GB1469384A - Tetracyclines - Google Patents
TetracyclinesInfo
- Publication number
- GB1469384A GB1469384A GB2627075A GB2627075A GB1469384A GB 1469384 A GB1469384 A GB 1469384A GB 2627075 A GB2627075 A GB 2627075A GB 2627075 A GB2627075 A GB 2627075A GB 1469384 A GB1469384 A GB 1469384A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrogen atom
- group
- carbon atoms
- represented
- methylthioalkyl
- 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
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1469384 Alkyl- and methylthioalkyl-tetracyclines SOC FARMACEUTICI ITALIA SpA 20 June 1975 [25 June 1974] 26270/75 Heading C2C A tetracycline of the general Formula I wherein R 1 represents a hydrogen atom, a hydroxy group or an acyloxy group having from 1 to 4 carbon atoms; R 2 represents a hydrogen atom or a methyl group; R 3 represents a hydrogen atom when R 2 represents a methyl group or otherwise represents a hydrogen atom, an alkyl group having from 1 to 4 carbon atoms, a methylthioalkyl group having from 2 to 5 carbon atoms or a dimethylamino group; R 4 represents a hydrogen atom when R 3 represents a dimethylamino group or otherwise represents a hydrogen atom, an alkyl group having from 1 to 4 carbon atoms or a methylthioalkyl group having from 2 to 5 carbon atoms; and R 5 represents a hydrogen atom, is reacted in the presence of a strong acid and in the absence of water with a sulphide of the general formula wherein R represents a hydrogen atom or an alkyl group having up to 3 carbon atoms, thereby to introduce according to the following stipulations one or more methylthioalkyl substituents of the formula(e) CH 3 -S-CHR- wherein R is as above defined: (a) if R 2 , R 3 and R 4 all represented hydrogen atoms, for one of R 3 and R 4 , both of R 3 and R 4 or all of R 3 , R 4 and R 5 , (b) if R 2 represented a methyl group and R 4 represented a hydrogen atom, for R 4 or both of R 4 and R 5 , (c) if R 2 represented a methyl group and R 4 did not represent a hydrogen atom, for R 5 , (d) if R 2 and R 3 both represented hydrogen atoms and R 4 did not represent a hydrogen atom, for R 3 or both of R 3 and R 5 , (e) if R 3 represented a dimethylamino group, for R 5 , (f) if R 3 represented neither a dimethylamino group nor a hydrogen atom and R 4 represented a hydrogen atom, for R 4 or both of R 4 and R 5 , (g) if R 3 represented neither a dimethylamino group nor a hydrogen atom and R<SP>4</SP> did not represent a hydrogen atom, for R 5 , and the methylthioalkyltetracycline derivative is either isolated or demethylthionated by refluxing in a solvent with Raney nickel to give the corresponding alkyltetracycline derivative (in which the or each alkyl substituent is of the formula RCH 2 -). Tetracycline derivatives of the general Formula I wherein R 1 represents a hydrogen atom, a hydroxy group or an acyloxy group having from 1 to 4 carbon atoms; R 2 represents a hydrogen atom or a methyl group; R 3 represents a hydrogen atom, an alkyl group having from 1 to 4 carbon atoms, a methylthioalkyl group having from 2 to 5 carbon atoms or a dimethylamino group; and R 4 and R 5 each represents a hydrogen atom, an alkyl group having from 1 to 4 carbon atoms or a methylthioalkyl group having from 2 to 5 carbon atoms: with the provisos that R 3 and R 4 do not simultaneously represent hydrogen atoms, that when R 2 represents a methyl group R 3 represents a hydrogen atom, that when R 3 represents a dimethylamino group R 4 represents a hydrogen atom and R 5 does not represent a hydrogen atom, and that when R 5 represents a hydrogen atom R 3 and R 4 do not represent (i) a hydrogen atom and a butyl group respectively, or (ii) a methyl group and a butyl group respectively, or (iii) a methyl group and a hydrogen atom respectively, are novel.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2435974 | 1974-06-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1469384A true GB1469384A (en) | 1977-04-06 |
Family
ID=11213252
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2627075A Expired GB1469384A (en) | 1974-06-25 | 1975-06-20 | Tetracyclines |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS5119757A (en) |
| DE (1) | DE2527568A1 (en) |
| FR (1) | FR2279720A1 (en) |
| GB (1) | GB1469384A (en) |
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002004407A2 (en) | 2000-07-07 | 2002-01-17 | Trustees Of Tufts College | 7-substituted tetracycline compounds |
| US7001918B2 (en) | 2001-03-13 | 2006-02-21 | Paratek Pharmaceuticals, Inc. | 7-pyrrolyl tetracycline compounds and methods of use thereof |
| US7056902B2 (en) | 2002-01-08 | 2006-06-06 | Paratek Pharmaceuticals, Inc. | 4-dedimethylamino tetracycline compounds |
| US7094806B2 (en) | 2000-07-07 | 2006-08-22 | Trustees Of Tufts College | 7, 8 and 9-substituted tetracycline compounds |
| US7323492B2 (en) | 2001-08-02 | 2008-01-29 | Paratek Pharmaceuticals, Inc. | 7-pyrollyl 9-aminoacyl tetracycline compounds and methods of use thereof |
| US7326696B2 (en) | 2002-03-08 | 2008-02-05 | Paratek Pharmaceuticals, Inc. | Amino-methyl substituted tetracycline compounds |
| US7612053B2 (en) | 2000-05-15 | 2009-11-03 | Paratek Pharmaceuticals, Inc. | 7-Substituted fused ring tetracycline compounds |
| US7696186B2 (en) | 2001-03-13 | 2010-04-13 | Paratek Pharmaceuticals, Inc. | 7,9-substituted tetracycline compounds |
| US7696187B2 (en) | 1999-09-14 | 2010-04-13 | Trustees Of Tufts College | Methods of preparing substituted tetracyclines with transition metal-based chemistries |
| US7820641B2 (en) | 2002-03-21 | 2010-10-26 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds |
| US7851460B2 (en) | 2000-06-16 | 2010-12-14 | Trustees Of Tufts College | 7-phenyl-substituted tetracycline compounds |
| US8048867B2 (en) | 2000-07-07 | 2011-11-01 | Trustees Of Tufts College | 9-substituted minocycline compounds |
| US8106225B2 (en) | 1999-09-14 | 2012-01-31 | Trustees Of Tufts College | Methods of preparing substituted tetracyclines with transition metal-based chemistries |
| AU2005244988B2 (en) * | 2004-05-21 | 2012-02-02 | President And Fellows Of Harvard College | Synthesis of tetracyclines and analogues thereof |
| US8318706B2 (en) | 2006-12-21 | 2012-11-27 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds |
| US8513223B2 (en) | 2006-12-21 | 2013-08-20 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds for treatment of inflammatory skin disorders |
| US8518912B2 (en) | 2007-11-29 | 2013-08-27 | Actelion Pharmaceuticals Ltd. | Phosphonic acid derivates and their use as P2Y12 receptor antagonists |
| AU2012202559B2 (en) * | 2004-05-21 | 2014-07-17 | President And Fellows Of Harvard College | Synthesis of tetracyclines and analogues thereof |
| US9533943B2 (en) | 2003-07-09 | 2017-01-03 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds |
| EP3354637B1 (en) * | 2015-02-13 | 2021-05-26 | Hovione Scientia Limited | New polymorphic forms of minocycline base and processes for their preparation |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2318580A1 (en) * | 1998-01-23 | 1999-07-29 | Mark L. Nelson | Pharmaceutically active compounds and methods of use thereof |
| CA2648668C (en) | 2006-04-07 | 2015-06-23 | The President And Fellows Of Harvard College | Synthesis of tetracyclines and analogues thereof |
| EP3056487B1 (en) | 2006-10-11 | 2018-02-21 | President and Fellows of Harvard College | Synthesis of enone intermediate |
| EP2424834B1 (en) | 2009-04-30 | 2018-07-11 | President and Fellows of Harvard College | Synthesis of tetracyclines and intermediates thereof |
-
1975
- 1975-06-20 JP JP7540375A patent/JPS5119757A/en active Pending
- 1975-06-20 DE DE19752527568 patent/DE2527568A1/en not_active Withdrawn
- 1975-06-20 GB GB2627075A patent/GB1469384A/en not_active Expired
- 1975-06-24 FR FR7519665A patent/FR2279720A1/en active Granted
Cited By (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8106225B2 (en) | 1999-09-14 | 2012-01-31 | Trustees Of Tufts College | Methods of preparing substituted tetracyclines with transition metal-based chemistries |
| US7696187B2 (en) | 1999-09-14 | 2010-04-13 | Trustees Of Tufts College | Methods of preparing substituted tetracyclines with transition metal-based chemistries |
| US7612053B2 (en) | 2000-05-15 | 2009-11-03 | Paratek Pharmaceuticals, Inc. | 7-Substituted fused ring tetracycline compounds |
| US8288570B2 (en) | 2000-05-15 | 2012-10-16 | Paratek Pharmaceuticals, Inc. | 7-iodo tetracyclines and related methods |
| US7893282B2 (en) | 2000-05-15 | 2011-02-22 | Paratek Pharmaceuticals, Inc. | 7-substituted fused ring tetracycline compounds |
| US8168810B2 (en) | 2000-06-16 | 2012-05-01 | Trustees Of Tufts College | 7-phenyl-substituted tetracycline compounds |
| US7851460B2 (en) | 2000-06-16 | 2010-12-14 | Trustees Of Tufts College | 7-phenyl-substituted tetracycline compounds |
| US8048867B2 (en) | 2000-07-07 | 2011-11-01 | Trustees Of Tufts College | 9-substituted minocycline compounds |
| WO2002004407A2 (en) | 2000-07-07 | 2002-01-17 | Trustees Of Tufts College | 7-substituted tetracycline compounds |
| US9090541B2 (en) | 2000-07-07 | 2015-07-28 | Paratek Pharmaceuticals, Inc. | 9-substituted minocycline compounds |
| US7696188B2 (en) | 2000-07-07 | 2010-04-13 | Trustees Of Tufts College | 7,8 and 9-substituted tetracycline compounds |
| WO2002004407A3 (en) * | 2000-07-07 | 2002-04-04 | Tufts College | 7-substituted tetracycline compounds |
| US7094806B2 (en) | 2000-07-07 | 2006-08-22 | Trustees Of Tufts College | 7, 8 and 9-substituted tetracycline compounds |
| US8492365B2 (en) | 2000-07-07 | 2013-07-23 | Trustees Of Tufts College | 7-substituted tetracycline compounds |
| US8258120B2 (en) | 2000-07-07 | 2012-09-04 | Paratek Pharmaceuticals, Inc. | 9-substituted minocycline compounds |
| US8252777B2 (en) | 2000-07-07 | 2012-08-28 | Trustees Of Tufts College | 7, 8 and 9-substituted tetracycline compounds |
| US7875649B2 (en) | 2000-07-07 | 2011-01-25 | Trustees Of Tufts College | 7, 8 and 9-substituted tetracycline compounds |
| US6818635B2 (en) | 2000-07-07 | 2004-11-16 | Paratek Pharmaceuticals, Inc. | 7-substituted tetracycline compounds |
| AU2001271642B2 (en) * | 2000-07-07 | 2006-01-05 | Paratek Pharmaceuticals, Inc. | 7-substituted tetracycline compounds |
| EP2289871A1 (en) * | 2000-07-07 | 2011-03-02 | Paratek Pharmaceuticals, Inc. | 7-substituted tetracycline compounds |
| US7696358B2 (en) | 2001-03-13 | 2010-04-13 | Paratek Pharmaceuticals, Inc. | Five-membered heterocyclyl tetracycline compounds and methods of use thereof |
| US7897784B2 (en) | 2001-03-13 | 2011-03-01 | Paratek Pharmaceuticals, Inc. | Process for preparing five-membered heterocyclyl tetracycline compounds and methods of use thereof |
| US7001918B2 (en) | 2001-03-13 | 2006-02-21 | Paratek Pharmaceuticals, Inc. | 7-pyrrolyl tetracycline compounds and methods of use thereof |
| US7696186B2 (en) | 2001-03-13 | 2010-04-13 | Paratek Pharmaceuticals, Inc. | 7,9-substituted tetracycline compounds |
| US8304445B2 (en) | 2001-03-13 | 2012-11-06 | Paratek Pharmaceuticals, Inc. | 7-pyrazolyl tetracycline compounds and methods of use thereof |
| US8211937B2 (en) | 2001-08-02 | 2012-07-03 | Paratek Pharmaceuticals, Inc. | 7-pyrollyl 9-aminoacyl tetracycline compounds and methods of use thereof |
| US7323492B2 (en) | 2001-08-02 | 2008-01-29 | Paratek Pharmaceuticals, Inc. | 7-pyrollyl 9-aminoacyl tetracycline compounds and methods of use thereof |
| US7056902B2 (en) | 2002-01-08 | 2006-06-06 | Paratek Pharmaceuticals, Inc. | 4-dedimethylamino tetracycline compounds |
| US7326696B2 (en) | 2002-03-08 | 2008-02-05 | Paratek Pharmaceuticals, Inc. | Amino-methyl substituted tetracycline compounds |
| US7820641B2 (en) | 2002-03-21 | 2010-10-26 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds |
| US9533943B2 (en) | 2003-07-09 | 2017-01-03 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds |
| AU2005244988C1 (en) * | 2004-05-21 | 2012-06-28 | President And Fellows Of Harvard College | Synthesis of tetracyclines and analogues thereof |
| AU2012202559B2 (en) * | 2004-05-21 | 2014-07-17 | President And Fellows Of Harvard College | Synthesis of tetracyclines and analogues thereof |
| AU2005244988B2 (en) * | 2004-05-21 | 2012-02-02 | President And Fellows Of Harvard College | Synthesis of tetracyclines and analogues thereof |
| US8513223B2 (en) | 2006-12-21 | 2013-08-20 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds for treatment of inflammatory skin disorders |
| US9012433B2 (en) | 2006-12-21 | 2015-04-21 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds |
| US8318706B2 (en) | 2006-12-21 | 2012-11-27 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds |
| US9481639B2 (en) | 2006-12-21 | 2016-11-01 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds for treatment of inflammatory skin disorders |
| US8518912B2 (en) | 2007-11-29 | 2013-08-27 | Actelion Pharmaceuticals Ltd. | Phosphonic acid derivates and their use as P2Y12 receptor antagonists |
| EP3354637B1 (en) * | 2015-02-13 | 2021-05-26 | Hovione Scientia Limited | New polymorphic forms of minocycline base and processes for their preparation |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2279720A1 (en) | 1976-02-20 |
| FR2279720B1 (en) | 1977-12-02 |
| JPS5119757A (en) | 1976-02-17 |
| DE2527568A1 (en) | 1976-01-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |