CA1160627A - 9-deoxy-6,9-epoxyprostaglandins - Google Patents
9-deoxy-6,9-epoxyprostaglandinsInfo
- Publication number
- CA1160627A CA1160627A CA000270416A CA270416A CA1160627A CA 1160627 A CA1160627 A CA 1160627A CA 000270416 A CA000270416 A CA 000270416A CA 270416 A CA270416 A CA 270416A CA 1160627 A CA1160627 A CA 1160627A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- trinor
- phenyl
- inclusive
- methyl
- Prior art date
- 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
Links
- 238000000034 method Methods 0.000 claims abstract description 69
- 230000008569 process Effects 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims description 122
- -1 inclusive Chemical group 0.000 claims description 78
- 125000004432 carbon atom Chemical group C* 0.000 claims description 51
- 125000000217 alkyl group Chemical group 0.000 claims description 41
- 239000000203 mixture Substances 0.000 claims description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 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 claims description 23
- 125000001153 fluoro group Chemical group F* 0.000 claims description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 239000007858 starting material Substances 0.000 claims description 17
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 15
- 239000011734 sodium Substances 0.000 claims description 14
- 229910052708 sodium Inorganic materials 0.000 claims description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 13
- 239000003153 chemical reaction reagent Substances 0.000 claims description 12
- XXQBEVHPUKOQEO-UHFFFAOYSA-N potassium superoxide Chemical compound [K+].[K+].[O-][O-] XXQBEVHPUKOQEO-UHFFFAOYSA-N 0.000 claims description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 238000005914 dehydroiodination reaction Methods 0.000 claims description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 7
- 150000003512 tertiary amines Chemical class 0.000 claims description 7
- 150000002084 enol ethers Chemical class 0.000 claims description 6
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- 235000015424 sodium Nutrition 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 235000011118 potassium hydroxide Nutrition 0.000 claims description 5
- 229910000144 sodium(I) superoxide Inorganic materials 0.000 claims description 5
- 150000001768 cations Chemical class 0.000 claims description 4
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 claims description 4
- 229940071536 silver acetate Drugs 0.000 claims description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical group C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 4
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 3
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 230000002083 iodinating effect Effects 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 235000011056 potassium acetate Nutrition 0.000 claims description 3
- 235000015497 potassium bicarbonate Nutrition 0.000 claims description 3
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims description 3
- 239000011736 potassium bicarbonate Substances 0.000 claims description 3
- 229940094025 potassium bicarbonate Drugs 0.000 claims description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
- 235000011181 potassium carbonates Nutrition 0.000 claims description 3
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 3
- CUNPJFGIODEJLQ-UHFFFAOYSA-M potassium;2,2,2-trifluoroacetate Chemical compound [K+].[O-]C(=O)C(F)(F)F CUNPJFGIODEJLQ-UHFFFAOYSA-M 0.000 claims description 3
- 125000005207 tetraalkylammonium group Chemical group 0.000 claims description 3
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 2
- 239000004300 potassium benzoate Substances 0.000 claims description 2
- 235000010235 potassium benzoate Nutrition 0.000 claims description 2
- 229940103091 potassium benzoate Drugs 0.000 claims description 2
- 239000001632 sodium acetate Substances 0.000 claims description 2
- 235000017281 sodium acetate Nutrition 0.000 claims description 2
- 239000004299 sodium benzoate Substances 0.000 claims description 2
- 235000010234 sodium benzoate Nutrition 0.000 claims description 2
- 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 2
- PJDMFGSFLLCCAO-FCBYNYORSA-N methyl (z)-7-[3,5-dihydroxy-2-[(e)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoate Chemical compound CCCCCC(O)\C=C\C1C(O)CC(O)C1C\C=C/CCCC(=O)OC PJDMFGSFLLCCAO-FCBYNYORSA-N 0.000 claims 1
- 150000003180 prostaglandins Chemical class 0.000 abstract description 41
- 239000000543 intermediate Substances 0.000 abstract description 5
- 230000000144 pharmacologic effect Effects 0.000 abstract description 4
- 239000004593 Epoxy Substances 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 84
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 63
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 55
- 239000000047 product Substances 0.000 description 55
- 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
- 239000000243 solution Substances 0.000 description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 238000002360 preparation method Methods 0.000 description 26
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 23
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
- 150000004702 methyl esters Chemical class 0.000 description 22
- 238000004809 thin layer chromatography Methods 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 230000000875 corresponding effect Effects 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
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 18
- 150000002596 lactones Chemical class 0.000 description 17
- 239000003921 oil Substances 0.000 description 17
- 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
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 229960002986 dinoprostone Drugs 0.000 description 15
- 241001465754 Metazoa Species 0.000 description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
- 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 13
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 13
- 230000000694 effects Effects 0.000 description 13
- XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 13
- 239000008096 xylene Substances 0.000 description 13
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- 230000009102 absorption Effects 0.000 description 11
- 238000010521 absorption reaction Methods 0.000 description 11
- 230000037396 body weight Effects 0.000 description 11
- 239000012267 brine Substances 0.000 description 11
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
- 241000282414 Homo sapiens Species 0.000 description 10
- 241000124008 Mammalia Species 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 229910052938 sodium sulfate Inorganic materials 0.000 description 10
- 229960003010 sodium sulfate Drugs 0.000 description 10
- 235000011152 sodium sulphate Nutrition 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
- 238000004587 chromatography analysis Methods 0.000 description 9
- 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 9
- 230000002829 reductive effect Effects 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- FDSGHYHRLSWSLQ-UHFFFAOYSA-N dichloromethane;propan-2-one Chemical compound ClCCl.CC(C)=O FDSGHYHRLSWSLQ-UHFFFAOYSA-N 0.000 description 8
- 125000002346 iodo group Chemical group I* 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 238000010898 silica gel chromatography Methods 0.000 description 8
- 229940086542 triethylamine Drugs 0.000 description 8
- 230000010339 dilation Effects 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 230000002496 gastric effect Effects 0.000 description 7
- 239000005457 ice water Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 230000009466 transformation Effects 0.000 description 7
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 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 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- 239000000443 aerosol Substances 0.000 description 6
- 239000002260 anti-inflammatory agent Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 230000000903 blocking effect Effects 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
- 238000001802 infusion Methods 0.000 description 6
- 238000001990 intravenous administration Methods 0.000 description 6
- 208000037805 labour Diseases 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- 230000003595 spectral effect Effects 0.000 description 6
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 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 6
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 5
- 241000282412 Homo Species 0.000 description 5
- 230000003110 anti-inflammatory effect Effects 0.000 description 5
- 150000001540 azides Chemical class 0.000 description 5
- 230000008512 biological response Effects 0.000 description 5
- 210000004369 blood Anatomy 0.000 description 5
- 239000008280 blood Substances 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
- 230000012173 estrus Effects 0.000 description 5
- 238000005755 formation reaction Methods 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 238000001819 mass spectrum Methods 0.000 description 5
- 239000000463 material Substances 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
- 239000002599 prostaglandin synthase inhibitor Substances 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 5
- 208000031638 Body Weight Diseases 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 208000018262 Peripheral vascular disease Diseases 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- HAXFWIACAGNFHA-UHFFFAOYSA-N aldrithiol Chemical compound C=1C=CC=NC=1SSC1=CC=CC=N1 HAXFWIACAGNFHA-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 239000012634 fragment Substances 0.000 description 4
- 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
- 238000002329 infrared spectrum Methods 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 239000012280 lithium aluminium hydride Substances 0.000 description 4
- NSVFAVFBJYCRAC-UHFFFAOYSA-N n,n-diethylethanamine;ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O.CCN(CC)CC NSVFAVFBJYCRAC-UHFFFAOYSA-N 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 210000002460 smooth muscle Anatomy 0.000 description 4
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000000844 transformation Methods 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
- FOBVMYJQWZOGGJ-XYRJXBATSA-N 17-phenyl-18,19,20-trinor-prostaglandin E2 Chemical compound C([C@H](O)\C=C\[C@@H]1[C@H](C(=O)C[C@H]1O)C\C=C/CCCC(O)=O)CC1=CC=CC=C1 FOBVMYJQWZOGGJ-XYRJXBATSA-N 0.000 description 3
- TUXYZHVUPGXXQG-UHFFFAOYSA-M 4-bromobenzoate Chemical compound [O-]C(=O)C1=CC=C(Br)C=C1 TUXYZHVUPGXXQG-UHFFFAOYSA-M 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 229910008338 Si—(CH3) Inorganic materials 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 206010000210 abortion Diseases 0.000 description 3
- 231100000176 abortion Toxicity 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 150000008064 anhydrides 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
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 210000003754 fetus Anatomy 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
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Classifications
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- 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
Landscapes
- 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)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000349869A CA1185969A (en) | 1976-02-04 | 1980-04-14 | 5Z-9-DEOXY-6,9-EPOXY-.DELTA. 5-PGF IN1.alpha. XX, SODIUM SALT |
Applications Claiming Priority (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US65511076A | 1976-02-04 | 1976-02-04 | |
| US655,110 | 1976-02-04 | ||
| US71677176A | 1976-08-23 | 1976-08-23 | |
| US71697276A | 1976-08-23 | 1976-08-23 | |
| US71696976A | 1976-08-23 | 1976-08-23 | |
| US71677076A | 1976-08-23 | 1976-08-23 | |
| US71696076A | 1976-08-23 | 1976-08-23 | |
| US716,771 | 1976-08-23 | ||
| US716,969 | 1976-08-23 | ||
| US716,770 | 1976-08-23 | ||
| US716,960 | 1976-08-23 | ||
| US716,972 | 1976-08-23 | ||
| US72554876A | 1976-09-22 | 1976-09-22 | |
| US725,548 | 1976-09-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1160627A true CA1160627A (en) | 1984-01-17 |
Family
ID=27569874
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000270416A Expired CA1160627A (en) | 1976-02-04 | 1977-01-25 | 9-deoxy-6,9-epoxyprostaglandins |
| CA000349868A Expired CA1160628A (en) | 1976-02-04 | 1978-10-26 | 6-KETO AND 5-HEMIKETAL-PGF IN1.alpha. XX, METHYL ESTERS |
| CA000349870A Expired CA1179335A (en) | 1976-02-04 | 1978-10-26 | 5Z-9-DEOXY-6,9-EPOXY-5-IODO-PGF 1N/.alpha. XX |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000349868A Expired CA1160628A (en) | 1976-02-04 | 1978-10-26 | 6-KETO AND 5-HEMIKETAL-PGF IN1.alpha. XX, METHYL ESTERS |
| CA000349870A Expired CA1179335A (en) | 1976-02-04 | 1978-10-26 | 5Z-9-DEOXY-6,9-EPOXY-5-IODO-PGF 1N/.alpha. XX |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS5936911B2 (de) |
| BE (1) | BE851122A (de) |
| CA (3) | CA1160627A (de) |
| CH (2) | CH632245A5 (de) |
| DE (1) | DE2702553C2 (de) |
| FR (3) | FR2359125B1 (de) |
| GB (1) | GB1554044A (de) |
| HK (1) | HK9385A (de) |
| IL (1) | IL51189A (de) |
| MX (1) | MX4811E (de) |
| NL (2) | NL185515C (de) |
| NZ (1) | NZ183050A (de) |
| SE (1) | SE435281B (de) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH629493A5 (en) * | 1976-05-11 | 1982-04-30 | Wellcome Found | Processes for preparing novel prostaglandin derivatives |
| 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 |
| 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 |
| 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 |
| 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 |
| CH648556A5 (de) * | 1981-03-11 | 1985-03-29 | Hoffmann La Roche | Fluorprostacycline. |
| 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 |
| US5221763A (en) * | 1987-04-30 | 1993-06-22 | R-Tech Ueno, Ltd. | Prostaglandins of the F series |
| CA1324129C (en) * | 1987-04-30 | 1993-11-09 | Ryuzo Ueno | Prostaglandins of the f series |
| US5591887A (en) * | 1987-04-30 | 1997-01-07 | R-Tech Ueno, Ltd. | Prostaglandins of the F series |
| 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 |
| AU619543B2 (en) * | 1988-05-11 | 1992-01-30 | Sucampo Ag | Use of 15-ketoprostaglandin e or f compounds for uterine contraction |
| RU2540330C2 (ru) | 2009-07-28 | 2015-02-10 | Оно Фармасьютикал Ко., Лтд. | Бициклическое соединение и его применение для медицинских целей |
| 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)
| 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 |
| CH629493A5 (en) * | 1976-05-11 | 1982-04-30 | Wellcome Found | Processes for preparing novel prostaglandin derivatives |
| 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/en 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 JP JP52010332A patent/JPS5936911B2/ja not_active Expired
- 1977-02-03 FR FR7703076A patent/FR2359125B1/fr not_active Expired
- 1977-02-04 CH CH141677A patent/CH632245A5/de not_active IP Right Cessation
- 1977-02-04 BE BE174693A patent/BE851122A/xx 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 CA000349868A patent/CA1160628A/en not_active Expired
- 1978-10-26 CA CA000349870A patent/CA1179335A/en 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 |
|---|---|
| FR2359125A1 (fr) | 1978-02-17 |
| FR2362833B1 (de) | 1980-08-08 |
| SE7701045L (sv) | 1977-08-05 |
| NL185515B (nl) | 1989-12-01 |
| BE851122A (fr) | 1977-08-04 |
| HK9385A (en) | 1985-02-08 |
| FR2362834A1 (fr) | 1978-03-24 |
| DE2702553A1 (de) | 1977-08-18 |
| JPS5936911B2 (ja) | 1984-09-06 |
| NZ183050A (en) | 1979-06-08 |
| CH632245A5 (en) | 1982-09-30 |
| SE435281B (sv) | 1984-09-17 |
| FR2359125B1 (fr) | 1985-11-15 |
| CH637949A5 (en) | 1983-08-31 |
| NL185515C (nl) | 1990-05-01 |
| JPS5295644A (en) | 1977-08-11 |
| NL7700896A (nl) | 1977-08-08 |
| IL51189A (en) | 1985-08-30 |
| CA1160628A (en) | 1984-01-17 |
| IL51189A0 (en) | 1977-02-28 |
| NL8300921A (nl) | 1983-07-01 |
| MX4811E (es) | 1982-10-19 |
| DE2702553C2 (de) | 1986-02-20 |
| CA1179335A (en) | 1984-12-11 |
| FR2362834B1 (de) | 1980-08-08 |
| FR2362833A1 (fr) | 1978-03-24 |
| GB1554044A (en) | 1979-10-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |