CA2103845A1 - 9-[(substituted glycyl)-amido]-6-demethyl-6-deoxytetracyclines - Google Patents

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

Info

Publication number
CA2103845A1
CA2103845A1 CA002103845A CA2103845A CA2103845A1 CA 2103845 A1 CA2103845 A1 CA 2103845A1 CA 002103845 A CA002103845 A CA 002103845A CA 2103845 A CA2103845 A CA 2103845A CA 2103845 A1 CA2103845 A1 CA 2103845A1
Authority
CA
Canada
Prior art keywords
deoxytetracyclines
demethyl
amido
substituted glycyl
glycyl
Prior art date
Legal status (The legal status 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 status listed.)
Granted
Application number
CA002103845A
Other languages
French (fr)
Other versions
CA2103845C (en
Inventor
Phaik-Eng Sum
Ving J. Lee
Raymond T. Testa
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Wyeth Holdings LLC
Original Assignee
Phaik-Eng Sum
Ving J. Lee
Raymond T. Testa
American Cyanamid Company
Wyeth Holdings Corporation
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.)
Filing date
Publication date
Application filed by Phaik-Eng Sum, Ving J. Lee, Raymond T. Testa, American Cyanamid Company, Wyeth Holdings Corporation filed Critical Phaik-Eng Sum
Publication of CA2103845A1 publication Critical patent/CA2103845A1/en
Application granted granted Critical
Publication of CA2103845C publication Critical patent/CA2103845C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/40—Acylated substituent nitrogen atom
    • 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
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/24—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups 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 carbon skeleton
    • C07C237/26—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups 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 carbon skeleton of a ring being part of a condensed ring system formed by at least four rings, e.g. tetracycline
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C239/00—Compounds containing nitrogen-to-halogen bonds; Hydroxylamino compounds or ethers or esters thereof
    • C07C239/08—Hydroxylamino compounds or their ethers or esters
    • C07C239/18—Hydroxylamino compounds or their ethers or esters having nitrogen atoms of hydroxylamino groups further bound to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C239/00—Compounds containing nitrogen-to-halogen bonds; Hydroxylamino compounds or ethers or esters thereof
    • C07C239/08—Hydroxylamino compounds or their ethers or esters
    • C07C239/20—Hydroxylamino compounds or their ethers or esters having oxygen atoms of hydroxylamino groups etherified
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/15—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
    • C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
    • C07D295/24—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
    • C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
    • C07C2603/44—Naphthacenes; Hydrogenated naphthacenes
    • C07C2603/46—1,4,4a,5,5a,6,11,12a- Octahydronaphthacenes, e.g. tetracyclines

Abstract

The invention provides compounds of the formula:
(see formula I) wherein R, R1 and W are defined in the specification.
These compounds are useful as antibiotic agents.
CA002103845A 1992-08-13 1993-08-11 9-[(substituted glycyl)-amido]-6-demethyl-6-deoxytetracyclines Expired - Fee Related CA2103845C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US07/928,590 US5442059A (en) 1992-08-13 1992-08-13 9-[(substituted glycyl)amido)]-6-demethyl-6-deoxytetracyclines
US07/928,590 1992-08-13

Publications (2)

Publication Number Publication Date
CA2103845A1 true CA2103845A1 (en) 1994-02-14
CA2103845C CA2103845C (en) 2005-05-17

Family

ID=25456487

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002103845A Expired - Fee Related CA2103845C (en) 1992-08-13 1993-08-11 9-[(substituted glycyl)-amido]-6-demethyl-6-deoxytetracyclines

Country Status (28)

Country Link
US (3) US5442059A (en)
EP (1) EP0582829B1 (en)
JP (1) JP3633640B2 (en)
KR (1) KR100309541B1 (en)
CN (1) CN1033971C (en)
AT (1) ATE205472T1 (en)
AU (1) AU680616B2 (en)
BR (1) BR1100987A (en)
CA (1) CA2103845C (en)
CZ (1) CZ288174B6 (en)
DE (1) DE69330733T2 (en)
DK (1) DK0582829T3 (en)
ES (1) ES2161220T3 (en)
FI (1) FI116055B (en)
HK (1) HK1009960A1 (en)
HU (3) HU212265B (en)
IL (3) IL106672A (en)
MX (1) MX9304756A (en)
NO (1) NO304884B1 (en)
NZ (1) NZ248342A (en)
PH (1) PH30006A (en)
PL (3) PL173448B1 (en)
PT (1) PT582829E (en)
RU (1) RU2123999C1 (en)
SG (1) SG52326A1 (en)
SK (1) SK281974B6 (en)
TW (1) TW269678B (en)
ZA (1) ZA935890B (en)

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HU211501A9 (en) 1995-11-28
ES2161220T3 (en) 2001-12-01
PL300068A1 (en) 1994-02-21
SK281974B6 (en) 2001-09-11
US5495030A (en) 1996-02-27
HU215445B (en) 2000-12-28
IL106672A0 (en) 1993-12-08
HU9401974D0 (en) 1994-09-28
HU9302335D0 (en) 1993-10-28
FI933568A0 (en) 1993-08-12
CZ157493A3 (en) 1994-03-16
PH30006A (en) 1996-10-29
IL119698A0 (en) 1997-02-18
PT582829E (en) 2002-01-30
HUT71594A (en) 1996-01-29
US5567692A (en) 1996-10-22
BR1100987A (en) 1999-12-07
DE69330733D1 (en) 2001-10-18
FI933568A (en) 1994-02-14
ATE205472T1 (en) 2001-09-15
DE69330733T2 (en) 2002-07-04
KR100309541B1 (en) 2002-08-31
PL174108B1 (en) 1998-06-30
RU2123999C1 (en) 1998-12-27
HU212265B (en) 1996-04-29
TW269678B (en) 1996-02-01
IL119698A (en) 1998-09-24
EP0582829A1 (en) 1994-02-16
EP0582829B1 (en) 2001-09-12
CN1033971C (en) 1997-02-05
CN1087899A (en) 1994-06-15
IL106672A (en) 1998-02-22
SG52326A1 (en) 1998-09-28
US5442059A (en) 1995-08-15
NO932873L (en) 1994-02-14
PL173448B1 (en) 1998-03-31
HK1009960A1 (en) 1999-06-11
NO304884B1 (en) 1999-03-01
JPH06199758A (en) 1994-07-19
HUT66660A (en) 1994-12-28
DK0582829T3 (en) 2001-10-15
ZA935890B (en) 1994-03-11
FI116055B (en) 2005-09-15
PL174073B1 (en) 1998-06-30
SK84893A3 (en) 1994-06-08
NZ248342A (en) 1995-07-26
JP3633640B2 (en) 2005-03-30
NO932873D0 (en) 1993-08-12
AU4461193A (en) 1994-02-17
MX9304756A (en) 1994-02-28
KR940003908A (en) 1994-03-14
CA2103845C (en) 2005-05-17
CZ288174B6 (en) 2001-05-16
AU680616B2 (en) 1997-08-07

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