HU204276B - Process for producing new 1-oxa-2-oxo-4-methylen-8-aza-spiro(4,5)decane derivatives and pharmaceutical compositions containing them - Google Patents
Process for producing new 1-oxa-2-oxo-4-methylen-8-aza-spiro(4,5)decane derivatives and pharmaceutical compositions containing them Download PDFInfo
- Publication number
- HU204276B HU204276B HU894094A HU409489A HU204276B HU 204276 B HU204276 B HU 204276B HU 894094 A HU894094 A HU 894094A HU 409489 A HU409489 A HU 409489A HU 204276 B HU204276 B HU 204276B
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- Hungary
- Prior art keywords
- formula
- defined above
- oxo
- derivative
- compounds
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 27
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 7
- CMOXGGUMLQGLTG-UHFFFAOYSA-N 4-methylidene-1-oxa-8-azaspiro[4.5]decan-2-one Chemical class C=C1CC(=O)OC11CCNCC1 CMOXGGUMLQGLTG-UHFFFAOYSA-N 0.000 title 1
- 239000002253 acid Substances 0.000 claims abstract description 21
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000003545 alkoxy group 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 5
- 150000001875 compounds Chemical class 0.000 claims description 59
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 30
- -1 diphenyl alkene derivative Chemical class 0.000 claims description 24
- 150000003839 salts Chemical group 0.000 claims description 20
- 238000002360 preparation method Methods 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 17
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000011541 reaction mixture Substances 0.000 claims description 10
- 239000012948 isocyanate Substances 0.000 claims description 8
- 150000002513 isocyanates Chemical class 0.000 claims description 8
- CYCSGNGCLXFNFZ-UHFFFAOYSA-N (4-ethynylpiperidin-4-yl) carbamate Chemical class NC(=O)OC1(C#C)CCNCC1 CYCSGNGCLXFNFZ-UHFFFAOYSA-N 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- SKGCHBGIBOPGHV-UHFFFAOYSA-N 1,3-dioxolan-2-imine Chemical class N=C1OCCO1 SKGCHBGIBOPGHV-UHFFFAOYSA-N 0.000 claims description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 5
- ASPBBYVNTMIKLA-UHFFFAOYSA-N 2,8-diazaspiro[4.5]decan-3-one Chemical compound C1NC(=O)CC21CCNCC2 ASPBBYVNTMIKLA-UHFFFAOYSA-N 0.000 claims description 5
- GVZFMFFUAZKMOB-UHFFFAOYSA-N 4-ethynylpiperidin-4-ol Chemical class C#CC1(O)CCNCC1 GVZFMFFUAZKMOB-UHFFFAOYSA-N 0.000 claims description 5
- GEMSTPWCYFPJOS-UHFFFAOYSA-N 4-methylidene-8-azaspiro[4.5]decan-2-one Chemical class C=C1CC(=O)CC11CCNCC1 GEMSTPWCYFPJOS-UHFFFAOYSA-N 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 238000007363 ring formation reaction Methods 0.000 claims description 5
- SEUNTAIZLCAWDW-UHFFFAOYSA-N 1-oxa-8-azaspiro[4.5]decan-2-one Chemical class O1C(=O)CCC11CCNCC1 SEUNTAIZLCAWDW-UHFFFAOYSA-N 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- VWADBHVASFOEHX-UHFFFAOYSA-N 1-(4-hydroxypiperidin-4-yl)ethanone Chemical class CC(=O)C1(O)CCNCC1 VWADBHVASFOEHX-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
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- 208000020016 psychiatric disease Diseases 0.000 claims description 2
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- 239000012453 solvate Substances 0.000 claims description 2
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
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- 125000001475 halogen functional group Chemical group 0.000 abstract 2
- WYDMNGYRWISCLZ-UHFFFAOYSA-N 1-[3,3-bis(4-fluorophenyl)prop-2-enyl]-4-ethynylpiperidin-4-ol;hydrochloride Chemical compound Cl.C1CC(O)(C#C)CCN1CC=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 WYDMNGYRWISCLZ-UHFFFAOYSA-N 0.000 abstract 1
- VLVWUSGOTSWICZ-UHFFFAOYSA-N [1-[4,4-bis(4-fluorophenyl)but-3-enyl]-4-ethynylpiperidin-4-yl] n-benzylcarbamate Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)=CCCN1CCC(C#C)(OC(=O)NCC=2C=CC=CC=2)CC1 VLVWUSGOTSWICZ-UHFFFAOYSA-N 0.000 abstract 1
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- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000000411 inducer Substances 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000001034 iron oxide pigment Substances 0.000 description 1
- TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229960004194 lidocaine Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 230000003137 locomotive effect Effects 0.000 description 1
- 230000006742 locomotor activity Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000005905 mesyloxy group Chemical group 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 230000004006 stereotypic behavior Effects 0.000 description 1
- 230000002739 subcortical effect Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000005550 wet granulation Methods 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Priority Applications (56)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| YU150489A YU150489A (sh) | 1989-08-10 | 1989-07-27 | Uređaj za ispitivanje odevnih predmeta na nepromočivost |
| HU903233A HU206677B (en) | 1989-08-10 | 1989-08-10 | Process for producing new 4,4-disubstituted piperidine derivatives and pharmaceutical compositions containing them |
| HU894094A HU204276B (en) | 1989-08-10 | 1989-08-10 | Process for producing new 1-oxa-2-oxo-4-methylen-8-aza-spiro(4,5)decane derivatives and pharmaceutical compositions containing them |
| KR1019900012170A KR940003491B1 (ko) | 1989-08-10 | 1990-08-08 | 4,4-이중 치환된 피페리딘 유도체와 그 제조방법 및 상기 화합물을 함유하는 약제학적 조성물 |
| KR1019900012168A KR940002826B1 (ko) | 1989-08-10 | 1990-08-08 | 4-메틸렌-2-옥소-8-아자스피로[4,5]데칸 유도체, 그것의 이성질체, 산부가염, 제4급 암모늄염과 그것의 제조방법 및 그것을 함유하는 약제학적 조성물 |
| KR1019900012169A KR940000830B1 (ko) | 1989-08-10 | 1990-08-08 | 2-옥소-3, 8-디아자스피로[4,5]데칸 유도체와 그 제조방법 및 그것을 함유하는 약제학적 조성물 |
| AT9090308783T ATE104671T1 (de) | 1989-08-10 | 1990-08-09 | 4-methylen-1-oxa-2-oxo-8azaspiro(4,5>decanderivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische zubereitungen. |
| ES90308783T ES2052179T3 (es) | 1989-08-10 | 1990-08-09 | Derivados de 4-metilen-1-oxa-2-oxo-8-azaespiro(4,5)decano, composiciones farmaceuticas que los contienen y procesos para prepararlos. |
| JP2209362A JPH0381277A (ja) | 1989-08-10 | 1990-08-09 | ２―オキソ―３，８―ジアザスピロ〔４，５〕デカン誘導体，それを含む医薬組成物及びその製造方法 |
| DD90343364A DD299425A5 (de) | 1989-08-10 | 1990-08-09 | Neue 4,4-disubstituierte piperidin-derivate und verfahren zu ihrer herstellung |
| AU60806/90A AU624261B2 (en) | 1989-08-10 | 1990-08-09 | Novel 4,4-disubstituted piperidine derivatives, pharmaceutical compositions containing them and process for preparing the same |
| JP2209363A JPH0383985A (ja) | 1989-08-10 | 1990-08-09 | 新規４―メチレン―２―オキソ―８―アザスピロ〔４，５〕デカン誘導体，それらを含む医薬組成物およびそれらの調整方法 |
| IS3612A IS3612A7 (is) | 1989-08-10 | 1990-08-09 | Novel úrefni 2-oxo-3,8-diazaspiro/4,5/decane, lyfjablöndur, sem innihalda þau og aðferðir til að framleiða þær |
| IE288590A IE902885A1 (en) | 1989-08-10 | 1990-08-09 | Novel 2-oxo-3, 8-diazaspiro[4,5]decane derivatives,¹pharmaceutical compositions containing them and process for¹preparing the same |
| NZ234843A NZ234843A (en) | 1989-08-10 | 1990-08-09 | 2-oxo-1-oxa-3,8-diazaspiro(4,5)decane derivatives and pharmaceutical compositions |
| CA002023015A CA2023015A1 (en) | 1989-08-10 | 1990-08-09 | 4-methylene-2-oxo-8-azaspiro /4,5/decane derivatives, pharmaceutical compositions containing them and process for preparing the same |
| ZA906300A ZA906300B (en) | 1989-08-10 | 1990-08-09 | Novel 2-oxo-3,8-diazaspiro(4,5)decane derivatives,pharmaceutical compositions containing them and process for preparing same |
| DE69007900T DE69007900T2 (de) | 1989-08-10 | 1990-08-09 | 4,4-Disubstituierte Piperidinderivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zubereitungen. |
| AU60803/90A AU621771B2 (en) | 1989-08-10 | 1990-08-09 | Novel 2-oxo-3,8-diazaspiro(4,5)decane derivatives, pharmaceutical compositions containing them and process for preparing the same |
| JP2209361A JPH0377866A (ja) | 1989-08-10 | 1990-08-09 | 新規４，４‐二置換ピペリジン誘導体、それらを含む医薬組成物およびそれらの調製方法 |
| AT90308779T ATE113951T1 (de) | 1989-08-10 | 1990-08-09 | 1-oxa-2-oxo-3,8-diazaspiro(4,5>decanderivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische zubereitungen. |
| NO90903511A NO903511L (no) | 1989-08-10 | 1990-08-09 | Nye 2-oxo-3,8-diazaspiro(4,5)decanderivater, farmasoeytiske preparater som inneholder dem og fremgangsmaate for fremstilling av dem. |
| EP90308783A EP0413516B1 (en) | 1989-08-10 | 1990-08-09 | 4-Methylene-1-oxa-2-oxo-8-azaspiro[4,5]decane derivatives, pharmaceutical compositions containing them and processes for preparing them |
| NZ234847A NZ234847A (en) | 1989-08-10 | 1990-08-09 | Piperidine derivatives and pharmaceutical compositions |
| AT90308782T ATE103896T1 (de) | 1989-08-10 | 1990-08-09 | 4,4-disubstituierte piperidinderivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische zubereitungen. |
| YU154090A YU154090A (sh) | 1989-08-10 | 1990-08-09 | Novi derivati 2-okso-3,8-diazaspiro /4,5/dekana i postupak za njihovo dobijanje |
| DE69014008T DE69014008T2 (de) | 1989-08-10 | 1990-08-09 | 1-Oxa-2-oxo-3,8-diazaspiro[4,5]decanderivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zubereitungen. |
| DD90343359A DD299431A5 (de) | 1989-08-10 | 1990-08-09 | Neue 2-oxo-3,8-diaza-spiro[4,5]dekan-derivate und verfahren zur herstellung dieser verbindungen |
| DD90343354A DD299428A5 (de) | 1989-08-10 | 1990-08-09 | Neue 2-oxo-4-methylen-8-aza-spiro[4,5]dekan-derivate und verfahren zu ihrer herstellung |
| IL9532590A IL95325A (en) | 1989-08-10 | 1990-08-09 | History of G, G) -8-diphenylalkenyl (-3-hydroxy-4-methyl 2-oxo-1-oxa-3,8-diazaspiro] 4,5 [decane, preparation and pharmaceutical preparations containing them |
| DE69008275T DE69008275T2 (de) | 1989-08-10 | 1990-08-09 | 4-Methylen-1-oxa-2-oxo-8-azaspiro[4,5]decanderivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zubereitungen. |
| EP90308779A EP0412821B1 (en) | 1989-08-10 | 1990-08-09 | 1-oxa-2-oxo-3,8-diazaspiro[4,5]decane derivatives, pharmaceutical compositions containing them and processes for preparing them |
| IN687/CAL/90A IN170979B (enExample) | 1989-08-10 | 1990-08-09 | |
| NZ234846A NZ234846A (en) | 1989-08-10 | 1990-08-09 | 4-methylene-1-oxa-2-oxo-3-(oxa or aza)-8-azaspiro(4,5)- decane derivatives and pharmaceutical compositions |
| ZA906299A ZA906299B (en) | 1989-08-10 | 1990-08-09 | Novel 4-methylene-2-oxo-8-azaspiro(4,5)decane derivatives,pharmaceutical compositions containing them and process for preparing same |
| EP90308782A EP0412822B1 (en) | 1989-08-10 | 1990-08-09 | 4,4-Disubstituted piperidine derivatives, processes for their preparation and pharmaceutical compositions thereof |
| ZA906304A ZA906304B (en) | 1989-08-10 | 1990-08-09 | Novel 4,4-disubstituted piperidine derivatives,pharmaceutical compositions containing them and process for preparing same |
| DK90308783.1T DK0413516T3 (da) | 1989-08-10 | 1990-08-09 | 4-Methylen-1-oxa-2-oxo-8-azaspiro(4,5)-decanderivater fremgangsmåder til deres fremstilling og farmaceutiske præparater med indhold deraf |
| IL9532390A IL95323A (en) | 1989-08-10 | 1990-08-09 | History of Pipridine 4,4- Transformed, preparation and pharmaceutical preparations containing them |
| ES90308782T ES2063282T3 (es) | 1989-08-10 | 1990-08-09 | Derivados de piperidina 4,4-disubstituidos, procesos para su preparacion y composiciones farmaceuticas de los mismos. |
| SG1995903969A SG59864G (en) | 1989-08-10 | 1990-08-09 | 1-oxa-2-oxo-3,8-diazaspirol[4,5] decane derivatives pharmaceutical compositions containing them and processes for preparing them |
| AU60804/90A AU621238B2 (en) | 1989-08-10 | 1990-08-09 | Novel 4-methylene-2-oxo-8-azaspiro(4,5)decane derivatives, pharmaceutical compositions containing them and process for preparing the same |
| IL9532490A IL95324A (en) | 1989-08-10 | 1990-08-09 | History of G, G) 9-Diphenylalkanyl (4-methylene-2-oxo-1-oxa-8-azaspiro [4,5] decane, preparation and pharmaceutical preparations containing them |
| CA002023018A CA2023018C (en) | 1989-08-10 | 1990-08-09 | 2-oxo-3,8-diazaspiro /4,5/decane derivatives, pharmaceutical compositions containing them and process for preparing the same |
| ES90308779T ES2063923T3 (es) | 1989-08-10 | 1990-08-09 | Derivados de 1-oxa-2-oxo-3,8-diazaespiro(4,5)decano, composiciones farmaceuticas que los contienen y procesos para prepararlos. |
| DK90308782.3T DK0412822T3 (da) | 1989-08-10 | 1990-08-09 | 4,4-Disubstituerede piperidinderivater, fremgangsmåder til deres fremstilling samt farmaceutiske præparater med indhold deraf |
| CN90106974A CN1025031C (zh) | 1989-08-10 | 1990-08-10 | 新的2-氧代-3，8-二氮杂螺[4，5]癸烷衍生物的制备方法 |
| PL90286443A PL163899B1 (pl) | 1989-08-10 | 1990-08-10 | Sposób wytwarzania nowych pochodnych 1-oksa-2-keto-3,8-diazaspiro[4,5] dekanu PL PL PL |
| US07/566,279 US5132309A (en) | 1989-08-10 | 1990-08-10 | 2-oxo-3,8-diazaspiro(4,5)decane derivatives, pharmaceutical compositions containing them and process for preparing same |
| US07/566,278 US5132303A (en) | 1989-08-10 | 1990-08-10 | 4-methylene-2-oxo-8-azaspiro[4,5]decane derivatives, pharmaceutical compositions containing them and process for preparing same |
| FI903974A FI93456C (fi) | 1989-08-10 | 1990-08-10 | Menetelmä uusien terapeuttisesti käyttökelpoisten 2-okso-3,8-diatsaspiro/4,5/dekaanijohdannaisten valmistamiseksi |
| MYPI90001343A MY107240A (en) | 1989-08-10 | 1990-08-10 | Novel 2-oxo-3, 8-diazaspiro [4,5] decane derivatives, pharmaceuticals compositions containing them and process for preparing same. |
| US07/566,273 US5118693A (en) | 1989-08-10 | 1990-08-10 | 4,4-disubstituted piperidine derivatives, pharmaceutical compositions containing them and process for preparing same |
| PL90291648A PL164662B1 (pl) | 1989-08-10 | 1990-08-10 | Sposób wytwarzania nowych pochodnych 1-oksa-2-keto-3,8-diazaspiro[4,5]dekanu PL PL PL |
| IN550/CAL/93A IN172010B (enExample) | 1989-08-10 | 1991-07-22 | |
| HK118295A HK118295A (en) | 1989-08-10 | 1995-07-20 | 1-oxa-2-oxo-3,8-diazaspiro[4,5]decane derivatives, pharmaceutical compositions containing them and processes for preparing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU894094A HU204276B (en) | 1989-08-10 | 1989-08-10 | Process for producing new 1-oxa-2-oxo-4-methylen-8-aza-spiro(4,5)decane derivatives and pharmaceutical compositions containing them |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT55785A HUT55785A (en) | 1991-06-28 |
| HU204276B true HU204276B (en) | 1991-12-30 |
Family
ID=10966866
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU894094A HU204276B (en) | 1989-08-10 | 1989-08-10 | Process for producing new 1-oxa-2-oxo-4-methylen-8-aza-spiro(4,5)decane derivatives and pharmaceutical compositions containing them |
| HU903233A HU206677B (en) | 1989-08-10 | 1989-08-10 | Process for producing new 4,4-disubstituted piperidine derivatives and pharmaceutical compositions containing them |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU903233A HU206677B (en) | 1989-08-10 | 1989-08-10 | Process for producing new 4,4-disubstituted piperidine derivatives and pharmaceutical compositions containing them |
Country Status (26)
| Country | Link |
|---|---|
| US (2) | US5132309A (enExample) |
| EP (2) | EP0413516B1 (enExample) |
| JP (2) | JPH0381277A (enExample) |
| KR (2) | KR940000830B1 (enExample) |
| CN (1) | CN1025031C (enExample) |
| AT (2) | ATE113951T1 (enExample) |
| AU (2) | AU621771B2 (enExample) |
| CA (2) | CA2023018C (enExample) |
| DD (2) | DD299431A5 (enExample) |
| DE (2) | DE69008275T2 (enExample) |
| DK (1) | DK0413516T3 (enExample) |
| ES (2) | ES2052179T3 (enExample) |
| FI (1) | FI93456C (enExample) |
| HK (1) | HK118295A (enExample) |
| HU (2) | HU204276B (enExample) |
| IE (1) | IE902885A1 (enExample) |
| IL (2) | IL95324A (enExample) |
| IN (1) | IN170979B (enExample) |
| IS (1) | IS3612A7 (enExample) |
| MY (1) | MY107240A (enExample) |
| NO (1) | NO903511L (enExample) |
| NZ (2) | NZ234843A (enExample) |
| PL (2) | PL164662B1 (enExample) |
| SG (1) | SG59864G (enExample) |
| YU (2) | YU150489A (enExample) |
| ZA (3) | ZA906299B (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE152623T1 (de) * | 1986-12-17 | 1997-05-15 | Glaxo Group Ltd | Verwendung von heterozyklischen derivaten zur herstellung von arzneimitteln |
| YU150489A (sh) * | 1989-08-10 | 1992-12-21 | W.L. Gore & Co. Gmbh. | Uređaj za ispitivanje odevnih predmeta na nepromočivost |
| HU204529B (en) * | 1989-08-10 | 1992-01-28 | Richter Gedeon Vegyeszet | Process for producing new 1-oxa-2-oxo-8-aza-spiro(4,5)decane derivatives and pharmaceutical compositions containing them |
| US5534520A (en) * | 1990-04-10 | 1996-07-09 | Fisher; Abraham | Spiro compounds containing five-membered rings |
| US5852029A (en) * | 1990-04-10 | 1998-12-22 | Israel Institute For Biological Research | Aza spiro compounds acting on the cholinergic system with muscarinic agonist activity |
| EP0492020A1 (en) * | 1990-12-21 | 1992-07-01 | Merrell Dow Pharmaceuticals Inc. | Use of certain esters of hexahydro-8-hydroxy-2,6-methano-2H-quinolizin-3(4H)-one and related compounds for treating cognitive disorders |
| GB9206989D0 (en) * | 1992-03-31 | 1992-05-13 | Glaxo Group Ltd | Chemical compounds |
| US5756743A (en) * | 1996-04-10 | 1998-05-26 | Hoechst Marion Roussel Inc. | Spiro cyclopent b!indole-piperidines! |
| US6100256A (en) * | 1996-12-02 | 2000-08-08 | Merck Sharp & Dohme Ltd. | Use of NK-1 receptors antagonists for treating schizophrenic disorders |
| US6974825B1 (en) | 1996-12-20 | 2005-12-13 | Astrazeneca Canada Inc. | Compounds with analgesic effect |
| SE9604786D0 (sv) | 1996-12-20 | 1996-12-20 | Astra Pharma Inc | New compounds |
| SE9904675D0 (sv) | 1999-12-20 | 1999-12-20 | Astra Pharma Inc | Novel compounds |
| SE0101771D0 (sv) | 2001-05-18 | 2001-05-18 | Astrazeneca Ab | Novel compounds |
| SE0101769D0 (sv) | 2001-05-18 | 2001-05-18 | Astrazeneca Ab | Novel compounds |
| SE0101770D0 (sv) * | 2001-05-18 | 2001-05-18 | Astrazeneca Ab | Novel compounds |
| SE0101773D0 (sv) * | 2001-05-18 | 2001-05-18 | Astrazeneca Ab | Novel compounds |
| KR20030087248A (ko) * | 2002-05-08 | 2003-11-14 | (주)씨엔아이 | 온라인을 통한 상거래 기초항목의 설정기능을 갖는 상거래관리장치 |
| CN102459278A (zh) * | 2009-06-16 | 2012-05-16 | 默沙东公司 | 取代的-1,3,8-三氮杂螺[4.5]癸烷-2,4-二酮 |
| GB201416346D0 (en) * | 2014-09-16 | 2014-10-29 | Shire Internat Gmbh | Spirocyclic derivatives |
| GB201416352D0 (en) * | 2014-09-16 | 2014-10-29 | Shire Internat Gmbh | Spirocyclic derivatives |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL127065C (enExample) * | 1964-04-22 | |||
| CH601304A5 (enExample) * | 1974-02-12 | 1978-07-14 | Buskine Sa | |
| BE790675A (fr) * | 1971-10-29 | 1973-04-27 | Science Union & Cie | Nouveaux derives de l'oxa-1 diaza-3,8 spiro (4,5) decane |
| FR2615515B1 (fr) * | 1987-05-22 | 1989-06-30 | Adir | Nouveaux derives du spiro 4, 5 decane, leur procede de preparation et les compositions pharmaceutiques les renfermant |
| YU150489A (sh) * | 1989-08-10 | 1992-12-21 | W.L. Gore & Co. Gmbh. | Uređaj za ispitivanje odevnih predmeta na nepromočivost |
| HU204529B (en) * | 1989-08-10 | 1992-01-28 | Richter Gedeon Vegyeszet | Process for producing new 1-oxa-2-oxo-8-aza-spiro(4,5)decane derivatives and pharmaceutical compositions containing them |
| HU204530B (en) * | 1989-08-10 | 1992-01-28 | Richter Gedeon Vegyeszet | Process for producing new 1-oxa-2-oxo-8-aza-spiro(4,5)decane derivatives and pharmaceutical compositions containing them |
-
1989
- 1989-07-27 YU YU150489A patent/YU150489A/sh unknown
- 1989-08-10 HU HU894094A patent/HU204276B/hu not_active IP Right Cessation
- 1989-08-10 HU HU903233A patent/HU206677B/hu not_active IP Right Cessation
-
1990
- 1990-08-08 KR KR1019900012169A patent/KR940000830B1/ko not_active Expired - Fee Related
- 1990-08-08 KR KR1019900012168A patent/KR940002826B1/ko not_active Expired - Fee Related
- 1990-08-09 JP JP2209362A patent/JPH0381277A/ja active Pending
- 1990-08-09 IL IL9532490A patent/IL95324A/en not_active IP Right Cessation
- 1990-08-09 DE DE69008275T patent/DE69008275T2/de not_active Expired - Fee Related
- 1990-08-09 NZ NZ234843A patent/NZ234843A/en unknown
- 1990-08-09 NO NO90903511A patent/NO903511L/no unknown
- 1990-08-09 DE DE69014008T patent/DE69014008T2/de not_active Expired - Fee Related
- 1990-08-09 IS IS3612A patent/IS3612A7/is unknown
- 1990-08-09 ES ES90308783T patent/ES2052179T3/es not_active Expired - Lifetime
- 1990-08-09 IN IN687/CAL/90A patent/IN170979B/en unknown
- 1990-08-09 AT AT90308779T patent/ATE113951T1/de not_active IP Right Cessation
- 1990-08-09 EP EP90308783A patent/EP0413516B1/en not_active Expired - Lifetime
- 1990-08-09 ZA ZA906299A patent/ZA906299B/xx unknown
- 1990-08-09 DD DD90343359A patent/DD299431A5/de not_active IP Right Cessation
- 1990-08-09 AT AT9090308783T patent/ATE104671T1/de not_active IP Right Cessation
- 1990-08-09 ZA ZA906304A patent/ZA906304B/xx unknown
- 1990-08-09 CA CA002023018A patent/CA2023018C/en not_active Expired - Fee Related
- 1990-08-09 AU AU60803/90A patent/AU621771B2/en not_active Ceased
- 1990-08-09 YU YU154090A patent/YU154090A/sh unknown
- 1990-08-09 NZ NZ234846A patent/NZ234846A/en unknown
- 1990-08-09 AU AU60804/90A patent/AU621238B2/en not_active Ceased
- 1990-08-09 SG SG1995903969A patent/SG59864G/en unknown
- 1990-08-09 IL IL9532590A patent/IL95325A/en not_active IP Right Cessation
- 1990-08-09 ES ES90308779T patent/ES2063923T3/es not_active Expired - Lifetime
- 1990-08-09 EP EP90308779A patent/EP0412821B1/en not_active Expired - Lifetime
- 1990-08-09 DK DK90308783.1T patent/DK0413516T3/da active
- 1990-08-09 CA CA002023015A patent/CA2023015A1/en not_active Abandoned
- 1990-08-09 IE IE288590A patent/IE902885A1/en unknown
- 1990-08-09 DD DD90343354A patent/DD299428A5/de not_active IP Right Cessation
- 1990-08-09 ZA ZA906300A patent/ZA906300B/xx unknown
- 1990-08-09 JP JP2209363A patent/JPH0383985A/ja active Pending
- 1990-08-10 MY MYPI90001343A patent/MY107240A/en unknown
- 1990-08-10 US US07/566,279 patent/US5132309A/en not_active Expired - Fee Related
- 1990-08-10 PL PL90291648A patent/PL164662B1/pl unknown
- 1990-08-10 FI FI903974A patent/FI93456C/fi not_active IP Right Cessation
- 1990-08-10 CN CN90106974A patent/CN1025031C/zh not_active Expired - Fee Related
- 1990-08-10 US US07/566,278 patent/US5132303A/en not_active Expired - Fee Related
- 1990-08-10 PL PL90286443A patent/PL163899B1/pl unknown
-
1995
- 1995-07-20 HK HK118295A patent/HK118295A/en not_active IP Right Cessation
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| HMM4 | Cancellation of final prot. due to non-payment of fee |