CA1062159A - Sustained release forms of certain oxazepines for parenteral administration - Google Patents
Sustained release forms of certain oxazepines for parenteral administrationInfo
- Publication number
- CA1062159A CA1062159A CA255,781A CA255781A CA1062159A CA 1062159 A CA1062159 A CA 1062159A CA 255781 A CA255781 A CA 255781A CA 1062159 A CA1062159 A CA 1062159A
- Authority
- CA
- Canada
- Prior art keywords
- chloro
- dibenz
- piperazinyl
- oxazepine
- 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
- 238000007911 parenteral administration Methods 0.000 title abstract description 6
- 239000012730 sustained-release form Substances 0.000 title abstract description 6
- 150000000221 oxazepines Chemical class 0.000 title abstract 2
- 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 26
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- QWGDMFLQWFTERH-UHFFFAOYSA-N amoxapine Chemical compound C12=CC(Cl)=CC=C2OC2=CC=CC=C2N=C1N1CCNCC1 QWGDMFLQWFTERH-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000000203 mixture Substances 0.000 claims description 28
- 239000008159 sesame oil Substances 0.000 claims description 24
- 235000011803 sesame oil Nutrition 0.000 claims description 24
- 239000003921 oil Substances 0.000 claims description 13
- 235000019198 oils Nutrition 0.000 claims description 13
- 230000002035 prolonged effect Effects 0.000 claims description 8
- 230000000694 effects Effects 0.000 claims description 7
- SFJGCXYXEFWEBK-UHFFFAOYSA-N oxazepine Chemical compound O1C=CC=CC=N1 SFJGCXYXEFWEBK-UHFFFAOYSA-N 0.000 claims description 6
- 239000003349 gelling agent Substances 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 5
- 239000012458 free base Substances 0.000 abstract description 3
- 238000013268 sustained release Methods 0.000 abstract description 2
- 239000000725 suspension Substances 0.000 description 38
- 239000002585 base Substances 0.000 description 31
- 238000002360 preparation method Methods 0.000 description 16
- UGMCXQCYOVCMTB-UHFFFAOYSA-K dihydroxy(stearato)aluminium Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[Al](O)O UGMCXQCYOVCMTB-UHFFFAOYSA-K 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 14
- 238000009472 formulation Methods 0.000 description 13
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 10
- 238000013019 agitation Methods 0.000 description 7
- -1 enanthate ester Chemical class 0.000 description 7
- 239000000243 solution Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 235000019483 Peanut oil Nutrition 0.000 description 5
- 210000003169 central nervous system Anatomy 0.000 description 5
- 239000002285 corn oil Substances 0.000 description 5
- 235000005687 corn oil Nutrition 0.000 description 5
- 239000000312 peanut oil Substances 0.000 description 5
- 241000282472 Canis lupus familiaris Species 0.000 description 4
- LRWSFOSWNAQHHW-UHFFFAOYSA-N Fluphenazine enanthate Chemical compound C1CN(CCOC(=O)CCCCCC)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 LRWSFOSWNAQHHW-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical class CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000002385 cottonseed oil Substances 0.000 description 4
- 235000012343 cottonseed oil Nutrition 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 229960000787 fluphenazine enanthate Drugs 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
- 230000009974 thixotropic effect Effects 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000004570 mortar (masonry) Substances 0.000 description 3
- CJKPKVLFYAXEBS-UHFFFAOYSA-N 2,3,6,7-tetrahydrooxazepine Chemical compound C1CC=CCNO1 CJKPKVLFYAXEBS-UHFFFAOYSA-N 0.000 description 2
- 241000282693 Cercopithecidae Species 0.000 description 2
- PLDUPXSUYLZYBN-UHFFFAOYSA-N Fluphenazine Chemical compound C1CN(CCO)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 PLDUPXSUYLZYBN-UHFFFAOYSA-N 0.000 description 2
- 206010039897 Sedation Diseases 0.000 description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 150000004668 long chain fatty acids Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000003176 neuroleptic agent Substances 0.000 description 2
- 230000000701 neuroleptic effect Effects 0.000 description 2
- 150000002990 phenothiazines Chemical class 0.000 description 2
- 230000036280 sedation Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000001384 succinic acid Substances 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- WXLCDTBTIVJDCE-UHFFFAOYSA-N 1,4-oxazepine Chemical compound O1C=CC=NC=C1 WXLCDTBTIVJDCE-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 1
- 206010001488 Aggression Diseases 0.000 description 1
- 208000009132 Catalepsy Diseases 0.000 description 1
- 241000282668 Cebus Species 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 208000020401 Depressive disease Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 206010015995 Eyelid ptosis Diseases 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
- 241000124008 Mammalia Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 206010047853 Waxy flexibility Diseases 0.000 description 1
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
- 229940083916 aluminum distearate Drugs 0.000 description 1
- KMJRBSYFFVNPPK-UHFFFAOYSA-K aluminum;dodecanoate Chemical compound [Al+3].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O KMJRBSYFFVNPPK-UHFFFAOYSA-K 0.000 description 1
- RDIVANOKKPKCTO-UHFFFAOYSA-K aluminum;octadecanoate;hydroxide Chemical compound [OH-].[Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O RDIVANOKKPKCTO-UHFFFAOYSA-K 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 230000003474 anti-emetic effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 239000002111 antiemetic agent Substances 0.000 description 1
- 239000000164 antipsychotic agent Substances 0.000 description 1
- 239000002249 anxiolytic agent Substances 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
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000001914 calming effect Effects 0.000 description 1
- 239000003576 central nervous system agent Substances 0.000 description 1
- 229940125693 central nervous system agent Drugs 0.000 description 1
- 208000015114 central nervous system disease Diseases 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- NPUACKRELIJTFM-UHFFFAOYSA-N cr gas Chemical compound C1=NC2=CC=CC=C2OC2=CC=CC=C21 NPUACKRELIJTFM-UHFFFAOYSA-N 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229960002690 fluphenazine Drugs 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 229940105132 myristate Drugs 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical class CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000003182 parenteral nutrition solution Substances 0.000 description 1
- 229950000688 phenothiazine Drugs 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 201000003004 ptosis Diseases 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
- A61K47/12—Carboxylic acids; Salts or anhydrides thereof
-
- 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
- A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
-
- 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)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Dermatology (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/596,488 US4016273A (en) | 1975-07-16 | 1975-07-16 | Sustained release forms of certain oxazepines for parenteral administration |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1062159A true CA1062159A (en) | 1979-09-11 |
Family
ID=24387483
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA255,781A Expired CA1062159A (en) | 1975-07-16 | 1976-06-28 | Sustained release forms of certain oxazepines for parenteral administration |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4016273A (en:Method) |
| BE (1) | BE844203A (en:Method) |
| CA (1) | CA1062159A (en:Method) |
| DE (1) | DE2630394A1 (en:Method) |
| DK (1) | DK319776A (en:Method) |
| FI (1) | FI762053A7 (en:Method) |
| FR (1) | FR2317912A1 (en:Method) |
| GB (1) | GB1525425A (en:Method) |
| NL (1) | NL7607918A (en:Method) |
| PT (1) | PT65358B (en:Method) |
| SE (1) | SE7608114L (en:Method) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6617321B2 (en) * | 1997-09-30 | 2003-09-09 | Eli Lilly And Company | 2-methyl-thieno-benzodiazepine formulation |
| US6199634B1 (en) | 1998-08-27 | 2001-03-13 | Viatchelav Ivanovich Selyakov | Method and apparatus for controlling the permeability of mineral bearing earth formations |
| IL152360A0 (en) * | 2000-04-19 | 2003-05-29 | Genentech Inc | Sustained release formulations |
| WO2002013870A2 (en) * | 2000-08-17 | 2002-02-21 | Mitokor, Inc. | Formulation for administering therapeutic lipophilic molecules |
| DE10059020A1 (de) * | 2000-11-28 | 2002-05-29 | Gruenenthal Gmbh | Parenteral applizierbare Darreichungsformen |
| IL159048A0 (en) * | 2001-06-21 | 2004-05-12 | Genentech Inc | Sustained release formulation |
| US6972195B2 (en) * | 2002-09-27 | 2005-12-06 | Rongxiang Xu | Composition and method for culturing potentially regenerative cells and functional tissue-organs in vitro |
| CN1827766B (zh) * | 2001-06-28 | 2010-08-25 | 徐荣祥 | 体外细胞的培养方法 |
| US6685971B2 (en) * | 2001-06-28 | 2004-02-03 | Rongxiang Xu | Method and composition for repairing and promoting regeneration of mucosal tissue in the gastrointestinal tract |
| BRPI0418304A (pt) * | 2004-01-07 | 2007-05-02 | Trimeris Inc | peptìdeo sintético, uso do mesmo, composição farmacêutica, seqüência de nucleotìdeos, e, métodos para inibição da transmissão de hiv para uma célula, para inibição da fusão de hiv, e para tratamento de um indivìduo infectado com hiv |
| JP4940152B2 (ja) * | 2005-01-05 | 2012-05-30 | イーライ リリー アンド カンパニー | パモ酸オランザピン二水和物 |
| CN101415723B (zh) * | 2006-02-02 | 2014-06-25 | 特里梅里斯公司 | 具有改良生物学特性的hiv融合抑制肽 |
| ES2346005T3 (es) * | 2006-07-27 | 2010-10-07 | Cognis Ip Management Gmbh | Procedimiento para la obtencion de glicerina. |
| WO2008124013A1 (en) * | 2007-04-03 | 2008-10-16 | Trimeris, Inc. | Novel formulations for delivery of antiviral peptide therapeutics |
| JP2010540528A (ja) * | 2007-09-25 | 2010-12-24 | トリメリス，インコーポレーテッド | 治療的抗ウイルス性ペプチドの新規合成方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3116203A (en) * | 1962-03-14 | 1963-12-31 | Hoffmann La Roche | Oleaginous systems |
| US3164520A (en) * | 1962-10-29 | 1965-01-05 | Olin Mathieson | Injectable steroid compositions containing at least 75% benzyl benzoate |
| NL140242B (nl) * | 1963-03-01 | 1973-11-15 | Wander Ag Dr A | Werkwijze voor het bereiden van op de 11-plaats door een basische groep gesubstitueerde dibenz (b.f.)(1.4) oxazepinen. |
| US3538216A (en) * | 1964-02-20 | 1970-11-03 | Lab De Rech Physiques S A R L | Injectable compositions of a drug suspended in an emulsion |
| GB1192812A (en) * | 1966-05-20 | 1970-05-20 | American Cyanamid Co | 2-Chloro-11-(1-Piperazinyl)Dibenz[b,f]-[1,4]Oxazepine, Non-Toxic Acid Addition Salts thereof, and Therapeutic Compositions containing said Oxazepine or Salts |
| US3546220A (en) * | 1966-08-01 | 1970-12-08 | Abbott Lab | 2,3-dihydro-1h-pyrido-(2,3-b)(1,4)thiazines |
| US3549621A (en) * | 1968-04-29 | 1970-12-22 | Harry Louis Yale | 12-substituted-6h-dibenz(b,f)(1,4)oxazocin-11(12h) ones |
| US3891647A (en) * | 1970-08-06 | 1975-06-24 | Wander Ag Dr A | 2-trifluoromethyl-sulphonyl-11-substituted-piperazinyl-dibenz {8 b,f{9 {8 1,4{9 {0 oxazepine |
| US3773768A (en) * | 1970-10-26 | 1973-11-20 | American Cyanamid Co | 7-amino-2-chloro-11-(4-methyl-1-piperazinyl)dibenz(b,f)(1,4)oxazepine and salts thereof |
-
1975
- 1975-07-16 US US05/596,488 patent/US4016273A/en not_active Expired - Lifetime
-
1976
- 1976-06-28 CA CA255,781A patent/CA1062159A/en not_active Expired
- 1976-06-28 GB GB26914/76A patent/GB1525425A/en not_active Expired
- 1976-07-06 DE DE19762630394 patent/DE2630394A1/de not_active Withdrawn
- 1976-07-12 PT PT65358A patent/PT65358B/pt unknown
- 1976-07-15 FI FI762053A patent/FI762053A7/fi not_active Application Discontinuation
- 1976-07-15 SE SE7608114A patent/SE7608114L/xx not_active Application Discontinuation
- 1976-07-15 DK DK319776A patent/DK319776A/da not_active Application Discontinuation
- 1976-07-16 NL NL7607918A patent/NL7607918A/xx not_active Application Discontinuation
- 1976-07-16 BE BE168963A patent/BE844203A/xx unknown
- 1976-07-16 FR FR7621862A patent/FR2317912A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| US4016273A (en) | 1977-04-05 |
| NL7607918A (nl) | 1977-01-18 |
| PT65358A (en) | 1976-08-01 |
| GB1525425A (en) | 1978-09-20 |
| BE844203A (fr) | 1977-01-17 |
| SE7608114L (sv) | 1977-01-17 |
| FI762053A7 (en:Method) | 1977-01-17 |
| DK319776A (da) | 1977-01-17 |
| FR2317912A1 (fr) | 1977-02-11 |
| DE2630394A1 (de) | 1977-02-03 |
| FR2317912B1 (en:Method) | 1979-04-13 |
| PT65358B (en) | 1978-01-09 |
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