CA1197255A - Compounds having antineoplastic activity, process for the preparation thereof and pharmaceutical composition therefrom - Google Patents
Compounds having antineoplastic activity, process for the preparation thereof and pharmaceutical composition therefromInfo
- Publication number
- CA1197255A CA1197255A CA000429066A CA429066A CA1197255A CA 1197255 A CA1197255 A CA 1197255A CA 000429066 A CA000429066 A CA 000429066A CA 429066 A CA429066 A CA 429066A CA 1197255 A CA1197255 A CA 1197255A
- Authority
- CA
- Canada
- Prior art keywords
- selenium
- compounds
- eleostearic acid
- tsel
- antineoplastic activity
- 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 15
- 150000001875 compounds Chemical class 0.000 title abstract description 17
- 230000000118 anti-neoplastic effect Effects 0.000 title abstract description 5
- 239000008194 pharmaceutical composition Substances 0.000 title abstract description 5
- 238000002360 preparation method Methods 0.000 title abstract description 5
- 239000011669 selenium Substances 0.000 claims abstract description 37
- 229910052711 selenium Inorganic materials 0.000 claims abstract description 36
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims abstract description 32
- CUXYLFPMQMFGPL-UHFFFAOYSA-N (9Z,11E,13E)-9,11,13-Octadecatrienoic acid Natural products CCCCC=CC=CC=CCCCCCCCC(O)=O CUXYLFPMQMFGPL-UHFFFAOYSA-N 0.000 claims abstract description 12
- CUXYLFPMQMFGPL-SUTYWZMXSA-N all-trans-octadeca-9,11,13-trienoic acid Chemical compound CCCC\C=C\C=C\C=C\CCCCCCCC(O)=O CUXYLFPMQMFGPL-SUTYWZMXSA-N 0.000 claims abstract description 12
- 239000002383 tung oil Substances 0.000 claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims abstract description 6
- 239000000126 substance Substances 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 5
- 125000003748 selenium group Chemical group *[Se]* 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 2
- 150000003957 organoselenium compounds Chemical class 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 1
- 241001465754 Metazoa Species 0.000 abstract description 15
- 150000002894 organic compounds Chemical class 0.000 abstract description 3
- 238000010792 warming Methods 0.000 abstract description 3
- 230000001613 neoplastic effect Effects 0.000 abstract description 2
- 235000011649 selenium Nutrition 0.000 description 23
- 229940091258 selenium supplement Drugs 0.000 description 23
- 206010028980 Neoplasm Diseases 0.000 description 18
- 241000699670 Mus sp. Species 0.000 description 16
- 241000700159 Rattus Species 0.000 description 11
- 238000010521 absorption reaction Methods 0.000 description 7
- 230000008034 disappearance Effects 0.000 description 6
- 230000001925 catabolic effect Effects 0.000 description 5
- 206010003445 Ascites Diseases 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 210000004907 gland Anatomy 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 201000011510 cancer Diseases 0.000 description 3
- 230000000875 corresponding effect Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- 210000002700 urine Anatomy 0.000 description 3
- BPYKTIZUTYGOLE-IFADSCNNSA-N Bilirubin Chemical compound N1C(=O)C(C)=C(C=C)\C1=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(C(C)=C(\C=C/3C(=C(C=C)C(=O)N\3)C)N2)CCC(O)=O)N1 BPYKTIZUTYGOLE-IFADSCNNSA-N 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- 206010027476 Metastases Diseases 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 206010052428 Wound Diseases 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 230000001195 anabolic effect Effects 0.000 description 2
- 229940034982 antineoplastic agent Drugs 0.000 description 2
- 238000001574 biopsy Methods 0.000 description 2
- 210000001731 descending colon Anatomy 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 230000001965 increasing effect Effects 0.000 description 2
- 238000007918 intramuscular administration Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 230000001926 lymphatic effect Effects 0.000 description 2
- 230000009401 metastasis Effects 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 150000005671 trienes Chemical class 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical compound C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 206010010071 Coma Diseases 0.000 description 1
- 206010010075 Coma hepatic Diseases 0.000 description 1
- 206010014940 Eosinopenia Diseases 0.000 description 1
- 208000007882 Gastritis Diseases 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 description 1
- 208000007542 Paresis Diseases 0.000 description 1
- 240000002834 Paulownia tomentosa Species 0.000 description 1
- 235000010678 Paulownia tomentosa Nutrition 0.000 description 1
- 241000220324 Pyrus Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 206010039509 Scab Diseases 0.000 description 1
- 206010070863 Toxicity to various agents Diseases 0.000 description 1
- 210000000683 abdominal cavity Anatomy 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000011888 autopsy Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000000093 cytochemical effect Effects 0.000 description 1
- 210000000805 cytoplasm Anatomy 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- KTRGHLZBDIJZLQ-UHFFFAOYSA-N elatine Natural products CCN1CC2(CCC(OC)C34C2C(OC)C5(OCOC56CC(OC)C7CC3(O)C6C7OC)C14)OC(=O)c8ccccc8N9C(=O)CC(C)C9=O KTRGHLZBDIJZLQ-UHFFFAOYSA-N 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 201000001059 hepatic coma Diseases 0.000 description 1
- 208000007386 hepatic encephalopathy Diseases 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 201000002364 leukopenia Diseases 0.000 description 1
- 231100001022 leukopenia Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229940070020 other anabolic agent in atc Drugs 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 235000021017 pears Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 238000002271 resection Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 229940001474 sodium thiosulfate Drugs 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000001173 tumoral effect Effects 0.000 description 1
- 238000005353 urine analysis Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C391/00—Compounds containing selenium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D345/00—Heterocyclic compounds containing rings having selenium or tellurium atoms as the only ring hetero atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Electroluminescent Light Sources (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT21552A/82 | 1982-05-28 | ||
| IT8221552A IT8221552A0 (it) | 1982-05-28 | 1982-05-28 | Nuovi composti ad attivita'antineoplastica, procedimetno per la loro preparazione e relative composizioni farmaceutiche. |
| IT20672A/83 | 1983-04-19 | ||
| IT20672/83A IT1164188B (it) | 1983-04-19 | 1983-04-19 | Nuovi composti ad attivita' antineoplastica,procedimento per la loro preparazione e relative composizioni farmaceutiche |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1197255A true CA1197255A (en) | 1985-11-26 |
Family
ID=26327610
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000429066A Expired CA1197255A (en) | 1982-05-28 | 1983-05-27 | Compounds having antineoplastic activity, process for the preparation thereof and pharmaceutical composition therefrom |
Country Status (18)
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1161213B (it) * | 1983-03-08 | 1987-03-18 | Fcn Srl | Composizioni farmaceutiche ad attivita' antineoplastica |
| US4824955A (en) * | 1985-11-15 | 1989-04-25 | Nippon Kayaku Kabushiki Kaisha | Selenium oxy chloride-pyridine or bipyridine complexes |
| CH676667A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1988-03-07 | 1991-02-28 | Onco Pharm Dev Ag | |
| WO1990003175A1 (en) * | 1988-09-27 | 1990-04-05 | Avram, Elena | Selenium compositions for treatment of disease |
| DE4320694C2 (de) * | 1993-06-22 | 1999-11-11 | Biosyn Arzneimittel Gmbh | Vewendung von Selenverbindungen zur äußeren Anwendung bei Warzen |
| RU2177321C1 (ru) * | 2001-01-22 | 2001-12-27 | Новицкий Юрий Алексеевич | Селеновое каротинопротеиновое органическое вещество для регулирования метаболических процессов (его варианты) |
| RU2176916C1 (ru) * | 2001-01-22 | 2001-12-20 | Новицкий Юрий Алексеевич | Селеновое гликопротеиновое элементорганическое вещество, обладающее иммуностимулирующим действием (его варианты) |
| US6632837B1 (en) * | 2002-10-21 | 2003-10-14 | Elena Avram | Compositions containing a selenium monobromide-oil reaction product and epichlorohydrin and methods of making the same |
| US20050197399A1 (en) * | 2003-05-13 | 2005-09-08 | Marwan Fakih | Method of augmenting the antitumor activity of anticancer agents |
| US20060258697A1 (en) * | 2003-05-13 | 2006-11-16 | Rustum Youcef M | Method of augmenting the antitumor activity of anticancer agents |
| US20050026852A1 (en) * | 2003-05-13 | 2005-02-03 | Rustum Youcef M. | Method of augmenting the antitumor activity of anticancer agents |
| US7534818B1 (en) | 2003-09-15 | 2009-05-19 | Health Research, Inc. | Method of reducing alopecia and bladder toxicity of cyclophosphamide |
| CN1329519C (zh) * | 2006-03-29 | 2007-08-01 | 王景恒 | 富含有机硒的γ－亚麻酸干菌粉及其生产工艺 |
| KR101588441B1 (ko) * | 2015-07-22 | 2016-02-03 | 정재락 | 유기 셀레늄의 제조방법 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2152642A (en) * | 1939-04-04 | Treatment of teng oil |
-
1983
- 1983-05-19 EP EP83104923A patent/EP0095663B1/en not_active Expired
- 1983-05-19 US US06/496,111 patent/US4564634A/en not_active Expired - Fee Related
- 1983-05-19 DE DE8383104923T patent/DE3361690D1/de not_active Expired
- 1983-05-24 FI FI831857A patent/FI78070C/fi not_active IP Right Cessation
- 1983-05-26 PT PT76767A patent/PT76767B/pt not_active IP Right Cessation
- 1983-05-26 NO NO831870A patent/NO157505C/no unknown
- 1983-05-26 AR AR293150A patent/AR230421A1/es active
- 1983-05-26 GR GR71471A patent/GR77469B/el unknown
- 1983-05-26 AU AU14999/83A patent/AU552556B2/en not_active Ceased
- 1983-05-26 PH PH28972A patent/PH24229A/en unknown
- 1983-05-27 DK DK241183A patent/DK241183A/da not_active Application Discontinuation
- 1983-05-27 ES ES522757A patent/ES8407321A1/es not_active Expired
- 1983-05-27 KR KR1019830002383A patent/KR910002534B1/ko not_active Expired
- 1983-05-27 CA CA000429066A patent/CA1197255A/en not_active Expired
- 1983-05-27 IE IE1260/83A patent/IE54929B1/en not_active IP Right Cessation
- 1983-05-27 NZ NZ204394A patent/NZ204394A/en unknown
- 1983-05-27 IN IN672/CAL/83A patent/IN157041B/en unknown
- 1983-05-27 YU YU1186/83A patent/YU44975B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0095663A1 (en) | 1983-12-07 |
| NO157505B (no) | 1987-12-21 |
| IE54929B1 (en) | 1990-03-28 |
| KR910002534B1 (ko) | 1991-04-23 |
| PT76767A (en) | 1983-06-01 |
| ES522757A0 (es) | 1984-09-16 |
| IN157041B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1986-01-04 |
| EP0095663B1 (en) | 1986-01-02 |
| NO157505C (no) | 1988-03-30 |
| NZ204394A (en) | 1985-08-16 |
| US4564634A (en) | 1986-01-14 |
| DK241183A (da) | 1983-11-29 |
| YU44975B (en) | 1991-06-30 |
| PT76767B (en) | 1986-03-27 |
| FI831857A0 (fi) | 1983-05-24 |
| DE3361690D1 (en) | 1986-02-13 |
| AR230421A1 (es) | 1984-04-30 |
| ES8407321A1 (es) | 1984-09-16 |
| FI78070C (fi) | 1989-06-12 |
| KR840004760A (ko) | 1984-10-24 |
| AU1499983A (en) | 1983-12-01 |
| FI78070B (fi) | 1989-02-28 |
| GR77469B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-09-24 |
| YU118683A (en) | 1986-04-30 |
| PH24229A (en) | 1990-05-04 |
| AU552556B2 (en) | 1986-06-05 |
| NO831870L (no) | 1983-11-29 |
| FI831857L (fi) | 1983-11-29 |
| DK241183D0 (da) | 1983-05-27 |
| IE831260L (en) | 1983-11-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEC | Expiry (correction) | ||
| MKEX | Expiry |