CA1069823A - Solution of a oxazepine for oral or parenteral administration - Google Patents
Solution of a oxazepine for oral or parenteral administrationInfo
- Publication number
- CA1069823A CA1069823A CA256,154A CA256154A CA1069823A CA 1069823 A CA1069823 A CA 1069823A CA 256154 A CA256154 A CA 256154A CA 1069823 A CA1069823 A CA 1069823A
- Authority
- CA
- Canada
- Prior art keywords
- oxazepine
- chloro
- solution
- dibenz
- methyl
- 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.)
- Expired
Links
- SFJGCXYXEFWEBK-UHFFFAOYSA-N oxazepine Chemical compound O1C=CC=CC=N1 SFJGCXYXEFWEBK-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 238000007911 parenteral administration Methods 0.000 title abstract description 4
- XJGVXQDUIWGIRW-UHFFFAOYSA-N loxapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2OC2=CC=C(Cl)C=C12 XJGVXQDUIWGIRW-UHFFFAOYSA-N 0.000 claims abstract description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 44
- 239000000243 solution Substances 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 8
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 claims description 7
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims description 7
- 229920000053 polysorbate 80 Polymers 0.000 claims description 7
- 229940068968 polysorbate 80 Drugs 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 1
- 239000012141 concentrate Substances 0.000 description 15
- 235000008504 concentrate Nutrition 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 239000002585 base Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 235000013305 food Nutrition 0.000 description 7
- 239000003182 parenteral nutrition solution Substances 0.000 description 7
- 241000700159 Rattus Species 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 239000008215 water for injection Substances 0.000 description 6
- -1 4-methyl-l-piperazinyl Chemical group 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- CJKPKVLFYAXEBS-UHFFFAOYSA-N 2,3,6,7-tetrahydrooxazepine Chemical compound C1CC=CCNO1 CJKPKVLFYAXEBS-UHFFFAOYSA-N 0.000 description 4
- 238000001647 drug administration Methods 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 231100000252 nontoxic Toxicity 0.000 description 3
- 230000003000 nontoxic effect Effects 0.000 description 3
- WXLCDTBTIVJDCE-UHFFFAOYSA-N 1,4-oxazepine Chemical compound O1C=CC=NC=C1 WXLCDTBTIVJDCE-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 208000009132 Catalepsy Diseases 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 206010047853 Waxy flexibility Diseases 0.000 description 2
- 235000013361 beverage Nutrition 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- WTEVQBCEXWBHNA-YFHOEESVSA-N neral Chemical compound CC(C)=CCC\C(C)=C/C=O WTEVQBCEXWBHNA-YFHOEESVSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 235000015205 orange juice Nutrition 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- ICBZSKCTKKUQSY-YUWZRIFDSA-N 4-[(1r,2s)-1-hydroxy-2-(methylamino)propyl]phenol;hydrochloride Chemical compound Cl.CN[C@@H](C)[C@H](O)C1=CC=C(O)C=C1 ICBZSKCTKKUQSY-YUWZRIFDSA-N 0.000 description 1
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 description 1
- 240000000560 Citrus x paradisi Species 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000003509 anti-fertility effect Effects 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 1
- 210000001124 body fluid Anatomy 0.000 description 1
- 239000010839 body fluid Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 229940116592 central nervous system diagnostic radiopharmaceuticals Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- WTEVQBCEXWBHNA-JXMROGBWSA-N citral A Natural products CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 235000015203 fruit juice Nutrition 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 235000015201 grapefruit juice Nutrition 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000008297 liquid dosage form Substances 0.000 description 1
- 235000021056 liquid food Nutrition 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 230000000701 neuroleptic effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 235000013997 pineapple juice Nutrition 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- General Health & Medical Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Dermatology (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60233175A | 1975-08-06 | 1975-08-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1069823A true CA1069823A (en) | 1980-01-15 |
Family
ID=24410918
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA256,154A Expired CA1069823A (en) | 1975-08-06 | 1976-07-02 | Solution of a oxazepine for oral or parenteral administration |
Country Status (19)
| Country | Link |
|---|---|
| JP (1) | JPS5221313A (en:Method) |
| AR (1) | AR210501A1 (en:Method) |
| AT (1) | AT345464B (en:Method) |
| AU (1) | AU500641B2 (en:Method) |
| BE (1) | BE844903A (en:Method) |
| CA (1) | CA1069823A (en:Method) |
| DE (1) | DE2633943A1 (en:Method) |
| DK (1) | DK147727C (en:Method) |
| EG (1) | EG12425A (en:Method) |
| ES (1) | ES450520A1 (en:Method) |
| FI (1) | FI762171A7 (en:Method) |
| FR (1) | FR2320102A1 (en:Method) |
| GB (1) | GB1546933A (en:Method) |
| IL (1) | IL49996A (en:Method) |
| NL (1) | NL7608575A (en:Method) |
| NO (1) | NO146457C (en:Method) |
| PT (1) | PT65400B (en:Method) |
| SE (1) | SE431716B (en:Method) |
| ZA (1) | ZA764052B (en:Method) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8404735B2 (en) | 2009-03-18 | 2013-03-26 | Omnipharm Limited | Parasiticidal formulation |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2739254B1 (fr) * | 1995-09-29 | 1997-12-19 | Rhone Merieux | Composition antiparasitaire pour le traitement et la protection des animaux de compagnie |
| FR2739255B1 (fr) * | 1995-09-29 | 1998-09-04 | Rhone Merieux | Composition antiparasitaire pour le traitement et la protection des animaux de compagnie |
| IE80657B1 (en) * | 1996-03-29 | 1998-11-04 | Merial Sas | Insecticidal combination to control mammal fleas in particular fleas on cats and dogs |
-
1976
- 1976-07-02 CA CA256,154A patent/CA1069823A/en not_active Expired
- 1976-07-07 ZA ZA764052A patent/ZA764052B/xx unknown
- 1976-07-08 IL IL49996A patent/IL49996A/xx unknown
- 1976-07-09 GB GB28752/76A patent/GB1546933A/en not_active Expired
- 1976-07-09 AU AU15775/76A patent/AU500641B2/en not_active Expired
- 1976-07-13 AR AR263933A patent/AR210501A1/es active
- 1976-07-22 PT PT65400A patent/PT65400B/pt unknown
- 1976-07-28 DE DE19762633943 patent/DE2633943A1/de not_active Withdrawn
- 1976-07-29 FI FI762171A patent/FI762171A7/fi not_active Application Discontinuation
- 1976-08-02 NL NL7608575A patent/NL7608575A/xx not_active Application Discontinuation
- 1976-08-04 EG EG475/76A patent/EG12425A/xx active
- 1976-08-05 SE SE7608810A patent/SE431716B/xx unknown
- 1976-08-05 AT AT581376A patent/AT345464B/de not_active IP Right Cessation
- 1976-08-05 FR FR7623990A patent/FR2320102A1/fr not_active Withdrawn
- 1976-08-05 DK DK354076A patent/DK147727C/da not_active IP Right Cessation
- 1976-08-05 NO NO762713A patent/NO146457C/no unknown
- 1976-08-05 BE BE169573A patent/BE844903A/xx not_active IP Right Cessation
- 1976-08-06 ES ES450520A patent/ES450520A1/es not_active Expired
- 1976-08-06 JP JP51093257A patent/JPS5221313A/ja active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8404735B2 (en) | 2009-03-18 | 2013-03-26 | Omnipharm Limited | Parasiticidal formulation |
| US8580837B2 (en) | 2009-03-18 | 2013-11-12 | Fidopharm, Inc. | Parasiticidal formulation |
| US8829038B2 (en) | 2009-03-18 | 2014-09-09 | Velcera, Inc. | Parasiticidal formulation |
Also Published As
| Publication number | Publication date |
|---|---|
| NO146457B (no) | 1982-06-28 |
| IL49996A0 (en) | 1976-09-30 |
| NO762713L (en:Method) | 1977-02-08 |
| AU1577576A (en) | 1978-01-12 |
| ZA764052B (en) | 1977-06-29 |
| DK354076A (da) | 1977-02-07 |
| PT65400B (en) | 1978-01-27 |
| DK147727C (da) | 1985-06-17 |
| BE844903A (fr) | 1977-02-07 |
| NO146457C (no) | 1982-10-06 |
| IL49996A (en) | 1981-01-30 |
| GB1546933A (en) | 1979-05-31 |
| DE2633943A1 (de) | 1977-02-17 |
| AR210501A1 (es) | 1977-08-15 |
| PT65400A (en) | 1976-08-01 |
| AU500641B2 (en) | 1979-05-31 |
| ES450520A1 (es) | 1978-05-01 |
| FR2320102A1 (fr) | 1977-03-04 |
| SE431716B (sv) | 1984-02-27 |
| EG12425A (en) | 1979-06-30 |
| JPS5221313A (en) | 1977-02-17 |
| SE7608810L (sv) | 1977-02-07 |
| AT345464B (de) | 1978-09-25 |
| DK147727B (da) | 1984-11-26 |
| ATA581376A (de) | 1978-01-15 |
| NL7608575A (nl) | 1977-02-08 |
| FI762171A7 (en:Method) | 1977-02-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |