JPS6317823B2 - - Google Patents
Info
- Publication number
- JPS6317823B2 JPS6317823B2 JP52060932A JP6093277A JPS6317823B2 JP S6317823 B2 JPS6317823 B2 JP S6317823B2 JP 52060932 A JP52060932 A JP 52060932A JP 6093277 A JP6093277 A JP 6093277A JP S6317823 B2 JPS6317823 B2 JP S6317823B2
- Authority
- JP
- Japan
- Prior art keywords
- azide
- haloalkyl
- chloroethyl
- reacted
- nitrosocarbamoyl
- 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
- 150000001875 compounds Chemical class 0.000 claims description 22
- 150000001540 azides Chemical class 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 12
- -1 haloalkyl isocyanate Chemical class 0.000 claims description 11
- WFPZPJSADLPSON-UHFFFAOYSA-N dinitrogen tetraoxide Chemical compound [O-][N+](=O)[N+]([O-])=O WFPZPJSADLPSON-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 8
- 238000007034 nitrosation reaction Methods 0.000 claims description 6
- 239000012948 isocyanate Substances 0.000 claims description 5
- 230000009935 nitrosation Effects 0.000 claims description 5
- NVKGVBZZSJFQLM-UHFFFAOYSA-N 1-(2-chloroethyl)-1-nitrosourea Chemical compound NC(=O)N(N=O)CCCl NVKGVBZZSJFQLM-UHFFFAOYSA-N 0.000 claims description 4
- YJZJEQBSODVMTH-UHFFFAOYSA-N 1-(2-chloroethyl)-3-(2-hydroxyethyl)-1-nitrosourea Chemical compound OCCNC(=O)N(N=O)CCCl YJZJEQBSODVMTH-UHFFFAOYSA-N 0.000 claims description 3
- TWPVZHSICVXGGP-UHFFFAOYSA-N 1-diazo-3-nitrosourea Chemical compound [N-]=[N+]=NC(=O)NN=O TWPVZHSICVXGGP-UHFFFAOYSA-N 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical class [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000001414 amino alcohols Chemical class 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- BESOTRXDCHQLBP-UHFFFAOYSA-N 2-[[2-chloroethyl(nitroso)carbamoyl]amino]acetamide Chemical compound NC(=O)CNC(=O)N(N=O)CCCl BESOTRXDCHQLBP-UHFFFAOYSA-N 0.000 claims description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- 150000003862 amino acid derivatives Chemical class 0.000 claims 3
- 239000003513 alkali Substances 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000000243 solution Substances 0.000 description 14
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 13
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 13
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 13
- DLGOEMSEDOSKAD-UHFFFAOYSA-N Carmustine Chemical compound ClCCNC(=O)N(N=O)CCCl DLGOEMSEDOSKAD-UHFFFAOYSA-N 0.000 description 9
- 229940045719 antineoplastic alkylating agent nitrosoureas Drugs 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- VQVHVJMFEBRIPO-UHFFFAOYSA-N 1-(2-chloroethyl)-3-diazo-1-nitrosourea Chemical compound ClCCN(N=O)C(=O)N=[N+]=[N-] VQVHVJMFEBRIPO-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000004809 thin layer chromatography Methods 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- SZRUDGOANPYZEE-UHFFFAOYSA-N 1-(2-chloroethyl)-3-(3-hydroxypropyl)-1-nitrosourea Chemical compound OCCCNC(=O)N(N=O)CCCl SZRUDGOANPYZEE-UHFFFAOYSA-N 0.000 description 4
- GWFHTEWTXYUKGE-UHFFFAOYSA-N 1-(2-chloroethyl)-3-diazourea Chemical compound ClCCNC(=O)N=[N+]=[N-] GWFHTEWTXYUKGE-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 4
- 206010028980 Neoplasm Diseases 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 239000002246 antineoplastic agent Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 201000011510 cancer Diseases 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 230000000973 chemotherapeutic effect Effects 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- OSTGTTZJOCZWJG-UHFFFAOYSA-N nitrosourea Chemical compound NC(=O)N=NO OSTGTTZJOCZWJG-UHFFFAOYSA-N 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- KFVXPKCLAGCJRX-UHFFFAOYSA-N 1-(2-chloroethyl)-3-nitrosourea Chemical compound ClCCNC(=O)NN=O KFVXPKCLAGCJRX-UHFFFAOYSA-N 0.000 description 2
- HDJGFKVGANUCBP-UHFFFAOYSA-N 3-diazo-1-(2-fluoroethyl)-1-nitrosourea Chemical compound FCCN(N=O)C(=O)N=[N+]=[N-] HDJGFKVGANUCBP-UHFFFAOYSA-N 0.000 description 2
- ARSRBNBHOADGJU-UHFFFAOYSA-N 7,12-dimethyltetraphene Chemical compound C1=CC2=CC=CC=C2C2=C1C(C)=C(C=CC=C1)C1=C2C ARSRBNBHOADGJU-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 206010006187 Breast cancer Diseases 0.000 description 2
- 208000026310 Breast neoplasm Diseases 0.000 description 2
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 2
- VFZRZRDOXPRTSC-UHFFFAOYSA-N DMBA Natural products COC1=CC(OC)=CC(C=O)=C1 VFZRZRDOXPRTSC-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 206010039491 Sarcoma Diseases 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229940009456 adriamycin Drugs 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N anhydrous n-heptane Natural products CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 235000015115 caffè latte Nutrition 0.000 description 2
- BLNJZMQZYXWQGM-UHFFFAOYSA-N carbamoyl azide Chemical class NC(=O)N=[N+]=[N-] BLNJZMQZYXWQGM-UHFFFAOYSA-N 0.000 description 2
- 230000002252 carbamoylating effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229940125898 compound 5 Drugs 0.000 description 2
- 229940127089 cytotoxic agent Drugs 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- VXNJKAJSDRUFMZ-UHFFFAOYSA-N 1-(2-fluoroethyl)-3-(2-hydroxyethyl)-1-nitrosourea Chemical compound OCCNC(=O)N(N=O)CCF VXNJKAJSDRUFMZ-UHFFFAOYSA-N 0.000 description 1
- BCMYXYHEMGPZJN-UHFFFAOYSA-N 1-chloro-2-isocyanatoethane Chemical compound ClCCN=C=O BCMYXYHEMGPZJN-UHFFFAOYSA-N 0.000 description 1
- WKNMKGVLOWGGOU-UHFFFAOYSA-N 2-aminoacetamide;hydron;chloride Chemical compound Cl.NCC(N)=O WKNMKGVLOWGGOU-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical group CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 150000004008 N-nitroso compounds Chemical class 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000005115 alkyl carbamoyl group Chemical group 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 238000007098 aminolysis reaction Methods 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000021235 carbamoylation Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- JRZBPELLUMBLQU-UHFFFAOYSA-N carbonazidic acid Chemical compound OC(=O)N=[N+]=[N-] JRZBPELLUMBLQU-UHFFFAOYSA-N 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 229940047583 cetamide Drugs 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000039 congener Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000000824 cytostatic agent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 210000003722 extracellular fluid Anatomy 0.000 description 1
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000010575 fractional recrystallization Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 229940090009 myleran Drugs 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/17—Amides, e.g. hydroxamic acids having the group >N—C(O)—N< or >N—C(S)—N<, e.g. urea, thiourea, carmustine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2623420A DE2623420C2 (de) | 1976-05-25 | 1976-05-25 | Verfahren zur Herstellung unsymmetrisch 13-disubstituierter Nitrosoharnstoffe |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS535118A JPS535118A (en) | 1978-01-18 |
| JPS6317823B2 true JPS6317823B2 (US07652168-20100126-C00075.png) | 1988-04-15 |
Family
ID=5978961
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6093277A Granted JPS535118A (en) | 1976-05-25 | 1977-05-24 | Process for adjusting asymmetrically 1*33diisubstituted nitrosourea |
| JP61171484A Granted JPS6226263A (ja) | 1976-05-25 | 1986-07-21 | Ｎ−ハロゲンアルキル−ｎ−ニトロソカルバモイルアジドの製造法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61171484A Granted JPS6226263A (ja) | 1976-05-25 | 1986-07-21 | Ｎ−ハロゲンアルキル−ｎ−ニトロソカルバモイルアジドの製造法 |
Country Status (27)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0323616U (US07652168-20100126-C00075.png) * | 1989-07-19 | 1991-03-12 |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2623420C2 (de) * | 1976-05-25 | 1978-07-06 | Stiftung Deutsches Krebsforschungszentrum, 6900 Heidelberg | Verfahren zur Herstellung unsymmetrisch 13-disubstituierter Nitrosoharnstoffe |
| DE2845574A1 (de) | 1978-10-19 | 1980-04-24 | Deutsches Krebsforsch | Durch heterocyclische ringe oder alkylreste substituierte analoga von ccnu und verfahren zu deren herstellung |
| JPS57116043A (en) * | 1981-01-12 | 1982-07-19 | Tetsuo Suami | New nitrosourea derivative and its preparation |
| US20040072889A1 (en) * | 1997-04-21 | 2004-04-15 | Pharmacia Corporation | Method of using a COX-2 inhibitor and an alkylating-type antineoplastic agent as a combination therapy in the treatment of neoplasia |
| AU1374601A (en) * | 1999-11-12 | 2001-05-30 | Angiotech International Ag | Compositions and methods for treating disease utilizing a combination of radioactive therapy and cell-cycle inhibitors |
| KR100441764B1 (ko) * | 2000-12-30 | 2004-07-27 | 한국과학기술연구원 | 비닐카바모일아지드 유도체 |
| EP1385779B2 (en) † | 2001-02-21 | 2020-06-24 | Ben Z. Cohen | Accurate dosing pump and accessories therefor |
| US20030216758A1 (en) * | 2001-12-28 | 2003-11-20 | Angiotech Pharmaceuticals, Inc. | Coated surgical patches |
| EP2181704B1 (en) | 2002-12-30 | 2015-05-06 | Angiotech International Ag | Drug delivery from rapid gelling polymer composition |
| RU2695787C1 (ru) * | 2018-11-07 | 2019-07-26 | Федеральное государственное бюджетное учреждение "Национальный медицинский исследовательский центр онкологии имени Н.Н. Петрова" Министерства здравоохранения Российской Федерации | Применение соединения 2-[3-(2-хлорэтил)-3-нитрозоуреидо]-1,3-пропандиол для лечения her2-положительных опухолей в эксперименте |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2623420C2 (de) * | 1976-05-25 | 1978-07-06 | Stiftung Deutsches Krebsforschungszentrum, 6900 Heidelberg | Verfahren zur Herstellung unsymmetrisch 13-disubstituierter Nitrosoharnstoffe |
| DE2659862C3 (de) * | 1976-05-25 | 1979-09-20 | Stiftung Deutsches Krebsforschungszentrum, 6900 Heidelberg | N-(2-Chloräthyl)-N-nitrosocarbamoylazid und Verfahren zu dessen Herstellung |
-
1976
- 1976-05-25 DE DE2623420A patent/DE2623420C2/de not_active Expired
-
1977
- 1977-05-18 YU YU1243/77A patent/YU40901B/xx unknown
- 1977-05-20 FR FR7715503A patent/FR2361357A1/fr active Granted
- 1977-05-22 IL IL52142A patent/IL52142A/xx unknown
- 1977-05-23 GB GB1398/80A patent/GB1585822A/en not_active Expired
- 1977-05-23 HU HU77DE987A patent/HU176768B/hu not_active IP Right Cessation
- 1977-05-23 DD DD7700199064A patent/DD130035A5/xx unknown
- 1977-05-23 GB GB21715/77A patent/GB1585821A/en not_active Expired
- 1977-05-23 LU LU77389A patent/LU77389A1/xx unknown
- 1977-05-24 CA CA279,049A patent/CA1092143A/en not_active Expired
- 1977-05-24 NO NO771804A patent/NO151410C/no unknown
- 1977-05-24 JP JP6093277A patent/JPS535118A/ja active Granted
- 1977-05-24 SE SE7706074A patent/SE434152B/xx not_active IP Right Cessation
- 1977-05-24 CH CH623377A patent/CH639947A5/de not_active IP Right Cessation
- 1977-05-24 DK DK227277A patent/DK165786C/da active
- 1977-05-25 AU AU25495/77A patent/AU525278B2/en not_active Expired
- 1977-05-25 IE IE1082/77A patent/IE45286B1/en not_active IP Right Cessation
- 1977-05-25 US US05/800,452 patent/US4150146A/en not_active Expired - Lifetime
- 1977-05-25 AT AT373177A patent/AT360551B/de not_active IP Right Cessation
- 1977-05-25 BE BE177911A patent/BE855043A/xx not_active IP Right Cessation
- 1977-05-25 ES ES459137A patent/ES459137A1/es not_active Expired
- 1977-05-25 ZA ZA00786785A patent/ZA786785B/xx unknown
- 1977-05-25 FI FI771665A patent/FI771665A/fi not_active Application Discontinuation
- 1977-05-25 IT IT24002/77A patent/IT1085808B/it active
- 1977-05-25 MC MC771246A patent/MC1142A1/xx unknown
- 1977-05-25 SU SU772484357A patent/SU963464A3/ru active
- 1977-05-25 ZA ZA00773144A patent/ZA773144B/xx unknown
- 1977-05-25 NL NLAANVRAGE7705769,A patent/NL187066C/xx not_active IP Right Cessation
- 1977-05-25 HU HU77DE935A patent/HU173579B/hu not_active IP Right Cessation
-
1978
- 1978-02-27 FR FR7805483A patent/FR2372800A1/fr active Granted
-
1979
- 1979-03-21 US US06/022,714 patent/US4228086A/en not_active Expired - Lifetime
- 1979-08-27 SU SU792806959A patent/SU973019A3/ru active
-
1980
- 1980-05-30 NO NO801626A patent/NO151744C/no unknown
-
1981
- 1981-11-04 YU YU2619/81A patent/YU41264B/xx unknown
-
1982
- 1982-03-17 SE SE8201694A patent/SE453081B/sv not_active IP Right Cessation
- 1982-06-30 HK HK287/82A patent/HK28782A/xx unknown
- 1982-06-30 HK HK288/82A patent/HK28882A/xx unknown
-
1986
- 1986-07-21 JP JP61171484A patent/JPS6226263A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0323616U (US07652168-20100126-C00075.png) * | 1989-07-19 | 1991-03-12 |
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