CA1196632A - 5,6-dihydro-prostacyclin analogs - Google Patents

5,6-dihydro-prostacyclin analogs

Info

Publication number: CA1196632A
Authority: CA; Canada
Prior art keywords: carbon atoms; formula; alkyl; hydrogen; alpha
Prior art date: 1976-06-01
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

CA000279106A

Other languages

English (en)

French (fr)

Inventor

Norman A. Nelson

Udo F. Axen

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.)

1976-06-01

Filing date

1977-05-25

Publication date

1985-11-12

1977-05-25 Application filed by Upjohn Co filed Critical Upjohn Co

1985-11-12 Application granted granted Critical

1985-11-12 Publication of CA1196632A publication Critical patent/CA1196632A/en

Status Expired legal-status Critical Current

Links

RJADQDXZYFCVHV-JQMWNLLFSA-N 5-[(2s,4r,5r,6ar)-5-hydroxy-4-[(e,3s)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydro-2h-cyclopenta[b]furan-2-yl]pentanoic acid Chemical class O1[C@@H](CCCCC(O)=O)CC2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@H]21 RJADQDXZYFCVHV-JQMWNLLFSA-N 0.000 title abstract description 3
150000001875 compounds Chemical class 0.000 claims abstract description 317
238000000034 method Methods 0.000 claims abstract description 117
230000008569 process Effects 0.000 claims abstract description 37
125000004432 carbon atom Chemical group C* 0.000 claims description 232
-1 1-ethoxyethyl Chemical group 0.000 claims description 208
125000000217 alkyl group Chemical group 0.000 claims description 174
239000001257 hydrogen Substances 0.000 claims description 171
229910052739 hydrogen Inorganic materials 0.000 claims description 171
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 148
150000004702 methyl esters Chemical class 0.000 claims description 124
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 120
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 104
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 84
125000001153 fluoro group Chemical group F* 0.000 claims description 75
239000002253 acid Substances 0.000 claims description 70
238000006243 chemical reaction Methods 0.000 claims description 51
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 50
125000001309 chloro group Chemical group Cl* 0.000 claims description 50
150000004292 cyclic ethers Chemical class 0.000 claims description 31
238000002360 preparation method Methods 0.000 claims description 27
125000003710 aryl alkyl group Chemical group 0.000 claims description 26
125000000753 cycloalkyl group Chemical group 0.000 claims description 25
230000002829 reductive effect Effects 0.000 claims description 24
239000012279 sodium borohydride Substances 0.000 claims description 20
229910000033 sodium borohydride Inorganic materials 0.000 claims description 20
125000002947 alkylene group Chemical group 0.000 claims description 19
125000001246 bromo group Chemical group Br* 0.000 claims description 19
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
125000002346 iodo group Chemical group I* 0.000 claims description 19
125000004429 atom Chemical group 0.000 claims description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 16
239000000126 substance Substances 0.000 claims description 16
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 claims description 11
229940100892 mercury compound Drugs 0.000 claims description 10
150000002731 mercury compounds Chemical class 0.000 claims description 10
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 10
125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 10
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 9
238000005695 dehalogenation reaction Methods 0.000 claims description 9
125000003545 alkoxy group Chemical group 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 7
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 7
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 6
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 6
230000002140 halogenating effect Effects 0.000 claims description 4
238000007269 dehydrobromination reaction Methods 0.000 claims description 2
150000002431 hydrogen Chemical group 0.000 claims 13
238000006894 reductive elimination reaction Methods 0.000 claims 5
229910052736 halogen Inorganic materials 0.000 claims 4
150000002367 halogens Chemical class 0.000 claims 4
XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 claims 4
125000004043 oxo group Chemical group O=* 0.000 claims 4
YMRWVEHSLXJOCD-SCOYTADVSA-N (z)-7-[(1r,2r,3r,5s)-3,5-dihydroxy-2-[(e,3r)-3-hydroxy-4,4-dimethyloct-1-enyl]cyclopentyl]hept-5-enoic acid Chemical compound CCCCC(C)(C)[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C/CCCC(O)=O YMRWVEHSLXJOCD-SCOYTADVSA-N 0.000 claims 2
PXGPLTODNUVGFL-YNNPMVKQSA-N prostaglandin F2alpha Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C/CCCC(O)=O PXGPLTODNUVGFL-YNNPMVKQSA-N 0.000 claims 2
CETIHWQNYUHBHT-UHFFFAOYSA-N 2-bromo-2-chloro-2-iodoacetic acid Chemical compound BrC(C(=O)O)(I)Cl CETIHWQNYUHBHT-UHFFFAOYSA-N 0.000 claims 1
229960002986 dinoprostone Drugs 0.000 claims 1
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
CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 claims 1
239000000543 intermediate Substances 0.000 abstract description 18
230000000144 pharmacologic effect Effects 0.000 abstract description 9
DZUXGQBLFALXCR-CDIPTNKSSA-N prostaglandin F1alpha Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1CCCCCCC(O)=O DZUXGQBLFALXCR-CDIPTNKSSA-N 0.000 abstract description 3
DZUXGQBLFALXCR-UHFFFAOYSA-N (+)-(9alpha,11alpha,13E,15S)-9,11,15-trihydroxyprost-13-en-1-oic acid Natural products CCCCCC(O)C=CC1C(O)CC(O)C1CCCCCCC(O)=O DZUXGQBLFALXCR-UHFFFAOYSA-N 0.000 abstract 1
235000013350 formula milk Nutrition 0.000 description 217
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 203
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 141
239000000203 mixture Substances 0.000 description 139
239000000243 solution Substances 0.000 description 117
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 113
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 110
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 96
239000000741 silica gel Substances 0.000 description 87
229910002027 silica gel Inorganic materials 0.000 description 87
239000000047 product Substances 0.000 description 81
238000004809 thin layer chromatography Methods 0.000 description 80
238000005481 NMR spectroscopy Methods 0.000 description 77
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 75
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
229940093499 ethyl acetate Drugs 0.000 description 67
235000019439 ethyl acetate Nutrition 0.000 description 67
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 58
239000012267 brine Substances 0.000 description 58
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 58
230000003595 spectral effect Effects 0.000 description 58
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 57
239000012074 organic phase Substances 0.000 description 51
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 50
230000009102 absorption Effects 0.000 description 45
238000010521 absorption reaction Methods 0.000 description 45
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 43
230000000875 corresponding effect Effects 0.000 description 41
239000003921 oil Substances 0.000 description 39
229910052799 carbon Inorganic materials 0.000 description 37
229960001123 epoprostenol Drugs 0.000 description 35
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 34
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 34
KAQKFAOMNZTLHT-VVUHWYTRSA-N epoprostenol Chemical compound O1C(=CCCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 KAQKFAOMNZTLHT-VVUHWYTRSA-N 0.000 description 31
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
229960004132 diethyl ether Drugs 0.000 description 30
HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical compound O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 description 29
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
150000002148 esters Chemical class 0.000 description 24
238000003756 stirring Methods 0.000 description 24
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 23
230000000903 blocking effect Effects 0.000 description 23
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 23
238000010898 silica gel chromatography Methods 0.000 description 23
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 22
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 22
150000002500 ions Chemical class 0.000 description 21
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
DCERHCFNWRGHLK-UHFFFAOYSA-N C[Si](C)C Chemical compound C[Si](C)C DCERHCFNWRGHLK-UHFFFAOYSA-N 0.000 description 19
FDSGHYHRLSWSLQ-UHFFFAOYSA-N dichloromethane;propan-2-one Chemical compound ClCCl.CC(C)=O FDSGHYHRLSWSLQ-UHFFFAOYSA-N 0.000 description 19
239000007858 starting material Substances 0.000 description 19
241001465754 Metazoa Species 0.000 description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
238000004587 chromatography analysis Methods 0.000 description 18
239000002904 solvent Substances 0.000 description 18
PXGPLTODNUVGFL-BRIYLRKRSA-N (E,Z)-(1R,2R,3R,5S)-7-(3,5-Dihydroxy-2-((3S)-(3-hydroxy-1-octenyl))cyclopentyl)-5-heptenoic acid Chemical compound CCCCC[C@H](O)C=C[C@H]1[C@H](O)C[C@H](O)[C@@H]1CC=CCCCC(O)=O PXGPLTODNUVGFL-BRIYLRKRSA-N 0.000 description 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 17
229960001701 chloroform Drugs 0.000 description 17
239000011541 reaction mixture Substances 0.000 description 17
239000000499 gel Substances 0.000 description 16
229910052708 sodium Inorganic materials 0.000 description 16
239000011734 sodium Substances 0.000 description 16
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 15
229940022663 acetate Drugs 0.000 description 15
239000003153 chemical reaction reagent Substances 0.000 description 15
230000009467 reduction Effects 0.000 description 14
238000006722 reduction reaction Methods 0.000 description 14
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 13
150000008064 anhydrides Chemical class 0.000 description 13
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 13
238000011282 treatment Methods 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 12
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
239000004593 Epoxy Substances 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
GCTFWCDSFPMHHS-UHFFFAOYSA-M Tributyltin chloride Chemical compound CCCC[Sn](Cl)(CCCC)CCCC GCTFWCDSFPMHHS-UHFFFAOYSA-M 0.000 description 12
150000001408 amides Chemical class 0.000 description 12
230000000694 effects Effects 0.000 description 12
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 12
150000002596 lactones Chemical class 0.000 description 12
239000000463 material Substances 0.000 description 12
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 12
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 12
150000003839 salts Chemical group 0.000 description 12
239000000377 silicon dioxide Substances 0.000 description 12
229960003010 sodium sulfate Drugs 0.000 description 12
229910052938 sodium sulfate Inorganic materials 0.000 description 12
235000011152 sodium sulphate Nutrition 0.000 description 12
125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 12
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 12
CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 11
229910000343 potassium bisulfate Inorganic materials 0.000 description 11
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
229920006395 saturated elastomer Polymers 0.000 description 11
239000011780 sodium chloride Substances 0.000 description 11
239000000725 suspension Substances 0.000 description 11
239000008280 blood Substances 0.000 description 10
210000004369 blood Anatomy 0.000 description 10
230000037396 body weight Effects 0.000 description 10
JCSGAUKCDAVARS-SOUFLCLCSA-N chembl2106517 Chemical compound C1([C@@H](O)[C@H]2C3)=CC=CC(O)=C1C(=O)C2=C(O)[C@@]1(O)[C@@H]3[C@H](N(C)C)C(O)=C(C(N)=O)C1=O JCSGAUKCDAVARS-SOUFLCLCSA-N 0.000 description 10
239000000706 filtrate Substances 0.000 description 10
229910052943 magnesium sulfate Inorganic materials 0.000 description 10
235000019341 magnesium sulphate Nutrition 0.000 description 10
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 9
241000282414 Homo sapiens Species 0.000 description 9
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 9
125000004494 ethyl ester group Chemical group 0.000 description 9
239000011630 iodine Substances 0.000 description 9
229910052740 iodine Inorganic materials 0.000 description 9
235000007686 potassium Nutrition 0.000 description 9
229960003975 potassium Drugs 0.000 description 9
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
241000124008 Mammalia Species 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
239000008346 aqueous phase Substances 0.000 description 8
239000012071 phase Substances 0.000 description 8
229910052700 potassium Inorganic materials 0.000 description 8
239000011591 potassium Substances 0.000 description 8
150000003180 prostaglandins Chemical class 0.000 description 8
229940001482 sodium sulfite Drugs 0.000 description 8
235000010265 sodium sulphite Nutrition 0.000 description 8
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 7
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 7
UQDAEORWFCPQCU-UHFFFAOYSA-N acetic acid;oxolane;hydrate Chemical compound O.CC(O)=O.C1CCOC1 UQDAEORWFCPQCU-UHFFFAOYSA-N 0.000 description 7
150000001768 cations Chemical class 0.000 description 7
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 7
230000010339 dilation Effects 0.000 description 7
MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 7
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 7
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 7
239000005457 ice water Substances 0.000 description 7
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 7
150000002825 nitriles Chemical class 0.000 description 7
229940094443 oxytocics prostaglandins Drugs 0.000 description 7
239000007787 solid Chemical class 0.000 description 7
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 7
230000001131 transforming effect Effects 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
238000007792 addition Methods 0.000 description 6
239000000443 aerosol Substances 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
150000001450 anions Chemical class 0.000 description 6
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 6
239000007795 chemical reaction product Substances 0.000 description 6
NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 6
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
150000002170 ethers Chemical class 0.000 description 6
229940052303 ethers for general anesthesia Drugs 0.000 description 6
239000000284 extract Substances 0.000 description 6
230000007062 hydrolysis Effects 0.000 description 6
238000006460 hydrolysis reaction Methods 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 6
238000001802 infusion Methods 0.000 description 6
208000037805 labour Diseases 0.000 description 6
239000012280 lithium aluminium hydride Substances 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
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LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
NFHRNKANAAGQOH-UHFFFAOYSA-N triphenylstannane Chemical compound C1=CC=CC=C1[SnH](C=1C=CC=CC=1)C1=CC=CC=C1 NFHRNKANAAGQOH-UHFFFAOYSA-N 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
230000001562 ulcerogenic effect Effects 0.000 description 1
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
210000002700 urine Anatomy 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
230000002792 vascular Effects 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
201000002282 venous insufficiency Diseases 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
- C07D307/935—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/10—Mercury compounds

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (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)
Plural Heterocyclic Compounds (AREA)

CA000279106A 1976-06-01 1977-05-25 5,6-dihydro-prostacyclin analogs Expired CA1196632A (en)

Applications Claiming Priority (8)

Application Number	Priority Date	Filing Date
US69140076A	1976-06-01	1976-06-01
US69139976A	1976-06-01	1976-06-01
US691,400		1976-06-01
US691,399		1976-06-01
US78814677A	1977-04-19	1977-04-19
US78814777A	1977-04-19	1977-04-19
US788,147		1977-04-19
US788,146		1977-04-19

Publications (1)

Publication Number	Publication Date
CA1196632A true CA1196632A (en)	1985-11-12

Family

ID=27505431

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000279106A Expired CA1196632A (en)	1976-06-01	1977-05-25	5,6-dihydro-prostacyclin analogs

Country Status (13)

Country	Link
JP (1)	JPS5936912B2 (sv)
AU (1)	AU508891B2 (sv)
BE (1)	BE855224A (sv)
CA (1)	CA1196632A (sv)
CH (1)	CH640847A5 (sv)
DE (1)	DE2724555A1 (sv)
FR (1)	FR2353543B1 (sv)
GB (1)	GB1554048A (sv)
IE (1)	IE45604B1 (sv)
IL (1)	IL52099A (sv)
MX (1)	MX4813E (sv)
NL (1)	NL7705991A (sv)
SE (3)	SE436744B (sv)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL51189A (en) *	1976-02-04	1985-08-30	Upjohn Co	Prostaglandin analogs
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
DE2743283A1 (de) *	1977-09-27	1979-04-05	Hoechst Ag	Neue prostacyclin-analoga
DE2811950A1 (de) *	1978-03-18	1979-12-13	Hoechst Ag	Neue analoga von prostacyclin
US4237060A (en)	1979-03-23	1980-12-02	Hoffmann-La Roche Inc.	Prostacyclin analogs
KR20020016938A (ko) *	1999-08-05	2002-03-06	야스이 쇼사꾸	함질소화합물을 유효성분으로 하는 신경장해개선제

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH629493A5 (en) *	1976-05-11	1982-04-30	Wellcome Found	Processes for preparing novel prostaglandin derivatives

1977
- 1977-04-10 MX MX77100668U patent/MX4813E/es unknown
- 1977-05-11 AU AU25086/77A patent/AU508891B2/en not_active Ceased
- 1977-05-16 IL IL52099A patent/IL52099A/xx unknown
- 1977-05-20 GB GB21363/77A patent/GB1554048A/en not_active Expired
- 1977-05-25 CA CA000279106A patent/CA1196632A/en not_active Expired
- 1977-05-27 CH CH660877A patent/CH640847A5/de not_active IP Right Cessation
- 1977-05-27 SE SE7706245A patent/SE436744B/sv not_active IP Right Cessation
- 1977-05-31 DE DE19772724555 patent/DE2724555A1/de not_active Withdrawn
- 1977-05-31 FR FR7716615A patent/FR2353543B1/fr not_active Expired
- 1977-05-31 BE BE178059A patent/BE855224A/xx not_active IP Right Cessation
- 1977-06-01 JP JP52063395A patent/JPS5936912B2/ja not_active Expired
- 1977-06-01 IE IE1133/77A patent/IE45604B1/en unknown
- 1977-06-01 NL NL7705991A patent/NL7705991A/xx not_active Application Discontinuation
1978
- 1978-10-26 SE SE7811142A patent/SE432101B/sv unknown
1982
- 1982-03-16 SE SE8201649A patent/SE8201649L/sv not_active Application Discontinuation

Also Published As

Publication number	Publication date
MX4813E (es)	1982-10-19
SE8201649L (sv)	1982-03-16
SE436744B (sv)	1985-01-21
JPS5936912B2 (ja)	1984-09-06
IE45604B1 (en)	1982-10-06
SE7811142L (sv)	1978-11-28
IL52099A0 (en)	1977-07-31
CH640847A5 (en)	1984-01-31
AU508891B2 (en)	1980-04-03
FR2353543B1 (fr)	1986-02-21
IE45604L (en)	1977-12-01
NL7705991A (nl)	1977-12-05
GB1554048A (en)	1979-10-17
SE7706245L (sv)	1977-12-16
SE432101B (sv)	1984-03-19
BE855224A (fr)	1977-11-30
AU2508677A (en)	1978-11-16
JPS52156854A (en)	1977-12-27
DE2724555A1 (de)	1977-12-15
IL52099A (en)	1985-03-31
FR2353543A1 (fr)	1977-12-30

Legal Events

Date	Code	Title	Description
2002-11-12	MKEX	Expiry

Publication	Publication Date	Title
US4123441A (en)	1978-10-31	Enlarged-hetero-ring prostacyclin analogs
US4029681A (en)	1977-06-14	13,14-Didehydro-PG analogs
US4158667A (en)	1979-06-19	6-Keto PGF analogs
CA1160628A (en)	1984-01-17	6-KETO AND 5-HEMIKETAL-PGF IN1.alpha. XX, METHYL ESTERS
US4238414A (en)	1980-12-09	2-Decarboxy-2-aminomethyl-6a-carba-PGI2 compounds
US4016184A (en)	1977-04-05	9-Deoxy-9,10-didehydro-PGD1 compounds
US4033989A (en)	1977-07-05	9-Deoxy-PGF2 Analogs
IE48178B1 (en)	1984-10-17	Prostacyclin analogs
US4205178A (en)	1980-05-27	6-Keto prostaglandin E-type compounds
US4013695A (en)	1977-03-22	4,4,5,5-Tetradehydro-PGE1 analogs
CA1077473A (en)	1980-05-13	2-decarboxy-2-aminomethyl-prostaglandin analogs
US4060534A (en)	1977-11-29	9-Deoxy-9-methylene-PGF compounds
USRE29926E (en)	1979-03-06	2-Decarboxy-2-hydroxy-methyl-16-fluoro-PGE1 compounds
CA1196632A (en)	1985-11-12	5,6-dihydro-prostacyclin analogs
US4490537A (en)	1984-12-25	Enlarged-hetero-ring prostacyclin analogs
US4499293A (en)	1985-02-12	PGI2 Salts
US4125713A (en)	1978-11-14	Certain 5,6-dihydra-prostacyclin analogs
US4028419A (en)	1977-06-07	2-Decarboxy-2-hydroxymethyl-cis-4,5-didehydro-PGE, compounds
US4124601A (en)	1978-11-07	Certain 5-halo-6,9α-epoxy-14-bromo(or chloro)-PGF1 compounds
CA1159452A (en)	1983-12-27	(5e)-9-deoxy-6,9-epoxy-prostaglandin derivatives
CA1184906A (en)	1985-04-02	9-deoxy-5,9-epoxy-prostaglandins
US4125712A (en)	1978-11-14	Certain 5,6-dihydro-prostacyclin analogs
US4490549A (en)	1984-12-25	Enlarged-hetero-ring prostacyclin analogs
US4099015A (en)	1978-07-04	2,2-Difluoro-13,14-didehydro-11-deoxy-17-phenyl-18,19,20-trinor-PGE2 compounds
US4490548A (en)	1984-12-25	Enlarged-hetero-ring prostacyclin analogs