CA1047491A

CA1047491A - Prostaglandin-type compounds and process for their preparation

Prostaglandin-type compounds and process for their preparation

Info

Publication number: CA1047491A
Authority: CA; Canada
Prior art keywords: inclusive; carbon atoms; hydrogen; formula; alkyl
Prior art date: 1972-09-15
Legal status : Expired

Application number

CA180,595A

Other languages

English (en)

French (fr)

Other versions

CA180595S (en

Inventor

Ernest W. Yankee

Current Assignee

Pharmacia and Upjohn Co

Original Assignee

Upjohn Co

Priority date

1972-09-15

Filing date

1973-09-10

Publication date

1979-01-30

1973-09-10 Application filed by Upjohn Co filed Critical Upjohn Co

1979-01-30 Application granted granted Critical

1979-01-30 Publication of CA1047491A publication Critical patent/CA1047491A/en

Status Expired legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 222
238000000034 method Methods 0.000 title claims abstract description 138
230000008569 process Effects 0.000 title claims abstract description 22
238000002360 preparation method Methods 0.000 title description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 104
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 42
-1 inclusive Chemical group 0.000 claims description 110
239000001257 hydrogen Substances 0.000 claims description 84
229910052739 hydrogen Inorganic materials 0.000 claims description 84
239000000203 mixture Substances 0.000 claims description 83
125000004432 carbon atom Chemical group C* 0.000 claims description 82
125000000217 alkyl group Chemical group 0.000 claims description 66
239000002253 acid Chemical group 0.000 claims description 53
150000002148 esters Chemical group 0.000 claims description 43
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 41
239000000047 product Substances 0.000 claims description 39
150000002431 hydrogen Chemical class 0.000 claims description 23
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
125000003710 aryl alkyl group Chemical group 0.000 claims description 12
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 12
125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 11
125000001309 chloro group Chemical group Cl* 0.000 claims description 10
125000000753 cycloalkyl group Chemical group 0.000 claims description 10
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 5
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
239000003638 chemical reducing agent Substances 0.000 claims description 5
125000003884 phenylalkyl group Chemical group 0.000 claims description 5
125000001153 fluoro group Chemical group F* 0.000 claims description 4
239000000126 substance Substances 0.000 claims description 4
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
230000001590 oxidative effect Effects 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims 4
239000007795 chemical reaction product Substances 0.000 claims 3
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 3
229930194542 Keto Natural products 0.000 claims 2
230000002152 alkylating effect Effects 0.000 claims 2
125000000468 ketone group Chemical group 0.000 claims 2
125000000686 lactone group Chemical group 0.000 claims 2
150000001298 alcohols Chemical class 0.000 claims 1
230000005764 inhibitory process Effects 0.000 abstract description 4
238000006467 substitution reaction Methods 0.000 abstract description 4
208000010110 spontaneous platelet aggregation Diseases 0.000 abstract description 2
230000000767 anti-ulcer Effects 0.000 abstract 1
230000000144 pharmacologic effect Effects 0.000 abstract 1
235000013350 formula milk Nutrition 0.000 description 116
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 104
150000004702 methyl esters Chemical class 0.000 description 99
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 96
239000000243 solution Substances 0.000 description 78
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 70
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 66
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 62
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 50
230000000875 corresponding effect Effects 0.000 description 48
229960002986 dinoprostone Drugs 0.000 description 48
238000006243 chemical reaction Methods 0.000 description 41
238000004809 thin layer chromatography Methods 0.000 description 41
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 38
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 34
239000000741 silica gel Substances 0.000 description 34
229910002027 silica gel Inorganic materials 0.000 description 34
229960001866 silicon dioxide Drugs 0.000 description 34
230000003595 spectral effect Effects 0.000 description 33
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 32
239000000543 intermediate Substances 0.000 description 29
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
239000012074 organic phase Substances 0.000 description 27
239000012267 brine Substances 0.000 description 26
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 26
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 25
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 22
229910052938 sodium sulfate Inorganic materials 0.000 description 22
229960003010 sodium sulfate Drugs 0.000 description 22
235000011152 sodium sulphate Nutrition 0.000 description 22
150000003180 prostaglandins Chemical class 0.000 description 21
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 20
230000002829 reductive effect Effects 0.000 description 20
238000003756 stirring Methods 0.000 description 20
235000002639 sodium chloride Nutrition 0.000 description 19
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 18
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 17
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 17
150000003839 salts Chemical class 0.000 description 17
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
230000000903 blocking effect Effects 0.000 description 16
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
241001465754 Metazoa Species 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 15
239000011734 sodium Substances 0.000 description 15
229910052708 sodium Inorganic materials 0.000 description 15
HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical compound O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 description 14
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 14
150000007513 acids Chemical class 0.000 description 14
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 14
229910052757 nitrogen Inorganic materials 0.000 description 14
230000003287 optical effect Effects 0.000 description 13
150000003166 prostaglandin E2 derivatives Chemical class 0.000 description 13
229920006395 saturated elastomer Polymers 0.000 description 13
239000002904 solvent Substances 0.000 description 13
125000000026 trimethylsilyl group Chemical class [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 13
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 12
239000003153 chemical reaction reagent Substances 0.000 description 12
239000007788 liquid Substances 0.000 description 12
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 11
239000003085 diluting agent Substances 0.000 description 11
229960005419 nitrogen Drugs 0.000 description 11
229940094443 oxytocics prostaglandins Drugs 0.000 description 11
XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 11
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
230000037396 body weight Effects 0.000 description 10
230000000694 effects Effects 0.000 description 10
238000000605 extraction Methods 0.000 description 10
238000001802 infusion Methods 0.000 description 10
229910052751 metal Inorganic materials 0.000 description 10
239000002184 metal Substances 0.000 description 10
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
150000002118 epoxides Chemical class 0.000 description 9
235000019441 ethanol Nutrition 0.000 description 9
238000005227 gel permeation chromatography Methods 0.000 description 9
238000006460 hydrolysis reaction Methods 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
230000009467 reduction Effects 0.000 description 9
238000010898 silica gel chromatography Methods 0.000 description 9
230000009466 transformation Effects 0.000 description 9
YVHAIVPPUIZFBA-UHFFFAOYSA-N Cyclopentylacetic acid Chemical compound OC(=O)CC1CCCC1 YVHAIVPPUIZFBA-UHFFFAOYSA-N 0.000 description 8
229910052782 aluminium Inorganic materials 0.000 description 8
150000001412 amines Chemical class 0.000 description 8
239000000499 gel Substances 0.000 description 8
230000007062 hydrolysis Effects 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
239000000376 reactant Substances 0.000 description 8
239000000377 silicon dioxide Substances 0.000 description 8
239000007858 starting material Substances 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
241000219210 Plexaura homomalla Species 0.000 description 7
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
150000001768 cations Chemical class 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
239000000284 extract Substances 0.000 description 7
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 7
229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
229960001407 sodium bicarbonate Drugs 0.000 description 7
235000017557 sodium bicarbonate Nutrition 0.000 description 7
WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 7
229910000342 sodium bisulfate Inorganic materials 0.000 description 7
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
239000012027 Collins reagent Substances 0.000 description 6
241000282414 Homo sapiens Species 0.000 description 6
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
241000124008 Mammalia Species 0.000 description 6
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
241000283973 Oryctolagus cuniculus Species 0.000 description 6
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
241000700159 Rattus Species 0.000 description 6
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000000538 analytical sample Substances 0.000 description 6
125000004429 atom Chemical group 0.000 description 6
230000008512 biological response Effects 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
210000004369 blood Anatomy 0.000 description 6
239000008280 blood Substances 0.000 description 6
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 6
230000000332 continued effect Effects 0.000 description 6
238000001704 evaporation Methods 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
150000002440 hydroxy compounds Chemical class 0.000 description 6
229910052700 potassium Inorganic materials 0.000 description 6
239000011591 potassium Substances 0.000 description 6
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 6
NPRDHMWYZHSAHR-UHFFFAOYSA-N pyridine;trioxochromium Chemical compound O=[Cr](=O)=O.C1=CC=NC=C1.C1=CC=NC=C1 NPRDHMWYZHSAHR-UHFFFAOYSA-N 0.000 description 6
239000007787 solid Substances 0.000 description 6
KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical group FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
230000029936 alkylation Effects 0.000 description 5
238000005804 alkylation reaction Methods 0.000 description 5
150000008064 anhydrides Chemical class 0.000 description 5
210000001772 blood platelet Anatomy 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
238000005886 esterification reaction Methods 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
150000002596 lactones Chemical class 0.000 description 5
150000002632 lipids Chemical class 0.000 description 5
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 5
230000003389 potentiating effect Effects 0.000 description 5
239000012279 sodium borohydride Substances 0.000 description 5
229910000033 sodium borohydride Inorganic materials 0.000 description 5
150000003512 tertiary amines Chemical class 0.000 description 5
238000000844 transformation Methods 0.000 description 5
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
241000282472 Canis lupus familiaris Species 0.000 description 4
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 4
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
241000219209 Plexaura Species 0.000 description 4
MYHXHCUNDDAEOZ-UHFFFAOYSA-N Prostaglandin A&2% Natural products CCCCCC(O)C=CC1C=CC(=O)C1CC=CCCCC(O)=O MYHXHCUNDDAEOZ-UHFFFAOYSA-N 0.000 description 4
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
238000010521 absorption reaction Methods 0.000 description 4
150000001299 aldehydes Chemical class 0.000 description 4
238000010171 animal model Methods 0.000 description 4
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
125000002704 decyl group Chemical group [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])* 0.000 description 4
WLXALCKAKGDNAT-UHFFFAOYSA-N diazoethane Chemical compound CC=[N+]=[N-] WLXALCKAKGDNAT-UHFFFAOYSA-N 0.000 description 4
FDSGHYHRLSWSLQ-UHFFFAOYSA-N dichloromethane;propan-2-one Chemical compound ClCCl.CC(C)=O FDSGHYHRLSWSLQ-UHFFFAOYSA-N 0.000 description 4
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 4
125000004494 ethyl ester group Chemical group 0.000 description 4
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 4
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 4
239000012442 inert solvent Substances 0.000 description 4
238000001990 intravenous administration Methods 0.000 description 4
238000010253 intravenous injection Methods 0.000 description 4
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
208000037805 labour Diseases 0.000 description 4
239000000463 material Substances 0.000 description 4
238000002156 mixing Methods 0.000 description 4
125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 4
239000012071 phase Substances 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
230000002035 prolonged effect Effects 0.000 description 4
MYHXHCUNDDAEOZ-FOSBLDSVSA-N prostaglandin A2 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1C=CC(=O)[C@@H]1C\C=C/CCCC(O)=O MYHXHCUNDDAEOZ-FOSBLDSVSA-N 0.000 description 4
150000003155 prostaglandin A2 derivatives Chemical class 0.000 description 4
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 4
125000001453 quaternary ammonium group Chemical group 0.000 description 4
230000028327 secretion Effects 0.000 description 4
238000000926 separation method Methods 0.000 description 4
NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 4
210000002460 smooth muscle Anatomy 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
230000000638 stimulation Effects 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
229910052725 zinc Inorganic materials 0.000 description 4
239000011701 zinc Substances 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
PFJVIOBMBDFBCJ-UHFFFAOYSA-N (1z)-1-diazobutane Chemical compound CCCC=[N+]=[N-] PFJVIOBMBDFBCJ-UHFFFAOYSA-N 0.000 description 3
UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 3
229930182837 (R)-adrenaline Natural products 0.000 description 3
MLOSJPZSZWUDSK-UHFFFAOYSA-N 4-carboxybutyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCC(=O)O)C1=CC=CC=C1 MLOSJPZSZWUDSK-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
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