NO131782B - - Google Patents

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Info

Publication number: NO131782B
Authority: NO; Norway
Prior art keywords: methylene; tetracycline; desmethyl; desoxy; acid
Prior art date: 1969-08-08

Application number

NO3021/70A

Other languages

English (en)

Norwegian (no)

Other versions

NO131782C (fr

Inventor

L Bernardi

R De Castiglione

V Colonna

Original Assignee

Farmaceutici Italia

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.)

1969-08-08

Filing date

1970-08-05

Publication date

1975-04-21

1970-08-05 Application filed by Farmaceutici Italia filed Critical Farmaceutici Italia

1975-04-21 Publication of NO131782B publication Critical patent/NO131782B/no

1975-07-30 Publication of NO131782C publication Critical patent/NO131782C/no

Links

239000004098 Tetracycline Substances 0.000 claims description 31
229960002180 tetracycline Drugs 0.000 claims description 31
238000000034 method Methods 0.000 claims description 11
150000001875 compounds Chemical class 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 7
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 5
229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 5
231100000252 nontoxic Toxicity 0.000 claims description 4
230000003000 nontoxic effect Effects 0.000 claims description 4
150000007513 acids Chemical class 0.000 claims description 3
229940098779 methanesulfonic acid Drugs 0.000 claims description 3
125000002252 acyl group Chemical group 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
239000003638 chemical reducing agent Substances 0.000 claims description 2
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
239000000047 product Substances 0.000 description 12
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 11
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
239000000243 solution Substances 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
229960000583 acetic acid Drugs 0.000 description 8
238000002211 ultraviolet spectrum Methods 0.000 description 8
150000002148 esters Chemical class 0.000 description 7
239000012458 free base Substances 0.000 description 7
238000002329 infrared spectrum Methods 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
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 6
238000004458 analytical method Methods 0.000 description 6
229940042016 methacycline Drugs 0.000 description 6
239000003208 petroleum Substances 0.000 description 5
YCPXWRQRBFJBPZ-UHFFFAOYSA-N 5-sulfosalicylic acid Chemical compound OC(=O)C1=CC(S(O)(=O)=O)=CC=C1O YCPXWRQRBFJBPZ-UHFFFAOYSA-N 0.000 description 4
239000000203 mixture Substances 0.000 description 4
229930101283 tetracycline Natural products 0.000 description 4
235000019364 tetracycline Nutrition 0.000 description 4
150000003522 tetracyclines Chemical class 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000004289 sodium hydrogen sulphite Substances 0.000 description 3
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 3
239000011877 solvent mixture Substances 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
239000005909 Kieselgur Substances 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
230000000844 anti-bacterial effect Effects 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000008280 blood Substances 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
239000012895 dilution Substances 0.000 description 2
238000010790 dilution Methods 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000000284 extract Substances 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
-1 methyl isobutyl Chemical group 0.000 description 2
WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
230000001681 protective effect Effects 0.000 description 2
238000001179 sorption measurement Methods 0.000 description 2
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
OXQGTIUCKGYOAA-UHFFFAOYSA-N 2-Ethylbutanoic acid Chemical compound CCC(CC)C(O)=O OXQGTIUCKGYOAA-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
101100129500 Caenorhabditis elegans max-2 gene Proteins 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
241000699670 Mus sp. Species 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
239000004100 Oxytetracycline Substances 0.000 description 1
241000191967 Staphylococcus aureus Species 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000000538 analytical sample Substances 0.000 description 1
238000010171 animal model Methods 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
229940124350 antibacterial drug Drugs 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
239000002021 butanolic extract Substances 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000004042 decolorization Methods 0.000 description 1
229940061607 dibasic sodium phosphate Drugs 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000011521 glass Substances 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000002609 medium Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
229960002446 octanoic acid Drugs 0.000 description 1
229960000625 oxytetracycline Drugs 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
DJEHXEMURTVAOE-UHFFFAOYSA-M potassium bisulfite Chemical compound [K+].OS([O-])=O DJEHXEMURTVAOE-UHFFFAOYSA-M 0.000 description 1
239000004293 potassium hydrogen sulphite Substances 0.000 description 1
235000010259 potassium hydrogen sulphite Nutrition 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
229960004989 tetracycline hydrochloride Drugs 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 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
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NO3021/70A 1969-08-08 1970-08-05 NO131782C (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT2069969		1969-08-08

Publications (2)

Publication Number	Publication Date
NO131782B true NO131782B (fr)	1975-04-21
NO131782C NO131782C (fr)	1975-07-30

Family

ID=11170732

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO3021/70A NO131782C (fr)	1969-08-08	1970-08-05

Country Status (12)

Country	Link
AT (1)	AT297931B (fr)
BE (1)	BE754596A (fr)
BR (1)	BR6915437D0 (fr)
CA (1)	CA931946A (fr)
CH (1)	CH539612A (fr)
ES (1)	ES382541A1 (fr)
FR (1)	FR2068473B1 (fr)
GB (1)	GB1287493A (fr)
NL (1)	NL7011074A (fr)
NO (1)	NO131782C (fr)
SE (1)	SE360071B (fr)
ZA (1)	ZA705429B (fr)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1430859A (fr) *	1960-05-23	1966-05-25
US3145228A (en) *	1962-09-06	1964-08-18	Pfizer & Co C	5-alkoxy-and 5-benzyloxy-tetracycline, derivatives and analogues thereof

0
- BE BE754596D patent/BE754596A/fr unknown
1969
- 1969-12-19 BR BR215437/69A patent/BR6915437D0/pt unknown
1970
- 1970-07-27 NL NL7011074A patent/NL7011074A/xx unknown
- 1970-08-03 FR FR7028566A patent/FR2068473B1/fr not_active Expired
- 1970-08-03 GB GB37360/70A patent/GB1287493A/en not_active Expired
- 1970-08-05 CA CA089945A patent/CA931946A/en not_active Expired
- 1970-08-05 NO NO3021/70A patent/NO131782C/no unknown
- 1970-08-05 ZA ZA705429A patent/ZA705429B/xx unknown
- 1970-08-06 AT AT716470A patent/AT297931B/de not_active IP Right Cessation
- 1970-08-07 ES ES382541A patent/ES382541A1/es not_active Expired
- 1970-08-07 CH CH1195770A patent/CH539612A/de not_active IP Right Cessation
- 1970-08-07 SE SE10847/70A patent/SE360071B/xx unknown

Also Published As

Publication number	Publication date
CA931946A (en)	1973-08-14
ES382541A1 (es)	1972-12-01
BE754596A (fr)	1971-02-08
NL7011074A (fr)	1971-02-10
GB1287493A (en)	1972-08-31
FR2068473A1 (fr)	1971-08-27
FR2068473B1 (fr)	1974-08-30
BR6915437D0 (pt)	1973-01-25
NO131782C (fr)	1975-07-30
CH539612A (de)	1973-07-31
SE360071B (fr)	1973-09-17
AT297931B (de)	1972-04-10
ZA705429B (en)	1971-04-28

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