NO126298B - - Google Patents

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Publication number: NO126298B
Authority: NO; Norway
Prior art keywords: oxytetracycline; solution; solutions; magnesium; polyvinylpyrrolidone
Prior art date: 1966-05-31

Application number

NO00168375A

Other languages

English (en)

Norwegian (no)

Inventor

Hubert Antonius Weber

Adrianus Pieter Molenaar

Original Assignee

Koninklijke Gist Spiritus

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.)

1966-05-31

Filing date

1967-05-30

Publication date

1973-01-22

1967-05-30 Application filed by Koninklijke Gist Spiritus filed Critical Koninklijke Gist Spiritus

1973-01-22 Publication of NO126298B publication Critical patent/NO126298B/no

Links

239000000243 solution Substances 0.000 claims description 66
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 32
239000004100 Oxytetracycline Substances 0.000 claims description 31
229960000625 oxytetracycline Drugs 0.000 claims description 31
235000019366 oxytetracycline Nutrition 0.000 claims description 31
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 description 31
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 24
235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 24
239000001267 polyvinylpyrrolidone Substances 0.000 claims description 23
239000000395 magnesium oxide Substances 0.000 claims description 11
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 11
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 11
238000000034 method Methods 0.000 claims description 8
239000007864 aqueous solution Substances 0.000 claims description 7
150000002681 magnesium compounds Chemical class 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 4
239000011777 magnesium Substances 0.000 claims description 3
229910052749 magnesium Inorganic materials 0.000 claims description 3
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
159000000003 magnesium salts Chemical class 0.000 claims 1
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 16
238000002347 injection Methods 0.000 description 14
239000007924 injection Substances 0.000 description 14
229960004368 oxytetracycline hydrochloride Drugs 0.000 description 11
VYGBQXDNOUHIBZ-UHFFFAOYSA-L sodium formaldehyde sulphoxylate Chemical compound [Na+].[Na+].O=C.[O-]S[O-] VYGBQXDNOUHIBZ-UHFFFAOYSA-L 0.000 description 11
MWKJTNBSKNUMFN-UHFFFAOYSA-N trifluoromethyltrimethylsilane Chemical compound C[Si](C)(C)C(F)(F)F MWKJTNBSKNUMFN-UHFFFAOYSA-N 0.000 description 11
150000001875 compounds Chemical class 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000004098 Tetracycline Substances 0.000 description 5
230000003115 biocidal effect Effects 0.000 description 5
239000000047 product Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
235000019364 tetracycline Nutrition 0.000 description 5
150000003522 tetracyclines Chemical class 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
239000000908 ammonium hydroxide Substances 0.000 description 4
239000012530 fluid Substances 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
229960002180 tetracycline Drugs 0.000 description 4
229930101283 tetracycline Natural products 0.000 description 4
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
238000010255 intramuscular injection Methods 0.000 description 3
239000007927 intramuscular injection Substances 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
230000001225 therapeutic effect Effects 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
UDIPTWFVPPPURJ-UHFFFAOYSA-M Cyclamate Chemical compound [Na+].[O-]S(=O)(=O)NC1CCCCC1 UDIPTWFVPPPURJ-UHFFFAOYSA-M 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
239000010425 asbestos Substances 0.000 description 2
239000011575 calcium Substances 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000000625 cyclamic acid and its Na and Ca salt Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000003589 local anesthetic agent Substances 0.000 description 2
229910001629 magnesium chloride Inorganic materials 0.000 description 2
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
239000000203 mixture Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 2
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 2
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
229910052895 riebeckite Inorganic materials 0.000 description 2
XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 2
229960001462 sodium cyclamate Drugs 0.000 description 2
235000010265 sodium sulphite Nutrition 0.000 description 2
230000001954 sterilising effect Effects 0.000 description 2
238000003860 storage Methods 0.000 description 2
RREANTFLPGEWEN-MBLPBCRHSA-N 7-[4-[[(3z)-3-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]imino-5-fluoro-2-oxoindol-1-yl]methyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(\N=C/3C4=CC(F)=CC=C4N(CN4CCN(CC4)C=4C(=CC=5C(=O)C(C(O)=O)=CN(C=5C=4)C4CC4)F)C\3=O)=NC=2)N)=C1 RREANTFLPGEWEN-MBLPBCRHSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000000654 additive Substances 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
239000008280 blood Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
229910001424 calcium ion Inorganic materials 0.000 description 1
125000005521 carbonamide group Chemical group 0.000 description 1
125000005265 dialkylamine group Chemical group 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
229910001425 magnesium ion Inorganic materials 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
208000004396 mastitis Diseases 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
230000017074 necrotic cell death Effects 0.000 description 1
230000001338 necrotic effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000002674 ointment Substances 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
229960003924 oxytetracycline dihydrate Drugs 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
210000002381 plasma Anatomy 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
239000004289 sodium hydrogen sulphite Substances 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
239000004296 sodium metabisulphite Substances 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
229940072172 tetracycline antibiotic Drugs 0.000 description 1
229940040944 tetracyclines Drugs 0.000 description 1
238000011287 therapeutic dose Methods 0.000 description 1
239000002562 thickening agent 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
- A61K31/74—Synthetic polymeric materials
- A61K31/785—Polymers containing nitrogen
- A61K31/787—Polymers containing nitrogen containing heterocyclic rings having nitrogen as a ring hetero atom
- A61K31/79—Polymers of vinyl pyrrolidone
- 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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material 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)
Medicinal Preparation (AREA)

NO00168375A 1966-05-31 1967-05-30 NO126298B (zh)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
NL6607516A NL6607516A (zh)	1966-05-31	1966-05-31

Publications (1)

Publication Number	Publication Date
NO126298B true NO126298B (zh)	1973-01-22

Family

ID=19796753

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO00168375A NO126298B (zh)	1966-05-31	1967-05-30

Country Status (22)

Country	Link
US (1)	US3557280A (zh)
JP (1)	JPS5010373B1 (zh)
AT (1)	AT272522B (zh)
BE (1)	BE699091A (zh)
CH (1)	CH490087A (zh)
CS (1)	CS151454B2 (zh)
DE (1)	DE1617576C3 (zh)
DK (1)	DK117587B (zh)
ES (1)	ES340956A1 (zh)
FI (1)	FI43622B (zh)
FR (1)	FR5953M (zh)
GB (1)	GB1131007A (zh)
GR (1)	GR33861B (zh)
IL (1)	IL28009A (zh)
IT (1)	IT1140250B (zh)
LU (1)	LU53788A1 (zh)
MY (1)	MY7100015A (zh)
NL (1)	NL6607516A (zh)
NO (1)	NO126298B (zh)
SE (1)	SE354417B (zh)
SU (1)	SU510986A3 (zh)
YU (1)	YU31326B (zh)

Families Citing this family (77)

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1966
- 1966-05-31 NL NL6607516A patent/NL6607516A/xx unknown
- 1966-11-08 FR FR82837A patent/FR5953M/fr not_active Expired
1967
- 1967-05-16 GB GB22620/67A patent/GB1131007A/en not_active Expired
- 1967-05-18 SE SE06961/67A patent/SE354417B/xx unknown
- 1967-05-18 IL IL28009A patent/IL28009A/en unknown
- 1967-05-22 GR GR670133861A patent/GR33861B/el unknown
- 1967-05-24 ES ES340956A patent/ES340956A1/es not_active Expired
- 1967-05-25 SU SU1158241A patent/SU510986A3/ru active
- 1967-05-26 BE BE699091D patent/BE699091A/xx not_active IP Right Cessation
- 1967-05-26 US US641483A patent/US3557280A/en not_active Expired - Lifetime
- 1967-05-26 DE DE1617576A patent/DE1617576C3/de not_active Expired
- 1967-05-30 FI FI1517/67A patent/FI43622B/fi active
- 1967-05-30 YU YU1086/67A patent/YU31326B/xx unknown
- 1967-05-30 NO NO00168375A patent/NO126298B/no unknown
- 1967-05-30 AT AT502267A patent/AT272522B/de active
- 1967-05-30 DK DK282167AA patent/DK117587B/da unknown
- 1967-05-30 IT IT37118/67A patent/IT1140250B/it active
- 1967-05-31 LU LU53788A patent/LU53788A1/xx unknown
- 1967-05-31 CH CH766867A patent/CH490087A/de not_active IP Right Cessation
- 1967-05-31 CS CS3970A patent/CS151454B2/cs unknown
- 1967-05-31 JP JP42034292A patent/JPS5010373B1/ja active Pending
1971
- 1971-12-30 MY MY15/71A patent/MY7100015A/xx unknown

Also Published As

Publication number	Publication date
YU31326B (en)	1973-04-30
BE699091A (zh)	1967-11-27
IL28009A (en)	1970-08-19
US3557280A (en)	1971-01-19
NL6607516A (zh)	1967-12-01
GB1131007A (en)	1968-10-16
FR5953M (zh)	1968-04-16
AT272522B (de)	1969-07-10
ES340956A1 (es)	1968-06-16
DE1617576A1 (de)	1972-04-27
GR33861B (el)	1968-02-09
SE354417B (zh)	1973-03-12
SU510986A3 (ru)	1976-04-15
DE1617576B2 (de)	1980-04-10
IT1140250B (it)	1986-09-24
CS151454B2 (zh)	1973-10-19
MY7100015A (en)	1971-12-31
LU53788A1 (zh)	1967-07-31
DK117587B (da)	1970-05-11
CH490087A (de)	1970-05-15
FI43622B (zh)	1971-02-01
DE1617576C3 (de)	1980-12-11
JPS5010373B1 (zh)	1975-04-21

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