CA1292993C - Ester de l'acide acetique avec l'haloperidol - Google Patents

Ester de l'acide acetique avec l'haloperidol

Info

Publication number: CA1292993C
Authority: CA; Canada
Prior art keywords: acetic acid; oil; acid ester; pharmaceutical composition; haloperidol
Prior art date: 1987-09-11
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.): Expired - Lifetime

Application number

CA000546747A

Other languages

English (en)

Inventor

Jens Kristian Perregaard

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

H Lundbeck AS

Original Assignee

H Lundbeck AS

Priority date (The priority date 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 date listed.)

1987-09-11

Filing date

1987-09-11

Publication date

1991-12-10

1987-09-11 Application filed by H Lundbeck AS filed Critical H Lundbeck AS

1987-09-11 Priority to CA000546747A priority Critical patent/CA1292993C/fr

1991-12-10 Application granted granted Critical

1991-12-10 Publication of CA1292993C publication Critical patent/CA1292993C/fr

2008-12-10 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 title claims abstract description 46
150000002168 ethanoic acid esters Chemical class 0.000 title claims abstract description 12
229960003878 haloperidol Drugs 0.000 title abstract description 20
150000003839 salts Chemical class 0.000 claims abstract description 16
238000000034 method Methods 0.000 claims abstract description 11
239000002253 acid Substances 0.000 claims abstract description 10
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
208000028017 Psychotic disease Diseases 0.000 claims abstract description 4
238000002360 preparation method Methods 0.000 claims abstract description 4
239000003921 oil Substances 0.000 claims description 9
235000019198 oils Nutrition 0.000 claims description 9
150000001875 compounds Chemical class 0.000 claims description 8
239000008159 sesame oil Substances 0.000 claims description 5
235000011803 sesame oil Nutrition 0.000 claims description 5
150000001242 acetic acid derivatives Chemical class 0.000 claims description 4
239000004480 active ingredient Substances 0.000 claims description 4
239000000725 suspension Substances 0.000 claims description 3
239000002552 dosage form Substances 0.000 claims description 2
239000012458 free base Substances 0.000 claims description 2
235000015112 vegetable and seed oil Nutrition 0.000 claims description 2
239000008158 vegetable oil Substances 0.000 claims description 2
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
JBKHQXLMZYBILY-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-1-(4-fluorophenyl)butan-2-one Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCC(=O)CC1=CC=C(F)C=C1 JBKHQXLMZYBILY-UHFFFAOYSA-N 0.000 claims 1
241000282414 Homo sapiens Species 0.000 abstract description 4
241001465754 Metazoa Species 0.000 abstract description 4
150000002148 esters Chemical class 0.000 abstract description 2
239000000203 mixture Substances 0.000 description 10
238000002347 injection Methods 0.000 description 8
239000007924 injection Substances 0.000 description 8
210000003205 muscle Anatomy 0.000 description 7
239000000243 solution Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
241000282887 Suidae Species 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
239000003176 neuroleptic agent Substances 0.000 description 2
230000000701 neuroleptic effect Effects 0.000 description 2
239000004006 olive oil Substances 0.000 description 2
235000008390 olive oil Nutrition 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
SKTFQHRVFFOHTQ-UHFFFAOYSA-N 8-bromo-1,3-dimethyl-7h-purine-2,6-dione Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC(Br)=N2 SKTFQHRVFFOHTQ-UHFFFAOYSA-N 0.000 description 1
102100026189 Beta-galactosidase Human genes 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
206010015719 Exsanguination Diseases 0.000 description 1
108010059881 Lactase Proteins 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
244000000231 Sesamum indicum Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
ZFXYFBGIUFBOJW-UHFFFAOYSA-N Theophylline Natural products O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
206010047700 Vomiting Diseases 0.000 description 1
DQMKFVKNNDMGTA-UHFFFAOYSA-N [4-(4-chlorophenyl)-1-[4-(4-fluorophenyl)-4-oxobutyl]piperidin-4-yl] acetate Chemical compound C1CC(OC(=O)C)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 DQMKFVKNNDMGTA-UHFFFAOYSA-N 0.000 description 1
230000005856 abnormality Effects 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
230000000561 anti-psychotic effect Effects 0.000 description 1
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 1
229960004046 apomorphine Drugs 0.000 description 1
239000002585 base Substances 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
108010005774 beta-Galactosidase Proteins 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000037396 body weight Effects 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
235000005687 corn oil Nutrition 0.000 description 1
239000002285 corn oil Substances 0.000 description 1
239000002385 cottonseed oil Substances 0.000 description 1
235000012343 cottonseed oil Nutrition 0.000 description 1
WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
150000001954 decanoic acid esters Chemical class 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000003405 delayed action preparation Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003480 eluent Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229940116108 lactase Drugs 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
230000002045 lasting effect Effects 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
238000005259 measurement Methods 0.000 description 1
230000000116 mitigating effect Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
230000017074 necrotic cell death Effects 0.000 description 1
230000001338 necrotic effect Effects 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000008188 pellet Substances 0.000 description 1
230000003236 psychic effect Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
201000000980 schizophrenia Diseases 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
238000007864 suspending Methods 0.000 description 1
239000012085 test solution Substances 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
-1 theophylline acetic acids Chemical class 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
230000008673 vomiting Effects 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA000546747A 1987-09-11 1987-09-11 Ester de l'acide acetique avec l'haloperidol Expired - Lifetime CA1292993C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000546747A CA1292993C (fr)	1987-09-11	1987-09-11	Ester de l'acide acetique avec l'haloperidol

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000546747A CA1292993C (fr)	1987-09-11	1987-09-11	Ester de l'acide acetique avec l'haloperidol

Publications (1)

Publication Number	Publication Date
CA1292993C true CA1292993C (fr)	1991-12-10

Family

ID=4136427

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000546747A Expired - Lifetime CA1292993C (fr)	1987-09-11	1987-09-11	Ester de l'acide acetique avec l'haloperidol

Country Status (1)

Country	Link
CA (1)	CA1292993C (fr)

1987
- 1987-09-11 CA CA000546747A patent/CA1292993C/fr not_active Expired - Lifetime

Legal Events

Date	Code	Title	Description
2008-12-10	MKEX	Expiry

Publication	Publication Date	Title
US4855307A (en)	1989-08-08	Acetic acid ester of haloperidol
KR960000431B1 (ko)	1996-01-06	안정한된 약제 조성물
US4830853A (en)	1989-05-16	Drug compositions stabilized against oxidation
US6239164B1 (en)	2001-05-29	Pyrrolidine carboxylate and pyrrolidine amide hair revitalizing agents
DE2738646C2 (de)	1985-08-08	Piperidyl-indol-Derivate, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Zusammensetzungen
JPH01165524A (ja)	1989-06-29	局所適用のための医薬又は化粧品組成物
CY1255A (en)	1984-08-31	Long-acting parenteral compositions of haloperidol and bromperidol derivatives
DE60225434T2 (de)	2009-03-12	Cumarin derivate und ihre verwendung als antikoagulantien
EP1713466B1 (fr)	2009-03-18	Composition antiparasitaire contenant un sel organique amine de closantel
CA1292993C (fr)	1991-12-10	Ester de l'acide acetique avec l'haloperidol
CH392542A (de)	1965-05-31	Verfahren zur Herstellung von basischen Amiden
EP0031584A2 (fr)	1981-07-08	Aminopropènes et aminopropanes substitués en position 2 et compositions anti-microbiennes et anti-inflammatoires
IE45178B1 (en)	1982-06-30	Phenothiazines
US4442106A (en)	1984-04-10	Quinoline derivatives, pharmaceutical compositions containing such compounds, and methods of treating cardiovascular conditions with them
JPH06107539A (ja)	1994-04-19	チロシナーゼ阻害剤
DE102005012875B4 (de)	2006-11-16	Verwendung von Amino substituierten 8-N-Benzimidazolen
JPS59184125A (ja)	1984-10-19	抗糸状菌剤
DE1906322A1 (de)	1969-09-25	Neue alpha-Alkyl-5-hydroxytryptophanester
US3088869A (en)	1963-05-07	Antiemetic compositions and methods of treating nausea and vomiting
CH641775A5 (fr)	1984-03-15	N-(1-methyl 2-pyrrolidinyl methyl) 2,3-dimethoxy 5-methylsulfamoyl benzamide et ses derives, son procede de preparation et composition le renferment.
CA1265520A (fr)	1990-02-06	Derives d'apovincaminol, procede de preparation et composes pharmaceutiques les contenant
AU608261B2 (en)	1991-03-28	Oleic acid esters
DE19833105A1 (de)	2000-01-27	Substituierte Phenylamidine, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung
US4254131A (en)	1981-03-03	Treatment of pain, fever, and inflammation with compositions containing 2-(substitutedpiperidinomethyl)propane and propene nitriles
US4847280A (en)	1989-07-11	Novel treatment