SU668597A3 - Способ получени производных простановой кислоты - Google Patents
Способ получени производных простановой кислотыInfo
- Publication number
- SU668597A3 SU668597A3 SU731978756A SU1978756A SU668597A3 SU 668597 A3 SU668597 A3 SU 668597A3 SU 731978756 A SU731978756 A SU 731978756A SU 1978756 A SU1978756 A SU 1978756A SU 668597 A3 SU668597 A3 SU 668597A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acid
- mixture
- methoxy
- oxo
- hydroxy
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims 28
- 238000000034 method Methods 0.000 title claims 4
- 239000000203 mixture Substances 0.000 claims 35
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 22
- 150000004702 methyl esters Chemical class 0.000 claims 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 18
- 239000000047 product Substances 0.000 claims 15
- 150000001875 compounds Chemical class 0.000 claims 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 12
- -1 alkyl radical Chemical class 0.000 claims 12
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical class OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 7
- 239000010410 layer Substances 0.000 claims 7
- 229910052760 oxygen Inorganic materials 0.000 claims 7
- 239000001301 oxygen Substances 0.000 claims 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 6
- 125000000468 ketone group Chemical group 0.000 claims 5
- 239000000243 solution Substances 0.000 claims 5
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 4
- 239000007864 aqueous solution Substances 0.000 claims 4
- 125000004494 ethyl ester group Chemical group 0.000 claims 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Chemical class OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 238000002329 infrared spectrum Methods 0.000 claims 4
- WGJJROVFWIXTPA-OALUTQOASA-N prostanoic acid Chemical class CCCCCCCC[C@H]1CCC[C@@H]1CCCCCCC(O)=O WGJJROVFWIXTPA-OALUTQOASA-N 0.000 claims 4
- 239000000741 silica gel Substances 0.000 claims 4
- 229910002027 silica gel Inorganic materials 0.000 claims 4
- 239000008096 xylene Substances 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- RCDZLZBSLHFWAJ-PKOBYXMFSA-N CCCCCC(C=C[C@@H]1[C@@H](CC=CCCCC(O)=O)C(OC)=CC1)=O Chemical compound CCCCCC(C=C[C@@H]1[C@@H](CC=CCCCC(O)=O)C(OC)=CC1)=O RCDZLZBSLHFWAJ-PKOBYXMFSA-N 0.000 claims 3
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 238000004587 chromatography analysis Methods 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims 3
- 235000019341 magnesium sulphate Nutrition 0.000 claims 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 claims 3
- 235000006408 oxalic acid Nutrition 0.000 claims 3
- 238000002360 preparation method Methods 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- 229910052709 silver Inorganic materials 0.000 claims 3
- 239000004332 silver Substances 0.000 claims 3
- 235000011121 sodium hydroxide Nutrition 0.000 claims 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical class COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 2
- VPQUYTWCUVLHLA-KRWDZBQOSA-N 7-[(5R)-2-methoxy-5-(3-oxooct-1-enyl)cyclopenten-1-yl]hept-5-enoic acid Chemical compound COC1=C(CC=CCCCC(=O)O)[C@H](CC1)C=CC(CCCCC)=O VPQUYTWCUVLHLA-KRWDZBQOSA-N 0.000 claims 2
- OYFGVONASXRUSR-ZENAZSQFSA-N 7-[(5R)-5-(3-hydroxyoct-1-enyl)-2-methoxycyclopenten-1-yl]hept-5-enoic acid Chemical compound OC(C=C[C@H]1CCC(=C1CC=CCCCC(=O)O)OC)CCCCC OYFGVONASXRUSR-ZENAZSQFSA-N 0.000 claims 2
- FDFWUSLHOJFYNR-LJJQOFDWSA-N OC(C=C[C@H]1CC=C([C@@H]1CC=CCCCC(=O)O)OC)CCCCC Chemical compound OC(C=C[C@H]1CC=C([C@@H]1CC=CCCCC(=O)O)OC)CCCCC FDFWUSLHOJFYNR-LJJQOFDWSA-N 0.000 claims 2
- 150000007513 acids Chemical class 0.000 claims 2
- 239000003513 alkali Substances 0.000 claims 2
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 claims 2
- MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 claims 2
- 238000009835 boiling Methods 0.000 claims 2
- 238000001816 cooling Methods 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- XEHVFKKSDRMODV-UHFFFAOYSA-N ethynyl Chemical compound C#[C] XEHVFKKSDRMODV-UHFFFAOYSA-N 0.000 claims 2
- 238000001704 evaporation Methods 0.000 claims 2
- 230000008020 evaporation Effects 0.000 claims 2
- 235000019253 formic acid Nutrition 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 150000002576 ketones Chemical class 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 150000002901 organomagnesium compounds Chemical class 0.000 claims 2
- 230000020477 pH reduction Effects 0.000 claims 2
- 230000000144 pharmacologic effect Effects 0.000 claims 2
- 150000003254 radicals Chemical class 0.000 claims 2
- 238000000926 separation method Methods 0.000 claims 2
- 239000011780 sodium chloride Substances 0.000 claims 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 2
- 229920002554 vinyl polymer Polymers 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- GNLJBJNONOOOQC-UHFFFAOYSA-N $l^{3}-carbane;magnesium Chemical compound [Mg]C GNLJBJNONOOOQC-UHFFFAOYSA-N 0.000 claims 1
- FGOJCPKOOGIRPA-UHFFFAOYSA-N 1-o-tert-butyl 4-o-ethyl 5-oxoazepane-1,4-dicarboxylate Chemical compound CCOC(=O)C1CCN(C(=O)OC(C)(C)C)CCC1=O FGOJCPKOOGIRPA-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims 1
- YXUOAGJJLPONFT-JLMWTWJWSA-N C(#C)C(C=C[C@H]1CCC([C@@H]1CC=CCCCC)=O)(CCCCC)O Chemical compound C(#C)C(C=C[C@H]1CCC([C@@H]1CC=CCCCC)=O)(CCCCC)O YXUOAGJJLPONFT-JLMWTWJWSA-N 0.000 claims 1
- NOTFZGFABLVTIG-UHFFFAOYSA-N Cyclohexylethyl acetate Chemical compound CC(=O)OCCC1CCCCC1 NOTFZGFABLVTIG-UHFFFAOYSA-N 0.000 claims 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 claims 1
- 235000011054 acetic acid Nutrition 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 150000004791 alkyl magnesium halides Chemical class 0.000 claims 1
- 239000012736 aqueous medium Substances 0.000 claims 1
- 235000010357 aspartame Nutrition 0.000 claims 1
- 230000021523 carboxylation Effects 0.000 claims 1
- 238000006473 carboxylation reaction Methods 0.000 claims 1
- 239000000470 constituent Substances 0.000 claims 1
- 150000001940 cyclopentanes Chemical class 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 238000006114 decarboxylation reaction Methods 0.000 claims 1
- 150000001993 dienes Chemical class 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 claims 1
- 238000002474 experimental method Methods 0.000 claims 1
- 239000000706 filtrate Substances 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 229910052500 inorganic mineral Chemical class 0.000 claims 1
- RMGJCSHZTFKPNO-UHFFFAOYSA-M magnesium;ethene;bromide Chemical compound [Mg+2].[Br-].[CH-]=C RMGJCSHZTFKPNO-UHFFFAOYSA-M 0.000 claims 1
- LROBJRRFCPYLIT-UHFFFAOYSA-M magnesium;ethyne;bromide Chemical compound [Mg+2].[Br-].[C-]#C LROBJRRFCPYLIT-UHFFFAOYSA-M 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 239000011707 mineral Chemical class 0.000 claims 1
- 235000010755 mineral Nutrition 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 239000012044 organic layer Substances 0.000 claims 1
- 125000002734 organomagnesium group Chemical group 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 238000007127 saponification reaction Methods 0.000 claims 1
- 239000000377 silicon dioxide Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 150000003509 tertiary alcohols Chemical class 0.000 claims 1
- 238000002211 ultraviolet spectrum Methods 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7246324A FR2211223B1 (hr) | 1972-12-27 | 1972-12-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU668597A3 true SU668597A3 (ru) | 1979-06-15 |
Family
ID=9109325
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU731978756A SU668597A3 (ru) | 1972-12-27 | 1973-12-24 | Способ получени производных простановой кислоты |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS5724343B2 (hr) |
| BE (1) | BE808969A (hr) |
| CA (1) | CA1018972A (hr) |
| CH (2) | CH590226A5 (hr) |
| DD (1) | DD108268A5 (hr) |
| DE (1) | DE2364706C2 (hr) |
| ES (1) | ES421790A1 (hr) |
| FR (1) | FR2211223B1 (hr) |
| GB (1) | GB1438130A (hr) |
| IE (1) | IE38875B1 (hr) |
| IL (1) | IL43832A (hr) |
| NL (1) | NL7317745A (hr) |
| SU (1) | SU668597A3 (hr) |
| ZA (1) | ZA739650B (hr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4091015A (en) * | 1972-10-27 | 1978-05-23 | American Home Products Corporation | 15-Substituted prostanoic acids |
| US3922302A (en) * | 1973-07-26 | 1975-11-25 | American Home Prod | 15-Ethynyl-11-deoxy PGE |
| US4022821A (en) * | 1974-04-18 | 1977-05-10 | American Home Products Corporation | 15-Substituted prostanoic acid |
| US4065494A (en) * | 1975-04-17 | 1977-12-27 | American Home Products Corporation | 15-Substituted prostanoic acids |
-
1972
- 1972-12-27 FR FR7246324A patent/FR2211223B1/fr not_active Expired
-
1973
- 1973-12-17 IL IL43832A patent/IL43832A/en unknown
- 1973-12-21 ZA ZA00739650A patent/ZA739650B/xx unknown
- 1973-12-21 BE BE139155A patent/BE808969A/xx not_active IP Right Cessation
- 1973-12-21 DD DD175629A patent/DD108268A5/xx unknown
- 1973-12-24 CA CA188,897A patent/CA1018972A/fr not_active Expired
- 1973-12-24 SU SU731978756A patent/SU668597A3/ru active
- 1973-12-26 JP JP14414673A patent/JPS5724343B2/ja not_active Expired
- 1973-12-26 ES ES421790A patent/ES421790A1/es not_active Expired
- 1973-12-27 CH CH1435676A patent/CH590226A5/xx not_active IP Right Cessation
- 1973-12-27 GB GB5981973A patent/GB1438130A/en not_active Expired
- 1973-12-27 DE DE2364706A patent/DE2364706C2/de not_active Expired
- 1973-12-27 CH CH1816573A patent/CH590225A5/xx not_active IP Right Cessation
- 1973-12-27 NL NL7317745A patent/NL7317745A/xx not_active Application Discontinuation
- 1973-12-28 IE IE02339/73A patent/IE38875B1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA1018972A (fr) | 1977-10-11 |
| CH590226A5 (hr) | 1977-07-29 |
| IL43832A0 (en) | 1974-03-14 |
| NL7317745A (hr) | 1974-07-01 |
| DE2364706A1 (de) | 1974-07-04 |
| FR2211223A1 (hr) | 1974-07-19 |
| IE38875L (en) | 1974-06-27 |
| FR2211223B1 (hr) | 1976-04-23 |
| AU6396873A (en) | 1975-07-03 |
| DE2364706C2 (de) | 1982-07-08 |
| GB1438130A (hr) | 1976-06-03 |
| JPS5724343B2 (hr) | 1982-05-24 |
| JPS5046649A (hr) | 1975-04-25 |
| ZA739650B (en) | 1975-02-26 |
| IE38875B1 (en) | 1978-06-21 |
| ES421790A1 (es) | 1976-04-01 |
| BE808969A (fr) | 1974-06-21 |
| IL43832A (en) | 1977-03-31 |
| CH590225A5 (hr) | 1977-07-29 |
| DD108268A5 (hr) | 1974-09-12 |
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