GB1043858A - Streptonigrin derivatives and preparation thereof - Google Patents
Streptonigrin derivatives and preparation thereofInfo
- Publication number
- GB1043858A GB1043858A GB3901/65A GB390165A GB1043858A GB 1043858 A GB1043858 A GB 1043858A GB 3901/65 A GB3901/65 A GB 3901/65A GB 390165 A GB390165 A GB 390165A GB 1043858 A GB1043858 A GB 1043858A
- Authority
- GB
- United Kingdom
- Prior art keywords
- streptonigrin
- monoxime
- azastreptonigrin
- dimethylsulphate
- trimethyl ester
- 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
- PVYJZLYGTZKPJE-UHFFFAOYSA-N streptonigrin Chemical class C=1C=C2C(=O)C(OC)=C(N)C(=O)C2=NC=1C(C=1N)=NC(C(O)=O)=C(C)C=1C1=CC=C(OC)C(OC)=C1O PVYJZLYGTZKPJE-UHFFFAOYSA-N 0.000 title abstract 13
- 150000002148 esters Chemical class 0.000 abstract 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 4
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 abstract 3
- NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 239000003242 anti bacterial agent Substances 0.000 abstract 2
- 229940088710 antibiotic agent Drugs 0.000 abstract 2
- 230000003327 cancerostatic effect Effects 0.000 abstract 2
- SQQXRXKYTKFFSM-UHFFFAOYSA-N chembl1992147 Chemical compound OC1=C(OC)C(OC)=CC=C1C1=C(C)C(C(O)=O)=NC(C=2N=C3C4=NC(C)(C)N=C4C(OC)=C(O)C3=CC=2)=C1N SQQXRXKYTKFFSM-UHFFFAOYSA-N 0.000 abstract 2
- GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 abstract 2
- 150000002923 oximes Chemical class 0.000 abstract 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract 2
- 150000003839 salts Chemical group 0.000 abstract 2
- AGNGYMCLFWQVGX-AGFFZDDWSA-N (e)-1-[(2s)-2-amino-2-carboxyethoxy]-2-diazonioethenolate Chemical compound OC(=O)[C@@H](N)CO\C([O-])=C\[N+]#N AGNGYMCLFWQVGX-AGFFZDDWSA-N 0.000 abstract 1
- VTACPFVLSHWTGG-UHFFFAOYSA-N 1-propan-2-yl-1h-indene Chemical compound C1=CC=C2C(C(C)C)C=CC2=C1 VTACPFVLSHWTGG-UHFFFAOYSA-N 0.000 abstract 1
- LPXQRXLUHJKZIE-UHFFFAOYSA-N 8-azaguanine Chemical compound NC1=NC(O)=C2NN=NC2=N1 LPXQRXLUHJKZIE-UHFFFAOYSA-N 0.000 abstract 1
- 229960005508 8-azaguanine Drugs 0.000 abstract 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 abstract 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 abstract 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 1
- 239000002841 Lewis acid Substances 0.000 abstract 1
- 241001465754 Metazoa Species 0.000 abstract 1
- 206010028980 Neoplasm Diseases 0.000 abstract 1
- FYAMXEPQQLNQDM-UHFFFAOYSA-N Tris(1-aziridinyl)phosphine oxide Chemical compound C1CN1P(N1CC1)(=O)N1CC1 FYAMXEPQQLNQDM-UHFFFAOYSA-N 0.000 abstract 1
- 239000003377 acid catalyst Substances 0.000 abstract 1
- 229940035676 analgesics Drugs 0.000 abstract 1
- 239000000730 antalgic agent Substances 0.000 abstract 1
- 229940045687 antimetabolites folic acid analogs Drugs 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 229950011321 azaserine Drugs 0.000 abstract 1
- 229910052793 cadmium Inorganic materials 0.000 abstract 1
- 229910052791 calcium Inorganic materials 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- -1 dimethylsulphate quaternary ammonium salt Chemical class 0.000 abstract 1
- 150000002224 folic acids Chemical class 0.000 abstract 1
- 239000003326 hypnotic agent Substances 0.000 abstract 1
- 230000000147 hypnotic effect Effects 0.000 abstract 1
- 239000004615 ingredient Substances 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- 150000007517 lewis acids Chemical class 0.000 abstract 1
- 229960005015 local anesthetics Drugs 0.000 abstract 1
- HAWPXGHAZFHHAD-UHFFFAOYSA-N mechlorethamine Chemical class ClCCN(C)CCCl HAWPXGHAZFHHAD-UHFFFAOYSA-N 0.000 abstract 1
- 229960004961 mechlorethamine Drugs 0.000 abstract 1
- 229960001428 mercaptopurine Drugs 0.000 abstract 1
- 229910021645 metal ion Inorganic materials 0.000 abstract 1
- 229960004857 mitomycin Drugs 0.000 abstract 1
- 229910052759 nickel Inorganic materials 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract 1
- 235000015320 potassium carbonate Nutrition 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 238000006722 reduction reaction Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- IUCJMVBFZDHPDX-UHFFFAOYSA-N tretamine Chemical compound C1CN1C1=NC(N2CC2)=NC(N2CC2)=N1 IUCJMVBFZDHPDX-UHFFFAOYSA-N 0.000 abstract 1
- 229950001353 tretamine Drugs 0.000 abstract 1
- 229960005088 urethane Drugs 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention relates to (a) streptonigrin monoxime, its mono-alkyl and trimethyl ester and the dimethylsulphate quaternary salt of the trimethyl ester, (b) isopropylidene azastreptonigrin, its mono-alkyl and trimethyl ester and the dimethylsulphate quaternary salt of the trimethylester, (c) dihydroazastreptonigrin, (d) azastreptonigrin and complexes of (a), (b), (c) and (d) with polyvalent metal ions, e.g. Ca, Cd, Ce, Cr, Cu, Fe, Ni and Zn. Streptonigrin monoxime is obtained by reacting streptonigrin with hydroxylamine in a solvent such as pyridine. Monoalkyl esters are produced by reacting the oxime with an alcohol and an acid catalyst especially a Lewis acid. The trimethyl ester is produced by reaction with diazomethane. The dimethylsulphate quaternary ammonium salt of the trimethyl ester is produced by treating the oxime with dimethylsulphate and K2CO3 in acetone solution. Isopropylidene azastreptonigrin is prepared by treating dihydroazastreptonigrin with acetone in the presence of air oxidation. Catalyctic or chemical reduction of the monoxime produces the unstable dihydroazastreptonigrin which oxidizes in air or oxygen to azastreptonigrin. Streptonigrin has the formula <FORM:1043858/C2/1> Streptonigrin monoxime has the formula <FORM:1043858/C2/2> wherein X is the C and D rings above.ALSO:A pharmaceutical composition for the treatment of tumours in man and animals comprises streptonigrin monoxime or isopropylindene azastreptonigrin (antibiotics) and a carrier for oral or parenteral use. Optional ingredients are other antibiotics, hypnotics, analgesics, local anaesthetics and carcinostatic agents e.g. nitrogen mustard type 6-mercaptopurine, 8-azaguanine, urethane, 6-diazo-5-oxo-1-norleucine, azaserine, triethylenemelamine mitomycin C, triethylenephosphoramide, 1, 4-dimethyl-sulphonyloxybutane and carcinostatic folic acid analogues.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00376296A US3804947A (en) | 1962-06-25 | 1964-06-15 | Isopropylidene azastreptonigrin and streptonigrin-monoxime |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1043858A true GB1043858A (en) | 1966-09-28 |
Family
ID=23484423
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3901/65A Expired GB1043858A (en) | 1964-06-15 | 1965-01-28 | Streptonigrin derivatives and preparation thereof |
Country Status (4)
| Country | Link |
|---|---|
| BR (1) | BR6566653D0 (en) |
| DE (1) | DE1244792B (en) |
| FR (1) | FR4019M (en) |
| GB (1) | GB1043858A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5158960A (en) * | 1991-05-24 | 1992-10-27 | E. R. Squibb & Sons, Inc. | 10'-Desmethoxystreptonigrin |
-
1965
- 1965-01-28 FR FR3599A patent/FR4019M/fr not_active Expired
- 1965-01-28 GB GB3901/65A patent/GB1043858A/en not_active Expired
- 1965-01-28 DE DEP35959A patent/DE1244792B/en active Pending
- 1965-01-28 BR BR166653/65A patent/BR6566653D0/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5158960A (en) * | 1991-05-24 | 1992-10-27 | E. R. Squibb & Sons, Inc. | 10'-Desmethoxystreptonigrin |
| US5320955A (en) * | 1991-05-24 | 1994-06-14 | E. R. Squibb & Sons, Inc. | 10'desmethoxystreptonigrin production by Streptomyces albus |
Also Published As
| Publication number | Publication date |
|---|---|
| BR6566653D0 (en) | 1973-08-02 |
| DE1244792B (en) | 1967-07-20 |
| FR4019M (en) | 1966-03-21 |
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