LU84561A1 - 2-(4-((4,4,-dialcoyl-2,6-piperidinedione-1-yl)butyl)-1-piperazinyl)pyrimidines - Google Patents
2-(4-((4,4,-dialcoyl-2,6-piperidinedione-1-yl)butyl)-1-piperazinyl)pyrimidines Download PDFInfo
- Publication number
- LU84561A1 LU84561A1 LU84561A LU84561A LU84561A1 LU 84561 A1 LU84561 A1 LU 84561A1 LU 84561 A LU84561 A LU 84561A LU 84561 A LU84561 A LU 84561A LU 84561 A1 LU84561 A1 LU 84561A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- formula
- compound
- pharmaceutically acceptable
- addition salts
- acid addition
- Prior art date
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- -1 BUTYL Chemical class 0.000 title claims description 11
- 150000003230 pyrimidines Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 77
- 238000000034 method Methods 0.000 claims description 33
- 239000002253 acid Substances 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 21
- 230000008569 process Effects 0.000 claims description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 17
- 238000010992 reflux Methods 0.000 claims description 13
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 12
- 231100000252 nontoxic Toxicity 0.000 claims description 11
- 230000003000 nontoxic effect Effects 0.000 claims description 11
- 239000002249 anxiolytic agent Substances 0.000 claims description 9
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 230000000949 anxiolytic effect Effects 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 241000124008 Mammalia Species 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 5
- KNCYXPMJDCCGSJ-UHFFFAOYSA-N piperidine-2,6-dione Chemical compound O=C1CCCC(=O)N1 KNCYXPMJDCCGSJ-UHFFFAOYSA-N 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 208000019901 Anxiety disease Diseases 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 230000036506 anxiety Effects 0.000 claims description 3
- 230000037396 body weight Effects 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 239000012429 reaction media Substances 0.000 claims description 3
- 238000007910 systemic administration Methods 0.000 claims description 3
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 150000003949 imides Chemical class 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims 2
- 230000001681 protective effect Effects 0.000 claims 2
- HIJQFTSZBHDYKW-UHFFFAOYSA-N 4,4-dimethyloxane-2,6-dione Chemical compound CC1(C)CC(=O)OC(=O)C1 HIJQFTSZBHDYKW-UHFFFAOYSA-N 0.000 claims 1
- QOIGKGMMAGJZNZ-UHFFFAOYSA-N gepirone Chemical compound O=C1CC(C)(C)CC(=O)N1CCCCN1CCN(C=2N=CC=CN=2)CC1 QOIGKGMMAGJZNZ-UHFFFAOYSA-N 0.000 claims 1
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- 230000000694 effects Effects 0.000 description 12
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- 230000015572 biosynthetic process Effects 0.000 description 11
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 10
- 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 9
- 229960002495 buspirone Drugs 0.000 description 9
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- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 8
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 8
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 230000000561 anti-psychotic effect Effects 0.000 description 6
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- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
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- GXXFECFLKWGTNP-UHFFFAOYSA-N 5-fluoro-2-piperazin-1-ylpyrimidine Chemical compound N1=CC(F)=CN=C1N1CCNCC1 GXXFECFLKWGTNP-UHFFFAOYSA-N 0.000 description 5
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 239000006188 syrup Substances 0.000 description 4
- 235000020357 syrup Nutrition 0.000 description 4
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 3
- MRBFGEHILMYPTF-UHFFFAOYSA-N 1-(2-Pyrimidyl)piperazine Chemical compound C1CNCCN1C1=NC=CC=N1 MRBFGEHILMYPTF-UHFFFAOYSA-N 0.000 description 3
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 3
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
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- QQCSGYBVHXFEFG-UHFFFAOYSA-N 1-(4-bromobutyl)-4,4-dimethylpiperidine-2,6-dione Chemical compound CC1(C)CC(=O)N(CCCCBr)C(=O)C1 QQCSGYBVHXFEFG-UHFFFAOYSA-N 0.000 description 2
- YKNAWJOYASYWEV-UHFFFAOYSA-N 1-(4-bromobutyl)-4-methyl-4-propylpiperidine-2,6-dione Chemical compound CCCC1(C)CC(=O)N(CCCCBr)C(=O)C1 YKNAWJOYASYWEV-UHFFFAOYSA-N 0.000 description 2
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- FPIFDKJZXXMJRK-UHFFFAOYSA-N 1-[4-[4-(5-hydroxypyrimidin-2-yl)piperazin-1-yl]butyl]-4,4-dimethylpiperidine-2,6-dione Chemical compound O=C1CC(C)(C)CC(=O)N1CCCCN1CCN(C=2N=CC(O)=CN=2)CC1 FPIFDKJZXXMJRK-UHFFFAOYSA-N 0.000 description 1
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- SXAMGRAIZSSWIH-UHFFFAOYSA-N 2-[3-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,2,4-oxadiazol-5-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NOC(=N1)CC(=O)N1CC2=C(CC1)NN=N2 SXAMGRAIZSSWIH-UHFFFAOYSA-N 0.000 description 1
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229950001675 spiperone Drugs 0.000 description 1
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- 125000001424 substituent group Chemical group 0.000 description 1
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- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
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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)
- Psychiatry (AREA)
- Anesthesiology (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 |
| US33468881 | 1981-12-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LU84561A1 true LU84561A1 (fr) | 1983-09-08 |
Family
ID=23308351
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU84561A LU84561A1 (fr) | 1981-12-28 | 1982-12-29 | 2-(4-((4,4,-dialcoyl-2,6-piperidinedione-1-yl)butyl)-1-piperazinyl)pyrimidines |
Country Status (26)
Families Citing this family (51)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US4581357A (en) * | 1983-02-07 | 1986-04-08 | Mead Johnson & Company | Antipsychotic 5-fluoro-pyrimidin-2-yl piperazine compound |
| 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 |
| US5187276A (en) * | 1983-06-18 | 1993-02-16 | Troponwerke Gmbh & Co. Kg. | 2-pyrimidinyl-1-piperazine derivatives |
| 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 |
| NL8601494A (nl) * | 1985-06-22 | 1987-01-16 | Sandoz Ag | Thiazolen, hun bereiding en farmaceutische preparaten die ze bevatten. |
| US4826843A (en) * | 1985-07-08 | 1989-05-02 | Bristol-Myers | Cerebral function enhancing diazinylpiperidine derivatives |
| NZ216720A (en) * | 1985-07-08 | 1990-09-26 | Bristol Myers Co | Diazinylpiperidine derivatives and pharmaceutical compositions |
| US4777254A (en) * | 1986-12-02 | 1988-10-11 | American Home Products Corp. | Cyclic imides as H1 -antagonists |
| US4771053A (en) * | 1987-03-02 | 1988-09-13 | Bristol-Myers Company | Method for alleviation of primary depressive disorders |
| 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 |
| US5001130A (en) * | 1988-02-18 | 1991-03-19 | Bristol-Myers Company | Psychotropic heterobicycloalkylpiperazine derivatives |
| US5116970A (en) * | 1988-02-18 | 1992-05-26 | New James S | Psychotropic heterobicycloalkylpiperazine derivatives: 2. fused pyridazinones |
| 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 |
| US5077295A (en) * | 1988-09-16 | 1991-12-31 | Pfizer Inc. | Antipsychoic 4-(4-(3-benzisothiazolyl)-1-piperazinyl)buytl bridged bicycle imides |
| 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 |
| 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 |
| US5824680A (en) * | 1991-08-31 | 1998-10-20 | Bayer Aktiengesellschaft | Ipsapirone for the treatment of alzheimer's disease by improving memory |
| 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 |
| US5521313A (en) * | 1994-05-05 | 1996-05-28 | Bristol-Myers Squibb Company | Process for preparing certain azapirones |
| CA2146593A1 (en) * | 1994-05-05 | 1995-11-06 | Jack Melton | Large-scale process for azapirone synthesis |
| 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 |
| WO2000006163A1 (en) * | 1998-07-30 | 2000-02-10 | 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 |
| HUP0204050A3 (en) * | 2000-01-19 | 2004-09-28 | Akzo Nobel Nv | Drug combination for the treatment of depression and related disorders comprising mirtazapine and gepirone |
| WO2002016347A1 (en) * | 2000-08-22 | 2002-02-28 | Akzo Nobel N.V. | Active metabolite of gepirone |
| AU2002230411A1 (en) * | 2000-11-29 | 2002-06-11 | Eli Lilly And Company | 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 |
| BRPI0412348A (pt) * | 2003-07-30 | 2006-09-05 | Xenon Pharmaceuticals Inc | derivados de piperazina e seu uso como agentes terapêuticos |
| US7671072B2 (en) * | 2003-11-26 | 2010-03-02 | Pfizer Inc. | Aminopyrazole derivatives as GSK-3 inhibitors |
| WO2006052227A1 (en) * | 2004-11-05 | 2006-05-18 | 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 |
| CN101861317B (zh) * | 2007-03-29 | 2013-07-31 | A.B.英特尔法玛有限公司 | 抗组胺类抗过敏剂及其制备方法 |
| 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 |
| DK251079A (da) | 1978-06-20 | 1979-12-21 | Synthelabo | Fremgangsmaade til fremstilling af phenylpiperazinderivater |
| 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 JP JP57225098A patent/JPS58118582A/ja active Granted
- 1982-12-23 ES ES518510A patent/ES8405786A1/es not_active Expired
- 1982-12-23 CY CY137982A patent/CY1379A/en unknown
- 1982-12-23 DK DK573182A patent/DK162389C/da not_active IP Right Cessation
- 1982-12-23 GB GB08236593A patent/GB2114122B/en not_active Expired
- 1982-12-23 NL NL8204970A patent/NL193283C/nl not_active IP Right Cessation
- 1982-12-23 FI FI824442A patent/FI70891C/fi not_active IP Right Cessation
- 1982-12-23 IE IE3067/82A patent/IE54619B1/en not_active IP Right Cessation
- 1982-12-24 FR FR8221750A patent/FR2518993B1/fr not_active Expired
- 1982-12-27 DE DE3248160A patent/DE3248160C2/de not_active Expired - Lifetime
- 1982-12-27 SE SE8207425A patent/SE453088B/sv not_active IP Right Cessation
- 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 AT AT0469882A patent/AT382373B/de not_active IP Right Cessation
- 1982-12-28 CH CH7594/82A patent/CH656383A5/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
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