CY1255A - Long-acting parenteral compositions of haloperidol and bromperidol derivatives - Google Patents
Long-acting parenteral compositions of haloperidol and bromperidol derivatives Download PDFInfo
- Publication number
- CY1255A CY1255A CY1255A CY125580A CY1255A CY 1255 A CY1255 A CY 1255A CY 1255 A CY1255 A CY 1255A CY 125580 A CY125580 A CY 125580A CY 1255 A CY1255 A CY 1255A
- Authority
- CY
- Cyprus
- Prior art keywords
- composition
- haloperidol
- bromperidol
- long
- administration
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 29
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical group C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 title description 23
- RKLNONIVDFXQRX-UHFFFAOYSA-N Bromperidol Chemical class C1CC(O)(C=2C=CC(Br)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 RKLNONIVDFXQRX-UHFFFAOYSA-N 0.000 title description 11
- 229960003878 haloperidol Drugs 0.000 title description 11
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 18
- 230000000506 psychotropic effect Effects 0.000 claims description 7
- 239000008159 sesame oil Substances 0.000 claims description 7
- 235000011803 sesame oil Nutrition 0.000 claims description 7
- 235000019445 benzyl alcohol Nutrition 0.000 claims description 6
- 150000001954 decanoic acid esters Chemical class 0.000 claims description 5
- 239000003755 preservative agent Substances 0.000 claims description 5
- 230000002335 preservative effect Effects 0.000 claims description 5
- 238000007918 intramuscular administration Methods 0.000 claims description 4
- 238000007920 subcutaneous administration Methods 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
- 230000000845 anti-microbial effect Effects 0.000 claims description 2
- 238000007911 parenteral administration Methods 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 239000004599 antimicrobial Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- BLDQVNWZPYYSRH-UHFFFAOYSA-N piperidin-1-yl decanoate Chemical compound CCCCCCCCCC(=O)ON1CCCCC1 BLDQVNWZPYYSRH-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 229960004037 bromperidol Drugs 0.000 description 8
- 238000002560 therapeutic procedure Methods 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 238000000034 method Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- GUTXTARXLVFHDK-UHFFFAOYSA-N Haloperidol decanoate Chemical compound C1CC(OC(=O)CCCCCCCCC)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 GUTXTARXLVFHDK-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 206010047700 Vomiting Diseases 0.000 description 3
- ZINCPWWBSRSXBH-UHFFFAOYSA-N [4-(4-bromophenyl)-1-[4-(4-fluorophenyl)-4-oxobutyl]piperidin-4-yl] decanoate Chemical compound C1CC(OC(=O)CCCCCCCCC)(C=2C=CC(Br)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 ZINCPWWBSRSXBH-UHFFFAOYSA-N 0.000 description 3
- IPIVAXLHTVNRBS-UHFFFAOYSA-N decanoyl chloride Chemical compound CCCCCCCCCC(Cl)=O IPIVAXLHTVNRBS-UHFFFAOYSA-N 0.000 description 3
- 239000002895 emetic Substances 0.000 description 3
- 229960005007 haloperidol decanoate Drugs 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- LKPFBGKZCCBZDK-UHFFFAOYSA-N n-hydroxypiperidine Chemical class ON1CCCCC1 LKPFBGKZCCBZDK-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000004089 psychotropic agent Substances 0.000 description 3
- SKYZYDSNJIOXRL-BTQNPOSSSA-N (6ar)-6-methyl-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinoline-10,11-diol;hydrochloride Chemical compound Cl.C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 SKYZYDSNJIOXRL-BTQNPOSSSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229960004046 apomorphine Drugs 0.000 description 2
- 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 2
- 229960003990 apomorphine hydrochloride Drugs 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 229960004284 bromperidol decanoate Drugs 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000007794 irritation Effects 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 229960002341 trifluperidol Drugs 0.000 description 2
- GPMXUUPHFNMNDH-UHFFFAOYSA-N trifluperidol Chemical compound C1CC(O)(C=2C=C(C=CC=2)C(F)(F)F)CCN1CCCC(=O)C1=CC=C(F)C=C1 GPMXUUPHFNMNDH-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 230000002964 excitative effect Effects 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical class OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 229940001470 psychoactive drug Drugs 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
Classifications
-
- 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
- C07D211/06—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 no double bonds between ring members or between ring members and non-ring members
- C07D211/36—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 no 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/52—Oxygen atoms attached in position 4 having an aryl radical as the second substituent in position 4
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Anesthesiology (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8082679A JPS568318A (en) | 1979-06-28 | 1979-06-28 | Non oral long acting composition of haloperidol and bromperidol derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CY1255A true CY1255A (en) | 1984-08-31 |
Family
ID=13729223
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CY1255A CY1255A (en) | 1979-06-28 | 1980-06-03 | Long-acting parenteral compositions of haloperidol and bromperidol derivatives |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS568318A (enrdf_load_stackoverflow) |
| BE (1) | BE883994A (enrdf_load_stackoverflow) |
| CY (1) | CY1255A (enrdf_load_stackoverflow) |
| DE (1) | DE3024305A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2460932A1 (enrdf_load_stackoverflow) |
| GB (1) | GB2054371B (enrdf_load_stackoverflow) |
| HK (1) | HK83384A (enrdf_load_stackoverflow) |
| KE (1) | KE3427A (enrdf_load_stackoverflow) |
| NL (1) | NL190775C (enrdf_load_stackoverflow) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8621892D0 (en) * | 1986-09-11 | 1986-10-15 | Lundbeck & Co As H | Organic compound |
| DK238190D0 (da) * | 1990-10-03 | 1990-10-03 | Lundbeck & Co As H | Depotderivater |
| ES2077547T3 (es) * | 1992-11-17 | 2000-06-16 | Yoshitomi Pharmaceutical | Microesfera de liberacion sostenida que contiene un antipsicotico y procedimiento de produccion. |
| AU5157798A (en) * | 1996-10-31 | 1998-05-22 | United States Of America, Represented By The Secretary, Department Of Health And Human Services, The | Sustained-release derivatives of hydroxylated analogs of substituted 1-{2{bis(aryl)methoxy}ethyl}-piperazines and -homopiperazines and their use as noncompetitive antagonists of dopamine reuptake |
| RU2178297C1 (ru) * | 2001-02-02 | 2002-01-20 | Открытое акционерное общество "Химико-фармацевтический комбинат "Акрихин" | Фармацевтическая композиция, обладающая антипсихотическим и противорвотным действием, и способ ее получения |
| JP2008519840A (ja) | 2004-11-10 | 2008-06-12 | ジェンザイム・コーポレイション | 糖尿病の処置方法 |
| EP2923699B1 (en) | 2006-05-09 | 2018-06-20 | Genzyme Corporation | Methods of treating fatty liver disease comprising inhibiting glucosphingolipid synthesis |
| EP2594565B1 (en) | 2007-05-31 | 2018-10-24 | Genzyme Corporation | 2-acylaminopropanol-type glucosylceramide synthase inhibitors |
| MX2010003603A (es) | 2007-10-05 | 2010-06-02 | Genzyme Corp | Metodo para el tratamiento de enfermedades de riñon poliquisticas con derivados de ceramida. |
| US8389517B2 (en) | 2008-07-28 | 2013-03-05 | Genzyme Corporation | Glucosylceramide synthase inhibition for the treatment of collapsing glomerulopathy and other glomerular disease |
| RU2578947C2 (ru) | 2008-10-03 | 2016-03-27 | Джензайм Корпорейшн | Ингибиторы глюкозилцерамидсинтазы 2-ациламинопропанольного типа |
| CN103561746B (zh) | 2011-03-18 | 2018-05-29 | 奥克梅斯制药爱尔兰有限公司 | 包含脱水山梨糖醇酯的药物组合物 |
| CN103301461B (zh) * | 2012-03-08 | 2018-09-07 | 江苏豪森药业集团有限公司 | 一种长效注射制剂及其制备方法和用途 |
| EP2827867B1 (en) | 2012-03-19 | 2019-11-06 | Alkermes Pharma Ireland Limited | Pharmaceutical compositions comprising glycerol esters |
| US9999670B2 (en) | 2012-03-19 | 2018-06-19 | Alkermes Pharma Ireland Limited | Pharmaceutical compositions comprising benzyl alcohol |
| EP2827868B8 (en) | 2012-03-19 | 2019-12-18 | Alkermes Pharma Ireland Limited | Pharmaceutical compositions comprising fatty acid esters |
| NZ631345A (en) | 2012-09-19 | 2017-06-30 | Alkermes Pharma Ireland Ltd | Pharmaceutical compositions having improved storage stability |
| US9452131B2 (en) | 2014-03-20 | 2016-09-27 | Alkermes Pharma Ireland Limited | Aripiprazole formulations having increased injection speeds |
| JP7384812B2 (ja) | 2018-03-05 | 2023-11-21 | アルカームス ファーマ アイルランド リミテッド | アリピプラゾール投与戦略 |
| CN113117092A (zh) * | 2020-01-14 | 2021-07-16 | 中国科学院上海药物研究所 | 一种非水缓释递药系统 |
| HUP2100259A1 (hu) | 2021-07-07 | 2023-01-28 | Richter Gedeon Nyrt | Cariprazine tartalmú szabályozott hatóanyag-leadású injekciós készítmények |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3408356A (en) * | 1965-08-31 | 1968-10-29 | Squibb & Sons Inc | Long chain esters of 4'-fluoro-4-[4-hydroxy-4-(alpha, alpha, alpha-trifluorotolyl)piperi-dino]butyrophenone and the like |
| DE1695194A1 (de) * | 1966-07-11 | 1971-03-18 | Hoffmann La Roche | Verfahren zur Herstellung von Piperidinderivaten |
| US3850935A (en) * | 1971-10-16 | 1974-11-26 | Sumitomo Chemical Co | Process for producing piperidine derivatives by degrading quaternary piperidinium salts |
-
1979
- 1979-06-28 JP JP8082679A patent/JPS568318A/ja active Pending
-
1980
- 1980-06-03 GB GB8018117A patent/GB2054371B/en not_active Expired
- 1980-06-03 CY CY1255A patent/CY1255A/en unknown
- 1980-06-20 NL NL8003583A patent/NL190775C/xx not_active IP Right Cessation
- 1980-06-25 BE BE0/201165A patent/BE883994A/fr not_active IP Right Cessation
- 1980-06-27 FR FR8014443A patent/FR2460932A1/fr active Granted
- 1980-06-27 DE DE19803024305 patent/DE3024305A1/de active Granted
-
1984
- 1984-07-20 KE KE3427A patent/KE3427A/xx unknown
- 1984-11-01 HK HK833/84A patent/HK83384A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NL190775B (nl) | 1994-03-16 |
| FR2460932B1 (enrdf_load_stackoverflow) | 1984-11-16 |
| FR2460932A1 (fr) | 1981-01-30 |
| HK83384A (en) | 1984-11-09 |
| DE3024305A1 (de) | 1981-01-22 |
| GB2054371A (en) | 1981-02-18 |
| KE3427A (en) | 1984-08-10 |
| GB2054371B (en) | 1983-08-03 |
| JPS568318A (en) | 1981-01-28 |
| DE3024305C2 (enrdf_load_stackoverflow) | 1989-12-07 |
| BE883994A (fr) | 1980-12-29 |
| NL8003583A (nl) | 1980-12-30 |
| NL190775C (nl) | 1994-08-16 |
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