SU1145925A3 - Способ получени производных простаноиновой кислоты - Google Patents

Способ получени производных простаноиновой кислоты Download PDF

Info

Publication number: SU1145925A3
Authority: SU; USSR - Soviet Union
Prior art keywords: acid; mixture; compound; mol; hydroxy
Prior art date: 1980-08-12

Application number

SU813320103A

Other languages

English (en)

Russian (ru)

Inventor

Жеро Стефан

Клеофакс Жанин

Баррьер Жан-Клод

Сиер Андре

Original Assignee

Санофи (Фирма)

Priority date (The priority date 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 date listed.)

1980-08-12

Filing date

1981-08-12

Publication date

1985-03-15

1981-08-12 Application filed by Санофи (Фирма) filed Critical Санофи (Фирма)

1985-03-15 Application granted granted Critical

1985-03-15 Publication of SU1145925A3 publication Critical patent/SU1145925A3/ru

Links

238000000034 method Methods 0.000 title claims abstract description 14
239000002253 acid Substances 0.000 title claims description 9
150000001875 compounds Chemical class 0.000 claims abstract description 32
239000000203 mixture Substances 0.000 claims abstract description 23
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 18
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 17
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 10
239000003960 organic solvent Substances 0.000 claims abstract description 6
238000007327 hydrogenolysis reaction Methods 0.000 claims abstract description 4
238000004519 manufacturing process Methods 0.000 claims 1
238000002360 preparation method Methods 0.000 abstract description 8
WGJJROVFWIXTPA-OALUTQOASA-N prostanoic acid Chemical class CCCCCCCC[C@H]1CCC[C@@H]1CCCCCCC(O)=O WGJJROVFWIXTPA-OALUTQOASA-N 0.000 abstract description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
239000000243 solution Substances 0.000 description 21
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
238000004587 chromatography analysis Methods 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
239000003208 petroleum Substances 0.000 description 8
229910052938 sodium sulfate Inorganic materials 0.000 description 8
235000011152 sodium sulphate Nutrition 0.000 description 8
239000012299 nitrogen atmosphere Substances 0.000 description 7
239000002904 solvent Substances 0.000 description 7
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
239000007858 starting material Substances 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane group Chemical group CCCCCCC[C@H]1CCCO[C@@H]1CCCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 description 6
AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical compound [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 5
150000004678 hydrides Chemical class 0.000 description 5
239000005457 ice water Substances 0.000 description 5
239000003921 oil Substances 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
239000012429 reaction media Substances 0.000 description 5
230000001603 reducing effect Effects 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
229960000583 acetic acid Drugs 0.000 description 4
230000002776 aggregation Effects 0.000 description 4
238000004220 aggregation Methods 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 4
239000012230 colorless oil Substances 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
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 3
-1 5-carboxypentyl Chemical group 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
229910052786 argon Inorganic materials 0.000 description 3
229940079593 drug Drugs 0.000 description 3
239000003814 drug Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
235000019253 formic acid Nutrition 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
239000012071 phase Substances 0.000 description 3
238000000926 separation method Methods 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
210000003437 trachea Anatomy 0.000 description 3
JBMFRGUHVZMUDI-YQVWRLOYSA-N 7-[(1S,2R,3R)-2-heptoxy-3-hydroxycyclopentyl]heptanoic acid Chemical compound CCCCCCCO[C@H]1[C@H](O)CC[C@@H]1CCCCCCC(O)=O JBMFRGUHVZMUDI-YQVWRLOYSA-N 0.000 description 2
MEQBAHKBSLEMIJ-ROUUACIJSA-N 7-[(1S,2S)-2-heptoxycyclopentyl]heptanoic acid Chemical compound C(CCCCCC[C@H]1CCC[C@@H]1OCCCCCCC)(=O)O MEQBAHKBSLEMIJ-ROUUACIJSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
241000700199 Cavia porcellus Species 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
108090000190 Thrombin Proteins 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
230000009471 action Effects 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
239000008280 blood Substances 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
229910010277 boron hydride Inorganic materials 0.000 description 2
239000003245 coal Substances 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
238000001035 drying Methods 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
238000011534 incubation Methods 0.000 description 2
CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 2
230000009467 reduction Effects 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
229960004072 thrombin Drugs 0.000 description 2
ZNZISHNDYHTHKL-UHFFFAOYSA-N 1-benzylcyclopentan-1-ol Chemical compound C=1C=CC=CC=1CC1(O)CCCC1 ZNZISHNDYHTHKL-UHFFFAOYSA-N 0.000 description 1
RZYCTWZLJOQWRN-ROUUACIJSA-N 5-[(1s,2s)-2-octylcyclopentyl]pentyl hydrogen carbonate Chemical compound CCCCCCCC[C@H]1CCC[C@@H]1CCCCCOC(O)=O RZYCTWZLJOQWRN-ROUUACIJSA-N 0.000 description 1
UCTWMZQNUQWSLP-UHFFFAOYSA-N Adrenaline Natural products CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
235000019738 Limestone Nutrition 0.000 description 1
STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical group CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 1
HCRWXCXWUZRCJE-RGBJRUIASA-N OC(C(=O)O)CCCCC[C@H]1CCC[C@@H]1OCCCCCCC Chemical compound OC(C(=O)O)CCCCC[C@H]1CCC[C@@H]1OCCCCCCC HCRWXCXWUZRCJE-RGBJRUIASA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
DSGABDNOPMWXIG-UHFFFAOYSA-M [Na+].[Cl-].CN(C)C=O Chemical compound [Na+].[Cl-].CN(C)C=O DSGABDNOPMWXIG-UHFFFAOYSA-M 0.000 description 1
125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000004931 aggregating effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229910000085 borane Inorganic materials 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
230000003182 bronchodilatating effect Effects 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
MLUCVPSAIODCQM-UHFFFAOYSA-N but-2-enal Chemical group CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
229960000905 indomethacin Drugs 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000006028 limestone Substances 0.000 description 1
238000012544 monitoring process Methods 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
239000012053 oil suspension Substances 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
230000008569 process Effects 0.000 description 1
229960003712 propranolol Drugs 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000004044 response Effects 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/10—Spiro-condensed systems
- 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
- 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
- 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
- C07C405/0008—Analogues having the carboxyl group in the side-chains replaced by other functional groups
- C07C405/0033—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing sulfur
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/60—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in six-membered rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
- C07C45/66—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups by dehydration
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/02—Five-membered rings
- C07D339/06—Five-membered rings having the hetero atoms in positions 1 and 3, e.g. cyclic dithiocarbonates
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/08—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing alicyclic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/08—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing alicyclic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Animal Behavior & Ethology (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Bioinformatics & Cheminformatics (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)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)

SU813320103A 1980-08-12 1981-08-12 Способ получени производных простаноиновой кислоты SU1145925A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB8026240		1980-08-12

Publications (1)

Publication Number	Publication Date
SU1145925A3 true SU1145925A3 (ru)	1985-03-15

Family

ID=10515399

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU813320103A SU1145925A3 (ru)	1980-08-12	1981-08-12	Способ получени производных простаноиновой кислоты

Country Status (8)

Country	Link
JP (1)	JPS5754141A (fr)
KR (2)	KR840002175B1 (fr)
AT (1)	AT378179B (fr)
BE (1)	BE889905A (fr)
HU (1)	HU185645B (fr)
MA (1)	MA19238A1 (fr)
SU (1)	SU1145925A3 (fr)
ZA (1)	ZA814947B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3346655C1 (de)	1983-12-23	1985-01-24	Braun Ag, 6000 Frankfurt	Vorrichtung zur Umwandlung der Drehbewegung eines Exzenters in eine hin- und hergehende Bewegung
DE3346657C1 (de) *	1983-12-23	1985-01-24	Braun Ag, 6000 Frankfurt	Schwinghebelantrieb fuer elektrische Kleingeraete

1981
- 1981-07-20 ZA ZA814947A patent/ZA814947B/xx unknown
- 1981-08-04 KR KR1019810002839A patent/KR840002175B1/ko not_active Expired
- 1981-08-05 MA MA19438A patent/MA19238A1/fr unknown
- 1981-08-10 BE BE0/205621A patent/BE889905A/fr not_active IP Right Cessation
- 1981-08-11 HU HU812316A patent/HU185645B/hu unknown
- 1981-08-11 JP JP56126548A patent/JPS5754141A/ja active Pending
- 1981-08-12 AT AT0354581A patent/AT378179B/de active
- 1981-08-12 SU SU813320103A patent/SU1145925A3/ru active
1984
- 1984-09-21 KR KR1019840005809A patent/KR850000670B1/ko not_active Expired

Also Published As

Publication number	Publication date
KR850000670B1 (ko)	1985-05-09
JPS5754141A (fr)	1982-03-31
ZA814947B (en)	1982-07-28
BE889905A (fr)	1982-02-10
KR830006158A (ko)	1983-09-17
HU185645B (en)	1985-03-28
AT378179B (de)	1985-06-25
KR840002175B1 (ko)	1984-11-26
ATA354581A (de)	1984-11-15
KR850002757A (ko)	1985-05-15
MA19238A1 (fr)	1982-04-01

Publication	Publication Date	Title
SU1128830A3 (ru)	1984-12-07	Способ получени производных аминоэтанола или их солей
EP0045118B1 (fr)	1984-04-04	Intermédiaires pour la synthèse de bicyclo (2,2,1) heptanes et bicyclo (2,2,1) hept-2Z-ènes
NO167302B (no)	1991-07-15	Fremgangsmaate for fremstilling av biologisk aktive sammensetninger.
CH636096A5 (de)	1983-05-13	Bicyclische prostaglandine, verfahren zu ihrer herstellung und pharmazeutische praeparate.
CH635813A5 (fr)	1983-04-29	1,9-dihydroxyoctahydrophenanthrenes et medicament les contenant.
US4320136A (en)	1982-03-16	8-Aza-16,16-difluoroprostanoids
EP0051917B1 (fr)	1986-02-19	Dérivés de benzofuranne-éthanolamine, leurs procédés de préparation et leur usage en médicine
FI62528C (fi)	1983-01-10	Ett nytt foerfarande foer framstaellning av 1-(3,5-dihydroxifenyl)-1-hydroxi-2-(1-metyl-2-(4-hydroxifenyl)-etyl)-aminoetan
SU731895A3 (ru)	1980-04-30	Способ получени аналогов простагландина или их солей
SU1547707A3 (ru)	1990-02-28	Способ получени транс-этил-1,2,3,4-тетрагидро-6,7-метилендиокси-4-оксо-1-/3,4,5-триметоксифенил/нафталин-2-карбоксилата
US3873566A (en)	1975-03-25	3-Pyrazolidinones and pyrazolidines
US3957794A (en)	1976-05-18	3-Amino-2,3,3a,6,7,7a-hexahydro-thieno[3,2-b]pyridin-(4H)5-one
Bindra et al.	1978	An efficient route to intermediates for the synthesis of 11-deoxyprostaglandins
FI70009B (fi)	1986-01-31	Foerfarande foer framstaellning av nya 1,5-disubstituerad-2-pyrrolidonfoereningar vilka har prostaglandinliknande biologiska egenskaper
Shibasaki et al.	1980	Total synthesis of the carbon analog of Δ6-PGI1
HU211554A9 (en)	1995-12-28	Circulation-active dibenzo/1,5/dioxocin-5-ones
JPH0453877B2 (fr)	1992-08-27
EP0001270A1 (fr)	1979-04-04	Analogues de la prostacycline, leurs procédés de préparation et leur utilisation pour le traitement des maladies de la circulation
SU520038A3 (ru)	1976-06-30	Способ получени (1-бис-аралкил-аминоалкил)аралкоксибензиловых спиртов или их солей, рацематов или оптически-активных антиподов
EP0050849B1 (fr)	1984-01-11	Dérivés d'acides prostanoiques 4,5-insaturés
US5068345A (en)	1991-11-26	Oxazolidinone aldol adduct
US4910322A (en)	1990-03-20	Synthesis of geminal dinitro compounds
US4009172A (en)	1977-02-22	2,3,3A,6,7,7A-Hexahydro-thieno[3,2-b]pyridin-(4H)5-ones
SU614746A3 (ru)	1978-07-05	Способ получени аналога простагландина
US3644502A (en)	1972-02-22	Prostaglandin synthesis