AT394853B - Verfahren zur herstellung von neuen mitosanderivaten - Google Patents
Verfahren zur herstellung von neuen mitosanderivaten Download PDFInfo
- Publication number
- AT394853B AT394853B AT0206483A AT206483A AT394853B AT 394853 B AT394853 B AT 394853B AT 0206483 A AT0206483 A AT 0206483A AT 206483 A AT206483 A AT 206483A AT 394853 B AT394853 B AT 394853B
- Authority
- AT
- Austria
- Prior art keywords
- mitomycin
- compound
- general formula
- dose
- group
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 93
- 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 description 76
- 150000001875 compounds Chemical class 0.000 claims description 45
- 229960004857 mitomycin Drugs 0.000 claims description 39
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 15
- -1 amino, methoxy, hydroxy Chemical group 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical class CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 241000699670 Mus sp. Species 0.000 claims description 9
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- 241001465754 Metazoa Species 0.000 claims description 8
- 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 claims description 8
- 230000000259 anti-tumor effect Effects 0.000 claims description 8
- 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 claims description 8
- 206010028980 Neoplasm Diseases 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 230000004083 survival effect Effects 0.000 claims description 6
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000012429 reaction media Substances 0.000 claims description 4
- 241000699666 Mus <mouse, genus> Species 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 239000012430 organic reaction media Substances 0.000 claims description 3
- 231100000419 toxicity Toxicity 0.000 claims description 3
- 230000001988 toxicity Effects 0.000 claims description 3
- 208000001382 Experimental Melanoma Diseases 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 238000010171 animal model Methods 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 230000005764 inhibitory process Effects 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 241000124008 Mammalia Species 0.000 claims 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 1
- 239000007943 implant Substances 0.000 claims 1
- 238000002347 injection Methods 0.000 claims 1
- 239000007924 injection Substances 0.000 claims 1
- 238000007912 intraperitoneal administration Methods 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 81
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 22
- 238000002329 infrared spectrum Methods 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000003818 flash chromatography Methods 0.000 description 6
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-RALIUCGRSA-N pyridine-d5 Chemical compound [2H]C1=NC([2H])=C([2H])C([2H])=C1[2H] JUJWROOIHBZHMG-RALIUCGRSA-N 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 239000006188 syrup Substances 0.000 description 6
- 235000020357 syrup Nutrition 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- 238000004809 thin layer chromatography Methods 0.000 description 5
- 229930192392 Mitomycin Natural products 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- IWVFFVBJTCPIIG-UHFFFAOYSA-N 2,2-dimethoxy-1-methylpyrrolidine Chemical compound COC1(OC)CCCN1C IWVFFVBJTCPIIG-UHFFFAOYSA-N 0.000 description 3
- HRHKSTOGXBBQCB-UHFFFAOYSA-N Mitomycin E Natural products O=C1C(N)=C(C)C(=O)C2=C1C(COC(N)=O)C1(OC)C3N(C)C3CN12 HRHKSTOGXBBQCB-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 150000001241 acetals Chemical class 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 208000032839 leukemia Diseases 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- HRHKSTOGXBBQCB-VFWICMBZSA-N methylmitomycin Chemical compound O=C1C(N)=C(C)C(=O)C2=C1[C@@H](COC(N)=O)[C@@]1(OC)[C@H]3N(C)[C@H]3CN12 HRHKSTOGXBBQCB-VFWICMBZSA-N 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- SEZWJRWTCIPRSV-UHFFFAOYSA-N [N]C(N)=O Chemical group [N]C(N)=O SEZWJRWTCIPRSV-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 239000002246 antineoplastic agent Substances 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000000855 fermentation Methods 0.000 description 2
- 230000004151 fermentation Effects 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000011987 methylation Effects 0.000 description 2
- 238000007069 methylation reaction Methods 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 229950004406 porfiromycin Drugs 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- SBFJSZPNSCJDKI-UHFFFAOYSA-N 1-(diethoxymethyl)piperidine Chemical compound CCOC(OCC)N1CCCCC1 SBFJSZPNSCJDKI-UHFFFAOYSA-N 0.000 description 1
- JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 description 1
- SCNPZYFBDOEUPZ-UHFFFAOYSA-N 4-(diethoxymethyl)morpholine Chemical compound CCOC(OCC)N1CCOCC1 SCNPZYFBDOEUPZ-UHFFFAOYSA-N 0.000 description 1
- 206010003445 Ascites Diseases 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- 241001529936 Murinae Species 0.000 description 1
- FIWILGQIZHDAQG-UHFFFAOYSA-N NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F Chemical compound NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F FIWILGQIZHDAQG-UHFFFAOYSA-N 0.000 description 1
- 101000689402 Phasmahyla jandaia Phylloseptin-J5 Proteins 0.000 description 1
- WKYZYLKGCNBEMG-WUDYKRTCSA-N [(1as,8s,8ar,8bs)-6-hydroxy-8a-methoxy-5-methyl-4,7-dioxo-1,1a,2,4,7,8,8a,8b-octahydroazireno[2',3':3,4]pyrrolo[1,2-a]indol-8-yl]methyl carbamate Chemical compound C1N2C(C(=C(C)C(=O)C3=O)O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 WKYZYLKGCNBEMG-WUDYKRTCSA-N 0.000 description 1
- 208000009956 adenocarcinoma Diseases 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 235000019365 chlortetracycline Nutrition 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000002038 ethyl acetate fraction Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- QMRIWYCCTCNABA-UHFFFAOYSA-N indole-4,7-quinone Chemical compound O=C1C=CC(=O)C2=C1C=CN2 QMRIWYCCTCNABA-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- AGJSNMGHAVDLRQ-HUUJSLGLSA-N methyl (2s)-2-[[(2r)-2-[[(2s)-2-[[(2r)-2-amino-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,3-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoate Chemical compound SC[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(=O)N[C@@H](CCSC)C(=O)OC)CC1=CC=C(O)C(C)=C1C AGJSNMGHAVDLRQ-HUUJSLGLSA-N 0.000 description 1
- AGJSNMGHAVDLRQ-IWFBPKFRSA-N methyl (2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-amino-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,3-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoate Chemical compound SC[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCSC)C(=O)OC)CC1=CC=C(O)C(C)=C1C AGJSNMGHAVDLRQ-IWFBPKFRSA-N 0.000 description 1
- 238000002638 palliative care Methods 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
- 238000005406 washing Methods 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)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT0076188A AT397091B (de) | 1982-06-04 | 1988-03-22 | Verfahren zur herstellung von neuen mitosan-derivaten |
| AT0076288A AT397092B (de) | 1982-06-04 | 1988-03-22 | Verfahren zur herstellung von neuen mitosan-derivaten |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38514982A | 1982-06-04 | 1982-06-04 | |
| US06/492,903 US4487769A (en) | 1982-06-04 | 1983-05-09 | Amidines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ATA206483A ATA206483A (de) | 1991-12-15 |
| AT394853B true AT394853B (de) | 1992-07-10 |
Family
ID=27010906
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT0206483A AT394853B (de) | 1982-06-04 | 1983-06-06 | Verfahren zur herstellung von neuen mitosanderivaten |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US4487769A (en]) |
| KR (1) | KR870000932B1 (en]) |
| AR (1) | AR241438A1 (en]) |
| AT (1) | AT394853B (en]) |
| AU (1) | AU571179B2 (en]) |
| CA (1) | CA1230333A (en]) |
| CH (1) | CH657856A5 (en]) |
| DD (1) | DD210275A5 (en]) |
| DE (1) | DE3319992A1 (en]) |
| DK (2) | DK161023C (en]) |
| ES (3) | ES8407493A1 (en]) |
| FI (1) | FI78700C (en]) |
| FR (1) | FR2528048B1 (en]) |
| GB (1) | GB2121796B (en]) |
| GR (1) | GR78277B (en]) |
| HU (1) | HU198936B (en]) |
| IE (1) | IE56107B1 (en]) |
| IL (1) | IL68852A0 (en]) |
| IT (1) | IT1206452B (en]) |
| LU (1) | LU84843A1 (en]) |
| NL (1) | NL8301949A (en]) |
| NO (1) | NO161676C (en]) |
| NZ (1) | NZ204352A (en]) |
| OA (1) | OA07452A (en]) |
| PT (1) | PT76810B (en]) |
| SE (1) | SE455504B (en]) |
| YU (2) | YU42866B (en]) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US4579737A (en) * | 1983-05-09 | 1986-04-01 | Bristol-Myers Company | Bis-amidines |
| US4642352A (en) * | 1983-12-23 | 1987-02-10 | Bristol-Myers Company | Acylamino mitosanes |
| US4814445A (en) * | 1984-09-04 | 1989-03-21 | Bristol-Myers Company | Process for preparing mitomycin analogs |
| AU581673B2 (en) * | 1984-09-04 | 1989-03-02 | Bristol-Myers Company | Substituted 7-oxomitosanes |
| JPS61176590A (ja) * | 1985-01-31 | 1986-08-08 | Kyowa Hakko Kogyo Co Ltd | ７−ｎ−アミノメチレンマイトマイシン誘導体、製造法及び抗腫瘍剤 |
| US4639528A (en) * | 1985-02-21 | 1987-01-27 | Bristol-Myers Company | Crystalline form of 7-(dimethylaminomethylene-amino-9a-methoxymitosane |
| AT396688B (de) * | 1985-02-21 | 1993-11-25 | Bristol Myers Squibb Co | Verfahren zur herstellung von kristallinem |
| ZA86308B (en) * | 1985-02-25 | 1986-11-26 | Bristol Myers Co | In-vial deposition of 7-(dimethylaminomethylene)amino-9a-methoxy-mitosane |
| US4652644A (en) * | 1985-04-29 | 1987-03-24 | Bristol-Myers Company | Process for preparation of N7 -amidino substituted mitomycin C derivatives |
| JPH066592B2 (ja) * | 1986-04-18 | 1994-01-26 | 協和醗酵工業株式会社 | マイトマイシン誘導体 |
| US4791113A (en) * | 1986-05-14 | 1988-12-13 | Kyowa Hakko Kogyo Kabushiki Kaisha | Mitomycin derivatives as antileukemia agents |
| JPS6354380A (ja) * | 1986-08-26 | 1988-03-08 | Kyowa Hakko Kogyo Co Ltd | マイトマイシン誘導体 |
| JPS63150282A (ja) * | 1986-12-13 | 1988-06-22 | Kyowa Hakko Kogyo Co Ltd | マイトマイシン誘導体 |
| IL86665A0 (en) * | 1987-06-12 | 1988-11-30 | Bristol Myers Co | Mitomycin analogs |
| IL89203A0 (en) * | 1988-02-11 | 1989-09-10 | Univ Houston | 7-substituted hydrazine mitomycin analogs and pharmaceutical compositions containing them |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3660578A (en) * | 1957-04-06 | 1972-05-02 | Kyowa Hakko Kogyo Kk | Mitomycin c |
| US3121084A (en) * | 1962-09-17 | 1964-02-11 | Du Pont | Selected n, n, n'-trisubstituted amidines and their preparation by reaction of compounds with-nh2 groups with amide acetals |
| NL129868C (en]) * | 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 |
| JPS5439098A (en) * | 1977-08-31 | 1979-03-24 | Kyowa Hakko Kogyo Co Ltd | Mitomycin c derivatives |
| US4268676A (en) * | 1979-12-05 | 1981-05-19 | University Patents, Inc. | Mitomycin analogs |
| 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 |
| JPS6073085A (ja) * | 1983-09-28 | 1985-04-25 | Matsushita Refrig Co | ロ−タリ−コンプレツサ |
| US4642352A (en) * | 1983-12-23 | 1987-02-10 | Bristol-Myers Company | Acylamino mitosanes |
-
1983
- 1983-05-09 US US06/492,903 patent/US4487769A/en not_active Expired - Fee Related
- 1983-05-25 NZ NZ204352A patent/NZ204352A/en unknown
- 1983-05-26 AU AU15014/83A patent/AU571179B2/en not_active Ceased
- 1983-05-27 FR FR8308807A patent/FR2528048B1/fr not_active Expired
- 1983-06-01 NL NL8301949A patent/NL8301949A/nl not_active Application Discontinuation
- 1983-06-01 DE DE19833319992 patent/DE3319992A1/de active Granted
- 1983-06-01 IL IL68852A patent/IL68852A0/xx not_active IP Right Cessation
- 1983-06-01 FI FI831972A patent/FI78700C/fi not_active IP Right Cessation
- 1983-06-02 GB GB08315205A patent/GB2121796B/en not_active Expired
- 1983-06-03 CA CA000429642A patent/CA1230333A/en not_active Expired
- 1983-06-03 IE IE1320/83A patent/IE56107B1/en not_active IP Right Cessation
- 1983-06-03 LU LU84843A patent/LU84843A1/fr unknown
- 1983-06-03 HU HU834817A patent/HU198936B/hu unknown
- 1983-06-03 NO NO832022A patent/NO161676C/no unknown
- 1983-06-03 PT PT76810A patent/PT76810B/pt not_active IP Right Cessation
- 1983-06-03 DD DD83251741A patent/DD210275A5/de not_active IP Right Cessation
- 1983-06-03 GR GR71552A patent/GR78277B/el unknown
- 1983-06-03 OA OA58018A patent/OA07452A/xx unknown
- 1983-06-03 ES ES522948A patent/ES8407493A1/es not_active Expired
- 1983-06-03 DK DK253083A patent/DK161023C/da not_active IP Right Cessation
- 1983-06-03 YU YU1241/83A patent/YU42866B/xx unknown
- 1983-06-03 SE SE8303160A patent/SE455504B/sv not_active IP Right Cessation
- 1983-06-03 IT IT8321461A patent/IT1206452B/it active
- 1983-06-04 KR KR1019830002499A patent/KR870000932B1/ko not_active Expired
- 1983-06-06 AT AT0206483A patent/AT394853B/de not_active IP Right Cessation
- 1983-06-10 CH CH3099/83A patent/CH657856A5/de not_active IP Right Cessation
-
1984
- 1984-02-09 ES ES529585A patent/ES529585A0/es active Granted
- 1984-02-09 ES ES529584A patent/ES529584A0/es active Granted
-
1985
- 1985-08-16 AR AR85301300A patent/AR241438A1/es active
-
1986
- 1986-02-05 YU YU164/86A patent/YU43427B/xx unknown
-
1990
- 1990-11-27 DK DK281490A patent/DK162167C/da not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ELJ | Ceased due to non-payment of the annual fee | ||
| EEIH | Change in the person of patent owner | ||
| UEP | Publication of translation of european patent specification |