SK74199A3 - 1,4-diazabicyclo [2.2.2] oct-2-ylmethyl derivatives, their preparation and therapeutic application - Google Patents

1,4-diazabicyclo [2.2.2] oct-2-ylmethyl derivatives, their preparation and therapeutic application Download PDF

Info

Publication number: SK74199A3
Authority: SK; Slovakia
Prior art keywords: diazabicyclo; compound; formula; compounds; preparation
Prior art date: 1996-12-04

Application number

SK741-99A

Other languages

English (en)

Slovak (sk)

Inventor

Alistair Lochead

Samir Jegham

Alain Nedelec

Axelle Solignac

Original Assignee

Synthelabo

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.)

1996-12-04

Filing date

1997-12-02

Publication date

2000-02-14

1997-12-02 Application filed by Synthelabo filed Critical Synthelabo

2000-02-14 Publication of SK74199A3 publication Critical patent/SK74199A3/sk

Links

238000002360 preparation method Methods 0.000 title claims description 4
-1 1,4-diazabicyclo [2.2.2] oct-2-ylmethyl Chemical class 0.000 title description 5
230000001225 therapeutic effect Effects 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 39
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
125000005843 halogen group Chemical group 0.000 claims abstract description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
239000000203 mixture Substances 0.000 claims description 11
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
238000000034 method Methods 0.000 claims description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 4
HXGLXQDKRXSLFI-UHFFFAOYSA-N ethyl 1,4-diazabicyclo[2.2.2]octane-3-carboxylate Chemical compound C1CN2C(C(=O)OCC)CN1CC2 HXGLXQDKRXSLFI-UHFFFAOYSA-N 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
MPJZCYUPWINKPK-UHFFFAOYSA-N 1,4-diazabicyclo[2.2.2]octan-3-ylmethanol Chemical compound C1CN2C(CO)CN1CC2 MPJZCYUPWINKPK-UHFFFAOYSA-N 0.000 claims description 3
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 3
239000000654 additive Substances 0.000 claims description 3
150000002148 esters Chemical class 0.000 claims description 3
OENICUBCLXKLJQ-UHFFFAOYSA-N ethyl 2,3-dibromopropanoate Chemical compound CCOC(=O)C(Br)CBr OENICUBCLXKLJQ-UHFFFAOYSA-N 0.000 claims description 3
IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 claims description 2
230000000996 additive effect Effects 0.000 claims description 2
239000003814 drug Substances 0.000 claims 1
239000012458 free base Substances 0.000 claims 1
229910052739 hydrogen Inorganic materials 0.000 claims 1
239000001257 hydrogen Substances 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 claims 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
108020003175 receptors Proteins 0.000 abstract description 11
239000003446 ligand Substances 0.000 abstract description 5
230000002295 serotoninergic effect Effects 0.000 abstract description 4
239000000387 serotonin 5-HT4 receptor agonist Substances 0.000 abstract description 3
125000003277 amino group Chemical group 0.000 abstract description 2
239000003369 serotonin 5-HT3 receptor antagonist Substances 0.000 abstract description 2
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 36
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000000872 buffer Substances 0.000 description 9
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
208000035475 disorder Diseases 0.000 description 6
239000000243 solution Substances 0.000 description 6
208000019901 Anxiety disease Diseases 0.000 description 5
229940076279 serotonin Drugs 0.000 description 5
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000007983 Tris buffer Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
238000011534 incubation Methods 0.000 description 4
239000013049 sediment Substances 0.000 description 4
ILXAOQAXSHVHTM-UHFFFAOYSA-M sodium;2-amino-2-(hydroxymethyl)propane-1,3-diol;chloride Chemical compound [Na+].[Cl-].OCC(N)(CO)CO ILXAOQAXSHVHTM-UHFFFAOYSA-M 0.000 description 4
239000000725 suspension Substances 0.000 description 4
210000001519 tissue Anatomy 0.000 description 4
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241000700199 Cavia porcellus Species 0.000 description 3
206010012289 Dementia Diseases 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
230000036506 anxiety Effects 0.000 description 3
230000027455 binding Effects 0.000 description 3
238000009472 formulation Methods 0.000 description 3
239000012528 membrane Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
ZNJHFNUEQDVFCJ-UHFFFAOYSA-M sodium;2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid;hydroxide Chemical compound [OH-].[Na+].OCCN1CCN(CCS(O)(=O)=O)CC1 ZNJHFNUEQDVFCJ-UHFFFAOYSA-M 0.000 description 3
230000009870 specific binding Effects 0.000 description 3
238000003756 stirring Methods 0.000 description 3
238000005303 weighing Methods 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
206010026749 Mania Diseases 0.000 description 2
229920002873 Polyethylenimine Polymers 0.000 description 2
208000028017 Psychotic disease Diseases 0.000 description 2
241000700159 Rattus Species 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
MOZPSIXKYJUTKI-RLXJOQACSA-N [1-[2-(methanesulfonamido)ethyl]piperidin-4-yl]methyl 1-(tritritiomethyl)indole-3-carboxylate Chemical compound C12=CC=CC=C2N(C([3H])([3H])[3H])C=C1C(=O)OCC1CCN(CCNS(C)(=O)=O)CC1 MOZPSIXKYJUTKI-RLXJOQACSA-N 0.000 description 2
239000005557 antagonist Substances 0.000 description 2
230000006399 behavior Effects 0.000 description 2
210000004556 brain Anatomy 0.000 description 2
AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical compound [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 2
229960004484 carbachol Drugs 0.000 description 2
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
210000003169 central nervous system Anatomy 0.000 description 2
210000003710 cerebral cortex Anatomy 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
210000001072 colon Anatomy 0.000 description 2
201000010099 disease Diseases 0.000 description 2
238000001035 drying Methods 0.000 description 2
210000003238 esophagus Anatomy 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000012634 fragment Substances 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000012280 lithium aluminium hydride Substances 0.000 description 2
230000009871 nonspecific binding Effects 0.000 description 2
239000000047 product Substances 0.000 description 2
239000003523 serotonin 4 antagonist Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000013222 sprague-dawley male rat Methods 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
230000002485 urinary effect Effects 0.000 description 2
KPJZHOPZRAFDTN-ZRGWGRIASA-N (6aR,9R)-N-[(2S)-1-hydroxybutan-2-yl]-4,7-dimethyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxamide Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@H](CO)CC)C2)=C3C2=CN(C)C3=C1 KPJZHOPZRAFDTN-ZRGWGRIASA-N 0.000 description 1
FTTATHOUSOIFOQ-UHFFFAOYSA-N 1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine Chemical compound C1NCCN2CCCC21 FTTATHOUSOIFOQ-UHFFFAOYSA-N 0.000 description 1
NAIHEECEPHODMQ-UHFFFAOYSA-N 1,4-diazabicyclo[2.2.2]octan-3-ylmethyl benzoate Chemical class C1N(CC2)CCN2C1COC(=O)C1=CC=CC=C1 NAIHEECEPHODMQ-UHFFFAOYSA-N 0.000 description 1
NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical group C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 1
ZMYAKSMZTVWUJB-UHFFFAOYSA-M 2,3-dibromopropanoate Chemical compound [O-]C(=O)C(Br)CBr ZMYAKSMZTVWUJB-UHFFFAOYSA-M 0.000 description 1
108091005482 5-HT4 receptors Proteins 0.000 description 1
KGEWUGWPCVDMCP-UHFFFAOYSA-N 5-amino-6-chloro-2,3-dihydro-1,4-benzodioxine-8-carboxylic acid Chemical compound O1CCOC2=C1C(C(O)=O)=CC(Cl)=C2N KGEWUGWPCVDMCP-UHFFFAOYSA-N 0.000 description 1
206010000060 Abdominal distension Diseases 0.000 description 1
208000007848 Alcoholism Diseases 0.000 description 1
206010003805 Autism Diseases 0.000 description 1
208000020706 Autistic disease Diseases 0.000 description 1
208000032841 Bulimia Diseases 0.000 description 1
206010006550 Bulimia nervosa Diseases 0.000 description 1
206010007270 Carcinoid syndrome Diseases 0.000 description 1
241000700198 Cavia Species 0.000 description 1
206010058842 Cerebrovascular insufficiency Diseases 0.000 description 1
206010008631 Cholera Diseases 0.000 description 1
208000030814 Eating disease Diseases 0.000 description 1
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208000019454 Feeding and Eating disease Diseases 0.000 description 1
208000017228 Gastrointestinal motility disease Diseases 0.000 description 1
206010021639 Incontinence Diseases 0.000 description 1
208000019695 Migraine disease Diseases 0.000 description 1
206010028813 Nausea Diseases 0.000 description 1
208000012902 Nervous system disease Diseases 0.000 description 1
208000025966 Neurological disease Diseases 0.000 description 1
206010033864 Paranoia Diseases 0.000 description 1
208000027099 Paranoid disease Diseases 0.000 description 1
208000018737 Parkinson disease Diseases 0.000 description 1
208000025865 Ulcer Diseases 0.000 description 1
206010047700 Vomiting Diseases 0.000 description 1
230000004913 activation Effects 0.000 description 1
239000000556 agonist Substances 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
230000003042 antagnostic effect Effects 0.000 description 1
230000000259 anti-tumor effect Effects 0.000 description 1
230000004596 appetite loss Effects 0.000 description 1
206010003119 arrhythmia Diseases 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
238000004166 bioassay Methods 0.000 description 1
208000024330 bloating Diseases 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
UBAZGMLMVVQSCD-UHFFFAOYSA-N carbon dioxide;molecular oxygen Chemical compound O=O.O=C=O UBAZGMLMVVQSCD-UHFFFAOYSA-N 0.000 description 1
210000000748 cardiovascular system Anatomy 0.000 description 1
208000026106 cerebrovascular disease Diseases 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
208000010877 cognitive disease Diseases 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
230000008602 contraction Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
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238000004821 distillation Methods 0.000 description 1
239000008298 dragée Substances 0.000 description 1
206010013663 drug dependence Diseases 0.000 description 1
230000002526 effect on cardiovascular system Effects 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
208000021302 gastroesophageal reflux disease Diseases 0.000 description 1
210000005095 gastrointestinal system Anatomy 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
230000001939 inductive effect Effects 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
210000000936 intestine Anatomy 0.000 description 1
208000002551 irritable bowel syndrome Diseases 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
239000010410 layer Substances 0.000 description 1
235000021266 loss of appetite Nutrition 0.000 description 1
208000019017 loss of appetite Diseases 0.000 description 1
238000003760 magnetic stirring Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
229960001186 methysergide Drugs 0.000 description 1
206010027599 migraine Diseases 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
230000008693 nausea Effects 0.000 description 1
210000001577 neostriatum Anatomy 0.000 description 1
230000000926 neurological effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
231100000862 numbness Toxicity 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
208000020016 psychiatric disease Diseases 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
201000000980 schizophrenia Diseases 0.000 description 1
230000001932 seasonal effect Effects 0.000 description 1
210000000813 small intestine Anatomy 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
239000000126 substance Substances 0.000 description 1
208000011117 substance-related disease Diseases 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
230000009747 swallowing Effects 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
NRTLTGGGUQIRRT-UHFFFAOYSA-N triethylazanium;bromide Chemical compound [Br-].CC[NH+](CC)CC NRTLTGGGUQIRRT-UHFFFAOYSA-N 0.000 description 1
HDDNYFLPWFSBLN-ZSHCYNCHSA-N tropanyl 3,5-dimethylbenzoate Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C1=CC(C)=CC(C)=C1 HDDNYFLPWFSBLN-ZSHCYNCHSA-N 0.000 description 1
231100000397 ulcer Toxicity 0.000 description 1
230000008673 vomiting Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- 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
- 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
- A61P25/06—Antimigraine agents
- 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
- 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
- A61P25/22—Anxiolytics
- 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
- A61P25/24—Antidepressants
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- 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
- 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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Chemical & Material Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Hospice & Palliative Care (AREA)
Urology & Nephrology (AREA)
Otolaryngology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

SK741-99A 1996-12-04 1997-12-02 1,4-diazabicyclo [2.2.2] oct-2-ylmethyl derivatives, their preparation and therapeutic application SK74199A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9614847A FR2756563B1 (fr)	1996-12-04	1996-12-04	Derives de benzoate de 1,4-diazabicyclo[2.2.2]oct-2-yl- methyle, leur preparation et leur application en therapeutique
PCT/FR1997/002174 WO1998024790A1 (fr)	1996-12-04	1997-12-02	Derives de benzoate de 1,4-diazabicyclo[2.2.2]oct-2-ylmethyle, leur preparation et leur application en therapeutique

Publications (1)

Publication Number	Publication Date
SK74199A3 true SK74199A3 (en)	2000-02-14

Family

ID=9498306

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK741-99A SK74199A3 (en)	1996-12-04	1997-12-02	1,4-diazabicyclo [2.2.2] oct-2-ylmethyl derivatives, their preparation and therapeutic application

Country Status (19)

Country	Link
US (1)	US6057321A (fr)
EP (1)	EP0942910A1 (fr)
JP (1)	JP2001504855A (fr)
KR (1)	KR20000069283A (fr)
CN (1)	CN1239962A (fr)
AU (1)	AU7624598A (fr)
BG (1)	BG103432A (fr)
BR (1)	BR9714215A (fr)
CA (1)	CA2271072A1 (fr)
CZ (1)	CZ193799A3 (fr)
EE (1)	EE9900218A (fr)
FR (1)	FR2756563B1 (fr)
HU (1)	HUP9904206A3 (fr)
IL (1)	IL129927A0 (fr)
NO (1)	NO992676L (fr)
NZ (1)	NZ336044A (fr)
SK (1)	SK74199A3 (fr)
TR (1)	TR199901068T2 (fr)
WO (1)	WO1998024790A1 (fr)

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CA2223588C (fr)	1995-06-07	2004-01-06	Noven Pharmaceuticals, Inc.	Compositions transdermiques contenant des medicaments de faible poids moleculaire liquides a temperature ambiante
WO2004090030A1 (fr) *	2003-04-08	2004-10-21	Ciba Specialty Chemicals Holding Inc.	Dispersants polymeres photostabilisants dans des dispersions de pigments
US7880683B2 (en) *	2004-08-18	2011-02-01	Ruckus Wireless, Inc.	Antennas with polarization diversity
US8198386B2 (en)	2007-04-16	2012-06-12	Daikin Industries, Ltd.	Fluorine-containing elastomer composition and sealing material made of same
CN101842375A (zh) *	2007-09-03	2010-09-22	巴斯夫欧洲公司	制备teda衍生物的方法
CN102046629A (zh) *	2008-05-30	2011-05-04	东曹株式会社	羟基烷基三亚乙基二胺类化合物的制造方法以及使用该化合物的用于制造聚氨酯树脂的催化剂组合物
US20110077376A1 (en) *	2008-05-30	2011-03-31	Katsumi Tokumoto	Process for producing hydroxyalkyltriethylenediamine, and catalyst composition for the production of polyurethane resin using it
CN101671336B (zh) *	2009-09-23	2013-11-13	辽宁利锋科技开发有限公司	芳杂环并嘧啶衍生物和类似物及其制备方法和用途
JP5504835B2 (ja) *	2009-11-13	2014-05-28	東ソー株式会社	ヒドロキシアルキルピペラジン類及び／又はヒドロキシメチルトリエチレンジアミン類の製造方法
JP5549847B2 (ja) *	2009-11-16	2014-07-16	東ソー株式会社	Ｎ−（２−アルコキシメチル）トリエチレンジアミン類の製造法
JP5707912B2 (ja) *	2010-12-08	2015-04-30	東ソー株式会社	Ｎ−（ジヒドロキシアルキル）ジエチレントリアミン類の組成物、及びそれを用いた２−ヒドロキシ（アルキル）トリエチレンジアミン類の製造方
JP6393959B2 (ja)	2012-05-31	2018-09-26	東ソー株式会社	ポリウレタン樹脂製造用触媒組成物及びそれを用いたポリウレタン樹脂の製造方法
JP6252152B2 (ja) *	2013-12-11	2017-12-27	東ソー株式会社	二環式アミン化合物の製造方法
KR20220055152A (ko)	2020-10-26	2022-05-03	인하대학교 산학협력단	급성 융모양막염 진단용 조성물 및 이를 이용한 급성 융모양막염 진단방법

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TW282460B (fr) *	1993-12-28	1996-08-01	Yamanouchi Pharma Co Ltd
FR2735475B1 (fr) *	1995-06-13	1997-07-11	Synthelabo	Derives de n-((1,4-diazabicyclo(2.2.2)oct-2-yl)methyl) benzamide, leur preparation et leur application en therapeutique

1996
- 1996-12-04 FR FR9614847A patent/FR2756563B1/fr not_active Expired - Fee Related
1997
- 1997-12-02 KR KR1019997004915A patent/KR20000069283A/ko not_active Withdrawn
- 1997-12-02 TR TR1999/01068T patent/TR199901068T2/xx unknown
- 1997-12-02 NZ NZ336044A patent/NZ336044A/xx unknown
- 1997-12-02 AU AU76245/98A patent/AU7624598A/en not_active Abandoned
- 1997-12-02 WO PCT/FR1997/002174 patent/WO1998024790A1/fr not_active Ceased
- 1997-12-02 CA CA002271072A patent/CA2271072A1/fr not_active Abandoned
- 1997-12-02 IL IL12992797A patent/IL129927A0/xx unknown
- 1997-12-02 US US09/319,413 patent/US6057321A/en not_active Expired - Fee Related
- 1997-12-02 BR BR9714215-8A patent/BR9714215A/pt not_active Application Discontinuation
- 1997-12-02 HU HU9904206A patent/HUP9904206A3/hu unknown
- 1997-12-02 JP JP52527298A patent/JP2001504855A/ja active Pending
- 1997-12-02 SK SK741-99A patent/SK74199A3/sk unknown
- 1997-12-02 EP EP97948976A patent/EP0942910A1/fr not_active Withdrawn
- 1997-12-02 CN CN97180353A patent/CN1239962A/zh active Pending
- 1997-12-02 CZ CZ991937A patent/CZ193799A3/cs unknown
- 1997-12-02 EE EEP199900218A patent/EE9900218A/xx unknown
1999
- 1999-05-26 BG BG103432A patent/BG103432A/xx unknown
- 1999-06-02 NO NO992676A patent/NO992676L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
CZ193799A3 (cs)	1999-09-15
FR2756563A1 (fr)	1998-06-05
NO992676L (no)	1999-07-29
EP0942910A1 (fr)	1999-09-22
TR199901068T2 (xx)	1999-07-21
HUP9904206A2 (hu)	2000-06-28
EE9900218A (et)	1999-12-15
HUP9904206A3 (en)	2000-07-28
CN1239962A (zh)	1999-12-29
KR20000069283A (ko)	2000-11-25
US6057321A (en)	2000-05-02
NO992676D0 (no)	1999-06-02
BG103432A (en)	2000-06-30
CA2271072A1 (fr)	1998-06-11
JP2001504855A (ja)	2001-04-10
BR9714215A (pt)	2000-04-18
NZ336044A (en)	2000-03-27
AU7624598A (en)	1998-06-29
WO1998024790A1 (fr)	1998-06-11
FR2756563B1 (fr)	1998-12-24
IL129927A0 (en)	2000-02-29

Publication	Publication Date	Title
CA2030718C (fr)	1998-05-12	Composes tricycliques
CA1150253A (fr)	1983-07-19	Dibenzoimidazoazepines, -oxazepines et -thiazepines et compositions pharmaceutiques qui en renferment
PL183933B1 (pl)	2002-08-30	Związki spiroazabicyklo, sposób wytwarzania związku spiroazabicyklo i kompozycja farmaceutyczna
SK74199A3 (en)	2000-02-14	1,4-diazabicyclo [2.2.2] oct-2-ylmethyl derivatives, their preparation and therapeutic application
JPH02503317A (ja)	1990-10-11	化合物
JPH04290884A (ja)	1992-10-15	α−オキソアセトアミド誘導体
EP1562945A1 (fr)	2005-08-17	Derives de 1,4-diazabicyclo (3,2,2)nonane, preparation et utilisations therapeutiques de ces derives
EP0485962A2 (fr)	1992-05-20	Composés tricycliques
AU704388B2 (en)	1999-04-22	N-((1,4-diazabicyclo(2.2.2)oct-2-yl)methyl)benzamide derivatives, their preparation and their application in therapeutics
SK34196A3 (en)	1996-10-02	Piperidine derivatives, preparation method thereof, piperidine derivatives as medicaments and pharmaceutical compositions containing these derivatives
PL210861B1 (pl)	2012-03-30	Pochodna beta-karboliny,kompozycja farmaceutyczna zawierająca pochodną beta-karboliny oraz zastosowanie pochodnej beta-karboliny
JPH05504358A (ja)	1993-07-08	置換尿素化合物及びそれらの製法及び使用
PL172860B1 (pl)	1997-12-31	Nowe pochodne piperydyny i sposób wytwarzania nowych pochodnych piperydyny PL PL
EP1053235A1 (fr)	2000-11-22	Derives d'oxazol utilises comme agonistes du recepteur 1a de la serotonine
US6057340A (en)	2000-05-02	Oxazole derivatives as serotonin-1A receptor agonists
US5081128A (en)	1992-01-14	2,3-dihydro-1h-isoindole derivatives and their application in therapy
AU762526B2 (en)	2003-06-26	Novel type condensed pyridazinone compounds
US5086179A (en)	1992-02-04	Process for the preparation of optically pure amides
FR2756564A1 (fr)	1998-06-05	Derives d'acide quinoleine-8-carboxylique, leur preparation et leur application en therapeutique
MXPA96002306A (en)	1998-07-03	Derivatives of n - [(1,4-diazabiciclo [2.2.2] oct-2-il) methyl] benzamide, its preparation and its application in terapeut
HK1013651A (en)	1999-09-03	N-[(1,4-diazabicyclo [2.2.2] oct-2-yl) methyl] benzamide derivatives, their preparation and their application in therapeutics
HU210353A9 (hu)	1995-03-28	Új triciklusos vegyületek és ezeket tartalmazó gyógyszerkészítmények Az átmeneti oltalom a(z) 1-43. és 48. igénypontokra vonatkozik.