DD298391A5 - Verfahren zur herstellung von pyridinderivaten - Google Patents
Verfahren zur herstellung von pyridinderivaten Download PDFInfo
- Publication number
- DD298391A5 DD298391A5 DD90339534A DD33953490A DD298391A5 DD 298391 A5 DD298391 A5 DD 298391A5 DD 90339534 A DD90339534 A DD 90339534A DD 33953490 A DD33953490 A DD 33953490A DD 298391 A5 DD298391 A5 DD 298391A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- tetrahydro
- lower alkyl
- group
- aryl
- quinoline
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 54
- 238000002360 preparation method Methods 0.000 title claims description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 99
- -1 heteroaromatic N-oxides Chemical class 0.000 claims abstract description 41
- 239000002253 acid Substances 0.000 claims abstract description 21
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 55
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 44
- 150000001412 amines Chemical class 0.000 claims description 33
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 33
- 125000003118 aryl group Chemical group 0.000 claims description 31
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000006239 protecting group Chemical group 0.000 claims description 5
- 150000003254 radicals Chemical class 0.000 claims description 5
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- YQDGQEKUTLYWJU-UHFFFAOYSA-N 5,6,7,8-tetrahydroquinoline Chemical compound C1=CC=C2CCCCC2=N1 YQDGQEKUTLYWJU-UHFFFAOYSA-N 0.000 claims description 3
- 125000004608 5,6,7,8-tetrahydroquinolinyl group Chemical group N1=C(C=CC=2CCCCC12)* 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 239000002243 precursor Substances 0.000 claims description 3
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 3
- SHQUNUAMNCPZNJ-UHFFFAOYSA-N 5,6,7,8-tetrahydroquinolin-2-amine Chemical compound C1CCCC2=NC(N)=CC=C21 SHQUNUAMNCPZNJ-UHFFFAOYSA-N 0.000 claims 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 2
- 150000005010 aminoquinolines Chemical class 0.000 claims 2
- QASPDCZPPDUIIE-UHFFFAOYSA-N 2,2-difluoro-2-phenylacetamide Chemical compound NC(=O)C(F)(F)C1=CC=CC=C1 QASPDCZPPDUIIE-UHFFFAOYSA-N 0.000 claims 1
- NIWBCQQIJSJEON-UHFFFAOYSA-N 3-methyl-n,n-dipropyl-5,6,7,8-tetrahydroquinolin-7-amine Chemical compound CC1=CN=C2CC(N(CCC)CCC)CCC2=C1 NIWBCQQIJSJEON-UHFFFAOYSA-N 0.000 claims 1
- QBJUMRBOQCCGNO-UHFFFAOYSA-N 4-chloro-n,n-dipropyl-5,6,7,8-tetrahydroquinolin-7-amine Chemical compound C1=CN=C2CC(N(CCC)CCC)CCC2=C1Cl QBJUMRBOQCCGNO-UHFFFAOYSA-N 0.000 claims 1
- NTCXZWXWETZTKK-UHFFFAOYSA-N 4-methyl-n,n-dipropyl-5,6,7,8-tetrahydroquinolin-7-amine Chemical compound C1=CN=C2CC(N(CCC)CCC)CCC2=C1C NTCXZWXWETZTKK-UHFFFAOYSA-N 0.000 claims 1
- WRFZQXPAFCXTTC-UHFFFAOYSA-N 5,6,7,8-tetrahydroquinolin-7-amine Chemical compound C1=CN=C2CC(N)CCC2=C1 WRFZQXPAFCXTTC-UHFFFAOYSA-N 0.000 claims 1
- VHBGBUXLJDSOHK-UHFFFAOYSA-N 7-pyrrolidin-1-yl-5,6,7,8-tetrahydroquinoline Chemical compound C1CCCN1C1CC2=NC=CC=C2CC1 VHBGBUXLJDSOHK-UHFFFAOYSA-N 0.000 claims 1
- 125000000928 benzodioxinyl group Chemical group O1C(=COC2=C1C=CC=C2)* 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- OIXOVXLTNUIOTR-UHFFFAOYSA-N n-benzyl-5,6,7,8-tetrahydroquinolin-7-amine Chemical compound C1CC2=CC=CN=C2CC1NCC1=CC=CC=C1 OIXOVXLTNUIOTR-UHFFFAOYSA-N 0.000 claims 1
- ZEWIZKPYVPPIPL-UHFFFAOYSA-N n-methyl-5,6,7,8-tetrahydroquinolin-7-amine Chemical compound C1=CN=C2CC(NC)CCC2=C1 ZEWIZKPYVPPIPL-UHFFFAOYSA-N 0.000 claims 1
- MFXVTMONKNGVJT-UHFFFAOYSA-N n-methyl-n-(2-phenylethyl)-5,6,7,8-tetrahydroquinolin-7-amine Chemical compound C1CC2=CC=CN=C2CC1N(C)CCC1=CC=CC=C1 MFXVTMONKNGVJT-UHFFFAOYSA-N 0.000 claims 1
- IYXFYNBZOPUPJY-UHFFFAOYSA-N n-methyl-n-propyl-5,6,7,8-tetrahydroquinolin-7-amine Chemical compound C1=CN=C2CC(N(C)CCC)CCC2=C1 IYXFYNBZOPUPJY-UHFFFAOYSA-N 0.000 claims 1
- CHMVJJXGTCFYLK-UHFFFAOYSA-N n-phenyl-5,6,7,8-tetrahydroquinolin-7-amine Chemical compound C1CC2=CC=CN=C2CC1NC1=CC=CC=C1 CHMVJJXGTCFYLK-UHFFFAOYSA-N 0.000 claims 1
- HWJSLPJGXRDBEO-UHFFFAOYSA-N n-propyl-5,6,7,8-tetrahydroquinolin-7-amine Chemical compound C1=CN=C2CC(NCCC)CCC2=C1 HWJSLPJGXRDBEO-UHFFFAOYSA-N 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 7
- 229940030600 antihypertensive agent Drugs 0.000 abstract description 4
- 239000002220 antihypertensive agent Substances 0.000 abstract description 4
- 150000003222 pyridines Chemical class 0.000 abstract description 4
- 239000000556 agonist Substances 0.000 abstract description 3
- 239000005557 antagonist Substances 0.000 abstract description 3
- 208000019901 Anxiety disease Diseases 0.000 abstract description 2
- 208000022531 anorexia Diseases 0.000 abstract description 2
- 230000036506 anxiety Effects 0.000 abstract description 2
- 206010061428 decreased appetite Diseases 0.000 abstract description 2
- 239000004031 partial agonist Substances 0.000 abstract description 2
- 102100022738 5-hydroxytryptamine receptor 1A Human genes 0.000 abstract 1
- 101710138638 5-hydroxytryptamine receptor 1A Proteins 0.000 abstract 1
- 208000015114 central nervous system disease Diseases 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 110
- 239000000047 product Substances 0.000 description 106
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 96
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 90
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 81
- 239000003921 oil Substances 0.000 description 79
- 235000019198 oils Nutrition 0.000 description 79
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 74
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 69
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 48
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 43
- 239000000284 extract Substances 0.000 description 41
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
- 239000012458 free base Substances 0.000 description 39
- 239000000203 mixture Substances 0.000 description 39
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 36
- 238000004587 chromatography analysis Methods 0.000 description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 28
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
- 239000007787 solid Substances 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 20
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 19
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 18
- ROLKDXFFBNOIDS-UHFFFAOYSA-N 5,6-dihydroquinoline Chemical compound C1=CN=C2C=CCCC2=C1 ROLKDXFFBNOIDS-UHFFFAOYSA-N 0.000 description 17
- 239000011734 sodium Substances 0.000 description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000000741 silica gel Substances 0.000 description 15
- 229910002027 silica gel Inorganic materials 0.000 description 15
- 229960000583 acetic acid Drugs 0.000 description 14
- 239000012043 crude product Substances 0.000 description 14
- 239000007788 liquid Substances 0.000 description 14
- 229920006395 saturated elastomer Polymers 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 11
- 239000012074 organic phase Substances 0.000 description 11
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 125000003277 amino group Chemical group 0.000 description 10
- OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 10
- 239000004480 active ingredient Substances 0.000 description 9
- 150000001408 amides Chemical class 0.000 description 9
- 239000012141 concentrate Substances 0.000 description 9
- 235000008504 concentrate Nutrition 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 230000002378 acidificating effect Effects 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 239000012299 nitrogen atmosphere Substances 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 239000003638 chemical reducing agent Substances 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 6
- 238000001665 trituration Methods 0.000 description 6
- 239000007868 Raney catalyst Substances 0.000 description 5
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 5
- 229910000564 Raney nickel Inorganic materials 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 125000003282 alkyl amino group Chemical group 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 5
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 5
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 239000006260 foam Substances 0.000 description 5
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 230000027455 binding Effects 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
- 210000003169 central nervous system Anatomy 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 125000002560 nitrile group Chemical group 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 102000005962 receptors Human genes 0.000 description 4
- 108020003175 receptors Proteins 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 3
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 3
- 235000019502 Orange oil Nutrition 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Natural products OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- RPBLEVAVQBCBFI-UHFFFAOYSA-N hydroxy(propyl)azanium;chloride Chemical compound Cl.CCCNO RPBLEVAVQBCBFI-UHFFFAOYSA-N 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000010502 orange oil Substances 0.000 description 3
- 238000007911 parenteral administration Methods 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 229940124530 sulfonamide Drugs 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 2
- FUGDCKXBUZFEON-UHFFFAOYSA-N 2-(2,6-difluorophenyl)acetic acid Chemical compound OC(=O)CC1=C(F)C=CC=C1F FUGDCKXBUZFEON-UHFFFAOYSA-N 0.000 description 2
- CZKLEJHVLCMVQR-UHFFFAOYSA-N 4-fluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C=C1 CZKLEJHVLCMVQR-UHFFFAOYSA-N 0.000 description 2
- FJNCXZZQNBKEJT-UHFFFAOYSA-N 8beta-hydroxymarrubiin Natural products O1C(=O)C2(C)CCCC3(C)C2C1CC(C)(O)C3(O)CCC=1C=COC=1 FJNCXZZQNBKEJT-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 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
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000011777 magnesium 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
- 239000011976 maleic acid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- FCVMPRQTRCSXKE-UHFFFAOYSA-N methanol propan-2-ol Chemical compound OC.CC(C)O.CC(C)O.CC(C)O FCVMPRQTRCSXKE-UHFFFAOYSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- WCYMWQIUHPXBKM-UHFFFAOYSA-N n,n-diethylethanamine;ethoxyethane Chemical compound CCOCC.CCN(CC)CC WCYMWQIUHPXBKM-UHFFFAOYSA-N 0.000 description 1
- XLXLFOCZPYSAKF-UHFFFAOYSA-N n-(1-phenylethyl)hydroxylamine;hydrochloride Chemical compound Cl.ONC(C)C1=CC=CC=C1 XLXLFOCZPYSAKF-UHFFFAOYSA-N 0.000 description 1
- FZZZQLZHUMHCOX-UHFFFAOYSA-N n-(4-methyl-5,6,7,8-tetrahydroquinolin-7-yl)-n-propylhydroxylamine Chemical compound C1=CN=C2CC(N(O)CCC)CCC2=C1C FZZZQLZHUMHCOX-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- BHIIWXJHALLFBD-UHFFFAOYSA-N oxolane;propan-2-ol Chemical compound CC(C)O.C1CCOC1 BHIIWXJHALLFBD-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000012057 packaged powder Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- WJCXADMLESSGRI-UHFFFAOYSA-N phenyl selenohypochlorite Chemical compound Cl[Se]C1=CC=CC=C1 WJCXADMLESSGRI-UHFFFAOYSA-N 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229920006316 polyvinylpyrrolidine Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000013014 purified material Substances 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000000018 receptor agonist Substances 0.000 description 1
- 229940044601 receptor agonist Drugs 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 1
- 238000005055 short column chromatography Methods 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 239000002562 thickening agent Substances 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
- 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
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/38—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB898907865A GB8907865D0 (en) | 1989-04-07 | 1989-04-07 | Tetrahydroquinoline derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD298391A5 true DD298391A5 (de) | 1992-02-20 |
Family
ID=10654625
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD90339534A DD298391A5 (de) | 1989-04-07 | 1990-04-06 | Verfahren zur herstellung von pyridinderivaten |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US5075303A (fr) |
| EP (1) | EP0395244B1 (fr) |
| JP (1) | JP2945064B2 (fr) |
| KR (1) | KR0156569B1 (fr) |
| AT (1) | ATE149031T1 (fr) |
| AU (1) | AU625845B2 (fr) |
| CA (1) | CA2014062C (fr) |
| DD (1) | DD298391A5 (fr) |
| DE (1) | DE69029954T2 (fr) |
| DK (1) | DK0395244T3 (fr) |
| ES (1) | ES2099703T3 (fr) |
| FI (1) | FI95373C (fr) |
| GB (2) | GB8907865D0 (fr) |
| GR (1) | GR3023396T3 (fr) |
| HK (1) | HK121994A (fr) |
| HU (1) | HU217128B (fr) |
| IE (1) | IE63627B1 (fr) |
| IL (1) | IL94011A (fr) |
| NZ (1) | NZ233222A (fr) |
| PH (1) | PH27590A (fr) |
| PT (1) | PT93673B (fr) |
| ZA (1) | ZA902662B (fr) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5273994A (en) * | 1990-04-09 | 1993-12-28 | Adir Et Compagnie | 3-aminochroman compounds |
| FR2660657B1 (fr) * | 1990-04-09 | 1993-05-07 | Adir | Nouveaux derives du 3-aminochromane, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| GB9019942D0 (en) * | 1990-09-12 | 1990-10-24 | Wyeth John & Brother Ltd | Azetidine derivatives |
| US5532243A (en) * | 1992-02-14 | 1996-07-02 | The Dupont Merck Pharmaceutical Company | Antipsychotic nitrogen-containing bicyclic compounds |
| GB9304632D0 (en) * | 1993-03-06 | 1993-04-21 | Wyeth John & Brother Ltd | Amide derivatives |
| EP0743855A1 (fr) * | 1994-01-03 | 1996-11-27 | Acea Pharmaceuticals, Inc. | 8-aza, 6-aza et 6,8-diaza-1,4-dihydroquinoxaline-2,3-diones et leur utilisation comme antagonistes du recepteur de la glycine ou du nmda |
| US5609849A (en) * | 1994-03-11 | 1997-03-11 | The Trustees Of The University Of Pennsylvania | Serotonin (5-HT1A) receptor ligands and imaging agents |
| US6180632B1 (en) * | 1997-05-28 | 2001-01-30 | Aventis Pharmaceuticals Products Inc. | Quinoline and quinoxaline compounds which inhibit platelet-derived growth factor and/or p56lck tyrosine kinases |
| US7105513B2 (en) * | 2002-08-07 | 2006-09-12 | Sanofi-Avertis Deutschland Gmbh | Acylated, heteroaryl-condensed cycloalkenylamines and their use as pharmaceuticals |
| AU2010227311B2 (en) * | 2009-03-23 | 2014-06-05 | Cipla Limited | Process for the preparation of doxazosin and salts thereof |
| KR101987514B1 (ko) * | 2011-10-18 | 2019-06-10 | 아스텔라스세이야쿠 가부시키가이샤 | 이환식 헤테로환 화합물 |
| US9933417B2 (en) | 2014-04-01 | 2018-04-03 | Howard Hughes Medical Institute | Azetidine-substituted fluorescent compounds |
| US12440581B2 (en) | 2019-09-19 | 2025-10-14 | Howard Hughes Medical Institute | Fluorophores for super-resolution imaging |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH566315A5 (fr) * | 1972-04-04 | 1975-09-15 | Ciba Geigy Ag | |
| GB1463583A (en) * | 1974-03-05 | 1977-02-02 | Wyeth John & Brother Ltd | Halo and hydroxy compounds |
| GB1463582A (en) * | 1974-03-05 | 1977-02-02 | Wyeth John & Brother Ltd | Pyridine derivatives |
| FI68821C (fi) * | 1977-07-18 | 1985-11-11 | Sandoz Ag | Analogifoerfarande foer framstaellning av nya tetralinderivat vilka saenker blodtryck och oekar blodetsgenomstroemning |
| SE8004002L (sv) * | 1980-05-29 | 1981-11-30 | Arvidsson Folke Lars Erik | Terapeutiskt anvendbara tetralinderivat |
| US4748182A (en) * | 1986-03-05 | 1988-05-31 | Merrell Dow Pharmaceuticals Inc. | Aromatic 2-aminoalkyl-1,2-benzoisothiazol-3(2H)one-1,1-dioxide derivatives and their use as anti-hypertensive and anxiolytic agents |
| DK111387A (da) * | 1986-03-05 | 1987-09-06 | Otsuka Pharma Co Ltd | Carbostyrilderivater og salte deraf, laegemiddel indeholdende saadanne derivater samt fremgangsmaade til fremstilling af derivaterne |
| JPS63107990A (ja) * | 1986-05-14 | 1988-05-12 | Nippon Shinyaku Co Ltd | キノリンカルボン酸誘導体 |
| DE3718317A1 (de) * | 1986-12-10 | 1988-06-16 | Bayer Ag | Substituierte basische 2-aminotetraline |
| DE3719924A1 (de) * | 1986-12-22 | 1988-06-30 | Bayer Ag | 8-substituierte 2-aminotetraline |
| US4878941A (en) * | 1987-12-29 | 1989-11-07 | Fmc Corporation | Herbicides |
| US4894084A (en) * | 1987-12-29 | 1990-01-16 | Fmc Corporation | Substituted quinolinonyl and dihydroquinolinonyl triazolinone herbicides |
-
1989
- 1989-04-07 GB GB898907865A patent/GB8907865D0/en active Pending
-
1990
- 1990-04-05 AU AU52971/90A patent/AU625845B2/en not_active Ceased
- 1990-04-05 NZ NZ233222A patent/NZ233222A/en unknown
- 1990-04-05 IL IL9401190A patent/IL94011A/en not_active IP Right Cessation
- 1990-04-05 PT PT93673A patent/PT93673B/pt not_active IP Right Cessation
- 1990-04-05 ZA ZA902662A patent/ZA902662B/xx unknown
- 1990-04-06 DD DD90339534A patent/DD298391A5/de unknown
- 1990-04-06 HU HU902108A patent/HU217128B/hu not_active IP Right Cessation
- 1990-04-06 CA CA002014062A patent/CA2014062C/fr not_active Expired - Fee Related
- 1990-04-06 KR KR1019900004697A patent/KR0156569B1/ko not_active Expired - Fee Related
- 1990-04-06 ES ES90303708T patent/ES2099703T3/es not_active Expired - Lifetime
- 1990-04-06 JP JP2092961A patent/JP2945064B2/ja not_active Expired - Fee Related
- 1990-04-06 IE IE125290A patent/IE63627B1/en not_active IP Right Cessation
- 1990-04-06 DE DE69029954T patent/DE69029954T2/de not_active Expired - Fee Related
- 1990-04-06 PH PH40345A patent/PH27590A/en unknown
- 1990-04-06 DK DK90303708.3T patent/DK0395244T3/da active
- 1990-04-06 AT AT90303708T patent/ATE149031T1/de not_active IP Right Cessation
- 1990-04-06 EP EP90303708A patent/EP0395244B1/fr not_active Expired - Lifetime
- 1990-04-06 US US07/505,957 patent/US5075303A/en not_active Expired - Lifetime
- 1990-04-06 GB GB9007889A patent/GB2230007B/en not_active Expired - Fee Related
- 1990-04-06 FI FI901761A patent/FI95373C/fi not_active IP Right Cessation
-
1994
- 1994-11-03 HK HK121994A patent/HK121994A/xx not_active IP Right Cessation
-
1997
- 1997-05-09 GR GR970401050T patent/GR3023396T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2945064B2 (ja) | 1999-09-06 |
| FI901761A0 (fi) | 1990-04-06 |
| GB2230007B (en) | 1992-10-14 |
| HU217128B (hu) | 1999-11-29 |
| PT93673B (pt) | 1996-08-30 |
| FI95373B (fi) | 1995-10-13 |
| ATE149031T1 (de) | 1997-03-15 |
| EP0395244B1 (fr) | 1997-02-19 |
| IE63627B1 (en) | 1995-05-17 |
| KR0156569B1 (ko) | 1998-11-16 |
| DE69029954D1 (de) | 1997-03-27 |
| PH27590A (en) | 1993-08-18 |
| GB9007889D0 (en) | 1990-06-06 |
| US5075303A (en) | 1991-12-24 |
| HU902108D0 (en) | 1990-08-28 |
| GB8907865D0 (en) | 1989-05-24 |
| GB2230007A (en) | 1990-10-10 |
| HK121994A (en) | 1994-11-11 |
| KR900016138A (ko) | 1990-11-12 |
| DE69029954T2 (de) | 1997-05-28 |
| ES2099703T3 (es) | 1997-06-01 |
| AU5297190A (en) | 1990-10-11 |
| NZ233222A (en) | 1991-07-26 |
| HUT54658A (en) | 1991-03-28 |
| JPH02290852A (ja) | 1990-11-30 |
| GR3023396T3 (en) | 1997-08-29 |
| AU625845B2 (en) | 1992-07-16 |
| EP0395244A1 (fr) | 1990-10-31 |
| CA2014062C (fr) | 2000-06-13 |
| IL94011A (en) | 1994-06-24 |
| CA2014062A1 (fr) | 1990-10-07 |
| FI95373C (fi) | 1996-01-25 |
| DK0395244T3 (da) | 1997-03-17 |
| PT93673A (pt) | 1990-11-20 |
| ZA902662B (en) | 1991-02-27 |
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