FI59394C - Foerfarande foer 11a-klorering av oxitetracyklin - Google Patents
Foerfarande foer 11a-klorering av oxitetracyklin Download PDFInfo
- Publication number
- FI59394C FI59394C FI2072/74A FI207274A FI59394C FI 59394 C FI59394 C FI 59394C FI 2072/74 A FI2072/74 A FI 2072/74A FI 207274 A FI207274 A FI 207274A FI 59394 C FI59394 C FI 59394C
- Authority
- FI
- Finland
- Prior art keywords
- oxytetracycline
- hemiketal
- chlorination
- chloro
- acid
- Prior art date
Links
- 239000002253 acid Substances 0.000 claims description 20
- 239000004100 Oxytetracycline Substances 0.000 claims description 16
- 229960000625 oxytetracycline Drugs 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 15
- 238000005660 chlorination reaction Methods 0.000 claims description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 239000011541 reaction mixture Substances 0.000 claims description 11
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 claims description 8
- 239000012442 inert solvent Substances 0.000 claims description 7
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 5
- 239000011707 mineral Substances 0.000 claims description 5
- 239000012320 chlorinating reagent Substances 0.000 claims description 4
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 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 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 235000019366 oxytetracycline Nutrition 0.000 description 3
- 229960004368 oxytetracycline hydrochloride Drugs 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 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 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 101100336126 Mus musculus Gatad1 gene Proteins 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- JBIWCJUYHHGXTC-AKNGSSGZSA-N doxycycline Chemical compound O=C1C2=C(O)C=CC=C2[C@H](C)[C@@H]2C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@@H]1[C@H]2O JBIWCJUYHHGXTC-AKNGSSGZSA-N 0.000 description 1
- 150000002085 enols Chemical group 0.000 description 1
- -1 ethylene dimethyl Chemical group 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- HPOKESDSMZRZLC-UHFFFAOYSA-N propan-2-one;hydrochloride Chemical compound Cl.CC(C)=O HPOKESDSMZRZLC-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- MOODSJOROWROTO-UHFFFAOYSA-N salicylsulfuric acid Chemical compound OC(=O)C1=CC=CC=C1OS(O)(=O)=O MOODSJOROWROTO-UHFFFAOYSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229940071103 sulfosalicylate Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- MWKJTNBSKNUMFN-UHFFFAOYSA-N trifluoromethyltrimethylsilane Chemical compound C[Si](C)(C)C(F)(F)F MWKJTNBSKNUMFN-UHFFFAOYSA-N 0.000 description 1
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
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38496973A | 1973-08-02 | 1973-08-02 | |
| US38496973 | 1973-08-02 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI207274A7 FI207274A7 (pl) | 1975-02-03 |
| FI59394B FI59394B (fi) | 1981-04-30 |
| FI59394C true FI59394C (fi) | 1981-08-10 |
Family
ID=23519498
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI2072/74A FI59394C (fi) | 1973-08-02 | 1974-07-05 | Foerfarande foer 11a-klorering av oxitetracyklin |
Country Status (28)
| Country | Link |
|---|---|
| JP (1) | JPS5835982B2 (pl) |
| AR (1) | AR199626A1 (pl) |
| AT (1) | AT333426B (pl) |
| AU (1) | AU476600B2 (pl) |
| BE (1) | BE817406A (pl) |
| CA (1) | CA1008068A (pl) |
| CH (1) | CH582650A5 (pl) |
| CS (1) | CS183754B2 (pl) |
| DD (1) | DD113527A5 (pl) |
| DE (1) | DE2433608C2 (pl) |
| DK (1) | DK153400C (pl) |
| ES (1) | ES428365A1 (pl) |
| FI (1) | FI59394C (pl) |
| FR (1) | FR2239450B1 (pl) |
| GB (1) | GB1465542A (pl) |
| HK (1) | HK28479A (pl) |
| HU (1) | HU170051B (pl) |
| IE (1) | IE39803B1 (pl) |
| IL (1) | IL45119A (pl) |
| KE (1) | KE2934A (pl) |
| LU (1) | LU70504A1 (pl) |
| MY (1) | MY7900241A (pl) |
| NL (1) | NL177596C (pl) |
| PH (1) | PH10821A (pl) |
| PL (1) | PL94201B1 (pl) |
| SE (1) | SE416727B (pl) |
| YU (1) | YU39463B (pl) |
| ZA (1) | ZA744126B (pl) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2984686A (en) * | 1960-12-19 | 1961-05-16 | Pfizer & Co C | 6-deoxy-6-demethyl-6-methylene-5-oxytetracyclines |
-
1974
- 1974-02-04 GB GB512474A patent/GB1465542A/en not_active Expired
- 1974-06-24 SE SE7408295A patent/SE416727B/xx not_active IP Right Cessation
- 1974-06-24 CA CA203,251A patent/CA1008068A/en not_active Expired
- 1974-06-25 IL IL45119A patent/IL45119A/en unknown
- 1974-06-26 YU YU1788/74A patent/YU39463B/xx unknown
- 1974-06-26 IE IE1360/74A patent/IE39803B1/xx unknown
- 1974-06-26 ZA ZA00744126A patent/ZA744126B/xx unknown
- 1974-06-27 PH PH15989A patent/PH10821A/en unknown
- 1974-07-05 FI FI2072/74A patent/FI59394C/fi active
- 1974-07-05 AU AU70885/74A patent/AU476600B2/en not_active Expired
- 1974-07-09 BE BE1006064A patent/BE817406A/xx not_active IP Right Cessation
- 1974-07-09 JP JP49078645A patent/JPS5835982B2/ja not_active Expired
- 1974-07-09 NL NLAANVRAGE7409249,A patent/NL177596C/xx not_active IP Right Cessation
- 1974-07-09 FR FR7423842A patent/FR2239450B1/fr not_active Expired
- 1974-07-10 DE DE2433608A patent/DE2433608C2/de not_active Expired
- 1974-07-10 CH CH950974A patent/CH582650A5/xx not_active IP Right Cessation
- 1974-07-10 DK DK370074A patent/DK153400C/da not_active IP Right Cessation
- 1974-07-11 LU LU70504A patent/LU70504A1/xx unknown
- 1974-07-12 AT AT579274A patent/AT333426B/de not_active IP Right Cessation
- 1974-07-17 PL PL1974172793A patent/PL94201B1/pl unknown
- 1974-07-17 ES ES428365A patent/ES428365A1/es not_active Expired
- 1974-07-17 HU HUPI426A patent/HU170051B/hu not_active IP Right Cessation
- 1974-07-18 DD DD179987A patent/DD113527A5/xx unknown
- 1974-07-18 CS CS7400005144A patent/CS183754B2/cs unknown
- 1974-07-18 AR AR254757A patent/AR199626A1/es active
-
1979
- 1979-03-16 KE KE2934A patent/KE2934A/xx unknown
- 1979-05-03 HK HK284/79A patent/HK28479A/xx unknown
- 1979-12-30 MY MY241/79A patent/MY7900241A/xx unknown
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