CH619944A5 - - Google Patents

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Info

Publication number: CH619944A5
Authority: CH; Switzerland
Prior art keywords: formula; compound; formaldehyde; acid; reaction
Prior art date: 1976-02-20

Application number

CH213877A

Other languages

English (en)

French (fr)

Inventor

Istvan Dr Toemoeskoezi

Gabor Dr Kovacs

Istvan Szekely

Vilmos Dr Simonidesz

Mariann Lovasz-Gaspar

Borbala Keresztes-Ordoeg

Julia Dr Remport-Radoczi

Istvan Dr Stadler

Zsuzsa Dr Visky-Gombos

Csaba Dr Szantay

Original Assignee

Chinoin Gyogyszer Es Vegyeszet

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.)

1976-02-20

Filing date

1977-02-21

Publication date

1980-10-31

1977-02-21 Application filed by Chinoin Gyogyszer Es Vegyeszet filed Critical Chinoin Gyogyszer Es Vegyeszet

1980-10-31 Publication of CH619944A5 publication Critical patent/CH619944A5/fr

Links

150000001875 compounds Chemical class 0.000 claims description 63
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 50
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 28
238000006243 chemical reaction Methods 0.000 claims description 25
239000000203 mixture Substances 0.000 claims description 24
238000000034 method Methods 0.000 claims description 17
239000002253 acid Substances 0.000 claims description 15
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
238000002360 preparation method Methods 0.000 claims description 10
-1 bicyclic lactone Chemical class 0.000 claims description 9
125000002252 acyl group Chemical group 0.000 claims description 7
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
150000002596 lactones Chemical class 0.000 claims description 4
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 2
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
239000007864 aqueous solution Substances 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
239000012429 reaction media Substances 0.000 claims description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 2
125000004429 atom Chemical group 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 60
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 25
230000015572 biosynthetic process Effects 0.000 description 21
239000000047 product Substances 0.000 description 17
238000003786 synthesis reaction Methods 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
238000010478 Prins reaction Methods 0.000 description 12
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
229960000583 acetic acid Drugs 0.000 description 9
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
239000002904 solvent Substances 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
229940094443 oxytocics prostaglandins Drugs 0.000 description 7
150000003180 prostaglandins Chemical class 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
238000003756 stirring Methods 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
229930040373 Paraformaldehyde Natural products 0.000 description 6
238000010586 diagram Methods 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000000243 solution Substances 0.000 description 6
238000006136 alcoholysis reaction Methods 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
229920002866 paraformaldehyde Polymers 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229960001866 silicon dioxide Drugs 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000021736 acetylation Effects 0.000 description 3
238000006640 acetylation reaction Methods 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
230000006196 deacetylation Effects 0.000 description 3
238000003381 deacetylation reaction Methods 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
230000005012 migration Effects 0.000 description 3
238000013508 migration Methods 0.000 description 3
230000003647 oxidation Effects 0.000 description 3
238000007254 oxidation reaction Methods 0.000 description 3
230000000704 physical effect Effects 0.000 description 3
229940127293 prostanoid Drugs 0.000 description 3
150000003814 prostanoids Chemical class 0.000 description 3
230000000707 stereoselective effect Effects 0.000 description 3
BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical group C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
239000003377 acid catalyst Substances 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000003513 alkali Substances 0.000 description 2
150000001336 alkenes Chemical class 0.000 description 2
150000004703 alkoxides Chemical class 0.000 description 2
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
230000004071 biological effect Effects 0.000 description 2
239000012267 brine Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
239000011521 glass Substances 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
230000001590 oxidative effect Effects 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000001632 sodium acetate Substances 0.000 description 2
235000017281 sodium acetate Nutrition 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
230000009466 transformation Effects 0.000 description 2
PXGPLTODNUVGFL-BRIYLRKRSA-N (E,Z)-(1R,2R,3R,5S)-7-(3,5-Dihydroxy-2-((3S)-(3-hydroxy-1-octenyl))cyclopentyl)-5-heptenoic acid Chemical compound CCCCC[C@H](O)C=C[C@H]1[C@H](O)C[C@H](O)[C@@H]1CC=CCCCC(O)=O PXGPLTODNUVGFL-BRIYLRKRSA-N 0.000 description 1
KFUSEUYYWQURPO-UHFFFAOYSA-N 1,2-dichloroethene Chemical compound ClC=CCl KFUSEUYYWQURPO-UHFFFAOYSA-N 0.000 description 1
VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 1
150000000093 1,3-dioxanes Chemical class 0.000 description 1
HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 1
XOTUAMWIFRDGMZ-UHFFFAOYSA-N 2-chloroprop-2-enoyl chloride Chemical compound ClC(=C)C(Cl)=O XOTUAMWIFRDGMZ-UHFFFAOYSA-N 0.000 description 1
MLOSJPZSZWUDSK-UHFFFAOYSA-N 4-carboxybutyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCC(=O)O)C1=CC=CC=C1 MLOSJPZSZWUDSK-UHFFFAOYSA-N 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
238000005698 Diels-Alder reaction Methods 0.000 description 1
206010022998 Irritability Diseases 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
238000007239 Wittig reaction Methods 0.000 description 1
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
238000007259 addition reaction Methods 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
238000011914 asymmetric synthesis Methods 0.000 description 1
238000009835 boiling Methods 0.000 description 1
244000309464 bull Species 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000011097 chromatography purification Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000012691 depolymerization reaction Methods 0.000 description 1
XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 1
229960002986 dinoprostone Drugs 0.000 description 1
238000004821 distillation Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003480 eluent Substances 0.000 description 1
238000010828 elution Methods 0.000 description 1
238000006735 epoxidation reaction Methods 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000008098 formaldehyde solution Substances 0.000 description 1
239000012634 fragment Substances 0.000 description 1
RTYRONIMTRDBLT-UHFFFAOYSA-N hept-5-en-2-one Chemical compound CC=CCCC(C)=O RTYRONIMTRDBLT-UHFFFAOYSA-N 0.000 description 1
229940088597 hormone Drugs 0.000 description 1
239000005556 hormone Substances 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
150000001261 hydroxy acids Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000005259 measurement Methods 0.000 description 1
238000006140 methanolysis reaction Methods 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000000178 monomer Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
229920006324 polyoxymethylene Polymers 0.000 description 1
XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 1
DZUXGQBLFALXCR-CDIPTNKSSA-N prostaglandin F1alpha Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1CCCCCCC(O)=O DZUXGQBLFALXCR-CDIPTNKSSA-N 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
150000003476 thallium compounds Chemical class 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
238000006257 total synthesis reaction Methods 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
238000000844 transformation Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
- C07D307/935—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical 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)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Furan Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH213877A 1976-02-20 1977-02-21 CH619944A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU76CI1644A HU173711B (hu)	1976-02-20	1976-02-20	Sposob poluchenija biciklicheskikh proizvodnykh laktonov ispol'zuemykh intermediarnymi soedineijami v sinteze prostaglandinov

Publications (1)

Publication Number	Publication Date
CH619944A5 true CH619944A5 (de)	1980-10-31

Family

ID=10994602

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH213877A CH619944A5 (de)	1976-02-20	1977-02-21

Country Status (8)

Country	Link
US (1)	US4126622A (de)
JP (1)	JPS52105163A (de)
CA (1)	CA1116175A (de)
CH (1)	CH619944A5 (de)
FI (1)	FI69073C (de)
GB (1)	GB1566510A (de)
HU (1)	HU173711B (de)
SE (1)	SE435282B (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0249953A1 (de) *	1986-06-19	1987-12-23	Nissan Chemical Industries Ltd.	Optisch aktive Bicyclocarbonsäuren und ihre Derivate
JP3097145B2 (ja) *	1991-02-27	2000-10-10	日産化学工業株式会社	コーリーラクトンジオールの光学分割方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1353922A (en) *	1971-04-13	1974-05-22	Ici Ltd	Bicycloheptene derivatives

1976
- 1976-02-20 HU HU76CI1644A patent/HU173711B/hu not_active IP Right Cessation
1977
- 1977-02-15 SE SE7701666A patent/SE435282B/xx not_active IP Right Cessation
- 1977-02-18 CA CA272,051A patent/CA1116175A/en not_active Expired
- 1977-02-18 FI FI770531A patent/FI69073C/fi not_active IP Right Cessation
- 1977-02-18 GB GB6977/77A patent/GB1566510A/en not_active Expired
- 1977-02-21 JP JP1799277A patent/JPS52105163A/ja active Granted
- 1977-02-21 CH CH213877A patent/CH619944A5/fr not_active IP Right Cessation
- 1977-02-22 US US05/770,998 patent/US4126622A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
FI770531A7 (de)	1977-08-21
HU173711B (hu)	1979-07-28
CA1116175A (en)	1982-01-12
FI69073B (fi)	1985-08-30
SE7701666L (sv)	1977-08-21
SE435282B (sv)	1984-09-17
JPS52105163A (en)	1977-09-03
GB1566510A (en)	1980-04-30
US4126622A (en)	1978-11-21
FI69073C (fi)	1985-12-10
JPS6143353B2 (de)	1986-09-26

Legal Events

Date	Code	Title	Description
1987-10-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
FR2738565A1 (fr)	1997-03-14	Produits extraits d'une plante du genre commiphora, en particulier de la plante commiphora mukul, et extraits en contenant et leurs applications notamment en cosmetique
CH632505A5 (fr)	1982-10-15	Nouveaux composes a noyau cyclopropanique, procede de preparation et utilisation a la preparation de derives cyclopropaniques a chaine dihalovinylique.
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EP0715615B1 (de)	1998-10-07	Verfahren zur herstellung von (+)-(1r)-cis-3-oxo-2-pentyl-1-cyclopentanessigsäure
CH624101A5 (de)	1981-07-15
CH644101A5 (fr)	1984-07-13	Analogues de la prostaglandine e(1) et compositions pharmaceutiques les contenant.
CH623303A5 (de)	1981-05-29
FR2582648A1 (fr)	1986-12-05	Intermediaires carbacycline optiquement actifs et procedes de leur preparation
EP0013995B1 (de)	1982-12-29	Verfahren zur Herstellung acetylenischer macrocyclischer Ketone
EP0432021A1 (de)	1991-06-12	Zwischenprodukte, Verfahren zu deren Herstellung und deren Verwendung zur Herstellung der Vitamine A und E
EP0153212B1 (de)	1988-07-13	4,4-Dimethyl-Tetrahydro-2H-Pyran-2-on-Derivate, Verfahren zu deren Herstellung und deren Verwendung für die Synthese von cyclopropanischen Derivaten
EP0024241A1 (de)	1981-02-25	Sulfonierte Verbindungen, die einen Lactonring enthalten, und die Herstellung von Cyclopropanderivaten
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FR3063729B1 (fr)	2019-06-07	Nouvelle composition d'isomeres du 7,9-dodecadienyl-1-acetate et son procede de fabrication
FI69073C (fi)	1985-12-10	Foerfarande foer framstaellning av optiskt aktiva eller racemiska laktondiolderivat
BE867095A (fr)	1978-11-16	Nouveaux derives sesquiterpeniques utiles notamment comme inhibiteurs du systeme complementaire et leurs procedes de preparation
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EP0544588A1 (de)	1993-06-02	Zwischenprodukte für die Herstellung von Vitamin A und E und von Carotenoiden
US4204999A (en)	1980-05-27	Process for making bicyclic lactone derivatives for use as intermediates in the synthesis of prostaglandins
EP0430808A1 (de)	1991-06-05	Dihydropyranderivate, ihre Verfahren zur Herstellung und ihre Verwendung
EP0012390A2 (de)	1980-06-25	Verfahren zur Herstellung von Muscon und Pyran-Zwischenprodukte
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CH621784A5 (de)	1981-02-27