NO117304B - - Google Patents
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- Publication number
- NO117304B NO117304B NO64153509A NO15350964A NO117304B NO 117304 B NO117304 B NO 117304B NO 64153509 A NO64153509 A NO 64153509A NO 15350964 A NO15350964 A NO 15350964A NO 117304 B NO117304 B NO 117304B
- Authority
- NO
- Norway
- Prior art keywords
- mitomycin
- derivatives
- analysis
- mitosan
- found
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical class CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- -1 cinnamoyl Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 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 description 10
- 239000000126 substance Substances 0.000 description 7
- UZUUQCBCWDBYCG-UHFFFAOYSA-N Mitomycin B Natural products O=C1C(OC)=C(C)C(=O)C2=C1C(COC(N)=O)C1(O)N2CC2C1N2C UZUUQCBCWDBYCG-UHFFFAOYSA-N 0.000 description 6
- HYFMSAFINFJTFH-UHFFFAOYSA-N Mitomycin-A Natural products O=C1C(OC)=C(C)C(=O)C2=C1C(COC(N)=O)C1(OC)N2CC2NC21 HYFMSAFINFJTFH-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- HYFMSAFINFJTFH-NGSRAFSJSA-N mitomycin A Chemical compound O=C1C(OC)=C(C)C(=O)C2=C1[C@@H](COC(N)=O)[C@]1(OC)N2C[C@@H]2N[C@@H]21 HYFMSAFINFJTFH-NGSRAFSJSA-N 0.000 description 6
- UZUUQCBCWDBYCG-DQRAMIIBSA-N mitomycin B Chemical compound O=C1C(OC)=C(C)C(=O)C2=C1[C@H](COC(N)=O)[C@]1(O)N2C[C@H]2[C@@H]1N2C UZUUQCBCWDBYCG-DQRAMIIBSA-N 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 229960004857 mitomycin Drugs 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- 239000003242 anti bacterial agent Substances 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 229940088710 antibiotic agent Drugs 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 231100001231 less toxic Toxicity 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- YJLUBHOZZTYQIP-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)NN=N2 YJLUBHOZZTYQIP-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229930192392 Mitomycin Natural products 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000187747 Streptomyces Species 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2927063 | 1963-06-07 | ||
| JP3093263 | 1963-06-19 | ||
| JP3093363 | 1963-06-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO117304B true NO117304B (de) | 1969-07-28 |
Family
ID=27286496
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO64153509A NO117304B (de) | 1963-06-07 | 1964-06-03 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3514452A (de) |
| BE (1) | BE648956A (de) |
| BR (1) | BR6459795D0 (de) |
| CH (3) | CH465627A (de) |
| DE (5) | DE1795476A1 (de) |
| DK (2) | DK114837B (de) |
| GB (1) | GB1071393A (de) |
| NL (3) | NL6406466A (de) |
| NO (1) | NO117304B (de) |
| SE (2) | SE320980B (de) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3420846A (en) * | 1964-08-25 | 1969-01-07 | Kyowa Hakko Kogyo Kk | 7-substituted mitomycin a |
| JPS5240B2 (de) * | 1973-12-17 | 1977-01-05 | ||
| JPS5439098A (en) * | 1977-08-31 | 1979-03-24 | Kyowa Hakko Kogyo Co Ltd | Mitomycin c derivatives |
| US4460599A (en) * | 1979-12-05 | 1984-07-17 | University Patents, Inc. | Mitomycin analogs |
| US4268676A (en) * | 1979-12-05 | 1981-05-19 | University Patents, Inc. | Mitomycin analogs |
| NZ199617A (en) * | 1981-05-15 | 1985-08-30 | University Patents Inc | Azirino(2',3',:3,4)pyrrolo(1,2-a)indole-4,7-dione derivatives and pharmaceutical compositions |
| US4487769A (en) * | 1982-06-04 | 1984-12-11 | Bristol-Myers Company | Amidines |
| US4803212A (en) * | 1983-04-11 | 1989-02-07 | Bristol-Myers Company | Amino disulfides |
| US4579737A (en) * | 1983-05-09 | 1986-04-01 | Bristol-Myers Company | Bis-amidines |
| US4567256A (en) * | 1983-05-09 | 1986-01-28 | Bristol-Myers Company | Amidine process |
| US4642352A (en) * | 1983-12-23 | 1987-02-10 | Bristol-Myers Company | Acylamino mitosanes |
| US4691023A (en) * | 1984-02-24 | 1987-09-01 | Bristol-Myers Company | Amino disulfides |
| US4866180A (en) * | 1984-02-24 | 1989-09-12 | Bristol-Myers Company | Amino disulfide thiol exchange products |
| EP0179092A4 (de) * | 1984-04-10 | 1987-08-05 | Baxter Travenol Lab | Mitomycinlösungen. |
| US5098926A (en) * | 1984-09-04 | 1992-03-24 | University Patents, Inc. | 6-substituted mitomycin analogs |
| DE3674043D1 (de) * | 1985-04-10 | 1990-10-18 | Kyowa Hakko Kogyo Kk | Pharmakologisch aktive mitomycinderivate. |
| IL86665A0 (en) * | 1987-06-12 | 1988-11-30 | Bristol Myers Co | Mitomycin analogs |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE624559A (de) * | ||||
| US3332944A (en) * | 1964-11-02 | 1967-07-25 | American Cyanamid Co | Antibiotic derivatives of mitomycins a, b, c and porfiromycin |
-
0
- NL NL129868D patent/NL129868C/xx active
-
1964
- 1964-06-03 US US372213A patent/US3514452A/en not_active Expired - Lifetime
- 1964-06-03 NO NO64153509A patent/NO117304B/no unknown
- 1964-06-05 DE DE19641795476 patent/DE1795476A1/de active Pending
- 1964-06-05 DE DE19641795474 patent/DE1795474A1/de active Pending
- 1964-06-05 BR BR159795/64A patent/BR6459795D0/pt unknown
- 1964-06-05 DE DE19641795475 patent/DE1795475A1/de active Pending
- 1964-06-05 DE DE19641445979 patent/DE1445979B1/de active Pending
- 1964-06-05 DE DE19641795473 patent/DE1795473B1/de active Pending
- 1964-06-06 CH CH739564A patent/CH465627A/fr unknown
- 1964-06-06 DK DK283864AA patent/DK114837B/da unknown
- 1964-06-06 CH CH11167A patent/CH486476A/fr not_active IP Right Cessation
- 1964-06-06 CH CH11067A patent/CH486475A/fr not_active IP Right Cessation
- 1964-06-08 NL NL6406466A patent/NL6406466A/xx unknown
- 1964-06-08 BE BE648956D patent/BE648956A/xx unknown
- 1964-06-08 SE SE8241/66A patent/SE320980B/xx unknown
- 1964-06-08 GB GB23662/64A patent/GB1071393A/en not_active Expired
- 1964-06-08 SE SE8240/66A patent/SE323388B/xx unknown
-
1965
- 1965-10-22 DK DK542965AA patent/DK124264B/da unknown
-
1969
- 1969-08-08 NL NL6912123A patent/NL6912123A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1071393A (en) | 1967-06-07 |
| DE1445979B1 (de) | 1972-05-04 |
| DK124264B (da) | 1972-10-02 |
| BR6459795D0 (pt) | 1973-07-17 |
| DE1795474A1 (de) | 1970-08-20 |
| NL129868C (de) | |
| US3514452A (en) | 1970-05-26 |
| CH486476A (fr) | 1970-02-28 |
| DE1795476A1 (de) | 1970-08-20 |
| SE323388B (de) | 1970-05-04 |
| NL6406466A (de) | 1964-12-08 |
| NL6912123A (de) | 1969-11-25 |
| BE648956A (de) | 1964-10-01 |
| DE1795473B1 (de) | 1972-03-09 |
| SE320980B (de) | 1970-02-23 |
| DK114837B (da) | 1969-08-11 |
| DE1795475A1 (de) | 1970-08-27 |
| CH486475A (fr) | 1970-02-28 |
| CH465627A (fr) | 1968-11-30 |
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