ZA200502216B - Heterocyclic substituted piperazines for the treatment of schizophrenia. - Google Patents
Heterocyclic substituted piperazines for the treatment of schizophrenia. Download PDFInfo
- Publication number
- ZA200502216B ZA200502216B ZA200502216A ZA200502216A ZA200502216B ZA 200502216 B ZA200502216 B ZA 200502216B ZA 200502216 A ZA200502216 A ZA 200502216A ZA 200502216 A ZA200502216 A ZA 200502216A ZA 200502216 B ZA200502216 B ZA 200502216B
- Authority
- ZA
- South Africa
- Prior art keywords
- disorders
- disorder
- quinolin
- piperazin
- dihydro
- Prior art date
Links
- 201000000980 schizophrenia Diseases 0.000 title claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 title claims description 8
- 150000004885 piperazines Chemical class 0.000 title description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 32
- 125000001153 fluoro group Chemical group F* 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- -1 nitro, cyano, amino Chemical group 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 239000011593 sulfur Substances 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Chemical group 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical group C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
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- 238000000034 method Methods 0.000 claims 8
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- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims 4
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
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- GVGLGOZIDCSQPN-PVHGPHFFSA-N Heroin Chemical compound O([C@H]1[C@H](C=C[C@H]23)OC(C)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4OC(C)=O GVGLGOZIDCSQPN-PVHGPHFFSA-N 0.000 claims 4
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- 208000025748 atypical depressive disease Diseases 0.000 claims 4
- 229940049706 benzodiazepine Drugs 0.000 claims 4
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 claims 4
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- 229960002715 nicotine Drugs 0.000 claims 4
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims 4
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 claims 4
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- SRAQFALNAGNAQE-UHFFFAOYSA-N 6-[2-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]ethyl]-4,4,8-trimethyl-1,3-dihydroquinolin-2-one Chemical compound N1C(=O)CC(C)(C)C2=C1C(C)=CC(CCN1CCN(CC1)C=1C3=CC=CC=C3SN=1)=C2 SRAQFALNAGNAQE-UHFFFAOYSA-N 0.000 claims 2
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- PYLOOAAZCQAYIV-UHFFFAOYSA-N 6-[2-[4-(1,2-benzoxazol-3-yl)piperazin-1-yl]ethyl]-3,3,4-trimethyl-1,4-dihydroquinolin-2-one Chemical compound C1=CC=C2C(N3CCN(CC3)CCC=3C=C4C(C(C(=O)NC4=CC=3)(C)C)C)=NOC2=C1 PYLOOAAZCQAYIV-UHFFFAOYSA-N 0.000 claims 1
- HMMNBVXJFGFCOH-UHFFFAOYSA-N 6-[2-[4-(1,2-benzoxazol-3-yl)piperazin-1-yl]ethyl]-3,3-dimethyl-1,4-dihydroquinolin-2-one Chemical compound C1=CC=C2C(N3CCN(CC3)CCC=3C=C4CC(C(NC4=CC=3)=O)(C)C)=NOC2=C1 HMMNBVXJFGFCOH-UHFFFAOYSA-N 0.000 claims 1
- VUUTVDVGKRASMV-UHFFFAOYSA-N 6-[2-[4-(1,2-benzoxazol-3-yl)piperazin-1-yl]ethyl]-3-methyl-3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC=C2C(N3CCN(CC3)CCC=3C=C4CC(C(NC4=CC=3)=O)C)=NOC2=C1 VUUTVDVGKRASMV-UHFFFAOYSA-N 0.000 claims 1
- ICYAYJZMSZYRTH-UHFFFAOYSA-N 6-[2-[4-(1,2-benzoxazol-3-yl)piperazin-1-yl]ethyl]-4,4-dimethyl-1,3-dihydroquinolin-2-one Chemical compound C1=CC=C2C(N3CCN(CC3)CCC3=CC=C4NC(=O)CC(C4=C3)(C)C)=NOC2=C1 ICYAYJZMSZYRTH-UHFFFAOYSA-N 0.000 claims 1
- ZGXRKIVHNAJFGW-UHFFFAOYSA-N 6-[2-[4-(1h-indazol-3-yl)piperazin-1-yl]ethyl]-3,4-dimethyl-3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC=C2C(N3CCN(CC3)CCC=3C=C4C(C)C(C(NC4=CC=3)=O)C)=NNC2=C1 ZGXRKIVHNAJFGW-UHFFFAOYSA-N 0.000 claims 1
- LZDIGLUPIQGJDJ-UHFFFAOYSA-N 6-[2-[4-(1h-indazol-3-yl)piperazin-1-yl]ethyl]-3-methyl-3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC=C2C(N3CCN(CC3)CCC=3C=C4CC(C(NC4=CC=3)=O)C)=NNC2=C1 LZDIGLUPIQGJDJ-UHFFFAOYSA-N 0.000 claims 1
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- JHBMJIYNOSDZEY-UHFFFAOYSA-N 6-[2-[4-(1h-indazol-3-yl)piperazin-1-yl]ethyl]-4-methyl-3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC=C2C(N3CCN(CC3)CCC3=CC=C4NC(=O)CC(C4=C3)C)=NNC2=C1 JHBMJIYNOSDZEY-UHFFFAOYSA-N 0.000 claims 1
- AKILNVRTEPFPLQ-UHFFFAOYSA-N 6-[3-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]propyl]-3,3-dimethyl-1,4-dihydroquinolin-2-one Chemical compound C1=CC=C2C(N3CCN(CC3)CCCC=3C=C4CC(C(NC4=CC=3)=O)(C)C)=NSC2=C1 AKILNVRTEPFPLQ-UHFFFAOYSA-N 0.000 claims 1
- BVHBZOKJMIKPOZ-UHFFFAOYSA-N 6-[3-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]propyl]-3-methyl-3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC=C2C(N3CCN(CC3)CCCC=3C=C4CC(C(NC4=CC=3)=O)C)=NSC2=C1 BVHBZOKJMIKPOZ-UHFFFAOYSA-N 0.000 claims 1
- WJMJAABZHXLYBK-UHFFFAOYSA-N 6-[3-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]propyl]-4-methyl-3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC=C2C(N3CCN(CC3)CCCC3=CC=C4NC(=O)CC(C4=C3)C)=NSC2=C1 WJMJAABZHXLYBK-UHFFFAOYSA-N 0.000 claims 1
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- FWIJCAZWYWIOGO-UHFFFAOYSA-N 6-[3-[4-(1,2-benzoxazol-3-yl)piperazin-1-yl]propyl]-3-methyl-3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC=C2C(N3CCN(CC3)CCCC=3C=C4CC(C(NC4=CC=3)=O)C)=NOC2=C1 FWIJCAZWYWIOGO-UHFFFAOYSA-N 0.000 claims 1
- JRIIIUATLVQNQZ-UHFFFAOYSA-N 6-[3-[4-(1,2-benzoxazol-3-yl)piperazin-1-yl]propyl]-7-chloro-4,4-dimethyl-1,3-dihydroquinolin-2-one Chemical compound C1=CC=C2C(N3CCN(CC3)CCCC3=C(Cl)C=C4NC(=O)CC(C4=C3)(C)C)=NOC2=C1 JRIIIUATLVQNQZ-UHFFFAOYSA-N 0.000 claims 1
- XLXQCJTZPKZZHA-UHFFFAOYSA-N 6-[3-[4-(1h-indazol-3-yl)piperazin-1-yl]propyl]-3-methyl-3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC=C2C(N3CCN(CC3)CCCC=3C=C4CC(C(NC4=CC=3)=O)C)=NNC2=C1 XLXQCJTZPKZZHA-UHFFFAOYSA-N 0.000 claims 1
- DSXFKXJQTXWPRC-UHFFFAOYSA-N 6-[3-[4-(1h-indazol-3-yl)piperazin-1-yl]propyl]-4,4-dimethyl-1,3-dihydroquinolin-2-one Chemical compound C1=CC=C2C(N3CCN(CC3)CCCC3=CC=C4NC(=O)CC(C4=C3)(C)C)=NNC2=C1 DSXFKXJQTXWPRC-UHFFFAOYSA-N 0.000 claims 1
- DYETXXQBGKPREH-UHFFFAOYSA-N 6-[3-[4-(1h-indazol-3-yl)piperazin-1-yl]propyl]-4-methyl-3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC=C2C(N3CCN(CC3)CCCC3=CC=C4NC(=O)CC(C4=C3)C)=NNC2=C1 DYETXXQBGKPREH-UHFFFAOYSA-N 0.000 claims 1
- 241000237519 Bivalvia Species 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 208000020186 Schizophreniform disease Diseases 0.000 claims 1
- 208000028810 Shared psychotic disease Diseases 0.000 claims 1
- 208000011963 Substance-induced psychotic disease Diseases 0.000 claims 1
- 231100000393 Substance-induced psychotic disorder Toxicity 0.000 claims 1
- 208000022257 bipolar II disease Diseases 0.000 claims 1
- 235000020639 clam Nutrition 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000626 neurodegenerative effect Effects 0.000 claims 1
- 208000022610 schizoaffective disease Diseases 0.000 claims 1
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 description 2
- 102000004980 Dopamine D2 Receptors Human genes 0.000 description 1
- 108090001111 Dopamine D2 Receptors Proteins 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 239000000164 antipsychotic agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41147502P | 2002-09-17 | 2002-09-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200502216B true ZA200502216B (en) | 2005-09-26 |
Family
ID=35476681
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200502216A ZA200502216B (en) | 2002-09-17 | 2005-03-16 | Heterocyclic substituted piperazines for the treatment of schizophrenia. |
Country Status (4)
| Country | Link |
|---|---|
| CN (1) | CN1701072A (es) |
| CR (1) | CR7735A (es) |
| TN (1) | TNSN05074A1 (es) |
| ZA (1) | ZA200502216B (es) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8653069B2 (en) | 2008-07-28 | 2014-02-18 | Jiangsu Hengyi Pharmaceutical Co., Ltd. | Aralkyl substituted piperidine or piperazine derivatives and their use for treating schizophrenia |
| CA2735400A1 (en) * | 2008-09-22 | 2010-03-25 | F. Hoffmann-La Roche Ag | Piperazine d3 and 5-ht2a receptor modulators |
| CN102718758A (zh) * | 2011-03-31 | 2012-10-10 | 江苏恒谊药业有限公司 | 喹啉酮衍生物及其作为抗精神分裂症药物的应用 |
| CN103130737B (zh) * | 2011-12-05 | 2015-12-02 | 江苏恒谊药业有限公司 | 环己烷胺类化合物及其作为抗精神分裂症药物的应用 |
| WO2020230802A1 (ja) * | 2019-05-14 | 2020-11-19 | 杏林製薬株式会社 | ４－オキソピロリジン－３－カルボン酸アミド誘導体の製造方法 |
| CN112142737B (zh) * | 2019-06-29 | 2022-03-18 | 武汉珈瑜科技有限公司 | 一种治疗精神分裂症药物盐酸盐的固体形式 |
-
2003
- 2003-09-05 CN CN 03825236 patent/CN1701072A/zh active Pending
-
2005
- 2005-03-11 CR CR7735A patent/CR7735A/es not_active Application Discontinuation
- 2005-03-16 ZA ZA200502216A patent/ZA200502216B/en unknown
- 2005-03-17 TN TNP2005000074A patent/TNSN05074A1/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CR7735A (es) | 2005-06-15 |
| CN1701072A (zh) | 2005-11-23 |
| TNSN05074A1 (fr) | 2007-05-14 |
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