NO751974L - - Google Patents

Info

Publication number: NO751974L
Authority: NO; Norway
Prior art keywords: trans; hydroxy; octenyl; compound according; cis
Prior art date: 1974-06-05

Application number

NO751974A

Other languages

English (en)

Norwegian (no)

Inventor

K G Untch

Original Assignee

Syntex Inc

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.)

1974-06-05

Filing date

1975-06-04

Publication date

1975-12-08

1975-06-04 Application filed by Syntex Inc filed Critical Syntex Inc

1975-12-08 Publication of NO751974L publication Critical patent/NO751974L/no

Links

150000001875 compounds Chemical class 0.000 claims description 69
-1 sulfinyl-trans-2-octenyl compounds Chemical class 0.000 claims description 18
238000002360 preparation method Methods 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 15
125000004432 carbon atom Chemical group C* 0.000 claims description 13
125000000217 alkyl group Chemical group 0.000 claims description 11
238000000034 method Methods 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
229920006395 saturated elastomer Polymers 0.000 claims description 5
231100000252 nontoxic Toxicity 0.000 claims description 4
230000003000 nontoxic effect Effects 0.000 claims description 4
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 claims description 3
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
150000001412 amines Chemical class 0.000 claims description 2
XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 claims description 2
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical class ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
230000003301 hydrolyzing effect Effects 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 16
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
239000002253 acid Substances 0.000 description 12
229940094443 oxytocics prostaglandins Drugs 0.000 description 12
150000003180 prostaglandins Chemical class 0.000 description 10
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
239000000243 solution Substances 0.000 description 9
229960001340 histamine Drugs 0.000 description 8
125000001424 substituent group Chemical group 0.000 description 8
150000007513 acids Chemical class 0.000 description 7
239000000203 mixture Substances 0.000 description 7
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
239000007788 liquid Substances 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
239000006228 supernatant Substances 0.000 description 6
229940124630 bronchodilator Drugs 0.000 description 5
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
241000124008 Mammalia Species 0.000 description 4
102000019280 Pancreatic lipases Human genes 0.000 description 4
108050006759 Pancreatic lipases Proteins 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
239000000463 material Substances 0.000 description 4
229940116369 pancreatic lipase Drugs 0.000 description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
239000000523 sample Substances 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
238000012360 testing method Methods 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
RSGBMGFQNOGIPC-UHFFFAOYSA-N (4-methylphenyl) thiohypochlorite Chemical compound CC1=CC=C(SCl)C=C1 RSGBMGFQNOGIPC-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
239000000443 aerosol Substances 0.000 description 3
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 3
239000000168 bronchodilator agent Substances 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
150000001940 cyclopentanes Chemical class 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000001914 filtration Methods 0.000 description 3
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
239000003755 preservative agent Substances 0.000 description 3
238000000926 separation method Methods 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
BZWJDKJBAVXCMH-UHFFFAOYSA-N 1-diazopropane Chemical compound CCC=[N+]=[N-] BZWJDKJBAVXCMH-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical class N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical class 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 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000000872 buffer Substances 0.000 description 2
RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
210000001715 carotid artery Anatomy 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
WLXALCKAKGDNAT-UHFFFAOYSA-N diazoethane Chemical compound CC=[N+]=[N-] WLXALCKAKGDNAT-UHFFFAOYSA-N 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
125000004185 ester group Chemical group 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
230000001939 inductive effect Effects 0.000 description 2
229910052742 iron Inorganic materials 0.000 description 2
125000000468 ketone group Chemical group 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
150000004702 methyl esters Chemical class 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
239000011736 potassium bicarbonate Substances 0.000 description 2
235000015497 potassium bicarbonate Nutrition 0.000 description 2
229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
230000002997 prostaglandinlike Effects 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000002904 solvent Substances 0.000 description 2
FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical class ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 2
230000009897 systematic effect Effects 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
238000007738 vacuum evaporation Methods 0.000 description 2
WVTOJNFZIVWNIY-UHFFFAOYSA-N (4-chlorophenyl) thiohypochlorite Chemical compound ClSC1=CC=C(Cl)C=C1 WVTOJNFZIVWNIY-UHFFFAOYSA-N 0.000 description 1
FLZPTLSRDKJVLE-UHFFFAOYSA-N 1,2-dimethoxyethane-1,2-diol Chemical compound COC(O)C(O)OC FLZPTLSRDKJVLE-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
CTHZICXYLKQMKI-FOSBLDSVSA-N 11-Deoxy-PGE2 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1CCC(=O)[C@@H]1C\C=C/CCCC(O)=O CTHZICXYLKQMKI-FOSBLDSVSA-N 0.000 description 1
HYBPXYQCXNOTFK-DUSCRHDRSA-N 11-Deoxy-PGF1alpha Chemical compound CCCCC[C@H](O)\C=C\[C@H]1CC[C@H](O)[C@@H]1CCCCCCC(O)=O HYBPXYQCXNOTFK-DUSCRHDRSA-N 0.000 description 1
CTHZICXYLKQMKI-UHFFFAOYSA-N 11-deoxyprostaglandin E2 Natural products CCCCCC(O)C=CC1CCC(=O)C1CC=CCCCC(O)=O CTHZICXYLKQMKI-UHFFFAOYSA-N 0.000 description 1
LUTDLYPHDVQSHT-UHFFFAOYSA-N 2-hydroxycyclopentan-1-one Chemical compound OC1CCCC1=O LUTDLYPHDVQSHT-UHFFFAOYSA-N 0.000 description 1
AGYVLJKQIZOYBJ-UHFFFAOYSA-N 2-methylpropyl thiohypochlorite Chemical compound CC(C)CSCl AGYVLJKQIZOYBJ-UHFFFAOYSA-N 0.000 description 1
CDGZBXSRVMXAMG-UHFFFAOYSA-N 3-methylbutyl thiohypochlorite Chemical compound CC(C)CCSCl CDGZBXSRVMXAMG-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
101100188551 Arabidopsis thaliana OCT2 gene Proteins 0.000 description 1
239000004475 Arginine Substances 0.000 description 1
208000009079 Bronchial Spasm Diseases 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical class [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
241000700198 Cavia Species 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 1
ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
239000004367 Lipase Substances 0.000 description 1
102000004882 Lipase Human genes 0.000 description 1
108090001060 Lipase Proteins 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical class [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
208000037093 Menstruation Disturbances Diseases 0.000 description 1
AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
WINXNKPZLFISPD-UHFFFAOYSA-M Saccharin sodium Chemical compound [Na+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 WINXNKPZLFISPD-UHFFFAOYSA-M 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
241000282887 Suidae Species 0.000 description 1
RNJDTXXKXAXYMK-UHFFFAOYSA-N [chloro(difluoro)methyl] thiohypochlorite Chemical compound FC(F)(Cl)SCl RNJDTXXKXAXYMK-UHFFFAOYSA-N 0.000 description 1
KDRSHFSCTSFYGH-UHFFFAOYSA-N [dichloro(fluoro)methyl] thiohypochlorite Chemical compound FC(Cl)(Cl)SCl KDRSHFSCTSFYGH-UHFFFAOYSA-N 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
239000004411 aluminium Chemical class 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical class [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
229910052921 ammonium sulfate Inorganic materials 0.000 description 1
235000011130 ammonium sulphate Nutrition 0.000 description 1
230000003509 anti-fertility effect Effects 0.000 description 1
229940121363 anti-inflammatory agent Drugs 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
229960003121 arginine Drugs 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
239000007975 buffered saline Substances 0.000 description 1
UJXBZCDDWHNWNG-UHFFFAOYSA-N butyl thiohypochlorite Chemical compound CCCCSCl UJXBZCDDWHNWNG-UHFFFAOYSA-N 0.000 description 1
VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 1
229960001948 caffeine Drugs 0.000 description 1
239000011575 calcium Chemical class 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
SWYHWRRXAKMZLK-UHFFFAOYSA-N chloromethyl thiohypochlorite Chemical compound ClCSCl SWYHWRRXAKMZLK-UHFFFAOYSA-N 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
235000008504 concentrate Nutrition 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
XRFDWTWFFLOKAV-UHFFFAOYSA-N cyclohexyl thiohypochlorite Chemical compound ClSC1CCCCC1 XRFDWTWFFLOKAV-UHFFFAOYSA-N 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
WEZMXIQSRUEFJL-UHFFFAOYSA-N cyclopentyl thiohypochlorite Chemical compound ClSC1CCCC1 WEZMXIQSRUEFJL-UHFFFAOYSA-N 0.000 description 1
238000007257 deesterification reaction Methods 0.000 description 1
230000000994 depressogenic effect Effects 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000010828 elution Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
229960004756 ethanol Drugs 0.000 description 1
UHMZHYUCMREDRI-UHFFFAOYSA-N ethyl thiohypochlorite Chemical compound CCSCl UHMZHYUCMREDRI-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
PKLOCXCFMPIHTB-UHFFFAOYSA-N hexyl thiohypochlorite Chemical compound CCCCCCSCl PKLOCXCFMPIHTB-UHFFFAOYSA-N 0.000 description 1
229940088597 hormone Drugs 0.000 description 1
239000005556 hormone Substances 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
239000008101 lactose Substances 0.000 description 1
229940040461 lipase Drugs 0.000 description 1
235000019421 lipase Nutrition 0.000 description 1
229960003646 lysine Drugs 0.000 description 1
239000011777 magnesium Chemical class 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
231100000544 menstrual irregularity Toxicity 0.000 description 1
230000005906 menstruation Effects 0.000 description 1
DDCYYCUMAFYDDU-UHFFFAOYSA-N methyl thiohypochlorite Chemical compound CSCl DDCYYCUMAFYDDU-UHFFFAOYSA-N 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
229930014626 natural product Natural products 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
239000006174 pH buffer Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
NIIOVMOMNIFUSO-UHFFFAOYSA-N pentyl thiohypochlorite Chemical compound CCCCCSCl NIIOVMOMNIFUSO-UHFFFAOYSA-N 0.000 description 1
RYFZYYUIAZYQLC-UHFFFAOYSA-N perchloromethyl mercaptan Chemical compound ClSC(Cl)(Cl)Cl RYFZYYUIAZYQLC-UHFFFAOYSA-N 0.000 description 1
JWUKZUIGOJBEPC-UHFFFAOYSA-N phenyl thiohypochlorite Chemical compound ClSC1=CC=CC=C1 JWUKZUIGOJBEPC-UHFFFAOYSA-N 0.000 description 1
125000002467 phosphate group Chemical class [H]OP(=O)(O[H])O[*] 0.000 description 1
239000006187 pill Substances 0.000 description 1
239000011591 potassium Chemical class 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000035935 pregnancy Effects 0.000 description 1
238000012746 preparative thin layer chromatography Methods 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
239000000047 product Substances 0.000 description 1
MAUIZVRLYLDWDK-UHFFFAOYSA-N propan-2-yl thiohypochlorite Chemical compound CC(C)SCl MAUIZVRLYLDWDK-UHFFFAOYSA-N 0.000 description 1
239000003380 propellant Substances 0.000 description 1
DNAHRRFQXGRERW-UHFFFAOYSA-N propyl thiohypochlorite Chemical compound CCCSCl DNAHRRFQXGRERW-UHFFFAOYSA-N 0.000 description 1
ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000011160 research Methods 0.000 description 1
230000000241 respiratory effect Effects 0.000 description 1
229940125723 sedative agent Drugs 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000004289 sodium hydrogen sulphite Substances 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
210000003437 trachea Anatomy 0.000 description 1
RQYLOOVORNJDQX-UHFFFAOYSA-N trifluoromethyl thiohypochlorite Chemical compound FC(F)(F)SCl RQYLOOVORNJDQX-UHFFFAOYSA-N 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
238000002604 ultrasonography Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- 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
- C07C405/0033—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing sulfur
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (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)

NO751974A 1974-06-05 1975-06-04 NO751974L (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US47635774A	1974-06-05	1974-06-05

Publications (1)

Publication Number	Publication Date
NO751974L true NO751974L (fr)	1975-12-08

Family

ID=23891522

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO751974A NO751974L (fr)	1974-06-05	1975-06-04

Country Status (15)

Country	Link
JP (1)	JPS5111744A (fr)
AT (1)	AT348155B (fr)
AU (1)	AU8179075A (fr)
BE (1)	BE829819A (fr)
CH (1)	CH615419A5 (fr)
DE (1)	DE2524657A1 (fr)
DK (1)	DK245175A (fr)
ES (1)	ES438239A1 (fr)
FR (1)	FR2273525A1 (fr)
GB (1)	GB1497466A (fr)
IL (1)	IL47356A (fr)
NL (1)	NL7506668A (fr)
NO (1)	NO751974L (fr)
SE (1)	SE7506390L (fr)
ZA (1)	ZA753249B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1541962A (en) *	1976-02-25	1979-03-14	Sagami Chem Res	Prostaglandin precursors and processes for preparing the same
US7710866B2 (en)	2001-09-27	2010-05-04	Alcatel-Lucent Canada Inc.	Method and apparatus for optimization of redundant link usage in a multi-shelf network element

1975
- 1975-05-20 ZA ZA3249A patent/ZA753249B/xx unknown
- 1975-05-26 IL IL47356A patent/IL47356A/xx unknown
- 1975-05-30 DK DK245175A patent/DK245175A/da not_active Application Discontinuation
- 1975-06-03 GB GB23975/75A patent/GB1497466A/en not_active Expired
- 1975-06-03 BE BE156987A patent/BE829819A/fr unknown
- 1975-06-03 AU AU81790/75A patent/AU8179075A/en not_active Expired
- 1975-06-03 DE DE19752524657 patent/DE2524657A1/de active Pending
- 1975-06-04 FR FR7517496A patent/FR2273525A1/fr active Granted
- 1975-06-04 ES ES438239A patent/ES438239A1/es not_active Expired
- 1975-06-04 SE SE7506390A patent/SE7506390L/xx unknown
- 1975-06-04 JP JP50067442A patent/JPS5111744A/ja active Pending
- 1975-06-04 AT AT425275A patent/AT348155B/de not_active IP Right Cessation
- 1975-06-04 NO NO751974A patent/NO751974L/no unknown
- 1975-06-05 NL NL7506668A patent/NL7506668A/xx not_active Application Discontinuation
- 1975-06-05 CH CH726975A patent/CH615419A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
CH615419A5 (en)	1980-01-31
ES438239A1 (es)	1977-05-16
AU8179075A (en)	1976-12-09
NL7506668A (nl)	1975-12-09
JPS5111744A (en)	1976-01-30
BE829819A (fr)	1975-12-03
ZA753249B (en)	1977-01-26
IL47356A (en)	1978-06-15
ATA425275A (de)	1978-06-15
SE7506390L (sv)	1975-12-08
FR2273525B1 (fr)	1979-08-10
FR2273525A1 (fr)	1976-01-02
AT348155B (de)	1979-02-12
GB1497466A (en)	1978-01-12
DE2524657A1 (de)	1976-04-15
DK245175A (da)	1975-12-06
IL47356A0 (en)	1975-07-28

Publication	Publication Date	Title
CA1322197C (fr)	1993-09-14	Derives 9-halogene-(z)-prostaglandine, procede pour leur production et leur utilisation comme agents pharmaceutiques
CA1223255A (fr)	1987-06-23	Derives de carbacycline, leur preparation et leur emploi en pharmacie
US4178457A (en)	1979-12-11	(dl)-16-Phenoxy- and 16-substituted phenoxy-9-keto prostatrienoic acid derivatives and processes for the production thereof
US8389748B2 (en)	2013-03-05	Method for preparing prostaglandin derivative
AU669226B2 (en)	1996-05-30	Prostaglandine derivative
JP5511389B2 (ja)	2014-06-04	４’−エチニルｄ４Ｔの製造方法
JPS5929193B2 (ja)	1984-07-18	４，４，５，５−テトラデヒドロｐｇｆ１
US3931279A (en)	1976-01-06	5-Oxa prostaglandin F2.sub.α analogs
WO1992018473A1 (fr)	1992-10-29	Analogue de prostaglandine e¿1?
WO1994002457A1 (fr)	1994-02-03	Derive de prostaglandine
CH619691A5 (fr)	1980-10-15
NO751974L (fr)	1975-12-08
NO763451L (fr)	1977-04-22
NO852319L (no)	1985-12-13	Fremgangsmaate for fremstilling av 13-aza-14-okso-txa2-analog-forbindelser.
US3970685A (en)	1976-07-20	(DL)-13-Substituted sulfinyl-prostaglandin-like compounds
JP2003321442A (ja)	2003-11-11	新規なジフルオロプロスタグランジンアミド誘導体
US3997587A (en)	1976-12-14	D1- and 8R-9-fluoro-prostadienoic acid derivatives
CA1038378A (fr)	1978-09-12	Derives de la 13 - cis prostaglandine et methode de preparation
NO752734L (fr)	1976-02-06
US3969381A (en)	1976-07-13	13,14-Dihydro-16-fluoro prostaglandin B1 analogs
US3969376A (en)	1976-07-13	13,14-Dihydro-16-fluoro prostaglandin E1 analogs
JPS6212775A (ja)	1987-01-21	〔５，６〕‐シス‐１，３‐オキサチアン誘導体、その製造法、および該化合物を含有する医薬組成物
US3969379A (en)	1976-07-13	13,14-Dihydro-16-fluoro prostaglandin A1 analogs
WO1989001936A1 (fr)	1989-03-09	Procede de production d'intermediaires de prostaglandines
JP2872468B2 (ja)	1999-03-17	イソカルバサイクリン誘導体、その製造法および光親和性標識法