LU85199A1 - Analogues de mitomycine - Google Patents
Analogues de mitomycine Download PDFInfo
- Publication number
- LU85199A1 LU85199A1 LU85199A LU85199A LU85199A1 LU 85199 A1 LU85199 A1 LU 85199A1 LU 85199 A LU85199 A LU 85199A LU 85199 A LU85199 A LU 85199A LU 85199 A1 LU85199 A1 LU 85199A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- methyl
- carbamate
- dione
- azirino
- hexahydro
- Prior art date
Links
- 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 3
- -1 3-hydroxy- l-pyrrolidinyl Chemical group 0.000 claims description 124
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 89
- 150000001875 compounds Chemical class 0.000 claims description 73
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 54
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- 238000000034 method Methods 0.000 claims description 40
- QMRIWYCCTCNABA-UHFFFAOYSA-N indole-4,7-quinone Chemical compound O=C1C=CC(=O)C2=C1C=CN2 QMRIWYCCTCNABA-UHFFFAOYSA-N 0.000 claims description 17
- 241001465754 Metazoa Species 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 9
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 230000001613 neoplastic effect Effects 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 238000011282 treatment Methods 0.000 claims description 6
- 230000037396 body weight Effects 0.000 claims description 5
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 4
- 125000005936 piperidyl group Chemical group 0.000 claims description 4
- 239000002671 adjuvant Substances 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 9
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 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 33
- 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 33
- 238000004458 analytical method Methods 0.000 description 32
- 238000002844 melting Methods 0.000 description 32
- 230000008018 melting Effects 0.000 description 32
- 238000000354 decomposition reaction Methods 0.000 description 30
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
- 150000003254 radicals Chemical class 0.000 description 18
- 239000007787 solid Substances 0.000 description 12
- 229910000027 potassium carbonate Inorganic materials 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 229930192392 Mitomycin Natural products 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
- 230000003115 biocidal effect Effects 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000000118 anti-neoplastic effect Effects 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000003178 carboxy group Chemical class [H]OC(*)=O 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- DZGWFCGJZKJUFP-UHFFFAOYSA-N tyramine Chemical compound NCCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-N 0.000 description 2
- PRZSMDYEVUSNJM-SLFFLAALSA-N (1r,4as,10ar)-1-(hydroxymethyl)-1,4a-dimethyl-7-propan-2-yl-3,4,10,10a-tetrahydro-2h-phenanthren-9-one Chemical compound OC[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3C(=O)C[C@H]21 PRZSMDYEVUSNJM-SLFFLAALSA-N 0.000 description 1
- ZRTGHKVPFXNDHE-UHFFFAOYSA-N (3-methyl-1,2-thiazol-5-yl)azanium;chloride Chemical compound [Cl-].CC=1C=C([NH3+])SN=1 ZRTGHKVPFXNDHE-UHFFFAOYSA-N 0.000 description 1
- GPRYKVSEZCQIHD-UHFFFAOYSA-N 1-(4-aminophenyl)ethanone Chemical compound CC(=O)C1=CC=C(N)C=C1 GPRYKVSEZCQIHD-UHFFFAOYSA-N 0.000 description 1
- GIAFURWZWWWBQT-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanol Chemical compound NCCOCCO GIAFURWZWWWBQT-UHFFFAOYSA-N 0.000 description 1
- WGPFDZRLUUOFTI-UHFFFAOYSA-N 2-(2-nitroimidazol-1-yl)ethanamine Chemical compound NCCN1C=CN=C1[N+]([O-])=O WGPFDZRLUUOFTI-UHFFFAOYSA-N 0.000 description 1
- UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical compound C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 description 1
- NSYKYZBOQLCIHR-UHFFFAOYSA-N 2-nitro-1,3-benzothiazole Chemical compound C1=CC=C2SC([N+](=O)[O-])=NC2=C1 NSYKYZBOQLCIHR-UHFFFAOYSA-N 0.000 description 1
- XPQIPUZPSLAZDV-UHFFFAOYSA-N 2-pyridylethylamine Chemical compound NCCC1=CC=CC=N1 XPQIPUZPSLAZDV-UHFFFAOYSA-N 0.000 description 1
- LGDHZCLREKIGKJ-UHFFFAOYSA-N 3,4-dimethoxyaniline Chemical compound COC1=CC=C(N)C=C1OC LGDHZCLREKIGKJ-UHFFFAOYSA-N 0.000 description 1
- WNRGWPVJGDABME-UHFFFAOYSA-N 3,5-Dimethoxyaniline Chemical compound COC1=CC(N)=CC(OC)=C1 WNRGWPVJGDABME-UHFFFAOYSA-N 0.000 description 1
- NJXPYZHXZZCTNI-UHFFFAOYSA-N 3-aminobenzonitrile Chemical compound NC1=CC=CC(C#N)=C1 NJXPYZHXZZCTNI-UHFFFAOYSA-N 0.000 description 1
- YBAZINRZQSAIAY-UHFFFAOYSA-N 4-aminobenzonitrile Chemical compound NC1=CC=C(C#N)C=C1 YBAZINRZQSAIAY-UHFFFAOYSA-N 0.000 description 1
- OEQQFQXMCPMEIH-UHFFFAOYSA-N 4-chloro-1,3-benzothiazol-2-amine Chemical compound C1=CC=C2SC(N)=NC2=C1Cl OEQQFQXMCPMEIH-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 1
- 101100005765 Arabidopsis thaliana CDF1 gene Proteins 0.000 description 1
- 101100007579 Arabidopsis thaliana CPP1 gene Proteins 0.000 description 1
- 206010003445 Ascites Diseases 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 208000028018 Lymphocytic leukaemia Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- PQGAHNJECSVDEI-UHFFFAOYSA-N [CH2]CCCCC Chemical compound [CH2]CCCCC PQGAHNJECSVDEI-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000005189 alkyl hydroxy group Chemical group 0.000 description 1
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 1
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229940034982 antineoplastic agent Drugs 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 125000005518 carboxamido group Chemical class 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 125000004966 cyanoalkyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000004990 dihydroxyalkyl group Chemical group 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- PKWIYNIDEDLDCJ-UHFFFAOYSA-N guanazole Chemical compound NC1=NNC(N)=N1 PKWIYNIDEDLDCJ-UHFFFAOYSA-N 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229960004931 histamine dihydrochloride Drugs 0.000 description 1
- PPZMYIBUHIPZOS-UHFFFAOYSA-N histamine dihydrochloride Chemical compound Cl.Cl.NCCC1=CN=CN1 PPZMYIBUHIPZOS-UHFFFAOYSA-N 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- 230000015654 memory Effects 0.000 description 1
- 229940057952 methanol Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 229960004857 mitomycin Drugs 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- ODHSPTHLPCXPTL-UHFFFAOYSA-N n'-(5-nitropyridin-2-yl)ethane-1,2-diamine Chemical compound NCCNC1=CC=C([N+]([O-])=O)C=N1 ODHSPTHLPCXPTL-UHFFFAOYSA-N 0.000 description 1
- PEMGGJDINLGTON-UHFFFAOYSA-N n-(3-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(N)=C1 PEMGGJDINLGTON-UHFFFAOYSA-N 0.000 description 1
- CHMBIJAOCISYEW-UHFFFAOYSA-N n-(4-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(N)C=C1 CHMBIJAOCISYEW-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 231100000926 not very toxic Toxicity 0.000 description 1
- 125000003431 oxalo group Chemical group 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 description 1
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 229960003732 tyramine Drugs 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
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US46461283A | 1983-02-07 | 1983-02-07 | |
| US46461283 | 1983-02-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LU85199A1 true LU85199A1 (fr) | 1984-05-30 |
Family
ID=23844605
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU85199A LU85199A1 (fr) | 1983-02-07 | 1984-02-07 | Analogues de mitomycine |
Country Status (29)
| Country | Link |
|---|---|
| JP (1) | JPS59152384A (en)) |
| KR (1) | KR900006854B1 (en)) |
| AT (1) | AT385509B (en)) |
| AU (1) | AU571193B2 (en)) |
| BE (1) | BE898856A (en)) |
| CA (1) | CA1252789A (en)) |
| CH (1) | CH658658A5 (en)) |
| DD (1) | DD233844A5 (en)) |
| DE (1) | DE3403922A1 (en)) |
| DK (1) | DK161890C (en)) |
| ES (1) | ES8607305A1 (en)) |
| FI (1) | FI80698C (en)) |
| FR (1) | FR2540500B1 (en)) |
| GB (1) | GB2134514B (en)) |
| GR (1) | GR81455B (en)) |
| HU (1) | HU190236B (en)) |
| IE (1) | IE56814B1 (en)) |
| IL (1) | IL70897A (en)) |
| IT (1) | IT1178855B (en)) |
| LU (1) | LU85199A1 (en)) |
| NL (1) | NL8400338A (en)) |
| NO (1) | NO161374C (en)) |
| NZ (1) | NZ206932A (en)) |
| OA (1) | OA07654A (en)) |
| PH (1) | PH20249A (en)) |
| PT (1) | PT78067B (en)) |
| SE (1) | SE461982B (en)) |
| YU (1) | YU44984B (en)) |
| ZA (1) | ZA84788B (en)) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4487769A (en) * | 1982-06-04 | 1984-12-11 | Bristol-Myers Company | Amidines |
| CA1282069C (en) * | 1985-09-12 | 1991-03-26 | Damon L. Meyer | Antibody complexes of hapten-modified diagnostic or therapeutic agents |
| JPS63150282A (ja) * | 1986-12-13 | 1988-06-22 | Kyowa Hakko Kogyo Co Ltd | マイトマイシン誘導体 |
| JPS63246379A (ja) * | 1987-03-31 | 1988-10-13 | Kyowa Hakko Kogyo Co Ltd | ７−ｎ，８−ｎ−エチレンマイトマイシン８−イミン類 |
| DE69127345D1 (de) * | 1990-11-13 | 1997-09-25 | Kyowa Hakko Kogyo Kk | Mitomycinderivate |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| JPS5686184A (en) * | 1979-12-17 | 1981-07-13 | Kyowa Hakko Kogyo Co Ltd | Novel mitomycin c derivative |
| 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 |
| US4642352A (en) * | 1983-12-23 | 1987-02-10 | Bristol-Myers Company | Acylamino mitosanes |
-
1984
- 1984-01-25 NZ NZ206932A patent/NZ206932A/en unknown
- 1984-01-27 GB GB08402233A patent/GB2134514B/en not_active Expired
- 1984-02-02 ZA ZA84788A patent/ZA84788B/xx unknown
- 1984-02-03 AU AU24073/84A patent/AU571193B2/en not_active Ceased
- 1984-02-03 NL NL8400338A patent/NL8400338A/nl not_active Application Discontinuation
- 1984-02-04 DE DE19843403922 patent/DE3403922A1/de not_active Withdrawn
- 1984-02-06 AT AT0037684A patent/AT385509B/de not_active IP Right Cessation
- 1984-02-06 CH CH550/84A patent/CH658658A5/de not_active IP Right Cessation
- 1984-02-06 PH PH30204A patent/PH20249A/en unknown
- 1984-02-06 GR GR73720A patent/GR81455B/el unknown
- 1984-02-06 HU HU84483A patent/HU190236B/hu not_active IP Right Cessation
- 1984-02-06 DK DK052484A patent/DK161890C/da active
- 1984-02-06 DD DD84259885A patent/DD233844A5/de not_active IP Right Cessation
- 1984-02-06 ES ES529478A patent/ES8607305A1/es not_active Expired
- 1984-02-06 PT PT78067A patent/PT78067B/pt not_active IP Right Cessation
- 1984-02-06 CA CA000446811A patent/CA1252789A/en not_active Expired
- 1984-02-06 IE IE272/84A patent/IE56814B1/en not_active IP Right Cessation
- 1984-02-06 NO NO840433A patent/NO161374C/no unknown
- 1984-02-07 JP JP59021505A patent/JPS59152384A/ja active Pending
- 1984-02-07 IL IL70897A patent/IL70897A/xx unknown
- 1984-02-07 KR KR1019840000574A patent/KR900006854B1/ko not_active Expired
- 1984-02-07 SE SE8400628A patent/SE461982B/sv not_active IP Right Cessation
- 1984-02-07 IT IT67113/84A patent/IT1178855B/it active
- 1984-02-07 YU YU217/84A patent/YU44984B/xx unknown
- 1984-02-07 BE BE0/212351A patent/BE898856A/fr not_active IP Right Cessation
- 1984-02-07 LU LU85199A patent/LU85199A1/fr unknown
- 1984-02-07 FR FR8401845A patent/FR2540500B1/fr not_active Expired
- 1984-02-07 FI FI840502A patent/FI80698C/fi not_active IP Right Cessation
- 1984-02-07 OA OA58227A patent/OA07654A/xx unknown
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