FI933567A - Nya 7-(substituerad)-8-(substituerad)-9-(substituerad amino)-6-demetyl-6-deoxitetracykliner - Google Patents

Nya 7-(substituerad)-8-(substituerad)-9-(substituerad amino)-6-demetyl-6-deoxitetracykliner Download PDF

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Publication number
FI933567A
FI933567A FI933567A FI933567A FI933567A FI 933567 A FI933567 A FI 933567A FI 933567 A FI933567 A FI 933567A FI 933567 A FI933567 A FI 933567A FI 933567 A FI933567 A FI 933567A
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FI
Finland
Prior art keywords
substituted
deoxytetracycline
nya
demethyl
amino
Prior art date
Application number
FI933567A
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English (en)
Other versions
FI933567A0 (fi
Inventor
Phaik-Eng Sum
Ving J Lee
Joseph J Hlavka
Raymond T Testa
Original Assignee
American Cyanamid Co
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 American Cyanamid Co filed Critical American Cyanamid Co
Publication of FI933567A0 publication Critical patent/FI933567A0/fi
Publication of FI933567A publication Critical patent/FI933567A/fi

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    • 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
    • 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
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C243/10—Hydrazines
    • C07C243/20—Hydrazines having nitrogen atoms of hydrazine groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
    • C07C245/20—Diazonium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C247/00—Compounds containing azido groups
    • C07C247/16—Compounds containing azido groups with azido groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C247/18—Compounds containing azido groups with azido groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by carboxyl groups
    • 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
    • C07C271/24—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a ring other than a six-membered aromatic ring
    • 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
    • C07C271/60—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups having oxygen atoms of carbamate groups bound to nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
    • C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Communicable Diseases (AREA)
  • Public Health (AREA)
  • Oncology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Seasonings (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Peptides Or Proteins (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
FI933567A 1992-08-13 1993-08-12 Nya 7-(substituerad)-8-(substituerad)-9-(substituerad amino)-6-demetyl-6-deoxitetracykliner FI933567A (fi)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US92859892A 1992-08-13 1992-08-13

Publications (2)

Publication Number Publication Date
FI933567A0 FI933567A0 (fi) 1993-08-12
FI933567A true FI933567A (fi) 1994-02-14

Family

ID=25456505

Family Applications (1)

Application Number Title Priority Date Filing Date
FI933567A FI933567A (fi) 1992-08-13 1993-08-12 Nya 7-(substituerad)-8-(substituerad)-9-(substituerad amino)-6-demetyl-6-deoxitetracykliner

Country Status (24)

Country Link
US (4) US5430162A (fi)
EP (1) EP0582810B1 (fi)
JP (1) JP3639313B2 (fi)
KR (1) KR100309540B1 (fi)
CN (1) CN1048719C (fi)
AT (1) ATE215530T1 (fi)
AU (1) AU674524B2 (fi)
CA (1) CA2103861C (fi)
CZ (1) CZ289195B6 (fi)
DE (1) DE69331774T2 (fi)
DK (1) DK0582810T3 (fi)
ES (1) ES2173876T3 (fi)
FI (1) FI933567A (fi)
HU (2) HU213269B (fi)
IL (4) IL119750A (fi)
NO (1) NO302568B1 (fi)
NZ (1) NZ248359A (fi)
PH (1) PH31210A (fi)
PL (4) PL174022B1 (fi)
PT (1) PT582810E (fi)
RU (1) RU2127255C1 (fi)
SG (1) SG47520A1 (fi)
SK (1) SK281871B6 (fi)
ZA (1) ZA935892B (fi)

Families Citing this family (59)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
USRE40183E1 (en) 1991-10-04 2008-03-25 Wyeth Holdings Corporation 7-Substituted-9-substituted amino-6-demethyl-6-deoxytetracyclines
US5494903A (en) * 1991-10-04 1996-02-27 American Cyanamid Company 7-substituted-9-substituted amino-6-demethyl-6-deoxytetracyclines
SG47520A1 (en) * 1992-08-13 1998-04-17 American Cyanamid Co New method for the production of 9-amino-6-demethyl-6-deoxytetracycline
US5442059A (en) * 1992-08-13 1995-08-15 American Cyanamid Company 9-[(substituted glycyl)amido)]-6-demethyl-6-deoxytetracyclines
US5420272A (en) * 1992-08-13 1995-05-30 American Cyanamid Company 7-(substituted)-8-(substituted)-9-](substituted glycyl)amido]-6-demethyl-6-deoxytetracyclines
US5248797A (en) * 1992-08-13 1993-09-28 American Cyanamid Company Method for the production of 9-amino-6-demethyl-6-deoxytetracycline
US6506740B1 (en) * 1998-11-18 2003-01-14 Robert A. Ashley 4-dedimethylaminotetracycline derivatives
EA016099B1 (ru) * 1999-09-14 2012-02-28 Трастис Оф Тафтс Коллидж Замещенный аналог тетрациклина (варианты) и способ получения замещенного аналога тетрациклина
US6946118B1 (en) 1999-09-14 2005-09-20 Orapharma, Inc. Formulations for treating or preventing mucositis
US8106225B2 (en) * 1999-09-14 2012-01-31 Trustees Of Tufts College Methods of preparing substituted tetracyclines with transition metal-based chemistries
WO2001074761A1 (en) * 2000-03-31 2001-10-11 Trustees Of Tufts College 7-and 9-carbamate, urea, thiourea, thiocarbamate, and heteroaryl-amino substituted tetracycline compounds
WO2001093891A1 (en) * 2000-06-02 2001-12-13 Yu Liu Non-antibacterial tetracycline as anti-fungal agents
US20020132798A1 (en) * 2000-06-16 2002-09-19 Nelson Mark L. 7-phenyl-substituted tetracycline compounds
WO2001098236A2 (en) * 2000-06-16 2001-12-27 Trustees Of Tufts College 7-phenyl-substituted tetracycline compounds
US6624168B2 (en) * 2000-07-07 2003-09-23 Trustees Of Tufts College 7,8 and 9-substituted tetracycline compounds
EP3461808A1 (en) * 2000-07-07 2019-04-03 Trustees of Tufts College 9-substituted minocycline compounds
EA006170B1 (ru) * 2000-07-07 2005-10-27 Трастис Оф Тафтс Коллидж Замещенные соединения тетрациклина (варианты), фармацевтическая композиция и способ лечения чувствительного к тетрациклину состояния субъекта
US7094806B2 (en) 2000-07-07 2006-08-22 Trustees Of Tufts College 7, 8 and 9-substituted tetracycline compounds
EP1241160A1 (en) 2001-03-13 2002-09-18 Glaxo Group Limited Tetracycline derivatives and their use as antibiotic agents
WO2002072532A1 (en) 2001-03-13 2002-09-19 Paratek Pharmaceuticals, Inc. 7, 9-substituted tetracycline compounds
WO2002072506A2 (en) 2001-03-13 2002-09-19 Paratek Pharmaceuticals, Inc. 7-pyrollyl tetracycline compounds and methods of use thereof
US7553828B2 (en) * 2001-03-13 2009-06-30 Paratek Pharmaceuticals, Inc. 9-aminomethyl substituted minocycline compounds
DE60235083D1 (de) * 2001-04-24 2010-03-04 Paratek Pharm Innc Substituierte tetracyclin-verbindungen zur behandlung von malaria
JP2004537544A (ja) 2001-07-13 2004-12-16 パラテック ファーマシューティカルズ インコーポレイテッド 標的治療活性を有するテトラサイクリン化合物
US20060194773A1 (en) * 2001-07-13 2006-08-31 Paratek Pharmaceuticals, Inc. Tetracyline compounds having target therapeutic activities
WO2003055441A2 (en) * 2001-08-02 2003-07-10 Paratek Pharmaceuticals, Inc. Medicaments
US7056902B2 (en) * 2002-01-08 2006-06-06 Paratek Pharmaceuticals, Inc. 4-dedimethylamino tetracycline compounds
IL163931A0 (en) * 2002-03-08 2005-12-18 Paratek Pharm Innc Amino-methyl substituted tetracyline compounds
IL164180A0 (en) * 2002-03-21 2005-12-18 Paratek Pharm Innc Substituted tetracycline compounds
CA2500134A1 (en) * 2002-05-06 2003-11-13 Collagenex Pharmaceuticals, Inc. Methods of simultaneously treating mucositis and fungal infection
AU2003256284A1 (en) * 2002-06-20 2004-01-06 Orapharma, Inc. Rapidly disintegrating formulations for treating or preventing mucositis
EP2345637A3 (en) 2002-07-12 2012-02-15 Paratek Pharmaceuticals, Inc. 3, 10, and 12a substituted tetracycline compounds
CA2502464A1 (en) * 2002-10-24 2004-05-06 Paratek Pharmaceuticals, Inc. Substituted tetracycline compounds for the treatment of malaria
US20060287283A1 (en) * 2003-07-09 2006-12-21 Paratek Pharmaceuticals, Inc. Prodrugs of 9-aminomethyl tetracycline compounds
EA201001081A1 (ru) * 2003-07-09 2011-02-28 Пэрэтек Фамэсьютикэлс, Инк. Соединения тетрациклина, фармацевтическая композиция и способ лечения чувствительного к тетрациклину состояния у субъекта
WO2005070878A1 (en) * 2004-01-15 2005-08-04 Paratek Pharmaceuticals, Inc. Aromatic a-ring derivatives of tetracycline compounds
US7807842B2 (en) 2004-05-21 2010-10-05 President And Fellows Of Harvard College Synthesis of tetracyclines and analogues thereof
EP2301916A3 (en) 2004-10-25 2011-09-28 Paratek Pharmaceuticals, Inc. 4-aminotetracyclines and methods of use thereof
EP2269978A3 (en) 2004-10-25 2011-09-21 Paratek Pharmaceuticals, Inc. Substituted tetracycline compounds
US7534766B2 (en) 2004-11-05 2009-05-19 Wyeth Glucuronide metabolites and epimers thereof of tigecycline
CA2597212A1 (en) * 2005-02-04 2006-08-10 Paratek Pharmaceuticals, Inc. 11a, 12-derivatives of tetracycline compounds
US20060183758A1 (en) * 2005-02-17 2006-08-17 Cb Research And Development, Inc. Method for synthesis of AZA-annelated pyrroles, thiophenes, and furans
AR057649A1 (es) 2005-05-27 2007-12-12 Wyeth Corp Formas solidas cristalinas de tigeciclina y metodos para preparar las mismas
AR057033A1 (es) * 2005-05-27 2007-11-14 Wyeth Corp Tigeciclina y metodos para preparar 9-nitrominociclina
AR057034A1 (es) * 2005-05-27 2007-11-14 Wyeth Corp Metodos para purificar tigeciclina
AR057032A1 (es) * 2005-05-27 2007-11-14 Wyeth Corp Tigeciclina y metodos de preparacion
AR057324A1 (es) * 2005-05-27 2007-11-28 Wyeth Corp Tigeciclina y metodos para preparar 9-aminominociclina
US20070093455A1 (en) * 2005-07-21 2007-04-26 Paul Abato 10-substituted tetracyclines and methods of use thereof
BRPI0620430A2 (pt) * 2005-12-22 2011-11-08 Wyeth Corp métodos para tratar infecções do trato gastrointestinal com tigeciclina
WO2007075794A2 (en) * 2005-12-22 2007-07-05 Wyeth Oral formulations comprising tigecycline
CA2652346A1 (en) 2006-05-15 2007-11-22 Paratek Pharmaceuticals, Inc. Methods of regulating expression of genes or of gene products using substituted tetracycline compounds
AR061485A1 (es) * 2006-06-15 2008-08-27 Serenex Inc Composiciones estabilizadas de tetraciclina
MY153749A (en) 2007-11-29 2015-03-13 Actelion Pharmaceuticals Ltd Phosphonic acid derivates and their use as p2y12 receptor antagonists
ES2655911T3 (es) 2008-08-08 2018-02-22 Tetraphase Pharmaceuticals, Inc. Compuestos de tetraciclina sustituidos con C7-fluoro
EP2424834B1 (en) 2009-04-30 2018-07-11 President and Fellows of Harvard College Synthesis of tetracyclines and intermediates thereof
PL2427425T3 (pl) 2009-05-08 2017-08-31 Tetraphase Pharmaceuticals, Inc. Związki tetracyklinowe
HUE037852T2 (hu) 2009-08-28 2018-09-28 Tetraphase Pharmaceuticals Inc Tetraciklin-vegyületek
PL2890673T3 (pl) 2012-08-31 2019-06-28 Tetraphase Pharmaceuticals, Inc. Związki tetracyklinowe
CN117903083A (zh) 2016-10-19 2024-04-19 四相制药公司 艾若威四环素的结晶形式

Family Cites Families (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
USRE26271E (en) * 1967-09-26 Reductive alkylation process
US2482055A (en) * 1948-02-11 1949-09-13 American Cyanamid Co Aureomycin and preparation of same
US3007965A (en) * 1959-02-13 1961-11-07 American Cyanamid Co New tetracyclines produced by streptomyces aureofaciens
US3043875A (en) * 1959-10-22 1962-07-10 Pfizer & Co C Halogenated tetracycline derivatives and processes for their preparation
FR1430859A (fi) * 1960-05-23 1966-05-25
US3338963A (en) * 1960-10-28 1967-08-29 American Cyanamid Co Tetracycline compounds
US3829453A (en) * 1961-08-18 1974-08-13 Pfizer Octahydroanthracene-2-aminoacetic acids and esters and mixed anhydrides thereof
US3360557A (en) * 1963-05-10 1967-12-26 American Cyanamid Co 9-hydroxytetracyclines and a process of preparing same
USRE26253E (en) * 1963-05-17 1967-08-15 And z-alkylamino-g-deoxytetracycline
US3341585A (en) * 1966-05-06 1967-09-12 American Cyanamid Co Substituted 7-and/or 9-amino-6-deoxytetracyclines
US3360561A (en) * 1967-06-19 1967-12-26 American Cyanamid Co Nitration of tetracyclines
US3518306A (en) * 1968-02-19 1970-06-30 American Cyanamid Co 7- and/or 9-(n-nitrosoalkylamino)-6-demethyl-6-deoxytetracyclines
US3579579A (en) * 1968-04-18 1971-05-18 American Cyanamid Co Substituted 7- and/or 9-amino-6-demethyl-6-deoxytetracyclines
US4806529A (en) * 1982-11-18 1989-02-21 Trustees Of Tufts College, Tufts University Tetracycline activity enhancement
US4518960A (en) * 1982-11-23 1985-05-21 Burroughs Corporation Speed independent selector switch employing M-out-of-N codes
US5420272A (en) * 1992-08-13 1995-05-30 American Cyanamid Company 7-(substituted)-8-(substituted)-9-](substituted glycyl)amido]-6-demethyl-6-deoxytetracyclines
US5284963A (en) * 1992-08-13 1994-02-08 American Cyanamid Company Method of producing 7-(substituted)-9-[(substituted glycyl)-amidol]-6-demethyl-6-deoxytetra-cyclines
SG47520A1 (en) * 1992-08-13 1998-04-17 American Cyanamid Co New method for the production of 9-amino-6-demethyl-6-deoxytetracycline
US5328902A (en) * 1992-08-13 1994-07-12 American Cyanamid Co. 7-(substituted)-9-[(substituted glycyl)amido]-6-demethyl-6-deoxytetracyclines

Also Published As

Publication number Publication date
US5495018A (en) 1996-02-27
US5886175A (en) 1999-03-23
AU674524B2 (en) 1997-01-02
EP0582810A1 (en) 1994-02-16
SG47520A1 (en) 1998-04-17
NO932872D0 (no) 1993-08-12
HU211303A9 (en) 1995-11-28
HUT64945A (en) 1994-03-28
CZ289195B6 (cs) 2001-11-14
CA2103861A1 (en) 1994-02-14
PL175487B1 (pl) 1999-01-29
NZ248359A (en) 1996-03-26
HU9302333D0 (en) 1993-10-28
CN1048719C (zh) 2000-01-26
DE69331774T2 (de) 2002-11-14
FI933567A0 (fi) 1993-08-12
IL119750A (en) 1998-09-24
PL174230B1 (pl) 1998-07-31
CN1090267A (zh) 1994-08-03
KR100309540B1 (ko) 2002-04-24
NO932872L (no) 1994-02-14
SK281871B6 (sk) 2001-08-06
HU213269B (en) 1997-04-28
SK85793A3 (en) 1994-04-06
US5430162A (en) 1995-07-04
ZA935892B (en) 1994-03-10
ES2173876T3 (es) 2002-11-01
NO302568B1 (no) 1998-03-23
PL174127B1 (pl) 1998-06-30
ATE215530T1 (de) 2002-04-15
IL106677A0 (en) 1993-12-08
JP3639313B2 (ja) 2005-04-20
DK0582810T3 (da) 2002-06-03
PT582810E (pt) 2002-08-30
DE69331774D1 (de) 2002-05-08
CZ157593A3 (en) 1994-02-16
EP0582810B1 (en) 2002-04-03
CA2103861C (en) 2004-07-27
US5512553A (en) 1996-04-30
PH31210A (en) 1998-05-05
PL300066A1 (en) 1994-02-21
PL174022B1 (pl) 1998-06-30
IL106677A (en) 1998-06-15
KR940003925A (ko) 1994-03-14
RU2127255C1 (ru) 1999-03-10
IL119751A (en) 1998-09-24
JPH06228072A (ja) 1994-08-16
AU4460193A (en) 1994-02-17
IL119750A0 (en) 1997-03-18

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