DD219021A3 - Verfahren zur herstellung von 11a-chlor-5-hydroxy-tetracyclin-6,12-hemiketal - Google Patents

Verfahren zur herstellung von 11a-chlor-5-hydroxy-tetracyclin-6,12-hemiketal Download PDF

Info

Publication number: DD219021A3
Authority: DD; German Democratic Republic
Prior art keywords: chloro; chlorinating; hydroxy; hemiketal; tetracycline
Prior art date: 1982-08-24

Application number

DD24273682A

Other languages

German (de)

English (en)

Inventor

Wolfgang Krueger

Gisela Krueger

Original Assignee

Jenapharm Veb

Priority date (The priority date 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 date listed.)

1982-08-24

Filing date

1982-08-24

Publication date

1985-02-20

1982-08-24 Application filed by Jenapharm Veb filed Critical Jenapharm Veb

1982-08-24 Priority to DD24273682A priority Critical patent/DD219021A3/de

1983-05-19 Priority to CS833524A priority patent/CS251657B1/cs

1985-02-20 Publication of DD219021A3 publication Critical patent/DD219021A3/de

Links

238000004519 manufacturing process Methods 0.000 title abstract description 3
238000000034 method Methods 0.000 claims abstract description 22
239000012320 chlorinating reagent Substances 0.000 claims abstract description 14
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 claims abstract description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
238000006243 chemical reaction Methods 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 4
239000004100 Oxytetracycline Substances 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 3
-1 alkali metal salt Chemical class 0.000 claims description 3
239000007795 chemical reaction product Substances 0.000 claims description 3
229960000625 oxytetracycline Drugs 0.000 claims description 3
238000002955 isolation Methods 0.000 claims description 2
SJUGPXBWZCQTKM-UHFFFAOYSA-N n-chloro-4-methylbenzenesulfonamide;sodium Chemical compound [Na].CC1=CC=C(S(=O)(=O)NCl)C=C1 SJUGPXBWZCQTKM-UHFFFAOYSA-N 0.000 claims description 2
238000001556 precipitation Methods 0.000 claims description 2
235000019366 oxytetracycline Nutrition 0.000 claims 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 claims 2
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 abstract description 10
150000002085 enols Chemical group 0.000 abstract description 5
150000001447 alkali salts Chemical class 0.000 abstract description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
239000000047 product Substances 0.000 description 7
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
VDQQXEISLMTGAB-UHFFFAOYSA-N chloramine T Chemical compound [Na+].CC1=CC=C(S(=O)(=O)[N-]Cl)C=C1 VDQQXEISLMTGAB-UHFFFAOYSA-N 0.000 description 6
238000005660 chlorination reaction Methods 0.000 description 6
239000000203 mixture Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
238000001139 pH measurement Methods 0.000 description 3
150000001408 amides Chemical class 0.000 description 2
230000003139 buffering effect Effects 0.000 description 2
238000005259 measurement Methods 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
UWMJRBYGKZOPCC-UHFFFAOYSA-N 1-chloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)NC1=O UWMJRBYGKZOPCC-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
239000004098 Tetracycline Substances 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
239000000645 desinfectant Substances 0.000 description 1
NSNHWTBQMQIDCF-UHFFFAOYSA-N dihydrate;hydrochloride Chemical compound O.O.Cl NSNHWTBQMQIDCF-UHFFFAOYSA-N 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
229960003924 oxytetracycline dihydrate Drugs 0.000 description 1
229960004368 oxytetracycline hydrochloride Drugs 0.000 description 1
SPVPCIOVNUPSLF-UHFFFAOYSA-N pyridine-2-carbaldehyde;dihydrochloride Chemical compound Cl.Cl.O=CC1=CC=CC=N1 SPVPCIOVNUPSLF-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
239000000725 suspension Substances 0.000 description 1
229960002180 tetracycline Drugs 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
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Crystals, And After-Treatments Of Crystals (AREA)

DD24273682A 1982-08-24 1982-08-24 Verfahren zur herstellung von 11a-chlor-5-hydroxy-tetracyclin-6,12-hemiketal DD219021A3 (de)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
DD24273682A DD219021A3 (de)	1982-08-24	1982-08-24	Verfahren zur herstellung von 11a-chlor-5-hydroxy-tetracyclin-6,12-hemiketal
CS833524A CS251657B1 (en)	1982-08-24	1983-05-19	Preparation method of the 11a-chlorine-5-hydroxytetracyclone-6,12-hemiketale

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DD24273682A DD219021A3 (de)	1982-08-24	1982-08-24	Verfahren zur herstellung von 11a-chlor-5-hydroxy-tetracyclin-6,12-hemiketal

Publications (1)

Publication Number	Publication Date
DD219021A3 true DD219021A3 (de)	1985-02-20

Family

ID=5540820

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD24273682A DD219021A3 (de)	1982-08-24	1982-08-24	Verfahren zur herstellung von 11a-chlor-5-hydroxy-tetracyclin-6,12-hemiketal

Country Status (2)

Country	Link
CS (1)	CS251657B1 (cs)
DD (1)	DD219021A3 (cs)

1982
- 1982-08-24 DD DD24273682A patent/DD219021A3/de not_active IP Right Cessation
1983
- 1983-05-19 CS CS833524A patent/CS251657B1/cs unknown

Also Published As

Publication number	Publication date
CS352483A1 (en)	1985-07-16
CS251657B1 (en)	1987-07-16

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Date	Code	Title	Description
2001-06-21	ENJ	Ceased due to non-payment of renewal fee