CA1072956A - Derives de l'acide prostenoique a utilisation pharmaceutique - Google Patents

Derives de l'acide prostenoique a utilisation pharmaceutique

Info

Publication number: CA1072956A
Authority: CA; Canada
Prior art keywords: alpha; trans; oxo; methyl; isopropylideneprost
Prior art date: 1974-09-19
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

CA235,783A

Other languages

English (en)

Inventor

Kiyoshi Sakai

Koichi Kojima

Junya Ide

Shinsaku Kobayashi

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.)

Sankyo Co Ltd

Original Assignee

Sankyo Co Ltd

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.)

1974-09-19

Filing date

1975-09-18

Publication date

1980-03-04

1974-09-19 Priority claimed from JP10814374A external-priority patent/JPS5434724B2/ja

1975-05-21 Priority claimed from JP6052075A external-priority patent/JPS5835184B2/ja

1975-09-18 Application filed by Sankyo Co Ltd filed Critical Sankyo Co Ltd

1980-03-04 Application granted granted Critical

1980-03-04 Publication of CA1072956A publication Critical patent/CA1072956A/fr

Status Expired legal-status Critical Current

Links

NNOJWZIBHANBJD-OALUTQOASA-N 7-[(1S,2S)-2-octylcyclopentyl]hept-2-enoic acid Chemical class CCCCCCCC[C@H]1CCC[C@@H]1CCCCC=CC(O)=O NNOJWZIBHANBJD-OALUTQOASA-N 0.000 title claims abstract description 6
239000002253 acid Substances 0.000 claims abstract description 136
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 21
125000000217 alkyl group Chemical group 0.000 claims abstract description 20
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 20
150000003839 salts Chemical class 0.000 claims abstract description 14
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
230000001590 oxidative effect Effects 0.000 claims abstract description 8
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 5
150000001875 compounds Chemical class 0.000 claims description 176
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 89
239000000203 mixture Substances 0.000 claims description 78
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 75
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 69
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 68
-1 2-tetrahydropyranyloxy Chemical group 0.000 claims description 59
238000000034 method Methods 0.000 claims description 59
230000008569 process Effects 0.000 claims description 43
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 34
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 34
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 30
239000000126 substance Substances 0.000 claims description 21
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 17
239000003810 Jones reagent Substances 0.000 claims description 16
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 16
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 11
229910052700 potassium Inorganic materials 0.000 claims description 11
229960003975 potassium Drugs 0.000 claims description 11
239000011591 potassium Substances 0.000 claims description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
229910000027 potassium carbonate Inorganic materials 0.000 claims description 8
235000011181 potassium carbonates Nutrition 0.000 claims description 8
238000004440 column chromatography Methods 0.000 claims description 7
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims description 6
QPMJENKZJUFOON-PLNGDYQASA-N ethyl (z)-3-chloro-2-cyano-4,4,4-trifluorobut-2-enoate Chemical compound CCOC(=O)C(\C#N)=C(/Cl)C(F)(F)F QPMJENKZJUFOON-PLNGDYQASA-N 0.000 claims description 6
238000004809 thin layer chromatography Methods 0.000 claims description 6
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
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 3
229940086066 potassium hydrogencarbonate Drugs 0.000 claims description 3
235000007686 potassium Nutrition 0.000 claims 2
239000000376 reactant Substances 0.000 claims 2
239000003795 chemical substances by application Substances 0.000 abstract description 7
230000003182 bronchodilatating effect Effects 0.000 abstract description 6
230000000026 anti-ulcerogenic effect Effects 0.000 abstract description 2
238000006243 chemical reaction Methods 0.000 description 128
239000000243 solution Substances 0.000 description 89
239000003921 oil Substances 0.000 description 82
239000007788 liquid Substances 0.000 description 81
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 79
238000002329 infrared spectrum Methods 0.000 description 78
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 77
239000002904 solvent Substances 0.000 description 73
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 66
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 61
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 45
239000000284 extract Substances 0.000 description 42
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 42
238000001228 spectrum Methods 0.000 description 36
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 30
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 28
239000000047 product Substances 0.000 description 28
235000019439 ethyl acetate Nutrition 0.000 description 27
229940093499 ethyl acetate Drugs 0.000 description 26
239000011541 reaction mixture Substances 0.000 description 26
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 25
125000006239 protecting group Chemical class 0.000 description 25
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 23
230000002829 reductive effect Effects 0.000 description 19
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
229910052708 sodium Inorganic materials 0.000 description 17
239000011734 sodium 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
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
238000003756 stirring Methods 0.000 description 16
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
238000007796 conventional method Methods 0.000 description 15
238000001816 cooling Methods 0.000 description 15
WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 14
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 13
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 13
239000003153 chemical reaction reagent Substances 0.000 description 13
150000003180 prostaglandins Chemical class 0.000 description 13
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
239000000741 silica gel Substances 0.000 description 12
229910002027 silica gel Inorganic materials 0.000 description 12
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 10
229960001760 dimethyl sulfoxide Drugs 0.000 description 10
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
239000005457 ice water Substances 0.000 description 8
239000003960 organic solvent Substances 0.000 description 8
239000007800 oxidant agent Substances 0.000 description 8
238000012360 testing method Methods 0.000 description 8
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Natural products OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 7
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 7
239000002585 base Substances 0.000 description 7
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
229910052786 argon Inorganic materials 0.000 description 6
239000003638 chemical reducing agent Substances 0.000 description 6
239000012043 crude product Substances 0.000 description 6
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 6
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
239000012312 sodium hydride Substances 0.000 description 6
229910000104 sodium hydride Inorganic materials 0.000 description 6
239000000725 suspension Substances 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 5
238000001035 drying Methods 0.000 description 5
238000001704 evaporation Methods 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
238000001819 mass spectrum Methods 0.000 description 5
TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical compound Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 description 5
239000001117 sulphuric acid Substances 0.000 description 5
235000011149 sulphuric acid Nutrition 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
229940126062 Compound A Drugs 0.000 description 4
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 4
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 4
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
239000013078 crystal Substances 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
230000002496 gastric effect Effects 0.000 description 4
150000004678 hydrides Chemical class 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
230000007935 neutral effect Effects 0.000 description 4
150000007524 organic acids Chemical class 0.000 description 4
230000003647 oxidation Effects 0.000 description 4
238000007254 oxidation reaction Methods 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
239000003223 protective agent Substances 0.000 description 4
238000006722 reduction reaction Methods 0.000 description 4
230000028327 secretion Effects 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
239000007858 starting material Substances 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
101150041968 CDC13 gene Proteins 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
238000007239 Wittig reaction Methods 0.000 description 3
UCTLHLZWKJIXJI-LXIBVNSESA-N [(3s,8r,9s,10r,13s,14s)-17-chloro-16-formyl-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1h-cyclopenta[a]phenanthren-3-yl] acetate Chemical compound C([C@@H]12)C[C@]3(C)C(Cl)=C(C=O)C[C@H]3[C@@H]1CC=C1[C@]2(C)CC[C@H](OC(=O)C)C1 UCTLHLZWKJIXJI-LXIBVNSESA-N 0.000 description 3
NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 description 3
239000003513 alkali Substances 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
230000037396 body weight Effects 0.000 description 3
MOOAHMCRPCTRLV-UHFFFAOYSA-N boron sodium Chemical compound [B].[Na] MOOAHMCRPCTRLV-UHFFFAOYSA-N 0.000 description 3
239000007810 chemical reaction solvent Substances 0.000 description 3
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000010828 elution Methods 0.000 description 3
230000032050 esterification Effects 0.000 description 3
238000005886 esterification reaction Methods 0.000 description 3
125000000623 heterocyclic group Chemical group 0.000 description 3
150000002430 hydrocarbons Chemical group 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
238000010253 intravenous injection Methods 0.000 description 3
229960001317 isoprenaline Drugs 0.000 description 3
229910052744 lithium Inorganic materials 0.000 description 3
239000000463 material Substances 0.000 description 3
235000010755 mineral Nutrition 0.000 description 3
239000011707 mineral Substances 0.000 description 3
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 3
238000010992 reflux Methods 0.000 description 3
229960002052 salbutamol Drugs 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
VYMPLPIFKRHAAC-UHFFFAOYSA-N 1,2-ethanedithiol Chemical compound SCCS VYMPLPIFKRHAAC-UHFFFAOYSA-N 0.000 description 2
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 2
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
239000012027 Collins reagent Substances 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
239000012448 Lithium borohydride Substances 0.000 description 2
ZFLPOPCZMXGUOJ-UHFFFAOYSA-N Methyl citronellate Chemical compound COC(=O)CC(C)CCC=C(C)C ZFLPOPCZMXGUOJ-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000000443 aerosol Substances 0.000 description 2
229910001854 alkali hydroxide Inorganic materials 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 2
125000004183 alkoxy alkyl group Chemical group 0.000 description 2
239000004411 aluminium Substances 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
229910000091 aluminium hydride Inorganic materials 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
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210000002784 stomach Anatomy 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
RGYLYUZOGHTBRF-BIHRQFPBSA-N tetragastrin Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@@H](N)CC=1C2=CC=CC=C2NC=1)CCSC)C(N)=O)C1=CC=CC=C1 RGYLYUZOGHTBRF-BIHRQFPBSA-N 0.000 description 1
125000002306 tributylsilyl group Chemical group C(CCC)[Si](CCCC)(CCCC)* 0.000 description 1
FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
CMSYDJVRTHCWFP-UHFFFAOYSA-N triphenylphosphane;hydrobromide Chemical compound Br.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 CMSYDJVRTHCWFP-UHFFFAOYSA-N 0.000 description 1
MDDPTCUZZASZIQ-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]alumane Chemical compound [Al+3].CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-] MDDPTCUZZASZIQ-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 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
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4015—Esters of acyclic unsaturated acids
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CA235,783A 1974-09-19 1975-09-18 Derives de l'acide prostenoique a utilisation pharmaceutique Expired CA1072956A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP10814374A JPS5434724B2 (fr)	1974-09-19	1974-09-19
JP6052075A JPS5835184B2 (ja)	1975-05-21	1975-05-21	プロスタグランジンユウドウタイノセイホウ

Publications (1)

Publication Number	Publication Date
CA1072956A true CA1072956A (fr)	1980-03-04

Family

ID=26401594

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA235,783A Expired CA1072956A (fr)	1974-09-19	1975-09-18	Derives de l'acide prostenoique a utilisation pharmaceutique

Country Status (9)

Country	Link
CA (1)	CA1072956A (fr)
CH (1)	CH621773A5 (fr)
DE (1)	DE2541883C2 (fr)
DK (1)	DK418675A (fr)
ES (1)	ES441126A1 (fr)
FR (1)	FR2285124A1 (fr)
GB (1)	GB1499018A (fr)
NL (1)	NL170413C (fr)
SE (1)	SE413023B (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2635985A1 (de) *	1976-08-06	1978-02-09	Schering Ag	Prostansaeurederivat und verfahren zu ihrer herstellung
IT1078774B (it) *	1976-09-07	1985-05-08	Lpb Ist Farm	Derivato dell acido 19 metil 9 cheto 15 idrossi prost 18 enoico
GB2048254B (en) *	1979-04-02	1983-05-25	Upjohn Co	19,20 -didehydro-19-hydroxy and 19-oxo-prostaglandin derivatives

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ZA711840B (en) *	1970-04-20	1972-01-26	Upjohn Co	Pge3-type compounds

1975
- 1975-09-12 GB GB37626/75A patent/GB1499018A/en not_active Expired
- 1975-09-18 SE SE7510466A patent/SE413023B/xx not_active IP Right Cessation
- 1975-09-18 CA CA235,783A patent/CA1072956A/fr not_active Expired
- 1975-09-18 FR FR7528588A patent/FR2285124A1/fr active Granted
- 1975-09-18 DK DK418675A patent/DK418675A/da not_active Application Discontinuation
- 1975-09-19 NL NLAANVRAGE7511127,A patent/NL170413C/xx not_active IP Right Cessation
- 1975-09-19 DE DE2541883A patent/DE2541883C2/de not_active Expired
- 1975-09-19 CH CH1217075A patent/CH621773A5/de not_active IP Right Cessation
- 1975-09-19 ES ES441126A patent/ES441126A1/es not_active Expired

Also Published As

Publication number	Publication date
SE413023B (sv)	1980-03-31
CH621773A5 (en)	1981-02-27
GB1499018A (en)	1978-01-25
FR2285124A1 (fr)	1976-04-16
DK418675A (da)	1976-03-20
ES441126A1 (es)	1977-06-01
NL7511127A (nl)	1976-03-23
NL170413B (nl)	1982-06-01
SE7510466L (sv)	1976-03-22
FR2285124B1 (fr)	1979-09-14
DE2541883A1 (de)	1976-04-01
DE2541883C2 (de)	1984-03-29
NL170413C (nl)	1982-11-01

Legal Events

Date	Code	Title	Description
1997-03-04	MKEX	Expiry

Publication	Publication Date	Title
US4064351A (en)	1977-12-20	9-OXO-15 ξ-HYDROXY-20-ALKYLIDENEPROST-13(TRANS)-ENOIC ACID DERIVATIVES
US4322435A (en)	1982-03-30	Prostacyclin compounds
CA1079725A (fr)	1980-06-17	Analogues de la prostaglandine-acetylene et procede de production
NO155537B (no)	1987-01-05	Analogifremgangsmaate ved fremstilling av terapeutisk aktive, nye carbacycliner.
GB2070596A (en)	1981-09-09	Carbacyclin Analogues
CA1077473A (fr)	1980-05-13	Analogues de la 2-decarboxy-2-aminomethyl-prostaglandine
CA1248525A (fr)	1989-01-10	Carbacyclines, procede de production et utilisation comme medicaments
EP0134246B1 (fr)	1989-08-23	Prostacyclines et leur procede de preparation
CA1267892A (fr)	1990-04-17	Methodes et produits intermediaires pour la preparation des derives 16-phenoxy et 16-phenoxy substitue de l'acide prostatrienoique, et de leur stereoisomeres
US4338249A (en)	1982-07-06	Cyclopenta[b]furan-2-one and -2-ol intermediates for 16-fluoro-13,14-didehydro-prostaglandins
GB2048254A (en)	1980-12-10	19,20-didehydro, 19-hydroxy and 19-oxo-prostaglandin derivatives
US4777184A (en)	1988-10-11	Prostaglandin derivatives, their preparation and use
US4078021A (en)	1978-03-07	Dimethyl 2-oxo-6-cyanohexyl-phosphonate
CA1251202A (fr)	1989-03-14	Derives de carbacyline
EP0010360B1 (fr)	1982-06-02	Dérivés du prostane, procédés pour leur préparation et leurs compositions pharmaceutiques
US4018803A (en)	1977-04-19	13,14-Didehydro-PG3 compounds
IE43815B1 (en)	1981-06-03	11-desoxy-15-substituted-16,17,18,19,20-pentanorprostaglandins
US3953466A (en)	1976-04-27	4(Tetrazol-5-yl)-butyltriphenylphosphonium halide compounds
US4041064A (en)	1977-08-09	16-Methyl prost-5-en-13-ynoic acid derivatives
US4086258A (en)	1978-04-25	13,14-Didehydro-PGA1 compounds
US4251669A (en)	1981-02-17	Analogues of prostanoic acids
CA1060006A (fr)	1979-08-07	LES 11.alpha.-CYANOPROSTAGLANDINES SUBSTITUEES EN 15 ET COMPOSES SEMBLABLES
US4296121A (en)	1981-10-20	Novel prostaglandin derivatives of the Δ2-PGF2 and Δ2-PGE2 series and process for their manufacture
US4110341A (en)	1978-08-29	Dithio prostaglandin derivatives
GB1583146A (en)	1981-01-21	Homoprostaglandins