CH617187A5 - - Google Patents
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- Publication number
- CH617187A5 CH617187A5 CH523979A CH523979A CH617187A5 CH 617187 A5 CH617187 A5 CH 617187A5 CH 523979 A CH523979 A CH 523979A CH 523979 A CH523979 A CH 523979A CH 617187 A5 CH617187 A5 CH 617187A5
- Authority
- CH
- Switzerland
- Prior art keywords
- compounds
- octenyl
- oxocyclopentane
- trans
- hydroxy
- Prior art date
Links
- -1 2-tetrahydropyranyl Chemical group 0.000 claims description 69
- 150000001875 compounds Chemical class 0.000 claims description 46
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 230000000269 nucleophilic effect Effects 0.000 claims description 2
- 150000003018 phosphorus compounds Chemical class 0.000 claims description 2
- 150000003335 secondary amines Chemical class 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 238000003776 cleavage reaction Methods 0.000 claims 1
- 125000001033 ether group Chemical group 0.000 claims 1
- 150000002440 hydroxy compounds Chemical class 0.000 claims 1
- 230000007017 scission Effects 0.000 claims 1
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 150000003180 prostaglandins Chemical class 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 229960001340 histamine Drugs 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 238000004809 thin layer chromatography Methods 0.000 description 5
- 241000124008 Mammalia Species 0.000 description 4
- 229940124630 bronchodilator Drugs 0.000 description 4
- 238000006243 chemical reaction Methods 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
- WGJJROVFWIXTPA-OALUTQOASA-N prostanoic acid Chemical compound CCCCCCCC[C@H]1CCC[C@@H]1CCCCCCC(O)=O WGJJROVFWIXTPA-OALUTQOASA-N 0.000 description 4
- 150000003839 salts Chemical class 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
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 239000000443 aerosol Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000000168 bronchodilator agent Substances 0.000 description 3
- 150000001940 cyclopentanes Chemical class 0.000 description 3
- 230000007794 irritation Effects 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- 230000002997 prostaglandinlike Effects 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000699694 Gerbillinae Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 239000006172 buffering agent Substances 0.000 description 2
- 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 2
- 210000001072 colon 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
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 210000003205 muscle Anatomy 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000012746 preparative thin layer chromatography Methods 0.000 description 2
- 230000002335 preservative effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- OAYOLVJSPVSUJU-UHFFFAOYSA-N (2,4-dichlorophenyl) thiohypochlorite Chemical compound ClSC1=CC=C(Cl)C=C1Cl OAYOLVJSPVSUJU-UHFFFAOYSA-N 0.000 description 1
- VPNUCTPEIZDTGG-UHFFFAOYSA-N (2,5-dichlorophenyl) thiohypochlorite Chemical compound ClSC1=CC(Cl)=CC=C1Cl VPNUCTPEIZDTGG-UHFFFAOYSA-N 0.000 description 1
- WVTOJNFZIVWNIY-UHFFFAOYSA-N (4-chlorophenyl) thiohypochlorite Chemical compound ClSC1=CC=C(Cl)C=C1 WVTOJNFZIVWNIY-UHFFFAOYSA-N 0.000 description 1
- GMVPRGQOIOIIMI-UHFFFAOYSA-N (8R,11R,12R,13E,15S)-11,15-Dihydroxy-9-oxo-13-prostenoic acid Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CCCCCCC(O)=O GMVPRGQOIOIIMI-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
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-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
- 208000009079 Bronchial Spasm Diseases 0.000 description 1
- 241001631457 Cannula Species 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 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
- 208000037093 Menstruation Disturbances Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 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
- 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
- 229960000711 alprostadil Drugs 0.000 description 1
- 230000003509 anti-fertility effect Effects 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000007853 buffer solution Substances 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
- 239000002775 capsule Substances 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 230000035606 childbirth Effects 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
- 230000002517 constrictor effect Effects 0.000 description 1
- GVCZADNZARGKQT-UHFFFAOYSA-N cycloheptyl thiohypochlorite Chemical compound ClSC1CCCCCC1 GVCZADNZARGKQT-UHFFFAOYSA-N 0.000 description 1
- XRFDWTWFFLOKAV-UHFFFAOYSA-N cyclohexyl thiohypochlorite Chemical compound ClSC1CCCCC1 XRFDWTWFFLOKAV-UHFFFAOYSA-N 0.000 description 1
- WEZMXIQSRUEFJL-UHFFFAOYSA-N cyclopentyl thiohypochlorite Chemical compound ClSC1CCCC1 WEZMXIQSRUEFJL-UHFFFAOYSA-N 0.000 description 1
- 230000003001 depressive effect Effects 0.000 description 1
- 210000001731 descending colon Anatomy 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000000839 emulsion Substances 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
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas 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
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 210000004731 jugular vein Anatomy 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 210000002429 large intestine Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 231100000544 menstrual irregularity Toxicity 0.000 description 1
- 230000005906 menstruation Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- DDCYYCUMAFYDDU-UHFFFAOYSA-N methyl thiohypochlorite Chemical compound CSCl DDCYYCUMAFYDDU-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000006179 pH buffering agent 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
- 230000000144 pharmacologic effect Effects 0.000 description 1
- JWUKZUIGOJBEPC-UHFFFAOYSA-N phenyl thiohypochlorite Chemical compound ClSC1=CC=CC=C1 JWUKZUIGOJBEPC-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate 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
- GMVPRGQOIOIIMI-DWKJAMRDSA-N prostaglandin E1 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O GMVPRGQOIOIIMI-DWKJAMRDSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 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
- 238000004904 shortening Methods 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical class ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 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
- 230000009897 systematic effect Effects 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
-
- 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
- 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
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P31/00—Preparation of compounds containing a five-membered ring having two side-chains in ortho position to each other, and having at least one oxygen atom directly bound to the ring in ortho position to one of the side-chains, one side-chain containing, not directly bound 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 at least one oxygen atom bound in gamma-position to the ring, e.g. prostaglandins
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU59068/80A AU5906880A (en) | 1979-06-05 | 1980-06-05 | Process for dyeing and tanning in a single bath |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/476,362 US3970685A (en) | 1974-06-05 | 1974-06-05 | (DL)-13-Substituted sulfinyl-prostaglandin-like compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH617187A5 true CH617187A5 (fr) | 1980-05-14 |
Family
ID=23891540
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH726775A CH611880A5 (fr) | 1974-06-05 | 1975-06-05 | |
| CH523979A CH617187A5 (fr) | 1974-06-05 | 1979-06-05 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH726775A CH611880A5 (fr) | 1974-06-05 | 1975-06-05 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3970685A (fr) |
| JP (1) | JPS5111743A (fr) |
| AT (1) | AT348156B (fr) |
| BE (1) | BE829820A (fr) |
| CA (1) | CA1039277A (fr) |
| CH (2) | CH611880A5 (fr) |
| DE (1) | DE2524619A1 (fr) |
| DK (1) | DK245075A (fr) |
| ES (2) | ES438237A1 (fr) |
| FR (1) | FR2273519A1 (fr) |
| GB (1) | GB1496845A (fr) |
| IL (1) | IL47354A (fr) |
| NL (1) | NL7506666A (fr) |
| NO (1) | NO751975L (fr) |
| SE (1) | SE7506388L (fr) |
| ZA (1) | ZA753247B (fr) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7605381A (nl) * | 1975-05-26 | 1976-11-30 | Schering Ag | Werkwijze voor het bereiden van prostaanderi- vaten en werkwijze voor het bereiden van een geneesmiddel met prostaglandinewerking. |
| US4159343A (en) * | 1975-05-26 | 1979-06-26 | Schering Aktiengesellschaft | Prostane derivatives |
| US4026909A (en) * | 1975-07-14 | 1977-05-31 | The Upjohn Company | Cis-13-PGF2.sub.α analogs |
| US4022912A (en) * | 1976-02-09 | 1977-05-10 | Miles Laboratories, Inc. | Use of 1-decarboxy-1-hydroxymethyl-PGE1 in therapeutic bronchodilation |
| GB1541962A (en) * | 1976-02-25 | 1979-03-14 | Sagami Chem Res | Prostaglandin precursors and processes for preparing the same |
| US4066675A (en) * | 1976-03-22 | 1978-01-03 | Merck & Co., Inc. | 9-thia- and oxothia- and 9-dioxothia-11,12-seco-prostaglandins and processes |
| JPS62152008A (ja) * | 1985-12-25 | 1987-07-07 | Fanuc Ltd | 送り速度制御方法 |
-
1974
- 1974-06-05 US US05/476,362 patent/US3970685A/en not_active Expired - Lifetime
-
1975
- 1975-05-20 ZA ZA3247A patent/ZA753247B/xx unknown
- 1975-05-20 CA CA227,373A patent/CA1039277A/fr not_active Expired
- 1975-05-26 IL IL47354A patent/IL47354A/xx unknown
- 1975-05-30 DK DK245075A patent/DK245075A/da not_active Application Discontinuation
- 1975-06-03 GB GB23973/75A patent/GB1496845A/en not_active Expired
- 1975-06-03 DE DE19752524619 patent/DE2524619A1/de active Pending
- 1975-06-03 BE BE156988A patent/BE829820A/fr unknown
- 1975-06-04 ES ES438237A patent/ES438237A1/es not_active Expired
- 1975-06-04 NO NO751975A patent/NO751975L/no unknown
- 1975-06-04 JP JP50067440A patent/JPS5111743A/ja active Pending
- 1975-06-04 SE SE7506388A patent/SE7506388L/xx unknown
- 1975-06-04 FR FR7517498A patent/FR2273519A1/fr not_active Withdrawn
- 1975-06-04 AT AT425375A patent/AT348156B/de not_active IP Right Cessation
- 1975-06-05 CH CH726775A patent/CH611880A5/xx not_active IP Right Cessation
- 1975-06-05 NL NL7506666A patent/NL7506666A/xx not_active Application Discontinuation
-
1977
- 1977-01-03 ES ES454767A patent/ES454767A1/es not_active Expired
-
1979
- 1979-06-05 CH CH523979A patent/CH617187A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| SE7506388L (sv) | 1975-12-08 |
| ES438237A1 (es) | 1977-05-16 |
| IL47354A (en) | 1979-01-31 |
| IL47354A0 (en) | 1975-07-28 |
| AT348156B (de) | 1979-02-12 |
| ZA753247B (en) | 1977-01-26 |
| DK245075A (da) | 1975-12-06 |
| GB1496845A (en) | 1978-01-05 |
| DE2524619A1 (de) | 1976-01-02 |
| ATA425375A (de) | 1978-06-15 |
| CH611880A5 (fr) | 1979-06-29 |
| US3970685A (en) | 1976-07-20 |
| BE829820A (fr) | 1975-12-03 |
| ES454767A1 (es) | 1978-01-01 |
| NO751975L (fr) | 1975-12-08 |
| JPS5111743A (en) | 1976-01-30 |
| NL7506666A (nl) | 1975-12-09 |
| AU8179175A (en) | 1976-12-09 |
| CA1039277A (fr) | 1978-09-26 |
| FR2273519A1 (fr) | 1976-01-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |