JPS58118582A - ２−〔４−〔（４，４−ジアルキル−２，６−ピペリジンジオン−１−イル）ブチル〕−１−ピペラジニル〕ピリミジン - Google Patents
２−〔４−〔（４，４−ジアルキル−２，６−ピペリジンジオン−１−イル）ブチル〕−１−ピペラジニル〕ピリミジンInfo
- Publication number
- JPS58118582A JPS58118582A JP57225098A JP22509882A JPS58118582A JP S58118582 A JPS58118582 A JP S58118582A JP 57225098 A JP57225098 A JP 57225098A JP 22509882 A JP22509882 A JP 22509882A JP S58118582 A JPS58118582 A JP S58118582A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- acid addition
- addition salt
- pyrimidinyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 49
- 238000000034 method Methods 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 19
- 231100000252 nontoxic Toxicity 0.000 claims description 10
- 230000003000 nontoxic effect Effects 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 7
- 208000019901 Anxiety disease Diseases 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 239000011230 binding agent Substances 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- YDQAUSHJSHIVAD-UHFFFAOYSA-N 4-(4-pyrimidin-2-ylpiperazin-1-yl)butan-1-amine Chemical compound C1CN(CCCCN)CCN1C1=NC=CC=N1 YDQAUSHJSHIVAD-UHFFFAOYSA-N 0.000 claims description 2
- 238000007910 systemic administration Methods 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 125000002577 pseudohalo group Chemical group 0.000 claims 4
- 241000124008 Mammalia Species 0.000 claims 2
- 230000037396 body weight Effects 0.000 claims 2
- VNEBWJSWMVTSHK-UHFFFAOYSA-L disodium;3-hydroxynaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(O)=CC2=C1 VNEBWJSWMVTSHK-UHFFFAOYSA-L 0.000 claims 2
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- 239000012442 inert solvent Substances 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- CNMOHEDUVVUVPP-UHFFFAOYSA-N piperidine-2,3-dione Chemical compound O=C1CCCNC1=O CNMOHEDUVVUVPP-UHFFFAOYSA-N 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 41
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- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 8
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
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- QWCRAEMEVRGPNT-UHFFFAOYSA-N buspirone Chemical compound C1C(=O)N(CCCCN2CCN(CC2)C=2N=CC=CN=2)C(=O)CC21CCCC2 QWCRAEMEVRGPNT-UHFFFAOYSA-N 0.000 description 5
- 238000004364 calculation method Methods 0.000 description 5
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- MRBFGEHILMYPTF-UHFFFAOYSA-N 1-(2-Pyrimidyl)piperazine Chemical compound C1CNCCN1C1=NC=CC=N1 MRBFGEHILMYPTF-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
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- 150000008064 anhydrides Chemical class 0.000 description 3
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 3
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- LNOQURRKNJKKBU-UHFFFAOYSA-N ethyl piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCNCC1 LNOQURRKNJKKBU-UHFFFAOYSA-N 0.000 description 3
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- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 102000015554 Dopamine receptor Human genes 0.000 description 2
- 108050004812 Dopamine receptor Proteins 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
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- 238000012216 screening Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000012289 standard assay Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000004006 stereotypic behavior Effects 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
- C07D211/86—Oxygen atoms
- C07D211/88—Oxygen atoms attached in positions 2 and 6, e.g. glutarimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
- C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/56—One oxygen atom and one sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/32—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07D487/10—Spiro-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Anesthesiology (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/334,688 US4423049A (en) | 1981-12-28 | 1981-12-28 | 2-[4-[(4,4-Dialkyl-2,6-piperidinedion-1-yl)butyl]-1-piperazinyl]pyrimidines |
| US334688 | 1994-11-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58118582A true JPS58118582A (ja) | 1983-07-14 |
| JPH0368875B2 JPH0368875B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1991-10-30 |
Family
ID=23308351
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57225098A Granted JPS58118582A (ja) | 1981-12-28 | 1982-12-23 | ２−〔４−〔（４，４−ジアルキル−２，６−ピペリジンジオン−１−イル）ブチル〕−１−ピペラジニル〕ピリミジン |
| JP3216768A Pending JPH06293753A (ja) | 1981-12-28 | 1991-03-29 | ２−〔４−〔（４，４−ジアルキル−２、６−ピペリジン ジオン−１−イル）ブチル〕−１−ピペラジニル〕ピリミジン含有組成物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3216768A Pending JPH06293753A (ja) | 1981-12-28 | 1991-03-29 | ２−〔４−〔（４，４−ジアルキル−２、６−ピペリジン ジオン−１−イル）ブチル〕−１−ピペラジニル〕ピリミジン含有組成物 |
Country Status (26)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63243028A (ja) * | 1987-03-02 | 1988-10-07 | ブリストルーマイヤーズ スクイブ カンパニー | 基本的うつ病を軽減するためのうつ病治療剤 |
| JPH06293753A (ja) * | 1981-12-28 | 1994-10-21 | Bristol Myers Squibb Co | ２−〔４−〔（４，４−ジアルキル−２、６−ピペリジン ジオン−１−イル）ブチル〕−１−ピペラジニル〕ピリミジン含有組成物 |
Families Citing this family (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4581357A (en) * | 1983-02-07 | 1986-04-08 | Mead Johnson & Company | Antipsychotic 5-fluoro-pyrimidin-2-yl piperazine compound |
| US5187276A (en) * | 1983-06-18 | 1993-02-16 | Troponwerke Gmbh & Co. Kg. | 2-pyrimidinyl-1-piperazine derivatives |
| DE3321969A1 (de) * | 1983-06-18 | 1984-12-20 | Troponwerke GmbH & Co KG, 5000 Köln | 2-pyrimidinyl-1-piperazin-derivate, verfahren zu ihrer herstellung und diese enthaltende arzneimittel |
| US4668687A (en) * | 1984-07-23 | 1987-05-26 | Bristol-Myers Company | Psychogeriatric 1-(2-pyrimidinyl)piperazinyl derivatives of 1-pyrrolidin-2-ones |
| CA1250291A (en) * | 1984-07-23 | 1989-02-21 | Bristol-Myers Company | Psychogeriatric 1-(2-pyrimidinyl)-piperazinyl derivatives of 1-pyrrolidin-2-ones |
| HUT43600A (en) * | 1985-06-22 | 1987-11-30 | Sandoz Ag | Process for production of new thiazole derivatives and medical compound containing those |
| NZ216720A (en) * | 1985-07-08 | 1990-09-26 | Bristol Myers Co | Diazinylpiperidine derivatives and pharmaceutical compositions |
| US4826843A (en) * | 1985-07-08 | 1989-05-02 | Bristol-Myers | Cerebral function enhancing diazinylpiperidine derivatives |
| US4777254A (en) * | 1986-12-02 | 1988-10-11 | American Home Products Corp. | Cyclic imides as H1 -antagonists |
| US4782060A (en) * | 1987-07-29 | 1988-11-01 | Bristol-Myers Company | Gepirone for alleviation of panic disorders |
| US4880930A (en) * | 1987-11-30 | 1989-11-14 | New James S | Psychotropic acyclic amide derivatives |
| US5116970A (en) * | 1988-02-18 | 1992-05-26 | New James S | Psychotropic heterobicycloalkylpiperazine derivatives: 2. fused pyridazinones |
| US5001130A (en) * | 1988-02-18 | 1991-03-19 | Bristol-Myers Company | Psychotropic heterobicycloalkylpiperazine derivatives |
| US4780466A (en) * | 1988-03-17 | 1988-10-25 | Hoechst-Roussel Pharmaceuticals, Inc. | Arylpiperazinylalkoxy derivatives of cyclic imides |
| US5242911A (en) * | 1988-06-17 | 1993-09-07 | Pfizer Inc. | Bridged bicyclic imides as anxiolytics and antidepressants |
| HUT61760A (en) * | 1988-09-16 | 1993-03-01 | Pfizer | Process for producing bridged, bicyclic imides comprising 4-/4-(3-benzisothiazolyl)-1-piperazinyl/-butyl group and pharmaceutical compositions comprising such compounds |
| FR2654934B1 (fr) * | 1989-11-29 | 1994-09-30 | Midy Spa | Utilisation de derive [4-(2-pyrimidinyl)-1-piperazinyl] butyliques pour la preparation de medicaments destines a combattre les troubles de la motricite intestinale. |
| US5098904A (en) * | 1990-06-27 | 1992-03-24 | Bristol-Myers Squibb Company | Cerebral function enhancing pyrimidinyl derivatives |
| WO1992010200A1 (en) * | 1990-12-14 | 1992-06-25 | New York University | Functional interactions between glial s-100b and central nervous system serotonergic neurons |
| US5824680A (en) * | 1991-08-31 | 1998-10-20 | Bayer Aktiengesellschaft | Ipsapirone for the treatment of alzheimer's disease by improving memory |
| DE4135551A1 (de) * | 1991-08-31 | 1993-03-04 | Schering Ag | Verwendung von antagonisten oder partiellen agonisten am 5-ht1a-rezeptor zur behandlung und praevention von kognitiven stoerungen |
| GB9223153D0 (en) * | 1992-11-05 | 1992-12-16 | Wyeth John & Brother Ltd | Piperazine derivatives |
| FR2701260B1 (fr) * | 1993-02-05 | 1995-05-05 | Esteve Labor Dr | Dérivés de 2-[4-(4-azolylbutyl)-1-pipérazinyl]-5-hydroxypyrimidine, leur préparation et leur application en tant que médicaments. |
| US5338738A (en) * | 1993-04-19 | 1994-08-16 | Bristol-Myers Squibb Company | Cerebral function enhancers: acyclic amide derivatives of pyrimidinylpiperidines |
| FR2705098B1 (fr) * | 1993-05-10 | 1995-08-04 | Esteve Labor Dr | Procédé de préparation de 2-{4-[4-(chloro-1-pyrazolyl)butyl]1-pipérazinyl}pyrimidine (Lesopitron) . |
| HU217129B (hu) * | 1993-07-16 | 1999-11-29 | EGIS Gyógyszergyár Rt. | Eljárás nagy tisztaságú buspiron gyógyászati hatóanyag előállítására |
| US5538985A (en) * | 1994-01-27 | 1996-07-23 | Mitsui Toatsu Chemicals, Inc. | Pyrrolidinone derivatives |
| CA2146593A1 (en) * | 1994-05-05 | 1995-11-06 | Jack Melton | Large-scale process for azapirone synthesis |
| US5521313A (en) * | 1994-05-05 | 1996-05-28 | Bristol-Myers Squibb Company | Process for preparing certain azapirones |
| US5478572A (en) * | 1994-09-06 | 1995-12-26 | Bristol-Myers Squibb Co. | Gepirone dosage form |
| US6312717B1 (en) | 1998-07-07 | 2001-11-06 | Bristol-Myers Squibb Company | Method for treatment of anxiety and depression |
| AU4683499A (en) * | 1998-07-30 | 2000-02-21 | Bristol-Myers Squibb Company | Improved method for treatment of sleep-related respiratory disorders |
| US6566361B2 (en) | 1999-06-30 | 2003-05-20 | Laboratories, Upsa | Azapirone pain treatment |
| US6534507B1 (en) | 1999-12-20 | 2003-03-18 | Fabre-Kramer Pharmaceuticals, Inc. | Methods for treating psychological disorders using bioactive metabolites of gepirone |
| CN100367965C (zh) * | 1999-12-20 | 2008-02-13 | 法布瑞－克雷默制药有限公司 | 吉吡隆代谢物在制备改善哺乳动物不良心理状态的组合物上的应用 |
| BR0107721A (pt) * | 2000-01-19 | 2002-10-01 | Akzo Nobel Nv | Combinação, uso de mirtapazina e gepirona, método para o tratamento de depressão ou de um distúrbio relacionado em um indivìduo de uma espécie vertebrada, e, kit de paciente que contém meios para a administração de doses unitárias dosadas |
| WO2002016347A1 (en) * | 2000-08-22 | 2002-02-28 | Akzo Nobel N.V. | Active metabolite of gepirone |
| CA2427098A1 (en) * | 2000-11-29 | 2002-06-06 | John Mehnert Schaus | 1-(2-m-methanesulfonamidophenylethyl)-4-(m-trifluoromethylphenyl)piperazine and pharmaceutically acceptable salts and solvates thereof and their use in the treatment of incontinence |
| US20040002500A1 (en) * | 2002-06-28 | 2004-01-01 | Fabre Kramer Pharmaceutical, Inc. | Methods for treating attention deficit disorder |
| US20040147581A1 (en) * | 2002-11-18 | 2004-07-29 | Pharmacia Corporation | Method of using a Cox-2 inhibitor and a 5-HT1A receptor modulator as a combination therapy |
| US7456180B2 (en) * | 2003-07-30 | 2008-11-25 | Xenon Pharmaceuticals Inc. | Piperazine derivatives and their use as therapeutic agents |
| CA2547283C (en) * | 2003-11-26 | 2010-11-09 | Pfizer Products Inc. | Aminopyrazole derivatives as gsk-3 inhibitors |
| AU2004324868B2 (en) * | 2004-11-05 | 2010-04-29 | Fabre Kramer Holdings Inc | High-dosage extended-release formulation of gepirone |
| US20060099267A1 (en) * | 2004-11-05 | 2006-05-11 | Fabre-Kramer Pharmaceuticals, Inc. | High-dosage extended-release formulation of gepirone |
| EP2159226B1 (de) * | 2007-03-29 | 2016-08-31 | Joint-stock Company "Obninsk Chemical Pharmaceutical Company" | Antihistamin- und antiallergienmittel sowie verfahren zu seiner herstellung |
| WO2011030139A1 (en) * | 2009-09-11 | 2011-03-17 | Astrazeneca Ab | 4- (pyrimidin-2-yl) -piperazine and 4- (pyrimidin-2-yl) -piperidine derivatives as gpr119 modulators |
| IT201900000657A1 (it) | 2019-01-16 | 2020-07-16 | Procos Spa | Processo per la sintesi di gepirone |
| GB202014736D0 (en) * | 2020-09-18 | 2020-11-04 | Imperial College Innovations Ltd | Novel compounds and their use in therapy |
| CN119409681A (zh) * | 2024-03-28 | 2025-02-11 | 北京华素制药股份有限公司 | 一种盐酸丁螺环酮的制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3398151A (en) * | 1966-02-01 | 1968-08-20 | Mead Johnson & Co | Azaspirodecanediones and azaspiroundecanediones |
| BE759371A (fr) * | 1969-11-24 | 1971-05-24 | Bristol Myers Co | Azaspirodecanediones heterocycliques et procedes pour leur preparation |
| US3976776A (en) * | 1972-12-06 | 1976-08-24 | Mead Johnson & Company | Tranquilizer process employing N-(heteroarcyclic)piperazinylalkylazaspiroalkanediones |
| US4182763A (en) * | 1978-05-22 | 1980-01-08 | Mead Johnson & Company | Buspirone anti-anxiety method |
| IL57569A0 (en) | 1978-06-20 | 1979-10-31 | Synthelabo | Phenylpiperazine derivative,their preparation and pharmaceutical compositions containing them |
| US4423049A (en) * | 1981-12-28 | 1983-12-27 | Mead Johnson & Company | 2-[4-[(4,4-Dialkyl-2,6-piperidinedion-1-yl)butyl]-1-piperazinyl]pyrimidines |
-
1981
- 1981-12-28 US US06/334,688 patent/US4423049A/en not_active Expired - Lifetime
-
1982
- 1982-11-19 ZA ZA828549A patent/ZA828549B/xx unknown
- 1982-11-22 CA CA000416088A patent/CA1244426A/en not_active Expired
- 1982-12-02 AU AU91083/82A patent/AU555797B2/en not_active Expired
- 1982-12-08 GR GR70021A patent/GR77045B/el unknown
- 1982-12-08 KR KR8205503A patent/KR870001045B1/ko not_active Expired
- 1982-12-22 IT IT49719/82A patent/IT1158039B/it active
- 1982-12-23 GB GB08236593A patent/GB2114122B/en not_active Expired
- 1982-12-23 ES ES518510A patent/ES8405786A1/es not_active Expired
- 1982-12-23 NL NL8204970A patent/NL193283C/nl not_active IP Right Cessation
- 1982-12-23 CY CY137982A patent/CY1379A/en unknown
- 1982-12-23 JP JP57225098A patent/JPS58118582A/ja active Granted
- 1982-12-23 DK DK573182A patent/DK162389C/da not_active IP Right Cessation
- 1982-12-23 IE IE3067/82A patent/IE54619B1/en not_active IP Right Cessation
- 1982-12-23 FI FI824442A patent/FI70891C/fi not_active IP Right Cessation
- 1982-12-24 FR FR8221750A patent/FR2518993B1/fr not_active Expired
- 1982-12-27 SE SE8207425A patent/SE453088B/sv not_active IP Right Cessation
- 1982-12-27 DE DE3248160A patent/DE3248160C2/de not_active Expired - Lifetime
- 1982-12-27 PT PT76036A patent/PT76036B/pt unknown
- 1982-12-28 BE BE0/209826A patent/BE895504A/fr not_active IP Right Cessation
- 1982-12-28 CH CH7594/82A patent/CH656383A5/de not_active IP Right Cessation
- 1982-12-28 AT AT0469882A patent/AT382373B/de not_active IP Right Cessation
- 1982-12-29 LU LU84561A patent/LU84561A1/fr unknown
-
1983
- 1983-08-12 ES ES524945A patent/ES524945A0/es active Granted
-
1987
- 1987-03-27 SG SG297/87A patent/SG29787G/en unknown
- 1987-03-31 KE KE3709A patent/KE3709A/xx unknown
-
1988
- 1988-01-21 HK HK52/88A patent/HK5288A/xx not_active IP Right Cessation
-
1991
- 1991-03-29 JP JP3216768A patent/JPH06293753A/ja active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06293753A (ja) * | 1981-12-28 | 1994-10-21 | Bristol Myers Squibb Co | ２−〔４−〔（４，４−ジアルキル−２、６−ピペリジン ジオン−１−イル）ブチル〕−１−ピペラジニル〕ピリミジン含有組成物 |
| JPS63243028A (ja) * | 1987-03-02 | 1988-10-07 | ブリストルーマイヤーズ スクイブ カンパニー | 基本的うつ病を軽減するためのうつ病治療剤 |
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