LV10433B - Hexahydroazepine derivatives, a process for their preparation and pharmaceutical compositions containing them - Google Patents

Hexahydroazepine derivatives, a process for their preparation and pharmaceutical compositions containing them Download PDF

Info

Publication number: LV10433B
Authority: LV; Latvia
Prior art keywords: formula; compound; group; give; necessary
Prior art date: 1990-06-14

Application number

LVP-93-141A

Other languages

English (en)

Latvian (lv)

Other versions

LV10433A (lv

Inventor

Lavastre Serge

Maignan Jean-Pierre

Paul Raymond

Poncelet Martine

Santucci Vincent

Original Assignee

Sanofi Elf

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.)

1990-06-14

Filing date

1993-02-25

Publication date

1995-08-20

1993-02-25 Application filed by Sanofi Elf filed Critical Sanofi Elf

1995-02-20 Publication of LV10433A publication Critical patent/LV10433A/xx

1995-08-20 Publication of LV10433B publication Critical patent/LV10433B/en

Links

ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical class C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 title claims abstract description 14
238000000034 method Methods 0.000 title claims description 17
238000002360 preparation method Methods 0.000 title claims description 12
239000008194 pharmaceutical composition Substances 0.000 title claims description 11
150000003839 salts Chemical class 0.000 claims abstract description 24
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
239000001257 hydrogen Substances 0.000 claims abstract description 13
150000007522 mineralic acids Chemical class 0.000 claims abstract description 10
150000007524 organic acids Chemical class 0.000 claims abstract description 10
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 8
229910052736 halogen Chemical group 0.000 claims abstract description 6
150000002367 halogens Chemical group 0.000 claims abstract description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
235000005985 organic acids Nutrition 0.000 claims abstract description 5
150000002431 hydrogen Chemical group 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 78
239000000203 mixture Substances 0.000 claims description 18
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 14
-1 vinyl compound Chemical class 0.000 claims description 11
238000005984 hydrogenation reaction Methods 0.000 claims description 10
239000004480 active ingredient Substances 0.000 claims description 8
239000003054 catalyst Substances 0.000 claims description 7
UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 3
238000009833 condensation Methods 0.000 claims description 2
230000005494 condensation Effects 0.000 claims description 2
AXZATFVMYUESDZ-UHFFFAOYSA-N azepane formaldehyde Chemical compound N1CCCCCC1.C=O AXZATFVMYUESDZ-UHFFFAOYSA-N 0.000 claims 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
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241000699670 Mus sp. Species 0.000 description 3
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LGQCVMYAEFTEFN-DQYPLSBCSA-N tocris-1079 Chemical compound C1C2=CC=C(O)C=C2[C@]2(C)[C@H](C)[C@H]1N(CC=C)CC2 LGQCVMYAEFTEFN-DQYPLSBCSA-N 0.000 description 3
125000006273 (C1-C3) alkyl group Chemical group 0.000 description 2
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BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
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229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
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DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
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229940045803 cuprous chloride Drugs 0.000 description 2
229960000632 dexamfetamine Drugs 0.000 description 2
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000000969 carrier Substances 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
239000003086 colorant Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
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125000004093 cyano group Chemical group *C#N 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
238000006704 dehydrohalogenation reaction Methods 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
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239000000706 filtrate Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
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230000000855 fungicidal effect Effects 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
229930195712 glutamate Natural products 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000002357 guanidines Chemical class 0.000 description 1
229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
125000001188 haloalkyl group Chemical group 0.000 description 1
125000004995 haloalkylthio group Chemical group 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
239000007902 hard capsule Substances 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
238000002372 labelling Methods 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
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238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000012528 membrane Substances 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
229960002216 methylparaben Drugs 0.000 description 1
239000003094 microcapsule Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
230000003387 muscular Effects 0.000 description 1
239000003176 neuroleptic agent Substances 0.000 description 1
230000000701 neuroleptic effect Effects 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
229940127240 opiate Drugs 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
150000002923 oximes Chemical group 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 1
229950010883 phencyclidine Drugs 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229940068917 polyethylene glycols Drugs 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
239000000843 powder Substances 0.000 description 1
UMSVPCYSAUKCAZ-UHFFFAOYSA-N propane;hydrochloride Chemical compound Cl.CCC UMSVPCYSAUKCAZ-UHFFFAOYSA-N 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
229960003415 propylparaben Drugs 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
238000012216 screening Methods 0.000 description 1
150000007659 semicarbazones Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000015424 sodium Nutrition 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007901 soft capsule Substances 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
230000002459 sustained effect Effects 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 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
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
239000004562 water dispersible granule Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/04—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with only hydrogen atoms, halogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- 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
- C07D295/06—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 halogen atoms or nitro radicals
- C07D295/073—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 halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- 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
- C07D295/06—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 halogen atoms or nitro radicals
- C07D295/067—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 halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents attached to the same carbon chain, which is not interrupted by carbocyclic rings
- 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
- 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
- C07D295/092—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 with aromatic radicals attached to the 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
- C07D295/10—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 doubly bound oxygen or sulphur atoms
- C07D295/104—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 doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/108—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 doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Neurology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Biomedical Technology (AREA)
Pharmacology & Pharmacy (AREA)
Psychiatry (AREA)
Animal Behavior & Ethology (AREA)
Neurosurgery (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Diaphragms For Electromechanical Transducers (AREA)
Control Of Transmission Device (AREA)
Data Exchanges In Wide-Area Networks (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

LVP-93-141A 1990-06-14 1993-02-25 Hexahydroazepine derivatives, a process for their preparation and pharmaceutical compositions containing them LV10433B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR909007434A FR2663328B1 (fr)	1990-06-14	1990-06-14	Derives d'hexahydroazepines, un procede pour leur preparation et compositions pharmaceutiques les contenant.

Publications (2)

Publication Number	Publication Date
LV10433A LV10433A (lv)	1995-02-20
LV10433B true LV10433B (en)	1995-08-20

Family

ID=9397608

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LVP-93-141A LV10433B (en)	1990-06-14	1993-02-25	Hexahydroazepine derivatives, a process for their preparation and pharmaceutical compositions containing them

Country Status (29)

Country	Link
US (2)	US5231092A (de)
EP (1)	EP0461986B1 (de)
JP (1)	JP2620422B2 (de)
KR (1)	KR100213531B1 (de)
AT (1)	ATE132861T1 (de)
AU (1)	AU647481B2 (de)
BR (1)	BR1100207A (de)
CA (1)	CA2044484C (de)
CZ (1)	CZ285696B6 (de)
DE (1)	DE69116237T2 (de)
DK (1)	DK0461986T3 (de)
ES (1)	ES2084792T3 (de)
FI (1)	FI101301B (de)
FR (1)	FR2663328B1 (de)
GR (1)	GR3019197T3 (de)
HU (2)	HU222490B1 (de)
IE (1)	IE74709B1 (de)
IL (1)	IL98479A (de)
LT (1)	LT3550B (de)
LV (1)	LV10433B (de)
MX (1)	MX9203360A (de)
MY (1)	MY135774A (de)
NO (1)	NO180195C (de)
NZ (1)	NZ238516A (de)
PL (1)	PL165842B1 (de)
PT (1)	PT97944B1 (de)
RU (2)	RU2070194C1 (de)
UA (1)	UA27222C2 (de)
ZA (1)	ZA914572B (de)

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FR2751645B1 (fr) *	1996-07-29	1998-12-24	Sanofi Sa	Amines pour la fabrication de medicaments destines a empecher la proliferation de cellules tumorales
US6005102A (en)	1997-10-15	1999-12-21	American Home Products Corporation	Aryloxy-alkyl-dialkylamines
FR2794742B1 (fr) *	1999-06-11	2005-06-03	Sanofi Synthelabo	Nouveaux derives du benzene, un procede pour leur preparation et les compositions pharmaceutiques les contenant
FR2795724B1 (fr) *	1999-07-02	2002-12-13	Sanofi Synthelabo	Nouveaux derives du benzene, un procede pour leur preparation et les compositions pharmaceutiques les contenant
WO2007047978A2 (en)	2005-10-21	2007-04-26	Braincells, Inc.	Modulation of neurogenesis by pde inhibition
EP2314289A1 (de)	2005-10-31	2011-04-27	Braincells, Inc.	Gaba-rezeptor-vermittelte modulation von neurogenese
US20100216734A1 (en)	2006-03-08	2010-08-26	Braincells, Inc.	Modulation of neurogenesis by nootropic agents
EP2021000A2 (de)	2006-05-09	2009-02-11	Braincells, Inc.	Neurogenese mittels angiotensin-modulation
US7678808B2 (en)	2006-05-09	2010-03-16	Braincells, Inc.	5 HT receptor mediated neurogenesis
US20100184806A1 (en)	2006-09-19	2010-07-22	Braincells, Inc.	Modulation of neurogenesis by ppar agents
ES2528026T3 (es)	2007-05-30	2015-02-03	Ind-Swift Laboratories Limited	Sales de oxalato de ivabridina cristalino y polimorfos de los mismos
RU2349579C1 (ru) *	2007-07-09	2009-03-20	Институт нефтехимии и катализа РАН	Способ получения n,n-диметил-3-фенил-2-пропин-1-амина
US20100216805A1 (en)	2009-02-25	2010-08-26	Braincells, Inc.	Modulation of neurogenesis using d-cycloserine combinations
CN116437960A (zh)	2020-09-17	2023-07-14	梅莱蒂奥斯治疗	用于治疗病毒感染的化合物

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US2881165A (en) *	1956-06-29	1959-04-07	Nl Combinatie Chem Ind	alpha-alpha-diphenyl-gamma-hexamethyleneiminobutyramide
DE1545561A1 (de) *	1965-08-23	1969-12-11	Acraf	Verfahren zur Herstellung von pharmakologisch aktiven N,N-disubstituierten 1-Aryl-3-aminopropinen
US4104383A (en) *	1973-11-02	1978-08-01	C M Industries	Derivatives of phenylpropenylamine
GB1475314A (en) *	1973-11-02	1977-06-01	Cm Ind	Phenyl-propylamine derivatives
DE3019497A1 (de) *	1980-05-22	1981-11-26	Bayer Ag, 5090 Leverkusen	Aminopropiophenon-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide
US4415581A (en) *	1982-04-09	1983-11-15	Hoechst-Roussel Pharmaceuticals Inc.	1-[3-6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-4-hydroxy-4-phenylpiperidines to treat psychoses
AU4261285A (en) *	1984-06-01	1985-12-05	Tokyo Tanabe Company Limited	1-propanone derivatives
DE3508398A1 (de) *	1985-03-08	1986-11-06	Hoechst Ag, 6230 Frankfurt	Fungizide mittel auf der basis von 3-(hetero)-arylpropylaminen sowie neue (hetero)-aryl-propylamine und verfahren zu ihrer herstellung
US4709094A (en)	1986-07-10	1987-11-24	State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon	Sigma brain receptor ligands and their use

1990
- 1990-06-14 FR FR909007434A patent/FR2663328B1/fr not_active Expired - Fee Related
1991
- 1991-06-10 IE IE196391A patent/IE74709B1/en not_active IP Right Cessation
- 1991-06-11 DK DK91401531.8T patent/DK0461986T3/da active
- 1991-06-11 ES ES91401531T patent/ES2084792T3/es not_active Expired - Lifetime
- 1991-06-11 EP EP91401531A patent/EP0461986B1/de not_active Expired - Lifetime
- 1991-06-11 DE DE69116237T patent/DE69116237T2/de not_active Expired - Fee Related
- 1991-06-11 AT AT91401531T patent/ATE132861T1/de not_active IP Right Cessation
- 1991-06-12 NZ NZ238516A patent/NZ238516A/xx not_active IP Right Cessation
- 1991-06-12 PT PT97944A patent/PT97944B1/pt not_active IP Right Cessation
- 1991-06-13 IL IL9847991A patent/IL98479A/en not_active IP Right Cessation
- 1991-06-13 CA CA002044484A patent/CA2044484C/en not_active Expired - Fee Related
- 1991-06-13 NO NO912283A patent/NO180195C/no unknown
- 1991-06-13 RU SU4895622/04A patent/RU2070194C1/ru not_active IP Right Cessation
- 1991-06-13 US US07/714,832 patent/US5231092A/en not_active Expired - Lifetime
- 1991-06-13 CZ CS911818A patent/CZ285696B6/cs not_active IP Right Cessation
- 1991-06-13 RU RU94038042/04A patent/RU2133741C1/ru not_active IP Right Cessation
- 1991-06-13 UA UA4895622A patent/UA27222C2/uk unknown
- 1991-06-14 PL PL91290675A patent/PL165842B1/pl not_active IP Right Cessation
- 1991-06-14 FI FI912899A patent/FI101301B/fi active IP Right Grant
- 1991-06-14 AU AU78434/91A patent/AU647481B2/en not_active Ceased
- 1991-06-14 JP JP3143212A patent/JP2620422B2/ja not_active Expired - Fee Related
- 1991-06-14 ZA ZA914572A patent/ZA914572B/xx unknown
- 1991-06-14 MY MYPI91001068A patent/MY135774A/en unknown
- 1991-06-14 KR KR1019910009879A patent/KR100213531B1/ko not_active Expired - Fee Related
- 1991-06-14 HU HU9101983A patent/HU222490B1/hu active IP Right Grant
1992
- 1992-06-25 MX MX9203360A patent/MX9203360A/es unknown
1993
- 1993-02-25 LV LVP-93-141A patent/LV10433B/en unknown
- 1993-04-14 US US08/045,722 patent/US5296596A/en not_active Expired - Lifetime
- 1993-06-23 LT LTIP704A patent/LT3550B/lt not_active IP Right Cessation
1995
- 1995-06-30 HU HU95P/P00617P patent/HU211616A9/hu unknown
1996
- 1996-03-05 GR GR960400601T patent/GR3019197T3/el unknown
1997
- 1997-04-02 BR BR1100207-7A patent/BR1100207A/pt active IP Right Grant

Also Published As

Publication number	Publication date
RU2070194C1 (ru)	1996-12-10
PL165842B1 (pl)	1995-02-28
IL98479A (en)	1995-11-27
IE911963A1 (en)	1991-12-18
HUT61736A (en)	1993-03-01
AU7843491A (en)	1991-12-19
MY135774A (en)	2008-06-30
UA27222C2 (uk)	2000-08-15
PL290675A1 (en)	1992-03-23
HK1000598A1 (en)	1998-04-09
CZ285696B6 (cs)	1999-10-13
PT97944B1 (pt)	1999-05-31
IE74709B1 (en)	1997-07-30
FI912899A0 (fi)	1991-06-14
NO180195B (no)	1996-11-25
US5296596A (en)	1994-03-22
EP0461986A1 (de)	1991-12-18
PT97944B (pt)	1998-11-30
NO180195C (no)	1997-03-05
CA2044484A1 (en)	1991-12-15
DK0461986T3 (da)	1996-05-28
RU2133741C1 (ru)	1999-07-27
EP0461986B1 (de)	1996-01-10
GR3019197T3 (en)	1996-06-30
HU222490B1 (hu)	2003-07-28
LTIP704A (en)	1995-01-31
FI912899L (fi)	1991-12-15
ATE132861T1 (de)	1996-01-15
HU211616A9 (en)	1995-12-28
ZA914572B (en)	1992-03-25
NZ238516A (en)	1993-09-27
FI101301B1 (fi)	1998-05-29
DE69116237T2 (de)	1996-07-25
PT97944A (pt)	1992-03-31
KR100213531B1 (ko)	1999-08-02
DE69116237D1 (de)	1996-02-22
CZ181891A3 (en)	1994-01-19
HU9101983D0 (en)	1991-12-30
LT3550B (en)	1995-11-27
ES2084792T3 (es)	1996-05-16
AU647481B2 (en)	1994-03-24
RU94038042A (ru)	1996-09-10
LV10433A (lv)	1995-02-20
JP2620422B2 (ja)	1997-06-11
NO912283L (no)	1991-12-16
NO912283D0 (no)	1991-06-13
KR920000728A (ko)	1992-01-29
IL98479A0 (en)	1992-07-15
FR2663328B1 (fr)	1994-08-05
BR1100207A (pt)	1999-10-05
CA2044484C (en)	1998-05-26
FI101301B (fi)	1998-05-29
JPH04321676A (ja)	1992-11-11
FR2663328A1 (fr)	1991-12-20
MX9203360A (es)	1992-07-01
US5231092A (en)	1993-07-27

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