CA1160628A - 6-CETO ET 5-HEMICETAL-PCF IN1.alpha. XX, ESTERS METHYLIQUES - Google Patents

6-CETO ET 5-HEMICETAL-PCF IN1.alpha. XX, ESTERS METHYLIQUES

Info

Publication number: CA1160628A
Authority: CA; Canada
Prior art keywords: formula; trinor; methyl; phenyl; compounds
Prior art date: 1976-02-04
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

Application number

CA000349868A

Other languages

English (en)

Inventor

Udo F. Axen

Frank H. Lincoln

Roy A. Johnson

Robert C. Kelly

John E. Pike

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Pharmacia and Upjohn Co

Original Assignee

Upjohn Co

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.)

1976-02-04

Filing date

1978-10-26

Publication date

1984-01-17

1978-10-26 Application filed by Upjohn Co filed Critical Upjohn Co

1984-01-17 Application granted granted Critical

1984-01-17 Publication of CA1160628A publication Critical patent/CA1160628A/fr

Status Expired legal-status Critical Current

Links

150000004702 methyl esters Chemical class 0.000 title description 22
150000001875 compounds Chemical class 0.000 claims abstract description 133
238000000034 method Methods 0.000 claims abstract description 64
230000008569 process Effects 0.000 claims abstract description 11
-1 keto compound Chemical class 0.000 claims description 77
125000004432 carbon atom Chemical group C* 0.000 claims description 54
125000000217 alkyl group Chemical group 0.000 claims description 40
229910052739 hydrogen Inorganic materials 0.000 claims description 35
239000001257 hydrogen Substances 0.000 claims description 33
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
125000001153 fluoro group Chemical group F* 0.000 claims description 21
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
125000001309 chloro group Chemical group Cl* 0.000 claims description 8
239000000126 substance Substances 0.000 claims description 8
229930194542 Keto Natural products 0.000 claims description 6
125000003710 aryl alkyl group Chemical group 0.000 claims description 6
238000006460 hydrolysis reaction Methods 0.000 claims description 6
125000002947 alkylene group Chemical group 0.000 claims description 5
150000001768 cations Chemical class 0.000 claims description 4
230000007062 hydrolysis Effects 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
238000005695 dehalogenation reaction Methods 0.000 claims description 3
230000002083 iodinating effect Effects 0.000 claims description 3
125000000468 ketone group Chemical group 0.000 claims 4
150000002431 hydrogen Chemical group 0.000 claims 2
KFGOFTHODYBSGM-ZUNNJUQCSA-N 6-oxoprostaglandin F1alpha Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1CC(=O)CCCCC(O)=O KFGOFTHODYBSGM-ZUNNJUQCSA-N 0.000 claims 1
MEQIINSNZUAJET-UHFFFAOYSA-N methyl 2,3,3-triphenylpropanoate Chemical compound C=1C=CC=CC=1C(C(=O)OC)C(C=1C=CC=CC=1)C1=CC=CC=C1 MEQIINSNZUAJET-UHFFFAOYSA-N 0.000 claims 1
150000003180 prostaglandins Chemical class 0.000 abstract description 39
239000000543 intermediate Substances 0.000 abstract description 5
230000000144 pharmacologic effect Effects 0.000 abstract description 4
239000004593 Epoxy Substances 0.000 abstract description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 85
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 56
239000000047 product Substances 0.000 description 56
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 49
239000000203 mixture Substances 0.000 description 37
PXGPLTODNUVGFL-BRIYLRKRSA-N (E,Z)-(1R,2R,3R,5S)-7-(3,5-Dihydroxy-2-((3S)-(3-hydroxy-1-octenyl))cyclopentyl)-5-heptenoic acid Chemical class 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 36
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
239000000243 solution Substances 0.000 description 32
238000002360 preparation method Methods 0.000 description 27
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 23
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
238000004809 thin layer chromatography Methods 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
230000000875 corresponding effect Effects 0.000 description 19
125000002887 hydroxy group Chemical group [H]O* 0.000 description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 18
150000002596 lactones Chemical group 0.000 description 18
239000003921 oil Substances 0.000 description 17
239000007858 starting material Substances 0.000 description 17
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 16
239000002253 acid Substances 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 14
238000011282 treatment Methods 0.000 description 14
229960002986 dinoprostone Drugs 0.000 description 13
BJXHXZDHQUYRMA-UHFFFAOYSA-N (-)-prostaglandin E2-1,15-lactone Natural products C1=CC(CCCCC)OC(=O)CCCC=CCC2C(=O)CC(O)C12 BJXHXZDHQUYRMA-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 12
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
230000037396 body weight Effects 0.000 description 12
230000000694 effects Effects 0.000 description 12
239000011734 sodium Substances 0.000 description 12
UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
239000008096 xylene Substances 0.000 description 12
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230000009102 absorption Effects 0.000 description 11
238000010521 absorption reaction Methods 0.000 description 11
239000012267 brine Substances 0.000 description 11
229940094443 oxytocics prostaglandins Drugs 0.000 description 11
239000000741 silica gel Substances 0.000 description 11
229910002027 silica gel Inorganic materials 0.000 description 11
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
241001465754 Metazoa Species 0.000 description 10
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
XXQBEVHPUKOQEO-UHFFFAOYSA-N potassium superoxide Chemical compound [K+].[K+].[O-][O-] XXQBEVHPUKOQEO-UHFFFAOYSA-N 0.000 description 10
XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 10
229910052708 sodium Inorganic materials 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 10
239000003153 chemical reaction reagent Substances 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
230000002829 reductive effect Effects 0.000 description 9
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
238000004587 chromatography analysis Methods 0.000 description 8
FDSGHYHRLSWSLQ-UHFFFAOYSA-N dichloromethane;propan-2-one Chemical compound ClCCl.CC(C)=O FDSGHYHRLSWSLQ-UHFFFAOYSA-N 0.000 description 8
150000002148 esters Chemical class 0.000 description 8
230000002496 gastric effect Effects 0.000 description 8
125000002346 iodo group Chemical group I* 0.000 description 8
238000010992 reflux Methods 0.000 description 8
238000010898 silica gel chromatography Methods 0.000 description 8
229910052938 sodium sulfate Inorganic materials 0.000 description 8
229960003010 sodium sulfate Drugs 0.000 description 8
235000011152 sodium sulphate Nutrition 0.000 description 8
238000003756 stirring Methods 0.000 description 8
229910052720 vanadium Inorganic materials 0.000 description 8
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 7
230000015572 biosynthetic process Effects 0.000 description 7
230000010339 dilation Effects 0.000 description 7
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 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
238000001802 infusion Methods 0.000 description 7
238000001990 intravenous administration Methods 0.000 description 7
239000012074 organic phase Substances 0.000 description 7
229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
235000017557 sodium bicarbonate Nutrition 0.000 description 7
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
239000002904 solvent Substances 0.000 description 7
229940086542 triethylamine Drugs 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 6
OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 6
239000000443 aerosol Substances 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
239000012043 crude product Substances 0.000 description 6
125000000753 cycloalkyl group Chemical group 0.000 description 6
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
239000000377 silicon dioxide Substances 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 5
241000282412 Homo Species 0.000 description 5
BJXHXZDHQUYRMA-ARSRFYASSA-N PGE2 1,15-lactone Chemical compound C/1=C\[C@H](CCCCC)OC(=O)CCC\C=C/C[C@H]2C(=O)C[C@@H](O)[C@H]\12 BJXHXZDHQUYRMA-ARSRFYASSA-N 0.000 description 5
150000001540 azides Chemical class 0.000 description 5
230000000903 blocking effect Effects 0.000 description 5
210000004369 blood Anatomy 0.000 description 5
239000008280 blood Substances 0.000 description 5
150000002084 enol ethers Chemical class 0.000 description 5
230000012173 estrus Effects 0.000 description 5
238000005755 formation reaction Methods 0.000 description 5
239000005457 ice water Substances 0.000 description 5
239000012280 lithium aluminium hydride Substances 0.000 description 5
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 5
NSVFAVFBJYCRAC-UHFFFAOYSA-N n,n-diethylethanamine;ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O.CCN(CC)CC NSVFAVFBJYCRAC-UHFFFAOYSA-N 0.000 description 5
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
230000003595 spectral effect Effects 0.000 description 5
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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HAXFWIACAGNFHA-UHFFFAOYSA-N aldrithiol Chemical compound C=1C=CC=NC=1SSC1=CC=CC=N1 HAXFWIACAGNFHA-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
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125000004122 cyclic group Chemical group 0.000 description 4
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
201000010099 disease Diseases 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
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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 4
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229960003390 magnesium sulfate Drugs 0.000 description 4
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238000001819 mass spectrum Methods 0.000 description 4
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VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
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238000001953 recrystallisation Methods 0.000 description 4
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WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 4
229910000144 sodium(I) superoxide Inorganic materials 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 4
230000009466 transformation Effects 0.000 description 4
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
229920002554 vinyl polymer Polymers 0.000 description 4
LLVVDFDWPQHXBA-QEJIITRLSA-N 11-Deoxy-16,16-dimethyl-PGE2 Chemical compound CCCCC(C)(C)[C@H](O)\C=C\[C@H]1CCC(=O)[C@@H]1C\C=C/CCCC(O)=O LLVVDFDWPQHXBA-QEJIITRLSA-N 0.000 description 3
LLQBSJQTCKVWTD-QPJJXVBHSA-N 13,14-Dihydro PGF2a Chemical compound CCCCCC(O)CCC1C(O)CC(O)C1C\C=C\CCCC(O)=O LLQBSJQTCKVWTD-QPJJXVBHSA-N 0.000 description 3
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125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 2
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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
- 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
- C07C405/0041—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing nitrogen
- 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
- C07D307/937—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans with hydrocarbon or substituted hydrocarbon radicals directly attached in position 2, e.g. prostacyclins
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/94—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom

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Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Bioinformatics & Cheminformatics (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Furan Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Epoxy Compounds (AREA)

CA000349868A 1976-02-04 1978-10-26 6-CETO ET 5-HEMICETAL-PCF IN1.alpha. XX, ESTERS METHYLIQUES Expired CA1160628A (fr)

Applications Claiming Priority (14)

Application Number	Priority Date	Filing Date
US65511076A	1976-02-04	1976-02-04
US655,110		1976-02-04
US71677176A	1976-08-23	1976-08-23
US71696076A	1976-08-23	1976-08-23
US71696976A	1976-08-23	1976-08-23
US71677076A	1976-08-23	1976-08-23
US71697276A	1976-08-23	1976-08-23
US716,771		1976-08-23
US716,960		1976-08-23
US716,770		1976-08-23
US716,969		1976-08-23
US72554876A	1976-09-22	1976-09-22
US725,548		1976-09-22
US716,972		1985-03-28

Publications (1)

Publication Number	Publication Date
CA1160628A true CA1160628A (fr)	1984-01-17

Family

ID=27569874

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
CA000270416A Expired CA1160627A (fr)	1976-02-04	1977-01-25	9-desoxy-6,9-epoxyprostaglandines
CA000349870A Expired CA1179335A (fr)	1976-02-04	1978-10-26	5Z-9-DESOXY-6,9-EPOXY-5-IODO-PGF 1N/.alpha. XX
CA000349868A Expired CA1160628A (fr)	1976-02-04	1978-10-26	6-CETO ET 5-HEMICETAL-PCF IN1.alpha. XX, ESTERS METHYLIQUES

Family Applications Before (2)

Application Number	Title	Priority Date	Filing Date
CA000270416A Expired CA1160627A (fr)	1976-02-04	1977-01-25	9-desoxy-6,9-epoxyprostaglandines
CA000349870A Expired CA1179335A (fr)	1976-02-04	1978-10-26	5Z-9-DESOXY-6,9-EPOXY-5-IODO-PGF 1N/.alpha. XX

Country Status (13)

Country	Link
JP (1)	JPS5936911B2 (fr)
BE (1)	BE851122A (fr)
CA (3)	CA1160627A (fr)
CH (2)	CH632245A5 (fr)
DE (1)	DE2702553C2 (fr)
FR (3)	FR2359125B1 (fr)
GB (1)	GB1554044A (fr)
HK (1)	HK9385A (fr)
IL (1)	IL51189A (fr)
MX (1)	MX4811E (fr)
NL (2)	NL185515C (fr)
NZ (1)	NZ183050A (fr)
SE (1)	SE435281B (fr)

Families Citing this family (31)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2351113A1 (fr) *	1976-05-11	1977-12-09	Wellcome Found	Derives de prostaglandines et medicaments contenant ces derives
GB1583961A (en) *	1976-05-11	1981-02-04	Wellcome Found	Prostacyclin and derivatives thereof
GB1595056A (en) *	1976-10-12	1981-08-05	Wellcome Found	Pharmaceutical combination
AU511711B2 (en) *	1976-12-30	1980-09-04	Upjohn Company, The	6-Oxo and 5, 6-Dihalo prostaglandin analogues
FI71138C (fi) *	1976-12-31	1986-11-24	Erba Farmitalia	Foerfarande foer framstaellning av terapeutiskt aktiva bisykliska prostaglandiner
US4178367A (en)	1977-02-21	1979-12-11	Ono Pharmaceutical Co. Ltd.	Prostaglandin I2 analogues
AU524786B2 (en) *	1977-03-07	1982-10-07	The Upjohn Company	Prostacyclins
JPS53136513A (en) *	1977-05-06	1978-11-29	Ono Pharmaceut Co Ltd	Stabilization of prostaglandin-x-related compounds
US4219647A (en)	1977-09-22	1980-08-26	Josef Fried	Certain amides of prostacyclin and related compounds
JPS6022710B2 (ja) *	1977-09-16	1985-06-03	小野薬品工業株式会社	プロスタグランジン類似化合物
DE2743283A1 (de) *	1977-09-27	1979-04-05	Hoechst Ag	Neue prostacyclin-analoga
IT1088036B (it)	1977-11-25	1985-06-04	Erba Carlo Spa	15-epi-prostaciclina e prostaciclina analoghi
US4705806A (en) *	1978-02-13	1987-11-10	Morton Jr Douglas R	Prostacyclin analogs
DE2811950A1 (de) *	1978-03-18	1979-12-13	Hoechst Ag	Neue analoga von prostacyclin
HU179001B (en)	1978-05-29	1982-08-28	Chinoin Gyogyszer Es Vegyeszet	Process for preparing 5-halo-6,9alpha-oxido-prostaglandin derivatives
IT1099575B (it) *	1978-07-20	1985-09-18	Erba Carlo Spa	20-metil-13,14-deidro-pgi2' suoi sali e suoi 16s- e 16r-metil derivati
DE2834248A1 (de) *	1978-08-04	1980-02-28	Hoechst Ag	Neue prostaglandinderivate in der delta 2-pgf tief 2 und delta 2-pge tief 2 -reihe
US4180657A (en) *	1978-08-14	1979-12-25	The Upjohn Company	Acyl-substituted phenyl esters of prostacyclin-type compounds
JPS56122372A (en) *	1980-03-03	1981-09-25	Toray Ind Inc	Prostaglandin i2 derivative
DE3029984C2 (de) *	1980-08-08	1983-12-15	Grünenthal GmbH, 5190 Stolberg	2-Oxabicyclo [3.3.0] octanderivate und diese enthaltende Arzneimittel
CH651033A5 (de) *	1981-03-11	1985-08-30	Hoffmann La Roche	Fluorprostacycline.
AT381309B (de) *	1982-05-27	1986-09-25	Gruenenthal Gmbh	Verfahren zur herstellung von 5z-formen von 2,3,4 -trinor-1,5-inter-m-phenylen-prostacyclinderiva en
JPS595155A (ja) *	1982-06-30	1984-01-12	Ono Pharmaceut Co Ltd	プロスタグランジンｄ類似化合物
CA1324129C (fr) *	1987-04-30	1993-11-09	Ryuzo Ueno	Prostaglandines de la serie f
US5591887A (en) *	1987-04-30	1997-01-07	R-Tech Ueno, Ltd.	Prostaglandins of the F series
US5221763A (en) *	1987-04-30	1993-06-22	R-Tech Ueno, Ltd.	Prostaglandins of the F series
AU619543B2 (en) *	1988-05-11	1992-01-30	Sucampo Ag	Use of 15-ketoprostaglandin e or f compounds for uterine contraction
US5185374A (en) *	1988-05-11	1993-02-09	K.K. Ueno Seiyaku Oyo Kenkyujo	Use of 15-ketoprostaglandin E or F compounds for uterine contraction
HUE028874T2 (en)	2009-07-28	2017-01-30	Ono Pharmaceutical Co	Bicyclic Compound and Use Thereof for Medical Purposes
US9029574B2 (en)	2011-01-27	2015-05-12	Ono Pharmaceutical Co., Ltd.	Bicyclic compound and use thereof for medical purposes
CN116143742B (zh) *	2023-02-27	2024-10-18	广州楷石生物科技有限公司	依前列醇一氧化氮供体药物

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2351112A1 (fr) *	1975-10-21	1977-12-09	Wellcome Found	Derive de prostaglandine et medicament contenant ce derive
FR2351113A1 (fr) *	1976-05-11	1977-12-09	Wellcome Found	Derives de prostaglandines et medicaments contenant ces derives
MX4813E (es) *	1976-06-01	1982-10-19	Upjohn Co	Procedimiento para preparar analogos de prostaglandinas
AU511711B2 (en) *	1976-12-30	1980-09-04	Upjohn Company, The	6-Oxo and 5, 6-Dihalo prostaglandin analogues

1976
- 1976-12-30 IL IL51189A patent/IL51189A/xx unknown
1977
- 1977-01-11 NZ NZ183050A patent/NZ183050A/xx unknown
- 1977-01-22 DE DE2702553A patent/DE2702553C2/de not_active Expired
- 1977-01-25 CA CA000270416A patent/CA1160627A/fr not_active Expired
- 1977-01-27 GB GB3314/77A patent/GB1554044A/en not_active Expired
- 1977-01-28 NL NLAANVRAGE7700896,A patent/NL185515C/xx not_active IP Right Cessation
- 1977-02-01 SE SE7701045A patent/SE435281B/xx not_active IP Right Cessation
- 1977-02-03 FR FR7703076A patent/FR2359125B1/fr not_active Expired
- 1977-02-03 JP JP52010332A patent/JPS5936911B2/ja not_active Expired
- 1977-02-04 BE BE174693A patent/BE851122A/fr not_active IP Right Cessation
- 1977-02-04 CH CH141677A patent/CH632245A5/de not_active IP Right Cessation
- 1977-10-26 FR FR7732283A patent/FR2362834A1/fr active Granted
- 1977-10-26 FR FR7732282A patent/FR2362833A1/fr active Granted
- 1977-11-04 MX MX775413U patent/MX4811E/es unknown
1978
- 1978-10-26 CA CA000349870A patent/CA1179335A/fr not_active Expired
- 1978-10-26 CA CA000349868A patent/CA1160628A/fr not_active Expired
1982
- 1982-04-02 CH CH206082A patent/CH637949A5/de not_active IP Right Cessation
1983
- 1983-07-01 NL NL8300921A patent/NL8300921A/nl not_active Application Discontinuation
1985
- 1985-01-31 HK HK93/85A patent/HK9385A/xx unknown

Also Published As

Publication number	Publication date
FR2359125B1 (fr)	1985-11-15
GB1554044A (en)	1979-10-17
NL185515B (nl)	1989-12-01
CH637949A5 (en)	1983-08-31
JPS5936911B2 (ja)	1984-09-06
FR2359125A1 (fr)	1978-02-17
NL7700896A (nl)	1977-08-08
JPS5295644A (en)	1977-08-11
DE2702553A1 (de)	1977-08-18
BE851122A (fr)	1977-08-04
FR2362834A1 (fr)	1978-03-24
CA1179335A (fr)	1984-12-11
IL51189A0 (en)	1977-02-28
DE2702553C2 (de)	1986-02-20
MX4811E (es)	1982-10-19
CA1160627A (fr)	1984-01-17
FR2362833B1 (fr)	1980-08-08
HK9385A (en)	1985-02-08
CH632245A5 (en)	1982-09-30
FR2362834B1 (fr)	1980-08-08
FR2362833A1 (fr)	1978-03-24
SE7701045L (sv)	1977-08-05
NL185515C (nl)	1990-05-01
IL51189A (en)	1985-08-30
NZ183050A (en)	1979-06-08
SE435281B (sv)	1984-09-17
NL8300921A (nl)	1983-07-01

Legal Events

Date	Code	Title	Description
2001-01-17	MKEX	Expiry

Publication	Publication Date	Title
CA1160628A (fr)	1984-01-17	6-CETO ET 5-HEMICETAL-PCF IN1.alpha. XX, ESTERS METHYLIQUES
US4123441A (en)	1978-10-31	Enlarged-hetero-ring prostacyclin analogs
US4158667A (en)	1979-06-19	6-Keto PGF analogs
US4131738A (en)	1978-12-26	6-Hydroxy-PGE1 compounds
US4029681A (en)	1977-06-14	13,14-Didehydro-PG analogs
US4097489A (en)	1978-06-27	9-Deoxy-9α,6-nitrilo or 6,9α-imino-PGF compounds
US4180657A (en)	1979-12-25	Acyl-substituted phenyl esters of prostacyclin-type compounds
US4205178A (en)	1980-05-27	6-Keto prostaglandin E-type compounds
JPS5811438B2 (ja)	1983-03-02	プロスタグランジン類似体
US4098805A (en)	1978-07-04	9-deoxy-9-methylene-pgf-type amides
US4499293A (en)	1985-02-12	PGI2 Salts
US3767695A (en)	1973-10-23	Prostaglandin e1, f1, and a1 analogs
US4128713A (en)	1978-12-05	6,7-Didehydro-PGI1 compounds
US4490537A (en)	1984-12-25	Enlarged-hetero-ring prostacyclin analogs
CA1159452A (fr)	1983-12-27	Derives de (5e)-9-desoxy-6,9-epoxy-prostaglandine
US4125713A (en)	1978-11-14	Certain 5,6-dihydra-prostacyclin analogs
US4124601A (en)	1978-11-07	Certain 5-halo-6,9α-epoxy-14-bromo(or chloro)-PGF1 compounds
US4281113A (en)	1981-07-28	2,5-Inter-o-phenylene-3,4-dinor-6,9α-epoxy-6.beta.-5-iodo-PGF1 compounds
US4118584A (en)	1978-10-03	9-Deoxy-9-methylene-16-phenyl-PGF compounds
CA1196632A (fr)	1985-11-12	Analogues de 5,6 - dihydro-prostacycline
US4579958A (en)	1986-04-01	5-fluoro-3-oxa-6,7-didehydro-PGI1 compounds
US4490549A (en)	1984-12-25	Enlarged-hetero-ring prostacyclin analogs
US4490548A (en)	1984-12-25	Enlarged-hetero-ring prostacyclin analogs
US4169841A (en)	1979-10-02	Alkenyl-substituted 9-deoxy-6,9-α-epoxymethano-PG analogs
US4126744A (en)	1978-11-21	4-Oxo-PGI1 compounds