NL8204275A - Nieuwe cyclische iminen, hun bereiding, alsmede farmaceutische samenstellingen welke hen bevatten. - Google Patents

Nieuwe cyclische iminen, hun bereiding, alsmede farmaceutische samenstellingen welke hen bevatten. Download PDF

Info

Publication number: NL8204275A
Authority: NL; Netherlands
Prior art keywords: general formula; compound; process according; group; acid addition
Prior art date: 1981-11-06

Application number

NL8204275A

Other languages

English (en)

Dutch (nl)

Original Assignee

Egyt Gyogyszervegyeszeti Gyar

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.)

1981-11-06

Filing date

1982-11-04

Publication date

1983-06-01

1982-11-04 Application filed by Egyt Gyogyszervegyeszeti Gyar filed Critical Egyt Gyogyszervegyeszeti Gyar

1983-06-01 Publication of NL8204275A publication Critical patent/NL8204275A/nl

Links

238000002360 preparation method Methods 0.000 title claims description 27
239000008194 pharmaceutical composition Substances 0.000 title claims description 9
150000001875 compounds Chemical class 0.000 claims description 83
-1 Cyclic imine Chemical class 0.000 claims description 57
238000000034 method Methods 0.000 claims description 40
150000003839 salts Chemical class 0.000 claims description 40
239000000460 chlorine Substances 0.000 claims description 24
239000002253 acid Substances 0.000 claims description 23
238000006243 chemical reaction Methods 0.000 claims description 19
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
239000002904 solvent Substances 0.000 claims description 13
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 11
239000007858 starting material Substances 0.000 claims description 11
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
229910052801 chlorine Inorganic materials 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 8
125000001841 imino group Chemical group [H]N=* 0.000 claims description 8
238000009835 boiling Methods 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 6
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 6
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
229940113088 dimethylacetamide Drugs 0.000 claims description 6
239000011541 reaction mixture Substances 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
239000007788 liquid Substances 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
239000007787 solid Substances 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
231100000252 nontoxic Toxicity 0.000 claims description 3
230000003000 nontoxic effect Effects 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
125000003277 amino group Chemical group 0.000 claims description 2
238000010531 catalytic reduction reaction Methods 0.000 claims description 2
239000003586 protic polar solvent Substances 0.000 claims description 2
239000004480 active ingredient Substances 0.000 claims 2
150000002431 hydrogen Chemical class 0.000 claims 2
239000012442 inert solvent Substances 0.000 claims 1
239000003960 organic solvent Substances 0.000 claims 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
239000000047 product Substances 0.000 description 11
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
238000004458 analytical method Methods 0.000 description 9
ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 9
239000000203 mixture Substances 0.000 description 8
LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 description 8
239000002585 base Substances 0.000 description 7
238000001953 recrystallisation Methods 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
238000005481 NMR spectroscopy Methods 0.000 description 6
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IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 6
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238000005160 1H NMR spectroscopy Methods 0.000 description 4
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LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 4
230000000694 effects Effects 0.000 description 4
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239000013078 crystal Substances 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
206010003658 Atrial Fibrillation Diseases 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
101000713575 Homo sapiens Tubulin beta-3 chain Proteins 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
102100036790 Tubulin beta-3 chain Human genes 0.000 description 2
239000013543 active substance Substances 0.000 description 2
230000017531 blood circulation Effects 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical group C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
230000007423 decrease Effects 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
230000002600 fibrillogenic effect Effects 0.000 description 2
210000002837 heart atrium Anatomy 0.000 description 2
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-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
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
231100000419 toxicity Toxicity 0.000 description 2
230000001988 toxicity Effects 0.000 description 2
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-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
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
206010003662 Atrial flutter Diseases 0.000 description 1
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208000024172 Cardiovascular disease Diseases 0.000 description 1
101150065749 Churc1 gene Proteins 0.000 description 1
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
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206010019233 Headaches Diseases 0.000 description 1
208000035154 Hyperesthesia Diseases 0.000 description 1
NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 1
206010028813 Nausea Diseases 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
102100038239 Protein Churchill Human genes 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
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NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
241000700157 Rattus norvegicus Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
208000001871 Tachycardia Diseases 0.000 description 1
230000036982 action potential Effects 0.000 description 1
239000000654 additive Substances 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
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GCGYREODZIZPLJ-UHFFFAOYSA-N azepan-1-ium;chloride Chemical compound Cl.C1CCCNCC1 GCGYREODZIZPLJ-UHFFFAOYSA-N 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
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239000000872 buffer Substances 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
235000010216 calcium carbonate Nutrition 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
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150000001735 carboxylic acids Chemical class 0.000 description 1
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239000000969 carrier Substances 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
OJYGBLRPYBAHRT-IPQSZEQASA-N chloralose Chemical compound O1[C@H](C(Cl)(Cl)Cl)O[C@@H]2[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]21 OJYGBLRPYBAHRT-IPQSZEQASA-N 0.000 description 1
229950009941 chloralose Drugs 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
239000013256 coordination polymer Substances 0.000 description 1
210000004351 coronary vessel Anatomy 0.000 description 1
WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
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125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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239000000706 filtrate Substances 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
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235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
238000007429 general method Methods 0.000 description 1
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125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
125000000879 imine group Chemical group 0.000 description 1
150000002466 imines Chemical class 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 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
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WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/15—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

NL8204275A 1981-11-06 1982-11-04 Nieuwe cyclische iminen, hun bereiding, alsmede farmaceutische samenstellingen welke hen bevatten. NL8204275A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
HU330881		1981-11-06
HU813308A HU183721B (en)	1981-11-06	1981-11-06	Process for producing new cyclic imine derivatives

Publications (1)

Publication Number	Publication Date
NL8204275A true NL8204275A (nl)	1983-06-01

Family

ID=10963511

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8204275A NL8204275A (nl)	1981-11-06	1982-11-04	Nieuwe cyclische iminen, hun bereiding, alsmede farmaceutische samenstellingen welke hen bevatten.

Country Status (18)

Country	Link
US (1)	US4530923A (it)
JP (1)	JPS5885879A (it)
AT (1)	AT382371B (it)
BE (1)	BE894889A (it)
CA (1)	CA1197241A (it)
CH (1)	CH652399A5 (it)
DD (1)	DD206992A5 (it)
DE (1)	DE3240908A1 (it)
DK (1)	DK494282A (it)
ES (1)	ES517049A0 (it)
FI (1)	FI77241C (it)
FR (1)	FR2516080B1 (it)
GB (1)	GB2111485B (it)
HU (1)	HU183721B (it)
IT (1)	IT1218328B (it)
NL (1)	NL8204275A (it)
SE (1)	SE8206230L (it)
SU (1)	SU1272986A3 (it)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ES513980A0 (es) *	1982-07-14	1983-04-16	Medichem Sa	Un procedimiento para la obtencion de la 2-(hexahidroazepin)-n-(2,6-dimetilfenil)acetamida.
ATE439131T1 (de) *	2001-08-30	2009-08-15	Chemocentryx Inc	Bicyclische verbindungen als hemmer der chemokin- bindung an us28

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1552758A (it) *	1963-07-01	1969-01-10
FR6571M (it) *	1967-08-03	1968-12-23
CA956632A (en) *	1969-05-16	1974-10-22	Yoshitomi Pharmaceutical Industries	Phenoxy-aminopropanol derivatives
BE790133A (fr) *	1971-10-16	1973-04-16	Basf Ag	Nouveaux derives de la trimethylhydroquinone, leur preparation et leursutilisations therapeutiques
DE2300543A1 (de) *	1973-01-08	1974-07-11	Basf Ag 6700 Ludwigshafen	Neue derivate des trimethylphenols und verfahren zu ihrer herstellung
JPS50106947A (it) *	1974-02-06	1975-08-22
CS195321B2 (en) *	1975-12-23	1980-01-31	Ciba Geigy Ag	Plant growth suppressing agents
US4191765A (en) *	1976-05-25	1980-03-04	Hoechst Aktiengesellschaft	1-Aryloxy-2-hydroxy-3-aminopropanes
DE2915250A1 (de) *	1979-04-14	1980-10-30	Basf Ag	Salze von alpha -aminoacetaniliden
DE3004360A1 (de) *	1980-02-06	1981-09-24	Chem. pharmaz. Fabrik Dr. Hermann Thiemann GmbH, 4670 Lünen	1,3-dicarbonyl-2-hydroxy- und -alkoxy-5-(amino-acetamido)-benzolverbindungen, verfahren zu ihrer herstellung und ihre verwendung

1981
- 1981-11-06 HU HU813308A patent/HU183721B/hu not_active IP Right Cessation
1982
- 1982-10-12 FI FI823470A patent/FI77241C/fi not_active IP Right Cessation
- 1982-10-20 US US06/435,493 patent/US4530923A/en not_active Expired - Fee Related
- 1982-11-02 ES ES517049A patent/ES517049A0/es active Granted
- 1982-11-02 SE SE8206230A patent/SE8206230L/xx not_active Application Discontinuation
- 1982-11-03 BE BE1/10630A patent/BE894889A/fr not_active IP Right Cessation
- 1982-11-04 FR FR8218475A patent/FR2516080B1/fr not_active Expired
- 1982-11-04 NL NL8204275A patent/NL8204275A/nl not_active Application Discontinuation
- 1982-11-05 GB GB08231604A patent/GB2111485B/en not_active Expired
- 1982-11-05 IT IT8224085A patent/IT1218328B/it active
- 1982-11-05 CH CH6448/82A patent/CH652399A5/de not_active IP Right Cessation
- 1982-11-05 AT AT0403982A patent/AT382371B/de not_active IP Right Cessation
- 1982-11-05 DD DD82244611A patent/DD206992A5/de unknown
- 1982-11-05 DK DK494282A patent/DK494282A/da not_active Application Discontinuation
- 1982-11-05 CA CA000415034A patent/CA1197241A/en not_active Expired
- 1982-11-05 DE DE19823240908 patent/DE3240908A1/de not_active Withdrawn
- 1982-11-06 JP JP57193985A patent/JPS5885879A/ja active Pending
1983
- 1983-10-13 SU SU833651388A patent/SU1272986A3/ru active

Also Published As

Publication number	Publication date
GB2111485B (en)	1985-07-17
FI823470L (fi)	1983-05-07
AT382371B (de)	1987-02-25
FI77241B (fi)	1988-10-31
FR2516080A1 (fr)	1983-05-13
SE8206230D0 (sv)	1982-11-02
DK494282A (da)	1983-05-07
ES8404328A1 (es)	1984-05-01
ATA403982A (de)	1986-07-15
HU183721B (en)	1984-05-28
FR2516080B1 (fr)	1985-11-22
CA1197241A (en)	1985-11-26
BE894889A (fr)	1983-05-03
ES517049A0 (es)	1984-05-01
CH652399A5 (de)	1985-11-15
FI77241C (fi)	1989-02-10
DE3240908A1 (de)	1983-05-19
IT8224085A0 (it)	1982-11-05
US4530923A (en)	1985-07-23
SE8206230L (sv)	1983-05-07
GB2111485A (en)	1983-07-06
JPS5885879A (ja)	1983-05-23
SU1272986A3 (ru)	1986-11-23
IT1218328B (it)	1990-04-12
FI823470A0 (fi)	1982-10-12
DD206992A5 (de)	1984-02-15

Legal Events

Date	Code	Title	Description
1985-01-01	A85	Still pending on 85-01-01
1990-01-02	BV	The patent application has lapsed

Publication	Publication Date	Title
TWI254039B (en)	2006-05-01	Ortho, meta-substituted bisaryl compounds, processes for their preparation, their use as medicaments, and pharmaceutical preparations comprising them
US4959366A (en)	1990-09-25	Anti-arrhythmic agents
CA1155116A (en)	1983-10-11	Phenyl piperazine derivatives having antiagressive activity
DE2649605B2 (de)	1980-07-10	p-substituierte l-Phenoxy-3-amino-2-propanole, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel
Augstein et al.	1965	Some cardiovascular effects of a series of aryloxyalkylamines. I
CA1134827A (en)	1982-11-02	Heterocyclic oxypropanolamine derivatives
EP0022118B1 (fr)	1983-06-01	Nouveaux dérivés de sulfonyl-aniline, leur procédé de préparation et leur application en thérapeutique
CS271343B2 (en)	1990-09-12	Method of new diphenylamine derivatives production
US4500529A (en)	1985-02-19	Method of treating cardiac disorders with N-(aryloxyalkyl)-N'-(aminoalkyl)ureas
DE69810960T2 (de)	2003-09-11	2-phenoxyanilin-derivate
JP3606326B2 (ja)	2005-01-05	欝病、不安神経症およびパーキンソン病を治療するための１−アリールシクロアルキルスルフィド、スルホキシドおよびスルホン
US4558155A (en)	1985-12-10	N-(Aryloxyalkyl)-N'-(aminoalkyl)thioureas
GB1579316A (en)	1980-11-19	Secondary amino tetrazolyloxypropanols
US4530923A (en)	1985-07-23	N-acetamilide, N-(phenoxy-2-propanol)- and N-(phenylamino-2-propanol)-cyclicamines
EP0066987B1 (en)	1986-08-27	N-(aryloxyalkyl)-n'-(amino-alkyl) ureas
CA1119170A (en)	1982-03-02	2-adamantyl hydrazines, their preparation and pharmaceutical compositions containing them
US4061640A (en)	1977-12-06	2-(Benzamido piperidine) quinolyl derivatives
CA1142926A (en)	1983-03-15	Ethers of 1-(2-propynyloxy) 2-amino-3-propanol
IE873441L (en)	1988-06-19	Indolecarboxamide derivatives.
US4053603A (en)	1977-10-11	Benzylisoquinoline derivatives, and use as anti-arrhythmic drugs
GB2098599A (en)	1982-11-24	N-(2,6-disubstituted phenyl)-alkanediamines
Heinzelman et al.	1953	Physiologically active amines. Tertiary amines and quaternary salts related to β-(o-methoxyphenyl)-isopropyl-N-methylamine
DK145041B (da)	1982-08-09	Analogifremgangsmaade til fremstilling af et benzophenonderivat eller syreadditionssalte deraf
Gainer	1946	Mechanisms of addition of organolithium compounds to quinoline and isoquinoline
JPH07118229A (ja)	1995-05-09	尿素誘導体およびその製造法