CH506495A - Verfahren zur Herstellung von Tetracyclinderivaten - Google Patents

Verfahren zur Herstellung von Tetracyclinderivaten

Info

Publication number: CH506495A
Authority: CH; Switzerland
Prior art keywords: tetracycline; sodium; chlorotetracycline; methanol; formaldehyde
Prior art date: 1966-01-29

Application number

CH134767A

Other languages

German (de)

English (en)

Inventor

Banci Feriano

Tubaro Ezio

Original Assignee

Stabilimenti Chimico Farmaceut

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.)

1966-01-29

Filing date

1967-01-27

Publication date

1971-04-30

1966-11-26 Priority claimed from IT4314066A external-priority patent/IT1045401B/it

1967-01-27 Application filed by Stabilimenti Chimico Farmaceut filed Critical Stabilimenti Chimico Farmaceut

1971-04-30 Publication of CH506495A publication Critical patent/CH506495A/de

Links

239000004098 Tetracycline Substances 0.000 title claims abstract description 40
235000019364 tetracycline Nutrition 0.000 title claims abstract description 40
150000003522 tetracyclines Chemical class 0.000 title claims abstract description 35
229940040944 tetracyclines Drugs 0.000 title abstract description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 125
229960002180 tetracycline Drugs 0.000 claims abstract description 34
229930101283 tetracycline Natural products 0.000 claims abstract description 34
150000001412 amines Chemical class 0.000 claims abstract description 17
150000001875 compounds Chemical class 0.000 claims abstract description 8
125000000217 alkyl group Chemical group 0.000 claims abstract description 4
125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 135
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 45
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 32
CYDMQBQPVICBEU-UHFFFAOYSA-N chlorotetracycline Natural products C1=CC(Cl)=C2C(O)(C)C3CC4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O CYDMQBQPVICBEU-UHFFFAOYSA-N 0.000 claims description 30
239000000203 mixture Substances 0.000 claims description 23
238000000034 method Methods 0.000 claims description 21
239000011734 sodium Substances 0.000 claims description 17
-1 sodium ethylaminomethanesulfonate Chemical compound 0.000 claims description 11
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 10
239000004099 Chlortetracycline Substances 0.000 claims description 8
239000007864 aqueous solution Substances 0.000 claims description 8
229960004475 chlortetracycline Drugs 0.000 claims description 8
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 description 8
235000019365 chlortetracycline Nutrition 0.000 claims description 7
239000002904 solvent Substances 0.000 claims description 7
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 6
229910052708 sodium Inorganic materials 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
159000000000 sodium salts Chemical class 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 4
KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
CYDMQBQPVICBEU-XRNKAMNCSA-N chlortetracycline Chemical compound C1=CC(Cl)=C2[C@](O)(C)[C@H]3C[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 CYDMQBQPVICBEU-XRNKAMNCSA-N 0.000 claims 8
239000000463 material Substances 0.000 claims 1
SBZTWDUPVMDONZ-UHFFFAOYSA-M sodium;2-aminoethanesulfinate Chemical compound [Na+].NCCS([O-])=O SBZTWDUPVMDONZ-UHFFFAOYSA-M 0.000 claims 1
UZHDDUOPWFLWPC-UHFFFAOYSA-M sodium;aminomethanesulfonate Chemical compound [Na+].NCS([O-])(=O)=O UZHDDUOPWFLWPC-UHFFFAOYSA-M 0.000 claims 1
LTSRSKFZDFKNRK-UHFFFAOYSA-M sodium;methylaminomethanesulfonate Chemical compound [Na+].CNCS([O-])(=O)=O LTSRSKFZDFKNRK-UHFFFAOYSA-M 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 8
210000004185 liver Anatomy 0.000 abstract description 5
GUXHBMASAHGULD-SEYHBJAFSA-N (4s,4as,5as,6s,12ar)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1([C@H]2O)=C(Cl)C=CC(O)=C1C(O)=C1[C@@H]2C[C@H]2[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]2(O)C1=O GUXHBMASAHGULD-SEYHBJAFSA-N 0.000 abstract description 4
FMTDIUIBLCQGJB-UHFFFAOYSA-N Demethylchlortetracyclin Natural products C1C2C(O)C3=C(Cl)C=CC(O)=C3C(=O)C2=C(O)C2(O)C1C(N(C)C)C(O)=C(C(N)=O)C2=O FMTDIUIBLCQGJB-UHFFFAOYSA-N 0.000 abstract description 4
230000007665 chronic toxicity Effects 0.000 abstract description 4
231100000160 chronic toxicity Toxicity 0.000 abstract description 4
230000007059 acute toxicity Effects 0.000 abstract description 3
231100000403 acute toxicity Toxicity 0.000 abstract description 3
239000007859 condensation product Substances 0.000 abstract description 2
230000007850 degeneration Effects 0.000 abstract description 2
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 2
229910006080 SO2X Inorganic materials 0.000 abstract 1
JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 abstract 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 63
239000000047 product Substances 0.000 description 30
239000000243 solution Substances 0.000 description 27
DHPRQBPJLMKORJ-XRNKAMNCSA-N (4s,4as,5as,6s,12ar)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide Chemical compound C1=CC(Cl)=C2[C@](O)(C)[C@H]3C[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 DHPRQBPJLMKORJ-XRNKAMNCSA-N 0.000 description 20
239000007795 chemical reaction product Substances 0.000 description 18
238000004458 analytical method Methods 0.000 description 12
239000000460 chlorine Substances 0.000 description 9
QYAPHLRPFNSDNH-MRFRVZCGSA-N (4s,4as,5as,6s,12ar)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide;hydrochloride Chemical compound Cl.C1=CC(Cl)=C2[C@](O)(C)[C@H]3C[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 QYAPHLRPFNSDNH-MRFRVZCGSA-N 0.000 description 8
VVIUBCNYACGLLV-UHFFFAOYSA-N hypotaurine Chemical compound [NH3+]CCS([O-])=O VVIUBCNYACGLLV-UHFFFAOYSA-N 0.000 description 8
OGQYJDHTHFAPRN-UHFFFAOYSA-N 2-fluoro-6-(trifluoromethyl)benzonitrile Chemical compound FC1=CC=CC(C(F)(F)F)=C1C#N OGQYJDHTHFAPRN-UHFFFAOYSA-N 0.000 description 6
229960003185 chlortetracycline hydrochloride Drugs 0.000 description 6
238000010521 absorption reaction Methods 0.000 description 5
230000002378 acidificating effect Effects 0.000 description 5
SHWIJIJNPFXOFS-UHFFFAOYSA-N thiotaurine Chemical compound NCCS(O)(=O)=S SHWIJIJNPFXOFS-UHFFFAOYSA-N 0.000 description 5
241000699670 Mus sp. Species 0.000 description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
230000000844 anti-bacterial effect Effects 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
238000000338 in vitro Methods 0.000 description 4
229910052717 sulfur Inorganic materials 0.000 description 4
239000011593 sulfur Substances 0.000 description 4
NWXMGUDVXFXRIG-WESIUVDSSA-N (4s,4as,5as,6s,12ar)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide Chemical compound C1=CC=C2[C@](O)(C)[C@H]3C[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 NWXMGUDVXFXRIG-WESIUVDSSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
241000191938 Micrococcus luteus Species 0.000 description 3
239000002253 acid Substances 0.000 description 3
OBESRABRARNZJB-UHFFFAOYSA-N aminomethanesulfonic acid Chemical compound NCS(O)(=O)=O OBESRABRARNZJB-UHFFFAOYSA-N 0.000 description 3
239000003242 anti bacterial agent Substances 0.000 description 3
XMEVHPAGJVLHIG-FMZCEJRJSA-N chembl454950 Chemical compound [Cl-].C1=CC=C2[C@](O)(C)[C@H]3C[C@H]4[C@H]([NH+](C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O XMEVHPAGJVLHIG-FMZCEJRJSA-N 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000002329 infrared spectrum Methods 0.000 description 3
RVPUETSFKVWTTO-UHFFFAOYSA-N methylaminomethanesulfonic acid Chemical compound CNCS(O)(=O)=O RVPUETSFKVWTTO-UHFFFAOYSA-N 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 3
229960004989 tetracycline hydrochloride Drugs 0.000 description 3
DHPRQBPJLMKORJ-RQWFMOQPSA-N (4s,4as,6s,12ar)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide Chemical compound C1=CC(Cl)=C2[C@](O)(C)C3C[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 DHPRQBPJLMKORJ-RQWFMOQPSA-N 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000000538 analytical sample Substances 0.000 description 2
229940088710 antibiotic agent Drugs 0.000 description 2
230000003115 biocidal effect Effects 0.000 description 2
239000003814 drug Substances 0.000 description 2
238000000921 elemental analysis Methods 0.000 description 2
229960004279 formaldehyde Drugs 0.000 description 2
229940098779 methanesulfonic acid Drugs 0.000 description 2
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000000523 sample Substances 0.000 description 2
FQACZEDGFYNXLY-UHFFFAOYSA-M sodium 2-oxidosulfonothioylethanamine Chemical compound NCCS(=O)([O-])=S.[Na+] FQACZEDGFYNXLY-UHFFFAOYSA-M 0.000 description 2
UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
JBOWGOOXLSDXHE-UHFFFAOYSA-N (2-hydroxyethylamino)methanesulfonic acid Chemical compound OCCNCS(O)(=O)=O JBOWGOOXLSDXHE-UHFFFAOYSA-N 0.000 description 1
RMVMLZHPWMTQGK-SOUFLCLCSA-N (4s,4as,5as,6s,12ar)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1([C@H]2O)=CC=CC(O)=C1C(O)=C1[C@@H]2C[C@H]2[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]2(O)C1=O RMVMLZHPWMTQGK-SOUFLCLCSA-N 0.000 description 1
OAPVUSSHCBRCOL-KBHRXELFSA-N (4s,4as,5as,6s,12ar)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide;hydrochloride Chemical compound Cl.C1([C@H]2O)=C(Cl)C=CC(O)=C1C(O)=C1[C@@H]2C[C@H]2[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]2(O)C1=O OAPVUSSHCBRCOL-KBHRXELFSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
229940093475 2-ethoxyethanol Drugs 0.000 description 1
241000588747 Klebsiella pneumoniae Species 0.000 description 1
206010067125 Liver injury Diseases 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241000700157 Rattus norvegicus Species 0.000 description 1
229910006127 SO3X Inorganic materials 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
YYIRFACMCRVDLL-UHFFFAOYSA-N butylaminomethanesulfonic acid Chemical compound CCCCNCS(O)(=O)=O YYIRFACMCRVDLL-UHFFFAOYSA-N 0.000 description 1
JCSGAUKCDAVARS-UHFFFAOYSA-N demethyltetracycline Natural products CN(C1C(=C(C(C2(C(=C3C(C4=C(C=CC=C4C(C3CC12)O)O)=O)O)O)=O)C(=O)N)O)C JCSGAUKCDAVARS-UHFFFAOYSA-N 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
229960003276 erythromycin Drugs 0.000 description 1
KYEDOONOJDZEFS-UHFFFAOYSA-N ethylaminomethanesulfonic acid Chemical compound CCNCS(O)(=O)=O KYEDOONOJDZEFS-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
159000000011 group IA salts Chemical class 0.000 description 1
231100000234 hepatic damage Toxicity 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
229960000318 kanamycin Drugs 0.000 description 1
229930027917 kanamycin Natural products 0.000 description 1
SBUJHOSQTJFQJX-NOAMYHISSA-N kanamycin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N SBUJHOSQTJFQJX-NOAMYHISSA-N 0.000 description 1
229930182823 kanamycin A Natural products 0.000 description 1
230000008818 liver damage Effects 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
150000003334 secondary amides Chemical class 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000007787 solid Substances 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
239000004552 water soluble powder Substances 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
- C07C233/00—Carboxylic acid amides

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH134767A 1966-01-29 1967-01-27 Verfahren zur Herstellung von Tetracyclinderivaten CH506495A (de)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
IT48966		1966-01-29
IT187866		1966-01-29
IT187766		1966-01-29
IT4314066A IT1045401B (it)	1966-11-26	1966-11-26	Deri ati delle tetracicline procedimento per la loro preparazione ed uso terapeutico

Publications (1)

Publication Number	Publication Date
CH506495A true CH506495A (de)	1971-04-30

Family

ID=27452640

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH134767A CH506495A (de)	1966-01-29	1967-01-27	Verfahren zur Herstellung von Tetracyclinderivaten

Country Status (5)

Country	Link
CH (1)	CH506495A (da)
DK (1)	DK123093B (da)
FR (2)	FR6634M (da)
GB (1)	GB1112514A (da)
NL (1)	NL6701234A (da)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2054443B1 (da) *	1969-07-01	1973-08-10	Rouchy Maurice

1967
- 1967-01-18 GB GB259367A patent/GB1112514A/en not_active Expired
- 1967-01-20 DK DK35367A patent/DK123093B/da unknown
- 1967-01-26 NL NL6701234A patent/NL6701234A/xx unknown
- 1967-01-27 CH CH134767A patent/CH506495A/de not_active IP Right Cessation
- 1967-01-27 FR FR92784A patent/FR6634M/fr not_active Expired
- 1967-01-27 FR FR92783A patent/FR1509566A/fr not_active Expired

Also Published As

Publication number	Publication date
DK123093B (da)	1972-05-15
FR1509566A (fr)	1968-01-12
FR6634M (da)	1969-01-20
GB1112514A (en)	1968-05-08
NL6701234A (da)	1967-07-31

Legal Events

Date	Code	Title	Description
1977-08-31	PL	Patent ceased

Publication	Publication Date	Title
DE2332878C2 (de)	1983-07-28	Salze von Cephalosporinen mit Arginin und Lysin, ihre Herstellung und injizierbare pharmazeutische Zubereitungen
DE2819479C2 (da)	1992-04-30
EP0014976A1 (de)	1980-09-03	N-substituierte 2-Cyanaziridine, Verfahren zu deren Herstellung sowie diese Substanzen enthaltende Arzneimittel, entsprechend substituierte Aziridin-2-carbonsäureamide und deren Herstellung
DE1670935B2 (de)	1975-04-24	2-Methyl-3-carbonsäureamidochinoxalin-1,4-di-N-oxide, ein Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende antibakterielle Mittel
DE2515629A1 (de)	1975-10-23	Paromomycin-derivate, verfahren zu ihrer herstellung und arzneimittel
DE2509260C3 (de)	1979-05-03	a-(23,43,6-Penta-O-acetyl-D-gluconyl-thioureido)benzylpenicillin
DE2101378A1 (de)	1971-07-22	Neue pharmazeutische Zusammensetzungen zur Behandlung von Bakterieninfektionen
DE2815442C2 (da)	1989-05-11
CH623335A5 (da)	1981-05-29
CH506495A (de)	1971-04-30	Verfahren zur Herstellung von Tetracyclinderivaten
DE1813918C3 (de)	1979-02-15	2-Hydroxymethyl-3-carbonsäureamido--chinoxalin-M-di-N-oxide, ein Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende antibakterielle Mittel
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