DE2601646C2 - - Google Patents

Info

Publication number: DE2601646C2
Authority: DE; Germany
Prior art keywords: following; chcl3; hydrogen; methoxy; radical
Prior art date: 1975-01-24
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

DE2601646A

Other languages

German (de)

English (en)

Other versions

DE2601646A1 (de

Inventor

Umberto Guzzi

Romeo Mailand/Milano It Ciabatti

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.)

GRUPPO LEPETIT SpA MAILAND/MILANO IT

Original Assignee

GRUPPO LEPETIT SpA MAILAND/MILANO IT

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.)

1975-01-24

Filing date

1976-01-17

Publication date

1987-07-02

1976-01-17 Application filed by GRUPPO LEPETIT SpA MAILAND/MILANO IT filed Critical GRUPPO LEPETIT SpA MAILAND/MILANO IT

1976-07-29 Publication of DE2601646A1 publication Critical patent/DE2601646A1/de

1987-07-02 Application granted granted Critical

1987-07-02 Publication of DE2601646C2 publication Critical patent/DE2601646C2/de

Status Granted legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims description 62
-1 alkyl radical Chemical class 0.000 claims description 44
239000000203 mixture Substances 0.000 claims description 33
238000000034 method Methods 0.000 claims description 24
125000004432 carbon atom Chemical group C* 0.000 claims description 16
229910052739 hydrogen Inorganic materials 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
125000004043 oxo group Chemical group O=* 0.000 claims description 10
150000003180 prostaglandins Chemical class 0.000 claims description 10
239000003153 chemical reaction reagent Substances 0.000 claims description 8
150000003254 radicals Chemical class 0.000 claims description 8
229910000033 sodium borohydride Inorganic materials 0.000 claims description 8
239000012279 sodium borohydride Substances 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
230000002829 reductive effect Effects 0.000 claims description 6
150000001768 cations Chemical class 0.000 claims description 4
125000006239 protecting group Chemical group 0.000 claims description 4
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
VELDYOPRLMJFIK-UHFFFAOYSA-N cyclopentanecarbaldehyde Chemical compound O=CC1CCCC1 VELDYOPRLMJFIK-UHFFFAOYSA-N 0.000 claims description 3
229910052744 lithium Inorganic materials 0.000 claims description 3
WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 claims description 2
ZKCZXVODRKOWIY-UHFFFAOYSA-N diphenylstannane Chemical compound C=1C=CC=CC=1[SnH2]C1=CC=CC=C1 ZKCZXVODRKOWIY-UHFFFAOYSA-N 0.000 claims description 2
150000002431 hydrogen Chemical group 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 86
239000002253 acid Substances 0.000 description 62
239000000047 product Substances 0.000 description 54
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
238000010521 absorption reaction Methods 0.000 description 35
150000004702 methyl esters Chemical class 0.000 description 35
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 26
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 22
239000003921 oil Substances 0.000 description 20
230000003287 optical effect Effects 0.000 description 19
239000000243 solution Substances 0.000 description 19
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
238000000862 absorption spectrum Methods 0.000 description 13
239000011541 reaction mixture Substances 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
229960001340 histamine Drugs 0.000 description 11
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
241000282472 Canis lupus familiaris Species 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
230000001262 anti-secretory effect Effects 0.000 description 8
150000002148 esters Chemical class 0.000 description 8
239000007858 starting material Substances 0.000 description 8
210000002784 stomach Anatomy 0.000 description 8
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 7
150000001299 aldehydes Chemical class 0.000 description 7
230000000052 comparative effect Effects 0.000 description 7
239000012074 organic phase Substances 0.000 description 7
230000000704 physical effect Effects 0.000 description 7
239000002243 precursor Substances 0.000 description 7
230000035935 pregnancy Effects 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
238000012360 testing method Methods 0.000 description 7
150000007513 acids Chemical class 0.000 description 6
238000002474 experimental method Methods 0.000 description 6
241000699800 Cricetinae Species 0.000 description 5
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
125000003545 alkoxy group Chemical group 0.000 description 5
238000009833 condensation Methods 0.000 description 5
230000005494 condensation Effects 0.000 description 5
230000000694 effects Effects 0.000 description 5
238000001802 infusion Methods 0.000 description 5
230000003529 luteolytic effect Effects 0.000 description 5
229910052698 phosphorus Inorganic materials 0.000 description 5
239000011574 phosphorus Substances 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
238000012746 preparative thin layer chromatography Methods 0.000 description 5
230000028327 secretion Effects 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
241000700159 Rattus Species 0.000 description 4
230000027119 gastric acid secretion Effects 0.000 description 4
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical class [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 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
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
125000005907 alkyl ester group Chemical group 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
150000001450 anions Chemical class 0.000 description 3
238000013375 chromatographic separation Methods 0.000 description 3
125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 3
230000002496 gastric effect Effects 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
229940094443 oxytocics prostaglandins Drugs 0.000 description 3
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 3
VBQCHPIMZGQLAZ-UHFFFAOYSA-N phosphorane Chemical class [PH5] VBQCHPIMZGQLAZ-UHFFFAOYSA-N 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
230000003248 secreting effect Effects 0.000 description 3
239000000725 suspension Substances 0.000 description 3
125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
239000012027 Collins reagent Substances 0.000 description 2
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 2
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
206010000210 abortion Diseases 0.000 description 2
231100000176 abortion Toxicity 0.000 description 2
230000010933 acylation Effects 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
238000010533 azeotropic distillation Methods 0.000 description 2
239000002585 base Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
230000037396 body weight Effects 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000006482 condensation reaction Methods 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
210000003754 fetus Anatomy 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000012433 hydrogen halide Substances 0.000 description 2
229910000039 hydrogen halide Inorganic materials 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
235000010446 mineral oil Nutrition 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
125000003259 prostaglandin group Chemical group 0.000 description 2
230000002997 prostaglandinlike Effects 0.000 description 2
NPRDHMWYZHSAHR-UHFFFAOYSA-N pyridine;trioxochromium Chemical compound O=[Cr](=O)=O.C1=CC=NC=C1.C1=CC=NC=C1 NPRDHMWYZHSAHR-UHFFFAOYSA-N 0.000 description 2
239000011347 resin Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000007920 subcutaneous administration Methods 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
238000001356 surgical procedure Methods 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
YIWGJFPJRAEKMK-UHFFFAOYSA-N 1-(2H-benzotriazol-5-yl)-3-methyl-8-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carbonyl]-1,3,8-triazaspiro[4.5]decane-2,4-dione Chemical compound CN1C(=O)N(c2ccc3n[nH]nc3c2)C2(CCN(CC2)C(=O)c2cnc(NCc3cccc(OC(F)(F)F)c3)nc2)C1=O YIWGJFPJRAEKMK-UHFFFAOYSA-N 0.000 description 1
WZAWFKKYWRMNLU-UHFFFAOYSA-N 1-dimethoxyphosphoryl-3-methoxy-3-methylheptan-2-one Chemical compound CCCCC(C)(OC)C(=O)CP(=O)(OC)OC WZAWFKKYWRMNLU-UHFFFAOYSA-N 0.000 description 1
CKGAPNASZQDWOE-UHFFFAOYSA-N 1-dimethoxyphosphoryl-3-methoxyheptan-2-one Chemical compound CCCCC(OC)C(=O)CP(=O)(OC)OC CKGAPNASZQDWOE-UHFFFAOYSA-N 0.000 description 1
125000004797 2,2,2-trichloroethoxy group Chemical group ClC(CO*)(Cl)Cl 0.000 description 1
YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
JPVUWCPKMYXOKW-UHFFFAOYSA-N 4-phenylbenzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1C1=CC=CC=C1 JPVUWCPKMYXOKW-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
208000032544 Cicatrix Diseases 0.000 description 1
HZCDANOFLILNSA-UHFFFAOYSA-N Dimethyl hydrogen phosphite Chemical compound COP(=O)OC HZCDANOFLILNSA-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
239000007818 Grignard reagent Substances 0.000 description 1
241000699673 Mesocricetus auratus Species 0.000 description 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
PQGAHNJECSVDEI-UHFFFAOYSA-N [CH2]CCCCC Chemical compound [CH2]CCCCC PQGAHNJECSVDEI-UHFFFAOYSA-N 0.000 description 1
YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 description 1
125000004036 acetal group Chemical group 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
150000001241 acetals Chemical class 0.000 description 1
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
230000009858 acid secretion Effects 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
230000003276 anti-hypertensive effect Effects 0.000 description 1
238000010945 base-catalyzed hydrolysis reactiony Methods 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
MKJQIOMCOYQKNP-UHFFFAOYSA-N bromomethane;magnesium Chemical compound [Mg].BrC MKJQIOMCOYQKNP-UHFFFAOYSA-N 0.000 description 1
229940124630 bronchodilator Drugs 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
238000012790 confirmation Methods 0.000 description 1
238000001103 continuous-wave nuclear magnetic resonance spectrum Methods 0.000 description 1
239000012043 crude product Substances 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
230000034994 death Effects 0.000 description 1
231100000517 death Toxicity 0.000 description 1
238000010828 elution Methods 0.000 description 1
210000003238 esophagus Anatomy 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
230000035558 fertility Effects 0.000 description 1
230000004720 fertilization Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
150000004795 grignard reagents Chemical class 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000000268 heptanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000001077 hypotensive effect Effects 0.000 description 1
239000005457 ice water Substances 0.000 description 1
210000003405 ileum Anatomy 0.000 description 1
238000002513 implantation Methods 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000007788 liquid Substances 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
XYDYWTJEGDZLTH-UHFFFAOYSA-N methylenetriphenylphosphorane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=C)C1=CC=CC=C1 XYDYWTJEGDZLTH-UHFFFAOYSA-N 0.000 description 1
235000019799 monosodium phosphate Nutrition 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
CPYJUVWVXLWTPP-UHFFFAOYSA-N octan-1-one Chemical compound CCCCCCC[C]=O CPYJUVWVXLWTPP-UHFFFAOYSA-N 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N oxalic acid Substances OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000012071 phase Substances 0.000 description 1
125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical class O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
210000002826 placenta Anatomy 0.000 description 1
230000003169 placental effect Effects 0.000 description 1
239000010970 precious metal Substances 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
WGJJROVFWIXTPA-OALUTQOASA-N prostanoic acid Chemical compound CCCCCCCC[C@H]1CCC[C@@H]1CCCCCCC(O)=O WGJJROVFWIXTPA-OALUTQOASA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
210000001187 pylorus Anatomy 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000002040 relaxant effect Effects 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
231100000241 scar Toxicity 0.000 description 1
230000037387 scars Effects 0.000 description 1
210000000582 semen Anatomy 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000008399 tap water Substances 0.000 description 1
235000020679 tap water Nutrition 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
210000003437 trachea Anatomy 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
238000011121 vaginal smear Methods 0.000 description 1
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
PGOLTJPQCISRTO-UHFFFAOYSA-N vinyllithium Chemical compound [Li]C=C PGOLTJPQCISRTO-UHFFFAOYSA-N 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- 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
- 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

Landscapes

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

DE19762601646 1975-01-24 1976-01-17 Neue prostaglandin-analoga Granted DE2601646A1 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB3248/75A GB1538871A (en)	1975-01-24	1975-01-24	Prostaglandins

Publications (2)

Publication Number	Publication Date
DE2601646A1 DE2601646A1 (de)	1976-07-29
DE2601646C2 true DE2601646C2 (xx)	1987-07-02

Family

ID=9754749

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE19762601646 Granted DE2601646A1 (de)	1975-01-24	1976-01-17	Neue prostaglandin-analoga

Country Status (28)

Country	Link
JP (1)	JPS6024098B2 (xx)
AR (1)	AR212328A1 (xx)
AT (1)	AT351186B (xx)
BE (1)	BE837865A (xx)
CA (1)	CA1076569A (xx)
CH (1)	CH609682A5 (xx)
CS (1)	CS187333B2 (xx)
DD (1)	DD122517A5 (xx)
DE (1)	DE2601646A1 (xx)
DK (1)	DK27376A (xx)
FI (1)	FI64578C (xx)
FR (1)	FR2298322A1 (xx)
GB (1)	GB1538871A (xx)
GR (1)	GR58537B (xx)
HU (1)	HU174185B (xx)
IE (1)	IE43821B1 (xx)
IL (1)	IL48870A (xx)
LU (1)	LU74240A1 (xx)
NL (1)	NL185203C (xx)
NO (1)	NO147714C (xx)
NZ (1)	NZ179816A (xx)
PH (1)	PH14040A (xx)
PT (1)	PT64737B (xx)
RO (1)	RO71901A (xx)
SE (1)	SE446726B (xx)
SU (1)	SU607550A3 (xx)
YU (1)	YU40805B (xx)
ZA (1)	ZA7681B (xx)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4064350A (en) *	1976-11-22	1977-12-20	G. D. Searle & Co.	15,16-Dihydroxyprostaglandins
US4194055A (en) *	1976-03-03	1980-03-18	American Cyanamid Company	15,16-dioxy prostenoic acids and esters
IT1162731B (it) *	1979-04-10	1987-04-01	Lepetit Spa	16-metil-16-metossi-5,6-diidro-prosta-glandine della serie e1 ad attivita'antisecretoria
JPS56162014A (en) *	1980-05-16	1981-12-12	Nippon Denso Co Ltd	Measuring device for flow rate of gas

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1392716A (en) *	1971-05-11	1975-04-30	Ici Ltd	Moulding
US4304907A (en) *	1972-05-10	1981-12-08	The Upjohn Company	Bicyclo lactone intermediates for prostaglandin analogs

1975
- 1975-01-24 GB GB3248/75A patent/GB1538871A/en not_active Expired
1976
- 1976-01-05 FI FI760002A patent/FI64578C/fi not_active IP Right Cessation
- 1976-01-07 ZA ZA00760081A patent/ZA7681B/xx unknown
- 1976-01-09 GR GR49742A patent/GR58537B/el unknown
- 1976-01-15 YU YU111/76A patent/YU40805B/xx unknown
- 1976-01-16 CS CS76305A patent/CS187333B2/cs unknown
- 1976-01-17 DE DE19762601646 patent/DE2601646A1/de active Granted
- 1976-01-19 IL IL48870A patent/IL48870A/xx unknown
- 1976-01-21 AT AT36776A patent/AT351186B/de not_active IP Right Cessation
- 1976-01-21 RO RO7684563A patent/RO71901A/ro unknown
- 1976-01-22 IE IE120/76A patent/IE43821B1/en unknown
- 1976-01-22 PH PH18006A patent/PH14040A/en unknown
- 1976-01-22 DD DD190915A patent/DD122517A5/xx unknown
- 1976-01-22 FR FR7601707A patent/FR2298322A1/fr active Granted
- 1976-01-23 BE BE163765A patent/BE837865A/xx not_active IP Right Cessation
- 1976-01-23 CH CH83176A patent/CH609682A5/xx not_active IP Right Cessation
- 1976-01-23 PT PT64737A patent/PT64737B/pt unknown
- 1976-01-23 CA CA244,132A patent/CA1076569A/en not_active Expired
- 1976-01-23 NZ NZ179816A patent/NZ179816A/xx unknown
- 1976-01-23 JP JP51006567A patent/JPS6024098B2/ja not_active Expired
- 1976-01-23 SE SE7600729A patent/SE446726B/xx not_active IP Right Cessation
- 1976-01-23 NL NLAANVRAGE7600696,A patent/NL185203C/xx not_active IP Right Cessation
- 1976-01-23 DK DK27376*#A patent/DK27376A/da not_active Application Discontinuation
- 1976-01-23 AR AR262009A patent/AR212328A1/es active
- 1976-01-23 HU HU76LE788A patent/HU174185B/hu not_active IP Right Cessation
- 1976-01-23 SU SU762311606A patent/SU607550A3/ru active
- 1976-01-23 LU LU74240A patent/LU74240A1/xx unknown
- 1976-01-23 NO NO760214A patent/NO147714C/no unknown

Also Published As

Publication number	Publication date
IE43821B1 (en)	1981-06-03
FI64578C (fi)	1983-12-12
GR58537B (en)	1977-10-31
IL48870A0 (en)	1976-03-31
GB1538871A (en)	1979-01-24
PT64737B (fr)	1977-08-12
NO147714B (no)	1983-02-21
PH14040A (en)	1980-12-12
LU74240A1 (xx)	1976-07-23
SU607550A3 (ru)	1978-05-15
NO760214L (xx)	1976-07-27
NL7600696A (nl)	1976-07-27
JPS5198249A (xx)	1976-08-30
AR212328A1 (es)	1978-06-30
CS187333B2 (en)	1979-01-31
FI760002A (xx)	1976-07-25
NL185203C (nl)	1990-02-16
IL48870A (en)	1979-11-30
SE7600729L (sv)	1976-07-25
ZA7681B (en)	1976-12-29
JPS6024098B2 (ja)	1985-06-11
YU11176A (en)	1982-10-31
DK27376A (da)	1976-07-25
BE837865A (fr)	1976-07-23
FI64578B (fi)	1983-08-31
ATA36776A (de)	1978-12-15
DD122517A5 (xx)	1976-10-12
IE43821L (en)	1976-07-24
HU174185B (hu)	1979-11-28
CA1076569A (en)	1980-04-29
AT351186B (de)	1979-07-10
FR2298322B1 (xx)	1979-09-21
NO147714C (no)	1983-06-01
YU40805B (en)	1986-06-30
FR2298322A1 (fr)	1976-08-20
DE2601646A1 (de)	1976-07-29
PT64737A (fr)	1976-02-01
CH609682A5 (en)	1979-03-15
SE446726B (sv)	1986-10-06
RO71901A (ro)	1982-02-26
NZ179816A (en)	1978-04-03
NL185203B (nl)	1989-09-18

Legal Events

Date	Code	Title
1983-03-17	8110	Request for examination paragraph 44
1987-07-02	D2	Grant after examination
1988-01-07	8364	No opposition during term of opposition

Publication	Publication Date	Title
DE2652256C2 (de)	1985-10-31	Polyprenylalkohole und diese enthaltende pharmazeutische Zusammensetzungen
DE69204627T2 (de)	1996-05-02	Prostaglandine.
DE2437388A1 (de)	1975-02-13	Prostansaeurederivate
DE2223365C3 (de)	1981-06-04	Prostansäurederivate, Verfahren zu ihrer Herstellung, solche Derivate enthaltende pharmazeutische und veterinäre Zusammensetzungen sowie Zwischenprodukte zur Herstellung dieser Derivate
DE2356383A1 (de)	1974-05-30	Chemische zwischenprodukte, die sich zur herstellung von prostaglandinen und prostaglandinartigen verbindungen eignen
DE2416193A1 (de)	1975-10-23	Neue prostaglandin-analoge und verfahren zu ihrer herstellung
DE2234709C2 (de)	1982-06-03	Prostanoesäurederivate und Verfahren zu deren Herstellung
DE2601646C2 (xx)	1987-07-02
DE2322142C2 (de)	1982-07-01	Prostansäurederivate, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische oder veterinäre Zuammensetzungen
DE2150361A1 (de)	1972-04-13	Prostanoesaeurederivate
DE2739277A1 (de)	1978-03-16	11-deoxy-11-oxaprostaglandinverbindungen
DE2721534A1 (de)	1977-12-15	Omega-nor-aromatische-13,14-dehydro-prostaglandine, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische und veterinaermittel
DE2610503C2 (de)	1986-09-18	Optisch aktive 13,14-Dehydro-11- desoxy-prostaglandine, Verfahren zu ihrer Herstellung und sie enthaltendes pharmazeutisches Mittel
DE2743283A1 (de)	1979-04-05	Neue prostacyclin-analoga
DE1618946A1 (de)	1972-06-08	Neue organische Verbindungen und Verfahren zur Herstellung neuer organischer Verbindungen
DE2611788C2 (de)	1986-03-27	Fluorprostaglandine, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Mittel
DE3012306C2 (xx)	1990-03-22
DE68909143T2 (de)	1994-01-13	Prostaglandin-Vorläufer und ihre Herstellung.
CH624930A5 (xx)	1981-08-31
EP0081047B1 (de)	1985-12-18	Verfahren zur Herstellung eines optisch aktiven Lactons und neue Ausgangsprodukte in diesem Verfahren
DE2415765C2 (xx)	1988-06-16
DE2715921A1 (de)	1977-10-27	Neue zwischenprodukte und verfahren zur herstellung von thromboxan b tief 2
DE2716075A1 (de)	1978-02-23	Neue zwischenprodukte und verfahren zur herstellung von thromboxan-analoga
DE2344838C3 (de)	1982-03-18	18-Oxa- und 19-Oxa-prostaglandinverbindungen sowie 20-Oxa- und 19-Oxa-omega-homo-prostaglandinverbindungen und Verfahren zu deren Herstellung
DE2739770C3 (de)	1982-02-04	19-Methyl-9-keto-15-hydroxy-prost-18-ensäure-Derivate, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel