SE468212B - Nya 6-substituerade mitomycinanaloger samt farmaceutisk komposition daerav med antineoplastisk verkan - Google Patents
Nya 6-substituerade mitomycinanaloger samt farmaceutisk komposition daerav med antineoplastisk verkanInfo
- Publication number
- SE468212B SE468212B SE8504113A SE8504113A SE468212B SE 468212 B SE468212 B SE 468212B SE 8504113 A SE8504113 A SE 8504113A SE 8504113 A SE8504113 A SE 8504113A SE 468212 B SE468212 B SE 468212B
- Authority
- SE
- Sweden
- Prior art keywords
- methoxy
- methyl
- hydroxymethyl
- hexahydro
- azirino
- Prior art date
Links
- 239000008194 pharmaceutical composition Chemical class 0.000 title claims description 4
- NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical class 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 title description 12
- 230000000118 anti-neoplastic effect Effects 0.000 title description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 75
- -1 propargyloxy Chemical group 0.000 claims description 66
- 150000001875 compounds Chemical class 0.000 claims description 62
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 50
- OIYWKBOYJXEVBU-UHFFFAOYSA-N carbamic acid 1H-indole-4,7-dione Chemical compound C(N)(O)=O.N1C=CC=2C(C=CC(C12)=O)=O OIYWKBOYJXEVBU-UHFFFAOYSA-N 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 17
- 241001465754 Metazoa Species 0.000 claims description 14
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 11
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 230000001613 neoplastic effect Effects 0.000 claims description 7
- RCADAQCLGCHYTA-UHFFFAOYSA-N OC(NC1=CC(C(C=CC2=O)=O)=C2N1)=O Chemical compound OC(NC1=CC(C(C=CC2=O)=O)=C2N1)=O RCADAQCLGCHYTA-UHFFFAOYSA-N 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 230000037396 body weight Effects 0.000 claims description 5
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 5
- 125000000466 oxiranyl group Chemical group 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 150000002926 oxygen Chemical class 0.000 claims description 4
- GOMJIKMERGJKAF-UHFFFAOYSA-N 1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-8a-methoxy-5-methyl-6-[2-(2-hydroxyethyldithio)ethoxy]azirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione carbamate Chemical compound NC(O)=O.C1N2C(C(C(C)=C(OCCSSCCO)C3=O)=O)=C3C(CO)C2(OC)C2C1N2 GOMJIKMERGJKAF-UHFFFAOYSA-N 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 239000002671 adjuvant Substances 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000005879 dioxolanyl group Chemical group 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 3
- 125000001137 3-hydroxypropoxy group Chemical group [H]OC([H])([H])C([H])([H])C([H])([H])O* 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000005336 allyloxy group Chemical group 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- ZUXZDRSQADGNPN-UHFFFAOYSA-N carbamic acid 2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),3,5,7,11-pentaene-10,13-dione Chemical compound NC(O)=O.O=C1C=CC(=O)C2=C1C=C1N2C=C2N=C21 ZUXZDRSQADGNPN-UHFFFAOYSA-N 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- WJGSXHSIJZGVEB-UHFFFAOYSA-N 1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-8a-methoxy-5-methyl-6-(3-chloropropoxy)-azirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione carbamate Chemical compound NC(O)=O.C1N2C(C(C(C)=C(OCCCCl)C3=O)=O)=C3C(CO)C2(OC)C2C1N2 WJGSXHSIJZGVEB-UHFFFAOYSA-N 0.000 claims 1
- UBCCPRSQFKJWDL-UHFFFAOYSA-N 1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-8a-methoxy-5-methyl-6-(allyloxy)-azirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione carbamate Chemical compound NC(O)=O.C1N2C(C(C(C)=C(OCC=C)C3=O)=O)=C3C(CO)C2(OC)C2C1N2 UBCCPRSQFKJWDL-UHFFFAOYSA-N 0.000 claims 1
- NPMCKXSLEHWPFD-UHFFFAOYSA-N 1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-8a-methoxy-5-methyl-6-(cyclobutylmethoxy)-azirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione carbamate Chemical compound NC(O)=O.OCC1C2(OC)C3NC3CN2C(C(C=2C)=O)=C1C(=O)C=2OCC1CCC1 NPMCKXSLEHWPFD-UHFFFAOYSA-N 0.000 claims 1
- PVRRSGKLWJKENC-UHFFFAOYSA-N 1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-8a-methoxy-5-methyl-6-[(2-pyranyl)methoxy]-azirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione carbamate Chemical compound NC(O)=O.OCC1C2(OC)C3NC3CN2C(C(C=2C)=O)=C1C(=O)C=2OCC1OC=CC=C1 PVRRSGKLWJKENC-UHFFFAOYSA-N 0.000 claims 1
- CXEQPPPHYGMJJA-UHFFFAOYSA-N 1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-8a-methoxy-5-methyl-6-[2-(2-methoxyethoxy)ethoxy]-azirino [2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione carbamate Chemical compound NC(O)=O.O=C1C(OCCOCCOC)=C(C)C(=O)C2=C1C(CO)C1(OC)N2CC2NC21 CXEQPPPHYGMJJA-UHFFFAOYSA-N 0.000 claims 1
- FNPWLDZKVYQOQW-UHFFFAOYSA-N 1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-8a-methoxy-5-methyl-6-{[2-(2-ethoxy)ethoxy]ethoxy}-azirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione carbamate Chemical compound NC(O)=O.O=C1C(OCCOCCOCC)=C(C)C(=O)C2=C1C(CO)C1(OC)N2CC2NC21 FNPWLDZKVYQOQW-UHFFFAOYSA-N 0.000 claims 1
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- 125000005055 alkyl alkoxy group Chemical group 0.000 claims 1
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
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- 239000000243 solution Substances 0.000 description 48
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- 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 21
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- 229910052757 nitrogen Inorganic materials 0.000 description 21
- 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 20
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- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000012750 in vivo screening Methods 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 208000003747 lymphoid leukemia Diseases 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000005936 piperidyl group Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
-
- 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
-
- 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
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/647,055 US4888341A (en) | 1984-09-04 | 1984-09-04 | 6-substituted mitomycin analogs |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE8504113D0 SE8504113D0 (sv) | 1985-09-04 |
| SE8504113L SE8504113L (sv) | 1986-03-05 |
| SE468212B true SE468212B (sv) | 1992-11-23 |
Family
ID=24595518
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8504113A SE468212B (sv) | 1984-09-04 | 1985-09-04 | Nya 6-substituerade mitomycinanaloger samt farmaceutisk komposition daerav med antineoplastisk verkan |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4888341A (ja) |
| JP (1) | JPS6168489A (ja) |
| KR (1) | KR900006855B1 (ja) |
| AT (1) | AT391318B (ja) |
| AU (1) | AU593773B2 (ja) |
| BE (1) | BE903168A (ja) |
| CA (1) | CA1249278A (ja) |
| CH (1) | CH666036A5 (ja) |
| DE (1) | DE3531197A1 (ja) |
| DK (1) | DK399985A (ja) |
| ES (2) | ES8800225A1 (ja) |
| FI (1) | FI81581C (ja) |
| FR (1) | FR2569697B1 (ja) |
| GB (1) | GB2164036B (ja) |
| GR (1) | GR852066B (ja) |
| HU (1) | HU194884B (ja) |
| IT (1) | IT1203633B (ja) |
| LU (1) | LU86059A1 (ja) |
| NL (1) | NL8502203A (ja) |
| NO (1) | NO162618C (ja) |
| PT (1) | PT81084B (ja) |
| SE (1) | SE468212B (ja) |
| ZA (1) | ZA854452B (ja) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU581673B2 (en) * | 1984-09-04 | 1989-03-02 | Bristol-Myers Company | Substituted 7-oxomitosanes |
| US4927943A (en) * | 1984-09-04 | 1990-05-22 | Bristol-Myers Company | Substituted 7-oxomitosanes |
| US5097036A (en) * | 1984-09-04 | 1992-03-17 | Bristol-Myers Company | Substituted 7-oxomitosanes |
| CA1282069C (en) * | 1985-09-12 | 1991-03-26 | Damon L. Meyer | Antibody complexes of hapten-modified diagnostic or therapeutic agents |
| EP0284380B1 (en) * | 1987-03-25 | 1992-06-10 | Kyowa Hakko Kogyo Kabushiki Kaisha | Mitomycin derivatives |
| US5023253A (en) * | 1987-12-21 | 1991-06-11 | University Patents, Inc. | 6-substituted mitomycin analogs |
| US5099016A (en) * | 1988-11-07 | 1992-03-24 | Bristol-Myers Company | Substituted 7-oxomitosanes |
| EP0485904B1 (en) * | 1990-11-13 | 1997-08-20 | Kyowa Hakko Kogyo Co., Ltd. | Mitomycin derivatives |
| DE10212359B4 (de) * | 2002-03-20 | 2005-10-06 | Peter Lisec | Verfahren und Vorrichtung zum maschinellen Applizieren eines Abstandhalterbandes auf eine Glasscheibe |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA770608A (en) * | 1967-10-31 | Matsui Masanao | 1a-substituted mitomycin | |
| CA770128A (en) * | 1967-10-24 | Matsui Masanao | 7-HYDROXY-9.alpha.-METHOXY MITOSANE AND PROCESS FOR PREPARING THE SAME | |
| US3306821A (en) * | 1962-09-04 | 1967-02-28 | Upjohn Co | Porfiromycin derivatives and method of making same |
| NL132363C (ja) * | 1964-07-10 | |||
| DE1570030A1 (de) * | 1964-07-11 | 1970-04-09 | Kyowa Hakko Kogyo Kk | Verfahren zur Herstellung von in 1a-Stellung substituierten Mitomycinverbindungen |
| JPS5748985A (en) * | 1980-09-09 | 1982-03-20 | Kyowa Hakko Kogyo Co Ltd | Novel mitomycin derivative |
| US4746746A (en) * | 1983-02-07 | 1988-05-24 | University Patents, Inc. | Mitomycin analogs |
| US4803212A (en) * | 1983-04-11 | 1989-02-07 | Bristol-Myers Company | Amino disulfides |
| AU581673B2 (en) * | 1984-09-04 | 1989-03-02 | Bristol-Myers Company | Substituted 7-oxomitosanes |
| US4814445A (en) * | 1984-09-04 | 1989-03-21 | Bristol-Myers Company | Process for preparing mitomycin analogs |
-
1984
- 1984-09-04 US US06/647,055 patent/US4888341A/en not_active Expired - Fee Related
-
1985
- 1985-06-13 ZA ZA854452A patent/ZA854452B/xx unknown
- 1985-07-05 KR KR1019850004843A patent/KR900006855B1/ko not_active IP Right Cessation
- 1985-07-18 GB GB08518099A patent/GB2164036B/en not_active Expired
- 1985-07-23 AT AT0218185A patent/AT391318B/de not_active IP Right Cessation
- 1985-07-24 CA CA000487369A patent/CA1249278A/en not_active Expired
- 1985-08-07 AU AU45882/85A patent/AU593773B2/en not_active Ceased
- 1985-08-07 NL NL8502203A patent/NL8502203A/nl not_active Application Discontinuation
- 1985-08-09 IT IT67722/85A patent/IT1203633B/it active
- 1985-08-19 FI FI853181A patent/FI81581C/fi not_active IP Right Cessation
- 1985-08-27 GR GR852066A patent/GR852066B/el unknown
- 1985-08-29 LU LU86059A patent/LU86059A1/fr unknown
- 1985-08-31 DE DE19853531197 patent/DE3531197A1/de not_active Withdrawn
- 1985-09-02 FR FR858513003A patent/FR2569697B1/fr not_active Expired - Fee Related
- 1985-09-02 DK DK399985A patent/DK399985A/da not_active Application Discontinuation
- 1985-09-03 PT PT81084A patent/PT81084B/pt not_active IP Right Cessation
- 1985-09-03 NO NO853468A patent/NO162618C/no unknown
- 1985-09-03 HU HU853336A patent/HU194884B/hu not_active IP Right Cessation
- 1985-09-03 JP JP60195692A patent/JPS6168489A/ja active Pending
- 1985-09-03 ES ES546690A patent/ES8800225A1/es not_active Expired
- 1985-09-03 BE BE0/215534A patent/BE903168A/fr not_active IP Right Cessation
- 1985-09-03 CH CH3790/85A patent/CH666036A5/de not_active IP Right Cessation
- 1985-09-04 SE SE8504113A patent/SE468212B/sv not_active IP Right Cessation
-
1987
- 1987-05-28 ES ES557566A patent/ES8800227A1/es not_active Expired
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