GB1108310A - Derivatives of 6-methylene-tetracycline and process for their preparation - Google Patents
Derivatives of 6-methylene-tetracycline and process for their preparationInfo
- Publication number
- GB1108310A GB1108310A GB16398/65A GB1639865A GB1108310A GB 1108310 A GB1108310 A GB 1108310A GB 16398/65 A GB16398/65 A GB 16398/65A GB 1639865 A GB1639865 A GB 1639865A GB 1108310 A GB1108310 A GB 1108310A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amino
- alkyl
- salts
- alkylamino
- carbon atoms
- 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
- 239000004098 Tetracycline Substances 0.000 title abstract 4
- 229960002180 tetracycline Drugs 0.000 title abstract 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 6
- 150000003839 salts Chemical class 0.000 abstract 5
- 125000003282 alkyl amino group Chemical group 0.000 abstract 4
- -1 piperidino, pyrrolidino, morpholino, piperazino, N - methylpiperazino Chemical group 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 239000002585 base Substances 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 235000019364 tetracycline Nutrition 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- 229930040373 Paraformaldehyde Natural products 0.000 abstract 2
- 229920002866 paraformaldehyde Polymers 0.000 abstract 2
- 229930101283 tetracycline Natural products 0.000 abstract 2
- 150000003522 tetracyclines Chemical class 0.000 abstract 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 abstract 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- 150000000996 L-ascorbic acids Chemical class 0.000 abstract 1
- 235000021314 Palmitic acid Nutrition 0.000 abstract 1
- 229930182555 Penicillin Natural products 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 239000012736 aqueous medium Substances 0.000 abstract 1
- 235000010323 ascorbic acid Nutrition 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 235000015165 citric acid Nutrition 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 235000012208 gluconic acid Nutrition 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 150000007529 inorganic bases Chemical class 0.000 abstract 1
- 235000014655 lactic acid Nutrition 0.000 abstract 1
- 150000002689 maleic acids Chemical class 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 235000021313 oleic acid Nutrition 0.000 abstract 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 abstract 1
- 235000019161 pantothenic acid Nutrition 0.000 abstract 1
- 150000002948 pantothenic acids Chemical class 0.000 abstract 1
- 150000002960 penicillins Chemical class 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 235000011007 phosphoric acid Nutrition 0.000 abstract 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 235000002906 tartaric acid Nutrition 0.000 abstract 1
- 229940040944 tetracyclines Drugs 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/65—Tetracyclines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Novel 6-methylene tetracycline derivatives of the general formula <FORM:1108310/C2/1> wherein X is H or Cl, B is H or Cl and X1 is H or OH, X and X1 being H when B is Cl, and R is amino, o -carboxy (lower, i.e. up to 6 carbon atoms) alkylamino, o -amino-o -carboxy (lower) alkylamino, o - carboxamido (lower) alkylamino, o -amino-o -carboxamido (lower) alkyl amino or NR1R2 wherein R1 is alkyl of 1-17 carbon atoms, benzyl, phenethyl, cyclohexyl, hydroxyalkyl of 2-4 carbon atoms, o -amino (lower) alkyl, o (lower) dialkylamino (lower) alkyl; R2 is H or R1; R1 and R2 in combination with the amino group are piperidino, pyrrolidino, morpholino, piperazino, N - methylpiperazino, 2,6 - dimethylmorpholino, N - (b -hydroxyethyl) piperazino or <FORM:1108310/C2/2> and their acid addition and base salts are prepared by reacting a compound of formula <FORM:1108310/C2/3> wherein X, B and X1 are as above defined either with a compound having the formula ZR or its acid addition salt, in which R is as above defined, and Z is H or H2NCH2- in the presence of formaldehyde or paraformaldehyde or, with an addition product of formaldehyde or paraformaldehyde and the compound ZR, and, if desired, forming an acid or a base salt of the product with an inorganic or organic acid or base. The reaction may be carried out in an aqueous medium to which a water-soluble organic solvent may be added at a temperature from 0 DEG to 30 DEG C., the reactants being present in equimolar proportions. Salts of the tetracyclines may be formed with HCl, H2SO4, H3PO4, CH3CO2H, butyric, palmitic, oleic, citric, gluconic, lactic, tartaric, ascorbic or pantothenic acids, penicillins, succinic half ester of D-(-)-threo-2-dichloroacetamino-1-p-nitrophenyl-1,3-propanediol, phytic and maleic acids and also with inorganic or organic bases e.g. alkali metal, alkaline earth metal, ammonium or organic amine salts. The novel 6-demethylene tetracycline derivatives of general Formula I and salts thereof may be formulated into pharmaceutical compositions. Reference has been directed by the Comptroller to Specification 995,031.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36401364A | 1964-04-30 | 1964-04-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1108310A true GB1108310A (en) | 1968-04-03 |
Family
ID=23432664
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB16398/65A Expired GB1108310A (en) | 1964-04-30 | 1965-04-15 | Derivatives of 6-methylene-tetracycline and process for their preparation |
Country Status (2)
| Country | Link |
|---|---|
| FR (1) | FR4662M (en) |
| GB (1) | GB1108310A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002004405A3 (en) * | 2000-07-07 | 2002-03-14 | Tufts College | 13-substituted methacycline compounds |
| US6500812B2 (en) | 1999-09-14 | 2002-12-31 | Paratek Pharmaceuticals, Inc. | 13-substituted methacycline compounds |
| US6849615B2 (en) | 1999-09-14 | 2005-02-01 | Paratek Pharmaceuticals, Inc. | 13-substituted methacycline compounds |
| US7521437B2 (en) | 2000-06-16 | 2009-04-21 | Trustees Of Tufts College | 7-phenyl-substituted tetracycline compounds |
| 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 |
-
1965
- 1965-04-15 GB GB16398/65A patent/GB1108310A/en not_active Expired
- 1965-04-27 FR FR14908A patent/FR4662M/fr not_active Expired
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6500812B2 (en) | 1999-09-14 | 2002-12-31 | Paratek Pharmaceuticals, Inc. | 13-substituted methacycline compounds |
| US6849615B2 (en) | 1999-09-14 | 2005-02-01 | Paratek Pharmaceuticals, Inc. | 13-substituted methacycline compounds |
| US7521437B2 (en) | 2000-06-16 | 2009-04-21 | Trustees Of Tufts College | 7-phenyl-substituted 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 |
| EP2204361A1 (en) | 2000-07-07 | 2010-07-07 | Trustees Of Tufts College | 13-substituted methacycline compounds |
| WO2002004405A3 (en) * | 2000-07-07 | 2002-03-14 | Tufts College | 13-substituted methacycline compounds |
| EP1661883A1 (en) | 2000-07-07 | 2006-05-31 | Trustees Of Tufts College | 13-substituted methacycline compounds |
| JP2004502751A (en) * | 2000-07-07 | 2004-01-29 | トラスティーズ・オブ・タフツ・カレッジ | 13-substituted metacycline compounds |
| 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 |
| US9012433B2 (en) | 2006-12-21 | 2015-04-21 | 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| FR4662M (en) | 1966-12-12 |
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