CA1036618A - Preparation du tris (2-hydroxyethyle) ammonium-ortho-cresosyacetate - Google Patents
Preparation du tris (2-hydroxyethyle) ammonium-ortho-cresosyacetateInfo
- Publication number
- CA1036618A CA1036618A CA204,161A CA204161A CA1036618A CA 1036618 A CA1036618 A CA 1036618A CA 204161 A CA204161 A CA 204161A CA 1036618 A CA1036618 A CA 1036618A
- Authority
- CA
- Canada
- Prior art keywords
- preparation
- tris
- ammonium
- ortho
- desired product
- 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 17
- 230000008569 process Effects 0.000 title claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 title 1
- 239000007983 Tris buffer Substances 0.000 title 1
- YUXPJMWDDQCARU-UHFFFAOYSA-N 2-[bis(2-hydroxyethyl)amino]ethanol;2-(2-methylphenoxy)acetic acid Chemical compound OCCN(CCO)CCO.CC1=CC=CC=C1OCC(O)=O YUXPJMWDDQCARU-UHFFFAOYSA-N 0.000 claims abstract description 8
- QJVXBRUGKLCUMY-UHFFFAOYSA-N 2-(2-methylphenoxy)acetic acid Chemical compound CC1=CC=CC=C1OCC(O)=O QJVXBRUGKLCUMY-UHFFFAOYSA-N 0.000 claims abstract description 6
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000000126 substance Substances 0.000 claims abstract description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 abstract description 45
- 206010028980 Neoplasm Diseases 0.000 abstract description 32
- 201000011510 cancer Diseases 0.000 abstract description 9
- 238000002347 injection Methods 0.000 abstract description 5
- 239000007924 injection Substances 0.000 abstract description 5
- 239000008063 pharmaceutical solvent Substances 0.000 abstract description 3
- 239000008023 pharmaceutical filler Substances 0.000 abstract description 2
- 241001465754 Metazoa Species 0.000 description 23
- 241000700159 Rattus Species 0.000 description 16
- 238000011282 treatment Methods 0.000 description 15
- 241000699670 Mus sp. Species 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 241000283973 Oryctolagus cuniculus Species 0.000 description 12
- 206010039491 Sarcoma Diseases 0.000 description 11
- 230000002269 spontaneous effect Effects 0.000 description 6
- 201000009030 Carcinoma Diseases 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 208000002908 Brown-Pearce carcinoma Diseases 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 230000012010 growth Effects 0.000 description 4
- 230000002440 hepatic effect Effects 0.000 description 4
- 210000004877 mucosa Anatomy 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 210000001519 tissue Anatomy 0.000 description 4
- 230000004614 tumor growth Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 3
- 230000005856 abnormality Effects 0.000 description 3
- 230000000118 anti-neoplastic effect Effects 0.000 description 3
- 230000002354 daily effect Effects 0.000 description 3
- 230000006698 induction Effects 0.000 description 3
- 208000025036 lymphosarcoma Diseases 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 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
- 201000000274 Carcinosarcoma Diseases 0.000 description 2
- 206010027476 Metastases Diseases 0.000 description 2
- 208000001792 Sarcoma 37 Diseases 0.000 description 2
- 208000005718 Stomach Neoplasms Diseases 0.000 description 2
- 230000002622 anti-tumorigenesis Effects 0.000 description 2
- 210000001772 blood platelet Anatomy 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 210000003743 erythrocyte Anatomy 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- 210000004072 lung Anatomy 0.000 description 2
- 235000012054 meals Nutrition 0.000 description 2
- 230000001613 neoplastic effect Effects 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 210000000664 rectum Anatomy 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 201000000498 stomach carcinoma Diseases 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 206010000117 Abnormal behaviour Diseases 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 102000001554 Hemoglobins Human genes 0.000 description 1
- 108010054147 Hemoglobins Proteins 0.000 description 1
- 208000006268 Sarcoma 180 Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 235000019789 appetite Nutrition 0.000 description 1
- 230000036528 appetite Effects 0.000 description 1
- 238000011888 autopsy Methods 0.000 description 1
- 238000004820 blood count Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 231100000762 chronic effect Toxicity 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 210000002808 connective tissue Anatomy 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 210000004907 gland Anatomy 0.000 description 1
- 230000003862 health status Effects 0.000 description 1
- 238000010562 histological examination Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 230000004807 localization Effects 0.000 description 1
- 210000005075 mammary gland Anatomy 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000037023 motor activity Effects 0.000 description 1
- 239000004081 narcotic agent Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 230000000771 oncological effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000588 tumorigenic Toxicity 0.000 description 1
- 230000000381 tumorigenic effect Effects 0.000 description 1
- 230000005760 tumorsuppression Effects 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 230000009278 visceral effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
- C07C59/70—Ethers of hydroxy-acetic acid, e.g. substitutes on the ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU1946758 | 1973-07-05 | ||
| SU1954859A SU515742A1 (ru) | 1973-08-06 | 1973-08-06 | Способ получени трис (2-оксиэтил) аммоний-0-крезоксиацетата |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1036618A true CA1036618A (fr) | 1978-08-15 |
Family
ID=26665493
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA204,161A Expired CA1036618A (fr) | 1973-07-05 | 1974-07-05 | Preparation du tris (2-hydroxyethyle) ammonium-ortho-cresosyacetate |
Country Status (6)
| Country | Link |
|---|---|
| CA (1) | CA1036618A (fr) |
| CH (1) | CH599918A5 (fr) |
| DE (2) | DE2432393C3 (fr) |
| FR (2) | FR2235681B1 (fr) |
| GB (2) | GB1452340A (fr) |
| SE (1) | SE399250B (fr) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4283419A (en) * | 1978-11-01 | 1981-08-11 | Voronkov Mikhail G | Preparation for raising the fertility of animals |
| RU2098088C1 (ru) * | 1996-04-10 | 1997-12-10 | Валерий Михайлович Дьяков | Способ получения лекарственного средства (трекрезана) с иммунотропным действием |
| RU2623034C1 (ru) * | 2016-07-28 | 2017-06-21 | Федеральное государственное бюджетное учреждение науки Иркутский институт химии им. А.Е. Фаворского Сибирского отделения Российской академии наук | Противоопухолевое средство |
| RU2700941C1 (ru) * | 2019-07-05 | 2019-09-24 | Федеральное государственное бюджетное учреждение "Национальный медицинский исследовательский центр реабилитации и курортологии" Министерства здравоохранения Российской Федерации (ФГБУ "НМИЦ РК" Минздрава России) | Способ предупреждения развития помутнения роговицы при ее механических травмах |
| RU2703302C1 (ru) * | 2019-07-05 | 2019-10-16 | Федеральное государственное бюджетное учреждение "Национальный медицинский исследовательский центр реабилитации и курортологии" Министерства здравоохранения Российской Федерации (ФГБУ "НМИЦ РК" Минздрава России) | Применение раствора оксиэтиламмония метилфеноксиацетата |
| RU2701178C1 (ru) * | 2019-07-10 | 2019-09-25 | Федеральное государственное бюджетное учреждение "Национальный медицинский исследовательский центр реабилитации и курортологии" Министерства здравоохранения Российской Федерации (ФГБУ "НМИЦ РК" Минздрава России) | Способ ускорения заживления роговицы при ее механических травмах |
-
1974
- 1974-06-27 FR FR7422518A patent/FR2235681B1/fr not_active Expired
- 1974-06-27 FR FR7422519A patent/FR2235682B1/fr not_active Expired
- 1974-07-02 GB GB2920674A patent/GB1452340A/en not_active Expired
- 1974-07-02 GB GB2920574A patent/GB1452339A/en not_active Expired
- 1974-07-04 SE SE7408836A patent/SE399250B/xx not_active IP Right Cessation
- 1974-07-04 CH CH915174A patent/CH599918A5/xx not_active IP Right Cessation
- 1974-07-05 DE DE19742432393 patent/DE2432393C3/de not_active Expired
- 1974-07-05 CA CA204,161A patent/CA1036618A/fr not_active Expired
- 1974-07-05 DE DE19742432392 patent/DE2432392C3/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2432392B2 (de) | 1977-09-01 |
| DE2432393C3 (de) | 1979-01-25 |
| SE7408836L (fr) | 1975-01-07 |
| DE2432392C3 (de) | 1978-04-27 |
| FR2235681B1 (fr) | 1977-06-03 |
| DE2432393B2 (de) | 1978-06-01 |
| DE2432393A1 (de) | 1975-01-30 |
| FR2235682B1 (fr) | 1977-06-03 |
| CH599918A5 (fr) | 1978-06-15 |
| SE399250B (sv) | 1978-02-06 |
| FR2235681A1 (fr) | 1975-01-31 |
| GB1452340A (en) | 1976-10-13 |
| GB1452339A (en) | 1976-10-13 |
| DE2432392A1 (de) | 1975-01-30 |
| FR2235682A1 (fr) | 1975-01-31 |
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