GB1323362A - Cyclopeptides derived from polymyxins and their preparation - Google Patents
Cyclopeptides derived from polymyxins and their preparationInfo
- Publication number
- GB1323362A GB1323362A GB3763270A GB3763270A GB1323362A GB 1323362 A GB1323362 A GB 1323362A GB 3763270 A GB3763270 A GB 3763270A GB 3763270 A GB3763270 A GB 3763270A GB 1323362 A GB1323362 A GB 1323362A
- Authority
- GB
- United Kingdom
- Prior art keywords
- leu
- dab
- formula
- pyridyl
- polymyxin
- 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
- 108010040201 Polymyxins Proteins 0.000 title abstract 5
- 108010069514 Cyclic Peptides Proteins 0.000 title 1
- 102000001189 Cyclic Peptides Human genes 0.000 title 1
- 229940041153 polymyxins Drugs 0.000 title 1
- -1 n-octanoyl Chemical group 0.000 abstract 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- OGNSCSPNOLGXSM-UHFFFAOYSA-N 2,4-diaminobutyric acid Chemical group NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 abstract 2
- ZJAFQAPHWPSKRZ-UHFFFAOYSA-N 4-nitrobenzenecarboperoxoic acid Chemical compound OOC(=O)C1=CC=C([N+]([O-])=O)C=C1 ZJAFQAPHWPSKRZ-UHFFFAOYSA-N 0.000 abstract 2
- 235000014469 Bacillus subtilis Nutrition 0.000 abstract 2
- 108090000790 Enzymes Proteins 0.000 abstract 2
- 102000004190 Enzymes Human genes 0.000 abstract 2
- 108091005804 Peptidases Proteins 0.000 abstract 2
- 239000004365 Protease Substances 0.000 abstract 2
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 abstract 2
- 108010056079 Subtilisins Proteins 0.000 abstract 2
- 102000005158 Subtilisins Human genes 0.000 abstract 2
- 150000001413 amino acids Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000004076 pyridyl group Chemical group 0.000 abstract 2
- LCPYQJIKPJDLLB-ZJUUUORDSA-N (2s)-2-[[(2r)-2-azaniumyl-4-methylpentanoyl]amino]-4-methylpentanoate Chemical compound CC(C)C[C@@H](N)C(=O)N[C@H](C(O)=O)CC(C)C LCPYQJIKPJDLLB-ZJUUUORDSA-N 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract 1
- 108010078777 Colistin Proteins 0.000 abstract 1
- MTCFGRXMJLQNBG-UWTATZPHSA-N D-Serine Chemical compound OC[C@@H](N)C(O)=O MTCFGRXMJLQNBG-UWTATZPHSA-N 0.000 abstract 1
- 229930195711 D-Serine Natural products 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 abstract 1
- 150000001204 N-oxides Chemical class 0.000 abstract 1
- 108010093965 Polymyxin B Proteins 0.000 abstract 1
- 108010059712 Pronase Proteins 0.000 abstract 1
- 108090000787 Subtilisin Proteins 0.000 abstract 1
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 abstract 1
- 239000004473 Threonine Substances 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 229940024606 amino acid Drugs 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 abstract 1
- 229960003346 colistin Drugs 0.000 abstract 1
- 108010059677 colistinase Proteins 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 238000007327 hydrogenolysis reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 229960000310 isoleucine Drugs 0.000 abstract 1
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 abstract 1
- 125000000741 isoleucyl group Chemical group [H]N([H])C(C(C([H])([H])[H])C([H])([H])C([H])([H])[H])C(=O)O* 0.000 abstract 1
- 125000001909 leucine group Chemical group [H]N(*)C(C(*)=O)C([H])([H])C(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 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 Chemical compound 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 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 abstract 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 abstract 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N phenylalanine group Chemical group N[C@@H](CC1=CC=CC=C1)C(=O)O COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 abstract 1
- 229920000024 polymyxin B Polymers 0.000 abstract 1
- 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 abstract 1
- KNIWPHSUTGNZST-UHFFFAOYSA-N polymyxin E2 Natural products CC(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 KNIWPHSUTGNZST-UHFFFAOYSA-N 0.000 abstract 1
- 229960005266 polymyxin b Drugs 0.000 abstract 1
- 229920001184 polypeptide Polymers 0.000 abstract 1
- 108090000765 processed proteins & peptides Proteins 0.000 abstract 1
- 102000004196 processed proteins & peptides Human genes 0.000 abstract 1
- 125000006239 protecting group Chemical group 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- 125000000341 threoninyl group Chemical group [H]OC([H])(C([H])([H])[H])C([H])(N([H])[H])C(*)=O 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/06—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents
- C07K1/061—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents using protecting groups
- C07K1/063—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents using protecting groups for alpha-amino functions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/06—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents
- C07K1/061—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents using protecting groups
- C07K1/064—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents using protecting groups for omega-amino or -guanidino functions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/12—Cyclic peptides with only normal peptide bonds in the ring
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Life Sciences & Earth Sciences (AREA)
- Analytical Chemistry (AREA)
- Peptides Or Proteins (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR6926912A FR2055903A5 (enrdf_load_stackoverflow) | 1969-08-05 | 1969-08-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1323362A true GB1323362A (en) | 1973-07-11 |
Family
ID=9038672
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3763270A Expired GB1323362A (en) | 1969-08-05 | 1970-08-04 | Cyclopeptides derived from polymyxins and their preparation |
Country Status (12)
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2128617A (en) * | 1982-10-06 | 1984-05-02 | Martti Vaara | Polypeptides for use in antibacterial therapy |
| WO2008017734A1 (en) | 2006-08-11 | 2008-02-14 | Northern Antibiotics Oy | Polymyxin derivatives and uses thereof |
| US7807637B2 (en) | 2006-08-11 | 2010-10-05 | Northern Antibiotics Oy | Polymyxin derivatives and uses thereof |
| US8193148B2 (en) | 2008-02-08 | 2012-06-05 | Northern Antibiotics Ltd. | Short fatty acid tail polymyxin derivatives and uses thereof |
| US8329645B2 (en) | 2008-02-08 | 2012-12-11 | Northern Antibiotics Ltd. | Polymyxin derivatives and uses thereof |
| US9096649B2 (en) | 2008-02-08 | 2015-08-04 | Northern Antibiotics Ltd. | Polymyxin derivatives and uses thereof |
| RU2675819C1 (ru) * | 2015-01-15 | 2018-12-25 | Нозерн Антибиотикс Ой | Производные полимиксина и их применение |
-
0
- BE BE754411A patent/BE754411A/xx unknown
-
1969
- 1969-08-05 FR FR6926912A patent/FR2055903A5/fr not_active Expired
-
1970
- 1970-07-28 NL NL7011150.A patent/NL164900C/xx not_active IP Right Cessation
- 1970-08-04 ZA ZA705377A patent/ZA705377B/xx unknown
- 1970-08-04 CA CA089,920*7A patent/CA950391A/en not_active Expired
- 1970-08-04 GB GB3763270A patent/GB1323362A/en not_active Expired
- 1970-08-04 JP JP45067805A patent/JPS4829149B1/ja active Pending
- 1970-08-04 CH CH1173470A patent/CH513817A/fr not_active IP Right Cessation
- 1970-08-04 SE SE10691/70A patent/SE369713B/xx unknown
- 1970-08-04 ZA ZA705378A patent/ZA705378B/xx unknown
- 1970-08-05 DE DE19702038997 patent/DE2038997A1/de active Pending
- 1970-08-05 CS CS5473A patent/CS152369B2/cs unknown
- 1970-08-05 AT AT712970A patent/AT295746B/de not_active IP Right Cessation
- 1970-08-05 AT AT712870A patent/AT299977B/de active
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2128617A (en) * | 1982-10-06 | 1984-05-02 | Martti Vaara | Polypeptides for use in antibacterial therapy |
| WO2008017734A1 (en) | 2006-08-11 | 2008-02-14 | Northern Antibiotics Oy | Polymyxin derivatives and uses thereof |
| US7807637B2 (en) | 2006-08-11 | 2010-10-05 | Northern Antibiotics Oy | Polymyxin derivatives and uses thereof |
| US8680234B2 (en) | 2006-08-11 | 2014-03-25 | Northern Antibiotics Oy | Polymyxin derivatives and uses thereof |
| US9067974B2 (en) | 2006-08-11 | 2015-06-30 | Northern Antibiotics Oy | Polymyxin derivatives and uses thereof |
| US8193148B2 (en) | 2008-02-08 | 2012-06-05 | Northern Antibiotics Ltd. | Short fatty acid tail polymyxin derivatives and uses thereof |
| US8329645B2 (en) | 2008-02-08 | 2012-12-11 | Northern Antibiotics Ltd. | Polymyxin derivatives and uses thereof |
| US8642535B2 (en) | 2008-02-08 | 2014-02-04 | Northern Antibiotics Ltd. | Short fatty acid tail polymyxin derivatives and uses thereof |
| US9090669B2 (en) | 2008-02-08 | 2015-07-28 | Northern Antibiotics Ltd. | Short fatty acid tail polymyxin derivatives and uses thereof |
| US9096649B2 (en) | 2008-02-08 | 2015-08-04 | Northern Antibiotics Ltd. | Polymyxin derivatives and uses thereof |
| RU2675819C1 (ru) * | 2015-01-15 | 2018-12-25 | Нозерн Антибиотикс Ой | Производные полимиксина и их применение |
Also Published As
| Publication number | Publication date |
|---|---|
| BE754411A (fr) | 1971-02-04 |
| CS152369B2 (enrdf_load_stackoverflow) | 1973-12-19 |
| SE369713B (enrdf_load_stackoverflow) | 1974-09-16 |
| CH513817A (fr) | 1971-10-15 |
| ZA705378B (en) | 1971-04-28 |
| CA950391A (en) | 1974-07-02 |
| ZA705377B (en) | 1971-04-28 |
| AT299977B (de) | 1972-07-10 |
| NL164900B (nl) | 1980-09-15 |
| NL164900C (nl) | 1981-02-16 |
| FR2055903A5 (enrdf_load_stackoverflow) | 1971-05-14 |
| JPS4829149B1 (enrdf_load_stackoverflow) | 1973-09-07 |
| AT295746B (de) | 1972-01-10 |
| DE2038997A1 (de) | 1971-02-18 |
| NL7011150A (enrdf_load_stackoverflow) | 1971-02-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |