PL83459B1 - - Google Patents
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- Publication number
- PL83459B1 PL83459B1 PL1972157620A PL15762072A PL83459B1 PL 83459 B1 PL83459 B1 PL 83459B1 PL 1972157620 A PL1972157620 A PL 1972157620A PL 15762072 A PL15762072 A PL 15762072A PL 83459 B1 PL83459 B1 PL 83459B1
- Authority
- PL
- Poland
- Prior art keywords
- tris
- tetracycline
- band
- tetracyclines
- derivatives
- Prior art date
Links
- 239000004098 Tetracycline Substances 0.000 claims description 18
- 235000019364 tetracycline Nutrition 0.000 claims description 15
- 150000003522 tetracyclines Chemical class 0.000 claims description 15
- 239000007983 Tris buffer Substances 0.000 claims description 12
- 229940040944 tetracyclines Drugs 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 8
- 229960002180 tetracycline Drugs 0.000 claims description 8
- 229930101283 tetracycline Natural products 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 5
- 235000019366 oxytetracycline Nutrition 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- NWXMGUDVXFXRIG-WESIUVDSSA-N (4s,4as,5as,6s,12ar)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide Chemical compound C1=CC=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]4(O)C(=O)C3=C(O)C2=C1O NWXMGUDVXFXRIG-WESIUVDSSA-N 0.000 claims 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 1
- 235000019365 chlortetracycline Nutrition 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- IZXGZAJMDLJLMF-UHFFFAOYSA-N methylaminomethanol Chemical compound CNCO IZXGZAJMDLJLMF-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 7
- 239000000243 solution Substances 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000004100 Oxytetracycline Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229960000625 oxytetracycline Drugs 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- XIYOPDCBBDCGOE-IWVLMIASSA-N (4s,4ar,5s,5ar,12ar)-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methylidene-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide Chemical compound C=C1C2=CC=CC(O)=C2C(O)=C2[C@@H]1[C@H](O)[C@H]1[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]1(O)C2=O XIYOPDCBBDCGOE-IWVLMIASSA-N 0.000 description 2
- OGQYJDHTHFAPRN-UHFFFAOYSA-N 2-fluoro-6-(trifluoromethyl)benzonitrile Chemical compound FC1=CC=CC(C(F)(F)F)=C1C#N OGQYJDHTHFAPRN-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 229960003185 chlortetracycline hydrochloride Drugs 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000010253 intravenous injection Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229940042016 methacycline Drugs 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- IWVCMVBTMGNXQD-PXOLEDIWSA-N oxytetracycline Chemical compound C1=CC=C2[C@](O)(C)[C@H]3[C@H](O)[C@H]4[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-PXOLEDIWSA-N 0.000 description 2
- 229960004368 oxytetracycline hydrochloride Drugs 0.000 description 2
- IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 2
- MWKJTNBSKNUMFN-UHFFFAOYSA-N trifluoromethyltrimethylsilane Chemical compound C[Si](C)(C)C(F)(F)F MWKJTNBSKNUMFN-UHFFFAOYSA-N 0.000 description 2
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
- 101100328518 Caenorhabditis elegans cnt-1 gene Proteins 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 238000005902 aminomethylation reaction Methods 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 210000002159 anterior chamber Anatomy 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- XMEVHPAGJVLHIG-FMZCEJRJSA-N chembl454950 Chemical compound [Cl-].C1=CC=C2[C@](O)(C)[C@H]3C[C@H]4[C@H]([NH+](C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O XMEVHPAGJVLHIG-FMZCEJRJSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 231100000344 non-irritating Toxicity 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 210000003625 skull Anatomy 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 239000004296 sodium metabisulphite Substances 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229960004989 tetracycline hydrochloride Drugs 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D277/38—Nitrogen atoms
- C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4153371A GB1401178A (en) | 1971-09-06 | 1971-09-06 | Complexes of tetracyclines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL83459B1 true PL83459B1 (online.php) | 1975-12-31 |
Family
ID=10420133
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1972157620A PL83459B1 (online.php) | 1971-09-06 | 1972-09-06 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4418060A (online.php) |
| JP (1) | JPS587610B2 (online.php) |
| BE (1) | BE788479A (online.php) |
| CS (1) | CS226153B2 (online.php) |
| DE (1) | DE2243776C2 (online.php) |
| FR (1) | FR2154464B1 (online.php) |
| GB (1) | GB1401178A (online.php) |
| HK (1) | HK58877A (online.php) |
| PL (1) | PL83459B1 (online.php) |
| YU (1) | YU225972A (online.php) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE788479A (fr) | 1971-09-06 | 1973-01-02 | Medimpex Gyogyszerkulkereskede | Complexes du tris(hydroxymethyl)aminomethane avec les tetracyclines formant des solutions neutres, stables, tres actives etnon toxiques |
| PT1676579E (pt) * | 1998-05-08 | 2009-03-24 | Univ Miami | Utilização de tetraciclinas sub-antimicrobianas para o tratamento de rosácea ocular |
| EP1153010A1 (en) | 1999-02-08 | 2001-11-14 | Checkpoint Genetics, Inc. | $i(N)-SUBSTITUTED AMINO ACIDS, ANTIOXIDANT PHARMACEUTICAL COMPOSITIONS CONTAINING SAME AND METHODS USING SAME |
| NZ544826A (en) * | 2003-07-25 | 2008-07-31 | Warner Chilcott Co Inc | A doxycycline metal complex in a solid dosage form |
| US7807842B2 (en) * | 2004-05-21 | 2010-10-05 | President And Fellows Of Harvard College | Synthesis of tetracyclines and analogues thereof |
| CN101128206A (zh) * | 2005-01-21 | 2008-02-20 | 沃纳奇尔科特公司 | 固体剂型形式的四环素类金属络合物 |
| EP2016044B1 (en) * | 2006-04-07 | 2020-06-10 | President and Fellows of Harvard College | Pentacycline derivatives for the treatment of infections |
| EP2479169B1 (en) | 2006-10-11 | 2014-12-03 | President and Fellows of Harvard College | Synthesis of Enone Intermediate |
| WO2010126607A2 (en) | 2009-04-30 | 2010-11-04 | President And Fellows Of Harvard College | Synthesis of tetracyclines and intermediates thereto |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE754346A (fr) * | 1969-08-06 | 1971-01-18 | Bru Jean | Composition pharmaceutique a base de tetracycline presentee sous une forme effervescente |
| BE788479A (fr) | 1971-09-06 | 1973-01-02 | Medimpex Gyogyszerkulkereskede | Complexes du tris(hydroxymethyl)aminomethane avec les tetracyclines formant des solutions neutres, stables, tres actives etnon toxiques |
-
0
- BE BE788479D patent/BE788479A/xx not_active IP Right Cessation
-
1971
- 1971-09-06 GB GB4153371A patent/GB1401178A/en not_active Expired
-
1972
- 1972-09-05 CS CS726077A patent/CS226153B2/cs unknown
- 1972-09-05 FR FR7231461A patent/FR2154464B1/fr not_active Expired
- 1972-09-06 YU YU02259/72A patent/YU225972A/xx unknown
- 1972-09-06 DE DE2243776A patent/DE2243776C2/de not_active Expired
- 1972-09-06 PL PL1972157620A patent/PL83459B1/pl unknown
- 1972-09-06 JP JP47089455A patent/JPS587610B2/ja not_active Expired
-
1977
- 1977-11-24 HK HK588/77A patent/HK58877A/xx unknown
-
1979
- 1979-09-17 US US06/076,337 patent/US4418060A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| FR2154464A1 (online.php) | 1973-05-11 |
| DE2243776A1 (de) | 1973-03-22 |
| YU225972A (en) | 1982-02-28 |
| GB1401178A (en) | 1975-07-16 |
| JPS587610B2 (ja) | 1983-02-10 |
| CS226153B2 (en) | 1984-03-19 |
| BE788479A (fr) | 1973-01-02 |
| HK58877A (en) | 1977-12-02 |
| US4418060A (en) | 1983-11-29 |
| FR2154464B1 (online.php) | 1975-10-31 |
| DE2243776C2 (de) | 1983-01-27 |
| JPS4861610A (online.php) | 1973-08-29 |
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