DE1518440C3 - Verfahren zur Herstellung eines Salzes eines Sulfomethylderivates von Polymyxin B oder E - Google Patents
Verfahren zur Herstellung eines Salzes eines Sulfomethylderivates von Polymyxin B oder EInfo
- Publication number
- DE1518440C3 DE1518440C3 DE1518440A DE1518440A DE1518440C3 DE 1518440 C3 DE1518440 C3 DE 1518440C3 DE 1518440 A DE1518440 A DE 1518440A DE 1518440 A DE1518440 A DE 1518440A DE 1518440 C3 DE1518440 C3 DE 1518440C3
- Authority
- DE
- Germany
- Prior art keywords
- polymyxin
- solution
- sulfomethyl
- formaldehyde
- value
- 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
- -1 sulfomethyl Chemical class 0.000 title claims description 12
- 108010093965 Polymyxin B Proteins 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 7
- 229920000024 polymyxin B Polymers 0.000 title claims description 7
- 229960005266 polymyxin b Drugs 0.000 title claims description 7
- 108010078777 Colistin Proteins 0.000 title claims description 6
- 150000003839 salts Chemical class 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 2
- 239000000243 solution Substances 0.000 claims description 36
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 108010040201 Polymyxins Proteins 0.000 claims description 14
- 239000002244 precipitate Substances 0.000 claims description 11
- 230000032683 aging Effects 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000000047 product Substances 0.000 claims description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 4
- JORAUNFTUVJTNG-BSTBCYLQSA-N n-[(2s)-4-amino-1-[[(2s,3r)-1-[[(2s)-4-amino-1-oxo-1-[[(3s,6s,9s,12s,15r,18s,21s)-6,9,18-tris(2-aminoethyl)-3-[(1r)-1-hydroxyethyl]-12,15-bis(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptazacyclotricos-21-yl]amino]butan-2-yl]amino]-3-h Polymers CC(C)CCCCC(=O)N[C@@H](CCN)C(=O)N[C@H]([C@@H](C)O)CN[C@@H](CCN)C(=O)N[C@H]1CCNC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCN)NC(=O)[C@H](CCN)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CCN)NC1=O.CCC(C)CCCCC(=O)N[C@@H](CCN)C(=O)N[C@H]([C@@H](C)O)CN[C@@H](CCN)C(=O)N[C@H]1CCNC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCN)NC(=O)[C@H](CCN)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CCN)NC1=O JORAUNFTUVJTNG-BSTBCYLQSA-N 0.000 claims description 4
- YKQOSKADJPQZHB-YNWHQGOSSA-N n-[(2s)-4-amino-1-[[(2s,3r)-1-[[(2s)-4-amino-1-oxo-1-[[(3s,6s,9s,12s,15r,18s,21s)-6,9,18-tris(2-aminoethyl)-3-[(1s)-1-hydroxyethyl]-12,15-bis(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptazacyclotricos-21-yl]amino]butan-2-yl]amino]-3-h Polymers CCC(C)CCCC(=O)N[C@@H](CCN)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCN)C(=O)N[C@H]1CCNC(=O)[C@H]([C@H](C)O)NC(=O)[C@H](CCN)NC(=O)[C@H](CCN)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CCN)NC1=O YKQOSKADJPQZHB-YNWHQGOSSA-N 0.000 claims description 4
- 230000007935 neutral effect Effects 0.000 claims description 4
- XDJYMJULXQKGMM-UHFFFAOYSA-N polymyxin E1 Natural products CCC(C)CCCCC(=O)NC(CCN)C(=O)NC(C(C)O)C(=O)NC(CCN)C(=O)NC1CCNC(=O)C(C(C)O)NC(=O)C(CCN)NC(=O)C(CCN)NC(=O)C(CC(C)C)NC(=O)C(CC(C)C)NC(=O)C(CCN)NC1=O XDJYMJULXQKGMM-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
- 230000000844 anti-bacterial effect Effects 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 238000002347 injection Methods 0.000 claims description 3
- 239000007924 injection Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000000129 anionic group Chemical group 0.000 claims description 2
- 229920001184 polypeptide Polymers 0.000 claims description 2
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 2
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 230000001988 toxicity Effects 0.000 claims description 2
- 231100000419 toxicity Toxicity 0.000 claims description 2
- 230000037396 body weight Effects 0.000 claims 5
- 229940041153 polymyxins Drugs 0.000 claims 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 4
- 241000699670 Mus sp. Species 0.000 claims 3
- 239000003513 alkali Substances 0.000 claims 3
- 239000007853 buffer solution Substances 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- JIDVGUQUQSOHOL-UHFFFAOYSA-N myxin Chemical compound C1=CC=C2[N+]([O-])=C3C(OC)=CC=CC3=[N+]([O-])C2=C1O JIDVGUQUQSOHOL-UHFFFAOYSA-N 0.000 claims 2
- 241000894006 Bacteria Species 0.000 claims 1
- 208000035143 Bacterial infection Diseases 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 241000142520 Myxine Species 0.000 claims 1
- 241000251748 Myxinidae Species 0.000 claims 1
- 230000007059 acute toxicity Effects 0.000 claims 1
- 231100000403 acute toxicity Toxicity 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 208000022362 bacterial infectious disease Diseases 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 238000004090 dissolution Methods 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 238000001990 intravenous administration Methods 0.000 claims 1
- 210000003734 kidney Anatomy 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 108010073734 polymyxin D Proteins 0.000 claims 1
- 239000003910 polypeptide antibiotic agent Substances 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 230000009897 systematic effect Effects 0.000 claims 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 239000011734 sodium Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 3
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 3
- 235000010262 sodium metabisulphite Nutrition 0.000 description 3
- 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 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- 239000008351 acetate buffer Substances 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 239000008098 formaldehyde solution Substances 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- 239000004296 sodium metabisulphite Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring 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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 230000002123 temporal effect Effects 0.000 description 1
- 230000000699 topical effect Effects 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/50—Cyclic peptides containing at least one abnormal peptide link
- C07K7/54—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring
- C07K7/60—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring the cyclisation occurring through the 4-amino group of 2,4-diamino-butanoic acid
- C07K7/62—Polymyxins; Related peptides
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biochemistry (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Gastroenterology & Hepatology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB47190/62A GB1062895A (en) | 1962-12-13 | 1962-12-13 | Sulphomethyl derivatives of polymxin |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1518440A1 DE1518440A1 (de) | 1969-06-12 |
| DE1518440B2 DE1518440B2 (de) | 1973-03-01 |
| DE1518440C3 true DE1518440C3 (de) | 1973-09-27 |
Family
ID=10444070
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1518440A Expired DE1518440C3 (de) | 1962-12-13 | 1963-12-10 | Verfahren zur Herstellung eines Salzes eines Sulfomethylderivates von Polymyxin B oder E |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3317506A (enExample) |
| AT (1) | AT249266B (enExample) |
| BE (1) | BE641002A (enExample) |
| BR (1) | BR6355349D0 (enExample) |
| CH (1) | CH438579A (enExample) |
| DE (1) | DE1518440C3 (enExample) |
| DK (1) | DK107559C (enExample) |
| ES (1) | ES294436A1 (enExample) |
| FR (2) | FR1605453A (enExample) |
| GB (1) | GB1062895A (enExample) |
| LU (1) | LU44997A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3476738A (en) * | 1967-12-04 | 1969-11-04 | Upjohn Co | Pentakis(n-(sulfomethyl))circulin and salts thereof |
| US3622665A (en) * | 1969-07-02 | 1971-11-23 | Upjohn Co | Process for treating gram-negative bacterial diseases with pentakis {8 n-sulfomethyl{9 {0 circulin or salt thereof |
| US9724278B2 (en) | 2008-06-13 | 2017-08-08 | Colgate-Palmolive Company | Oral compositions and uses thereof |
| RU2015132569A (ru) | 2013-01-11 | 2017-02-14 | Кселлия Фармасьютикалз Апс | Полимиксины, композиции с ними, способы получения и способы применения |
| EP3166960B1 (en) | 2014-07-09 | 2019-08-07 | Xellia Pharmaceuticals ApS | Low substituted polymyxins and compositions thereof |
| US10532080B2 (en) | 2014-10-03 | 2020-01-14 | Xellia Pharmaceuticals Aps | Sulfomethylated polymixin compositions |
| SG11201702666SA (en) | 2014-10-03 | 2017-04-27 | Xellia Pharmaceuticals Aps | Inhalation device |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2599950A (en) * | 1947-04-30 | 1952-06-10 | American Cyanamid Co | Method of preparing polymyxin |
| US3044934A (en) * | 1960-05-19 | 1962-07-17 | Burroughs Wellcome Co | Parenteral administration of methanesulphonate of polymyxin a, b or e |
| US3228836A (en) * | 1962-10-09 | 1966-01-11 | Warner Lambert Pharmaceutical | Aldehyde complexes of colistin and polymyxin antibiotics |
-
1962
- 1962-12-13 GB GB47190/62A patent/GB1062895A/en not_active Expired
-
1963
- 1963-12-04 US US328049A patent/US3317506A/en not_active Expired - Lifetime
- 1963-12-04 CH CH1488163A patent/CH438579A/de unknown
- 1963-12-09 BE BE641002A patent/BE641002A/xx unknown
- 1963-12-10 DE DE1518440A patent/DE1518440C3/de not_active Expired
- 1963-12-11 BR BR155349/63A patent/BR6355349D0/pt unknown
- 1963-12-11 AT AT993063A patent/AT249266B/de active
- 1963-12-11 LU LU44997A patent/LU44997A1/xx unknown
- 1963-12-12 DK DK580063AA patent/DK107559C/da active
- 1963-12-12 ES ES0294436A patent/ES294436A1/es not_active Expired
- 1963-12-12 FR FR957003A patent/FR1605453A/fr not_active Expired
-
1964
- 1964-03-10 FR FR966818A patent/FR3405M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1518440A1 (de) | 1969-06-12 |
| BE641002A (enExample) | 1964-06-09 |
| DE1518440B2 (de) | 1973-03-01 |
| FR3405M (fr) | 1965-07-05 |
| DK107559C (da) | 1967-06-12 |
| FR1605453A (en) | 1976-02-27 |
| LU44997A1 (enExample) | 1964-06-11 |
| US3317506A (en) | 1967-05-02 |
| BR6355349D0 (pt) | 1973-07-19 |
| AT249266B (de) | 1966-09-12 |
| CH438579A (de) | 1967-06-30 |
| GB1062895A (en) | 1967-03-22 |
| ES294436A1 (es) | 1964-06-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| SH | Request for examination between 03.10.1968 and 22.04.1971 | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 |