SU581860A3 - Способ получени ацильных производных диангидрогекситов - Google Patents
Способ получени ацильных производных диангидрогекситовInfo
- Publication number
- SU581860A3 SU581860A3 SU7502302301A SU2302301A SU581860A3 SU 581860 A3 SU581860 A3 SU 581860A3 SU 7502302301 A SU7502302301 A SU 7502302301A SU 2302301 A SU2302301 A SU 2302301A SU 581860 A3 SU581860 A3 SU 581860A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- benzene
- absolute
- added
- methanol
- mixture
- Prior art date
Links
- 125000002252 acyl group Chemical group 0.000 title description 10
- 238000000034 method Methods 0.000 title description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 67
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 239000000047 product Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 230000010933 acylation Effects 0.000 description 4
- 238000005917 acylation reaction Methods 0.000 description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- -1 furanoyl Chemical group 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- QZBZLPMIDXVHPN-UHFFFAOYSA-N 2-(1-nitrocyclohexa-2,4-dien-1-yl)acetic acid Chemical compound [N+](=O)([O-])C1(CC=CC=C1)CC(=O)O QZBZLPMIDXVHPN-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 241001137251 Corvidae Species 0.000 description 1
- 235000019738 Limestone Nutrition 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000016571 aggressive behavior Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000003217 anti-cancerogenic effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 229960004217 benzyl alcohol Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- QUBQYFYWUJJAAK-UHFFFAOYSA-N oxymethurea Chemical group OCNC(=O)NCO QUBQYFYWUJJAAK-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 235000015108 pies Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- NRTLTGGGUQIRRT-UHFFFAOYSA-N triethylazanium;bromide Chemical compound [Br-].CC[NH+](CC)CC NRTLTGGGUQIRRT-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/16—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by esterified hydroxyl radicals
-
- 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
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/14—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by free hydroxyl radicals
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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU74MA00002630A HU172826B (hu) | 1974-12-24 | 1974-12-24 | Sposob poluchenija novykh acilnykh proizvodnykh 1,2-5,6-diangidro-geksitov s protivoopukholevoj aktivnost'ju |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU581860A3 true SU581860A3 (ru) | 1977-11-25 |
Family
ID=10998754
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU7502302301A SU581860A3 (ru) | 1974-12-24 | 1975-12-24 | Способ получени ацильных производных диангидрогекситов |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS51125201A (enExample) |
| AT (1) | AT345303B (enExample) |
| BE (1) | BE837054A (enExample) |
| CH (1) | CH620208A5 (enExample) |
| CS (1) | CS220403B1 (enExample) |
| DD (1) | DD124803A1 (enExample) |
| DE (1) | DE2557033C2 (enExample) |
| DK (1) | DK156271C (enExample) |
| FI (1) | FI61187C (enExample) |
| FR (1) | FR2295743A1 (enExample) |
| GB (1) | GB1490649A (enExample) |
| HU (1) | HU172826B (enExample) |
| NL (1) | NL7514991A (enExample) |
| NO (1) | NO144632C (enExample) |
| PL (1) | PL101458B1 (enExample) |
| SU (1) | SU581860A3 (enExample) |
| YU (1) | YU40449B (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU182227B (en) * | 1980-11-04 | 1983-12-28 | Chinoin Gyogyszer Es Vegyeszet | Process for preparing hexitols containing free carboxyl group |
| HU195754B (en) * | 1984-01-18 | 1988-07-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing 1,2-5,6-dianhydro-3,4-diacyl-dulcitol |
| JPH0228032A (ja) * | 1988-07-14 | 1990-01-30 | Suzuki Motor Co Ltd | 自動車 |
| EP2605650A4 (en) * | 2010-08-18 | 2014-05-21 | Del Mar Pharmaceuticals | COMPOSITIONS AND METHODS FOR INCREASING THE THERAPEUTIC UTILITY OF SUBOPTIMALLY ADMINISTERED CHEMICAL COMPOUNDS INCLUDING SUBSTITUTED HEXITOLS SUCH AS DIANHYDROGALACTITOL AND DIACETYL DIANHYDROGALACTITOL |
| US9901563B2 (en) | 2013-03-11 | 2018-02-27 | Delmar Pharmaceuticals, Inc. | Compositions to improve the therapeutic benefit of suboptimally administered chemical compounds including substituted hexitols such as dianhydrogalactitol and diacetyldianhydrogalactitol |
-
1974
- 1974-12-24 HU HU74MA00002630A patent/HU172826B/hu not_active IP Right Cessation
-
1975
- 1975-12-18 DE DE2557033A patent/DE2557033C2/de not_active Expired
- 1975-12-19 AT AT966175A patent/AT345303B/de not_active IP Right Cessation
- 1975-12-22 FR FR7539338A patent/FR2295743A1/fr active Granted
- 1975-12-23 NL NL7514991A patent/NL7514991A/xx not_active Application Discontinuation
- 1975-12-23 GB GB52713/75A patent/GB1490649A/en not_active Expired
- 1975-12-23 NO NO754374A patent/NO144632C/no unknown
- 1975-12-23 FI FI753643A patent/FI61187C/fi not_active IP Right Cessation
- 1975-12-23 CH CH1673675A patent/CH620208A5/de not_active IP Right Cessation
- 1975-12-23 DK DK589775A patent/DK156271C/da not_active IP Right Cessation
- 1975-12-23 DD DD190504A patent/DD124803A1/xx not_active IP Right Cessation
- 1975-12-23 YU YU3269/75A patent/YU40449B/xx unknown
- 1975-12-23 PL PL1975185921A patent/PL101458B1/pl unknown
- 1975-12-23 CS CS758837A patent/CS220403B1/cs unknown
- 1975-12-24 SU SU7502302301A patent/SU581860A3/ru active
- 1975-12-24 JP JP50154665A patent/JPS51125201A/ja active Granted
- 1975-12-24 BE BE163090A patent/BE837054A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NO144632B (no) | 1981-06-29 |
| FI61187C (fi) | 1982-06-10 |
| JPS6129952B2 (enExample) | 1986-07-10 |
| FI753643A7 (enExample) | 1976-06-25 |
| NO754374L (enExample) | 1976-06-25 |
| AT345303B (de) | 1978-09-11 |
| FR2295743A1 (fr) | 1976-07-23 |
| NL7514991A (nl) | 1976-06-28 |
| DK156271C (da) | 1989-12-11 |
| CH620208A5 (en) | 1980-11-14 |
| FI61187B (fi) | 1982-02-26 |
| NO144632C (no) | 1981-10-07 |
| DK156271B (da) | 1989-07-24 |
| BE837054A (fr) | 1976-04-16 |
| ATA966175A (de) | 1978-01-15 |
| JPS51125201A (en) | 1976-11-01 |
| CS220403B1 (en) | 1983-04-29 |
| DK589775A (da) | 1976-06-25 |
| PL101458B1 (pl) | 1978-12-30 |
| DD124803A1 (enExample) | 1977-03-16 |
| YU326975A (en) | 1982-02-28 |
| FR2295743B1 (enExample) | 1978-11-10 |
| DE2557033C2 (de) | 1983-12-22 |
| GB1490649A (en) | 1977-11-02 |
| YU40449B (en) | 1986-02-28 |
| DE2557033A1 (de) | 1976-07-22 |
| HU172826B (hu) | 1978-12-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS5834474B2 (ja) | チアゾリジン誘導体の製造法 | |
| US2734904A (en) | Xcxnhxc-nh | |
| PL213967B1 (pl) | Sposób wytwarzania kombrestatyn oraz zwiazek posredni | |
| SU581860A3 (ru) | Способ получени ацильных производных диангидрогекситов | |
| JPS5922711B2 (ja) | ベンゾオキサゾリノン誘導体の製造法 | |
| US2772280A (en) | Synthesis of 4-amino-3-isoxazolidone and its derivatives | |
| JP2579383B2 (ja) | マロン酸モノｔ‐ブチルエステルの製造法 | |
| US5608086A (en) | Process for the preparation of intermediates for the synthesis of glucose-6-phosphatase inhibitors, and novel intermediates | |
| JPH05238990A (ja) | １，４，５，８−テトラキス（ヒドロキシメチル）ナフタレン誘導体およびその製造方法 | |
| SU511004A3 (ru) | Способ получени производных 2-оксиметил-1,3,4-оксадиазола | |
| NO146862B (no) | Jodbenzenderivater for anvendelse som roentgenkontrastmidler | |
| US5354891A (en) | Method of producing aromatic amine derivatives | |
| US4057544A (en) | α-Alkylsulfobenzyl penicillins | |
| US4304918A (en) | Process for preparing benzoxazolyl propionic acid derivatives | |
| JPS6324994B2 (enExample) | ||
| RU2084441C1 (ru) | Способ получения кислотно-аддитивных солей труднорастворимых карбоновых кислот и аминов или аминокислот | |
| KR950006149B1 (ko) | 신규 n-(2-할로알카노일옥시)석신이미드 유도체 및 그 제조방법 | |
| JP2671401B2 (ja) | α‐アミノチオアセトアミド誘導体およびその製造法 | |
| JP2809481B2 (ja) | ２―アルコキシカルボニル―３―ピリジンカルボン酸誘導体、その製造法及び除草剤 | |
| JPH01238548A (ja) | ナフタレン―１，４，５，８―テトラカルボン酸テトラアルキルエステルの製造方法 | |
| JPH01168664A (ja) | シクロヘキセノン誘導体およびその製造法 | |
| JPS63280084A (ja) | １−アルキル−３−カルボキシ−４−シンノロン類の製造方法 | |
| JP2500316B2 (ja) | １，４，５，８―テトラキス（ハロゲノメチル）ナフタレン誘導体、およびその製造方法 | |
| JPS603382B2 (ja) | イソインドリン誘導体の新規な製造法 | |
| JP3200203B2 (ja) | キノリンカルボン酸誘導体およびその製法 |