NO133102B - - Google Patents
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- Publication number
- NO133102B NO133102B NO1387/71A NO138771A NO133102B NO 133102 B NO133102 B NO 133102B NO 1387/71 A NO1387/71 A NO 1387/71A NO 138771 A NO138771 A NO 138771A NO 133102 B NO133102 B NO 133102B
- Authority
- NO
- Norway
- Prior art keywords
- sulfosalicylate
- doxycycline
- salt
- base
- oxytetracycline
- Prior art date
Links
- MOODSJOROWROTO-UHFFFAOYSA-N salicylsulfuric acid Chemical compound OC(=O)C1=CC=CC=C1OS(O)(=O)=O MOODSJOROWROTO-UHFFFAOYSA-N 0.000 claims description 29
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
- 229940071103 sulfosalicylate Drugs 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 13
- 239000004100 Oxytetracycline Substances 0.000 claims description 11
- 229960000625 oxytetracycline Drugs 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000012431 aqueous reaction media Substances 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 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 description 18
- 229960003722 doxycycline Drugs 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 9
- IHGRARUXKULRDG-CVHRZJFOSA-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;2-hydroxy-5-sulfobenzoic acid Chemical compound OC(=O)C1=CC(S(O)(=O)=O)=CC=C1O.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 IHGRARUXKULRDG-CVHRZJFOSA-N 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- 238000005984 hydrogenation reaction Methods 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- WXHLLJAMBQLULT-UHFFFAOYSA-N 2-[[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl]amino]-n-(2-methyl-6-sulfanylphenyl)-1,3-thiazole-5-carboxamide;hydrate Chemical compound O.C=1C(N2CCN(CCO)CC2)=NC(C)=NC=1NC(S1)=NC=C1C(=O)NC1=C(C)C=CC=C1S WXHLLJAMBQLULT-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 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 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 229940042016 methacycline Drugs 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- VXPSARQTYDZXAO-CCHMMTNSSA-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;hydron;chloride Chemical compound Cl.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 VXPSARQTYDZXAO-CCHMMTNSSA-N 0.000 description 1
- PTNZGHXUZDHMIQ-CVHRZJFOSA-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;hydrochloride Chemical compound Cl.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 PTNZGHXUZDHMIQ-CVHRZJFOSA-N 0.000 description 1
- OWFJMIVZYSDULZ-PXOLEDIWSA-N (4s,4ar,5s,5ar,6s,12ar)-4-(dimethylamino)-1,5,6,10,11,12a-hexahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide 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)C3=C(O)C2=C1O OWFJMIVZYSDULZ-PXOLEDIWSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000004098 Tetracycline Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229950011479 hyclate Drugs 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229940051860 methacycline hydrochloride Drugs 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- -1 sulfosalicyl salt Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229960002180 tetracycline Drugs 0.000 description 1
- 229930101283 tetracycline Natural products 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 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
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/60—Reduction reactions, e.g. hydrogenation
- B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
- B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
- B01J2231/645—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes of C=C or C-C triple bonds
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10209470A | 1970-12-28 | 1970-12-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO133102B true NO133102B (he) | 1975-12-01 |
| NO133102C NO133102C (he) | 1976-03-10 |
Family
ID=22288092
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO1387/71A NO133102C (he) | 1970-12-28 | 1971-04-14 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US3795707A (he) |
| JP (1) | JPS535299B1 (he) |
| BE (1) | BE777357A (he) |
| CA (1) | CA972745A (he) |
| CH (1) | CH567456A5 (he) |
| DE (1) | DE2117442B2 (he) |
| DK (1) | DK139576B (he) |
| ES (1) | ES391290A1 (he) |
| FI (1) | FI53302B (he) |
| FR (1) | FR2120866A5 (he) |
| GB (1) | GB1370797A (he) |
| IE (1) | IE35673B1 (he) |
| IL (1) | IL37883A (he) |
| NL (1) | NL7113277A (he) |
| NO (1) | NO133102C (he) |
| SE (1) | SE373836B (he) |
| ZA (1) | ZA716574B (he) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3906043A (en) * | 1969-06-12 | 1975-09-16 | Israel Marcus | Water-soluble tetracyclines |
| US4061676A (en) * | 1970-07-03 | 1977-12-06 | Ivan Villax | Recovery of doxycycline and products thereof |
| DK386784A (da) * | 1983-08-17 | 1985-02-18 | Hovione Int Ltd | Fremgangsmaade til fremstilling af alfa-6-desoxy-tetracykliner |
| US5371076A (en) * | 1993-04-02 | 1994-12-06 | American Cyanamid Company | 9-[(substituted glycyl)amido]-6-(substituted)-5-hydroxy-6-deoxytetracyclines |
| US20020132798A1 (en) * | 2000-06-16 | 2002-09-19 | Nelson Mark L. | 7-phenyl-substituted tetracycline compounds |
| EP2311797A1 (en) * | 2002-01-08 | 2011-04-20 | Paratek Pharmaceuticals, Inc. | 4-dedimethylamino tetracycline compounds |
| WO2003079984A2 (en) | 2002-03-21 | 2003-10-02 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds |
| US20060287283A1 (en) * | 2003-07-09 | 2006-12-21 | Paratek Pharmaceuticals, Inc. | Prodrugs of 9-aminomethyl tetracycline compounds |
| EP2298323A3 (en) * | 2003-07-09 | 2011-05-11 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH365484A (fr) * | 1956-05-28 | 1962-11-15 | American Cyanamid Co | Procédé de préparation d'une substance antibiotique |
| FR1430859A (he) * | 1960-05-23 | 1966-05-25 | ||
| US3397231A (en) * | 1967-04-12 | 1968-08-13 | Pfizer & Co C | Refining of alpha-6-deoxy-5-oxytetracycline |
| CA945546A (en) * | 1970-07-03 | 1974-04-16 | Ivan Villax | Recovery of doxycycline and products thereof |
-
1970
- 1970-12-28 US US00102094A patent/US3795707A/en not_active Expired - Lifetime
-
1971
- 1971-04-07 DK DK166871AA patent/DK139576B/da unknown
- 1971-04-08 DE DE2117442A patent/DE2117442B2/de not_active Withdrawn
- 1971-04-13 SE SE7104704A patent/SE373836B/xx unknown
- 1971-04-14 NO NO1387/71A patent/NO133102C/no unknown
- 1971-05-18 ES ES391290A patent/ES391290A1/es not_active Expired
- 1971-06-03 FI FI1538/71A patent/FI53302B/fi active
- 1971-09-28 IE IE1209/71A patent/IE35673B1/xx unknown
- 1971-09-28 NL NL7113277A patent/NL7113277A/xx unknown
- 1971-09-30 ZA ZA716574A patent/ZA716574B/xx unknown
- 1971-10-06 JP JP7797071A patent/JPS535299B1/ja active Pending
- 1971-10-06 CA CA124,593A patent/CA972745A/en not_active Expired
- 1971-10-08 IL IL37883A patent/IL37883A/he unknown
- 1971-10-29 GB GB5036671A patent/GB1370797A/en not_active Expired
- 1971-12-10 CH CH1810371A patent/CH567456A5/xx not_active IP Right Cessation
- 1971-12-24 FR FR7146558A patent/FR2120866A5/fr not_active Expired
- 1971-12-28 BE BE777357A patent/BE777357A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK139576C (he) | 1979-08-27 |
| BE777357A (fr) | 1972-04-17 |
| ES391290A1 (es) | 1972-01-16 |
| NO133102C (he) | 1976-03-10 |
| US3795707A (en) | 1974-03-05 |
| DK139576B (da) | 1979-03-12 |
| JPS535299B1 (he) | 1978-02-25 |
| IE35673B1 (en) | 1976-04-14 |
| IE35673L (en) | 1972-06-28 |
| NL7113277A (he) | 1972-06-30 |
| SE373836B (he) | 1975-02-17 |
| IL37883A0 (en) | 1971-12-29 |
| ZA716574B (en) | 1973-05-30 |
| DE2117442B2 (de) | 1980-06-04 |
| FI53302B (he) | 1977-12-30 |
| GB1370797A (en) | 1974-10-16 |
| IL37883A (he) | 1974-12-31 |
| CH567456A5 (he) | 1975-10-15 |
| DE2117442A1 (de) | 1972-07-27 |
| CA972745A (en) | 1975-08-12 |
| FR2120866A5 (he) | 1972-08-18 |
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