PT78399B - Process for preparing amino disulfides - Google Patents
Process for preparing amino disulfides Download PDFInfo
- Publication number
- PT78399B PT78399B PT78399A PT7839984A PT78399B PT 78399 B PT78399 B PT 78399B PT 78399 A PT78399 A PT 78399A PT 7839984 A PT7839984 A PT 7839984A PT 78399 B PT78399 B PT 78399B
- Authority
- PT
- Portugal
- Prior art keywords
- carbon atoms
- substituted
- group
- preparation
- starting compounds
- Prior art date
Links
- WHALSQRTWNBBCV-UHFFFAOYSA-N s-aminosulfanylthiohydroxylamine Chemical class NSSN WHALSQRTWNBBCV-UHFFFAOYSA-N 0.000 title description 4
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 43
- 125000001424 substituent group Chemical group 0.000 claims abstract 11
- 238000000034 method Methods 0.000 claims description 36
- -1 hydroxy, amino Chemical group 0.000 claims description 32
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 238000002360 preparation method Methods 0.000 claims description 20
- 239000007858 starting material Substances 0.000 claims description 19
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 29
- 125000000217 alkyl group Chemical group 0.000 claims 12
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 11
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 239000011593 sulfur Substances 0.000 claims 7
- 125000001589 carboacyl group Chemical group 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 5
- 239000001301 oxygen Substances 0.000 claims 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 125000002947 alkylene group Chemical group 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 125000000753 cycloalkyl group Chemical class 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000001624 naphthyl group Chemical group 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 2
- 239000005977 Ethylene Substances 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- 125000005236 alkanoylamino group Chemical group 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000006501 nitrophenyl group Chemical group 0.000 claims 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- NDOVLWQBFFJETK-UHFFFAOYSA-N 1,4-thiazinane 1,1-dioxide Chemical compound O=S1(=O)CCNCC1 NDOVLWQBFFJETK-UHFFFAOYSA-N 0.000 claims 1
- YHIIJNLSGULWAA-UHFFFAOYSA-N 1,4-thiazinane 1-oxide Chemical compound O=S1CCNCC1 YHIIJNLSGULWAA-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims 1
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims 1
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000005059 halophenyl group Chemical group 0.000 claims 1
- 229960005016 naphazoline Drugs 0.000 claims 1
- 125000000962 organic group Chemical group 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 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 abstract description 24
- 206010028980 Neoplasm Diseases 0.000 abstract description 7
- 125000002228 disulfide group Chemical group 0.000 abstract 2
- 238000010171 animal model Methods 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- 229960004857 mitomycin Drugs 0.000 description 12
- 241000699670 Mus sp. Species 0.000 description 9
- 230000004083 survival effect Effects 0.000 description 8
- 150000003573 thiols Chemical class 0.000 description 8
- 241000699666 Mus <mouse, genus> Species 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000012265 solid product Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 208000032839 leukemia Diseases 0.000 description 4
- 201000001441 melanoma Diseases 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 241001529936 Murinae Species 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 210000000265 leukocyte Anatomy 0.000 description 3
- 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 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- AXFZADXWLMXITO-UHFFFAOYSA-N N-acetylcysteamine Chemical compound CC(=O)NCCS AXFZADXWLMXITO-UHFFFAOYSA-N 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- 239000012430 organic reaction media Substances 0.000 description 2
- 239000013641 positive control Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- MXTPRJXPLFGHEE-UHFFFAOYSA-N 1-amino-2-sulfosulfanylethane Chemical compound NCCSS(O)(=O)=O MXTPRJXPLFGHEE-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- RNEYKYHGNZITRA-UHFFFAOYSA-N 2-(benzyldisulfanyl)ethanamine Chemical compound NCCSSCC1=CC=CC=C1 RNEYKYHGNZITRA-UHFFFAOYSA-N 0.000 description 1
- RLOQUHLKVVCCCM-UHFFFAOYSA-N 2-(butyldisulfanyl)ethanamine Chemical compound CCCCSSCCN RLOQUHLKVVCCCM-UHFFFAOYSA-N 0.000 description 1
- RTMAIGIMPXARBE-UHFFFAOYSA-N 2-(decyldisulfanyl)ethanamine Chemical compound CCCCCCCCCCSSCCN RTMAIGIMPXARBE-UHFFFAOYSA-N 0.000 description 1
- BQVVGRSJXINYEE-UHFFFAOYSA-N 2-(hexyldisulfanyl)ethanamine Chemical compound CCCCCCSSCCN BQVVGRSJXINYEE-UHFFFAOYSA-N 0.000 description 1
- FRKYZCJUJLRHAO-UHFFFAOYSA-N 2-(octyldisulfanyl)ethanamine Chemical compound CCCCCCCCSSCCN FRKYZCJUJLRHAO-UHFFFAOYSA-N 0.000 description 1
- WTGGJAWHQCMISE-UHFFFAOYSA-N 2-(phenyldisulfanyl)ethanamine Chemical compound NCCSSC1=CC=CC=C1 WTGGJAWHQCMISE-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 206010003445 Ascites Diseases 0.000 description 1
- 241000972773 Aulopiformes Species 0.000 description 1
- 206010065553 Bone marrow failure Diseases 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- 208000030453 Drug-Related Side Effects and Adverse reaction Diseases 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 229930192392 Mitomycin Natural products 0.000 description 1
- 206010072927 Mucolipidosis type I Diseases 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 206010070863 Toxicity to various agents Diseases 0.000 description 1
- 102100029469 WD repeat and HMG-box DNA-binding protein 1 Human genes 0.000 description 1
- 101710097421 WD repeat and HMG-box DNA-binding protein 1 Proteins 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000012156 elution solvent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 210000004698 lymphocyte Anatomy 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003039 myelosuppressive effect Effects 0.000 description 1
- 210000000440 neutrophil Anatomy 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 235000019515 salmon Nutrition 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- QSUJAUYJBJRLKV-UHFFFAOYSA-M tetraethylazanium;fluoride Chemical compound [F-].CC[N+](CC)(CC)CC QSUJAUYJBJRLKV-UHFFFAOYSA-M 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 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
- C07D487/12—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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US48401683A | 1983-04-11 | 1983-04-11 | |
| US06/581,291 US4803212A (en) | 1983-04-11 | 1984-02-24 | Amino disulfides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PT78399A PT78399A (en) | 1984-05-01 |
| PT78399B true PT78399B (en) | 1986-07-17 |
Family
ID=27047825
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT78399A PT78399B (en) | 1983-04-11 | 1984-04-10 | Process for preparing amino disulfides |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4803212A (OSRAM) |
| KR (1) | KR890001488B1 (OSRAM) |
| AT (1) | AT387019B (OSRAM) |
| AU (1) | AU577523B2 (OSRAM) |
| CA (1) | CA1285567C (OSRAM) |
| CH (1) | CH661273A5 (OSRAM) |
| CY (1) | CY1533A (OSRAM) |
| DE (1) | DE3413489A1 (OSRAM) |
| DK (1) | DK170071B1 (OSRAM) |
| ES (1) | ES531338A0 (OSRAM) |
| FI (1) | FI78701C (OSRAM) |
| FR (1) | FR2543953B1 (OSRAM) |
| GB (1) | GB2140799B (OSRAM) |
| GR (1) | GR79579B (OSRAM) |
| HK (1) | HK82690A (OSRAM) |
| IE (1) | IE57348B1 (OSRAM) |
| IT (1) | IT1176003B (OSRAM) |
| LU (1) | LU85295A1 (OSRAM) |
| MX (1) | MX9202850A (OSRAM) |
| MY (1) | MY102071A (OSRAM) |
| NL (1) | NL8401104A (OSRAM) |
| PT (1) | PT78399B (OSRAM) |
| SE (1) | SE461735B (OSRAM) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4487769A (en) * | 1982-06-04 | 1984-12-11 | Bristol-Myers Company | Amidines |
| US4866180A (en) * | 1984-02-24 | 1989-09-12 | Bristol-Myers Company | Amino disulfide thiol exchange products |
| JPS60255789A (ja) * | 1984-06-01 | 1985-12-17 | Kyowa Hakko Kogyo Co Ltd | マイトマイシン誘導体，その製造法および抗腫瘍剤 |
| US4888341A (en) * | 1984-09-04 | 1989-12-19 | University Patents, Inc. | 6-substituted mitomycin analogs |
| 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 |
| EP0197799B1 (en) * | 1985-04-10 | 1990-09-12 | Kyowa Hakko Kogyo Kabushiki Kaisha | Pharmacologically active mitomycin derivatives |
| 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 |
| ZA886812B (en) * | 1987-11-23 | 1989-07-26 | Bristol Myers Co | Anti-tumor prodrugs |
| US5075454A (en) * | 1990-03-08 | 1991-12-24 | Bristol-Myers Squibb Company | 7-(diphenylmethyl)oxy-9a-methoxymitosane |
| US5175303A (en) * | 1990-03-08 | 1992-12-29 | Bristol-Myers Squibb Company | Preparation of 7-(diphenylmethyl)oxy-9A-methoxymitosane |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3660578A (en) * | 1957-04-06 | 1972-05-02 | Kyowa Hakko Kogyo Kk | Mitomycin c |
| NL129868C (OSRAM) * | 1963-06-07 | |||
| DE1570029A1 (de) * | 1964-07-09 | 1970-04-09 | Kyowa Hakko Kogyo Kk | Verfahren zur Herstellung von Mitosanverbindungen |
| NL130086C (OSRAM) * | 1964-07-14 | 1970-06-15 | ||
| 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 |
| GB2093643A (en) * | 1981-02-17 | 1982-09-02 | Standard Telephones Cables Ltd | DC-to-DC converter |
| 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 |
| DE3376114D1 (en) * | 1982-12-07 | 1988-05-05 | Kyowa Hakko Kogyo Kk | Mitomycin analogues |
| US4642352A (en) * | 1983-12-23 | 1987-02-10 | Bristol-Myers Company | Acylamino mitosanes |
| AU581673B2 (en) * | 1984-09-04 | 1989-03-02 | Bristol-Myers Company | Substituted 7-oxomitosanes |
-
1984
- 1984-02-24 US US06/581,291 patent/US4803212A/en not_active Expired - Fee Related
- 1984-03-21 AU AU25951/84A patent/AU577523B2/en not_active Ceased
- 1984-04-04 GR GR74313A patent/GR79579B/el unknown
- 1984-04-06 NL NL8401104A patent/NL8401104A/nl not_active Application Discontinuation
- 1984-04-06 FR FR8405504A patent/FR2543953B1/fr not_active Expired
- 1984-04-06 FI FI841380A patent/FI78701C/fi not_active IP Right Cessation
- 1984-04-06 ES ES531338A patent/ES531338A0/es active Granted
- 1984-04-09 DK DK183984A patent/DK170071B1/da not_active IP Right Cessation
- 1984-04-09 CA CA000451556A patent/CA1285567C/en not_active Expired - Fee Related
- 1984-04-10 DE DE19843413489 patent/DE3413489A1/de active Granted
- 1984-04-10 IE IE878/84A patent/IE57348B1/en not_active IP Right Cessation
- 1984-04-10 IT IT20478/84A patent/IT1176003B/it active
- 1984-04-10 CH CH1806/84A patent/CH661273A5/de not_active IP Right Cessation
- 1984-04-10 LU LU85295A patent/LU85295A1/fr unknown
- 1984-04-10 SE SE8401999A patent/SE461735B/sv not_active IP Right Cessation
- 1984-04-10 PT PT78399A patent/PT78399B/pt not_active IP Right Cessation
- 1984-04-10 GB GB08409242A patent/GB2140799B/en not_active Expired
- 1984-04-11 KR KR1019840001908A patent/KR890001488B1/ko not_active Expired
- 1984-04-11 AT AT0122384A patent/AT387019B/de not_active IP Right Cessation
-
1987
- 1987-09-29 MY MYPI87002183A patent/MY102071A/en unknown
-
1990
- 1990-10-11 HK HK826/90A patent/HK82690A/xx not_active IP Right Cessation
- 1990-11-16 CY CY1533A patent/CY1533A/en unknown
-
1992
- 1992-06-12 MX MX9202850A patent/MX9202850A/es unknown
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