JPS6218548B2 - - Google Patents

Info

Publication number: JPS6218548B2
Authority: JP; Japan
Prior art keywords: formula; carbon atoms; trans; group; reference example
Prior art date: 1976-07-16
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

JP52085555A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5334754A (en

Inventor

Barutoman Uiruherumu

Reruhi Ururitsuhi

Toifueru Heruman

Sherukensu Berunuaruto

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.)

Hoechst AG

Original Assignee

Hoechst AG

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.)

1976-07-16

Filing date

1977-07-16

Publication date

1987-04-23

1977-07-16 Application filed by Hoechst AG filed Critical Hoechst AG

1978-03-31 Publication of JPS5334754A publication Critical patent/JPS5334754A/ja

1987-04-23 Publication of JPS6218548B2 publication Critical patent/JPS6218548B2/ja

Status Granted legal-status Critical Current

Links

-1 chlorophenoxy Chemical group 0.000 claims description 124
150000001875 compounds Chemical class 0.000 claims description 55
125000004432 carbon atom Chemical group C* 0.000 claims description 49
239000001257 hydrogen Substances 0.000 claims description 23
229910052739 hydrogen Inorganic materials 0.000 claims description 23
125000000217 alkyl group Chemical group 0.000 claims description 18
125000006239 protecting group Chemical group 0.000 claims description 15
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
239000001301 oxygen Substances 0.000 claims description 11
229910052760 oxygen Inorganic materials 0.000 claims description 11
125000000753 cycloalkyl group Chemical group 0.000 claims description 10
150000002431 hydrogen Chemical class 0.000 claims description 10
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
125000003545 alkoxy group Chemical group 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 8
229910021645 metal ion Inorganic materials 0.000 claims description 6
150000003512 tertiary amines Chemical class 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical group 0.000 claims description 4
125000000547 substituted alkyl group Chemical group 0.000 claims description 3
238000005903 acid hydrolysis reaction Methods 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 96
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 42
238000006243 chemical reaction Methods 0.000 description 42
239000000243 solution Substances 0.000 description 39
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
238000000034 method Methods 0.000 description 29
239000002904 solvent Substances 0.000 description 29
239000002253 acid Substances 0.000 description 25
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 22
238000005481 NMR spectroscopy Methods 0.000 description 19
150000001299 aldehydes Chemical class 0.000 description 18
238000003756 stirring Methods 0.000 description 18
239000000203 mixture Substances 0.000 description 17
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
150000002148 esters Chemical class 0.000 description 14
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
239000000047 product Substances 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
238000004587 chromatography analysis Methods 0.000 description 10
239000003921 oil Substances 0.000 description 10
235000019198 oils Nutrition 0.000 description 10
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 9
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
239000003054 catalyst Substances 0.000 description 9
150000004702 methyl esters Chemical class 0.000 description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
230000002378 acidificating effect Effects 0.000 description 8
239000012141 concentrate Substances 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
150000003180 prostaglandins Chemical class 0.000 description 7
238000006467 substitution reaction Methods 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 6
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 6
239000003638 chemical reducing agent Substances 0.000 description 6
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 6
150000004678 hydrides Chemical class 0.000 description 6
239000005457 ice water Substances 0.000 description 6
125000000468 ketone group Chemical group 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
238000010992 reflux Methods 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
125000003342 alkenyl group Chemical group 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 5
150000002168 ethanoic acid esters Chemical class 0.000 description 5
239000007788 liquid Substances 0.000 description 5
230000007935 neutral effect Effects 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
235000006408 oxalic acid Nutrition 0.000 description 5
229940094443 oxytocics prostaglandins Drugs 0.000 description 5
239000012071 phase Substances 0.000 description 5
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 5
238000000746 purification Methods 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
239000002585 base Substances 0.000 description 4
229940079593 drug Drugs 0.000 description 4
239000003814 drug Substances 0.000 description 4
150000002576 ketones Chemical class 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
125000003003 spiro group Chemical group 0.000 description 4
239000000126 substance Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
238000004809 thin layer chromatography Methods 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
239000000052 vinegar Substances 0.000 description 4
235000021419 vinegar Nutrition 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
229910015900 BF3 Inorganic materials 0.000 description 3
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 3
QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
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 3
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000003863 ammonium salts Chemical class 0.000 description 3
239000000538 analytical sample Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
229910000019 calcium carbonate Inorganic materials 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000012043 crude product Substances 0.000 description 3
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
150000004252 dithioacetals Chemical class 0.000 description 3
150000004662 dithiols Chemical class 0.000 description 3
238000001035 drying Methods 0.000 description 3
239000000284 extract Substances 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
125000001153 fluoro group Chemical group F* 0.000 description 3
230000014509 gene expression Effects 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
150000002430 hydrocarbons Chemical group 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
229910052744 lithium Inorganic materials 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
150000002902 organometallic compounds Chemical class 0.000 description 3
230000003647 oxidation Effects 0.000 description 3
238000007254 oxidation reaction Methods 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
238000010898 silica gel chromatography Methods 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
210000002784 stomach Anatomy 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
125000001544 thienyl group Chemical group 0.000 description 3
AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 2
ZQXCQTAELHSNAT-UHFFFAOYSA-N 1-chloro-3-nitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(C(F)(F)F)=C1 ZQXCQTAELHSNAT-UHFFFAOYSA-N 0.000 description 2
BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 2
NGKLOPGFJZNOSQ-UHFFFAOYSA-N 3-oxo-2-(5-oxopentyl)cyclopentane-1-carbonitrile Chemical compound O=CCCCCC1C(C#N)CCC1=O NGKLOPGFJZNOSQ-UHFFFAOYSA-N 0.000 description 2
ZSBDGXGICLIJGD-UHFFFAOYSA-N 4-phenoxyphenol Chemical compound C1=CC(O)=CC=C1OC1=CC=CC=C1 ZSBDGXGICLIJGD-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical group CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
239000002250 absorbent Substances 0.000 description 2
230000002745 absorbent Effects 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
125000003158 alcohol group Chemical group 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
125000003302 alkenyloxy group Chemical group 0.000 description 2
125000005108 alkenylthio group Chemical group 0.000 description 2
150000001350 alkyl halides Chemical class 0.000 description 2
125000004414 alkyl thio group Chemical group 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 2
230000036772 blood pressure Effects 0.000 description 2
229910000085 borane Inorganic materials 0.000 description 2
229910052796 boron Inorganic materials 0.000 description 2
XSEUMFJMFFMCIU-UHFFFAOYSA-N buformin Chemical compound CCCC\N=C(/N)N=C(N)N XSEUMFJMFFMCIU-UHFFFAOYSA-N 0.000 description 2
229960004111 buformin Drugs 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 2
239000006071 cream Substances 0.000 description 2
JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 2
239000003480 eluent Substances 0.000 description 2
238000010828 elution Methods 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
150000002084 enol ethers Chemical class 0.000 description 2
OMCUKJXJGMDVDL-UHFFFAOYSA-N ethyl 1-(5-acetyloxypentyl)-2-oxocyclopentane-1-carboxylate Chemical compound CC(=O)OCCCCCC1(C(=O)OCC)CCCC1=O OMCUKJXJGMDVDL-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000012467 final product Substances 0.000 description 2
238000009472 formulation Methods 0.000 description 2
238000005227 gel permeation chromatography Methods 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
229940088597 hormone Drugs 0.000 description 2
239000005556 hormone Substances 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
229910052987 metal hydride Inorganic materials 0.000 description 2
150000004681 metal hydrides Chemical class 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
239000007800 oxidant agent Substances 0.000 description 2
XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 2
YEMKIGUKNDOZEG-UHFFFAOYSA-N phosphonoacetaldehyde Chemical compound OP(O)(=O)CC=O YEMKIGUKNDOZEG-UHFFFAOYSA-N 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
230000002997 prostaglandinlike Effects 0.000 description 2
239000000523 sample Substances 0.000 description 2
238000007127 saponification reaction Methods 0.000 description 2
230000007017 scission Effects 0.000 description 2
230000001568 sexual effect Effects 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000003797 solvolysis reaction Methods 0.000 description 2
239000007858 starting material Substances 0.000 description 2
150000003462 sulfoxides Chemical class 0.000 description 2
125000005297 thienyloxy group Chemical group S1C(=CC=C1)O* 0.000 description 2
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JWHOQZUREKYPBY-UHFFFAOYSA-N rubonic acid Natural products CC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CCC(=O)C(C)(C)C5CC(=O)C34C)C2C1)C(=O)O JWHOQZUREKYPBY-UHFFFAOYSA-N 0.000 description 1
235000021003 saturated fats Nutrition 0.000 description 1
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
230000028327 secretion Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
229910052979 sodium sulfide Inorganic materials 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
239000002600 sunflower oil Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
150000003555 thioacetals Chemical class 0.000 description 1
HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
229960005371 tolbutamide Drugs 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
230000017105 transposition Effects 0.000 description 1
235000021081 unsaturated fats Nutrition 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
150000003722 vitamin derivatives Chemical class 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1
125000005023 xylyl group Chemical group 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/08—1,3-Dioxanes; Hydrogenated 1,3-dioxanes condensed with carbocyclic rings or ring systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/02—Five-membered rings
- C07D339/06—Five-membered rings having the hetero atoms in positions 1 and 3, e.g. cyclic dithiocarbonates
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4018—Esters of cycloaliphatic acids

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
Molecular Biology (AREA)
Veterinary Medicine (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Bioinformatics & Cheminformatics (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

JP8555577A 1976-07-16 1977-07-16 Novel cyclopentane derivatives and process for preparing same Granted JPS5334754A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2632097A DE2632097C2 (de)	1976-07-16	1976-07-16	Cyclopentanderivate, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel

Publications (2)

Publication Number	Publication Date
JPS5334754A JPS5334754A (en)	1978-03-31
JPS6218548B2 true JPS6218548B2 (de)	1987-04-23

Family

ID=5983219

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP8555577A Granted JPS5334754A (en)	1976-07-16	1977-07-16	Novel cyclopentane derivatives and process for preparing same

Country Status (13)

Country	Link
JP (1)	JPS5334754A (de)
AU (1)	AU2705677A (de)
BE (2)	BE856914A (de)
DE (1)	DE2632097C2 (de)
DK (1)	DK322177A (de)
ES (1)	ES460623A1 (de)
FR (1)	FR2358392A1 (de)
GB (1)	GB1589525A (de)
IL (1)	IL52523A0 (de)
LU (1)	LU77767A1 (de)
NL (1)	NL7707695A (de)
SE (1)	SE7708245L (de)
ZA (2)	ZA774254B (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2834249A1 (de) *	1978-08-04	1980-02-28	Hoechst Ag	Neue prostaglandinderivate in der delta 2-11-desoxy-pgf tief 2 bzw. pge tief 2 -reihe
US20230097470A1 (en) *	2021-08-23	2023-03-30	Chirogate International Inc.	Processes and intermediates for the preparations of carboprost and carboprost tromethamine, and carboprost tromethamine prepared therefrom

1976
- 1976-07-16 DE DE2632097A patent/DE2632097C2/de not_active Expired
1977
- 1977-07-11 ES ES460623A patent/ES460623A1/es not_active Expired
- 1977-07-11 NL NL7707695A patent/NL7707695A/xx not_active Application Discontinuation
- 1977-07-14 IL IL52523A patent/IL52523A0/xx unknown
- 1977-07-14 LU LU77767A patent/LU77767A1/xx unknown
- 1977-07-15 AU AU27056/77A patent/AU2705677A/en active Pending
- 1977-07-15 DK DK322177A patent/DK322177A/da not_active Application Discontinuation
- 1977-07-15 ZA ZA00774254A patent/ZA774254B/xx unknown
- 1977-07-15 ZA ZA00774255A patent/ZA774255B/xx unknown
- 1977-07-15 SE SE7708245A patent/SE7708245L/xx unknown
- 1977-07-16 JP JP8555577A patent/JPS5334754A/ja active Granted
- 1977-07-18 GB GB30061/77A patent/GB1589525A/en not_active Expired
- 1977-07-18 FR FR7721921A patent/FR2358392A1/fr active Granted
- 1977-07-18 BE BE179437A patent/BE856914A/xx unknown
- 1977-07-18 BE BE179433A patent/BE856910A/xx unknown

Also Published As

Publication number	Publication date
FR2358392B1 (de)	1980-02-08
FR2358392A1 (fr)	1978-02-10
NL7707695A (nl)	1978-01-18
ZA774255B (en)	1978-06-28
LU77767A1 (de)	1978-02-08
BE856914A (fr)	1978-01-18
AU2705677A (en)	1979-01-18
GB1589525A (en)	1981-05-13
DK322177A (da)	1978-01-17
JPS5334754A (en)	1978-03-31
BE856910A (fr)	1978-01-18
DE2632097A1 (de)	1978-01-19
SE7708245L (sv)	1978-01-17
IL52523A0 (en)	1977-10-31
DE2632097C2 (de)	1985-08-14
ES460623A1 (es)	1978-05-16
ZA774254B (en)	1978-06-28

Publication	Publication Date	Title
US4024179A (en)	1977-05-17	Substituted ω-pentanorprostaglandins
DE2902442A1 (de)	1979-08-30	9-deoxy-9a-methylen-isostere von pgi tief 2 , verfahren zu ihrer herstellung und sie enthaltende pharmazeutische und veterinaermedizinische mittel
NO147836B (no)	1983-03-14	Nye 16-aryloksy-substituerte omega-tetranorprostaglandiner for anvendelse som fruktbarhetsregulerende middel, svangerskapsavbrytende middel eller middel for synkronisering av brunstcyklusen hos husdyr
EP0540400A1 (de)	1993-05-05	Chinoline Derivate, nützlich als Angiotensin-II-Antagonisten
JPS61155384A (ja)	1986-07-15	テトラヒドロチエニル置換プロスタグランジン類縁体
US3881017A (en)	1975-04-29	9-Thiaprostaglandin compositions
CH619691A5 (de)	1980-10-15
US4182903A (en)	1980-01-08	13-Azaprostaglandins
JPH06502390A (ja)	1994-03-17	シクロペンタン誘導体、その製法及びその薬剤学的使用
LU80016A1 (fr)	1980-02-14	Procede de preparation de nouvelles 4-pyrones substituees en positions 2,3 et 6 et medicament les contenant
US4088775A (en)	1978-05-09	15-Ethylenedioxy-prostanoic acid derivatives and esters thereof and intermediates thereof
US4219483A (en)	1980-08-26	4-Pyrone prostaglandin antagonists
CH624934A5 (de)	1981-08-31
JPS6218548B2 (de)	1987-04-23
US5057621A (en)	1991-10-15	11-substituted-16-phenoxy and 16-substituted phenoxy-prostatrienoic acid derivatives
CA1196632A (en)	1985-11-12	5,6-dihydro-prostacyclin analogs
DE2610503C2 (de)	1986-09-18	Optisch aktive 13,14-Dehydro-11- desoxy-prostaglandine, Verfahren zu ihrer Herstellung und sie enthaltendes pharmazeutisches Mittel
US4644068A (en)	1987-02-17	Bicyclo[3.3.0]octenylaldehyde derivatives
US4404372A (en)	1983-09-13	15-Substituted-ω-pentanorprostaglandin derivatives
CA1250835A (en)	1989-03-07	.alpha. CHAIN DIENIC PROSTANOIC ACID DERIVATIVES
FR2515642A1 (fr)	1983-05-06	Nouvelles (11r)-11-deoxy-11-alkyl-6-oxo-prostaglandines et compositions pharmaceutiques les contenant
US4258053A (en)	1981-03-24	Thienyl-prostaglandins and process for their manufacture
DE2737807A1 (de)	1978-03-09	C tief 1 -p-biphenylester von omega-pentanorprostaglandinen
DE2541883C2 (de)	1984-03-29	9-Oxo-15xi-hydroxy-20-alkylidenprost-13(trans)-ensäurederivate und Verfahren zu ihrer Herstellung und diese enthaltendes Arzneimittel
JPS625904B2 (de)	1987-02-07