-naphthacenecarboxamide dihydrochloride;
[4S-(4alpha,12aalpha)]-4,7-bis(dimethylamino)-1,4,4a, 5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-9-[[[(2-pyridi nylmethyl)amino]acetyl]amino]-2-naphthacenecarboxamide dihydrochloride;
[4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydr o-3,10,12,12a-tetrahydroxy-9-[[[(2-hydroxyethyl)amino]acetyl]amino]-1,11-di oxo-2-naphthacenecarboxamide monohydrochloride;
[4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydr o-3,10,12,12a-tetrahydroxy-9-[[[(2-hydroxyethyl)methylamino]acetyl]amino-1, 11-dioxo-2-naphthacenecarboxamide;
[4S-(4alpha,12aalpha)]-4,7- Bis(dimethylamino)-1,4,4a,5,5a, 6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-9-[[[(4-(hydroxybutyl)amino]ac etyl]amino]-1-11-dioxo-2-naphthacenecarboxamide;
[4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydr o-3,10,12,12a-tetrahydroxy-1,11-dioxo-9-[[[2,2,2-trifluoroethyl)amino]-2-na phthacenecarboxamide;
[4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-9-[[[(2-fluoroethyl)amino]ace tyl]amino]-1,4,4a,5,5a,6, 11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxam ide;
[4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydr o-3,10,12,12a-tetrahydroxy-1,11-dioxo-9-[[[[2-(1-piperidinyl)ethyl]amino]ac etyl]amino]-2-naphthacenecarboxamide;
[4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydr o-3,10,12,12a-tetrahydroxy-9-[[[methyl-2-propynylamino]acetyl]amino]-1,11-d ioxo-2-naphthacenecarboxamide;
[4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-1,4,4a, 5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1, 11-dioxo-9-[[[(phenylmethoxy)-amino]acetyl]amino]-2-naphthacenecarboxamide

12 more elements

Dependencies are inferred from the claim text.

Facts

Application: 08/201,306Filed 24 Feb 1994 · division
Priority: 13 Aug 1992
Granted: 28 Mar 1995
Term ends: Not estimatedThe source records don’t support an estimate.

Classification12 codes

C07D 295/30
Nitrogen atoms: non-acylated
A61P 31/04
Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics: antibacterial agents
C07C 237/26
Having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the…:…
C07D 207/16
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,…:…

Family

Serial928,589Parent of this division · filed 13 Aug 1992
US 5,328,902 AParent of this division
US 5,401,729 AThis patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

The invention provides compounds of the formula: ##STR1## wherein R, R.sup.3, R.sup.4 and W are defined in the specification. These compounds are useful as antibiotic agents.

A compound selected from the group consisting of:

[4S- (4alpha,12aalpha)]-9-[[[(Cyclopropylmethyl)amino]acetyl]amino]-4-, 7-bis(dimethylamino)-1,4,4a,5,5a,6,11, 12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide dihydrochloride;
[4S-(4alpha,12aalpha)]-9-[[[(2,2-diethoxyethyl)amino]acetyl]amino]-4,7-bis( dimethylamino)-1,4,4a,5,5a,6,11, 12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide dihydrochloride;
[4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-1,4,4a,5,5a, 6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-9-[[[2-(methoxyethyl)amino]ace tyl]amino]-1,11-dioxo-2-naphthacenecarboxamide dihydrochloride;
[4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydr o-3,10,12,12a-tetrahydroxy-9-[[[(3-methoxypropyl)amino]acetyl]amino]-1,11-d ioxo-2-naphthacenecarboxamide dihydrochloride;
[4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-9-[[(heptylamino)acetyl]amino ]-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naph thacenecarboxamide dihydrochloride;
[4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-1,4,4a, 5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-9-[[(undecylam ino)acetyl]amino]-2-naphthacenecarboxamide dihydrochloride;
[4S-(4alpha,12aalpha)]-4,7-bis(dimethylamino)-1,4,4a, 5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-9-[[[(2-pyridi nylmethyl)amino]acetyl]amino]-2-naphthacenecarboxamide dihydrochloride;
[4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydr o-3,10,12,12a-tetrahydroxy-9-[[[(2-hydroxyethyl)amino]acetyl]amino]-1,11-di oxo-2-naphthacenecarboxamide monohydrochloride;
[4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydr o-3,10,12,12a-tetrahydroxy-9-[[[(2-hydroxyethyl)methylamino]acetyl]amino-1, 11-dioxo-2-naphthacenecarboxamide;
[4S-(4alpha,12aalpha)]-4,7- Bis(dimethylamino)-1,4,4a,5,5a, 6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-9-[[[(4-(hydroxybutyl)amino]ac etyl]amino]-1-11-dioxo-2-naphthacenecarboxamide;
[4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydr o-3,10,12,12a-tetrahydroxy-1,11-dioxo-9-[[[2,2,2-trifluoroethyl)amino]-2-na phthacenecarboxamide;
[4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-9-[[[(2-fluoroethyl)amino]ace tyl]amino]-1,4,4a,5,5a,6, 11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxam ide;
[4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydr o-3,10,12,12a-tetrahydroxy-1,11-dioxo-9-[[[[2-(1-piperidinyl)ethyl]amino]ac etyl]amino]-2-naphthacenecarboxamide;
[4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydr o-3,10,12,12a-tetrahydroxy-9-[[[methyl-2-propynylamino]acetyl]amino]-1,11-d ioxo-2-naphthacenecarboxamide;
[4S-(4alpha,12aalpha)]-4,7-Bis(dimethylamino)-1,4,4a, 5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1, 11-dioxo-9-[[[(phenylmethoxy)-amino]acetyl]amino]-2-naphthacenecarboxamide

12 more elements

Facts

Application

08/201,306Filed 24 Feb 1994 · division

Priority

13 Aug 1992

Granted

28 Mar 1995

Term ends

Not estimatedThe source records don’t support an estimate.

Classification12 codes

C07D 295/30
Nitrogen atoms: non-acylated
A61P 31/04
Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics: antibacterial agents
C07C 237/26
Having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the…:…
C07D 207/16
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,…:…