WO2000056323A1 - Treatment of certain cancers associated with weight gain - Google Patents
Treatment of certain cancers associated with weight gain Download PDFInfo
- Publication number
- WO2000056323A1 WO2000056323A1 PCT/US2000/007361 US0007361W WO0056323A1 WO 2000056323 A1 WO2000056323 A1 WO 2000056323A1 US 0007361 W US0007361 W US 0007361W WO 0056323 A1 WO0056323 A1 WO 0056323A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- compound
- formula
- cyclobutyl
- chlorophenyl
- cancer
- Prior art date
Links
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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
-
- 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Definitions
- This invention relates to a method of treating certain cancers associated with weight gain.
- R, and R 2 are independently H or methyl, is administered in conjunction with a pharmaceutically acceptable diluent or carrier to a human in need thereof.
- Cancers which may advantageously be treated with a compound of formula I include colon cancer, breast cancer, endometrial cancer and gallbladder cancer.
- a preferred compound of formula I is N,N-dimethyl-1-[1-(4- chlorophenyl)cyclobutyl]-3-methylbutylamine or a salt thereof, for example the hydrochloride salt.
- a preferred form of this hydrochloride is its monohydrate.
- N,N-dimethyl-1-[1-(4-chlorophenyl)cyclobutyl]-3- methylbutylamine hydrochloride in the treatment of obesity is described in published PCT application WO90/06110.
- a particularly preferred form of this compound is N, N-dimethyl-1 -[1 -(4-chlorophenyl)cyclobutyl]-3-methylbutylamine hydrochloride monohydrate (sibutramine hydrochloride) which is described in European Patent Number 230742.
- N, N-dimethyl-1 -[1 -(4- chlorophenyl)cyclobutyl]-3-methyibutylamine and salts thereof for improving the glucose tolerance of humans having Impaired Glucose Tolerance or Non-Insulin Dependent Diabetes Mellitus is described in published PCT application WO95/20949.
- I contain a chiral centre.
- a compound of formula I may exist in two enantiomeric forms.
- the present invention includes the use of the individual enantiomers and mixtures of the enantiomers.
- the enantiomers may be resolved by methods known to those skilled in the art, for example by formation of diastereoisomeric salts or complexes which may be separated, for example, by crystallisation; via formation of diastereoisomeric derivatives which may be separated, for example, by crystallisation, gas-liquid or liquid chromatography; selective reaction of one enantiomer with an enantiomer- specific reagent, for example enzymatic oxidation or reduction, followed by separation of the modified and unmodified enantiomers; or gas-liquid or liquid chromatography in a chiral environment, for example on a chiral support, for example silica with a bound chiral ligand or in the presence of a chiral solvent.
- enantiomers may be synthesised by asymmetric synthesis using optically active reagents, substrates, catalysts or solvents, or by converting one enantiomer to the other by asymmetric transformation.
- Preferred compounds of formula I are N, ⁇ dimethyl-1-[1-(4-chlorophenyl)- cyclobutyl]-3-methylbutylamine, N- ⁇ 1-[1-(4-chlorophenyl)cyciobutyl]-3- methylbutyl ⁇ -N- methylamine, and 1-[1-(4-chlorophenyl)cyclobutyl]-3- methylbutylamine including racemates, individual enantiomers and mixtures thereof, and pharmaceutically acceptable salts thereof.
- the individual enantiomers can be prepared by enantioselective synthesis from optically active precursors, or by resolving the racemic compound which can be prepared as described above.
- Enantiomers of secondary amines of the formula I can also be prepared by preparing the racemate of the corresponding primary amine, resolving the latter into the individual enantiomers, and then converting the optically pure primary amine enantiomer into the required secondary amine by methods described in British Patent Specification 2098602.
- hydrochloride salts are preferred in each case, but the free bases and other pharmaceutically acceptable salts are also suitable.
- the compound of formula I may be administered in any of the known pharmaceutical dosage forms.
- the amount of the compound to be administered will depend on a number of factors including the age of the patient, the severity of the condition and the past medical history of the patient and always lies within the sound discretion of the administering physician but it is generally envisaged that the dosage of the compound to be administered will be in the range 0.1 to 50 mg preferably 1 to 30 mg per day given in one or more doses.
- Oral dosage forms are the preferred compositions for use in the present invention and these are the known pharmaceutical forms for such administration, for example tablets, capsules, granules, syrups and aqueous or oil suspensions.
- the excipients used in the preparation of these compositions are the excipients known in the pharmacist's art.
- Tablets may be prepared from a mixture of the active compound with fillers, for example calcium phosphate; disintegrating agents, for example maize starch; lubricating agents, for example magnesium stearate; binders, for example microcrystaliine cellulose or polyvinylpyrroiidone and other optional ingredients known in the art to permit tableting the mixture by known methods.
- the tablets may, if desired, be coated using known methods and excipients which may include enteric coating using for example hydroxypropylmethylcellulose phthalate.
- the tablets may be formulated in a manner known to those skilled in the art so as to give a sustained release of the compounds of the present invention.
- Such tablets may, if desired, be provided with enteric coatings by known methods, for example by the use of cellulose acetate phthalate.
- capsules for example hard or soft gelatin capsules, containing the active compound with or without added excipients, may be prepared by known methods and, if desired, provided with enteric coatings in a known manner.
- the contents of the capsule may be formulated using known methods so as to give sustained release of the active compound.
- the tablets and capsules may conveniently each contain 1 to 50 mg of the active compound.
- dosage forms for oral administration include, for example, aqueous suspensions containing the active compound in an aqueous medium in the presence of a non-toxic suspending agent such as sodium carboxy- methylcellulose, and oily suspensions containing a compound of the present invention in a suitable vegetable oil, for example arachis oil.
- the active compound may be formulated into granules with or without additional excipients.
- the granules may be ingested directly by the patient or they may be added to a suitable liquid carrier (for example, water) before ingestion.
- the granules may contain disintegrants, eg an effervescent couple formed from an acid and a carbonate or bicarbonate salt to facilitate dispersion in the liquid medium.
- the therapeutically active compounds of formula I may be formulated into a composition which the patient retains in his mouth so that the active compound is administered through the mucosa of the mouth.
- Dosage forms suitable for rectal administration are the known pharmaceutical forms for such administration, for example, suppositories with cocoa butter or polyethylene glycol bases.
- Dosage forms suitable for parenteral administration are the known pharmaceutical forms for such administration, for example sterile suspensions or sterile solutions in a suitable solvent.
- Dosage forms for topical administration may comprise a matrix in which the pharmacologically active compounds of the present invention are dispersed so that the compounds are held in contact with the skin in order to administer the compounds transdermally.
- a suitable transdermal composition may be prepared by mixing the pharmaceutically active compound with a topical vehicle, such as a mineral oil, petrolatum and/or a wax, e.g. paraffin wax or beeswax, together with a potential transdermal accelerant such as dimethyl sulphoxide or propylene glycol.
- the active compounds may be dispersed in a pharmaceutically acceptable cream, gel or ointment base.
- the amount of active compound contained in a topical formulation should be such that a therapeutically effective amount of the compound is delivered during the period of time for which the topical formulation is intended to be on the skin.
- the therapeutically active compound of formula I may be formulated into a composition which is dispersed as an aerosol into the patients oral or nasal cavity.
- Such aerosols may be administered from a pump pack or from a pressurised pack containing a volatile propellant.
- the therapeutically active compounds of formula I used in the method of the present invention may also be administered by continuous infusion either from an external source, for example by intravenous infusion or from a source of the compound placed within the body.
- Internal sources include implanted reservoirs containing the compound to be infused which is continuously released for example by osmosis and implants which may be (a) liquid such as an oily suspension of the compound to be infused for example in the form of a very sparingly water-soluble derivative such as a dodecanoate salt or a lipophilic ester or (b) solid in the form of an implanted support, for example of a synthetic resin or waxy material, for the compound to be infused.
- the support may be a single body containing all the compound or a series of several bodies each containing part of the compound to be delivered.
- the amount of active compound present in an internal source should be such that a therapeutically effective amount of the compound is delivered over a long period of time.
- the active compound may, if desired, be associated with other compatible pharmacologically active ingredients.
- the invention further provides the use of compounds of formula I in the manufacture of a medicament for treating certain cancers associated with obesity, for example colon cancer, breast cancer, endometrial cancer and gallbladder cancer.
- the invention further provides a pharmaceutical composition for treating colon cancer, breast cancer, endometrial cancer and gallbladder cancer, comprising a compound of formula I in conjunction with a pharmaceutically acceptable diluent or carrier.
- Monoamine reuptake inhibitors have been used to treat certain of the disorders described in the present invention.
- these compounds are known to suffer from a number of disadvantages. Firstly such compounds are not effective in all patients. Secondly where the compounds are effective they may not provide a complete cure of the disorder. Thirdly, there are many undesirable side-effects known with this type of compound. Such side-effects include nausea, sexual dysfunction, light headedness, somnolence, sweating, tremor, dry mouth, asthenia, insomnia, diarrhoea, headache, vomiting, anxiety, drowsiness, dizziness, fever, rash or allergic reactions, arthraigia, myalgia, convulsions, hypomania and mania.
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- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Emergency Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Gastroenterology & Hepatology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (12)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BR0009161-8A BR0009161A (pt) | 1999-03-19 | 2000-03-17 | Tratamento de certos cânceres associados a ganho de peso |
SK1337-2001A SK13372001A3 (sk) | 1999-03-19 | 2000-03-17 | Použitie zlúčeniny a farmaceutická kompozícia ju obsahujúca |
EP00915015A EP1171106A1 (en) | 1999-03-19 | 2000-03-17 | Treatment of certain cancers associated with weight gain |
KR1020017011855A KR20010113765A (ko) | 1999-03-19 | 2000-03-17 | 체중 증가와 관련된 특정 암의 치료방법 |
AU36320/00A AU3632000A (en) | 1999-03-19 | 2000-03-17 | Treatment of certain cancers associated with weight gain |
MXPA01009470A MXPA01009470A (es) | 1999-03-19 | 2000-03-17 | Tratamiento de ciertos canceres asociados con el aumento de peso. |
CA002367045A CA2367045A1 (en) | 1999-03-19 | 2000-03-17 | Treatment of certain cancers associated with weight gain |
PL00351958A PL351958A1 (en) | 1999-03-19 | 2000-03-17 | Treatment of some tumours associated with gain in weight |
JP2000606228A JP2002539255A (ja) | 1999-03-19 | 2000-03-17 | 体重増加に関係する癌の治療 |
IL14523900A IL145239A0 (en) | 1999-03-19 | 2000-03-17 | Treatment of certain cancers associated with weight gain |
NO20014478A NO20014478L (no) | 1999-03-19 | 2001-09-14 | Behandling av visse kreftformer forbundet med vektökning |
BG105998A BG105998A (en) | 1999-03-19 | 2001-10-10 | Treatment of certain cancers associated with weight gain |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US12525099P | 1999-03-19 | 1999-03-19 | |
US60/125,250 | 1999-03-19 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2000056323A1 true WO2000056323A1 (en) | 2000-09-28 |
Family
ID=22418838
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2000/007361 WO2000056323A1 (en) | 1999-03-19 | 2000-03-17 | Treatment of certain cancers associated with weight gain |
Country Status (19)
Country | Link |
---|---|
EP (1) | EP1171106A1 (ko) |
JP (1) | JP2002539255A (ko) |
KR (1) | KR20010113765A (ko) |
CN (1) | CN1399545A (ko) |
AU (1) | AU3632000A (ko) |
BG (1) | BG105998A (ko) |
BR (1) | BR0009161A (ko) |
CA (1) | CA2367045A1 (ko) |
CZ (1) | CZ20013281A3 (ko) |
HU (1) | HUP0200497A2 (ko) |
IL (1) | IL145239A0 (ko) |
MX (1) | MXPA01009470A (ko) |
NO (1) | NO20014478L (ko) |
NZ (1) | NZ514012A (ko) |
PL (1) | PL351958A1 (ko) |
SK (1) | SK13372001A3 (ko) |
TR (1) | TR200102692T2 (ko) |
WO (1) | WO2000056323A1 (ko) |
ZA (1) | ZA200107687B (ko) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004096202A1 (en) * | 2003-04-28 | 2004-11-11 | Cipla Limited | Pharmaceutical formulation comprising anti-obesity agent and acidulant |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5068440A (en) * | 1985-12-17 | 1991-11-26 | Boots Company, Plc | Process for the manufacture of N,N-dimethyl-1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutylamine hydrochloride monohydrate |
US5459164A (en) * | 1994-02-03 | 1995-10-17 | Boots Pharmaceuticals, Inc. | Medical treatment |
-
2000
- 2000-03-17 AU AU36320/00A patent/AU3632000A/en not_active Abandoned
- 2000-03-17 KR KR1020017011855A patent/KR20010113765A/ko not_active Application Discontinuation
- 2000-03-17 TR TR2001/02692T patent/TR200102692T2/xx unknown
- 2000-03-17 BR BR0009161-8A patent/BR0009161A/pt not_active Application Discontinuation
- 2000-03-17 HU HU0200497A patent/HUP0200497A2/hu unknown
- 2000-03-17 WO PCT/US2000/007361 patent/WO2000056323A1/en not_active Application Discontinuation
- 2000-03-17 IL IL14523900A patent/IL145239A0/xx unknown
- 2000-03-17 CZ CZ20013281A patent/CZ20013281A3/cs unknown
- 2000-03-17 PL PL00351958A patent/PL351958A1/xx not_active Application Discontinuation
- 2000-03-17 CN CN00807533A patent/CN1399545A/zh active Pending
- 2000-03-17 SK SK1337-2001A patent/SK13372001A3/sk unknown
- 2000-03-17 MX MXPA01009470A patent/MXPA01009470A/es unknown
- 2000-03-17 JP JP2000606228A patent/JP2002539255A/ja not_active Withdrawn
- 2000-03-17 NZ NZ514012A patent/NZ514012A/xx not_active Application Discontinuation
- 2000-03-17 CA CA002367045A patent/CA2367045A1/en not_active Abandoned
- 2000-03-17 EP EP00915015A patent/EP1171106A1/en not_active Withdrawn
-
2001
- 2001-09-14 NO NO20014478A patent/NO20014478L/no unknown
- 2001-09-18 ZA ZA200107687A patent/ZA200107687B/en unknown
- 2001-10-10 BG BG105998A patent/BG105998A/xx unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5068440A (en) * | 1985-12-17 | 1991-11-26 | Boots Company, Plc | Process for the manufacture of N,N-dimethyl-1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutylamine hydrochloride monohydrate |
US5459164A (en) * | 1994-02-03 | 1995-10-17 | Boots Pharmaceuticals, Inc. | Medical treatment |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004096202A1 (en) * | 2003-04-28 | 2004-11-11 | Cipla Limited | Pharmaceutical formulation comprising anti-obesity agent and acidulant |
Also Published As
Publication number | Publication date |
---|---|
TR200102692T2 (tr) | 2002-03-21 |
EP1171106A1 (en) | 2002-01-16 |
NZ514012A (en) | 2001-09-28 |
BG105998A (en) | 2002-06-28 |
CN1399545A (zh) | 2003-02-26 |
PL351958A1 (en) | 2003-07-14 |
CA2367045A1 (en) | 2000-09-28 |
JP2002539255A (ja) | 2002-11-19 |
IL145239A0 (en) | 2002-06-30 |
SK13372001A3 (sk) | 2002-07-02 |
KR20010113765A (ko) | 2001-12-28 |
NO20014478L (no) | 2001-10-29 |
NO20014478D0 (no) | 2001-09-14 |
CZ20013281A3 (cs) | 2002-07-17 |
HUP0200497A2 (en) | 2002-08-28 |
MXPA01009470A (es) | 2004-03-19 |
AU3632000A (en) | 2000-10-09 |
BR0009161A (pt) | 2002-01-22 |
ZA200107687B (en) | 2002-12-18 |
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