CA1068285A - 6-oxatetracycline and 6-thiatetracycline compounds and process for their preparation - Google Patents

6-oxatetracycline and 6-thiatetracycline compounds and process for their preparation

Info

Publication number
CA1068285A
CA1068285A CA234,780A CA234780A CA1068285A CA 1068285 A CA1068285 A CA 1068285A CA 234780 A CA234780 A CA 234780A CA 1068285 A CA1068285 A CA 1068285A
Authority
CA
Canada
Prior art keywords
compound
dimethylamino
amino
thiatetracycline
agent
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.)
Expired
Application number
CA234,780A
Other languages
English (en)
French (fr)
Inventor
Jurgen Seubert
Rolf Bergmann
Werner Rogalski
Joachim Gante
Richard Kirchlechner
Helmut Wahlig
Rudolf Gottschlich
Rosmarie Steinigeweg
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.)
Merck Patent GmbH
Original Assignee
Merck Patent GmbH
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 Merck Patent GmbH filed Critical Merck Patent GmbH
Application granted granted Critical
Publication of CA1068285A publication Critical patent/CA1068285A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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, directly attached to ring carbon atoms
    • C07D215/20—Oxygen atoms
    • C07D215/22—Oxygen atoms attached in position 2 or 4
    • C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
    • C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/18—Ring systems of four or more rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78—Ring systems having three or more relevant rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
    • C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
    • C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Pyrane Compounds (AREA)
CA234,780A 1974-09-06 1975-09-04 6-oxatetracycline and 6-thiatetracycline compounds and process for their preparation Expired CA1068285A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE2442829A DE2442829A1 (de) 1974-09-06 1974-09-06 Tetracyclische verbindungen und verfahren zu ihrer herstellung

Publications (1)

Publication Number Publication Date
CA1068285A true CA1068285A (en) 1979-12-18

Family

ID=5925100

Family Applications (1)

Application Number Title Priority Date Filing Date
CA234,780A Expired CA1068285A (en) 1974-09-06 1975-09-04 6-oxatetracycline and 6-thiatetracycline compounds and process for their preparation

Country Status (21)

Country Link
US (1) US4024272A (US07223432-20070529-C00017.png)
JP (1) JPS5154564A (US07223432-20070529-C00017.png)
AT (1) AT344890B (US07223432-20070529-C00017.png)
BE (1) BE833048A (US07223432-20070529-C00017.png)
CA (1) CA1068285A (US07223432-20070529-C00017.png)
CS (1) CS191275B2 (US07223432-20070529-C00017.png)
DD (1) DD121637A5 (US07223432-20070529-C00017.png)
DE (1) DE2442829A1 (US07223432-20070529-C00017.png)
DK (1) DK397875A (US07223432-20070529-C00017.png)
ES (1) ES440765A1 (US07223432-20070529-C00017.png)
FR (1) FR2283690A1 (US07223432-20070529-C00017.png)
GB (1) GB1467206A (US07223432-20070529-C00017.png)
HU (2) HU173491B (US07223432-20070529-C00017.png)
IE (1) IE41675B1 (US07223432-20070529-C00017.png)
IL (1) IL48044A (US07223432-20070529-C00017.png)
IT (1) IT7948216A0 (US07223432-20070529-C00017.png)
LU (1) LU73332A1 (US07223432-20070529-C00017.png)
NL (1) NL7510505A (US07223432-20070529-C00017.png)
PL (1) PL96677B1 (US07223432-20070529-C00017.png)
SE (1) SE7509880L (US07223432-20070529-C00017.png)
ZA (1) ZA755699B (US07223432-20070529-C00017.png)

Families Citing this family (75)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2746044C2 (de) * 1977-10-13 1979-09-06 Merck Patent Gmbh, 6100 Darmstadt Verfahren zur Herstellung von e-Thiatetracyclinracematen mit natürlicher Konfiguration und ihren optischen Antipoden
US4672138A (en) * 1980-10-20 1987-06-09 Hoechst Roussel Pharmaceuticals Inc. Phenyl substituted carbamothioic acid esters
US4436748A (en) * 1980-10-20 1984-03-13 Hoechst-Roussel Pharmaceuticals Inc. Benzo[b]thiophenes
US5589470A (en) * 1990-02-26 1996-12-31 Trustees Of Tufts College Reducing tetracycline resistance in living cells
US5064821A (en) * 1982-11-18 1991-11-12 Trustees Of Tufts College Method and compositions for overcoming tetracycline resistance within living cells
US4806529A (en) * 1982-11-18 1989-02-21 Trustees Of Tufts College, Tufts University Tetracycline activity enhancement
EP0416564A3 (en) * 1989-09-05 1992-03-11 Kao Corporation Novel aroyl ketone derivative, uv ray absorber comprising the same, and cosmetic composition containing the same
US6756365B2 (en) * 1991-11-06 2004-06-29 Trustees Of Tufts College Reducing tetracycline resistance in living cells
FR2795722A1 (fr) * 1999-07-02 2001-01-05 Rhodia Chimie Sa Procede de preparation d'une arylhydrazine hydroxylee, produits intermediaires et leur procede d'obtention
US6849615B2 (en) 1999-09-14 2005-02-01 Paratek Pharmaceuticals, Inc. 13-substituted methacycline compounds
US8106225B2 (en) * 1999-09-14 2012-01-31 Trustees Of Tufts College Methods of preparing substituted tetracyclines with transition metal-based chemistries
MXPA02002595A (es) 1999-09-14 2003-07-21 Tufts College Metodo para preparar tetraciclinas sustituidas con quimicas a base de metal de transicion.
US6500812B2 (en) 1999-09-14 2002-12-31 Paratek Pharmaceuticals, Inc. 13-substituted methacycline compounds
US6833365B2 (en) * 2000-01-24 2004-12-21 Trustees Of Tufts College Tetracycline compounds for treatment of Cryptosporidium parvum related disorders
ES2288945T3 (es) * 2000-03-31 2008-02-01 Trustees Of Tufts College Compuestos de tetraciclina 7 y 9-carbamato, urea, tiourea, tiocarbamato y heteroaril-amino sustituidos.
US6642270B2 (en) * 2000-05-15 2003-11-04 Paratek Pharmaceuticals, Inc. 7-substituted fused ring tetracycline compounds
US20020132798A1 (en) * 2000-06-16 2002-09-19 Nelson Mark L. 7-phenyl-substituted tetracycline compounds
AU2001268475A1 (en) * 2000-06-16 2002-01-02 Trustees Of Tufts College 7-phenyl-substituted tetracycline compounds
US20040224927A1 (en) * 2000-06-16 2004-11-11 Trustees Of Tufts College 7-N-substituted phenyl tetracycline compounds
US7094806B2 (en) 2000-07-07 2006-08-22 Trustees Of Tufts College 7, 8 and 9-substituted tetracycline compounds
CN1690047B (zh) 2000-07-07 2010-10-06 塔夫茨大学信托人 9-取代的二甲胺四环素化合物
BR0112268A (pt) 2000-07-07 2003-05-27 Tufts College Composto de metaciclina 13-substituìda, método para tratar um estado responsivo a tetraciclina em um mamìfero, composição farmacêutica, e, método papa sintetizar um composto de metaciclina 13-substituìda
US20050143353A1 (en) * 2000-07-07 2005-06-30 Paratek Pharmaceuticals, Inc. 13-Substituted methacycline compounds
EP2289871A1 (en) 2000-07-07 2011-03-02 Paratek Pharmaceuticals, Inc. 7-substituted tetracycline compounds
ATE504562T1 (de) 2000-07-07 2011-04-15 Tufts College 7-, 8- und 9-substitutierte tetracyclinverbindungen
IL157860A0 (en) 2001-03-13 2004-03-28 Paratek Pharm Innc 7,9-substituted tetracycline compounds
US7553828B2 (en) 2001-03-13 2009-06-30 Paratek Pharmaceuticals, Inc. 9-aminomethyl substituted minocycline compounds
AU2002250331A1 (en) * 2001-03-13 2002-09-24 Paratek Pharmaceuticals, Inc. 7-pyrollyl tetracycline compounds and methods of use thereof
EP1241160A1 (en) * 2001-03-13 2002-09-18 Glaxo Group Limited Tetracycline derivatives and their use as antibiotic agents
WO2002072022A2 (en) 2001-03-14 2002-09-19 Paratek Pharmaceuticals, Inc. Substituted tetracycline compounds as antifungal agents
US7045507B2 (en) 2001-03-14 2006-05-16 Paratek Pharmaceuticals, Inc. Substituted tetracycline compounds as synergistic antifungal agents
US8088820B2 (en) * 2001-04-24 2012-01-03 Paratek Pharmaceuticals, Inc. Substituted tetracycline compounds for the treatment of malaria
US20040092490A1 (en) 2001-04-24 2004-05-13 Michael Draper Substituted tetracycline compounds for the treatment of malaria
EP1474380A4 (en) 2002-01-08 2007-04-18 Paratek Pharm Innc 4-DESDIMETHYL AMINO TETRA CYCLINE COMPOUNDS
US6730697B2 (en) * 2002-02-07 2004-05-04 Aventis Pharma Deutschland Gmbh Dihydrothiaphenanthrenecarbonylguanidines: composition, process of making, and use as medicament or diagnostic aid
CN102531948A (zh) 2002-03-08 2012-07-04 帕拉特克药品公司 氨基-甲基取代的四环素类化合物
AU2003218243B2 (en) * 2002-03-21 2010-04-01 Paratek Pharmaceuticals, Inc. Substituted tetracycline compounds
EP2345637A3 (en) * 2002-07-12 2012-02-15 Paratek Pharmaceuticals, Inc. 3, 10, and 12a substituted tetracycline compounds
JP2006503898A (ja) 2002-10-24 2006-02-02 パラテック ファーマシューティカルズ， インク． マラリア治療のための置換テトラサイクリン化合物
EP2319829A1 (en) 2003-07-09 2011-05-11 Paratek Pharmaceuticals, Inc. 9-substituted tetracycline compounds
AU2004259661B2 (en) 2003-07-09 2011-11-10 Paratek Pharmaceuticals, Inc. Prodrugs of 9-aminomethyl tetracycline compounds
US20060287283A1 (en) * 2003-07-09 2006-12-21 Paratek Pharmaceuticals, Inc. Prodrugs of 9-aminomethyl tetracycline compounds
CA2553510C (en) 2004-01-15 2012-09-25 Paratek Pharmaceuticals, Inc. Aromatic a-ring derivatives of tetracycline compounds
TWI261038B (en) * 2004-08-11 2006-09-01 Bo-Cheng Chen Bicycle gear-shifting handgrip
EP2284153A3 (en) 2004-10-25 2012-03-14 Paratek Pharmaceuticals, Inc. Substituted tetracycline compounds
EP1805134B1 (en) 2004-10-25 2012-06-20 Paratek Pharmaceuticals, Inc. 4-aminotetracyclines and methods of use thereof
AU2006210406C1 (en) * 2005-02-04 2013-03-07 Paratek Pharmaceuticals, Inc. 11a, 12-derivatives of tetracycline compounds
WO2007014154A2 (en) * 2005-07-21 2007-02-01 Paratek Pharmaceuticals, Inc. 10-substituted tetracyclines and methods of use thereof
EP2298324A1 (en) 2006-01-24 2011-03-23 Paratek Pharmaceuticals, Inc. Methods of increasing oral bioavailability of tetracyclines
CA2649221A1 (en) * 2006-04-17 2007-10-25 Evgeny Tsiperman Isolation of tetracycline derivatives
US8198470B2 (en) * 2006-04-24 2012-06-12 Teva Pharmaceutical Industries Ltd. Crystalline form II of tigecycline and processes for preparation thereof
CA2649075A1 (en) * 2006-04-24 2007-11-08 Teva Pharmaceutical Industries Ltd. Tigeycline crystalline forms and processes for preparation thereof
CA2652347A1 (en) * 2006-05-15 2007-11-22 Paratek Pharmaceuticals, Inc. Methods of regulating expression of genes or of gene products using substituted tetracycline compounds
WO2008045507A2 (en) 2006-10-11 2008-04-17 Paratek Pharmaceuticals, Inc. Substituted tetracycline compounds for treatment of bacillus anthracis infections
US8198469B2 (en) * 2006-11-29 2012-06-12 Teva Pharmaceutical Industries Ltd. Crystalline forms of tigecycline and processes for preparation thereof
BRPI0706517A2 (pt) * 2006-11-30 2011-03-29 Teva Pharma processos para preparação de f 9-haloacetamidominociclinas
JP5583411B2 (ja) 2006-12-21 2014-09-03 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 細菌感染、ウイルス感染、および寄生虫感染の治療のためのテトラサイクリン誘導体
PL2120963T3 (pl) 2006-12-21 2019-05-31 Paratek Pharm Innc Podstawione związki tetracyklinowe do leczenia zaburzeń zapalnych skóry
US20080214869A1 (en) * 2007-03-01 2008-09-04 Sergei Fine Processes for purification of tigecycline
US7935687B2 (en) * 2007-04-12 2011-05-03 Paratek Pharmaceuticals, Inc. Methods for treating spinal muscular atrophy using tetracycline compounds
WO2008134048A2 (en) 2007-04-27 2008-11-06 Paratek Pharmaceuticals, Inc. Methods for synthesizing and purifying aminoalkyl tetracycline compounds
ATE555079T1 (de) 2007-07-06 2012-05-15 Paratek Pharm Innc Verfahren zur synthese von 9-substituiertem minocyclin
EP2262754A4 (en) * 2008-03-05 2012-03-14 Paratek Pharm Innc MINOCYCLINE COMPOUNDS AND METHODS OF USE THEREOF
PT2271348T (pt) 2008-03-28 2018-04-16 Paratek Pharm Innc Formulação de comprimido oral de composto de tetraciclina
CA2721399A1 (en) * 2008-04-14 2009-10-22 Paratek Pharmaceuticals, Inc. Substituted tetracycline compounds
TWI680117B (zh) 2008-05-23 2019-12-21 派洛泰克藥物股份有限公司 四環素化合物之甲苯磺酸鹽及同素異形體
WO2010033939A1 (en) * 2008-09-19 2010-03-25 Paratek Pharmaceuticals, Inc. Tetracycline compounds for the treatment of rheumatoid arthritis and related methods of treatment
WO2010118435A2 (en) 2009-04-10 2010-10-14 Tufts Medical Center, Inc. Par-1 activation by metalloproteinase-1 (mmp-1)
DK2427425T3 (en) 2009-05-08 2017-06-12 Tetraphase Pharmaceuticals Inc tetracycline
SI2707003T1 (sl) 2011-05-12 2019-10-30 Paratek Pharm Innc Kristalinične soli amida (4S,4AS,5AR,12AS)-4-dimetilamino-3,10,12,12A-tetrahidroksi-7-((metoksi (metil)amino)-metil)-1,11-diokso-1,4,4A,5,5A,6,11,12A-oktahidro-naftacen -2-karboksilne kisline in postopki za uporabo le-teh
CN108276404A (zh) * 2012-08-31 2018-07-13 四相制药公司 四环素化合物
JP6269300B2 (ja) * 2014-05-01 2018-01-31 国立大学法人大阪大学 スルホキシドの脱酸素用触媒、及び該脱酸素用触媒を用いたスルフィドの製造方法
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
EP3534908A4 (en) 2016-11-01 2020-05-27 Paratek Pharmaceuticals, Inc. 9-AMINOMETHYL-MINOCYCLINE COMPOUNDS AND USE THEREOF IN THE TREATMENT OF AMBULANTLY ACQUIRED BACTERIAL PNEUMONIA (CABP)
KR102662461B1 (ko) 2017-07-21 2024-04-30 알미랄 엘엘씨 비염증성 병변의 치료

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2437487A1 (de) * 1974-08-03 1976-02-19 Merck Patent Gmbh 7-methoxy-6-thia-tetracycline und verfahren zu ihrer herstellung

Also Published As

Publication number Publication date
ES440765A1 (es) 1977-06-16
CS191275B2 (en) 1979-06-29
FR2283690A1 (fr) 1976-04-02
FR2283690B1 (US07223432-20070529-C00017.png) 1980-03-28
AT344890B (de) 1978-08-10
DK397875A (da) 1976-03-07
PL96677B1 (pl) 1978-01-31
GB1467206A (en) 1977-03-16
JPS5154564A (US07223432-20070529-C00017.png) 1976-05-13
AU8459975A (en) 1977-03-10
HU173491B (hu) 1979-05-28
DE2442829A1 (de) 1976-03-18
SE7509880L (sv) 1976-03-08
ATA689275A (de) 1977-12-15
DD121637A5 (US07223432-20070529-C00017.png) 1976-08-12
LU73332A1 (US07223432-20070529-C00017.png) 1976-04-13
ZA755699B (en) 1976-08-25
BE833048A (nl) 1976-03-03
IT7948216A0 (it) 1979-03-05
IL48044A (en) 1978-12-17
IE41675B1 (en) 1980-02-27
NL7510505A (nl) 1976-03-09
IE41675L (en) 1976-03-06
US4024272A (en) 1977-05-17
IL48044A0 (en) 1975-11-25
HU176136B (en) 1980-12-28

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