FI58919C - Foerfarande foer framstaellning av pyrazolo(5,1-a)isokinoliner och 5,6-dihydropyrazolo(5,1-a)isokinoliner med antireproduktiv aktivitet - Google Patents

Foerfarande foer framstaellning av pyrazolo(5,1-a)isokinoliner och 5,6-dihydropyrazolo(5,1-a)isokinoliner med antireproduktiv aktivitet Download PDF

Info

Publication number: FI58919C
Authority: FI; Finland
Prior art keywords: formula; group; isoquinoline; alkoxy; pyrazolo
Prior art date: 1974-11-23

Application number

FI753046A

Other languages

English (en)

Finnish (fi)

Other versions

FI753046A7 (2

FI58919B (fi

Inventor

Amedeo Omodei-Sale

Emilio Toia

Giulio Galliani

Leonard J Lerner

Original Assignee

Lepetit Spa

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1974-11-23

Filing date

1975-10-31

Publication date

1981-05-11

1975-10-31 Application filed by Lepetit Spa filed Critical Lepetit Spa

1976-05-24 Publication of FI753046A7 publication Critical patent/FI753046A7/fi

1981-01-30 Application granted granted Critical

1981-01-30 Publication of FI58919B publication Critical patent/FI58919B/fi

1981-05-11 Publication of FI58919C publication Critical patent/FI58919C/fi

Links

230000000694 effects Effects 0.000 title claims description 13
VXHPZUDEECSUNB-UHFFFAOYSA-N pyrazolo[5,1-a]isoquinoline Chemical class C12=CC=CC=C2C=CN2C1=CC=N2 VXHPZUDEECSUNB-UHFFFAOYSA-N 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 40
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
238000000034 method Methods 0.000 claims description 9
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 6
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
150000002537 isoquinolines Chemical class 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
238000010992 reflux Methods 0.000 claims description 5
229910052783 alkali metal Inorganic materials 0.000 claims description 4
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
XAAKCCMYRKZRAK-UHFFFAOYSA-N isoquinoline-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=NC=CC2=C1 XAAKCCMYRKZRAK-UHFFFAOYSA-N 0.000 claims description 4
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
239000003377 acid catalyst Substances 0.000 claims description 3
150000001340 alkali metals Chemical class 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 2
239000012024 dehydrating agents‎ Substances 0.000 claims description 2
CXBNMPMLFONTPO-UHFFFAOYSA-N acetic benzoic anhydride Chemical class CC(=O)OC(=O)C1=CC=CC=C1 CXBNMPMLFONTPO-UHFFFAOYSA-N 0.000 claims 2
239000002262 Schiff base Substances 0.000 claims 1
150000004753 Schiff bases Chemical class 0.000 claims 1
FZNCGRZWXLXZSZ-CIQUZCHMSA-N Voglibose Chemical compound OCC(CO)N[C@H]1C[C@](O)(CO)[C@@H](O)[C@H](O)[C@H]1O FZNCGRZWXLXZSZ-CIQUZCHMSA-N 0.000 claims 1
229910000102 alkali metal hydride Inorganic materials 0.000 claims 1
150000008046 alkali metal hydrides Chemical class 0.000 claims 1
150000003973 alkyl amines Chemical class 0.000 claims 1
239000003054 catalyst Substances 0.000 claims 1
125000004970 halomethyl group Chemical group 0.000 claims 1
-1 methoxy, ethoxy, propoxy, isopropoxy, isobutoxy Chemical group 0.000 description 20
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
241001465754 Metazoa Species 0.000 description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 10
239000000243 solution Substances 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
239000000203 mixture Substances 0.000 description 8
230000035935 pregnancy Effects 0.000 description 8
239000002585 base Substances 0.000 description 7
210000003754 fetus Anatomy 0.000 description 7
150000003839 salts Chemical class 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
241000700159 Rattus Species 0.000 description 6
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
238000002425 crystallisation Methods 0.000 description 5
230000008025 crystallization Effects 0.000 description 5
238000002513 implantation Methods 0.000 description 5
239000000047 product Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
125000003545 alkoxy group Chemical group 0.000 description 4
230000003509 anti-fertility effect Effects 0.000 description 4
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
239000000155 melt Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000007792 addition Methods 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000012280 lithium aluminium hydride Substances 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
210000000582 semen Anatomy 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000003826 tablet Substances 0.000 description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
210000004291 uterus Anatomy 0.000 description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
241000699800 Cricetinae Species 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
238000010171 animal model Methods 0.000 description 2
SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
230000004071 biological effect Effects 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
229910000019 calcium carbonate Inorganic materials 0.000 description 2
239000002775 capsule Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
HQABEHZXAJHCLV-UHFFFAOYSA-N isoquinolin-1-ylmethanol Chemical compound C1=CC=C2C(CO)=NC=CC2=C1 HQABEHZXAJHCLV-UHFFFAOYSA-N 0.000 description 2
SHLPPXXKRFINFY-UHFFFAOYSA-N isoquinolin-2-ium;bromide Chemical compound Br.C1=NC=CC2=CC=CC=C21 SHLPPXXKRFINFY-UHFFFAOYSA-N 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
WJHGJDGITRCZLH-UHFFFAOYSA-N methyl isoquinoline-1-carboxylate Chemical compound C1=CC=C2C(C(=O)OC)=NC=CC2=C1 WJHGJDGITRCZLH-UHFFFAOYSA-N 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
230000003389 potentiating effect Effects 0.000 description 2
239000008159 sesame oil Substances 0.000 description 2
235000011803 sesame oil Nutrition 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000000375 suspending agent Substances 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
239000000454 talc Substances 0.000 description 2
235000012222 talc Nutrition 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
210000001215 vagina Anatomy 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 1
XVKPSEFSSWWBOI-UHFFFAOYSA-N 2-(3-methoxyphenyl)pyrazolo[5,1-a]isoquinoline Chemical compound COC1=CC=CC(C2=NN3C=CC4=CC=CC=C4C3=C2)=C1 XVKPSEFSSWWBOI-UHFFFAOYSA-N 0.000 description 1
DWKTWYNUPKCPEN-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-5,6-dihydropyrazolo[5,1-a]isoquinoline Chemical compound C=1C=CC(C2=NN3CCC4=CC=CC=C4C3=C2)=CC=1OCC1=CC=CC=C1 DWKTWYNUPKCPEN-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
GTPKPSRAWYANLF-UHFFFAOYSA-N 2-amino-3,4-dihydroisoquinolin-1-one;4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.C1=CC=C2C(=O)N(N)CCC2=C1 GTPKPSRAWYANLF-UHFFFAOYSA-N 0.000 description 1
125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
HXUIDZOMTRMIOE-UHFFFAOYSA-M 3-oxo-3-phenylpropionate Chemical compound [O-]C(=O)CC(=O)C1=CC=CC=C1 HXUIDZOMTRMIOE-UHFFFAOYSA-M 0.000 description 1
RJQCSUWRABVKPI-UHFFFAOYSA-N 5,6-dihydropyrazolo[5,1-a]isoquinoline Chemical compound C12=CC=CC=C2CCN2C1=CC=N2 RJQCSUWRABVKPI-UHFFFAOYSA-N 0.000 description 1
UAMJFNYPMAUVKF-UHFFFAOYSA-N 5,6-dihydropyrazolo[5,1-a]isoquinoline-1-carboxylic acid Chemical compound C1=CC=C2C3=C(C(=O)O)C=NN3CCC2=C1 UAMJFNYPMAUVKF-UHFFFAOYSA-N 0.000 description 1
206010000234 Abortion spontaneous Diseases 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 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
239000005995 Aluminium silicate Substances 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
241000282693 Cercopithecidae Species 0.000 description 1
208000032544 Cicatrix Diseases 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
GKKZMYDNDDMXSE-UHFFFAOYSA-N Ethyl 3-oxo-3-phenylpropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC=C1 GKKZMYDNDDMXSE-UHFFFAOYSA-N 0.000 description 1
208000009628 Fetal Resorption Diseases 0.000 description 1
239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
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 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
241000699673 Mesocricetus auratus Species 0.000 description 1
238000011887 Necropsy Methods 0.000 description 1
MMCLIIBNXYBJEL-UHFFFAOYSA-N OC=1C=C(C=CC1)C1=NN2C(C3=CC=CC=C3CC2)=C1.C1=NC=CC2=CC=CC=C12 Chemical compound OC=1C=C(C=CC1)C1=NN2C(C3=CC=CC=C3CC2)=C1.C1=NC=CC2=CC=CC=C12 MMCLIIBNXYBJEL-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
230000005856 abnormality Effects 0.000 description 1
239000004015 abortifacient agent Substances 0.000 description 1
231100000641 abortifacient agent Toxicity 0.000 description 1
206010000210 abortion Diseases 0.000 description 1
231100000176 abortion Toxicity 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
238000011888 autopsy Methods 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
229940077388 benzenesulfonate Drugs 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
229960002903 benzyl benzoate Drugs 0.000 description 1
230000000740 bleeding effect Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000006172 buffering agent Substances 0.000 description 1
235000010216 calcium carbonate Nutrition 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
239000000969 carrier Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
230000020335 dealkylation Effects 0.000 description 1
238000006900 dealkylation reaction Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
231100000673 dose–response relationship Toxicity 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000000605 extraction Methods 0.000 description 1
230000035558 fertility Effects 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
229940125697 hormonal agent Drugs 0.000 description 1
230000003054 hormonal effect Effects 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
229940071826 hydroxyethyl cellulose Drugs 0.000 description 1
239000007943 implant Substances 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-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
IUTDICPUOGGCKH-UHFFFAOYSA-N isoquinoline-1-carbonyl chloride Chemical compound C1=CC=C2C(C(=O)Cl)=NC=CC2=C1 IUTDICPUOGGCKH-UHFFFAOYSA-N 0.000 description 1
YZDXFUGIDTUCDA-UHFFFAOYSA-N isoquinoline-1-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=NC=CC2=C1 YZDXFUGIDTUCDA-UHFFFAOYSA-N 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
229940067606 lecithin Drugs 0.000 description 1
239000007788 liquid Substances 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
230000013011 mating Effects 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
229960002900 methylcellulose Drugs 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
208000015994 miscarriage Diseases 0.000 description 1
VBTQNRFWXBXZQR-UHFFFAOYSA-N n-bromoacetamide Chemical compound CC(=O)NBr VBTQNRFWXBXZQR-UHFFFAOYSA-N 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
210000002826 placenta Anatomy 0.000 description 1
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
231100000241 scar Toxicity 0.000 description 1
230000037387 scars Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
241000894007 species Species 0.000 description 1
208000000995 spontaneous abortion Diseases 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Investigating Or Analysing Biological Materials (AREA)
Peptides Or Proteins (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Other In-Based Heterocyclic Compounds (AREA)

FI753046A 1974-11-23 1975-10-31 Foerfarande foer framstaellning av pyrazolo(5,1-a)isokinoliner och 5,6-dihydropyrazolo(5,1-a)isokinoliner med antireproduktiv aktivitet FI58919C (fi)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB50855/74A GB1484615A (en)	1974-11-23	1974-11-23	Tricyclic n-containing derivatives
GB5085574		1974-11-23

Publications (3)

Publication Number	Publication Date
FI753046A7 FI753046A7 (2)	1976-05-24
FI58919B FI58919B (fi)	1981-01-30
FI58919C true FI58919C (fi)	1981-05-11

Family

ID=10457662

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
FI753046A FI58919C (fi)	1974-11-23	1975-10-31	Foerfarande foer framstaellning av pyrazolo(5,1-a)isokinoliner och 5,6-dihydropyrazolo(5,1-a)isokinoliner med antireproduktiv aktivitet
FI753045A FI58918C (fi)	1974-11-23	1975-10-31	Foerfarande foer framstaellning av imidazo(2,1-a)isokinoliner och 5,6-dihydro-imidazo(2,1-a)isokinoliner med antireproduktiv aktivitet

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
FI753045A FI58918C (fi)	1974-11-23	1975-10-31	Foerfarande foer framstaellning av imidazo(2,1-a)isokinoliner och 5,6-dihydro-imidazo(2,1-a)isokinoliner med antireproduktiv aktivitet

Country Status (25)

Country	Link
US (1)	US4075342A (2)
JP (1)	JPS5516513B2 (2)
AR (2)	AR210476A1 (2)
AT (2)	AT346332B (2)
BE (1)	BE835836A (2)
CA (2)	CA1068274A (2)
CH (2)	CH614444A5 (2)
DD (2)	DD122819A5 (2)
DE (1)	DE2551868C2 (2)
DK (2)	DK152756C (2)
ES (2)	ES442864A1 (2)
FI (2)	FI58919C (2)
FR (1)	FR2291747A1 (2)
GB (1)	GB1484615A (2)
GR (2)	GR58292B (2)
IE (1)	IE43567B1 (2)
IL (1)	IL48389A (2)
IN (2)	IN142014B (2)
LU (2)	LU73849A1 (2)
NL (1)	NL165741C (2)
NO (2)	NO143577C (2)
SE (2)	SE421620B (2)
SU (3)	SU578883A3 (2)
YU (1)	YU37328B (2)
ZA (1)	ZA756792B (2)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4075343A (en) *	1976-09-13	1978-02-21	Pfizer Inc.	Anti-allergenic 5-alkoxyimidazo[1,2-A]quinoline-2-carboxylic acids and derivatives thereof
US4313950A (en) *	1978-10-30	1982-02-02	Gruppo Lepetit S.P.A.	Antireproductive tricyclic ortho-fused nitrogen containing compounds
GR70248B (2) *	1978-10-30	1982-09-01	Lepetit Spa
EP0012866B1 (en) *	1978-12-21	1983-01-19	Gruppo Lepetit S.P.A.	New 3h-naphtho(1,2-d)imidazoles, processes for preparing them, compounds for use as antiinflammatory and antimicrobial agents and compositions for that use containing them
US4644002A (en) *	1979-02-09	1987-02-17	Roussel Uclaf	Imidazo[2,1-C]quinolines, useful as antiallergic agents
IT1150955B (it) *	1980-06-06	1986-12-17	Lepetit Spa	Derivati 3h-naft(1.2-d)-imidazolici il procedimento per la loro preparazione, il loro uso come agenti antiinfiammatori e le composizioni farmaceutiche che li contengono
DE3314843A1 (de) *	1983-04-23	1984-10-25	Beiersdorf Ag, 2000 Hamburg	1-amidino-2,3,3a,8-tetrahydro-1h-pyrazolo (5,1-a)isoindol, verfahren zu dessen herstellung, diese verbindung enthaltende zubereitungen und zwischenprodukte
GB8415540D0 (en) *	1984-06-18	1984-07-25	Fujisawa Pharmaceutical Co	Imidazoisoquinoline compounds
EP0607076A1 (fr) *	1993-01-15	1994-07-20	Synthelabo	Dérivés de 9h-imidazo 1,2-a benzimidazole-3-acétamide à activité GABA
CA2213197C (en) *	1995-02-15	2001-08-07	Neurogen Corporation	Certain bridged 4-phenyl-2-aminomethylimidazoles; new dopamine receptor subtype specific ligands
US5948912A (en) *	1995-02-15	1999-09-07	Neurogen Corporation	Certain bridged 4-phenyl-2-aminomethylimidazoles; new dopamine receptor subtype specific ligands
TW416953B (en)	1996-09-25	2001-01-01	Takeda Chemical Industries Ltd	Tricyclic compounds for eliciting a prostaglandin I2 receptor agonistic effect, their production and use
NZ528820A (en) *	2001-04-19	2007-01-26	Eisai Co Ltd	2-iminopyrrolidine derivatives
US20040198791A1 (en) *	2001-06-05	2004-10-07	Yoshinari Sato	Fused imidazole derivative
EP2444393A1 (en) *	2003-02-19	2012-04-25	Eisai R&D Management Co., Ltd.	Methods for producing cyclic benzamidine derivatives
EP1797072A4 (en) *	2004-09-17	2009-09-09	Exelixis Inc	PYRAZOLKINASE MODULATORS AND USE METHOD
US11142504B2 (en)	2016-03-07	2021-10-12	Northwestern University	Substituted heterocycles as c-MYC targeting agents
EP3426636B1 (en) *	2016-03-07	2021-12-29	Northwestern University	Specific 2-(4-(phenoxy)-1h-pyrazol-3-yl)phenol derivatives as inhibitors of c-myc/dna binding activity for treating cancer
US11420957B2 (en)	2019-06-17	2022-08-23	Northwestern University	Substituted heterocycles as c-MYC targeting agents
CN110294758B (zh) *	2019-07-06	2021-10-22	湘潭大学	2-取代5，6-二氢吡唑并[5，1-α]异喹啉、衍生物及其合成方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1244501A (en) *	1968-03-09	1971-09-02	Aspro Nicholas Ltd	Heterocyclic amines
GB1347493A (en) *	1971-02-11	1974-02-27	Aspro Nicholas Ltd	Benzazine derivatives

1974
- 1974-11-23 GB GB50855/74A patent/GB1484615A/en not_active Expired
1975
- 1975-10-27 IN IN2064/CAL/75A patent/IN142014B/en unknown
- 1975-10-27 IN IN2063/CAL/1975A patent/IN141710B/en unknown
- 1975-10-28 ZA ZA00756792A patent/ZA756792B/xx unknown
- 1975-10-30 GR GR49241A patent/GR58292B/el unknown
- 1975-10-30 GR GR49242A patent/GR58293B/el unknown
- 1975-10-31 IL IL48389A patent/IL48389A/xx unknown
- 1975-10-31 FI FI753046A patent/FI58919C/fi not_active IP Right Cessation
- 1975-10-31 FI FI753045A patent/FI58918C/fi not_active IP Right Cessation
- 1975-11-03 NL NL7512848.A patent/NL165741C/xx not_active IP Right Cessation
- 1975-11-06 US US05/629,339 patent/US4075342A/en not_active Expired - Lifetime
- 1975-11-17 NO NO753853A patent/NO143577C/no unknown
- 1975-11-17 NO NO753854A patent/NO143578C/no unknown
- 1975-11-18 YU YU2927/75A patent/YU37328B/xx unknown
- 1975-11-19 DE DE2551868A patent/DE2551868C2/de not_active Expired
- 1975-11-20 AT AT884675A patent/AT346332B/de not_active IP Right Cessation
- 1975-11-20 DK DK522175A patent/DK152756C/da not_active IP Right Cessation
- 1975-11-20 DK DK522275A patent/DK522275A/da not_active Application Discontinuation
- 1975-11-20 AT AT884575A patent/AT344176B/de active
- 1975-11-21 CA CA240,176A patent/CA1068274A/en not_active Expired
- 1975-11-21 CH CH1514575A patent/CH614444A5/xx not_active IP Right Cessation
- 1975-11-21 SU SU7502191056A patent/SU578883A3/ru active
- 1975-11-21 FR FR7535716A patent/FR2291747A1/fr active Granted
- 1975-11-21 BE BE162093A patent/BE835836A/xx not_active IP Right Cessation
- 1975-11-21 IE IE2541/75A patent/IE43567B1/en unknown
- 1975-11-21 CH CH1514475A patent/CH614208A5/xx not_active IP Right Cessation
- 1975-11-21 CA CA240,175A patent/CA1068273A/en not_active Expired
- 1975-11-21 JP JP14010775A patent/JPS5516513B2/ja not_active Expired
- 1975-11-21 AR AR261307A patent/AR210476A1/es active
- 1975-11-21 DD DD189610A patent/DD122819A5/xx unknown
- 1975-11-21 LU LU73849A patent/LU73849A1/xx unknown
- 1975-11-21 SE SE7513138A patent/SE421620B/xx unknown
- 1975-11-21 LU LU73850A patent/LU73850A1/xx unknown
- 1975-11-21 SU SU7502191054A patent/SU569290A3/ru active
- 1975-11-21 SE SE7513137A patent/SE421619B/xx not_active IP Right Cessation
- 1975-11-21 AR AR261306A patent/AR209459A1/es active
- 1975-11-21 ES ES442864A patent/ES442864A1/es not_active Expired
- 1975-11-21 DD DD189609A patent/DD122818A5/xx unknown
- 1975-11-21 ES ES442863A patent/ES442863A1/es not_active Expired
1976
- 1976-08-30 SU SU762391456A patent/SU582764A3/ru active

Also Published As

Publication number	Publication date
JPS5516513B2 (2)	1980-05-02
IL48389A0 (en)	1975-12-31
LU73850A1 (2)	1976-06-11
FI753045A7 (2)	1976-05-24
CA1068274A (en)	1979-12-18
DD122818A5 (2)	1976-11-05
AR210476A1 (es)	1977-08-15
SU582764A3 (ru)	1977-11-30
AT346332B (de)	1978-11-10
JPS5175098A (2)	1976-06-29
NO143578B (no)	1980-12-01
CH614444A5 (2)	1979-11-30
SE7513138L (sv)	1976-05-24
SE421619B (sv)	1982-01-18
DE2551868C2 (de)	1982-07-15
NO753854L (2)	1976-05-25
FI58918C (fi)	1981-05-11
LU73849A1 (2)	1976-06-11
DK152756C (da)	1988-09-26
FI753046A7 (2)	1976-05-24
FR2291747A1 (fr)	1976-06-18
SE7513137L (sv)	1976-05-24
GR58293B (en)	1977-09-20
FR2291747B1 (2)	1978-11-17
ES442863A1 (es)	1977-08-16
ATA884575A (de)	1977-11-15
NO753853L (2)	1976-05-25
ZA756792B (en)	1976-10-27
GB1484615A (en)	1977-09-01
GR58292B (en)	1977-09-20
SU578883A3 (ru)	1977-10-30
NO143577B (no)	1980-12-01
AR209459A1 (es)	1977-04-29
IN142014B (2)	1977-05-21
IE43567B1 (en)	1981-04-08
YU292775A (en)	1983-04-27
IL48389A (en)	1979-01-31
DK152756B (da)	1988-05-09
ES442864A1 (es)	1977-08-16
YU37328B (en)	1984-08-31
FI58918B (fi)	1981-01-30
CA1068273A (en)	1979-12-18
DK522175A (da)	1976-05-24
FI58919B (fi)	1981-01-30
NL7512848A (nl)	1976-05-25
AT344176B (de)	1978-07-10
DD122819A5 (2)	1976-11-05
CH614208A5 (2)	1979-11-15
DK522275A (da)	1976-05-24
ATA884675A (de)	1978-03-15
NO143578C (no)	1981-03-11
IN141710B (2)	1977-04-09
NL165741C (nl)	1981-05-15
IE43567L (en)	1976-05-23
NL165741B (nl)	1980-12-15
DE2551868A1 (de)	1976-08-12
NO143577C (no)	1981-03-11
US4075342A (en)	1978-02-21
BE835836A (fr)	1976-03-16
AU8620475A (en)	1977-05-05
SE421620B (sv)	1982-01-18
SU569290A3 (ru)	1977-08-15

Legal Events

Date	Code	Title	Description
2004-08-31	MM	Patent lapsed	Owner name: GRUPPO LEPETIT S.P.A.

Publication	Publication Date	Title
FI58919C (fi)	1981-05-11	Foerfarande foer framstaellning av pyrazolo(5,1-a)isokinoliner och 5,6-dihydropyrazolo(5,1-a)isokinoliner med antireproduktiv aktivitet
US4148897A (en)	1979-04-10	1,2-Dihydronaphthalene derivatives and pharmaceutical composition
CZ219895A3 (en)	1996-03-13	The use of substituted derivatives of 4-phenyl-6-aminonicotinic acid as medicaments
EP0005365B1 (en)	1982-01-06	Pyrano and thiopyrano (3,4-b) indole derivatives, processes for their preparation and pharmaceutical compositions containing them
JPS62161781A (ja)	1987-07-17	フラボン誘導体、その製造法及びそれを含む医薬
US4072754A (en)	1978-02-07	Hydratropic acid derivatives and process for the production thereof
US4596821A (en)	1986-06-24	Treatment of gray matter edema with 3-(2,3-dihydro-1H-inden-5-yl)-4-hydroxy-1H-pyrrole-2,5-diones
US4604403A (en)	1986-08-05	Use of substituted-3(2,3-dihydro-1H-inden-5-yl)-4-hydroxy-1H-pyrrole-2,5-diones for treating grey matter edema
US4605664A (en)	1986-08-12	Use of substituted-3-(2,3-dihydro-1H-inden-5-yl)-4-hydroxy-1H-pyrrole-2,5-diones for treatment of grey matter edema
US4382936A (en)	1983-05-10	Cerebral vasodilator eburnane derivatives
US4634717A (en)	1987-01-06	Substituted-3-(2,3-dihydro-1H-inden-5-yl)-4-hydroxy-1H-pyrrole-2,5-diones, useful for treating persons with gray matter edema
US4305954A (en)	1981-12-15	Antiinflammatory 3,4-dihydro(or 1,4-dihydro)-2-[(substituted)thio]-[1]benzopyrano[3,4-d]imidazoles and their corresponding sulfoxides and sulfones
US4605663A (en)	1986-08-12	Use of substituted-3-(2,3-dihydro-1H-inden-5-yl)-4-hydroxy-1H-pyrrole-2,5-diones, for treatment of grey matter edema
US3895113A (en)	1975-07-15	Antifertility methods employing triazoloisoquinoline derivatives
FI57107B (fi)	1980-02-29	Foerfarande foer framstaellning av nya s-triazolo(5,1-a)isoindoler med befruktningsfoerhindrande verkan
US4024149A (en)	1977-05-17	2-Phenyl-pyrazolo-[1,5-a]quinoline compounds
US4362891A (en)	1982-12-07	Alkanoic acid derivatives
US4680414A (en)	1987-07-14	Substituted-3-(2,3-dihydro-1H-inden-5-yl)-4-hydroxy-1H-pyrrole-2,5-diones
US4081449A (en)	1978-03-28	Heterocyclic esters of alkylphenyl benzopyranopyridines
US4275066A (en)	1981-06-23	Antireproductive tricyclic ortho-fused nitrogen containing compounds
US4721719A (en)	1988-01-26	Dihydropyridinelactols and their use as medicaments which influence blood sugar
US5310750A (en)	1994-05-10	Heterocyclic compounds useful as α2 -adrenoceptor antagonists
US3972883A (en)	1976-08-03	1,6-Dimethyl-8β-[2' or 3'-pyrroyloxyethyl or substituted pyrroyloxyethyl]-10α-methoxyergolene compounds
US4559356A (en)	1985-12-17	2-(Inden-2-yl)-imidazoline derivatives, process for their preparation and pharmaceutical compositions containing them
EP0168181B1 (en)	1990-08-29	Cyclic amides