WO1998054186A1 - Salts of aromatic sulphonic acids - Google Patents
Salts of aromatic sulphonic acids Download PDFInfo
- Publication number
- WO1998054186A1 WO1998054186A1 PCT/EP1998/003022 EP9803022W WO9854186A1 WO 1998054186 A1 WO1998054186 A1 WO 1998054186A1 EP 9803022 W EP9803022 W EP 9803022W WO 9854186 A1 WO9854186 A1 WO 9854186A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- salt
- aromatic
- methyl
- oxepino
- dibenz
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- 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
-
- 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
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Definitions
- the invention pertains to a salt of the compound trans-5-chloro-2,3,3a, 12b-tetrahydro-2- methyl-lH-dibenz[2,3 :6,7]oxepino[4,5-c]pyrrole and a salt forming agent.
- the compound is described as having CNS-depressant activity and antihistamine and antiserotonin activities.
- Org 5222 which is trans-5-chloro-2,3,3aJ2b-tetrahydro-2-methyl-lH- dibenz[2,3:6,7]oxepino[4,5-c]pyrrole(Z)-2-butenedio :e (1 : 1), is a very potent dopamine and serotonin antagonist and antihistaminic with potential antipsychotic activity.
- the compound is crystalline (otherwise the compound will be metastable, due to which it cannot be predicted what, at a certain point in time, the amount of biologically desired compound is) and that it has a low solubility in water.
- the latter is important for attaining the required sustained release.
- the maleate, (the (Z)-2-butenedioate Org 5222), which is crystalline, has a solubility of 3 mg/ml (21°C) which means that also higher doses, intended for controlled sustained release, will be taken up in the patient's blood immediately.
- the free base (Org 33254) has ' a relatively low solubility of less then 0.1 mg/ml, but is instable.
- the pamoate (Org 33388) is amorphous
- the hemipamoate (Org 39058) is a mixture of amorphous and crystalline material.
- the melting point is not too low (preferably above 80°C), as this may lead to temperature-induced problems when making tablets or granules.
- Salt-forming agents are therefore generally chosen empirically, and also in later literature, e.g. International Journal of Pharmaceutics, 33 (1986) 201-217, it has been recognized that, notably for properties such as hygroscopicity, stability and solubility, it is difficult to select the salt forming agent beforehand.
- the salt-forming agent selected is an aromatic sulphonic acid.
- aromatic sulphonic acid any pharmaceutically acceptable aromatic sulphonic acid is suitable, some aromatic moieties are clearly preferred.
- the aromatic moiety may advantageously be of the type having a single phenyl ring.
- Preferred acids of this type being benzene sulphonic acid and toluene sulphonic acid
- the preferred salts of the invention are the besylate and the tosylate.
- the besylate is the preferred salt of the invention, but naphthalene sulphonic acid is also a suitable candidate for the acid, resulting in the corresponding napsylate.
- the most preferred salt of the invention is the besylate.
- the salts of the present invention can be prepared analogously to those described in US 4, 145,434.
- a suitable solvent such as ethanol
- a solution of the appropriate aromatic sulphonic acid preferably in the same solvent or in a solvent miscible with the solvent for said compound.
- the mixture then can be allowed to stand for sufficient time to let the corresponding salt according to the invention crystallize (which occurs spontaneously). If desired the obtained crystals can further undergo conventional washing and drying and/or purifying steps, e.g. simple recrystallization followed by drying.
- compositions of the invention are useful in treating mammals, including humans, suffering from all diseases susceptible to treatment by trans- 5-chloro-2J,3aJ2b-tetrahydro-2-methyl-lH-dibenz[2J :6,7]oxepino[4,5-c]pyrrole.
- diseases include mental disorders, such as tension, excitation, anxiety, psychosis, and schizophrenia.
- the compositions may also be used for antidopamine, antihistamine and for antiserotonin related diseases.
- the salts of the present invention have a utility as a medicine per se, and they may be administered in any form, although, as described in WO 95/23600, peroral administration may lead to cardiotoxic side-effects.
- peroral administration may lead to cardiotoxic side-effects.
- other forms of administration are preferred, e.g. subcutaneous administration, injection, or by means of sublingual or buccal pharmaceutical composition as described in WO 95/23600.
- All of these single dosage forms of pharmaceutical compositions containing the salt of the present invention comprise one dosage unit of trans-5-chloro-2,3,3a, 12b-tetrahydro-2- methyl-lH-dibenz[2,3:6,7]oxepino[4,5-c]pyrrole as an active ingredient.
- a dosage unit may contain between 0.005 mg and 15 mg of the active ingredient.
- the dosage unit contains of from about 0.03 to 0.50 mg of trans-5-chloro-2,3,3a, 12b-tetrahydro-2- methyl-lH-dibenz[2,3:6,7]oxepino[4,5-c]pyrrole.
- Any suitable, pharmaceutically acceptable carrier material may be applied, and pharmaceutically acceptable auxiliaries be added. All of these pharmaceutically acceptable excipients such as carriers and auxiliaries are known to the person skilled in the art and do not require elucidation here.
- the salt be administered by means of a depot injection, i.e. at a dose higher than that in a single dosage form.
- Typical doses for such preparations comprise 10 to 40 mg of the active ingredient.
- the depot preparations of the present invention in its simplest form may comprise water as a carrier, the low aqueous solubility of the salt of course making it preferable for it to be dispersed rather than dissolved.
- conventional adjuvants may be used, e.g. Tween (surfactant), propylene glycol, lecithin, etc.
- Other pharmaceutically acceptable carriers are also suitable, e.g.
- Example 2 The procedure of Example 1 was repeated, employing a great many different acids, all known for their suitability as a salt-forming agent for a pharmacon. The results attained are given in the following table:
- aromatic sulphonates of the invention form an exception in combining the desired properties of being crystalline, having a high melting point and displaying such a low solubility in water as to be held water-insoluble.
- Example II The procedure of Example I was repeated, substituting toluene-4-sulphonic acid for benzene sulphonic acid. Thus the corresponding toluene sulphonate (tosylate) was obtained.
- Example II The procedure of Example I was repeated, substituting naphthalene- 1 -sulphonic acid and naphthalene-2-sulphonic acid for benzene sulphonic acid. Thus the corresponding naphthalene sulphonates (napsylates) were obtained.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP50020299A JP2001526702A (ja) | 1997-05-26 | 1998-05-19 | 芳香族スルホン酸の塩類 |
CA002290070A CA2290070A1 (en) | 1997-05-26 | 1998-05-19 | Salts of aromatic sulphonic acids |
HU0002106A HUP0002106A3 (en) | 1997-05-26 | 1998-05-19 | Aromatic sulfonates of trans-5-chloro-2,3,3a,12b-tetrahydro-2-methyl-1h-dibenz-[2,3:6,7]oxepino[4,5-c]pyrrole and pharmaceutical compositions containing it |
AU77675/98A AU7767598A (en) | 1997-05-26 | 1998-05-19 | Salts of aromatic sulphonic acids |
KR1019997010957A KR20010012985A (ko) | 1997-05-26 | 1998-05-19 | 방향족 술폰산의 염 |
PL98337027A PL337027A1 (en) | 1997-05-26 | 1998-05-19 | Salts of aromatic sulphonic acids |
BR9809162-0A BR9809162A (pt) | 1997-05-26 | 1998-05-19 | Sal de trans-5-cloro-2, 3, 3a, 12b-tetrahidro-2-metil-1h-dibenz [2,3:6,7] oxepino[4,5-c] pirrol e agente formador de sal, composto, composição farmacêutica, e, preparação de injeção armazenável |
EP98925632A EP0984968A1 (en) | 1997-05-26 | 1998-05-19 | Salts of aromatic sulphonic acids |
NO995770A NO995770D0 (no) | 1997-05-26 | 1999-11-25 | Salter av aromatiske sulfonsyrer |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP97201596.0 | 1997-05-26 | ||
EP97201596 | 1997-05-26 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1998054186A1 true WO1998054186A1 (en) | 1998-12-03 |
Family
ID=8228372
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1998/003022 WO1998054186A1 (en) | 1997-05-26 | 1998-05-19 | Salts of aromatic sulphonic acids |
Country Status (12)
Country | Link |
---|---|
EP (1) | EP0984968A1 (pt) |
JP (1) | JP2001526702A (pt) |
KR (1) | KR20010012985A (pt) |
CN (1) | CN1257504A (pt) |
AU (1) | AU7767598A (pt) |
BR (1) | BR9809162A (pt) |
CA (1) | CA2290070A1 (pt) |
HU (1) | HUP0002106A3 (pt) |
NO (1) | NO995770D0 (pt) |
PL (1) | PL337027A1 (pt) |
TR (1) | TR199902727T2 (pt) |
WO (1) | WO1998054186A1 (pt) |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7312203B2 (en) | 2002-05-21 | 2007-12-25 | GlaxoSmithKline istraziva{hacek over (c)}ki Centar Zagreb d.o.o. | 1-aza-dibenzoazulenes as inhibitors of tumour necrosis factor production and intermediates for the preparation thereof |
US7550498B2 (en) | 2002-05-23 | 2009-06-23 | Glaxosmithkline Istrazivacki Centar Zagreb D.O.O. | 1,2-Diaza-dibenzoazulenes as inhibitors of tumour necrosis factor production and intermediates for the preparation thereof |
WO2010149727A2 (en) | 2009-06-24 | 2010-12-29 | N.V. Organon | Injectable formulations containing asenapine and method of treatment using same |
JP2011016849A (ja) * | 2002-07-15 | 2011-01-27 | Novartis Ag | イロペリドンの結晶を含有する注射用デポ製剤 |
WO2012150538A1 (en) | 2011-05-02 | 2012-11-08 | Olon Spa | Crystalline salts of asenapine |
EP2524921A1 (en) | 2011-05-17 | 2012-11-21 | Sandoz AG | Novel Crystalline Salts of Asenapine |
EP2524920A1 (en) | 2011-05-17 | 2012-11-21 | Sandoz AG | Novel Crystalline Asenapine Hydrochloride Salt Forms |
EP2524919A1 (en) | 2011-05-17 | 2012-11-21 | Sandoz AG | Novel crystalline salts of Asenapine with organic Di-acids and Tri-acids |
US8815293B2 (en) | 2001-10-30 | 2014-08-26 | Novartis Ag | Organic compounds |
US10898449B2 (en) | 2016-12-20 | 2021-01-26 | Lts Lohmann Therapie-Systeme Ag | Transdermal therapeutic system containing asenapine |
US11033512B2 (en) | 2017-06-26 | 2021-06-15 | Lts Lohmann Therapie-Systeme Ag | Transdermal therapeutic system containing asenapine and silicone acrylic hybrid polymer |
US11337932B2 (en) | 2016-12-20 | 2022-05-24 | Lts Lohmann Therapie-Systeme Ag | Transdermal therapeutic system containing asenapine and polysiloxane or polyisobutylene |
US11648213B2 (en) | 2018-06-20 | 2023-05-16 | Lts Lohmann Therapie-Systeme Ag | Transdermal therapeutic system containing asenapine |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1802301A1 (en) * | 2004-10-15 | 2007-07-04 | Pfizer Inc. | Treatment of bipolar disorders and associated symptoms |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4145434A (en) * | 1976-05-24 | 1979-03-20 | Akzona Incorporated | Tetracyclic derivatives and pharmaceutical compositions of matter |
-
1998
- 1998-05-19 HU HU0002106A patent/HUP0002106A3/hu unknown
- 1998-05-19 WO PCT/EP1998/003022 patent/WO1998054186A1/en not_active Application Discontinuation
- 1998-05-19 EP EP98925632A patent/EP0984968A1/en not_active Withdrawn
- 1998-05-19 KR KR1019997010957A patent/KR20010012985A/ko not_active Application Discontinuation
- 1998-05-19 BR BR9809162-0A patent/BR9809162A/pt not_active Application Discontinuation
- 1998-05-19 PL PL98337027A patent/PL337027A1/xx unknown
- 1998-05-19 AU AU77675/98A patent/AU7767598A/en not_active Abandoned
- 1998-05-19 JP JP50020299A patent/JP2001526702A/ja active Pending
- 1998-05-19 CA CA002290070A patent/CA2290070A1/en not_active Abandoned
- 1998-05-19 TR TR1999/02727T patent/TR199902727T2/xx unknown
- 1998-05-19 CN CN98805420A patent/CN1257504A/zh active Pending
-
1999
- 1999-11-25 NO NO995770A patent/NO995770D0/no not_active Application Discontinuation
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4145434A (en) * | 1976-05-24 | 1979-03-20 | Akzona Incorporated | Tetracyclic derivatives and pharmaceutical compositions of matter |
Cited By (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8815293B2 (en) | 2001-10-30 | 2014-08-26 | Novartis Ag | Organic compounds |
US7312203B2 (en) | 2002-05-21 | 2007-12-25 | GlaxoSmithKline istraziva{hacek over (c)}ki Centar Zagreb d.o.o. | 1-aza-dibenzoazulenes as inhibitors of tumour necrosis factor production and intermediates for the preparation thereof |
US7550498B2 (en) | 2002-05-23 | 2009-06-23 | Glaxosmithkline Istrazivacki Centar Zagreb D.O.O. | 1,2-Diaza-dibenzoazulenes as inhibitors of tumour necrosis factor production and intermediates for the preparation thereof |
US8293765B2 (en) | 2002-07-15 | 2012-10-23 | Novartis Ag | Injectable depot formulation comprising crystals of iloperidone |
JP2011016849A (ja) * | 2002-07-15 | 2011-01-27 | Novartis Ag | イロペリドンの結晶を含有する注射用デポ製剤 |
US8614232B2 (en) | 2002-07-15 | 2013-12-24 | Novartis Ag | Injectable depot formulation comprising crystals of iloperidone |
US8227488B2 (en) | 2002-07-15 | 2012-07-24 | Novartis Ag | Injectable depot formulation comprising crystals of iloperidone |
CN102596172A (zh) * | 2009-06-24 | 2012-07-18 | Msd欧斯股份有限公司 | 含有阿塞那平的注射剂和使用其的治疗方法 |
WO2010149727A3 (en) * | 2009-06-24 | 2011-04-21 | N.V. Organon | Injectable formulations containing asenapine and method of treatment using same |
WO2010149727A2 (en) | 2009-06-24 | 2010-12-29 | N.V. Organon | Injectable formulations containing asenapine and method of treatment using same |
US8658687B2 (en) | 2009-06-24 | 2014-02-25 | Merck Sharp & Dohme Corp. | Injectable formulations containing asenapine and method of treatment using same |
WO2012150538A1 (en) | 2011-05-02 | 2012-11-08 | Olon Spa | Crystalline salts of asenapine |
EP2524919A1 (en) | 2011-05-17 | 2012-11-21 | Sandoz AG | Novel crystalline salts of Asenapine with organic Di-acids and Tri-acids |
WO2012156384A1 (en) | 2011-05-17 | 2012-11-22 | Sandoz Ag | Novel crystalline salts of asenapine |
WO2012156382A1 (en) | 2011-05-17 | 2012-11-22 | Sandoz Ag | Novel crystalline asenapine hydrochloride salt forms |
WO2012156383A1 (en) | 2011-05-17 | 2012-11-22 | Sandoz Ag | Novel crystalline salts of asenapine with organic di-acids and tri-acids |
EP2524920A1 (en) | 2011-05-17 | 2012-11-21 | Sandoz AG | Novel Crystalline Asenapine Hydrochloride Salt Forms |
EP2524921A1 (en) | 2011-05-17 | 2012-11-21 | Sandoz AG | Novel Crystalline Salts of Asenapine |
US10898449B2 (en) | 2016-12-20 | 2021-01-26 | Lts Lohmann Therapie-Systeme Ag | Transdermal therapeutic system containing asenapine |
US10980753B2 (en) | 2016-12-20 | 2021-04-20 | Lts Lohmann Therapie-Systeme Ag | Transdermal therapeutic system containing asenapine |
US11337932B2 (en) | 2016-12-20 | 2022-05-24 | Lts Lohmann Therapie-Systeme Ag | Transdermal therapeutic system containing asenapine and polysiloxane or polyisobutylene |
US11033512B2 (en) | 2017-06-26 | 2021-06-15 | Lts Lohmann Therapie-Systeme Ag | Transdermal therapeutic system containing asenapine and silicone acrylic hybrid polymer |
US11648213B2 (en) | 2018-06-20 | 2023-05-16 | Lts Lohmann Therapie-Systeme Ag | Transdermal therapeutic system containing asenapine |
Also Published As
Publication number | Publication date |
---|---|
BR9809162A (pt) | 2000-08-01 |
AU7767598A (en) | 1998-12-30 |
NO995770L (no) | 1999-11-25 |
HUP0002106A3 (en) | 2001-11-28 |
PL337027A1 (en) | 2000-07-31 |
JP2001526702A (ja) | 2001-12-18 |
CN1257504A (zh) | 2000-06-21 |
TR199902727T2 (xx) | 2000-07-21 |
NO995770D0 (no) | 1999-11-25 |
HUP0002106A2 (hu) | 2000-11-28 |
EP0984968A1 (en) | 2000-03-15 |
CA2290070A1 (en) | 1998-12-03 |
KR20010012985A (ko) | 2001-02-26 |
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