FI58918C - Foerfarande foer framstaellning av imidazo(2,1-a)isokinoliner och 5,6-dihydro-imidazo(2,1-a)isokinoliner med antireproduktiv aktivitet - Google Patents
Foerfarande foer framstaellning av imidazo(2,1-a)isokinoliner och 5,6-dihydro-imidazo(2,1-a)isokinoliner med antireproduktiv aktivitet Download PDFInfo
- Publication number
- FI58918C FI58918C FI753045A FI753045A FI58918C FI 58918 C FI58918 C FI 58918C FI 753045 A FI753045 A FI 753045A FI 753045 A FI753045 A FI 753045A FI 58918 C FI58918 C FI 58918C
- Authority
- FI
- Finland
- Prior art keywords
- formula
- isoquinoline
- imidazo
- alkoxy
- alkyl
- Prior art date
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- 230000000694 effects Effects 0.000 title claims description 12
- 150000002537 isoquinolines Chemical class 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims description 36
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 22
- -1 2,5-dimethoxyphenyl Chemical group 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 125000005336 allyloxy group Chemical group 0.000 claims description 6
- BYLPZVAKOZYZPH-UHFFFAOYSA-N imidazo[2,1-a]isoquinoline Chemical class C1=CC=C2C3=NC=CN3C=CC2=C1 BYLPZVAKOZYZPH-UHFFFAOYSA-N 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- OSILBMSORKFRTB-UHFFFAOYSA-N isoquinolin-1-amine Chemical compound C1=CC=C2C(N)=NC=CC2=C1 OSILBMSORKFRTB-UHFFFAOYSA-N 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 125000005490 tosylate group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical group BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 claims 1
- 231100000331 toxic Toxicity 0.000 claims 1
- 230000002588 toxic effect Effects 0.000 claims 1
- 241001465754 Metazoa Species 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 210000003754 fetus Anatomy 0.000 description 7
- 230000035935 pregnancy Effects 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 230000003509 anti-fertility effect Effects 0.000 description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 4
- 238000002513 implantation Methods 0.000 description 4
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- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- BHVYXFROIATQQJ-UHFFFAOYSA-N 2-(3-methoxyphenyl)imidazo[2,1-a]isoquinoline Chemical compound COC1=CC=CC(C=2N=C3C4=CC=CC=C4C=CN3C=2)=C1 BHVYXFROIATQQJ-UHFFFAOYSA-N 0.000 description 2
- GQSHFYGCUBUDCI-UHFFFAOYSA-N 3h-imidazo[4,5-h]isoquinoline Chemical class C1=CN=CC2=C(NC=N3)C3=CC=C21 GQSHFYGCUBUDCI-UHFFFAOYSA-N 0.000 description 2
- 241000699800 Cricetinae Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 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
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000005843 halogen group Chemical group 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
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000008159 sesame oil Substances 0.000 description 2
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- 235000020357 syrup Nutrition 0.000 description 2
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- 239000000454 talc Substances 0.000 description 2
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
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- 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
- DXQRYFLJALBVOM-UHFFFAOYSA-N 2-(2-chlorophenyl)imidazo[2,1-a]isoquinoline Chemical compound ClC1=CC=CC=C1C1=CN(C=CC=2C3=CC=CC=2)C3=N1 DXQRYFLJALBVOM-UHFFFAOYSA-N 0.000 description 1
- JNJGNJXCTIUHCW-UHFFFAOYSA-N 2-(2-methoxyphenyl)imidazo[2,1-a]isoquinoline Chemical compound COC1=CC=CC=C1C1=CN(C=CC=2C3=CC=CC=2)C3=N1 JNJGNJXCTIUHCW-UHFFFAOYSA-N 0.000 description 1
- ZHOVVTLZEFCCSV-UHFFFAOYSA-N 2-(3-prop-2-enoxyphenyl)imidazo[2,1-a]isoquinoline Chemical compound C=CCOC1=CC=CC(C=2N=C3C4=CC=CC=C4C=CN3C=2)=C1 ZHOVVTLZEFCCSV-UHFFFAOYSA-N 0.000 description 1
- RIWBAVICDRBVGP-UHFFFAOYSA-N 2-(4-bromophenyl)imidazo[2,1-a]isoquinoline Chemical compound C1=CC(Br)=CC=C1C1=CN(C=CC=2C3=CC=CC=2)C3=N1 RIWBAVICDRBVGP-UHFFFAOYSA-N 0.000 description 1
- LKENZGMGOAVEHZ-UHFFFAOYSA-N 2-phenylimidazo[2,1-a]isoquinoline Chemical class N1=C2C3=CC=CC=C3C=CN2C=C1C1=CC=CC=C1 LKENZGMGOAVEHZ-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- AZSVMMHTRNMWNY-UHFFFAOYSA-N 3-methyl-2-phenylimidazo[2,1-a]isoquinoline Chemical compound N1=C2C3=CC=CC=C3C=CN2C(C)=C1C1=CC=CC=C1 AZSVMMHTRNMWNY-UHFFFAOYSA-N 0.000 description 1
- GMSPBBGIMCSHSZ-UHFFFAOYSA-N 5,6-dihydroimidazo[2,1-a]isoquinoline Chemical class C12=CC=CC=C2CCN2C1=NC=C2 GMSPBBGIMCSHSZ-UHFFFAOYSA-N 0.000 description 1
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- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance 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
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 229940095064 tartrate Drugs 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-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)
- Other In-Based Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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 |
|---|---|
| FI753045A7 FI753045A7 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-05-24 |
| FI58918B FI58918B (fi) | 1981-01-30 |
| FI58918C true FI58918C (fi) | 1981-05-11 |
Family
ID=10457662
Family Applications (2)
| 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 |
| 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 |
Family Applications After (1)
| 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 |
Country Status (25)
Families Citing this family (20)
| 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 |
| GR70248B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1978-10-30 | 1982-09-01 | Lepetit Spa | |
| US4313950A (en) * | 1978-10-30 | 1982-02-02 | Gruppo Lepetit S.P.A. | Antireproductive tricyclic ortho-fused nitrogen containing compounds |
| DE2964567D1 (en) * | 1978-12-21 | 1983-02-24 | Lepetit Spa | 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 |
| AU4867496A (en) * | 1995-02-15 | 1996-09-04 | 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 |
| US7304083B2 (en) * | 2001-04-19 | 2007-12-04 | Eisai R&D Management Co., Ltd. | 2-iminoimidazole derivatives (2) |
| WO2002098863A1 (fr) * | 2001-06-05 | 2002-12-12 | Fujisawa Pharmaceutical Co., Ltd. | Derive d'imidazole fondu |
| AU2004218187C1 (en) * | 2003-02-19 | 2011-04-07 | 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 |
| 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 |
| US11142504B2 (en) | 2016-03-07 | 2021-10-12 | Northwestern University | Substituted heterocycles as c-MYC targeting agents |
| WO2020257261A1 (en) | 2019-06-17 | 2020-12-24 | 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)
| 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 FI FI753045A patent/FI58918C/fi not_active IP Right Cessation
- 1975-10-31 IL IL48389A patent/IL48389A/xx unknown
- 1975-10-31 FI FI753046A patent/FI58919C/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 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
- 1975-11-20 AT AT884675A patent/AT346332B/de not_active IP Right Cessation
- 1975-11-21 FR FR7535716A patent/FR2291747A1/fr active Granted
- 1975-11-21 CA CA240,176A patent/CA1068274A/en not_active Expired
- 1975-11-21 CH CH1514475A patent/CH614208A5/xx not_active IP Right Cessation
- 1975-11-21 SU SU7502191054A patent/SU569290A3/ru active
- 1975-11-21 SE SE7513138A patent/SE421620B/xx unknown
- 1975-11-21 BE BE162093A patent/BE835836A/xx not_active IP Right Cessation
- 1975-11-21 AR AR261306A patent/AR209459A1/es active
- 1975-11-21 JP JP14010775A patent/JPS5516513B2/ja not_active Expired
- 1975-11-21 DD DD189610A patent/DD122819A5/xx unknown
- 1975-11-21 LU LU73850A patent/LU73850A1/xx unknown
- 1975-11-21 DD DD189609A patent/DD122818A5/xx unknown
- 1975-11-21 CH CH1514575A patent/CH614444A5/xx not_active IP Right Cessation
- 1975-11-21 ES ES442864A patent/ES442864A1/es not_active Expired
- 1975-11-21 ES ES442863A patent/ES442863A1/es not_active Expired
- 1975-11-21 CA CA240,175A patent/CA1068273A/en not_active Expired
- 1975-11-21 SU SU7502191056A patent/SU578883A3/ru active
- 1975-11-21 LU LU73849A patent/LU73849A1/xx unknown
- 1975-11-21 IE IE2541/75A patent/IE43567B1/en unknown
- 1975-11-21 AR AR261307A patent/AR210476A1/es active
- 1975-11-21 SE SE7513137A patent/SE421619B/xx not_active IP Right Cessation
-
1976
- 1976-08-30 SU SU762391456A patent/SU582764A3/ru active
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: GRUPPO LEPETIT S.P.A. |