DD228259A5 - Verfahren zur herstellung von 7-acylamino-9a-methoxymitosanen - Google Patents
Verfahren zur herstellung von 7-acylamino-9a-methoxymitosanen Download PDFInfo
- Publication number
- DD228259A5 DD228259A5 DD84271473A DD27147384A DD228259A5 DD 228259 A5 DD228259 A5 DD 228259A5 DD 84271473 A DD84271473 A DD 84271473A DD 27147384 A DD27147384 A DD 27147384A DD 228259 A5 DD228259 A5 DD 228259A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- amino
- group
- mitomycin
- methoxymitosane
- methoxymitosan
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 230000008569 process Effects 0.000 title claims abstract description 10
- 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 claims abstract description 124
- 229960004857 mitomycin Drugs 0.000 claims abstract description 67
- 150000001875 compounds Chemical class 0.000 claims abstract description 66
- -1 2-methoxyethoxy Chemical group 0.000 claims description 37
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 29
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 22
- 239000000460 chlorine Substances 0.000 claims description 17
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 150000001450 anions Chemical class 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
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- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 4
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000012312 sodium hydride Substances 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
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- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000000638 benzylaminocarbonyl group Chemical group C(C1=CC=CC=C1)NC(=O)* 0.000 claims description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
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- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 125000006633 tert-butoxycarbonylamino group Chemical group 0.000 claims description 2
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- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 4
- 208000001382 Experimental Melanoma Diseases 0.000 description 4
- 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 4
- 241000699666 Mus <mouse, genus> Species 0.000 description 4
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- 238000000862 absorption spectrum Methods 0.000 description 4
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- 241001529936 Murinae Species 0.000 description 3
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- 238000005192 partition Methods 0.000 description 1
- AGUWUIVKDXDKBT-UHFFFAOYSA-N phenyl 2-chloroacetate Chemical compound ClCC(=O)OC1=CC=CC=C1 AGUWUIVKDXDKBT-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- HDGICZVUXOQTPV-UHFFFAOYSA-N phenylsulfanyl acetate Chemical compound CC(=O)OSC1=CC=CC=C1 HDGICZVUXOQTPV-UHFFFAOYSA-N 0.000 description 1
- 150000008039 phosphoramides Chemical class 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 150000003566 thiocarboxylic acids Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 230000004580 weight loss 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
- C07D487/02—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 two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Oncology (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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/564,806 US4642352A (en) | 1983-12-23 | 1983-12-23 | Acylamino mitosanes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD228259A5 true DD228259A5 (de) | 1985-10-09 |
Family
ID=24255968
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD84271473A DD228259A5 (de) | 1983-12-23 | 1984-12-21 | Verfahren zur herstellung von 7-acylamino-9a-methoxymitosanen |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US4642352A (sh) |
| JP (1) | JPS60169481A (sh) |
| KR (1) | KR910009329B1 (sh) |
| AR (1) | AR244231A1 (sh) |
| AT (1) | AT386828B (sh) |
| AU (1) | AU561376B2 (sh) |
| BE (1) | BE901377A (sh) |
| CA (1) | CA1239645A (sh) |
| CH (1) | CH665641A5 (sh) |
| DD (1) | DD228259A5 (sh) |
| DE (1) | DE3447003C2 (sh) |
| DK (1) | DK169477B1 (sh) |
| ES (1) | ES8603485A1 (sh) |
| FI (1) | FI81099C (sh) |
| FR (1) | FR2557112B1 (sh) |
| GB (1) | GB2151627B (sh) |
| GR (1) | GR82567B (sh) |
| HU (1) | HU193245B (sh) |
| IE (1) | IE57835B1 (sh) |
| IL (1) | IL73876A (sh) |
| IT (1) | IT1178792B (sh) |
| LU (1) | LU85711A1 (sh) |
| MY (1) | MY100976A (sh) |
| NL (1) | NL8403852A (sh) |
| NO (1) | NO163570C (sh) |
| NZ (1) | NZ210254A (sh) |
| OA (1) | OA07911A (sh) |
| PT (1) | PT79741B (sh) |
| SE (1) | SE8406577L (sh) |
| SU (1) | SU1364239A3 (sh) |
| YU (1) | YU45688B (sh) |
| ZA (1) | ZA849907B (sh) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4487769A (en) * | 1982-06-04 | 1984-12-11 | Bristol-Myers Company | Amidines |
| NZ206932A (en) * | 1983-02-07 | 1987-08-31 | University Patents Inc | Certain 6-(heterocyclyl or amino) mitosanes and pharmaceutical compositions |
| US4803212A (en) * | 1983-04-11 | 1989-02-07 | Bristol-Myers Company | Amino disulfides |
| FR2571373A1 (fr) * | 1984-10-09 | 1986-04-11 | Bristol Myers Co | Procede de preparation de derives n7-substitues de la mitomycine c |
| CA1282069C (en) * | 1985-09-12 | 1991-03-26 | Damon L. Meyer | Antibody complexes of hapten-modified diagnostic or therapeutic agents |
| JPS6354380A (ja) * | 1986-08-26 | 1988-03-08 | Kyowa Hakko Kogyo Co Ltd | マイトマイシン誘導体 |
| ZA886812B (en) * | 1987-11-23 | 1989-07-26 | Bristol Myers Co | Anti-tumor prodrugs |
| US4874779A (en) * | 1988-06-29 | 1989-10-17 | Bristol-Myers Company | Mitomycin phosphate derivatives |
| US5214804A (en) * | 1992-01-27 | 1993-06-01 | Carey Michael J | Protective mask with scarf |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE655399A (sh) * | ||||
| US27384A (en) * | 1860-03-06 | Slide-valve for steam-engines | ||
| CA771155A (en) * | 1967-11-07 | Matsui Masanao | Phosphorus-containing derivatives of mitomycin c | |
| US3660578A (en) * | 1957-04-06 | 1972-05-02 | Kyowa Hakko Kogyo Kk | Mitomycin c |
| NL129868C (sh) * | 1963-06-07 | |||
| DE1570029A1 (de) * | 1964-07-09 | 1970-04-09 | Kyowa Hakko Kogyo Kk | Verfahren zur Herstellung von Mitosanverbindungen |
| US3420846A (en) * | 1964-08-25 | 1969-01-07 | Kyowa Hakko Kogyo Kk | 7-substituted mitomycin a |
| US3332944A (en) * | 1964-11-02 | 1967-07-25 | American Cyanamid Co | Antibiotic derivatives of mitomycins a, b, c and porfiromycin |
| FR1540921A (fr) * | 1965-05-18 | 1968-10-04 | Kyowa Hakko Kogyo Kk | Procédé de préparation de dérivés de thio-urée de la mitomycine c |
| US3410867A (en) * | 1965-11-22 | 1968-11-12 | Kyowa Hakko Kogyo Kk | Mitomycin derivatives |
| JPS5439098A (en) * | 1977-08-31 | 1979-03-24 | Kyowa Hakko Kogyo Co Ltd | Mitomycin c derivatives |
| DE2966984D1 (en) * | 1978-07-18 | 1984-06-20 | Kyowa Hakko Kogyo Kk | New mitomycins and processes for production thereof |
| US4268676A (en) * | 1979-12-05 | 1981-05-19 | University Patents, Inc. | Mitomycin analogs |
| US4444768A (en) * | 1980-03-04 | 1984-04-24 | Ciba-Geigy Corporation | Pyrimido[1,6-a]indoles, pharmaceutical preparations containing them, and methods of treating pain and inflammation with them |
| 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 |
| JPS58201791A (ja) | 1982-05-19 | 1983-11-24 | Katsuo Unno | ヘマトポルフイリン誘導体 |
| US4487769A (en) * | 1982-06-04 | 1984-12-11 | Bristol-Myers Company | Amidines |
-
1983
- 1983-12-23 US US06/564,806 patent/US4642352A/en not_active Expired - Fee Related
-
1984
- 1984-11-20 NZ NZ210254A patent/NZ210254A/en unknown
- 1984-11-20 AU AU35710/84A patent/AU561376B2/en not_active Ceased
- 1984-12-06 AR AR84298866A patent/AR244231A1/es active
- 1984-12-11 FR FR8418904A patent/FR2557112B1/fr not_active Expired
- 1984-12-12 CA CA000469874A patent/CA1239645A/en not_active Expired
- 1984-12-19 NO NO845100A patent/NO163570C/no unknown
- 1984-12-19 YU YU215284A patent/YU45688B/sh unknown
- 1984-12-19 ES ES538804A patent/ES8603485A1/es not_active Expired
- 1984-12-19 ZA ZA849907A patent/ZA849907B/xx unknown
- 1984-12-19 NL NL8403852A patent/NL8403852A/nl not_active Application Discontinuation
- 1984-12-19 FI FI845037A patent/FI81099C/fi not_active IP Right Cessation
- 1984-12-20 CH CH6091/84A patent/CH665641A5/de not_active IP Right Cessation
- 1984-12-20 IL IL73876A patent/IL73876A/xx not_active IP Right Cessation
- 1984-12-21 HU HU844801A patent/HU193245B/hu not_active IP Right Cessation
- 1984-12-21 DD DD84271473A patent/DD228259A5/de not_active IP Right Cessation
- 1984-12-21 SU SU843826167A patent/SU1364239A3/ru active
- 1984-12-21 OA OA58488A patent/OA07911A/xx unknown
- 1984-12-21 AT AT0407484A patent/AT386828B/de not_active IP Right Cessation
- 1984-12-21 DE DE3447003A patent/DE3447003C2/de not_active Expired - Fee Related
- 1984-12-21 PT PT79741A patent/PT79741B/pt not_active IP Right Cessation
- 1984-12-21 BE BE0/214237A patent/BE901377A/fr not_active IP Right Cessation
- 1984-12-21 IT IT24227/84A patent/IT1178792B/it active
- 1984-12-21 IE IE3318/84A patent/IE57835B1/en not_active IP Right Cessation
- 1984-12-21 DK DK621484A patent/DK169477B1/da active
- 1984-12-21 JP JP59268757A patent/JPS60169481A/ja active Granted
- 1984-12-21 SE SE8406577A patent/SE8406577L/xx unknown
- 1984-12-21 GR GR82567A patent/GR82567B/el unknown
- 1984-12-21 LU LU85711A patent/LU85711A1/fr unknown
- 1984-12-21 GB GB08432513A patent/GB2151627B/en not_active Expired
- 1984-12-22 KR KR1019840008275A patent/KR910009329B1/ko not_active Expired
-
1987
- 1987-09-29 MY MYPI87002232A patent/MY100976A/en unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ENJ | Ceased due to non-payment of renewal fee |