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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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 (https=) |
| DE (1) | DE1244792B (https=) |
| FR (1) | FR4019M (https=) |
| GB (1) | GB1043858A (https=) |
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 BR BR166653/65A patent/BR6566653D0/pt unknown
- 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/de active Pending
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 |
|---|---|
| DE1244792B (de) | 1967-07-20 |
| BR6566653D0 (pt) | 1973-08-02 |
| FR4019M (https=) | 1966-03-21 |
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