LU86685A1 - Derives antibiotiques et procede pour les purifier - Google Patents

Derives antibiotiques et procede pour les purifier Download PDF

Info

Publication number: LU86685A1
Authority: LU; Luxembourg
Prior art keywords: antibiotic; imidazolidinone; isomer; sodium; stage
Prior art date: 1985-11-25

Application number

LU86685A

Other languages

English (en)

French (fr)

Original Assignee

Bristol Myers Co

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.)

1985-11-25

Filing date

1986-11-24

Publication date

1987-07-24

1986-11-24 Application filed by Bristol Myers Co filed Critical Bristol Myers Co

1987-07-24 Publication of LU86685A1 publication Critical patent/LU86685A1/fr

Links

230000003115 biocidal effect Effects 0.000 title claims description 55
238000000034 method Methods 0.000 title claims description 33
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 45
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
239000000203 mixture Substances 0.000 claims description 36
159000000000 sodium salts Chemical class 0.000 claims description 30
-1 aralkyl ketone Chemical class 0.000 claims description 27
YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims description 27
239000011734 sodium Substances 0.000 claims description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
239000000243 solution Substances 0.000 claims description 14
229910052708 sodium Inorganic materials 0.000 claims description 13
239000002904 solvent Substances 0.000 claims description 13
150000002576 ketones Chemical class 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 11
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 10
150000001875 compounds Chemical class 0.000 claims description 10
239000000376 reactant Substances 0.000 claims description 10
125000003118 aryl group Chemical group 0.000 claims description 9
238000006243 chemical reaction Methods 0.000 claims description 9
150000008624 imidazolidinones Chemical class 0.000 claims description 8
238000002347 injection Methods 0.000 claims description 8
239000007924 injection Substances 0.000 claims description 8
229910052751 metal Inorganic materials 0.000 claims description 8
239000002184 metal Substances 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 7
239000007788 liquid Substances 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 7
239000012453 solvate Substances 0.000 claims description 7
239000000829 suppository Substances 0.000 claims description 7
125000002723 alicyclic group Chemical group 0.000 claims description 6
239000007787 solid Substances 0.000 claims description 6
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 claims description 5
229940124587 cephalosporin Drugs 0.000 claims description 5
VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical group [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 claims description 5
101000687448 Homo sapiens REST corepressor 1 Proteins 0.000 claims description 4
102100024864 REST corepressor 1 Human genes 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 3
UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 claims description 2
101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 claims description 2
239000007864 aqueous solution Substances 0.000 claims description 2
150000003997 cyclic ketones Chemical class 0.000 claims description 2
238000006053 organic reaction Methods 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
238000000746 purification Methods 0.000 claims description 2
239000000725 suspension Substances 0.000 claims 3
RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 1
239000012295 chemical reaction liquid Substances 0.000 claims 1
230000037406 food intake Effects 0.000 claims 1
XFIMQDGBHJULGY-WFDQOPGTSA-N (6r,7r)-7-[[(2r)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-8-oxo-3-[(z)-prop-1-enyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;hydrate Chemical compound O.C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)\C=C/C)C(O)=O)=CC=C(O)C=C1.C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)\C=C/C)C(O)=O)=CC=C(O)C=C1 XFIMQDGBHJULGY-WFDQOPGTSA-N 0.000 description 20
239000000047 product Substances 0.000 description 18
238000003756 stirring Methods 0.000 description 11
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
239000000126 substance Substances 0.000 description 9
230000015572 biosynthetic process Effects 0.000 description 8
150000001780 cephalosporins Chemical class 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical class CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 description 4
229930186147 Cephalosporin Natural products 0.000 description 4
239000003242 anti bacterial agent Substances 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 4
230000000694 effects Effects 0.000 description 4
238000001914 filtration Methods 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000013078 crystal Substances 0.000 description 3
239000012065 filter cake Substances 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
239000000843 powder Substances 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
238000000926 separation method Methods 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
238000007239 Wittig reaction Methods 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
238000000862 absorption spectrum Methods 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
229940088710 antibiotic agent Drugs 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
239000002775 capsule Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
UOCJDOLVGGIYIQ-PBFPGSCMSA-N cefatrizine Chemical class S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)[C@H](N)C=2C=CC(O)=CC=2)CC=1CSC=1C=NNN=1 UOCJDOLVGGIYIQ-PBFPGSCMSA-N 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
238000003306 harvesting Methods 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 2
150000004682 monohydrates Chemical class 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000000651 prodrug Substances 0.000 description 2
229940002612 prodrug Drugs 0.000 description 2
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
229920002554 vinyl polymer Polymers 0.000 description 2
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
125000006017 1-propenyl group Chemical group 0.000 description 1
PJIBBTJBVQZPKJ-UHFFFAOYSA-N 1-trimethylsilylpropane-1-sulfonic acid Chemical compound CCC([Si](C)(C)C)S(O)(=O)=O PJIBBTJBVQZPKJ-UHFFFAOYSA-N 0.000 description 1
229920003084 Avicel® PH-102 Polymers 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
229930182555 Penicillin Natural products 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
238000002441 X-ray diffraction Methods 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
JVVXZOOGOGPDRZ-SLFFLAALSA-N [(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methanamine Chemical compound NC[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 JVVXZOOGOGPDRZ-SLFFLAALSA-N 0.000 description 1
239000000654 additive Substances 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
150000001336 alkenes Chemical class 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
150000001412 amines Chemical class 0.000 description 1
AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical class C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000012984 antibiotic solution Substances 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
239000008135 aqueous vehicle Substances 0.000 description 1
150000003934 aromatic aldehydes Chemical class 0.000 description 1
238000013475 authorization Methods 0.000 description 1
239000002585 base Substances 0.000 description 1
UPABQMWFWCMOFV-UHFFFAOYSA-N benethamine Chemical compound C=1C=CC=CC=1CNCCC1=CC=CC=C1 UPABQMWFWCMOFV-UHFFFAOYSA-N 0.000 description 1
JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
229960002420 cefatrizine Drugs 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
150000001782 cephems Chemical class 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000010575 fractional recrystallization Methods 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000009776 industrial production Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
238000005259 measurement Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
229940037201 oris Drugs 0.000 description 1
ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical compound [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 description 1
239000008188 pellet Substances 0.000 description 1
235000019371 penicillin G benzathine Nutrition 0.000 description 1
229940056360 penicillin g Drugs 0.000 description 1
150000002960 penicillins Chemical class 0.000 description 1
238000000053 physical method Methods 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
238000002953 preparative HPLC Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Substances [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 1
235000011121 sodium hydroxide Nutrition 0.000 description 1
NASFKTWZWDYFER-UHFFFAOYSA-N sodium;hydrate Chemical compound O.[Na] NASFKTWZWDYFER-UHFFFAOYSA-N 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
230000029305 taxis Effects 0.000 description 1
238000012360 testing method Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
238000002211 ultraviolet spectrum Methods 0.000 description 1
238000003828 vacuum filtration Methods 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical group C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/22—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with radicals containing only hydrogen and carbon atoms, attached in position 3
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/02—Preparation
- C07D501/12—Separation; Purification
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/58—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3 with a nitrogen atom, which is a member of a hetero ring, attached in position 7

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Cephalosporin Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

LU86685A 1985-11-25 1986-11-24 Derives antibiotiques et procede pour les purifier LU86685A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US80127285		1985-11-25
US06/801,272 US4727070A (en)	1985-11-25	1985-11-25	3-Propenzl cephalosporin isomer separation process and derivative

Publications (1)

Publication Number	Publication Date
LU86685A1 true LU86685A1 (fr)	1987-07-24

Family

ID=25180645

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU86685A LU86685A1 (fr)	1985-11-25	1986-11-24	Derives antibiotiques et procede pour les purifier

Country Status (17)

Country	Link
US (1)	US4727070A (de)
KR (1)	KR930007809B1 (de)
AR (1)	AR242582A1 (de)
AT (1)	AT392643B (de)
CA (1)	CA1272715A (de)
CS (1)	CS262442B2 (de)
DD (2)	DD269850A5 (de)
DK (1)	DK563586A (de)
ES (1)	ES2002919A6 (de)
FI (1)	FI85024C (de)
GR (1)	GR862787B (de)
HU (2)	HU202536B (de)
LU (1)	LU86685A1 (de)
NO (1)	NO167460C (de)
PT (1)	PT83798B (de)
SU (1)	SU1493110A3 (de)
YU (2)	YU46182B (de)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4847373A (en) *	1987-02-26	1989-07-11	Bristol-Myers Company	Production of 3-allyl- and 3-butenyl-3-cephems
US5128336A (en) *	1988-03-23	1992-07-07	Eli Lilly And Company	3-(substituted)-1-carba(dethia)-3-cephems
DK0630380T3 (da)	1992-02-05	2001-12-10	Biochemie Gmbh	Fremgangsmåde til rensning af et 3-cephem-4-carboxylsyrederivat
MXPA03006958A (es) *	2001-02-05	2003-11-18	Upjohn Co	Composicion para administracion rectal de farmaco antibacterial de oxazolidinona.
US20060173176A1 (en) *	2002-10-08	2006-08-03	Yatendra Kumar	Process for the preparation of (z)-isomer enriched 7-amino-3-propen-1-yl-3-cephem-4-carboxylic acid
US6903211B2 (en) *	2002-10-30	2005-06-07	Orchid Chemicals & Pharmaceuticals Limited	Process for the preparation of 3-propenyl cephalosporin DMF solvate
EP1678186A4 (de) *	2003-10-30	2007-04-25	Cj Corp	Verfahren zur herstellung von cephem-derivaten
EP1535712B1 (de) *	2003-11-28	2009-01-14	Xenocs S.A.	Verfahren zur Herstellung einer Abformungsmatrize, sowie Abformungsmatrize
ES2338335T3 (es)	2004-11-01	2010-05-06	Hetero Drugs Limited	Nuevo procedimiento de preparacion de intermedio cefprozilo.

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS54112892A (en) *	1978-02-23	1979-09-04	Shionogi & Co Ltd	Substituted imidazolidinyl-3-chloro-3-cephem-4-carboxylic acid
US4520022A (en) *	1983-01-28	1985-05-28	Bristol-Myers Company	Substituted vinyl cephalosporins

1985
- 1985-11-25 US US06/801,272 patent/US4727070A/en not_active Expired - Lifetime
1986
- 1986-11-20 FI FI864738A patent/FI85024C/fi not_active IP Right Cessation
- 1986-11-21 AR AR86305969A patent/AR242582A1/es active
- 1986-11-21 YU YU199286A patent/YU46182B/sh unknown
- 1986-11-21 CA CA000523539A patent/CA1272715A/en not_active Expired - Lifetime
- 1986-11-21 GR GR862787A patent/GR862787B/el unknown
- 1986-11-24 NO NO864683A patent/NO167460C/no not_active IP Right Cessation
- 1986-11-24 DK DK563586A patent/DK563586A/da not_active Application Discontinuation
- 1986-11-24 KR KR1019860009895A patent/KR930007809B1/ko not_active Expired - Lifetime
- 1986-11-24 ES ES8603151A patent/ES2002919A6/es not_active Expired
- 1986-11-24 DD DD86315425A patent/DD269850A5/de unknown
- 1986-11-24 CS CS868555A patent/CS262442B2/cs not_active IP Right Cessation
- 1986-11-24 PT PT83798A patent/PT83798B/pt unknown
- 1986-11-24 DD DD86296598A patent/DD261163A5/de unknown
- 1986-11-24 SU SU864028601A patent/SU1493110A3/ru active
- 1986-11-24 LU LU86685A patent/LU86685A1/fr unknown
- 1986-11-25 HU HU88449A patent/HU202536B/hu unknown
- 1986-11-25 HU HU864866A patent/HU196212B/hu unknown
- 1986-11-25 AT AT3149/86A patent/AT392643B/de not_active IP Right Cessation
1987
- 1987-06-29 YU YU121087A patent/YU46215B/sh unknown

Also Published As

Publication number	Publication date
GR862787B (en)	1987-03-24
DK563586A (da)	1987-05-26
DD269850A5 (de)	1989-07-12
DK563586D0 (da)	1986-11-24
ES2002919A6 (es)	1988-10-01
KR930007809B1 (ko)	1993-08-20
YU46215B (sh)	1993-05-28
KR870004990A (ko)	1987-06-04
FI864738L (fi)	1987-05-26
AT392643B (de)	1991-05-10
US4727070A (en)	1988-02-23
FI864738A0 (fi)	1986-11-20
SU1493110A3 (ru)	1989-07-07
NO167460C (no)	1991-11-06
YU46182B (sh)	1993-05-28
YU199286A (en)	1987-12-31
ATA314986A (de)	1990-10-15
CS262442B2 (en)	1989-03-14
AR242582A1 (es)	1993-04-30
PT83798B (pt)	1989-11-30
HUT42896A (en)	1987-08-28
YU121087A (en)	1988-12-31
CA1272715A (en)	1990-08-14
HU202536B (en)	1991-03-28
NO864683D0 (no)	1986-11-24
PT83798A (en)	1986-12-01
NO167460B (no)	1991-07-29
FI85024B (fi)	1991-11-15
FI85024C (fi)	1992-02-25
DD261163A5 (de)	1988-10-19
HU196212B (en)	1988-10-28
CS855586A2 (en)	1988-06-15

Publication	Publication Date	Title
CH639974A5 (fr)	1983-12-15	Spiro-oxazolidine-diones.
CH643546A5 (fr)	1984-06-15	Procede pour la preparation de derives d'hydantoine.
JPH0471073B2 (de)	1992-11-12
LU86685A1 (fr)	1987-07-24	Derives antibiotiques et procede pour les purifier
EP0462009A1 (de)	1991-12-18	Cephalosporine mit in der Lage 3 ein Propenylradikal, substituiert durch eine quaternäre Ammoniumgruppe, ihr Verfahren zur Herstellung, ihre Anwendung als Medikamente, ihre sie enthaltende Präparate und ihre Zwischenprodukte
LU85473A1 (fr)	1985-04-17	Nouvelles 1,5-benzothiazepines d'utilite cardiovasculaire,procedes pour leur preparation et compositions pharmaceutiques en contenant
FR2585705A1 (fr)	1987-02-06	Sels de cephalosporine et compositions injectables
FR2612517A1 (fr)	1988-09-23	Derives de benzoxazine, procedes de preparation de ces derives et compositions pharmaceutiques les contenant
CA1194873A (fr)	1985-10-08	Procede de preparation de nouveaux produits derives de l'acide 2-amino thiazolyl 2-oxyimino acetamido bicyclo-octene carboxylique
FR2527608A1 (fr)	1983-12-02	Nouveaux composes heterocycliques, leur preparation et leur utilisation comme medicaments
FR2505834A1 (fr)	1982-11-19	Derives de la thiazolidine
FR2480286A1 (fr)	1981-10-16	Nouveaux derives de theophyllinylmethyldioxolane, leurs procedes de preparation et leur application en therapeutique
EP0043756B1 (de)	1984-05-09	1,2,4-Triazinylthiomethyl-3-cephem-sulfoxyde, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Präparate
LU82215A1 (fr)	1980-09-24	Procede et composes intermediaires pour la prouduction du 1,1-dioxyde d'acide penicillanique et de ses esters
FR2499981A1 (fr)	1982-08-20	Acides amino-2 halogenobenzoyl-3 methylphenylacetiques et leurs esters et sels utiles comme medicaments anti-inflammatoires et analgesiques
MC1036A1 (fr)	1975-05-30	Procédé de préparation de composés de mercaptopyrrole condensés
FR2536072A1 (fr)	1984-05-18	Nouveaux derives de la quinazoline, leur preparation et leur utilisation comme medicaments
BE821243A (fr)	1975-04-18	Derives de la penicilline
CH646146A5 (fr)	1984-11-15	Derive du 1alpha,25-dihydroxy cholecalciferol et son procede de preparation.
EP0126013B1 (de)	1987-09-23	Zyklische Dithioacetamide, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zusammensetzungen
BE895076R (fr)	1983-05-19	1-oxydes et 1, 1-dioxydes de 1,2,5-thiadiazoles 3,4-disubstitues
FR2626177A1 (fr)	1989-07-28	Nouveaux derives de l'ergoline, leur preparation et leur utilisation comme medicaments
BE896797A (fr)	1983-11-21	Nouveaux composes heterocycliques, leur preparation et leur utilisation comme medicaments.
BE890499A (fr)	1982-03-25	Nouvelles cephalosporines, leur procede de preparation et leur application en therapeutique
BE832797A (fr)	1976-02-27	Nouvelles cephanycines et leur utilisation