GB1100885A - Oxytetracycline esters and preparation thereof - Google Patents
Oxytetracycline esters and preparation thereofInfo
- Publication number
- GB1100885A GB1100885A GB161667A GB161667A GB1100885A GB 1100885 A GB1100885 A GB 1100885A GB 161667 A GB161667 A GB 161667A GB 161667 A GB161667 A GB 161667A GB 1100885 A GB1100885 A GB 1100885A
- Authority
- GB
- United Kingdom
- Prior art keywords
- esters
- mono
- alkyl
- carbalkoxy
- solvent
- 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
- IWVCMVBTMGNXQD-PXOLEDIWSA-N oxytetracycline Chemical class 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 title abstract 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 abstract 7
- 150000002148 esters Chemical class 0.000 abstract 7
- -1 di-substituted phenyl Chemical group 0.000 abstract 6
- 125000004423 acyloxy group Chemical group 0.000 abstract 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- 239000012442 inert solvent Substances 0.000 abstract 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract 3
- 239000002904 solvent Substances 0.000 abstract 3
- 125000004169 (C1-C6) alkyl group Chemical class 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 239000004098 Tetracycline Substances 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000001475 halogen functional group Chemical class 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- 229960002180 tetracycline Drugs 0.000 abstract 2
- 235000019364 tetracycline Nutrition 0.000 abstract 2
- 229930101283 tetracycline Natural products 0.000 abstract 2
- SGKRLCUYIXIAHR-AKNGSSGZSA-N (4s,4ar,5s,5ar,6r,12ar)-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1=CC=C2[C@H](C)[C@@H]([C@H](O)[C@@H]3[C@](C(O)=C(C(N)=O)C(=O)[C@H]3N(C)C)(O)C3=O)C3=C(O)C2=C1O SGKRLCUYIXIAHR-AKNGSSGZSA-N 0.000 abstract 1
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- 239000000908 ammonium hydroxide Substances 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 230000008020 evaporation Effects 0.000 abstract 1
- 238000001704 evaporation Methods 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 150000004702 methyl esters Chemical class 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- 239000012452 mother liquor Substances 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 230000001376 precipitating effect Effects 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 150000003522 tetracyclines Chemical class 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US43997465A | 1965-03-15 | 1965-03-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1100885A true GB1100885A (en) | 1968-01-24 |
Family
ID=23746905
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB161667A Expired GB1100885A (en) | 1965-03-15 | 1965-08-02 | Oxytetracycline esters and preparation thereof |
| GB3301365A Expired GB1100884A (en) | 1965-03-15 | 1965-08-02 | Oxytetracycline esters and preparation thereof |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3301365A Expired GB1100884A (en) | 1965-03-15 | 1965-08-02 | Oxytetracycline esters and preparation thereof |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE685168A (enrdf_load_stackoverflow) |
| BR (1) | BR6677270D0 (enrdf_load_stackoverflow) |
| CH (1) | CH481065A (enrdf_load_stackoverflow) |
| FR (1) | FR5665M (enrdf_load_stackoverflow) |
| GB (2) | GB1100885A (enrdf_load_stackoverflow) |
| NL (1) | NL152543B (enrdf_load_stackoverflow) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010126607A3 (en) * | 2009-04-30 | 2011-07-21 | President And Fellows Of Harvard College | Synthesis of tetracyclines and intermediates thereto |
| EP2345637A3 (en) * | 2002-07-12 | 2012-02-15 | Paratek Pharmaceuticals, Inc. | 3, 10, and 12a substituted tetracycline compounds |
| US8293920B2 (en) | 2006-10-11 | 2012-10-23 | President And Fellows Of Harvard College | Synthesis of enone intermediate |
| US8486921B2 (en) | 2006-04-07 | 2013-07-16 | President And Fellows Of Harvard College | Synthesis of tetracyclines and analogues thereof |
| US8598148B2 (en) | 2004-05-21 | 2013-12-03 | President And Fellows Of Harvard College | Synthesis of tetracyclines and analogues thereof |
-
1965
- 1965-08-02 GB GB161667A patent/GB1100885A/en not_active Expired
- 1965-08-02 GB GB3301365A patent/GB1100884A/en not_active Expired
-
1966
- 1966-02-18 BR BR17727066A patent/BR6677270D0/pt unknown
- 1966-02-23 CH CH259566A patent/CH481065A/de not_active IP Right Cessation
- 1966-02-23 FR FR50780A patent/FR5665M/fr not_active Expired
- 1966-02-24 NL NL6602413A patent/NL152543B/xx unknown
- 1966-08-05 BE BE685168D patent/BE685168A/xx unknown
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8481513B2 (en) | 2002-07-12 | 2013-07-09 | Paratek Pharmaceuticals, Inc. | 3, 10, and 12a substituted tetracycline compounds |
| EP2345637A3 (en) * | 2002-07-12 | 2012-02-15 | Paratek Pharmaceuticals, Inc. | 3, 10, and 12a substituted tetracycline compounds |
| US8598148B2 (en) | 2004-05-21 | 2013-12-03 | President And Fellows Of Harvard College | Synthesis of tetracyclines and analogues thereof |
| US9365493B2 (en) | 2004-05-21 | 2016-06-14 | President And Fellows Of Harvard College | Synthesis of tetracyclines and analogues thereof |
| US9884830B2 (en) | 2004-05-21 | 2018-02-06 | President And Fellows Of Harvard College | Synthesis of tetracyclines and analogues thereof |
| US10669244B2 (en) | 2004-05-21 | 2020-06-02 | President And Fellows Of Harvard College | Synthesis of tetracyclines and analogues thereof |
| US11192866B2 (en) | 2004-05-21 | 2021-12-07 | President And Fellows Of Harvard College | Synthesis of tetracyclines and analogues thereof |
| US8486921B2 (en) | 2006-04-07 | 2013-07-16 | President And Fellows Of Harvard College | Synthesis of tetracyclines and analogues thereof |
| US8293920B2 (en) | 2006-10-11 | 2012-10-23 | President And Fellows Of Harvard College | Synthesis of enone intermediate |
| US8580969B2 (en) | 2006-10-11 | 2013-11-12 | President And Fellows Of Harvard College | Synthesis of enone intermediate |
| US8907104B2 (en) | 2006-10-11 | 2014-12-09 | President And Fellows Of Harvard College | Synthesis of enone intermediate |
| WO2010126607A3 (en) * | 2009-04-30 | 2011-07-21 | President And Fellows Of Harvard College | Synthesis of tetracyclines and intermediates thereto |
| US9073829B2 (en) | 2009-04-30 | 2015-07-07 | President And Fellows Of Harvard College | Synthesis of tetracyclines and intermediates thereto |
| US9688644B2 (en) | 2009-04-30 | 2017-06-27 | President And Fellows Of Harvard College | Synthesis of Tetracyclines and intermediates thereto |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1100884A (en) | 1968-01-24 |
| NL152543B (nl) | 1977-03-15 |
| FR5665M (enrdf_load_stackoverflow) | 1968-01-02 |
| NL6602413A (enrdf_load_stackoverflow) | 1966-09-16 |
| BR6677270D0 (pt) | 1973-09-18 |
| BE685168A (enrdf_load_stackoverflow) | 1967-02-06 |
| CH481065A (de) | 1969-11-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1412130A (en) | 3-substituted-morphinan derivatives | |
| ES341123A1 (es) | Un procedimiento para preparar acidos (indazol-3-il)-oxial-canoicos. | |
| GB1100885A (en) | Oxytetracycline esters and preparation thereof | |
| GB1348093A (en) | Dialkyl-4-hydroxyphenylcarboxylates of tris-hydroxyalkyl-iso cyanurate | |
| ES360566A1 (es) | Un metodo de obtencion de alfa-cetoglutarato de piridoxina y sus derivados. | |
| GB1131498A (en) | Niconitic acid esters | |
| GB1129158A (en) | Coronary dilating compositions | |
| ES464122A1 (es) | Un procedimiento para la preparacion de eteres de acido cla-vulanico. | |
| ES301503A1 (es) | Un procedimiento para la preparaciën de un compuesto derivado del acido nicotinico | |
| GB980777A (en) | ª‡-amino-substituted penicillins | |
| GB894460A (en) | Improvements in or relating to penicillins | |
| ES329449A1 (es) | Un procedimiento para la preparacion de penicilinas. | |
| ES317079A1 (es) | Un procedimiento para la preparaciën en penicilinas | |
| ES402700A1 (es) | Metodo de preparacion de resinas. | |
| GB1000506A (en) | 1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocines | |
| US2910487A (en) | Process for preparing 2-acetoxysteroids | |
| GB860292A (en) | Tetraiodoanthranilic acid and derivatives thereof, and their preparation and compositions containing them | |
| GB1209432A (en) | Ethane-phosphonic acid esters | |
| GB1022201A (en) | A process for preparing 2,6-dichlorobenzonitrile | |
| GB1003478A (en) | 8-hydroxy-quinoline derivatives | |
| GB1251069A (enrdf_load_stackoverflow) | ||
| GB892777A (en) | Gibberellins | |
| GB1164594A (en) | Biologically Active Substituted S-Traizines | |
| GB1034498A (en) | A process for preparing inosine and derivatives thereof | |
| GB1223981A (en) | New salt of fumagillin |