HU211214B - Method for producing novel 9-amino-7-(substituted)-6-demethyl-6-desoxy-tetracycline derivatives and medical preparatives containing them - Google Patents
Method for producing novel 9-amino-7-(substituted)-6-demethyl-6-desoxy-tetracycline derivatives and medical preparatives containing them Download PDFInfo
- Publication number
- HU211214B HU211214B HU9203143A HU9203143A HU211214B HU 211214 B HU211214 B HU 211214B HU 9203143 A HU9203143 A HU 9203143A HU 9203143 A HU9203143 A HU 9203143A HU 211214 B HU211214 B HU 211214B
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- HU
- Hungary
- Prior art keywords
- amino
- methylpropyl
- dimethylamino
- butyl
- dioxo
- Prior art date
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- 239000004098 Tetracycline Substances 0.000 title description 36
- 229960002180 tetracycline Drugs 0.000 title description 30
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 78
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- 239000001257 hydrogen Substances 0.000 claims description 42
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 36
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 33
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 33
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 32
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
- -1 η-propyl Chemical group 0.000 claims description 30
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 24
- 239000007787 solid Substances 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 20
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 20
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 19
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 19
- 238000002360 preparation method Methods 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 15
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 15
- 239000003054 catalyst Substances 0.000 claims description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 10
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- PBIUDEUWYGBHDW-UHFFFAOYSA-N 2-chloro-1-pyridin-3-ylethanone;hydrochloride Chemical compound Cl.ClCC(=O)C1=CC=CN=C1 PBIUDEUWYGBHDW-UHFFFAOYSA-N 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
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- 239000007868 Raney catalyst Substances 0.000 claims description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 2
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- 230000002378 acidificating effect Effects 0.000 claims description 2
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- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 claims description 2
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- QBERHIJABFXGRZ-UHFFFAOYSA-M rhodium;triphenylphosphane;chloride Chemical compound [Cl-].[Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QBERHIJABFXGRZ-UHFFFAOYSA-M 0.000 claims description 2
- 238000009901 transfer hydrogenation reaction Methods 0.000 claims description 2
- 229910017053 inorganic salt Inorganic materials 0.000 claims 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 claims 1
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- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 229910052703 rhodium Inorganic materials 0.000 claims 1
- 239000010948 rhodium Substances 0.000 claims 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
- 235000011150 stannous chloride Nutrition 0.000 claims 1
- 239000001119 stannous chloride Substances 0.000 claims 1
- 235000019364 tetracycline Nutrition 0.000 description 35
- 150000003522 tetracyclines Chemical class 0.000 description 34
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
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- 238000000338 in vitro Methods 0.000 description 11
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- 150000002431 hydrogen Chemical class 0.000 description 7
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 7
- FFTVPQUHLQBXQZ-KVUCHLLUSA-N (4s,4as,5ar,12ar)-4,7-bis(dimethylamino)-1,10,11,12a-tetrahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1C2=C(N(C)C)C=CC(O)=C2C(O)=C2[C@@H]1C[C@H]1[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]1(O)C2=O FFTVPQUHLQBXQZ-KVUCHLLUSA-N 0.000 description 6
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Classifications
-
- 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
- A61P31/04—Antibacterial agents
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- 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)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Communicable Diseases (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Seasonings (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Quinoline Compounds (AREA)
- Pyridine Compounds (AREA)
- Luminescent Compositions (AREA)
- Peptides Or Proteins (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Moulding By Coating Moulds (AREA)
- Tires In General (AREA)
- Spinning Or Twisting Of Yarns (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU9302833A HU212267B (en) | 1991-10-04 | 1992-10-02 | Process for preparing 9-nitro-7-(substituted)-6-demethyl-6-desoxytetracyclin derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/771,697 US5281628A (en) | 1991-10-04 | 1991-10-04 | 9-amino-7-(substituted)-6-demethyl-6-deoxytetracyclines |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| HU9203143D0 HU9203143D0 (en) | 1992-12-28 |
| HUT64298A HUT64298A (en) | 1993-12-28 |
| HU211214B true HU211214B (en) | 1995-11-28 |
Family
ID=25092681
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU9203143A HU211214B (en) | 1991-10-04 | 1992-10-02 | Method for producing novel 9-amino-7-(substituted)-6-demethyl-6-desoxy-tetracycline derivatives and medical preparatives containing them |
| HU95P/P00602P HU211922A9 (en) | 1991-10-04 | 1995-06-29 | Novel 9-amino-7-(substituted)-6-demethyl-6-deoxytetracyclines |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU95P/P00602P HU211922A9 (en) | 1991-10-04 | 1995-06-29 | Novel 9-amino-7-(substituted)-6-demethyl-6-deoxytetracyclines |
Country Status (24)
| Country | Link |
|---|---|
| US (3) | US5281628A (enExample) |
| EP (1) | EP0535346B1 (enExample) |
| JP (1) | JP3183729B2 (enExample) |
| KR (1) | KR100261528B1 (enExample) |
| CN (1) | CN1053182C (enExample) |
| AT (1) | ATE129697T1 (enExample) |
| AU (1) | AU651734B2 (enExample) |
| CA (1) | CA2079703C (enExample) |
| CZ (1) | CZ285015B6 (enExample) |
| DE (1) | DE69205792T2 (enExample) |
| DK (1) | DK0535346T3 (enExample) |
| ES (1) | ES2081005T3 (enExample) |
| FI (1) | FI111716B (enExample) |
| GR (1) | GR3017978T3 (enExample) |
| HU (2) | HU211214B (enExample) |
| IL (1) | IL103319A (enExample) |
| MX (1) | MX9205573A (enExample) |
| NO (1) | NO300129B1 (enExample) |
| NZ (1) | NZ244556A (enExample) |
| PH (1) | PH30343A (enExample) |
| PL (2) | PL170939B1 (enExample) |
| SK (1) | SK281113B6 (enExample) |
| TW (1) | TW222616B (enExample) |
| ZA (1) | ZA927608B (enExample) |
Families Citing this family (55)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5494903A (en) | 1991-10-04 | 1996-02-27 | American Cyanamid Company | 7-substituted-9-substituted amino-6-demethyl-6-deoxytetracyclines |
| USRE40183E1 (en) | 1991-10-04 | 2008-03-25 | Wyeth Holdings Corporation | 7-Substituted-9-substituted amino-6-demethyl-6-deoxytetracyclines |
| WO1993024650A1 (en) * | 1992-05-28 | 1993-12-09 | Monash University | Therapeutic compositions |
| US5442059A (en) * | 1992-08-13 | 1995-08-15 | American Cyanamid Company | 9-[(substituted glycyl)amido)]-6-demethyl-6-deoxytetracyclines |
| US5328902A (en) * | 1992-08-13 | 1994-07-12 | American Cyanamid Co. | 7-(substituted)-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 |
| US5371076A (en) * | 1993-04-02 | 1994-12-06 | American Cyanamid Company | 9-[(substituted glycyl)amido]-6-(substituted)-5-hydroxy-6-deoxytetracyclines |
| US5834450A (en) * | 1994-02-17 | 1998-11-10 | Pfizer Inc. | 9- (substituted amino) -alpha-6-deoxy-5-oxy tetracycline derivatives, their preparation and their use as antibiotics |
| JP2002501026A (ja) * | 1998-01-23 | 2002-01-15 | トルスティーズ オブ トゥフツ カレッジ | 薬学的に活性の化合物及びその利用法 |
| US8106225B2 (en) * | 1999-09-14 | 2012-01-31 | Trustees Of Tufts College | Methods of preparing substituted tetracyclines with transition metal-based chemistries |
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