DE1617576C3 - Verfahren zur Herstellung eines Injektionspräparates auf Basis einer wäßrigen Lösung eines Oxytetracyclin-Magnesium-Komplexes - Google Patents
Verfahren zur Herstellung eines Injektionspräparates auf Basis einer wäßrigen Lösung eines Oxytetracyclin-Magnesium-KomplexesInfo
- Publication number
- DE1617576C3 DE1617576C3 DE1617576A DEK0062395A DE1617576C3 DE 1617576 C3 DE1617576 C3 DE 1617576C3 DE 1617576 A DE1617576 A DE 1617576A DE K0062395 A DEK0062395 A DE K0062395A DE 1617576 C3 DE1617576 C3 DE 1617576C3
- Authority
- DE
- Germany
- Prior art keywords
- oxytetracycline
- hours
- polyvinylpyrrolidone
- injection
- solution
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 238000002347 injection Methods 0.000 title claims description 39
- 239000007924 injection Substances 0.000 title claims description 39
- 238000002360 preparation method Methods 0.000 title claims description 20
- 239000011777 magnesium Substances 0.000 title claims description 7
- 229910052749 magnesium Inorganic materials 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 6
- 239000007864 aqueous solution Substances 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 34
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 34
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 34
- 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 24
- 150000003839 salts Chemical class 0.000 claims description 6
- 150000002681 magnesium compounds Chemical class 0.000 claims description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
- 239000000243 solution Substances 0.000 description 56
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 22
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 14
- 239000000395 magnesium oxide Substances 0.000 description 12
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 12
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 12
- 229960004368 oxytetracycline hydrochloride Drugs 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
- 210000002700 urine Anatomy 0.000 description 9
- 230000036765 blood level Effects 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000004098 Tetracycline Substances 0.000 description 5
- 229940091250 magnesium supplement Drugs 0.000 description 5
- 235000019364 tetracycline Nutrition 0.000 description 5
- 150000003522 tetracyclines Chemical class 0.000 description 5
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
- 239000000725 suspension Substances 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
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000007794 irritation Effects 0.000 description 3
- 239000003589 local anesthetic agent Substances 0.000 description 3
- 159000000003 magnesium salts Chemical class 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 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
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 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 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 238000010255 intramuscular injection Methods 0.000 description 2
- 239000007927 intramuscular injection Substances 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229960002337 magnesium chloride Drugs 0.000 description 2
- 229910001629 magnesium chloride Inorganic materials 0.000 description 2
- 229940050906 magnesium chloride hexahydrate Drugs 0.000 description 2
- DHRRIBDTHFBPNG-UHFFFAOYSA-L magnesium dichloride hexahydrate Chemical compound O.O.O.O.O.O.[Mg+2].[Cl-].[Cl-] DHRRIBDTHFBPNG-UHFFFAOYSA-L 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 230000017074 necrotic cell death Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- GHCZTIFQWKKGSB-UHFFFAOYSA-N 2-hydroxypropane-1,2,3-tricarboxylic acid;phosphoric acid Chemical compound OP(O)(O)=O.OC(=O)CC(O)(C(O)=O)CC(O)=O GHCZTIFQWKKGSB-UHFFFAOYSA-N 0.000 description 1
- 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
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000004099 Chlortetracycline Substances 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
- 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
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 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 description 1
- 229960004475 chlortetracycline Drugs 0.000 description 1
- 235000019365 chlortetracycline Nutrition 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- IYBQHJMYDGVZRY-UHFFFAOYSA-N lidocaine hydrochloride Chemical compound [Cl-].CC[NH+](CC)CC(=O)NC1=C(C)C=CC=C1C IYBQHJMYDGVZRY-UHFFFAOYSA-N 0.000 description 1
- 229960005015 local anesthetics Drugs 0.000 description 1
- -1 magnesium chloride Chemical class 0.000 description 1
- 150000002696 manganese Chemical class 0.000 description 1
- 208000004396 mastitis Diseases 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229960003924 oxytetracycline dihydrate Drugs 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 239000003058 plasma substitute Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001698 pyrogenic effect Effects 0.000 description 1
- 229910052895 riebeckite Inorganic materials 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
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229940040944 tetracyclines Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 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
- A61K31/74—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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL6607516A NL6607516A (enExample) | 1966-05-31 | 1966-05-31 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1617576A1 DE1617576A1 (de) | 1972-04-27 |
| DE1617576B2 DE1617576B2 (de) | 1980-04-10 |
| DE1617576C3 true DE1617576C3 (de) | 1980-12-11 |
Family
ID=19796753
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1617576A Expired DE1617576C3 (de) | 1966-05-31 | 1967-05-26 | Verfahren zur Herstellung eines Injektionspräparates auf Basis einer wäßrigen Lösung eines Oxytetracyclin-Magnesium-Komplexes |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US3557280A (enExample) |
| JP (1) | JPS5010373B1 (enExample) |
| AT (1) | AT272522B (enExample) |
| BE (1) | BE699091A (enExample) |
| CH (1) | CH490087A (enExample) |
| CS (1) | CS151454B2 (enExample) |
| DE (1) | DE1617576C3 (enExample) |
| DK (1) | DK117587B (enExample) |
| ES (1) | ES340956A1 (enExample) |
| FI (1) | FI43622B (enExample) |
| FR (1) | FR5953M (enExample) |
| GB (1) | GB1131007A (enExample) |
| GR (1) | GR33861B (enExample) |
| IL (1) | IL28009A (enExample) |
| IT (1) | IT1140250B (enExample) |
| LU (1) | LU53788A1 (enExample) |
| MY (1) | MY7100015A (enExample) |
| NL (1) | NL6607516A (enExample) |
| NO (1) | NO126298B (enExample) |
| SE (1) | SE354417B (enExample) |
| SU (1) | SU510986A3 (enExample) |
| YU (1) | YU31326B (enExample) |
Families Citing this family (77)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5418330B2 (enExample) * | 1973-03-16 | 1979-07-06 | ||
| US3966905A (en) * | 1973-05-29 | 1976-06-29 | Barnes-Hind Pharmaceuticals, Inc. | Stabilized catechol amine solutions |
| US3929989A (en) * | 1974-06-14 | 1975-12-30 | Wendt Lab Inc | Stable suspension of calcium-magnesium oxytetracycline for intrauterine administration in treatment of bovine metritis |
| GB1538903A (en) * | 1975-04-11 | 1979-01-24 | Nelson Res & Dev | Carrier for a topically applied physiologically active agent or cosmetic agent |
| US4018889A (en) * | 1976-01-02 | 1977-04-19 | Pfizer Inc. | Oxytetracycline compositions |
| DE2602363C2 (de) * | 1976-01-22 | 1984-04-12 | Bayer Ag, 5090 Leverkusen | Wäßrige, injizierbare Niclofolan- Formulierungen |
| GB1592053A (en) * | 1976-12-16 | 1981-07-01 | Norbrook Lab Ltd | Oxytetracycline compositions |
| US4213963A (en) * | 1978-12-14 | 1980-07-22 | Janssen Pharmaceutica N.V. | Fluspirilene-containing compositions |
| US4259331A (en) * | 1979-04-16 | 1981-03-31 | Pfizer Inc. | Oxytetracycline compositions |
| US4386083A (en) * | 1980-04-10 | 1983-05-31 | Walter Hacke | Injectable oxytetracycline compositions |
| US4399127A (en) * | 1980-04-10 | 1983-08-16 | Diamond Shamrock Corporation | Injectable oxytetracycline compositions |
| IE74244B1 (en) * | 1985-10-01 | 1997-07-16 | Bimeda Res Dev Ltd | A process for preparing an antibiotic composition |
| US5071643A (en) * | 1986-10-17 | 1991-12-10 | R. P. Scherer Corporation | Solvent system enhancing the solubility of pharmaceuticals for encapsulation |
| US6756365B2 (en) * | 1991-11-06 | 2004-06-29 | Trustees Of Tufts College | Reducing tetracycline resistance in living cells |
| EP0626171A1 (de) * | 1993-05-26 | 1994-11-30 | Winfried Dörnhöfer | Injektionslösung für die intravenöse oder intramuskuläre Verabreichung an Tiere |
| US6383515B2 (en) | 1999-05-28 | 2002-05-07 | Sawyer Maryjean | Solvent system for enhancing solubility |
| US6500812B2 (en) | 1999-09-14 | 2002-12-31 | Paratek Pharmaceuticals, Inc. | 13-substituted methacycline compounds |
| US8106225B2 (en) * | 1999-09-14 | 2012-01-31 | Trustees Of Tufts College | Methods of preparing substituted tetracyclines with transition metal-based chemistries |
| EP1666453A1 (en) | 1999-09-14 | 2006-06-07 | Trustees Of Tufts College | Methods of preparing substituted tetracyclines with transition metal-based chemistries |
| US6849615B2 (en) | 1999-09-14 | 2005-02-01 | Paratek Pharmaceuticals, Inc. | 13-substituted methacycline compounds |
| CA2397863A1 (en) * | 2000-01-24 | 2001-07-26 | Trustees Of Tufts College | Tetracycline compounds for treatment of cryptosporidium parvum related disorders |
| ES2288945T3 (es) * | 2000-03-31 | 2008-02-01 | Trustees Of Tufts College | Compuestos de tetraciclina 7 y 9-carbamato, urea, tiourea, tiocarbamato y heteroaril-amino sustituidos. |
| DE60102815D1 (de) * | 2000-05-15 | 2004-05-19 | Paratek Pharm Innc | 7-substituierte kondensierte ring-tetrazyclin- verbindungen |
| US20040224927A1 (en) * | 2000-06-16 | 2004-11-11 | Trustees Of Tufts College | 7-N-substituted phenyl tetracycline compounds |
| US20020132798A1 (en) * | 2000-06-16 | 2002-09-19 | Nelson Mark L. | 7-phenyl-substituted tetracycline compounds |
| AU2001268475A1 (en) * | 2000-06-16 | 2002-01-02 | Trustees Of Tufts College | 7-phenyl-substituted tetracycline compounds |
| EP1301465A2 (en) | 2000-07-07 | 2003-04-16 | Trustees Of Tufts College | 13-substituted methacycline compounds |
| SI1301467T1 (sl) | 2000-07-07 | 2007-02-28 | Tufts College | 9-substituirane minociklinske spojine |
| DE60144375D1 (de) | 2000-07-07 | 2011-05-19 | Trustees Of Tufts College Medford | 7-, 8- und 9-substitutierte tetracyclinverbindungen |
| US7094806B2 (en) | 2000-07-07 | 2006-08-22 | Trustees Of Tufts College | 7, 8 and 9-substituted tetracycline compounds |
| EA006170B1 (ru) * | 2000-07-07 | 2005-10-27 | Трастис Оф Тафтс Коллидж | Замещенные соединения тетрациклина (варианты), фармацевтическая композиция и способ лечения чувствительного к тетрациклину состояния субъекта |
| US20050143353A1 (en) * | 2000-07-07 | 2005-06-30 | Paratek Pharmaceuticals, Inc. | 13-Substituted methacycline compounds |
| US6683068B2 (en) * | 2001-03-13 | 2004-01-27 | Paratek Pharmaceuticals, Inc. | 7, 9-substituted tetracycline compounds |
| AU2002250331A1 (en) * | 2001-03-13 | 2002-09-24 | Paratek Pharmaceuticals, Inc. | 7-pyrollyl tetracycline compounds and methods of use thereof |
| US6841546B2 (en) | 2001-03-14 | 2005-01-11 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds as antifungal agents |
| CA2440757A1 (en) | 2001-03-14 | 2002-09-19 | Michael Draper | Substituted tetracycline compounds as synergistic antifungal agents |
| DE60235083D1 (de) | 2001-04-24 | 2010-03-04 | Paratek Pharm Innc | Substituierte tetracyclin-verbindungen zur behandlung von malaria |
| US8088820B2 (en) * | 2001-04-24 | 2012-01-03 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds for the treatment of malaria |
| JP2005514410A (ja) | 2002-01-08 | 2005-05-19 | パラテック ファーマシューティカルズ インコーポレイテッド | ４−デジメチルアミノテトラサイクリン化合物 |
| JP2005526754A (ja) | 2002-03-08 | 2005-09-08 | パラテック ファーマシューティカルズ インコーポレイテッド | アミノメチル置換されたテトラサイクリン化合物 |
| JP2005520846A (ja) | 2002-03-21 | 2005-07-14 | パラテック ファーマシューティカルズ インコーポレイテッド | 置換されたテトラサイクリン化合物。 |
| EP1534300A4 (en) | 2002-07-12 | 2008-04-23 | Paratek Pharm Innc | TETRACYCLINE COMPOUNDS SUBSTITUTED IN 3, 10, AND 12A |
| AU2003287218C1 (en) | 2002-10-24 | 2010-07-15 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds for the treatment of malaria |
| WO2004071490A1 (en) * | 2003-02-12 | 2004-08-26 | R & P Korea Co., Ltd. | Solvent system of hardly soluble drug with improved elution rate |
| CA2531732C (en) | 2003-07-09 | 2012-04-10 | Paratek Pharmaceuticals, Inc. | Prodrugs of 9-aminomethyl tetracycline compounds |
| US20060287283A1 (en) * | 2003-07-09 | 2006-12-21 | Paratek Pharmaceuticals, Inc. | Prodrugs of 9-aminomethyl tetracycline compounds |
| EP2319828A3 (en) | 2003-07-09 | 2011-07-06 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds |
| EP2332904A3 (en) | 2004-01-15 | 2012-04-11 | Paratek Pharmaceuticals, Inc. | Derivatives of tetracycline compounds |
| TWI261038B (en) * | 2004-08-11 | 2006-09-01 | Bo-Cheng Chen | Bicycle gear-shifting handgrip |
| EP2287148A3 (en) | 2004-10-25 | 2011-10-26 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds |
| EP1805134B1 (en) * | 2004-10-25 | 2012-06-20 | Paratek Pharmaceuticals, Inc. | 4-aminotetracyclines and methods of use thereof |
| JP2008530023A (ja) * | 2005-02-04 | 2008-08-07 | パラテック ファーマシューティカルズ インコーポレイテッド | テトラサイクリン化合物の１１ａ，１２−誘導体 |
| DE102005012595A1 (de) * | 2005-03-18 | 2006-09-21 | Lanxess Deutschland Gmbh | Herstellung von Tri(chlorpropyl)phosphat |
| WO2007014154A2 (en) * | 2005-07-21 | 2007-02-01 | Paratek Pharmaceuticals, Inc. | 10-substituted tetracyclines and methods of use thereof |
| CA2622704A1 (en) * | 2005-09-19 | 2007-03-29 | Albemarle Corporation | Highly concentrated pourable aqueous solutions of potassium ibuprofen their preparation and their uses |
| EP1991236A2 (en) | 2006-01-24 | 2008-11-19 | Paratek Pharmaceuticals, Inc. | Methods of increasing oral bioavailability of tetracyclines |
| WO2007120913A2 (en) * | 2006-04-17 | 2007-10-25 | Teva Pharmaceutical Industries Ltd. | Isolation of tetracycline derivatives |
| CN101479235B (zh) * | 2006-04-24 | 2013-09-18 | 特瓦制药工业有限公司 | 替加环素晶形及其制备方法 |
| US8198470B2 (en) * | 2006-04-24 | 2012-06-12 | Teva Pharmaceutical Industries Ltd. | Crystalline form II of tigecycline and processes for preparation thereof |
| AU2007249695A1 (en) * | 2006-05-15 | 2007-11-22 | Paratek Pharmaceuticals, Inc. | Methods of regulating expression of genes or of gene products using substituted tetracycline compounds |
| WO2008045507A2 (en) | 2006-10-11 | 2008-04-17 | Paratek Pharmaceuticals, Inc. | Substituted tetracycline compounds for treatment of bacillus anthracis infections |
| PT2109602E (pt) | 2006-12-21 | 2014-05-23 | Paratek Pharm Innc | Derivados de tetraciclina para o tratamento de infecções bacterianas, virais e parasitárias |
| SI2120963T1 (sl) | 2006-12-21 | 2019-02-28 | Paratek Pharmaceuticals, Inc. | Substituirane spojine tetraciklina za zdravljenje vnetnih kožnih motenj |
| US7935687B2 (en) * | 2007-04-12 | 2011-05-03 | Paratek Pharmaceuticals, Inc. | Methods for treating spinal muscular atrophy using tetracycline compounds |
| CA2688662A1 (en) | 2007-04-27 | 2008-11-06 | Paratek Pharmaceuticals, Inc. | Methods for synthesizing and purifying aminoalkyl tetracycline compounds |
| ATE555079T1 (de) | 2007-07-06 | 2012-05-15 | Paratek Pharm Innc | Verfahren zur synthese von 9-substituiertem minocyclin |
| CN102015602A (zh) | 2008-03-05 | 2011-04-13 | 帕拉特克药品公司 | 米诺环素化合物及其使用方法 |
| PT2271348T (pt) | 2008-03-28 | 2018-04-16 | Paratek Pharm Innc | Formulação de comprimido oral de composto de tetraciclina |
| US20100022483A1 (en) * | 2008-04-14 | 2010-01-28 | Paratek Pharmaceuticals, Inc. | Substituted Tetracycline Compounds |
| TW202021946A (zh) | 2008-05-19 | 2020-06-16 | 美商派洛泰克藥物股份有限公司 | 四環素化合物之甲苯磺酸鹽及同素異形體 |
| US9629809B2 (en) | 2008-07-21 | 2017-04-25 | Si Group, Inc. | High content sodium ibuprofen granules, their preparation and their use in preparing non-effervescent solid dosage forms |
| JP5553830B2 (ja) | 2008-07-21 | 2014-07-16 | アルベマール・コーポレーシヨン | 高含量イブプロフェンナトリウム顆粒、その調製、および非発泡性固体剤形を調製する際のその使用 |
| AP2011005631A0 (en) * | 2008-09-19 | 2011-04-30 | Paratek Pharmaceuticals Ind | Tetracycline compounds for the treatment of rheumatoid arthritis and related methods of treatment. |
| EP3061460A1 (en) | 2009-04-10 | 2016-08-31 | Tufts Medical Center, Inc. | Par-1 activation by metalloproteinase-1 (mmp-1) |
| WO2012155146A1 (en) | 2011-05-12 | 2012-11-15 | Paratek Pharmaceuticals, Inc. | Crystalline salts of (4s,4as,5ar,12as)-4-dimethylamino-3,10,12,12a-tetrahydroxy-7-[(methoxy(methyl)amino)-methyl]-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide and methods of using the same |
| CN110087655A (zh) | 2016-11-01 | 2019-08-02 | 帕拉特克药品公司 | 9-氨基甲基米诺环素化合物及其在治疗社区获得性细菌性肺炎(cabp)中的用途 |
| WO2019016609A1 (en) | 2017-07-21 | 2019-01-24 | Allergan Pharmaceuticals International Limited | TREATMENT OF NON-INFLAMMATORY LESIONS |
-
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 DE DE1617576A patent/DE1617576C3/de not_active Expired
- 1967-05-26 US US641483A patent/US3557280A/en not_active Expired - Lifetime
- 1967-05-30 FI FI1517/67A patent/FI43622B/fi active
- 1967-05-30 NO NO00168375A patent/NO126298B/no unknown
- 1967-05-30 DK DK282167AA patent/DK117587B/da unknown
- 1967-05-30 AT AT502267A patent/AT272522B/de active
- 1967-05-30 YU YU1086/67A patent/YU31326B/xx unknown
- 1967-05-30 IT IT37118/67A patent/IT1140250B/it active
- 1967-05-31 CH CH766867A patent/CH490087A/de not_active IP Right Cessation
- 1967-05-31 JP JP42034292A patent/JPS5010373B1/ja active Pending
- 1967-05-31 LU LU53788A patent/LU53788A1/xx unknown
- 1967-05-31 CS CS3970A patent/CS151454B2/cs unknown
-
1971
- 1971-12-30 MY MY15/71A patent/MY7100015A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK117587B (da) | 1970-05-11 |
| DE1617576A1 (de) | 1972-04-27 |
| ES340956A1 (es) | 1968-06-16 |
| NL6607516A (enExample) | 1967-12-01 |
| DE1617576B2 (de) | 1980-04-10 |
| SU510986A3 (ru) | 1976-04-15 |
| CS151454B2 (enExample) | 1973-10-19 |
| MY7100015A (en) | 1971-12-31 |
| YU31326B (en) | 1973-04-30 |
| IL28009A (en) | 1970-08-19 |
| NO126298B (enExample) | 1973-01-22 |
| FI43622B (enExample) | 1971-02-01 |
| CH490087A (de) | 1970-05-15 |
| BE699091A (enExample) | 1967-11-27 |
| LU53788A1 (enExample) | 1967-07-31 |
| GR33861B (el) | 1968-02-09 |
| IT1140250B (it) | 1986-09-24 |
| GB1131007A (en) | 1968-10-16 |
| SE354417B (enExample) | 1973-03-12 |
| JPS5010373B1 (enExample) | 1975-04-21 |
| US3557280A (en) | 1971-01-19 |
| FR5953M (enExample) | 1968-04-16 |
| AT272522B (de) | 1969-07-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1617576C3 (de) | Verfahren zur Herstellung eines Injektionspräparates auf Basis einer wäßrigen Lösung eines Oxytetracyclin-Magnesium-Komplexes | |
| EP0136470B1 (de) | Injizierbare Lösung zur Behandlung von Entzündungen | |
| WO2001078732A1 (de) | Lagerstabile infusionslösung des ciprofloxacins | |
| DE60101979T2 (de) | Lösung enthaltend N-[O-(p-pivaloyloxybenzenesulfonylamino)benzoyl]glyzin Mononatriumsalz Tetrahydrat und diese Lösung enthaltendes Arzneimittel | |
| DE3751589T2 (de) | Anthracyclin-Glucosid enthaltende einspritzbare gebrauchsfertige Lösungen gegen Krebs. | |
| CH647677A5 (de) | 4'-(acridinylamino)-methansulfon-anisidid enthaltende pharmazeutische zusammensetzung. | |
| DE2639849A1 (de) | Verfahren zur herstellung stabiler praeparate wasserloeslicher salze von dehydroepiandrosteronsulfat zur parenteralen verabreichung | |
| DE1467749A1 (de) | Verfahren zur Herstellung von stabilen Tetracyclinpraeparaten | |
| DE3700379C2 (enExample) | ||
| DE69232409T2 (de) | Ungepufferte, vorgemischte ranitidin-formulierung | |
| DE2546474A1 (de) | Injizierbares pharmazeutisches thyroxinpraeparat und verfahren zu dessen herstellung | |
| DE69231098T2 (de) | Lyophilisierte zusammensetzung, die s(+)-4,4'-(1-methyl-1,2-ethandiyl)-bis(2,6-piperazindion)enthält | |
| DE2723936A1 (de) | Ophthalmische loesung fuer die glaucom-behandlung | |
| DE1792448C3 (de) | Verfahren zur Herstellung von zur parenteralen Verabreichung geeigneten stabilen Lösungen von therapeutisch anwendbaren Benzodiazepinderivaten | |
| AT241028B (de) | Verfahren zur Herstellung eines eisenhaltigen Präparats für intramuskuläre Injektion | |
| DE2538678A1 (de) | Injizierbare loesungen | |
| DE69000268T2 (de) | Stabilisiertes antitumormittel. | |
| DE1417343C (de) | Flüssige stabile Arzneimittel auf der Basis von Magnesiumkomplexsalzen des Oxytetracycline. Arun: Chas. Pfizer & Co Inc., Brooklyn, N.Y. (V.St.A.); Ttr: Beil, Dr. W.; Hoeppener, A.; Rechtsanwälte, 6230 Frankfurt-Höchst | |
| AT218175B (de) | Röntgenkontrastmittel zur Sichtbarmachung der Gallenwege | |
| DE3343818C2 (enExample) | ||
| DE1901915C3 (de) | Arzneimittel auf der Basis von a -Aminobenzylpenicillintrihydrat | |
| AT142713B (de) | Verfahren zur Herstellung von in Lösungen haltbaren Präparaten, die anaesthesierend wirkende und gefäßverengende Mittel enthalten. | |
| DE2026864C (de) | 2-Äthyl- oder 2-Propylthioisonikotinsäureamid enthaltende InjektionsJösungen | |
| AT261812B (de) | Verfahren zur Herstellung einer stabilen Lösung von 6-Desmethyl-tetracyclin oder 7-Chlor-6-desmethyl-tetracyclin | |
| DE2461570A1 (de) | Antibakterielle pharmazeutische ohren- und augenformulierungen und verfahren zu ihrer herstellung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |