GB1237228A - MANNICH BASES OF alpha-6-DEOXY-5-OXYTETRACYCLINE - Google Patents
MANNICH BASES OF alpha-6-DEOXY-5-OXYTETRACYCLINEInfo
- Publication number
- GB1237228A GB1237228A GB6120668A GB6120668A GB1237228A GB 1237228 A GB1237228 A GB 1237228A GB 6120668 A GB6120668 A GB 6120668A GB 6120668 A GB6120668 A GB 6120668A GB 1237228 A GB1237228 A GB 1237228A
- Authority
- GB
- United Kingdom
- Prior art keywords
- salts
- amino
- deoxy
- formaldehyde
- mannich bases
- 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
- RREANTFLPGEWEN-MBLPBCRHSA-N 7-[4-[[(3z)-3-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]imino-5-fluoro-2-oxoindol-1-yl]methyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(\N=C/3C4=CC(F)=CC=C4N(CN4CCN(CC4)C=4C(=CC=5C(=O)C(C(O)=O)=CN(C=5C=4)C4CC4)F)C\3=O)=NC=2)N)=C1 RREANTFLPGEWEN-MBLPBCRHSA-N 0.000 title abstract 3
- 239000004100 Oxytetracycline Substances 0.000 title abstract 3
- 229960000625 oxytetracycline Drugs 0.000 title abstract 3
- 150000003839 salts Chemical class 0.000 abstract 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 6
- -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 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 239000000376 reactant Substances 0.000 abstract 2
- 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
- HCXJFMDOHDNDCC-UHFFFAOYSA-N 5-$l^{1}-oxidanyl-3,4-dihydropyrrol-2-one Chemical group O=C1CCC(=O)[N]1 HCXJFMDOHDNDCC-UHFFFAOYSA-N 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical group CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 229930182555 Penicillin Natural products 0.000 abstract 1
- 239000004098 Tetracycline Substances 0.000 abstract 1
- 125000002252 acyl group Chemical group 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
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 239000012736 aqueous medium Substances 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
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 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
- 150000002148 esters Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 150000002689 maleic acids Chemical class 0.000 abstract 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 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
- 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
- 150000002960 penicillins Chemical class 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000005544 phthalimido group Chemical group 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 229960002180 tetracycline Drugs 0.000 abstract 1
- 229930101283 tetracycline Natural products 0.000 abstract 1
- 235000019364 tetracycline Nutrition 0.000 abstract 1
- 150000003522 tetracyclines Chemical class 0.000 abstract 1
Classifications
-
- 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
- C07D295/12—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 singly or doubly bound nitrogen atoms
-
- 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
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01F—MAGNETS; INDUCTANCES; TRANSFORMERS; SELECTION OF MATERIALS FOR THEIR MAGNETIC PROPERTIES
- H01F38/00—Adaptations of transformers or inductances for specific applications or functions
- H01F38/20—Instruments transformers
- H01F38/22—Instruments transformers for single phase AC
- H01F38/28—Current transformers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Power Engineering (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1,237,228. Mannich bases of α-6-deoxy-5-oxy tetracycline. CHAS. PFIZER & CO. Inc. 23 Dec., 1968 [25 March, 1968], No. 61206/68. Heading C2A. Mannich bases of α-deoxy-5-oxytetracycline having the formula wherein R is amino, #-carhoxyalkylamino, #- amino- #-carboxyalkylamino, #-carboxamidoalkylamino, # - amino - # - carboxamidoalkylamino, or NR 1 R 2 wherein R 1 is C 1-17 alkyl, benzyl, phenethyl, cyclohexyl, C 2-4 hydroxyalkyl, #-aminoalkyl, #-alkylaminoalkyl or #- dialkylaminoalkyl (the above mentioned alkyl groups having from 1 to 6 carbon atoms); R 2 is hydrogen or R 1 ; R 1 and R 2 when taken together in combination with the associated amino group are piperidino, pyrrolidino, morpholino, piperazino, N-methylpiperazino, 2,6-dimethylmorpholino, N - (# - hydroxyethyl)piperazino or and their acid addition and base salts may be prepared by reacting a compound having the formula with a compound ZR or its acid addition salt, Z is H in the presence of formaldehyde or its equivalent as reactant or Z is Y-CH2- wherein Y is chloro, bromo, hydroxyl, C 1-6 alkoxyl, SO 3 -, hydrosulphido, phthalimido, succinimido, alkyl or acyl malonic ester group in the absence of formaldehyde, and, if desired, forming an acid or base salt of the product. When formaldehyde or its equivalent is a reactant the reaction may be carried out in an aqueous medium which may contain a water-soluble organic solvent at 0‹ to 30‹ C. The alkali metal, e.g. Na and K, ammonium, alkaline earth metal, e.g. Ca salts and salts with organic amines as well as salts with hydrochloric, sulphuric, phosphoric, acetic, butyric, palmitic, oleic, citric, gluconic, lactic, tartaric, ascorbic, pantothenic, penicillins, succinic half ester of D-(-)-threo-2-dichloroacetamino - 1 - p - nitrophenyl - 1,3 - propanediol, phytic and maleic acids are referred to. Pharmaceutical compositions for parenteral and oral administration comprise the above tetracycline derivatives or salts thereof and a carrier. Reference has been directed by the Comptroller to Specification 1,178,358.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691914194 DE1914194A1 (en) | 1968-03-25 | 1969-03-20 | New alpha-6-deoxy-5-oxytetracyclines |
| NL6904515A NL6904515A (en) | 1968-03-25 | 1969-03-24 | |
| BE730315D BE730315A (en) | 1968-03-25 | 1969-03-24 | |
| FR6908542A FR2004651A1 (en) | 1968-03-25 | 1969-03-24 | (A) Cmpds. of general formula (I): R = NH2, omega-carboxy- (1-6C) alkylamino, omega-aminocarboxy (1-6C) alkylamino, omega-carbonamido-(1-6C) alkylamino, |
| CH441869A CH495955A (en) | 1968-03-25 | 1969-03-24 | Process for the preparation of α-6-deoxy-5-oxy-tetracycline Mannich bases |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US71558968A | 1968-03-25 | 1968-03-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1237228A true GB1237228A (en) | 1971-06-30 |
Family
ID=24874682
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2883868A Expired GB1178358A (en) | 1968-03-25 | 1968-06-17 | Mannich Bases of alpha-6-Deoxy-5-Oxytetracycline. |
| GB6120668A Expired GB1237228A (en) | 1968-03-25 | 1968-12-23 | MANNICH BASES OF alpha-6-DEOXY-5-OXYTETRACYCLINE |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2883868A Expired GB1178358A (en) | 1968-03-25 | 1968-06-17 | Mannich Bases of alpha-6-Deoxy-5-Oxytetracycline. |
Country Status (3)
| Country | Link |
|---|---|
| AT (1) | AT291437B (en) |
| BR (1) | BR6907383D0 (en) |
| GB (2) | GB1178358A (en) |
-
1968
- 1968-06-17 GB GB2883868A patent/GB1178358A/en not_active Expired
- 1968-12-23 GB GB6120668A patent/GB1237228A/en not_active Expired
-
1969
- 1969-03-21 BR BR20738369A patent/BR6907383D0/en unknown
- 1969-03-24 AT AT286869A patent/AT291437B/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| BR6907383D0 (en) | 1973-03-13 |
| GB1178358A (en) | 1970-01-21 |
| AT291437B (en) | 1971-07-12 |
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