CA1108182A - Bis(nitrosoureido)-polyol derivatives and process for their preparation - Google Patents
Bis(nitrosoureido)-polyol derivatives and process for their preparationInfo
- Publication number
- CA1108182A CA1108182A CA307,574A CA307574A CA1108182A CA 1108182 A CA1108182 A CA 1108182A CA 307574 A CA307574 A CA 307574A CA 1108182 A CA1108182 A CA 1108182A
- Authority
- CA
- Canada
- Prior art keywords
- chloroethyl
- dideoxy
- bis
- process according
- nitrosoureido
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 59
- 230000008569 process Effects 0.000 title claims abstract description 45
- 229920005862 polyol Polymers 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- -1 nitrosoureido Chemical group 0.000 title claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 57
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
- 150000003077 polyols Chemical class 0.000 claims abstract description 7
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 125000000018 nitroso group Chemical group N(=O)* 0.000 claims abstract description 3
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 32
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 28
- 239000004386 Erythritol Substances 0.000 claims description 24
- 229940009714 erythritol Drugs 0.000 claims description 24
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 claims description 22
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 18
- 239000000460 chlorine Substances 0.000 claims description 16
- 235000010288 sodium nitrite Nutrition 0.000 claims description 16
- BCMYXYHEMGPZJN-UHFFFAOYSA-N 1-chloro-2-isocyanatoethane Chemical compound ClCCN=C=O BCMYXYHEMGPZJN-UHFFFAOYSA-N 0.000 claims description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 9
- UNXHWFMMPAWVPI-IMJSIDKUSA-N L-threitol Chemical compound OC[C@H](O)[C@@H](O)CO UNXHWFMMPAWVPI-IMJSIDKUSA-N 0.000 claims description 9
- 235000019414 erythritol Nutrition 0.000 claims description 9
- 235000019253 formic acid Nutrition 0.000 claims description 9
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 238000004440 column chromatography Methods 0.000 claims description 4
- CDAISMWEOUEBRE-CDRYSYESSA-N scyllo-inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O CDAISMWEOUEBRE-CDRYSYESSA-N 0.000 claims description 4
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 claims description 4
- HYXRUUHQXNAFAJ-ZXZARUISSA-N (2s,3r)-1,4-diaminobutane-2,3-diol Chemical compound NC[C@H](O)[C@H](O)CN HYXRUUHQXNAFAJ-ZXZARUISSA-N 0.000 claims description 3
- UNXHWFMMPAWVPI-QWWZWVQMSA-N D-threitol Chemical compound OC[C@@H](O)[C@H](O)CO UNXHWFMMPAWVPI-QWWZWVQMSA-N 0.000 claims description 3
- ANLMVXSIPASBFL-XGNJAFTASA-N (1r,3s,4r,6s)-4,6-diaminocyclohexane-1,2,3,5-tetrol Chemical compound N[C@H]1C(O)[C@@H](N)[C@H](O)C(O)[C@@H]1O ANLMVXSIPASBFL-XGNJAFTASA-N 0.000 claims description 2
- XDPGXUIEXVDTAK-KVTDHHQDSA-N (2r,3r,4r,5r)-1,6-diaminohexane-2,3,4,5-tetrol Chemical compound NC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CN XDPGXUIEXVDTAK-KVTDHHQDSA-N 0.000 claims description 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 10
- 239000000126 substance Substances 0.000 claims 10
- 235000013350 formula milk Nutrition 0.000 claims 8
- 229910052801 chlorine Inorganic materials 0.000 claims 6
- JSBOOJIFKJXLAF-OCAPTIKFSA-N 1-(2-chloroethyl)-3-[(2s,3r)-4-(2-chloroethylcarbamoylamino)-2,3-dihydroxybutyl]urea Chemical compound ClCCNC(=O)NC[C@H](O)[C@H](O)CNC(=O)NCCCl JSBOOJIFKJXLAF-OCAPTIKFSA-N 0.000 claims 4
- LLMKXBFBKPFYMX-ZYUZMQFOSA-N 1-(2-chloroethyl)-3-[(2r,3r,4r,5r)-6-(2-chloroethylcarbamoylamino)-2,3,4,5-tetrahydroxyhexyl]urea Chemical compound ClCCNC(=O)NC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CNC(=O)NCCCl LLMKXBFBKPFYMX-ZYUZMQFOSA-N 0.000 claims 2
- DGHOCXJONPLHGT-OCAPTIKFSA-N 1-(2-chloroethyl)-3-[(2s,3r)-4-[[2-chloroethyl(nitroso)carbamoyl]amino]-2,3-dihydroxybutyl]-1-nitrosourea Chemical compound ClCCN(N=O)C(=O)NC[C@H](O)[C@H](O)CNC(=O)N(CCCl)N=O DGHOCXJONPLHGT-OCAPTIKFSA-N 0.000 claims 2
- JSBOOJIFKJXLAF-UHFFFAOYSA-N 1-(2-chloroethyl)-3-[4-(2-chloroethylcarbamoylamino)-2,3-dihydroxybutyl]urea Chemical compound ClCCNC(=O)NCC(O)C(O)CNC(=O)NCCCl JSBOOJIFKJXLAF-UHFFFAOYSA-N 0.000 claims 2
- DGHOCXJONPLHGT-UHFFFAOYSA-N 1-(2-chloroethyl)-3-[4-[[2-chloroethyl(nitroso)carbamoyl]amino]-2,3-dihydroxybutyl]-1-nitrosourea Chemical compound ClCCN(N=O)C(=O)NCC(O)C(O)CNC(=O)N(CCCl)N=O DGHOCXJONPLHGT-UHFFFAOYSA-N 0.000 claims 2
- QELOJZNVHQXTMT-ZYUZMQFOSA-N 3-(2-chloroethyl)-1-[(2r,3r,4r,5r)-6-[2-chloroethylcarbamoyl(nitroso)amino]-2,3,4,5-tetrahydroxyhexyl]-1-nitrosourea Chemical compound ClCCNC(=O)N(N=O)C[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CN(N=O)C(=O)NCCCl QELOJZNVHQXTMT-ZYUZMQFOSA-N 0.000 claims 2
- VJQMZEJRWWLMAQ-OCAPTIKFSA-N 3-(2-chloroethyl)-1-[(2s,3r)-4-[2-chloroethylcarbamoyl(nitroso)amino]-2,3-dihydroxybutyl]-1-nitrosourea Chemical compound ClCCNC(=O)N(N=O)C[C@H](O)[C@H](O)CN(N=O)C(=O)NCCCl VJQMZEJRWWLMAQ-OCAPTIKFSA-N 0.000 claims 2
- VJQMZEJRWWLMAQ-UHFFFAOYSA-N 3-(2-chloroethyl)-1-[4-[2-chloroethylcarbamoyl(nitroso)amino]-2,3-dihydroxybutyl]-1-nitrosourea Chemical compound ClCCNC(=O)N(N=O)CC(O)C(O)CN(N=O)C(=O)NCCCl VJQMZEJRWWLMAQ-UHFFFAOYSA-N 0.000 claims 2
- TZQPAZWGRJYTLN-KVTDHHQDSA-N (2r,3r,4r,5r)-hexane-2,3,4,5-tetrol Chemical compound C[C@@H](O)[C@@H](O)[C@H](O)[C@@H](C)O TZQPAZWGRJYTLN-KVTDHHQDSA-N 0.000 claims 1
- HYXRUUHQXNAFAJ-UHFFFAOYSA-N 1,4-diaminobutane-2,3-diol Chemical compound NCC(O)C(O)CN HYXRUUHQXNAFAJ-UHFFFAOYSA-N 0.000 claims 1
- MQOLEWLIPXPTQK-ZYUZMQFOSA-N 1-(2-chloroethyl)-3-[(2r,3r,4r,5r)-6-[[2-chloroethyl(nitroso)carbamoyl]amino]-2,3,4,5-tetrahydroxyhexyl]-1-nitrosourea Chemical compound ClCCN(N=O)C(=O)NC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CNC(=O)N(CCCl)N=O MQOLEWLIPXPTQK-ZYUZMQFOSA-N 0.000 claims 1
- UYXBAEBEXLEPKR-JGVFFNPUSA-N 1-(2-chloroethyl)-3-[(2s,3r)-4-[2-chloroethylcarbamoyl(nitroso)amino]-2,3-dihydroxybutyl]-1-nitrosourea Chemical compound ClCCN(N=O)C(=O)NC[C@H](O)[C@H](O)CN(N=O)C(=O)NCCCl UYXBAEBEXLEPKR-JGVFFNPUSA-N 0.000 claims 1
- UYXBAEBEXLEPKR-UHFFFAOYSA-N 1-(2-chloroethyl)-3-[4-[2-chloroethylcarbamoyl(nitroso)amino]-2,3-dihydroxybutyl]-1-nitrosourea Chemical compound ClCCN(N=O)C(=O)NCC(O)C(O)CN(N=O)C(=O)NCCCl UYXBAEBEXLEPKR-UHFFFAOYSA-N 0.000 claims 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 claims 1
- 150000002513 isocyanates Chemical class 0.000 claims 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 claims 1
- VFKZTMPDYBFSTM-UHFFFAOYSA-N mitobronitol Chemical compound BrCC(O)C(O)C(O)C(O)CBr VFKZTMPDYBFSTM-UHFFFAOYSA-N 0.000 claims 1
- 230000001085 cytostatic effect Effects 0.000 abstract description 2
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
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- 201000011510 cancer Diseases 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000000824 cytostatic agent Substances 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate 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
- 238000001035 drying Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- FBPFZTCFMRRESA-UHFFFAOYSA-N hexane-1,2,3,4,5,6-hexol Chemical compound OCC(O)C(O)C(O)C(O)CO FBPFZTCFMRRESA-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 229960001855 mannitol Drugs 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- ZFIVKAOQEXOYFY-ZXZARUISSA-N meso-diepoxybutane Chemical compound C1O[C@H]1[C@H]1OC1 ZFIVKAOQEXOYFY-ZXZARUISSA-N 0.000 description 1
- CDAISMWEOUEBRE-GNIYUCBRSA-N muco-inositol Chemical class O[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)[C@H]1O CDAISMWEOUEBRE-GNIYUCBRSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical compound ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 description 1
- 235000019392 nitrosyl chloride Nutrition 0.000 description 1
- 239000007935 oral tablet Substances 0.000 description 1
- 231100000418 oral toxicity Toxicity 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 1
- 229940074439 potassium sodium tartrate Drugs 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- HEBKCHPVOIAQTA-ZXFHETKHSA-N ribitol Chemical compound OC[C@H](O)[C@H](O)[C@H](O)CO HEBKCHPVOIAQTA-ZXFHETKHSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000011006 sodium potassium tartrate Nutrition 0.000 description 1
- QZTRPUHEJOJLDL-UHFFFAOYSA-M sodium;2,2,2-trifluoroacetic acid;nitrite Chemical compound [Na+].[O-]N=O.OC(=O)C(F)(F)F QZTRPUHEJOJLDL-UHFFFAOYSA-M 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 229960002920 sorbitol Drugs 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000563 toxic property Toxicity 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/66—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to halogen atoms or to nitro or nitroso groups
- C07C275/68—N-nitroso ureas
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/28—Radicals substituted by nitrogen atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUGO-1386 | 1977-12-29 | ||
| HU77GO1386A HU176101B (en) | 1977-12-29 | 1977-12-29 | Process for producing bis-bracket-nitrozo-ureido-bracket closed-polyol derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1108182A true CA1108182A (en) | 1981-09-01 |
Family
ID=10996842
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA307,574A Expired CA1108182A (en) | 1977-12-29 | 1978-07-17 | Bis(nitrosoureido)-polyol derivatives and process for their preparation |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US4237273A (en, 2012) |
| JP (1) | JPS5495517A (en, 2012) |
| AT (1) | AT360045B (en, 2012) |
| AU (1) | AU523845B2 (en, 2012) |
| BE (1) | BE868988A (en, 2012) |
| BG (1) | BG30016A3 (en, 2012) |
| CA (1) | CA1108182A (en, 2012) |
| CH (1) | CH639363A5 (en, 2012) |
| CS (1) | CS201010B2 (en, 2012) |
| DD (1) | DD137224A5 (en, 2012) |
| DE (1) | DE2831094A1 (en, 2012) |
| DK (1) | DK155047C (en, 2012) |
| ES (1) | ES471778A1 (en, 2012) |
| FI (1) | FI69058C (en, 2012) |
| FR (1) | FR2415096A1 (en, 2012) |
| GB (1) | GB2011382B (en, 2012) |
| GR (1) | GR64891B (en, 2012) |
| HU (1) | HU176101B (en, 2012) |
| IL (1) | IL55138A (en, 2012) |
| IT (1) | IT1097647B (en, 2012) |
| NL (1) | NL7807587A (en, 2012) |
| NO (1) | NO149960C (en, 2012) |
| PL (1) | PL112198B1 (en, 2012) |
| PT (1) | PT68301A (en, 2012) |
| RO (1) | RO77027A (en, 2012) |
| SE (1) | SE446529B (en, 2012) |
| YU (1) | YU41314B (en, 2012) |
| ZA (1) | ZA783980B (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2459231A1 (fr) | 1979-06-19 | 1981-01-09 | Anvar | Nouveaux derives de la cystamine utiles comme medicaments |
| JPS5775993A (en) * | 1980-10-30 | 1982-05-12 | Tetsuo Suami | Novel nitrosourea derivative and its preparation |
| EP0428849A3 (en) * | 1989-09-28 | 1991-07-31 | Hoechst Aktiengesellschaft | Retroviral protease inhibitors |
| AU8320691A (en) * | 1990-07-06 | 1992-02-04 | Smithkline Beecham Corporation | Inhibitors of retroviral proteases |
| DE10026698A1 (de) | 2000-05-30 | 2001-12-06 | Basf Ag | Selbstemulgierende Wirkstoffformulierung und Verwendung dieser Formulierung |
| US8025899B2 (en) | 2003-08-28 | 2011-09-27 | Abbott Laboratories | Solid pharmaceutical dosage form |
| US8377952B2 (en) | 2003-08-28 | 2013-02-19 | Abbott Laboratories | Solid pharmaceutical dosage formulation |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH518270A (de) * | 1969-03-07 | 1972-01-31 | Hoffmann La Roche | Verfahren zur Herstellung von Nitrosoharnstoffverbindungen |
| JPS5135382B2 (en, 2012) * | 1972-08-04 | 1976-10-01 | ||
| JPS50128266A (en, 2012) * | 1974-03-26 | 1975-10-09 | ||
| JPS5126876A (en) * | 1974-08-08 | 1976-03-05 | Suami T | Shinkina nitorosonyosojudotaino seizohoho |
| US4066750A (en) * | 1976-08-02 | 1978-01-03 | Astra Chemical Products Ab | Lactosyl substituted ureides in ruminant feedstuff |
| JPS5331664A (en) * | 1976-09-02 | 1978-03-25 | Suami T | Production of novel nitroso urea derivatives |
| JPS5395917A (en) * | 1977-02-03 | 1978-08-22 | Tokyo Tanabe Co | Process for preparing nitrosourea derivative of glucopyranose |
| US4148921A (en) * | 1977-07-13 | 1979-04-10 | Suami T | Antitumor agents |
-
1977
- 1977-12-29 HU HU77GO1386A patent/HU176101B/hu unknown
-
1978
- 1978-07-11 AT AT500178A patent/AT360045B/de not_active IP Right Cessation
- 1978-07-12 ZA ZA00783980A patent/ZA783980B/xx unknown
- 1978-07-12 GR GR56762A patent/GR64891B/el unknown
- 1978-07-13 SE SE7807804A patent/SE446529B/xx not_active IP Right Cessation
- 1978-07-13 CS CS784690A patent/CS201010B2/cs unknown
- 1978-07-13 AU AU38027/78A patent/AU523845B2/en not_active Expired
- 1978-07-13 GB GB7829687A patent/GB2011382B/en not_active Expired
- 1978-07-13 FR FR7820939A patent/FR2415096A1/fr active Granted
- 1978-07-13 FI FI782238A patent/FI69058C/fi not_active IP Right Cessation
- 1978-07-13 IL IL55138A patent/IL55138A/xx unknown
- 1978-07-14 DK DK317878A patent/DK155047C/da not_active IP Right Cessation
- 1978-07-14 BG BG040404A patent/BG30016A3/xx unknown
- 1978-07-14 NO NO782447A patent/NO149960C/no unknown
- 1978-07-14 PT PT68301A patent/PT68301A/pt unknown
- 1978-07-14 DE DE19782831094 patent/DE2831094A1/de active Granted
- 1978-07-14 NL NL7807587A patent/NL7807587A/xx not_active Application Discontinuation
- 1978-07-14 CH CH764278A patent/CH639363A5/de not_active IP Right Cessation
- 1978-07-14 IT IT25682/78A patent/IT1097647B/it active
- 1978-07-14 YU YU1699/78A patent/YU41314B/xx unknown
- 1978-07-14 BE BE189274A patent/BE868988A/xx not_active IP Right Cessation
- 1978-07-14 DD DD78206731A patent/DD137224A5/xx not_active IP Right Cessation
- 1978-07-15 JP JP8569978A patent/JPS5495517A/ja active Granted
- 1978-07-15 ES ES471778A patent/ES471778A1/es not_active Expired
- 1978-07-15 RO RO7894680A patent/RO77027A/ro unknown
- 1978-07-15 PL PL1978208436A patent/PL112198B1/pl unknown
- 1978-07-17 US US05/925,822 patent/US4237273A/en not_active Expired - Lifetime
- 1978-07-17 CA CA307,574A patent/CA1108182A/en not_active Expired
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |